The Pesticide Manual PDF

A World Compendium
The Pesticide Manual

Sixteenth Edition
Supplementary Entries Extended
Editor: C. MacBean
Promoting the science and practice of sustainable crop production
2012 BCPC (British Crop Production Council)
All rights reserved. No part of this publication may be reproduced, stored in a retrieval system,
or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or
otherwise, without the prior permission of the copyright owner.
British Library Cataloguing in Publication Data. A catalogue record of this book is available from
the British Library.
ISBN 978 1 901396 86 7
First published 1968 Seventh edition 1983 Thirteenth edition 2003
Second edition 1971 Eighth edition 1987 Fourteenth edition 2006
Third edition 1972 Ninth edition 1991 Fifteenth edition 2009
Fourth edition 1974 Tenth edition* 1994
Fifth edition 1977 Eleventh edition 1997
Sixth edition 1979 Twelfth edition 2000
* The tenth edition incorporated The Agrochemicals Handbook, previously published by
The Royal Society of Chemistry.
Published by: BCPC, 7 Omni Business Centre, Omega Park, Alton, Hampshire, GU34 2QD, UK
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Disclaimer: Every effort has been made to ensure that all information in this edition of
The Pesticide Manual is correct at the time of going to press. However, the editor and the
publisher do not accept liability for any error or omission in the content, or for any loss,
damage or any other accident arising from the use of the products listed therein. Before
handling, storing or using any approved crop protection product, it is essential to follow the
instructions on the label.
iii
Supplementary Entries
These entries include (i) superseded materials, believed to be no longer manufactured,
or marketed, for crop protection use; (ii) some materials that are in the public domain
and believed to be in late stages of development; and (iii) materials that reached late
development but were ultimately not marketed.
These entries are short descriptions. For chemical materials, they may include the
following information:
Sequential entry number.
A header name, with an indication of the type of name (such as common name, chemical
name, etc.).
Chemical Abstracts Service Registry Number (CAS RN).
Approved common name (if different from the name in the header, or if other common
names have been approved by national bodies).
Molecular formula (M.f.).
Other names.
Code numbers (development codes).
The main former product or products.
For an explanation of this information see the Guide to Using the Main Entries, p. viii of
The Pesticide Manual Sixteenth Edition.
It is diffcult, in some cases, to be sure whether or not all commercial activity in a
substance has ceased; some of these superseded materials are known to be still in use
for non-agricultural purposes. The Editor will be grateful for details of any materials in this
section that are still in commercial, agricultural use; he can be contacted via the publishers,
or at pm@bcpc.org.
AC 94,377 1
AC 94,377
Plant growth regulator
NOMENCLATURE:
IUPAC name 1-(4-chloro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)cyclohexane-1-
carboxamide; 1-phthalimidocyclohexane-1-carboxamide
Chemical Abstracts name 1-(4-chloro-1,3-dihydro-1,3-dioxo-[2H]-isoindol-2-yl)-
cyclohexanecarboxamide CAS RN [51971676] Development codes AC 94,377;
CL 94,377 (both Cyanamid)
Smiles code NC(=O)C1(CCCCC1)N
2
C(=O)c3cccc(Cl)c3C2=O
PHYSICAL CHEMISTRY: Mol. wt. 306.7 M.f. C
15
H
15
ClN
2
O
3
Form White
crystalline solid. M.p. 193195 C Solubility In water 30 ppm (25 C). In acetone <2%,
N-methylpyrrolidone 35%, dichloromethane <2%, DMSO >20% (all 20 C).
COMMERCIALISATION:
History Evaluated by American Cyanamid Co.
APPLICATIONS:
Biochemistry Not known. Activity mimics that of gibberellic acid in various
phytohormone bioassays (J. C. Suttle & J. F. Hultstrand, Plant Physiology, 80 (5), 115 (1986)).
Uses Growth promoter, increasing the stem number, stem length and commercial
acceptability of cut stems in hybrid tea roses. Benefcial effects have been reported in other
crops. Formulation types SC.
PRODUCTS:
Discontinued products Surestem* (BASF).
MAMMALIAN TOXICOLOGY:
Oral Acute oral LD
50
for male and female rats >5000 mg/kg. Skin and eye Acute
percutaneous LD
50
for male and female rabbits >2000 mg/kg. Mildly irritating to eyes;
non-irritating to skin (male rabbits). Other Non-mutagenic in the Ames test, microbial
mutagenicity assay, and host-mediated assay.
Details PM12, Entry 3.
N
Cl
O
O
NH
2
O
2
The Pesticide Manual Sixteenth Edition BCPC 2012
acetic acid
ACD 10614; ACD 10435
Herbicide
NOMENCLATURE:
IUPAC name 1,1,1,7,7,7-hexafuoro-4-methyl-2,6-bis(trifuoromethyl)hept-3-ene-2,6-diol
(i) and tautomer 1,1,1,7,7,7-hexafuoro-4-methylene-2,6-bis(trifuoromethyl)heptane-2,6-
diol (ii); forming monosodium 1,1,1,7,7,7-hexafuoro-4-methyl-2,6-bis(trifuoromethyl)
hept-3-ene-2,6-diolate and monosodium 1,1,1,7,7,7-hexafuoro-4-methylene-2,6-
bis(trifuoromethyl)heptane-2,6-diolate
Chemical Abstracts name 1,1,1,7,7,7-hexafuoro-4-methyl-2,6-bis(trifuoromethyl)-3-
heptene-2,6-diol (i) and 1,1,1,7,7,7-hexafuoro-4-methylene-2,6-bis(trifuoromethyl)-2,6-
heptanediol (ii) CAS RN [756912] (i); [16202918] (ii); [19493948] monosodium
salts Development codes ACD 10 614 (i + ii); ACD 10 435 (monosodium salts)
10
H
8
F
12
O
2
Form Monosodium
salts form a colourless solid. M.p. 143145 C; monosodium salts >300 C Solubility
Practically insoluble in water, benzene, dichloromethane, xylene; soluble in alkali, acetone,
diethyl ether, DMF, DMSO, dioxane, bis(2-methoxyethyl) ether. Sodium salt soluble in water,
acetone, diethyl ether, dioxane, ethanol; insoluble in benzene, hexane.
COMMERCIALISATION:
History Herbicide evaluated by Allied Chemical Corp., Agrochemical Division (later
Hopkins Agricultural Chemical Co.).
APPLICATIONS:
Mode of action Selective herbicide. Uses Both the diol and its monosodium salt pre-em.
at 2.36.8 kg/ha controlled weeds selectively in cereals, maize, sorghum and soya beans;
and post-em. at 2.3 kg/ha in maize, sorghum, soya beans and wheat. Formulation types
EC (diol); GR (diol); SP (hydrated sodium salt); WP (diol).
Oral Diol: Acute oral LD
50
for fasted albino rats 17.8 mg/kg. Monosodium salt: 20.2 mg/kg.
Skin and eye Acute percutaneous LD
50
for albino rabbits 141 mg/kg.
Details PM4, p. 296.
acetic acid
Herbicide
See also The Manual of Biocontrol Agents 4th edn entry: 2:151
NOMENCLATURE:
CAS RN [64197]
PRODUCTS:
Other products Natures Glory Weed & Grass Killer (Ecoval).
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS:
EU Rev. Rep. SANCO/2602/08 (2008) EU Status (1107/2009) 2008/127/EC
acrylonitrile 3
acetoprole
Acaricide, insecticide, nematicide
NOMENCLATURE:
Common name (m) ac(toprole) (F-ISO); acetoprole (BSI, E-ISO)
IUPAC name ()-1-[5-amino-1-(2,6-dichloro-,,-trifuoro-p-tolyl)-4-(methylsulfnyl)
pyrazol-3-yl]ethanone
Chemical Abstracts name 1-[5-amino-1-[2,6-dichloro-4-(trifuoromethyl)
phenyl]-4-(methylsulfnyl)-1H-pyrazol-3-yl]ethanone CAS RN [209861585]
Development codes RPA 115782
13
H
10
Cl
2
F
3
N
3
O
2
S
COMMERCIALISATION:
Manufacturers Rhne-Poulenc
acrylonitrile
Insecticide
NOMENCLATURE:
Common name acrylonitrile (BSI, E-ISO, F-ISO, ESA, accepted in lieu of a common name)
IUPAC name acrylonitrile
Chemical Abstracts name 2-propenenitrile Other names vinyl cyanide
CAS RN [107131] EC no 2034665 Smiles code C=CC#N
3
H
3
N M.p. 82 C B.p. 77 C V.p.
1.37 107 mPa (25 C) S.g./density 0.801 (425 C); gaseous, 1.83 (air = 1) Solubility
In water ca. 8% (room temperature). Unlimited miscibility with common organic solvents.
Stability Readily polymerised, sometimes explosively. Addition of stabilizers is necessary.
F.p. 0 C. Mixtures with air having 317% vol./vol. acrylonitrile are fammable.
COMMERCIALISATION:
History Developed as a fumigant insecticide (The Chemistry of Acrylonitrile) by American
Cyanamid Co.
APPLICATIONS:
Biochemistry Respiratory action similar to that of hydrogen cyanide.
Mode of action Fumigant insecticide Uses Fumigant insecticide (ca. 510 g/m
3
) for
the control of pests in living areas and warehouses, machines in milling, baking, and food
processing. Formulation types TC.
PRODUCTS:
Discontinued products VCN* (Stauffer); Ventox* (Detia Degesch).
ANALYSIS:
In air, by absorption of the fumes in a measured quantity of air in an alkaline solution of
laurylmercaptan in isopropanol; the mercaptan is introduced at the double bond. Oxidation
of excess mercaptan to the disulfde with iodine solution and back-titration of the unused
4
afdopyropen
iodine or electrophotometric determination (J. Haslam & G. Newlands Analyst, 1955,
80, 50). Residues: cyanogen bromide, formed by the action of bromine (in uv light) on
acrylonitrile generated in a nitrogen stream, forms a dye with benzidine-pyridine which
can be determined colorimetrically (Man. Pestic. Residue Anal., 120). For gc determination
see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 259260. For spectrophotometric
determination of the pyridine-acrylonitrile complex see M. E. Hall & J. W. Stevens
(Anal. Chem. 1977, 49, 22772279). Methods reviewed by J. L. Daft in Comp. Anal. Profles,
Chapter 11.
EHC 28 (1983). JMPR Evaln. 5 (1965). HSG 1 (1986). ICSC 0092 (2001). CICAD 39 (2002).
IARC 71 (1999).
IARC Class 2B
Oral Acute oral LD
50
for rats 93 mg/kg. Skin and eye Liquid acrylonitrile permeates
through the skin. Inhalation Exposure to air containing 635 and 110 ml/m
3
is lethal
to rats and dogs, respectively, within 4 hours. ADI/RfD (JMPR) No ADI [1965]; (EPA)
RfD 0.01 mg/kg b.w. [1993]. Other It may be a carcinogen. Toxicity Class WHO (a.i.) FM.
ECClassifcation F; R11| R45| T; R23/24/25| Xi; R37/38, R41| R43| N; R51, R53| concn.
dep.
ECOTOXICOLOGY:
Bees Toxicity to bees not signifcant.
Details PM5, p. 3.
afdopyropen
Insecticide
NOMENCLATURE:
Common name afdopyropen (pa ISO)
IUPAC name [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropylcarbonyloxy)-
O
O
N
O
HO O
O
CH
3
H
2
C
H
3
C
O
O
H
CH
3
H
OH
AKH-7088 5
1,2,3,4,4a,5,6,6a,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-py-
ridyl)-11H,12H-benzo[f]pyrano[4,3-b]chromen-4-yl]methyl cyclopropanecarboxylate
Chemical Abstracts name [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)
oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-
11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl
cyclopropanecarboxylate CAS RN [915972177] Development codes ME5343
Smiles code O=C(OC(C1=CN=CC=C1)=C2)C3=C2O[C@@]([C@@H](O)C4)(C)
[C@@]([C@H]3O)([H])[C@]5(C)[C@@]4([H])[C@](C)(COC(C6CC6)=O)[C@@H]
(OC(C7CC7)=O)CC5
33
H
39
NO
9
AKH-7088
Herbicide
NOMENCLATURE:
IUPAC name methyl (EZ)-1-[5-(2-chloro-,,-trifuoro-p-tolyloxy)-2-nitrophenyl]-2-
methoxyethylideneamino-oxyacetate
Chemical Abstracts name methyl [[[1-[5-[2-chloro-4-(trifuoromethyl)phenoxy]-
2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate CAS RN [104459827]
Development codes AKH-7088 Smiles code COCC(=NOCC(=O)OC)
c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1[N+](=O)[O-]
19
H
16
ClF
3
N
2
O
7
Form Colourless
crystals. M.p. 57.758.1 C Solubility In water 1 mg/l (20 C). In dichloromethane >50%,
toluene 15% (both 20 C).
COMMERCIALISATION:
History Discovered in 1984 by Asahi Chemical Industry Co. Ltd. Reported by Y. Hayashi
et al. (Proc. Br. Crop Prot. Conf. Weeds, 1989, 1, 5358).
APPLICATIONS:
Biochemistry (E)- and (Z)- isomers show similar biological activity. Uses Post-emergence
control of broad-leaved weeds, including velvetleaf, cockleburs, and Jimson weed, in soya
beans, at 0.10.2 kg/ha.
Oral Acute oral LD
50
for rats 5000 mg/kg. Skin and eye Acute percutaneous LD
50
for rats
2000 mg/kg. Moderate skin irritation; non-irritating to eyes (male rabbits). Other Non-
mutagenic in the Ames test.
F
3
C
Cl
O NO
2
C
CH
2
OCH
3
NOCH
2
CO
2
CH
3
6
aldimorph
aldimorph
Fungicide
FRAC 5, G2; SBI class II, amine: morpholine
NOMENCLATURE:
Common name aldimorphe ((m) F-ISO); aldimorph (BSI, E-ISO)
IUPAC name 4-alkyl-2,5 (or 2,6) -dimethylmorpholine, mixed compounds where the
alkyl substituent may be octyl, decyl, dodecyl, tetradecyl or hexadecyl and where the main
component is 4-dodecyl-2,6-dimethylmorpholine
Chemical Abstracts name aldimorph CAS RN [91315150]
Development codes B 8243
18
H
37
NO (main component) Form
Colourless liquid. M.p. 27 to 19 C B.p. 110140 C /0.1 mbar V.p. 5.5 10
1
mPa
(21.8 C) Solubility In water c. 20 mg/l (25 C). Stability Very stable between pH 3 and
pH 10. Stable to light. On heating abovec. 60 C, gives a weak brown coloration.
COMMERCIALISATION:
Manufacturers Hermania
APPLICATIONS:
Biochemistry Ergosterol biosynthesis inhibitor, by inhibition of sterol reduction (sterol-
14
-reductase) and isomerisation (
8
to
7
-isomerase). Mode of action Systemic,
long-term, also curative action. Absorbed through leaves and roots. Inhibits formation
of haustoria in Erysiphe graminis. Uses Controls mildew on spring and winter barley.
Formulation types EC.
PRODUCTS:
Discontinued products Falimorph* (Fahlberg-List).
ANALYSIS:
Product analysis by acidimetric titration in non-aqueous medium. Residues by
extraction wth methanol, transfer to hexane, column chromatographic clean-up on
aluminium oxide, and colorimetric determination at 540 nm of coloured substances
released by hydrochloric acid from the methyl orange-active ingredient salt.
EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Oral Acute oral LD
50
for rats >3000 mice 9700 mg/kg. Skin and eye Dermal LD
50
for
guinea pigs 1430 mg/kg. Skin irritant. NOEL In 90 d feeding trials on rats, highest dose
without activity was 2 mg/kg b.w. daily. ADI/RfD (BfR) 0.01 mg/kg b.w. [1991]
Other Possible teratogen.
aldoxycarb 7
ECOTOXICOLOGY:
Fish LC
50
(96 h) for carp 2.83, salmon 0.38 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants The a.i. content in barley and wheat decreases from 18 mg/kg at application to 0.14
mg/kg after 30 d and 0.1 mg/kg after 45 and 57 d.
aldoxycarb
Acaricide, insecticide, nematicide
IRAC 1A
NOMENCLATURE:
Common name aldoxycarb (BSI, E-ISO, ANSI, ESA); aldoxycarbe ((m) F-ISO)
IUPAC name 2-mesyl-2-methylpropionaldehyde O-methylcarbamoyloxime; 2-methyl-2-
methylsulfonylpropionaldehyde O-methylcarbamoyloxime
Chemical Abstracts name 2-methyl-2-(methylsulfonyl)propanal O-[(methylamino)
carbonyl]oxime Other names aldicarb sulfone; sulfocarb CAS RN [1646884]
Development codes UC 21 865 Smiles code CNC(=O)ON=CC(C)(C)S(=O)(=O)C
7
H
14
N
2
O
4
S Form White crystalline
powder with a sulfurous odour. M.p. 140142 C V.p. 12 mPa (25 C) Henry 2.67
10
4
Pa m
3
mol
1
(calc.) Solubility In water c. 10 g/l (25 C). In chloroform 32, acetonitrile
74, methanol 30, dichloromethane 41, acetone 50 (all in g/l). Stability Stable, but
decomposition occurs above 140 C. Rapidly hydrolysed in acidic or alkaline media.
COMMERCIALISATION:
History Insecticide and nematicide reported by M. H. J. Weiden et al. (J. Econ. Entomol.,
1965, 58, 154). Introduced by Union Carbide Corp. (later Rhne-Poulenc Agrochimie).
Patents US 3217037 Manufacturers Rhne-Poulenc
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic; taken up through
roots. Uses Control of aphids, thrips, mites, nematodes, leafhoppers and other pests on
cotton, tobacco, peanuts, maize, potatoes, cole crops and vegetables. Could be applied as
a soil treatment, foliar spray, seed dressing or transplant water treatment. Phytotoxicity
Soya beans and french bean seedlings are not tolerant. Formulation types WP; GR;
SC; FS. Compatibility Not fully known, but has been found to be compatible with most
common herbicides, insecticides, nematicides and fungicides used on tobacco.
PRODUCTS:
Discontinued products Standak* (Rhne-Poulenc).
CH C
CH
3
CH
3
N O C
NHCH
3
O
CH
3
SO
2
8
aldrin
ANALYSIS:
Product analysis by i.r. spectrometry (CIPAC Handbook, 1980, 1A, 1094). Residues
determined by glc with FPD (R. T. Krause, J. Assoc. Offc. Anal. Chem., 1980, 63, 1114;
R. R. Romine, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 147; J. H. Smelt et al., loc. cit.).
In drinking water by rplc and fuorimetry of liberated methylamine (Environ. Chem. Methods).
EHC 64 (1986); a review of carbamate pesticides in general.
Oral Acute oral LD
50
for male rats 21.4 mg/kg. Skin and eye Acute percutaneous LD
50

for rats 1000, rabbits 200 mg/kg. No skin or eye irritation in standard tests. Inhalation
LC
50
(4 h) for rats 0.14 mg/l air (dust). NOEL In life-span feeding trials, NOEL for mice
9.6, rats 2.4 mg/kg. ADI/RfD (EPA) 0.001 mg/kg b.w. [1993]. Other No teratogenic,
reproductive or mutagenic effects observed. Toxicity Class WHO (a.i.) Ib EPA
(formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks 33.5 mg/kg. Dietary LC
50
(5 d) for mallard ducks
>10 000 mg/kg diet, bobwhite quail 5706 mg/kg diet. Fish LC
50
(96 h) for trout 40, bluegill
sunfsh 55.5 mg/l. Bees Low toxicity to bees.
ENVIRONMENTAL FATE:
Animals Degradation in animals is by hydrolysis of the carbamate ester to aldoxycarb
oxime, and elimination of the methylcarbamate group to give aldoxycarb nitrile.
Plants Degradation in plants is the same as in animals. Soil/Environment See aldicarb.
aldrin
Insecticide
IRAC 2A
NOMENCLATURE:
Common name HHDN (for pure material) (BSI, E-ISO, F-ISO, JMAF; exception USA);
aldrin (for material containing 95% HHDN) (BSI, E-ISO, ESA, JMAF); aldrine (for material
containing 95% HHDN) ((m) F-ISO)
IUPAC name (1R,4S,4aS,5S,8R,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-
1,4:5,8-dimethanonaphthalene; 1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-exo-1,4-
endo-5,8-dimethanonaphthalene
Chemical Abstracts name (1,4,4a,5,8,8a)-1,2,3,4,10,10-hexachloro-
1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene CAS RN [309002]
Cl
Cl
Cl
Cl
Cl
Cl
aldrin 9
EC no 2062158 Development codes Compound 118 (Hyman)
Smiles code ClC1=C(Cl)C2(Cl)C3C4CC(C=C4)C3C1(Cl)C2(Cl)Cl
12
H
8
Cl
6
Form Pure HHDN is a
colourless crystalline solid; aldrin is a tan to dark brown waxy solid. M.p. 104104.5 C
(HHDN); (aldrin 4960 C) B.p. 145 C /2 mmHg V.p. 8.6 mPa (20 C) Solubility In
water 0.027 mg/l (27 C). In acetone, benzene and xylene >600 g/l (27 C). Stability
Thermally stable up to 200 C. Stable between pH 4 and 8. Reacts with concentrated acids
and phenols in the presence of oxidising agents to give dieldrin.
COMMERCIALISATION:
History Insecticide reported by C. W. Kearns et al. (J. Econ. Entomol., 1949, 42, 27).
Introduced by J. Hyman & Co. and by Shell International Chemical Co., Ltd. Patents US
2635977 (to Hyman)
APPLICATIONS:
Biochemistry Antagonist of the GABA receptor-chloride channel complex.
Mode of action Non-systemic insecticide with contact, stomach, and respiratory action.
Uses Control of soil-dwelling insects including termites and ants at 0.55.0 kg/ha. Also
used for wood preservation. Formulation types DP; EC; WP; GR.
PRODUCTS:
Discontinued products Aldrex* (Shell); Octalene* (Sandoz).
ANALYSIS:
TC and formulation analysis by i.r. spectrometry (CIPAC Handbook, 1983, 1B, 1706;
AOAC Methods, 18th Ed., 961.05), by tlc (ibid., 972.05), by potentiometric titration of
liberated chloride ion (CIPAC Handbook, 1994, F, 190), or by glc. Residues determined by glc,
tlc or paper chromatography (AOAC Methods, 18th Ed., 970.52), or by glc with ECD (Anal.
Methods Pestic. Plant Growth Regul., 1972, 6, 268; Analyst (London), 1979, 104, 425; P.A.Greve &
W. B. F. Grevenstuk, Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1115; G. M. Telling,
J. Chromatogr., 1977, 137, 405; M. A. Luke et al., J. Assoc. Off. Anal. Chem., 1981, 64, 1187). See
also Pestic. Anal. Man., I, 208, 303, 503. In drinking water by glc with ECD (AOAC Methods,
18th Ed., 990.06).
EHC 91 (1989). JMPR Mtg. 65 (1992); JMPR Evaln. I 66 (1992); JMPR Evaln. 29 (1977). HSG 21
(1989). PDS 41 (1979). ICSC.774 (1998). IARC 5 (1974); Suppl. 7 (1987).
EU Status (1107/2009) Considered to be outside the scope of the Directive; already
banned, 79/117/EC, as amended by Regulation 850/2004.
IARC Class 3
Oral Acute oral LD
50
for rats 3867, guinea pigs 33, rabbits 5080, dogs 6595 mg/kg.
50
for rabbits 1525, rats 98 mg/kg. Toxic by skin
absorption. NOEL LOAEL 0.025 mg/kg b.w. (EPA IRIS) ADI/RfD (JMPR) 0.0001 mg/kg
b.w. (PTDI) [1994] (aldrin + dieldrin); (EPA) cRfD 0.00003 mg/kg b.w. [1988].
Water GV 0.03 ;g/l (sum of aldrin+dieldrin). Other Because aldrin is rapidly epoxidised
10
allidochlor
in living tissue, forming dieldrin (q.v.), the long term toxicology of dieldrin to laboratory
animals can be regarded as representative of aldrin. Toxicity Class WHO (a.i.) Ib EPA
(formulation) I ECClassifcation T; R24/25, R48/24/25| R40| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 6.59, mallard 52 mg/kg. Fish LC
50
(24 h) 0.018
0.089 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In living organisms, aldrin is rapidly epoxidised to dieldrin (q.v.).
Soil/Environment In soil and water, undergoes epoxidation to dieldrin (q.v.). Details
PM8, Entry 00120.
allidochlor
Herbicide
NOMENCLATURE:
Common name allidochlor (BSI, E-ISO); alidochlore ((m) F-ISO); CDAA (WSSA, JMAF)
IUPAC name N,N-diallyl-2-chloroacetamide
Chemical Abstracts name 2-chloro-N,N-di-2-propenylacetamide CAS RN [93710]
EC no 2022707 Development codes CP 6343 (Monsanto)
Smiles code ClCC(=O)N(CC=C)CC=C
8
H
12
ClNO Form Amber-coloured oil.
B.p. 74 C /0.3 mmHg V.p. 1250 mPa (20 C) K
ow
logP = 0.97 (Agchem. Desk Ref.) S.g./
density 1.088 (25 C) Solubility In water 20 g/kg (25 C). In chlorobenzene, chloroform,
cyclohexanone, ethanol, and xylene >500 g/kg (25 C); in hexane >200 g/kg (36 C).
Stability Stable to uv light; decomposes at 125 C.
COMMERCIALISATION:
History Herbicide reported by P. C. Hamm & A. J. Speziale (J. Agric. Food Chem., 1956, 4,
518). Introduced by Monsanto Co. Patents US 2864683
APPLICATIONS:
Biochemistry Inhibition of cell respiration. Mode of action Selective herbicide Uses A
selective pre-em. herbicide used to control annual grasses and certain broad-leaved weeds
in beans (various types), cabbages, celery, certain fruits, maize, onions, certain ornamentals,
sugar cane and sweet potatoes. Incorporated into soil after pre-em. application; also used
post-em. and absorbed by cotyledons of grass seedlings. Formulation types EC; GR.
PRODUCTS:
Discontinued products Randox* (Monsanto); Discontinued mixtures Randox-T*
(+ trichlorobenzyl chloride) (Monsanto).
ANALYSIS:
Product and residue analysis is by glc.
allyl alcohol 11
Oral Acute oral LD
50
50
for
rabbits 830 mg tech./kg. Corrosive to skin and eyes (rabbits). NOEL In 90 d feeding
trials, no adverse effect observed in rats and dogs at 200 mg/kg diet (highest rate tested).
Toxicity Class WHO (a.i.) IIECClassifcation Xn; R21/22| Xi; R36/38| N; R51, R53
ECOTOXICOLOGY:
Fish LC
50
for rainbow trout 2.0 mg/l. Bees Not toxic to bees when used as prescribed.
ENVIRONMENTAL FATE:
Plants In plants, it is readily metabolised to glycollic acid and diallylamine.
Soil/Environment Rapid hydrolytic cleavage of chlorine atom with formation of water-
soluble metabolites. There is oxidative attack on the allyl group. Glycolic acid is also a
metabolite. Loss from soil is mainly by microbial activity, but soil incorporation is needed
because of its volatility. Duration of activity 36 weeks, depending on soil.
allyl alcohol
Herbicide
NOMENCLATURE:
Common name allyl alcohol (BSI, ISO, accepted in lieu of common name)
IUPAC name allyl alcohol; prop-2-en-1-ol
Chemical Abstracts name 2-propen-1-ol CAS RN [107186] EC no 2034707
3
H
6
O Form Colourless, mobile liquid
with a pungent odour. M.p. forms a glass at 190 C B.p. 96.9 C V.p. 2.31 10
6
mPa
(20 C)
S.g./density 0.8535 at 20 C Solubility Miscible with water and common organic
solvents. Stability Polymerises on storage and therefore requires the addition of a
stabiliser. Stable in uv light. F.p. 32 C (open cup)
COMMERCIALISATION:
History Its experimental use as a herbicide frst reported in 1950.
APPLICATIONS:
Mode of action Inhibits germination. Uses Herbicide for control of weed and grass
seeds. Applied to nursery, forestry, vegetable, tobacco, and other seeds beds, at 85170
g in 50 000100 000 l water/ha. Also for the partial sterilisation of glasshouse soil (E. M.
Emmert & J. E. Klinker, Ky. Agric. Exp. Stn. Prog. Rep., 1950) at 18.4 g in 6.1 l water/m
2
of soil.
Formulation types TC.
ANALYSIS:
CH
2
CH
H
2
C
OH
12
allyxycarb
Product analysis by measurement of the bromine added across the double-bond or
acetylation of the hydroxyl group in the presence of pyridine. For a polarographic
determination see M. Jaworski and J. Bogaczek (Chem. Anal. (Warsaw) 1969, 14, 12471251),
reported in Fresenius Z. Anal. Chem. 1971, 257, 70. It may be detected by trapping in water
or sulfuric acid and oxidising to acrylaldehyde by chromic-sulfuric acid. For detection of
residues in soil before sowing, the biological cress root test is mostly applied.
ICSC 0095 (2000). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
for rats 64, mice 85 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits 89 mg/kg; absorbed rapidly through the skin. Lachrymatory and intensely
irritating to skin and mucous membranes. Inhalation High inhalation toxicity. NOEL
Highest oral dose without activity for male and female rats 4.8 and 6.2 mg/kg daily (15 w).
ADI/RfD (EPA) cRfD 0.005 mg/kg b.w. [1989]. Other Maximum acceptable concentration
in work-place atmosphere over an 8-hour work period 5 mg/m
3
. Toxicity Class WHO
(a.i.) IbECClassifcation R10| T; R23/24/25| Xi; R36/37/38| N; R50
ECOTOXICOLOGY:
Fish Toxic to fsh. Bees Not toxic to bees when used as prescribed.
ENVIRONMENTAL FATE:
Soil/Environment Metabolism not known. It disappears for the most part through
evaporation. Duration of activity 310 days depending on temperature, soil type, and
humidity.
Details PM6, p. 9.
allyxycarb
Insecticide
NOMENCLATURE:
Common name allyxycarb (BSI, E-ISO); allyxycarbe (F-ISO); APC (JMAF)
IUPAC name 4-diallylamino-3,5-xylyl methylcarbamate
Chemical Abstracts name 4-(di-2-propenylamino)-3,5-dimethylphenyl methylcarbamate
CAS RN [6392467] Development codes Bayer 50 282; A 546
Smiles code CNC(=O)Oc1cc(C)c(N(CC=C)CC=C)c(C)c1
16
H
22
N
2
O
2
COMMERCIALISATION:
History Insecticide introduced by Bayer AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor.
amibuzin 13
EHC 64 (1986; a review of carbamate pesticides in general).
Toxicity Class WHO (a.i.) O
Details PM4, p. 10.
alorac
NOMENCLATURE:
Common name alorac (BSI, E-ISO, (m) F-ISO)
IUPAC name (Z)-perchloro-4-oxopent-2-enoic acid;
(Z)-2,3,5,5,5-pentachloro-4-oxopent-2-enoic acid
Chemical Abstracts name (Z)-2,3,5,5,5-pentachloro-4-oxo-2-pentenoic acid
CAS RN [19360022] Smiles code OC(=O)/C(=C(/Cl)\C(=O)C(Cl)(Cl)Cl)/Cl;
without stereochemistry:OC(=O)C(=C(Cl)C(=O)C(Cl)(Cl)Cl)Cl
5
HCl
5
O
3
COMMERCIALISATION:
History Plant growth regulator.
ametridione
Herbicide
NOMENCLATURE:
Common name am(tridione) ((m) F-ISO); ametridione (BSI, E-ISO)
IUPAC name 1-amino-6-ethylthio-3-neopentyl-1,3,5-triazine-2,4(1H,3H)-dione
Chemical Abstracts name 1-amino-3-(2,2-dimethylpropyl)-6-(ethylthio)-1,3,5-triazine-
2,4(1H,3H)-dione CAS RN [78168931] Development codes BAY SSH 0860
Smiles code CCSc1nc(=O)n(CC(C)(C)C)c(=O)n1N
10
H
18
N
4
O
2
S
COMMERCIALISATION:
History Herbicide evaluated by Bayer AG.
amibuzin
Herbicide
NOMENCLATURE:
Common name amibuzine ((f) F-ISO); amibuzin (BSI, E-ISO)
IUPAC name 6-tert-butyl-3-dimethylamino-4-methyl-1,2,4-triazin-5(4H)-one
14
amidochlor
Chemical Abstracts name 3-(dimethylamino)-6-(1,1-dimethylethyl)-4-methyl-1,2,4-
triazin-5(4H)-one CAS RN [76636107] Development codes DIC 3202
Smiles code CN(C)c1nnc(c(=O)n1C)C(C)(C)C
10
H
18
N
4
O
COMMERCIALISATION:
History Herbicide developed by Bayer AG.
amidithion
Acaricide, insecticide
IRAC 1B
NOMENCLATURE:
Common name amidiphos ((m) France); amidithion (BSI, E-ISO, (m) F-ISO, ESA, ex-ANSI)
IUPAC name S-2-methoxyethylcarbamoylmethyl O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-(2-methoxyethyl)acetamide
Chemical Abstracts name S-[2-[(2-methoxyethyl)amino]-2-oxoethyl] O,O-dimethyl
phosphorodithioate CAS RN [919766] Development codes Ciba 2446
Smiles code COCCNC(=O)CSP(=S)(OC)OC
7
H
16
NO
4
PS
2
COMMERCIALISATION:
History Acaricide and insecticide (V. Dittrich & F. Bachman, Proc. Br. Insectic. Fungic. Conf.,
2nd, 1963, p. 421). Introduced by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
EHC 63 (1986; a general review of organophosphorus insecticides).
Toxicity Class WHO (a.i.) OECClassifcation Xn; R22
Details PM2, p. 16.
amidochlor
NOMENCLATURE:
Common name amidochlor (ANSI)
IUPAC name N-acetamidomethyl-2-chloro-2,6-diethylacetanilide
Chemical Abstracts name N-[(acetylamino)methyl]-2-chloro-N-(2,6-diethylphenyl)
acetamide CAS RN [40164678] Development codes MON 4620; CP-76 963
aminocarb 15
Smiles code CCc1cccc(CC)c1N(CNC(=O)C)C(=O)CCl
15
H
21
ClN
2
O
2
COMMERCIALISATION:
History Plant growth regulator introduced by Monsanto Co.
PRODUCTS:
Discontinued products Limit* (Monsanto).
amidothioate
IRAC 1B
NOMENCLATURE:
Common name amidothioate (JMAF)
IUPAC name O-2-chloro-4-methylthiophenyl O-methyl ethylphosphoramidothioate
Chemical Abstracts name O-[2-chloro-4-(methylthio)phenyl] O-methyl
ethylphosphoramidothioate CAS RN [54381269] Development codes NK-11
Smiles code CCNP(=S)(OC)Oc1ccc(SC)cc1Cl
10
H
15
ClNO
2
PS
2
COMMERCIALISATION:
History Acaricide introduced by Nippon Kayaku Co., Ltd.
APPLICATIONS:
aminocarb
Insecticide
IRAC 1A
NOMENCLATURE:
Common name aminocarb (BSI, E-ISO, ESA); aminocarbe ((m) F-ISO)
IUPAC name 4-dimethylamino-m-tolyl methylcarbamate
Chemical Abstracts name 4-(dimethylamino)-3-methylphenyl methylcarbamate
Other names DTMC CAS RN [2032599] EC no 2179907
Development codes Bayer 44 646; A 363
Smiles code CNC(=O)Oc1ccc(N(C)C)c(C)c1
11
H
16
N
2
O
2
Form Colourless
crystalline solid. M.p. 9394 C V.p. 2.3 mPa (EPA, 1988) Solubility In water 915 mg/
kg (20 C) (Agchem. Desk Ref.). Moderately soluble in aromatic solvents; soluble in polar
organic solvents.
COMMERCIALISATION:
16
amiprofos-methyl
History Insecticide reported by G. Unterstenhfer (Meded. Landbouwhogesch.
Opzoekingsstn. Staat Gent, 1963, 28, 758). Introduced by Bayer AG. Patents DE 1145162
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide
with contact and stomach action. Uses Mainly used against lepidopterous larvae and
other chewing insects; generally recommended at 75 g/100 l. Formulation types WP.
Compatibility Incompatible with highly alkaline pesticides.
PRODUCTS:
Discontinued products Matacil* (Bayer); Metacil* (Bayer).
ANALYSIS:
Product analysis by rplc (CIPAC Handbook, 1988, D, 7) or lc (AOAC Methods, 18th Ed., 985.02;
J. Assoc. Off. Anal. Chem., 1985, 68, 372, 6.A256.A30) or by uv spectroscopy (H. Niessen
& H. Frehse, Pfanz.-Nachr. Bayer (Engl. Ed.), 1963, 16, 205). Residues determined by uv
spectroscopy or by glc of a derivative (R. J. Argauer, J. Agric. Food Chem., 1969, 17, 888; E. R.
Holden et al., ibid., p.56; L. I. Butler & L. M. McDonough, ibid., 1968, 16, 403). See also Pestic.
Anal. Man., I, 302.
EHC 64 (1986; a review of carbamate pesticides in general). JMPR Evaln. 33 (1979).
ICSC 0097 (1994).
Oral Acute oral LD
50
50

for rats 275 mg/kg. NOEL In 2 y feeding trials, rats receiving 200 mg/kg diet showed no
symptom of poisoning. ADI/RfD (JMPR) No ADI [1979]. Other Acute i.p. LD
50
for rats
21 mg/kg. Toxicity Class WHO (a.i.) IbECClassifcation T; R24/25| N; R50, R53
ECOTOXICOLOGY:
Bees Toxic to bees.
amiprofos-methyl
Herbicide
HRAC K1 WSSA 3; phosphoroamidate
NOMENCLATURE:
Common name amiprofos-methyl (BSI, E-ISO, (m) F-ISO)
IUPAC name O-methyl O-2-nitro-p-tolyl isopropylphosphoramidothioate
Chemical Abstracts name O-methyl O-(4-methyl-2-nitrophenyl) (1-methylethyl)
phosphoramidothioate Other names amiprophos-methyl CAS RN [36001884]
Development codes BAY NTN 6867; NTN 2925
Smiles code COP(=S)(NC(C)C)Oc1ccc(C)cc1[N+](=O)[O-]
11
H
17
N
2
O
4
PS
ampropylfos 17
COMMERCIALISATION:
History Herbicide reported by M. Aya et al. (Zasso Kenkyu, 1973, (15), p. 20). Evaluated by
Bayer AG.
APPLICATIONS:
Biochemistry Microtubule assembly inhibition.
amiton; amiton hydrogen oxalate
IRAC 1B
NOMENCLATURE:
Common name amiton (BSI)
IUPAC name S-2-diethylaminoethyl O,O-diethyl phosphorothioate
Chemical Abstracts name S-[2-(diethylamino)ethyl] O,O-diethyl phosphorothioate
CAS RN [78535] amiton; [3734972] amiton hydrogen oxalate
Development codes R 5158 (amiton); R 6199 (amiton hydrogen oxalate)
PHYSICAL CHEMISTRY: Mol. wt. 269.3; (oxalate 359.4) M.f. C
10
H
24
NO
3
PS; (oxalate
C
12
H26NO7PS)
COMMERCIALISATION:
History Insecticide and acaricide reported by R. Ghosh & J. F. Newman (Chem. Ind.
(London), 1955, p. 118) and by G. L. Baldit (J. Sci. Food Agric., 1958, 9, 516). Evaluated by Plant
Protection Ltd (later ICI Agrochemicals).
APPLICATIONS:
PRODUCTS:
Discontinued products Tetram* (oxalate) (ICI).
ampropylfos
Fungicide
NOMENCLATURE:
Common name ampropylfos (BSI, E-ISO, (m) F-ISO)
IUPAC name (RS)-1-aminopropylphosphonic acid
HO P
OH
CHCH
2
CH
3
O NH
2
18
ampropylfos
Chemical Abstracts name ()-(1-aminopropyl)phosphonic acid
CAS RN [16606647] Development codes PNL-62
Smiles code CCC(N)P(=O)(O)O
3
H
10
NO
3
P Form White solid.
M.p. 264270 C V.p. 3.7 10
3
mPa (90 C) K
ow
logP = 3 S.g./density 0.5 Solubility
In water 139 g/l (21 C). In methanol 0.46, isopropanol 0.003, hexane, toluene,
dichloromethane, ethyl acetate, and acetone 0.0001 (all in g/l, 21 C). Stability Stable 2
y (pH 47, 20 C); stable >31 d
(pH 9, 25 C); stable 3 d (pH 4, 100 C). pKa pKa2 5.9, pKa3 10.4
COMMERCIALISATION:
History Fungicide discovered by KenoGard AB (later Rhne-Poulenc Agrochimie).
APPLICATIONS: Uses Control of covered smut, loose smut, Fusarium spp., leaf stripe,
and net blotch in barley, and leaf stripe and loose smut in oats. Formulation types SC.
PRODUCTS:
Discontinued mixtures Ravyl* (+ anthraquinone + myclobutanil) (Bayer).
ANALYSIS:
Product by hplc with uv detection at 220 nm.
Oral Acute oral LD
50
for rats >5000 mg/kg. Skin and eye Acute percutaneous LD
50
for
rats >2000 mg/kg. Non-sensitising to skin (guinea pigs). Non-irritating to skin of rabbits.
Inhalation LC
50
for rats >4 mg/l air. NOEL (90 d) for rats 100 mg/kg daily (only minimal
changes at 300 mg/kg daily). In 90 d feeding trials, 0.1% PNL 62 in the diet had no effect
on dogs after 13 w treatment (effects at 0.5% were minimal and there is no evidence
of systemic or target organ toxicity). Non-teratogenic to rats at 1000 mg/kg daily. Non-
teratogenic to rabbits at 10 mg/kg daily. Other Intravenous LD
50
for rats c. 1250 mg/kg.
Non-mutagenic in the Ames test and other mutagenicity tests.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail and mallard ducks >2000 mg/kg. Dietary LC
50
for
bobwhite quail and mallard ducks >5000 mg/kg. No observed neurotoxicity to hens.
Fish LC
50
(96 h) for rainbow trout, bluegill sunfsh, and mirror carp >135 mg/l.
Daphnia LC
50
(24 and 48 h) >100 mg/l. Algae EC
50
for Selenastrum capricornutum 54 mg/l.
Worms LC
50
for Eisenia foetida >1000 mg/kg.
ENVIRONMENTAL FATE:
Animals After oral administration to rats of a single dose of 200 mg ampropylfos/kg b.w.
there is a rapid absorption (about 50%) with peak concentration 1 h after dosage, and a
fast decline in a bioexponential manner with DT
50
c. 2 h in plasma, 50 h in blood. Similar
anabasine 19
decline is found after intravenous administration in rats. Whole body autoradiograms of
rats showed that
14
C-labelled ampropylfos is widely distributed in tissues as well as being
taken up to some extent into bone and blood cells. There is no evidence of
14
C-labelled
ampropylfos-related material crossing either the placental or blood brain barriers.
Plants Uptake of
14
C-labelled ampropylfos (applied as a seed dressing formulation at a
level of 400 mg/kg seed) from seeds of winter barley is very low.
Soil/Environment Ampropylfos is strongly bound to soil. The percentage of applied
14
C-labelled ampropylfos eluted from three standard soil types was 0.61 (sand), 0.035
(loamy sand), 0.925 (sandy loam) (
14
C-labelled ampropylfos applied in an amount
corresponding to a feld application rate of 1500 g/ha and water added equivalent to
200 mm rain). Ampropylfos is readily biodegradable in freshwater to levels of 81% and 79%
within 35 days at 22.5 2.5 C using unacclimatised and acclimatised inocula, respectively.
No photodegradation of ampropylfos was observed in artifcial sunlight after 34 days of
continuous irradiation in pH 5, pH 7, and pH 9 buffered aqueous solutions at 25 C (1 day
of artifcial sunlight was equivalent to 1.25 days of natural sunlight).
anabasine
Insecticide
NOMENCLATURE:
Common name anabasine (JMAF)
IUPAC name (S)-3-(piperidin-2-yl)pyridine
Chemical Abstracts name (S)-3-(2-piperidinyl)pyridine Other names 2-(3-pyridyl)
piperidine CAS RN [494520]; [13078041] racemate
Smiles code C1CCC(NC1)c2cccnc2
10
H
14
N
2
M.p. Freezes 9 C B.p. 281 C
S.g./density 1.048 (20 C) Solubility Miscible with water and most organic solvents.
COMMERCIALISATION:
Production Obtained, as racemic material, from Nicotiana glauca. History Insecticide
isolated in 1931 from Anabasis aphylla.
APPLICATIONS:
Biochemistry Agonist of nicotine acetylcholine receptors.
20
anilazine
anilazine
Fungicide
FRAC M8, M; multi-site: triazine fungicide
NOMENCLATURE:
Common name anilazine (BSI, E-ISO, (f) F-ISO); triazine (JMAF)
IUPAC name 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine; 2-chloro-N-(4,6-
dichloro-1,3,5-triazin-2-yl)aniline
Chemical Abstracts name 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine
CAS RN [101053] EC no 2029105 Development codes B-622 (Ethyl Corp.)
Smiles code Clc1ccccc1Nc2nc(Cl)nc(Cl)n2
9
H
5
Cl
3
N
4
Form Colourless to tan
crystals. M.p. 159 C
V.p. 8.2 10
4
mPa (20 C) K
ow
logP = 3.02 (20 C) Henry 2.82 10
5
Pa m
3
mol
1

(calc.) S.g./density 1.8 (20 C) Solubility In water 8 mg/l (20 C). In acetone 100,
chlorobenzene 60, toluene 50, xylene 40 (all in g/l, 30 C). In dichloromethane 90,
isopropanol 8, hexane 1.7 (all in g/l, 20 C). Stability Stable in neutral and slightly acidic
media. Hydrolysed on heating with alkalis; DT
50
(22 C) 730 h (pH 4), 790 h (pH 7), 22 h
(pH 9).
COMMERCIALISATION:
History Fungicide reported by C. N. Wolf et al. (Science, 1955, 121, 61). Introduced by the
Ethyl Corp. and later by Nippon Soda Co., Ltd and by Bayer AG. Patents US 2720480 (to
Ethyl Corp.) Manufacturers Bayer CropScience
APPLICATIONS:
Biochemistry Multi-site action. Mode of action Non-systemic foliar fungicide, with
protective action. Uses Control of Septoria spp. of wheat (glume blotch and on leaves)
was the main area of use. Also used for the control of early and late blights of potatoes
and tomatoes; anthracnose in cucurbits; leaf spot diseases (Alternaria, Cercospora, and
Septoria spp.) in many crops; Helminthosporium spp. in wheat and barley; brown patch,
dollar spot, snow mould, and other diseases of turf; Botrytis, Colletotrichum, Leptosphaeria,
and Pyrenophora spp. on many crops; etc. Also used on vegetables, ornamentals, berry fruit,
melons, water melons, coffee, and tobacco. Formulation types WP; SC. Compatibility
Incompatible with oils and alkaline materials.
PRODUCTS:
Discontinued products Dyrene* (Bayer); Kemate* (Bayer); Triazine* (Nippon Soda);
Triazin Jet* (Nippon Soda).
N N
N NH
Cl
Cl
Cl
anisuron 21
ANALYSIS:
Product analysis by lc (AOAC Methods, 18th Ed., 988.04; CIPAC Handbook, 1992, E, 5) or by
hydrolysis and measurement of the chloride liberated (P. F. Kane & K. G. Gillespie, J. Agric.
Food Chem., 1960, 8, 29). Methods for determination of residues were available from Bayer.
JMPR Mtg. 65 (1992); JMPR Evaln. I 66 (1992); JMPR Evaln. II 58 (1989).
Oral Acute oral LD
50
50
for
rats >5000 mg/kg. Severe eye irritant; mild skin irritant (rabbits). Inhalation LC
50
for rats
(4 h) >0.25 mg/l air (aerosol), (1 h) >0.7 mg/l air (dust). NOEL (2 y) for rats 2000, mice
1250 mg/kg diet; (18 mo) for dogs 40 mg/kg b.w. ADI/RfD (JMPR) 0.1 mg/kg b.w. [1989];
(EPA) 0.0004 mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) U; (WHO Recommended
Classifcation gives O) EPA (formulation) II ECClassifcation Xi; R36/38| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Virginia quail >2000 mg/kg b.w. LC
50
>5000 mg/kg. Fish LC
50
(96 h) for rainbow trout and golden orfe 0.15 mg/l. Daphnia LC
50

(48 h) 0.07 mg/l. Bees Not harmful to bees at recommended application rates.
ENVIRONMENTAL FATE:
Animals Elimination is quick; almost 98% is excreted within 72 h in the urine and faeces.
Plants In plants, one or both chlorine atoms in the triazine ring are substituted by
amino or thio groups, through reaction with amino acids, peptides, coenzymes, and other
endogenous substances in the cellular system of the plant (R. G. Owens Ann. New York Acad.
Sci. 1969, 160, 114132). Soil/Environment DT
50
in damp soilc. 12 h. Readily degraded in
different soils.
anisuron
Herbicide
NOMENCLATURE:
Common name anisuron (BSI) IUPAC name 1-(3,4-dichlorophenyl)-1-(4-
methoxybenzoyl)-3,3-dimethylurea Chemical Abstracts name N-(3,4-dichlorophenyl)-
N-[(dimethylamino)carbonyl]-4-methoxybenzamide CAS RN [2689432]
Smiles code COc1ccc(cc1)C(=O)N(C(=O)N(C)C)c2ccc(Cl)c(Cl)c2
17
H
16
Cl
2
N
2
O
3
COMMERCIALISATION:
History Herbicide.
22
antu
antu
Rodenticide
NOMENCLATURE:
Common name antu (BSI, E-ISO, (m) F-ISO, JMAF)
IUPAC name 1-(1-naphthyl)-2-thiourea
Chemical Abstracts name 1-naphthalenylthiourea Other names -naphthylthiourea
CAS RN [86884] EC no 2017063 Smiles code NC(=S)Nc1cccc2ccccc12
11
H
10
N
2
S Form Colourless
crystals; (tech. is a blue-grey powder). M.p. 198 C Solubility In water 600 mg/l (room
temperature). In acetone 24.3, triethyleneglycol 86 (both g/l, room temperature). Stability
Stable on exposure to air and to sunlight.
COMMERCIALISATION:
History Toxicity to rodents reported by C. F. Richter (J. Am. Med. Assoc., 1945, 129, 927;
Proc. Soc. Exp. Biol. Med., 1946, 63, 364). Patents US 2390848
APPLICATIONS: Uses A rodenticide specifc for adult Rattus norvegicus for which the
toxic dose is
68 mg/kg. It is less toxic to other Rattus spp. and tolerance is developed in rats by
repeated administration of sub-lethal doses. Formulation types RB; CP.
ANALYSIS:
Product analysis is by reaction with silver nitrate and titration of the liberated nitric acid.
(CIPAC Handbook, 1970, 1, 16; AOAC Methods, 18th Ed., 948.03, see 10th Ed., 4.132). Residues
determined by colorimetry of a derivative (E. Bremais & K. G. Bergner, Pharm. Zentralhalle,
1950, 89, 115).
ICSC.973 (2000). IARC 30 (1983); suppl. 7 (1987).
IARC Class 3
Oral Acute oral LD
50
for Norwegian rats 68 mg/kg; less toxic for other rat species;
surviving rats develop tolerance. Acute oral LD
50
for monkeys 4250, dogs 38 mg/kg.
Relatively safe for domestic animals; induces vomiting in dogs. Pigs are very sensitive.
Very low human toxicity. Other Naphthylamines, present as impurities, are carcinogenic.
Toxicity Class WHO (a.i.) IbECClassifcation T+; R28| R40
ECOTOXICOLOGY:
Birds Chickens are very sensitive.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, 40% is eliminated within 20 h. Metabolised
by lung and liver microsomal preparations into 1-naphthylurea and sulfur.
arsenous oxide 23
aramite
Acaricide
NOMENCLATURE:
Common name aramite (JMAF)
IUPAC name 2-(4-tert-butylphenoxy)-1-methylethyl 2-chloroethyl sulfte
Chemical Abstracts name 2-chloroethyl 2-[4-(1,1-dimethylethyl)phenoxy]-1-
methylethyl sulfte CAS RN [140578] Development codes 88-R
Smiles code CC(COc1ccc(cc1)C(C)(C)C)OS(=O)OCCCl
15
H
23
ClO
4
S
COMMERCIALISATION:
History Acaricide reported by W. D. Harris & J. W. Zukel (J. Agric. Food Chem., 1954, 2, 140).
Introduced by Uniroyal Chemical Co., Inc.
PRODUCTS:
Discontinued products Aramite* (Uniroyal); Niagaramite* (FMC).
ANALYSIS:
Residues determined colorimetrically (AOAC Methods, 18th Ed., 959.10, see 12th Ed.,
29.06729.071).
IARC 5 (1974). EU Status (1107/2009) Never notifed to the EU.
IARC Class 2B Toxicity Class WHO (a.i.) O
Details PM3, p. 73.
arsenous oxide
Rodenticide
NOMENCLATURE:
Common name arsenious acid (JMAF); arsenous oxide (E-ISO, accepted in lieu of a
common name); oxyde arsenieux (F-ISO, accepted in lieu of a common name.)
IUPAC name diarsenic trioxide; arsenic trioxide
Chemical Abstracts name arsenic oxide (As2O3) Other names arsenious oxide;
white arsenic CAS RN [1327533] EC no 2154814
Smiles code o1[as]2o[as]3o[as]1o[as](o2)o3
PHYSICAL CHEMISTRY: Mol. wt. 395.7 M.f. As
4
O
6
Form Colourless solid which
exists in rhombic, octahedral and amorphous forms. The amorphous form is unstable,
reverting to the octahedral. M.p. 272 C, subliming 125150 C (octahedral); 312 C
(rhombic) V.p. 8.8 kPa (312 C) (rhombic form) Solubility In water 17 g/l (16 C).
Practically insoluble in chloroform, diethyl ether, ethanol. Stability Stable in air but
oxidised slowly in acid media. Dissolves in alkali to form arsenites.
24
asomate
COMMERCIALISATION:
History Used as a rodenticide since the 16th century.
APPLICATIONS: Uses Used in baits to control Rattus norvegicus, R. rattus and Mus
musculus. It has also been used as a sheep dip to control ectoparasites. Formulation
types PA .
ANALYSIS:
Product analysis by titration with iodine (WHO Specifcations Insectic. (2nd Ed.). Residues
determined by atomic absorption spectroscopy (AOAC Methods, 14th Ed., 25.00125.007)
by colorimetry (ibid., 25.04125.055) or by the Gutzeit method (ibid., 25.045; 12th Ed.,
25.00625.009).
EHC 224 (2001). HSG 70 (1992). ICSC.378 (1997). IARC 23 (1980), Suppl 7 (1987).
IARC Class 1 (evaluation applies to arsenic compounds as a whole, not necessarily to all
individual compounds within the group)
Oral Acute oral LD
50
for rats 180200 mg a.i. (in carbohydrate or protein)/kg, 300 mg (in
bacon fat)/kg, 20 mg (in aqueous solution)/kg (E. Packman et al., J. Agric. Food Chem., 1961,
9, 271); for mice 34.463.5 mg/kg (J. W. E. Harrison, AMA Arch. Ind. Health, 1958, 17, 118).
Other It is extremely toxic to man, the minimum lethal dose is 2 mg/kg (H. O. Calvery,
J. Am. Med. Assoc., 1938, 111, 1722). It is non-cumulative and is eliminated from the animal
body in 742 d. Evidence of carcinogenicity in humans. Toxicity Class WHO (a.i.) Ia
(sodium arsenite Class Ib)ECClassifcation R45| T+; R28| C; R34| N; R50, R53
asomate
Chemosterilant
NOMENCLATURE:
IUPAC name arsinetriyl tris(dimethyldithiocarbamate); 1-{[bis(dimethylthiocarbamoyls
ulfanyl)arsanyl]sulfanyl}-N,N-dimethylmethanethioamide; tris(dimethylthiocarbamoylthio)
arsine Chemical Abstracts name N,N-dimethylcarbamodithioic acid anhydrosulfde with
arsenotrithious acid (3:1); tris(dimethyldithiocarbamato)arsenic
As
S S
S
N
S
CH
3
H
3
C
N
Me
Me
S
N
S H
3
C
CH
3
atraton 25
Other names TDDA; TTCA CAS RN [3586605]
Smiles code S=C(N(C)C)S[As](SC(N(C)C)=S)SC(N(C)C)=S
9
H
18
AsN
3
S
6
Form Yellow-green
crystals.
APPLICATIONS:
Mode of action Preventative and curative fungicide. Uses Used on apples and pears,
powdery mildew of cucumber, grapes etc. Also for rice blast. Formulation types WP.
Oral Acute oral LD
50
for rats 335-370 mg/kg. Skin and eye Strong skin irritant.
athidathion
Insecticide
IRAC 1B
NOMENCLATURE:
Common name athidathion (BSI, E-ISO, (m) F-ISO)
IUPAC name O,O-diethyl S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl
phosphorodithioate; 2-diethoxyphosphinothioylthiomethyl-5-methoxy-1,3,4-thiadiazol-
2(3H)-one
Chemical Abstracts name O,O-diethyl S-[(5-methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)
methyl] phosphorodithioate CAS RN [19691806] Development codes G 13 006
Smiles code CCOP(=S)(OCC)SCn1nc(OC)sc1=O
8
H
15
N
2
O
4
PS
3
COMMERCIALISATION:
History Insecticide reported by K. Rfenacht (Helv. Chim. Acta, 1968, 51, 518). Introduced
by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
PRODUCTS:
Discontinued products Deltacron* (Geigy).
atraton
Herbicide
NOMENCLATURE:
Common name atraton (BSI, E-ISO, (f) F-ISO); atratone ((f) France, former name (BSI))
IUPAC name N
2
-ethyl-N4-isopropyl-6-methoxy-1,3,5-triazine-2,4-diamine
26
azafenidin
Chemical Abstracts name N-ethyl-6-methoxy-N-(1-methylethyl)-1,3,5-triazine-2,4-
diamine CAS RN [1610179] Development codes G 32 293
Smiles code CCNc1nc(NC(C)C)nc(OC)n1
9
H
17
N
5
O M.p. 9496 C V.p. 3.8 mPa
(20 C) Henry 4.46 10
4
Pa m
3
mol
1
(calc.) Solubility In water 0.18% (20 C). Soluble
in ketones, esters, ether, alcohols and other organic solvents. Stability Stable in neutral,
weakly acidic and weakly basic media. Hydrolysed by warm acids and alkalis.
COMMERCIALISATION:
History Herbicide reported by E. Knsli (Phytiatr.-Phytopharm., 1958, 7, 81). Introduced by
J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
Biochemistry Interferes with photosynthesis and other enzymic processes. Uses
Selective herbicide used to protect sugar cane. Was also a component in total herbicide
mixtures. Formulation types WP; EC.
ANALYSIS:
Product by extraction with ether and titration of one amino group with perchloric acid
(Anal. Methods Pestic. Plant Growth Regul., 4, 28, 173). Residues by extraction with methylene
chloride, hydrolysis with 0.1 N sulphuric acid, and spectrophotometric determination
of the hydroxy derivative at 240 nm (Anal. Methods Pestic. Plant Growth Regul. 4, 28). For
determination by tlc, spectrophotometry, and gc, see Man. Pestic. Residue Anal., 6AC. For
gc determination with prometon as internal standard, see Anal. Methods Pestic. Plant Growth
Regul. 1972, 6, 597599. In drinking water by glc with NPD (AOAC Methods, 18th Ed.,
991.07).
Oral Acute oral LD
50
for rats 14652400, mice 905 mg/kg. Skin and eye Feeding 50%
atraton to rats at 10 and 200 mg/kg b.w. for 90 d produces no signs of illness.
ENVIRONMENTAL FATE:
Soil/Environment Replacement of the methoxy group at C-2 by hydrolysis via the
hydroxyl group. Dealkylation of the amino substituents at C-4 and C-6. Possibly opening of
the triazine ring.
azafenidin
Herbicide
N
N
N
O
Cl
Cl
O CH
2
C
CH
azafenidin 27
HRAC E WSSA 14; triazolinone
NOMENCLATURE:
Common name azaf(nidine) ((f) F-ISO); azafenidin (BSI, E-ISO)
IUPAC name 2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-
triazolo[4,3-a]pyridin-3(2H)-one
Chemical Abstracts name 2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-5,6,7,8-
tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one CAS RN [68049832]
Development codes R6447; DPX-R6447; IN-R6447 (all DuPont)
Smiles code Clc1cc(Cl)c(cc1OCC#C)n2nc3CCCCn3c2=O
PHYSICAL CHEMISTRY:
Composition Tech. isc. 97% pure. Mol. wt. 338.2 M.f. C
15
H
13
Cl
2
N
3
O
2
Form White
powdered solid; (tech. is a rust-coloured solid with a pungent odour). M.p. 168168.5 C
V.p. 1 10
6
mPa (20 C) K
ow
logP = 2.7 S.g./density 1.4 (20 C) Solubility In water 16
ppm (pH 7). Stability Stable to hydrolysis; aqueous photolysis DT
50
c. 12 h.
COMMERCIALISATION:
History Evaluated by E. I. du Pont de Nemours & Co. Reported by L. Amuti et al. (Proc. Br.
Crop Prot. Conf. Weeds 1997, 1, p. 59).
Manufacturers DuPont
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Absorbed through
the roots and shoots. Weakly xylem or phloem mobile, hence has limited post-emergence
activity. However, it improves the effcacy of other post-emergence herbicides, such as
glyphosate, and increases the speed of action of contact herbicides. Uses Intended for
use as a pre-emergence, and, in mixture, post-emergence, herbicide in citrus, grapes, olives,
sugar cane and other perennial crops; active on both annual and perennial weeds, and
applied at 240 g/ha. Formulation types WG .
PRODUCTS:
Discontinued products Evolus* (Europe) (DuPont); Milestone* (USA) (DuPont).
EU Status (1107/2009) Not approved, 2002/949/EC.
Oral Acute oral LD
50
50
for
rabbits >2000 mg/kg. Not an eye or skin irritant. Not a skin sensitiser. Inhalation LC
50
for
rats >5.3 mg/l. NOEL (90 d) for male and female rats 50, male mice 50, female mice 300,
dogs 10 ppm. Other Negative in Ames test. ECClassifcation T; R48/22| R61, R62| N;
R50, R53| concn. dep.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail and mallard ducks >2250 mg/kg. LC
50
(8 d) for
bobwhite quail and mallard ducks >5620 ppm. Fish LC
50
(96 h) for rainbow trout 33,
bluegill sunfsh 48 mg/l. Daphnia EC
50
(48 h) 38 mg/l. Algae EC
50
(120 h) for Selenastrum
capricornutum 0.94 ;g/l. Bees LD
50
(oral) >20 g/bee; (contact) >100 g/bee.
28
aziprotryne
ENVIRONMENTAL FATE:
Soil/Environment Degrades in soil by microbial and photolytic processes. In the feld, in
a range of 4 soils, mean DT
50
c. 25 d, mean DT90c. 169 d. Mean K
oc
298; there was minimal
movement in soil column leaching studies and azafenidin is not expected to leach into
groundwater. It is expected to dissipate rapidly through photolysis in natural waters.
aziprotryne
Herbicide
NOMENCLATURE:
Common name aziprotryne (BSI, E-ISO, (f) F-ISO); aziprotryn (USA)
IUPAC name 4-azido-N-isopropyl-6-methylthio-1,3,5-triazin-2-ylamine
Chemical Abstracts name 4-azido-N-(1-methylethyl)-6-(methylthio)-1,3,5-triazin-2-
amine CAS RN [4658280] Development codes C 7019
Smiles code CSc1nc(NC(C)C)nc(N=[N]=[N])n1
7
H
11
N
7
S Form Colourless crystalline
powder. M.p. 94.595.5 C V.p. 0.267 mPa (20 C) Henry 1.09 10
3
Pa m
3
mol
1

dichloromethane 37, ethyl acetate 12, isopropanol 14, benzene 4 (all in g/kg, 20 C).
Stability Stable in neutral and slightly acidic media. Hydrolysed slowly in slightly alkaline
media.
COMMERCIALISATION:
History Herbicide reported by D. H. Green et al. (C. R. Journ. Etud. Herbic. Conf.
COLUMA, 4th, 1967, 1, 1). Introduced by Ciba AG (later Novartis Crop Protection AG).
Patents BE 656233; GB 1093376 Manufacturers Novartis
APPLICATIONS:
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II receptor
site. Mode of action Selective herbicide, absorbed through the roots and foliage. Uses
Control of a wide range of annual broad-leaved weeds and some grasses in brassicas
(except caulifowers), onions, leeks, garlic, shallots, fennel, peas, beans, black salsify, and
oilseed rape. Applied pre- or post-emergence. Phytotoxicity Phytotoxic to caulifowers.
Formulation types WP.
PRODUCTS:
Discontinued products Brasoran* (Novartis); Mesoranil* (Ciba-Geigy).
N N
N CH
3
S NHCH(CH
3
)
2
N
3
azobenzene 29
ANALYSIS:
Product analysis by glc. Residues determined by glc using MCD.
Oral Acute oral LD
50
50

for rats >3000 mg/kg. Mild eye irritant; non-irritating to skin. Inhalation LC
50
(6 h) for rats
>0.208 mg/l. NOEL (90 d) for rats 50 mg/kg daily; for dogs 50 mg/kg daily.
Toxicity Class WHO (a.i.) U EPA (formulation) III
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and quail >4000 mg/kg. Fish LC
50
(96 h) for
bluegill sunfsh and largemouth bass >1 mg/l. Bees Not toxic to bees.
azithiram
Fungicide
NOMENCLATURE:
Common name azithiram (BSI, E-ISO); azithirame ((m) F-ISO)
IUPAC name bis(3,3-dimethylthiocarbazoyl) disulfde; N,N-bis(dimethylamino)thiuram
disulfde
Chemical Abstracts name 2,2,2,2-tetramethylthioperoxydicarbonic dihydrazide
([[(CH3)2NNH]C(S)]2S2) CAS RN [5834946] Development codes PP447
Smiles code CN(C)NC(=S)SSC(=S)NN(C)C
6
H
14
N
4
S
4
COMMERCIALISATION:
History Fungicide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).
azobenzene
Acaricide
NOMENCLATURE:
Common name azobenzene (BSI, E-ISO, F-ISO, accepted in lieu of a common name)
IUPAC name azobenzene
Chemical Abstracts name diphenyldiazene CAS RN [103333]
Smiles code N(=Nc1ccccc1)c2ccccc2
12
H
10
N
2
COMMERCIALISATION:
History Acaricidal activity reported by W. E. Blauvelt (N. Y. State Flower Grow. Bull., 1945,
30
azoxybenzene
No. 2). Was mainly used in glasshouses as a smoke.
ECClassifcation R45; R40| Xn; R20/22 R48/22| N; R50/53
Details PM4, p. 27.
azothoate
IRAC 1B
NOMENCLATURE:
Common name azothoate (BSI, E-ISO, (m) F-ISO)
IUPAC name O-4-(4-chlorophenylazo)phenyl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-[4-[(4-chlorophenyl)azo]phenyl] O,O-dimethyl
phosphorothioate CAS RN [5834968] EC no 2274193
Development codes L 1058 Smiles code COP(=S)(OC)Oc1ccc(N=Nc2ccc(Cl)cc2)cc1
14
H
14
ClN
2
O
3
PS
COMMERCIALISATION:
History Insecticide and acaricide introduced by Montecatini S.p.A. (later Agrimont S.p.A.).
APPLICATIONS:
Toxicity Class WHO (a.i.) OECClassifcation Xn; R20/22
azoxybenzene
NOMENCLATURE:
IUPAC name azoxybenzene
Chemical Abstracts name diphenyldiazene 1-oxide Other names fenazox
CAS RN [495487] EC no 2078021
12
H
10
N
2
O Form Pale yellow needles.
M.p. 3838.5 C V.p. 13 mPa (20 C) S.g./density 1.159 (20 C) Solubility In water 3.4
mg/kg (25 C). In ethanol 285, groundnut oil 760 g/kg (26 C); in ligroin 435 g/kg (10 C).
Stability Converted to o-hydroxyazobenzene by irradiation, and to p-hydroxyazobenzene
in acidic media. Stable in strongly alkaline media.
COMMERCIALISATION:
Manufacturers Fahlberg-List
barban 31
APPLICATIONS:
Mode of action Non-systemic, with contact action. Uses Control of mites and whitefy
on fruit trees, vines, hops, soya beans, ornamentals, vegetables and glasshouse crops.
PRODUCTS:
Discontinued products Fentoxan* (Fahlberg-List).
ANALYSIS:
Product by glc with FID. Residues by tlc, or by glc with ECD.
Oral Acute oral LD
50
50
for
rabbits 1350 mg/kg. NOEL (90 d) for rats 1 mg/kg daily. Other Non-carcinogenic and
non-mutagenic. ECClassifcation Xn; R20/22
ECOTOXICOLOGY:
Fish LC
50
(96 h) for carp 3, rainbow trout 2.7 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants Rapidly metabolised, initially to o-hydroxyazobenzene.
barban
Herbicide
NOMENCLATURE:
Common name chlorinat* (former exception, USSR); CBN (JMAF); barbanate (Republic
of South Africa); barbane ((m) F-ISO); barban (BSI, E-ISO, ANSI, WSSA)
IUPAC name 4-chlorobut-2-ynyl 3-chlorocarbanilate
Chemical Abstracts name 4-chloro-2-butynyl (3-chlorophenyl)carbamate
CAS RN [101279] EC no 2029304 Development codes CS-847 (Spencer
Chemicals) Smiles code ClCC#CCOC(=O)Nc1cccc(Cl)c1
11
H
9
Cl
2
NO
2
Form Cystalline solid;
(tech. is a tan solid).
M.p. 7576 C; (tech., 60 C) V.p. 0.05 mPa (25 C) Henry 1.17 10
3
Pa m
3
mol
1
(calc.)
S.g./density 1.403 (25 C, tech.) Solubility In water 11 mg/l (25 C). In benzene 327,
1,2-dichloroethane 546, hexane 1.4, kerosene 3.9, xylene 279 (all in g/l, 25 C).
Stability Tech. decomposes at 224 C. Stable under normal conditions of use; hydrolysis is
very rapid in alkali with displacement of the terminal chlorine substituent, DT
50
58 sec (pH
13, 25 C).
COMMERCIALISATION:
History Herbicide reported by A. D. Brown (Proc. North Cent. Weed Control Conf., 1958, 15,
98). Introduced by the Spencer Chemical Co. and later Velsicol Chemical Corp. Patents
US 2906614
32
barban
APPLICATIONS:
Biochemistry Acts by interfering with cell division. Mode of action Selective herbicide,
absorbed principally by the foliage, with limited translocation in the apoplast. Uses A
selective post-em. herbicide controlling wild oats in barley at the 1.52.5 leaf stage, and
broad beans, feld fax, lentils, lucerne, mustard, oilseed rape, saffower, soya beans, sugar
beet, sunfowers, wheat, Russian wild rye and other grasses.
Phytotoxicity Phytotoxic to oats and some varieties of rye. Formulation types EC.
PRODUCTS:
Discontinued products B25* (FBC); Carbyne* (Spencer Chemicals).
ANALYSIS:
Product analysis by uv spectrometry (K. J. Bombaugh & W. C. Bull, J. Agric. Food Chem., 1961,
9, 386). Residues determined by hplc or by hydrolysis to 3-chloroaniline derivatives which
are measured by glc (R. J. Harris & R. J. Whiteoak, Analyst (London), 1972, 97, 294). See also
Pestic. Anal. Man., II, 180.268. In water, by lc with uv detection (AOAC Methods, 18th Ed.,
992.14).
EHC 64 (1986) is a general review of pesticides with a carbamate chemical structure. EU
Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Oral Acute oral LD
50
for rats 13761429 mg/kg. Skin and eye Acute percutaneous LD50
for rabbits >20 000, rats >1600 mg/kg. Mildly irritating to the skin of rabbits and produces
a delayed skin sensitisation in guinea-pigs. It has been reported as a skin sensitiser in man;
skin contact should be avoided by using plastic protective clothing. Inhalation LC
50
(4
h) for rats >28 mg/l air. NOEL (2 y) for rats 150 mg/kg diet, for dogs 5 mg/kg diet. In a
3-generation reproduction study in rats, NOEL 957 mg/kg diet Other Not teratogenic in
rats at 87 mg/kg daily. Non-mutagenic to mammals by in vivo and in vitro tests.
Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and bobwhite quail >10 000 mg/kg diet.
Fish LC50 (96 h) for rainbow trout 0.6, bluegill sunfsh 1.2, goldfsh and guppies 1.3 mg/l.
Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats and rabbits, barban is not easily absorbed through the skin. In rats,
metabolism involves hydrolysis of the carbamate group, with formation of well known
m-chloroaniline metabolites. There is no accumulation of barban or its metabolites in
tissue, and they are rapidly excreted, principally in the urine. Plants Degraded rapidly in
most plants. Metabolites include 3-chloroaniline and a glutathione conjugate.
Soil/Environment In soil, degradation involves hydrolytic cleavage of the chlorobutynyl
group, followed by decomposition of the carbamic acid so formed, with evolution of CO
2
,
to give 3-chloroaniline. Duration of residual activity in soil, following an application rate of
3 l/ha, is c. 23 months.
barium polysulfde 33
barium carbonate
Rodenticide
NOMENCLATURE:
Common name barium carbonate (JMAF) IUPAC name barium carbonate (I)
Chemical Abstracts name (I) CAS RN [513779] EC no 2081673
Smiles code [Ba+2].[O-]C(=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 197.3 M.f. CBaO
3
COMMERCIALISATION:
History Used as a rodenticide for many years.
Toxicity Class WHO (a.i.) OECClassifcation barium salts (with exceptions) are Xn;
R20/22 (concentration-dependent)
Details PM5, p. 28.
barium polysulfde
Fungicide, insecticide
NOMENCLATURE:
Common name barium polysulfde (E-ISO, is accepted in lieu of a common name);
polysulfure de baryum (F-ISO)
IUPAC name barium polysulfde (I)
Chemical Abstracts name (I) CAS RN [50864670]
PHYSICAL CHEMISTRY:
M.f. BaS
x
COMMERCIALISATION:
History Insecticide and fungicide introduced by Bayer AG.
PRODUCTS:
Discontinued products Florbario* (Sariaf); Solbar* (Bayer); Tiobar* (Farmoplant).
ECClassifcation barium salts (with exceptions) are Xn; R20/22 (concentration-
dependent)
34
Bayer 22/190
Bayer 22/190
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name O-3-chloro-4-nitrophenyl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-(3-chloro-4-nitrophenyl) O,O-dimethyl phosphorothioate
Other names chlorthion CAS RN [500287] EC no 2079025
Development codes Bayer 22/190
Smiles code COP(=S)(OC)Oc1ccc([N+](=O)[O-])c(Cl)c1
8
H
9
ClNO
5
PS M.p. 21 C B.p. 136 C
/0.3 mbar; 112 C /0.05 mbar V.p. 5.5 10
1
mPa (20 C) Henry 4.09 10
3
Pa m
3
mol
1
(calc.) S.g./density 1.433 (420 C) Solubility In water 40 mg/l (20 C). Readily
soluble in common organic solvents with the exception of mineral oils. Stability Rapidly
hydrolysed in alkaline media, more slowly in the presence of acids.
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Insecticide with contact,
stomach, and respiratory action. Uses Insecticidal control of aphids and sucking and
biting insects in general in fruit, vine, and feld cultivation and forestry, especially control
of the mangold fy and sawfy. Phytotoxicity Phytotoxic to a few varieties of apple (e.g.
McIntosh). Formulation types WP; DP .
PRODUCTS:
Discontinued products Chlorthion* (Bayer).
ANALYSIS:
Product by extraction with ether or petroluem ether, washing with 1% sodium carbonate
solution, reduction of the nitro group with zinc dust in glacial acetic acid/hydrochloric acid
(9:1), and titration of the amine with sodium nitrite and iodine-starch (WHO Specifcations
for Pesticide, 2nd edn, Geneva, 1961). Residues: depending on the moisture content of the
sample, extraction with either acetone or chloroform, clean-up by liquid-liquid extraction
or column chromatography, and gc determination with ECD (Man. Pestic. Residue Anal.,22).
For colorimetric determination see Anal. Methods Pestic. Plant Growth Regul., 2,78, and for gc
with ECD see Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 322324.
JMPR Evaln. 4 (1965).
Oral Acute oral LD
50
for rats 6251500 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats 15004500 mg/kg. NOEL Administration of 10, 20, and 50 mg/kg diet for
Bayer 32394 35
120 d produces no histopathological changes, apart from cholinesterase inhibition at
10 mg/kg. ADI/RfD (JMPR) No ADI [1965] ECClassifcation Xn; R20/21/22| N; R50,
R53| concn. dep.
ECOTOXICOLOGY:
Fish Toxic to fsh and animals of fsh diet. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Rapidly hydrolysed to dimethyl thiophosphate and 3-chloro-4-
nitrophenol. To a limited extent, there is oxidation to the phosphate and hydrolysis to
phosphoric acid and 3-chloronitrophenol.
Bayer 22408
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name O,O-diethyl naphthalene-1,8-dicarboximido-oxyphosphonothioate;
O,O-diethyl naphthalimido-oxyphosphonothioate; N-diethoxyphosphinothioyl=
oxynaphthalene-1,8-dicarboximide
Chemical Abstracts name 2-[(diethoxyphosphinothioyl)oxy]-1H-benz[de]isoquinoline-
1,3(2H)-dione CAS RN [2668920] Development codes Bayer 22408; S 125
Smiles code CCOP(=S)(OCC)ON1C(=O)c2cccc3cccc(C1=O)c23
16
H
16
NO
5
PS
COMMERCIALISATION:
History Insecticide, discovered by W. Lorenz, evaluated by Bayer AG.
APPLICATIONS:
Bayer 32394
Fungicide
NOMENCLATURE:
IUPAC name tris(1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexacyanoferrate
Chemical Abstracts name tris[1-dodecyl-3-methyl-2-phenyl-1H-
benzimidazolium] hexakis(cyano-C)ferrate CAS RN [7276586], formerly
[64070979] and [16071899] Development codes Bayer 32394; B 169
Ferricyanide Smiles code CCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.
CCCCCCCCCCCCn1c(c2ccccc2)[n+](C)c3ccccc13.CCCCCCCCCCCCn1c(c2ccccc2)
[n+](C)c3ccccc13.N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N
36
bencarbazone
84
H
111
FeN
12
COMMERCIALISATION:
History Fungicide introduced by Bayer AG.
APPLICATIONS:
Mode of action Protective fungicide.
PRODUCTS:
Discontinued products Fungilon* (Bayer).
bencarbazone
Herbicide
NOMENCLATURE:
Common name bencarbazone (BSI, E-ISO, (f) F-ISO)
IUPAC name 4-[4,5-dihydro-4-methyl-5-oxo-3-(trifuoromethyl)-1H-1,2,4-triazol-1-yl]-2-
[(ethylsulfonyl)amino]-5-fuorobenzenecarbothioamide
Chemical Abstracts name 4-[4,5-dihydro-4-methyl-5-oxo-3-(trifuoromethyl)-1H-1,2,4-
triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fuorobenzenecarbothioamide
CAS RN [173980171] Development codes TM-435; HWH 4991
13
H
13
F
4
N
5
O
3
S
2
Form Yellowish-grey
powder. M.p. 202 C
K
ow
logP = 0.179 (pH 7.5) Solubility In water 0.105 g/l (pH 7). Stability Hydrolysis
DT
50
>500 h (pH 4), 241 h (pH 7), 174 h (pH 9) (all at 50 C).
COMMERCIALISATION:
History Herbicide discovered by Bayer CropScience; licensed to Tomen Agro (later Arysta
LifeScience Corporation) in 2001.
APPLICATIONS: Uses Evaluated for post-emergence control of broad-leaved weeds in
maize and cereals.
Oral Acute oral LD
50
for rats >2500 mg/kg. Skin and eye Not a skin or eye irritant. Is a
skin sensitiser (guinea pigs). Inhalation LC
50
(4 h) for rats >5045 mg/l. NOEL (13 w) for
dogs 6 mg/kg.
C
NH
2
S
F
NHSO
2
CH
2
CH
3
N
N
N
CF
3
O
CH
3
benodanil 37
ECOTOXICOLOGY:
Birds LD
50
(14 d) for bobwhite quail >2000 mg/kg daily. Fish LC
50
(96 h, static) for trout
>100 mg/l. Daphnia EC
50
(48 h, static) >10 mg/l. Algae IC50 (72 h, static) for Selenastrum
capricornutum 2 mg/l. Worms LC
50
(14 d) for earthworms >1000 mg/kg dry soil.
benclothiaz
Nematicide
NOMENCLATURE:
Common name benclothiaze ((m) F-ISO); benclothiaz (BSI, E-ISO)
IUPAC name 7-chloro-1,2-benzothiazole
Chemical Abstracts name 7-chloro-1,2-benzisothiazole CAS RN [89583904]
Development codes CGA 235 860
7
H
4
ClNS
COMMERCIALISATION:
History Nematicide evaluated by Novartis AG.
benodanil
Fungicide
FRAC 7, C2
NOMENCLATURE:
Common name benodanil (BSI, E-ISO, (m) F-ISO) IUPAC name 2-iodobenzanilide
Chemical Abstracts name 2-iodo-N-phenylbenzamide CAS RN [15310017]
Development codes BAS 3170F (BASF) Smiles code Ic1ccccc1C(=O)Nc2ccccc2
13
H
10
INO Form Colourless crystals.
M.p. 137 C V.p. <0.010 mPa (20 C) Henry <1.6 10
4
Pa m
3
mol
1
(20 C, calc.)
Solubility In water 20 mg/l (20 C). In acetone 401, ethyl acetate 120, ethanol 93,
chloroform 77 (all in g/kg, 20 C).
Stability Stable 50 C; no hydrolysis (20 C) at pH 1 or pH 13.
N
S
Cl
C
I
O
N
H
38
benquinox
COMMERCIALISATION:
History Fungicide reported by E. H. Pommer et al., at the 39th Deutsche
Pfanzenschutztagung, Stuttgart, 1973 and by F. Lcher et al. (Meded. Fac. Landbouwwet.
Rijksuniv. Gent, 1974, 39, 1079). Introduced by BASF AG.
APPLICATIONS:
Biochemistry SDHI: inhibits mitochondrial function by disrupting complex II (succinate
dehydrogenase) in the respiratory electron transport chain. Mode of action Systemic
and contact fungicide with protective and curative action. Uses Control of rust diseases of
cereals, coffee, vegetables, and ornamentals; rust and fairy rings on turf; Rhizoctonia spp. on
cotton, potatoes, cereals, rice, soya beans, ornamentals, vegetables, tobacco, and turf; and
Typhula incarnata in cereals. Formulation types WP.
PRODUCTS:
Discontinued products Calirus* (BASF).
ANALYSIS:
Product by hplc. Residues by glc with ECD.
Oral Acute oral LD
50
for rats and guinea pigs >6400 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits).
NOEL (90 d) for rats >100 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation) IV
ECOTOXICOLOGY:
Fish LC
50
(96 h) for trout 6.4 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment In loamy and humous sandy soils DT
50
c. 34 weeks.
benquinox
Fungicide
NOMENCLATURE:
Common name tserenox (USSR); benquinox (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-(4-hydroxyiminocyclohexa-2,5-dienylidene)benzohydrazide;
1,4-benzoquinone 1-benzoylhydrazone 4-oxime
Chemical Abstracts name benzoic acid
[4-(hydroxyimino)-2,5-cyclohexadien-1-ylidene]hydrazide Other names COBH
CAS RN [495738] EC no 2078079 Development codes Bayer 15 080
Smiles code ON=C1C=CC(=NNC(=O)c2ccccc2)C=C1
13
H
11
N
3
O
2
Form Yellow-brown
crystals. M.p. 195 C (decomp.)
bentaluron 39
V.p. Non-volatile Solubility In water 5 mg/l (room temperature). Dissolves readily in
aqueous alkalis with the formation of salts. Soluble in common organic solvents, readily
soluble in formamide. Stability Very stable under normal conditions. Hydrolysed by strong
acids and alkalis.
COMMERCIALISATION:
History Fungicide reported by P. E. Frohberger (Phytopath. Z., 1956, 37, 427). Introduced by
Bayer AG.
APPLICATIONS: Uses Fungicidal dressing to protect seeds and seedlings from soil
fungi. Not used against cereal seed-borne diseases. Phytotoxicity Should not be used as a
leaf fungicide.
PRODUCTS:
Discontinued products Ceredon* (Bayer); Cereline* (Bayer);
Discontinued mixtures Ceredon T* (+ thiram) (Bayer); Rhizoctol combi*
(+ methylarsenic sulfde) (Bayer); Rhizoctol slurry* (+ methylarsenic sulfde) (Bayer);
Tillantox* (+ phenylmercury chloride) (Bayer).
Oral Acute oral LD
50
for ratsc. 100 mg/kg. Toxicity Class WHO (a.i.) O
ECClassifcation T; R25| Xn; R21
ECOTOXICOLOGY:
Fish Toxic to fsh. LC
50
(48 h) for carp 0.048 mg/l. Bees Not known; irrelevant as regards
the seed dressing agent.
Details PM4, p. 35.
bentaluron
Fungicide
NOMENCLATURE:
Common name bentaluron (BSI, E-ISO, (m) F-ISO) IUPAC name 1-(1,3-benzothiazol-
2-yl)-3-isopropylurea; 1-benzothiazol-2-yl-3-isopropylurea
Chemical Abstracts name N-2-benzothiazolyl-N-(1-methylethyl)urea
CAS RN [28956641] Development codes CGA 18 734
Smiles code CC(C)NC(=O)Nc1nc2ccccc2s1
11
H
13
N
3
OS
COMMERCIALISATION:
History Fungicide evaluated by Ciba AG (later Ciba-Geigy AG).
40
benzamorf
benzadox; benzadox-ammonium
Herbicide
NOMENCLATURE:
Common name benzadox (BSI, ANSI, WSSA) IUPAC name benzamido-oxyacetic acid
Chemical Abstracts name [(benzoylamino)oxy]acetic acid
CAS RN [5251934] benzadox Development codes MC 0035 (Murphy); S 6173
(Gulf) Smiles code benzadox:OC(=O)CONC(=O)c1ccccc1
PHYSICAL CHEMISTRY: Mol. wt. 195.2; (ammonium salt 212.2) M.f. C
9
H
9
NO
4
;
(ammonium salt C
9
H
12
N
2
O
4
)
COMMERCIALISATION:
History Herbicidal activity reported (Farm Chem., 1967, 130, 86). Introduced by Gulf Oil
Corp. and by Murphy Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Topcide* (Gulf).
Details PM4, p. 38.
benzamacril; benzamacril-isobutyl
Fungicide
NOMENCLATURE:
Common name benzamacril (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-[benzyl(methyl)amino]-2-cyanoacrylic acid; 2-cyano-3-(N-
methylbenzylamino)acrylic acid
Chemical Abstracts name 2-cyano-3-[methyl(phenyl)amino]-2-propenoic acid
CAS RN [88107271] benzamacril-isobutyl; [127087869] benzamacril
Smiles code benzamacril-isobutyl:CC(C)COC(=O)C(=CN(C)Cc1ccccc1)C#N
PHYSICAL CHEMISTRY: Mol. wt. 216.2; (isobutyl ester 272.4) M.f. C
12
H
12
N
2
O
2
;
(isobutyl ester C
16
H
20
N
2
O
2
)
COMMERCIALISATION:
History Fungicide evaluated by FBC Limited (later Schering Agriculture).
benzamorf
Fungicide
NOMENCLATURE:
Common name benzamorf (BSI, E-ISO); benzamorphe ((m) F-ISO)
IUPAC name morpholinium 4-dodecylbenzenesulfonate
benzfendizone 41
Chemical Abstracts name 4-dodecylbenzenesulfonic acid compound with
morpholine (1:1) CAS RN [12068085] Development codes BAS 276F (BASF)
Smiles code CCCCCCCCCCCCc1ccc(cc1)S(=O)(=O)[O-].C1COCC[NH2+]1
22
H
39
NO
4
S
COMMERCIALISATION:
History Fungicide introduced by BASF AG.
APPLICATIONS:
Mode of action Lipophilic fungicide.
benzfendizone
Herbicide
HRAC E WSSA 14; pyrimidindione
NOMENCLATURE:
Common name benzfendizone (BSI, E-ISO, (f) F-ISO)
IUPAC name methyl 2-{5-ethyl-2-[4-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-
trifuoromethylpyrimidin-1-yl)phenoxymethyl]phenoxy}propionate
Chemical Abstracts name methyl 2-[2-[[4-[3,6-dihydro-3-methyl-2,6-dioxo-4-
(trifuoromethyl)-1(2H)-pyrimidinyl]phenoxy]methyl]-5-ethylphenoxy]propanoate
CAS RN [158755954] Development codes FMC 143686; F3686
Smiles code CCc1ccc(COc2ccc(cc2)n3c(=O)cc(n(C)c3=O)C(F)(F)F)c(OC(C)C(=O)OC)c1
25
H
25
F
3
N
2
O
6
COMMERCIALISATION:
History Herbicide evaluated by FMC.
APPLICATIONS:
Biochemistry Inhibitor of protoporphyrinogen oxidase. Uses Evaluated for post-
emergence control of grass and broad-leaved weeds in orchards and no-till situations; also
as a cotton defoliant and potato desiccant.
N N
CH
3
CH
2
O
O
O
O
CH
3
CF
3
CH
3
CH
3
O
2
C
42
benzofuor
benzipram
Herbicide
NOMENCLATURE:
Common name benzipram (BSI, E-ISO, ANSI, WSSA); benziprame ((m) F-ISO)
IUPAC name N-benzyl-N-isopropyl-3,5-dimethylbenzamide
Chemical Abstracts name 3,5-dimethyl-N-(1-methylethyl)-N-(phenylmethyl)benzamide
CAS RN [35256861] Development codes S-18 510
Smiles code CC(C)N(Cc1ccccc1)C(=O)c2cc(C)cc(C)c2
19
H
23
NO
COMMERCIALISATION:
History Herbicide introduced by Gulf Oil Corp.
5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone
Insecticide synergist
NOMENCLATURE:
IUPAC name 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone
Chemical Abstracts name 5-(5-benzo-1,3-dioxolyl)-3-hexyl-2-cyclohexen-1-one
Other names piperonyl cyclonene CAS RN [8066124]
19
H
24
O
3
COMMERCIALISATION:
History Synergist for insecticides.
benzofuor
Herbicide
NOMENCLATURE:
Common name benzofuor (BSI, ANSI, WSSA, E-ISO, (m) F-ISO)
IUPAC name 4-ethylthio-2-(trifuoromethyl)methanesulfonanilide; 4-ethylthio-,,-
trifuoromethanesulfon-o-toluidide
Chemical Abstracts name N-[4-(ethylthio)-2-(trifuoromethyl)phenyl]
methanesulfonamide CAS RN [68672173] Development codes MBR 18 337
Smiles code CCSc1ccc(NS(=O)(=O)C)c(c1)C(F)(F)F
10
H
12
F
3
NO
2
S
2
COMMERCIALISATION:
History Herbicide and plant growth regulator introduced by 3M Company.
benzoylprop; benzoylprop-ethyl 43
benzoylprop; benzoylprop-ethyl
Herbicide
NOMENCLATURE:
Common name benzoylprop (BSI, E-ISO, (m) F-ISO, WSSA)
IUPAC name N-benzoyl-N-(3,4-dichlorophenyl)-DL-alanine (I)
Chemical Abstracts name (I) CAS RN [22212551] benzoylprop-ethyl; [2221256
2] benzoylprop EC no 2448455 benzoylprop-ethyl Development codes WL 17 731
(ester)
PHYSICAL CHEMISTRY:
Composition Tech. is 93%. Mol. wt. 338.2; (ethyl ester 366.2) M.f. C
16
H
13
Cl
2
NO
3
; ethyl
ester C
18
H
17
Cl
2
NO
3

Form Tech. benzoylprop-ethyl is an off-white crystalline powder. M.p. 7071 C (ester)
V.p. 0.0047 mPa (20 C, ester) Solubility In water c. 20 mg/l (25 C, ester). In acetone
700750, Shellsol A 250300 (both g/l, 25 C, for ester). Stability Stable photochemically,
and hydrolytically over at least the range pH 3 to pH 6.
COMMERCIALISATION:
History Benzoylprop-ethyl is a herbicide reported by T. Chapman et al. (Symp. New. Herbic.,
3rd, 1969, p. 40). Introduced by Shell Research Ltd. Patents GB 1164160
APPLICATIONS:
Mode of action Selective herbicide Uses Applied at 1.01.5 kg/ha to wheat, it gives an
8595% control of wild oat (Avena barbata, A. fatua, A. ludoviciana, A. sterilis). Field beans,
oilseed rape and culinary mustard may also be safely treated. Crop competition ensures
the effective control of wild oat, the stem elongation of which is inhibited (B. Jeffcoat & W.
N. Harries, Pestic. Sci., 1973, 4, 891). Formulation types EC.
PRODUCTS:
Discontinued products Suffx* (Shell).
ANALYSIS:
Product analysis (ester) by glc (CIPAC Handbook, 1983, 1B, 1732) or by i.r. spectroscopy.
Residues determined by glc with ECD (A. N. Wright & B. L. Mathews, Pestic. Sci., 1976, 7, 339).
Oral Acute oral LD
50
for rats 1555, for mice 716 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >1000 mg/kg. NOEL In 90 d feeding trials, no change of
toxicological signifcance in rats receiving 1000 mg/kg diet or dogs 300 mg/kg diet.
Toxicity Class WHO (a.i.) III (for ethyl ester)ECClassifcation Xn; R22| N; R50, R53
(for DL-benzoylprop-ethyl)
ENVIRONMENTAL FATE:
The fate of the compound in plants, soils and animals has been reported (K. I. Beynon et al.,
44
benzthiazuron
Pestic. Sci., 1974, 5, 429, 443, 451; J. V. Crayford et al., ibid., 1976, 7, 559).
benzthiazuron
Herbicide
NOMENCLATURE:
Common name benzthiazuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-(1,3-benzothiazol-2-yl)-3-methylurea; 1-benzothiazol-2-yl-3-methylurea
Chemical Abstracts name N-2-benzothiazolyl-N-methylurea CAS RN [1929880]
EC no 2176859 Development codes Bayer 60 618
Smiles code CNC(=O)Nc1nc2ccccc2s1
9
H
9
N
3
OS Form Colourless powder.
M.p. Decomposes (without melting) at 305-313 C V.p. 1.3 mPa (92 C, extrapolated)
Solubility In water 15 mg/l (20 C). In organic solvents such as acetone, chlorobenzene,
DMF, xylene, isobutanol
510 mg/l; dichloromethane 3, toluene 1, isopropanol 4 (all in g/l, 20 C).
Stability Hydrolysed by strong acids and alkalis.
COMMERCIALISATION:
History Herbicide reported by H. Hack (International Meeting on Selective Weed Control
in Sugar Beet Crops, Marly-le-Roi, 910 March 1967). Introduced in the Netherlands
(1967) by Bayer AG. Patents BE 647740; GB 1004469
APPLICATIONS:
Biochemistry Photosynthetic electron transport inhibitor at the photosystem II
receptor site. Interferes with cellular division at the level of RNA biosynthesis, and inhibits
photosynthesis. Mode of action Selective herbicide, absorbed mainly by the roots. Uses
Pre-emergence control of many germinating annual broad-leaved weeds in sugar beet,
fodder beet, and spinach at 3.26.4 kg/ha. Formulation types WP. Compatibility
Incompatible with quintozene and disulfoton.
PRODUCTS:
Discontinued products Gatnon* (Bayer).
ANALYSIS:
Product analysis by i.r. spectroscopy. Residues determined by uv spectroscopy (H. J. Jarczyk
& K. Vogeler, Pfanz.-Nachr. Bayer (Engl. Ed.), 1967, 20, 575).
N
S
NHCONHCH
3
binapacryl 45
Oral Acute oral LD
50
for male rats >2500, male mice >1000, male dogs >1000 mg/kg.
50
for rats >500 mg/kg. Irritating to eyes; non-
irritating to skin. NOEL (90 d) for rats 1000 mg/kg. In 60 d feeding trials, rats receiving
130 mg/kg daily showed no ill-effects. Toxicity Class WHO (a.i.) III
ECClassifcation Xn; R22
ECOTOXICOLOGY:
Fish Non-toxic to fsh.
ENVIRONMENTAL FATE:
Soil/Environment Soil DT
50
c. 1012 weeks.
bethoxazin
Algicide, fungicide
NOMENCLATURE:
Common name bethoxazine ((f) F-ISO); bethoxazin (BSI, E-ISO (not Japan))
IUPAC name 3-benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine 4-oxide
Chemical Abstracts name 3-benzo[b]thien-2-yl-5,6-dihydro-1,4,2-oxathiazine
4-oxide CAS RN [163269305] EC no 4310306 Development codes R 102622
Smiles code O=S1C(C2=CC3=CC=CC=C3S2)=NOCC1
11
H
9
NO
2
S
2
COMMERCIALISATION:
Manufacturers Janssen
binapacryl
Acaricide, fungicide
FRAC 29, C5; dinitrophenyl crotonate
NOMENCLATURE:
Common name binapacryl (BSI, E-ISO, (m) F-ISO, ANSI, ESA, JMAF)
IUPAC name 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate
Chemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenyl 3-methyl-2-
butenoate CAS RN [485314] EC no 2076129 Development codes Hoe 02 784
Smiles code CCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)C=C(C)C)[N+](=O)[O-]
S
O
N
O
S
46
binapacryl
PHYSICAL CHEMISTRY:
Composition Tech. is 97%. Mol. wt. 322.3 M.f. C
15
H
18
N
2
O
6
Form Colourless
crystalline powder. M.p. 6667 C; (tech., 6569 C) V.p. 13 mPa (60 C) S.g./density
1.2 (20 C); (tech. 1.251.28 (20 C)) Solubility In water c. 1 mg/l (pH 5, 20 C). In
hexanec. 0.4, dichloromethane, ethyl acetate, toluene >500, methanolc. 21 (all in g/l, 20 C).
Stability Slowly decomposed by uv light; unstable in alkali and concentrated acids, and
suffers slight hydrolysis on long contact with water.
COMMERCIALISATION:
History Acaricide and fungicide reported by L. Emmel & M. Czech (Anz. Schaedlingskd.,
1960, 33, 145). Introduced by Hoechst AG. Patents GB 855736; DE 1099787
APPLICATIONS:
Biochemistry Uncouples mitochondrial oxidative phosphorylation.
Mode of action Non-systemic acaricide with contact action. Also a contact fungicide
which acts by preventing germination of the conidia, and thus blocking reinfection.
Uses Effective against powdery mildews; used mainly against all stages of spider mites
and powdery mildews of apples, citrus, cotton, pears and top fruit at 2550 g/100 l.
Phytotoxicity Phytotoxic to blackcurrants, cyclamens, and to hydrangeas under glass.
Formulation types EC; WP; SC. Compatibility Incompatible with alkalis. May be
phytotoxic when mixed with some organophosphorus compounds.
PRODUCTS:
Discontinued products Acricid* (Hoechst); Endosan* (Hoechst); Morocide*
(Hoechst); Morrocid* (Hoechst).
ANALYSIS:
Product analysis by hydrolysis to the parent phenol (dinoseb, q.v.) measured by colorimetry
(D. S. Farrington et al., Analyst (London), 1983, 108, 353) or by titration with titanium
trichloride. Residues determined by the former method (Pestic. Anal. Manual, 1979, I, 201-A,
201G; P. B. Baker & R. A. Hoodless, Analyst (London), 1973, 98, 172; R. W. Buxton &
T. A. Mohr, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 235; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 314).
JMPR Evaln. II 46 (1985). ICSC.835 (1997). EU Status (1107/2009) Considered to be
outside the scope of the Directive; already banned, 79/117/EEC as amended by 90/533/EEC.
Oral Acute oral LD
50
for rats 150225, male mice 16003200, female guinea pigs 300, dogs
450640 mg/kg. Skin and eye Acute percutaneous LD
50
(acetone solution) for rabbits and
mice 750 mg/kg. Slight eye irritant.
NOEL In 2 y feeding trials, rats receiving 500 mg/kg diet and dogs receiving 50 mg/kg diet
showed no ill-effects. ADI/RfD (JMPR) No ADI [1985]. Toxicity Class WHO (a.i.) II
ECClassifcation R61| Xn; R21/22| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for chickens 800 mg/kg. Fish Max. tolerated dose for guppies 0.5,
biopermethrin 47
carp 1.0, trout 2.0 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, hydrolysed to dinoseb (q.v.).
Soil/Environment Duration of activity in soil is 1525 d.
biopermethrin
Insecticide
IRAC 3 A single isomer, component of permethrin.
NOMENCLATURE:
Common name bioperm(thrine) ((f) F-ISO); biopermethrin (BSI, E-ISO)
IUPAC name 3-phenoxybenzyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethy
lcyclopropanecarboxylate; 3-phenoxybenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-
dimethylcyclopropanecarboxylate
Chemical Abstracts name (1R-trans)-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-
2,2-dimethylcyclopropanecarboxylate; (3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-
dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate Other names permethrin-B;
1R-trans-permethrin CAS RN [51877748] Development codes NRDC 147; RU
22090 Smiles code CC1(C)C(C=C(Cl)Cl)C1C(=O)OCc2cccc(Oc3ccccc3)c2
21
H
20
Cl
2
O
3
APPLICATIONS:
Biochemistry Acts on the nervous system of insects, and disturbs the function of
neurons by interaction with the sodium channel.
ANALYSIS:
Analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Anal. Profles.
Permethrin isomers in drinking water by glc with ECD (AOAC Methods, 18th Ed., 990.06).
See A. J. Gray & D. M. Soderlund, Chapt. 5 in Insecticides.
O
CH
2
C CH
CH
3
CH
3
Cl
C
O
O
Cl
H
H
48
biphenyl
biphenyl
Fungicide
FRAC 14, F3; aromatic hydrocarbon
NOMENCLATURE:
Common name biphenyl (BSI, E-ISO, F-ISO, accepted in lieu of common name)
IUPAC name biphenyl
Chemical Abstracts name 1,1-biphenyl Other names diphenyl CAS RN [92524]
EC no 2021635 Smiles code c1ccc(cc1)c2ccccc2
12
H
10
Form Colourless crystals.
M.p. 70.5 C B.p. 256 C V.p. 4 Pa (20 C) (CICAD) K
ow
logP = 3.884.04 (CICAD) S.g./
density 1.041 Solubility In water 4.45 mg/l (20 C) (CICAD). Readily soluble in ethanol,
diethyl ether, and other organic solvents. Stability Very stable in acidic and alkaline media.
F.p. 106 C
COMMERCIALISATION:
History Fungicidal activity against citrus-rotting fungi described by G. B. Ramsey et al. (Bot.
Gaz., 1944, 106, 74).
APPLICATIONS:
Biochemistry Proposed mode of action is lipid peroxidation. Mode of action Fungistat
which inhibits sporulation. Uses Used to impregnate citrus fruit wraps to prevent fungal
attack. Formulation types Impregnated material.
ANALYSIS:
Residues determined by uv spectrometry (F. A. Gunther et al., Analyst (London), 1963, 88, 36;
F. A. Gunther & D. E. Ott, ibid., 1966, 91, 475; S. Norman et al., J. Assoc. Off. Anal. Chem., 1966,
49, 590; AOAC Methods, 18th Ed., 968.25), by glc (H. Pyysalo et al., J. Chromatogr., 1979, 168,
512; Man. Pestic. Residue Anal., p. 6) or by hplc (J. E. Farrow et al., Analyst (London), 1977, 102,
752). See also Pestic. Anal. Man., I, 302.
JMPR Evaln. 7 (1966), 9 (1967). ICSC.106 (1994). CICAD 6 (1999).
Oral Acute oral LD
50
for rats 3280, rabbits 2400, cats >2600 mg/kg. Depression of the
central nervous system, paralysis, and convulsions have been observed in experimental
animals. Inhalation Prolonged exposure of humans to vapour concentrations >0.005 mg/l
air is considered dangerous (J. Deichmann et al., J. Ind. Hyg. Toxicol., 1947, 29, 1).
NOEL NOAEL for rats 50 mg/kg b.w. daily (EPA IRIS).
bis(2-chloroethyl) ether 49
ADI/RfD (JMPR) 0.125 mg/kg b.w. [1967]; (EPA) cRfD 0.05 mg/kg b.w. [1989].
Toxicity Class WHO (a.i.) U EPA (formulation) III ECClassifcation Xi; R36/37/38| N;
R50, R53
ECOTOXICOLOGY:
Fish LC
50
(96 h) for fsh 1.54.7 mg/l, with rainbow trout and fathead minnow the most
sensitive species (CICAD). Daphnia LC
50
(8 h) 0.36 mg/l.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, metabolites identifed include
4-hydroxybiphenyl and other phenolic compounds (H. D. West et al., Arch. Biochem. Biophys.,
1956, 60, 1420). Plants Residues in fruit have been reviewed (A. Rajzman, Residue Rev.,
1964, 8, 1; S. W. Souci & G. Maier-Haarlnder, ibid., 1966, 16, 103).
bis(2-chloroethyl) ether
Insecticide
NOMENCLATURE:
Common name dichloroethyl ether (ESA)
IUPAC name bis(2-chloroethyl) ether; di-(2-chloroethyl) ether
Chemical Abstracts name 1,1-oxybis[2-chloroethane] Other names DCEE
CAS RN [111444] EC no 2038701 Smiles code ClCCOCCCl
4
H
8
Cl
2
O
COMMERCIALISATION:
History Insecticidal activity reported by R. C. Roark & R. T. Cotton (USDA Tech. Bull., 1929,
No. 162); used to fumigate soil.
APPLICATIONS:
Mode of action Fumigant insecticide.
PRODUCTS:
Discontinued products Chlorex* (Union Carbide).
EHC 201 (1998). ICSC.417 (2000). IARC 9 (1975); 71 (1999).
IARC Class 3 ECClassifcation R40| T+; R26/27/28; concn. dep.
50
bis(methylmercury) sulfate
1,1-bis(4-chlorophenyl)-2-ethoxyethanol
Acaricide
NOMENCLATURE:
IUPAC name 1,1-bis(4-chlorophenyl)-2-ethoxyethanol
Chemical Abstracts name 4-chloro--(4-chlorophenyl)--(ethoxymethyl)
benzenemethanol CAS RN [6012835] Development codes Geigy 337; G 23 645
Smiles code CCOCC(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
16
H
16
Cl
2
O
2
COMMERCIALISATION:
History Acaricide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
PRODUCTS:
Discontinued products Etoxinol* (Ciba-Geigy).
Oral Acute oral LD
50
for rats >5000 mg/kg (Shibuya).
bis(methylmercury) sulfate
Fungicide
NOMENCLATURE:
IUPAC name bis(methylmercury) sulfate
Chemical Abstracts name dimethyl--sulfatodimercury CAS RN [3810819]
Smiles code C[Hg]OS(=O)(=O)O[Hg]C
2
H
6
Hg
2
O
4
S
COMMERCIALISATION:
PRODUCTS:
Discontinued products Aretannieuw* (Bayer); Cerewet* (Bayer).
JMPR Evaln. 9 (1967) EU Status (1107/2009) Alkyl mercury compounds considered to
be outside the scope of the Directive; already banned, 79/117/EEC.
IARC Class methylmercury compounds are classifed 2B
ECClassifcation Not specifed, but organic mercury generally is assigned T+; R26/27/28|
R33| N; R50, R53, concentration-dependent. PIC Not specifcally listed in the relevant
DGD, but all mercury compounds are included in the PIC procedure.
Details PM2, p. 47.
bisthiosemi 51
bisthiosemi
Rodenticide
NOMENCLATURE:
Common name bisthiosemi (JMAF)
IUPAC name 1,1-methylenedi(thiosemicarbazide)
Chemical Abstracts name 2,2-methylenebis(hydrazinecarbothioamide)
CAS RN [39603480] Development codes NK-15 561
Smiles code NC(=S)NNCNNC(=S)N
3
H
10
N
6
S
2
M.p. Decomposes at
171174 C Solubility Almost insoluble in water and common organic solvents. Soluble
in DMSO. Stability Decomposes slowly in water, and more rapidly in acidic or alkaline
conditions.
COMMERCIALISATION:
History Rodenticide introduced by Nippon Kayaku Co., Ltd. Patents JP 50020126; GB
1351710; US 3826841
APPLICATIONS: Uses Control of Rattus norvegicus, Rattus rattus, and Microtus montebelli.
Formulation types RB .
PRODUCTS:
Discontinued products Kayanex* (Nippon Kayaku).
ANALYSIS:
Product analysis by hydrolysis to thiosemicarbazide which is measured colorimetrically as a
derivative.
Oral Acute oral LD
50
for mice 30.450, guinea pigs 3236, catsc. 150, dogs >1500 mg/kg.
NOEL (90 d) for mice 100 mg/kg diet; for rats 50 mg/kg diet.
Toxicity Class WHO (a.i.) II
ECOTOXICOLOGY:
Birds Acute oral LD
50
for chickens 120150 mg/kg.
52
bis(tributyltin) oxide
bis(tributyltin) oxide
Fungicide
NOMENCLATURE:
IUPAC name bis(tributyltin) oxide
Chemical Abstracts name hexabutyldistannoxane CAS RN [56359]
Smiles code CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC
24
H
54
OSn
2
Form Colourless to pale
yellow oil. M.p. 45 C
B.p. 180 C /2 mmHg V.p. Negligible (20 C) S.g./density 1.14 Solubility In water
c. 100 mg/l; in sea water 60 mg/l (room temperature). Miscible with most organic solvents.
Stability Stable to storage in dark, closed containers; forms bis(tributyltin) carbonate on
exposure to air.
COMMERCIALISATION:
History Fungicide reported by J. G. A. Luijten & G. J. M. van der Kerk, Investigations
Organotin. Introduced (1966) by M & T Chemicals Ltd.
APPLICATIONS: Uses Mainly used as a toxicant in marine antifouling paints, to control
Algae in industrial cooling water and as a wood preservative. Phytotoxic and unsuitable
for use on growing crops or on cultivated soil.
ANALYSIS:
Product analysis by wet oxidation, reduction to tin(II) measured by titration with potassium
iodate. Residues determined by hydrolysis to tin(II) salts estimated by colorimetry with
dithiol (R. E. D. Clark, Analyst (London), 1936, 61, 242; 1937, 62, 661).
EHC 116 (1990); a general review of tributyl tin compounds. PDS 65 (1985). ICSC.282
(1998). CICAD 14 (1999). EU Status (1107/2009) Not approved, as tributyltinoxyde,
Commission Regulation 2076/2002.
Oral Acute oral LD
50
for rats 194 mg a.i. (as aqueous suspension)/kg (J. Elsea & O. E.
Paynter, AMA Arch. Ind. Health, 1958, 18, 214). Skin and eye Absorbed by skin and may
cause irritation. NOEL BMD10 (18 mo) immunotoxicity for rats 0.03 mg/kg b.w. daily (J. G.
Vos, et al., 1990. Toxicol. Appl. Pharmacol. (1990) 105, 144155, cited by EPA).
ADI/RfD (EPA) cRfD 0.003 mg/kg b.w. [1997]. Water GV Excluded from GV derivation
(U). Toxicity Class WHO (a.i.) Ib
Sn CH
3
(CH
2
)
3
CH
3
(CH
2
)
3
CH
3
(CH
2
)
3
O Sn (CH
2
)
3
CH
3
(CH
2
)
3
CH
3
(CH
2
)
3
CH
3
blasticidin-S; benzylaminobenzenesulfonate (BABS) salt 53
blasticidin-S; benzylaminobenzenesulfonate (BABS) salt
Fungicide
See also The Manual of Biocontrol Agents entry: 2:160
FRAC 23, D2; enopyranuronic acid antibiotic
NOMENCLATURE:
Common name blasticidin-S (JMAF)
IUPAC name 1-(4-amino-1,2-dihydro-2-oxopyrimidin-1-yl)-4-[(S)-3-amino-5-(1-
methylguanidino)valeramido]-1,2,3,4-tetradeoxy--D-erythro-hex-2-enopyranuronic acid
Chemical Abstracts name (S)-4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-
oxopentyl]amino]-1-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,2,3,4-tetradeoxy--D-erythro-
hex-2-enopyranuronic acid (blasticidin); 4-[(phenylmethyl)amino]benzenesulfonic acid,
compound with (S)-4-[[3-amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]
amino]-1-[4-amino-2-oxo-1(2H)-pyrimidinyl]-1,2,3,4-tetradeoxy--D-erythro-hex-2-
enopyranuronic acid (BABS salt) Other names Bla-S
CAS RN [2079007] blasticidin, formerly [11002929] and [12767554];
[51775281] BABS salt Development codes BcS-3
Smiles code CN(CC[C@@H](N)CC(=O)N[C@H]1/C=C\[C@H](OC1C(=O)
O)n2ccc(N)nc2=O)C(=N)N; without stereochemistry:CN(CCC(N)CC(=O)
NC1C=CC(OC1C(=O)O)n2ccc(N)nc2=O)C(=N)N; BABS salt, without
stereochemistry:CN(CC[C@H](N)CC(=O)N[C@H]1C=C[C@@H](OC1C(=O)O)
n2ccc(N)nc2=O)C(=N)N.OS(=O)(=O)c1ccc(NCc2ccccc2)cc1
N
N
NH
2
O
O
HO
2
C
NH
NH
2
C CH
2
CH
2
CH
2
CO
H
CH
3
N H
2
NC
NH
blasticidin S
SO
3
H
NH
CH
2
benzylaminobenzenesulfonic acid
54
blasticidin-S; benzylaminobenzenesulfonate (BABS) salt
PHYSICAL CHEMISTRY: Mol. wt. 422.4; 685.6 (BABS salt) M.f. C
17
H
26
N
8
O
5
; BABS
salt C
30
H
39
N
9
O
8
S
Form Colourless needles; (tech., light brown solid). M.p. 235-236 C (decomp.)
Solubility In water >30 g/l (20 C). In acetic acid >30 g/l (20 C). Practically insoluble in
acetone, benzene, carbon tetrachloride, chloroform, cyclohexane, dioxane, ethanol, diethyl
ether, ethyl acetate, methanol, pyridine, xylene. Stability Stable at pH 57; unstable at pH
<4 and in alkali. Stable to light. Specifc rotation []11D +108.4 (c = 1.0 in water)
pKa pKa1 2.4 (carboxyl), pKa2 4.6, pKa3 8.0, pKa4 >12.5 (three bases)
COMMERCIALISATION:
Production By the fermentation of Streptomyces griseochromogenes. History Antibiotic
discovered by K. Fukunaga et al. (Bull. Agric. Chem. Soc. Jpn, 1955, 19, 18), its fungicidal
properties reported by T. Misato et al. (Nippon Shokubutsu Byori Gakkaiho, 1959, 24,
302) and its structure elucidated by N. Otake (Agric. Biol. Chem., 1967, 30, 132). Its
benzylaminobenzenesulfonate salt was introduced by Kaken Chemical Co., Ltd (later Kaken
Pharmaceutical Co. Ltd), Kumiai Chemical Industry Co., Ltd, and Nihon Nohyaku Co., Ltd.
APPLICATIONS:
Biochemistry Protein synthesis inhibitor. Mode of action Contact fungicide with
protective and curative action. Uses The BABS salt was used for control of rice blast
(Pyricularia oryzae), by foliar application at 1040 g/ha. Phytotoxicity Damage can
be caused to alfalfa, aubergines, clover, potatoes, soya beans, tobacco, and tomatoes.
Excessive application produces yellow spots on rice leaves. Formulated as the
benzylaminobenzenesulfonate salt, to reduce phytotoxicity. Formulation types DP; EC;
WP. Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Bla-S* (BABS salt) (Nihon Nohyaku).
ANALYSIS:
Product analysis by bioassay with Bacillus cereus IAM-1729. Residues determined by
bioassay with Fulvia fulva ACI-1164.
Oral Acute oral LD
50
for male rats 56.8, female rats 55.9, male mice 51.9, female
mice 60.1 mg/kg. BABS salt, acute oral LD
50
for rats 53.3 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >500 mg/kg. Severe eye irritant. NOEL (2 y) for rats 1 mg/kg
diet. Other Non-mutagenic in bacterial reversion tests. Toxicity Class WHO (a.i.) Ib EPA
(formulation) II ECClassifcation T+; R28
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp >40 mg/l. Daphnia LC
50
(3 h) for D. pulex >40 mg/l.
ENVIRONMENTAL FATE:
Animals Almost all of
3
H-blasticidin-S administered to mice was excreted in the urine and
faeces within 24 h. Plants In rice plants, cytomycin and deaminohydroxy blasticidin-S were
identifed as the main metabolites. Soil/Environment In soil, DT
50
<2 d (two soil types,
o.c. 2.53%, 9.6%; moisture 42.6%, 87%, respectively; pH 6.0, 25 C).
1-bromo-2-chloroethane 55
bromfenvinfos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name bromfenvinfos (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-bromo-1-(2,4-dichlorophenyl)vinyl diethyl phosphate [(E)- to (Z)- ratio
c. 1:18]
Chemical Abstracts name 2-bromo-1-(2,4-dichlorophenyl)ethenyl diethyl phosphate
CAS RN [33399007] unstated stereochemistry; [58580146] (E)- isomer; [5858013
5] (Z)- isomer Development codes IPO-62
Smiles code CCOP(=O)(OCC)OC(=CBr)c1ccc(Cl)cc1Cl
12
H
14
BrCl
2
O
4
P
COMMERCIALISATION:
History Insecticide.
APPLICATIONS:
3-bromo-1-chloroprop-1-ene
Insecticide
NOMENCLATURE:
IUPAC name 3-bromo-1-chloroprop-1-ene
Chemical Abstracts name 3-bromo-1-chloro-1-propene CAS RN [3737006]
Development codes CBP-55 Smiles code CC(=CCl)Br
3
H
4
BrCl
COMMERCIALISATION:
History Fumigant insecticide for soil introduced by Shell Development Co.
APPLICATIONS: Uses Soil-fumigant insecticide
1-bromo-2-chloroethane
Insecticide
NOMENCLATURE:
IUPAC name 1-bromo-2-chloroethane (I)
Chemical Abstracts name (I) Other names ethylene chlorobromide; sym-
chlorobromoethane CAS RN [107040] Smiles code ClCCBr
2
H
4
BrCl
56
bromocyclen
COMMERCIALISATION:
History Insecticide used to fumigate soil, reported by M. W. Stone & F. B. Foley (J. Econ.
Entomol., 1951, 44, 711).
APPLICATIONS: Uses Soil-fumigant insecticide.
bromobonil
Herbicide
NOMENCLATURE:
Common name bromobonil (BSI, E-ISO, (m) F-ISO)
IUPAC name 2,6-dibromo-4-cyanophenyl tetrahydrofurfuryl carbonate
Chemical Abstracts name 2,6-dibromo-4-cyanophenyl (tetrahydro-2-furanyl)methyl
carbonate CAS RN [25671469] unstated stereochemistry
Smiles code Brc1cc(C#N)cc(Br)c1OC(=O)OCC2CCCO
2
13
H
11
Br
2
NO
4
COMMERCIALISATION:
History Herbicide evaluated by Boehringer & Sohn (became Shell Agrar).
bromocyclen
Acaricide, insecticide, ixodicide
NOMENCLATURE:
Common name bromocyclen (BSI, E-ISO, BPC); bromocycl(ne) ((m) F-ISO)
IUPAC name 5-bromomethyl-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene;
5-bromomethyl-1,2,3,4,7,7-hexachloro-8,9,10-trinorborn-2-ene
Chemical Abstracts name 5-(bromomethyl)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-
2-ene CAS RN [1715408] Smiles code ClC1=C(Cl)C2(Cl)C(CBr)CC1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. isc. 90%. Mol. wt. 393.8 M.f. C
8
H
5
BrCl
6
COMMERCIALISATION:
History Veterinary insecticide and acaricide introduced by Hoechst AG.
APPLICATIONS: Uses An insecticide and acaricide effective against ectoparasites such
as Chorioptes, Cnemidocoptes, Notoedres, Otodectes, Psoroptes, Sarcoptes spp. and Cheyletiella
parasitivorax on cats, cattle, dogs, horses, pigs, sheep and some birds. The host may be
dusted, bathed or treated with an aerosol of bromocyclen. Formulation types AE; DP;
WP.
PRODUCTS:
Discontinued products Aludan* (Hoechst); Alugan* (Hoechst); Bromodan* (Hoechst).
bromofenoxim 57
Oral Acute oral LD
50
for rats 12 500 mg/kg. Toxicity Class WHO (a.i.) U
bromofenoxim
Herbicide
HRAC C3 WSSA 6
NOMENCLATURE:
Common name bromofenoxim (BSI, E-ISO, WSSA); bromoph(noxime) ((f) F-ISO)
IUPAC name 3,5-dibromo-4-hydroxybenzaldehyde 2,4-dinitrophenyloxime
Chemical Abstracts name 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)
oxime CAS RN [13181174], formerly [37273851] EC no 2361296
Development codes C 9122
Smiles code Oc1c(Br)cc(C=NOc2ccc(cc2[N+](=O)[O-])[N+](=O)[O-])cc1Br
13
H
7
Br
2
N
3
O
6
Form Cream-coloured
crystals. M.p. 196197 C
V.p. <1 10
5
mPa (20 C) K
ow
logP = 3.17 (pH 7.0) Henry 7.68 10
6
Pa m
3
mol
1

(pH 3.8, 20 C, calc.) S.g./density 2.15 (20 C) Solubility In water 0.6 (pH 3.8), 9.0
(pH 10) (both in mg/l, 20 C). In hexane 200, isopropanol 400, acetone 9900, n-octanol 200
(all in mg/l, 20 C). Stability On hydrolysis, DT
50
(70 C) 41.4 h (pH 1), 9.6 h (pH 5),
0.76 h (pH 9). pKa 5.46, weak acid
COMMERCIALISATION:
History Herbicide reported by D. H. Green et al. (Symp. New Herbic., 3rd, 1969, p. 77).
Introduced by Ciba AG (later Novartis Crop Protection AG). Patents BE 675444; GB
1096037 Manufacturers Novartis
APPLICATIONS:
Biochemistry Generates bromoxynil (q.v.). Mode of action Selective herbicide with
contact action. Absorbed by the leaves and stems, with some translocation. Uses Post-
emergence control of many annual broad-leaved weeds in cereals, maize, grass-seed crops,
grassland, and newly-seeded turf at rates in the range 1.02.5 kg/ha. Used in combination
with other herbicides to extend the spectrum and period of activity. Formulation types
WP; SC.
HO
Br
Br
CH O
NO
2
N NO
2
58
bromophos
PRODUCTS:
Discontinued products Dicoprime* (Ciba-Geigy); Faneron* (Novartis).
ANALYSIS:
Product analysis by hplc. Residues determined by hplc.
Oral Acute oral LD
50
for rats 1217, dogs >1000, mice 940 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >3000 mg/kg. Mild skin and eye irritant (rabbits).
Inhalation LC
50
(6 h) for rats >0.242 mg/l air. NOEL (2 y) for rats 100 mg/kg diet
(3.8 mg/kg b.w. daily); (3 mo) for dogs 100 mg/kg diet (3 mg/kg b.w. daily), for mice
10 mg/kg diet (0.63 mg/kg b.w.. daily). ADI/RfD (BfR) 0.0015 mg/kg b.w. [1989].
Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassifcation Xn; R22| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for Japanese quail 5560, bobwhite quail 4000, mallard ducklings
2800 ppm. Fish LC
50
(96 h) for rainbow trout 0.18, carp 0.088 mg/l. Daphnia LC
50
(48 h)
1.2 mg/l. Algae EC
50
(96 h) for Algae 2.2 mg/l. Bees WP non-toxic; SC toxic.
Worms LC
50
(14 d) for earthworms c. 1300 mg/kg. Otherbenefcial No effect on soil
respiration, ammonifcation or nitrifcation.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, dinitrophenol and
hydroxydibromobenzonitrile are formed, and are more slowly metabolised further and
excreted in the urine; unchanged parent is the primary excretion product in the faeces.
Plants In plants, 3,5-dibromo-4-hydroxybenzoic acid has been identifed as a metabolite.
There is some conversion to bromoxynil. Soil/Environment Of low mobility with little
or no persistence in the soil; DT
50
0.55 d. K
oc
1100.
bromophos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name bromophos (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name O-4-bromo-2,5-dichlorophenyl O,O-dimethyl phosphorothioate
Br
Cl
Cl
O P
S
OCH
3
OCH
3
bromophos 59
Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl) O,O-
dimethyl phosphorothioate CAS RN [2104963] EC no 2182773
Development codes S-1942 Smiles code COP(=S)(OC)Oc1cc(Cl)c(Br)cc1Cl
8
H
8
BrCl
2
O
3
PS Form Yellow crystals.
M.p. 5354 C
B.p. 140142 C /0.01 mmHg V.p. 17 mPa (20 C) Henry 8.89 Pa m
3
mol
1
(20 C, calc.)
Solubility In water 0.7 (20 C), 40 (25 C) (both in mg/l). In acetone 1090,
dichloromethane 1120, xylene 900, methanol 100 (all in g/l, 20 C). Stability Stable in
solution up to pH 9 and in aqueous suspension, but hydrolysed in alkaline media.
COMMERCIALISATION:
History Insecticide reported by R. Immel & G. Geisthardt (Meded. Landbouwhogesch.
Opzoekingsstn. Staat Gent, 1964, 29, 1242), and reviewed by D. Eichler (Residue Rev., 1972, 41,
65). Introduced by C. H. Boehringer Sohn/Cela GmbH (later Shell Agrar GmbH). Patents
DE 1174104; GB 956343
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide with
contact and stomach action. Uses Control of Diptera, Hemiptera, some Lepidoptera,
Coleoptera, and other insects in fruit, vegetables, feld crops, ornamentals, and forestry.
Important uses included control of cabbage root fies, carrot fies, onion fies, beet leaf
miners, wheat bulb fies, frit fies, and bean seed fies. Also used for control of stored-
product insect pests; in public health for control of fies, mosquitoes, etc.; as a household
insecticide; for control of insects in animal houses; and as an animal dip.
Phytotoxicity Phytotoxic to cotton and vines. Some varieties of pear, cabbage, and
ornamentals, and glasshouse crops may be injured. Formulation types AE; DP; EC; WP;
GR; KN; Seed treatment. Compatibility Not compatible with sulfur, organometallic
compounds and alkaline pesticides.
PRODUCTS:
Discontinued products Farel* (Shell); Nexion* (Shell).
ANALYSIS:
Product by oxidation with bromide-bromate solution, and titration of the excess bromate
with sodium thiosulfate (CIPAC Handbook, 1983, 1B, 1738; R. D. Weeren and D. Eichler Anal.
Methods Pestic. Plant Growth Regul. 1978, 10, 3334). Residues by glc with phosphorus-
specifc FID (R. D. Weeren Anal. Methods Pestic. Plant Growth Regul. 1978, 10, 3540;
M. A. Luke et al., J. Assoc. Off. Anal. Chem. 1981, 64, 1187. Analyst (London), 1980, 105, 515); by
fuorogenic labelling with dansyl chloride and tlc (S. Traore & J. J. Aaron Talanta 1981, 28(10),
765767). See also Pestic. Anal. Man., I, 503. Determination of the halogenated phenol
produced by hydrolysis can be used for both product and residue analysis.
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Evaln. I 45
(1985); JMPR Evaln. 43 (1984). PDS 76 (1994). EU Status (1107/2009) Not approved,
60
bromophos-ethyl
Oral Acute oral LD
50
for rats 37508000, mice 33115850, rabbits 720, guinea pigs
50
for rabbits 2188 mg/kg. NOEL (2 y)
for rats 0.63 mg/kg daily, for dogs 1.5 mg/kg daily. ADI/RfD (JMPR) 0.04 mg/kg b.w. [1977].
Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassifcation Xn; R22| N; R50,
R53| concn. dep.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hens 9700 mg/kg. Fish LC
50
for guppies 0.5, rainbow trout
0.050.5 mg/l. Bees LD
50
(oral) 18.819.6 mg/kg.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, >90% of the dose is eliminated within
24 h, principally in the urine. The pricipal metabolites are the desmethyl compound and the
phenol (FAO/WHO datasheet 76 (1994)). Plants In tomato plants, the main metabolite is
the phenol (M. Stiasni et al., J. Agr. Fd. Chem. (1969) 17, 1017, cited by FAO/WHO 28).
bromophos-ethyl
IRAC 1B
NOMENCLATURE:
Common name bromophos-ethyl (BSI, E-ISO, F-ISO, ESA)
IUPAC name O-4-bromo-2,5-dichlorophenyl O,O-diethyl phosphorothioate
Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl)
O,O-diethyl phosphorothioate CAS RN [4824786] EC no 2253990
Development codes S-2225 (Boehringer, Cela GmbH)
Smiles code CCOP(=S)(OCC)Oc1cc(Cl)c(Br)cc1Cl
10
H
12
BrCl
2
O
3
PS Form Colourless to
pale yellow liquid.
B.p. 122123 C /0.00l mmHg V.p. 6.1 mPa (30 C) S.g./density 1.521.55 (20 C)
Solubility In water 0.14 mg/l (20 C). Completely miscible with most common organic
solvents. Stability Stable in aqueous suspension at pH <9; hydrolysed at higher pH.
COMMERCIALISATION:
History Insecticide reported by M. S. Mulla et al. (Mosq. News, 1964, 24, 312), and reviewed
by D. Eichler (Residue Rev., 1972, 41, 65). Introduced by C. H. Boehringer Sohn/Cela GmbH
(later Shell Agrar GmbH). Patents DE 1174104; GB 956343
Br
Cl
Cl
O P
S
OCH
2
CH
3
OCH
2
CH
3
brompyrazon 61
APPLICATIONS:
and acaricide with contact and stomach action. Uses Control of Diptera, Hemiptera,
some Lepidoptera, Coleoptera, some other insects, and mites in fruit, vegetables, feld
crops, ornamentals, and forestry. Also used in public health for control of fies, mosquito
larvae, etc.; for control of insects in animal houses; and as an animal ectoparasiticide.
Formulation types EC; WP; GR; KN; UL . Compatibility Not compatible with sulfur
and organometallic compounds.
PRODUCTS:
Discontinued products Filariol* (Celamerck); Nexagan* (Shell).
ANALYSIS:
Product by oxidation with bromide-bromate solution, and titration of the excess bromate
with sodium thiosulfate (R. Weeren & D. Eichler Anal. Methods Pestic. Plant Growth Regul.
1978, 10, 3334). Residues by glc with phosphorus-specifc FID (R. D. Weeren & D. Eichler
Anal. Methods Pestic. Plant Growth Regul. 1978, 10, 3540; D. C. Abbott et al., Pestic. Sci. 1970,
1, 10). Determination of the halogenated phenol produced by hydrolysis can be used for
both product and residue analysis.
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Evaln. 29 (1977).
Oral Acute oral LD
50
LD
50
for rabbits 100600 mg/kg. Inhalation LC
50
(1.7 h) for rats 2.5 mg/l. NOEL (2 y) for
rats 78 mg/kg daily, for dogs 0.26 mg/kg daily. ADI/RfD (JMPR) 0.003 mg/kg b.w. [1975].
Toxicity Class WHO (a.i.) Ib EPA (formulation) II ECClassifcation T; R25| Xn; R21| N;
R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for quail 200 mg/kg. Fish LC
50
(96 h) for guppies 0.140.24, rainbow
trout >0.4 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, 8590% of the dose is eliminated
within 4 d in the faeces and urine. The principal metabolite is 4-bromo-2,5-dichlorophenol.
brompyrazon
Herbicide
NOMENCLATURE:
Common name brompyrazon (BSI (from 1984), E-ISO); brompyrazone (BSI (before
1984), (f) F-ISO)
62
bromuron
IUPAC name 5-amino-4-bromo-2-phenylpyridazin-3(2H)-one
Chemical Abstracts name 5-amino-4-bromo-2-phenyl-3(2H)-pyridazinone
CAS RN [3042840] Development codes BAS 2430H (BASF)
Smiles code Nc1cnn(c2ccccc2)c(=O)c1Br
10
H
8
BrN
3
O Form Yellowish
crystalline powder. M.p. 223224 C Solubility In water 200 mg/l (20 C). In benzene 0.3,
chloroform 2, ethanol 11 (all in g/kg, 20 C).
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Weed Res., 1962, 2, 177). Introduced by BASF AG.
APPLICATIONS:
Mode of action Selective herbicide. Uses A mixture with isonoruron controls Alopecurus
myosuroides, Apera spica-venti and annual broad-leaved weeds pre-em. or post-em. in cereals.
PRODUCTS:
Discontinued mixtures Basanor* (+ isonoruron) (BASF).
Oral Acute oral LD
50
for rats >6400 mg Basanor/kg. Skin and eye The formulation
caused only slight reddening 24 h after application to the shaved skin of rabbits.
ECOTOXICOLOGY:
Fish LC
50
for guppies 1020 mg/l.
Details PM5, p. 55.
bromuron
Herbicide
NOMENCLATURE:
IUPAC name N-(4-bromophenyl)-N-dimethylurea (I)
Chemical Abstracts name (I) CAS RN [3408977] Development codes FL 173
(Fahlberg-List)
9
H
11
BrN
2
O Form Colourless crystals.
M.p. 172174 C
V.p. 0.5 mPa (25 C) Henry 5 10
5
Pa m
3
mol
1
(calc.) S.g./density 1.28 at 25 C
Solubility In water 0.237 g/l (22.5 C). In acetone 76.4, benzene 3.1, chloroform 35.8,
1,2-dichloroethane 7.2, hexane 0.4 (all in g/kg, 25 C). Stability Stable under normal
conditions at pH 7. Decomposes in strong acids and alkalis. Stable to light.
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Photosynthesis inhibitor. Uses Pre-emergence control of annual weeds.
Used, preferably in combination with other herbicides, in potatoes and vegetables.
Formulation types WP
BTS 44584 63
PRODUCTS:
Discontinued products Faluron* (Fahlberg-List).
ANALYSIS:
Product and residue analysis by tlc (M. Koennig et al., Nachrichtenbl. Pfanzenschutz DDR
1987, 41, 55).
Oral Acute oral LD
50
50
for rats
>20 000 mg/kg. Non-irritating to skin. NOEL (90 d) for rats 5 mg/kg daily.
ECOTOXICOLOGY:
Fish LC
50
(96 h) for guppies 112 mg/l; (48 h) for guppies 138 mg/l.
ENVIRONMENTAL FATE:
50
c. 112118 d.
BTS 44584
NOMENCLATURE:
IUPAC name dimethyl(4-piperidinocarbonyloxy-2,5-xylyl)sulfonium toluene-4-sulfonate
Chemical Abstracts name [2,5-dimethyl-4-[(4-piperidinylcarbonyl)oxy]
phenyl]dimethylsulfonium 4-methylbenzenesulfonate CAS RN [68721608]
Development codes BTS 44584 Smiles code C[S+](C)c1cc(C)c(OC(=O)N
2
CCCCC2)
cc1C.Cc1ccc(cc1)S(=O)(=O)[O-]
23
H
31
NO
5
S
2
COMMERCIALISATION:
History Plant growth regulator reported by J. F. Garrod et al. (Monograph Brit. Plant Growth
Regulator Group, 1980, No. 4, p. 67). Evaluated by Boots Co., Ltd (later Schering Agriculture).
Patents GB 1593541.
APPLICATIONS: Uses Retards growth of various crops, including beans,
chrysanthemums, cotton, soya beans and sunfowers. Formulation types SP.
Oral Acute oral LD
50
for rats >400 mg/kg.
S
+
O
O
N S
O
O
O
-
dimethyl(4-piperidinocarbonyloxy-2,5-xylyl)sulfonium toluene-4-sulfonate
64
bufencarb
bufencarb
Insecticide
NOMENCLATURE:
Common name bufencarbe ((m) F-ISO); bufencarb (for a reaction product) (BSI, E-ISO,
ANSI, ESA)
IUPAC name of the main components are: (i) 3-(1-methylbutyl)phenyl methylcarbamate
(I); and (ii) 3-(1-ethylpropyl)phenyl methylcarbamate (II)
Chemical Abstracts name (I) and (II) CAS RN [8065369] bufencarb; [2282340]
(i); [672048] (ii) Development codes Ortho 5353
PHYSICAL CHEMISTRY:
Composition Produced by the action of methyl isocyanate on a reaction mixture of
alkylated phenols, tech. bufencarb comprisesc. 65% of a 3:1 mixture of (i) and (ii) and 35%
of insecticidally-inactive related isomers (mainly the 2- and 4-alkyl analogues). Mol. wt.
221.3 M.f. C
13
H
19
NO
2
Form Tech. mixture is a yellow to amber coloured solid. M.p. 26
39 C (tech.) B.p. c. 125 C /0.04 mmHg V.p. 4.0 mPa (30 C) S.g./density 1.024 (26 C,
tech.) Solubility In water <50 mg/l (room temperature). Very soluble in methanol, xylene;
less so in hexane. Stability Stable in acid or neutral solutions, but hydrolysis increases
with pH or temperature.
COMMERCIALISATION:
History Insecticide introduced by Chevron Chemical Company LLC. Patents US
3062864, US 3062867
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Insecticide with contact
and stomach action. Uses Insecticide, effective at 0.52.0 kg/ha against a range of soil-
and foliage-inhabiting insects, particularly Chilo plejadellus, Crambus caliginosellus larvae,
Dysmicoccus brevipes, Lissorhoptrus oryzophilus, Nephotettix nigropictus, rice planthoppers.
Formulation types DP; EC; GR .
PRODUCTS:
Discontinued products Bux* (Chevron); Bux Ten* (Chevron).
ANALYSIS:
Product analysis is by glc (B. Tucker, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 179).
Residues may be determined by glc (idem, ibid.) or by rplc (AOAC Methods, 18th Ed.,
985.23). See also Pestic. Anal. Man., I, 401.
Oral Acute oral LD
50
for rats 87 mg tech./kg. Skin and eye Acute percutaneous LD
50
for
rabbits 680 mg/kg. Minimal eye irritation (rabbits). NOEL In 90 d feeding trials, no effect
was noted with beagle dogs and albino rats receiving 500 mg/kg diet.
buminafos 65
Toxicity Class WHO (a.i.) IIECClassifcation T; R24/25| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for pheasants and ducks >27 000 mg/kg. Fish LC
50
(96 h) for
goldfsh 0.56, catfsh 1.95, trout 0.064 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Degraded in soil.
buminafos
NOMENCLATURE:
Common name buminafos (BSI, E-ISO, (m) F-ISO)
IUPAC name dibutyl 1-butylaminocyclohexylphosphonate
Chemical Abstracts name dibutyl 1-(butylamino)cyclohexylphosphonate
CAS RN [51249059] Smiles code CCCCNC1(CCCCC1)P(=O)(OCCCC)OCCCC
18
H
38
NO
3
P M.p. c. 25 C B.p.
9599 C /1 mmHg V.p. c. 100 mPa (20 C) Henry 2 10
1
Pa m
3
mol
1
(20 C, calc.)
S.g./density 0.969 (20 C)
Solubility In water 170 mg/l (room temperature). Readily miscible with common organic
solvents (e.g. acetone, methanol, xylene, etc.). Immiscible with diesel oil.
Stability Hydrolysed by strong acids and alkalis. Aqueous hydrolysis DT
50
13 d (pH 6),
20 h (pH 8), 2.75 h (pH 11).
COMMERCIALISATION:
History Plant growth regulator evaluated by VEB Chemiekombinat Bitterfeld. Later
marketed by Luxan B.V.
APPLICATIONS:
Mode of action Non-selective contact herbicide, absorbed by the leaves and roots. Uses
Control of annual grass and broad-leaved weeds in vegetables, beet, ornamental plants and
shrubs, strawberries, herbs, fruit-tree nurseries, and land to be used for horticulture. Also
used for destruction of potato haulms; for cleaning and removal of side-shoots in hops; as
a cotton defoliant; and as a desiccant for Leguminosae and seed crops of brassicas, spinach,
onions, and beet. Formulation types EC.
PRODUCTS:
Discontinued products Trakefon* (Luxan); Trakephon* (Asepta).
ANALYSIS:
Product by nmr spectrophotometry. Residues by tlc.
Oral Acute oral LD
50
50
for rats
66
butathiofos
12 00015 000, rabbits 50008000 mg/kg. Irritating to skin and eyes. NOEL (130 d) for rats
140 mg/kg daily.
ECOTOXICOLOGY:
Fish LC
50
(96 h) for guppies 7 mg/l. Bees Not hazardous to bees if used as directed.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, rapidly metabolised by dealkylation
at the oxygen and nitrogen atoms, followed by deamination. Soil/Environment Soil DT
50
c. 811 d.
butacarb
Insecticide
NOMENCLATURE:
Common name butacarb (BSI, E-ISO); butacarbe ((m) F-ISO)
IUPAC name 3,5-di-tert-butylphenyl methylcarbamate
Chemical Abstracts name 3,5-bis(1,1-dimethylethyl)phenyl methylcarbamate
CAS RN [2655198] Development codes RD 14 639; BTS 14 639
Smiles code CNC(=O)Oc1cc(cc(c1)C(C)(C)C)C(C)(C)C
16
H
25
NO
2
COMMERCIALISATION:
History Acaricide reported by J. Fraser et al. (J. Sci. Food Agric., 1967, 18, 372), used as
mixture with gamma-HCH against animal ectoparasites. Introduced by Boots Co., Ltd
(later Schering Agrochemicals).
APPLICATIONS:
Details PM5, p. 59.
butathiofos
Insecticide
P
O
O
O
S
N
N
O-2-tert-butylpyrimidin-5-yl O,O-diethyl phosphorothioate
butenachlor 67
IRAC 1B
NOMENCLATURE:
Common name butathiofos (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name O-2-tert-butylpyrimidin-5-yl O,O-diethyl phosphorothioate
Chemical Abstracts name O-[2-(1,1-dimethylethyl)-5-pyrimidinyl] O,O-diethyl
phosphorothioate CAS RN [90338208] Development codes Dowco 429; XRD 429
Smiles code CCOP(=S)(OCC)Oc1cnc(nc1)C(C)(C)C
12
H
21
N
2
O
3
PS Form Colourless oil.
B.p. 290 C V.p. 22 mPa (25 C) K
ow
logP = 4 (pH 7) Solubility In water 19.4 mg/l
(20 C). In acetone, cyclohexanone, DMF, methanol, xylene >500, digol 98, propane-1,2-diol
58 (all in g/l, 20 C).
COMMERCIALISATION:
History Insecticide evaluated by DowElanco.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses A pre-plant. treatment (c. 250 g/ha)
controls Diabrotica spp. and other soil-dwelling pests in maize. Formulation types GR .
PRODUCTS:
Discontinued products Butafos* (Dow).
ANALYSIS:
Product and residue analysis by hplc.
Oral Acute oral LD
50
for mice 15, rats 3.2 mg/kg. Skin and eye Acute percutaneous LD
50

for rats 12.625.2 mg/kg. NOEL (2 y) for rats 0.01 mg/kg daily.
ECOTOXICOLOGY:
Daphnia LC
50
0.30 mg/l. Bees Acute toxicity to honeybees 7.7 ng/bee.
butenachlor
Herbicide
NOMENCLATURE:
Common name but(nachlore) ((m) F-ISO); butenachlor (BSI, E-ISO)
IUPAC name (Z)-N-but-2-enyloxymethyl-2-chloro-2,6-diethylacetanilide
CH
2
CH
3
N
CH
2
CH
3
COCH
2
Cl
CH
2
C C
CH
3
H H
CH
2
O
68
buthidazole
Chemical Abstracts name (Z)-2-chloro-N-[(2-butenyloxy)methyl]-N-(2,6-
diethylphenyl)acetamide CAS RN [87310563] Development codes KH-218
Smiles code CCc1cccc(CC)c1N(COCC=CC)C(=O)CCl
17
H
24
ClNO
2
Form Light-yellow liquid.
M.p. 12.9 C B.p. 167 C /399 Pa V.p. 0.93 mPa (25 C) K
ow
logP = 3.51 (hplc method)
Henry 1 10
2
Pa m
3
mol
1
(calc.) S.g./density 1.0998 Solubility In water 29 mg/l
(27 C). Miscible with acetone, ethanol, ethyl acetate, and hexane. Stability Stable in acidic,
neutral, and weakly alkaline media. Unstable in sunlight.
COMMERCIALISATION:
History Herbicide introduced by Agro-Kanesho Co., Ltd. Patents US 4798618; JP
1518580 Manufacturers Agro-Kanesho
APPLICATIONS:
Biochemistry Inhibits cell division by blocking protein synthesis. It is reported that
chloroacetamides inhibit synthesis of very long chain fatty acids (J. Schmalfuss et al., Abstr.
Meeting WSSA, Toronto, 40, 117118, 2000; P. Bger, Abstr. III Int. Weed Control Congr., Brazil,
2000). Mode of action Selective herbicide, absorbed primarily by germinating shoots, and
secondarily by roots, with translocation throughout the plant, giving higher concentrations
in vegetative parts than in reproductive parts. Uses Pre-emergence control of most grass
and some broad-leaved weeds, and many aquatic weeds, in both seeded and transplanted
rice at 0.751.0 kg/ha. Formulation types GR .
ANALYSIS:
Product analysis by glc. Residues determined by glc with NPD.
Oral Acute oral LD
50
for male rats 1630, female rats 1875, male mice 6417, female mice
50
for rats >2000 mg/kg. Slightly
irritating to eyes and skin. Inhalation LC
50
(4 h) for rats 3.34 mg/l air. NOEL (90 d) for
rats 20, dogs 25 mg/kg. Non-teratogenic and no reproductive effects evident.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail and mallard ducks >2000 mg/kg. Fish LC
50

(96 h) for mirror carp 0.48, Japanese killifsh 0.42 mg/l.
ENVIRONMENTAL FATE:
50
25 d.
buthidazole
Herbicide
NOMENCLATURE:
Common name buthidazole (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-1-methyl-2-imidazolidone
buthiobate 69
Chemical Abstracts name 3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-
1-methyl-2-imidazolidinone CAS RN [55511983] Development codes Vel-5026
Smiles code CN1CC(O)N(C1=O)c2nnc(s2)C(C)(C)C
PHYSICAL CHEMISTRY:
10
H
16
N
4
O
2
S Form Colourless crystals;
(tech. is a tan powder). M.p. 133134 C V.p. 0.0053 mPa (25 C) Henry 2.09 10-7 Pa
m
3
mol
1
(calc.)
S.g./density 1.28 (25 C) Solubility In water 6.5 g/kg (25 C). In acetone 150, DMF
208, toluene 45, xylene, 10 (all in g/kg, 25 C). Stability Decomposes at 237 C; relatively
resistant to uv degradation.
COMMERCIALISATION:
History Herbicide reported by R. F. Anderson (Proc. Int. Velsicol Symp., 8th, 1974).
Introduced by Velsicol Chemical Corp. (later Sandoz AG). Patents US 3904640
APPLICATIONS:
Mode of action Contact herbicide. Uses Residual pre- and post-emergence herbicide
in industrial and non-crop areas at 4.56.5 kg/ha depending on rainfall. Used at lower
rates against broad-leaved weeds and annual grasses in maize, pineapple and sugar cane.
Formulation types GR; WP.
PRODUCTS:
Discontinued products Ravage* (Sandoz).
ANALYSIS:
Product analysis and soil residue determinations are by hplc.
Oral Acute oral LD
50
50

for rabbits >20 000 mg/kg. Non-irritant to skin and eyes (rabbits). Inhalation LC
50
(4 h)
for rats >20.8 mg/l (dust). NOEL (2 y) for rats 300 mg/kg diet; liver tumours reported in
mice at 1000 mg/kg diet. Not teratogenic in rabbits at 90 mg/kg daily. NOEL for rats
(3 generations) 1500 mg/kg diet. Other Non-mutagenic to mammalian cells.
Toxicity Class WHO (a.i.) III
ENVIRONMENTAL FATE:
Soil/Environment DT
50
>50 d.
buthiobate
Fungicide
NOMENCLATURE:
Common name buthiobate (BSI, E-ISO, (m) F-ISO)
IUPAC name butyl 4-tert-butylbenzyl N-(3-pyridyl)dithiocarbonimidate
Chemical Abstracts name butyl [4-(1,1-dimethylethyl)phenyl]methyl
70
buthiuron
3-pyridinylcarbonimidodithioate CAS RN [51308544] Development codes S-1358
(Sumitomo Chemical) Smiles code CCCCSC(=Nc1cccnc1)SCc2ccc(cc2)C(C)(C)C
21
H
28
N
2
S
2
Form Tech. is a red-brown
viscous liquid. M.p. 3133 C (tech.) V.p. 0.06 mPa (20 C) S.g./density 1.0865 (25 C,
tech.) Solubility In water 1 mg/l (25 C). In methanol and xylene >1 kg/kg (23 C).
COMMERCIALISATION:
History Fungicide reported by T. Kato et al. (Agric. Biol. Chem., 1975, 39, 169). Introduced by
Sumitomo Chemical Co., Ltd. Patents GB 1335617; US 3832351
APPLICATIONS:
Biochemistry Ergosterol biosynthesis inhibitor. Mode of action Fungicide with
protective and curative action, and long persistence. Uses Fungicide with rain fastness. It
was effective against powdery mildew on beans, fruit, ornamentals, vegetables and other
crops. Applied at 15250 mg/l. Phytotoxicity Some varieties of beans may be injured at
high concentrations. Formulation types EC; WP.
PRODUCTS:
Discontinued products Denmert* (Sumitomo Chemical).
ANALYSIS:
Product analysis by glc (S. Irie et al., Nippon Nogei Kagaku Kaishi, 1977, 51, 331).
Oral Acute oral LD
50
for male rats 4400, female rats 3200 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >5000 mg/kg. Not a skin or eye irritant (rabbits).
Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks >10 000, bobwhite quail 21 800 mg/kg. Fish LC
50

(48 h) for carp 6.4 mg/l.
buthiuron
Herbicide
NOMENCLATURE:
Common name buthiuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-(5-butylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea
Chemical Abstracts name N-[5-(butylsulfonyl)-1,3,4-thiadiazol-2-yl]-N,N-dimethylurea
CAS RN [30043551] Development codes MET 1489
Smiles code CCCCS(=O)(=O)c1nnc(s1)N(C)C(=O)NC
9
H
16
N
4
O
3
S
2
COMMERCIALISATION:
butocarboxim 71
butocarboxim
IRAC 1A; oxime carbamate
NOMENCLATURE:
Common name butocarboxim (BSI, E-ISO); butocarboxime ((f) F-ISO)
IUPAC name 3-(methylthio)butanone O-methylcarbamoyloxime
Chemical Abstracts name 3-(methylthio)-2-butanone O-[(methylamino)carbonyl]oxime
CAS RN [34681102] EC no 2521393 Development codes Co 755 (Wacker)
Smiles code CNC(=O)ON=C(C)C(C)SC
PHYSICAL CHEMISTRY:
Composition Tech. grade is liquid and obtained as an 85% tech. concentrate in xylene
containing the (E)- and (Z)- isomers in a ratio of 8590:1510. Mol. wt. 190.3 M.f.
C
7
H
14
N
2
O
2
S Form Pale brown, viscous liquid (tech.). Crystalline at lower temperatures.
M.p. 37 C ((E)- isomer); ((Z)- isomer is an oil at room temperature) V.p. 10.6 mPa
(20 C) (tech., without residual xylene) K
ow
logP = 1.1 Henry 5.76 10
5
Pa m
3
mol
1

(calc.) S.g./density 1.12 (20 C) Solubility In water 35 g/l (20 C). Completely miscible
with aromatic hydrocarbons, esters, and ketones. Low solubility in aliphatic hydrocarbons
(11 g/l) and carbon tetrachloride. Stability Stable at pH 57 (up to 50 C), but hydrolysed
by strong acids and alkalis. Stable to sunlight and oxygen. Thermally stable up to 100 C.
COMMERCIALISATION:
History Insecticide reported by M. Vulic et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1973, 38, 1175). Structure/activity of analogues discussed (T. A. Magee & L. E. Limpel, J. Agric.
Food Chem., 1977, 25, 1376). Introduced by Wacker-Chemie GmbH. Patents DE 2036491;
US 3816532; GB 1353202
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide with
contact and stomach action. Absorbed by the leaves and roots. Uses Control of aphids,
thrips, whitefies, mealybugs, and other sucking insects (with secondary action against
spider mites) on fruit trees (including citrus), vegetables, cereals, cotton, hops, tobacco, and
ornamentals (including ornamentals cultivated by hydroponics). Formulation types AE;
EC; SL .
(E)-
(Z)-
CH
3
C
CH
CH
3
N
O C
NH
O
CH
3
SCH
3
CH
3
C
CH
CH
3
N
O C
NH
O
CH
3
SCH
3
72
butonate
PRODUCTS:
Discontinued products Drawin* (Wacker); Hydrosekt* (Luxan).
ANALYSIS:
Product analysis by i.r. spectrometry or by hplc. Residues of butocarboxim, its sulfoxide
and sulfone (butoxycarboxim) determined by glc with TID. Details available from Wacker-
Chemie GmbH.
EHC 64 (1986) is a general review of pesticides with a carbamate chemical structure.
JMPR Evaln. I 48 (1986). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
50

for albino rabbits 360 mg/kg. Irritating to eyes. Inhalation LC
50
(4 h) for rats 1 mg/l air.
NOEL (2 y) for rats 100 mg/kg diet; (90 d) for dogs 100 mg/kg diet. No carcinogenic or
mutagenic activity in routine tests at the highest dose (300 mg/kg diet) in rats during 2 y,
nor any effect on fertility, growth rate or mortality. ADI/RfD (JMPR) No ADI [1985]; (BfR)
0.02 mg/kg b.w. [1990]. Other Not mutagenic in the Ames assay. Toxicity Class WHO
(a.i.) Ib EPA (formulation) II ECClassifcation R10| T; R23/24/25| Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds LD
50
for mallard ducks 64 mg/kg. LC
50
(8 d) for Japanese quail 1180 mg/kg diet.
Fish LC
50
(96 h) for rainbow trout 29 mg/l. LC
50
(24 h) for rainbow trout 35, goldfsh 55,
guppies 70 mg/l. Daphnia LC
50
(24 h) 3.25.6 mg/l. Algae NOEL for Algae 62.5 mg/l.
Bees Toxic to bees; LD
50
1 g/bee.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, metabolised to butoxycarboxim, and
excreted in the urine as butoxycarboxim and its degradation products. Plants In plants,
degradation is the same as in soil. Soil/Environment In soil, the methylamine moiety is
split off, and the sulfur atom is oxidised to sulfoxide and sulfone. DT
50
in soil 18 d; DT
50

for metabolites 1644 d.
butonate
Insecticide
IRAC 1B
NOMENCLATURE:
Common name butonate (BSI, E-ISO, (m) F-ISO); butilchlorofos* (former exception
USSR) IUPAC name 2,2,2-trichloro-1-(dimethoxyphosphinoyl)ethyl butyrate
Chemical Abstracts name 2,2,2-trichloro-1-(dimethoxyphosphinyl)ethyl butanoate
CAS RN [126227] Smiles code CCCC(=O)OC(C(Cl)(Cl)Cl)P(=O)(OC)OC
butopyronoxyl 73
8
H
14
Cl
3
O
5
P
COMMERCIALISATION:
History Insecticide reported by B. W. Arthur & J. E. Casida (J. Agric. Food Chem., 1958, 6,
360). Introduced by Prentiss Drug & Chemical Co.
APPLICATIONS:
Details PM4, p. 61.
butopyronoxyl
Insect repellent
NOMENCLATURE:
Common name butopyronoxyl (US Pharmacopoeia)
IUPAC name butyl 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylate (I)
Chemical Abstracts name (I) Other names dihydropyrone; butyl mesityloxide oxalate
CAS RN [532343] Smiles code CCCCOC(=O)/C/1=C/C(=O)CC(C)(C)O1;
without stereochemistry: CCCCOC(=O)C1=CC(=O)CC(C)(C)O1
PHYSICAL CHEMISTRY:
Composition Tech. contains 85% butopyronoxyl with 2% mesityl oxide; the remainder
is mainly dibutyl oxalate and butanol. It exists mainly as the dihydropyrone (I) but with the
open chain enol (II) in equilibrium (S.A. Hall et al., J. Am. Chem. Soc., 1945, 67, 1224). Mol. wt.
226.3 M.f. C
12
H
18
O
4
Form Yellow to pale red liquid with a mild aromatic odour. B.p. 90%
distils between 256270 C S.g./density 1.0521.060 (20 C)
Solubility Practically insoluble in water and glycerol. Slightly soluble in ethylene glycol,
refned petroleum oils; miscible with chloroform, ethanol, diethyl ether, glacial acetic acid.
COMMERCIALISATION:
History Insect repellent introduced by US Industrial Chemicals Inc. and by Kilgore
Chemicals. Patents US 2138540
PRODUCTS:
Discontinued products Indalone* (FMC).
Oral Acute oral LD
50
for rats 7840, guinea pigs 3200 mg/kg. Skin and eye Acute
percutaneous LD
50
for rabbits 10 000 mg/kg. Not a skin irritant but may cause a stinging
sensation. NOEL In 2 y feeding trials, some growth retardation was observed in rats
receiving 80 g/kg diet. Toxicity Class WHO (a.i.) U
Details PM6, p. 66.
74
butoxy(polypropylene glycol)
2-(2-butoxyethoxy)ethyl piperonylate
NOMENCLATURE:
IUPAC name 2-(2-butoxyethoxy)ethyl piperonylate
Chemical Abstracts name 2-(2-butoxyethoxy)ethyl 1,3-benzodioxole-5-carboxylate
Other names BCP CAS RN [136630]
Smiles code CCCCOCCOCCOC(=O)c1ccc2OCOc2c1
16
H
22
O
6
COMMERCIALISATION:
History Synergist for pyrethrum introduced by Bush Boake & Allen.
APPLICATIONS: Uses A pyrethrum synergist.
PRODUCTS:
Discontinued products Bucarpolate* (Bush Boake & Allen).
2-(2-butoxyethoxy)ethyl thiocyanate
Insecticide
NOMENCLATURE:
IUPAC name 2-(2-butoxyethoxy)ethyl thiocyanate (I)
Chemical Abstracts name (I) Other names butyl Carbitol thiocyanate; butyl
Carbitol rhodanate; beta-butoxy-beta-thiocyanodiethyl ether CAS RN [112561]
Smiles code CCCCOCCOCCSC#N
9
H
17
NO
2
S
COMMERCIALISATION:
History Insecticide reported by D. F. Murphy & C. H. Peet (J. Econ. Entomol., 1932, 25, 123).
Introduced by Rohm & Haas Co.
PRODUCTS:
Discontinued products Lethane 384* (Rohm & Haas).
ECClassifcation R10| T; R24/25
butoxy(polypropylene glycol)
Insect repellent
NOMENCLATURE:
Common name butoxy(polypropylene glycol) (ESA)
IUPAC name -hydroxypropyl-o-butoxypoly[oxy(1-methylethylene)]
Chemical Abstracts name -butyl-o-hydroxypoly[oxy(methyl-1,2-ethanediyl)]
butroxydim 75
CAS RN [9003138]
COMMERCIALISATION:
History Fly repellent. Introduced by Union Carbide Corp.
PRODUCTS:
Discontinued products Crag Fly Repellent* (Union Carbide).
butroxydim
Herbicide
HRAC A WSSA 1; cyclohexanedione oxime
NOMENCLATURE:
Common name butroxydime ((m) F-ISO); butroxydim (BSI, E-ISO)
IUPAC name 5-(3-butyryl-2,4,6-trimethylphenyl)-2-(1-ethoxyiminopropyl)-3-
hydroxycyclohex-2-enone
Chemical Abstracts name 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[2,4,6-trimethyl-
3-(1-oxobutyl)phenyl]-2-cyclohexen-1-one CAS RN [138164122] EC no 4147903
Development codes ICIA0500 (ICI)
Smiles code CCCC(=O)c1c(C)cc(C)c(C2CC(=C(C(=NOCC)CC)C(=O)C2)O)c1C
24
H
33
NO
4
Form Off-white powdery
solid. M.p. 80.8 C
V.p. 1 10
3
mPa (20 C) K
ow
logP = 1.90 (pH 7, 25 C) Henry 5.79 10
5
Pa m
3
mol
1

(calc.) S.g./density 1.20 (tech., 25 C) Solubility In water 6.9 mg/l (pH 5.5, 20 C). In
dichloromethane >500, acetone 450, toluene 480, acetonitrile 380, methanol 90, hexane 30
(all in g/l). Stability Hydrolysis DT
50
10.5 d (pH 5), >240 d (pH 7), stable (pH 9) (all 25 C).
pKa 4.36 (23 C), weak acid
COMMERCIALISATION:
History First sold in 1995. Divested to Crop Care Australasia Pty Ltd in 2002.
APPLICATIONS:
Biochemistry Fatty acid synthesis inhibitor, by inhibition of acetyl CoA carboxylase
(ACCase). Mode of action Post-emergence herbicide. Uses A post-emergence grass
herbicide for use on broad-leaved crops, at 2575 g/ha. Formulation types WG .
PRODUCTS:
Discontinued products Falcon* (Crop Care).
CH
2
CH
3
N
OCH
2
CH
3
OH
O CH
3
CH
3
CH
3
CH
3
(CH
2
)
2
O
76
buturon
ANALYSIS:
Residues determined by hplc with uv detection, or by hplc-ms.
Oral LD
50
for male rats 3476, female rats 1635 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats >2000 mg/kg. Moderate skin irritant; mild eye irritant (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation LC
50
(4 h) for rats >2.99 mg/l. NOEL NOAEL (1 y)
for dogs 5 mg/kg b.w. daily; NOEL (2 y) for rats 2.5, mice 10 mg/kg b.w. daily (liver tumours
only in males at high dose); NOEL developmental for rats 5, rabbits 15 mg/kg b.w. daily.
ADI/RfD 0.025 mg/kg. Other Genotoxicity negative. Not oncogenic (rats).
Toxicity Class WHO (a.i.) III.ECClassifcation (T; R61| R22| R38| N; R50, R53)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks >2000, bobwhite quail 1221 mg/kg. Sub-acute
dietary LC
50
(5 d) for mallard ducks >5200, bobwhite quail 5200 mg/kg. Fish LC
50
(96 h)
for rainbow trout >6.9, bluegill sunfsh 8.8 mg/l. Daphnia LC
50
(48 h) >3.7 mg/l. Algae
EbC50 for Selenastrum capricornutum 0.71 mg/l. Bees LD
50
(contact, 24 h) >200 g/bee.
Worms LC
50
(14 d) for Eisenia foetida >1000 mg/kg.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, >90% of the dose is excreted within 7 d.
Various oxidative transformations of the butyryl chain dominate the metabolic pathway.
Neither parent nor metabolites bioaccumulate in tissues. Plants Rapidly metabolised
in plants. Soil/Environment Soil K
oc
61270 (stronger adsorption in low pH soils).
Rapid degradation in aerobic soil, lab. DT
50
c. 9 d (20 C, 40% MHC, pH 7.0, 4.09% o.m.);
metabolites include 5-(3-butyryl-2,4,6-trimethylphenyl)-3-hydroxy-2-(1-iminopropyl)
cyclohex-2-enone, 6-(3-butyryl-2,4,6-trimethylphenyl)-2-ethyl-4,5,6,7-tetrahydro-4-oxo-
1,3-benzoxazole, 2-(3-butyryl-2,4,6-trimethylphenyl)glutaric acid and 5-(3-butyryl-2,4,6-
trimethylphenyl)-3-hydroxy-2-propionylcyclohex-2-enone.
buturon
Herbicide
NOMENCLATURE:
Common name buturon (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(4-chlorophenyl)-1-methyl-1-(1-methylprop-2-ynyl)urea
Chemical Abstracts name N-(4-chlorophenyl)-N-methyl-N-(1-methyl-2-propynyl)urea
CAS RN [3766607] Development codes H 95 (BASF) Smiles code CC(C#C)N(C)
C(=O)Nc1ccc(Cl)cc1
12
H
13
ClN
2
O Form Colourless solid.
M.p. 145146 C; (tech., 132142 C) V.p. 0.01 mPa (20 C) Henry 7.89 10
5
Pa m
3
mol
1
(calc.) Solubility In water 30 mg/l (20 C). In acetone 279, benzene 9.8, methanol
128 (all in g/kg, 20 C).
sec-butylamine 77
Stability Stable under normal conditions (1<pH<13), but slowly decomposes in boiling
water.
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Meded. Landbouwhogesch. Opzoekingsstn. Staat
Gent, 1964, 29, 719). Introduced by BASF AG. Patents DE 1108977
APPLICATIONS:
Biochemistry Inhibits photosynthesis. Mode of action Selective, systemic herbicide;
uptake is predominantly via the roots. Uses A pre-em. and post-em. herbicide, absorbed
mainly by the roots and recommended for use at 0.51.5 kg/ha in cereals and maize for
the control of shallow-germinating grasses and broad-leaved weeds. Formulation types
WP.
PRODUCTS:
Discontinued products Eptapur* (BASF); Discontinued mixtures Basftox*
(+ isonoruron) (BASF).
ANALYSIS:
Product analysis by hydrolysis and potentiometric titration of the 4-chloroaniline produced.
Residues determined by hydrolysis and colorimetric estimation of the 4-chloroaniline
produced.
Oral Acute oral LD
50
for rats 3000 mg/kg. Skin and eye Applications (20 h) to the backs
of rabbits produced a slight erythema but the ears were unaffected. NOEL In 120 d
feeding trials, rats receiving 500 mg/kg diet showed no ill-effect. Other I.p. LD
50
for mice
c. 500 mg/kg. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Plants It is rapidly degraded in plants. Soil/Environment In soil, bacterial degradation
under the infuence of CO
2
, probably involving 4-chloroaniline formation. Twelve weeks
after use, no active substance is biologically detectable.
sec-butylamine
Fungicide
NOMENCLATURE:
Common name (RS)-sec-butylamine (proposed E-ISO, in lieu of a common name)
IUPAC name (RS)-sec-butylamine; (RS)-2-aminobutane
Chemical Abstracts name 2-butanamine CAS RN [13952846] (RS)-sec-butylamine;
CH
3
CH
2
CH(CH
3
)NH
2
78
sec-butylamine
[13250129] (R)-sec-butylamine; [513495] (S)-sec-butylamine EC no 2377327 (RS)-
isomer; 2362326 (R)- isomer; 2081647 (S)- isomer
Smiles code CCC(C)N
PHYSICAL CHEMISTRY:
4
H
11
N Form Colourless liquid, with
an ammoniacal odour. M.p. <100 C B.p. 6365 C V.p. 18 kPa (20 C) K
ow
logP =
0.74 S.g./density 0.724 (20 C) Solubility Miscible with water and with most organic
solvents. With acids, forms water-soluble salts. Stability Stable at room temperature.
Exothermic reaction with acids. pKa Base, forming water-soluble salts with acids. F.p.
19.5 C (DIN 51755)
COMMERCIALISATION:
History Fungicidal properties of this fumigant reported by J. W. Eckert & M. J. Kolbezen
(Nature (London), 1962, 194, 188). Introduced by BASF AG in 1971; registration transferred
to Hortichem in 1992 (now Certis UK).
APPLICATIONS:
Mode of action Fumigant fungicide. Uses Fungicidal fumigation of seed and ware
potatoes for control of skin spot and gangrene. As fungicidal dips or sprays on harvested
fruit, e.g. control of citrus blue and green moulds and stem rot of oranges. Prevention of
Botrytis on chrysanthemums and gladioli during storage and transit.
Formulation types SL .
PRODUCTS:
Discontinued products Butafume* (BASF); Deccotane* (post-harvest) (Decco
Cerexagri); Tutane* (DowElanco).
ANALYSIS:
Product analysis by acid-base titration. Residues determined by glc of a derivative (Anal.
Methods Pestic. Plant Growth Regul., 1976, 8, 251; E. W. Day et al., J. Assoc. Off. Anal. Chem., 1968,
51, 39; Resid. Anal. Methods). See also Pestic. Anal. Man., II, 186.450.
JMPR Evaln. 37 (1981). ICSC.401 (1999). EU Status (1107/2009) Not approved,
Oral Acute oral LD
50
for rats 380, dogs 225 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits >2500 mg/kg. Irritating to skin and eyes. Inhalation Vapours dangerous if
inhaled. NOEL In 2 y feeding trials, teratogenicity studies, reproduction studies, rats and
dogs receiving 2500 mg/kg diet suffered no ill-effect. In teratogenicity studies, NOEL: for
rats 2500 mg/kg diet; for rabbits 5000 mg/kg diet. In reproduction studies in rats, NOEL
2500 mg/kg diet. ADI/RfD (JMPR) Temporary ADI withdrawn [1984].
Toxicity Class WHO (a.i.) II.ECClassifcation F; R11| Xn; R20/22| C; R35| N; R50 (for
(R)-, (S)-, or (RS)- isomers)
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
for young bluegill sunfsh >50 mg/l.
Daphnia EC
50
/LC
50
(48 h) 40.4 mg/l. Algae EC
50
/LC
50
(72 h) 0.54 mg/l.
calcium and lead arsenate 79
cadmium calcium copper zinc chromate sulfate
Fungicide
NOMENCLATURE:
IUPAC name cadmium calcium copper zinc chromate sulfate (I)
Development codes Fungicide 531
COMMERCIALISATION:
History Fungicide introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
PRODUCTS:
Discontinued products Crab Turf Fungicide* (Union Carbide).
EHC 200 (1998) is a general review of copper and copper compounds.
calcium and lead arsenate
Herbicide, insecticide
NOMENCLATURE:
Chemical Abstracts name tricalcium arsenate CAS RN [7778441]; [7778394]
(arsenic acid)
PHYSICAL CHEMISTRY: Mol. wt. 398.1 M.f. As
2
Ca
3
O
8
M.p. 35 C (arsenic acid)
V.p. 0.0 (for acid or salt?) Solubility Insoluble in water and organic solvents. The wettable
powder, when made up in aqueous solution, should contain less than 0.5% of dissolved
As
2
O
5
, which originates from impurities. Stability Moisture and carbon dioxide cause slow
decomposition to calcium carbonate and (phytotoxic) dicalcium hydrogen arsenate. In the
presence of acids, water-soluble, strongly phytotoxic arsenic acid is produced. pKa pKa1
2.3, pKa2 7.1 (J. Ag. & Food Chem., 24, 717 (1976)) (for acid).
APPLICATIONS: Uses Pre-emergence herbicidal treatment of turf and lawns to
control crabgrass. Controls chickweed, annual bluegrass, and certain soil insects, including
Japanese beetle. Phytotoxicity Foliage of stone fruit is particularly susceptible. Plant
damage can occur in the presence of water-soluble arsenic compounds. Formulation
types DP; WP; RB; GR .
PRODUCTS:
Discontinued products Pencal* (Pennwalt); Security* (Woolfolk); Security*
(Woolfolk).
ANALYSIS:
Product analysis described (AOAC Methods, 18th Ed., 921.05, 921.06, 922.03, 925.03,
963.06); lead arsenate ibid., 920.16920.21. Residue analysis by mineralisation of the sample,
distillation of the arsenic, and determination colorimetrically at 540 nm, as the arsine
complex with silver diethyldithiocarbamate (Man. Pestic. Residue Anal., 230).
80
calcium cyanamide
EHC 224 (2001). JMPR Evaln. 11 (1968), 31 (1978) for lead arsenate. HSG 70 (1992).
ICSC.765 (1999) for calcium arsenate; ICSC.911 (1997) for lead arsenate. IARC 87 (2006)
(inorganic lead); 23 (1980), Suppl 7 (1987) (arsenic compounds).
IARC Class 1 (evaluation applies to arsenic compounds as a whole, not necessarily to all
individual compounds within the group); 2A (inorganic lead)
Oral Acute oral LD
50
for rats 20 mg/kg; (lead saltc. 10 mg/kg). NOEL 0.42 mg/kg b.w. (EPA
Tracking). ADI/RfD (JMPR) No ADI [1968], also for lead salt; (EPA) 0.0042 mg/kg b.w.
[1968]. Other Acute oral LD
50
for rats 20, rabbits 50, dogs 38 mg/kg. Dermal resorption is
minimal. Toxicity Class WHO (a.i.) Ib (also for lead salt)
ECClassifcation R45| T; R23/25| N; R50, R53 (for arsenic acid and salts)
ECOTOXICOLOGY:
Fish Very toxic to fsh. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Inorganically-bound arsenic remains unchanged for a long time in the
soil. The alleged microbial reduction to arsine and volatilisation is disputed.
calcium cyanamide
Fertiliser, fungicide, herbicide
NOMENCLATURE:
IUPAC name calcium cyanamide
Chemical Abstracts name calcium cyanamide CAS RN [156627]
EC no 2058618 Smiles code [Ca+2].[N-]=C=[N-]
PHYSICAL CHEMISTRY: Mol. wt. 80.10 M.f. CCaN
2
M.p. c. 1200 C (sublimes
11501200 C)
S.g./density 2.29 (420 C) Solubility Insoluble in water, but gradually hydrolyses.
Insoluble in organic solvents. Stability Very stable under dry storage conditions.
Decomposed in moist conditions and in the presence of acids, to calcium hydrogen
cyanamide, cyanamide, and urea.
COMMERCIALISATION:
History Used as a fertiliser since 1905. Later introduced as herbicide and defoliant by
American Cyanamid Co., but these uses now discontinued.
APPLICATIONS:
Mode of action Pre- and post-emergence herbicide and defoliant, with secondary
fungicidal action. Produces hydrogen cyanamide upon contact with soil moisture, which
is toxic to plants, seeds, and disease organisms. Uses Fertiliser with secondary control of
weeds in cereals, maize, vines, feld crops, vegetables, and in meadows and pastures. Also
fungicidal control of eyespot in cereals, and club root in brassicas. Cyanamide (q.v. in Main
cambendichlor 81
entries) is used as a herbicide and plant growth regulator. Phytotoxicity The chlorophyll
of most plants is sensitive, especially in humid conditions. Formulation types GR .
PRODUCTS:
Discontinued products Cyanamid* (Cyanamid).
ANALYSIS:
Product analysis by determination of nitrogen by the Kjeldahl process. Residues in
soil by extraction with 0.1 N hydrochloric acid, distillation, clean-up on aluminium
oxide and determination of the red complex formed with Na
2
NH
4
[Fe(CN)
5
NH
3
]
spectrophotometrically at 530 nm.
ICSC.639 (2006) EU Status (1107/2009) Vote for non-inclusion, SCFCAH 05/2008.
Oral Acute oral LD
50
for rats 1400 mg/kg. Skin and eye Mild skin irritant.
Inhalation LC
50
(4 h) for rats >0.15 mg/l air. Irritation of the mucous membranes of the
respiratory tract is evident after inhalation of the dust. Toxicity Class WHO (a.i.) O
ECClassifcation Xn; R22| Xi; R37, R41
ECOTOXICOLOGY:
Fish Not signifcantly toxic to fsh provided the pH of the water does not exceed 88.5.
ENVIRONMENTAL FATE:
Soil/Environment Taken up into plants and fermentatively degraded. After 9 days, no
cyanamide nitrogen is detectable in potatoes.
Details PM5, p. 72.
cambendichlor
Herbicide
NOMENCLATURE:
Common name cambendichlor (BSI, E-ISO, ANSI, WSSA); cambendichlore ((m) F-ISO)
IUPAC name 2,2-(phenylimino)diethylene bis(3,6-dichloro-o-anisate)
Chemical Abstracts name (phenylimino)di-2,1-ethanediyl bis(3,6-dichloro-
2-methoxybenzoate) CAS RN [56141005] Development codes Vel 4207
Smiles code COc1c(Cl)ccc(Cl)c1C(=O)OCCN(CCOC(=O)c2c(Cl)ccc(Cl)c2OC)
c3ccccc3
26
H
23
Cl
4
NO
6
COMMERCIALISATION:
History Herbicide introduced by Velsicol Chemical Corp. (later Sandoz AG).
82
camphechlor
camphechlor
Insecticide
NOMENCLATURE:
Common name polychlorcamphene (USSR); camphechlor (BSI, E-ISO); camph(chlore)
((m) F-ISO); toxaphene (Belgium, Canada, USA)
IUPAC name a reaction mixture of chlorinated camphenes containing 6769% chlorine
Chemical Abstracts name toxaphene CAS RN [8001352] EC no 2322833
Development codes Hercules 3956
PHYSICAL CHEMISTRY:
Composition Composition examined by J. E. Casida et al. (J. Agric. Food Chem., 1974,
22, 653; 1975, 23, 991); 26 components account for about 40% of the product. Mol.
wt. 431.8 (approx.) M.f. C
10
H
10
Cl
8
(approx.) Form A yellow wax of mild terpene-like
odour. M.p. Softens 7095 C V.p. 2700053000 mPa (25 C) S.g./density 1.65 (25 C)
Solubility In water c. 3 mg/l (room temperature). Readily soluble in organic solvents
including petroleum oils. Stability Dehydrochlorinated by heat, by strong sunlight and by
certain catalysts such as iron.
COMMERCIALISATION:
History Insecticide reported by W. LeRoy Parker & J. R. Beacher (Del. Univ. Agric. Exp. Stn.
Bull., 1947, No. 264). Introduced by Hercules Inc. Patents US 2565471; US 2657164
APPLICATIONS:
Mode of action Non-systemic, contact and ingested insecticide with some acaricidal
action. Uses Control of many insects in cereals, cotton, fruit, maize, vegetables and the
control of Cassia obtusifolia in soya beans. Has also been used for the control of animal
ectoparasites. A heptachlorobornane and a mixture of two octachlorobornanes are
more toxic to insects and mice than other components, and are similarly biodegradable.
Phytotoxicity Phytotoxic to cucurbits and some varieties of plum and damson.
Formulation types EC. Compatibility Not compatible with strongly alkaline pesticides.
PRODUCTS:
Discontinued products Agronex Hepta* (Epro); Altox* (Hercules); Attac* (BFC);
Toxaphene* (except in countries where used as common name) (Hercules).
ANALYSIS:
Product analysis by total chlorine (CIPAC Handbook, 1970, 1, 132) or by tlc (AOAC Methods
18th Ed., 972.05). Residues determined by glc with ECD (Anal. Methods Pestic. Plant Growth
Regul., 1972, 6, 514), by gel permeation chromatography and glc (AOAC Methods, 14th Ed.,
29.03729.043) or by spectrometry of a derivative (C. L. Dunn, Anal. Methods Pestic., Plant
Growth Regul. Food Addit., 1964, 2, 523). See also Pestic. Anal. Man., I, 208, 504.
EHC 45 (1984). JMPR Evaln. 21 (1973). HSG 40 (1990). PDS 20 (1975). ICSC.843 (1997).
IARC 79 (2001). EU Status (1107/2009) Considered to be outside the scope of the
Directive; already banned, 79/117/EEC as amended by 83/131/EEC and by Commission
Regulation 850/2004.
carbanolate 83
IARC Class 2B
Oral Acute oral LD
50
50
for
rats 7801075 mg/kg. NOEL (2 y) for dogs 10 ppm (0.25 mg/kg b.w.) (EPA Tracking).
ADI/RfD (JMPR) No ADI [1973]; (EPA) 0.00025 mg/kg b.w. [1986]. Water GV Excluded
from GV derivation (U). Toxicity Class WHO (a.i.) IIECClassifcation R40| T; R25| Xn;
R21| Xi; R37/38| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Toxic to birds. Fish LC
50
for young rainbow trout 0.2, young pike 0.1 mg/l.
Bees Low toxicity to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, camphechlor accumulates temporarily
in body fat, but is rapidly eliminated, partly as the unchanged substance and partly as
dechlorinated and partially dechlorinated metabolites. Soil/Environment In soil, becomes
tightly bound and is highly resistant to leaching. Persistent in soil (DT
50
varies between 70 d
and 12 y, depending on soil type and climate).
carbamorph
Fungicide
NOMENCLATURE:
Common name carbamorph (BSI, E-ISO); carbamorphe ((m) F-ISO)
IUPAC name morpholinomethyl dimethyldithiocarbamate
Chemical Abstracts name 4-morpholinylmethyl dimethylcarbamodithioate
CAS RN [31848110] Development codes MC 833
Smiles code CN(C)C(=S)SCN1CCOCC1
8
H
16
N
2
OS
2
COMMERCIALISATION:
History Fungicide introduced by Murphy Chemical Co. (later DowElanco).
carbanolate
Insecticide, ixodicide
NOMENCLATURE:
Common name carbanolate (BSI, E-ISO, (m) F-ISO, ESA, JMAF)
IUPAC name 6-chloro-3,4-xylyl methylcarbamate
84
carbon disulfde
Chemical Abstracts name 2-chloro-4,5-dimethylphenyl methylcarbamate
CAS RN [671045] Development codes U 12 927
Smiles code CNC(=O)Oc1cc(C)c(C)cc1Cl
10
H
12
ClNO
2
COMMERCIALISATION:
History Veterinary insecticide and ixodicide introduced by Upjohn Co. (later Nor-Am).
APPLICATIONS:
PRODUCTS:
Discontinued products Banol* (Upjohn).
ANALYSIS:
Residues by glc of a derivative (AOAC Methods, 18th Ed., 975.40).
carbasulam
Herbicide
NOMENCLATURE:
Common name carbasulame ((m) F-ISO); carbasulam (BSI, E-ISO)
IUPAC name methyl 4-(methoxycarbonylsulfamoyl)carbanilate
Chemical Abstracts name methyl [[4-[(methoxycarbonyl)amino]phenyl]
sulfonyl]carbamate CAS RN [1773371] Development codes M&B 9555
Smiles code COC(=O)Nc1ccc(cc1)S(=O)(=O)NC(=O)OC
10
H
12
N
2
O
6
S
COMMERCIALISATION:
History Herbicide evaluated by May & Baker Ltd (later Rhne-Poulenc Agrochimie).
carbon disulfde
Insecticide, nematicide
NOMENCLATURE:
Common name carbon disulfde (ESA); carbon disulphide (BSI, E-ISO, accepted in lieu of
common name); sulfure de carbone (F-ISO)
carbon tetrachloride 85
IUPAC name carbon disulfde
Chemical Abstracts name carbon disulfde Other names carbon bisulphide
CAS RN [75150] EC no 2008436 Smiles code S=C=S
PHYSICAL CHEMISTRY: Mol. wt. 76.13 M.f. CS
2
Form Colourless mobile liquid.
Its impurities have an unpleasant odour. M.p. 108.6 C B.p. 46.3 C V.p. 4.7 107 mPa
(25 C) K
ow
logP = 1.84 (Agchem. Desk Ref.) S.g./density 1.2628 (20 C); gas, 2.63 (air
= 1) Solubility In water 2.2 g/l (32 C). Miscible with chloroform, diethyl ether, ethanol.
F.p.c. 20 C; ignites spontaneously >100 C
COMMERCIALISATION:
History Used as insecticide in 1854 by Garreau (see Science, 1926, 64, 326).
APPLICATIONS:
Mode of action Fumigant insecticide and nematicide. Uses For fumigation of nursery
stock and for soil treatment against insects and nematodes. It was also used in some
countries as an insecticide in mixtures with carbon tetrachloride (to reduce fre hazard)
for fumigating stored grain.
PRODUCTS:
Discontinued products Weevil Tox* (Stauffer).
ANALYSIS:
Product analysis by glc (AOAC Methods, 18th Ed., 966.05). Residues in grain may be
determined by glc (S. G. Heuser & K. A. Scudmore, J. Sci. Food Agric., 1969, 20, 566) or by
colorimetry of a derivative (C. L. Dunning, J. Assoc. Off. Agric. Chem., 1957, 40, 168). See also
Pestic. Anal. Man., II, 180.467. The concentration in air may be measured by drawing the air
through an ethanolic solution of diethylamine and copper(II) acetate and colorimetry of
the complex produced. Methods reviewed by J. L. Daft in Comp. Anal. Profles,Chapter 11.
EHC 10 (1979). JMPR Evaln. I 45 (1985); JMPR Evaln. 17 (1971). ICSC.022 (2000). CICAD 46
(2002). EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Inhalation The vapour is highly poisonous, producing giddiness and vomiting in 30 min at
6.8 mg/l air; repeated daily exposures to 0.227 mg/l air caused ill health.
NOEL Inhalation NOEL for rats 20 ppm (11 mg/kg b.w.) (EPA Tracking). ADI/RfD (JMPR)
No ADI [1965]; (EPA) RfD 0.1 mg/kg b.w. [1985]. Toxicity Class WHO (a.i.) FM
ECClassifcation F; R11| R62, R63| T; R48/23| Xi; R36/38 (concentration-dependent)
carbon tetrachloride
Insecticide
NOMENCLATURE:
Common name carbon tetrachloride (BSI, E-ISO, ESA, traditional name); t(trachlorure
de carbone) (F-ISO, accepted in lieu of a common name)
86
carbon tetrachloride
IUPAC name carbon tetrachloride; tetrachloromethane
Chemical Abstracts name tetrachloromethane CAS RN [56235]
EC no 2002628 Smiles code ClC(Cl)(Cl)Cl
PHYSICAL CHEMISTRY: Mol. wt. 153.8 M.f. CC
l4
Form Colourless liquid.
M.p. 23 C B.p. 76 C V.p. 15 kPa (25 C) Henry 8.24 103 Pa m
3
mol
1
(calc.) S.g./
density 1.588 (25 C); gaseous, 5.32 (air = 1) Solubility In water 280 mg/kg (25 C).
Miscible with most organic solvents. Stability Though generally inert, it is decomposed by
water at high temperatures.
F.p. Non-fammable and non-explosive
COMMERCIALISATION:
History Use as insecticidal fumigant described by W. E. Britton (Conn. Agric. Exp. Stn. Rep.,
1908, No. 31).
APPLICATIONS:
Mode of action Fumigant insecticide Uses Shows weak insecticidal activity, but was used
for grain disinfestation when long exposures are possible, its main advantages being low
absorption by treated grain. It was often used in mixtures with more potent fumigants,
such as ethylene dichloride, to reduce the fre hazard of the latter. It has also been used as
an anthelmintic in veterinary practice.
ANALYSIS:
Product analysis by glc (AOAC Methods, 14th Ed., 6.1596.164). Residues in stored cereals
determined by glc with ECD (ibid., 18th Ed., 977.18; K. A. Scudamore, Anal. Methods Pestic.
Plant Growth Regul., 1988, 16, 207, 222; Anal. Methods Residues Pestic., 1988, Part I, M8; Analyst
(London), 1974, 99, 570). Methods reviewed by J L Daft in Comp. Anal. Profles,Chapter 11.
EHC 208 (1999). JMPR Evaln. I 45 (1985); JMPR Evaln. 33 (1979). HSG 108 (1998). ICSC.024
(2000). IARC 20 (1979); 71 (1999).
IARC Class 2B
Oral Acute oral LD
50
for rats 57309770, mice 12 800, rabbits 63809975 mg/kg.
50
for rats 5070 mg/kg (ESA, Special
Publication,1978). NOEL NOAEL for rats 0.71 mg/kg b.w. daily (EPA IRIS).
ADI/RfD (JMPR) No ADI [1965]; (EPA) cRfD 0.0007 mg/kg b.w. [1991]. Other It is a
general anaesthetic, prolonged exposure causing irritation of the mucous membranes,
headache and nausea; repeated exposure to high concentrations causes liver damage.
ECClassifcation R40| T; R23/24/25, R48/23| R52, R53| N; R59| concn. dep.
carbophenothion 87
carbophenothion
IRAC 1B
NOMENCLATURE:
Common name carbophenothion (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name S-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate
Chemical Abstracts name S-[[(4-chlorophenyl)thio]methyl] O,O-
diethyl phosphorodithioate CAS RN [786196] EC no 2123241
Development codes R-1303 (Stauffer) Smiles code CCOP(=S)(OCC)SCSc1ccc(Cl)cc1
PHYSICAL CHEMISTRY:
11
H
16
ClO
2
PS
3
Form Colourless liquid
with a mercaptan-like odour; (tech. is a pale amber liquid). B.p. 82 C /0.01 mmHg V.p.
1.07 mPa (25 C)
K
ow
logP = 4.75 (Agchem. Desk Ref.) S.g./density 1.271 (25 C); 1.285 (20 C, tech.)
Solubility In water <1 mg/l (room temperature). Miscible with most organic solvents,
e.g. alcohols, esters, ketones, xylene, mineral oils. Miscible with vegetable oils. Stability
Thermally stable up to 80 C. Relatively stable to hydrolysis, particularly in alkaline media.
COMMERCIALISATION:
History Insecticide and acaricide (Agric. Chem., 1956, 11(11), 91). Introduced by Stauffer
Chemical Co. (later ICI Americas). Patents US 2793224
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide and
acaricide with contact and stomach action. Long residual activity. Uses Control of aphids
and spider mites on citrus fruit and cotton; and spider mites, aphids, suckers, Lepidoptera,
and other insect pests in fruit, nut crops, vines, olives, fgs, vegetables, beet, maize, sorghum,
clover, alfalfa, cucurbits, soya beans, ornamentals, turf, and other crops. Used as a seed
treatment for control of wheat bulb fies in wheat. Used in combination with petroleum
oil for control of overwintering aphids, scale insects, and mites on dormant deciduous
fruit trees. Also used as an animal ectoparasiticide. Phytotoxicity Slightly phytotoxic. Leaf
damage may occur on susceptible apples (Delicious), and on roses under glass, especially
under warm, moist conditions. Grapefruits, kumquats, citrons, and some varieties of grape
may also suffer injury. Formulation types EC; WP; GR; DP; Seed treatment.
PRODUCTS:
Discontinued products Trithion* (Stauffer).
Cl S CH
2
S P
S
OCH
2
CH
3
OCH
2
CH
3
88
carboxazole
ANALYSIS:
Product by glc with FID (Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 519521).
Residues by glc with TID or FPD (AOAC Methods, 18th Ed., 974.22, 968.24; J. A. Burke J.
Assoc. Off. Anal. Chem. 1965, 48, 10371058; Anal. Methods Pestic. Plant Growth Regul. 1972, 6,
521528; D. C. Abbott et al., Pestic. Sci., 1970, 1, 10).
EHC 63 (1986) is a general review of organophosphorus insecticides. JMPR Evaln. 41
(1983). ICSC.410 (1997). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
for male rats 79.4, female rats 20, mice 218 mg/kg.
50
for rabbits 1850, male rats 54, female rats 27 mg/
kg. NOEL LOEL (2 y) for dogs 5 ppm (0.125 mg/kg b.w.) (EPA Tracking). ADI/RfD (JMPR)
0.0005 mg/kg b.w. [1980]; (EPA) 0.00013 mg/kg b.w. [1987]. Toxicity Class WHO (a.i.) Ib
EPA (formulation) I ECClassifcation T; R24/25| N; R50, R53
ECOTOXICOLOGY:
Fish Very toxic to fsh. Bees Moderately toxic to bees.
ENVIRONMENTAL FATE:
Animals Readily degraded in rats, primarily to water soluble products which are
excreted in the urine (FAO/WHO 28). Plants On leaf surfaces, oxidation occurs to the
phosphorothioate (B. J. Luberoff et al., Agric. Chem., 1958, 13(3), 83).
Soil/Environment Undergoes oxidation to the sulfone, sulfoxide, thiol, thiosulfone, and
thiosulfoxide, presumably combined with dealkylation and hydrolysis.
carboxazole
Herbicide
NOMENCLATURE:
Common name carboxazole (BSI, E-ISO, (m) F-ISO)
IUPAC name methyl 5-tert-butyl-1,2-oxazol-3-ylcarbamate; methyl 5-tert-butylisoxazol-
3-ylcarbamate
Chemical Abstracts name methyl [5-(1,1-dimethylethyl)-3-isoxazolyl]carbamate
CAS RN [55808134] Development codes SSH-42
Smiles code COC(=O)Nc1cc(on1)C(C)(C)C
9
H
14
N
2
O
3
COMMERCIALISATION:
History Herbicide evaluated by Shionogi & Co. Ltd.
CGA 80 000 89
CECA
Fungicide
NOMENCLATURE:
Common name CECA (JMAF)
IUPAC name 2-chloro-N-(2-cyanoethyl)acetamide (I)
Chemical Abstracts name (I) CAS RN [17756819] Development codes NF 21
Smiles code ClCC(=O)NCCC#N
5
H
7
ClN
2
O
COMMERCIALISATION:
History Fungicide introduced by Nippon Soda Co., Ltd.
PRODUCTS:
Discontinued products Udonkor* (Nippon Soda).
CGA 80 000
Fungicide
NOMENCLATURE:
IUPAC name (RS)--[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]--butyrolactone
Chemical Abstracts name ()-N-(3-chloro-2,6-dimethylphenyl)-2-methoxy-N-
(tetrahydr-2-oxo-3-furanyl)acetamide CAS RN [79555809] racemate; [67932858]
unstated stereochemistry Development codes CGA 80 000
Smiles code COCC(=O)N(C1CCOC1=O)c2c(C)ccc(Cl)c2C
15
H
18
ClNO
4
M.p. 94.9 C V.p. 5 10
4

mPa (20 C) K
ow
logP = 1.5 (unspecifed organic phase, reversed-phase tlc) Henry 2.29
10
7
Pa m
3
mol
1
(calc.) Solubility In water 680 mg/l (20 C). Stability Stable to hydrolysis
at pH 1 to 5; DT
50
154 d (pH 7), 19 d (pH 8) (20 C).
COMMERCIALISATION:
History Fungicide reported by P. Margot et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 2,
527). Evaluated by Ciba-Geigy AG.
APPLICATIONS:
Mode of action Systemic fungicide. Uses Control of soil-borne late blight and root rot
on tobacco, citrus, avocado, carrots, soft fruit, and ornamentals. Formulation types GR;
SC.
PRODUCTS:
Discontinued products Vangard* (Cyanamid).
Oral Acute oral LD
50
50
for rats
>2000 mg/kg. Not a skin or eye irritant. Marginal skin sensitiser (guinea-pigs).
Inhalation LC
50
(4 h) >1.7 mg/l air.
90
chinomethionat
ECOTOXICOLOGY:
Fish Non-toxic. Bees Non-toxic.
chinomethionat
IRAC UN
NOMENCLATURE:
Common name chinomethionat (E-ISO); no name (USA); quinoxalines (JMAF);
chinom(thionate) ((m) F-ISO); quinomethionate (BSI); oxythioquinox (Australia, ESA)
IUPAC name S,S-(6-methylquinoxaline-2,3-diyl) dithiocarbonate; 6-methyl-1,3-
dithiolo[4,5-b]quinoxalin-2-one
Chemical Abstracts name 6-methyl-1,3-dithiolo[4,5-b]quinoxalin-2-one
CAS RN [2439012] EC no 2194553 Development codes Bayer 36 205;
Bayer SAS 2074 Offcial codes ENT 25 606 Smiles code Cc1ccc2nc3sc(=O)sc3nc2c1
10
H
6
N
2
OS
2
Form Yellow crystals.
M.p. 170 C V.p. 0.026 mPa (20 C) K
ow
logP = 3.78 (20 C) Henry 6.09 10
3
Pa m
3
mol
1
(calc.) S.g./density 1.556 (20 C) Solubility In water 1 mg/l (20 C). In toluene 25,
dichloromethane 40, hexane 1.8, isopropanol 0.9, cyclohexanone 18, DMF 10, petroleum
oils 4 (all in g/l, 20 C). Soluble in hot benzene and dioxane. Stability Relatively stable
under normal conditions. Hydrolysed in alkaline media; DT
50
(22 C) 10 d (pH 4), 80 h (pH
7), 225 min (pH 9).
COMMERCIALISATION:
History Acaricide and fungicide reported by K. Sasse (Hoefchen-Briefe (Engl. Ed.), 1960,
13, 197; K. Sasse et al., Angew. Chem., 1960, 72, 973). Introduced by Bayer AG. Patents DE
1100372; BE 580478
APPLICATIONS:
Mode of action Selective non-systemic contact fungicide with protective and eradicant
action. Uses Control of powdery mildews and spider mites on fruit (including citrus),
ornamentals, cucurbits, cotton, coffee, tea, tobacco, walnuts, vegetables, and glasshouse
crops; and American gooseberry mildew on gooseberries and currants.
Phytotoxicity Phytotoxic to certain varieties of apple, pear, currant, rose, and
ornamentals. Formulation types DP; FU; SC. WP. Compatibility Incompatible with
mineral oils (phytotoxicity may result), and with formulations based on thiram.
N
N
S
S
O
CH
3
chinomethionat 91
PRODUCTS:
Discontinued products Morestan* (Bayer CropScience);
Discontinued mixtures Morestan VP* (+ dichlorvos) (Nippon Soda).
ANALYSIS:
Product analysis by hplc (CIPAC Handbook, 1985, 1C, 2019; AOAC Methods, 18th Ed., 986.08)
or by uv spectrometry (details available from Bayer CropScience). Residues determined
by glc (Man. Pestic. Residue Anal., p. 13; A. Ambrus et al., J. Assoc. Off. Anal. Chem., 1981, 64,
733; R. T. Krause & E. M. August, ibid., 1983, 66, 1018), or by colorimetry after conversion
to a derivative (H. Tietz et al., ibid., 1962, 15, 166; C. A. Anderson, Anal. Methods Pestic., Plant
Growth Regul. Food Addit., 1967, 5, 277). See also Pestic. Anal. Man., I, 302; ibid., II 180.338.
Methods for the determination of residues are also available from Bayer CropScience.
JMPR Evaln. 43 (1984); JMPR Evaln. II 52 (1987). EU Status (1107/2009) Not approved,
Oral Acute oral LD
50
percutaneous LD
50
for rats >5000 mg/kg. Slightly irritating to skin; severely irritating to
eyes (rabbits). Inhalation LC
50
(4 h) for male rats >4.7, female rats 2.2 mg/l (dust).
NOEL (2 y) for rats 40, male mice 270, female mice <90 mg/kg diet; (1 y) for dogs 25 mg/
kg diet (0.625 mg/kg b.w.). ADI/RfD (JMPR) 0.006 mg/kg b.w. [1987]; (EPA) 0.006 mg/kg
b.w. [1999]. Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassifcation R62|
Xn; R20/21/22, R48/22| Xi; R36| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 196 mg/kg. Dietary LC
50
(5 d) for bobwhite quail
2409, mallard ducks >5000 mg/kg diet. Fish LC
50
(96 h) for bluegill sunfsh 0.0334, rainbow
trout 0.131, golden orfe 0.24 mg/l. Daphnia LC
50
(48 h) 0.12 mg/l. Algae ErC50 (96 h) for
Scenedesmus 0.14 mg/l. Bees Not toxic to bees; LD
50
>100 g/bee. Worms LC
50
(14 d)
>1000 mg/kg.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, chinomethionat is rapidly metabolised,
andc. 90% is eliminated within 3 days in the faeces and urine. The main metabolite
is chinomethionat acid (dimethylmercaptoquinoxaline-6-carboxylic acid), which also
occurs in the conjugated form. Plants After application to fruit, no penetration of the
a.i. or metabolites in the fruit pulp was observed. The only metabolite detected was
dihydromethylquinoxalinedithiol. Soil/Environment K
oc
4590 (3 soil types from sandy
loam to high organic matter). DT
50
in standard soil land 2 13 d.
92
chlomethoxyfen
chlobenthiazone
Fungicide
NOMENCLATURE:
Common name chlobenthiazone (BSI, E-ISO, (f) F-ISO)
IUPAC name 4-chloro-3-methyl-1,3-benzothiazol-2(3H)-one; 4-chloro-3-
methylbenzothiazol-2(3H)-one Chemical Abstracts name 4-chloro-3-methyl-
2(3H)-benzothiazolone CAS RN [63755055] Development codes S-1901
Smiles code Cn1c(=O)sc2cccc(Cl)c12
8
H
6
ClNOS Form Colourless crystals.
M.p. 131132 C
V.p. 172 mPa (20 C) Henryc. 7.47 10
1
Pa m
3
mol
1
(calc.) Solubility In water 46 mg/
kg (21.5 C). In acetone, methanol, xylene 330, chloroform, cyclohexanone 500, ethyl
acetate 200 (all in g/kg, 21.5 C). Stability Stable in aqueous acid and alkali.
COMMERCIALISATION:
History Fungicide reported by S. Inoue et al. (Proc. 1981 Br. Crop. Prot. Conf. - Pests Dis.,
1981, 1, 19). Evaluated by Sumitomo Chemical Co., Ltd.
APPLICATIONS:
Mode of action Systemic fungicide. It inhibits the development of infection pegs from
appressoria. Uses Submerged applications of granules (2.43.2 kg/ha) or foliar applications
of a dust are effective in controlling Pyricularia oryzae in rice. Formulation types DP; GR .
Oral Acute oral LD
50
50
for rats and mice >2500 mg/kg. Not
irritant to the abraded skin of rabbits; minimally irritant to their eyes. NOEL In 0.5 y
feeding trials, rats receiving 100 mg/kg diet showed no ill-effect.
chlomethoxyfen
Herbicide
HRAC E WSSA 14; diphenyl ether
S
N
O
CH
3
Cl
Cl
OCH
3
O NO
2
Cl
chlomethoxyfen 93
NOMENCLATURE:
Common name chlom(thoxyf) ((m) F-ISO); chlormethoxynil (JMAF); chlomethoxyfen
(BSI, E-ISO) IUPAC name 5-(2,4-dichlorophenoxy)-2-nitroanisole
Chemical Abstracts name 4-(2,4-dichlorophenoxy)-2-methoxy-1-nitrobenzene;
2,4-dichloro-1-(3-methoxy-4-nitrophenoxy)benzene CAS RN [32861851]
Development codes X-52 Smiles code COc1cc(Oc2ccc(Cl)cc2Cl)ccc1[N+](=O)[O-]
13
H
9
Cl
2
NO
4
M.p. 113114 C B.p. 260 C /25 mmHg V.p. 1.87 mPa (25 C) K
ow
logP = 3.34 (20 C)
S.g./density 1.37
Solubility In water 0.3 mg/l (15 C). In acetone 200, DMSO 100, benzene 150 (all in g/kg,
15 C). Stability Stable to acids, alkalis, and light.
COMMERCIALISATION:
History Introduced as a herbicide by Nihon Nohyaku Co., Ltd. Patents JP 600441
Manufacturers Ishihara Sangyo
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Selective contact
herbicide, absorbed by the leaves and stems. Uses Pre-emergence control of Scirpus
spp., Echinochloa crus-galli, and other annual weeds in transplanted rice at 1.52.5 kg/ha.
Phytotoxicity May scorch old leaves. Formulation types WP; GR .
PRODUCTS:
Discontinued products Condore* (Ishihara Sangyo); Difenex* (Ishihara Sangyo);
Diphenex* (Ishihara Sangyo); Ekkusugoni* (Ishihara Sangyo, Nihon Nohyaku); Ikkokuso*
(Ishihara Sangyo).
ANALYSIS:
Product analysis by glc with FID (F. Yamane & K. Tsuchiya, Anal. Methods Pestic. Plant Growth
Regul., 1978, 10, 267). Residues determined by glc with ECD (idem, ibid.).
Oral Acute oral LD
50
for rats and mice >10 000 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats >5000 mg/kg. Inhalation LC
50
for rats >1.767 mg/l. Toxicity Class WHO
(a.i.) U EPA (formulation) IV
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp 11.2 mg/l. Daphnia LC
50
(24 h) >47.5 mg/l.
ENVIRONMENTAL FATE:
Animals Metabolised in rats to form glucurone and glutathione conjugates.
Soil/Environment In soil, DT
50
743 d. K
d
5251407.
94
chloramben
chloramben
Herbicide
HRAC O WSSA 4; benzoic acid (auxin)
NOMENCLATURE:
Common name chloramben (BSI, E-ISO, ANSI, WSSA); amben* (former WSSA name);
chloramb(n) ((m) F-ISO)
IUPAC name 3-amino-2,5-dichlorobenzoic acid
Chemical Abstracts name 3-amino-2,5-dichlorobenzoic acid CAS RN [133904]
Development codes ACP M-629 (Amchem) Smiles code Nc1cc(Cl)cc(C(=O)O)c1Cl
7
H
5
Cl
2
NO
2
M.p. 200201 C
V.p. 930 mPa (100 C) Solubility In water 700 mg/l (25 C). In DMF 1206, acetone,
methanol 223, ethanol 173, isopropanol 113, diethyl ether 70, chloroform 0.9, benzene
0.2 (all in g/kg, room temperature). Insoluble in carbon tetrachloride. Stability Thermally
stable up to the boiling point. Stable to oxidising agents, acids and alkalis. Decomposed by
sodium hypochlorite solutions. Sensitive to light. pKa 3.40 (ACS Adv. in Chem. Series no. 111,
cited in ARS PPD).
COMMERCIALISATION:
History Herbicide introduced by Amchem Products, Inc. (later Bayer AG). Patents US
3014063; US 3174842
APPLICATIONS:
Biochemistry Synthetic auxin (acting like indolylacetic acid). The N-glycoside was
isolated from soya beans in amounts equivalent to the chloramben applied, but little
was recovered from barley, a susceptible crop (S. R. Colby, Science, 1965, 150, 619).
Mode of action Selective systemic herbicide, absorbed by the seeds and roots, with
limited translocation. Inhibits root development of seedling weeds. Uses Used pre-planting
incorporated and pre-emergence, at 24 kg/ha, to control grasses and broad-leaved weeds
in seedling asparagus, navy beans, peanuts, maize, sweet potatoes, pumpkins, soya beans,
squash, sunfowers and certain ornamentals. Formulation types DS; GR; SL; SP.
PRODUCTS:
Discontinued products Amiben* (ammonium salt) (Aventis).
ANALYSIS:
Product analysis by uv spectrophotometry (AOAC Methods, 18th Ed., 971.06;
CIPAC Handbook, 1983, 1B, 1747) or volumetric methods. See also: H. S. Segal & M. L.
Cl
CO
2
H
Cl
NH
2
chloraniformethan 95
Sutherland, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 321; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 588. Residue analysis by glc of methyl ester.
Oral Acute oral LD
50
50
for
rats >3160 mg/kg. Mild skin and eye irritant (rabbits). NOEL (2 y) for rats 10 000 mg/kg
diet. ADI/RfD (EPA) cRfD 0.015 mg/kg b.w. [1988]. Toxicity Class WHO (a.i.) U EPA
(formulation) IV
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks 4640 mg/kg. Fish Not toxic to fsh. Bees Not
toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats, the major metabolites were 3-amino-5-chlorobenzoic acid,
3-aminobenzoic acid, 2,5-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid and
2,5-dichloroaniline. Plants In plants, chloramben is converted to a highly stable
N-glucoside, which retards further degradation. Soil/Environment Undergoes microbial
degradation in soil. Duration of activity isc. 68 w.
chloraniformethan
Fungicide
NOMENCLATURE:
Common name chloraniformethan (BSI, E-ISO); chloraniform(thane) ((m) F-ISO)
IUPAC name N-[2,2,2-trichloro-1-(3,4-dichloroanilino)ethyl]formamide
Chemical Abstracts name N-[2,2,2-trichloro-1-[(3,4-dichlorophenyl)amino]
ethyl]formamide CAS RN [20856579] Development codes Bayer 79 770
Smiles code Clc1ccc(NC(NC=O)C(Cl)(Cl)Cl)cc1Cl
9
H
7
Cl
5
N
2
O M.p. 134136 C V.p. <1
mPa (20 C);c. 1.3 mPa (40 C) Henry <2 10
3
Pa m
3
mol
1
(20 C, calc.) Solubility In
water 0.016 g/100 ml (20 C). In methanol 40, methyl isobutyl ketone 40.2, cyclohexanone
45, DMF 55, toluene 1.33, n-heptane 0.008 (all in g/100 g, 20 C). Stability Converted by
strong acids and alkalis to 3,4-dichloroaniline.
COMMERCIALISATION:
History Fungicide reported by A. O. Paulus et al. (Calif. Agric., 1968, 22(3), 10). Introduced
by Bayer AG.
APPLICATIONS:
Mode of action Fungicide with curative action. Uses Control of mildew, especially
Erysiphe species, in cereals and ornamentals (roses, chrysanthemums, begonias).
96
chloranil
PRODUCTS:
Discontinued products Imugan* (Bayer); Milfaron* (Bayer).
ANALYSIS:
Product by gc determination, as for residues (R. A. Hoodless & M. Sargent Analyst 1976,
101, 161166). residues by extraction of plant material by maceration with acetone,
clean-up, hydrolysis with sulfuric acid, steam distillation of the resultant 3, 4-dichloroaniline
from alkaline solution, diazotization, coupling with N-(1-naphthyl)ethylenediamine, and
colorimetric determination at 530 nm (K. Vogeler Pfanz.-Nachr. Bayer 1969, 22, 299304
and Man. Pestic. Residue Anal., 271).
Oral Acute oral LD
50
for male rats >2500, female mice >1000, cats >500, guinea pigs
50
for rats >500 mg/kg. 14 d activity
on the skin of rabbits has no detrimental effects on general condition, organs, etc.
NOEL Feeding of 10, 30, and 100 mg/kg b.w. for 14 w does not cause any symptoms of
toxicity; intake of 100 mg/kg produces liver hypertrophy. Toxicity Class WHO (a.i.) O
ECOTOXICOLOGY:
Fish LC
50
for goldfsh 110 mg/l.
Details PM4, p. 91.
chloranil
Fungicide
NOMENCLATURE:
Common name chloranil (BSI, E-ISO); chloranile (F-ISO); traditional names accepted in
lieu of a common name
IUPAC name tetrachloro-p-benzoquinone; 2,3,5,6-tetrachloro-1,4-benzoquinone
Chemical Abstracts name 2,3,5,6-tetrachloro-2,5-cyclohexadiene-1,4-dione
CAS RN [118752] EC no 2042744 Smiles code ClC1=C(Cl)C(=O)C(=C(Cl)
C1=O)Cl
6
Cl
4
O
2
M.p. 292 C (in closed tube)
V.p. 1300 mPa (70.7 C)
S.g./density 1.97 Solubility Practically insoluble in water. In acetone 33, ether 16, DMF
5.4, solvent naphtha 5.4, benzene 1.3, methanolc. 0.1, carbon tetrachloridec. 0.1, dibutyl
phthalatec. 0.1 (all in g/100 g). Stability Stable in closed containers. Slowly decomposed by
sunlight. Decomposed by alkalis; stable in acidic media.
COMMERCIALISATION:
History Fungicidal activity of chloranil, long known as a chemical reagent, reported by
H. S. Cunningham & E. G. Shavelle (Phytopathology, 1940, 30, 4). Introduced by Uniroyal
Chemical Co., Inc.
chloranocryl 97
APPLICATIONS:
Mode of action Fungicide and seed protectant with secondary insect repellent and
bactericidal effects. Uses Used particularly on vegetable and ornamental seeds. Active
against damping-off on beans. Formulation types WP; DP; DS .
PRODUCTS:
Discontinued products Spergon* (Uniroyal).
ANALYSIS:
Product by reduction of chloranil with potassium iodide and potentiometric titration of
the liberated iodine with sodium thiosulfate (Anal. Methods Pestic. Plant Growth Regul., 3, 29),
or total chlorine determination by the Stepanov method or Parr bomb decomposition.
Residues by extraction with benzene, clean-up, reaction with diphenyl-p-phenylenediamine
to give a blue colour, transfer of the dye into the aqueous-acid phase, and determination by
spectrophotometry at 700 nm (Anal. Methods Pestic. Plant Growth Regul., 3, 32).
Oral Acute oral LD
50
for ratc. 4 g/kg. Skin and eye Slight absorption through the skin;
nevertheless there is local irritation. NOEL Long-term feeding as 0.5% of diet causes no
damage to health. Other I.p. LD
50
c. 0.5 g/kg. Toxicity Class WHO (a.i.) O
ECClassifcation Xi; R36/38| N; R50, R53
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Soil/Environment In plants, the chlorine atoms are replaced by sulfhydryl groups. In
solution, under the infuence of sunlight, reduction to tetrachlorohydroquinone followed by
replacement of chlorine atoms with hydroxy groups.
Details PM5, p. 90.
chloranocryl
Herbicide
NOMENCLATURE:
Common name chloranocryl (BSI, E-ISO, (m) F-ISO); dicryl (Canada, WSSA, ex ANSI)
IUPAC name 3,4-dichloro-2-methylacrylanilide
Chemical Abstracts name N-(3,4-dichlorophenyl)-2-methyl-2-propenamide
CAS RN [2164092] Development codes FMC 4556
Smiles code CC(=C)C(=O)Nc1ccc(Cl)c(Cl)c1
10
H
9
Cl
2
NO
COMMERCIALISATION:
History Herbicide reported by S. W. Bingham & W. K. Porter (Weeds, 1961, 9, 282).
Introduced by FMC Corp.
98
chlorazine
APPLICATIONS:
Mode of action Contact herbicide.
PRODUCTS:
Discontinued products Dicryl* (FMC).
Details PM2, p. 85.
chlorazifop; chlorazifop-propargyl
Herbicide
NOMENCLATURE:
Common name chlorazifop (BSI, E-ISO, (m) F-ISO)
IUPAC name ()-2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]
propanoic acid CAS RN [60074251] chlorazifop, unstated stereochemistry;
[74310706] chlorazifop, racemate; [72492547] chlorazifop, (R)- isomer;
[72492558] chlorazifop, (S)- isomer; [72280525] chlorazifop-propargyl,
unstated stereochemistry, formerly [77107494]; [74267699] chlorazifop-
propargyl, (R)- isomer Development codes CGA 82 725 (chlorazifop-propargyl)
Smiles code chlorazifop:CC(Oc1ccc(Oc2ncc(Cl)cc2Cl)cc1)C(=O)O
PHYSICAL CHEMISTRY: Mol. wt. 328.2; (propargyl ester 366.2) M.f. C
14
H
11
Cl
2
NO
4
;
(propargyl ester C
17
H
13
Cl
2
NO
4
)
COMMERCIALISATION:
History Chlorazifop-propargyl evaluated as a herbicide by Ciba-Geigy AG (chlorazifop
also formed by hydrolysis of isoxapyrifop in vivo).
chlorazine
Herbicide
NOMENCLATURE:
Common name chlorazine (BSI, WSSA, ex ANSI)
IUPAC name 6-chloro-N
2
,N
2
,N
4
,N
4
-tetraethyl-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-chloro-N,N,N,N-tetraethyl-1,3,5-triazine-2,4-diamine
CAS RN [580483] Development codes G 25 804
Smiles code CCN(CC)c1nc(Cl)nc(n1)N(CC)CC
11
H
20
ClN
5
COMMERCIALISATION:
History Herbicide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
chlorbenside 99
chlorbenside
Acaricide
NOMENCLATURE:
Common name chlorbenside (BSI, E-ISO, F-ISO, ESA, ex ANSI)
IUPAC name 4-chlorobenzyl 4-chlorophenyl sulfde
Chemical Abstracts name 1-chloro-4-[[(4-chlorophenyl)methyl]thio]
benzene CAS RN [103173] Development codes HRS 860; RD 2195
Smiles code Clc1ccc(CSc2ccc(Cl)cc2)cc1
13
H
10
Cl
2
S M.p. 72.5 C B.p. 8384 C
/0.003 mbar V.p. 1.6 mPa (30 C) Solubility In water <1:5000. In alcohol 2.8%; readily
soluble in acetone and benzene. Stability Extremely stable to acids and alkalis. Oxidising
agents convert it to the sulfoxide and sulfone.
COMMERCIALISATION:
History Acaricide reported by J. E. Cranham et al. (Chem. Ind. (London), 1953, p. 1206)
and by D. J. Higgons & D. W. Kilbey (ibid., p. 1359). Introduced by The Boots Co., Ltd (later
Schering Agrochemicals).
APPLICATIONS:
Mode of action Specifc acaricide, with ovicidal and larvicidal properties. Little insecticidal
activity. Uses Control of most varieties of spider mites (weak activity against adults),
particularly in the pre-blossom stage in fruit cultivation and on ornamentals and nursery
stock. Phytotoxicity Cucumbers and other cucurbits are susceptible. Formulation
types WP; EC.
PRODUCTS:
Discontinued products Chlorparacide* (Boots); Chlorsulphacide* (Boots); Redon*
(Sariaf).
ANALYSIS:
Product by extraction with ether, hydrolysis to p-chlorophenol, steam distillation,
colorimetric determination at 510 nm after colour reaction with 4-aminoantipyrine in the
presence of potassium ferricyanide (Anal. Insectic. Acar.). Residues by extraction from plants
with benzene, oxidation to the sulfone, nitration, colour reaction with sodium methylate,
and colorimetric determination (J. T. Martin & R. F. Batt Annu. Rep. Long Ashton Res. Stat.
1955, 106110, partly by the method of H. Niessen & H. Frehse Gadamer 1969). For a
further colorimetric method see H. J. Hardon et al. (J. Sci. Food Agric. 1957, 8, 368370).
JMPR Evaln. 4 (1965). EU Status (1107/2009) Never notifed to the EU.
Oral Acute oral LD
50
for rats >10 000 mg/kg. Skin and eye Slight irritant action on skin
and eyes. NOEL A 5 mg/kg concentration can be tolerated for 3 w in the diet of dogs.
ADI/RfD (JMPR) 0.01 mg/kg b.w. [1965]. Toxicity Class WHO (a.i.) O
100
chlorbromuron
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Animals In warm-blooded organisms, elimination is as the glucuronic acid conjugate.
Soil/Environment Presumably degraded by enzymic hydrolysis.
Details PM3, p. 97.
chlorbicyclen
Insecticide
NOMENCLATURE:
Common name chlorbicyclen (BSI, E-ISO); chlorbicycl(ne) ((m) F-ISO)
IUPAC name 1,2,3,4,7,7-hexachloro-5,6-bis(chloromethyl)-8,9,10-trinorborn-2-ene
Chemical Abstracts name 1,2,3,4,7,7-hexachloro-5,6-bis(chloromethyl)
bicyclo[2.2.1]hept-2-ene CAS RN [2550756] Development codes Hercules 426
Smiles code ClCC1C(CCl)C2(Cl)C(=C(Cl)C1(Cl)C2(Cl)Cl)Cl
9
H
6
Cl
8
COMMERCIALISATION:
History Insecticide introduced by Hercules Inc. Agrochemicals (and later Nor-Am).
PRODUCTS:
Discontinued products Alodan* (Hercules).
chlorbromuron
Herbicide
HRAC C2 WSSA 7
NOMENCLATURE:
Common name chlorobromuron ((m) F-ISO); chlorbromuron (BSI, E-ISO, WSSA, ex-ANSI)
IUPAC name 3-(4-bromo-3-chlorophenyl)-1-methoxy-1-methylurea
Chemical Abstracts name N-(4-bromo-3-chlorophenyl)-N-methoxy-N-methylurea
CAS RN [13360457] EC no 2364119 Development codes C 6313 (Ciba)
Br
Cl
NH
C NOCH
3
O
CH
3
chlorbromuron 101
Smiles code CON(C)C(=O)Nc1ccc(Br)c(Cl)c1
9
H
10
BrClN
2
O
2
Form Colourless
powder. M.p. 9597 C
V.p. 0.053 mPa (20 C) K
ow
logP = 2.9 Henry 4 10
4
Pa m
3
mol
1
(calc.)
S.g./density 1.69 (20 C) Solubility In water 35 mg/l (20 C). In acetone 460,
dichloromethane 170, hexane 89, benzene 72, isopropanol 12 (all in g/kg, 20 C).
Stability Slowly hydrolysed in neutral, slightly acidic, and slightly alkaline media.
COMMERCIALISATION:
History Herbicide reported by D. H. Green et al. (Proc. Br. Weed Control Conf., 8th, 1966, 2,
363). Introduced by Ciba AG (later Syngenta AG). Patents BE 662268; GB 965313
APPLICATIONS:
receptor site. Mode of action Selective herbicide, absorbed by the roots and leaves.
Uses Herbicide suitable for: pre-emergence use on carrots, peas, potatoes, soya beans,
and sunfowers, at 1.02.5 kg/ha; post-emergence use on carrots and transplanted celery,
at 0.751.5 kg/ha. Phytotoxicity A number of crops may be injured by pre-emergence
applications, e.g. rice, beet, okra, fax, cucurbits, tomatoes, strawberries, etc. Formulation
types WP.
PRODUCTS:
Discontinued products Maloran* (Syngenta).
ANALYSIS:
Product analysis by glc. Residues determined by hydrolysis to 4-bromo-3-chloroaniline,
a derivative of which is determined by colorimetry, or by glc with ECD (G. Voss, Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 569).
Oral Acute oral LD
50
for rats >5000 mg tech./kg. Skin and eye Acute percutaneous LD
50

for rats >2000, rabbits >10 000 mg/kg. Not a skin or eye irritant. Inhalation LC
50
(6 h) for
rats >1.05 mg/l air. NOEL (90 d) for rats 316 mg/kg diet (21.0 mg/kg daily), dogs >316 mg/
kg diet (10.5 mg/kg daily). Toxicity Class WHO (a.i.) III (company classifcation); WHO
Recommended Classifcation gave U (now O) EPA (formulation) IV
ECOTOXICOLOGY:
Birds Dietary LC
50
(10 d) for pheasants and mallard ducks >10 250 mg/kg diet. Fish LC
50

(96 h) for rainbow trout 5, bluegill sunfsh 5, crucian carp 8 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, metabolism involves demethylation and deamination-decarboxylation to
the corresponding aniline molecule. Soil/Environment In biologically active soils, DT
50

828 w; strongly bound to soil (K
oc
908), indicating low leaching potential. In water, stable
against abiotic degradation, but in biologically active systems, DT
50
411 w.
102
chlorbufam
chlorbufam
Herbicide
NOMENCLATURE:
Common name chlorbufame ((m) F-ISO); chlorbufam (BSI, E-ISO); BIPC (JMAF)
IUPAC name 1-methylprop-2-ynyl 3-chlorocarbanilate; 1-methylprop-2-ynyl
3-chlorophenylcarbamate
Chemical Abstracts name 1-methyl-2-propynyl (3-chlorophenyl)carbamate
CAS RN [1967164] Smiles code CC(OC(=O)Nc1cccc(Cl)c1)C#C
11
H
10
ClNO
2
M.p. 4546 C
V.p. 2.1 mPa (20 C) Henry 8.70 10
4
Pa m
3
mol
1
(calc.) S.g./density 1.22 (tech.)
Solubility In water 540 mg/l (20 C). In methanol 286, acetone 280, ethanol 95 (all in g/kg,
20 C). Stability Unstable in strongly acidic and alkaline media (l>pH>13). Changes colour
when exposed to light. Alcohols may cause trans-esterifcation. Stable up to 40 C.
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Z. Pfanzenkr. Pfanzenpathol. Pfanzenschutz,
1960, 67, 577). Introduced by BASF AG. Patents DE 1034912; DE 1062482
Manufacturers BASF
APPLICATIONS:
Biochemistry Inhibits photosynthesis. Cell division inhibitor Uses Was normally used in
combination with other herbicides for pre-emergence control of grasses and broad-leaved
weeds in onions, leeks, garlic, shallots, carrots, beet, spinach, sunfowers, and bulb fowers.
Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products BiPC* (BASF); Discontinued mixtures Alipur* (+ cycluron)
(BASF).
ANALYSIS:
Product analysis by acid hydrolysis to 3-chloroaniline, determined by titration. Residues
determined by hydrolysis and colorimetry of the resulting 3-chloroaniline or by glc (Analyt.
von Pf. in Wasser, p. 67)
Oral Acute oral LD
50
for rats 2500 mg/kg. Skin and eye Mild skin irritant (rabbits).
NOEL (4 mo) for rats 400 mg/kg diet. Other Acute i.p. LD
50
for mice 250 mg/kg.
NH C
O
O
CH
3
CH C CH
Cl
chlordecone 103
ECOTOXICOLOGY:
chlordecone
Insecticide
NOMENCLATURE:
Common name chlordecone (BSI, E-ISO, (m) F-ISO)
IUPAC name perchloropentacyclo[5.3.0.02,6.03,9.04,8]decan-5-one
Chemical Abstracts name 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-
metheno-2H-cyclobuta[cd]pentalen-2-one CAS RN [143500] EC no 2056013
Development codes GC-1189
Smiles code ClC1(C2(Cl)C3(Cl)C
14
Cl)C5(Cl)C(=O)C4(Cl)C(Cl)(C25Cl)C3(Cl)Cl
10
Cl
10
O M.p. Decomposes (without
melting) around 350 C
V.p. 4 10
2
mPa (25 C) Stability Wide stability to alkalis. Decomposed by strong
mineral acids.
COMMERCIALISATION:
History Insecticide introduced by Allied Chemical Corp., Agricultural Div. (later Hopkins
Ltd).
APPLICATIONS:
Biochemistry Interferes with oxidative phosphorylation. Mode of action Insecticide
with stomach action and weak contact action. Secondary fungicidal effects. Uses
Insecticidal control of cockroaches and ants. Formulation types RB; WP.
PRODUCTS:
Discontinued products Kepone* (Hopkins).
ANALYSIS:
Product by gc determination as for residues, or by i.r. spectrophotometric determination
(6.1 m and 2.83.1 m) according to E. E. Gilbert et al. (J. Agric. Food Chem. 1966, 14,
115116). Residues in cereals by gc with a tritium ECD, see J. Burke & L. Giuffrida (J. Assoc.
Off. Anal. Chem. 1964, 47, 326342); also with microcoulometric detection and clean-up on
aluminium oxide, see D. Firestone et al. (ibid. 1963, 46, 384396) and J. F. Thompson et al.
(with ECD) (ibid. 1969, 52,12631272). See also Man. Pestic. Residue Anal., 247.
EHC 43 (1984). HSG 41 (1990). ICSC.432 (2003). IARC 20 (1979).
banned, 79/117/EEC, as amended by Regulation 850/2004.
IARC Class 2B
104
chlordimeform; chlordimeform hydrochloride
Oral Acute oral LD
50
for albino rats 126132, rabbits 71, dogs 250 mg/kg (5% solution in
corn oil). Skin and eye Dermal LD
50
for male rabbits 450 mg/kg. NOEL LD
50
for long-
term feeding 14 mg/kg b.w. daily. Toxicity Class WHO (a.i.) O
ECClassifcation T; R24/25| R40| N; R50, R53
ECOTOXICOLOGY:
Fish Toxic to fsh.
Details PM5, p. 94.
chlordimeform; chlordimeform hydrochloride
NOMENCLATURE:
Common name chlorophenamidine (JMAF); chlorodimeform (New Zealand);
chlordimeform (BSI, E-ISO, ANSI); chlordim(forme) ((m) F-ISO)
IUPAC name N
2
-(4-chloro-o-tolyl)-N1,N1-dimethylformamidine
Chemical Abstracts name N-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide
CAS RN [6164983] chlordimeform; [19750959] chlordimeform hydrochloride
EC no 2282005 chlordimeform; 2432691 chlordimeform hydrochloride
Development codes Schering 36 268; C 8514 (Ciba-Geigy)
PHYSICAL CHEMISTRY:
Composition Tech. is >96%. Mol. wt. 196.7; (hydrochloride 233.1) M.f. C
10
H
13
ClN
2
;
(hydrochloride C
10
H
14
Cl
2
N
2
)
Form Colourless crystals. M.p. 32 C; (hydrochloride 225227 C (decomp.))
B.p. 163165 C /14 mmHg V.p. Base: 48 mPa (20 C) K
ow
logP = 1.8 (base), 0.201
(hydrochloride) Henry 3.78 10
2
Pa m
3
mol
1
(20 C, calc.) S.g./density 1.10 (30 C)
Solubility Base: In water 250 mg/l (20 C). In acetone, benzene, chloroform, ethyl acetate,
hexane, methanol >200 g/l (20 C). Hydrochloride: In water >500 g/l. In benzene, hexane
1, chloroform 1020, methanol >300 (all in g/l). Stability Hydrolysed frst to 4-chloro-o-
tolylformamide and then to 4-chloro-o-toluidine; DT
50
112 d (pH 5), 7.5 d (pH 7), 0.5 d
(pH 9, 20 C) (ARS PPD).
COMMERCIALISATION:
History Acaricide reported by V. Dittrich (J. Econ. Entomol., 1966, 59, 889). Introduced by
Ciba AG (later Ciba-Geigy AG) and Schering AG. Patents GB 1039930; DE 1172081; US
3378437
APPLICATIONS:
Mode of action Systemic acaricide and insecticide with contact, stomach, and respiratory
action. Uses Chlordimeform controls eggs and larvae of Heliothis spp. on cotton at
150225 g/ha. Also effective against the eggs and early instars of other Lepidoptera, e.g.
Chilo suppressalis, Cydia pomonella, Spodoptera littoralis, Trichoplusia ni, at 0.21.0 kg/ha,
and is effective against mites and their eggs. Phytotoxicity Injury may occur on some
chloreturon 105
ornamentals, tomatoes, tobacco, cucurbits, brassicas, lettuce, beans, capsicums, aubergines,
and maize. Russetting may occur with pears. Formulation types EC; SP.
PRODUCTS:
Discontinued products Fundal* (as base or hydrochloride, depending on formulation)
(Schering); Galecron* (base) (Ciba-Geigy); Spanon* (Nihon Nohyaku); Spanone*
(Schering).
ANALYSIS:
Product analysis by acid-base titration or by glc (CIPAC Handbook, 1988, D, 28;
AOAC Methods 18th Ed., 985.05; J. Assoc. Off. Anal. Chem., 1985, 68, 371; G. Voss et al., Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 211). Residues determined by glc of a derivative
(idem, ibid.; H. Geissbhler et al., J. Agric. Food Chem., 1971, 19, 365).
EHC 199 (1998). JMPR Evaln. I 48 (1986); JMPR Evaln. II 52 (1987). ICSC.124 (base; 1994);
ICSC.125 (hydrochloride; 1994). IARC 30 (1983).
IARC Class 3
Oral Chlordimeform: Acute oral LD
50
for rats 340, rabbits 625 mg/kg. Chlordimeform
hydrochloride: Acute oral LD
50
LD
50
for rabbits >4000 mg hydrochloride/kg. Slight skin irritant (rabbits). NOEL (2 y) for
rats 0.1 mg/kg daily, for dogs 6.25 mg/kg daily. ADI/RfD (JMPR) Temporary ADI withdrawn
[1987]; (EPA) 0.001 mg/kg b.w. [1987]. Toxicity Class WHO (a.i.) II
ECClassifcation R40| Xn; R21/22| N; R50, R53 (chlordimeform): R40| Xn; R22| N; R50,
R53 (chlordimeform hydrochloride) PIC Yes.
ECOTOXICOLOGY:
Fish LC
50
(96 h) for trout 7.1, barbel 4.5, bluefll sunfsh 1 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, undergoes N-demethylation and
hydrolysis. The principal metabolite is p-chloro-o-toluidine. Plants Metabolism in plants
is similar to that in mammals. Soil/Environment In soil, degradation is similar to
metabolism in mammals.
chloreturon
Herbicide
NOMENCLATURE:
Common name chloreturon (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(3-chloro-4-ethoxyphenyl)-1,1-dimethylurea
Chemical Abstracts name N-(3-chloro-4-ethoxyphenyl)-N,N-dimethylurea
CAS RN [20782585] Smiles code CCOc1ccc(NC(=O)N(C)C)cc1Cl
106
chlorfenac; chlorfenac-sodium
11
H
15
ClN
2
O
2
COMMERCIALISATION:
History Herbicide reported by A. Aamisepp (Proc. Swed. Weed Conf., 1977, 18, F9-F13).
Evaluated by Hoechst AG.
chlorfenac; chlorfenac-sodium
Herbicide
NOMENCLATURE:
Common name chlorfenac (BSI, E-ISO, (m) F-ISO); fenac (WSSA)
IUPAC name (2,3,6-trichlorophenyl)acetic acid
Chemical Abstracts name 2,3,6-trichlorobenzeneacetic acid CAS RN [85347]
chlorfenac; [2439001] chlorfenac-sodium EC no 2015993
PHYSICAL CHEMISTRY: Mol. wt. 239.5; (sodium salt 261.5) M.f. C
8
H
5
Cl
3
O
2
; (sodium
salt C8H4Cl3NaO
2
)
Form Colourless solid. M.p. 156 C V.p. 1100 mPa (100 C) Solubility In water 200 mg/l
(28 C). Soluble in most organic solvents. Stability Photolytically decomposed by uv light.
Very stable in acidic media. Forms water-soluble salts with alkalis. pKa 3.70 (ARS PPD)
COMMERCIALISATION:
History Herbicide introduced by Amchem Products Inc. (later Rhne-Poulenc
Agrochimie) and Hooker Chemical Corp. Patents GB 860310
APPLICATIONS:
Mode of action Systemic herbicide, absorbed primarily by roots, with translocation. Uses
Usually applied as the sodium salt, it was used to control annual grasses, broad-leaved
weeds, Elymus repens, Convolvulus arvensis and other perennial weeds in industrial
and other non-crop situations at rates up to 18 kg a.e./ha. Also used pre-em. at
2.83.4 kg a.e./ha for weed control in sugar cane. Formulation types SL .
PRODUCTS:
Discontinued products Fenac* (Amchem); Fenatrol* (sodium salt) (Amchem).
ANALYSIS:
Product analysis by glc. Residues determined by glc of suitable derivatives (G. Yip, J. Assoc.
Off. Anal. Chem., 1972, 45, 367).
Oral Acute oral LD
50
50

for rabbits 14403160 mg/kg. NOEL In 2 y feeding trials, rats receiving 2000 mg/kg diet
showed no ill-effect. Toxicity Class WHO (a.i.) III
ECClassifcation Xn; R22| N; R51, R53
ECOTOXICOLOGY:
Fish Not toxic to fsh when used as recommended. Bees Not toxic to bees.
chlorfenethol 107
ENVIRONMENTAL FATE:
Soil/Environment Does not leach. In soil, undergoes slow microbial degradation and
persists for c. 12 y.
chlorfenazole
Fungicide
NOMENCLATURE:
Common name chlorf(nazole) ((m) F-ISO); chlorfenazole (BSI, E-ISO)
IUPAC name 2-(2-chlorophenyl)benzimidazole
Chemical Abstracts name 2-(2-chlorophenyl)-1H-benzimidazole
CAS RN [3574967] Development codes CUR 616
Smiles code Clc1ccccc1c2nc3ccccc3[nH]2
13
H
9
ClN
2
COMMERCIALISATION:
History Fungicide introduced by Celamerck GmbH & Co., KG (later Shell Agrar GmbH).
chlorfenethol
Acaricide
NOMENCLATURE:
Common name chlorfenethol (BSI, E-ISO, (m) E-ISO, ESA); BCPE (JMAF)
IUPAC name 1,1-bis(4-chlorophenyl)ethanol
Chemical Abstracts name 4-chloro--(4-chlorophenyl)--methylbenzenemethanol
Other names DMC; DCPC CAS RN [80068] EC no 2012463
Smiles code CC(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Composition May contain the 2,4- isomer. Mol. wt. 267.2 M.f. C
14
H
12
Cl
2
O Form
Colourless crystals. M.p. 69.570 C V.p. Not known exactly; said to be 4 to 8 times more
volatile than DDT. Solubility Practically insoluble in water. Readily soluble in most organic
solvents, particularly polar ones. Stability Stable to alkalis, but unstable to strong acids.
Heating leads to dehydration.
COMMERCIALISATION:
History Acaricide reported by O. Grummitt (Science, 1950, 111, 361). Introduced by
Sherwin-Williams & Co. and later by Nippon Soda Co. Ltd. Patents US 2430586.
APPLICATIONS:
Mode of action Non-systemic acaricide with predominantly ovicidal activity, having slow
uptake and retaining effectiveness over a long period. Uses Control of spider mites (in the
108
chlorfenprop; chlorfenprop-methyl
open and under glass) in fruit, vegetables, vines, hops, cotton, and ornamental cultivation.
PRODUCTS:
Discontinued products Dimite* (Sherwin-Williams); Qikron* (Nippon Soda);
Discontinued mixtures Milbex* (+ chlorfensulphide) (Nippon Soda); Mitran*
(+ chlorfenson) (Nippon Soda).
ANALYSIS:
Product analysis (1) separation from chlorfensulfde in commercial mixed formulations by
column chromatography on aluminium oxide and gravimetric determination.
(2) uv spectrophotometry in isooctane solution at 240 and 260 nm (Anal. Insectic. Acar.,
p. 432435). Residues by reaction with p-toluenesulfonic acid to give
1,1-bis(4-chlorophenyl)ethylene, and determination by gc with ECD.
Oral Acute oral LD
50
for rats 9261391 mg/kg. NOEL Rats tolerated 1000 mg/kg diet fed
for 10 d (L. Peters, Proc. Soc. Exp. Biol. Med., 1947, 72, 304). Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp 1.8 mg/l. Bees Not toxic to bees.
Details PM6, p. 97.
chlorfenprop; chlorfenprop-methyl
Herbicide
NOMENCLATURE:
Common name chlorfenprop (BSI, E-ISO, (m) F-ISO)
IUPAC name ()-2-chloro-3-(4-chlorophenyl)propionic acid
Chemical Abstracts name ()-,4-dichlorobenzenepropanoic acid
CAS RN [14437208] chlorfenprop (racemate), formerly [59604114]; [59604
103] chlorfenprop-methyl (racemate) EC no 2384135 chlorfenprop-methyl
Development codes Bayer 70 533
PHYSICAL CHEMISTRY: Mol. wt. 219.1; (methyl ester 233.1) M.f. C
9
H
8
Cl
2
O
2
;
(methyl ester C
10
H
10
Cl
2
O
2
) Form Colourless liquid (ester); light brown liquid (tech. ester).
M.p. >20 C (ester)
B.p. 110113 C /0.1 mmHg (ester) V.p. 930 mPa (50 C) (ester) S.g./density 1.30
(20 C, tech. ester) Solubility In water 40 mg/l (20 C, ester). Soluble in acetone, aromatic
hydrocarbons, diethyl ether and fatty oils.
COMMERCIALISATION:
History Herbicide reported by L. Eue (Z. Pfanzenkr. Pfanzenpathol. Pfanzenschutz, 1968,
Sonderheft IV, 211). Only the ()- enantiomer is herbicidal (T. Schmidt et al., Z. Naturforsch.
C. Biosci., 1976, 31C, 252). Chlorfenprop-methyl introduced by Bayer AG. Patents GB
1077194, FR 1476247.
chlorfenson 109
APPLICATIONS:
Mode of action Contact herbicide. Uses For post-emergence control of wild oats, in
cereals (not oats), fodder crops, peas and sugar beet; applied at 4 kg/ha. Only the (-)-
enantiomer is herbicidal (T. Schmidt et al.,
Z. Naturforsch. C. Biosci., 1976, 31C, 252). Formulation types EC.
PRODUCTS:
Discontinued products Bidisin* (Bayer).
ANALYSIS:
Product analysis is by glc. Residues are also determined by glc (H. J. Jarczyk, Pfanz. Nachr.-
Bayer (Engl. Ed.) 1968, 21,360).
ECClassifcation Xn; R21/22| N; R50, R53 (chlorfenprop-methyl)
chlorfenson
Acaricide
NOMENCLATURE:
Common name ovatran (Argentina); ephirsulphonate* (former exception, USSR);
CPCBS (JMAF); chlorof(nizon) ((m) France); chlorfenson (BSI, E-ISO, (m) F-ISO); ovex
(ANSI, Canada)
IUPAC name 4-chlorophenyl 4-chlorobenzenesulfonate
Chemical Abstracts name 4-chlorophenyl 4-chlorobenzenesulfonate Other names
chlorfenizon CAS RN [80331] EC no 2012704 Development codes K 6451
(Dow) Smiles code Clc1ccc(OS(=O)(=O)c2ccc(Cl)cc2)cc1
12
H
8
Cl
2
O
3
S Form Colourless
crystalline solid, with a characteristic odour; (tech. is a colourless to tan faky solid).
M.p. 86.5 C; (tech., c. 80 C) V.p. Negligible (25 C) Solubility Practically insoluble
in water (25 C). In acetone 1300, ethanol 10, xylene 780 (all in g/kg, 25 C). Stability
Hydrolysed by alkali.
COMMERCIALISATION:
History Acaricide reported by E. E. Kenaga & R. W. Hummer (J. Econ. Entomol., 1949, 42,
996). Introduced by Dow Chemical Co. (later DowElanco). Patents US 2528310
APPLICATIONS:
Mode of action A non-systemic acaricide with contact and stomach action and long
residual ovicidal activity. Uses Effective against mites of citrus and other fruit, ornamentals
and vegetable crops at 1732 g/100 l. Phytotoxicity Russetting may occur with apples and
110
chlorfensulphide
pears. Hops may be injured, and leaf drop may occur on roses. Formulation types WP.
PRODUCTS:
Discontinued products Ovitox* (Sipcam Phyteurop); Ovotran* (Dow); Sappiran*
(Nippon Soda); Trichlorfenson* (Bourgeois); Discontinued mixtures Erysit Super*
(+ prothoate) (Schering); Fac Super* (+ prothoate) (Sopra); Mitran* (+ chlorfenethol)
(Nippon Soda); Naftil* (+ carbaryl) (Pepro).
ANALYSIS:
Product analysis by alkaline hydrolysis and back titration (CIPAC Handbook, 1970, 1, 213; FAO
Plant Prot. Bull., 1964, 12, 17). Residues determined by glc or by colorimetry of a derivative
produced after alkaline hydrolysis (A. H. Kutschinski & E. N. Luce, Anal. Chem., 1952, 24,
1188; F. A. Gunther & L. R. Jepson, J. Econ. Entomol., 1954, 47, 1027).
JMPR Evaln. 4 (1965). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
for ratsc. 2000 mg/kg. Skin and eye Acute percutaneous LD
50
for
rats >10 000 mg/kg. It may cause skin irritation. NOEL In 130 d feeding trials, no effect
was observed on rats receiving 300 mg/kg diet. ADI/RfD (JMPR) 0.01 mg/kg b.w. [1965].
Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22| Xi; R38| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail 4600, chickens 3780 mg/kg. Fish LC
50
(48 h) for
carp 3.2 mg/l. Bees Not toxic to bees.
chlorfensulphide
Acaricide
NOMENCLATURE:
Common name CPAS (JMAF); chlorfensulfde ((m) F-ISO); chlorfensulphide (BSI, E-ISO)
IUPAC name 4-chlorophenyl 2,4,5-trichlorobenzenediazosulfde
Chemical Abstracts name [(4-chlorophenyl)thio](2,4,5-trichlorophenyl)diazene
CAS RN [2274740] Smiles code Clc1ccc(SN=Nc2cc(Cl)c(Cl)cc2Cl)cc1
12
H
6
Cl
4
N
2
S M.p. 123.5 C V.p. Very
low at room temperature Solubility Practically insoluble in water. Readily soluble in
acetone, soluble in benzene. Stability Extremely stable to acids and bases.
COMMERCIALISATION:
History Introduced as a component of an acaricide by Nippon Soda Co., Ltd.
APPLICATIONS:
Mode of action Non-systemic acaricide with contact action. Uses Control of spider
mites (in the open and under glass) in fruit, vines, hops, and ornamental cultivation.
chlorfuren; chlorfuren-methyl 111
PRODUCTS:
Discontinued mixtures Milbex* (+ chlorfenethol) (Nippon Soda).
ANALYSIS:
Product: separation of the components of the commercial product by column
chromatography on aluminium oxide and determination of chlorfensulfde
spectrophotometrically at 460 nm Residues by extraction and clean-up by column
chromatography, as above, and determination by gc with ECD.
Oral Acute oral LD
50
for rats 4000 mg/kg. NOEL In rats fed a diet containing 400 mg/kg
for 6 mo, no organ damage is produced and survival rate is unaffected; NOEL 800 mg/kg.
ECOTOXICOLOGY:
ENVIRONMENTAL FATE:
Animals In warm-blooded animals, transformed to the 2,4,4,5-tetrachlorodiphenylsulfde,
with some further oxidation to the corresponding sulfone. Plants In plants, it is rapidly
transformed to the 2,4,4,5-tetrachlorodiphenylsulfde.
chlorfurazole
Herbicide
NOMENCLATURE:
Common name chlorfurazole (BSI, E-ISO, (m) F-ISO)
IUPAC name 4,5-dichloro-2-trifuoromethylbenzimidazole
Chemical Abstracts name 4,5-dichloro-2-(trifuoromethyl)-1H-benzimidazole
CAS RN [3615212] Development codes NC 3363
Smiles code FC(F)(F)c1nc2c(Cl)c(Cl)ccc2[nH]1
8
H
3
Cl
2
F
3
N
2
COMMERCIALISATION:
History Herbicide evaluated by Fisons PLC (later Schering Agriculture).
chlorfuren; chlorfuren-methyl
NOMENCLATURE:
Common name chlorfuren (BSI, E-ISO); chlorfur(ne) ((m) F-ISO)
IUPAC name 2-chlorofuorene-9-carboxylic acid
112
chlornitrofen
Chemical Abstracts name 2-chloro-9H-fuorene-9-carboxylic acid CAS RN [24539
660] chlorfuren; [22909508] chlorfuren-methyl Development codes IT-5732
(chlorfuren-methyl)
PHYSICAL CHEMISTRY: Mol. wt. 244.7; (methyl ester 258.7) M.f. C
14
H
9
ClO
2
; (methyl
ester C
15
H
11
ClO
2
)
COMMERCIALISATION:
History Plant growth regulator introduced by E. Merck (later Shell Agrar GmbH).
chlornitrofen
Herbicide
NOMENCLATURE:
Common name chlornitrofen (BSI, E-ISO); chlornitrof(ne) (F-ISO); CNP (JMAF)
IUPAC name 4-nitrophenyl 2,4,6-trichlorophenyl ether
Chemical Abstracts name 1,3,5-trichloro-2-(4-nitrophenoxy)benzene
CAS RN [1836777] Development codes MO-338
Smiles code [O-][N+](=O)c1ccc(Oc2c(Cl)cc(Cl)cc2Cl)cc1
12
H
6
Cl
3
NO
3
Form Pale yellow crystals.
M.p. 107 C V.p. 3.2 mPa (20 C) K
ow
logP = 5.09 S.g./density 1.623 (23 C) Solubility
In water 0.25 mg/l (25 C). In xylene 360 g/kg (25 C). Stability Stable under neutral
conditions up to 250 C.
COMMERCIALISATION:
History Herbicide introduced in Japan (1966) by Mitsui Toatsu Chemicals, Inc. (later Mitsui
Chemicals, Inc.). Patents GB 1016648; US 3316080; IT 723364 Manufacturers Mitsui
Toatsu; Sinon
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Selective contact
herbicide. Uses Control of annual weeds in rice. Formulation types GR; EC.
PRODUCTS:
Discontinued products Mo* (Mitsui Toatsu).
ANALYSIS:
Product and residue analysis by glc with ECD (Noyaku-Seisan Gijutsu 1971, 23, 114).
Oral Acute oral LD
50
for rats and mice 10 000 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats >10 000 mg/kg. Inhalation LC
50
(4 h) for rats >0.52 mg/l air. NOEL (2 y) for
Cl O NO
2
Cl
Cl
chlorobenzilate 113
rats 0.61, mice 9.5 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation) IV
ECOTOXICOLOGY:
Birds Acute oral LD
50
for pheasants 2680 mg/kg. Fish LC
50
(48 h) for carp >40, killifsh
>100 mg/l. Daphnia LC
50
(3 h) >40 mg/l.
chlorobenzilate
Acaricide
NOMENCLATURE:
Common name chlorobenzilate (BSI, E-ISO, (m) F-ISO, ESA, JMAF)
IUPAC name ethyl 4,4-dichlorobenzilate
Chemical Abstracts name ethyl 4-chloro--(4-chlorophenyl)--hydroxybenzeneacetate
CAS RN [510156] EC no 2081102 Development codes G 23 992
Smiles code CCOC(=O)C(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
16
H
14
Cl
2
O
3
Form Colourless solid.
M.p. 3637.5 C
B.p. 156158 C /0.07 mmHg V.p. 0.12 mPa (20 C) K
ow
logP = 4.58
Henry 3.90 10
3
Pa m
3
mol
1
(calc.) S.g./density 1.2816 (20 C) Solubility In water
10 mg/l (20 C). Readily soluble in most organic solvents, e.g. in acetone, dichloromethane,
methanol, toluene 1000, n-octanol 700, hexane 600 (all in g/kg, 20 C). Stability Hydrolysis
DT
50
7 d (pH 9), 3 d (pH 7), stable (pH 5) (all 25 C) (ARS PPD).
COMMERCIALISATION:
History Acaricide reported by R. Gasser (Experientia, 1952, 8, 65). Introduced by J. R.
Geigy S.A. (later Ciba-Geigy AG). Patents BE 511234; GB 705037 Manufacturers
Makhteshim-Agan
APPLICATIONS:
Mode of action Non-systemic acaricide with contact action and with little insecticidal
action. Uses Used for control of many species of phytophagous mites on pome fruit, citrus
fruit, vines, soya beans, cotton, tea, and vegetables at 1.01.5 kg/ha. Also used for control
of bee mites in beehives. Phytotoxicity Peaches, plums, and some varieties of apple may
be injured. Russetting is possible with pears. Formulation types EC; WP. Compatibility
Incompatible with highly alkaline materials.
PRODUCTS:
Discontinued products Acaraben* (USA) (Ciba-Geigy); Akar* (Ciba-Geigy); Folbex*
(Ciba).
Cl C
CO
2
CH
2
CH
3
OH
Cl
114
1-chloro-2,4-dinitronaphthalene
ANALYSIS:
Product analysis by glc with FID (E. Bartsch et al., Residue Rev., 1971, 39, 1; A. Margot &
K. Stammbach, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 2, 65;
CIPAC Handbook, 1998, H, 81; AOAC Methods, 18th Ed., 971.08). Residues determined by
glc with MCD or ECD (Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1972, 6, 319;
G. Formica et al., Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1135; E. Bartsch et al.,
loc. cit.; Pestic. Anal. Manual 1979, I, 201-A, 201-G; 1979, II; R. Mestres et al., Trav. Soc. Pharm.
Montpellier, 1979, 39, 323). In drinking water by glc with ECD (AOAC Methods, 18th Ed.,
990.06).
JMPR Evaln. 35 (1980). IARC 30 (1983). EU Status (1107/2009) Not approved,
IARC Class 3
Oral Acute oral LD
50
50

for rats and rabbits >10 000 mg/kg. Irritating to eyes; non-irritating to skin (rabbits).
NOEL (2 y) for rats 40 mg/kg diet (c 2.7 mg/kg daily); for dogs 500 mg/kg diet (c. 16.0
mg/kg daily). ADI/RfD (JMPR) 0.02 mg/kg b.w. [1980]; (EPA) cRfD 0.02 mg/kg b.w. [1989].
Water GV Excluded from GV derivation (U). Toxicity Class WHO (a.i.) III EPA
(formulation) III ECClassifcation Xn; R22| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Practically non-toxic to birds. Fish LC
50
for rainbow trout 0.6, bluegill sunfsh 1.8
mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, the principal metabolites identifed were
p,p-dichlorobenzilic acid, p,p-dichlorobenzylhydrol, p-chlorobenzoic acid, and
p,p-dichlorobenzophenone.
1-chloro-2,4-dinitronaphthalene
Fungicide
NOMENCLATURE:
IUPAC name 1-chloro-2,4-dinitronaphthalene (I)
Smiles code [O-][N+](=O)c1cc([N+](=O)[O-])c2ccccc2c1Cl
10
H
5
ClN
2
O
4
COMMERCIALISATION:
History Fungicide.
chloromethiuron 115
chloromebuform
Acaricide
NOMENCLATURE:
Common name chloromebuform (BSI, E-ISO); chlorom(buforme) ((m) F-ISO)
IUPAC name N
1
-butyl-N
2
-(4-chloro-o-tolyl)-N
1
-methylformamidine
Chemical Abstracts name N-butyl-N-(4-chloro-2-methylphenyl)-N-
methylmethanimidamide; N-butyl-N-(4-chloro-o-tolyl)-N-methylformamidine
Smiles code CCCCN(C)C=Nc1ccc(Cl)cc1C
13
H
19
ClN
2
COMMERCIALISATION:
History Acaricide evaluated by Ciba-Geigy AG.
PRODUCTS:
Discontinued products Ektomin* (Ciba-Geigy).
chloromethiuron
Ixodicide
NOMENCLATURE:
Common name chloromethiuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(4-chloro-o-tolyl)-1,1-dimethyl(thiourea)
Chemical Abstracts name N-(4-chloro-2-methylphenyl)-N,N-dimethylthiourea
CAS RN [28217972] Development codes CGA 13 444; C-9140
Smiles code CN(C)C(=S)Nc1ccc(Cl)cc1C
10
H
13
ClN
2
S Form Colourless crystals.
M.p. 175 C V.p. 0.0011 mPa (20 C) Henry 5.03 10
6
Pa m
3
mol
1
(calc.) S.g./density
1.34 (20 C) Solubility In water 50 mg/l (20 C). In acetone 37, dichloromethane 40,
hexane 0.05, isopropanol 5 (all in g/kg, 20 C). Stability Slowly hydrolysed, DT
50
c. 1 y at
5<pH<9.
COMMERCIALISATION:
History Ixodicide reported by M. von Orelli et al. (Proc. World Vet. Congr., 20th, 1975, p. 659).
Introduced by Ciba-Geigy AG. Patents BE 678543; GB 1138714
Cl
CH
3
NHCSN(CH
3
)
2
116
3-(4-chlorophenyl)-5-methylrhodanine
APPLICATIONS: Uses Controls Ixodidae including strains resistant to other ixodicides.
Used on cattle, sheep, horses and dogs in plunge dips at 1.8 g/l. Formulation types SC.
PRODUCTS:
Discontinued products Dipofene* (Ciba-Geigy).
ANALYSIS:
Product analysis by acidimetric titration. Residues determined by glc with ECD.
Oral Acute oral LD
50
50

for rats >2150 mg/kg. Not irritant to skin; irritant to eyes (rabbits). NOEL (90 d) for rats
10 mg/kg diet (1 mg/kg daily), for dogs 50 mg/kg diet (2 mg/kg daily). Toxicity Class WHO
(a.i.) U
ECOTOXICOLOGY:
Fish LC
50
(96 h) for rainbow trout, bluegill sunfsh, carp >49 mg/l.
1-chloro-2-nitropropane
Fungicide
NOMENCLATURE:
IUPAC name 1-chloro-2-nitropropane (I)
Chemical Abstracts name (I) CAS RN [2425663] Development codes FMC 5916
Smiles code CC(CCl)[N+](=O)[O-]
3
H
6
ClNO
2
COMMERCIALISATION:
History Fungicide reported by Bushong (Seed Soil Treatment Newslett., 1962, 4, 39).
Introduced by FMC Corp.
APPLICATIONS:
Mode of action Fumigant soil fungicide.
PRODUCTS:
Discontinued products Lanstan* (FMC).
ICSC.423 (2001).
3-(4-chlorophenyl)-5-methylrhodanine
Fungicide, nematicide
NOMENCLATURE:
IUPAC name 3-(4-chlorophenyl)-5-methylrhodanine; 3-(4-chlorophenyl)-5-methyl-2-
thioxo-1,3-thiazolidin-4-one
chloropon 117
Chemical Abstracts name 3-(4-chlorophenyl)-5-methyl-2-thioxo-4-thiazolidinone
CAS RN [6012926] Development codes N 244
Smiles code CC1SC(=S)N(C1=O)c2ccc(Cl)cc2
10
H
8
ClNOS
2
COMMERCIALISATION:
History Fungicide and nematicide developed by Stauffer Chemical Co.
4-chlorophenyl phenyl sulfone
Acaricide
NOMENCLATURE:
IUPAC name 4-chlorophenyl phenyl sulfone
Chemical Abstracts name 1-chloro-4-(phenylsulfonyl)benzene CAS RN [80002]
Development codes R-242 Smiles code Clc1ccc(cc1)S(=O)(=O)c2ccccc2
12
H
9
ClO
2
S
COMMERCIALISATION:
History Acaricide introduced by Stauffer Chemical Co. (later ICI Americas).
PRODUCTS:
Discontinued products Sulphenone* (ICI).
ANALYSIS:
Residues determined by spectrometry (AOAC Methods, 18th Ed., 958.08, see 11th Ed.,
29.07529.081).
chloropon
Herbicide
NOMENCLATURE:
Common name chloropon (BSI, E-ISO, (m) F-ISO)
IUPAC name 2,2,3-trichloropropionic acid
Chemical Abstracts name 2,2,3-trichloropropanoic acid CAS RN [3278464]
Smiles code OC(=O)C(Cl)(Cl)CCl
3
H
3
Cl
3
O
2
COMMERCIALISATION:
History Herbicide.
118
chloropropylate
chloropropylate
Acaricide
IRAC 12C
NOMENCLATURE:
Common name chloropropylate (BSI, E-ISO, (m) F-ISO, ANSI, ESA, JMAF)
IUPAC name isopropyl 4,4-dichlorobenzilate
Chemical Abstracts name 1-methylethyl 4-chloro--(4-chlorophenyl)--
hydroxybenzeneacetate CAS RN [5836102] Development codes G 24 163
Smiles code CC(C)OC(=O)C(O)(c1ccc(Cl)cc1)c2ccc(Cl)cc2
17
H
16
Cl
2
O
3
M.p. 73 C B.p. 148150 C /0.5 mmHg V.p. 0.044 mPa (20 C) Henry 9.95 10
3
Pa m
3
mol
1
(calc.)
S.g./density 1.35 (20 C) Solubility In water 1.5 mg/l (20 C). In acetone,
dichloromethane 700, hexane 50, methanol 300, n-octanol 130, toluene 500 (all in g/l, 20C).
COMMERCIALISATION:
History Acaricide reported by F. Chabousson (Phytiatr.-Phytopharm., 1956, 5, 203).
Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents BE 511234; GB 705037
APPLICATIONS:
Biochemistry Inhibitor of oxidative phosphorylation; disruptor of ATP formation.
Mode of action Non-systemic acaricide with contact action. Uses At 3060 g/100 l on
cotton, fruit, nuts, ornamentals, sugar beet, tea and vegetables. Formulation types EC.
PRODUCTS:
Discontinued products Acaralate* (Ciba); Chlormite* (Ciba); Rospin* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc with FID (E. Bartsch et al., Residue Rev., 1971, 39, 1; CIPAC Handbook,
1998, H, 85; AOAC Methods, 18th Ed., 971.08). Residues determined by glc with MCD.
JMPR Evaln. 19 (1972). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
for rats >5000 mg tech./kg. Skin and eye Not irritant to skin and
eyes of rabbits. NOEL (2 y) for rats 40 mg/kg diet, for dogs 500 mg/kg diet.
ADI/RfD (JMPR) Temporary ADI withdrawn [1972]. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
50
(96 h) for bluegill sunfsh 0.66, goldfsh 0.6,
rainbow trout 0.45 mg/l. Bees Slightly toxic to honeybees.
chloroxuron 119
2-chlorovinyl diethyl phosphate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name 2-chlorovinyl diethyl phosphate
Chemical Abstracts name 2-chloroethenyl diethyl phosphate CAS RN [311477]
Development codes SD 1836; OS 1836 Smiles code CCOP(=O)(OCC)O/C=C/Cl;
without stereochemistry:CCOP(=O)(OCC)OC=CCl
6
H
12
ClO
4
P
COMMERCIALISATION:
History Insecticide developed by Shell Chemical Co.
APPLICATIONS:
chloroxuron
Herbicide
HRAC C2 WSSA 7; urea
NOMENCLATURE:
Common name chloroxuron (BSI, E-ISO, (m) F-ISO, ANSI, WSSA, JMAF);
chloroxifenidim* (former exception, USSR)
IUPAC name 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea
Chemical Abstracts name N-[4-(4-chlorophenoxy)phenyl]-N,N-dimethylurea
CAS RN [1982474] Development codes C 1983
Smiles code CN(C)C(=O)Nc1ccc(Oc2ccc(Cl)cc2)cc1
PHYSICAL CHEMISTRY: Mol. wt. 290.7 M.f. C15H15ClN
2
O
2
Form Colourless
powder. M.p. 151152 C
V.p. 2.39 10
4
mPa (20 C) K
ow
logP = 3.200 Henry 1.88 10
5
Pa m
3
mol
1
(calc.)
S.g./density 1.34 (20 C) Solubility In water 3.7 mg/l (20 C). In dichloromethane 106,
acetone 44, methanol 35, toluene 4 (all in g/kg, 20 C). Soluble in DMF and chloroform;
slightly soluble in benzene and diethyl ether. Stability Decomposed by uv light. No
signifcant hydrolysis occurred at 30 C at pH 1 or pH 13.
COMMERCIALISATION:
History Herbicide reported (Symp. New Herbic., 3rd, 1961, p. 88). Introduced by Ciba AG
(later Ciba-Geigy AG). Patents BE 593743; GB 913383
Cl O NHCON(CH
3
)
2
120
chloroxuron
APPLICATIONS:
site. Mode of action Selective herbicide, absorbed principally by the roots, but also by
the leaves, with limited translocation acropetally. Uses Pre- and post-emergence control
of annual broad-leaved weeds and some grasses in peas, beans, carrots, celery, celeriac,
onions, leeks, garlic, chives, fennel, parsley, dill, tomatoes, cucurbits, soya beans, strawberries,
ornamentals, fruit trees, and conifers. Control of mosses in ornamental and sports turf, on
paths and non-crop land, and in glasshouses. Formulation types WP.
PRODUCTS:
Discontinued products Tenoran* (Ciba-Geigy).
ANALYSIS:
Product analysis by determination of the dimethylamine produced by hydrolysis, or by
tlc (CIPAC Handbook, 1983, 1B, 1751; G. Voss et al., Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 569; AOAC Methods, 18th Ed., 977.06). Residues determined by hydrolysis to
4-(4-chlorophenoxy)aniline, derivatives of which are measured colorimetrically or by glc
with ECD (G. Voss et al., loc. cit.). Alternatively, glc with ECD may be used directly.
Oral Acute oral LD
50
for male rats 3700, female rats 5400, mice >1000, dogs
>10 000 mg/kg. Skin and eye Acute percutaneous LD
50
for rats >3000 mg/kg. Slightly
irritant to skin and eyes (rabbits). Inhalation LC
50
(6 h) for rats >1.35 mg/l air.
NOEL (120 d) for rats 30 mg/kg daily; (90 d) for dogs 400 mg/kg diet (16.7 mg/kg daily).
ECOTOXICOLOGY:
Birds Slightly toxic to birds. Fish LC
50
for bluegill sunfsh 28, rainbow trout >100, crucian
carp >150 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, chloroxuron undergoes degradation to the monomethylated and
demethylated derivatives, followed by decarboxylation of the phenoxyphenylurea to
(4-chlorophenoxy)aniline. Soil/Environment In soil, microbial degradation leads to the
monomethylated and demethylated derivatives, and then to the (4-chlorophenoxy)aniline
derivative; DT
50
10100 d. Duration of residual activity in soil isc. 4 months.
chlorphonium chloride 121
2-(4-chloro-3,5-xylyloxy)ethanol
Insecticide
NOMENCLATURE:
IUPAC name 2-(4-chloro-3,5-xylyloxy)ethanol
Chemical Abstracts name 2-(4-chloro-3,5-dimethylphenoxy)ethanol
CAS RN [5825796] Development codes Experimental Chemotherapeutant 1182
Smiles code Cc1cc(OCCO)cc(C)c1Cl
10
H
13
ClO
2
COMMERCIALISATION:
History Insecticide introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
chloroxynil
Herbicide
NOMENCLATURE:
Common name chloroxynil (BSI, E-ISO, (m) F-ISO)
IUPAC name 3,5-dichloro-4-hydroxybenzonitrile (I)
Smiles code Oc1c(Cl)cc(C#N)cc1Cl
7
H
3
Cl
2
NO
COMMERCIALISATION:
chlorphonium chloride
NOMENCLATURE:
Common name chlorfonium chloride ((m) F-ISO); chlorphonium chloride (BSI, E-ISO)
IUPAC name tributyl(2,4-dichlorobenzyl)phosphonium chloride
Chemical Abstracts name tributyl[(2,4-dichlorophenyl)methyl]phosphonium chloride
CAS RN [115786] EC no 2041054
Smiles code [Cl-].CCCC[P+](CCCC)(CCCC)Cc1ccc(Cl)cc1Cl
PHYSICAL CHEMISTRY: Mol. wt. 397.8; 362.3 (chlorphonium ion) M.f. C
19
H
32
Cl
3
P;
chlorphonium ion C19H32Cl
2
P Form Colourless crystals. M.p. 114120 C V.p. 9.33
Cl
Cl
Cl
CH
2
P[(CH
2
)
3
CH
3
]
3
122
chlorphoxim
10-2 mPa (20 C) Henry 3.52 10-8 Pa m
3
mol
1
(20 C, calc.) Solubility In water 960
g/l (20 C). In methanol 1030, acetone 200 (both in g/l, 20 C). Insoluble in diethyl ether
and hexane. Stability Stable under normal storage conditions.
COMMERCIALISATION:
History The chloride was introduced as a plant growth regulator by the Mobil Chemical
Co. Patents US 3268323
APPLICATIONS: Uses Used to reduce internodal length in chrysanthemums,
geraniums, petunias, and other responsive ornamentals; to increase the breaking of lateral
shoots in geraniums and petunias; and to increase the number of buds and fowers in
geraniums, azaleas, and rhododendrons. It was most effective as a soil treatment for potted
ornamentals. In addition, treatment of stock plants enhances the uniformity of cuttings
taken from them. Formulation types GR; SL .
PRODUCTS:
Discontinued products Phosfeur* (Perifeur); Phosfon* (Mobil).
Oral Acute oral LD
50
50
for
rabbits 750 mg/kg. Tech. product and formulations are irritating to eyes and skin.
Toxicity Class WHO (a.i.) II EPA (formulation) II ECClassifcation T; R25| Xn; R21| Xi;
R36/38
ECOTOXICOLOGY:
Fish LC
50
(96 h) for rainbow trout 115 mg/l. Bees Not hazardous to bees.
ENVIRONMENTAL FATE:
Soil/Environment DT
50
of chlorphonium in standard German soil 2.2 & 2.3 >28 months,
when stored under BBA conditions.
chlorphoxim
Insecticide
IRAC 1B
NOMENCLATURE:
Common name chlorphoxime ((f) F-ISO); chlorphoxim (BSI, E-ISO)
IUPAC name 2-(2-chlorophenyl)-2-(diethoxyphosphinothioyloxyimino)acetonitrile; O,O-
diethyl 2-chloro--cyanobenzylideneamino-oxyphosphonothioate
Chemical Abstracts name 7-(2-chlorophenyl)-4-ethoxy-3,5-dioxa-6-aza-4-phosphaoct-
6-ene-8-nitrile 4-sulfde; formerly 2-chloro--[(diethoxyphosphinothioyloxy)imino]
benzeneacetonitrile CAS RN [14816207] Development codes BAY SRA 7747;
chlorprazophos 123
Bayer 78182 Smiles code CCOP(=S)(OCC)ON=C(C#N)c1ccccc1Cl
12
H
14
ClN
2
O
3
PS Form Colourless
solid. M.p. 66.5 C B.p. Not distillable V.p. <1 mPa (20 C) Henry <1.96 10
1
Pa m
3
mol
1
(calc.) Solubility In water 1.7 mg/kg (20 C). In cyclohexane, toluene 400600 g/kg
(20 C).
COMMERCIALISATION:
History Insecticide reported by J. E. Hudson & W. O. Obudho (Mosq. News, 1972, 32, 37).
Introduced by Bayer AG. Patents DE 1238902
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Insecticide with contact
action, and long residual activity. Uses For control of mosquitoes and Simulium fies.
Formulation types UL; WP.
PRODUCTS:
Discontinued products Baythion C* (Bayer).
ANALYSIS:
Product analysis by hplc (CIPAC Handbook, 1988, D, 42). Residues determined by glc (D. B.
Leuck & M. C. Bowman, J. Econ. Entomol., 1973, 66, 798).
PDS 32 (1978).
Oral Acute oral LD
50
50
for
rats >500 mg/kg. NOEL In 90 d feeding trials, mice showed no effect at 50 mg/kg diet.
ECOTOXICOLOGY:
Birds Low toxicity to birds. Fish LC
50
(96 h) for rainbow trout 0.11.0 mg/l; (48 h) for
carp 8.5 mg/l.
chlorprazophos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name chlorprazophos (BSI, E-ISO, (m) F-ISO)
IUPAC name O-(3-chloro-7-methylpyrazolo[1,5-a]pyrimidin-2-yl) O,O-diethyl
phosphorothioate (I)
Chemical Abstracts name (I) CAS RN [36145081] Development codes HOX
2709 Smiles code CCOP(=S)(OCC)Oc1nn2c(C)ccnc2c1Cl
11
H
15
ClN
3
O
3
PS
124
chlorquinox
COMMERCIALISATION:
History Insecticide evaluated by Bayer AG.
APPLICATIONS:
chlorprocarb
Herbicide
NOMENCLATURE:
Common name chlorprocarb (BSI, E-ISO); chlorprocarbe ((m) F-ISO)
IUPAC name methyl 3-[1-(chloromethyl)propylcarbamoyloxy]carbanilate
Chemical Abstracts name 3-[(methoxycarbonyl)amino]phenyl [1-(chloromethyl)
propyl]carbamate; methyl m-hydroxycarbanilate [1-(chloromethyl)propyl]
carbamate ester CAS RN [23121995] Development codes BAS 379H (BASF)
Smiles code CCC(CCl)NC(=O)Oc1cccc(NC(=O)OC)c1
13
H
17
ClN
2
O
4
COMMERCIALISATION:
History Herbicide introduced by BASF AG.
chlorquinox
Fungicide
NOMENCLATURE:
Common name chlorquinox (BSI, E-ISO, (m) F-ISO)
IUPAC name 5,6,7,8-tetrachloroquinoxaline (I)
Smiles code Clc1c(Cl)c(Cl)c2nccnc2c1Cl
8
H
2
Cl
4
N
2
COMMERCIALISATION:
History Fungicide introduced by Fisons Ltd (later Schering Agrochemicals Ltd).
PRODUCTS:
Discontinued products Lucel* (Schering).
chlorthiamid 125
chlorthiamid
Herbicide
HRAC L WSSA 20; benzonitrile
NOMENCLATURE:
Common name DCBN (JMAF); chlorthiamid (BSI, E-ISO); chlortiamide ((f) F-ISO)
IUPAC name 2,6-dichlorothiobenzamide
Chemical Abstracts name 2,6-dichlorobenzenecarbothioamide CAS RN [1918134]
EC no 2176377 Development codes WL 5792 (Shell)
Smiles code NC(=S)c1c(Cl)cccc1Cl
7
H
5
Cl
2
NS Form Off-white solid.
M.p. 151152 C V.p. 0.13 mPa (20 C) K
ow
logP = 1.77 Henry 2.82 10
5
Pa m
3
mol
1

(calc.) S.g./density 1.59 (20 C) Solubility In water 950 mg/l (21 C). In aromatic and
chlorinated hydrocarbons
50100 g/kg. Stability Thermally stable up to 90 C. Stable in acidic solutions, but is
converted to dichlobenil in alkaline solutions.
COMMERCIALISATION:
History Herbicide reported by H. Stanford (Proc. Br. Weed Control Conf., 7th, 1964, p. 208).
Introduced by Shell Research Ltd. Discontinued by Hodogaya (2012). Patents GB 987253
Manufacturers Hodogaya
APPLICATIONS:
Biochemistry Precursor of dichlobenil. Mode of action Systemic herbicide, absorbed
by the roots and, to some extent, by the leaves, with translocation principally acropetally.
Inhibits germination of seeds. Uses Selective control of germinating weeds in pome fruit,
currants, gooseberries, raspberries, citrus fruit, vines, olives, lavender, and ornamental plants
and shrubs. Control of bracken, grass and broad-leaved weeds in forestry; and docks in
meadows and pastures. Total weed control on non-crop land, paths, industrial areas, etc.
Formulation types GR . Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Prefx* (Shell).
ANALYSIS:
Product by potentiometric titration with silver nitrate (CIPAC Handbook, 1980, 1A, 1158).
Residues by glc with ECD (K. I. Beynon et al., J. Sci. Food Agric., 1966, 17, 151155).
ICSC.852 (1996). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
C
Cl Cl
S NH
2
126
chlorthiophos
Oral Acute oral LD
50
50
for
rats >1000 mg/kg. NOEL (90 d) for rats 100 mg/kg diet. Toxicity Class WHO (a.i.) III
EPA (formulation) III ECClassifcation Xn; R22
ECOTOXICOLOGY:
Birds Acute oral LD
50
for duck 374 mg/kg. Fish LC
50
(96 h) for carp 42 mg/l. Daphnia
LC
50
50
(48 h) 17 mg/l. Bees LD
50
(oral, 48 h) 77.3 g/bee, LD
50

(contact, 96 h) >100 g/bee.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, there is rapid metabolism and 70%
elimination in the urine within 24 h. Soil/Environment In soil, chlorthiamid is
converted to dichlobenil (q.v.), which then gradually undergoes microbial degradation to
2,6-dichlorobenzamide and 2,6-dichlorobenzoic acid. Converted to dichlobenil in soil; DT
50

for chlorthiamid + dichlobenilc. 35 d under dry and 14 d under wet conditions. Duration
of residual activity in soil isc. 57 months. The fate in crops, soils and animals has been
reviewed (K. I. Beynon & A. N. Wright, Residue Rev., 1972, 43, 23).
chlorthiophos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name chlorthiophos (BSI, E-ISO, (m) F-ISO, ANSI, ESA, for an isomeric reaction
mixture)
IUPAC name O-2,5-dichloro-4-methylthiophenyl O,O-diethyl phosphorothioate (i, main
component); O-4,5-dichloro-2-methylthiophenyl O,O-diethyl phosphorothioate (ii, small
quantities); O-2,4-dichloro-5-methylthiophenyl O,O-diethyl phosphorothioate (iii, minor
component)
Chemical Abstracts name O-[2,5-dichloro-4-(methylthio)phenyl] O,O-diethyl
phosphorothioate (i); O-[4,5-dichloro-2-(methylthio)phenyl] O,O-diethyl phosphorothioate
(ii); O-[2,4-dichloro-5-(methylthio)phenyl] O,O-diethyl phosphorothioate (iii)
CAS RN [60238564] mixed isomers; [21923239] isomer (i)
EC no 2446636 for isomer (i) Development codes S 2957 (Boehringer, Cela GmbH)
Smiles code CCOP(=S)(OCC)Oc1cc(Cl)c(SC)cc1Cl
11
H
15
Cl
2
O
3
PS
2
Form Yellow-brown
liquid. M.p. Crystallises <25 C B.p. 153158 C /0.013 mmHg V.p. 0.53 mPa (25 C) S.g./
density 1.345 (20 C) Solubility In water c. 0.3 mg/l (20 C). Miscible with all common
organic solvents. Stability DT
50
42 d (pH <9).
COMMERCIALISATION:
History Insecticide reported by H. Holtmann & E. Raddatz (Proc. Br. Insectic. Fungic. Conf.,
chlozolinate 127
6th, 1971, 2, 485). Introduced by C. H. Boehringer Sohn/Cela GmbH (later Shell Agrar
GmbH). Patents DE 1298990; GB 1210826
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact and ingested
insecticide and acaricide. Uses Effective against Diptera, Hemiptera, Lepidoptera and with
some acaricidal activity. Rates 3001500 g/ha depend on pests and the crop. Formulation
types DP; EC; GR; WP.
PRODUCTS:
Discontinued products Celathion* (Shell Agrar).
ANALYSIS:
Product analysis is by bromometric titration. Residues may be determined by glc.
Oral Acute oral LD
50
for male rats 10.7, female rats 7.8, mice 91.4 mg/kg.
50
for male rats 153, female rats 121, rabbits
5058 mg/kg. NOEL (2 y), based on erythrocyte cholinesterase inhibition, for rats 1.6 mg/
kg diet; (1 y) for dogs 1 mg/kg diet. Toxicity Class WHO (a.i.) IaECClassifcation T+;
R28| T; R24| N; R50, R53| concn. dep. (for isomer (i))
ECOTOXICOLOGY:
Birds LC
50
(8 d) for bobwhite quail 213, mallard ducks 0.198 mg/kg diet. Fish LC
50
(96 h)
for bluegill 1.3, rainbow trout 0.019 mg/l.
chlozolinate
Fungicide
FRAC 2, E3; dicarboximide
NOMENCLATURE:
Common name chlozolinate (BSI, E-ISO, (m) F-ISO)
IUPAC name ethyl ()-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-oxazolidine-5-carboxylate
Chemical Abstracts name ()-ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-
5-oxazolidinecarboxylate CAS RN [84332865] racemate; [72391469] unstated
stereochemistry EC no 2827144 Development codes M 8164 (Agrimont)
Smiles code CCOC(=O)C1(C)OC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
Cl
Cl
O
O
N
O
CH
3
CO
2
CH
2
CH
3
128
chlozolinate
13
H
11
Cl
2
NO
5
Form Colourless, almost
odourless solid. M.p. 112.6 C V.p. 0.013 mPa (25 C, gas saturation method) K
ow
logP
= 3.15 (22 C) Henry 2.29 10
3
Pa m
3
mol
1
Solubility In water c. 2 ppm (25 C). In acetone, ethyl acetate and 1,2-dichloroethane
>250, ethanol c. 13, n-heptanec. 2, xylenec. 60 (all in g/kg, 22 C). Stability Stable to
250 C (under nitrogen). Stable to light. In solution, hydrolysis occurs at pH 59.
COMMERCIALISATION:
History Fungicide reported by Di Toro et al. (Atti Giornate Fitopatol., Siusi, 1980). Introduced
by Agrimont (later Isagro S.p.A.). Patents BE 874406; DE 2906574; IT 20579/78
Manufacturers Isagro
APPLICATIONS:
Biochemistry Affects mitogen-activated protein histidine kinase, in osmotic signal
transduction. Mode of action Contact fungicide with protective and curative action. Uses
Control of Botrytis spp., sclerotinia spp., and monilia spp. in ornamentals, vegetables, vines,
pome fruit, stone fruit, sunfowers and strawberries. Can be applied, at 7501000 g/ha, as a
foliar spray or as a soil drench. Formulation types SC. WP.
PRODUCTS:
Discontinued products Manderol* (Isagro); Serinal* (Isagro).
ANALYSIS:
Product and residues can be determined by glc. Details are available from Isagro.
EU Rev. Rep. 8397/VI/98 (1999). EU Status (1107/2009) Not approved, 2000/626/EC.
Oral Acute oral LD
50
for rats >4500, mice >10 000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >5000 mg/kg. Non-irritating to skin and eyes (rabbits). Not
a skin sensitiser (guinea pigs). Inhalation LC
50
(4 h) for rats >10 mg/l air. NOEL (90 d)
for rats 200 mg/kg diet; (1 y) for dogs 200 mg/kg diet. ADI/RfD (ECCO) 0.1 mg/kg
b.w. [1999]. Other Not mutagenic, not teratogenic. Toxicity Class WHO (a.i.) U EPA
(formulation) III ECClassifcation R40| N; R51, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for quail and mallard ducks >4500 mg/kg. Fish LC
50
(96 h) for trout
27.5 mg/l. Daphnia LC
50
50
(96 h) for Selenastrum capricornutum
30 mg/l. Bees LD
50
(oral) >100 g/bee. Otherbenefcial Harmless to Phytoseiulus
persimilis at up to 2 recommended application rate.
ENVIRONMENTAL FATE:
Animals Chlozolinate is readily absorbed, metabolised and excreted. Metabolites
identifed in urine of rats are: 3-(3,5-dichlorophenyl)-5-methyloxazolidin-2,4-dione,
N-(3,5-dichlorophenyl)-2-hydroxypropionamide, O-1-carboxyethyl-N-3,5-dichlorophenyl
carbamate, and N-(3,5-dichloro-2(or 4)-hydroxyphenyl)-2-hydroxypropionamide and its
sulfate and glucuronide conjugates. Plants In plants, chlozolinate undergoes hydrolysis and
decarboxylation processes, giving the same metabolites as those identifed in animals.
cispermethrin 129
Soil/Environment In silt-loam, sandy loam and clay loam soils, hydrolysis and
decarboxylation occur; aerobic DT
50
<7 h.
ciobutide
NOMENCLATURE:
Common name ciobutide (BSI, E-ISO, (m) F-ISO)
IUPAC name (RS)-2-cyano-2-phenylbutyramide
Chemical Abstracts name ()--cyano--ethylbenzeneacetamide
CAS RN [80544758] Smiles code CCC(C#N)(C(=O)N)c1ccccc1
11
H
12
N
2
O
COMMERCIALISATION:
History Plant growth regulator discovered by EGYT Pharmacochemical Works.
cispermethrin
Insecticide
An isomer pair, component of permethrin.
NOMENCLATURE:
IUPAC name 3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclo
propanecarboxylate; 3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethyl
cyclopropanecarboxylate
Chemical Abstracts name rel-(1R,3R)-(3-phenoxyphenyl)methyl 3-(2,2-dichloro
ethenyl)-2,2-dimethylcyclopropanecarboxylate; cis-()-(3-phenoxyphenyl)methyl
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate CAS RN [61949766],
formerly [52341330]; [54774457] (1R)-cis- resolved isomer; [54774468] (1S)-
cis- isomer Development codes FMC 35171; NRDC 148; NRDC 167 (for the (1R)-cis-
resolved isomer)
21
H
20
Cl
2
O
3
ANALYSIS:
O
CH
2
C CH
CH
3
CH
3
Cl
C
O
O
Cl
130
CL900167
CL 304,415
Herbicide safener
NOMENCLATURE:
IUPAC name 4-carboxymethylchroman-4-carboxylic acid
Chemical Abstracts name 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid
CAS RN [31541578], formely [217311610] Development codes CL 304,415
Smiles code OC(=O)CC1(CCOc2ccccc21)C(=O)O
12
H
12
O
5
COMMERCIALISATION:
History Herbicide safener, reported by G. E. Cary et al. (Proc. 8th IUPAC International
Congress of Pesticide Chemistry, Washington, 1994). Developed by American Cyanamid Co.
APPLICATIONS:
Biochemistry Increases the rate of metabolism of imazethapyr in maize. Uses Safens
maize against injury by imazethapyr and other imidazolinone herbicides.
CL900167
Acaricide
NOMENCLATURE:
Chemical Abstracts name 4-[(4-chloro-,,-trifuoro-m-tolyl)oxy]-6-[(,,,4-
tetrafuoro-m-tolyl)oxy]-pyrimidine Development codes CL 900,167 (Shell); AC
9
00,167
(Cyanamid)
18
H
8
ClF
7
N
2
O
2
M.p. 65 C V.p.c. 1
10
1
mPa S.g./density 1.033 (20 C) Solubility In water <0.1 ppm.
O
HO
2
C CH
2
CO
2
H
N N
O
F
F
F
F
O
F
F
F
Cl
cliodinate 131
climbazole
Fungicide
NOMENCLATURE:
Common name climbazole (BAN)
IUPAC name 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethylbutanone
Chemical Abstracts name 1-(4-chlorophenoxy)-1-(1H-imidazol-1-yl)-3,3-
dimethyl-2-butanone CAS RN [38083179] Development codes BAY MEB 6401
Smiles code CC(C)(C)C(=O)C(Oc1ccc(Cl)cc1)n2ccnc2
15
H
17
ClN
2
O
2
Form Colourless
crystalline solid. M.p. 95.5 C
V.p. 1.0 mPa (extrapolated to 50 C) Solubility In water 5.5 mg/l (20 C). In
cyclohexanone 400600, isopropanol 100200 g/kg (20 C).
COMMERCIALISATION:
History Fungicide introduced by Bayer AG. Patents BE 2600800
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. Uses A fungicide, effective against
Aspergillus, Candida, Paecilomyces and Penicillium spp. on various household materials, utensils
and parts of buildings.
PRODUCTS:
Discontinued products Baysan* (Bayer).
ANALYSIS:
Product analysis is by glc.
Oral Acute oral LD
50
for male rats 400 mg/kg.
cliodinate
Herbicide
NOMENCLATURE:
Common name cliodinate (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-chloro-3,5-di-iodo-4-pyridyl acetate
Chemical Abstracts name 2-chloro-3,5-di-iodo-4-pyridinyl acetate
CAS RN [69148125] Development codes ASD 2288
Smiles code CC(=O)Oc1c(I)cnc(Cl)c1I
7
H
4
ClI
2
NO
2
COMMERCIALISATION:
History Herbicide evaluated by Celamerck GmbH KG (later Shell Agrar GmbH).
132
cloethocarb
cloethocarb
IRAC 1A
NOMENCLATURE:
Common name clo(thocarb) ((m) F-ISO); cloethocarb (BSI, E-ISO)
IUPAC name 2-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate
Chemical Abstracts name 2-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate
CAS RN [51487695] Development codes BAS 263I (BASF)
Smiles code CNC(=O)Oc1ccccc1OC(CCl)OC
11
H
14
ClNO
4
M.p. 80 C;
(tech.: 6975 C) V.p. 0.01 mPa (20 C) Henry 2.00 10
6
Pa m
3
mol
1
(calc.)
Solubility In water 1.3 g/kg (20 C). In acetone, chloroform >1000, ethanol 153
(all in g/kg, 20 C). Stability Non-hygroscopic. Hydrolysed by strong acids or alkalis.
COMMERCIALISATION:
History Insecticide reported by V. Harries et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1978, 45, 739). Introduced by BASF AG. Patents DE 2231249; GB 1426233; US 3962316
Manufacturers BASF
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide and
nematicide with contact and stomach action. Absorbed by the roots and translocated to
the foliage. Uses Control of corn rootworms on maize; colorado beetle on potatoes; and
a variety of aphids, caterpillars, scales, nematodes etc. on peanuts, potatoes, rice, sugar cane,
tobacco, sorghum, coffee, wheat, oilseed rape and alfalfa. Could be applied as a granular soil
treatment, as a seed treatment, or as bait pellets. Formulation types GR; FS; BR .
PRODUCTS:
Discontinued products Lance* (BASF).
ANALYSIS:
Product analysis by hplc. Residues determined by alkaline hydrolysis to a derivative which is
determined by hplc.
Oral Acute oral LD
50
for rats 35.4, mice 70.4 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats 4000 mg/kg. NOEL (1 y) for dogs 0.5 mg/kg daily (capsule administration);
OCONHCH
3
OCHCH
2
Cl
OCH
3
clofencet-potassium; clofencet 133
for rats 25 mg/kg diet (c. 1 mg/kg daily); for mice 10 mg/kg diet (c. 1 mg/kg daily).
Toxicity Class WHO (a.i.) Ib EPA (formulation) II
ECOTOXICOLOGY:
Fish Moderately toxic to fsh. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Residual activity is 37 weeks.
clofencet-potassium; clofencet
NOMENCLATURE:
Common name clofencet (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name potassium 2-(4-chlorophenyl)-3-ethyl-2,5-dihydro-5-oxopyridazine-4-
carboxylate
Chemical Abstracts name potassium 2-(4-chlorophenyl)-3-ethyl-2,5-dihydro-5-oxo-
4-pyridazinecarboxylate CAS RN [82697710] clofencet-potassium; [129025543]
clofencet Development codes MON 21233 (Monsanto); RH 754 (Rohm & Haas);
RH0754 (Rohm & Haas); FC 4001 (Zeneca); ICIS 0754 (ICI) (all clofencet-potassium);
MON 21200 (Monsanto) (clofencet)
Smiles code CCc1c(C(=O)O)c(=O)cnn1c2ccc(Cl)cc2
PHYSICAL CHEMISTRY: Mol. wt. 316.8; 278.7 (clofencet) M.f. C
13
H
10
ClKN
2
O
3
;
clofencet C
13
H
11
ClN
2
O
3
M.p. 269 C (decomp.) V.p. <1 10
2
mPa (25 C) K
ow
logP =
2.2 (25 C)
Henry <5.7 10-9 Pa m
3
mol
1
(25 C, calc.) S.g./density 1.44 (20 C) Solubility In
water >552; >655 (pH 5), >696 (pH 7), >658 (pH 9) (all in g/l, 23 C). In methanol 16,
acetone <0.5, dichloromethane <0.4, toluene <0.4, ethyl acetate <0.5, n-hexane <0.6 (all
in g/l, 24 C). Stability Stable 14 d (54 C). Stable to hydrolysis in sterile aqueous pH 5, 7,
and 9 buffered solutions. Moderately persistent to aqueous photolysis; DT
50
increases with
pH. pKa 2.83 (20 C) (clofencet)
COMMERCIALISATION:
History Discovered by Rohm & Haas Co. (later Dow AgroSciences). Introduced by
Monsanto Co. for use in wheat in 1997.
APPLICATIONS:
Mode of action Systemic. Inhibits pollen formation. Uses The potassium salt is a
chemical hybridising agent for wheat. Applied at 35 kg/ha. Formulation types SC.
PRODUCTS:
Discontinued products Detasselor* (potassium salt) (Monsanto); Genesis* (potassium
salt) (Monsanto).
EPA Fact Sheet, Feb. 1997. EU Status (1107/2009) Not approved, 2004/129/EC.
134
clofop; clofop-isobutyl
Oral Acute oral LD
50
dermal LD
50
for rats >5000 mg/kg. Eye irritant; not a skin irritant (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation EC
50
for rats >3.8 mg/l. NOEL (1 y) for dogs 5.0 mg/kg
daily. ADI/RfD (EPA) cRfD 0.05 mg/kg b.w. [1997]
ECOTOXICOLOGY:
Birds Acute oral LD
50
for ducks >2000, quail 1414 mg/kg. Dietary LC
50
for ducks and quail
>4818 ppm. Fish LC
50
for bluegill sunfsh >1070, rainbow trout >990 ppb. Daphnia EC
50

>1193 mg/l. Algae EbC50 (96 h) for Selenastrum capricornutum 141 mg/l; ErC50 374 mg/l.
Other aquatic spp. IC50 (14 d) for Lemna gibba (G3) >6.1 mg/l. Bees LD
50
(48 h) (contact
and oral) >100 g/bee. Worms EC
50
>1000 ppm.
ENVIRONMENTAL FATE:
Animals In rats, clofencet was rapidly absorbed and excreted; >78% of the administered
14
C-label was eliminated in the urine within 24 h. Clofencet was eliminated mostly
unmetabolised and mainly in the urine. At 7 days post-dosing, <1% was retained in the
tissue. Plants Clofencet is poorly metabolised in wheat, >80% of the residue in wheat
seed, andc. 70% of the residue in wheat straw is unmetabolised clofencet.
Soil/Environment Metabolism of clofencet in laboratory soil studies is very slow. After
one year in loamy sand (pH 6.0, 4.5% o.m.) and silt loam (pH 7.7, 2.4% o.m.),c. 70% of
the applied clofencet remains; the main route of dissipation is soil binding. Clofencet is
fairly stable to soil photolysis (7481% of parent clofencet remains after 3032 d). DT
50

2028 d in aqueous solutions (pH 5, 7 and 9). In European feld dissipation studies, DT
50

in silty clay and silty clay loam soils (pH 6.67.8) 2566 d for three sites, although slower
degradation was seen at some sites. Batch equilibrium studies and pKa considerations
suggest that clofencet is very mobile in sand, loamy sand, and silt loam soils, but laboratory
and feld studies suggest that the signifcant soil binding which occurs with time mitigates
the tendency towards mobility. Clofencet has the potential for runoff or soil mobility but,
in practice, because of specialised use and stewardship practices, effects of mobility and
persistence are less likely to be signifcant.
clofop; clofop-isobutyl
Herbicide
NOMENCLATURE:
Common name clofop (BSI, E-ISO, (m) F-ISO, WSSA)
IUPAC name ()-2-[4-(4-chlorophenoxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-(4-chlorophenoxy)phenoxy]propanoic acid
CAS RN [59621497] racemic clofop; [26129328] clofop (unstated stereochemistry);
[51337714] clofop-isobutyl (unstated stereochemistry) Development codes Hoe 22 870
cloproxydim 135
PHYSICAL CHEMISTRY: Mol. wt. 292.7; (isobutyl ester 348.8) M.f. C
15
H
13
ClO
4
;
(isobutyl ester C
19
H
21
ClO
4
)
Form The ester is a colourless crystalline solid. M.p. 3940 C Solubility In water
180 mg/l (22 C). Highly soluble in acetone and xylene.
COMMERCIALISATION:
History Herbicide described by F. Schwerdtle et al. (Mitt. Biol. Bundesanst. Land-Forstwirtsch.
Berlin-Dahlem, 1975, 165, 171). Clofop-isobutyl introduced by Hoechst AG.
APPLICATIONS:
Mode of action Taken up through the leaves and roots and is selective in nearly all
cultivated dicotyledonous crops as well as in cereals. Details PM6, p. 125. Uses Clofop-
isobutyl is a post-emergence herbicide efffective against annual grasses such as Alopecurus
myosuroides, Echinochloa crus-galli, Eleusine, Panicum and Setaria spp.
Oral Acute oral LD
50
for male rats 1208 mg/kg. NOEL (90 d) for dogs and male rats
32 mg/kg diet. Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22 (clofop-isobutyl)
cloproxydim
Herbicide
NOMENCLATURE:
Common name clopropoxydim* (former WSSA); cloproxydim (BSI, ANSI, WSSA, E-ISO);
cloproxydime ((f) F-ISO)
IUPAC name ()-2-[1-(3-chloroallyloxy)iminobutyl]-5-(2-ethylthiopropyl)-3-
hydroxycyclohex-2-enone
Chemical Abstracts name 2-[1-[[(3-chloro-2-propenyl)oxy]imino]butyl]-5-
[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one CAS RN [95480334]
Development codes RE-36 290
Smiles code CCCC(=NOCC=CCl)C1=C(O)CC(CC(C)SCC)CC1=O
18
H
28
ClNO
3
S Form Liquid. V.p.
<0.013 mPa (20 C)
S.g./density 1.15 (20 C) Solubility Soluble in most organic solvents. Stability Unstable
in acid or alkaline solution, or on heating.
COMMERCIALISATION:
History Herbicide evaluated by Chevron Chemical Company LLC.
APPLICATIONS:
Mode of action Selective herbicide. Uses A post-em. herbicide controlling a wide range
of annual and perennial grasses in beans, cotton, potatoes, sugar beet, and most vegetable
crops. Formulation types EC.
136
coumafuryl
PRODUCTS:
Discontinued products Selectone* (Chevron).
Oral Acute oral LD
50
50

for rats >500 mg/kg. Other Non-mutagenic in the Ames assay.
copper bis(3-phenylsalicylate)
Fungicide
NOMENCLATURE:
IUPAC name copper bis(3-phenylsalicylate)
Chemical Abstracts name bis(2-hydroxy[1,1-biphenyl]-3-carboxylato-O
2
,O
0
)copper
CAS RN [5328041] Smiles code [Cu+2].Oc1c(cccc1c2ccccc2)C(=O)[O-].
Oc1c(cccc1c2ccccc2)C(=O)[O-]
26
H
18
CuO
6
COMMERCIALISATION:
History Fungicide.
copper zinc chromate
Fungicide
NOMENCLATURE:
IUPAC name copper zinc chromate (indefnite composition)
Development codes Crag Fungicide 658; Experimental Fungicide 658
COMMERCIALISATION:
History Fungicide evaluated by Union Carbide Corp. (later Rhne-Poulenc Agrochimie).
coumafuryl
Rodenticide
NOMENCLATURE:
Common name coumafuryl (BSI since 1984, E-ISO, (m) F-ISO); fumarin (BSI pre-1984,
Canada); tomarin* (Turkey pre-1984)
IUPAC name 3-[1-(2-furyl)-3-oxobutyl]-4-hydroxycoumarin
coumithoate 137
Chemical Abstracts name 3-[1-(2-furanyl)-3-oxobutyl]-4-hydroxy-2H-1-
benzopyran-2-one CAS RN [117522] unstated stereochemistry EC no 2041955
Smiles code CC(=O)CC(c1ccco1)c2c(O)c3ccccc3oc2=O
17
H
14
O
5
COMMERCIALISATION:
History Rodenticide developed by Amchem Chemical Co. (later Rhne-Poulenc
Agrochimie).
APPLICATIONS:
Mode of action Anticoagulant rodenticide.
EHC 175 (1995). EU Status (1107/2009) Not approved, 2004/129/EC.
ECClassifcation T; R25, R48/25| R52, R53
coumithoate
Insecticide
IRAC 1B
NOMENCLATURE:
Common name coumithoate (BSI, E-ISO, (m) F-ISO)
IUPAC name O,O-diethyl O-(7,8,9,10-tetrahydro-6-oxo-6H-benzo[c]chromen-3-yl)
phosphorothioate; 3-diethoxyphosphinothioyloxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
Chemical Abstracts name O,O-diethyl O-(7,8,9,10-tetrahydro-6-oxo-6H-dibenzo[b,d]
pyran-3-yl) phosphorothioate CAS RN [572485]
Smiles code CCOP(=S)(OCC)Oc1ccc2c3CCCCc3c(=O)oc2c1
17
H
21
O
5
PS
COMMERCIALISATION:
History Insecticide introduced by Montecatini S.p.A. (later Agrimont S.p.A.).
APPLICATIONS:
PRODUCTS:
Discontinued products Dithion* (Agrimont); Dition* (Agrimont).
ECClassifcation T; R25
138
credazine
CP 17029
Herbicide
NOMENCLATURE:
IUPAC name N
2
,N4-bis(3-methoxypropyl)-6-methylthio-1,3,5-triazine-2,4-diamine;
2,4-bis(3-methoxypropylamino)-6-(methylthio)-1,3,5-triazine
Chemical Abstracts name N,N-bis(3-methoxypropyl)-6-(methylthio)-1,3,5-triazine-2,4-
diamine Other names MPMT CAS RN [845523] Development codes CP 17 029
Smiles code COCCCNc1nc(NCCCOC)nc(SC)n1
12
H
23
N
5
O
2
S
COMMERCIALISATION:
History Herbicide introduced by Monsanto Co.
PRODUCTS:
Discontinued products Lambast* (Monsanto).
credazine
Herbicide
NOMENCLATURE:
Common name credazine (JMAF)
IUPAC name pyridazin-3-yl o-tolyl ether
Chemical Abstracts name 3-(2-methylphenoxy)pyridazine CAS RN [14491
599] Development codes H 722; SW-6701; SW-6721 (all Sankyo)
Smiles code Cc1ccccc1Oc2cccnn2
11
H
10
N
2
O Form Colourless needles.
M.p. 78 C Solubility In water 2 g/l (room temperature). Readily soluble in organic
solvents. Stability Stable to light, heat and humidity.
COMMERCIALISATION:
History Herbicide reported by T. Jojima et al. (Agric. Biol. Chem., 1968, 32, 1376; 1969, 33,
96). Introduced by Sankyo Co. Ltd. Patents JP 509596.
APPLICATIONS:
Mode of action Selective herbicide. Uses Selective soil herbicide, used in Japan for
the control of annual grasses and some broad-leaved weeds in tomatoes, pimentoes and
strawberries, at 23 kg ha.
PRODUCTS:
Discontinued products Kusakira* (Sankyo).
ANALYSIS:
Product analysis by glc. Residues are determined by glc after separation by tlc.
Oral Acute oral LD
50
for rats 3090, mice 569 mg/kg. Toxicity Class WHO (a.i.) U
crimidine 139
ENVIRONMENTAL FATE:
Plants In plants, the major metabolites are (2H)-pyridazin-3-one and 3-(1--D-
glucosyloxy)pyridazine (M. Nakagawa et al., Agric. Biol. Chem., 1971, 25, 764).
Soil/Environment Moderately persistent in soil (S. Yoshimura et al., Zasso Kenkyu, 1969,
No. 7, p. 84).
crimidine
Rodenticide
NOMENCLATURE:
Common name crimidine (BSI, E-ISO, (f) F-ISO)
IUPAC name 2-chloro-N,N,6-trimethylpyrimidin-4-amine
Chemical Abstracts name 2-chloro-N,N,6-trimethyl-4-pyrimidinamine
CAS RN [535897] EC no 2086226 Smiles code CN(C)c1cc(C)nc(Cl)n1
PHYSICAL CHEMISTRY:
Composition Tech. containsc. 20% of the non-rodenticidal 4-chloro-N,N,6-
trimethylpyrimidin-2-ylamine. Mol. wt. 171.6 M.f. C
7
H
10
ClN
3
Form Tech. is a brownish
wax. M.p. 87 C
B.p. 140147 C /4 mmHg Solubility In water 9.4 g/l (20 C). In dichloromethane
6001200, isopropanol 100200 (both g/l, 20 C).
COMMERCIALISATION:
History Rodenticide introduced in the early 1940s by Bayer AG. Patents US 2219858
APPLICATIONS: Formulation types AB.
PRODUCTS:
Discontinued products Castrix* (Bayer).
ANALYSIS:
Product and residue analysis is by hplc (E. Mllhoff, Pfanz.-Nachr. Bayer (Engl. Ed.), 1980, 33,
86).
Oral Acute oral LD
50
for rats 1.25, rabbits 5 mg/kg. Toxicity Class WHO (a.i.) O
ECClassifcation T+; R28
ECOTOXICOLOGY:
Birds It is not a cumulative poison; birds are not harmed by the ingestion of a few grains
of the formulation.
140
crotoxyphos
crotoxyphos
IRAC 1B
NOMENCLATURE:
Common name crotoxyphos (BSI, E-ISO, (m) F-ISO, ESA); crotoxyfos (BAN)
IUPAC name 1-phenylethyl 3-(dimethoxyphosphinoyloxy)isocrotonate; dimethyl (E)-1-
methyl-2-(1-phenylethoxycarbonyl)vinyl phosphate
Chemical Abstracts name (E)-1-phenylethyl 3-[(dimethoxyphosphinyl)oxy]-2-butenoate
CAS RN [7700176] EC no 2317205 Development codes SD 4294 (Shell)
Smiles code COP(=O)(OC)OC(=CC(=O)OC(C)c1ccccc1)C
PHYSICAL CHEMISTRY:
14
H
19
O
6
P Form Tech. is a light straw-
coloured liquid.
B.p. 135 C /0.03 mmHg (tech.) V.p. 1.9 mPa (20 C) Henry 5.97 10
4
Pa m
3
mol
1

(calc.) S.g./density 1.2 (20 C, tech.) Solubility In water 1 g/l (room temperature).
Soluble in acetone, ethanol, isopropanol, xylene. Stability DT
50
87 h (pH 1), 35 h (pH 9)
(38 C)
COMMERCIALISATION:
History Insecticide reported by C. P. Weidenback & R. L. Younger (J. Econ. Entomol., 1962,
55, 793). Introduced by the Shell Development Co. Patents US 3068268; US 3116201
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses An insecticide with a rapid action and
moderately persistent residual effect on a wide range of external insect pests of livestock
and was recommended for the control of fies, mites and ticks on cattle and pigs.
Formulation types EC. Compatibility Incompatible with most mineral carriers, except
synthetic silicas such as Colloidal Silica K320 and Hisil 233.
PRODUCTS:
Discontinued products Ciodrin* (Shell).
ANALYSIS:
Product analysis by i.r. spectroscopy or by glc. Residues determined by glc with FPD
(P. E. Porter, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 243; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 325).
Oral Acute oral LD
50
for rats 52.8, mice 90 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits 384 mg/kg. NOEL In 90 d feeding trials, no effect on growth nor
histopathological change observed for male rats receiving 900 mg/kg diet, and for female
rats receiving 300 mg/kg diet. Toxicity Class WHO (a.i.) IbECClassifcation T; R24/25|
N; R50, R53| concn. dep.
crufomate 141
ENVIRONMENTAL FATE:
Metabolism and breakdown in plant, animals and soil has been reviewed (K. I. Beynon et al.,
Residue Rev., 1973, 47, 55).
crufomate
Anthelmintic, insecticide
IRAC 1B
NOMENCLATURE:
Common name crufomate (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name 4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate
Chemical Abstracts name 2-chloro-4-(1,1-dimethylethyl)phenyl
methyl methylphosphoramidate CAS RN [299865] EC no 2060831
Development codes Dowco 132 Smiles code CNP(=O)(OC)Oc1ccc(cc1Cl)C(C)(C)C
12
H
19
ClNO
3
P Form Colourless
crystals. M.p. 60 C
Solubility Practically insoluble in water. Readily soluble in acetone, acetonitrile, benzene,
carbon tetrachloride; practically insoluble in light petroleum. Stability Stable at pH 7.0
but is incompatible with alkaline pesticides and is decomposed in strongly acidic media.
COMMERCIALISATION:
History Veterinary insecticide and anthelmintic reported by J. F. Landram & R. J. Shaver
(J. Parasitol., 1959, 45, 55). Introduced by Dow Chemical Co. (later DowElanco). Patents BE
579237.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide Uses
Systemic insecticide and anthelmintic used mainly for the treatment of cattle against
Warble fies, ectoparasites and helminths. Compatibility Incompatible with alkaline
pesticides.
PRODUCTS:
Discontinued products Ruelene* (DowElanco).
ANALYSIS:
Product analysis is by i.r. spectroscopy, with carbon disulfde as standard.
JMPR Evaln. 11 (1968), 19 (1972). ICSC.143 (1995).
Oral Acute oral LD
50
for rats 770950, rabbits 400600 mg/kg. ADI/RfD (JMPR)
0.1 mg/kg b.w. [1968]. Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R21/22| N;
R50, R53
142
cufraneb
CS 708
Insecticide
NOMENCLATURE:
IUPAC name 1,1-bis(4-chlorophenyl)-2-nitrobutane (i) + 1,1-bis(4-chlorophenyl)-2-
nitropropane (ii)
Chemical Abstracts name 1,1-(2-nitrobutylidene)bis[4-chlorobenzene] (i)
+ 1,1-(2-nitropropylidene)bis[4-chlorobenzene] (ii) CAS RN [117260] (i); [117271]
(ii); [8027007] (i) + (ii), formerly [8002822] Development codes CS 674A (i); CS
645A (ii); CS 708 (i + ii) Smiles code CCC(C(c1ccc(Cl)cc1)c2ccc(Cl)cc2)[N+](=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 324.2 (i); 310.2 (ii) M.f. C
16
H
15
Cl
2
NO
2
(i);
C
15
H
13
Cl
2
NO
2
(ii)
COMMERCIALISATION:
History Insecticide introduced by Commercial Solvents Corp.
PRODUCTS:
Discontinued products Bulan* ((i)) (Commercial Solvents); Dilan* ((i) + (ii))
(Commercial Solvents); Prolan* (Commercial Solvents).
cufraneb
NOMENCLATURE:
Common name cufraneb (BSI, E-ISO); cufran(be) ((m) F-ISO)
IUPAC name ethylenebis(dithiocarbamate) mixed metal complex containing not less
than 8.15% (m/m) of zinc, 8.05% (m/m) of manganese, 5.5% (m/m) of copper and 1.0%
(m/m) of iron
Chemical Abstracts name cufraneb (not defned in 9CI; see 8CI)
CAS RN [11096187]
COMMERCIALISATION:
History Fungicide introduced by Universal Crop Protection Ltd.
APPLICATIONS:
Biochemistry Non-specifc thiol reactant, inhibiting respiration. Mode of action Foliar,
preventive fungicide with secondary acaricidal activity. Uses Effective against Phytophthora
infestans in potatoes and tomatoes, Nectria galligena in pome fruit, Pseudomonas mors-
prunorum in cherries, Taphrina deformans in stone fruit and Pseudopeziza ribis in bush fruit.
Also controls citrus rust mites. Formulation types WP.
PRODUCTS:
Discontinued products Cufram Z* (UCP); Discontinued mixtures Macuprax*
(+ Bordeaux mixture) (Agtrol International).
cupric hydrazinium sulfate 143
ANALYSIS:
Identifed colorimetrically (CIPAC Handbook, 1994, F, 320).
EHC 78 (1988); a general review of dithiocarbamates and their degradation products. EHC
200 (1998) is a general review of copper and copper compounds.
Oral Acute oral LD
50
for rats 2700 mg/kg. Skin and eye Irritating to skin, eyes and
respiratory system. Toxicity Class EPA (formulation) III
ECOTOXICOLOGY:
m-cumenyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name m-cumenyl methylcarbamate; 3-isopropylphenyl methylcarbamate
Chemical Abstracts name 3-(1-methylethyl)phenyl methylcarbamate
Other names IPMC CAS RN [64006] Development codes AC 5727 (Hercules);
UC 10 854 (Union Carbide) Smiles code CNC(=O)Oc1cccc(c1)C(C)C
11
H
15
NO
2
COMMERCIALISATION:
History Insecticide introduced by Hercules Inc. (later Nor-Am) and Union Carbide Corp.
(later Rhne-Poulenc Agrochimie).
APPLICATIONS: Uses For use in rice.
cupric hydrazinium sulfate
Fungicide
NOMENCLATURE:
IUPAC name copper(II) dihydrazinium disulfate
Chemical Abstracts name bis(hydrazine)bis(hydrogen sulfato)copper Other names
cupric hydrazinium sulfate CAS RN [33271657] Development codes Mathieson 466
Smiles code [H+].[H+].N[NH2+][Cu+2][NH2+]N.[O-]S(=O)(=O)[O-].[O-]S(=O)(=O)[O-]
PHYSICAL CHEMISTRY: Mol. wt. 321.8 M.f. CuH
10
N
4
O
8
S
2
COMMERCIALISATION:
History Fungicide introduced by Olin Mathieson Chemical Corp.
144
cuprous chloride
PRODUCTS:
Discontinued products Omazene* (Olin).
cuprobam
Fungicide
NOMENCLATURE:
Common name cuprobame ((m) France); cuprobam (BSI)
IUPAC name tricopper dichloride dimethyldithiocarbamate
Chemical Abstracts name dichloro(dimethylcarbamodithioato)tricopper
CAS RN [7076633]
3
H
6
Cl
2
Cu
3
NS
2
COMMERCIALISATION:
History Fungicide.
cuprous chloride
NOMENCLATURE:
Chemical Abstracts name copper chloride CAS RN [7758896]
PHYSICAL CHEMISTRY:
Form Grey tan or green powder. M.p. >430 C V.p. 1.3 (546 C) S.g./density 4.14
Solubility In water 0.62 g/100 g.
COMMERCIALISATION:
History First registered in USA in 1998.
APPLICATIONS: Uses Incorporated into plastic plant pots, where it inhibits root
growth when seedling roots reach the pot wall; this prevents root circling.
PRODUCTS:
Other products Migratrol (Premium).
EHC 200 (1998) is a general review of copper and copper compounds. EPA Fact Sheet, Sep.
1998.
Oral Acute oral LD
50
50
for
rats 2002000 mg/kg. Eye and skin irritant. Skin sensitiser. Inhalation LC
50
for rats
220 mg/l. ADI/RfD (JECFA evaluation) copper compounds 0.5 mg/kg [1982].
cyanofenphos 145
cyanatryn
Herbicide
NOMENCLATURE:
Common name cyanatryn (BSI, E-ISO); cyanatryne ((f) F-ISO)
IUPAC name 2-(4-ethylamino-6-methylthio-1,3,5-triazin-2-ylamino)-2-
methylpropiononitrile
Chemical Abstracts name 2-[[4-(ethylamino)-6-(methylthio)-1,3,5-triazin-2-yl]amino]-
2-methylpropanenitrile CAS RN [21689849] Development codes WL 63 611
Smiles code CCNc1nc(NC(C)(C)C#N)nc(SC)n1
10
H
16
N
6
S
COMMERCIALISATION:
History Herbicide reported by V. V. Dovlatyan & F. V. Avetisyan (Arm. Khim. Zh., 1972, 25,
880) and evaluated by Shell Research Ltd.
2-cyano-3-(2,4-dichlorophenyl)acrylic acid
NOMENCLATURE:
IUPAC name 2-cyano-3-(2,4-dichlorophenyl)acrylic acid
Chemical Abstracts name 2-cyano-3-(2,4-dichlorophenyl)-2-propenoic acid
CAS RN [6013054] Development codes Ethyl 214 Smiles code OC(=O)/C(=C\
c1ccc(Cl)cc1Cl)/C#N;without stereochemistry:OC(=O)C(=Cc1ccc(Cl)cc1Cl)C#N
10
H
5
Cl
2
NO
2
COMMERCIALISATION:
History Plant growth regulator developed by Ethyl Corp. Agrochemicals (later Nor-Am).
cyanofenphos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name CYP (JMAF); cyanofenphos (BSI, E-ISO); cyanophenphos (F-ISO)
IUPAC name O-4-cyanophenyl O-ethyl phenylphosphonothioate
Chemical Abstracts name O-(4-cyanophenyl) O-ethyl phenylphosphonothioate
CAS RN [13067931] Development codes S-4087 (Sumitomo Chemical)
Smiles code CCOP(=S)(Oc1ccc(C#N)cc1)c2ccccc2
15
H
14
NO
2
PS Form Tech. is a white
or slightly yellowish solid. M.p. 7178 C (tech.) V.p. 0.00137 mPa (20 C) Solubility In
water 0.6 mg/l (30 C). In methanol 89 g/kg (30 C); in xylene 515 g/kg (27 C).
146
cyanthoate
COMMERCIALISATION:
History Insecticide reported by Y. Nishizawa (Bull. Agric. Chem. Soc. Japan, 1960, 24, 744).
Introduced by Sumitomo Chemical Co., Ltd. Patents JP 410930; JP 410925; GB 929738
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses An insecticide effective against penetrating
and chewing insects, cotton bollworms, gall midges, rice borers and other insects on fruits
and vegetables. Formulation types EC.
PRODUCTS:
Discontinued products Surecide* (Sumitomo Chemical).
ANALYSIS:
Product analysis by glc. Residues in milk and meat determined by glc with FPD (J. Miyamoto
et al., Nihon Noyaku Gakkaishi, 1977, 2, 1).
Oral Acute oral LD
50
50
for male
rats >1000, female rats 640 mg/kg. ADI/RfD (JMPR) Temporary ADI withdrawn (1983).
Toxicity Class WHO (a.i.) IIECClassifcation T; R25, R39/25| Xn; R21| Xi; R36| N;
R51, R53
cyanthoate
NOMENCLATURE:
Common name cyanthoate (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name S-[N-(1-cyano-1-methylethyl)carbamoylmethyl] O,O-diethyl
phosphorothioate; N-(1-cyano-1-methylethyl)-2-(diethoxyphosphinoylthio)acetamide
Chemical Abstracts name S-[2-[(1-cyano-1-methylethyl)amino]-2-oxoethyl] O,O-diethyl
phosphorothioate CAS RN [3734950] EC no 2230994 Development codes M 1568
Smiles code CCOP(=O)(OCC)SCC(=O)NC(C)(C)C#N
10
H
19
N
2
O
4
PS
COMMERCIALISATION:
History Insecticide and acaricide reported by F. Galbaiti (Proc. Br. Insectic. Fungic. Conf., 1st,
1961, 2, 507). Introduced by Montecatini S.p.A. (later Montedison S.p.A.).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact, ingested and systemic
insecticide and acaricide.
PRODUCTS:
Discontinued products Tartan* (Montedison).
cyclafuramid 147
Toxicity Class WHO (a.i.) OECClassifcation T+; R28| T; R24
cybutryne
Algistat
NOMENCLATURE:
Common name cybutryne (BSI, E-ISO, (m) F-ISO)
IUPAC name N
2
-tert-butyl-N
4
-cyclopropyl-6-methylthio-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-cyclopropyl-N-(1,1-dimethylethyl)-
6-(methylthio)-1,3,5-triazine-2,4-diamine CAS RN [28159980]
Smiles code CC(NC1=NC(NC2CC2)=NC(SC)=N1)(C)C
11
H
19
N
5
S
COMMERCIALISATION:
Manufacturers Zhejiang Zhongshan; Ciba
PRODUCTS:
Other products Irgarol 1510 (Ciba Specialty Chemicals).
cyclafuramid
Fungicide
NOMENCLATURE:
Common name cyclafuramid (BSI, E-ISO); cyclafuramide ((m) F-ISO)
IUPAC name N-cyclohexyl-2,5-dimethyl-3-furamide
Chemical Abstracts name N-cyclohexyl-2,5-dimethyl-3-furancarboxamide
CAS RN [34849428] Development codes BAS 327F (BASF)
Smiles code Cc1cc(C(=O)NC2CCCCC2)c(C)o1
13
H
19
NO
2
COMMERCIALISATION:
History Fungicide introduced by BASF AG.
N
N N
N
H
SCH
3
N
H
C(CH
3
)
3
148
cycloheximide
cycloheximide
Fungicide, plant growth regulator
NOMENCLATURE:
Common name cycloheximide (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]
glutarimide
Chemical Abstracts name [1S-[1(S*),3,5]]-4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-
hydroxyethyl]-2,6-piperidinedione CAS RN [66819]
Smiles code CC1CC(C)C(=O)C(C1)C(O)CC2CC(=O)NC(=O)C2
15
H
23
NO
4
M.p. 115.5117 C Solubility In water 21 g/l (2 C). Soluble in chloroform, isopropanol,
other common organic solvents; sparingly soluble in saturated hydrocarbons. Stability
Stable in neutral or acid solution, but rapidly decomposed by alkali at room temperature
to form 2,4-dimethylcyclohexanone. Specifc rotation []25D 6.8 (20 g/l water)
COMMERCIALISATION:
Production Produced in culture by Streptomyces griseus and was recovered as a by-
product of streptomycin manufacture. History Antifungal antibiotic isolated by A. Whiffen
et al. (J. Bacteriol., 1946, 52, 610), agricultural uses reviewed (J. H. Ford et al., Plant Dis. Rep.,
1958, 42, 680). Introduced for crop protection by the Upjohn Co. (later Nor-Am.).
APPLICATIONS: Uses It inhibits the growth, in culture, of many plant pathogenic fungi;
it was used to control powdery mildews on ornamentals, rusts and leafspot on grasses. Its
plant growth-regulating properties were used for promoting the abscission of fruit, e.g. olives
and oranges. Formulation types WP. Compatibility Chlordane is reported to cause a
rapid loss of activity.
PRODUCTS:
Discontinued products ActiAid* (Upjohn); Actidione* (Upjohn).
ANALYSIS:
Product analysis by bioassay (G. C. Prescott et al., J. Agric. Food Chem., 1956, 4, 343; W. W.
Kilgore, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 1).
ICSC.244 (1997).
Oral Acute oral LD
50
for rats 2, mice 133, guinea pigs 65, monkeys 60 mg/kg.
Toxicity Class WHO (a.i.) IaECClassifcation R68| R61| T+; R28| N; R51, R53
cyometrinil 149
cycluron
Herbicide
NOMENCLATURE:
Common name cycluron (BSI, E-ISO, (f) F-ISO, WSSA); COMU (JMAF)
IUPAC name 3-cyclo-octyl-1,1-dimethylurea
Chemical Abstracts name N-cyclooctyl-N,N-dimethylurea Other names OMU
CAS RN [2163691] Smiles code CN(C)C(=O)NC1CCCCCCC1
PHYSICAL CHEMISTRY:
11
H
22
N
2
M.p. 138 C;
(tech., 134138 C) Solubility In water 1.1 g/l (20 C). In acetone 67, benzene 55,
methanol 500 (all in g/kg, 20 C).
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Z. Pfanzenkr. Pfanzenpathol. Pfanzenschutz,
1960, 67, 577). Introduced by BASF AG. Patents DE 1027930, DE 1062482.
APPLICATIONS: Uses A mixture of cycluron and chlorbufam was used pre-em. at 36
l Alipur/ha to control annual weeds in sugar beet and vegetables.
PRODUCTS:
Discontinued mixtures Alipur* (+ chlorbufam) (BASF).
ANALYSIS:
Product analysis is by titration. Residues may be determined by glc of the dimethylamine
produced by hydrolysis.
Oral Acute oral LD
50
for rats 2600 mg/kg. Skin and eye There was no local irritation
to the backs of ears of white rabbits treated (20 h) with an aqueous solution (500 g/l).
cyometrinil
Herbicide safener
NOMENCLATURE:
Common name cyom(trinil) ((m) F-ISO); cyometrinil (BSI, WSSA, E-ISO)
IUPAC name (Z)-cyanomethoxyimino(phenyl)acetonitrile
Chemical Abstracts name (Z)--[cyanomethoxyimino]benzeneacetonitrile
CAS RN [78370215] (Z)- isomer; [63278331] unstated stereochemistry
Development codes CGA 43 089 Smiles code N#CCON=C(C#N)c1ccccc1
150
cypendazole
10
H
7
N
3
M.p. 5556 C V.p. 0.0465 mPa (20 C) Henry 9.07 10
5
Pa m
3
mol
1
(calc.) S.g./
density 1.260 Solubility In water
95 mg/l (20 C). In benzene 550, dichloromethane 700, methanol 230, isopropanol 74 (all
in g/kg, 20 C). Stability DT
50
(calc.) >200 d (pH 57), 19.4 d (pH 9) (20 C). Exothermic
decomposition >300 C.
COMMERCIALISATION:
History Herbicide safener for 2-chloroacetanilides, introduced by Ciba-Geigy AG.
Patents BE 845827, GB 1524596.
APPLICATIONS:
Biochemistry Enhances cytochrome P450-mediated oxidative metabolism of the
herbicide (see J. Davies & J. C. Caseley, Pestic. Sci. 1999, 55(11) 10431058). Uses Increases
the tolerance of some crop plants to chloroacetanilide herbicides.
PRODUCTS:
Discontinued products Concep* (Ciba-Geigy).
ANALYSIS:
Product analysis is by glc. Residues are determined by glc using TID.
Oral Acute oral LD
50
50

for rats >3100 mg/kg. Non-irritant to skin and eyes (rabbits). NOEL (90 d) for dogs
>100 mg/kg diet (3.1 mg/kg daily). Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds In laboratory trials it is slightly toxic to birds. Fish LC
50
(96 h) for rainbow trout 5.6,
carp 11.7, bluegill 10.9 mg/l.
cypendazole
Fungicide
NOMENCLATURE:
Common name cypendazole (BSI, E-ISO, (m) F-ISO, JMAF)
IUPAC name methyl 1-(5-cyanopentylcarbamoyl)benzimidazol-2-ylcarbamate
Chemical Abstracts name methyl [1-[[(5-cyanopentyl)amino]carbonyl]-1H-
benzimidazol-2-yl]carbamate CAS RN [28559004] Development codes DAM 18 654
Smiles code COC(=O)Nc1nc2ccccc2n1C(=O)NCCCCCC#N
16
H
19
N
5
O
3
COMMERCIALISATION:
History Systemic fungicide introduced by Bayer AG.
cyprazine 151
APPLICATIONS:
Mode of action Systemic fungicide.
PRODUCTS:
Discontinued products Folicidin* (Bayer).
cyperquat; cyperquat chloride
Herbicide
NOMENCLATURE:
Common name cyperquat (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 1-methyl-4-phenylpyridinium (I)
Chemical Abstracts name (I) CAS RN [48134754] cyperquat; [39794995]
cyperquat chloride Development codes S 21 634
PHYSICAL CHEMISTRY: Mol. wt. 170.2; (cyperquat chloride 205.7) M.f. C
12
H
12
N;
(cyperquat chloride C
12
H
12
ClN)
COMMERCIALISATION:
History Cyperquat chloride introduced as a herbicide by Gulf Oil Chemicals.
cyprazine
Herbicide
NOMENCLATURE:
Common name cyprazine (BSI, E-ISO, (f) F-ISO, ANSI, WSSA)
2
-cyclopropyl-N
4
-isopropyl-1,3,5-triazine-2,4-diamine; 2-chloro-
4-cyclopropylamino-6-isopropylamino-1,3,5-triazine
Chemical Abstracts name 6-chloro-N-cyclopropyl-N-(1-methylethyl)-1,3,5-triazine-2,4-
diamine CAS RN [22936863] Development codes S 6115
Smiles code CC(C)Nc1nc(Cl)nc(NC2CC2)n1
9
H
14
ClN
5
COMMERCIALISATION:
History Herbicide reported by O. C. Burnside et al. (Proc. North Cent. Weed Control Conf.,
1969, p. 21). Introduced by Gulf Oil Corp.
PRODUCTS:
Discontinued products Outfox* (Gulf); Discontinued mixtures Prefox*
(+ ethiolate) (Gulf).
152
cyprofuram
cyprazole
Herbicide
NOMENCLATURE:
Common name cyprazole (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]
cyclopropanecarboxamide (I)
Chemical Abstracts name (I) CAS RN [42089032] Development codes S 19 073
Smiles code CC(C)(CCl)c1nnc(NC(=O)C2CC2)s1
10
H
14
ClN
3
OS
COMMERCIALISATION:
History Herbicide introduced by Gulf Oil Chemicals.
cyprofuram
Fungicide
NOMENCLATURE:
Common name cyprofuram (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name ()--[N-(3-chlorophenyl)cyclopropanecarboxamido]--butyrolactone
Chemical Abstracts name N-(3-chlorophenyl)-N-(tetrahydro-2-oxo-3-furanyl)
cyclopropanecarboxamide CAS RN [69581335] unstated stereochemistry
EC no 2740509 Development codes SN 78 314 (Schering)
Smiles code Clc1cccc(c1)N(C2CCOC2=O)C(=O)C3CC3
14
H
14
ClNO
3
Form Colourless
crystalline solid. M.p. 9596 C V.p. 0.0066 mPa (25 C) Solubility In water 574 mg/l
(room temperature). In acetone, dichloromethane 500, cyclohexanone 330, ethanol 50,
n-octanol 17, xylene 60 (all in
g/kg, room temperature). Stability Stable in acid media, but hydrolysed under alkaline
conditions; DT
50
37 d (pH 7), 12 h (pH 9) (25 C).
COMMERCIALISATION:
History Fungicide reported by D. Baumert & H. Buschhaus (Meded. Fac. Landbouwwet.
Rijksuniv. Gent, 1982, 47, 979). Introduced by Schering AG. Patents GB 1603730
APPLICATIONS:
Mode of action Systemic fungicide. Uses Active against Oomycetes. It was
recommended against Plasmopara viticola and Phytophthora infestans but only in combination
with contact fungicides.
PRODUCTS:
Discontinued products Vinicur* (Schering).
DAEP 153
Oral Acute oral LD
50
for rats 174, mice 296314 mg/kg. Skin and eye Acute
percutaneous LD
50
for rabbits >1000 mg/kg. Toxicity Class WHO (a.i.) II
ECClassifcation T; R25| Xn; R21| N; R50, R53
cypromid
Herbicide
NOMENCLATURE:
Common name cypromid (BSI, E-ISO, ANSI, WSSA, JMAF); cypromide ((f) F-ISO)
IUPAC name 3,4-dichlorocyclopropanecarboxanilide
Chemical Abstracts name N-(3,4-dichlorophenyl)cyclopropanecarboxamide
CAS RN [2759719] Development codes S 6000
Smiles code Clc1ccc(NC(=O)C2CC2)cc1Cl
10
H
9
Cl
2
NO
COMMERCIALISATION:
History Herbicide reported by T. R. Hopkins et al. (Proc. Symp. New Herbic., 2nd, Paris,
1965, p. 187). Introduced by Gulf Oil Corp.
APPLICATIONS:
PRODUCTS:
Discontinued products Clobber* (Gulf).
DAEP
Insecticide
IRAC 1B
NOMENCLATURE:
Common name DAEP (JMAF)
IUPAC name N-(2-dimethoxyphosphinothioylthioethyl)acetamide; S-2-acetamidoethyl
O,O-dimethyl phosphorodithioate
Chemical Abstracts name S-[2-(acetylamino)ethyl] O,O-dimethyl phosphorodithioate
CAS RN [13265606] Smiles code COP(=S)(OC)SCCNC(=O)C
6
H
14
NO
3
PS
2
154
decafentin
COMMERCIALISATION:
History Insecticide developed by Nippon Soda Co., Ltd.
APPLICATIONS:
PRODUCTS:
Discontinued products Amiphos* (Nippon Soda).
DCPM
Acaricide
NOMENCLATURE:
Common name DCPM (JMAF)
IUPAC name bis(4-chlorophenoxy)methane
Chemical Abstracts name 1,1-[methylenebis(oxy)]bis[4-chlorobenzene]
Other names oxythane CAS RN [555895] Development codes K-1875
Smiles code Clc1ccc(OCOc2ccc(Cl)cc2)cc1
13
H
10
Cl
2
O
2
COMMERCIALISATION:
History Acaricide reported by L. R. Jeppson (J. Econ. Entomol., 1946, 39, 813). Introduced by
Dow Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Neotran* (Dow).
decafentin
Fungicide
NOMENCLATURE:
Common name decafentin (BSI, E-ISO, (m) F-ISO)
IUPAC name decyltriphenylphosphonium bromochlorotriphenylstannate(IV)
Chemical Abstracts name (TB-512)-decyltriphenylphosphonium
bromochlorotriphenylstannate(1-) CAS RN [15652387] Development codes A 36
Smiles code CCCCCCCCCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3.Cl[Sn-](Br)(c1ccccc1)
(c2ccccc2)c3ccccc3
46
H
51
BrClPSn
COMMERCIALISATION:
History Fungicide introduced by Celamerck GmbH & Co. (later Shell Agrar).
PRODUCTS:
Discontinued products Stanoram* (Shell Agrar).
defenuron 155
decarbofuran
Insecticide
NOMENCLATURE:
Common name decarbofuran (BSI, E-ISO, (m) F-ISO)
IUPAC name 2,3-dihydro-2-methylbenzofuran-7-yl methylcarbamate
Chemical Abstracts name 2,3-dihydro-2-methyl-7-benzofuranyl methylcarbamate
CAS RN [1563673] Development codes BAY 62 863
Smiles code CNC(=O)Oc1cccc2CC(C)Oc21
11
H
13
NO
3
COMMERCIALISATION:
APPLICATIONS:
ECClassifcation T; R23/24/25
defenuron
Herbicide
NOMENCLATURE:
Chemical Abstracts name N-phenyl-N-methylurea CAS RN [1007369]
Development codes IPO 4328
8
H
10
N
2
M.p. 148149.5 C
V.p. 1 10-2 mPa (20 C) Henry 1.18 10
6
Pa m
3
mol
1
(20 C, calc.)
S.g./density 1.222 (25 C) Solubility In water 1.27 g/l (20 C). In ethanol 7.2 g/l, benzene
0.1 g/100 g, methylene chloride 0.331 g/100 g (all at 23 C).
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Inhibits photosynthesis. Mode of action Active by both leaf and root
uptake. Uses Control of weeds in potatoes, cereals, maize, sunfower, peas, vines, fruit and
forestry; used in combination with triazine or other herbicides. Formulation types WP.
ANALYSIS:
Product by acid hydrolysis with a mixture of sulfuric and phosphoric acids; made alkaline
and the liberated methylamine distilled off and measured by titration. Residues by
extraction with methanol, clean up by column chromatography; then acid hydrolysis,
diazotisation and coupling of the aniline with N-(1-naphthyl)ethylenediamine, followed by
determination by tlc or colorimetry.
156
dehydroacetic acid
Oral Acute oral LD
50
for rats 3440 mg/kg. NOEL (90 d) for rats 180 mg/kg daily.
ECOTOXICOLOGY:
Fish LC
50
(120 h) for guppies 172 mg/l.
ENVIRONMENTAL FATE:
Plants Metabolism is by N-demethylation to N-phenylurea; both parent and metabolite are
conjugated as glycosides.
dehydroacetic acid
Fungicide
NOMENCLATURE:
IUPAC name 2-acetyl-5-methyl-3-oxopent-4-en-5-olide (i); 3-acetyl-6-methylpyran-2,4-
dione (ii) Chemical Abstracts name 3-acetyl-6-methyl-2H-pyran-2,4(3H)-dione (i);
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one (ii); 3-acetyl-2-hydroxy-6-methyl-4H-
pyran-4-one (iii) Other names DHA CAS RN [520456] (i); [771039] (ii);
[16807480] (iii); [4418262] sodium salt EC no 2082939; 2245801 sodium salt
Smiles code CC(=O)C1C(=O)OC(=CC1=O)C
8
H
8
O
4
Form Colourless powder.
M.p. 109111 C (subliming)
B.p. 269 C V.p. 2.5 10
5
mPa (100 C) Solubility In water 330 g/kg (25 C). In
propylene glycol 480, methanol 140 (both g/kg, 25 C); sparingly soluble in non-hydroxylic
organic solvents.
COMMERCIALISATION:
History Long-known as a chemical, fungicidal activity reported by P. A. Wolf (Food Technol.
(Chicago), 1950, 4, 294). Introduced by Dow Chemical Co.
APPLICATIONS: Uses Fungicide for prevention of mould growth on fresh and dried
fruit and vegetables, and for impregnation of food wrappings.
ANALYSIS:
Residue analysis is by extraction wth chloroform from acid solution, measuring the optical
density at 307 nm.
Oral Acute oral LD
50
for rats 1000 mg/kg. Sodium salt: Acute oral LD
50
for rats
1000 mg/kg. Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22. (Sodium salt Xn;
R22) Details PM6, p. 152.
demephion; demephion-O; demephion-S 157
delachlor
Herbicide
NOMENCLATURE:
Common name delachlor (BSI, E-ISO, ANSI); d(lachlore) ((m) F-ISO)
IUPAC name 2-chloro-N-(isobutoxymethyl)acet-2,6-xylidide
Chemical Abstracts name 2-chloro-N-(2,6-dimethylphenyl)-N-[(2-methylpropoxy)
methyl]acetamide CAS RN [24353580] Development codes CP 52 223
Smiles code CC(C)COCN(C(=O)CCl)c1c(C)cccc1C
15
H
22
ClNO
2
COMMERCIALISATION:
History Herbicide reported by R. F. Husted et al. (Proc. North Cent. Weed Control Conf.,
1967). Introduced by Monsanto Co.
demephion; demephion-O; demephion-S
IRAC 1B
NOMENCLATURE:
Common name demephion (for a reaction product comprising demephion-O and
demephion-S) (BSI); demephion-O (i), demephion-S (ii) (for thiono and thiolo isomers,
respy.) (BSI, E-ISO, (m) F-ISO)
IUPAC name (i) O,O-dimethyl O-2-methylthioethyl phosphorothioate; (ii) O,O-dimethyl
S-2-methylthioethyl phosphorothioate
Chemical Abstracts name (i) O,O-dimethyl O-[2-(methylthio)ethyl] phosphorothioate;
(ii) O,O-dimethyl S-[2-(methylthio)ethyl] phosphorothioate Other names methyl-
demeton-methyl CAS RN [682804] (i); [2587908] (ii); [8065621] (i) + (ii)
EC no 2116669 (i); 2199719 (ii)
5
H
13
O
3
PS
2
Form Straw-coloured
liquid. B.p. 107 C (decomp.)/
0.1 mmHg (i); 65 C (decomp.)/0.1 mmHg (ii) S.g./density 1.198 (20 C) (i); 1.218 (25 C)
(ii) Solubility In water 300 mg/l (i), 3000 mg/l (ii) (both room temperature). The mixture
is miscible with most aromatic solvents, chlorobenzene and ketones; immiscible with most
aliphatic hydrocarbons.
COMMERCIALISATION:
History Systemic acaricide and insecticide reported by H. Rueppold (Wiss. Z. Martin-
Luther Univ. Halle-Wittenberg Math.-Naturwiss. Reihe, 1955, 5, 219). Introduced initially by VEB
Farbenfabrik Wolfen. Patents DE 1014017.
158
demeton; demeton-O; demeton-S
APPLICATIONS:
acaricide. Uses Effective against sucking insects, at 170510 g/ha. Compatibility Not
compatible with strongly alkaline pesticides.
PRODUCTS:
Discontinued products Atlasetox* (Atlas); Cymetox* (Cyanamid); Pyracide* (BASF);
Tinox* (E. Europe) (VEB Farbenfabrik Wolfen).
ANALYSIS:
Product analysis by separating the two isomers using column chromatography;
demephion-O is then oxidised by perchloric acid and determined as phosphate;
demephion-S is hydrolysed by alkali, the solution acidifed and titrated with iodine. Residue
analysis is by isolation and oxidation to phosphate, which is measured colorimetrically by
standard procedures.
Toxicity Class WHO (a.i.) IaECClassifcation T+; R28| T; R24 (for (i) or (ii))
ENVIRONMENTAL FATE:
Plants Metabolised in plants to the sulfoxide, then slowly to the sulfone and to
phosphates.
demeton; demeton-O; demeton-S
IRAC 1B
NOMENCLATURE:
Common name mercaptofos* (i) (USSR); mercaptofos teolevy* (ii) (USSR);
mercaptostiol (ii) (USSR); mercaptofostion (i) (USSR); demeton-O (i), demeton-S (ii) (for
thiono and thiolo isomers, respy.) (BSI, E-ISO, (m) F-ISO); demeton (for a reaction product
comprising demeton-O and demeton-S) (BSI, ESA)
IUPAC name (i) O,O-diethyl O-2-ethylthioethyl phosphorothioate; (ii) O,O-diethyl S-2-
ethylthioethyl phosphorothioate
Chemical Abstracts name (i) O,O-diethyl O-[2-(ethylthio)ethyl] phosphorothioate; (ii)
O,O-diethyl S-[2-(ethylthio)ethyl] phosphorothioate Other names diethyl 2-ethylthioethyl
phosphorothionate (i); diethyl 2-ethylthioethyl phosphorothiolate (ii) CAS RN [298
033] demeton-O; [126750] demeton-S; [8065483] demeton, formerly [8000973]
EC no 2060538 demeton-O; 2048018 demeton-S
Development codes Bayer 10 756; E-1059
PHYSICAL CHEMISTRY:
Composition Reaction of 2-ethylthioethanol with O,O-diethyl phosphorochloridothioate
gives demeton asc. 65:35 mixture of (i) and (ii). Mol. wt. 258.3 M.f. C
8
H
19
O
3
PS
2

demeton; demeton-O; demeton-S 159
Form Pure demeton-O (i) and demeton-S (ii) are colourless oils. Tech. mixture is a light
yellow oil with a pronounced mercaptan-like odour. B.p. 123 C /1 mmHg (demeton-O);
128 C /1 mmHg (demeton-S) V.p. 38 mPa (20 C, demeton-O); 35 mPa (20 C,
demeton-S) Henry demeton-O; 1.64 10
1
Pa m
3
mol
1
(20 C, calc.); demeton-S: 4.52
10
3
Pa m
3
mol
1
(20 C, calc.) S.g./density demeton-O 1.119 (21 C); demeton-S 1.132
(21 C) Solubility Demeton-O (i) (room temperature): 60 mg/l water; soluble in most
organic solvents. Demeton-S (ii) (room temperature): 2 g/l water; soluble in most organic
solvents. Stability Demeton is hydrolysed by concentrated alkali, but is compatible with
most non-alkaline pesticides except water-soluble mercury compounds. The mechanism
of isomerisation of (i) to (ii) was examined by T. R. Fukuto & R. L. Metcalf (J. Am. Chem.
Soc., 1954, 76, 5103) and the self-alkylation of demeton described by D. F. Heath, (Nature
(London), 1957, 179, 377).
COMMERCIALISATION:
History Insecticide reported by G. Unterstenhfer (Meded. Landbouwhogesch.
Opzoekingsstn. Staat Gent, 1952, 17, 75). Introduced by Farbenfabriken Bayer AG (later Bayer
AG). Patents DE 836349; US 2571989
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic and contact insecticide
and acaricide, with some fumigant action. Demeton-S rapidly penetrates foliage. Uses
Demeton is effective against sap-feeding insects and mites. Formulation types EC.
Compatibility Demeton is compatible with most non-alkaline pesticides except water-
soluble mercury compounds.
PRODUCTS:
Discontinued products Isosystox* (demeton-S) (Bayer); Systox* (demeton) (Bayer).
ANALYSIS:
Product analysis by glc (J. G. F. Ernst, J. Chromatogr., 1977, 133, 245) or by alkaline hydrolysis
and titration of the excess of alkali (CIPAC Handbook, 1970, 1, 302) or of the thiol with
iodine (ibid., 1980, 1A, 1198). Residues determined by glc (D. C. Abbott et al., Pestic. Sci.,
1970, 1, 10; A. Ambrus et al., J. Assoc. Off. Anal. Chem., 1981, 64, 733) or by oxidation to
phosphoric acid which is measured by standard colorimetric procedures (D. MacDougall,
Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 2, 451; Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 483). See also Pestic. Anal. Man., I, 302.
JMPR Evaln. 25 (1975), 27 (1976), 43 (1984). PDS 60 (1987). ICSC.861 (demeton mixed
isomers; 2002); ICSC.864 (demeton-O-methyl; 2006).
Oral Demeton: Acute oral LD
50
for male rats 612, female rats 2.54.0 mg/kg. Demeton-O:
Acute oral LD
50
for male rats 30 mg/kg. Demeton-S: Acute oral LD
50
for rats 1.5 mg/
kg. Demeton-S sulfoxide: Acute oral LD
50
for rats 2.3 mg/kg. Demeton-S sulfone: Acute
oral LD
50
for rats 1.9 mg/kg. Skin and eye Acute percutaneous LD
50
for male rats 14 mg
demeton/kg. NOEL (1.83 y) for rats 2 mg/kg diet (0.1 mg/kg daily) (WHO Pestic. Residue
160
demeton-S-methylsulphon
Ser., 1974, 3, 217). ADI/RfD (JMPR) No ADI [1984]; (EPA) cRfD 0.00004 mg/kg b.w.
[1988] (demeton). Toxicity Class WHO (a.i.) IaECClassifcation T+; R27/28| N; R50
(demeton-O and demeton): T+; R27/28 (demeton-S)
ENVIRONMENTAL FATE:
Plants The thioether sulfur of both isomers is oxidised, metabolically, to the sulfoxide and
sulfone (R. B. March et al., J. Econ. Entomol., 1955, 48, 355).
Details PM8, Entry 03910
demeton-O-methyl
Acaricide
IRAC 1B
NOMENCLATURE:
CAS RN [867276] EC no 2127581
6
H
15
O
3
PS
2
APPLICATIONS:
PRODUCTS:
Discontinued products Knock-Out* (Crop Health).
JMPR Evaln. 27 (1976). ICSC.429 (1997).
demeton-S-methylsulphon
IRAC 1B
NOMENCLATURE:
Common name demeton-S-methylsulphon (E-ISO); d(m) ((m) F-ISO); demeton-S-
methyl sulphone (BSI)
IUPAC name S-2-ethylsulfonylethyl O,O-dimethyl phosphorothioate
Chemical Abstracts name S-[2-(ethylsulfonyl)ethyl] O,O-dimethyl phosphorothioate
CAS RN [17040196] EC no 2411095 Development codes Bayer 20 315; E 158;
M3/158 Smiles code CCS(=O)(=O)CCSP(=O)(OC)OC
6
H
15
O
5
PS
2
M.p. 51.6 C B.p. 115 C /0.0075 mmHg; 120 C /0.03 mmHg V.p. 0.056 mPa (20 C)
CH
3
CH
2
SO
2
CH
2
CH
2
S
P(OCH
3
)
2
O
demeton-S-methylsulphon 161
Henry >7.34 10-8 Pa m
3
mol
1
(calc.) S.g./density 1.416 (20 C)
Solubility In water >200 g/l (20 C). Soluble in alcohols, ketones, and most chlorinated
hydrocarbons, e.g. dichloromethane 200 g/l. In toluene 50100 mg/l. Stability Hydrolysed
slowly in acidic media, and rapidly in alkaline media.
COMMERCIALISATION:
History Insecticide introduced by Bayer AG. Patents DE 948241
APPLICATIONS:
acaricide with contact and stomach action. Uses Control of aphids, other sucking insects,
sawfies, and spider mites. Was normally used in combination with azinphos-methyl on fruit,
vines,ornamentals, potatoes, beet, cotton, and vegetables.
PRODUCTS:
Discontinued products Metaisosystoxsulfon* (Bayer).
ANALYSIS:
Product analysis by hydrolysis with alkali, the excess of which is determined by titration
(CIPAC Handbook, 1970, 1, 312). Residues determined by glc (M. C. Bowman et al., J. Assoc.
Off. Anal. Chem., 1969, 52, 157; J. H. van der Merwe & W. B. Taylor, Pfanz.-Nachr. Bayer (Engl.
Ed.), 1971, 24, 259).
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Mtg. 65 (1992);
JMPR Evaln. I 66 (1992); JMPR Evaln. II 58 (1989) EU Status (1107/2009) Not approved,
Oral Acute oral LD
50
for rats 37.5, micec. 30 mg/kg. Skin and eye Acute percutaneous
LD
50
for ratsc. 500 mg/kg. Inhalation LC
50
(4 h) for ratsc. 0.2 mg/l air (aerosol).
NOEL (2 y) for rats 1 mg/kg diet. ADI/RfD (JMPR) 0.0003 mg/kg b.w. for sum of
demeton-S-methyl, demeton-S-methylsulphon and oxydemeton-methyl [1989]. Other
Acute i.p. LD
50
for ratsc. 20.8 mg/kg. Toxicity Class WHO (a.i.) IbECClassifcation T;
R25| Xn; R21| N; R51, R53
ECOTOXICOLOGY:
Fish LC
50
for orfe 102 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, elimination is rapid, and predominantly
in the urine. Plants In plants, metabolism involves oxidation and hydrolysis, giving dimethyl
phosphate and phosphoric acid.
162
desmetryn
2,4-DEP
Herbicide
NOMENCLATURE:
Common name 2,4-DEP (WSSA)
IUPAC name mixture of (i) tris[2-(2,4-dichlorophenoxy)ethyl] phosphite (I) and (ii) bis[2-
(2,4-dichlorophenoxy)ethyl] phosphonate (II)
Chemical Abstracts name (I) + (II) CAS RN [39420343] (i) + (ii); [94848] (i)
Development codes 3Y9
24
H
21
Cl
6
O
6
P (i);
C16H15Cl4O5P (ii)
COMMERCIALISATION:
History Herbicide introduced by Uniroyal Chemical Co., Inc.
PRODUCTS:
Discontinued products Falone* (Uniroyal).
desmetryn
Herbicide
HRAC C1 WSSA 5; 1,3,5-triazine
NOMENCLATURE:
Common name no name (Portugal); desmetryn (BSI (since 1984), E-ISO, WSSA);
desmetryne ((f) F-ISO, JMAF, BSI (before 1984))
IUPAC name N
2
-isopropyl-N4-methyl-6-methylthio-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-methyl-N-(1-methylethyl)-6-(methylthio)-1,3,5-triazine-
2,4-diamine CAS RN [1014693] EC no 2138001 Development codes G 34 360
Smiles code CNc1nc(NC(C)C)nc(SC)n1
PHYSICAL CHEMISTRY:
8
H
15
N
5
S Form White powder. M.p. 84
86 C B.p. 339 C /98.4 kPa V.p. 0.133 mPa (20 C) K
ow
logP = 2.38 Henry 4.8 10
5
Pa
m
3
mol
1
(calc.) S.g./density 1.172 (20 C) Solubility In water 580 mg/l (20 C). Readily
soluble in most organic solvents, e.g. methanol 300, acetone 230, dichloromethane, toluene
200, hexane 2.6 (all in g/kg, 20 C). Stability No signifcant hydrolysis at 70 C detected at
5<pH<13. pKa 4.0, weak base
N N
N CH
3
S NHCH(CH
3
)
2
NHCH
3
desmetryn 163
COMMERCIALISATION:
History Herbicide reported by J. G. Elliott & T. I. Cox (Proc. Br. Weed Control Conf., 6th,
1962, 2, 759). Introduced by J. R. Geigy S.A. (later Novartis Crop Protection AG).
Patents CH 337019; GB 814948 Manufacturers Novartis
APPLICATIONS:
site. Mode of action Selective systemic herbicide, absorbed by the leaves and roots, with
translocation acropetally through the xylem, and accumulation in the apical meristems.
Uses Post-emergence control of fat-hen (Chenopodium album) and other annual
broad-leaved weeds and some grasses at 0.250.5 kg/ha in brassicas (except caulifowers
and broccoli), herbs, onions, leeks, and conifer seedbeds. Formulation types WP.
Compatibility There may be incompatibility with some insecticides.
PRODUCTS:
Discontinued products Semeron* (Novartis).
ANALYSIS:
Product analysis by glc (CIPAC Handbook, 1983, 1B, 1765). Residues determined by glc (K.
Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192).
Oral Acute oral LD
50
LD
50
for rats 2000 mg/kg. Not a skin or eye irritant (rabbits). Not a skin sensitiser when
applied epidermally; skin sensitiser when applied intradermally (guinea pigs). Inhalation
LC
50
(1 h) for rats >1563 mg/m
3
as WP 25. NOEL (90 d) for rats 20 mg/kg diet (1.5 mg/kg
daily); for dogs 200 mg/kg diet (6.6 mg/kg daily). ADI/RfD (BfR) 0.0014 mg/kg b.w. [1993].
Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassifcation Xn; R21/22| N;
R50, R53
ECOTOXICOLOGY:
Birds LC
50
(8 d) for Japanese quail >10 000 mg/kg. Fish LC
50
(96 h) for rainbow trout 2.2,
common carp 37 mg/l. Daphnia LC
50
50
(72 h) for Scenedesmus
subspicatus 0.004 mg/l. Bees Not toxic to bees; LD
50
(oral) >197 g/bee, (topical) >101
g/bee. Worms LC
50
(14 d) for earthworms 160 mg/kg soil.
ENVIRONMENTAL FATE:
Animals Major pathways in animal metabolism are hydrolysis of the methylthio group
to form the hydroxy derivative, sulfoxidation of the methylthio group, and side-chain
dealkylation. Plants Major pathways in plant metabolism are the hydrolysis of the
methylthio group to form the hydroxy derivative, conjugation with glutathione and side-
chain dealkylation. Soil/Environment Degradation involves oxidation of the methylthio
group to sulfoxide and sulfone, hydrolysis with the introduction of a 2-hydroxy group,
dealkylation at the substituted amino groups, cleavage of the amine moiety, and ring
164
dialifos
opening. Duration of residual activity in soil isc. 3 months, DT
50
c. 50 d. K
oc
150, moderately
mobile in soil. Degradation in aquatic systems is caused by microbial processes; desmetryn
is also removed from water by adsorption to the sediment.
dialifos
NOMENCLATURE:
Common name dialifor (ANSI, ESA, JMAF); dialifos (BSI, E-ISO); dialiphos ((m) F-ISO)
IUPAC name S-2-chloro-1-phthalimidoethyl O,O-diethyl phosphorodithioate; N-[2-chloro-
1-(diethoxyphosphinothioylthio)ethyl]phthalimide
Chemical Abstracts name S-[2-chloro-1-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)
ethyl] O,O-diethyl phosphorodithioate CAS RN [10311849] EC no 2336893
Development codes Hercules 14503 Smiles code CCOP(=S)(OCC)SC(CCl)N1C(=O)
c2ccccc2C1=O
14
H
17
ClNO
4
PS
2
Form Colourless
crystals. M.p. 6769 C V.p. 133 mPa (35 C) Solubility Practically insoluble in water
(<1 mg/l). In acetone 760, isophorone 400, chloroform 620, xylene 570, diethyl ether 500,
ethanol <10, hexane <10 (all in g/kg, 20 C). Stability Tech. is hydrolysed in alkaline media,
DT
50
2.5 h (pH 8, room temperature).
COMMERCIALISATION:
History Insecticide reported by W. R. Cothran et al. (J. Econ. Entomol., 1967, 60, 1151).
Introduced by Hercules Inc. (later Nor-Am Chemical Co.). Patents GB 1091738; US
3355353
APPLICATIONS:
acaricide with contact, stomach, and respiratory action. Uses Control of chewing and
sucking insects and spider mites on potatoes, vegetables, pome fruit, stone fruit, citrus fruit,
vines, nut trees, cotton, beet, oilseed rape, and roses. Formulation types EC.
PRODUCTS:
Discontinued products Torak* (AgrEvo, Cyanamid).
ANALYSIS:
Product by glc and uv spectrophotometry. Residues by GLC with phosphorus-specifc TID
(M. A. Luke et al., J. Assoc. Off. Anal. Chem. 1981, 64, 1187).
S
P(OCH
2
CH
3
)
2
S
N
CH
CH
2
Cl
O
O
di-allate 165
JMPR Evaln. I 45 (1985); JMPR Evaln. 27 (1976). EU Status (1107/2009) Not approved,
Oral Acute oral LD
50
for male rats 4353, female rats 5, male mice 39, female mice 65,
rabbits 5871, male dogs 97 mg/kg. Skin and eye Acute percutaneous LD
50
for rabbits 145
mg/kg. Mild skin and eye irritant (rabbits). NOEL In 90 d feeding trials, rats receiving 10
mg/kg diet showed inhibition of plasma and erythrocyte cholinesterases.
ADI/RfD (JMPR) ADI withdrawn (1982). Toxicity Class WHO (a.i.) II EPA (formulation) I
ECClassifcation T+; R28| T; R24| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks 940 mg/kg. Fish LC
50
(24 h) for rainbow trout
0.551.08 mg/l. Bees Low toxicity to honeybees, LD
50
0.0340.038 mg/bee.
di-allate
Herbicide
NOMENCLATURE:
Common name di-allate (BSI, E-ISO); diallate ((m) F-ISO, WSSA)
IUPAC name S-2,3-dichloroallyl diisopropylthiocarbamate
Chemical Abstracts name S-(2,3-dichloro-2-propenyl) bis(1-methylethyl)
carbamothioate CAS RN [2303164] EC no 2189611 Development codes CP 15
336 (Monsanto) Smiles code CC(C)N(C(C)C)C(=O)SCC(=CCl)Cl
PHYSICAL CHEMISTRY:
Composition It exists as geometric isomers which have been separated (F. H. A.
Rummens, Weed Sci., 1975, 23, 7). Mol. wt. 270.2 M.f. C
10
H
17
Cl
2
NOS Form Amber-
coloured liquid. M.p. 2530 C; <0 C ((Z)- isomer); 36 C ((E)- isomer) B.p. 97 C /0.15
mmHg V.p. 20 mPa (25 C) K
ow
logP = 3.29 (Agchem. Desk Ref.) Henry 3.86 10
1
Pa m
3
mol
1
(calc.) S.g./density 1.188 (25 C) Solubility In water 14 mg/l (25 C). Miscible with
acetone, ethanol, ethyl acetate, kerosene, isopropanol, xylene. Stability Stable to uv light;
decomposes >200 C. Stable to hydrolysis.
COMMERCIALISATION:
History Herbicide reported by L. H. Hannah (Proc. North Cent. Weed Control Conf., 1959, p.
50). Introduced by Monsanto Co. Patents US 3330643; US 3330821
APPLICATIONS:
Biochemistry Inhibits lipid metabolism. Mode of action Selective herbicide. It is
absorbed by the emerging wild oat coleoptile, toxicity being mainly at cell division. Uses A
pre- or post-planting incorporated herbicide which controls wild oats in barley, fax, forage
legumes, lentils, maize, peas, potatoes, soya beans and sugar beet. The (E)- isomer is less
effective than the (Z)- isomer in reducing height of wild oats (F. H. A. Rummens et al., Weed
166
diamidafos
Sci., 1975, 23, 11). Formulation types EC; GR .
PRODUCTS:
Discontinued products Avadex* (Monsanto); Discontinued mixtures Pyradex*
(+ chloridazon) (BASF).
ANALYSIS:
Product analysis by glc. Residues determined by glc.
EHC 76 (1988); a general review of thiocarbamates. IARC 30 (1983). EU Status
(1107/2009) Not approved, Commission Regulation 2076/2002.
IARC Class 3
Oral Acute oral LD
50
for rats 395, dogs 510 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits 20002500 mg/kg. Moderate irritant to skin and eyes (rabbits). NOEL
In 90 d feeding trials, rats receiving 400 mg/kg diet suffered weight loss, irritability,
hyperactivity and mild cardiac changes; but no death occurred at 1200 mg/kg diet. In beagle
dogs, adverse effects were observed at 600, but not at 125 mg/day. ADI/RfD (EPA) 0.005
mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) IIECClassifcation Xn; R22| R40| N; R50,
R53
ENVIRONMENTAL FATE:
Soil/Environment It competes with moisture for adsorption on soil; loss is mainly by
microbial breakdown, DT
50
30 d, provided it is fully incorporated in the soil.
diamidafos
IRAC 1B
NOMENCLATURE:
Common name diamidafos (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name phenyl N,N-dimethylphosphorodiamidate (I)
Chemical Abstracts name (I) CAS RN [1754581] Development codes Dowco
169 Smiles code CNP(=O)(NC)Oc1ccccc1
8
H
13
N
2
O
2
P
COMMERCIALISATION:
History Nematicide reported by C. R. Youngson & C. A. I. Goring (Down Earth, 1963,
18(4), 3). Introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
PRODUCTS:
Discontinued products Nellite* (DowElanco).
1,2-dibromo-3-chloropropane 167
diammonium ethylenebis(dithiocarbamate)
Fungicide
multi-site: alkylenebis(dithiocarbamate)
NOMENCLATURE:
IUPAC name diammonium ethylenebis(dithiocarbamate)
Chemical Abstracts name diammonium 1,2-ethanediylbis[carbamodithioate] Other
names amobam; amobam T (for the di-trolamine (bis-triethanolammonium) salt)
CAS RN [3566107]; [33233066] di-trolamine salt
Smiles code [S-]C(=S)NCCNC(=S)[S-].[NH4+].[NH4+]
4
H
14
N
4
S
4
M.p. 72.572.8 C
Solubility Soluble in water. Insoluble in xylene.
COMMERCIALISATION:
History Fungicide related to nabam and other dithiocarbamates. Manufactured and sold
principally in China.
APPLICATIONS:
Biochemistry Non-specifc thiol reactant, inhibiting respiration. Mode of action Broad
spectrum fungicide with protectant and curative action. Uses For control of spot disease,
anthracnose and mildew, on various crops such as rice, rubber, millet, sweet potato,
cucumber, cabbage and maize. Formulation types SL .
PRODUCTS:
Discontinued products Amobam* (Fike); Chem-O-Bam* (Tifa).
JMPR Mtg. 68 (1993); JMPR Evaln. I 69 (1993); JMPR Evaln. II 70 (1993) for metabolite
ethylenethiourea.
1,2-dibromo-3-chloropropane
Nematicide
NOMENCLATURE:
Common name DBCP (JMAF)
IUPAC name 1,2-dibromo-3-chloropropane (I)
CH
2
CH
2
C
NH S
S
C
NH
S
S
NH
4
NH
4
168
dibutyl adipate
Development codes OS1897 (Shell) Smiles code ClCC(Br)CBr
3
H
5
Br
2
Cl Form Amber to dark brown
liquid, with a mildly pungent odour. B.p. 196 C V.p. 1.07 10
5
mPa (21 C)
K
ow
logP = 2.63 (Agchem. Desk Ref.) Henry 2.53 101 Pa m
3
mol
1
2.08 (20 C) Solubility In water 1g/kg (room temperature). Miscible with hydrocarbon
oils, acetone, iso-propanol, methanol, 1,3-dichloropropane and 1,1,2-trichlorethane.
Stability Stable in neutral and acidic media; converted to 2-bromoallyl alcohol in alkali.
COMMERCIALISATION:
History Nematicidal activity reported by C. W. McBeth & G. B. Bergeson (Plant Dis.
Rep., 1955, 39, 223). Introduced by Dow Chemical Co. (later DowElanco) and Shell
Development Co.
APPLICATIONS: Uses Soil fumigant and nematicide, effective against a wide range
of nematodes, including root-knot nematodes, at 10125 kg/ha. Phytotoxicity Many
perennial plants tolerate high concentrations, but others, including potatoes and tobacco,
require a long aeration period before planting.
PRODUCTS:
Discontinued products Fumazone* (Dow); Nemagon* (Shell).
ANALYSIS:
Residues in drinking water by glc with linearised ECD (AOAC Methods, 18th Ed., 993.15).
ICSC.002 (2002). IARC 20 (1979); Suppl. 7 (1987); 71 (1999).
IARC Class 2B
Oral Acute oral LD
50
for rats 170300, mice 260400 mg/kg. Water GV 0.001 mg/l (see
note on carcinogens). Other Causes sterility in humans and is mutagenic and carcinogenic
in animals. Toxicity Class WHO (a.i.) IaECClassifcation R45; R46; R60| T; R25| Xn;
R48/20/22| R52, R53
ENVIRONMENTAL FATE:
Soil/Environment Does not persist is soil to the extent that it presents an accumulation
problem.
dibutyl adipate
Insect repellent
NOMENCLATURE:
IUPAC name dibutyl adipate
Chemical Abstracts name dibutyl hexanedioate CAS RN [105997]
Development codes Experimental Tick Repellent 3 Smiles code CCCCOC(=O)
CCCCC(=O)OCCCC
dibutyl succinate 169
14
H
26
O
4
COMMERCIALISATION:
History Insect repellent introduced by Union Carbide Corp. (later Rhne-Poulenc
Agrochimie).
dibutyl phthalate
Insect repellent
NOMENCLATURE:
Common name dibutyl phthalate (BSI, E-ISO); phtalate de butyle (F-ISO); ()
IUPAC name dibutyl phthalate
Chemical Abstracts name dibutyl 1,2-benzenedicarboxylate Other names DBP
CAS RN [84742] Smiles code CCCCOC(=O)c1ccccc1C(=O)OCCCC
16
H
22
O
4
COMMERCIALISATION:
History Activity as insect repellent reported by F. M. Snyder & F. A. Morton (J. Econ.
Entomol., 1947, 40, 586).
EHC 189 (1997). ICSC.036 (2002).
dibutyl succinate
Insect repellent
NOMENCLATURE:
IUPAC name dibutyl succinate
Chemical Abstracts name dibutyl butanedioate CAS RN [141037]
Smiles code CCCCOC(=O)CCC(=O)OCCCC
12
H
22
O
4
COMMERCIALISATION:
History Insect repellent introduced by Glenn Chemical Co.
PRODUCTS:
Discontinued products Tabatrex* (Glenn); Tabutrex* (Glenn).
170
dicapthon
dicamba-methyl
NOMENCLATURE:
Common name disugran (ANSI); dicamba-methyl (BSI, E-ISO, (m) F-ISO)
IUPAC name methyl 3,6-dichloro-o-anisate
Chemical Abstracts name methyl 3,6-dichloro-2-methoxybenzoate CAS RN [6597
780] Smiles code COC(=O)c1c(Cl)ccc(Cl)c1OC
9
H
8
Cl
2
O
3
COMMERCIALISATION:
History Plant growth regulator introduced by Velsicol Chemical Co. (later Sandoz AG).
PRODUCTS:
Discontinued products Racuza* (Sandoz).
dicapthon
Insecticide
IRAC 1B
NOMENCLATURE:
Common name dicapthon (ESA, ex-ANSI)
CAS RN [2463845] Development codes AC 4124 Smiles code COP(=S)(OC)
Oc1ccc(cc1Cl)[N+](=O)[O-]
8
H
9
ClNO
5
PS
COMMERCIALISATION:
History Insecticide reported by T. B. Davich & J. W. Apple (J. Econ. Entomol., 1951, 44, 528)
and by J. C. Gaines (ibid., p. 750). Introduced by American Cyanamid Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Dicapton* (Cyanamid).
dichlone 171
dichlone
Algicide, fungicide
NOMENCLATURE:
Common name dichlone (BSI, E-ISO, (m) F-ISO, JMAF)
IUPAC name 2,3-dichloro-1,4-naphthoquinone
Chemical Abstracts name 2,3-dichloro-1,4-naphthalenedione CAS RN [117
806] EC no 2042105 Development codes USR 604 (to Uniroyal)
Smiles code ClC1=C(Cl)C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY:
10
H
4
Cl
2
O
2
M.p. 193 C (subliming >32 C); tech., 188 C B.p. 275 C /2 mmHg V.p. 0.01 mPa (ARS
PPD) K
ow
logP = 5.62 (Agchem. Desk Ref.) Solubility In water 0.1 mg/l (25 C). In xylene
and 1,2-dichlorobenzene,c. 4%. Moderately soluble in acetone, diethyl ether, benzene,
ethyl acetate, acetic acid, DMF, and dioxane. Sparingly soluble in alcohols. Stability In the
dry state, stable to light and heat. In solution, slowly decomposed by light. Stable in acidic
media, but hydrolysed by alkalis.
COMMERCIALISATION:
History Fungicidal properties of this established chemical reported by W. P. ter Horst &
E. L. Felix (Ind. Eng. Chem., 1943, 35, 1255). Introduced by Uniroyal Chemical Co., Inc. and
by FMC Corp. Patents US 2302384; US 2349772 (to Uniroyal) Manufacturers Zhejiang
Heyi
APPLICATIONS:
Mode of action Foliar fungicide with protective action. Uses Fungicidal control in fruit,
vegetables, ornamentals, and feld crops. Particular uses included control of blossom blights,
scab on apples and pears, and brown rot of stone fruit. Also used to control blue-green
Algae in ponds, lakes, and swimming pools. Formulation types WP. Compatibility
Incompatible with petroleum oils, dinitro compounds, organomercury compounds, calcium
arsenate, lime sulfur, Bordeaux mixture, nicotine, and emulsifable concentrate formulations.
PRODUCTS:
Discontinued products Kolo* (FMC); Phygon* (Uniroyal).
ANALYSIS:
Product analysis by colorimetry after alkaline hydrolysis to the sodium salt of 2-chloro-
3-hydroxy-1,4-naphthoquinone (D. K. Gullstrom & H. P. Burchfeld, Anal. Chem., 1948, 20,
1174; J. R. Lane, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 141). Residues
O
O
Cl
Cl
172
dichlorfurenol; dichlorfurenol-methyl
determined by glc (Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 584) or by colorimetry
(AOAC Methods, 18th Ed., 965.36).
Oral Acute oral LD
50
50
for
rabbits 5000 mg/kg. Irritating to skin under warm conditions. NOEL In 2 y feeding trials,
rats receiving 1500 mg/kg diet showed no ill-effects. ADI/RfD (EPA) 0.08 mg/kg b.w.
[1989]. Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22| Xi; R36/38| N; R50,
R53
ECOTOXICOLOGY:
Fish LC
50
(48 h) for brown trout 0.31 mg/l. Daphnia LC
50
0.014 mg/l. Bees Not toxic to
bees.
ENVIRONMENTAL FATE:
Plants In plant cells, both chlorine atoms are replaced by sulfhydryl groups to give a
substituted dimercapto compound.
dichloralurea
Herbicide
NOMENCLATURE:
Common name DCU (WSSA); dichloralurea (BSI, E-ISO); dichloralur(e) (F-ISO); are
accepted in lieu of a common name
IUPAC name 1,3-bis(2,2,2-trichloro-1-hydroxyethyl)urea
Chemical Abstracts name N,N-bis(2,2,2-trichloro-1-hydroxyethyl)urea
CAS RN [116529] Development codes Crag Herbicide 2
Smiles code OC(NC(=O)NC(O)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl
5
H
6
Cl
6
N
2
O
3
COMMERCIALISATION:
History Herbicide introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
PRODUCTS:
Discontinued products Crag Herbicide 2* (Union Carbide).
dichlorfurenol; dichlorfurenol-methyl
NOMENCLATURE:
Common name dichlorfurenol (BSI from 1990, E-ISO); dichlorofur(nol) ((m) F-ISO);
dichlorfurecol* (BSI until 1990, Canada)
1,3-dichloro-1,1,3,3-tetrafuoroacetone hydrate 173
IUPAC name 2,7-dichloro-9-hydroxyfuorene-9-carboxylic acid
Chemical Abstracts name 2,7-dichloro-9-hydroxy-9H-fuorene-9-carboxylic acid
CAS RN [21634968] dichlorfurenol-methyl Development codes IT-5733
PHYSICAL CHEMISTRY:
Composition Dichlorfurenol-methyl is present as a minor component of tech.
chlorfurenol-methyl (q.v.). Mol. wt. 295.1; (methyl ester 309.2) M.f. C
14
H
8
Cl
2
O
3
; (methyl
ester C15H
10
Cl
2
O3)
COMMERCIALISATION:
History Dichlorfurenol-methyl introduced as a plant growth regulator by E. Merck (later
Shell Agrar GmbH).
dichlormate
Herbicide
NOMENCLATURE:
Common name dichlormate (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 3,4-dichlorobenzyl methylcarbamate
Chemical Abstracts name (3,4-dichlorophenyl)methyl methylcarbamate
CAS RN [1966581] dichlormate; [62046371] tech. grade containing 2,3-dichloro-
analogue Development codes UC 22 463A (pure dichlormate); UC 22 463 (TC grade)
Smiles code CNC(=O)OCc1ccc(Cl)c(Cl)c1
9
H
9
Cl
2
NO
2
COMMERCIALISATION:
History Herbicide reported by R. A. Herrett & R. V. Berthold (Science, 1965, 149, 191).
Introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.).
PRODUCTS:
Discontinued products Rowmate* (Union Carbide).
1,3-dichloro-1,1,3,3-tetrafuoroacetone hydrate
Fungicide
NOMENCLATURE:
IUPAC name 1,3-dichloro-1,1,3,3-tetrafuoropropane-2,2-diol (i); 1,3-dichloro-1,1,3,3,-
tetrafuoroacetone hydrate (ii)
Chemical Abstracts name 1,3-dichloro-1,1,3,3-tetrafuoro-2,2-propanediol (i);
1,3-dichloro-1,1,3,3-tetrafuoro-2-propanone hydrate (ii) CAS RN [993588] (i);
[127219] (ii) Development codes GC 9832
174
1,1-dichloro-2,2-bis(4-ethylphenyl)ethane
3
H
2
Cl
2
F
4
O
2
COMMERCIALISATION:
History Fungicide reported by D. W. George (Plant Dis. Rep., 1964, 48, 162). Introduced by
Allied Chemical Corp.
1,1-dichloro-1-nitroethane
Insecticide
NOMENCLATURE:
IUPAC name 1,1-dichloro-1-nitroethane (I)
Smiles code CC(Cl)(Cl)[N+](=O)[O-]
2
H
3
Cl
2
NO
2
COMMERCIALISATION:
History Insecticidal activity reported by W. C. OKane & H. W. Smith (J. Econ. Entomol.,
1941, 34, 438). Introduced by Commercial Solvents Corp.
APPLICATIONS:
PRODUCTS:
Discontinued products Ethide* (Commercial Solvents).
Oral Acute oral LD
50
for rats 410 mg/kg (Shibuya). ECClassifcation T; R23/24/25
1,1-dichloro-2,2-bis(4-ethylphenyl)ethane
Insecticide
NOMENCLATURE:
IUPAC name 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane
Chemical Abstracts name 1,1-(2,2-dichloroethylidene)bis[4-ethylbenzene]
Other names ethylan CAS RN [72560] Development codes Q-137 (Rohm &
Haas); Bayer 63138 Smiles code CCc1ccc(cc1)C(C(Cl)Cl)c2ccc(CC)cc2
18
H
20
Cl
2
Form Crystalline solid; (tech.
is a wax). M.p. 6061 C; (tech., 40 C) Solubility Practically insoluble in water. Soluble
in most aromatic solvents and in dichloromethane.
COMMERCIALISATION:
History Insecticide introduced by Rohm & Haas Co. Patents US 2464000, US 2881111,
US 2883428.
2,4-dichlorophenyl benzenesulfonate 175
APPLICATIONS:
Mode of action Non-systemic insecticide with useful specifcity. Uses For control of pear
psylla, and use against leafhoppers and various larvae on vegetable crops, at 116 kg/ha.
Also used domestically for the control of clothes moth and carpet beetles.
PRODUCTS:
Discontinued products Perthane* (Rohm & Haas).
ANALYSIS:
Residues determined by glc, tlc or paper chromatography (AOAC Methods 18th Ed., 970.52)
or by glc with ECD of a dehydrochlorinated derivative (ibid., 973.39). See also Pestic. Anal.
Man., I, 303, 304.
ENVIRONMENTAL FATE:
Soil/Environment Moderately persistent in soil.
O-2,5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name O-2,5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate
Chemical Abstracts name O-(2,5-dichloro-4-iodophenyl) O-ethyl
ethylphosphonothioate CAS RN [25177279] Development codes C 18 244
Smiles code CCOP(=S)(CC)Oc1cc(Cl)c(I)cc1Cl
10
H
12
Cl
2
IO
2
PS
COMMERCIALISATION:
History Insecticide introduced by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
2,4-dichlorophenyl benzenesulfonate
Acaricide
NOMENCLATURE:
IUPAC name 2,4-dichlorophenyl benzenesulfonate (I)
Chemical Abstracts name (I) Other names DCPBS CAS RN [97165]
Development codes EM-923; GC-923 Smiles code Clc1ccc(OS(=O)(=O)c2ccccc2)
c(Cl)c1
12
H
8
Cl
2
O
3
S
176
N-3,5-dichlorophenylsuccinimide
COMMERCIALISATION:
History Acaricide introduced by Allied Chemical Corp., Agrochemical Division (later
Hopkins Agricultural Chemical Co.).
PRODUCTS:
Discontinued products Genite* (Allied); Genitol* (Allied).
(RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)succinimide
Fungicide
NOMENCLATURE:
IUPAC name (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)succinimide
Chemical Abstracts name ()-1-(3,5-dichlorophenyl)-3-(methoxymethyl)-2,5-
pyrrolidinedione Other names metomeclan* (unadopted proposed common name)
CAS RN [81949884] Development codes Co 6054
Smiles code COCC1CC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
12
H
11
Cl
2
NO
3
COMMERCIALISATION:
History Fungicide evaluated by Wacker-Chemie GmbH.
PRODUCTS:
Discontinued products Drawifol* (Wacker).
N-3,5-dichlorophenylsuccinimide
Fungicide
NOMENCLATURE:
IUPAC name N-3,5-dichlorophenylsuccinimide
Chemical Abstracts name 1-(3,5-dichlorophenyl)-2,5-pyrrolidinedione
CAS RN [24096535] Development codes S-47127
Smiles code Clc1cc(Cl)cc(c1)N
2
C(=O)CCC2=O
10
H
7
Cl
2
NO
2
COMMERCIALISATION:
History Fungicide introduced by Sumitomo Chemical Co., Ltd.
PRODUCTS:
Discontinued products Ohric* (Sumitomo Chemical).
1,2-dichloropropane with 1,3-dichloropropene 177
1,2-dichloropropane
Insecticide
NOMENCLATURE:
IUPAC name 1,2-dichloropropane (I)
Chemical Abstracts name (I) Other names propylene dichloride; PDC
CAS RN [78875] EC no 2011522 Smiles code CC(Cl)CCl
3
H
6
Cl
2
M.p. Freezes 70 C B.p. 95.4 C V.p. 2.79 107 mPa (19.6 C) K
ow
logP = 2.28 (Agchem.
Desk Ref.) Henry 1.17 103 Pa m
3
mol
1
Solubility In water 2.7 g/kg (20 C). Miscible with ethanol, diethyl ether. Stability Stable
at pH 7 (25 C) (Agchem. Desk Ref.) F.p. 21 C (Cleveland open cup)
COMMERCIALISATION:
History Its properties as an insecticidal fungicide were described by I. E. Neifert et al. (U.S.
Dep. Agric. Bull., 1925, No. 1313).
APPLICATIONS:
Mode of action Fumigant insecticide. Uses Used in mixture with 1,3-dichloropropene.
Although far less toxic to nematodes (C. R. Youngston & C. I. A. Goring, Plant Dis. Rep., 1970,
54, 196; M. V. McKenry & I. J. Thomason, Hilgardia, 1974, 42, 422) it moves more freely in
soil, from which the greatest loss is by volatilisation (T. R. Roberts & G. Stoydin, Pestic. Sci.,
1976, 7, 325).
ANALYSIS:
Product and residue analysis is by glc. Methods reviewed by J L Daft in Comp. Anal.
Profles,Chapter 11.
EHC 146 (1993). HSG 76 (1992). IARC 41 (1986); 71 (1999). EU Status (1107/2009) Not
approved, Commission Regulation 2076/2002.
IARC Class 3
Inhalation It is strongly narcotic but low concentrations cause an irritation of the
respiratory tract. Exposure of guinea-pigs, rabbits and rats to the vapour has been studied
(L. A. Heppel et al., J. Ind. Hyg. Toxicol., 1946, 28, 1). Water GV 0.04 mg/l (provisional).
Toxicity Class WHO (a.i.) FMECClassifcation F; R11| Xn; R20/22
1,2-dichloropropane with 1,3-dichloropropene
NOMENCLATURE:
IUPAC name 1,2-dichloropropane + 1,3-dichloropropene
Chemical Abstracts name 1,2-dichloropropane + 1,3-dichloro-1-propene
178
1,2-dichloropropane with 1,3-dichloropropene
CAS RN [8003198] mixture; [78875] 1,2-dichloropropane; [54275
6] 1,3-dichloropropene Smiles code CC(Cl)CCl.ClC/C=C/Cl;without
stereochemistry:CC(Cl)CCl.ClCC=CCl
PHYSICAL CHEMISTRY:
Composition A mixture of chlorinated hydrocarbons containing 50% m/m (E)- and
(Z)-1,3-dichloropropenes, the other main constituent being 1,2-dichloropropane. It has an
organic chlorine content of 55.0% m/m.
Form Clear amber liquid, with a pungent odour. B.p. Flash distils 59115 C V.p. 4.6
10{6} mPa (20 C) S.g./density 1.171.22 (20 C) Solubility In water c. 2 g/kg
(room temperature). Fully miscible with esters, halogenated solvents, hydrocarbons and
ketones. Stability The mixture is stable at 500 C but reacts with dilute organic bases,
concentrated acids, halogens and some metal salts. F.p. 17.5 C (Abel closed cup)
COMMERCIALISATION:
History Properties as a soil fumigant described by W. Carter (Science, 1943, 97,
383). Introduced by Shell Chemical Co. and by Dow Chemical Co., later replaced by
1,3-dichloropropene.
APPLICATIONS:
Mode of action Fumigant insecticide and nematicide. Uses The mixture is a pre-plant
nematicide effective against soil nematodes including root knot, meadow, sting and dagger,
spiral and sugar beet nematodes. Because the components are highly phytotoxic, a 7-d pre-
planting interval was allowed for every 75 l applied/ha.
PRODUCTS:
Discontinued products DD* (Shell); Vidden D* (Dow).
ANALYSIS:
Product and residue analysis is by glc (T. R. Roberts & G. Stoydin, Pestic. Sci., 1976, 7, 325;
C. E. Castro, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 151; Anal. Methods
Pestic. Plant Growth Regul., 1972, 6, 710). Methods reviewed by J L Daft in Comp. Anal.
Profles,Chapter 11.
EHC 146 (1993). HSG 76 (1992). EFSA Sci. Rep. (2006) 72, 199. IARC 41 (1986); 71
(1999). EU Status (1107/2009) 1,3-dichloropropene not included, 2007/619/EC.
1,2-dichloropropane and the (Z)-isomer of 1,3-dichloropropene not included, Commission
Oral Acute oral LD
50
percutaneous LD
50
for rats 779, rabbits 2100 mg/kg. Extremely irritating to the skin and a
severe eye irritant. Also a moderate skin sensitiser. NOEL In 2 y feeding trials, no effects
related to the product were observed in rats receiving 120 mg product/kg diet. Water
GV See individual data for the components.
2,2-dichlorovinyl 2-ethylsulfnylethyl methyl phosphate 179
ENVIRONMENTAL FATE:
Soil/Environment It does not accumulate in the soil (M. V. McKenry & I. J. Thomason,
Hilgardia, 1974, 42, 393; T. R. Roberts & G. Stoydin, Pestic. Sci., 1976, 7, 325); and has no
permanent harmful effect on soil micro-organisms.
3,4-dichlorotetrahydrothiophene 1,1-dioxide
Nematicide
NOMENCLATURE:
IUPAC name 3,4-dichlorotetrahydrothiophene 1,1-dioxide (I)
Chemical Abstracts name (I) Other names dichlorothiolane dioxide
CAS RN [3001578] Smiles code ClC1CS(=O)(=O)CC1Cl
4
H
6
Cl
2
O
2
S
COMMERCIALISATION:
History Nematicide introduced by Diamond Shamrock Chemical Co. (later Fermenta).
PRODUCTS:
Discontinued products PRD Experimental Nematicide* (Fermenta).
2,2-dichlorovinyl 2-ethylsulfnylethyl methyl phosphate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name 2,2-dichlorovinyl 2-ethylsulfnylethyl methyl phosphate
Chemical Abstracts name 2,2-dichloroethenyl 2-(ethylsulfnyl)ethyl methyl phosphate
CAS RN [7076531] Development codes Nexion 1378 Smiles code CCS(=O)
CCOP(=O)(OC)OC=C(Cl)Cl
7
H
13
Cl
2
O
5
PS
COMMERCIALISATION:
History Insecticide introduced by Celamerck GmbH & Co. (later Shell Agrar GmbH).
APPLICATIONS:
ECClassifcation T; R23/24/25
180
diclobutrazol
dichlozoline
Fungicide
NOMENCLATURE:
Common name dichlozoline (BSI, E-ISO, (f) F-ISO, JMAF, ex ANSI)
IUPAC name 3-(3,5-dichlorophenyl)-5,5-dimethyl-1,3-oxazolidine-2,4-dione
Chemical Abstracts name 3-(3,5-dichlorophenyl)-5,5-dimethyl-2,4-oxazolidinedione
Other names DDOD CAS RN [24201589] Development codes CS 8890;
Ortho 8890 Smiles code CC1(C)OC(=O)N(C1=O)c2ccc(Cl)c(Cl)c2
11
H
9
Cl
2
NO
3
COMMERCIALISATION:
History Fungicide evaluated by Chevron Chemical Company LLC.
PRODUCTS:
Discontinued products Sclex* (Sumitomo Chemical).
diclobutrazol
Fungicide
NOMENCLATURE:
Common name diclobutrazol (BSI, E-ISO, (m) F-ISO)
IUPAC name (2RS,3RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)
pentan-3-ol
Chemical Abstracts name (R*,R*)-()--[(2,4-dichlorophenyl)methyl]--(1,1-
dimethylethyl)-1H-1,2,4-triazole-1-ethanol CAS RN [75736333] diclobutrazol;
[66345628] unstated stereochemistry EC no 2663241 unstated stereochemistry
Development codes PP296 Smiles code CC(C)(C)C(O)C(Cc1ccc(Cl)cc1Cl)n2cncn2
15
H
19
Cl
2
N
3
O Form Off-white
crystalline solid. M.p. 147149 C V.p. 0.0027 mPa (20 C) K
ow
logP = 3.81
Henry 1.25 10
4
Pa m
3
mol
1
(calc.) S.g./density 1.25 Solubility In water 7.1 mg/l
H
C
OH
CH
N
N
N
C(CH
3
)
3
CH
2
Cl
Cl
diclobutrazol 181
(pH 7, room temperature). In acetone, methanol, ethanol, chloroform <50 g/l. Moderately
soluble in DMF, cyclohexanone, monobutyl ether, and glycol ethers. Slightly soluble in
xylene. Stability Stable to acids and alkalis (pH 414). Also stable to heat (>90 d, 50 C),
air, sunlight, and moisture. pKa Basic, pKa <2
COMMERCIALISATION:
History Fungicide reported by K. J. Bent & A. M. Skidmore (Proc. Br. Crop Prot. Conf. - Pests
Dis., 1979, 2, 477). Introduced by ICI Agrochemicals (became Syngenta AG). Patents GB
1595698
APPLICATIONS:
Biochemistry Sterol demethylation (ergosterol biosynthesis) inhibitor.
Mode of action Systemic fungicide with curative and protective action. Translocated
within the plant predominantly acropetally. Also exhibits vapour action. Uses Control of
rusts on cereals and coffee; and powdery mildews on cereals, vines, apples, and cucurbits.
Phytotoxicity Should not be used on solanaceous crops. Formulation types SC.
PRODUCTS:
Discontinued products Vigil* (Zeneca); Discontinued mixtures Sopraphal*
(+ prochloraz) (Syngenta).
ANALYSIS:
Residues in crops determined by glc with ECD (Pestic. Anal. Man., I, 302).
Oral Acute oral LD
50
for rats 4000, mice >1000, guinea pigs 4000, rabbits 4000 mg/kg.
50
for rats and rabbits >1000 mg/kg. Mild skin and
eye irritant (rabbits). Not a skin sensitiser. NOEL (90 d) for rats 2.5 mg/kg daily; (6 mo)
for dogs 15 mg/kg daily. Other Acute i.p. LD
50
for ratsc. 500 mg/kg. Toxicity Class WHO
(a.i.) UECClassifcation Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks >9461 mg/kg. Fish LC
50
23.9 mg/l, (48 h) 15.1 mg/l, (96 h) 9.6 mg/l. Daphnia LC
50
(48 h) 9.3 mg/l. Bees LD
50
(oral
and contact) 0.05 mg/bee. Worms No adverse effect on earthworm populations 30245
d after application of sprays at 0.2 and 2.0 kg/ha. Otherbenefcial No adverse effect on
soil microarthropods 30245 d after application of sprays at 0.2 and 2.0 kg/ha.
ENVIRONMENTAL FATE:
Soil/Environment In straw, DT
50
c. 1 week.
182
diclomezine
diclomezine
Fungicide
FRAC 37, U; pyridazinone fungicide
NOMENCLATURE:
Common name diclom(zine) ((f) F-ISO); diclomezine (BSI, E-ISO)
IUPAC name 6-(3,5-dichloro-4-methylphenyl)pyridazin-3(2H)-one
Chemical Abstracts name 6-(3,5-dichloro-4-methylphenyl)-3(2H)-pyridazinone
CAS RN [62865365] Development codes F-850 (Sankyo); SF-7531 (Sankyo)
Smiles code Cc1c(Cl)cc(cc1Cl)c2ccc(=O)[nH]n2
11
H
8
Cl
2
N
2
M.p. 250.5253.5 C V.p. <1.3 10-2 mPa (60 C) Solubility In water 0.74 mg/l (25 C).
In methanol 2.0, acetone 3.4 (both in g/l, 23 C). Stability Slowly decomposed by sunlight.
Stable under acidic, neutral, and alkaline conditions.
COMMERCIALISATION:
History Fungicide reported by Y. Takahi (Jpn. Pestic. Inf., 1988, No. 52, p. 31). Introduced
in Japan (1988) by Sankyo Co., Ltd (agrochemicals interests now Mitsui Chemicals Inc.).
Patents US 4052395; GB 1533010; JP 1170243 Manufacturers Mitsui Chemicals Agro;
Sankyo Agro
APPLICATIONS:
Mode of action Fungicide with curative and protective action. Inhibits septum formation
and mycelial growth. Uses Control of Rhizoctonia and Sclerotium spp. in rice; white
mould and twig rot on peanuts; and Rhizoctonia disease of turf. Applied at 360480 g/ha.
Formulation types DP; SC. WP.
PRODUCTS:
Other mixtures Rabu-Monguard-Jorker (+ phthalide + silafuofen) (Hokko);
Discontinued products Monguard* (Sankyo Agro).
ANALYSIS:
Product analysis by hplc. Residues determined by glc of a derivative.
Oral Acute oral LD
50
for rats >12 000 mg/kg. Skin and eye Acute percutaneous LD
50
for
rats >5000 mg/kg. Not a skin irritant. Inhalation LC
50
(4 h) for rats 0.82 mg/l.
NOEL (2 y) for male rats 98.9, female rats 99.5 mg/kg daily. Other Non-mutagenic and
non-teratogenic. Toxicity Class WHO (a.i.) U.
CH
3
Cl
Cl
N N
O
H
dicyclonon 183
ECOTOXICOLOGY:
Birds Dietary LC
50
for bobwhite quail and mallard ducks >7000 ppm. Dietary LD
50
for
bobwhite quail >3000 mg/kg. Fish LC
50
(48 h) for carp >300 mg/l. Daphnia LC
50
(5 h)
>300 mg/l. Bees LD
50
(oral and contact) for honeybees >100 g/bee.
ENVIRONMENTAL FATE:
Soil/Environment Readily adsorbed on soil particles.
dicyclonon
Herbicide safener
NOMENCLATURE:
Common name dicyclonone ((f) F-ISO); dicyclonon (BSI, E-ISO)
IUPAC name (RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-
one
Chemical Abstracts name 1-(dichloroacetyl)hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]
pyrimidin-6(2H)-one CAS RN [79260712]; [110499257] (R)- isomer; [110499279]
(S)- isomer; the substance named dicyclonon in Chemical Abstracts Registry, with Registry
Number [85072828], is actually an isomer of dicyclonon, with a methyl group in position
7 instead of at the bridgehead position 8a. Development codes BAS 145138 (BASF)
12
H
18
Cl
2
N
2
O
2
COMMERCIALISATION:
Manufacturers BASF
APPLICATIONS:
herbicide, and its subsequent conjugation (see J. Davies & J. C. Caseley, Pestic. Sci. 1999,
55(11) 10431058). Uses Can be used to safen maize to a wide variety of herbicides.
(RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one
N
N
O
O
Cl
Cl
(RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one
Caution: Stereochemical terms discarded: s
184
dicyclopentadiene
dicyclopentadiene
Animal repellent
NOMENCLATURE:
IUPAC name 3a,4,7,7a-tetrahydro-1H-4,7-methano-indene
Chemical Abstracts name 3a,4,7,7a-tetrahydro-4,7-methano-1H-indene CAS RN [77
736] Smiles code C1C=CC2C3CC(C=C3)C
12
10
H
12
M.p. 32.7 C B.p. 64.5 C /14
mm
Hg V.p. 0.33 mPa (25 C) S.g./density 0.9766 (33 C)
Solubility Sparingly soluble in water. Readily soluble in acetone, dichloromethane, ethyl
acetate, hexane, and toluene. Stability Chemically very stable.
COMMERCIALISATION:
History Animal repellent introduced by Staehler.
APPLICATIONS: Uses As a repellent for animals such as hares, rabbits, and deer,
in winter or in summer. Applied in the form of impregnated strips on deciduous and
coniferous trees, or by spraying around ornamental plants and shrubs. Normally used in
combination with other materials. Formulation types SC.
ANALYSIS:
Product by glc with FID.
ICSC.873 (2005). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
50
for
rabbits 6720 mg/kg. Mild skin and eye irritant (rabbits). Inhalation LC
50
(4 h) for rats 660
mg/l air.
ECOTOXICOLOGY:
Fish LC
50
(96 h) for carp 62.2, rainbow trout 22.86 mg/l. Bees Not toxic to bees.
dieldrin 185
dieldrin
Insecticide
IRAC 2A
NOMENCLATURE:
Common name HEOD (for pure compound) (BSI, E-ISO, F-ISO, JMAF); dieldrine ((f)
F-ISO); dieldrin (USSR before 1984, Denmark); dieldrin (material containing >85% HEOD)
(BSI, E-ISO, BAN, ESA, JMAF, except Denmark)
IUPAC name (1R,4S,4aS,5R,6R,7S,8S,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-
octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
Chemical Abstracts name (1a,2,2a,3,6,6a,7,7a)-3,4,5,6,9,9-hexachloro-
1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth[2,3-b]oxirene
CAS RN [60571] EC no 2004845 Development codes Compound 497 (to
Hyman) Smiles code ClC1=C(Cl)C2(Cl)C3C4CC(C5OC54)C3C1(Cl)C2(Cl)Cl
12
H
8
Cl
6
O Form Tech. consists of buff
to light tan fakes with a mild odour. M.p. 175176 C; (tech. sets at >95 C) V.p. 0.4 mPa
(20 C) Henry 8.19 10
1
Pa m
3
mol
1
(calc.) S.g./density 1.62 (20 C) Solubility In
water 0.186 mg/l (20 C). Stability Stable to alkali, mild acids and to light. It reacts with
concentrated mineral acids, acid catalysts, acid oxidising agents and active metals (iron,
copper).
COMMERCIALISATION:
History Insecticide reported by C. W. Kearns et al. (J. Econ. Entomol., 1949, 42, 127).
Introduced by J. Hyman & Co. and later by the Shell International Chemical Co., Ltd.
Patents US 2676547
APPLICATIONS:
Mode of action Contact and ingested insecticide. Uses A presistent insecticide, used to
control locusts and tropical disease vectors, such as Glossina spp. Industrial uses included
timber preservation, termite-proofng of plastic and rubber coverings of electrical and
telecommunication cables, of plywood and building boards and as a termite barrier in
building construction. Formulation types EC; GR; WP.
PRODUCTS:
Discontinued products Octalox* (Hyman).
ANALYSIS:
Product analysis by glc, by i.r. spectrophotometry (CIPAC Handbook, 1983, 1B, 1780;
FAO Specifcation (CP/36), Organochlorine Insecticides 1973; AOAC Methods 18th Ed.,
961.05), by tlc (ibid., 972.05), or by potentiometric titration of liberated chloride ion
(CIPAC Handbook, 1994, F, 190). Residues determined by glc, tlc or paper chromatography
(AOAC Methods, 18th Ed., 970.52; ibid., 985.22), or by glc with ECD (Anal. Methods Pestic.
Plant Growth Regul., 1972, 6, 268; Analyst (London), 1979, 104, 425; P. A. Greve & W. B. F.
186
dienochlor
Grevenstuk, Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1975, 40, 1115; G. M. Telling et al., J.
Chromatogr., 1977, 137, 405; M. A. Luke et al., J. Assoc. Off. Anal. Chem., 1981, 64, 1187; ibid.,
1985, 68, 385, 29.A0129.A04). See also Pestic. Anal. Man., I, 204, 208, 301, 302, 303, 304, 402,
502. In drinking water by glc with ECD (AOAC Methods, 18th Ed., 990.06).
EHC 91 (1989). JMPR Mtg. 65 (1992); JMPR Evaln. 29 (1977). HSG 21 (1989). PDS 17 (1975).
ICSC.787 (1998). IARC 5 (1974); Suppl. 7 (1987). EU Status (1107/2009) Considered
to be outside the scope of the Directive; already banned, 79/117/EC, as amended by
IARC Class 3
Oral Acute oral LD
50
for rats 3787, rabbits 4550 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats 6090 mg/kg. NOEL In long-term exposure, NOEL for rats
and dogs 0.1 mg/kg diet (0.005 mg/kg daily). Data available indicate that dieldrin and aldrin
do not produce malignant tumours in rats, dogs, monkeys at all tolerated dose levels in
long-term feeding studies. The signifcance of the marginal increase in incidence of hepatic
tumours in mice, following lifetime exposure to dieldrin, is doubtful. ADI/RfD (JMPR)
0.0001 mg (total aldrin + dieldrin)/kg b. w. (PTDI) [1994]; (EPA) cRfD 0.00005 mg/kg b.w.
[1990]. Water GV 0.03 ;g/l (sum of aldrin+dieldrin). Toxicity Class WHO (a.i.) Ib
ECClassifcation T+; R27| T; R25, R48/25| R40| N; R50, R53 PIC Yes.
ENVIRONMENTAL FATE:
Animals Oxidised in the liver to a hydrophilic hydroxy compound, and is subsequently
eliminated in the urine as the glucuronic acid conjugate.
dienochlor
Acaricide
NOMENCLATURE:
Common name dienochlor (BSI, E-ISO); di(nochlore) ((m) F-ISO)
IUPAC name perchloro-1,1-bicyclopenta-2,4-diene
Chemical Abstracts name 1,1,2,2,3,3,4,4,5,5-decachlorobi-2,4-cyclopentadien-1-yl
CAS RN [2227170] Development codes SAN 804 I Smiles code ClC1=C(Cl)C(Cl)
(C(=C1Cl)Cl)C2(Cl)C(=C(Cl)C(=C2Cl)Cl)Cl
Cl
Cl
Cl
Cl Cl
Cl
Cl
Cl
Cl
Cl
dienochlor 187
10
Cl
10
Form Grey crystals; (tech.,
light yellow powder, sometimes with faint onion or garlic odour). M.p. 122123 C; (tech.,
111128 C) B.p. 250 C (decomp.) V.p. 0.29 mPa (extrapolated to 25 C) K
ow
logP =
3.23 (mean, 25 C) S.g./density 1.923 (tech., 25 C) Solubility Practically insoluble
in water (25 ppb). In iso-octane 7.89, toluene 59.00, acetonitrile 1.16, n-octanol 4.77,
tetrahydrofuran 98.32 (all in g tech./100 ml). Stability Tech. dienochlor was stable when
stored at 54 C for 14 d, and at 42 C for 2 y. Hydrolysis DT
50
(25 C) 30.5 d (pH 9), 93 d
(pH 7), 184 d (pH 5). DT
50
as thin flm solution in simulated sunlight 1.6 min.
COMMERCIALISATION:
History Acaricide reported by W. W. Allen et al. (J. Econ. Entomol., 1964, 57, 187).
Introduced by Hooker Chemical Corp. and later by Zoecon Corp., followed by Sandoz
AG (later Novartis Crop Protection AG). Patents US 2732409; US 2934470 (to Hooker)
Manufacturers Novartis
APPLICATIONS:
Mode of action Acaricide with predominantly contact action. Interferes with oviposition.
Long residual activity under glasshouse conditions. Uses Control of mites (Tetranychus
spp., Panonychus ulmi, and Polyphagotarsonemus latus) on roses, chrysanthemums, and other
ornamentals, normally under glass. Formulation types WP; EW .
PRODUCTS:
Discontinued products Pentac* (Novartis); Pentac Aquafow* (Dow).
ANALYSIS:
Product analysis by hplc spectroscopy. Residues determined by hplc. In soil, by gc/ECD
(Environ. Chem. Methods).
Oral Acute oral LD
50
for male albino rats >3160 mg tech./kg. Skin and eye Acute
percutaneous LD
50
for rabbits >3160, rats >2000 mg/kg. Mildly irritating to eyes and skin
(rabbits). Sensitising to skin. Inhalation LC
50
(4 h) for rats 0.08 mg/l air.
Toxicity Class WHO (a.i.) III EPA (formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
3966, bobwhite quail >5620 mg/kg diet. Fish LC
50
(96 h) for rainbow trout 0.050, bluegill
sunfsh 0.6 mg/l. Daphnia LC
50
(48 h) 1.2 mg/l. Algae NOEC (96 h) for Scenedesmus
subspicatus >30 mg/l. Bees LD
50
(contact) >36 g/bee. Worms LC
50
(7d and 14 d) >1000
mg/kg dry soil.
ENVIRONMENTAL FATE:
Animals Rapid degradation was observed in rats. Within 4 days, following a single oral
dose of 1 mg/kg, female rats excreted 2% and 88% of applied 14C in urine and faeces
188
diethatyl-ethyl; diethatyl
respectively. Plants Major degradation products are perchloroketones. Degradation is
mainly photochemical rather than metabolic; DT
50
23 d when plants are exposed to
sunlight. Soil/Environment Soil adsorption Kd 384 (silty loam, pH 6.1, 3.6% o.m.), 196
(loamy sand, pH 7.5, 0.5% o.m.), 269 (silty clay loam, pH 6.8, 11.8% o.m.), 311 (sandy loam,
pH 6.9, 1.3% o.m.). In soil DT
50
3.1 d.
diethamquat; diethamquat dichloride
Herbicide
NOMENCLATURE:
Common name diethamquat (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,1-bis(diethylcarbamoylmethyl)-4,4-bipyridinium
Chemical Abstracts name 1,1-bis[2-(diethylamino)-2-oxoethyl]-4,4-bipyridinium
CAS RN [4029021] dichloride, formerly [111156457]; [400852677] dication
Development codes PP831
PHYSICAL CHEMISTRY: Mol. wt. 384.5; (diethamquat dichloride 455.4)
M.f. C
22
H
32
N
4
O
2
; (diethamquat dichloride C22H32Cl
2
N4O
2
)
COMMERCIALISATION:
History Dichloride evaluated as herbicide by ICI Plant Protection Division (later ICI
Agrochemicals).
diethatyl-ethyl; diethatyl
Herbicide
NOMENCLATURE:
Common name (for the acid) diethatyl (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name (acid) N-chloroacetyl-N-(2,6-diethylphenyl)glycine
Chemical Abstracts name (acid) N-(chloroacetyl)-N-(2,6-diethylphenyl)glycine
CAS RN [38727558] ethyl ester; [38725950] acid Development codes (acid)
Hercules 22 234 Smiles code acid:CCc1cccc(CC)c1N(CC(=O)O)C(=O)
CCl;ester:CCOC(=O)CN(C(=O)CCl)c1c(CC)cccc1CC
PHYSICAL CHEMISTRY: Mol. wt. 311.8; (acid 283.8) M.f. C
16
H
22
ClNO
3
(ester);
C
14
H18ClNO3 (acid) Form Colourless crystals. M.p. 4950 C V.p. 0.43 mPa (30 C)
K
ow
logP = 3.599 (pH 6.6, 25 C) S.g./density 1.38 (25 C) Solubility In water 105 mg/l
(25 C). In methanol, ethanol 810, isopropanol 750, acetone, xylene 820, methyl isobutyl
ketone 830, chloroform 770, kerosene 200 (all in g/kg, room temperature).
Stability Hydrolysed under strongly acidic or alkaline conditions. Thermally stable up to
240 C. Tech. and formulations are stable for >2 y under normal conditions.
diethatyl-ethyl; diethatyl 189
COMMERCIALISATION:
History Herbicidal activity of the ethyl ester reported by S. K. Lehman (Proc. North Cent.
Weed Control Conf., 29th, 1972); introduced by Hercules Inc. Agrochemicals (later Nor-Am
Chemical Co.).
Manufacturers NOR-AM
APPLICATIONS:
Biochemistry Inhibits cell division by blocking protein synthesis. It is reported that
chloroacetamides inhibit synthesis of very long chain fatty acids (J. Schmalfuss et al., Abstr.
Meeting WSSA, Toronto, 40, 117118, 2000; P. Bger, Abstr. III Int. Weed Control Congr., Brazil,
2000). Mode of action Selective soil-herbicide, absorbed primarily by the emerging
shoots, and secondarily by the roots. Uses Pre-plant soil-incorporated or pre-emergence
control of annual grasses and some broad-leaved weeds in sugar beet, soya Beans, cotton,
sunfowers, potatoes, peanuts, phaseolus beans, fodder beet, beetroot, sugar cane, fax,
spinach, wheat, rice, and other crops at rates in the range 2.26.7 kg/ha.
PRODUCTS:
Discontinued products Antor* (diethatyl-ethyl) (AgrEvo).
ANALYSIS:
Product analysis by glc or hplc. Residues determined by glc.
Oral Acute oral LD
50
50
for rabbits >4000 mg/kg. Mild skin
and eye irritant (rabbits). NOEL (2 y) for rats and mice 1000 mg/kg diet, for dogs
50 mg/kg diet. In 3-generation study, NOEL for rats 200 mg/kg diet.
ECOTOXICOLOGY:
Birds Diethatyl-ethyl: acute oral LD
50
for mallard ducks and bobwhite quail >10 000 mg/
kg. Fish LC
50
(24 h) for bluegill 7.14 mg/l (NOEL 2.4 mg/l), for rainbow trout 10.3 mg/l
(NOEL 1.0 mg/l). LC
50
(96 h) for bluegill sunfsh 3.34, rainbow trout 1.82 mg/l. Bees Not
toxic to bees at 43.5 g/bee.
ENVIRONMENTAL FATE:
Plants In plants, diethatyl is rapidly metabolised (almost completely within 4 days), with
translocation of metabolites throughout the plant. Soil/Environment In soil, micro-
organisms appear to play a signifcant role in degradation. Residual activity persists for
c. 610 weeks.
190
diethyl 5-methylpyrazol-3-yl phosphate
dietholate
Herbicide safener
NOMENCLATURE:
Common name dietholate (WSSA)
IUPAC name O,O-diethyl O-phenyl phosphorothioate (I)
Chemical Abstracts name (I) CAS RN [32345292] Development codes R 33865
10
H
15
O
3
PS
APPLICATIONS:
Biochemistry Appears to act by inhibiting metabolism of the carbonyl linkage of EPTC
(T. B. Moorman et al., Soil Biol. Biochem., 1992, 24(2) 121). Uses Inhibits degradation of
thiocarbamate herbicides, in soils with high microbial activity. Also acts as an insecticide
synergist. (R. M. Hollingworth et al., Pure & Appl. Chem., 1995, 67, 14871532).
PRODUCTS:
Discontinued mixtures Eradicane Extra* (+ dichlormid + EPTC) (Zeneca).
O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate
Chemical Abstracts name O,O-diethyl O-(6-methyl-2-propyl-4-pyrimidinyl)
phosphorothioate CAS RN [5826915] Development codes G 24 622
Smiles code CCCc1nc(C)cc(OP(=S)(OCC)OCC)n1
12
H
21
N
2
O
3
PS
COMMERCIALISATION:
History Insecticide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
PRODUCTS:
Discontinued products Pyrazinon* (Ciba-Geigy).
diethyl 5-methylpyrazol-3-yl phosphate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name diethyl 5-methylpyrazol-3-yl phosphate
O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate 191
Chemical Abstracts name diethyl 5-methyl-1H-pyrazol-3-yl phosphate
Other names pyrazoxon CAS RN [108349] Development codes G 24 483
Smiles code CCOP(=O)(OCC)Oc1cc(C)[nH]n1
8
H
15
N
2
O
4
P
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Pyrazoxon* (Ciba-Geigy).
ECClassifcation T+; R26/27/28
O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate; O,O-
diethyl O-4-methylcoumarin-7-yl phosporothioate; 7-diethoxyphosphinothioyloxy-4-
methylcoumarin
Chemical Abstracts name O,O-diethyl O-(4-methyl-2-oxo-2H-1-benzopyran-7-
yl) phosphorothioate CAS RN [299456] Development codes E 838 (Bayer)
Smiles code CCOP(=S)(OCC)Oc1ccc2c(C)cc(=O)oc2c1
14
H
17
O
5
PS
COMMERCIALISATION:
History Insecticide reported by G. Schrader (Angew. Chem., 1952, Monogr. No. 62, 2nd Ed.).
Introduced by Bayer AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Ingested insecticide. Uses For
use against colorado beetle.
PRODUCTS:
Discontinued products Potasan* (Bayer); Discontinued mixtures Potasan G*
(+ gamma-HCH) (Bayer).
ECClassifcation T+; R26/27/28| N; R50, R53| concn. dep.
192
difenoxuron
difenopenten; difenopenten-ethyl
Herbicide
NOMENCLATURE:
Common name dif(nopent) ((m) F-ISO); difenopenten (BSI, E-ISO, ANSI, WSSA)
IUPAC name (E)-()-4-[4-(,,-trifuoro-p-tolyloxy)phenoxy]pent-2-enoic acid
Chemical Abstracts name (E)-()-4-[4-[4-(trifuoromethyl)phenoxy]phenoxy]-2-
pentenoic acid CAS RN [81416446] difenopenten; [71101058] difenopenten-ethyl
Development codes XE-773; KK-80 (both for difenopenten-ethyl)
PHYSICAL CHEMISTRY: Mol. wt. 352.3; (ethyl ester 380.4) M.f. C
18
H
15
F
3
O
4
; (ethyl
ester C20H19F3O4)
COMMERCIALISATION:
History Herbicide evaluated by Chevron Chemical Company LLC.
difenoxuron
Herbicide
NOMENCLATURE:
Common name difenoxuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea
Chemical Abstracts name N-[4-(4-methoxyphenoxy)phenyl]-N,N-
dimethylurea CAS RN [14214325] Development codes C 3470
Smiles code COc1ccc(Oc2ccc(NC(=O)N(C)C)cc2)cc1
16
H
18
N
2
O
3
M.p. 138139 C V.p. 1.24 10
6
mPa (20 C) Henry 1.78 10-8 Pa m
3
mol
1
(calc.)
S.g./density 1.30 (20 C) Solubility In water 20 mg/l (20 C). In dichloromethane 156,
acetone 63, isopropanol 10, benzene 8, hexane 0.05 (all in g/kg, 20 C). Stability No
signifcant hydrolysis occurs at 30 C and pH 1 or 13.
COMMERCIALISATION:
History Herbicide reported by L. Ebner & J. Schuler (Proc. Br. Weed Control Conf., 7th, 1964,
2, 711). Introduced by Ciba-Geigy AG. Patents BE 593743; GB 913383
APPLICATIONS:
site. Mode of action Selective herbicide, absorbed by the leaves and roots. Uses Control
O NHCON(CH
3
)
2
CH
3
O
dihydroazadirachtin 193
of annual broad-leaved weeds post-emergence in onions, leeks, garlic, and other alliums at
2.5 kg/ha. Formulation types WP.
PRODUCTS:
Discontinued products Lironion* (Ciba-Geigy).
ANALYSIS:
Product analysis by acidimetric titration. Residues determined by glc.
Oral Acute oral LD
50
50

for rats >2150 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC
50
(6 h) for
rats >0.66 mg/l air. NOEL (90 d) for rats 50 mg/kg daily, for dogs 200 mg/kg daily.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for trout 510 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
50
c. 12 d.
dihydroazadirachtin
Insecticide
NOMENCLATURE:
Chemical Abstracts name 22,23-dihydroazadirachtin; dimethyl [2aR-[2a,3,4(1aR*,2
S*,3aR???*,6aS*,7S*,7aS*),4a, 5,7aS*,8(E),10,10a,10b]]-10-(acetyloxy)-4-(hexahydro-
6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl)octahydro-3,5-
dihydroxy-4-methyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-1H,7H-naphtho[1,8-bc:4,4a-c]
difuran-5,10a(8H)-dicarboxylate CAS RN [108189588]; [37324451] (unspecifed
stereochemistry)
O
OH
CO
2
CH
3
O
O
CH
3
OC
O
O
OH
C
CH
3
CH
3
O
CH
3
O
O
O
HO
CH
3
H
O
CH
3
C
194
2,3-dihydro-5,6-diphenyl-1,4-oxathi-ine
35
H
46
O
16
APPLICATIONS:
Biochemistry Ecdysone antagonist. Uses For control of ants, aphids, Beetles, caterpillars,
crickets, etc, on horticultural and ornamental plants. Formulation types WG .
Oral Acute oral LD
50
for rats >5 g/kg. Skin and eye Acute percutaneous LD
50
for
rabbits >2 g/kg. Non-irritating to skin and eyes (rabbits); not a skin sensitiser (guinea
pigs). Inhalation LC
50
for rats >2.9 mg/l. Other Non-mutagenic in reverse mutation,
unscheduled DNA synthesis and CHO tests.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >816 mg/kg. Dietary LD
50
for bobwhite quail
>1875 mg/kg. Fish LD
50
(96 h) for rainbow trout 17.65, bluegill sunfsh 9 mg/kg.
Daphnia LD
50
11.6 mg/l Bees Relatively non-toxic to honeybees.
2,3-dihydro-5,6-diphenyl-1,4-oxathi-ine
NOMENCLATURE:
IUPAC name 2,3-dihydro-5,6-diphenyl-1,4-oxathi-ine
Chemical Abstracts name 2,3-dihydro-5,6-diphenyl-1,4-oxathiin
CAS RN [58041193] Development codes P 293 Smiles code C1CS/C(=C(\O1)/
c2ccccc2)/c3ccccc3;without stereochemistry:C1CSC(=C(O1)c2ccccc2)c3ccccc3
16
H
14
OS
COMMERCIALISATION:
History Plant growth regulator evaluated by Uniroyal Chemical Co., Inc.
2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide
Fungicide
NOMENCLATURE:
IUPAC name 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide
Chemical Abstracts name 2,3-dihydro-5-phenyl-1,4-dithiin 1,1,4,4-tetraoxide
CAS RN [34407879] Development codes P 368
Smiles code O=S/1(=O)CCS(=O)(=O)/C(=C1)/c2ccccc2;without
stereochemistry:O=S1(=O)CCS(=O)(=O)C(=C1)c2ccccc2
10
H
10
O
4
S
2
COMMERCIALISATION:
History Fungicide evaluated by Uniroyal Chemical Co., Inc.
dimefox 195
dimefox
IRAC 1B
NOMENCLATURE:
Common name dimefox (BSI, E-ISO, (m) F-ISO)
IUPAC name tetramethylphosphorodiamidic fuoride (I)
Chemical Abstracts name (I) Other names DMF CAS RN [115264]
EC no 2040768 Smiles code CN(C)P(=O)(F)N(C)C
PHYSICAL CHEMISTRY:
Composition Tech. contains schradan (q.v.) and tris(dimethylamino)phosphine oxide.
Mol. wt. 154.1 M.f. C
4
H
12
FN
2
OP Form Colourless liquid. B.p. 67 C /4 mmHg
V.p. 48000 mPa (25 C) K
ow
logP = 1.2 (chloroform/water) S.g./density 1.115 (20 C)
Solubility Miscible with water and most organic solvents. Stability Resistant to
hydrolysis by alkali but is hydrolysed by acids. Slowly oxidised by vigorous oxidising agents,
rapidly by chlorine.
COMMERCIALISATION:
History Insecticide and acaricide reported by H. Kkenthal & G. Schrader (B.I.O.S. Final
Report, 1946, 1095). Introduced by Fisons Pest Control Ltd (later Schering Agrochemicals).
Patents GB 688760, GB 741662.
APPLICATIONS:
acaricide. Uses As a soil treatment for hop plants against aphids and red spider mites.
Effective for 4256 d.
PRODUCTS:
Discontinued products PestoxXIV* (Fisons); TerraSytol* (DuPont);
Discontinued mixtures Sytam* (+ schradan) (with tris(dimethylamino)phosphine
oxide) (Murphy, Wacker); Terra Sytam* (+ schradan) (with tris(dimethylamino)phosphine
oxide) (Murphy, Wacker).
ANALYSIS:
Product analysis, see CIPAC Handbook, 1980, 1A, 329; mixture with schradan, ibid., 334.
Oral Acute oral LD
50
for rats 12 mg/kg. Toxicity Class WHO (a.i.) Ia
ECClassifcation T+; R27/28
196
dimethipin
dimethipin
Herbicide, plant growth regulator
NOMENCLATURE:
Common name no name (Japan); dimethipin (BSI, ANSI, E-ISO); dim(thipin) ((m) F-ISO)
IUPAC name 2,3-dihydro-5,6-dimethyl-1,4-dithi-ine 1,1,4,4-tetraoxide
Chemical Abstracts name 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetraoxide
CAS RN [55290647] Development codes N 252
Smiles code CC1=C(C)S(=O)(=O)CCS1(=O)=O
6
H
10
O
4
S
2
Form Tech. is a white,
crystalline solid. M.p. 167169 C V.p. 0.051 mPa (25 C) K
ow
logP = 0.17 (24 C)
Henry 2.33 10
6
Pa m
3
mol
1
(calc.) S.g./density 1.59 g/cm3 (23 C) Solubility In
water 4.6 g/l (25 C). In acetonitrile 180, methanol 10.7, toluene 8.979 (all in g/l, 25 C).
Stability Stable at pH 3, 6 and 9 (25 C). Stable for 1 y at 20 C, 14 d at 55 C. Stable to
light 7 d at 25 C. pKa 10.88, v. weak acid
COMMERCIALISATION:
History Plant growth regulator reported by R. B. Ames et al. (Proc. Beltwide Cotton
Produc. Res. Conf., 1974, p. 61). Introduced by Uniroyal Chemical Co., Inc. (became
Chemtura Corp.) in USA in 1982. Patents US 3920438 Manufacturers Chemtura
APPLICATIONS:
Biochemistry Interferes with protein synthesis in the plant epidermis.
Mode of action Defoliant and desiccant. Uses Defoliation of cotton, nursery stock,
rubber trees, and vines, at 260720 g/ha. Potato haulm desiccant, at 480720 g/ha. Reduces
seed moisture content at harvest of maize, rice, oilseed rape, fax, and sunfowers, at
240720 g/ha. Formulation types SC.
PRODUCTS:
Discontinued products Harvade* (Chemtura); Lintplus* (Chemtura);
Discontinued mixtures Leafess* (+ thidiazuron) (Chemtura).
ANALYSIS:
Product analysis by glc or i.r. spectrometry. Residues determined by gc/S-FPD (Resid. Anal.
Methods). See also Pestic. Anal. Man., II, 180.406, 186.2050. Details available from Chemtura.
JMPR Mtg. 101 (2004); JMPR Evaln. I 93 (2001); JMPR Evaln. II 88 (1999), 104 (2004).
S
S CH
3
CH
3
O O
O O
dimethirimol 197
Oral Acute oral LD
50
50
for
rabbits >5000 mg/kg. Extreme eye irritant; not a dermal irritant (rabbits). Weak sensitiser
(guinea pigs). Inhalation LC
50
(4 h) for rats 1.2 mg/l. NOEL In chronic feeding studies,
NOEL for rats 2, dogs 25 mg/kg b.w. daily. ADI/RfD (JMPR) 0.02 mg/kg b.w. [1999, 2004];
(EPA) cRfD 0.02 mg/kg b.w. [1990, 2005]. Toxicity Class WHO (a.i.) III EPA (formulation)
I (tech.), III (Harvade 5F and Harvade 25F)
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and bobwhite quail >5000 ppm. LC
50
for
mallard ducks 896 mg/kg. Fish LC
50
(96 h) for rainbow trout 52.8, bluegill sunfsh 20.9,
sheepshead minnows 17.8 mg/l. Daphnia LC
50
50
(5 d) for
Selenastrum capricornutum 5.12 mg/l. Other aquatic spp. LC
50
(96 h) for mysid shrimps
(Mysidopsis bahia) 13.9 mg/l. Bees LD
50
>100 g/bee (25% formulation). Worms LC
50

(14 d) for earthworms >39.4 ppm (25% formulation).
ENVIRONMENTAL FATE:
Plants Unchanged. Soil/Environment DT
50
in soilc. 104149 d. Kd 0.092; K
oc
3.27.
dimethirimol
Fungicide
FRAC 8, A2
NOMENCLATURE:
Common name dimethirimol (BSI, E-ISO, JMAF); dim(thyrimol) ((m) F-ISO)
IUPAC name 5-butyl-2-dimethylamino-6-methylpyrimidin-4-ol
Chemical Abstracts name 5-butyl-2-(dimethylamino)-6-methyl-4(1H)-pyrimidinone
CAS RN [5221534] Development codes PP675 (ICI)
Smiles code CCCCc1c(C)nc(nc1O)N(C)C
11
H
19
N
3
M.p. 102 C V.p. 1.46 mPa (30 C) K
ow
logP = 1.9 Henry <2.55 10
4
Pa m
3
mol
1
(25 C,
calc.) Solubility In water 1.2 g/l (25 C). Readily soluble in aqueous solutions of strong
acids. In chloroform 1200, xylene 360, ethanol 65, acetone 45 (all in g/l, 25 C).
Stability Stable in acidic and alkaline solutions. Decomposed by sunlight when in aqueous
solution; DT
50
c. 7 d. Dissolves in aqueous solutions of strong acids to form water-soluble
salts.
N
N
OH
CH
3
(CH
2
)
3
CH
3
N(CH
3
)
2
198
dimethrin
COMMERCIALISATION:
History Systemic fungicide reported by R. S. Elias et al. (Nature (London), 1968, 219, 1160).
Introduced by ICI Plant Protection Division (later Syngenta AG) and frst marketed in 1970.
Patents GB 1182584 Manufacturers Syngenta
APPLICATIONS:
Biochemistry Inhibits nucleic acid synthesis (adenosine deaminase).
Mode of action Systemic fungicide with protective and curative action. Absorbed by
the roots, with translocation in the xylem. Uses Soil application for control of powdery
mildews in cucurbits, tobacco, capsicums, tomatoes, and some ornamentals, at 0.52 kg/ha;
also as a foliar spray at 50100 g/ha.. Formulation types SL .
PRODUCTS:
Discontinued products Milcurb* (Syngenta).
ANALYSIS:
Product analysis by glc (J. E. Bagness & W. G. Sharples, Analyst (London), 1974, 99, 225).
Residues determined by hplc.
Oral Acute oral LD
50
for rats 2350, mice 8001600, guinea pigs 500 mg/kg.
50
for rats >400 mg/kg. Non-irritating to skin and
eyes (rabbits). NOEL (2 y) for dogs 25 mg/kg, for rats 300 mg/kg diet. Other Acute i.p.
LD
50
for rats 200400 mg/kg. Toxicity Class WHO (a.i.) U EPA (formulation) III
ECClassifcation (Xn; R21)
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(24 h) for young brown trout
42 mg/l, (48 h) 33 mg/l, (96 h) 28 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, metabolism involves demethylation of the dimethylamino group.
50
c. 120 d (sandy soil, glasshouse and John Innes composts).
dimethrin
Insecticide
IRAC 3
NOMENCLATURE:
Common name dimethrin (BSI, E-ISO, ANSI); dim(thrine) ((f) F-ISO)
IUPAC name 2,4-dimethylbenzyl (1RS)-cis,trans-2,2-dimethyl-3-(2-methylprop-1-
enyl)cyclopropanecarboxylate; 2,4-dimethylbenzyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-
3-(2-methylprop-1-enyl)cyclopropanecarboxylate; 2,4-dimethylbenzyl ()-cis-trans-
chrysanthemate
2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate 199
Chemical Abstracts name (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-
propenyl)cyclopropanecarboxylic acid CAS RN [70382] unstated stereochemistry
Smiles code CC(=CC1C(C(=O)OCc2ccc(C)cc2C)C1(C)C)C
19
H
26
O
2
COMMERCIALISATION:
History Insecticide synthesised by W. F. Barthel, activity reported by P. G. Piquett & W. A.
Gersdorff (J. Econ. Entomol., 1958, 51, 791).
APPLICATIONS:
JMPR Evaln. 4 (1965).
NOEL (1 y) for rats 300 mg/kg b.w. (EPA Tracking). ADI/RfD (JMPR) No ADI [1965];
(EPA) 0.3 mg/kg b.w. [1986].
2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (I)
Chemical Abstracts name (I) CAS RN [7122045] Development codes C 10 015
Smiles code CNC(=O)Oc1ccccc1C2OC(C)C(C)O
2
13
H
17
NO
4
COMMERCIALISATION:
History Insecticide reported by F. Bachmann & J. B. Legge (J. Sci. Food Agric., 1968 Suppl.,
p. 39). Introduced by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
insecticide.
PRODUCTS:
Discontinued products Fondaren* (Ciba-Geigy); Sapecron C* (Ciba).
200
dimetilan
5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate
Chemical Abstracts name 5,5-dimethyl-3-oxo-1-cyclohexen-1-yl
dimethylcarbamate Other names dimetan CAS RN [122156] EC no 2045258
Development codes G 19 258 Smiles code CN(C)C(=O)OC1=CC(=O)CC(C)(C)C1
11
H
17
NO
3
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Dimetan* (Geigy).
ECClassifcation T; R25
dimetilan
Insecticide
NOMENCLATURE:
Common name dimetilan (BSI, ESA)
IUPAC name 1-dimethylcarbamoyl-5-methylpyrazol-3-yl dimethylcarbamate
Chemical Abstracts name 1-[(dimethylamino)carbonyl]-5-methyl-1H-pyrazol-3-yl
dimethylcarbamate CAS RN [644644] EC no 2114200 Development codes G 22
870; GS 13 332 Smiles code CN(C)C(=O)Oc1cc(C)n(n1)C(=O)N(C)C
PHYSICAL CHEMISTRY:
Composition Tech. is >96%. Mol. wt. 240.3 M.f. C
10
H
16
N
4
O
3
Form Colourless solid;
(tech. is a light yellow to reddish-brown crystalline solid). M.p. 6871 C; (tech., 55
65 C) B.p. 200210/13 mmHg V.p. 13 mPa (20 C) Solubility Readily soluble in water,
chloroform, DMF; soluble in ethanol, acetone, xylene and other organic solvents.
Stability Hydrolysed by acids and by alkalis.
COMMERCIALISATION:
History Insecticide reported by H. Gysin (Chimia, 1954, 8, 205, 221). Introduced by J.
R. Geigy S.A. (later Ciba-Geigy AG). Patents CH 281946, CH 282655, GB 681376, US
2681879.
dimexano 201
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Ingested insecticide. Uses For
control of fies.
PRODUCTS:
Discontinued products Snip* (Ciba-Geigy).
ANALYSIS:
Product analysis is by glc with internal standard. Residues may be determined by glc with
MCD or by tlc. See also A. Margo & K. Stammbach, Anal. Methods Pestic. Plant Growth Regul.
Food Addit., 1964, 2, 183; Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 376.
Oral Acute oral LD
50
for rats 64, mice 6065 mg/kg. Livestock is more susceptible.
Toxicity Class WHO (a.i.) IbECClassifcation T; R25| Xn; R21| N; R50, R53
dimexano
NOMENCLATURE:
Common name dimexano (BSI (from 1984), E-ISO, (m) F-ISO); dimexan* (BSI before
1984)
IUPAC name O,O-dimethyl dithiobis(thioformate)
Chemical Abstracts name dimethyl thioperoxydicarbonate
Other names dimethylxanthic disulfde CAS RN [1468377] EC no 2159938
Smiles code COC(=S)SSC(=S)OC
PHYSICAL CHEMISTRY:
4
H
6
O
2
S
4
Form Tech. is a yellow oil,
with an objectionable odour. V.p. 4 10
5
mPa (21 C) S.g./density 1.394 (20 C, tech.)
Solubility Miscible with acetone, benzene, ethanol, hexane.
COMMERCIALISATION:
History Herbicide introduced by Vondelingenplaat N.V.
APPLICATIONS:
Mode of action Contact herbicide, plant growth regulator and desiccant. Uses At 9 kg/
ha pre-em. on drilled crops, controlling seeding dicotolydonous weeds; at 28 gk/ha as
a pre-harvest desiccant of onions and peas; and to control the growth and splitting of
carrots. Formulation types EC.
202
dinex; dinex-diclexine
PRODUCTS:
Discontinued products TriPE* (Vondelingenplaat).
ANALYSIS:
Product analysis is by colorimetry (D. G. Clarke et al., Anal. Chem., 1951, 23, 1842) after
reduction.
Oral Acute oral LD
50
for rats 340 mg tech./kg. Toxicity Class WHO (a.i.) O
ENVIRONMENTAL FATE:
Soil/Environment It does not persist in soil.
dimidazon
Herbicide
NOMENCLATURE:
Common name dimidazon (BSI, E-ISO); dimethazone* (withdrawn BSI name);
dimidazone ((m) F-ISO)
IUPAC name 4,5-dimethoxy-2-phenylpyridazin-3(2H)-one
Chemical Abstracts name 4,5-dimethoxy-2-phenyl-3(2H)-pyridazinone
CAS RN [3295781] Development codes BAS 255H (BASF)
Smiles code COc1cnn(c2ccccc2)c(=O)c1OC
12
H
12
N
2
O
3
COMMERCIALISATION:
History Herbicide introduced by BASF AG.
dinex; dinex-diclexine
NOMENCLATURE:
Common name dinex (BSI, E-ISO, (m) F-ISO); DN (JMAF); p(dinex) ((m) France)
IUPAC name 2-cyclohexyl-4,6-dinitrophenol (I)
Chemical Abstracts name (I) Other names DNOCHP (dinex) CAS RN [131895]
dinex; [317839] dinex-diclexine EC no 2050425 Development codes DN1 (dinex);
DN111 (dinex-diclexine)
PHYSICAL CHEMISTRY: Mol. wt. 266.3; (dinex-diclexine 447.6) M.f. C
12
H
14
N
2
O
5
;
(dinex-diclexine C24H37N3O5)
dinofenate 203
COMMERCIALISATION:
History Dinex was introduced as an acaricide and insecticide by Dow Chemical Co., Ltd
(later DowElanco), and its dicyclohexylammonium salt (dinex-diclexine) by Fisons Ltd
(later Schering Agriculture).
PRODUCTS:
Discontinued products DynoneII* (FBC).
ADI/RfD (EPA) 0.002 mg/kg b.w. [1987], based on other dinitrophenols.
Toxicity Class WHO (a.i.) OECClassifcation T; R23/24/25| N; R50, R53 (dinex and
dinex salts and esters)
dinocton
NOMENCLATURE:
Common name dinocton (BSI, E-ISO, (m) F-ISO, for a reaction product comprising
isomeric dinitro(octyl)phenyl methyl carbonates)
IUPAC name for main components: (i) 2,4-dinitro-6-(1-propylpentyl)phenyl methyl
carbonate (I); (ii) 2-(1-ethylhexyl)-4,6-dinitrophenyl methyl carbonate (II); (iii) 2,6-dinitro-4-
(1-propylpentyl)phenyl methyl carbonate (III); (iv) 4-(1-ethylhexyl)-2,6-dinitrophenyl methyl
carbonate (IV)
Chemical Abstracts name (I), (II), (III), (IV) Other names dinocton-6 (i) + (ii);
dinocton-4 (iii) + (iv) CAS RN [32534966] (i) + (ii); [19000589] (i); [19000523] (ii);
[32535083] (iii) + (iv); [6465516] (iii); [6465607] (iv)
Development codes MC 1945 (i) + (ii); MC 1947 (iii) + (iv); TD 8537 (iii) + (iv)
16
H
22
N
2
O
7
COMMERCIALISATION:
History Acaricide and fungicide reported by M. Pianka (Proc. Crop Prot. Symp., 2nd.,
Magdeburg, 1966). Evaluated by Murphy Chemical Co. (later DowElanco).
Toxicity Class WHO (a.i.) OECClassifcation Xn; R22| N; R50, R53
dinofenate
Herbicide
NOMENCLATURE:
Common name dinofenate (BSI)
IUPAC name 2-sec-butyl-4,6-dinitrophenyl 2,4-dinitrophenyl carbonate
204
dinoprop
Chemical Abstracts name 2,4-dinitrophenyl 2-(1-methylpropyl)-4,6-dinitrophenyl
carbonate CAS RN [61614628] Smiles code CCC(C)c1cc(cc([N+](=O)[O-])
c1OC(=O)Oc2ccc(cc2[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
17
H
14
N
4
O
11
COMMERCIALISATION:
History Herbicide evaluated by Pennwalt.
dinopenton
NOMENCLATURE:
Common name dinopenton (BSI, E-ISO, (m) F-ISO)
IUPAC name isopropyl 2-(1-methylbutyl)-4,6-dinitrophenyl carbonate
Chemical Abstracts name 2-(1-methylbutyl)-4,6-dinitrophenyl 1-methylethyl carbonate
CAS RN [5386572]
Smiles code CCCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)OC(C)C)[N+](=O)[O-]
15
H
20
N
2
O
7
COMMERCIALISATION:
History Acaricide reported at 5th Int. Pestic. Congr., London, 1963 (M. Pianka, J. Sci. Food
Agric., 1966, 17, 47). Evaluated by Murphy Chemical Ltd (later DowElanco).
dinoprop
Herbicide
NOMENCLATURE:
Common name dinoprop (BSI, E-ISO, (m) F-ISO)
IUPAC name 4,6-dinitro-o-cymen-3-ol
Chemical Abstracts name 3-methyl-2-(1-methylethyl)-4,6-dinitrophenol
Other names DNOIPP CAS RN [7257412] Smiles code CC(C)c1c(C)c(cc([N+]
(=O)[O-])c1O)[N+](=O)[O-]
10
H
12
N
2
O
5
COMMERCIALISATION:
History Herbicide and insecticide.
dinoseb 205
dinosam
Herbicide
NOMENCLATURE:
Common name dinosame ((m) F-ISO); dinosam (BSI, E-ISO)
IUPAC name 2-(1-methylbutyl)-4,6-dinitrophenol (I)
Chemical Abstracts name (I) Other names DNAP; DINOSAP CAS RN [409736
3] Smiles code CCCC(C)c1cc(cc([N+](=O)[O-])c1O)[N+](=O)[O-]
11
H
14
N
2
O
5
COMMERCIALISATION:
History Herbicide reported by A. S. Crafts (Plant Physiol., 1946, 21, 345). Introduced by
Standard Agricultural Chemicals Inc.
PRODUCTS:
Discontinued products Sinox General* (Standard).
ECClassifcation T; R23/24/25| N; R50, R53 (dinosam or its salts and esters)
dinoseb
HRAC M WSSA 24; dinitrophenol
NOMENCLATURE:
Common name dinoseb (BSI, E-ISO, ANSI, WSSA); dinos(be) ((m) F-ISO); DNBP (JMAF)
IUPAC name 2-sec-butyl-4,6-dinitrophenol
Chemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenol CAS RN [88
857] EC no 2018617 Development codes DN 289 (Dow); Hoe 26 150
Smiles code CCC(C)c1cc(cc([N+](=O)[O-])c1O)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
10
H
12
N
2
O
5
Form Orange solid;
(tech., orange-brown solid). M.p. 3842 C; (tech.: 3040 C) V.p. 0.13 mPa (room
temperature) (Adv. Chem. Series, ACS, cited in ARS PPD) K
ow
logP = 2.29 (unstated pH)
(Agchem. Desk Ref.) Henry 6.0 10
4
Pa m
3
mol
1
Solubility In water 52 mg/l (20 C). Soluble in most organic solvents and in petroleum
oils. In ethanol 480, heptane 270 (both in g/kg). pKa 4.62 F.p. 177 C
O
2
N
NO
2
OH
CHCH
2
CH
3
CH
3
206
dinoseb
COMMERCIALISATION:
History Herbicidal activity reported by A. S. Crafts (Science, 1945, 101, 417). Introduced by
Dow Chemical Co. (later DowElanco). Patents US 2192197 (to Dow); DE 1088757; GB
909732 (both to Hoechst)
APPLICATIONS:
Biochemistry Inhibits respiratory electron transport, and uncouples oxidative
phosphorylation. Mode of action Selective non-systemic herbicide with contact action.
Uses Dinoseb was used as the ammonium or an amine salt or acetate ester for post-
emergence weed control in cereals, undersown cereals, seedling alfalfa and peas at 2.5
kg/ha. Solutions of dinoseb in oil were used for pre-emergence control of annual weeds in
beans, peas and potatoes, for pre-harvest desiccation of hops, leguminous seed crops and
potatoes and for control of runners and suckers in raspberries and strawberries. Dinoseb
acetate was also used in combination with monolinuron pre-emergence in dwarf beans and
potatoes. Phytotoxicity Phytotoxic to cruciferous crops. Formulation types SL; EC; EO.
PRODUCTS:
Discontinued products Aretit* (Hoechst); Fanicide* (La Littorale); Farmon Desicoil
25* (Farm Protection); General Weedkiller* (Vertac); Ivosit* (Hoechst); Persevtox* (La
Quinoline); Premerge* (olamine and 2-hydroxypropylammonium salts) (Siapa, Tifa, Vertac);
Premerge 3* (olamine and diolamine salts) (Siapa, Tifa, Vertac); Selective Weedkiller*
(ammonium salt) (Vertac); Supersevtox* (diolamine and trolamine salts) (Schering).
ANALYSIS:
Product analysis by titration of a deriviative (CIPAC Handbook, 1994, F, 327) or by
colorimetry of solutions in alkali (D. S. Farrington et al., Analyst (London), 1983, 108, 353).
Residues determined by glc of a derivative (Anal. Methods Pestic. Plant Growth Regul., 1972, 6,
639). See also Pestic. Anal. Man., I, 208.
ICSC.149 (1994). EU Status (1107/2009) Considered to be outside the scope of the
Directive; already banned, 79/117/EEC as amended by 90/533/EEC.
Oral Acute oral LD
50
for rats 58, guinea pigs 25 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits 80200, guinea pigs 500 mg/kg. Mild skin and eye irritant (rabbits).
NOEL In 6 mo feeding trials, rats receiving 100 mg/kg diet showed no ill-effects.
ADI/RfD (EPA) cRfD 0.001 mg/kg b.w. [1989]. Water GV Excluded from GV derivation
(U). Other Very toxic to man (uncouples oxidative phosphorylation).
Toxicity Class WHO (a.i.) IbECClassifcation R44| T; R24/25| R61| R62| Xi; R36| N;
R50, R53 PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for chickens 26 mg/kg. Dietary LC
50
(5 d) for Japanese quail 409,
ring-necked pheasant 515 mg/kg diet. Fish Highly toxic to fsh. Bees Toxic to bees.
dinoseb acetate 207
ENVIRONMENTAL FATE:
Animals In mammals, undergoes oxidation of the sec-butyl side-chain, conjugation, and in
rats (but not in mice) reduction of either of the nitro groups and acetylation of the amino
group formed. Soil/Environment Under normal conditions of use, persistence in soil
isc. 26 weeks.
dinoseb acetate
Herbicide
NOMENCLATURE:
Common name dinoseb acetate (BSI, ISO-E, ANSI, WSSA); dinos(b ac) ((m) F-ISO);
DNBPA (JMAF)
IUPAC name 2-sec-butyl-4,6-dinitrophenyl acetate
Chemical Abstracts name 2-(1-methylpropyl)-4,6-dinitrophenyl acetate
CAS RN [2813958] Development codes Hoe 02904
Smiles code CCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
12
H
14
N
2
O
6
Form Brown oil with an
aromatic vinegar-like odour; (tech. is a viscous brown oil). M.p. 2627 C B.p. 170 C
/4 mmHg V.p. 28 mPa (43 C); 183 mPa (60 C) Solubility In water 2.2 g/l (20 C).
Readily soluble in aromatic solvents. Stability Hydrolysed by acids and alkalis, and slowly
hydrolysed in neutral media.
COMMERCIALISATION:
History Herbicidal activity reported by H. Hrtel (Meded. Landbouwhogesch. Opzoekingsstn.
Staat Gent, 1960, 25, 1422). Introduced by Hoechst AG (later AgrEvo GmbH).
APPLICATIONS:
Biochemistry Inhibits respiratory electron transport, and uncouples oxidative
phosphorylation. Mode of action Selective non-systemic herbicide with contact action.
Uses See dinoseb. Formulation types EC; WP. Compatibility Incompatible with
alkaline materials.
PRODUCTS:
Discontinued products Ivocit* (Hoechst); Phenotan* (Rhne-Poulenc).
ANALYSIS:
Product by spectrophotometry (D. S. Farrington et al., Analyst (London) 1983, 108 1284,
353360; CIPAC Handbook, 1970, 1, 337341). By coulometry (B. G. Kratochvil & I. M. Al-
Daher Analyst (London) 1981, 106(1264), 796799). Residues by GLC of a derivative with
ECD (Anal. Methods Pestic. Plant Growth Regul. 1972, 6, 639), or by spectrophotometry (ibid.
1967, 5, 390).
208
dinoterb
ICSC.882 (1997). EU Status (1107/2009) See dinoseb.
Oral Acute oral LD
50
for rats 6065 mg/kg. Inhalation LC
50
(4 h) for rats 1.3 mg/l air.
NOEL (2 y) for rats 100 mg/kg diet, for dogs 8 mg/kg diet. Other Very toxic to man
(uncouples oxidative phosphorylation). Toxicity Class WHO (a.i.) Ib
ECClassifcation R44| R61| R62| T; R24/25| Xi; R36| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Fish Toxic to fsh. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals Rapidly degraded to dinoseb (q.v.).
dinosulfon
NOMENCLATURE:
Common name dinosulfon (BSI, E-ISO, (m) F-ISO)
IUPAC name S-methyl O-2-(1-methylheptyl)-4,6-dinitrophenyl thiocarbonate
Chemical Abstracts name S-methyl O-[2-(1-methylheptyl)-4,6-
dinitrophenyl] carbonothioate CAS RN [5386776] unstated stereochemistry
Development codes MC 1143
Smiles code CCCCCCC(C)c1cc(cc([N+](=O)[O-])c1OC(=O)SC)[N+](=O)[O-]
16
H
22
N
2
O
6
S
COMMERCIALISATION:
History Acaricide and fungicide reported by M. Pianka & J. D. Edwards (J. Sci. Food
Agric., 1968, 19, 60) and M. Pianka & P. J. J. Sweet (ibid., pp. 672, 676). Evaluated by Murphy
Chemical Co. (later DowElanco).
dinoterb
Herbicide
HRAC M WSSA 24; dinitrophenol
NOMENCLATURE:
Common name dinoterbe ((m) F-ISO); dinoterb (BSI, E-ISO)
OH
C(CH
3
)
3
O
2
N
NO
2
dinoterb 209
IUPAC name 2-tert-butyl-4,6-dinitrophenol
Chemical Abstracts name 2-(1,1-dimethylethyl)-4,6-dinitrophenol
Other names DNTBP CAS RN [1420071] EC no 2158138
Development codes LS63 133 (Rhne-Poulenc) Smiles code CC(C)(C)c1cc(cc([N+]
(=O)[O-])c1O)[N+](=O)[O-]
10
H
12
N
2
O
5
Form Pale yellow solid,
with a phenol-like odour. M.p. 125.5126.5 C V.p. 20 mPa (20 C) Henry 1.07 Pa m
3
mol
1
(calc.) Solubility In water 4.5 mg/l (pH 5, 20 C). In cyclohexanone, ethyl acetate,
DMSOc. 200 g/kg. In alcohols, glycols, aliphatic hydrocarbonsc. 100 g/kg. Soluble in aqueous
alkalis with the formation of salts. Stability Stable below the melting point. Decomposes
above 220 C. Stable at least 34 d at pH 59 (22 C).
COMMERCIALISATION:
History Herbicide reported by G. A. Emery et al. (Proc. Conf. EWRC/COLUMA, 2nd,
1965, p. 41) (for acetate) and by P. Poignant & P. Crisinel (C. R. Journ. Etud. Herbic. Conf.
COLUMA, 4th, 1967, p. 196). Introduced by Ppro (now Bayer AG) and by Murphy
Chemical Ltd (who no longer manufacture or market it). Patents FR 1475686; FR
1532332; GB 1126658; US 3565601 (all to Ppro) Manufacturers Bayer CropScience
APPLICATIONS:
Biochemistry Oxidative phosphorylation uncoupler, leading to membrane disruption.
Mode of action Selective non-systemic herbicide with contact action. Uses Control of
annual broad-leaved weeds post-emergence in cereals, maize, alfalfa, and beet; and pre-
emergence in peas and beans. Also used for destruction of potato haulms.
Formulation types EC; SL .
ANALYSIS:
Product analysis by methylation with diazomethane followed by glc (CIPAC Handbook, 1983,
1B, 1797). Residues by glc; details available from Bayer CropScience.
EU Rev. Rep. 8083/VI/97 (1997). EU Status (1107/2009) Not approved, 98/269/EC.
Oral Acute oral LD
50
for rats 62, mice 25, rabbits 28 mg/kg. Skin and eye Acute
percutaneous LD
50
for guinea pigs 150 mg/kg. NOEL (2 y) for rats 0.375 mg/kg diet.
ADI/RfD (ECCO) No ADI [1997]. Toxicity Class WHO (a.i.) Ib.ECClassifcation
R61| T+; R28| T; R24| R44| N; R50, R53: (salts and esters are R61| T+; R28| T; R24| N; R50,
R53)
ECOTOXICOLOGY:
Fish LC
50
(96 h) for rainbow trout 0.0034 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, 98% is excreted in the faeces and urine
within 7 days.
210
diofenolan
dinoterbon
NOMENCLATURE:
Common name dinoterbon (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-tert-butyl-4,6-dinitrophenyl ethyl carbonate
Chemical Abstracts name 2-(1,1-dimethylethyl)-4,6-dinitrophenyl ethyl carbonate
CAS RN [6073729]
Smiles code CCOC(=O)Oc1c(cc(cc1C(C)(C)C)[N+](=O)[O-])[N+](=O)[O-]
13
H
16
N
2
O
7
COMMERCIALISATION:
History Acaricide and fungicide reported at 5th Int. Pestic. Congr., London, 1963 (M.
Pianka, J. Sci. Food Agric., 1966, 17, 47). Evaluated by Murphy Chemical Co. (later DowElanco).
diofenolan
Insecticide
NOMENCLATURE:
Common name diof(nolane) ((m) F-ISO); diofenolan (BSI, E-ISO)
IUPAC name A mixture of: (2RS,4SR)-4-(2-ethyl-1,3-dioxolan-4-ylmethoxy)phenyl phenyl
ether (5080%) and (2RS,4RS)-4-(2-ethyl-1,3-dioxolan-4-ylmethoxy)phenyl phenyl ether
(5020%)
Chemical Abstracts name A mixture of (2RS,4SR)-2-ethyl-4-[(4-phenoxyphenoxy)
methyl]-1,3-dioxolane and (2RS,4RS)-2-ethyl-4-[(4-phenoxyphenoxy)methyl]-
1,3-dioxolane CAS RN [63837332] Development codes CGA 059 205
Smiles code CCC1OCC(COc2ccc(Oc3ccccc3)cc2)O1
PHYSICAL CHEMISTRY:
Composition A mixture of 5080% (2RS,4SR)- isomer with 5020% (2RS,4RS)- isomer.
Mol. wt. 300.3 M.f. C
18
H
20
O
4
Form Clear, pale yellow viscous liquid. B.p. >250 C
/101.325 kPa (OECD 103) V.p. 1.1 10
1
mPa (25 C) (OECD 104) K
ow
logP = 4.8; 4.4
(cis- isomer); 4.3 (trans- isomer) (25 C) (OECD 117) Henry 6.74 10
3
Pa m
3
mol
1

(calc.) S.g./density 1.141 (20 C) Solubility In water 4.9 mg/l (25 C) (OECD 105).
Miscible with methanol, acetone, toluene, hexane, n-octanol. Stability Hydrolytically stable
at pH 7. Rapidly degraded by light. pKa No dissociation in range pH 111
O
O
O
CH
2
CH
3
O
CH
2
dioxabenzofos 211
COMMERCIALISATION:
History Reported by H. P. Streibert et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1994, 1, 23).
Introduced by Ciba-Geigy AG (later Novartis Crop Protection AG).
APPLICATIONS:
Mode of action Insect growth regulator with juvenile hormone activity. Inhibits
development of frst and second instar larvae of scales. Uses Active against most scale
insects and eggs of some Lepidoptera in citrus, pome fruit, stone fruit, grapes, mango, olives,
nuts, tea and ornamentals. Formulation types EC.
PRODUCTS:
Discontinued products Arbor* (Novartis); Aware* (Ciba); Context* (Ciba).
ANALYSIS:
By hplc with uv detection.
Oral Acute oral LD
50
50

for rats (24 h) >2000 mg/kg. Not irritant to skin or eyes (rabbits). Not a skin sensitiser.
Inhalation LC
50
3
. NOEL (3 mo) for rats 12 mg/kg b.w.;
NOAEL (3 mo) for dogs 12 mg/kg b.w.. ADI/RfD 0.006 mg/kg (provisional).
ECOTOXICOLOGY:
Birds Acute oral LC
50
for quail and ducks >2000 mg/kg. Fish LC
50
(96 h) for bluegill
sunfsh, catfsh, carp and trout 1.01.7 mg/l. Daphnia LC
50
(48 h) 0.5 mg/l. Algae LC
50
(72
h) 0.072 mg/l. Bees LD
50
(48 h, oral and contact) >96 mg/bee. Tech. material has a high
toxicity to the brood of the honeybee. Worms LC
50
(14 d) 204 mg/kg soil.
ENVIRONMENTAL FATE:
Animals Intestinal absorption 80%. Rapid elimination. Tissue residues low.
Soil/Environment Rapid dissipation: feld trials DT
50
c. 6 d; laboratory DT
50
<2 d. No
potential for mobility (RMF 0.15).
dioxabenzofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name dioxabenzofos (BSI, E-ISO, (m) F-ISO); salithion (JMAF)
O
P
O
OCH
3
S
212
dioxabenzofos
IUPAC name (RS)-2-methoxy-4H-1,3,25-benzodioxaphosphinine 2-sulfde; (RS)-2-
methoxy-4H-1,3,25-benzodioxaphosphorine 2-sulfde
Chemical Abstracts name ()-2-methoxy-4H-1,3,2-benzodioxaphosphorin
2-sulfde CAS RN [3811492] unstated stereochemistry EC no 2232923
Smiles code COP1(=S)OCc2ccccc2O1
8
H
9
O
3
PS Form Tech. is a light yellow
powder. M.p. 52.554 C V.p. 420 mPa (20 C) Henry 2.11 Pa m
3
mol
1
(calc.)
Solubility In water 43 mg/l (20 C). In acetonitrile, cyclohexanone, xylene >1 (all in kg/kg,
2123 C). Stability Stable in acidic to weakly alkaline media (pH 28).
COMMERCIALISATION:
History Insecticide reported by M. Eto & Y. Oshima (Agric. Biol. Chem., 1962, 26, 452).
Introduced by Sumitomo Chemical Co., Ltd. Patents JP 467645; JP 446747; GB 987378; FR
1360130
APPLICATIONS:
with contact, ingested and respiratory action. Uses Control of a wide range of boring,
chewing and sucking insects (Aphididae, Coccidae, Chilo spp., Curculionidae, Diaspididae,
Margarodidae, Lepidoptera, Plutella xylostella and Spodoptera spp.) in fruit, rice, tea,
tobacco and vegetables. Formulation types MG; EC; WP; GR; GP.
Compatibility Incompatible with strongly alkaline materials.
PRODUCTS:
Discontinued products Salithion* (Sumitomo Chemical).
ANALYSIS:
Product analysis by glc. Residues determined by glc with FPD (M. Eto & J. Miyamoto, Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 431).
EHC 63 (1986) is a general review of organophosphorus insecticides.
Oral Acute oral LD
50
for male rats 125, female rats 180, male mice 125 mg/kg.
50
for male rats 400, mice >1250 mg/kg.
Toxicity Class WHO (a.i.) IIECClassifcation T; R24/25, R39/25| N; R51, R53
ECOTOXICOLOGY:
Fish LC
50
dioxacarb 213
dioxacarb
Insecticide
IRAC 1A
NOMENCLATURE:
Common name dioxacarb (BSI, E-ISO, ANSI, ESA, JMAF); dioxacarbe ((m) F-ISO)
IUPAC name 2-(1,3-dioxolan-2-yl)phenyl methylcarbamate
Chemical Abstracts name 2-(1,3-dioxolan-2-yl)phenyl methylcarbamate
CAS RN [6988212] EC no 2302534 Development codes C 8353
Smiles code CNC(=O)Oc1ccccc1C2OCCO
2
11
H
13
NO
4
M.p. 114115 C V.p. 0.04 mPa (20 C) Henry 1.49 10
6
Pa m
3
mol
1
(calc.)
S.g./density 1.46 (20 C) Solubility In water 6 g/l (20 C). In acetone 280,
cyclohexanone 235, DMF 550, dichloromethane 345, ethanol 80, xylene 9, hexane 0.18 (all
in g/l, 20 C). Stability Relatively stable in neutral media, but decomposed in acidic and
alkaline media; DT
50
(calc., 20 C) 85 h (pH 5), 24.6 d (pH 7), 15 h (pH 9).
COMMERCIALISATION:
History Insecticide reported by F. Bachmann & J. B. Legge (J. Sci. Food Agric., Suppl., 1968,
p. 39). Introduced by Ciba AG (later Ciba-Geigy AG). Patents BE 670630; GB 1122633
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Insecticide with contact and
stomach action. Gives rapid knockdown. Uses Control of cockroaches (including those
resistant to organochlorine and organophosphorus insecticides), fies, Bed bugs, and other
public health pests in household use, animal houses, industrial areas, and stored products.
Control of chewing and sucking foliar insect pests on a range of crops. Particular uses
included control of colorado beetle on potatoes, leafhoppers and planthoppers on rice,
capsid bugs on cocoa, and various Beetles on oilseed rape. Formulation types WP; EC.
PRODUCTS:
Discontinued products Dimox* (Chimitox); Elocron* (Ciba-Geigy); Famid* (Ciba-
Geigy).
ANALYSIS:
Product analysis by acidimetric titration (A. Becker & W. Zeizler, Fresenius Z. Anal. Chem.,
1971, 257, 125). Residues determined by glc with ECD of a derivative.
O
O
O
C
O
CH
3
NH
214
dioxathion
EHC 64 (1986; a review of carbamate pesticides in general). EU Status (1107/2009) Not
Oral Acute oral LD
50
50
for
ratsc. 3000, rabbits 1950 mg/kg. Inhalation LC
50
for ratsc. 0.16 mg/l air. NOEL (90 d) for
rats 10 mg/kg daily; for dogs 2 mg/kg daily (marginal). Toxicity Class WHO (a.i.) II EPA
(formulation) II ECClassifcation T; R25| N; R51, R53
ECOTOXICOLOGY:
50
(96 h) for rainbow trout 29, carp 32 mg/l.
Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, dioxacarb is rapidly absorbed and
oxidised to the N-methylol and hydrolysed to the corresponding phenol. Both breakdown
products are eliminated as conjugates (e.g. glycosides), 8590% elimination occurring
within 24 h. Plants In plants, persists on foliage for c. 57 d. Soil/Environment
Dioxacarb is rapidly decomposed in soil. Persists on wall surfaces for up to 6 months.
dioxathion
IRAC 1B
NOMENCLATURE:
Common name dioxane phosphate (JMAF); delnav * (former exceptions: Turkey, USSR);
dioxathion (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name S,S-(1,4-dioxane-2,3-diyl) O,O,O,O-tetraethyl bis(phosphorodithioate)
Chemical Abstracts name S,S-1,4-dioxane-2,3-diyl bis(O,O-diethyl phosphorodithioate)
CAS RN [78342] EC no 2011077 Development codes Hercules AC258
Smiles code CCOP(=S)(OCC)SC1OCCOC1SP(=S)(OCC)OCC
PHYSICAL CHEMISTRY:
Composition Tech. is 6875%: 24% cis- , 48% trans- isomers,c. 30% related compounds.
Mol. wt. 456.5 M.f. C
12
H
26
O
6
P
2
S
4
Form Tech. is a brown liquid. S.g./density 1.257
(26 C) Solubility Insoluble in water. In hexane, kerosene 10 g/kg; soluble in most organic
solvents. Stability Stable in water at neutral pH, but hydrolysed by alkali or on heating.
Unstable to iron or tin surfaces or when mixed with certain carriers.
COMMERCIALISATION:
History Insecticide reported by W. R. Diveley et al. (J. Am. Chem. Soc., 1959, 81, 139). The
cis- is more toxic than the trans- isomer to fies and rats (B. W. Arthur & J. E. Casida, J.
diphenyl sulfone 215
Econ. Entomol., 1959, 52, 20). Introduced by Hercules Inc. (later by Nor-Am Chemical Co.).
Patents US 2725328; US 2815350
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact insecticide and
acaricide. Uses For treatment of livestock to control ectoparasites, including ticks and
biting fies. It was also used for residual control of chigoes, feas, mites and ticks in parks
and recreation areas. Formulation types EC.
PRODUCTS:
Discontinued products Delnav* (NOR-AM); Deltic* (NOR-AM).
ANALYSIS:
Product analysis by i.r. spectroscopy. Residues determined by glc (D. C. Abbott et al., Pestic.
Sci., 1970, 1, 10). See also Pestic. Anal. Man., II, 186.2450.
EHC 63 (1986; a general review of organophosphorus insecticides). JMPR Evaln. 11 (1968),
19 (1972). EU Status (1107/2009) Not approved, Commission Regulation 2076/2002.
Oral Acute oral LD
50
for male albino rats 43, female rats 23 mg/kg.
50
for male albino rats 235, female albino rats
63 mg/kg. NOEL Cholinesterase inhibition was observed in female rats receiving 10
mg/kg diet. ADI/RfD (JMPR) 0.0015 mg/kg b.w. [1968]. Toxicity Class WHO (a.i.) Ib
ECClassifcation T+; R26/28| T; R24| N; R50, R53| concn. dep.
diphenyl sulfone
Acaricide
NOMENCLATURE:
Common name diph(nylsulfone) (F-ISO, accepted in lieu of a common name.); diphenyl
sulfone (BSI, E-ISO)
IUPAC name diphenyl sulfone
Chemical Abstracts name 1,1-sulfonylbis[benzene] Other names DPS
CAS RN [127639] Smiles code O=S(=O)(c1ccccc1)c2ccccc2
12
H
10
O
2
S
COMMERCIALISATION:
History Acaricide reported by J. K. Eaton & R. G. Davies (Ann. Appl. Biol., 1950, 37, 471).
216
dipropetryn
dipropetryn
Herbicide
NOMENCLATURE:
Common name dipropetryn (BSI, E-ISO, ANSI, WSSA); diprop(tryne) ((f) F-ISO)
IUPAC name 6-ethylthio-N
2
,N4-diisopropyl-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-(ethylthio)-N,N-bis(1-methylethyl)-1,3,5-
triazine-2,4-diamine CAS RN [4147517] Development codes GS 16 068
Smiles code CCSc1nc(NC(C)C)nc(NC(C)C)n1
11
H
21
N
5
S Form Colourless powder.
M.p. 104106 C V.p. 0.097 mPa (20 C) K
ow
logP = 3.810 Henry 1.55 10
3
Pa m
3
mol
1

dichloromethane 300, toluene 220, methanol 190, n-octanol 130, hexane 9 (all in g/l, 20 C).
Stability Stable in neutral and alkaline media, but hydrolysed in strongly acidic media; DT
50

2428 d (pH 1, 25 C), >2.5 y (7<pH<13). Decomposed by uv light.
COMMERCIALISATION:
History Herbicide reported by G. A. Buchanan & D. L. Thurlow (Ala. Agr. Exp. Sta.
Highlights, 1968, 15(2), 7). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
Patents CH 337019; GB 814948
APPLICATIONS:
site. Mode of action Selective systemic herbicide, absorbed by the roots and foliage, with
rapid translocation acropetally through the xylem, accumulating in the apical meristems
and leaf tips. Uses Pre-emergence control of annual broad-leaved weeds and grasses in
cotton and water melons at 1.253.5 kg/ha. Formulation types FW; SC. WP.
PRODUCTS:
Discontinued products Cotofor* (Ciba-Geigy); Sancap* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc or by titration with perchloric acid in acetic acid. Residues
determined by glc with FPD (B. G. Tweedy & R. A. Kahrs, Anal. Methods Pestic. Plant Growth
Regul., 1978, 10, 493; K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192).
Oral Acute oral LD
50
LD
50
for rabbits >10 000 mg/kg. Mild skin irritant; non-irritating to eyes (rabbits). No skin
N N
N CH
3
CH
2
S NHCH(CH
3
)
2
NHCH(CH
3
)
2
disul; disul-sodium 217
sensitisation (guinea pigs). NOEL (98 d) for rats 400 mg/kg diet (27 mg/kg daily); (133 d)
for dogs 400 mg/kg diet (13 mg/kg daily). Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
50
(96 h) for rainbow trout 2.7, bluegill sunfsh
1.6 mg/l. Bees Practically non-toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Degradation involves dealkylation of the side-chains, splitting of the
ring, and evolution of CO
2
. Soil DT
50
c. 100 d.
dipyrithione
Fungicide
NOMENCLATURE:
Common name dipyrithione (BSI, E-ISO, (f) F-ISO, RINN)
IUPAC name di-2-pyridyl disulfde 1,1-dioxide
Chemical Abstracts name 2,2-dithiobis[pyridine] 1,1-dioxide CAS RN [3696284]
Development codes OSY-20 Smiles code O=n1ccccc1SSc2ccccn2=O
10
H
8
N
2
O
2
S
2
COMMERCIALISATION:
History Fungicide and bactericide discovered by Olin Chemicals and developed by
Yashima Chemical Industry Co. Ltd and Sankyo Co., Ltd.
APPLICATIONS: Uses Developed as a fungicide for use in rice.
PRODUCTS:
Discontinued products Omadine* (Yashima); Omadine disulfde* (Yashima); Omadine
DS* (Yashima).
disul; disul-sodium
Herbicide
NOMENCLATURE:
Common name sesone (WSSA); disul (E-ISO, (m) F-ISO); 2,4-DES (BSI, Australia, USSR)
IUPAC name 2-(2,4-dichlorophenoxy)ethyl hydrogen sulfate (I)
N S S
N
O
O
218
ditalimfos
Chemical Abstracts name (I) Other names SES CAS RN [149268] disul; [136
787] disul-sodium EC no 2052595 disul
PHYSICAL CHEMISTRY: Mol. wt. 287.1; (sodium salt 309.1) M.f. C
8
H
8
Cl
2
O
5
S;
(sodium salt C8H7Cl
2
NaO5S) Form The sodium salt forms colourless crystals.
M.p. 170 C (sodium salt) V.p. Negligible (sodium salt, room temperature)
Solubility In water 250 g/kg (sodium salt). Insoluble in most organic solvents except
methanol. The calcium salt is suffciently soluble to avoid precipitation from solutions
of 2,4-DES in hard water. Stability 2,4-DES-sodium is hydrolysed by alkali to form
2-(2,4-dichlorophenoxy)ethanol and sodium sulfate.
COMMERCIALISATION:
History Herbicide reported by L. J. King et al. (Contrib. Boyce Thompson Inst., 1950, 16,
191). Introduced by Union Carbide Corp. (later Rhne-Poulenc Ag.). Patents US 2573769
APPLICATIONS:
Biochemistry 2,4-DES-sodium is not itself phytotoxic, but is converted in moist soil
to 2-(2,4-dichlorophenoxy)ethanol which is oxidised to 2,4-D. Uses It was used as a
mixture with simazine to control annual weeds pre-em. in maize, soft fruits, roses, certain
established perennial crops and certain ornamental trees and shrubs.
PRODUCTS:
Discontinued products Crag Herbicide I* (disul) (Rhne-Poulenc); Crag
Sesone* (disul) (Rhne-Poulenc); Herbon* (sodium salt) (Atlas Interlates);
Discontinued mixtures Herbon Blue* (+ simazine) (Atlas).
ANALYSIS:
ANALYSIS: is by colorimetry of a derivative (J. N. Hogsett & G. L. Funk, Anal. Chem., 1954,
26, 849).
ICSC.142 (disul-sodium; 1995).
Oral Acute oral LD
50
for rats 730 mg/kg. NOEL In 2 y trials, rats receiving 2000 mg/kg
diet suffered no ill-effect. Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22| Xi;
R38, R41 (disul)
ditalimfos
Fungicide
NOMENCLATURE:
Common name ditalimphos ((m) F-ISO); ditalimfos (BSI, E-ISO, ANSI)
IUPAC name O,O-diethyl phthalimidophosphonothioate;
N-diethoxyphosphinothioylphthalimide
ditalimfos 219
Chemical Abstracts name O,O-diethyl (1,3-dihydro-1,3-dioxo-2H-
isoindol-2-yl)phosphonothioate CAS RN [5131248] EC no 2258758
Development codes Dowco 199 Smiles code CCOP(=S)(OCC)N1C(=O)
c2ccccc2C1=O
12
H
14
NO
4
PS Form Colourless plates
with a mild thiophosphate odour. M.p. 8384 C V.p. 1.93 10
1
mPa (25 C)
Solubility In water c. 133 mg/l (room temperature). Soluble in hexane, cyclohexane,
ethanol; very soluble in benzene, carbon tetrachloride, ethyl acetate and xylene.
Stability Stable to uv light; its stability is reduced at pH >8 or above its m.p. No
indication during storage of thiono-thiolo isomerisation which is characteristic of some
phosphorothioate esters.
COMMERCIALISATION:
History Fungicide reported by H. Tolkmith (Nature (London), 1966, 211, 522). Introduced
by Dow Chemical Co. (later DowElanco). Patents BE 661891, GB 1034493.
APPLICATIONS:
Mode of action Non-systemic foliar fungicide with protectant and curative activity.
Uses For control of powdery mildew on ornamentals (primarily roses) and vegetables
(cucurbits) under glass, as well as under feld conditions, at 3050 g/100 l; on apples, at
255- g/100 l; and cereals,at 500550 g/ha. Also used against Venturia inaequalis on apples
at 37.5100 g/100 l. Phytotoxicity Liable to russet certain apple cultivars, particularly
Golden Delicious.
Compatibility Not compatible with alkaline materials.
PRODUCTS:
Discontinued products Plondrel* (DowElanco).
ANALYSIS:
Product analysis is by uv spectroscopy. Residues by glc.
Oral Acute oral LD
50
for rats 49305660, male guinea pigs 5660 mg/kg.
Skin and eye Skin irritant; allergenic. Toxicity Class WHO (a.i.) U
ECClassifcation Xi; R38| R43
ECOTOXICOLOGY:
Birds Acute oral LD
50
for chickens 4500 mg/kg.
220
2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate
dithicrofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name dithicrofos (BSI, E-ISO, (m) F-ISO)
IUPAC name S-(6-chloro-3,4-dihydro-2H-1-benzothi-in-4-yl) O,O-diethyl
phosphorodithioate
Chemical Abstracts name S-(6-chloro-3,4-dihydro-2H-1-benzothiopyran-4-yl)
O,O-diethyl phosphorodithioate CAS RN [41219312] unstated stereochemistry
Development codes Hoe 19 510 Smiles code CCOP(=S)(OCC)SC1CCSc2ccc(Cl)
cc12
13
H
18
ClO
2
PS
3
COMMERCIALISATION:
History Insecticide evaluated by Hoechst AG.
APPLICATIONS:
2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate (I)
Chemical Abstracts name (I) CAS RN [21709444] Development codes C 13
963 Smiles code CN(C)C(=O)Oc1ccccc1C2SCCS2
12
H
15
NO
2
S
2
COMMERCIALISATION:
History Insecticide reported by F. Bachmann & J. B. Legge (J. Sci. Food Agric., Suppl., 1968,
p. 39). Evaluated by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
DMCP 221
DKA-24
Herbicide safener
NOMENCLATURE:
IUPAC name N1,N
2
-diallyl-N
2
-dichloroacetylglycinamide
Chemical Abstracts name 2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-2-
propenylacetamide CAS RN [97454007] Development codes DKA-24 (MV)
Smiles code ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C
10
H
14
Cl
2
N
2
O
2
Form Pale yellow liquid.
K
ow
logP = 1 Solubility In water 24.2 g/l (20 C). In acetone, chloroform, DMF >200 g/l.
Stability Stable 140 C, and between pH 4.5 and 8.3.
COMMERCIALISATION:
History Herbicide safener reported by J. Nagy & K. Balogh (Proc. Br. Crop Prot. Conf.
Weeds, 1985, 1, 107). Introduced by szakmagyarorszgi Vegyimvek Chemical Works,
North Hungary (later SagroChem Co., Ltd). Patents HU 2143821
APPLICATIONS: Uses A safener at 2001000 g/ha for thiocarbamate or
2-chloroacetanilide herbicides on maize. Formulation types EC.
Oral Acute oral LD
50
for rats 25002520, male mice 1010, female mice 1660 mg/kg.
50
for rats >5000 mg/kg. Non-irritating to eyes and
skin.
DMCP
Insecticide
NOMENCLATURE:
Common name DMCP (JMAF)
IUPAC name S-(4-chlorophenyl) O,O-dimethyl phosphorothioate
C
N CH
2
O
NH
C
O
HCCl
2
CH
2
=CHCH
2
CH
2
CH=CH
2
S(4-chlorophenyl) O,O-dimethyl phosphorothioate
P
O
O
O
S
Cl
S(4-chlorophenyl) O,O-dimethyl phosphorothioate
222
dodicin
CAS RN [3309873] Development codes B-3242
8
H
10
ClO
3
PS
COMMERCIALISATION:
History Insecticide marketed by Kumiai Chemical Industry Co. Ltd.
PRODUCTS:
Discontinued products Fujithion* (Kumiai).
DMPA
Herbicide
NOMENCLATURE:
Common name DMPA (WSSA)
IUPAC name O-2,4-dichlorophenyl O-methyl isopropylphosphoramidothioate
Chemical Abstracts name O-(2,4-dichlorophenyl) O-methyl (1-methylethyl)
phosphoramidothioate CAS RN [299854] Development codes K 22 023; Dowco
118 Smiles code COP(=S)(NC(C)C)Oc1ccc(Cl)cc1Cl
10
H
14
Cl
2
NO
2
PS
COMMERCIALISATION:
History Herbicide introduced by Dow Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Zytron* (DowElanco).
dodicin
Fungicide
NOMENCLATURE:
Common name dodicin (BSI, E-ISO, (f) F-ISO, BAN)
IUPAC name N-[2-(2-dodecylaminoethylamino)ethyl]glycine; 3,6,9-triazahenicosanoic
acid
Chemical Abstracts name N-[2-[[2-(dodecylamino)ethyl]amino]ethyl]glycine
CAS RN [6843976] Smiles code CCCCCCCCCCCCNCCNCCNCC(=O)O
18
H
39
N
3
O
2
COMMERCIALISATION:
History Fungicide and surface active agent.
drazoxolon 223
dofenapyn
Acaricide
NOMENCLATURE:
Common name dof(napyne) ((m) F-ISO); dofenapyn (BSI, E-ISO)
IUPAC name 4-(pent-4-ynyloxy)phenyl phenyl ether
Chemical Abstracts name 1-(4-pentynyloxy)-4-phenoxybenzene
AS RN [42873803] Development codes CGA 29 170
Smiles code C#CCCCOc1ccc(Oc2ccccc2)cc1
17
H
16
O
2
COMMERCIALISATION:
History Acaricide discovered by Ciba-Geigy AG.
PRODUCTS:
Discontinued products Acaban* (Ciba).
drazoxolon
Fungicide
NOMENCLATURE:
Common name drazoxolon (BSI, E-ISO, (m) F-ISO)
IUPAC name 4-(2-chlorophenylhydrazono)-3-methyl-1,2-oxazol-5(4H)-one;
4-(2-chlorophenylhydrazono)-3-methylisoxazol-5(4H)-one
Chemical Abstracts name 3-methyl-4,5-isoxazoledione 4-[(2-chlorophenyl)
hydrazone] CAS RN [5707697] EC no 2271978 Development codes PP781
Smiles code CC1=NOC(=O)C1=NNc2ccccc2Cl
10
H
8
ClN
3
O
2
M.p. 167 C V.p. 0.53 mPa (30 C) K
ow
logP = 2.6 Solubility In water <10 g/l (20 C).In
ethanol 10, chloroform 100, ketones 50, aromatic hydrocarbons 40 (all in g/kg). Practically
insoluble in acids and aliphatic hydrocarbons. Stability Stable in storage under normal
conditions. Stable to acids; dissolves in aqueous alkalis to form stable, soluble salts.
COMMERCIALISATION:
History Fungicide reported by M. J. Geoghegan (Proc. Br. Insectic. Fungic. Conf., 4th, 1967, 1,
451). Introduced by ICI Plant Protection Division (later Zeneca Agrochemicals).
Patents GB 999097
Cl
O
CH
3
N
O
N NH
224
DSP
APPLICATIONS:
Mode of action Foliar fungicide and seed treatment with protective and curative
action. Uses Control of powdery mildews on roses, blackcurrants, and other crops;
coffee rust; tea blister blight; Ganoderma spp. on rubber trees; etc. Also seed treatment
for control of Pythium and Fusarium spp. in peas, beans, peanuts, maize, cotton, and grass.
Phytotoxicity Mixtures with dodine are phytotoxic to apples. Formulation types SC.
FS . Compatibility Incompatible with lime sulfur.
PRODUCTS:
Discontinued products Ganocide* (ICI); Mil-Col* (Zeneca); SAIsan* (ICI).
ANALYSIS:
Product and residue analysis by colorimetry (S. H. Yuen, Anal. Methods Pestic. Plant Growth
Regul., 1973, 7, 665).
Oral Acute oral LD
50
for rats 126, mice 129, rabbits 100120, guinea pigs 12.525, dogs 17,
cats 50100 mg/kg. Skin and eye Non-irritating to skin and eyes, but some sensitisation
may occur, and prolonged contact should be avoided. Inhalation Rats exposed to 0.004
mg/l air for 15 daily periods of 6 h showed no toxic effect. Causes some lung irritation;
avoid vapour concentrations >0.0005 mg/l air. NOEL In 90 d feeding trials, rats receiving
30 mg/kg diet showed no ill-effects. Toxicity Class WHO (a.i.) IIECClassifcation T;
R25| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hensc. 100 mg/kg. Fish LC
50
(96 h) for brown trout 0.55 mg/l.
DSP
Insecticide
IRAC 1B
NOMENCLATURE:
Common name DSP (JMAF)
IUPAC name O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate;
4-diethoxyphosphinothioyloxy-N,N-dimethylbenzenesulfonamide
Chemical Abstracts name O-[4-[(dimethylamino)sulfonyl]phenyl] O,O-diethyl
phosphorothioate CAS RN [3078975] Development codes NK 0795
Smiles code CCOP(=S)(OCC)Oc1ccc(cc1)S(=O)(=O)N(C)C
12
H
20
NO
5
PS
2
COMMERCIALISATION:
History Insecticide introduced by Nippon Soda Co., Ltd.
eglinazine-ethyl; eglinazine 225
APPLICATIONS:
PRODUCTS:
Discontinued products Kayaace* (Nippon Soda).
EBP
Fungicide
IRAC 1B
NOMENCLATURE:
Common name EBP (JMAF)
IUPAC name S-benzyl O,O-diethyl phosphorothioate
Chemical Abstracts name O,O-diethyl S-(phenylmethyl) phosphorothioate
CAS RN [13286323] Smiles code CCOP(=O)(OCC)SCc1ccccc1
11
H
17
O
3
PS
COMMERCIALISATION:
History Fungicide introduced by Kumiai Chemical Industry Co., Ltd.
APPLICATIONS:
PRODUCTS:
Discontinued products Kitazin* (Kumiai).
eglinazine-ethyl; eglinazine
Herbicide
NOMENCLATURE:
Common name eglinazine (for acid) (BSI, E-ISO, (f) F-ISO, WSSA)
IUPAC name N-(4-chloro-6-ethylamino-1,3,5-triazin-2-yl)glycine (for acid)
Chemical Abstracts name N-[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]glycine (for
acid) CAS RN [6616804] ester; [68228193] acid Development codes MG-06
(ester)
N N
N Cl NHCH
2
CO
2
H
CH
3
CH
2
NH
226
EI 1642
PHYSICAL CHEMISTRY:
Composition Tech. isc. 96%. Mol. wt. 259.7; (acid 231.6) M.f. C
9
H
14
ClN
5
O
2
(ester);
C7H
10
ClN5O
2
(acid) Form Colourless crystals (ester). M.p. 228230 C (ester)
V.p. 0.027 mPa (20 C) (ester) Solubility In water 300 mg/l (25 C) (ester). In acetone
200, hexane 20, xylene 40 (all in g/l, 25 C) (ester). Stability Stable at room temperature
at pH 58. Hydrolysed on heating with acids or alkalis, forming the hydroxytriazine (which
is herbicidally inactive). Stable to light. Decomposes at 250 C.
COMMERCIALISATION:
History The ethyl ester introduced as a herbicide by Nitrokmia Ipartelepek.
APPLICATIONS: Uses Eglinazine-ethyl was used pre-emergence for control of loose
silky-bent (Apera spica-venti) and scentless mayweed (Matricaria perforata) in cereals at
3 kg/ha. Formulation types WP.
PRODUCTS:
Discontinued products MG06* (Nitrokmia).
ANALYSIS:
Product analysis by glc. Residues determined by glc with TID.
Oral Acute oral LD
50
for rats and mice >10 000, guinea pigs >3375 mg/kg.
50
for rats and rabbits >10 000 mg/kg. Non-irritating
to skin and eyes. Other Acute i.p. LD
50
for rats and mice >7100 mg/kg. No evidence of
cumulative toxicity. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
50
c. 1218 d.
EI 1642
Insecticide
NOMENCLATURE:
IUPAC name S-methyl N-(carbamoyloxy)thioacetimidate
Chemical Abstracts name methyl N-[(aminocarbonyl)oxy]ethanimidothioate
CAS RN [16960397] Development codes EI 1642
Smiles code CSC(=NOC(=O)N)C
4
H
8
N
2
O
2
M.p. 103104 C Solubility In water 45 g/kg (25 C). In acetone 170, ethanol 100,
methanol 300, isopropanol 30 (all in g/kg, 25 C); practically insoluble in kerosine, toluene.
COMMERCIALISATION:
History Insecticide evaluated by E. I. du Pont de Nemours & Co.
EL 177 227
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Effective as a foliar spray (150300 mg/l)
against aphids, lepidopterous and many other insect pests. Formulation types WP.
Oral The oral lethal dose for male rats isc. 60 mg/kg. Skin and eye Percutaneous lethal
dose for rabbits is >3400 mg/kg; it is not a skin irritant. NOEL In a 14 d trial with rats, ten
doses of 12 mg/kg showed no cumulative toxicity.
EL 177
Herbicide
NOMENCLATURE:
IUPAC name 1-tert-butyl-5-cyano-N-methylpyrazole-4-carboxamide
Chemical Abstracts name 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-
4-carboxamide CAS RN [98477077] Development codes EL-177; LYI 81 977
Smiles code CNC(=O)c1cnn(c1C#N)C(C)(C)C
10
H
14
N
4
O Form Crystalline solid.
M.p. 164166 C K
ow
logP = 1.3 Solubility Readily soluble in acetone, DMSO.
Stability Stable to light; and to hydrolysis at pH 3 and pH 7, slowly hydrolysed at pH 11.
COMMERCIALISATION:
History Herbicide reported by H. E. Chamberlain et al. (Proc. 1987 Br. Crop Prot. Conf. -
Weeds, 1, 35). Introduced by Eli Lilly.
Oral Acute oral LD
50
for mice and male rats >500 mg tech./kg, for female rats >50 mg/kg.
50
for rabbits >2000 mg/kg. Not a skin irritant; slight
eye irritant (rabbits). NOEL (42 d) for female rats 57 mg/kg daily, slight increase in liver
enzyme activity in males. Other Not teratogenic in rats at 250 mg/kg daily (highest dose
tested). Not mutagenic or genotoxic in Ames assay.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >500 mg/kg. Fish LC
50
(96 h) for bluegill sunfsh
>100 mg/l, rainbow trout >62 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Soil/water distribution coeffcient 0.31 (coarse-), 0.4 (medium-) and
0.45 (fne-textured soil).
228
endothion
EMPC
Insecticide
NOMENCLATURE:
Common name EMPC (JMAF)
IUPAC name 4-ethylthiophenyl methylcarbamate
Chemical Abstracts name 4-(ethylthio)phenyl methylcarbamate CAS RN [18809579]
Development codes NK-1 Smiles code CCSc1ccc(OC(=O)NC)cc1
10
H
13
NO
2
S
COMMERCIALISATION:
History Insecticide introduced by Nippon Kayaku Co., Ltd. Registration in Japan cancelled
in 1974.
APPLICATIONS:
PRODUCTS:
Discontinued products Toxamate* (Nippon Kayaku).
endothion
IRAC 1B
NOMENCLATURE:
Common name endothion (BSI, E-ISO, (m) F-ISO, ESA, ex ANSI)
IUPAC name S-5-methoxy-4-oxo-4H-pyran-2-ylmethyl O,O-dimethyl phosphorothioate;
2-dimethoxyphosphinoylthiomethyl-5-methoxypyran-4-one
Chemical Abstracts name S-[(5-methoxy-4-oxo-4H-pyran-2-yl)methyl]
O,O-dimethyl phosphorothioate CAS RN [2778043] EC no 2204723
Development codes 7175 RP (Rhne-Poulenc); AC 18 737 (Cyanamid); FMC 5767
(FMC) Smiles code COc1coc(CSP(=O)(OC)OC)cc1=O
9
H
13
O
6
PS
COMMERCIALISATION:
History Insecticide reported by F. Chaboussou & P. Ramadier (Rev. Zool. Agric. Appl., 1957,
55, 116). Introduced by Rhne-Poulenc Phytosanitaire and later by American Cyanamid Co.
and FMC Corp.
APPLICATIONS:
PRODUCTS:
Discontinued products Endocide* (Rhne-Poulenc).
endrin 229
Toxicity Class WHO (a.i.) OECClassifcation T; R24/25
endrin
Insecticide
NOMENCLATURE:
Common name nendrin (Republic of South Africa); endrine ((f) F-ISO); endrin (BSI,
E-ISO, ESA, JMAF)
IUPAC name (1R,4S,4aS,5S,6S,7R,8R,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-
octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene
Chemical Abstracts name (1a,2,2a,3,6,6a,7,7a)-3,4,5,6,9,9-hexachloro-
1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth[2,3-b]oxirene CAS RN [72208]
EC no 2007757 Development codes Experimental Insecticide 269 (Hyman)
Smiles code ClC1=C(Cl)C2(Cl)C3C4CC(C5OC54)C3C1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY:
12
H
8
Cl
6
O Form Colourless crystalline
solid; (tech. is a light tan solid). M.p. 226230 C (decomp.); (tech >200 C, decomp.) V.p.
2 10
5
mPa (20 C) S.g./density 1.64 (20 C) Solubility Negligible in water. Moderately
soluble in acetone, benzene; sparingly in alcohols, petroleum hydrocarbons. Stability Tech.
decomposes >200 C.
COMMERCIALISATION:
History Developed by Shell International Chemical Co. after introduction by J. Hyman &
Co. Patents US 2676132
APPLICATIONS:
Mode of action Contact insecticide. Uses Endrin is a foliar insecticide which acts against
a wide range of pests particularly Lepidoptera. It was used at 0.20.5 kg/ha on cotton,
maize, sugar cane, upland rice and many other crops. Formulation types EC; GR; WP.
PRODUCTS:
Discontinued products Endrex* (Shell); Mendrin* (Shell); Nendrin* (Velsicol).
ANALYSIS:
Product analysis by i.r. spectroscopy (CIPAC Handbook, 1983, 1B, 1805; FAO Specifcation
(CP/46); AOAC Methods 18th Ed., 961.05; Organochlorine Insecticides 1973), by tlc
(AOAC Methods 18th Ed., 972.05), or by potentiometric titration of liberated chloride ion
(CIPAC Handbook, 1994, F, 190), or by glc; mixtures with DDT and with parathion-methyl by
i.r. spectroscopy (CIPAC Handbook, 1983, 1B, 1760, 1819). Residues determined by glc, tlc
or paper chromatography (AOAC Methods, 18th Ed., 970.52), or by glc with ECD (Analyst
(London), 1979, 104, 425; G. M. Telling et al., J. Chromatogr., 1977, 137, 405; M. A. Luke et al., J.
230
enoxastrobin
Assoc. Off. Anal. Chem., 1981, 64, 1187; A. Ambrus et al., ibid., p. 733; Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 0393). In drinking water by glc with ECD (AOAC Methods, 18th Ed.,
990.06). See also Pestic. Anal. Man., I, 204, 208, 301, 302, 303, 502.
EHC 130 (1992). JMPR Mtg. 65 (1992); JMPR Evaln. 25 (1975). HSG 60 (1991). PDS 1 (1975).
ICSC.023 (2000). IARC 5 (1974). EU Status (1107/2009) Considered to be outside the
scope of the Directive; already banned, 79/117/EC, as amended by Regulation 850/2004.
IARC Class 3
Oral Acute oral LD
50
for rats 7.517.5 mg/kg. Skin and eye Acute percutaneous LD
50

for female rats 15 mg/kg. NOEL (2 y) for rats and dogs 1 mg/kg diet (0.025 mg/kg b.w.
for dogs); rats and mice showed no carcinogenic response. ADI/RfD (JMPR) 0.0002 mg/
kg b.w. (PTDI) [1994]; (EPA) cRfD 0.0003 mg/kg b.w. [1991]. Water GV 0.6 ;g/l Other
Produces neurotoxic effects. Toxicity Class WHO (a.i.) IbECClassifcation T+; R28| T;
R24| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for birds 0.755.64 mg/kg. Fish LC
50
(24 h) for fsh 0.755.6 mg/l.
ENVIRONMENTAL FATE:
Animals It is rapidly metabolised in animals to hydrophilic metabolites which are excreted
(M. R. Baldwin et al., Pestic. Sci., 1976, 7, 575). Continuous exposure to endrin in diets results
in only a limited accumulation in body fat.
enoxastrobin
Fungicide
NOMENCLATURE:
Common name enoxastrobin (pa ISO)
IUPAC name methyl 2-{2-[({[3-(4-chlorophenyl)-1-methylprop-2-enylidene]amino}oxy)
methyl]phenyl}-3-methoxyacrylate
Chemical Abstracts name methyl 2-[[[[3-(4-chlorophenyl)-1-methyl-2-propen-1-
ylidene]amino]oxy]methyl]--(methoxymethylene)benzeneaceate
CAS RN [238410112] Development codes SYPZ071 Smiles code C\C(/C=C/
C1=CC=C(Cl)C=C1)=N/OCC2=CC=CC=C2/C(C(OC)=O)=C\OC
22
H
22
ClNO
4
O
N
CH
3
Cl CO
2
Me
O
H
3
C
epofenonane 231
EPBP
Insecticide
IRAC 1B
NOMENCLATURE:
Common name EPBP (JMAF)
IUPAC name O-2,4-dichlorophenyl O-ethyl phenylphosphonothioate
Chemical Abstracts name O-(2,4-dichlorophenyl) O-ethyl phenylphosphonothioate
CAS RN [3792594] Development codes S-7 (Nissan)
Smiles code CCOP(=S)(Oc1ccc(Cl)cc1Cl)c2ccccc2
PHYSICAL CHEMISTRY:
14
H
13
Cl
2
O
2
PS Form Light brown
oil. B.p. 206 C /5 mmHg V.p. 5.09 10
5
mPa (200 C) S.g./density 1.312 (24 C)
Solubility Practically insoluble in water; soluble in most organic solvents.
COMMERCIALISATION:
History Insecticide introduced by Nissan Chemical Industries Ltd. Patents US 3318764
APPLICATIONS:
insecticide. Uses Used mainly to control soil-dwelling pests such as Agrotis fucosa,
Phyllotreta striolata, Rhizoglyphus echinopus and Hylemya spp. etc., using the dust at
1.83.0 kg/ha. Formulation types DP .
PRODUCTS:
Discontinued products S7* (Nissan); SSeven* (Nissan).
ANALYSIS:
Product analysis by glc. Residues determined by glc.
Oral Acute oral LD
50
for mice 275 mg/kg. Toxicity Class WHO (a.i.) II
epofenonane
Insecticide
NOMENCLATURE:
Common name epofenonane (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name 6,7-epoxy-3-ethyl-7-methylnonyl 4-ethylphenyl ether
Chemical Abstracts name 2-ethyl-3-[3-ethyl-5-(4-ethylphenoxy)pentyl]-2-
methyloxirane CAS RN [57342026] Development codes Ro 103108
Smiles code CCC(CCOc1ccc(CC)cc1)CCC2OC2(C)CC
20
H
32
O
2
232
erbon
COMMERCIALISATION:
History Insect growth regulator evaluated by Hoffmann-La Roche & Co.
epronaz
Herbicide
NOMENCLATURE:
Common name epronaz (BSI, E-ISO, (m) F-ISO)
IUPAC name N-ethyl-N-propyl-3-propylsulfonyl-1H-1,2,4-triazole-1-carboxamide
Chemical Abstracts name N-ethyl-N-propyl-3-(propylsulfonyl)-1H-1,2,4-triazole-
1-carboxamide CAS RN [59026083] Development codes BTS 30 843
Smiles code CCCN(CC)C(=O)n1cnc(n1)S(=O)(=O)CCC
11
H
20
N
4
O
3
S
COMMERCIALISATION:
History Herbicide reported by L. G. Copping & R. F. Brookes (Proc. Br. Weed Control Conf.,
12th, 1974, 2, 809). Evaluated by Boots Co., Ltd (later Schering Agriculture).
erbon
Herbicide
NOMENCLATURE:
Common name erbon (E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 2-(2,4,5-trichlorophenoxy)ethyl 2,2-dichloropropionate
Chemical Abstracts name 2-(2,4,5-trichlorophenoxy)ethyl 2,2-dichloropropanoate
CAS RN [136254] Smiles code CC(Cl)(Cl)C(=O)OCCOc1cc(Cl)c(Cl)cc1Cl
11
H
9
Cl
5
O
3
COMMERCIALISATION:
History Herbicide introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
Mode of action Total herbicide.
PRODUCTS:
Discontinued products Daron* (DowElanco).
Toxicity Class WHO (a.i.) OECClassifcation Xn; R22| N; R51, R53
etacelasil 233
ESBP
Fungicide
NOMENCLATURE:
Common name ESBP (JMAF)
IUPAC name S-benzyl O-ethyl phenylphosphonothioate
Chemical Abstracts name O-ethyl S-(phenylmethyl) phenylphosphonothioate
CAS RN [21722850] Smiles code CCOP(=O)(SCc1ccccc1)c2ccccc2
15
H
17
O
2
PS
COMMERCIALISATION:
History Fungicide introduced by Nissan Chemical Industries Ltd.
PRODUCTS:
Discontinued products Inezin* (Nissan).
etacelasil
NOMENCLATURE:
Common name etacelasil (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-chloroethyltris(2-methoxyethoxy)silane
Chemical Abstracts name 6-(2-chloroethyl)-6-(2-methoxyethoxy)-2,5,7,10-tetraoxa-6-
silaundecane CAS RN [37894465] EC no 2537047 Development codes CGA 13
586 Smiles code COCCO[Si](CCCl)(OCCOC)OCCOC
11
H
25
ClO
6
Si Form Colourless liquid.
B.p. 85 C /0.001 mmHg V.p. 27 mPa (20 C) Henry 3.42 10
4
Pa m
3
mol
1
(calc.)
S.g./density 1.10 (20 C) Solubility In water 25 g/l (20 C). Miscible with benzene,
methanol, hexane, dichloromethane and n-octanol. Stability On hydrolysis, DT
50
(calc.,
20 C) 50 min (pH 5), 160 min (pH 6), 43 min (pH 7), 23 min (pH 8).
COMMERCIALISATION:
History Abscission agent reported by J. Rufener & D. Piet (Riv. Ortoforofruttic. Ital.,
1974, 4, 274). Introduced by Ciba-Geigy AG. Patents BE 773498; GB 1371804
APPLICATIONS:
Mode of action Abscission agent which loosens fruit because of its ethylene-releasing
activity. Uses Loosening of olive fruit, which were then removed by mechanical shaking.
Formulation types SC. SL . Compatibility Not to be applied to trees recently sprayed
with copper fungicides or other pesticides containing stickers or surfactants.
PRODUCTS:
Discontinued products Alsol* (Ciba-Geigy).
234
etaconazole
ANALYSIS:
Product analysis by glc. Residues determined by glc with MCD.
Oral Acute oral LD
50
50

for rats >3100 mg/kg. Slight irritant to skin, not irritating to eyes (rabbits). Inhalation LC
50

(4 h) for rats >3.7 mg/l air. NOEL (90 d) for rats 20 mg/kg daily, for dogs 10 mg/kg daily.
Toxicity Class WHO (a.i.) IIIECClassifcation R61| Xn; R22, R48/22
ECOTOXICOLOGY:
Birds Non-toxic to birds. Fish LC
50
(96 h) for rainbow trout, crucian carp, bluegill sunfsh
>100 mg/l.
etaconazole
Fungicide
FRAC 3, G1; SBI Class I, DMI: triazole
NOMENCLATURE:
Common name (taconazole) ((m) F-ISO); etaconazole (BSI, E-ISO)
IUPAC name ()-1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-
triazole
Chemical Abstracts name 1-[[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl]
methyl]-1H-1,2,4-triazole CAS RN [60207934] unstated stereochemistry, formerly
[71245233] Development codes CGA 64 251
Smiles code CCC1COC(Cn2cncn2)(O1)c3ccc(Cl)cc3Cl
14
H
15
Cl
2
N
3
O
2
Form Colourless
crystals. M.p. 7593 C (depending on ratio of stereoisomers) V.p. 0.031 mPa (20 C)
Henry 1.27 10
4
Pa m
3
mol
1
80 mg/l (20 C). In acetone 300, dichloromethane 700, hexane 7.5, methanol 400,
isopropanol 100, toluene 250 (all in g/kg, 20 C). Stability Stable to hydrolysis, and at
<350 C.
COMMERCIALISATION:
History Fungicide reported by T. Staub et al. (Abstr. Int. Congr. Plant Protect., 1979, p. 310).
Introduced by Ciba-Geigy AG as an agricultural fungicide, having been invented by Janssen
Pharmaceutica, N.V. Patents GB 1522657; BE 835579
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. Mode of action Systemic, protective and
curative fungicide. Uses Used against Ascomycetes, Basidiomycetes and Deuteromycetes; it
has no activity on Oomycetes. It is especially active on powdery mildews, rusts, sclerotinia
and Venturia spp. on various crops. Post-harvest treatments are active against Fungi
etem 235
including Diplodia, Geotrichum and Penicillium spp. and others. (J. D. Van Geluwe et al., Abstr.
Int. Congr. Plant Protect., 1979, 495; J. D. Gilpatrick, ibid., p. 312). Formulation types WP.
PRODUCTS:
Discontinued products Sonax* (Ciba-Geigy); Vangard* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc with TID. Residues determined by glc with FID.
Oral Acute oral LD
50
50
for rats
>3100 mg/kg. Slight skin and eye irritant (rabbits). Toxicity Class WHO (a.i.) III
etem
Fungicide
An oxidation product of nabam (q.v.) (C. W. Pluijgers et al., Tetrahedron Lett., 1971,
1371; W. R. Benson et al., J. Assoc. Off. Anal. Chem., 1972, 55, 44; M. Alvarez et al.,
Tetrahedron Lett., 1973, 939). Also identifed as one of the oxidation products of other
ethylenebis(dithiocarbamates), e.g. maneb and zineb (R. A. Ludwig et al., Can. J. Bot., 1955,
33, 42).
NOMENCLATURE:
Common name ETM for (ii) (JMAF); etem for (i) (BSI); etem* for (ii) (BSI, before 1974)
IUPAC name (i) 5,6-dihydro-[3H]-imidazo[2,1-c]-[1,2,4]-dithiazole-3-thione; (ii)
1,3,6-thiadiazepane-2,7-dithione; ethylenethiuram monosulfde
Chemical Abstracts name (i) 5,6-dihydro-3H-imidazo[2,1-c]-1,2,4-dithiazole-3-thione;
(ii) hexahydro-1,3,6-thiadiazepine-2,7-dithione CAS RN [33813206] (i); [5782832] (ii)
EC no 2516844 Development codes UCP/21
PHYSICAL CHEMISTRY:
Composition Tech. may be contaminated by sulfur. Mol. wt. 176.3 (i); 178.3 (ii)
M.f. C
4
H
4
N
2
S
3
(i); C
4
H
6
N
2
S
3
(ii) Form Yellow crystalline powder. M.p. 121124 C
COMMERCIALISATION:
History Fungicide originally believed to be (ii), later corrected to (i). Evaluated by
Universal Crop Protection Ltd.
PRODUCTS:
Discontinued products Vegita* (Hokko, Kumiai).
S
S
N
N
S
236
ethidimuron
ANALYSIS:
Residue analysis is by glc (W. H. Newsome, J. Agric. Food Chem., 1975, 23, 348) or by
polarography (R. Engst & W. Schnaak, Z. Lebensm.-Unters. -Forsch., 1970, 144, 81).
ethidimuron
Herbicide
NOMENCLATURE:
Common name ethidimuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-(5-ethylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea
Chemical Abstracts name N-[5-(ethylsulfonyl)-1,3,4-thiadiazol-2-yl]-N,N-
dimethylurea Other names sulfodiazol CAS RN [30043493] EC no 2500106
Development codes MET 1486; BAY 107033
Smiles code CCS(=O)(=O)c1nnc(s1)N(C)C(=O)NC
7
H
12
N
4
O
3
S
2
M.p. 155.9156 C B.p. Decomposes on distillation V.p. 8 10
5
mPa (20 C) K
ow
logP
= 0.43 Henry 7.05 10-9 Pa m
3
mol
1
(calc.) Solubility In water 3 g/l (20 C). In hexane
<0.1, toluene 0.11.0, methanol 2, isopropanol 6, dichloromethane 106, chloroform 108,
acetone 150, acetonitrile 240 (all in g/kg, 20 C). Stability Stable in aqueous neutral and
acidic media, but unstable in alkaline media. Decomposes at 217 C.
COMMERCIALISATION:
History Herbicide reported by L. Eue et al. (C. R. Journ. Etud. Herbic. Conf. COLUMA, 4th,
1973, 1, 14). Introduced by Bayer AG. Patents BE 743615
APPLICATIONS:
site. Mode of action Non-selective herbicide, absorbed predominantly by the roots.
Uses Total herbicidal control on uncultivated land at 7 kg/ha, and in sugar cane plantations.
Formulation types WP; SC.
PRODUCTS:
Discontinued products Ustilan* (Bayer); Discontinued mixtures Novorail*
(+ amitrole + diuron) (CFPI).
N N
S
SO
2
CH
2
CH
3
N
C
CH
3
NH
O
CH
3
ethiolate 237
ANALYSIS:
Product analysis by i.r. spectrometry. Residues determined by glc with TID (H. J. Jarczyk,
Pfanz.-Nachr. Bayer (Engl. Ed.), 1979, 32, 186).
Oral Acute oral LD
50
for rats >5000, mice >2500, male dogs >5000 mg/kg.
50
for rats >1000 mg/kg. Non-irritating to skin and
eyes. Inhalation LC
50
(4 h) for rats, mice, and hamsters >0.24 mg/l air.
NOEL (90 d) for rats >1000 mg/kg diet. Toxicity Class WHO (a.i.) U EPA (formulation)
IV ECClassifcation R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail 300400, canaries 1000 mg/kg. Fish LC
50
(96 h)
for golden orfe >1000, goldfsh 400500, carp 200300 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
50
c. 34 months.
ethiolate
Herbicide
NOMENCLATURE:
Common name ethiolate (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name S-ethyl diethylthiocarbamate
Chemical Abstracts name S-ethyl diethylcarbamothioate CAS RN [2941551]
Smiles code CCSC(=O)N(CC)CC
7
H
15
NOS
COMMERCIALISATION:
History Herbicide introduced by Gulf Oil Chemicals Co.
PRODUCTS:
Discontinued mixtures Prefox* (+ cyprazine) (Gulf).
EHC 76 (1988); a general review of thiocarbamates.
238
ethirimol
ethirimol
Fungicide
FRAC 8, A2
NOMENCLATURE:
Common name ethirimol (BSI, E-ISO); (thyrimol) ((m) F-ISO)
IUPAC name 5-butyl-2-ethylamino-6-methylpyrimidin-4-ol
Chemical Abstracts name 5-butyl-2-(ethylamino)-6-methyl-4(1H)-pyrimidinone
(C.A. preferred tautomer) CAS RN [23947606] EC no 2459493
Development codes PP149 (ICI) Smiles code CCCCc1c(C)nc(NCC)nc1O
PHYSICAL CHEMISTRY:
Composition Tech. material is 97% pure. Mol. wt. 209.3 M.f. C
11
H
19
N
3
O
Form Colourless crystals. M.p. 159160 C (phase change atc. 140 C) V.p. 0.267 mPa
(25 C) K
ow
logP = 2.3 (pH 7, 20 C) Henry 2 10
4
(pH 5.2); 4 10
4
(pH 7.3); 4
10
4
(pH 9.3) Pa m
3
mol
1
(20 C) S.g./density 1.21 (25 C) Solubility In water 253 (pH
5.2), 150 (pH 7.3), 153 (pH 9.3) (all in mg/l, 20 C). In chloroform 150, ethanol 24, acetone
5 (all in g/kg, 20 C). Stability Stable to heat, and in acidic and alkaline solutions in the
dark. Aqueous solution exposed to sunlight and air had DT
50
c. 21 d. pKa 5, weak base
(K. Chamberlain et al., Pestic. Sci., 1996, 47, 265 and ref. therein).
COMMERCIALISATION:
History Fungicide reported by R. M. Bebbington et al. (Chem. Ind. (London), 1969, p. 1512).
Introduced by ICI Plant Protection Division (later Syngenta AG) and frst marketed in 1970.
Patents GB 1182584 Manufacturers Syngenta; Zhejiang Heyi
APPLICATIONS:
Biochemistry Inhibits nucleic acid synthesis (adenosine deaminase).
Mode of action Systemic fungicide with protective and curative action. Absorbed by the
roots and leaves, with translocation in the xylem, but not in the phloem. Uses Control of
powdery mildew on barley, wheat, and oats. Applied as a seed dressing, at 4 g/1000 g seed,
a foliar spray, at 250350 g/ha, or to the soil in the root zone. Also used for control of
powdery mildews on cucurbits. Formulation types EC; LS; SC.
PRODUCTS:
Discontinued products Milcurb Super* (Zeneca); Milgo* (Zeneca); Milstem* (Zeneca);
Discontinued mixtures Ferrax* (+ futriafol + thiabendazole) (seed) (Cheminova,
Syngenta); Halley* (+ hexaconazole) (Zeneca).
N
N NHCH
2
CH
3
CH
3
CH
3
(CH
2
)
3
OH
ethoate-methyl 239
ANALYSIS:
Product analysis by glc of a derivative (CIPAC Handbook, 1988, D, 72; J. E. Bagness & W. G.
Sharples, Analyst (London), 1974, 99, 225). Residues in crops determined by glc and in water
by hplc or by spectrometry (M. J. Edwards, Anal. Methods Pestic. Plant Growth Regul., 1976,
8, 285).
Oral Acute oral LD
50
for female rats 6340, mice 4000, female guinea pigs 5001000, male
rabbits 10002000 mg/kg. Skin and eye Acute percutaneous LD
50
Mild eye irritant; non-irritating to skin (rats). Not a skin sensitiser (guinea pigs).
Inhalation LC
50
for rats >4.92 mg/l. NOEL (2 y) for rats 200 mg/kg diet, for dogs 30 mg/
kg daily. Not carcinogenic or teratogenic. ADI/RfD (BfR) 0.1 mg/kg b.w. [1989]; (EPA) 0.05
mg/kg b.w. Toxicity Class WHO (a.i.) U EPA (formulation) IV ECClassifcation Xn; R21
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(96 h) for young brown trout 20,
rainbow trout 66 mg/l. Daphnia LC
50
(48 h) 53 mg/l. Bees LD
50
(oral) 1.6 mg/bee.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, metabolism involves hydroxylation of
the butyl group. Elimination is in the urine. Plants In plants, ethirimol undergoes rapid
degradation; 2-amino-5-butyl-6-hydroxy-4-methylpyrimidine is found as a metabolite. DT
50

in plantsc. 3 d. Soil/Environment Soil DT
50
14140 d (o.m. 1.010.1%, pH 7.88.1).
ethoate-methyl
IRAC 1B
NOMENCLATURE:
Common name ethoate-methyl (BSI, E-ISO); (thoate-m) (F-ISO)
IUPAC name S-ethylcarbamoylmethyl O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-ethylacetamide
Chemical Abstracts name S-[2-(ethylamino)-2-oxoethyl] O,O-dimethyl
phosphorodithioate CAS RN [116018] EC no 2041211 Development codes B/77
Smiles code CCNC(=O)CSP(=S)(OC)OC
6
H
14
NO
3
PS
2
COMMERCIALISATION:
History Insecticide and acaricide reported by G. Lemetre et al. (Not. Mal. Piante, 1963, No.
64). Introduced by Bombrini Parodi-Delfno (later Snia Viscosa).
240
ethylene dichloride
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact and systemic
insecticide and acaricide.
PRODUCTS:
Discontinued products Fitios* (Snia Viscosa).
Toxicity Class WHO (a.i.) OECClassifcation Xn; R21/22
ethylene bis(trichloroacetate)
Herbicide
NOMENCLATURE:
IUPAC name ethylene bis(trichloroacetate)
Chemical Abstracts name 1,2-ethanediyl bis(trichloroacetate) Other names
ethylene glycol bis(trichloroacetate) CAS RN [2514536] EC no 2197329
Smiles code ClC(Cl)(Cl)C(=O)OCCOC(=O)C(Cl)(Cl)Cl
6
H
4
Cl
6
O
4
COMMERCIALISATION:
History Herbicide introduced by Hooker Chemical Corp. (and later by Nor-Am).
APPLICATIONS:
Mode of action Total herbicide.
PRODUCTS:
Discontinued products Glytac* (Hooker).
Toxicity Class WHO (a.i.) OECClassifcation Xi; R38
ethylene dichloride
Insecticide
IRAC 8A
NOMENCLATURE:
Common name dichlorure d(thyl) (F-ISO, accepted in lieu of a common name); EDC
(JMAF); ethylene dichloride (BSI, E-ISO, ESA, accepted in lieu of a common name)
IUPAC name 1,2-dichloroethane (I)
ClCH
2
CH
2
Cl
N-ethylmercurio-4-toluenesulfonanilide 241
Smiles code ClCCCl
2
H
4
Cl
2
Form Colourless liquid, with
a chloroform-like odour. M.p. -36 C B.p. 83.5 C V.p. 10.4 kPa (20 C) Henry 2.39
10
2
Pa m
3
mol
1
(calc.) S.g./density 1.2569 (20 C) Solubility In water 4.3 g/l (room
temperature). Soluble in most organic solvents. F.p. 1215 C (Abel Pensky); lower and
upper limits of fammability in air 275 and 700 mg/l
COMMERCIALISATION:
History Reported as a component of insecticidal fumigants by R. T. Cotton & R. C. Roark
(J. Econ. Entomol., 1927, 20, 636).
APPLICATIONS:
Mode of action Fumigant insecticide. Uses An insecticidal fumigant used mainly in stored
products.
PRODUCTS:
Discontinued products EDC* (Toyo).
ANALYSIS:
Product analysis by glc (AOAC Methods, 18th Ed., 966.05). Residues in stored cereals
determined by glc with ECD (ibid., 977.18; K. A. Scudamore, Anal. Methods Pestic. Plant
Growth Regul., 1988, 16, 207, 231; Analyst (London), 1974, 99, 570; Anal. Methods Residues
Pestic., 1988, Part I). Methods reviewed by J. L. Daft in Comp. Anal. Profles,Chapter 11.
EHC 176 (1995). JMPR Evaln. 33 (1979). CAG. HSG 55 (1991). ICSC.250 (1995). IARC 20
(1979); 71 (1999). EU Status (1107/2009) Considered to be outside the scope of the
Directive; already banned, 79/117/EEC as amended by 87/181/EEC.
IARC Class 2B
Oral Acute oral LD
50
for rats 670890, mice 870950, rabbits 860970 mg/kg.
ADI/RfD (JMPR) No ADI [1994]. Water GV 0.03 mg/l (see note on carcinogens).
Toxicity Class WHO (a.i.) FMECClassifcation F; R11| Xn; R22| Xi; R36/37| N; R52,
R53| concn. dep. PIC Yes.
N-ethylmercurio-4-toluenesulfonanilide
Fungicide
NOMENCLATURE:
IUPAC name N-ethylmercurio-4-toluenesulfonanilide; N-(ethylmercury)-p-
toluenesulfonanilide
Chemical Abstracts name ethyl(4-methyl-N-phenylbenzenesulfonamidato-N)mercury
CAS RN [517168] Smiles code CC[Hg]N(c1ccccc1)S(=O)(=O)c2ccc(C)cc2
242
N-(2-ethyl-2H-pyrazol-3-yl)-N-phenylurea
15
H
17
HgNO
2
S
COMMERCIALISATION:
History Fungicide introduced by E. I. du Pont de Nemours & Co.
PRODUCTS:
Discontinued products Ceresan M* (DuPont); Granosan M* (DuPont).
N-(2-ethyl-2H-pyrazol-3-yl)-N-phenylurea
NOMENCLATURE:
IUPAC name N-(2-ethyl-2H-pyrazol-3-yl)-N-phenylurea
Chemical Abstracts name N-(1-ethyl-1H-pyrazol-5-yl)-N-phenylurea Other names
azoluron CAS RN [4058906] Smiles code CCn1nccc1NC(=O)Nc2ccccc2
12
H
14
N
4
M.p. 201202 C S.g./density 1.18 (25 C) Solubility In water 365 mg/l (25 C). In
acetone 20.3, chloroform 2.3 (both in g/l, 25 C). Soluble in ethanol; sparingly soluble in
diethyl ether; almost insoluble in benzene and hexane. Stability Stable under normal
conditions. Hydrolysed rapidly in strong acids and alkalis; DT
50
(pH 7) 180 d.
COMMERCIALISATION:
History Plant growth regulator introduced by Fahlberg-List to stimulate fower formation
in glasshouse tomatoes.
APPLICATIONS:
Biochemistry Plant growth regulator with cytokinin-like activity, stimulating cell division,
organ formation and cell elongation (i.e. internodes), as well as seed germination.
Uses In combination with gibberellic acid, used to stimulate fower formation in glasshouse
tomatoes, and thus to produce a higher yield of early tomatoes.
N
N
NHCONH
CH
2
CH
3
etnipromid 243
ANALYSIS:
Product by potentiometric titration with perchloric acid in acetic acid.
Oral Acute oral LD
50
for rats 2700 mg/kg. NOEL (90 d) for rats 25 mg/kg daily.
ENVIRONMENTAL FATE:
Plants Degradation in plants probably involves splitting of the urea bond, with
hydroxylation and glycosidation of the aromatic metabolites.
etinofen
Herbicide
NOMENCLATURE:
Common name (tinof) ((m) F-ISO); etinofen (BSI, E-ISO)
IUPAC name -ethoxy-4,6-dinitro-o-cresol
Chemical Abstracts name 2-(ethoxymethyl)-4,6-dinitrophenol CAS RN [2544947]
Smiles code CCOCc1cc(cc([N+](=O)[O-])c1O)[N+](=O)[O-]
9
H
10
N
2
O
6
COMMERCIALISATION:
History Herbicide introduced by C. H. Boehringer Sohn (later Shell Agrar).
PRODUCTS:
Discontinued products Dinethon* (Shell Agrar).
etnipromid
Herbicide
NOMENCLATURE:
Common name etnipromide ((m) F-ISO); etnipromid (BSI, E-ISO)
IUPAC name (RS)-2-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]-N-ethylpropionamide
Chemical Abstracts name ()-2-[5-(2,4-dichlorophenoxy)-2-nitrophenoxy]-
N-ethylpropanamide CAS RN [76120020] unstated stereochemistry
Development codes Hoe 39 106 Smiles code CCNC(=O)C(C)Oc1cc(Oc2ccc(Cl)
cc2Cl)ccc1[N+](=O)[O-]
17
H
16
Cl
2
N
2
O
5
COMMERCIALISATION:
History Herbicide evaluated by Hoechst AG.
244
etrimfos
etrimfos
IRAC 1B
NOMENCLATURE:
Common name etrimfos (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name O-6-ethoxy-2-ethylpyrimidin-4-yl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-(6-ethoxy-2-ethyl-4-pyrimidinyl) O,O-
dimethyl phosphorothioate CAS RN [38260547] EC no 2538559
Development codes SAN 197I Smiles code CCOc1cc(OP(=S)(OC)OC)nc(CC)n1
10
H
17
N
2
O
4
PS Form Colourless oil.
M.p. -3.35 C V.p. 6.5 mPa (20 C); 18 mPa (30 C); 49 mPa (40 C) K
ow
logP >3.3
S.g./density 1.195 (20 C) Solubility In water 40 mg/l (2324 C). Completely miscible
with acetone, acetonitrile, chloroform, DMSO, ethanol, diethyl ether, ethyl acetate, hexane,
kerosene, methanol, toluene, xylene. Stability Unstable when pure (c. 40% degradation
in 28 d at 4852 C), but dilute solutions in non-polar solvents and its formulations are
stable (c. 5% loss in 1 y at 1822 C). When stored in the dark at 2224 C for 28 d, no
decomposition occurred in hexane, toluene, chloroform, acetone;c. 3% decomposition in
methanol;c. 12% decomposition in ethyl acetate. Hydrolysis DT
50
(25 C) 0.4 d (pH 3), 16 d
(pH 6), 14 d (pH 9). High stability to light.
COMMERCIALISATION:
History Insecticide reported by H. J. Knutti & F. W. Reisser (Proc. Br. Insectic. Fungic. Conf.,
5th, 1975, 2, 675). Introduced by Sandoz Agro AG (later Novartis Crop Protection AG).
APPLICATIONS:
acaricide with contact and stomach action. Uses Control of Lepidoptera, Coleoptera,
Diptera, and some Hemiptera at 250750 g/ha on fruit trees (including citrus), vines, olives,
potatoes, vegetables, maize, alfalfa, ornamentals, tobacco. Control of Pyralidae in paddy rice
at 1.01.5 kg/ha. It was also used at 310 mg/kg for control of Lepidoptera, Coleoptera,
mites, and lice in stored products. Phytotoxicity May be phytotoxic to begonias, and, for
EC formulations, to cherries and some varieties of apple. Formulation types DP; EC; GR;
LS; UL . Compatibility Not compatible with pesticides which are strongly alkaline.
PRODUCTS:
Discontinued products Ekamet* (Novartis); Satisfar* (Novartis).
P(OCH
3
)
2
S
N
N
CH
3
CH
2
O
CH
3
CH
2
O
EXD 245
ANALYSIS:
Product analysis by glc. Residues determined by glc (Man. Pestic. Residue Anal., pp. 6, 19; Anal.
Methods Residues Pestic., 1988, Part I, M2, M5; J. C. Karpally et al., Anal. Methods Pestic. Plant
Growth Regul., 1980, 11, 125; Analyst (London), 1985, 110, 765).
EHC 63 (1986) is a general review of organophosphorus insecticides. JMPR Evaln. I 60
(1990); JMPR Evaln. 39 (1982). EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD
50
percutaneous LD
50
for rats >5000, male rabbits >500 mg/kg. Inhalation LC
50
(1 h) for rats
>200 mg a.i. (as 50% EC)/l air. NOEL (90 d) for rats 9 mg/kg diet; (6 mo) for dogs
12 mg/kg diet; (2 y) for rats 6, dogs 10 mg/kg diet. ADI/RfD (JMPR) 0.003 mg/kg b.w.
[1986]. Toxicity Class WHO (a.i.) II EPA (formulation) III ECClassifcation Xn; R22| N;
R50, R53| concn. dep.
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for quail 740 mg/kg diet. Fish LC
50
(96 h) for carp and guppies
5.5 mg/l, rainbow trout 24 ;g/l. Daphnia LC
50
(48 h) 0.0173 mg/l. Algae EC
50
(96 h) for
Scenedesmus subspicatus 2.9 mg/l. Bees Toxic to bees by contact.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, etrimfos is rapidly metabolised and
excreted, mainly in the urine. Metabolites include 6-ethoxy-4-hydroxy-2-ethylpyrimidine,
2-ethyl-4,6-dihydroxypyrimidine, 6-ethoxy-4-hydroxy-2-(1-hydroxyethyl)pyrimidine, and
other isomers. Plants In plants, etrimfos undergoes rapid metabolism to 6-ethoxy-4-
hydroxy-2-ethylpyrimidine, and small amounts of 2-ethyl-4,6-dihydroxypyrimidine and other
hydroxylated derivatives. Soil/Environment Soil DT
50
310 d (o.c. 2.8%, pH 6.8). The
principal degradation products are 6-ethoxy-4-hydroxy-2-ethylpyrimidine, small amounts of
2-ethyl-4,6-dihydroxypyrimidine and other hydroxylated derivatives, and CO
2
.
EXD
Herbicide
NOMENCLATURE:
Common name EXD (WSSA)
IUPAC name O,O-diethyl dithiobis(thioformate)
Chemical Abstracts name diethyl thioperoxydicarbonate; thioperoxydicarbonic
acid ([(HO)C(S)]2S2) diethyl ester Other names dixanthogen CAS RN [502556]
EC no 2079444 Smiles code CCOC(=S)SSC(=S)OCC
6
H
10
O
2
S
4
246
fenaminosulf
COMMERCIALISATION:
History Herbicide reported by E. K. Alban & L. McCombs (Proc. North Cent. Weed Control
Conf., 1949, p. 81). Introduced by Roberts Chemicals Inc. and Monsanto Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Herbisan* (Roberts Chemicals); Sulfasan* (Monsanto).
fenaminosulf
Fungicide
NOMENCLATURE:
Common name fenaminosulf (BSI, E-ISO); ph(naminosulf) ((m) F-ISO); DAPA (JMAF)
IUPAC name sodium 4-dimethylaminobenzenediazosulfonate
Chemical Abstracts name sodium [4-(dimethylamino)phenyl]diazenesulfonate
CAS RN [140567] EC no 2054194 Development codes Bayer 22 555; Bayer 5072
Smiles code [Na+].CN(C)c1ccc(N=NS(=O)(=O)[O-])cc1
8
H
10
N
3
NaO
3
S Form Yellowish-brown
powder. Solubility In water 40 g/kg (20 C). Soluble in DMF; insoluble in benzene, diethyl
ether, petroleum oils. Stability Stable 200 C. Its aqueous solution is intense orange and
is sensitive to light but is stabilised by sodium sulfte; stable in alkaline media.
COMMERCIALISATION:
History Fungicide reviewed by E. Urbschat (Angew. Chem., 1960, 72, 981). Introduced by
Bayer AG. Patents DE 1028828
APPLICATIONS:
Biochemistry Interferes with NADH-ubiquinone reductase (complex I). Uses Applied
to seed or soil for the control of Pythium, Aphanomyces and Phytophthora spp. in soil at
45110 g/100 kg seed (depending on the crop). Formulation types WP.
PRODUCTS:
Discontinued products Dexon* (Bayer); Lesan* (Bayer).
ANALYSIS:
Product analysis by polarography. Residues determined by colorimetry (D. MacDougall,
Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 3, 49).
fenapanil 247
Oral Acute oral LD
50
for rats 60, guinea pigs 150 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >100 mg/kg. Toxicity Class WHO (a.i.) II
ECClassifcation T; R25| Xn; R21| N; R52, R53
fenaminstrobin
Acaricide
NOMENCLATURE:
Common name fenaminstrobin (pa ISO)
IUPAC name methyl (E)-2-{-[2-(2,4-dichloroanilino)-6-(trifuoromethyl)pyrimidin-4-
yloxy]-o-tolyl}-3-methoxyacrylate
Chemical Abstracts name methyl (E)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-
(trifuoromethyl)-4-pyrimidinyl]oxy]methyl]--(methoxymethylene)benzeneacetate
CAS RN [1257598438] Development codes SYP1620
Smiles code CO\C=C(C(OC)=O)/C1=C(COC2=CC(C(F)(F)F)=NC(NC3=CC=C(Cl)
C=C3Cl)=N
2
)C=CC=C1
23
H
18
Cl
2
F
3
N
3
O
4
fenapanil
Fungicide
NOMENCLATURE:
Common name f(napanil) ((m) F-ISO); fenapanil (BSI, ANSI, E-ISO)
IUPAC name ()-2-(imidazol-1-ylmethyl)-2-phenylhexanenitrile; ()--butyl--
phenylimidazole-1-propanenitrile
Chemical Abstracts name -butyl--phenyl-1H-imidazole-1-
propanenitrile CAS RN [61019781] Development codes RH-2161
Smiles code CCCCC(Cn1ccnc1)(C#N)c2ccccc2
16
H
19
N
3
COMMERCIALISATION:
History Fungicide evaluated by Rohm & Haas Co.
CO
2
Me
O
H
3
C
O
N
N
HN
Cl
Cl
CF
3
248
fenazafor
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor.
PRODUCTS:
Discontinued products Sisthane* (Rohm & Haas).
fenasulam
Herbicide
NOMENCLATURE:
Common name fenasulam (BSI, E-ISO)
IUPAC name methyl 4-[2-(4-chloro-o-tolyloxy)acetamido]phenylsulfonylcarbamate;
methyl (N-4-chloro-o-tolyloxyacetylsulfanilyl)carbamate
Chemical Abstracts name methyl [[4-[[(4-chloro-2-methylphenoxy)acetyl]amino]
phenyl]sulfonyl]carbamate CAS RN [78357489] Development codes SSH-60
Smiles code COC(=O)NS(=O)(=O)c1ccc(NC(=O)COc2ccc(Cl)cc2C)cc1
17
H
17
ClN
2
O
6
S
COMMERCIALISATION:
History Herbicide evaluated by Shionogi and Co. Ltd.
fenazafor
Acaricide
NOMENCLATURE:
Common name fenazafor (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name phenyl 5,6-dichloro-2-trifuoromethylbenzimidazole-1-carboxylate
Chemical Abstracts name phenyl 5,6-dichloro-2-(trifuoromethyl)-1H-benzimidazole-1-
carboxylate CAS RN [14255880] EC no 2381349 Development codes NC 5016
Smiles code FC(F)(F)c1nc2cc(Cl)c(Cl)cc2n1C(=O)Oc3ccccc3
15
H
7
Cl
2
F
3
N
2
O
2
COMMERCIALISATION:
History Acaricide reported by D. T. Saggers & M. L. Clark (Nature (London), 1967, 215, 275).
Introduced by Fisons Pest Control Ltd (later Schering Agriculture).
APPLICATIONS:
Mode of action Contact acaricide.
PRODUCTS:
Discontinued products Lovozal* (Schering); Tarzol* (Fisons).
fenchlorazole-ethyl 249
Toxicity Class WHO (a.i.) OECClassifcation Xn; R21/22| N; R50, R53
fenchlorazole-ethyl
Herbicide safener
NOMENCLATURE:
Common name fenchlorazole (BSI, E-ISO, (m) F-ISO, for the carboxylic acid)
IUPAC name ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-
carboxylate
Chemical Abstracts name ethyl 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-
1H-1,2,4-triazole-3-carboxylate CAS RN [103112352]; [103112363] acid
EC no 4012905 Development codes Hoe 070542 (Hoechst); Hoe 072829 (acid)
Smiles code acid:OC(=O)c1nc(n(n1)c2ccc(Cl)cc2Cl)C(Cl)(Cl)Cl;ester:CCOC(=O)
c1nc(n(n1)c2ccc(Cl)cc2Cl)C(Cl)(Cl)Cl
12
H
8
Cl
5
N
3
O
2
; (acid
C
10
H4Cl5N3O
2
) Form White, practically odourless solid. M.p. 108112 C
V.p. 8.9 10
4
mPa (20 C) (OECD 104) Henry 3.71 10
4
Pa m
3
mol
1
(20 C, calc.)
S.g./density 1.7 (20 C) Solubility In water 0.9 mg/l (pH 4.5, 20 C). In n-hexane 2.5,
methanol 27, toluene 270, acetone 360, dichloromethane >500 (all in g/l, 20 C).
Stability Aqueous hydrolysis DT
50
115 d (pH 5), 5.5 d (pH 7), 0.079 d (pH 9).
COMMERCIALISATION:
History Herbicide safener reported by H. Bieringer et al. (Proc. 1989 Br. Crop Prot. Conf.
- Weeds, 1, 77). Fenchlorazole-ethyl introduced by Hoechst AG (later Bayer CropScience).
Manufacturers Anhui Huaxing; Bayer CropScience
APPLICATIONS:
Biochemistry Fenchlorazole-ethyl synergises the activity of fenoxaprop-ethyl (or
fenoxaprop-P-ethyl) in susceptible species by enhancing de-esterifcation to the acid,
which is the active form. It also enhances the tolerance of wheat by accelerating the
metabolic breakdown of fenoxaprop, leading to the formation of non-phytotoxic
degradation products (J. C. Hall & G. R. Stephenson, Proc. Br. Crop Prot. Conf. Weeds, 1995,
1, 261; J. C. Hall et al., Proc. 9th IUPAC Int. Congr. Pestic. Chem., London, 1998, 5E-005).
Mode of action Applied to the foliage of wheat in combination with the grass herbicide
fenoxaprop-ethyl or fenoxaprop-P-ethyl, it prevents growth retardation, leaf discoloration,
Cl N
N
N
CO
2
CH
2
CH
3
CCl
3
Cl
250
fenchlorphos
and chlorosis of the crop. Uses Used as a safener for fenoxaprop-ethyl or fenoxaprop-P-
ethyl in post-emergence control of grass weeds in wheat, durum wheat, rye, and triticale.
EU Status (1107/2009) Considered to be outside the scope of the Directive; considered
not to be a plant protection product.
Oral Acute oral LD
50
for rats >5000, mice >2000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats and rabbits >2000 mg/kg. Non-irritating to eyes and skin
(rabbits). Non-sensitising to skin (guinea pigs). Inhalation LC
50
(4 h) >1.52 mg/l.
NOEL (90 d) for rats 1280, male mice 80, female mice 320, dogs 80 mg/kg diet; (1 y) for
dogs 80 mg/kg diet. ADI/RfD (BfR) 0.0025 mg/kg b.w. [1991]. Toxicity Class WHO (a.i.)
UECClassifcation (R40)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks >2400 mg/kg. Fish LC
50
0.08 mg/l. Daphnia LC
50
(48 h) 1.8 mg/l. Bees Not harmful to bees; LC
50
(48 h)
>300 g/bee.
fenchlorphos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name fenchlorphos (BSI, E-ISO, (m) F-ISO, BAN); ronnel (ANSI, Canada, ESA,
and formerly France)
IUPAC name O,O-dimethyl O-2,4,5-trichlorophenyl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-(2,4,5-trichlorophenyl) phosphorothioate
CAS RN [299843] EC no 2060826 Development codes Dow ET-14; Dow ET-57
Smiles code COP(=S)(OC)Oc1cc(Cl)c(Cl)cc1Cl
8
H
8
Cl
3
O
3
PS Form Colourless
crystalline powder. M.p. Softens 3537 C; melts 4042 C V.p. 110 mPa (25 C)
Solubility In water 40 mg/l (room temperature). Readily soluble in most organic solvents
including refned kerosine. Stability Stable 60 C; stable in neutral and acidic media;
hydrolysed by dilute alkali to the demethyl compound.
COMMERCIALISATION:
History Systemic insecticide introduced by Dow Chemical Co. Patents US 2599516, GB
699064.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide. Uses As a
residual spray for the control of fies and other household pests. Also against ectoparasites
of cattle, sheep and pigs; as a pour-on and backrubber application for lice and hornfy
fenethacarb 251
control on cattle; as a dip against itch-mite (e.g. Psorergates ovis) and other ectoparasites
of sheep. Also against cattle ectoparasites and in various preparations (oils and aerosol
concentrates) as a wound dressing against blowly in livestock and for spot applications for
the control of ticks on cattle. Formulation types AE; EC; PO; SA.
Compatibility Incompatible with alkaline pesticides.
PRODUCTS:
Discontinued products Korlan* (Dow); Nankor* (Dow); Trolene* (Dow).
ANALYSIS:
Residues determined by glc, tlc or paper chromatography (AOAC Methods 18th Ed., 970.52).
See also Pestic. Anal. Man., I, 303.
ICSC.975 (1995). EU Status (1107/2009) Never notifed to the EU.
Oral Acute oral LD
50
for rats 1740 mg/kg. NOEL (2 y) for rats 1.5 mg/kg b.w. (EPA
Tracking). ADI/RfD (JMPR) 0.01 mg/kg b.w. (1968); (EPA) 0.015 mg/kg b.w. [1987].
Toxicity Class WHO (a.i.) IIECClassifcation Xn; R21/22| N; R50, R53
fenethacarb
Insecticide
NOMENCLATURE:
Common name fenethacarb (BSI, E-ISO); ph(n) ((m) F-ISO)
IUPAC name 3,5-diethylphenyl methylcarbamate (I)
Chemical Abstracts name (I) CAS RN [30087479] Development codes BAS
235I (BASF) Smiles code CCc1cc(CC)cc(OC(=O)NC)c1
12
H
17
NO
2
COMMERCIALISATION:
History Insecticide introduced by BASF AG.
APPLICATIONS:
252
fenfuthrin
fenfuthrin
Insecticide
IRAC 3
NOMENCLATURE:
Common name fenfuthrin (BSI, E-ISO); fenfuthrine ((f) F-ISO)
IUPAC name 2,3,4,5,6-pentafuorobenzyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethy
lcyclopropanecarboxylate; 2,3,4,5,6-pentafuorobenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-
Chemical Abstracts name (1R-trans)-(pentafuorophenyl)methyl
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate CAS RN [75867004]
Development codes NAK 1654 Smiles code CC1(C)C(C=C(Cl)Cl)C1C(=O)
OCc2c(F)c(F)c(F)c(F)c2F
15
H
11
Cl
2
F
5
O
2
Form Colourless
crystals. M.p. 44.7 C B.p. 130 C /0.075 mmHg V.p. 1 mPa (20 C) S.g./density 1.38
(20 C) Specifc rotation []20 16.8 (c = 1, chloroform)
COMMERCIALISATION:
History Insecticide reported by W. Behrenz & K. Naumann (Pfanz.-Nachr. Bayer (Engl. Ed.),
1982, 35, 309). Evaluated by Bayer AG.
APPLICATIONS:
neurons by interaction with the sodium channel. Uses It shows a wide range of insecticidal
activity against pests of stored products and in public hygiene. It has a good knock-down
activity against Diptera, especially Culicidae.
PRODUCTS:
Discontinued products Baynac* (Bayer).
Oral Acute oral LD
50
for male rats 90105, female rats 85120, male mice 119, female
mice 150 mg/kg. Skin and eye Acute percutaneous LD
50
(24 h) for male ratsc. 2500,
female rats 1535 mg/kg. Not a skin sensitiser (guinea-pigs). NOEL (90 d) for rats
200 mg/kg diet, for dogs 100 mg/kg diet Other Not mutagenic to mice.
O
O
Cl
Cl
F
F
F F
F
2,3,4,5,6-pentafluorobenzyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
fenoprop; fenoprop-butotyl 253
fenitropan
Fungicide
NOMENCLATURE:
Common name fenitropan (BSI, E-ISO); f(nitropane) ((m) F-ISO)
IUPAC name (1RS,2RS)-2-nitro-1-phenyltrimethylene di(acetate)
Chemical Abstracts name (1R*,2R*)-2-nitro-1-phenyl-1,3-propanediyl diacetate
CAS RN [65934943] stated stereochemistry; [65934954] unstated stereochemistry
Development codes EGYT 2248 Smiles code CC(=O)OCC(C(OC(=O)C)c1ccccc1)
[N+](=O)[O-]
13
H
15
NO
6
M.p. 7072 C Solubility In water 30 mg/l (20 C). In chloroform 1.25, isopropanol 10,
xylene 350 (all in g/l, 20 C).
COMMERCIALISATION:
History Fungicide reported by A. Kis-Tams et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1981,
1, 29). Introduced by EGYT Pharmacochemical Works. Patents GB 1561422; US 4160035
APPLICATIONS:
Mode of action Fungicide with contact action. Uses As a seed treatment for cereals,
maize, rice and sugar beet; applied at 48 g/100 cwt seed, or 46 kg/ha as a foliar spray.
Formulation types LS .
PRODUCTS:
Discontinued products Volparox* (EGYT).
Oral Acute oral LD
50
for male rats 3237, female rats 3852 mg/kg. NOEL (90 d) for rats
2000 mg/kg diet. Toxicity Class WHO (a.i.) U
fenoprop; fenoprop-butotyl
NOMENCLATURE:
Common name 2,4,5-TP (France (as alternative to ISO name), JMAF and formerly
USSR); silvex (ANSI, WSSA); fenoprop (BSI, E-ISO, (m) F-ISO)
IUPAC name ()-2-(2,4,5-trichlorophenoxy)propionic acid
CH
CH CH
2
NO
2
OCOCH
3
OCOCH
3
254
fenoprop; fenoprop-butotyl
Chemical Abstracts name ()-2-(2,4,5-trichlorophenoxy)propanoic acid
CAS RN [93721] fenoprop, unstated stereochemistry EC no 2022712
PHYSICAL CHEMISTRY: Mol. wt. 269.5; (butotyl ester 369.7) M.f. C
9
H
7
Cl
3
O
3
;
(butotyl ester C15H19Cl3O4) Form Colourless powder. M.p. 179181 C V.p. Its lower
alkyl esters are slightly volatile; fenoprop-butometyl (2-butoxy-1-methylethyl ester) is
practically non-volatile Solubility In water 140 mg/l (25 C). In acetone 180, methanol
134, diethyl ether 98, heptane 0.86 (all in g/kg, 25 C). The amine and alkali metal salts
are soluble in water, acetone, lower alcohols; insoluble in aromatic and chlorinated
hydrocarbons and most non-polar organic solvents. Its lower alkyl esters are sparingly
soluble in water; very soluble in most organic solvents. pKa 2.84
COMMERCIALISATION:
History The plant-growth regulating properties of its salts described by M. E. Synerholm
& P. W. Zimmerman (Contrib. Boyce Thompson Inst., 1945, 14, 91). Its esters introduced as
herbicides by Dow Chemical Co. (later DowElanco) and its salts as plant growth regulators
by Amchem Products Inc. (later Rhne-Poulenc Agrochimie).
APPLICATIONS:
Mode of action Systemic, selective herbicide, absorbed by leaves and stems.
Uses Recommended for brush control at 24 kg a.e./hl; to control aquatic weeds; to
control broad-leaved weeds in maize and sugar cane at lower rates. Sprays of amine
salts (1.4 a.e./hl) were used 714 d before harvest to reduce pre-harvest drop of apples.
Formulation types EC (esters); SL (amine salts).
PRODUCTS:
Discontinued products Fruitone T* (Amchem); Kuron* (Dow).
ANALYSIS:
Product analysis by glc (CIPAC Handbook, 1994, F, 292319; ibid., 1985, 1C, 2257); total acids
by titration or by glc (ibid., 1985, 1C, 2121, 2122). Free phenol impurity determined by hplc
(ibid., 1994, F, 362). Residues determined by glc with ECD (R. P. Marquardt, Anal. Methods
Pestic., Plant Growth Regul. Food Addit., 1964, 4, 211; Anal. Methods Pestic. Plant Growth Regul.,
1972, 6, 688). See also Pestic. Anal. Man., I, 208, 302.
IARC 41 (1986), Suppl. 7 (1987). EU Status (1107/2009) Not approved, Commission
IARC Class Chlorophenoxy herbicides classifed as 2B
Oral Acute oral LD
50
for rats 650 mg/kg, 5001000 mg mixed fenprop-butyl or propylene
glycol butyl ether esters/kg,c. 3940 mg a.e. (as fenoprop-trolamine)/kg.
50
for rabbits >3200 mg a.e. (as fenoprop-trolamine)/
kg. Fenoprop, the trolamine salt and undiluted esters are eye irritants. Water GV 9 g/l
Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22| Xi; R38| N; R50, R53 (acid): Xn;
R20/21/22| Xi; R38| N; R50, R53 (salts)
fenoxaprop-ethyl; fenoxaprop 255
fenoxacrim
Insecticide
NOMENCLATURE:
Common name f(noxacrim) ((m) F-ISO); fenoxacrim (BSI, E-ISO)
IUPAC name 3,4-dichloro-1,2,3,4-tetrahydro-6-hydroxy-1,3-dimethyl-2,4-
dioxopyrimidine-5-carboxanilide
Chemical Abstracts name N-(3,4-dichlorophenyl)hexahydro-1,3-dimethyl-2,4,6-trioxo-
5-pyrimidinecarboxamide (preferred tautomer) Other names HHP
CAS RN [65400988]
Smiles code CN1C(=O)C(C(=O)Nc2ccc(Cl)c(Cl)c2)C(=O)N(C)C1=O
13
H
11
Cl
2
N
3
O
4
COMMERCIALISATION:
History Insecticide discovered by Ciba-Geigy AG.
fenoxaprop-ethyl; fenoxaprop
Herbicide
HRAC A WSSA 1
NOMENCLATURE:
Common name (for acid) f(noxaprop) ((m) F-ISO); (for acid) fenoxaprop (BSI, ANSI,
E-ISO)
IUPAC name ethyl ()-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]propionate; ethyl
()-2-[4-(6-chlorobenzoxazol-2-yloxy)phenoxy]propionate
Chemical Abstracts name ethyl ()-2-[4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]
propanoate CAS RN [82110723] fenoxaprop-ethyl (racemate); [66441234]
fenoxaprop-ethyl (unstated stereochemistry); [95617097] fenoxaprop (racemate);
[73519558] fenoxaprop (unstated stereochemistry) EC no 2663629 fenoxaprop-ethyl
Development codes Hoe 033171; Hoe 053022 (acid)
18
H
16
ClNO
5
; (acid
C16H
12
ClNO
5
) Form Colourless solid. M.p. 8587 C V.p. 4.2 10
3
mPa (20 C)
K
ow
logP = 4.12 S.g./density 1.3 Solubility In water 0.9 mg/l (pH 7, 25 C). In acetone
>500, toluene >300, ethyl acetate >200, ethanol, cyclohexane, n-octanol >10 (all in g/
kg, 25 C). Stability Fenoxaprop-ethyl is stable for 6 months at 50 C. Not sensitive to
sunlight. Decomposed by aqueous acids and alkalis; DT
50
>1000 d (pH 5), 100 d (pH 7),
2.4 d (pH 9) (20 C).
Cl
N
O
O O CHCO
2
C
2
H
5
CH
3
256
fenoxaprop-ethyl; fenoxaprop
COMMERCIALISATION:
History Herbicide reported by H. Bieringer et al. (Proc. Br. Crop Prot. Conf. Weeds, 1982, 1,
11). The ethyl ester introduced by Hoechst AG (later AgrEvo GmbH).
Manufacturers AgrEvo
APPLICATIONS:
(ACCase). Mode of action Fenoxaprop-ethyl is a selective herbicide with contact and
systemic action, absorbed principally by the leaves, with translocation both acropetally and
basipetally to the roots or rhizomes. Uses Post-emergence control of many annual and
perennial grass weeds (including Sorghum halepense) in soya beans, cotton, sugar beet,
peanuts, potatoes, beans, sunfowers, vegetables, and other broad-leaved crops; and (when
applied with the herbicide safener fenchlorazole-ethyl) annual and perennial grass weeds
and wild oats in wheat, rye, and triticale. Formulation types EC.
PRODUCTS:
Discontinued products Acclaim* (Hoechst); Bugle* (Hoechst); Cheetah* (AgrEvo);
Cheetah R* (AgrEvo); Depon* (AgrEvo); Excel* (AgrEvo); Furore* (AgrEvo); Option*
(AgrEvo); Option II* (AgrEvo); Puma* (AgrEvo); Whip* (AgrEvo); WhipI* (AgrEvo);
Discontinued mixtures Cheyenne* (+ MCPA-2-ethylhexyl) (Hoechst); Fusion*
(+ fuazifop-P-butyl) (Zeneca); Horizon* (+ fuazifop-P-butyl) (AgrEvo).
ANALYSIS:
For analysis in residues, see Pestic. Anal. Man., II, 180.430.
J. Pesticide Sci. 1992, 17, 1723. EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD
50
for male mice 4670, female mice 5490, male rats 2357, female rats
50
for rabbits >1000, female rats >2000
mg/kg. Slight irritant to skin and eyes (rabbits). Inhalation LC
50
3
.
NOEL (3 y) for dogs 0.9 mg/kg b.w. (15 ppm). ADI/RfD (EPA) 0.0025 mg/kg b.w. [1986].
Toxicity Class WHO (a.i.) UECClassifcation R43| N; R50, R53 (fenoxaprop-ethyl)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail >5000, bobwhite quail >2510 mg/kg. Fish LC
50

(96 h) for river trout 0.48, bluegill sunfsh 0.31 mg/l. Daphnia LC
50
(48 h) 3.18 mg/l.
Bees LD
50
>0.00002 mg/bee
ENVIRONMENTAL FATE:
Plants In plants, fenoxaprop-ethyl is metabolised via fenoxaprop to 6-chloro-2,3-
dihydrobenzoxazol-2-one. Soil/Environment In soil, fenoxaprop-ethyl is rapidly
hydrolysed to fenoxaprop (A. E. Smith J. Agric. Food Chem. 1985, 33, 483); DT
50
110 d.
fenpiclonil 257
fenpiclonil
Fungicide
FRAC 12, E2; phenylpyrrole
NOMENCLATURE:
Common name fenpiclonil (BSI, E-ISO, (m) F-ISO)
IUPAC name 4-(2,3-dichlorophenyl)pyrrole-3-carbonitrile
Chemical Abstracts name 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile
CAS RN [74738173] Development codes CGA 142 705 (Ciba-Geigy)
Smiles code Clc1cccc(c2c[nH]cc2C#N)c1Cl
11
H
6
Cl
2
N
2
Form White crystals.
M.p. 144.9151.1 C V.p. 1.1 10-2 mPa (25 C) K
ow
logP = 3.86 (25 C)
Henry 5.4 10
4
Pa m
3
mol
1
4.8 mg/l (25 C). In ethanol 73, acetone 360, toluene 7.2, n-hexane 0.026, n-octanol 41 (all
in g/l, 25 C). Stability Not hydrolysed after 6 h at 100 C between pH 3 and 9. Stable up
to 250 C.
COMMERCIALISATION:
History Fungicide reported by D. Nevill et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 1,
65). Introduced in Switzerland (1988) by Ciba-Geigy AG (later Syngenta AG).
Patents EP 236272
APPLICATIONS:
Biochemistry Inhibits mitogen-activated protein kinase, in osmotic signal transduction.
Mode of action Slightly systemic, contact fungicide with long-lasting activity.
Uses Effective against seed-borne pathogens of cereals, especially Fusarium nivale and
Tilletia caries. On non-cereal crops, controls a wide range of seed- and soil-borne fungi
(Alternaria, Ascochyta, Aspergillus, Fusarium, Helminthosporium, Rhizoctonia and Penicillium
spp.). Having a different mode of action, fenpiclonil gives good control of all isolates of
F. nivale, including those resistant to carbendazim and related fungicides. On cereals and
peas, used at 20 g/100 kg seed; on potatoes, at 2050 g/t (depending on target pathogens).
Formulation types DS; FS; WS .
PRODUCTS:
Discontinued products Beret* (Syngenta); Electer* (Novartis); Galbas* (Novartis);
Gambit* (Novartis); Discontinued mixtures Arena* (+ tebuconazole) (seed treatment,
Germany) (Bayer); Larin* (+ imazalil + tebuconazole) (seed treatment, Germany)
(Syngenta).
Cl Cl
N
CN
H
258
fenpirithrin
ANALYSIS:
Residue determination by hplc. Details available from Syngenta.
Oral Acute oral LD
50
for rats, mice, and rabbits >5000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Non-
sensitising (guinea pigs). Inhalation LC
50
(4 h) for rats >1.5 mg/l air. NOEL for rats 1.25,
mice 20, dogs 100 mg/kg b.w. daily. ADI/RfD (BfR) 0.0125 mg/kg b.w. [1991]. Other Non-
teratogenic and non-mutagenic. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >2510 mg/kg. LC
50
for mallard ducks >5620,
bobwhite quail 3976 ppm. Fish LC
50
(96 h) for rainbow trout 0.8, carp 1.2, bluegill sunfsh
0.76, catfsh 1.3 mg/l. Daphnia LC
50
(48 h) 1.3 mg/l. Algae LC
50
(5 d) for Scenedesmus
subspicatus 0.22 mg/l. Bees Not toxic to honeybees; LD
50
(oral and contact) >5 g/bee.
Worms LC
50
(14 d) for Eisenia foetida 67 mg/kg soil. Otherbenefcial Harmless to
carabid beetles.
ENVIRONMENTAL FATE:
Animals Rapidly absorbed from the gastrointestinal tract into the general circulation;
rapidly excreted and almost completely eliminated, mostly in the faeces. The dominant
metabolic pathway is oxidation of the pyrrole ring at the 2-position. A minor pathway
is hydroxylation of the phenyl ring. All metabolites are excreted as conjugates, mainly as
glucuronides. Plants Degradation proceeds via oxidation of the pyrrole ring followed by
hydrolysis of the nitrile group. Opening of the pyrrole ring and hydroxylation of the phenyl
ring are further degradation steps. The parent is, however, the relevant residue; between
1315 minor metabolites were also observed. Soil/Environment Relatively persistent
in soil; formation of bound residues represents the major route for dissipation. In leaching
and adsorption/desorption experiments, the compound proved to be immobile in soil,
RMF 0.3. Photolytic DT
50
in water 70 min.
fenpirithrin
Insecticide
IRAC 3
NOMENCLATURE:
Common name fenpirithrin (BSI, ANSI, E-ISO); fenpirithrine ((f) F-ISO)
IUPAC name (RS)-cyano(6-phenoxy-2-pyridyl)methyl (1RS)-cis-trans-3-(2,2-
dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate; (RS)-cyano(6-phenoxy-2-pyridyl)
methyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name cyano(6-phenoxy-2-pyridinyl)methyl 3-(2,2-dichloroethenyl)-
fenridazon 259
2,2-dimethylcyclopropanecarboxylate CAS RN [68523182] unstated stereochemistry
Development codes Dowco 417
Smiles code CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c2cccc(Oc3ccccc3)n2
21
H
18
Cl
2
N
2
O
3
COMMERCIALISATION:
History Insecticide evaluated by Dow Chemical Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Vivithrin* (Dow).
fenridazon
NOMENCLATURE:
Common name fenridazon (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 1-(4-chlorophenyl)-1,4-dihydro-6-methyl-4-oxopyridazine-3-carboxylic acid
Chemical Abstracts name 1-(4-chlorophenyl)-1,4-dihydro-6-methyl-4-oxo-3-
pyridazinecarboxylic acid CAS RN [68254104]; [83588436] potassium salt
Development codes RH-0007 Smiles code Cc1cc(=O)c(nn1c2ccc(Cl)cc2)C(=O)O
12
H
9
ClN
2
O
3
COMMERCIALISATION:
History Plant growth regulator evaluated by Rohm & Haas Co.
PRODUCTS:
Discontinued products Hybrex* (potassium salt) (Monsanto).
ANALYSIS:
Residues by hplc/uv (Resid. Anal. Methods).
NOEL (3 generation) for rats 100 ppm (5 mg/kg b.w.) (EPA Tracking). ADI/RfD (EPA)
0.05 mg/kg b.w. [1994].
N
N C
O
OH
O CH
3
Cl
260
fenson
fenson
Acaricide
NOMENCLATURE:
Common name f(nizon) ((m) France); fenson (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name 4-chlorophenyl benzenesulfonate (I)
Chemical Abstracts name (I) Other names CPBS; PCPBS CAS RN [80386]
Smiles code Clc1ccc(OS(=O)(=O)c2ccccc2)cc1
12
H
9
ClO
3
S Form Colourless crystals;
(tech. is a pale pink powder). M.p. 6162 C; (tech., 5659 C) Solubility Sparingly soluble
in water. Soluble in organic polar and aromatic solvents. Stability Hydrolysed by alkali.
COMMERCIALISATION:
History Introduced by Murphy Chemical Ltd (later DowElanco).
APPLICATIONS:
Mode of action Contact acaricide. Uses Acaricide with ovicidal properties which was
normally used in combination with acaricides effective against the active stages of mites, to
control mites on apples and glasshouse crops, including vines. Formulation types WP.
PRODUCTS:
Discontinued products Murvesco* (Murphy).
ANALYSIS:
Product analysis by hydrolysis to 4-chlorophenol which is determined by acid-base titration
(CIPAC Handbook, 1970, 1, 392). Residues determined by colorimetry of a derivative (A. H.
Kutschinski & E. N. Luce, Anal. Chem., 1952, 24, 1188).
Oral Acute oral LD
50
50

for rats and rabbits >2000 mg/kg. Toxicity Class WHO (a.i.) IIIECClassifcation Xn;
R22| Xi; R36| N; R51, R53
fensulfothion 261
fensulfothion
IRAC 1B
NOMENCLATURE:
Common name fensulfothion (BSI, E-ISO, (m) F-ISO, ESA, Society of Nematologists USA)
IUPAC name O,O-diethyl O-4-methylsulfnylphenyl phosphorothioate
Chemical Abstracts name O,O-diethyl O-[4-(methylsulfnyl)phenyl]
phosphorothioate Other names DMSP CAS RN [115902] EC no 2041143
Development codes Bayer 25 141; S 767 Smiles code CCOP(=S)(OCC)Oc1ccc(cc1)
S(=O)C
11
H
17
O
4
PS
2
Form Yellowish-brown oil.
M.p. <25 C (Agchem. Desk Ref.) B.p. 138141 C /0.01 mmHg V.p. 4 mPa (US EPA, cited
in ARS PPD) K
ow
logP = 2.23 (Agchem. Desk Ref.) S.g./density 1.202 (20 C) Solubility
In water 1.54 g/l (25 C). Miscible with most organic solvents, except aliphatics. Stability
Subject to hydrolysis in alkaline media. Readily oxidised to the sulfone, and isomerises
readily to the O,S-diethyl isomer (E. Benjamini et al., J. Econ. Entomol., 1959, 52, 94, 99).
COMMERCIALISATION:
History Nematicide reported by B. Homeyer (Mitt. Biol. Bundesanst. Land-Forstwirtsch. Berlin-
Dahlem, 1967, 121, 50). Introduced by Bayer AG. Patents DE 1101406; US 3042703
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Nematicide and insecticide
with primarily contact action, but also some systemic activity. Uses Soil application for
control of root-knot, cyst-forming, and free-living nematodes, and also soil-dwelling insects
in cereals, maize, sorghum, cotton, rice, coffee, cocoa, peanuts, soya beans, sugar beet,
sugar cane, tomatoes, potatoes, sweet potatoes, oranges, strawberries, bananas, pineapples,
tobacco, ornamentals, and turf. Formulation types DP; GR; SL; SC. WP.
PRODUCTS:
Discontinued products Dasanit* (Bayer); Terracur* (Bayer); Terracur P* (Bayer).
ANALYSIS:
Product analysis by hplc with uv detection (AOAC Methods, 18th Ed., 983.09;
CIPAC Handbook, 1985, 1C, 2126), by glc with uv detection (ibid., 1988, D, 92), or by glc with
FID (AOAC Methods, 18th Ed., 986.07). Residues determined by glc (C. A. Anderson, Anal.
Methods Pestic. Plant Growth Regul., 1973, 7, 253; Man. Pestic. Residue Anal., pp. 3, 6, 8, 1317,
P(OCH
2
CH
3
)
2
S
O CH
3
SO
262
fenteracol
19; Anal. Methods Residues Pestic., 1988, Part I, M2, M5).
EHC 63 (1986) a general review of organophosphorus insecticides. JMPR Evaln. 39 (1982),
41 (1983). PDS 44 (1980). ICSC.406 (2001).
Oral Acute oral LD
50
for male rats 4.710.5, female rats 2.2, guinea pigs 9 mg/kg. Skin
and eye Acute percutaneous LD
50
(in xylene) for female rats 3.5, male rats 30 mg/kg.
Inhalation LC
50
(1 h) for male rats 0.113 mg/l air. NOEL In 16 mo feeding trials, rats
receiving 1 mg/kg diet showed no ill-effects. ADI/RfD (JMPR) 0.0003 mg/kg b.w. [1982];
(EPA) 0.00025 mg/kg b.w. [1989]. Toxicity Class WHO (a.i.) IaECClassifcation T+;
R27/28| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(5 d) for bobwhite quail
35, mallard ducks 43 mg/kg diet. Fish LC
50
(96 h) for bluegill sunfsh 0.12, rainbow trout
8.6, golden orfe 6.8 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, fensulfothion is readily oxidised.
fenteracol
Herbicide
NOMENCLATURE:
Common name fenteracol (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-(2,4,5-trichlorophenoxy)ethanol (I)
Chemical Abstracts name (I) Other names TCPE CAS RN [2122772]
Smiles code OCCOc1cc(Cl)c(Cl)cc1Cl
8
H
7
Cl
3
O
2
COMMERCIALISATION:
History Herbicide introduced by Budapest Chemical Works.
PRODUCTS:
Discontinued products Klorinol* (Budapest Chemical).
fenthiaprop; fenthiaprop-ethyl 263
fenthiaprop; fenthiaprop-ethyl
Herbicide
NOMENCLATURE:
Common name fenthiaprop (BSI, E-ISO); fentiaprop ((m) F-ISO)
IUPAC name ()-2-[4-(6-chloro-1,3-benzothiazol-2-yloxy)phenoxy]propionic acid;
()-2-[4-(6-chlorobenzothiazol-2-yloxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-[(6-chloro-2-benzothiazolyl)oxy]phenoxy]propanoic
acid CAS RN [95721123] fenthiaprop (racemate); [73519503] fenthiaprop (unstated
stereochemistry); [93921165] fenthiaprop-ethyl (racemate); [66441110] fenthiaprop-
ethyl (unstated stereochemistry) Development codes Hoe 35 609
PHYSICAL CHEMISTRY: Mol. wt. 349.8; (ethyl ester 377.8) M.f. C
16
H
12
ClNO
4
S; (ethyl
ester C18H16ClNO4S) Form Fenthiaprop-ethyl is a crystalline solid.
M.p. 5657.5 C (ethyl ester) V.p. 5.10 10
4
mPa (20 C, ethyl ester) Solubility Ester: In
water 0.8 mg/l (25 C). In acetone, ethyl acetate, toluene >500 g/kg, cyclohexane >40 g/kg,
ethanol, n-octanol >50 g/l.
COMMERCIALISATION:
History Herbicide reported by R. Handte et al. (Proc. Br. Crop Prot. Conf. Weeds, 1982, 1,
19). Ethyl ester, fenthiaprop-ethyl, introduced by Hoechst AG.
APPLICATIONS:
Mode of action Local and systemic herbicide; translocated acropetally and basipetally to
roots and rhizomes, where the growing points are destroyed. Uses A post-em. herbicide,
active against many annual and perennial grasses. It controls Alopecurus myosuroides, Avena
spp. and volunteer cereals at 180240 g/ha and Agropyron repens at 480720 g/l in oilseed
rape, potatoes and sugar beet. Formulation types EC.
PRODUCTS:
Discontinued products Joker* (ethyl ester) (Hoechst).
Oral Acute oral LD
50
50
for female rats 2000 mg/kg. Slight
irritant to skin and eyes (rabbits). NOEL (90 d) for rats 50 mg/kg diet.
264
fenuron
fentrifanil
Acaricide
NOMENCLATURE:
Common name fentrifanil (BSI, E-ISO, (m) F-ISO); hexafuoramin (Republic of South
Africa)
IUPAC name N-(6-chloro-,,-trifuoro-m-tolyl)-,,-trifuoro-4,6-dinitro-o-toluidine;
2-chloro-2,4-dinitro-5,6-bis(trifuoromethyl)diphenylamine
Chemical Abstracts name N-[2-chloro-5-(trifuoromethyl)phenyl]-2,4-dinitro-6-
(trifuoromethyl)benzenamine CAS RN [62441547] Development codes PP199
Smiles code [O-][N+](=O)c1cc([N+](=O)[O-])c(Nc2cc(ccc2Cl)C(F)(F)F)c(c1)C(F)(F)F
14
H
6
ClF
6
N
3
O
4
COMMERCIALISATION:
History Acaricide reported by N. Morton et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1977, 2,
349). Evaluated by ICI Plant Protection Div. (later ICI Agrochemicals).
APPLICATIONS: Uses Effective against Panonychus ulmi, Tetranychus spp. and eriophyid
mites on apples.
fenuron
Herbicide
NOMENCLATURE:
Common name fenidim* (former exception, USSR); no name (Portugal, Sweden);
fenuron (BSI, E-ISO, F-ISO, ANSI, WSSA)
IUPAC name 1,1-dimethyl-3-phenylurea
Chemical Abstracts name N,N-dimethyl-N-phenylurea Other names PDU
CAS RN [101428] Smiles code CN(C)C(=O)Nc1ccccc1
9
H
12
N
2
M.p. 133134 C V.p. 21 mPa (60 C) S.g./density 1.08 (20 C) Solubility In water
3.85 g/l (25 C). In ethanol 108.8, diethyl ether 5.5, acetone 80.2, benzene 3.1, chloroform
125, hexane 0.2, groundnut oil 1.0 (all in g/kg, 2025 C). Stability Stable to light and to
oxidation. Stable in neutral media, but hydrolysed by strong acids and alkalis.
COMMERCIALISATION:
History Herbicidal properties of fenuron described by H. C. Bucha & C. W. Todd (Science,
1951, 114, 493). Introduced by E. I. du Pont de Nemours & Co. Patents US 2655447,
NHCON(CH
3
)
2
fenuron-TCA 265
GB 691403, GB 692589 (all to DuPont) Manufacturers Hermania; MV; United
Phosphorus Ltd
APPLICATIONS:
site. Mode of action Non-selective systemic herbicide, absorbed predominantly by the
roots, with translocation acropetally in the xylem. Uses Control of woody plants and
deep-rooted perennial weeds, particularly on non-crop land. Often used in combination
with chlorpropham to extend the weed spectrum and range of crops.
PRODUCTS:
Discontinued products Dybar* (DuPont); Kayron* (Krishi Rasayan);
Discontinued mixtures Atlas Gold* (+ chlorpropham + propham) (Atlas); Atlas Red*
(+ chlorpropham) (Nufarm UK); Croptex Chrome* (+ chlorpropham) (Hortichem).
ANALYSIS:
Product analysis of fenuron based on hydrolysis (W. K. Lowen & H. M. Baker, Anal. Chem.,
1952, 24, 1476). Residues determined by colorimetry (R. L. Dalton & H. L. Pease, J. Assoc. Off.
Agric. Chem., 1962, 45, 377).
Oral Acute oral LD
50
for rats 6400 mg/kg. Skin and eye Non-irritating to skin.
NOEL In 90 d feeding trials, no apparent effect observed with rats receiving 500 mg/kg
diet. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Fish LC
50
(48 h) for guppies 610 mg/l.
ENVIRONMENTAL FATE:
Plants In plants, N-demethylation occurs step-by-step. Soil/Environment In soil, enzymic
and microbial degradation involves step-by-step N-demethylation.
fenuron-TCA
Herbicide
NOMENCLATURE:
Common name fenuron-TCA (WSSA)
IUPAC name 1,1-dimethyl-3-phenyluronium trichloroacetate
Chemical Abstracts name trichloroacetic acid compound with N,N-dimethyl-
N-phenylurea (1:1) CAS RN [4482557] Development codes GC-2603
Smiles code CN(C)C(=O)Nc1ccccc1.OC(=O)C(Cl)(Cl)Cl
11
H
13
Cl
3
N
2
O
3

266
famprop-methyl; famprop-isopropyl; famprop
Form Colourless crystals. M.p. 6568 C Solubility In water 4.8 g/l (room temperature).
In 1,2-dichloroethane 666, trichloroethylene 567 (both in g/kg, room temperature).
Sparingly soluble in petroleum oils.
COMMERCIALISATION:
History Fenuron-TCA introduced by Allied Chemical Corp., Agricultural Division (later
HACCO Inc.). Patents US 2782112, US 2801911 (both to Allied)
APPLICATIONS: Uses Fenuron-TCA combines the herbicidal actions of fenuron and
trichloroacetic acid, and was used for total weed control on non-crop areas and against
woody plants. Formulation types WP.
PRODUCTS:
Discontinued products Dozer* (HACCO); Urab* (HACCO).
Oral Acute oral LD
50
for rats 40005700 mg/kg. Skin and eye Skin, eye, and respiratory
tract irritant. Toxicity Class WHO (a.i.) UECClassifcation Xi; R38| N; R50, R53
famprop-methyl; famprop-isopropyl; famprop
Herbicide
HRAC Z WSSA 25
NOMENCLATURE:
Common name famprop (assigned to the acid) (BSI, E-ISO, (m) F-ISO, WSSA)
IUPAC name methyl N-benzoyl-N-(3-chloro-4-fuorophenyl)-DL-alaninate; N-benzoyl-N-
(3-chloro-4-fuorophenyl)-DL-alanine (acid)
Chemical Abstracts name N-benzoyl-N-(3-chloro-4-fuorophenyl)-DL-alanine methyl
ester CAS RN [52756259] methyl ester; [52756226] isopropyl ester; [58667633]
acid Development codes WL 29671 (methyl ester); WL 29 672 (isopropyl ester) (both
Shell) Smiles code famprop:CC(N(C(=O)c1ccccc1)c2ccc(F)c(Cl)c2)C(=O)O
PHYSICAL CHEMISTRY:
Composition Tech is 93%. Mol. wt. methyl ester 335.8; isopropyl ester 363.8; acid 321.7
M.f. C
17
H
15
ClFNO
3
(methyl ester); C
19
H
19
ClFNO
3
(isopropyl ester); C16H13ClFNO3
(acid) Form Colourless crystals; (tech., off-white crystals). M.p. 8486 C; (tech., 81
82 C) V.p. Flamprop-methyl: 0.047 mPa (20 C) K
ow
methyl ester, logP = 3.0; acid, logP =
3.09 (25 C, unionised, K. Chamberlain et al., Pestic Sci. 47, 265 (1996))
C
F
Cl
N
CHCO
2
H
CH
3 O
famprop-methyl; famprop-isopropyl; famprop 267
Henry 4.51 10
4
Pa m
3
mol
1
(famprop-methyl, calc.) Solubility Flamprop-methyl:
in water 35 mg/l (20 C). In acetone >500, cyclohexanone 414, o-xylene 258, carbon
tetrachloride 168, ethanol 135, hexane 7 (all in g/l, 20 C). Stability Stable to light and to
heat, and at pH 27. Hydrolysed in alkaline media (pH >7) to famprop and methanol.
pKa Acid, 3.7 (K. Chamberlain et al., Pestic. Sci., 1996, 47, 265 and refs. therein)
COMMERCIALISATION:
History Herbicidal properties of famprop-methyl reported by E. Haddock et al. (Proc. Br.
Weed Control Conf., 12th, 1974, 1, 9); compared with analogues by B. Jeffcoat et al. (Pestic.
Sci., 1977, 8, 1). Flamprop-isopropyl and famprop-methyl introduced by Shell Research Ltd
(later American Cyanamid Co.); later replaced by the single stereoisomers (famprop-M-
isopropyl and famprop-M-methyl). Patents GB 1437711
APPLICATIONS:
Biochemistry Selectivity depends on the rates of hydrolysis to famprop and detoxication
of the latter by formation of conjugates within the plant; the acid is translocated to
meristems where it inhibits plant growth. Mode of action Flamprop-methyl is a selective
systemic herbicide, absorbed by the leaves. Undergoes hydrolysis to famprop, which is
translocated readily to growing points. Uses Post-emergence control of wild Oats (Avena
spp.) in wheat, including crops undersown with clover or grass. Also controls Alopecurus
myosuroides. Formulation types EC. Compatibility If applied together with phenoxy
herbicides, the activity of famprop-methyl may be reduced.
PRODUCTS:
Discontinued products Barnon* (isopropyl ester) (Cyanamid).
ANALYSIS:
Product analysis by i.r. spectrometry or by glc. Residues determined by glc with ECD.
Oral Acute oral LD
50
for rats 1210, mice 720 mg/kg (famprop-methyl).
50
for rats >294 mg a.i./kg (as EC formulation). Non-
irritating and non-sensitising to skin. NOEL (2 y) for rats 2.5 mg a.i./kg diet, for dogs 10
mg/kg diet. Other Acute i.p. LD
50
for rats 350500 mg/kg. Toxicity Class WHO (a.i.) III
(allocated to the acid)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 4640, pheasants, mallard ducks, domestic fowl,
partridges, pigeons >1000 mg/kg (famprop-methyl). Fish LC
50
4.7 mg/l. Bees Non-toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, metabolism and elimination occur
within 4 d. Plants In plants, famprop-methyl is hydrolysed to the biologically-active
famprop, which then undergoes conversion to a biologically-inactive conjugate.
268
fuacrypyrim
fuacrypyrim
Acaricide
IRAC 20C
NOMENCLATURE:
Common name fuacrypyrime ((m) F-ISO); fuacrypyrim (BSI, E-ISO)
IUPAC name methyl (E)-2-{-[2-isopropoxy-6-(trifuoromethyl)pyrimidin-4-yloxy]-o-
tolyl}-3-methoxyacrylate
Chemical Abstracts name methyl (E)--(methoxymethylene)-2-[[[2-(1-methylethoxy)-
6-(trifuoromethyl)-4-pyrimidinyl]oxy]methyl]benzeneacetate CAS RN [229977
939]; [178813815] unspecifed stereochemistry Development codes NA-83
Smiles code without stereochemistry:COC=C(C(=O)OC)c1ccccc1COc2cc(nc(OC(C)
C)n2)C(F)(F)F
20
H
21
F
3
N
2
O
5
Form White, odourless
solid. M.p. 107.2108.6 C V.p. 2.69 10
3
mPa (20 C) (gas saturation method) K
ow
logP
= 4.51 (pH 6.8, 25 C) Henry 3.33 10
3
Pa m
3
mol
1
(20 C, calc.)
S.g./density 1.276 Solubility In water 3.44 10
4
g/l (pH 6.8, 20 C). In dichloromethane
579, acetone 278, xylene 119, acetonitrile 287, methanol 27.1, ethanol 15.1, ethyl acetate
232, n-hexane 1.84, n-heptane 1.60 (all in g/l, 20 C). Stability Stable at pH 4 and 7; DT
50

574 d (pH 9). Aqueous photolysis DT
50
26 d.
COMMERCIALISATION:
History Acaricide registered in 2001 and launched in 2002, by Nippon Soda Co. Ltd.
Manufacturers Nippon Soda
APPLICATIONS:
Biochemistry Mitochondrial complex III electron transport inhibitor (coupling site II).
Mode of action Acaricide with contact and stomach action. Uses Control of Panonychus,
at 10 g/100 l, for citrus; Panonychus and Tetranychus, at 15 g/100 l, for apples and pears.
Formulation types SC.
PRODUCTS:
Discontinued products Titaron* (Nippon Soda); Discontinued mixtures Oonata*
(+ chlorfenapyr) (Nippon Soda).
EU Status (1107/2009) Never notifed to the EU.
C
CH
O
O
O
CH
3
CH
2
O N
N
CF
3
O
CH
CH
3
CH
3
CH
3
fuazolate 269
Oral Acute oral LD
50
for male and female rats >5000 mg/kg. Skin and eye Acute
percutaneous LD
50
for male and female rats >2000 mg/kg. Weakly irritating for eyes; non-
irritating for skin (rabbits). Inhalation LC
50
(4 h) for male and female rats >5.09 mg/l.
NOEL (24 mo) for male rats 5.9 mg/kg b.w., for female rats 61.7 mg/kg b.w.; (18 mo) for
male mice 20 mg/kg b.w.., for female mice 30 mg/kg b.w.; (12 mo) for male and female dogs
10 mg/kg b.w.. ADI/RfD (FSC) 0.059 mg/kg b.w.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >2250 mg/kg. Dietary LC
50
for bobwhite quail
>5620 ppm. Fish LC
50
(96 h) for carp 0.195 ppm. Daphnia LC
50
(48 h) 0.094 ppm.
Algae EbC50 (72 h) for Selenastrum capricornutum 0.0173 ppm; ErC50 (72 h) for
Selenastrum capricornutum 0.14 ppm. Bees LC
50
(oral) >300 ppm; LD
50
(contact)
>10 g/bee. Worms LC
50
for earthworms 23 mg/kg soil. Otherbenefcial No effect on
Agistemus exsertus at 400 ppm.
fuazolate
Herbicide
HRAC E WSSA 14; phenylpyrazole herbicide
NOMENCLATURE:
Common name fuazolate (BSI, E-ISO, (m) F-ISO)
IUPAC name isopropyl 5-(4-bromo-1-methyl-5-trifuoromethylpyrazol-3-yl)-2-chloro-4-
fuorobenzoate
Chemical Abstracts name 1-methylethyl 5-[4-bromo-1-methyl-5-(trifuoromethyl)-
1H-pyrazol-3-yl]-2-chloro-4-fuorobenzoate CAS RN [174514079]
Development codes MON 48500 (Monsanto); JV 485 Smiles code CC(C)OC(=O)
c1cc(c2nn(C)c(c2Br)C(F)(F)F)c(F)cc1Cl
15
H
12
BrClF
4
N
2
O
2
Form Fluffy, white,
crystalline solid. M.p. 79.580.5 C V.p. 9.43 10
3
mPa (20 C) K
ow
logP = 5.44
Henry 7.89 10-2 Pa m
3
mol
1
(calc.) Solubility In water 53 ;g/l (20 C). Stability
Stable at pH 4 and pH 5; DT
50
4201 d (pH 7, calc.), 48.8 d (pH 9) (both 20 C).
COMMERCIALISATION:
History Reported by S. D. Prosch et al. (Proc. Br. Crop Prot. Conf. Weeds, 1997, 1, 45).
Discovered by Monsanto Co. and evaluated by Twinagro, a j.v. of Monsanto and Bayer AG.
N N
Cl F
Br
CF
3
CH
3
(CH
3
)
2
CHO
O
270
fuazuron
Patents US 5489571; US 5587485; WO 9206962 Manufacturers Twinagro
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Causes rapid
necrosis shortly after emergence of plants. Uses Under development for use as a pre-
emergence cereal herbicide, controlling grasses such as Alopecurus myosuroides, Lolium spp.,
Apera spica-venti, Poa annua and Phalaris spp., as well as broad-leaved weeds such as Galium
aparine, at 125175 g/ha.
Oral Acute oral LD
50
50

for rats >5000 mg/kg. Slightly irritating to eyes; not irritating to skin (rabbits). Not a skin
50
for rats >1.7 mg/l. Other Negative in Ames,
HGPRT/CHO, micronucleus and in vitro cytogenetic tests.
ECOTOXICOLOGY:
Birds Oral LD
50
for bobwhite quail and mallard ducks >2130 mg/kg. Dietary LC
50
for
bobwhite quail and mallard ducks >5330 mg/kg. Fish LC
50
(96 h) for rainbow trout and
bluegill sunfsh >0.045 mg/l. Daphnia EC
50
(48 h) >0.039 mg/l. Worms LC
50
(14 d) for
earthworms >1170 mg/kg dry soil.
ENVIRONMENTAL FATE:
Soil/Environment Laboratory DT
50
(3 feld and 1 standard soil) 1671 d. Strongly bound
to soil: Kd and K
oc
in clay loam (pH 5.1, o.c. 1.94%) 2.5 10
2
and 1.3 10
4
, respy., in loam
(pH 4.7, o.c. 4.24%) 2.9 10
2
and 0.7 10
4
, in silt loam (pH 6.3, o.c. 0.08%) 1.4 10
2
and
1.7 10
4
, in loamy sand (pH 5.8, o.c. 1.30%) 2.0 10
2
and 1.6 10
4
. Concentrations of
fuazolate in lysimeter leachates were <0.01 g/l.
fuazuron
Ixodicide
IRAC 15
NOMENCLATURE:
Common name fuazuron (BSI, E-ISO, (m) F-ISO, INN)
IUPAC name 1-[4-chloro-3-(3-chloro-5-trifuoromethyl-2-pyridyloxy)phenyl]-3-(2,6-
difuorobenzoyl)urea
Cl
F
F
NHCONHCO
O
N
Cl
CF
3
fuazuron 271
Chemical Abstracts name N-[[[4-chloro-3-[[3-chloro-5-(trifuoromethyl)-2-
pyridinyl]oxy]phenyl]amino]carbonyl]-2,6-difuorobenzamide CAS RN [86811587]
Development codes CGA 157 419 (Ciba-Geigy) Smiles code Fc1cccc(F)c1C(=O)
NC(=O)Nc2ccc(Cl)c(Oc3ncc(cc3Cl)C(F)(F)F)c2
20
H
10
Cl
2
F
5
N
3
O
3
Form White to pink,
odourless, fne crystalline powder. M.p. 219 C (decomp.) V.p. 1.2 10-7 mPa (20 C)
K
ow
logP = 5.1 (rp-tlc method) Henry <3.04 10
6
Pa m
3
mol
1
(calc.) S.g./density 1.59
(20 C) Solubility In water <0.02 ppm (20 C). In methanol 2.4, isopropanol 0.9 (both in
g/l, 20 C). Stability Stable up to 219 C. Hydrolysis DT
50
(25 C) 14 d (pH 3), 7 d (pH 5),
20 h (pH 7), 0.5 h (pH 9).
COMMERCIALISATION:
History Ixodicide.
Manufacturers Syngenta; E-tong
APPLICATIONS:
Biochemistry Interaction with chitin formation. Mode of action Systemic acarine
growth regulator with contact and stomach action. Uses Strategic control of the
cattle tick Boophilus microplus (including all known resistant strains) on beef cattle.
Formulation types PO.
PRODUCTS:
Discontinued products Acatak* (Syngenta).
ANALYSIS:
By hplc.
JECFA 48 (1997).
Oral Acute oral LD
50
for rats >5000 mg/kg (OECD 401). Skin and eye Acute
percutaneous LD
50
for rats >2000 mg/kg (OECD 402). Inhalation LC
50
(4 h) for rats
>5994 mg/m
3
(OECD 403). NOEL (1 y) for dogs 7.5 mg/kg b.w. daily; (life-time) for rats
400, mice (males and females) 4.5 mg/kg b.w. daily. In 2-generation reproduction tests
(rats), NOEL 100 ppm. No carcinogenic, mutagenic, teratogenic or reprotoxicity potential.
ADI/RfD (JMPR) 0.04 mg/kg b.w. [1997] (JECFA evaluation). Toxicity Class WHO (a.i.) III
(company classifcation)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail and mallard ducks >2000 mg/kg. LC
50
(8 d) for
bobwhite quail and mallard ducks >5200 ppm. Fish LC
50
for rainbow trout >15, carp >9.1
mg/l (OECD class "harmful"). Daphnia LC
50
0.0006 mg/l (OECD class "very toxic").
Algae NOEC for freshwater green Algae 27.9 mg/l (virtually non-toxic).
Bees OECD class "not toxic". Worms LC
50
(14 d) for earthworms >1000 mg/kg (not
toxic) (OECD 207).
272
fubenzimine
ENVIRONMENTAL FATE:
Animals See P. S. Tantiyaswasdikul in "Residues of some veterinary drugs in animal and
foods" FAO Food and Nutrition Papers 41/10 (1998). Plants Not relevant.
Soil/Environment Not investigated; environmental contamination is unlikely because of
pour-on application.
fubenzimine
Acaricide
NOMENCLATURE:
Common name fubenzimine (BSI, E-ISO, (f) F-ISO)
IUPAC name (2Z,4E,5Z)-N
2
,3-diphenyl-N4,N5-bis(trifuoromethyl)-1,3-thiazolidine-2,4,5-
triylidenetriamine
Chemical Abstracts name N-[3-phenyl-4,5-bis[(trifuoromethyl)imino]-2-
thiazolidinylidene]benzenamine CAS RN [37893020] unstated stereochemistry
EC no 2537031 Development codes BAY SLJ 0312 Smiles code FC(F)(F)
N=C1SC(=Nc2ccccc2)N(C1=NC(F)(F)F)c3ccccc3
17
H
10
F
6
N
4
S Form Orange-yellowish
powder. M.p. 118.7 C V.p. <1 mPa (20 C) Henry <2.60 10
1
Pa m
3
mol
1
(calc.)
Solubility In water 1.6 mg/l (20 C). In dichloromethane, toluene >200, hexane,
isopropanol 510 (all in g/l, 20 C). Stability DT
50
29.9 h (pH 4), 30 min (pH 7), 10 min
(pH 9) (22 C).
COMMERCIALISATION:
History Acaricide reported by G. Zoebelein et al. (Mitt. Biol. Bundesanst. Land-
Forstwirtsch., Berlin-Dahlem, 1979, 191, 283; Pfanz.-Nachr. Bayer (Engl. Ed.), 1980, 33, 169).
Introduced by Bayer AG.
APPLICATIONS:
Mode of action Contact acaricide; acting as a mite growth regulator. The developent of
larvae hatching from treated eggs and treated larvae and nymphs is retarded, and they fail
to emerge from the next quiescent stage. Treated adult mites have a shorted life and lay
fewer eggs. Uses Applied early at 500 mg/l, against Panonychus ulmi and Tetranychus spp. on
pome fruit, plums and damsons, also against P. citri, Phyllocoptruta oleivora and Tetranychus
spp. on citrus. Also shows some fungicidal activity. Formulation types WP.
PRODUCTS:
Discontinued products Cropotex* (Bayer).
ANALYSIS:
Residues determined by glc with ECD (G. Drger, ibid., 1981, 34, 180).
fucofuron 273
Oral Acute oral LD
50
for male rats >5000 mg (in acetone + oil)/kg, 2840 mg (in water
+ Cremophor EL)/kg, for female rats 37005000 mg (in acetone + oil)/kg, 2685 mg (in
water + Cremophor EL)/kg; for male mice >2500 mg/kg; for female rabbitsc. 360 mg/
kg; for female dogs >500 mg/kg. Skin and eye Acute percutaneous LD
50
(24 h) for rats
>5000 mg/kg. Not a skin irritant; causes moderate to severe conjunctival irritation to
rabbits. Inhalation (4 h) for rats >0.357 mg a.i. (as 50% WP)/l air. NOEL (90 d) for male
dogs 100 mg/kg diet, for rats 500 mg/kg diet Other Not mutagenic in dominant lethal
assays in mice; not embryotoxic or teratogenic in rabbits. Toxicity Class WHO (a.i.) U
ECClassifcation Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hens >5000, Japanese quail 45005000, canaries >1000 mg/kg.
fucofuron
Insecticide
NOMENCLATURE:
Common name fucofuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,3-bis(4-chloro-,,-trifuoro-m-tolyl)urea
Chemical Abstracts name N,N-bis[4-chloro-3-(trifuoromethyl)phenyl]urea
CAS RN [370503] Smiles code FC(F)(F)c1cc(NC(=O)Nc2ccc(Cl)c(c2)C(F)(F)F)
ccc1Cl
15
H
8
Cl
2
F
6
N
2
O
COMMERCIALISATION:
History Insecticide developed by Ciba-Geigy AG.
APPLICATIONS: Uses Insecticide used to control Tineidae larvae, which attack cotton
fabrics.
PRODUCTS:
Discontinued products Mitin N* (Ciba-Geigy).
Cl
CF
3
NHCONH
CF
3
Cl
274
fucycloxuron
fucycloxuron
IRAC 15; benzoylurea
NOMENCLATURE:
Common name fucycloxuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-[-(4-chloro--cyclopropylbenzylideneamino-oxy)-p-tolyl]-3-(2,6-
difuorobenzoyl)urea (ratio 5080% (E)- and 5020% (Z)- isomers)
Chemical Abstracts name N-[[[4-[[[[(4-chlorophenyl)cyclopropylmethylene]amino]
oxy]methyl]phenyl]amino]carbonyl]-2,6-difuorobenzamide CAS RN [94050529]
(E)- isomer; [94050530] (Z)- isomer; [113036887] unstated stereochemistry
Development codes PH 7023; DU 319722 (both Duphar); UBI-A1335
(Uniroyal) Offcial codes OMS 3041 Smiles code Fc1cccc(F)c1C(=O)NC(=O)
Nc2ccc(CON=C(C3CC3)c4ccc(Cl)cc4)cc2
PHYSICAL CHEMISTRY:
Composition Ratio 5080% (E)- and 5020% (Z)- isomers. Mol. wt. 483.9
M.f. C
25
H
20
ClF
2
N
3
O
3
Form Off-white to yellow crystals (tech.). M.p. 143.6 C (decomp.)
(for (E)-, (Z)- isomeric mixture) V.p. 5.4 10
5
mPa (25 C) (for (E)-, (Z)- isomeric
mixture) K
ow
logP = 6.97 (E)- isomer; 6.90 (Z)- isomer Henry 2.6 10-2 Pa m
3
mol
1

(25 C) Solubility In water <1 ;g/l (20 C). In cyclohexane 0.2, xylene 3.3, ethanol 3.8,
N-methylpyrrolidone 940 (all in g/l, 20 C) for (E)-, (Z)- isomeric mixture.
Stability Thermally stable, <2% decomposition after 24 hours storage at 50 C. No
degradation at pH 5, 7 or 9. Photolytically degraded, DT
50
c. 18 d.
COMMERCIALISATION:
History Acaricide and insecticide reported by A. C. Grosscurt et al. (Pestic. Sci., 1988, 22,
51). Introduced by Duphar B.V. (later Chemtura Corp.) in 1988. Patents EP 117320; US
4550202; US 4609676 Manufacturers Chemtura
APPLICATIONS:
Biochemistry Chitin synthesis inhibitor, type 0 (Lepidopteran). Mode of action Non-
systemic acaricide and insecticide which inhibits the moulting process in mites and insects.
It is only active against eggs and larval stages. Adult mites and insects are not affected.
Uses Control of eggs and larval stages of eriophyid and tetranychid mite species on a
variety of crops, including fruit crops, vegetables and ornamentals. Also controls larvae
CH
2
F
F
NHCONHCO
O N C
Cl
fucycloxuron 275
of a number of insects. Because of its relative selectivity, fucycloxuron is well-suited for
integrated control programmes. Recommended concentration for control of mites on fruit
crops is 0.010.015% a.i. On insects, good activity has been found against codling moth,
leaf miners and some leaf rollers in pome fruit, at the same concentration. In ornamentals
grown under glass/plastic, lower concentrations can be used. In grapes, the recommended
dosage is 125150 g/ha. Formulation types DC.
PRODUCTS:
Discontinued products Andalin* (Uniroyal).
ANALYSIS:
Product and residue analysis by hplc; details available from Chemtura.
Oral Acute oral LD
50
50
for
rats >2000 mg/kg. Non-irritating to skin; mild eye irritant (rabbits). Inhalation LC
50

(4 h) for rats >3.3 mg/l air. NOEL In 2 y feeding trials, NOAEL for rats 120 mg/kg diet. In a
2-generation reproduction study, NOAEL for rats 200 mg/kg diet. Non-mutagenic and non-
teratogenic. No evidence of carcinogenicity. Other Acute i.p. LD
50
for rats
2000 mg/kg. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks >2000 mg/kg. Dietary LC
50
(8 d) for mallard
ducks and bobwhite quail >6000 mg/kg diet. Fish LC
50
(96 h) for rainbow trout and
bluegill sunfsh >100 mg/l. Daphnia LC
50
(48 h) 0.27 g/l. Algae NOEC for Selenastrum
capricornutum >2.2 ;g/l. Other aquatic spp. LC
50
(96 h) for mysid shrimps (Mysidopsis
bahia) 340 ng/l. Bees Low toxicity to bees. Contact LD
50
for honeybees >100 g/bee.
Worms EC
50
(14 d) for earthworms >1000 mg/kg soil. Otherbenefcial Slightly to
moderately harmful to predatory mites (IOBC).
ENVIRONMENTAL FATE:
Animals Poorly absorbed from gastrointestinal tract; mainly excreted as unchanged
parent compound in the faeces. Flucycloxuron absorbed is metabolised and further
excreted in the urine, mainly as 2,6-difuorobenzoic acid and N-(4-carboxyphenyl)-N-(2,6-
difuorobenzoyl)urea. Plants Non-systemic. Not metabolised on plants.
Soil/Environment Strongly and irreversibly bound by soil/humic acid complex and
virtually immobile in soil. Soil DT
50
0.250.5 y.
276
fufenican
fuenetil
NOMENCLATURE:
Common name fuenetil (BSI, E-ISO, (m) F-ISO); fu(n) (France)
IUPAC name 2-fuoroethyl biphenyl-4-ylacetate
Chemical Abstracts name 2-fuoroethyl [1,1-biphenyl]-4-acetate CAS RN [4301502]
Development codes M 2060 Smiles code FCCOC(=O)Cc1ccc(cc1)c2ccccc2
16
H
15
FO
2
M.p. 60.5 C B.p. 177180 C /1 mmHg S.g./density 1.139 (68 C) Solubility In water
2.5 mg/l (25 C). In acetone >850, acetonitrile 810, benzene 760, ethanol 630, hexane 10,
methanol 80, olive oil <0.7 (all in g/l, 25 C). Stability Stable at pH 4, but hydrolysed at pH
7 and rapidly at pH 9.
COMMERCIALISATION:
History Insecticide reported by P. de Pietri-Tonelli et al. (Proc. Br. Insectic. Fungic. Conf., 3rd,
1965, p. 478). Introduced by Montecatini Edison S.p.A. (later Agrimont S.p.A.).
Patents IT 710046; US 3436418
APPLICATIONS:
Mode of action A selective, non-systemic acaricide and insecticide. Uses Applied in oil at
400600 mg/kg in late winter to control winter eggs of Panonychus ulmi, Bryobia praetiosa,
Aphididae, Psyllidae, some Lepidoptera and the winter stages of scale insects.
PRODUCTS:
Discontinued mixtures Lambrol* (+ petroleum oils) (Montecatini).
ANALYSIS:
Product analysis by glc or by hydrolysis to the corresponding acetic acid which was
measured. Residues determined by glc or by colorimetry.
Oral Acute oral LD
50
for rats 8.7, mice 57, monkeys 75 mg/kg. Skin and eye Acute
percutaneous LD
50
(10 d) for rabbits 7.5 mg/kg. NOEL (90 d) for rats 0.3 mg/kg daily.
Toxicity Class WHO (a.i.) OECClassifcation T+; R27/28
fufenican
Herbicide
NOMENCLATURE:
Common name fuf(nican) ((m) F-ISO); fufenican (BSI, E-ISO)
IUPAC name 2-(,,-trifuoro-m-tolyloxy)nicotinanilide
Chemical Abstracts name N-phenyl-2-[3-(trifuoromethyl)phenoxy]-3-
pyridinecarboximide CAS RN [78863624]
Smiles code FC(F)(F)c1cccc(Oc2ncccc2C(=O)Nc3ccccc3)c1
fufenprox 277
19
H
13
F
3
N
2
O
2
COMMERCIALISATION:
fufenoxystrobin
Fungicide
NOMENCLATURE:
Common name fufenoxystrobin (pa ISO)
IUPAC name methyl (2E)-2-{2-[(2-chloro-,,-trifuoro-p-tolyloxy)methyl]phenyl}-3-
methoxyacrylate
Chemical Abstracts name methyl (E)-2-[[2-chloro-4-(trifuoromethyl)phenoxy]
methyl]--(methoxymethylene)benzeneacetate
Smiles code CO\C=C(C(OC)=O)/C1=C(COC2=CC=C(C(F)(F)F)C=C2Cl)C=CC=C1
19
H
16
ClF
3
O4
fufenprox
Insecticide
IRAC 3
NOMENCLATURE:
Common name fufenprox (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(4-chlorophenoxy)benzyl (RS)-2-(4-ethoxyphenyl)-3,3,3-trifuoropropyl
ether
Chemical Abstracts name 1-(4-chlorophenoxy)-3-[[2-(4-ethoxyphenyl)-
3,3,3-trifuoropropoxy]methyl]benzene CAS RN [107713586]
CF
3
H
O
CH
3
O
CH
3
O
O
Cl
O
CH
3
CH
2
O
CF
3
O
Cl
278
fumezin
Development codes ICIA5682
Smiles code CCOc1ccc(cc1)C(COCc2cccc(Oc3ccc(Cl)cc3)c2)C(F)(F)F
24
H
22
ClF
3
O
3
Form Odourless,
transparent pale yellow-green liquid. B.p. 204 C /0.2 mmHg V.p. 1.3 10
4
mPa (20 C)
S.g./density 1.25 (25 C) Solubility In water 2.5 ;g/l (pH 7). Soluble (>500 g/l) in
hexane, toluene, acetone, dichloromethane, ethyl acetate, n-octanol, acetonitrile and
methanol.
COMMERCIALISATION:
History Insecticide reported by R. F. S. Gordon et al. (Proc. Br. Crop Prot. Conf. - Pests Dis.,
1992, 1, 81).
Manufacturers Zeneca
APPLICATIONS:
Mode of action Insecticide with fast action and residual effcacy. Uses Control of
Homoptera, Heteroptera, Coleoptera and Lepidoptera on rice, including rice hoppers.
Formulation types DL; GR; EW; EC.
Oral Acute oral LD
50
50
for
rats >2000 mg/kg. Mild skin and eye irritant (rabbits). Skin sensitiser (guinea pigs).
ECOTOXICOLOGY:
Fish LC
50
(96 h) for carp >10 mg tech./l, for red killifsh and Asian pond loach >10 mg/l as
0.5% dust or granule. Daphnia LC
50
for D. pulex (48 h) 0.00035 mg/l. Bees LD
50

0.03 g/bee; NOEL 0.002 g/kg. Worms LD
50
for Eisenia foetida >1000 mg/kg.
Otherbenefcial Low toxicity to predatory arthropods.
fumezin
Herbicide
NOMENCLATURE:
Common name fumezin (BSI, E-ISO); fum(zine) ((f) F-ISO)
IUPAC name 2-methyl-4-(,,-trifuoro-m-tolyl)-1,2,4-oxadiazinane-3,5-dione
Chemical Abstracts name 2-methyl-4-[3-(trifuoromethyl)phenyl]-2H-1,2,4-oxadiazine-
3,5(4H,6H)-dione CAS RN [25475734] Development codes BAS 348H (BASF)
Smiles code CN1OCC(=O)N(C1=O)c2cccc(c2)C(F)(F)F
11
H
9
F
3
N
2
O
3
COMMERCIALISATION:
History Herbicide evaluated by BASF AG.
fumipropyn 279
fumipropyn
Herbicide
NOMENCLATURE:
Common name fumipropyne ((m) F-ISO); fumipropyn (BSI, E-ISO)
IUPAC name ()-N-[4-chloro-2-fuoro-5-(1-methylprop-2-ynyl)oxyphenyl]cyclohex-1-
ene-1,2-dicarboximide
Chemical Abstracts name ()-2-[4-chloro-2-fuoro-5-[(1-methyl-2-propynyl)
oxy]phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione CAS RN [84478524]
Development codes S-23121 (Sumitomo Chemical) Smiles code CC(Oc1cc(N
2
C(=O)
C3=C(CCCC3)C2=O)c(F)cc1Cl)C#C
18
H
15
ClFNO
3
Form White to light
brown crystals. M.p. 115116.5 C V.p. 0.28 mPa (20 C) S.g./density 1.39
Solubility In water <1 mg/l (23 C). In acetone 50%, ethyl acetate 3350%, xylene 2030%,
methanol 510%, hexane >1% (all 23 C).
COMMERCIALISATION:
History Reported by T. Hamada et al. (Proc. Br. Crop Prot. Conf. Weeds 1989, 1, 41).
Herbicide introduced by Sumitomo Chemical Co. Ltd for control of broad-leaved weeds in
cereals.
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Systemic herbicide
rapidly absorbed into plant tissues. Rapid necrosis or desiccation of stems and leaves is
induced in the presence of light and oxygen. Soil application induces shoot necrosis.
Uses Control of broad-leaved weeds including Galium aparine, Veronica spp.,and Viola,in
cereals. Formulation types SC. EC.
ANALYSIS:
Product by glc. Residues by hplc.
Oral Acute oral LD
50
50

for rats >2000 mg/kg. Minimal eye irritation; not a skin irritant (rabbits). Other Non-
mutagenic in the Ames test.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp >1 mg/l.
N
O
O
F
Cl
O CH
C
CH
CH
3
280
fuoridamid
fuorbenside
Acaricide
NOMENCLATURE:
Common name fuorbenside (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name 4-chlorobenzyl 4-fuorophenyl sulfde
Chemical Abstracts name 1-chloro-4-[[(4-fuorophenyl)thio]methyl]
benzene CAS RN [405301] Development codes HRS 924; RD 2454
Smiles code Fc1ccc(SCc2ccc(Cl)cc2)cc1
13
H
10
ClFS Form Colourless crystals.
M.p. 36 C V.p. 10 mPa (20 C) Solubility Practically insoluble in water. Very soluble in
acetone and aromatic hydrocarbons; soluble in saturated hydrocarbons. Stability Resistant
to hydrolysis but readily oxidised to the corresponding sulfoxide and sulfone.
COMMERCIALISATION:
History Acaricide reported by N. G. Clark et al. (J. Sci. Food Agric., 1957, 8, 566). Introduced
by The Boots Co., Ltd Agriculture (later Schering Agriculture). Patents GB 748604
APPLICATIONS:
Mode of action Non-systemic acaricide. Uses Effective against adult mites, its high
volatility made it suitable for use in aerosols and in smokes. Formulation types Aerosols;
smokes.
PRODUCTS:
Discontinued products Fluorparacide* (Boots); Fluorsulphacide* (Boots).
ANALYSIS:
Residues determined by oxidation to the sulfone which is measured colorimetrically as a
derivative.
Oral Acute oral LD
50
for ratsc. 3000 mg/kg. NOEL In 2 y feeding trials, rats receiving
100 mg/kg diet suffered no ill effect, but in 21 d trials, those receiving 50 mg/kg daily
suffered slight liver and kidney enlargement.
fuoridamid
NOMENCLATURE:
Common name fuoridamide ((m) F-ISO); fuoridamid (BSI, E-ISO, ANSI)
IUPAC name 3-(1,1,1-trifuoromethanesulfonamido)acet-p-toluidide
Chemical Abstracts name N-[4-methyl-3-[[(trifuoromethyl)sulfonyl]amino]
phenyl]acetamide CAS RN [47000920] Development codes MBR-6033
Smiles code CC(=O)Nc1ccc(C)c(NS(=O)(=O)C(F)(F)F)c1
fuorodifen 281
10
H
11
F
3
N
2
O
3
S
COMMERCIALISATION:
History Plant growth regulator introduced by 3M Co.
PRODUCTS:
Discontinued products Sustar* (3M).
fuorodifen
Herbicide
NOMENCLATURE:
Common name fuorodifen (BSI, E-ISO, ANSI, WSSA, JMAF); fuorodif(ne) ((m) F-ISO)
IUPAC name 4-nitrophenyl ,,-trifuoro-2-nitro-p-tolyl ether
Chemical Abstracts name 2-nitro-1-(4-nitrophenoxy)-4-(trifuoromethyl)benzene
CAS RN [15457053] Development codes C 6989 (Ciba) Smiles code [O-][N+]
(=O)c1ccc(Oc2ccc(cc2[N+](=O)[O-])C(F)(F)F)cc1
13
H
7
F
3
N
2
O
5
Form Yellowish crystals.
M.p. 94.094.5 C V.p. 0.0093 mPa (20 C) Henry 1.53 10
3
Pa m
3
mol
1
(calc.)
dichloromethane 680, hexane 1.4, methanol 4.5, n-octanol 10, toluene 400 (all in g/l, 20 C).
Stability No signifcant hydrolysis occured during 28 d at pH 19 (70 C).
COMMERCIALISATION:
History Herbicide reported by L. Ebner et al. (Proc. Br. Weed Control Conf., 9th, 1968, 2,
1026). Introduced by Ciba AG (later Ciba-Geigy AG). Patents BE 628133; GB 1033163
APPLICATIONS:
Mode of action Contact herbicide. Uses A pre-em. and post-em. contact herbicide used
at 34 kg/ha. It was recommended pre-em. for use on drilled rice, but not for surface
seeded rice. Formulation types EC.
PRODUCTS:
Discontinued products Preforan* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc. Residues determined by glc with ECD.
Oral Acute oral LD
50
50

for rats >3000 mg/kg. Not irritant to skin; moderate irritant to eyes (rabbits).
Inhalation (6 h) for rats >0.99 mg/l air. NOEL (90 d) for rats 1000 mg/kg diet (67 mg/kg
daily), for dogs 316 mg/kg diet (10 mg/kg daily). Toxicity Class WHO (a.i.) U
282
fuoronitrofen
fuoromidine
Herbicide
NOMENCLATURE:
Common name fuoromidine (BSI (from 1984), E-ISO); furomidine ((f) F-ISO, (before
1984) BSI)
IUPAC name 6-chloro-2-trifuoromethyl-3H-imidazo[4,5-b]pyridine
Chemical Abstracts name 6-chloro-2-(trifuoromethyl)-1H-imidazo[4,5-b]pyridine
CAS RN [13577714] Development codes NC 4780
Smiles code FC(F)(F)c1nc2ncc(Cl)cc2[nH]1
7
H
3
ClF
3
N
3
COMMERCIALISATION:
History Herbicide evaluated by Fisons Ltd (later Schering Agriculture).
fuoronitrofen
Herbicide
NOMENCLATURE:
Common name fuoronitrofen (BSI, E-ISO); fuoronitrof(ne) ((m) F-ISO)
IUPAC name 2,4-dichloro-6-fuorophenyl 4-nitrophenyl ether
Chemical Abstracts name 1,5-dichloro-3-fuoro-2-(4-nitrophenoxy)benzene
CAS RN [13738631] Development codes Mo 500
Smiles code [O-][N+](=O)c1ccc(Oc2c(F)cc(Cl)cc2Cl)cc1
12
H
6
Cl
2
FNO
3
COMMERCIALISATION:
History Herbicide developed by Mitsui Toatsu Chemicals, Inc. (later Mitsui Chemicals, Inc.).
APPLICATIONS:
Biochemistry Inhibits protoporphyrinogen oxidase.
PRODUCTS:
Discontinued products Mo500* (Mitsui Toatsu).
Cl O NO
2
Cl
F
fuotrimazole 283
fuothiuron
Herbicide
NOMENCLATURE:
Common name fuothiuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(3-chloro-4-chlorodifuoromethylthiophenyl)-1,1-dimethylurea
Chemical Abstracts name N-[3-chloro-4-[(chlorodifuoromethyl)thio]phenyl]-
N,N-dimethylurea CAS RN [33439451] Development codes BAY KUE 2079A
Smiles code CN(C)C(=O)Nc1ccc(SC(F)(F)Cl)c(Cl)c1
10
H
10
Cl
2
F
2
N
2
OS Form Colourless
crystals. M.p. 113114 C V.p. <17 mPa (20 C) Henry <7.34 10
5
Pa m
3
mol
1
(calc.)
Solubility In water 73 g/l (20 C). In cyclohexanone 377, dichloromethane 316 (both in
g/l, 20 C).
COMMERCIALISATION:
History Herbicide introduced by Bayer AG. Patents GB 1314864; US 3931312
APPLICATIONS: Uses It was used at 2.5 g/ha to control dicotyledonous weeds in
paddy rice. Formulation types EC; GR .
PRODUCTS:
Discontinued products Clearcide* (Bayer).
Oral Acute oral LD
50
percutaneous LD
50
for rats >500 mg/kg. NOEL (90 d) for rats 40 mg/kg diet, for mice
20 mg/kg diet.
fuotrimazole
Fungicide
NOMENCLATURE:
Common name fuotrimazole (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-(3-trifuoromethyltrityl)-1H-1,2,4-triazole
Chemical Abstracts name 1-[diphenyl[3-(trifuoromethyl)phenyl]methyl]-1H-
1,2,4-triazole CAS RN [31251033] Development codes BAY BUE 0620
Smiles code FC(F)(F)c1cccc(c1)C(c2ccccc2)(c3ccccc3)n4cncn4
22
H
16
F
3
N
3
Form Colourless crystalline
solid. M.p. 132 C Solubility In water 0.0015 mg/l (20 C). In cyclohexanone 200,
dichloromethane 400, isopropanol 50, toluene 100 (all in g/kg, 20 C). Stability Stable in
0.1M sodium hydroxide, but undergoesc. 40% degradation in 0.2M sulfuric acid in 24 h.
COMMERCIALISATION:
History Fungicide reported by F. Grewe & K. H. Bchel (Mitt. Biol. Bundesanst. Land-
284
fupropacil
Forstwirtsch. Berlin-Dahlem, 1973, 151, 208). Introduced by Bayer AG.
Patents DE 1795249; US 3682950
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. Uses A fungicide with specifc action
against powdery mildew on barley, cucumbers, grapes, melons and peaches.
Formulation types EC; WP.
PRODUCTS:
Discontinued products Persulon* (Bayer).
ANALYSIS:
Product analysis by i.r. spectroscopy. Residues determined by glc with FID (W. Specht,
Pfanz.-Nachr. Bayer (Engl. Ed.), 1977, 30, 55; W. Specht & M. Tillkes ibid., 1980, 33, 61).
Oral Acute oral LD
50
50
for
rats >1000 mg/kg. NOEL (2 y) for rats 50 mg/kg diet; (90 d) for rats 800 mg/kg diet, for
dogs >5000 mg/kg diet. Toxicity Class WHO (a.i.) U
fupropacil
Herbicide
NOMENCLATURE:
Common name fupropacil (BSI, E-ISO, (m) F-ISO)
IUPAC name isopropyl 2-chloro-5-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-4-
trifuoromethylpyrimidin-1-yl)benzoate
Chemical Abstracts name 1-methylethyl 2-chloro-5-[3,6-dihydro-3-methyl-2,6-
dioxo-4-(trifuoromethyl)-1(2H)-pyrimidinyl]benzoate CAS RN [120890702]
Development codes UCC-C4243 (Uniroyal)
16
H
14
ClF
3
N
2
O
4
COMMERCIALISATION:
History Herbicide evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
Biochemistry Inhibitor of protoporphyrinogen oxidase. Uses Control of many broad-
leaved, and some annual grass weeds.
CO
2
CH(CH
3
)
2
N N
F
3
C O
O
CH
3
Cl
fupropadine; fupropadine hydrochloride 285
ENVIRONMENTAL FATE:
Soil/Environment Aerobic soil DT
50
79 d; the major metabolite was the corresponding
acid; there was negligible mineralisation to CO
2
.
fupropadine; fupropadine hydrochloride
Rodenticide
NOMENCLATURE:
Common name fupropadine (BSI, E-ISO, (f) F-ISO)
IUPAC name 4-tert-butyl-1-[3-(,,,,,-hexafuoro-3,5-xylyl)prop-2-ynyl]piperidine
Chemical Abstracts name 1-[3-[3,5-bis(trifuoromethyl)phenyl]-2-
propynyl]-4-(1,1-dimethylethyl)piperidine CAS RN [81613594] fupropadine
Development codes M&B 36 892
PHYSICAL CHEMISTRY: Mol. wt. 391.4; (hydrochloride 427.9) M.f. C2
0
H
23
F
6
N;
(hydrochloride C20H24ClF6N) Form The hydrochloride is a solid. M.p. 201202 C
(hydrochloride) Solubility In diethyl ether >150 g/l (5 C).
COMMERCIALISATION:
History Rodenticide reported by A. P. Buckle (J. Hyg., 1985, 95, 505) and by F. P. Rowe et al.
(ibid., p. 513). Introduced by May & Baker Ltd (later Rhne-Poulenc Agriculture).
Patents EP 41324
APPLICATIONS: Uses Control of brown rats (Rattus norvegicus, including those
resistant to anticoagulant rodenticides) around grain stores. Also controls house mice
(Mus musculus). See W. Parnell, BCPC Monograph, 1987, No. 37, p. 125.
Oral Acute oral LD
50
for mice 68 mg/kg.
CF
3
CF
3
C C CH
2
N C(CH
3
)
3
286
furazole
furazole
Herbicide safener
NOMENCLATURE:
Common name furazole (WSSA)
IUPAC name benzyl 2-chloro-4-trifuoromethyl-1,3-thiazole-5-carboxylate
Chemical Abstracts name phenylmethyl 2-chloro-4-(trifuoromethyl)-
5-thiazolecarboxylate CAS RN [72850647] EC no 2769423
Development codes MON 4606 (Monsanto)
Smiles code FC(F)(F)c1nc(Cl)sc1C(=O)OCc2ccccc2
PHYSICAL CHEMISTRY:
Composition Tech. is 98% pure. Mol. wt. 321.7 M.f. C
12
H
7
ClF
3
NO
2
S Form Colourless
crystals, with a slight sweet odour; (tech. is a yellow to tan solid). M.p. 5153 C
V.p. 3.9 10-2 mPa (25 C) Henry 2.51 10-2 Pa m
3
mol
1
(tech.) Solubility In water 0.5 mg/l (25 C). Soluble in most organic solvents, including
alcohols, ketones, and xylene. Stability Stable below 93 C. F.p. 392 C (tech.) (Tag closed
cup)
COMMERCIALISATION:
History Herbicide safener introduced by Monsanto Co. in 1994.
Manufacturers Monsanto
APPLICATIONS:
55(11) 10431058). Uses Used as a herbicide safener. When applied as a seed protectant
to grain sorghum, acts as a safener against the phytotoxic effects of herbicides containing
alachlor or metolachlor. Formulation types Seed treatment; WG .
PRODUCTS:
Discontinued products Screen* (Monsanto).
ANALYSIS:
Details from Monsanto.
EU Status (1107/2009) Considered to be outside the scope of the Directive; considered
not to be a plant protection product.
N
S
Cl
CF
3
C
O
O CH
2
fuvalinate 287
Oral Acute oral LD
50
50
for
rabbits >5010 mg/kg. Non-irritating to skin; slightly irritating to eyes (rabbits). Not a skin
sensitiser (guinea pigs). Inhalation No signifcant adverse health effects reported through
occupational exposure. NOEL (90 d) for dogs 300 mg/kg daily, for rats 5000 mg/kg diet.
ECClassifcation N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >2510 mg/kg. Dietary LC
50
(5 d) for mallard
ducks and bobwhite quail >5620 ppm. Fish LC
50
(96 h) for common carp 1.7, rainbow
trout 8.5, bluegill sunfsh 11 mg/l. Daphnia LC
50
(48 h) 6.3 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment Rapidly degraded in soil, with the formation of water-soluble
metabolites. Breakdown is primarily microbial, with chemical breakdown of lesser
importance.
fuvalinate
IRAC 3
NOMENCLATURE:
Common name fuvalinate (BSI, ANSI, E-ISO, (m) F-ISO)
IUPAC name (RS)--cyano-3-phenoxybenzyl N-(2-chloro-,,-trifuoro-p-tolyl)-DL-
valinate
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl N-[2-chloro-4-
(trifuoromethyl)phenyl]-DL-valinate CAS RN [69409945]
Smiles code CC(C)C(Nc1ccc(cc1Cl)C(F)(F)F)C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2
26
H
22
ClF
3
N
2
O
3
Form Tech. is a
viscous yellow oil. B.p. >450 C (extrapolated) V.p. <0.013 mPa (25 C) K
ow
logP >3.8
S.g./density 1.29 Solubility In water <0.005 mg/kg. Freely soluble in alcohols, aromatic
hydrocarbons, dichloromethane, diethyl ether. Stability DT
50
30 d (pH 3 and pH 6), 12 h
(pH 9) (25 C); 35 d (pH 3), 8 d (pH 6), 1 d (pH 9) (42 C). Stable in glass >1.5 y (42 C).
In sunlight thin flms on glass or silica gel suffered 50% loss inc. 2 d, an aqueous emulsion
(1.6 g/l) in glass in 12 d.
COMMERCIALISATION:
History Insecticide reported by C. A. Henrick et al. (Pestic. Sci., 1980, 11, 224) and by R. J.
Anderson (J. Agric. Food Chem., 1985, 33, 508). Fluvalinate introduced by Zoecon Corp. (later
Sandoz AG) and replaced by tau-fuvalinate (the D-valinate) [NOTE many references in the
literature have been made, in error, to fuvalinate rather than to tau-fuvalinate].
Patents US 4411912; US 4260633
288
FMC 1137
APPLICATIONS:
neurons by interaction with the sodium channel. Mode of action Contact insecticide
and acaricide. Uses A broad-range, foliar-applied insecticide and acaricide effective at
56168 g/ha against Aphididae, Cicadellidae, Lepidoptera, Thysanoptera, Tetranychidae and
Trialeurodes vaporariorum on ornamentals, vegetables, trees and vines.
PRODUCTS:
Other products Mavric (Nippon Soda); Discontinued products Kaiser* (Rocca);
Mavrik* (Zoecon).
ANALYSIS:
Product analysis of pyrethroids reviewed by E. Papadopoulou-Mourkidou in Comp. Anal.
Profles. By hplc (W. L. Fitch et al., Anal. Methods Pestic. Plant Growth Regul., 1984, 13, 79).
Residues determined by glc with ECD (idem, ibid.; AOAC Methods, 18th Ed., 998.01; Resid.
Anal. Methods; Environ. Chem. Methods). See also Pestic. Anal. Man., II, 180.427, 186.3400.
Oral Acute oral LD
50
50

for rats and rabbits >20 000 mg/kg. Mild skin irritant; mild to moderate eye irritant.
NOEL (2 y) for rats 1 mg/kg b.w. daily (EPA IRIS). ADI/RfD (BfR) 0.005 mg/kg b.w. [1990];
(EPA) cRfD 0.01 mg/kg b.w. [1991]. Toxicity Class WHO (a.i.) II
ENVIRONMENTAL FATE:
Soil/Environment In sandy loam under aerobic conditions DT
50
c. 6 d.
FMC 1137
IRAC 1B
NOMENCLATURE:
IUPAC name bis(diethoxyphosphinothioyl) disulfde (i) + bis(diisopropoxyphosphinothio
yl) disulfde (ii) 75:25 mixture
Chemical Abstracts name bis(diethoxyphosphinothioyl) disulfde (i) + bis[di-(1-
methylethoxy)phosphinothioyl] disulfde (ii) CAS RN [2901908] (i); [3031218] (ii)
Development codes FMC 1137; NIA 1137
8
H
20
O
4
P
2
S
4
(i);
C
12
H
28
O
4
P
2
S
4
(ii)
COMMERCIALISATION:
History Insecticide and acaricide introduced by FMC Corp.
APPLICATIONS:
FMC 21861 289
PRODUCTS:
Discontinued products Phostex* (FMC).
FMC 19873
Herbicide
NOMENCLATURE:
IUPAC name 6-tert-butyl-3-isopropyl[1,2]thiazolo[3,4-d]pyrimidin-4(5H)-one; 6-tert-
butyl-4,5-dihydro-3-isopropylisothiazolo[3,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-(1-methylethyl)isothiazolo[3,4-d]
pyrimidin-4(5H)-one CAS RN [40915864] Development codes FMC 19873
Smiles code CC(C)c1snc2nc([nH]c(=O)c12)C(C)(C)C
12
H
17
N
3
OS
COMMERCIALISATION:
History Herbicide evaluated by FMC Corp.
FMC 21844
Herbicide
NOMENCLATURE:
IUPAC name 6-tert-butyl-3-isopropyl-1,2-oxazolo[5,4-d]pyrimidin-4(5H)-one; 6-tert-
butyl-4,5-dihydro-3-isopropylisoxazolo[5,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-(1-methylethyl)isoxazolo[5,4-d]
Smiles code CC(C)c1noc2nc([nH]c(=O)c12)C(C)(C)C
12
H
17
N
3
O
2
COMMERCIALISATION:
FMC 21861
Herbicide
NOMENCLATURE:
IUPAC name 6-tert-butyl-3-propyl-1,2-oxazolo[5,4-d]pyrimidin-4(5H)-one; 6-tert-butyl-
4,5-dihydro-3-propylisoxazolo[5,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-propylisoxazolo[5,4-d]
290
FMC 25213
Smiles code CCCc1noc2nc([nH]c(=O)c12)C(C)(C)C
12
H
17
N
3
O
2
COMMERCIALISATION:
FMC 23486
Herbicide
NOMENCLATURE:
IUPAC name 6-tert-butyl-3-isopropyl[1,2]oxazolo[3,4-d]pyrimidin-4(5H)-one; 6-tert-
butyl-4,5-dihydro-3-isopropylisoxazolo[3,4-d]pyrimidin-4-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-(1-methylethyl)isoxazolo[3,4-d]
Smiles code CC(C)c1onc2nc([nH]c(=O)c12)C(C)(C)C
12
H
17
N
3
O
2
COMMERCIALISATION:
History Herbicide reported by W. M. Dest et al. (Proc. Northeast. Weed Sci. Soc., 1973, 27,
31). Evaluated by FMC Corp.
FMC 25213
Herbicide
NOMENCLATURE:
IUPAC name 2-ethyl-5-methyl-1,3-dioxan-5-yl 2-methylbenzyl ether; 2-ethyl-5-methyl-5-
(2-methylbenzyloxy)-1,3-dioxane
Chemical Abstracts name 2-ethyl-5-methyl-5-[(2-methylphenyl)methoxy]-1,3-
dioxane CAS RN [41129106] cis- isomer Development codes FMC 25213
Smiles code CCC1OCC(C)(CO1)OCc2ccccc2C
15
H
22
O
3
COMMERCIALISATION:
History Herbicide reported (Ann. Meet. South. Weed Sci. Soc., 27th, 1974) and evaluated
by FMC Corp.
fonofos 291
fonofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name fonofos (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name O-ethyl S-phenyl (RS)-ethylphosphonodithioate
Chemical Abstracts name ()-O-ethyl S-phenyl ethylphosphonodithioate
CAS RN [944229] unstated stereochemistry; [66767393] racemate; [62705719]
(R)- isomer; [62680039] (S)- isomer EC no 2134080 Development codes N-2790
(Stauffer) Smiles code CCOP(=S)(CC)Sc1ccccc1
PHYSICAL CHEMISTRY:
Composition Tech. is 99.5%. The chiral forms have been isolated (R. Allahyari et al., J.
Agric. Food Chem., 1977, 25, 471; P. W. Lee et al., Pestic. Biochem. Physiol., 1978, 8, 146, 158).
Mol. wt. 246.3 M.f. C
10
H
15
OPS
2
Form Clear, colourless liquid, with an aromatic odour.
B.p.c. 130 C /0.1 mmHg V.p. 28 mPa (25 C) K
ow
logP = 3.94 S.g./density 1.16 (25 C)
Solubility In water 13 mg/l (22 C). Miscible with organic solvents, e.g. acetone, ethanol,
methyl isobutyl ketone, xylene, kerosene. Stability Stable below 100 C. Hydrolysed in
acidic and alkaline media; DT
50
101 d (pH 4), 74127 d (pH 7, depending on buffer), 1.8 d
(pH 10) (40 C). In light DT
50
12 d (pH 5, 25 C). Specifc rotation Optical rotations of the
chiral forms are reversed on solution in carbon tetrachloride, cyclohexane, methanol
F.p. 179 C
COMMERCIALISATION:
History Insecticide reported by J. J. Menn & K. Szabo (J. Econ. Entomol., 1965, 58, 734).
Introduced by Stauffer Chemical Co. (later Zeneca Agrochemicals).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor; proinsecticide, activated by metabolic oxidative
desulfuration to the corresponding oxon. The (R)-isomer is more toxic to insects and mice
and a more potent inhibitor of cholinesterase than the (S)-isomer. Mode of action Soil
insecticide with contact and stomach action. Uses Control of soil insects (especially
mole crickets, corn rootworms, symphylids, wireworms, Vine weevil larvae, cockchafer
larvae, cabbage root fy, onion fy, carrot fy, wheat bulb fy, etc.) in cereals, maize, sorghum,
vegetables, ornamentals, fruit (including citrus and bananas), vines, olives, potatoes, sugar
beet, sugar cane, peanuts, tobacco, and turf at 1.01.5 kg/ha. Formulation types GR; MG;
EC; SC. CS; Seed treatment.
S
P
S
CH
2
CH
3
OCH
2
CH
3
292
fonofos
PRODUCTS:
Discontinued products Capfos* (Zeneca); Cudgel* (Zeneca); Dyfonate* (Zeneca);
Discontinued mixtures Edge* (+ pebulate) (Zeneca); Oslo* (+ anthraquinone + oxine-
copper) (Sopra).
ANALYSIS:
Product analysis by capillary glc (J. E. Barney et al., Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 269). Residues in crops, soil and water determined similarly (idem, ibid.; Environ.
Chem. Methods). See also Pestic. Anal. Man., I, 204; ibid., II, 180.221.
EHC 63 (1986) is a general review of organophosphorus insecticides. ICSC.708 (1997).
Oral Acute oral LD
50
for male rats 11.5, female rats 5.5 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats 147, rabbits 32261, guinea pigs 278 mg/kg. Non-irritating to
skin and eyes (rabbits). Weak skin sensitiser (guinea pigs). Inhalation LC
50
(4 h) for male
rats 51, female rats 17 g/l. NOEL (2 y) for rats 10 mg/kg diet (0.5 mg/kg b.w. daily);
for dogs 0.2 mg/kg b.w. daily. Not carcinogenic or teratogenic. ADI/RfD (EPA) cRfD
0.002 mg/kg b.w. [1991]. Toxicity Class WHO (a.i.) Ia EPA (formulation) I or II
ECClassifcation T+; R27/28| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks 128 mg/kg. Fish LC
50
0.05, bluegill sunfsh 0.028 mg/l. Daphnia LC
50
(48 h) 1 g/l. Bees Toxic to bees; LD
50

0.0087 mg/bee.
ENVIRONMENTAL FATE:
Animals Metabolism in animals is similar to that in plants. Plants In plants, metabolism
involves oxidation to the phosphonothioate, and hydrolytic cleavage of the thiophenol
residue. Soil/Environment Under aerobic conditions, fonofos at 10 ppm was degraded
at a moderate rate, DT
50
316 weeks in soils ranging from loamy sand to clay loam to peat;
adsorption K 15.3 (loam soil). The major degradate was O-ethyl ethanephosphonothioic
acid; other degradates included fonofos oxon, O-ethyl ethanephosphonic acid, O-ethyl
O-methylethyl phosphonate, diphenyl sulfde, methylphenyl sulfoxide and methylphenyl
sulfone.
formothion 293
formothion
IRAC 1B
NOMENCLATURE:
Common name formothion (BSI, E-ISO, (m) F-ISO, ESA, JMAF)
IUPAC name S-[formyl(methyl)carbamoylmethyl] O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-formyl-N-methylacetamide
Chemical Abstracts name S-[2-(formylmethylamino)-2-oxoethyl] O,O-
dimethyl phosphorodithioate CAS RN [2540821] EC no 2198186
Development codes J-38; SAN 6913I Smiles code COP(=S)(OC)SCC(=O)N(C)C=O
6
H
12
NO
4
PS
2
Form Odourless,
pale yellow, viscous liquid or crystalline mass. M.p. 2526 C B.p. Decomposes on
distillation. V.p. 0.113 mPa (20 C) S.g./density 1.361 (20 C) Solubility In water 2.6
g/l (24 C). Completely miscible with common organic solvents, e.g. alcohols, ethers,
ketones, chloroform, benzene, toluene, xylene; slightly soluble in hexane; very slightly
soluble in ligroin and paraffn oil. Stability EC hydrolysed by water to dimethoate and
(dimethoxyphosphinothioylthio)acetic acid; DT
50
1 d (pH 39, 23 C). Hydrolysed more
rapidly in alkaline media. Dilute solutions in non-polar organic solvents are stable. The a.i. is
degraded inc. 28 d at 54 C.
COMMERCIALISATION:
History Insecticide reported by C. Klotzsche (Mitt. Geb. Lebensmittelunters. Hyg., 1961,
52, 341). Introduced by Sandoz AG (later Novartis Crop Protection AG).
Patents US 3176035; US 3178337 Manufacturers Novartis
APPLICATIONS:
acaricide with contact and stomach action. Uses Effective at 250500 g/ha against a
wide range of sucking and mining insects such as Aphididae, bugs, Cicadellidae, Coccidae,
Diaspididae, Drosophilidae, Margarodidae, Psyllidae, Tephritidae and Thysanoptera, as well
as against some chewing insects (Cydia pomonella and Epilachna spp.) and spider mites
on a variety of feld crops, fruit trees, citrus and other tropical fruit, cotton, grapes, hops,
ornamentals, rice, sugar cane, tobacco and vegetables. Phytotoxicity Phytotoxic to some
varieties of peach, apricot and cherry. Formulation types EC; UL.
S
P(OCH
3
)
2
S
CH
C
NH
O
CH
3
CH
O
294
formparanate
PRODUCTS:
Discontinued products Afix* (Sandoz); Anthio* (Novartis);
Discontinued mixtures Anthiomix* (+ fenitrothion) (Novartis).
ANALYSIS:
Product analysis by glc with FID (CIPAC Handbook, 1998, H, 178), or by glc with FPD
(AOAC Methods, 18th Ed., 974.03). Residues determined by glc (A. Ambrus et al., J. Assoc. Off.
Anal. Chem., 1981, 64, 733; M. Wisson et al., Anal. Methods Pestic. Plant Growth Regul., 1976, 8,
123).
JMPR Evaln. I 72 (1994), 84 (1998). EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD
50
for rats 365500, mice 190195, rabbits 570, cats 213 mg/kg.
50
for male rats >1000 mg/kg. Slightly irritating to
skin (rabbits). Inhalation LC
50
(4 h) for rats 3.2 mg/l air (as Anthio 50ZP). NOEL In 2 y
feeding trials, rats and dogs receiving 80 mg/kg diet showed no adverse effects.
ADI/RfD (JMPR) ADI withdrawn [1996]. Water GV Excluded from GV derivation (U).
Toxicity Class WHO (a.i.) II EPA (formulation) II ECClassifcation Xn; R21/22
ECOTOXICOLOGY:
Birds Acute oral LD
50
for pigeons 630 mg/kg. Fish LC
50
(72 h) for carp 10 mg/l; (96
h) for rainbow trout 38.3 mg/l. Daphnia LC
50
50
(96 h) for
Scenedesmus subspicatus 42.3 mg/l. Bees Toxic to bees; LD
50
(oral) 1.537, (topical) 1.789,
(contact, deposit) 28.447 g/g b.w. Worms LC
50
(14 d) for earthworms 157.7 mg/kg soil.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, formothion is metabolised to
(dimethoxyphosphinthioylthio)acetic acid and polar metabolites, and elimination
occurs within 24 h. Plants In plants, formothion is metabolised to dimethoate (q.v.),
(dimethoxyphosphinthioylthio)acetic acid, bis(dimethylthiophosphoryl) disulfde, omethoate
(q.v.), and O,O-dimethyl hydrogen phosphorodithioate. Soil/Environment DT
50
in loamy
soil <1 d, forming dimethoate (q.v.) and (dimethoxyphosphinthioylthio)acetic acid, which
ultimately dissipate.
formparanate
NOMENCLATURE:
Common name formparanate (BSI, E-ISO); formoparanate ((m) F-ISO)
IUPAC name 4-dimethylaminomethyleneamino-m-tolyl methylcarbamate
fosmethilan 295
Chemical Abstracts name N,N-dimethyl-N-[2-methyl-4-[[(methylamino)carbonyl]oxy]
phenyl]methanimidamide CAS RN [17702577] Development codes UC 25 074
Smiles code CNC(=O)Oc1ccc(N=CN(C)C)c(C)c1
12
H17N3O
2
COMMERCIALISATION:
History Insecticide and acaricide evaluated by Union Carbide.
APPLICATIONS:
fosmethilan
Insecticide
IRAC 1B
NOMENCLATURE:
Common name fosm(thilane) ((m) F-ISO); fosmethilan (BSI, E-ISO)
IUPAC name S-[N-(2-chlorophenyl)butyramidomethyl] O,O-dimethyl phosphorodithioate;
2-chloro-N-(dimethoxyphosphinothioylthiomethyl)butyranilide
Chemical Abstracts name S-[[(2-chlorophenyl)(1-oxobutyl)amino]methyl] O,O-
dimethyl phosphorodithioate CAS RN [83733828] Development codes NE-79 168
Smiles code CCCC(=O)N(CSP(=S)(OC)OC)c1ccccc1Cl
13
H
19
ClNO
3
PS
2
Form Colourless
crystals. M.p. 42 C V.p. 12 mPa K
ow
logP = 0.56 Solubility In water 2.3 mg/l (20 C).
Stability On hydrolysis (20 C) DT
50
12.7 d (pH 4.5), 13.1 d (pH 7), 11.4 d (pH 8.3).
COMMERCIALISATION:
History Insecticide reported by K. Sagi et al. (Proc. 10th Int. Congr. Plant Prot., 1983, 1,
384).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Control of Diptera, Hemiptera,
Lepidoptera, Coleoptera, and Hymenoptera on pome fruit, stone fruit, vegetables, and feld
crops. Formulation types EC.
PRODUCTS:
Discontinued products Nevifos* (Neviki); Neviphos* (Chemolimpex).
P(OCH
3
)
2
S
CH
2
C
O
N
Cl
S
CH
3
(CH
2
)
2
296
fosthietan
Oral Acute oral LD
50
for male rats 110 mg/kg, female rats 49 mg/kg. Skin and eye Acute
percutaneous LD
50
for male rats >11 000, female rats 6000 mg/kg. Slight skin and eye
irritant (rabbits). Inhalation LC
50
for male rats >15 mg/l. Toxicity Class WHO (a.i.) Ib
ECOTOXICOLOGY:
Birds Acute oral LD
50
for pheasants 92, Japanese quail 6874 mg/kg. Dietary LC
50
(8 d) for
pheasants 1330, quail 11 250 mg/kg diet. Fish LC
50
(96 h) for carp 6, goldfsh 12 mg/l.
fospirate
Insecticide
IRAC 1B
NOMENCLATURE:
Common name fospirate (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name dimethyl 3,5,6-trichloro-2-pyridyl phosphate
Chemical Abstracts name dimethyl 3,4,5-trichloro-2-pyridinyl phosphate
CAS RN [5598527] Development codes Dowco 217
Smiles code COP(=O)(OC)Oc1nc(Cl)c(Cl)cc1Cl
7
H
7
Cl
3
NO
4
P
COMMERCIALISATION:
History Insecticide introduced by Dow Chemical Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Torelle* (Dow).
fosthietan
IRAC 1B
NOMENCLATURE:
Common name fosthietan (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name diethyl 1,3-dithietan-2-ylidenephosphoramidate (I)
Chemical Abstracts name (I); 2-(diethoxyphosphinylimino)-1,3-dithietane
CAS RN [21548323] EC no 2444377 Development codes AC 64 475
Smiles code CCOP(=O)(OCC)N=C1SCS1
6
H
12
NO
3
PS
2
Form Tech. is a yellow
frontalin 297
liquid, with a mercaptan-like odour. V.p. 0.86 mPa (25 C) Henry 4.15 10
6
Pa m
3
mol
1

(calc.) S.g./density 1.3 (25 C) Solubility In water 50 g/l (25 C). Soluble in acetone,
chloroform, methanol, toluene.
COMMERCIALISATION:
History Insecticide and nematicide described by W. K. Whitney & J. L. Aston (Proc. Br.
Insectic. Fungic. Conf. 8th, 1975, 2, 625). Introduced by American Cyanamid Co.
Patents US 3476837
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses A broad-range insecticide and nematicide,
effective with soil applications of 15 kg/ha. Formulation types GR; SL .
PRODUCTS:
Discontinued products Acconem* (Cyanamid); Geofos* (Cyanamid); Nematak*
(USA) (Cyanamid).
EHC 63 (1986; a general review of organophosphorus insecticides). EU Status
Oral Acute oral LD
50
for rats 5.7 mg tech./kg. Skin and eye Acute percutaneous LD
50

(24 h) for rabbits 54 mg/kg. Toxicity Class WHO (a.i.) OECClassifcation T+; R27/28
ENVIRONMENTAL FATE:
Soil/Environment In soil DT
50
(chemical degradation)c. 1042 d.
frontalin
Insect pheromone
See also The Manual of Biocontrol Agents entry: 4:403-4:405
An aggregation pheromone of the Western pine beetle (Dendroctonus brevicomis), the
spruce beetle (D. rufpennis), the Douglas fr beetle (D. pseuodtsugae), and the Southern
pine beetle (D. frontalis). For a general review, see G. Dupuis & N. Berland, http://www.
faidherbe.org/site/cours/dupuis/fronta4.htm.
NOMENCLATURE:
IUPAC name 1,5-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane
Chemical Abstracts name 1,5-dimethyl-6,8-dioxa-bicyclo[3.2.1]octane
O
(-)-frontalin
O
CH
3
CH
3
298
furalaxyl
CAS RN [28401390] (-)-frontalin, formerly [57917950], [22625043] and
[22625189]
PHYSICAL CHEMISTRY:
Composition The natural pheromone, (-)-frontalin, is the (1S,5R)- isomer (as drawn).
Mol. wt. 142.2 M.f. C
8
H
14
O
2
COMMERCIALISATION:
Manufacturers ChemTica; Contech
APPLICATIONS: Uses In mixture with alpha-pinene, used for control of spruce
beetle (Dendroctonus rufpennis) and Douglas fr beetle (Dendroctonus pseudotsugae); also, in
mixture with exo-brevocomin and myrcene for control of Western pine beetle
(D. brevicomis). Lures are attached to host trees, which attract both male and female
beetles. The tree is then felled and destroyed before the insect brood emerges. This
reduces attacks in non-baited areas, and reduces the population of beetles.
furalaxyl
Fungicide
FRAC 4, A1
NOMENCLATURE:
Common name furalaxyl (BSI, E-ISO, (m) F-ISO)
IUPAC name methyl N-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate
Chemical Abstracts name methyl N-(2,6-dimethylphenyl)-N-(2-furanylcarbonyl)-
DL-alaninate; N-(2,6-dimethylphenyl)-N-(2-furanylcarbonyl)-DL-alanine methyl ester
CAS RN [57646307] EC no 2608751 Development codes CGA 38 140 (Ciba-
Geigy) Smiles code COC(=O)C(C)N(C(=O)c1ccco1)c2c(C)cccc2C
17
H
19
NO
4
Form White, odourless
crystals. M.p. 70 C and 84 C (dimorphic) V.p. 0.07 mPa (20 C) K
ow
logP = 2.7
Henry 9.3 10
5
Pa m
3
mol
1
(calc.) S.g./density 1.22 (20 C) Solubility In water 230
mg/l (20 C). In dichloromethane 600, acetone 520, methanol 500, benzene 480, hexane 4
(all in g/kg, 20 C). Stability Relatively stable in neutral or weakly acidic media. Less stable
in alkaline media; on hydrolysis, DT
50
(20 C) (calc.) >200 d at pH 1 and pH 9, 22 d at
pH 10. Stable up to 300 C.
C
O
O
N
C
CH
3
CH
3
CH
3
CO
2
CH
3
furalaxyl 299
COMMERCIALISATION:
History Fungicide reported by F. J. Schwinn et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1977, 42, 1181). Introduced by Ciba-Geigy AG (later Syngenta AG) and frst marketed in
1977. Patents BE 827419; GB 1448810
APPLICATIONS:
Biochemistry It is assumed that it inhibits protein synthesis in fungi, by interference
with the synthesis of ribosomal RNA. Mode of action Systemic fungicide with protective
and curative action. Absorbed through the roots, stalk, and leaves, with translocation.
Uses Control of soil-borne diseases caused by Phytophthora and Pythium spp., and
other Oomycetes, on ornamentals. Formulation types GR; WP. Compatibility No
incompatibility known.
PRODUCTS:
Discontinued products Fonganil* (Ciba); Fongarid* (Syngenta).
ANALYSIS:
Product analysis by glc. Residues in plants and soils determined by glc with TID (D. J.
Caverley & J. Unwin, Analyst (London), 1980, 106, 389). Details available from Syngenta.
Oral Acute oral LD
50
LD
50
for rats >3100, rabbits 5508 mg/kg. Weak skin and eye irritant (rabbits). Non-
sensitising to skin (guinea pigs). NOEL (90 d) for rats 82 mg/kg daily; for dogs 1.8 mg/
kg b.w. daily. Other Not teratogenic, not mutagenic. Toxicity Class WHO (a.i.) III
ECClassifcation Xn; R22| R52, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
(8 d) for penguin ducks and Japanese quail >6000 mg/kg. LC
50
(8 d)
for Japanese quail >6000 ppm. Fish LC
50
(96 h) for rainbow trout 32.5, crucian carp 38.4,
guppies 8.7, catfsh 60.0 mg/l. Daphnia LC
50
50
for Scenedesmus
subspicatus 27 mg/l. Bees Not toxic to bees when used as directed; LD
50
(24 h, oral) 5 to
>20 g/bee. Worms LC
50
(14 d) for earthworms 510 mg/kg.
ENVIRONMENTAL FATE:
Animals After oral administration, furalaxyl is rapidly metabolised and eliminated via urine
and faeces. The metabolic pathways are independent of sex or dose level administered.
Residues in tissues were generally low, and there was no evidence for accumulation or
retention of furalaxyl or its metabolites. Plants Furalaxyl is metabolised to polar, water-
soluble, partially acidic, probably conjugated, degradation products. Soil/Environment In
soil, the compound dissipated with DT
50
3165 d (2025 C). Degradation is by cleavage of
the ester bond and by N-dealkylation.
300
furconazole
furcarbanil
Fungicide
NOMENCLATURE:
Common name furcarbanil (BSI, E-ISO, (m) F-ISO)
IUPAC name 2,5-dimethyl-3-furanilide
Chemical Abstracts name 2,5-dimethyl-N-phenyl-3-furancarboxamide
CAS RN [28562701] Development codes BAS 319F (BASF)
13
H
13
NO
2
COMMERCIALISATION:
History Fungicide evaluated by BASF AG.
furconazole
Fungicide
NOMENCLATURE:
Common name furconazole (BSI, E-ISO, (m) F-ISO)
IUPAC name (2RS,5RS;2RS,5SR)-5-(2,4-dichlorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-
ylmethyl)-2-furyl 2,2,2-trifuoroethyl ether
Chemical Abstracts name 1-[[2-(2,4-dichlorophenyl)tetrahydro-5-(2,2,2-
trifuoroethoxy)-2-furanyl]methyl]-1H-1,2,4-triazole CAS RN [112839335] unstated
stereochemistry Development codes LS 840 608 (Rhne-Poulenc)
Smiles code FC(F)(F)COC1CCC(O1)C(c2ccc(Cl)cc2Cl)n3cncn3
15
H
14
Cl
2
F
3
N
3
O
2
COMMERCIALISATION:
History Fungicide reported by Rhne-Poulenc Agrochimie.
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor. Mode of action Systemic fungicide with
protective and curative action. Uses Control of fungal diseases of fruit and vines.
Cl
OCH
2
CF
3
O
CH
2
Cl
N
N
N
furconazole-cis 301
furconazole-cis
Fungicide
NOMENCLATURE:
Common name furconazole-cis (BSI, E-ISO, (m) F-ISO)
IUPAC name (2RS,5RS)-5-(2,4-dichlorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-
ylmethyl)-2-furyl 2,2,2-trifuoroethyl ether
Chemical Abstracts name cis-1-[[2-(2,4-dichlorophenyl)tetrahydro-5-(2,2,2-
trifuoroethoxy)-2-furanyl]methyl]-1H-1,2,4-triazole CAS RN [112839324]
Development codes LS 840 606 (Rhne-Poulenc)
Smiles code FC(F)(F)COC1CCC(O1)C(c2ccc(Cl)cc2Cl)n3cncn3
15
H
14
Cl
2
F
3
N
3
O
2
Form Colourless
crystals. M.p. 86 C V.p. 0.0145 mPa (25 C) Solubility In water 21 mg/l. In organic
solvents 3701400 g/l.
COMMERCIALISATION:
History Fungicide reported by B. Zech et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 2,
503). Introduced by Rhne-Poulenc Agrochimie.
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor Mode of action Systemic fungicide with
protective and curative action. Uses For control of Ascomycetes, Basidiomycetes, and
Fungi Imperfecti (powdery mildew, rust, scab, leaf spot and other foliar pathogens) in fruit,
vines, cereals, and tropical crops. Formulation types EC; SC. WP.
Oral Acute oral LD
50
50

for rats >2000 mg/kg. Non-irritating to eyes and skin (rabbits). Other Non-mutagenic in
micronucleus and Ames assays. Toxicity Class WHO (a.i.) II
Cl
OCH
2
CF
3
O
CH
2
Cl
N
N
N
302
furmecyclox
furethrin
Insecticide
IRAC 3
NOMENCLATURE:
IUPAC name (RS)-3-furfuryl-2-methyl-4-oxocyclopent-2-enyl (1RS,2RS;1RS,2SR)-
2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate; Roth: (RS)-3-furfuryl-
2-methyl-4-oxocyclopent-2-enyl (1RS)-cis-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)
cyclopropanecarboxylate; 3-furfuryl-2-methyl-4-oxycyclopent-2-enyl ()-cis-trans-
chrysanthemate
Chemical Abstracts name ()-3-(2-furanylmethyl)-2-methyl-4-oxo-2-
cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other names furethrin CAS RN [17080023], formerly [7076495]
Smiles code CC(=CC1C(C(=O)OC/2CC(=O)/C(=C2/C)/Cc3ccco3)C1(C)C)C;without
stereochemistry:CC(=CC1C(C(=O)OC2CC(=O)C(=C2C)Cc3ccco3)C1(C)C)C
21
H
26
O
4
Form Pale yellow liquid.
B.p. 187188 C /0.4 mmHg Solubility Practically insoluble in water. Soluble in refned
kerosine.
COMMERCIALISATION:
History Insecticide (M. Matsui et al., J. Am. Chem. Soc., 1952, 74, 2181). The ester mixture
from the (RS)- alcohol and the (1R)-trans- acid is a more potent insecticide than the
complete mixture of stereoisomers (W. A. Gersdorff & N. Mitlin, J. Econ. Entomol., 1952, 45,
849).
APPLICATIONS:
neurons by interaction with the sodium channel. Mode of action Contact insecticide.
Uses An insecticide giving a rapid knockdown of Musca domestica.
furmecyclox
Fungicide
NOMENCLATURE:
Common name furm(cyclox) ((m) F-ISO); furmecyclox (BSI, E-ISO)
IUPAC name methyl N-cyclohexyl-2,5-dimethyl-3-furohydroxamate; methyl N-cyclohexyl-
2,5-dimethylfuran-3-carbohydroxamate
Chemical Abstracts name N-cyclohexyl-N-methoxy-2,5-dimethyl-3-furancarboxamide
CAS RN [60568050] EC no 2623020 Development codes BAS 389F (BASF)
Smiles code CON(C1CCCCC1)C(=O)c2cc(C)oc2C
14
H
21
NO
3
Form Crystalline solid.
M.p. 33 C V.p. 8.4 mPa (20 C) Henry 7.04 10
3
Pa m
3
mol
1
(calc.) Solubility In
furophanate 303
water 0.3 g/l (20 C). In acetone, chloroform, ethanol >1 kg/kg. Stability Decomposed by
sunlight and hydrolysed under strongly acidic and strongly alkaline conditions.
COMMERCIALISATION:
History Fungicide reported by E-H. Pommer & B. Zeeh (Pestic. Sci., 1977, 8, 320).
Introduced by BASF AG. Patents DE 2455082; GB 1517960; US 3993772
APPLICATIONS: Uses Used as a seed treatment for cereals, cotton (against Rhizoctonia
solani), potatoes and other crops. Also to protect wood against fungal decay.
Formulation types DS; Wet treatment.
PRODUCTS:
Discontinued products Campogran* (BASF); Epic* (Gustafson); XyligenB* (BASF).
ANALYSIS:
Product analysis by hplc. Residues determined by glc with FID.
Oral Acute oral LD
50
50
for rats
>5000 mg/kg. Potential skin irritant.. Toxicity Class WHO (a.i.) U
ECClassifcation R40| N; R50, R53
furophanate
Fungicide
NOMENCLATURE:
Common name furophanate (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name methyl 4-(2-furfurylideneaminophenyl)-3-thioallophanate
Chemical Abstracts name methyl [[[2-[(2-furanylmethylene)amino]phenyl]amino]
thioxomethyl]carbamate CAS RN [53878174] Development codes RH-3928
Smiles code COC(=O)NC(=S)Nc1ccccc1N=Cc2ccco2
14
H
13
N
3
O
3
S
COMMERCIALISATION:
304
gliotoxin
furyloxyfen
Herbicide
NOMENCLATURE:
Common name furyloxyf(ne) ((m) F-ISO); furyloxyfen (BSI, E-ISO)
IUPAC name ()-5-(2-chloro-,,-trifuoro-p-tolyloxy)-2-nitrophenyl tetrahydro-3-furyl
ether
Chemical Abstracts name ()-3-[5-[2-chloro-4-(trifuoromethoxy)phenoxy]-2-
nitrophenoxy]tetrahydrofuran CAS RN [80020413] unstated stereochemistry
Development codes MT-124 (Mitsui Toatsu)
Smiles code [O-][N+](=O)c1ccc(Oc2ccc(c(Cl)c2)C(F)(F)F)cc1OC3CCOC3
17
H
13
ClF
3
NO
5
COMMERCIALISATION:
History Herbicide developed by Mitsui Toatsu Chemicals, Inc.
APPLICATIONS:
Biochemistry Protoporphyrinogen inhibitor.
gliotoxin
Fungicide
NOMENCLATURE:
Common name gliotoxin ()
IUPAC name (3R,5aS,6S,10aR)-2,3,5a,6,10,10-hexahydro-6-hydroxy-3-hydroxymethyl-2-
methyl-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Chemical Abstracts name [3R-(3,5a,6,10a)]-2,3,5a,6-tetrahydro-6-hydroxy-
3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
CAS RN [67992] Smiles code CN1C(=O)C23CC4=CC=CC(O)C4N3C(=O)
C1(CO)SS2
13
H
14
N
2
O
4
S
2
M.p. 221 C (decomp.)
Solubility In water 700 mg/l (30 C). Moderately soluble in acetic acid, acetone,
chloroform, ethanol, methanol. Stability Easily oxidised and is inactivated in 10 min at
100 C; it is fairly stable in aqueous acids, but is rapidly inactivated in neutral or alkaline
solutions. Specifc rotation []25D 290 (800 mg/l ethanol)
CF
3
O
O NO
2
Cl
O
glyodin 305
COMMERCIALISATION:
Production Formed in cultures of Trichoderma viride, Gliocladium fmbriatum, Aspergillus
fumigatum and several Penicillium spp. History Antifungal antibiotic isolated by R. Weindling
& O. H. Emerson (Phytopathology, 1936, 26, 1068) and structure established by M. R. Bell (J.
Am. Chem. Soc., 1958, 80, 1001). Instability has limited its use in crop protection.
APPLICATIONS:
Biochemistry Antifungal antibiotic. Uses It is antifungal, at 4 mg/l inhibiting spore growth
of Botrytis allii and at 2 mg/l those of Fusarium coeruleum.
Other An intravenous injection of 45 mg/kg was lethal to rabbits (J. R. Johnson et al., ibid.,
1943, 65, 2005).
glyodin
NOMENCLATURE:
Common name glyodin (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-heptadecyl-2-imidazoline acetate; acetic acid - 2-heptadecyl-2-imidazoline
(1:1)
Chemical Abstracts name 2-heptadecyl-4,5-dihydro-1H-imidazolyl monoacetate
CAS RN [556229] Development codes Crag Fruit Fungicide 341
Smiles code CCCCCCCCCCCCCCCCCC1=NCC[NH2+]1.CC(=O)[O-]
22
H
44
N
2
O
2
Form Light orange
crystals. M.p. 6268 C S.g./density 1.035 (20 C) Solubility Practically insoluble in
water. In isopropanolc. 390 g/kg; practically insoluble in acetone, toluene. Stability Readily
hydrolysed by alkali to N-(2-aminoethyl)heptadecanamide.
COMMERCIALISATION:
History Fungicide reported by R. H. Wellman & S. E. A. McCallan (Contrib. Boyce
Thompson Inst., 1946, 14, 151). Introduced by Union Carbide Corp. Patents GB 598927;
US 2540170; US 2540171
APPLICATIONS:
Mode of action Protective fungicide and acaricide. Uses Sprays, after addition of
calcium carbonate to give the free base, were used to protect foliage from attack by fungi.
Formulation types SL . Compatibility Incompatible with oils or EC formulations.
PRODUCTS:
Discontinued products CragFungicide 341* (Union Carbide).
ANALYSIS:
Residues determined by spectrometry (AOAC Methods 18th Ed., 963.23) or by titration
with an anionic surfactant (E. F. Hillenbrand et al., Anal. Chem., 1951, 23, 626).
306
glyphosate-trimesium
NOEL In feeding trials, dogs tolerated 71 mg a.i. (as formulation)/kg diet; guinea-pigs
tolerated 153 mg/kg diet; rats tolerated 91 mg/kg diet (C. P. Carpenter, Arch. Ind. Hyg.
Occup. Med., 1951, 4, 494). Toxicity Class WHO (a.i.) O
glyphosate-trimesium
Herbicide
HRAC G WSSA 9
The trimethylsulfonium salt of glyphosate.
NOMENCLATURE:
IUPAC name trimethylsulfonium N-(phosphonomethyl)glycinate
Chemical Abstracts name N-(phosphonomethyl)glycine trimethylsulfonium salt
Other names sulfosate CAS RN [81591813] Development codes SC.224;
ICIA0224 (ICI)
6
H
16
NO
5
PS Form White solid.
M.p. Decomp. 150 C V.p. <0.01 mPa (20 C) K
ow
logP = 2.9 Henry <2 10-9 Pa m
3
mol
1
(calc.) S.g./density 1.42 Solubility In water >1000 g/l. In acetone, chlorobenzene,
ethanol, kerosene, xylene <5 (all in g tech./l).
COMMERCIALISATION:
History This discontinued salt of glyphosate introduced in Spain (1989) by ICI
Agrochemicals (later Syngenta AG).
PRODUCTS:
Discontinued products Coloso* (Syngenta); Ouragan* (Syngenta); Touchdown*
(Syngenta); Toupan* (Syngenta); Zapp* (Syngenta); Discontinued mixtures Allzett*
(+ diquat dibromide) (Otsuka).
ANALYSIS:
Residues by gc/FPD (Resid. Anal. Methods), or gc/ms (ibid.); see also Pestic. Anal. Man., II,
180.489. In soil, by gc/NPD (Environ. Chem. Methods). In water, by hplc/FLD (ibid.).
Oral Acute oral LD
50
for male rats 748, female rats 755, mice 1250 mg/kg. Skin and eye
Acute percutaneous LD
50
for rabbits >2000 mg/kg. Inhalation LC
50
(4 h) for rats 6.2 mg/l
air. NOEL (2 y) for rats 21 mg/kg b.w. No teratogenic effect observed. ADI/RfD (EC)
0.2 mg/kg b.w. [2001]; (EPA) 0.1 mg/kg b.w. [1994]. ECClassifcation Xn; R22| N; R51,
R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >2050, mallard ducks 950 mg tech./kg. Fish LC
50

(96 h) for trout 1800, bluegill sunfsh >3500 mg/l. Daphnia LC
50
(48 h) 12 mg/l. Algae
EC
50
19 mg/l. Bees LD
50
(oral) >0.4 mg/bee; (contact) 0.39 mg/bee. Worms LD
50
(14 d)
glyphosine 307
>1000 mg/kg soil. Otherbenefcial Harmless under feld conditions at feld application
rates to parasitic wasps (Aphidius rhopalosiphi), lycosid spiders and carabid beetles
(Pterostichus melanarius) (IOBC).
glyphosine
NOMENCLATURE:
Common name glyphosine (BSI, E-ISO, (f) F-ISO, ANSI)
IUPAC name N,N-bis(phosphonomethyl)glycine (I)
Development codes CP 41 845 (Monsanto)
Smiles code OC(=O)CN(CP(=O)(O)O)CP(=O)(O)O
4
H
11
NO
8
P
2
M.p. 200 C (decomp.) V.p. <1.33 10
4
mPa (100 C) S.g./density 1.8 Solubility In
water 350 g/l (20 C). Insoluble in benzene; very slightly soluble in ethanol. Stability Stable
to light. F.p. Non-fammable
COMMERCIALISATION:
History Increase in carbohydrate deposition in sugar cane described by C. A. Porter & L.
E. Ahlrichs (Hawaii Sugar Tech. Rep. 1971, 1972, 30, 71). Plant growth regulator introduced
by Monsanto Co. Patents US 3556762 Manufacturers CCA Biochemical
APPLICATIONS:
Mode of action Absorbed by foliage and translocated throughout the plant especially to
growing points. Uses A plant growth regulator used to hasten ripening of sugar cane and
to increase the sucrose content. Effective rates are 2.44.5 kg/ha. It was removed from the
juice during processing. Formulation types SP.
PRODUCTS:
Discontinued products Polaris* (Monsanto).
ANALYSIS:
Residues determined by glc of a derivative by FPD.
Oral Acute oral LD
50
for rats 7200 mg tech./kg. Skin and eye Non-irritant to skin and
corrosive to eyes (rabbits). NOEL In 2 y feeding trials, no adverse effect was observed at
rates up to 300 mg/kg diet in dogs, or 10 000 mg/kg diet in rats, and reproduction was not
affected. In 1.5 y trials, mice receiving 10 000 mg/kg diet showed no effect and no signifcant
tumour frequency. Toxicity Class WHO (a.i.) UECClassifcation Xi; R41
ENVIRONMENTAL FATE:
Soil/Environment Inactivated by microbial action in soils, DT
50
c. 60 d.
308
griseofulvin
griseofulvin
Fungicide
NOMENCLATURE:
Common name griseofulvin (BSI, E-ISO, BAN, JMAF); gris(ofulvine) ((f) F-ISO)
IUPAC name (2S,6R)-7-chloro-2,4,6-trimethoxy-6-methylspiro[benzofuran-2(3H),1-
cyclohex-2-ene]-3,4-dione; 7-chloro-2,4,6-trimethoxybenzofuran-2(3H)-spiro-1-
cyclohex-2-ene-3,4-dione
Chemical Abstracts name (1S)-trans-7-chloro-2,4,6-trimethoxy-6-
methylspiro[benzofuran-2(3H),1-[2]cyclohexene]-3,4-dione Other names "curling
factor" CAS RN [126078] Smiles code COC1=CC(=O)CC(C)C21Oc3c(C2=O)
c(OC)cc(OC)c3Cl
17
H
17
ClO
6
M.p. 222 C (subliming from 210 C) Solubility Practically insoluble in water. In DMSO
120140 g/l; low solubility in most organic solvents; practically insoluble in petroleum oils.
Stability Stable between pH 3.0 and pH 8.8. Specifc rotation [] +312 (acetone)
COMMERCIALISATION:
Production Isolated from cultures of Penicillium griseofulvum. History Antifungal
antibiotic isolated by A. E. Oxford et al. (Biochem. J., 1939, 33, 240), structure elucidated by
J. F. Grove et al. (Chem. Ind. (London), 1955, p. 160; J. Chem. Soc., 1956, p. 3949; Q. Rev. Chem.
Soc., 1963, 17, 1). Introduced by Glaxo Ltd, now restricted to veterinary and anthelmintic
uses.
APPLICATIONS:
Biochemistry Antifungal antibiotic. Mode of action A fungicide affecting the
morphogenesis of chitinous cell walls (P. W. Brian Ann. Bot. (London), 1949, 13, 59) with
some systemic activity (idem, Nature (London), 1951, 167, 347; S. H. Crowdy & D. Pramer,
Chem. Ind. (London), 1955, p. 160). Formulation types DP; EC; WP.
ANALYSIS:
Product analysis by uv spectrometry (G. C. Ashton & A. P. Brown, Analyst (London), 1956, 81,
220). Residues determined by bioassay (P. W. Brian, Trans. Br. Mycol. Soc., 1946, 29, 173).
IARC 79 (2001).
IARC Class 2B
halosafen 309
halacrinate
Fungicide
NOMENCLATURE:
Common name halacrinate (BSI, E-ISO, (m) F-ISO)
IUPAC name 7-bromo-5-chloro-8-quinolyl acrylate
Chemical Abstracts name 7-bromo-5-chloro-8-quinolinyl 2-propenoate
Smiles code Clc1cc(Br)c(OC(=O)C=C)c2ncccc12
12
H
7
BrClNO
2
Form Colourless
crystals. M.p. 100101 C V.p. 0.08 mPa (20 C) Henry 4.17 10
3
Pa m
3
mol
1
(calc.)
Solubility In water 6 mg/l (20 C). In benzene 370, dichloromethane 610, methanol 27
(all in g/l, 20 C). Stability Relatively stable in neutral or slightly acid media but is slowly
hydrolysed by alkali.
COMMERCIALISATION:
History Fungicide reported by J. M. Smith et al. (Proc. Br. Insectic. Fungic. Conf., 8th, 1975, 2,
421). Evaluated by Ciba-Geigy AG. Patents CH 528214; GB 1324296
APPLICATIONS:
Mode of action Protective and curative fungicide. Uses It was used, in mixture with
captafol, to control Erysiphe graminis and Septoria spp. at 0.50.75 kg/ha.
PRODUCTS:
Discontinued mixtures Tilt* (+ captafol) (Ciba-Geigy).
Oral Acute oral LD
50
50
for
rats >3170 mg/kg. Toxicity Class WHO (a.i.) O
halosafen
Herbicide
HRAC E WSSA 14; diphenyl ether
NOMENCLATURE:
Common name halosafen (BSI, ANSI, E-ISO); halosaf(ne) ((m) F-ISO)
IUPAC name 5-(2-chloro-,,,6-tetrafuoro-p-tolyloxy)-N-ethylsulfonyl-2-
nitrobenzamide
Chemical Abstracts name 5-[2-chloro-6-fuoro-4-(trifuoromethyl)phenoxy]-N-
(ethylsulfonyl)-2-nitrobenzamide CAS RN [77227691] Smiles code CCS(=O)(=O)
NC(=O)c1cc(Oc2c(F)cc(cc2Cl)C(F)(F)F)ccc1[N+](=O)[O-]
16
H
11
ClF
4
N
2
O
6
S
310
HC-252
COMMERCIALISATION:
History Herbicide evaluated by ICI Agrochemicals.
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor.
haloxydine
Herbicide
NOMENCLATURE:
Common name haloxydine (BSI, E-ISO, (f) F-ISO)
IUPAC name 3,5-dichloro-2,6-difuoropyridin-4-ol
Chemical Abstracts name 3,5-dichloro-2,6-difuoro-4-pyridinol CAS RN [2693610]
Development codes PP493 Smiles code Oc1c(Cl)c(F)nc(F)c1Cl
5
HCl
2
F
2
NO
COMMERCIALISATION:
History Herbicide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).
HC-252
Herbicide
NOMENCLATURE:
IUPAC name ethyl O-[2-chloro-5-(2-chloro-,,-trifuoro-p-tolyloxy)benzoyl]-L-lactate
Other names ethoxyfen-ethyl (non-approved name) CAS RN [131086425]
Development codes HC-252 (Budapest Chemical) Smiles code CCOC(=O)[C@@H]
(C)OC(=O)c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1Cl;without stereochemistry:CCOC(=O)
C(C)OC(=O)c1cc(Oc2ccc(cc2Cl)C(F)(F)F)ccc1Cl
19
H
15
Cl
2
F
3
O
5
(for ethyl ester)
Form Brown, oily, viscous liquid (tech.). Solubility Very soluble in acetone, methanol and
xylene.
F
3
C
Cl
O Cl
C
CO
2
CH
2
CH
3
O
O
C
CH
3
H
heptachlor 311
COMMERCIALISATION:
History Herbicide reported by J. Bakos et al. (Proc. Br. Crop Prot. Conf. Weeds, 1991, 1, 83).
Manufacturers Budapest Chemical
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor; acts by tetrapyrrole and
protoporphyrin accumulation. Tetrapyrroles are photosensitisers which cause photo-
oxidation, leading to leaf necrosis and plant death. Mode of action Contact herbicide.
Uses Control of broad-leaved weeds in winter wheat, winter barley, peas, soya beans and
peanuts. Formulation types EC.
Oral Acute oral LD
50
50
for rats >5000, rabbits >2000 mg/kg.
Non-irritating to skin; moderate eye irritant (rabbits). Inhalation LC
50
(14 d) for male rats
9679, female rats 9344 mg/m
3
air. Other Non-mutagenic in Salmonella micronucleus test,
in vitro chromosome aberration test, and in vitro mouse medulla micronucleus test.
ENVIRONMENTAL FATE:
Soil/Environment Since HC-252 is a contact herbicide, there is no soil residual effect,
and no soil persistence problems for following crops.
heptachlor
Insecticide
IRAC 2A
NOMENCLATURE:
Common name heptachlor (BSI, E-ISO, ESA, JMAF); heptachlore ((m) F-ISO)
IUPAC name 1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene
Chemical Abstracts name 1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methano-
1H-indene CAS RN [76448] EC no 2009623; 2138310 heptachlor epoxide
Development codes E 3314; Velsicol 104 Smiles code ClC1C=CC2C1C3(Cl)C(=C(Cl)
C2(Cl)C3(Cl)Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade isc. 72% heptachlor and 28% related compounds.
Mol. wt. 373.3 M.f. C
10
H
5
Cl
7
Form Crystalline solid; (tech., waxy solid). M.p. 9596 C;
(tech. 5560 C) B.p. 135145 C V.p. 53 mPa (25 C, pure)
Cl
Cl
Cl
Cl
Cl
Cl
Cl
312
heptachlor
K
ow
logP = 4.45.5 (Agchem. Desk Ref.) Henry 3.53 10
2
Pa m
3
mol
1
(calc.)
S.g./density 1.58 (20 C) (tech.) Solubility In water 0.056 mg/l (2529 C). Soluble
in many organic solvents, e.g. in acetone 75, benzene 106, xylene 102, cyclohexanone
119, carbon tetrachloride 113, ethanol 4.5 (all in g/100 ml). Tech. in cyclohexanone
1.65 kg/l, ethanol 62.5 g/l, deodorised kerosene 263 g/l, xylene 1.41 kg/l (2030 C).
Stability Stable in daylight, air, moisture, and moderate heat (up to 160 C). Not readily
dehydrochlorinated, but is susceptible to epoxidation. Hydrolysis DT
50
4.3 d (pH 5), 4.5 d
(pH 6, 7), 3.0 d (pH 8) (all 25 C) (cited in Agchem. Desk Ref.).
COMMERCIALISATION:
History It was isolated from tech. chlordane, and its insecticidal properties reported by W.
M. Rogoff & R. L. Metcalf (J. Econ. Entomol., 1951, 44, 910). Introduced by Velsicol Chemical
Corp. Patents US 3437664
APPLICATIONS:
Mode of action Non-systemic insecticide with contact, stomach, and some respiratory
action. Uses Control of termites, ants, and soil insects in cultivated and uncultivated soils.
Applied as a seed treatment, soil treatment, or directly to foliage. Also used for control of
household insects. Formulation types DP; EC; GR; WP; Seed treatment.
PRODUCTS:
Discontinued products Drinox* (Velsicol).
ANALYSIS:
Product analysis by glc with FID (AOAC Methods, 18th Ed., 968.04) or by determination of
a labile chlorine substituent (ibid., 962.07; CIPAC Handbook, 1970, 1, 420; FAO Specifcation
(CP/47); Organochlorine Insecticides, 1973). Residues determined by glc, tlc or paper
chromatography (AOAC Methods, 18th Ed., 970.52; A. Ambrus et al., J. Assoc. Off. Anal. Chem.,
1981, 64, 773; Analyst (London), 1979, 104, 425; H. K. Suzuki et al., Anal. Methods Pestic. Plant
Growth Regul., 1978, 10, 73; Man. Pestic. Residue Anal., pp. 5, 6, 810, 12, 19; Anal. Methods
Residues Pestic., 1988, Part I, M1, M12). In drinking water by glc with ECD (AOAC Methods,
18th Ed., 990.06). See also Pestic. Anal. Man., I, 104, 204, 208, 302, 303, 504.
EHC 38 (1984). JMPR Mtg. 71 (1994); JMPR Evaln. I 69 (1993), 72 (1994); JMPR Evaln. II 64
(1991). HSG 14 (1988). PDS 19 (1975). ICSC.743 (2003). CICAD 70 (2006). IARC 79 (2001).
banned, 79/117/EC, as amended by Regulation 850/2004.
IARC Class 2B
Oral Acute oral LD
50
for rats 147220, guinea pigs 116, mice 68 mg/kg.
50
for rabbits 2002000, rats 119250 mg/kg.
Irritating to eyes; not a skin irritant (rabbits). Inhalation LC
50
(4 h) for rats 2.0200 mg/l
air (aerosol). NOEL The target organ is the liver, with NOEL in rats 5 mg/kg diet, and
2-(2-heptadecyl-2-imidazolin-1-yl)ethanol 313
in dogs 0.51.0 mg/kg diet. A 3-generation feeding study gave NOEL in rats 7 mg/kg diet,
and in dogs (2-generation reproduction study) 1 mg/kg diet. Heptachlor epoxide is not
teratogenic in rabbits at 5 mg/kg daily. ADI/RfD (JMPR) 0.0001 mg/kg b.w. (PTDI) [1994];
(EPA) cRfD 0.0005 mg/kg b.w. [1992]. Water GV GV not established (O). Other Animal
experiments have indicated that heptachlor is carcinogenic in some mice and rat strains,
perhaps acting as a promoter, rather than an initiator, of carcinogenesis (S. S. Epstein, Sci.
Total Environ., 1976, 6, 103154). A committee of the United States National Academy
of Sciences ruled that heptachlor is a carcinogen to certain mouse strains. In vitro and
in vivo experiments showed that heptachlor is non-mutagenic, and there was also no
evidence of teratogenicity in rabbits. Toxicity Class WHO (a.i.) II EPA (formulation) II
ECClassifcation T; R24/25| R40| R33| N; R50, R53: (heptachlor epoxide T; R25| R40|
R33| N; R50, R53) PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducklings >2000 mg/kg. Dietary LC
50
(8 d) for bobwhite
quail 450700, Japanese quail 8095, pheasants 250275 mg/kg diet. Fish LC
50
(96 h) for
rainbow trout 7, bluegill sunfsh 26, fathead minnows 78130 ;g/l.
ENVIRONMENTAL FATE:
Animals The principal metabolites in animals are heptachlor epoxide (found in the tissues,
faeces, and urine), and 1-exo-hydroxychlordene epoxide, a hydrophilic metabolite excreted
in the urine. There is a strong tendency for the epoxide to accumulate in body fat.
Plants In plants, heptachlor epoxide is a metabolite. Soil/Environment In water,
heptachlor rapidly undergoes hydrolysis to 1-hydroxychlordene, which then undergoes
microbial epoxidation to 1-hydroxy-2,3-epoxychlordene. Similar degradation pathways
occur in moist soil. Soil DT
50
910 months when used at agricultural rates.
2-(2-heptadecyl-2-imidazolin-1-yl)ethanol
Fungicide
NOMENCLATURE:
IUPAC name 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol
Chemical Abstracts name 2-heptadecyl-4,5-dihydro-1H-imidazole-
1-ethanol CAS RN [95192] Development codes Fungicide 337
Smiles code CCCCCCCCCCCCCCCCCC1=NCCN1CCO
22
H
44
N
2
O
COMMERCIALISATION:
History Fungicide evaluated by Union Carbide Corp. (later Rhne-Poulenc Agrochimie).
314
heptenophos
heptafuthrin
Insecticide
NOMENCLATURE:
Common name heptafuthrin (pa ISO)
IUPAC name 2,3,5,6-tetrafuoro-4-(methoxymethyl)benzyl (1RS,3RS;1RS,3SR)-2,2-
dimethyl-3-[(1Z)-3,3,3-trifuoroprop-1-enyl]cyclopropanecarboxylate
Chemical Abstracts name [2,3,5,6-tetrafuoro-4-(methoxymethyl)phenyl]
methyl 2,2-dimethyl-3-[(1Z)-3,3,3-trifuoro-1-propen-1-yl]cyclopropanecarboxylate
CAS RN [1130296659]
Smiles code FC1=C(F)C(COC)=C(F)C(F)=C1COC(C2C(/C([H])=C([H])\C(F)(F)F)
C2(C)C)=O
18
H
17
F
7
O
3
heptenophos
Insecticide
IRAC 1B; organophosphate
NOMENCLATURE:
Common name heptenophos (BSI, E-ISO, (m) F-ISO)
IUPAC name 7-chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl dimethyl phosphate
Chemical Abstracts name 7-chlorobicyclo[3.2.0]hepta-2,6-dien-6-yl dimethyl
phosphate CAS RN [23560590] EC no 2457370 Development codes Hoe 02982
(Hoechst); AE F002982 (AgrEvo) Offcial codes OMS 1845
Smiles code without stereochemistry: COP(=O)(OC)OC1=C(Cl)C2C=CCC21
PHYSICAL CHEMISTRY:
Composition Tech. grade is 93% pure. Mol. wt. 250.6 M.f. C
9
H
12
ClO
4
P Form Light
brown liquid, with odour typical of a phosphate ester. B.p. 64 C /0.075 mmHg V.p. 65
mPa (15 C); 170 mPa (25 C) K
ow
logP = 2.32 (OECD 117) Henry 5.73 10
5
(20 C);
F
F
O
CH
3
F
F
O
O
H
3
C
CH
3
H
CF
3
H
P(OCH
3
)
2
O
Cl
O
heptenophos 315
2.33 10
4
(25 C) (both in Pa m
3
mol
1
) S.g./density 1.28 (20 C) Solubility In water
2.2 g tech./l (20 C). Readily miscible with most organic solvents, e.g. in acetone, methanol,
xylene >1, hexane 0.13 (all in kg/l, 25 C). Stability Hydrolysed in acidic and alkaline
media. F.p. 165 C (Cleveland, open); 152 C (Pensky-Martens, closed)
COMMERCIALISATION:
History First described under an erroneous structure (CAS RN [34783409], Biul.
Inst. Ochr. Rosl., 1971, No. 50, p. 109); insecticidal and acaricidal properties against crop
pests reported by R. T. Hewson (Proc. Br. Insectic. Fungic. Conf., 8th, 1975, 2, 697) and against
veterinary pests by W. Bonin (ibid., p. 705). Introduced by Hoechst AG. Patents DE
1643608; GB 1194603; US 3600474; US 3705240; US 3810919 (to Ciba-Geigy)
APPLICATIONS:
contact, stomach and respiratory action. Readily penetrates the plant tissues, and is rapidly
translocated to all parts of the plant, primarily acropetally. Uses An insecticide with quick
initial action and short residual effect. It penetrates plant tissue and is rapidly translocated,
controlling sucking insects (especially aphids) and certain Diptera in feld and glasshouse
crops. Application rates for Hostaquick (550 g/l EC): on fruit trees 0.05%, against woolly
aphids 0.1%, on vegetables and ornamentals 0.05%, in cereals 0.40.5 l/ha, on glasshouse
crops 0.050.1%. Also effective against ectoparasites (feas, lice, mites and ticks) of cattle,
dogs, pigs, sheep and pets. Phytotoxicity Non-phytotoxic when used as directed, except
to some varieties of apple, sweet cherry, and rose. Formulation types EC.
PRODUCTS:
Discontinued products Hostaquick* (crop protection use) (Aventis); Ragadan*
(veterinary use) (Intervet); Discontinued mixtures Decisquick* (+ deltamethrin) (Bayer
CropScience).
Oral Acute oral LD
50
for rats 96121, dogs 5001000 mg/kg b.w. daily. Skin and eye
Acute percutaneous LD
50
for rats >2000 mg/kg. Mild eye irritant. Inhalation LC
50
(4 h) for
rats 0.95 mg/l air. NOEL (2 y) for dogs 12, rats 15 mg/kg diet. ADI/RfD (BfR) 0.002 mg/kg
b.w. [1997]. Toxicity Class WHO (a.i.) Ib.ECClassifcation T; R25| N; R50, R53| concn.
dep.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail 1755 mg/kg (depending on carrier and sex)
for pure a.i. Fish LC
50
(96 h) for trout 0.056, carp 24 mg/l. Daphnia LC
50
(48 h) 2.2 g/l.
Algae EC
50
(72 h) 20 mg/l. Bees Toxic to bees. Worms LC
50
(14 d) for Eisenia foetida
98 mg/kg dry, artifcial soil. Otherbenefcial Harmless to Chrysoperla larvae.
316
heptopargil
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, 90% is excreted in the urine and 6% in the
faeces in metabolised form within 6 days. Plants Four days after application to lettuce,
the compound is completely metabolised to polar, water-soluble compounds without
accumulation of any intermediate. Soil/Environment In soil, rapidly degraded by micro-
organisms, DT
50
(feld) 1.4 d, DT90 (feld) 4.6 d, depending on temperature and soil type;
no accumulation. In lab. (aerobic), DT
50
<4 h, DT90 40 h (20 C). Degradation in water
phase of water sediment system is very quick, DT
50
2777 h.
heptopargil
NOMENCLATURE:
Common name heptopargil (BSI, E-ISO, (m) F-ISO)
IUPAC name (E)-(1RS,4RS)-bornan-2-one O-prop-2-ynyloxime
Chemical Abstracts name ()-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one O-2-
propynyloxime CAS RN [73886289] Development codes EGYT 2250
Smiles code CC1(C)C2CCC1(C)C(=NOCC#C)C2
13
H
19
NO Form Pale yellow oil.
B.p. 95 C /1 mmHg S.g./density 0.9867 (20 C) Solubility In water 1 g/l (20 C).
Miscible with protic and aprotic organic solvents.
COMMERCIALISATION:
History Plant growth regulator reported by A. Kis-Tams et al. (Proc. Br. Crop Prot. Conf.
Weeds, 1980, I, 173). Introduced by EGYT Pharmacochemical Works. Patents US 4244888
APPLICATIONS:
Biochemistry Acts by chlorophyll stabilization. Uses A crop yield enhancer applied as
seed treatment for maize, rice and sugar beet and by pre-emergence or post-emergence
applications in beans, alfalfa, maize, peas, sunfowers and various vegetables. Applied at
48 g/100 cwt seed, or 0.251.0 kg/ha. Formulation types EC; LS .
PRODUCTS:
Discontinued products Limbolid* (EGYT).
Oral Acute oral LD
50
for male rats 2100, female rats 2141 mg/kg. Inhalation LC
50
for rats
>1.4 mg/l air. Toxicity Class WHO (a.i.) III
CH
3
N
H
3
C
CH
3
O
CH
2
C
CH
hexachloroacetone 317
ECOTOXICOLOGY:
Fish Moderately toxic to fsh. Bees Moderately toxic to bees.
Hercules 3944
Fungicide
NOMENCLATURE:
IUPAC name 5-chloro-4-phenyl-1,2-dithiol-3-one
Chemical Abstracts name 5-chloro-4-phenyl-3H-1,2-dithiol-3-one
CAS RN [2425050] Development codes Hercules 3944
Smiles code Clc1ssc(=O)c1c2ccccc2
9
H
5
ClOS
2
COMMERCIALISATION:
History Fungicide reported by W. R. Sitterly (Plant Dis. Rep., 1961, 45, 200). Introduced by
Hercules Inc.
hexachloroacetone
Herbicide
NOMENCLATURE:
Common name HCA (WSSA); hexachloroacetone (E-ISO); hexachloracetone (F-ISO);
all are accepted in lieu of a common name
IUPAC name hexachloroacetone
Chemical Abstracts name 1,1,1,3,3,3-hexachloro-2-propanone CAS RN [116165]
EC no 2041295 Development codes GC 1106 Smiles code ClC(Cl)(Cl)C(=O)
C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
3
Cl
6
O Form Pale yellow liquid.
B.p. 203.6 C S.g./density 1.74 Solubility Slightly soluble in water (25 C). Miscible with
aliphatic and aromatic hydrocarbons, chlorobenzene, methanol, isopropanol, vegetable oils.
Stability Reacts slowly with water to form chloroform and trichloroacetic acid, a reaction
accelerated by alkali.
COMMERCIALISATION:
History Herbicide introduced by Allied Chemical Corp., Agricultural Division (later
Hopkins Chemical Co.). Patents US 2635117; US 2764479
APPLICATIONS:
Mode of action Total herbicide. Uses Used in combinations with petroleum oil or other
herbicides for total weed control in non-cropped land, at 5.522.5 kg/ha.
318
hexafuoroacetone trihydrate
PRODUCTS:
Discontinued mixtures Urox 379* (+ bromacil) (Allied).
ANALYSIS:
Product analysis is by i.r. spectrometry.
Oral Acute oral LD
50
for male albino rats 13701730 mg/kg. Skin and eye Acute
percutaneous LD
50
for male albino rabbits 19004060 mg/kg. Other It is slightly
lachrymatory. Toxicity Class WHO (a.i.) OECClassifcation Xn; R22| N; R51, R53
hexadecyl cyclopropanecarboxylate
Acaricide
NOMENCLATURE:
IUPAC name hexadecyl cyclopropanecarboxylate (I)
Chemical Abstracts name (I) Other names cycloprate* (rejected common
name proposal) CAS RN [54460467] Development codes ZR 856; TF-5166
Smiles code CCCCCCCCCCCCCCCCOC(=O)C1CC1
20
H
38
O
2
COMMERCIALISATION:
History Acaricide evaluated by Zoecon Corp. (later Sandoz AG).
PRODUCTS:
Discontinued products Zardex* (Sandoz).
hexafuoroacetone trihydrate
NOMENCLATURE:
IUPAC name (i) hexafuoroacetone trihydrate; (ii) 1,1,1,3,3,3-hexafuoropropane-2,2-diol
dihydrate
Chemical Abstracts name 1,1,1,3,3,3-hexafuoro-2-propanone; 1,1,1,3,3,3-hexafuoro-
2,2-propanediol CAS RN [34202692] for (i); [677714] for the diol
Development codes GC 7887
3
H
6
F
6
O
4
B.p.c. 105 C S.g./density 1.59 Solubility Soluble in water. Insoluble in most organic
solvents.
COMMERCIALISATION:
History Herbicide introduced by Allied Chemical Corp., Agricultural Division (later
Hopkins Agricultural Chemical Co.). Patents GB 1026036
hexafurate 319
APPLICATIONS:
Mode of action Total herbicide, desiccant and plant growth regulator. Uses At
1123 kg/ha, controls annual and perennial weeds, and woody plants, on uncropped land.
At 11 kg/ha it destroys potato haulm. Formulation types DC.
ICSC.057 (hexafuoroacetone; 2000).
Oral Acute oral LD
50
for male albino rats 176204 mg/kg. Skin and eye Acute
percutaneous LD
50
for male albino rabbits 108118 mg/kg.
hexafurate
Herbicide
NOMENCLATURE:
Common name hexafurate (WSSA)
IUPAC name potassium hexafuoroarsenate
Chemical Abstracts name potassium hexafuoroarsenate(1-) CAS RN [17029220]
Smiles code [K+].F[As-](F)(F)(F)(F)F
PHYSICAL CHEMISTRY: Mol. wt. 228.0 M.f. AsF
6
K Form Colourless crystals.
M.p. 436 C (decomp.) V.p. Non-volatile. S.g./density 3.29 Solubility In water 210 g/kg
(25 C, endothermic). Stability Resistant to uv radiation and to microbial breakdown.
F.p. Non-fammable
COMMERCIALISATION:
History First prepared by M. C. Marignac (Ann. Chem. Pharm., 1867, 145, 237), evaluated
as a herbicide by Pennwalt Corp. and Dow Chemical Co. Patents US 3189428; US
3419382
APPLICATIONS:
Mode of action Selective and systemic herbicide, absorbed by the roots. Uses Effective
at 2 kg/ha against prickly pear and other Opuntia spp.
PRODUCTS:
Discontinued products Nopalmate* (Pennwalt).
ANALYSIS:
Product analysis by measurement of fuoride by titration with thorium nitrate.
Arsenic and arsenic compounds are reviewed in EHC 224 (2001).
Oral Acute oral LD
50
50
for
rabbits >10 000 mg/kg. Moderately irritating to eyes; not irritating to skin (rabbits).
NOEL In 90 d feeding trials on rats, no harmful effect was observed at 1000 mg/kg diet.
320
2-hydrazinoethanol
Toxicity Class WHO (a.i.) OECClassifcation Not specifed, but arsenic compounds in
general (with exceptions) are assigned T; R23/25| N; R50, R53 (concentration-dependent)
hexylthiofos
Fungicide
NOMENCLATURE:
Common name hexylthiofos (BSI, E-ISO, (m) F-ISO)
IUPAC name O-cyclohexyl O,S-diethyl phosphorothioate (I)
Chemical Abstracts name (I) CAS RN [41495674] unstated stereochemistry
Development codes NTN 3318 Smiles code CCOP(=O)(OC1CCCCC1)SCC
10
H
21
O
3
PS
COMMERCIALISATION:
History Fungicide evaluated by Bayer AG.
holosulf
NOMENCLATURE:
Common name holosulf (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-chloroethanesulfnic acid (I)
Chemical Abstracts name (I) CAS RN [21780041] Development codes HOL 1302
Smiles code OS(=O)CCCl
2
H
5
ClO
2
S
COMMERCIALISATION:
History Plant growth regulator evaluated by Bayer AG.
APPLICATIONS:
Biochemistry Ethylene generator.
2-hydrazinoethanol
NOMENCLATURE:
IUPAC name 2-hydrazinoethanol; 2-hydroxyethylhydrazine
Chemical Abstracts name 2-hydrazinoethanol Other names BOH CAS RN [109
842] Smiles code NNCCO
HOCH
2
CH
2
NHNH
2
hyquincarb 321
2
H
8
N
2
O Form Colourless liquid.
M.p. -70 C B.p. 110130 C /17.5 mmHg Solubility Miscible with water and lower
alcohols (room temperature). Stability Stable in the cool and in the dark. Dilute solutions
easily oxidised.
COMMERCIALISATION:
History Introduced as a plant growth regulator by Olin Corp.
APPLICATIONS: Uses Used to promote fowering of Bromeliaceae.
Formulation types SL .
PRODUCTS:
Discontinued products Omafora* (Olin).
1-hydroxy-1H-pyridine-2-thione
Bactericide, fungicide
NOMENCLATURE:
IUPAC name 1-hydroxy-1H-pyridine-2-thione (i); tautomeric with pyridine-2-thiol
1-oxide (ii)
Chemical Abstracts name 1-hydroxy-2(1H)-pyridinethione (i); 2-pyridinethiol
1-oxide (ii) CAS RN [1121308] (i); [1121319] (ii); [32255906] manganese(II)
derivative; [13463417] zinc derivative Development codes OM 1563 (zinc salt)
Smiles code On1ccccc1=S
5
H
5
NOS Stability Forms strongly
chelated metal derivatives.
COMMERCIALISATION:
History Compounds reported by E. Shaw et al. (J. Am. Chem. Soc., 1950, 72, 4362). Various
metal salts investigated as fungicides (M. Szkolnik & J. M. Hamilton, Plant Dis. Rep., 1957, 41,
289, 293, 301) and evaluated by the Olin Mathieson Chemical Corp.
PRODUCTS:
Discontinued products Omadine* (Olin); Omadine OM1563* (zinc derivative)
(Olin); Omadine OM1564* (manganese(II) derivative) (Olin); Omadine OM1565* (iron
derivative) (Olin).
hyquincarb
Insecticide
NOMENCLATURE:
Common name hyquincarb (BSI, E-ISO, (m) F-ISO)
IUPAC name 5,6,7,8-tetrahydro-2-methyl-4-quinolyl dimethylcarbamate
Chemical Abstracts name 5,6,7,8-tetrahydro-2-methyl-4-quinolinyl dimethylcarbamate
322
2-imidazolidone
CAS RN [56716213] Development codes Hoe 25 682
Smiles code CN(C)C(=O)Oc1cc(C)nc2CCCCc12
13
H
18
N
2
O
2
COMMERCIALISATION:
History Insecticide reported by K-D. Bock (Proc. Br. Crop. Prot. Conf. - Pests Dis., 1977, 3,
1017). Evaluated by Hoechst AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide. Uses For
use against aphids.
ICIA0858
Fungicide
NOMENCLATURE:
Chemical Abstracts name N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide
CAS RN [112860045] Development codes ICIA0858; SC-0858
Smiles code COc1ccc(NC(=O)C2CC2)cn1
10
H
12
N
2
O
2
COMMERCIALISATION:
History Fungicide evaluated by Zeneca Agrochemicals.
APPLICATIONS: Uses Evaluated as a broad-spectrum fungicide.
2-imidazolidone
Insecticide
NOMENCLATURE:
IUPAC name 2-imidazolidone; imidazolidin-2-one
Chemical Abstracts name 2-imidazolidinone Other names ethyleneurea
CAS RN [120934] Smiles code O=C1NCCN1
3
H
6
N
2
M.p. 131132 C Solubility Readily soluble in water.
COMMERCIALISATION:
History Insect growth regulator reported by H. G. Simkover (J. Econ. Entomol., 1964, 57,
574). Evaluated by Shell Development Co. Patents US 3242044
C
NH
O
N OCH
3
inabenfde 323
APPLICATIONS:
Mode of action Insect growth regulator.
Oral Acute oral LD
50
for mice >5000 mg/kg.
inabenfde
NOMENCLATURE:
Common name inabenfde (BSI, E-ISO, (m) F-ISO)
IUPAC name 4-chloro-2-(-hydroxybenzyl)isonicotinanilide
Chemical Abstracts name N-[4-chloro-2-(hydroxyphenylmethyl)phenyl]-
4-pyridinecarboxamide CAS RN [82211243] unstated stereochemistry
Development codes CGR-811 (Chugai) Smiles code OC(c1ccccc1)c2cc(Cl)
ccc2NC(=O)c3ccncc3
19
H
15
ClN
2
O
2
Form Pale yellow-
brown or colourless crystals. M.p. 210212 C V.p. 0.063 mPa (20 C) K
ow
logP =
3.13 Solubility In water 1 mg/l (30 C). In acetone 3.6, ethyl acetate 1.43, xylene 0.58,
methanol 2.35, ethanol 1.61, chloroform 0.59, DMF 6.72, acetonitrile 0.58, tetrahydrofuran
1.61, hexane 8 10
4
(all in g/l, 30 C). Stability Stable to heat and sunlight. Slightly
unstable in alkaline media; after 2 weeks at 40 C, hydrolysed 16.2% (pH 2), 49.5% (pH 5),
83.9% (pH 7), 100% (pH 11).
COMMERCIALISATION:
History Plant growth regulator reported by K. Nakamura (Jpn. Pestic. Inf., 1987, No. 51,
p. 23). Introduced in Japan (1986) by Chugai Pharmaceutical Co., Ltd (agrochemical
interests now Eiko Kasei Co. Ltd). Patents EP 48998; US 4377407; JP 6341393
Manufacturers Dongbu HiTek; Eiko Kasei
APPLICATIONS:
Biochemistry Inhibits gibberellin biosynthesis. Mode of action Plant growth regulator
which shortens lower internodes and upper leaf blades. Uses Used to increase resistance
to lodging in rice, being applied to the soil surface under submerged conditions, at
1.52.4 kg/ha. Phytotoxicity Non-phytotoxic to rice. Formulation types GR; WP.
N C
NH
O
Cl
CH HO
324
ipazine
PRODUCTS:
Discontinued products Seritard* (Eiko Kasei).
ANALYSIS:
Product and residue analysis by hplc.
J. Pestic. Sci., 1988, 13, 391394.
Oral Acute oral LD
50
LD
50
for rats and mice >5000 mg/kg. Not a skin or eye irritant (rabbits). Not a skin
50
(4 h) for rats >0.46 mg/l air. NOEL In 6 mo
and 2 y toxicity studies on dogs and rats, no ill-effects were observed. In reproductive
toxicity (3 generations) and teratogenicity studies on rats and rabbits, no abnormalities
were observed. Other Not mutagenic in Ames assay. Toxicity Class WHO (a.i.) U EPA
(formulation) IV
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp >30, grey mullet 11 mg/l. Daphnia LC
50
(3 h) >30 mg/l.
ENVIRONMENTAL FATE:
Animals The major urinary metabolite in the rat is 4-hydroxyinabenfde (H. Kinoshita et
al., Xenobiotica, 1987, 17, 925). Plants Metabolised to inabenfde ketone.
Soil/Environment Under Japanese paddy feld conditions, DT
50
c. 4 mo.
iodobonil
Herbicide
NOMENCLATURE:
Common name iodobonil (BSI, E-ISO, (m) F-ISO)
IUPAC name allyl 4-cyano-2,5-di-iodophenyl carbonate; 4-(allyloxycarbonyloxy)-3,5-di-
iodobenzonitrile
Chemical Abstracts name 4-cyano-2,6-di-iodophenyl 2-propenyl carbonate
CAS RN [25671458] Smiles code Ic1cc(C#N)cc(I)c1OC(=O)OCC=C
11
H
7
I
2
NO
3
COMMERCIALISATION:
History Herbicide evaluated by C. H. Boehringer Sohn (later Shell Agrar GmbH).
ipazine
Herbicide
NOMENCLATURE:
Common name ipazine (BSI, E-ISO, (f) F-ISO, WSSA)
IPSP 325
2
,N
2
-diethyl-N4-isopropyl-1,3,5-triazine-2,4-diamine; 2-chloro-4-
diethylamino-6-isopropylamino-1,3,5-triazine
Chemical Abstracts name 6-chloro-N,N-diethyl-N-(1-methylethyl)-1,3,5-triazine-2,4-
diamine CAS RN [1912250] Development codes G 30 031
Smiles code CCN(CC)c1nc(Cl)nc(NC(C)C)n1
10
H
18
ClN
5
COMMERCIALISATION:
History Herbicide evaluated by J. R. Geigy S.A. (later Ciba-Geigy AG).
PRODUCTS:
Discontinued products Gesabal* (Ciba-Geigy).
iprymidam
Herbicide
NOMENCLATURE:
Common name iprymidam (BSI, E-ISO, (m) F-ISO)
IUPAC name 6-chloro-N4-isopropylpyrimidine-2,4-diamine
Chemical Abstracts name 6-chloro-N4-(1-methylethyl)-2,4-pyrimidinediamine
CAS RN [30182242] Development codes SAN 52 123H
Smiles code CC(C)Nc1cc(Cl)nc(N)n1
7
H
11
ClN
4
COMMERCIALISATION:
History Herbicide evaluated by Sandoz AG.
IPSP
Insecticide
IRAC 1B
NOMENCLATURE:
Common name IPSP (JMAF)
IUPAC name S-ethylsulfnylmethyl O,O-diisopropyl phosphorodithioate
P[OCH(CH
3
)
2
]
2
S
CH
2
S
O
CH
3
CH
2
S
326
isamidofos
Chemical Abstracts name S-[(ethylsulfnyl)methyl] O,O-bis(1-methylethyl)
phosphorodithioate CAS RN [5827054] Development codes PSP-204 (Hokko)
Smiles code CCS(=O)CSP(=S)(OC(C)C)OC(C)C
PHYSICAL CHEMISTRY:
9
H
21
O
3
PS
3
Form Yellow liquid (tech.).
V.p. 2 mPa (27 C) (tech.) S.g./density 1.1696 (20 C, tech.) Solubility In water
1.5 g/l (15 C). In hexane 71 g/l (20 C); freely soluble in acetone and xylene. Stability
DT
50
(25 C) 4 d (pH 7), 3 d (pH 9). Stable up to 100 C.
COMMERCIALISATION:
History Insecticide reported by D. Murrayama et al. (Mem. Fac. Agric. Hokkaido Univ.,
1966, 6, 73). Introduced by Hokko Chemical Industry Co., Ltd. Patents JP 531126; US
3408426; GB 1068628
APPLICATIONS:
Biochemistry Cholinesterase inhibitor Mode of action Systemic insecticide.
Uses Control of aphids on potatoes and other vegetables. Formulation types GR .
PRODUCTS:
Discontinued products Aphidan* (Hokko).
ANALYSIS:
Product by tlc with colorimetric determination. Residues by glc with FPD.
Oral Acute oral LD
50
for male rats 25, male mice 320 mg/kg. Skin and eye Acute
percutaneous LD
50
for male rats 28, female mice 1300 mg/kg. Toxicity Class WHO (a.i.) O
ECClassifcation T+; R27| T; R25| N; R50, R53| concn. dep.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp 20 mg/l.
isamidofos
Nematicide
NOMENCLATURE:
Common name isamidofos (BSI, E-ISO, (m) F-ISO)
IUPAC name O-ethyl S-(N-methylcarbaniloylmethyl) N-isopropylphosphoramidothioate
Chemical Abstracts name O-ethyl S-[2-(methylphenylamino)-2-
oxoethyl] (1-methylethyl)phosphoramidothioate CAS RN [66602877]
Development codes Hoe 36 275
Smiles code CCOP(=O)(NC(C)C)SCC(=O)N(C)c1ccccc1
isazofos 327
14
H
23
N
2
O
3
PS
COMMERCIALISATION:
History Nematicide evaluated by Hoechst AG.
isazofos
IRAC 1B
NOMENCLATURE:
Common name isazofos (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name O-5-chloro-1-isopropyl-1H-1,2,4-triazol-3-yl O,O-diethyl phosphorothioate
Chemical Abstracts name O-[5-chloro-1-(1-methylethyl)-1H-1,2,4-triazol-3-
yl] O,O-diethyl phosphorothioate CAS RN [42509808] EC no 2558638
Development codes CGA 12 223 Smiles code CCOP(=S)(OCC)Oc1nc(Cl)n(n1)C(C)C
9
H
17
ClN
3
O
3
PS Form Yellow liquid.
B.p. 120 C (36 Pa) V.p. 7.45 mPa (20 C) K
ow
logP = 2.99 Henry 1.39 10-2 Pa m
3
mol
1
(calc.) S.g./density 1.23 (20 C) Solubility In water 168 mg/l (20 C). Miscible
with organic solvents, e.g. chloroform, methanol, benzene. Stability Hydrolysed more
rapidly in alkalis than in acids; DT
50
(calc.) (20 C) 85 d (pH 5), 48 d (pH 7), 19 d (pH 9).
Decomposes above 200 C.
COMMERCIALISATION:
History Insecticide and nematicide reported by D. Dawes et al. (Meded. Fac. Landbouwwet.
Rijksuniv. Gent, 1974, 39, 727) and F. Bachmann & D. Dawes (ibid., p. 801). Developed by Ciba-
Geigy AG (later Novartis Crop Protection AG). Patents BE 792452; GB 1419131; GB
1419132 Manufacturers Novartis
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Nematicide and systemic
insecticide with contact and stomach action. Uses A soil-applied nematicide used on
bananas (against Radopholus similis and Cosmopolites sordidus), citrus, cotton, beet, maize,
rice, vegetables, sugar cane, and in turf against soil-dwelling insects.
Phytotoxicity Phytotoxic to potatoes and tobacco. Formulation types EC; GR .
PRODUCTS:
Discontinued products Brace* (Ciba-Geigy); Miral* (Novartis); Triumph* (Ciba-
Geigy); Victor* (Ciba-Geigy).
P(OCH
2
CH
3
)
2
S
N
N
N
(CH
3
)
2
CH
Cl
O
328
isobenzan
ANALYSIS:
Oral Acute oral LD
50
50
for
male rats >3100, female rats 118 mg/kg. Mild skin irritant; very slight eye irritant (rabbits).
Inhalation LC
50
(4 h) for rats 0.24 mg/l air. NOEL (90 d) for rats 2 mg/kg diet (0.2 mg/kg
daily), for dogs 2 mg/kg diet (0.05 mg/kg daily). ADI/RfD (EPA) 0.00002 mg/kg b.w. [1989].
Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassifcation T+; R26| T; R24/25|
Xn; R48/20| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Toxic to birds. Acute oral LD
50
for mallard ducks 61, bobwhite quail 11.1 mg/kg. LC
50

(8 d) for bobwhite quail 81 ppm. Fish LC
50
(96 h) for bluegill sunfsh 0.01, carp 0.22, trout
0.0080.019 mg/l. Daphnia LC
50
(48 h) 0.0014 mg/l. Bees Toxic to honeybees.
ENVIRONMENTAL FATE:
Animals It is extensively metabolised and rapidly excreted, primarily in the urine. No
accumulation takes place in the body. Soil/Environment DT
50
10 d (lab.).
isobenzan
Insecticide
IRAC 2A
NOMENCLATURE:
Common name telodrin (JMAF); isobenzan (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,3,4,5,6,7,8,8-octachloro-1,3,3a,4,7,7a-hexahydro-4,7-
methanoisobenzofuran (I)
Development codes SD 4402; WL 1650; CP 14957
Smiles code ClC1OC(Cl)C2C1C3(Cl)C(=C(Cl)C2(Cl)C3(Cl)Cl)Cl
9
H
4
Cl
8
O
COMMERCIALISATION:
History Insecticide evaluated by Shell International Chemical Co. Manufactured in the
Netherlands from 1958 to 1965.
APPLICATIONS:
PRODUCTS:
Discontinued products Telodrin* (Shell).
isocarbamid 329
EHC 129 (1991). HSG 61 (1991).
Toxicity Class WHO (a.i.) OECClassifcation T+; R27/28| N; R50
ENVIRONMENTAL FATE:
EHC 129 concluded isobenzan is a signifcant hazard to the environment and to exposed
workers.
isocarbamid
Herbicide
NOMENCLATURE:
Common name isocarbamid (BSI, E-ISO); isocarbamide ((m) F-ISO, WSSA)
IUPAC name N-isobutyl-2-oxoimidazolidine-1-carboxamide
Chemical Abstracts name N-(2-methylpropyl)-2-oxo-1-imidazolidinecarboxamide
CAS RN [30979487] Development codes BAY MNF 0166
Smiles code CC(C)CNC(=O)N1CCNC1=O
8
H
15
N
3
O
2
Form Colourless crystalline
solid. M.p. 9596 C V.p. <13000 mPa (50 C) Solubility In water 1.3 g/l (20 C). In
cyclohexanone 130, dichloromethane 281 (both g/kg, 20 C). Stability Stable in alkaline
and acid media.
COMMERCIALISATION:
History Herbicide reported by L. Eue et al. (Proc. Br. Weed Control Conf., 10th, 1970, 2, 610).
Introduced by Bayer AG. Patents DE 1795117; US 3875180
APPLICATIONS:
Mode of action Selective herbicide. Uses A selective herbicide for use in sugar beet and
fodder beet at rates of 34 kg/ha, in mixture with lenacil, for pre-em. application.
PRODUCTS:
Discontinued mixtures Merpelan AZ* (+ lenacil) (Bayer); Terratop* (+ lenacil) (Bayer).
ANALYSIS:
Residues determined by glc (H. J. Jarczyk, Pfanz.-Nachr. Bayer (Engl. Ed.), 1974, 27, 130).
Oral Acute oral LD
50
for male rats >2500, female dogs >500 mg/kg. Skin and eye Acute
percutaneous LD
50
for male rats >500 mg/kg. NOEL (90 d) for rats 800 mg/kg diet, for
dogs >5000 mg/kg diet. Toxicity Class WHO (a.i.) U
330
isodrin
isocil
Herbicide
NOMENCLATURE:
Common name isocil (BSI, E-ISO, (m) F-ISO, ANSI, WSSA); isoprocil (France, Republic of
South Africa)
IUPAC name 5-bromo-3-isopropyl-6-methyluracil
Chemical Abstracts name 5-bromo-6-methyl-3-(1-methylethyl)-2,4(1H,3H)-
pyrimidinedione CAS RN [314421] Development codes DuPont Herbicide 82
Smiles code CC(C)n1c(=O)[nH]c(C)c(Br)c1=O
8
H
11
BrN
2
O
2
M.p. 158159 C Solubility In water 2.1 g/l (25 C). Soluble in alkali, acetone, acetonitrile,
ethanol. Stability Stable 159 C but decomposed by concentrated acids.
COMMERCIALISATION:
History Herbicide reported by H. C. Bucha et al. (Science, 1962, 137, 537). Introduced by
E. I. du Pont de Nemours & Co. Patents US 3235357
APPLICATIONS:
Biochemistry Photosynthesis inhibitor. Mode of action Total herbicide. Uses At
1318 kg/ha, for control of perennial grasses and on non-cropped land.
PRODUCTS:
Discontinued products Hyvar* (DuPont).
Oral Acute oral LD
50
for male albino ratsc. 3400 mg/kg. Toxicity Class WHO (a.i.) O
isodrin
Insecticide
IRAC 2A
NOMENCLATURE:
Common name isodrin (BSI); isodrine ((f) France)
IUPAC name (1R,4S,5R,8S)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-hexahydro-1,4:5,8-
dimethanonaphthalene
Chemical Abstracts name (1,4,4a,5,8,8a)-1,2,3,4,10,10-hexachloro-1,4,4a,5,8,8a-
hexahydro-1,4:5,8-dimethanonaphthalene CAS RN [465736] EC no 2073662
Development codes Compound 711; SD-3418
Smiles code ClC1=C(Cl)C2(Cl)C3C4CC(C=C4)C3C1(Cl)C2(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 364.9 M.f. C
12
H
8
Cl
6
isofenphos 331
COMMERCIALISATION:
History Insecticide evaluated by Shell International Chemical Co.
APPLICATIONS:
Toxicity Class WHO (a.i.) OECClassifcation T+; R26/27/28| N; R50, R53| concn. dep.
isofenphos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name isofenphos (BSI, E-ISO); isophenphos ((m) F-ISO)
IUPAC name O-ethyl O-2-isopropoxycarbonylphenyl N-isopropylphosphoramidothioate;
isopropyl O-[ethoxy-N-isopropylamino(thiophosphoryl)]salicylate
Chemical Abstracts name 1-methylethyl 2-[[ethoxy[(1-methylethyl)amino]
phosphinothioyl]oxy]benzoate CAS RN [25311711] EC no 2468141
Development codes BAY SRA 12 869; BAY 92114 (Bayer) Smiles code CCOP(=S)
(NC(C)C)Oc1ccccc1C(=O)OC(C)C
15
H
24
NO
4
PS Form Colourless oil;
(tech. has a characteristic smell). V.p. 0.22 mPa (20 C); 0.44 mPa (25 C) K
ow
logP = 4.04
(21 C) Henry 4.2 10
3
Pa m
3
mol
1
(20 C) S.g./density 1.131 (20 C) Solubility In
water 18 mg/l (20 C). In isopropanol, hexane, dichloromethane, toluene >200 g/l (20 C).
Stability DT
50
for aqueous hydrolysis 2.8 y (pH 4), >1 y (pH 7), >1 y (pH 9) (22 C).
Photodegradation on soil surface in the laboratory is extremely rapid. Under natural light,
photodegradation is not so fast. F.p. >115 C (tech.)
COMMERCIALISATION:
History Insecticide reported by B. Homeyer (Meded. Fac. Landbouwwet. Rijksuniv. Gent,
1974, 39, 789). Introduced by Bayer AG. Patents DE 1668047 Manufacturers Bayer
APPLICATIONS:
contact and stomach action. Translocated from roots to a limited extent. Uses Control of
cabbage root fies, carrot fies, onion fies, corn rootworms, white grubs, wireworms, and
other soil insects in vegetables, oilseed rape, maize, bananas, turf, sugar cane, and other
C
OPOCH
2
CH
3
S
NHCH(CH
3
)
2
(CH
3
)
2
CHO O
332
isofenphos
crops; and also controls thrips in citrus and onions. Formulation types DS; EC; GR; WP.
PRODUCTS:
Discontinued products Amaze* (Bayer CropScience); Oftanol* (Bayer CropScience);
Pryfon* (Mobay); Discontinued mixtures Oftanol T* (+ thiram) (Bayer CropScience).
ANALYSIS:
Product analysis by glc with FID or TCD (CIPAC Handbook, 1988, D, 114; AOAC Methods,
18th Ed., 987.01). Residues determined by glc with FID (Man. Pestic. Residue Anal., p. 6; Anal.
Methods Residues Pestic., 1988, Part I, M5, M13; K. Wagner, Pfanz.-Nachr. Bayer (Engl. Ed.),
1976, 29, 67).
JMPR Evaln. I 66 (1992); JMPR Evaln. II 49 (1986). EU Status (1107/2009) Not approved,
Oral Acute oral LD
50
for male and female ratsc. 20, micec. 125 mg/kg. Skin and eye Acute
percutaneous LD
50
for male and female ratsc. 70 mg/kg. Slightly irritating to eyes and skin
(rabbits). Inhalation LC
50
(4 h) for male ratsc. 0.5 mg/l, female rats 0.3 mg/l air (aerosol).
NOEL (2 y) for rats 1 mg/kg diet (0.05 mg/kg b.w.), dogs 2, mice 1 mg/kg diet.
ADI/RfD (JMPR) 0.001 mg/kg b.w. [1986]; (EPA) cRfD 0.00008 mg/kg b.w., however
subsequent re-evaluation by EPA would lead to a valuec. 0.0003 mg/kg b.w. [1999].
Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassifcation T; R24/25| N; R50,
R53| concn. dep.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 8.7, mallard ducks 3236 mg/kg. Dietary LC
50

(5 d) for bobwhite quail 145, mallard ducks 4908 mg/kg diet. Fish LC
50
(96 h) for golden
orfe 6.49, bluegill sunfsh 2.2, rainbow trout 3.3 mg/l. Daphnia LC
50
(48 h) 0.00390.0073
mg/l. Algae ErC50 for Scenedesmus subspicatus 6.8 mg/l. Bees Toxic to bees.
Worms LC
50
for Eisenia foetida 404 mg/kg dry soil.
ENVIRONMENTAL FATE:
Animals For a study of metabolism in rats and in rat liver microsomal systems, see M.
Ueji & C. Tomizawa, J. Pestic. Sci., 1987, 12, 245, 269. Elimination is very quick; almost 95%
is excreted within 24 h, in urine and faeces. Plants The most important metabolites are
salicylic acid and dihydroxybenzol acid. Soil/Environment Mobility is medium to low.
Degradation in different soils is slow.
isolane 333
isofetamid
Fungicide
NOMENCLATURE:
Common name isofetamid (pa ISO)
IUPAC name N-[1,1-dimethyl-2-(4-isopropoxy-o-tolyl)-2-oxoethyl]-3-methylthiophene-2-
carboxamide
Chemical Abstracts name N-[1,1-dimethyl-2-[2-methyl-4-(1-methylethoxy)
phenyl]-2-oxoethyl]-3-methyl-2-thiophenecarboxamide CAS RN [875915789]
Development codes KF5411
Smiles code O=C(C(C)(C)NC(C1=C(C)C=CS1)=O)C2=CC=C(OC(C)C)C=C2C
20
H
25
NO
3
S
isolane
Insecticide
NOMENCLATURE:
Common name isolane ((m) France)
IUPAC name 1-isopropyl-3-methylpyrazol-5-yl dimethylcarbamate
Chemical Abstracts name 3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl
dimethylcarbamate CAS RN [119380] EC no 2043182
Development codes G 23 611 Smiles code CC(C)n1nc(C)cc1OC(=O)N(C)C
10
H
17
N
3
O
2
B.p. 105107 C /0.33 mmHg V.p. 133 mPa (20 C) S.g./density 1.07 (20 C)
Solubility Miscible with water and most organic solvents. Stability Hydrolysed by
concentrated acids or alkali.
COMMERCIALISATION:
History Insecticide reported by H. Gysin (Proc. 3rd Int. Congr. Phytopharm., Paris, 1952).
Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents CH 279533; CH 281967;
CH 282655
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact, systemic and fumigant
insecticide.
C H
3
CH
3
O
CH
3
CH
3
C H
3
N
CH
3
S
OH
O
334
isomethiozin
PRODUCTS:
Discontinued products Isolan* (Ciba-Geigy); Primin* (Geigy).
ANALYSIS:
Product analysis by acid hydrolysis and titrimetric estimation of the dimethylamine
produced (R. Suter et al., Fresenius Z. Anal. Chem., 1955, 147, 173). Residues determined by
colorimetry of the dimethylamine produced on hydrolysis (idem, ibid.; S. A. Hall et al., Anal.
Chem., 1951, 23, 1866).
Oral Acute oral LD
50
for rats 1150 mg (in aqueous solution)/kg; for mice 918 mg/kg.
isomethiozin
Herbicide
NOMENCLATURE:
Common name isomethiozin (BSI, E-ISO); isom(thiozine) ((f) F-ISO)
IUPAC name 6-tert-butyl-4-isobutylideneamino-3-methylthio-1,2,4-triazin-5(4H)-one
Chemical Abstracts name 6-(1,1-dimethylethyl)-4-[(2-methylpropylidene)amino]-3-
(methylthio)-1,2,4-triazin-5(4H)-one CAS RN [57052047] Development codes BAY
DIC 1577 Smiles code CSc1nnc(c(=O)n1N=CC(C)C)C(C)(C)C
12
H
20
N
4
OS Form Colourless crystals.
M.p. 159.3 C V.p. 0.047 mPa (20 C) Henry 1.26 10
3
Pa m
3
mol
1
(calc.) Solubility In
water 10 mg/kg (20 C). In cyclohexanone 103, dichloromethane 152 (both g/kg, 20 C).
COMMERCIALISATION:
History Herbicide reported by H. Hack (Mitt. Biol. Bundesanst. Land-Forstwirtsch. Berlin-
Dahlem, 1975, 165, 179; Pfanz.-Nachr. Bayer (Engl. Ed.), 1975, 28, 241). Introduced by Bayer
AG. Patents GB 1182801.
APPLICATIONS: Uses A post-em. herbicide in areas where there is a heavy infestation
of grass, also in winter wheat or, in combination with dichlorprop, in spring cereals (H.
Hack, Mitt. Biol. Bundesanst. Land-Forstwirtsch. Berlin-Dahlem, 1975, 165, 179; Pfanz.-Nachr.
Bayer (Engl. Ed.), 1975, 28, 241; W. Kolbe, ibid., p. 257). Formulation types WP.
PRODUCTS:
Discontinued products Tantizon* (Bayer); Discontinued mixtures Tantizon Combi*
(+ dichlorprop) (Bayer); Tantizon DP* (+ dichlorprop) (Bayer).
ANALYSIS:
isonoruron 335
Product analysis by i.r. spectrometry. Residues determined by glc with FID (H. J. Jarczyk,
ibid., p. 287).
Oral Acute oral LD
50
for rats >10 000, mice >2500 mg/kg. NOEL (90 d) for rats 100, dogs
500 mg/kg diet. Toxicity Class WHO (a.i.) U
isonoruron
Herbicide
NOMENCLATURE:
Common name isonoruron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,1-dimethyl-3-(perhydro-4,7-methanoinden-1-yl)urea (i) and 1,1-dimethyl-
3-(perhydro-4,7-methanoinden-2-yl)urea (ii)
Chemical Abstracts name N,N-dimethyl-N-(octahydro-4,7-methano-1H-inden-1-yl)
urea (i) and N,N-dimethyl-N-(octahydro-4,7-methano-1H-inden-2-yl)urea (ii); N,N-
dimethyl-N-[octahydro-4,7-methanoinden-1(or 2)-yl]urea (i + ii) CAS RN [28805789],
formerly [28346658] (i) + (ii)
13
H
22
N
2
O Form Colourless crystalline
powder. M.p. 150180 C Solubility In water 220 mg/l (20 C). In acetone 11, benzene
78, chloroform 138, ethanol 175 (all in g/kg, 20 C).
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Abstr. Int. Congr. Plant Prot., 1967, p. 446).
Introduced by BASF AG. Patents DE 1200062
APPLICATIONS:
Mode of action Selective herbicide. Uses A mixture of isonoruron and brompyrazon
was used pre- and post- em. to control Alopecurus myosuroides, Apera spica-venti and
annual broad-leaved weeds in winter cereals at 3.44.0 kg formulation/ha. A mixture of
isonoruron and buturon was used pre-em. for potatoes at 3.44.5 kg formulation/ha.
PRODUCTS:
Discontinued mixtures Basanor* (+ brompyrazon) (BASF); Basftox* (+ buturon)
(BASF).
ANALYSIS:
Product analysis of Basftox by uv spectrometry to determine buturon, and titration to
determine isonoruron.
Oral Acute oral LD
50
50
for rats
>2500 mg Basftox/kg; for rabbits >4000 mg/kg. NOEL No ill-effect was observed in
120 d feeding trials with rats receiving 400 mg/kg diet or with beagle dogs at 1600 mg/kg
diet. Toxicity Class WHO (a.i.) O
336
isopolinate
isopamphos
Fungicide
NOMENCLATURE:
IUPAC name 3-nonyloxypropylammonium methylphosphonate
Other names izopamfos CAS RN [94343563]
Smiles code CCCCCCCCCOCCC[NH3+].COP(=O)[O-]
PHYSICAL CHEMISTRY:
Composition The material is a mixture of nonyl isomers. Mol. wt. 297.4
M.f. C
13
H
32
NO
4
P Form Colourless, viscous oil with an amine-like smell.
COMMERCIALISATION:
History Fungicide developed by Borsod.
APPLICATIONS:
Mode of action Protectant and eradicant fungicide with some systemic activity. Uses As
a seed dresssing, effective alone or in combination with benzimidazole fungicides against
soil borne diseases on wheat or maize. As a foliar spray used against Peronospora spp.
and Phytophthora spp. in tobacco, tomatoes and potatoes. Formulation types SD; Water-
miscible.
PRODUCTS:
Discontinued products BF51* (Borsod).
Oral Acute oral LD
50
50
for rats
10 000 mg/kg. Inhalation Irritates mucous membranes.
isopolinate
Herbicide
NOMENCLATURE:
Common name isopolinate (BSI, E-ISO, (m) F-ISO)
IUPAC name S-isopropyl azepane-1-carbothioate
Chemical Abstracts name (S)-(1-methylethyl) hexahydro-1H-azepine-1-carbothioate
CAS RN [3134701] Development codes R-4574; CH-83
Smiles code CC(C)SC(=O)N1CCCCCC1
10
H
19
NOS
COMMERCIALISATION:
History Herbicide evaluated by Chugai Pharmaceutical Co. Ltd.
O
P CH
3
O O
H
C
9
H
19
O(CH
2
)
3
NH
3
isopropalin 337
isopropalin
Herbicide
NOMENCLATURE:
Common name isopropalin (BSI, E-ISO, ANSI, WSSA); isopropaline ((f) F-ISO)
IUPAC name 4-isopropyl-2,6-dinitro-N,N-dipropylaniline
Chemical Abstracts name 4-(1-methylethyl)-2,6-dinitro-N,N-dipropylbenzenamine
CAS RN [33820530] Development codes EL-179
Smiles code CCCN(CCC)c1c(cc(cc1[N+](=O)[O-])C(C)C)[N+](=O)[O-]
15
H
23
N
3
O
4
Form Orange liquid;
(tech. is a red-orange liquid). V.p. 1.9 mPa (30 C) Solubility In water 0.1 mg/l (25 C). In
acetone, hexane, benzene, chloroform, diethyl ether, acetonitrile, methanol >1 (all in kg/l,
25 C). Stability Stable in feld use, though decomposed by uv light in laboratory studies.
F.p. 40.6 C
COMMERCIALISATION:
History Herbicide reported by L. R. Guse (Proc. North Cent. Weed Control Conf., 1969, p.
44; G. J. Shoop, ibid., p. 19). Introduced in USA (1972) by Eli Lilly & Co. (later DowElanco).
Patents US 3257190
APPLICATIONS:
Mode of action Selective herbicide, which affects physiological growth processes
associated with seed germination. Uses Control of broad-leaved weeds and grasses in
transplanted tobacco, and in direct-seeded tomatoes and capsicums. Applied pre-planting,
with soil incorporation at 12 kg/ha. Formulation types EC.
PRODUCTS:
Discontinued products Paarlan* (DowElanco).
ANALYSIS:
ANALYSIS: by glc (W. S. Johnson & O. D. Decherer, Anal. Methods Pestic. Plant Growth
Regul., 1976, 8, 369).
Oral Acute oral LD
50
for mice and rats >5000 mg tech./kg; for dogs and rabbits >2000
mg/kg. Skin and eye Acute percutaneous LD
50
for rabbits >2000 mg/kg. Slightly irritating
to skin and eyes (rabbits). NOEL (90 d) for rats and dogs >250 mg/kg diet (15 mg/kg
(CH
3
)
2
CH
NO
2
N[(CH
2
)
2
CH
3
]
2
NO
2
338
isothioate
b.w. for rats). ADI/RfD (EPA) 0.015 mg/kg b.w. [1986]. Toxicity Class WHO (a.i.) U EPA
(formulation) IV
ECOTOXICOLOGY:
Birds Acute oral LD
50
for chickens >2000, mallard ducks >2000, bobwhite quail >1000,
Japanese quail >1000 mg/kg. Fish LC
50
(96 h) for goldfsh >0.15, fathead minnows >0.1
mg/l. Bees LD
50
for honeybees 0.011 mg/bee.
ENVIRONMENTAL FATE:
Plants In plants, there is no translocation of isopropalin or its degradation products to
the leaves or fruit, and no signifcant residues or specifc metabolites have been detected.
Soil/Environment In soil, isopropalin is strongly adsorbed, with negligible leaching. In soils
DT
50
<0.5 y. Micro-organisms are believed to play a role in the degradation, and there is
also some loss from volatilisation and from photodecomposition of material remaining on
the soil surface. See R. R. Romanowski Weed Sci. 1978, 26, 258.
isopyrimol
NOMENCLATURE:
Common name isopyrimol (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 1-(4-chlorophenyl)-2-methyl-1-pyrimidin-5-ylpropan-1-ol
Chemical Abstracts name -(4-chlorophenyl)--(1-methylethyl)-5-pyrimidinemethanol
CAS RN [55283697] Smiles code CC(C)C(O)(c1ccc(Cl)cc1)c2cncnc2
14
H
15
ClN
2
O
COMMERCIALISATION:
History Plant growth regulator evaluated by Eli Lilly.
isothioate
Insecticide
IRAC 1B
NOMENCLATURE:
Common name isothioate (BSI, JMAF, E-ISO, (m) F-ISO)
IUPAC name S-2-isopropylthioethyl O,O-dimethyl phosphorodithioate
Chemical Abstracts name O,O-dimethyl S-[2-[(1-methylethyl)thio]
ethyl] phosphorodithioate Other names MITP CAS RN [36614387]
Development codes Z-7272 Smiles code COP(=S)(OC)SCCSC(C)C
7
H
17
O
2
PS
3
Form Light yellowish-
2-isovalerylindan-1,3-dione 339
brown liquid, with an aromatic odour. V.p. 293 mPa (20 C) Solubility In water 97 mg/l
(25 C).
COMMERCIALISATION:
History Insecticide introduced by Nihon Nohyaku Co., Ltd. Patents JP 624714
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide, also with
vapour action. Uses Effective against aphids when used as a seed dressing or when applied
to foliage at 1.01.5 kg/ha. Formulation types Seed treatment; GR .
PRODUCTS:
Discontinued products Hosdon* (Nihon Nohyaku).
ANALYSIS:
Product analysis by tlc with estimation of the phosphorus in the spots by standard
colorimetric methods (T. Nakagawa & M. Kanauchi, Anal. Methods Pestic. Plant Growth Regul.,
1978, 10, 75) or by glc (idem, ibid.). Residue analysis by glc with FID (idem, ibid.).
Oral Acute oral LD
50
percutaneous LD
50
for male mice 240 mg/kg. Toxicity Class WHO (a.i.) Ib
ECClassifcation T; R24/25
isovaledione
Fungicide
NOMENCLATURE:
Common name isovaledione (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(3,5-dichlorophenyl)-1-isovalerylhydantoin
Chemical Abstracts name 3-(3,5-dichlorophenyl)-1-(3-methyl-1-oxobutyl)-
2,4-imidazolidinedione CAS RN [70017935] Development codes S-9373
Smiles code CC(C)CC(=O)N1CC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
14
H
14
Cl
2
N
2
O
3
COMMERCIALISATION:
History Fungicide evaluated by Sumitomo Chemical Co., Ltd.
2-isovalerylindan-1,3-dione
Insecticide, rodenticide
NOMENCLATURE:
IUPAC name 2-isovalerylindan-1,3-dione
Chemical Abstracts name 2-(3-methyl-1-oxobutyl)-1H-indene-1,3(2H)-dione
Other names PMP CAS RN [83283]
340
isoxachlortole
Smiles code CC(C)CC(=O)C1C(=O)c2ccccc2C1=O
14
H
14
O
3
Form Yellow crystalline solid.
M.p. 6768 C Solubility Practically insoluble in water; soluble in most organic solvents.
Alkali metal and ammonium salts are soluble in water.
COMMERCIALISATION:
History Insecticide reported by L. B. Kilgore et al. (Ind. Eng. Chem., 1942, 34, 494).
Introduced by Kilgore Chemical Co. Patents US 2228170
APPLICATIONS: Uses A slow-acting insecticide. Structure-activity of some analogues
was discussed by L. B. Kilgore et al., (Ind. Eng. Chem., 1942, 34, 494).
PRODUCTS:
Discontinued products Valone* (Kilgore).
EHC 175 (1995).
isoxachlortole
Herbicide
HRAC F2 WSSA 27; isoxazole
NOMENCLATURE:
Common name isoxachlortole (BSI, E-ISO, (m) F-ISO)
IUPAC name 4-chloro-2-mesylphenyl 5-cyclopropyl-1,2-oxazol-4-yl ketone
Chemical Abstracts name [4-chloro-2-(methylsulfonyl)phenyl](5-cyclopropyl-4-
isoxazolyl)methanone CAS RN [141112063] Development codes RPA 201735
(Rhne-Poulenc)
14
H
12
ClNO
4
S
COMMERCIALISATION:
History Herbicide evaluated by Rhne-Poulenc.
APPLICATIONS:
Biochemistry p-Hydroxyphenyl pyruvate dioxygenase inhibitor.
CH
3
SO
2
Cl
O
N
C
O
isoxapyrifop 341
isoxapyrifop
Herbicide
NOMENCLATURE:
Common name isoxapyrifop (BSI, E-ISO, (m) F-ISO)
IUPAC name (RS)-2-[2-(4-(3,5-dichloro-2-pyridyloxy)phenoxy)propionyl]isoxazolidine
Chemical Abstracts name ()-2-[2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]-1-
oxopropyl]isoxazolidine CAS RN [87757184] Development codes HOK-1566;
HOK-868 (both Hokko); RH-0898 (Rohm & Haas)
Smiles code CC(Oc1ccc(Oc2ncc(Cl)cc2Cl)cc1)C(=O)N3CCCO3
17
H
16
Cl
2
N
2
O
4
Form Colourless
crystals. M.p. 121122 C K
ow
logP = 3.36 Solubility In water 9.8 mg/l (25 C).
COMMERCIALISATION:
History Herbicide reported by H. Ohyama et al. (Proc. Br. Crop Prot. Conf. Weeds, 1989, 1,
59). Introduced by Hokko Chemical Industry Co., Ltd.
Manufacturers Hokko
APPLICATIONS:
(ACCase). Inhibits the growth of meristematic tissue. Mode of action Selective
systemic herbicide absorbed mainly through the foliage. Uses Post-emergence control
of grass weeds including Echinochloa, Brachiaria, Leptochloa, and Digitaria species in
rice, and Alopecurus, Setaria, and Alopecurus species in spring wheat and durum wheat.
Formulation types SC. WG .
Oral Acute oral LD
50
percutaneous LD
50
for rats >5000, for rabbits >2000 mg/kg. Slight irritation to eyes, non-
irritating to skin (rabbits). NOEL (1.5 y) for mice 0.02 mg/kg diet daily. Other Non-
mutagenic and non-teratogenic (rats and rabbits). Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail >5000 mg/kg. Not mutagenic in assays. Fish LC
50

(96 h) for bluegill sunfsh 1.4, rainbow trout 1.3 mg/l. Daphnia LC
50
(6 h) >10 mg/l.
ENVIRONMENTAL FATE:
Plants Degrades rapidly in crops. Soil/Environment Degrades rapidly in soil to a
pyridyloxyphenoxypropionic acid metabolite (PPPA), which in turn degrades more slowly.
DT
50
of the a.i. and PPPA in aerobic laboratory studies 14 d and 3090 d respectively.
N
Cl
Cl
O O CH
CH
3
C O
N
O
342
isoxathion
isoxathion
Insecticide
NOMENCLATURE:
Common name isoxathion (BSI, JMAF, E-ISO)
IUPAC name O,O-diethyl O-5-phenylisoxazol-3-yl phosphorothioate
Chemical Abstracts name O,O-diethyl O-(5-phenyl-3-isoxazolyl) phosphorothioate
CAS RN [18854018] EC no 2426248 Development codes E-48; SI-6711 (Sankyo)
Smiles code CCOP(=S)(OCC)Oc1cc(on1)c2ccccc2
PHYSICAL CHEMISTRY:
13
H
16
NO
4
PS Form Pale yellow liquid,
with an ester-like odour. B.p. 160 C /0.15 mmHg V.p. <0.133 mPa (25 C) K
ow
logP =
3.88 (pH 6.3) S.g./densityc. 1.23 Solubility In water 1.9 mg/l (25 C). Readily soluble in
organic solvents. Stability Unstable to alkalis. Decomposes at 160 C. F.p. 210 C
COMMERCIALISATION:
History Insecticide reported by N. Sampei et al. (Sankyo Kenkyusho Nempo, 1970, 22,
221). Introduced in Japan in 1972 by Sankyo Co., Ltd (agrochemicals interests now Mitsui
Chemicals Agro, Inc.). Patents JP 525850 Manufacturers Mitsui Chemicals Agro; Sankyo
Agro
APPLICATIONS:
stomach action. Uses Effective against Aphididae, Coccidae, Diaspididae and Margarodidae
(at 5001000 g/ha) in cabbages, citrus and ornamentals; against Agromyzidae, Cicadellidae,
Delphacidae, Ephydridae and Pyralidae (at 600900 g/ha) in paddy rice; against Coleoptera
(at 1.2 kg/ha) in turf and trees; and against Noctuidae and Pieridae (at 5001000 g/
ha) in pome fruit, citrus fruit and vegetables. Formulation types DP; EC; MG; WP.
PRODUCTS:
Discontinued products Karphos* (Sankyo Agro); Nekiriton K* (Sankyo Agro);
Discontinued mixtures Sanritto Karufosu Funzai* (+ simeconazole) (Sankyo Agro).
ANALYSIS:
Product analysis by glc with FID (T. Nakamura & K. Yamaoka, Anal. Methods Pestic. Plant
Growth Regul., 1978, 10, 83). Residues determined by glc with FPD or FTD (idem, ibid.).
O
P(OCH
2
CH
3
)
2
S
N
O
japonilure 343
EHC 63 (1986), a general review of organophosphorus insecticides.
Oral Acute oral LD
50
for male rats 242, female rats 180, male mice 112, female mice 137
50
for rats >2000 mg/kg. Not irritant to skin.
Inhalation LC
50
(4 h) for male rats 4.2, female rats 2.0 g/m
3
. NOEL (2 y) for rats 1.2 mg/
kg b.w.; (9 w) for man 0.03 mg/kg b.w. daily. ADI/RfD (FSC) 0.003 mg/kg. Other Non-
mutagenic, non-carcinogenic and non-teratogenic, and no adverse effects on reproduction.
Toxicity Class WHO (a.i.) Ib EPA (formulation) II ECClassifcation T; R24/25| N; R50,
R53
ECOTOXICOLOGY:
Birds LD
50
for 7-day-old chickens 21.6, 50-day-old chickens 19.0 mg/kg. Fish LC
50
(48 h)
for carp 1.7 mg/l. Daphnia LC
50
(3 h) for D. pulex 0.0052 mg/l. Bees LC
50
(contact)
0.082 g/bee.
ENVIRONMENTAL FATE:
Soil/Environment DT
50
in soil 37 d.
japonilure
Insect pheromone
The sex pheromone of the Japanese beetle (Popillia japonica).
NOMENCLATURE:
IUPAC name 5-[(Z)-dec-1-enyl]-(5R)-dihydrofuran-2(3H)-one
Chemical Abstracts name (R,Z)-5-(1-decenyl)dihydro-2(3H)-furanone
Other names nuranone CAS RN [64726916], formerly [133494641], [77518
559] and [111192531]; [64726938] (S)- isomer Smiles code CCCCCCCC/C=C\
[C@H]1CCC(=O)O1;without stereochemistry:CCCCCCCCC=CC1CCC(=O)O1
14
H
24
O
2
Form Colourless, oily liquid.
B.p. 130134 C /0.1 mmHg K
ow
logP = 0 (EPA Fact Sheet) Solubility In water <0.01%
(25 C). Soluble in aromatic and aliphatic hydrocarbons (EPA Fact Sheet). Stability Stable
for 30 d at 50 C; stable to light (48 h in sun) (EPA Fact Sheet). Specifc rotation []D21
69.0 (c = 1.42, CHCl3) F.p. >200 C
O
O
H
CH
3
(CH
2
)
7
H
344
jodfenphos
COMMERCIALISATION:
History First registered in USA in 1979.
Manufacturers Ace; Nitto Denko
APPLICATIONS:
Mode of action Acts as an attractant. Uses Used for trapping Japanese beetle, in
combination with a foral lure (phenethyl propionate: eugenol: geraniol in the proportions
3:7:3).
Inhalation For rats >1.35 mg/l (aerosol) (EPA Fact Sheet).
jodfenphos
Acaricide, insecticide, ixodicide
IRAC 1B
NOMENCLATURE:
Common name iodofenphos (BSI, (m) F-ISO, BAN, ESA, Canada, New Zealand);
jodfenphos (E-ISO)
IUPAC name O-2,5-dichloro-4-iodophenyl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-(2,5-dichloro-4-iodophenyl) O,O-dimethyl
phosphorothioate CAS RN [18181709] Development codes C 9491
Smiles code COP(=S)(OC)Oc1cc(Cl)c(I)cc1Cl
8
H
8
Cl
2
IO
3
PS Form Colourless
crystals. M.p. 76 C V.p. 0.106 mPa (20 C) Henry <2.19 10-2 Pa m
3
mol
1
(calc.)
S.g./density 2.0 (20 C) Solubility In water <2 mg/l (20 C). In acetone, toluene 450,
dichloromethane 810, benzene 610, isopropanol 230, hexane 33, methanol, n-octanol 30 (all
in g/l, 20 C). Stability Extremely stable in neutral, weakly acidic and weakly alkaline media.
Hydrolysed by strong acids and alkalis. Tech. stable to >160 C.
COMMERCIALISATION:
History Insecticide and acaricide reported by B. C. Haddow & T. G. Marks (Proc. Br. Insectic.
Fungic. Conf., 5th, 1969, 2, 531). Introduced by Ciba AG (later Ciba-Geigy AG).
Patents BE 672431; GB 1057609
APPLICATIONS:
acaricide with contact and stomach action. Uses Control of crawling and fying insects, e.g.
P(OCH
3
)
2
S
I
Cl
Cl
O
kelevan 345
fies, ants, silverfsh, bedbugs, cockroaches, mosquitoes, mites, lice, ticks, feas, Beetles, etc. in
public hygiene, storerooms and warehouses, household use, and animal and poultry houses.
Formulation types WP; SC. EC; DP .
PRODUCTS:
Discontinued products AlFRACon* (Ciba-Geigy); Elocril* (Ciba-Geigy); Nuvanol N*
(Ciba-Geigy); Waspex* (Rentokil).
ANALYSIS:
Product analysis by glc. Residues determined by glc with ECD or FPD (N. Burkhard & G.
Voss, Pestic. Sci., 1972, 3, 183).
EHC 63 (1986; a general review of organophosphorus insecticides). PDS 43 (1980).
Oral Acute oral LD
50
for rats 2100, mice 3000, rabbits 2000, dogs 3000 mg/kg.
50
for rats >2000, rabbits >500 mg/kg; slight irritant
to skin, not irritant to eyes of rabbits. Inhalation LC
50
(6 h) for rats >0.246 mg/l.
NOEL (90 d) for rats 5 mg/kg diet (0.38 mg/kg daily), for dogs 15 mg/kg diet (0.45 mg/kg
daily). Toxicity Class WHO (a.i.) U EPA (formulation) III
ECOTOXICOLOGY:
Birds Non-toxic to birds. Fish LC
50
(96 h) for rainbow trout 0.060.10, goldfsh 1.001.33,
bluegill sunfsh 0.420.75 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals Following an oral dose of jodfenphos in rats, 92% was eliminated within 24 h.
For details of metabolites see F. R. Johannsen and C. Knowles (J. Econ. Entomol. 1970, 63,
693697).
kelevan
Insecticide
NOMENCLATURE:
Common name k(l) ((m) F-ISO); kelevan (BSI, E-ISO)
IUPAC name ethyl 5-(1,2,3,4,6,7,8,9,10,10-decachloro-5-
hydroxypentacyclo[5.3.0.02,6.03,9.04,8]dec-5-yl)-4-oxovalerate; ethyl
5-(1,2,4,5,6,7,8,8,9,10-decachloro-3-hydroxypentacyclo[5.3.02,6.04,10.05,9]dec-3-yl)-4-
oxovalerate
Chemical Abstracts name ethyl 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-2-hydroxy-
-oxo-1,3,4-metheno-1H-cyclobuta[cd]pentalene-2-pentanoate CAS RN [4234791]
Development codes GC-9160 (Allied) Smiles code CCOC(=O)CCC(=O)CC1(O)
C2(Cl)C3(Cl)C4(Cl)C1(Cl)C5(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C45Cl
346
KH-502
PHYSICAL CHEMISTRY:
Mol. wt. 634.8 M.f. C
17
H
12
Cl
10
O
4
COMMERCIALISATION:
History Insecticide reported by E. E. Gilbert et al. (J. Agric. Food Chem., 1966, 14, 111);
development reviewed by H. Maier-Bode (Residue Rev., 1976, 63, 45). Invented by the Allied
Chemical Corp. and developed by C. F. Spiess & Sohn.
APPLICATIONS:
Mode of action Ingested insecticide. Uses Used to control Leptinotarsa decemlineata on
potatoes, Meligethes aeneus and Ceutorhynchus spp. (E. E. Gilbert et al., J. Agric. Food Chem.,
1966, 14, 111; H. Maier-Bode, Residue Rev., 1976, 63, 45). Formulation types WP.
PRODUCTS:
Discontinued products Despirol* (Spiess); Discontinued mixtures Despirol Plus*
(+ mancozeb) (Spiess).
ANALYSIS:
Residues determined by glc after oxidation to chlordecone (A. Westlake et al., J. Agric. Food
Chem., 1970, 18, 159).
EHC 66 (1986). HSG 2 (1987). EU Status (1107/2009) Never notifed to the EU.
Oral Acute oral LD
50
depends critically on the carrier used; for male rats 290->4000,
female rats 2402830, male rabbits 251 mg/kg. NOEL (90 d) for dogs 20100 mg/kg diet.
Toxicity Class WHO (a.i.) OECClassifcation T; R24| Xn; R22| N; R51, R53
ENVIRONMENTAL FATE:
EHC 66 concluded that kelevan should not be used unless indispensable.
KH-502
Insecticide
NOMENCLATURE:
IUPAC name O,O-diethyl O-(1-phenyl-3-trifuoromethyl-1H-pyrazol-5-yl)
phosphorothioate
Chemical Abstracts name O-[1-phenyl-3-(trifuoromethyl)-1H-pyrazol-5-yl] O,O-diethyl
phosphorothioate Other names fupyrazofos (BSI rejected name)
O
P(OCH
2
CH
3
)
2
S
N
N
CF
3
leptophos 347
CAS RN [122431247] Development codes KH-502
14
H
16
F
3
N
2
O
3
PS
COMMERCIALISATION:
History Insecticide, discovered by KRICT and developed by Sungbo Chemicals Co. Ltd.
Registered in S Korea in 1996.
APPLICATIONS:
Biochemistry Acetylcholinesterase inhibitor. Uses For use against brown plant hopper,
green peach aphid and diamond-back moth, on Chinese cabbage.
PRODUCTS:
Discontinued products SunBong* (Sungbo).
ENVIRONMENTAL FATE:
50
(aerobic) 13.6 d (J-H. Kim et al., Pestic. Sci. (1998) 54 (3) 237).
leptophos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name leptophos (BSI, E-ISO, (m) F-ISO, ANSI, ESA); MBCP (JMAF)
IUPAC name O-4-bromo-2,5-dichlorophenyl O-methyl phenylphosphonothioate
Chemical Abstracts name O-(4-bromo-2,5-dichlorophenyl) O-methyl
phenylphosphonothioate CAS RN [21609905] EC no 2444728
Development codes VCS 506 (Velsicol) Smiles code COP(=S)(Oc1cc(Cl)c(Br)cc1Cl)
c2ccccc2
13
H
10
BrCl
2
O
2
PS Form Colourless
amorphous solid. M.p. 70.270.6 C S.g./density 1.53 (25 C) Solubility In water 2.4
mg/l (25 C). In acetone 470, benzene 1300, cyclohexane 142, heptane 59, isopropanol 24
(all in g/l, 25 C). Stability Stable to acids for prolonged exposure at normal temperature,
but is slowly hydrolysed by alkali.
COMMERCIALISATION:
History Insecticide reported by A. K. Azab (Proc. Br. Insectic. Fungic. Conf., 5th, 1969, 2, 550).
Introduced by Velsicol Chemical Corp. Patents US 3459836
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide.
Uses The EC is effective against Lepidoptera, e.g. Spodoptera littoralis on cotton at 1.5
kg/ha; also on fruit and vegetables at 100 g/100 l. The GR, at 1.5 kg/ha, controls Ostrinia
nubilalis on maize. Formulation types DP; EC; GR; WP.
PRODUCTS:
Discontinued products Abar* (Velsicol); Phosvel* (Velsicol).
348
LS830556
ANALYSIS:
Product analysis by i.r. spectrometry or by glc. Residues determined by glc with FPD or
TID.
PDS 38 (1979).
Oral Acute oral LD
50
for male albino ratsc. 50 mg/kg. Phosphonate analogue: 105133
50
for albino rabbits >800 mg/kg. NOEL In
90 d feeding trials, no ill-effect was observed in rats receiving 10 mg/kg diet or dogs 30
mg/kg diet. ADI/RfD (JMPR) Temporary ADI withdrawn [1978]. Other Causes delayed
neurotoxicity. Toxicity Class WHO (a.i.) IaECClassifcation T; R25, R39/25| Xn; R21|
N; R50, R53
lirimfos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name lirimfos (BSI, E-ISO, (m) F-ISO)
IUPAC name O-6-ethoxy-2-isopropylpyrimidin-4-yl O,O-dimethyl phosphorothioate
Chemical Abstracts name O-[6-ethoxy-2-(1-methylethyl)-4-pyrimidinyl] O,O-
dimethyl phosphorothioate CAS RN [38260638] Development codes SAN 201I
Smiles code CCOc1cc(OP(=S)(OC)OC)nc(n1)C(C)C
11
H
19
N
2
O
4
PS
COMMERCIALISATION:
History Insecticide evaluated by Sandoz AG.
APPLICATIONS:
LS830556
Herbicide
NOMENCLATURE:
IUPAC name ({[mesyl(methyl)carbamoyl]methyl}amino)methylphosphonic acid
CH
2
P
O
OH
OH
NH CH
2
C
O
N
S
O
O
CH
3
CH
3
lythidathion 349
Chemical Abstracts name [[[2-methyl(methylsulfonyl)amino]-2-oxoethyl]amino]
methylphosphonic acid Other names phosametine (withdrawn BSI proposed
name) CAS RN [98565185] Development codes LS830 556 (Rhne-Poulenc)
Smiles code CN(C(=O)CNCP(=O)(O)O)S(=O)(=O)C
5
H
13
N
2
O
6
PS Form Crystals.
M.p. 213215 C V.p. <0.267 mPa Solubility In water 45 g/l (20 C). In acetic acid 20 g/l.
Stability Stable at pH <4.
COMMERCIALISATION:
History Herbicide introduced by Rhne-Poulenc Agrochimie. Patents FR 2549839
APPLICATIONS: Uses Control of grass and broad-leaved weeds in vines, orchards and
cereals. Formulation types WG .
Oral Acute oral LD
50
50
for
rabbits >4000 mg/kg.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail >2150 mg/kg. Fish LC
50
320 mg/l.
lythidathion
Insecticide
IRAC 1B
NOMENCLATURE:
Common name lythidathion (BSI, E-ISO, (m) F-ISO)
IUPAC name S-5-ethoxy-2,3-dihydro-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl
phosphorodithioate; 3-dimethoxyphosphinothioylthiomethyl-5-ethoxy-1,3,4-thiadiazol-
2(3H)-one
Chemical Abstracts name S-[5-ethoxy-2-oxo-1,3,4-thiadiazol-3(2H)-ylmethyl] O,O-
dimethyl phosphorodithioate CAS RN [2669321] Development codes GS 12 968
(Ciba-Geigy); NC 2962 (FBC) Smiles code CCOc1nn(CSP(=S)(OC)OC)c(=O)s1
7
H
13
N
2
O
4
PS
3
COMMERCIALISATION:
History Insecticide evaluated by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
350
mancopper
malonoben
Acaricide
NOMENCLATURE:
Common name malonoben (BSI, E-ISO, ANSI, ESA); malonob(ne) ((m) F-ISO)
IUPAC name 2-(3,5-di-tert-butyl-4-hydroxybenzylidene)malononitrile
Chemical Abstracts name [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]
propanedinitrile CAS RN [10537470] Development codes GCP-5126; S 15126 (both
Gulf) Smiles code CC(C)(C)c1cc(C=C(C#N)C#N)cc(c1O)C(C)(C)C
18
H
22
N
2
O Form Crystalline solid.
M.p. 140141 C
COMMERCIALISATION:
History Acaricide reported by H. Fukashi et al. (Agric. Biol. Chem., 1971, 35, 2003). Evaluated
by Gulf Oil Chemicals Co.
APPLICATIONS:
Biochemistry Uncouples respiratory phosphorylation (S. Muraoka & H. Terada, Biochim.
Biophys. Acta, 1972, 275, 271). Mode of action Ingested and contact acaricide.
Uses Effective against various mite species (Aculus, Brevipalpus, Eotetranychus,
Panonychus, Phyllocoptruta and Tetranychus) on beans, citrus, cotton, pome and stone fruit,
nut trees and ornamentals. Formulation types EC; SC. WP.
PRODUCTS:
Discontinued products GCP 51262 EC* (Gulf); GCP 512650 W* (Gulf); GPC 51264
L* (Gulf).
Oral Acute oral LD
50
50
for
rabbits 2000 mg/kg. Toxicity Class WHO (a.i.) O
mancopper
Fungicide
multi-site: alkylenebis(dithiocarbamate)
NOMENCLATURE:
Common name mancopper (BSI, E-ISO, F-ISO)
IUPAC name ethylenebis(dithiocarbamate) mixed metal complex containingc. 13.7%
manganese andc. 4% copper
Chemical Abstracts name [[1,2-ethanediylbis[carbamodithioato]](2-)]manganese
mixture with [[1,2-ethanediylbis[carbamodithioato]](2-)]copper CAS RN [53988935]
COMMERCIALISATION:
History Fungicide introduced by Rohm & Haas Co. (now Dow AgroSciences).
mebenil 351
APPLICATIONS:
Biochemistry Non-specifc thiol reactant, inhibiting respiration.
Mode of action Fungicide with protective action. Uses Control of downy mildew on
vines. Also used as a seed treatment for control of Septoria and Fusarium spp. on cereals.
Formulation types WP; Seed treatment.
PRODUCTS:
Discontinued products Dithane C-90* (Dow AgroSciences).
ANALYSIS:
Details from Dow AgroSciences.
EHC 78 (1988) is a general review of dithiocarbamates and their degradation products.
EHC 200 (1998) is a general review of copper and copper compounds. JMPR Mtg. 68
(1993); JMPR Evaln. I 69 (1993); JMPR Evaln. II 70 (1993) for ethylenethiourea.
Oral Acute oral LD
50
for rats 9600 mg/kg.
mazidox
Insecticide
IRAC 1B
NOMENCLATURE:
Common name mazidox (BSI, E-ISO, (m) F-ISO)
IUPAC name tetramethylphosphorodiamidic azide (I); tetramethylazidophosphonic
diamide
Chemical Abstracts name (I) CAS RN [7219785] Development codes NC 7
Smiles code CN(C)P(=O)(N=[N+]=[N-])N(C)C
4
H
12
N
5
OP
COMMERCIALISATION:
History Insecticide evaluated by Pest Control Ltd (became Schering Agrochemicals).
APPLICATIONS:
mebenil
Fungicide
NOMENCLATURE:
Common name mebenil (BSI, E-ISO, (m) F-ISO)
IUPAC name o-toluanilide
352
mecarbinzid
Chemical Abstracts name 2-methyl-N-phenylbenzamide
CAS RN [7055030] Development codes BAS 305F; BAS 3050F; BAS 3053F (all
BASF) Smiles code Cc1ccccc1C(=O)Nc2ccccc2
14
H
13
NO Form Crystalline solid.
M.p. 125 C V.p. 4.4 103 mPa (20 C) Solubility Soluble in most organic solvents, e.g.
acetone, DMF, DMSO, ethanol, methanol, 3,5,5-trimethylcyclohex-2-enone.
COMMERCIALISATION:
History Fungicide reported by E-H. Pommer and J. Kradel (Proc. Br. Insectic. Fungic. Conf.,
5th, 1969, 2, 563). Developed by BASF AG.
APPLICATIONS: Uses Effective against Basidiomycetes and for the control of Puccinia
spp. on cereals at 1.72.5 kg/ha, and for treating seed potatoes against Rhizoctonia spp. at
0.300.37 g/kg seed. Formulation types Seed treatment; WP.
Oral Acute oral LD
50
for rats 6000 mg/kg. Skin and eye Not a skin irritant.
mecarbinzid
Fungicide
NOMENCLATURE:
Common name mecarbinzide (BSI before 1984, (m) F-ISO); mecarbinzid (BSI from 1984,
E-ISO)
IUPAC name methyl 1-(2-methylthioethylcarbamoyl)benzimidazol-2-ylcarbamate
Chemical Abstracts name methyl 1-[[[2-(methylthio)ethyl]amino]carbonyl]-1H-
benzimidazol-2-ylcarbamate CAS RN [27386647] Development codes BAS 3201F
(BASF) Smiles code COC(=O)Nc1nc2ccccc2n1C(=O)NCCSC
13
H
16
N
4
O
3
S
COMMERCIALISATION:
History Fungicide evaluated by BASF AG.
APPLICATIONS:
Mode of action Systemic fungicide.
medinoterb acetate; medinoterb 353
mecarphon
Insecticide
IRAC 1B
NOMENCLATURE:
Common name mecarphon (BSI, E-ISO, (m) F-ISO)
IUPAC name methyl [methoxy(methyl)phosphinothioylthio]acetyl(methyl)carbamate;
S-(N-methoxycarbonyl-N-methylcarbamoylmethyl) O-methyl methylphosphonodithioate
Chemical Abstracts name methyl 3,7-dimethyl-6-oxo-2-oxa-4-thia-7-aza-3-
phosphaoctan-8-oate 3-sulfde; methyl [[methoxy(methylphosphinothioyl)thio]acetyl]
methylcarbamate (former 9CI) CAS RN [29173317] Development codes MC 2420
Smiles code COC(=O)N(C)C(=O)CSP(=S)(C)OC
7
H
14
NO
4
PS
2
M.p. 36 C Solubility In water 300 mg/l (20 C). Soluble in aromatic hydrocarbons,
chlorinated hydrocarbons, ethanol; insoluble in hexane.
COMMERCIALISATION:
History Insecticide reported by M. Pianka & W. S. Catling (Proc. Int. Congr. Entomol., 13th,
Moscow, 1968, 2, 263). Introduced by Murphy Chemical Co. (later DowElanco).
Patents GB 1268199
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact insecticide.
Uses Effective at 500 mg/l against Hemiptera, including scale insects, Drosophila spp. on
pome and stone fruit, citrus and olives. Formulation types EC; WP.
ANALYSIS:
Product analysis by glc. Residues determined by glc with ECD.
Oral Acute oral LD
50
50
for rats
720 mg/kg. Toxicity Class WHO (a.i.) O
medinoterb acetate; medinoterb
Herbicide
NOMENCLATURE:
Common name medinoterb (BSI, E-ISO); m(dinoterbe) ((m) F-ISO)
IUPAC name 6-tert-butyl-2,4-dinitro-m-cresol; 6-tert-butyl-3-methyl-2,4-dinitrophenol
Chemical Abstracts name 6-(1,1-dimethylethyl)-3-methyl-2,4-dinitrophenol
CAS RN [3996596] medinoterb; [2487016] medinoterb acetate EC no 2196346
acetate Development codes P 1488; MC 1488 (both for the acetate)
354
menazon
PHYSICAL CHEMISTRY:
Mol. wt. 254.2; (acetate 296.3) M.f. C
11
H
14
N
2
O
5
; (acetate C
13
H
16
N
2
O
6
)
Form Medinoterb acetate is a yellow crystalline solid. M.p. 8687 C (acetate) V.p. 53
mPa (40 C) (acetate) Solubility In water <10 mg/l (room temperature, acetate). The
acetate is slightly soluble in hexane; very soluble in acetone, xylene. Stability The acetate
is stable, though slowly hydrolysed by alkali (room temperature) and rapidly on heating.
COMMERCIALISATION:
History Herbicide reported by G. A. Emery et al. (Proc. 2nd EWRC Symp. New Herbic.,
1965, p. 141). Introduced by Murphy Chemical Co. (later DowElanco).
Patents GB 1080282
APPLICATIONS: Uses Medinoterb acetate is toxic to seedlings and was recommended
pre-em. at 0.561.1 kg/ha on sugar beet; also on cotton and leguminous crops.
ANALYSIS:
Product analysis by reduction of the nitro groups by titanium(II) sulfate. Residues
determined by colorimetry as medinoterb.
Oral Medinoterb acetate: Acute oral LD
50
for rats 42, rabbits 80 mg/kg.
Skin and eye Medinoterb acetate: Acute percutaneous LD
50
for rats 1300, guinea-pigs
>200 mg/kg. NOEL Medinoterb acetate: (90 d) for male rats 1 mg/kg daily, for female
rats 1.2 mg/kg daily. Toxicity Class WHO (a.i.) OECClassifcation T; R25| Xn; R21
(acetate)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hens 560 mg/kg (medinoterb acetate).
ENVIRONMENTAL FATE:
Soil/Environment Decomposed in soil in 120 d.
menazon
Insecticide
IRAC 1B
NOMENCLATURE:
Common name menazon (BSI, E-ISO, F-ISO, JMAF, ESA); azidithion (France)
IUPAC name S-4,6-diamino-1,3,5-triazin-2-ylmethyl O,O-dimethyl phosphorodithioate
Chemical Abstracts name S-[(4,6-diamino-1,3,5-triazin-2-yl)methyl] O,O-dimethyl
phosphorodithioate CAS RN [78579] EC no 2011234 Development codes PP175
(ICI) Smiles code COP(=S)(OC)SCc1nc(N)nc(N)n1
PHYSICAL CHEMISTRY:
6
H
12
N
5
O
2
PS
2
Form Colourless,
menazon 355
odourless crystals; (tech. has a mercaptan-like odour). It forms a crystalline hydrochloride.
M.p. 160162 C (decomp.) V.p. 0.13 mPa (25 C) Solubility In water 240 mg/l (20 C).
In 2-ethoxyethanol 200, 2-methoxyethanol 250, tetrahydrofurfuryl alcohol 150, ethylene
glycol 100 (all in g/kg, room temperature). Stability The solid is stable 50 C, but is
unstable under acid (pH <4) or alkaline (pH >8) conditions.
COMMERCIALISATION:
History Insecticide reported by A. Calderbank (Chem. Ind. (London), 1961, p. 630).
Introduced by ICI Plant Protection Division (later ICI Agrochemicals). Patents GB 899701
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide.
Uses Mainly as a tuber or seed treatment to protect seedlings, for foliage application, as
a soil drench and root dip. Formulation types SC. WP. Compatibility Not compatible
with strongly alkaline pesticides, and may be decomposed by the reactive surfaces of some
inert fllers.
PRODUCTS:
Discontinued products Saphicol* (ICI); Saphizon* (ICI); Sayfos* (ICI);
Discontinued mixtures Abol X* (+ gamma-HCH) (ICI).
ANALYSIS:
Product analysis by oxidation to phosphoric acid, estimated by colorimetry. Residues
determined after conversion to phosphoric acid and subsequent colorimetry (A.
Calderbank & J. B. Turner, Analyst (London), 1962, 87, 273; A. Calderbank, Anal. Methods Pestic.
Plant Growth Regul., 1973, 7, 317).
Oral Acute oral LD
50
for female rats 1950 mg/kg. Skin and eye Rabbits treated on their
shaved backs for 24 h with 500800 mg/kg suffered no local or systemic toxic effect.
NOEL (90 d) for rats 30 mg/kg diet; in a 2 y trial, rats receiving 4000, 1000 or 250 mg/kg
diet showed no signifcant effect other than partial inhibition of cholinesterase.
Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R22| N; R52, R53
356
mephosfolan
mephosfolan
IRAC 1B
NOMENCLATURE:
Common name mephosfolan (BSI, E-ISO); m(phospholan) ((m) F-ISO)
IUPAC name diethyl 4-methyl-1,3-dithiolan-2-ylidenephosphoramidate;
2-(diethoxyphosphinylimino)-4-methyl-1,3-dithiolane
Chemical Abstracts name diethyl (4-methyl-1,3-dithiolan-2-ylidene)phosphoramidate
CAS RN [950107] EC no 2134473 Development codes EI 47 470 (Cyanamid)
Smiles code CCOP(=O)(OCC)N=C1SCC(C)S1
8
H
16
NO
3
PS
2
Form Yellow to amber
liquid (tech.). B.p. 120 C /0.001 mmHg K
ow
logP = 1.045 Solubility In water 57 mg/l
(25 C). Soluble in ethanol, acetone, 1,2-dichloroethane, and benzene. Stability Stable in
aqueous solution under neutral conditions. Hydrolysed by acids and alkalis 2>pH>9.
COMMERCIALISATION:
History Insecticide and acaricide introduced by American Cyanamid Co.
Patents GB 974138 Manufacturers Cyanamid
APPLICATIONS:
acaricide with contact and stomach action. Absorbed by the roots and leaves.
Uses Control of aphids, thrips, bollWorms, jassids, mites, stem borers, whitefy, and leaf-
eating larvae on cotton, fruit, hops, maize, sorghum, rice, sugar cane, potatoes, vegetables,
tobacco, etc. Phytotoxicity Cotton foliage may be injured in high-rainfall conditions.
Formulation types EC; GR .
PRODUCTS:
Discontinued products Cytro-Lane* (Cyanamid).
ANALYSIS:
Product analysis by uv spectroscopy. Residues determined by glc (N. R. Pasarela & E. J.
Orloski, Anal. Methods Pestic. Plant Growth Regul., 1973, 7, 231; R. C. Blinn & J. E. Boyd, J. Assoc.
Off. Agric. Chem., 1964, 47, 1106).
EHC 63 (1986), a general review of organophosphorus insecticides. EU Status
P(OCH
2
CH
3
)
2
O
S
S
N
CH
3
mercuric oxide 357
Oral Acute oral LD
50
for rats 3.98.9 mg tech./kg; for albino mice 11.3 mg/kg.
50
(24 h) for male albino rabbits 28.7 mg tech./
kg, >5000 mg (as 2% GR)/kg. NOEL In 90 d feeding trials, male albino rats receiving 15
mg/kg diet showed a reduction in erythrocyte and brain cholinesterase activity, but there
was no signifcant effect on weight gain. Toxicity Class WHO (a.i.) Ia EPA (formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail 12.8 mg/kg. Fish LC
50
2.1, carp 54.5 mg/l. Bees Toxic to bees; LC
50
(topical) 3.5 g/bee.
mercuric oxide
Fungicide, wound protectant
NOMENCLATURE:
Common name oxyde mercurique (F-ISO, accepted in lieu of a common name);
mercuric oxide (E-ISO, accepted in lieu of a common name)
IUPAC name mercury(II) oxide; mercury oxide
Chemical Abstracts name mercury oxide (HgO) Other names yellow oxide of
mercury CAS RN [21908532], formerly [1344452] Smiles code O=[Hg]
PHYSICAL CHEMISTRY:
Mol. wt. 216.6 M.f. HgO Form Orange-red to bright red powder (yellow when fnely
divided). M.p. Decomposes atc. 500 C Solubility In water 53 mg/l (25 C). Insoluble in
organic solvents. Soluble in dilute acids, forming the corresponding mercury salts. Stability
Decomposes on exposure to light. Darkens atc. 400 C and decomposes into mercury and
oxygen atc. 500 C.
COMMERCIALISATION:
History Introduced by Sandoz AG (became Novartis Crop Protection AG, who ceased to
manufacture or market it).
APPLICATIONS: Uses Wound protectant for pruning cuts and other bark injuries,
and control of canker, on fruit trees, rubber trees, vines, and ornamental trees and shrubs.
Formulation types PA .
PRODUCTS:
Discontinued products Kankerdood* (Bayer); Kankertox* (Ciba); Santar* (Sandoz,
Zeneca).
ANALYSIS:
Product analysis by colorimetry (CIPAC Handbook, 1970, 1, 514), by titration (AOAC Methods,
18th Ed., 971.04) or by gravimetry (ibid., 922.05). Mercury impurities determined
HgO
358
mercurous chloride
(CIPAC Handbook, 1994, F, 264).
ICSC.981 (2001). CICAD 50 (2003). IARC 58 (1994). EU Status (1107/2009) Considered
to be outside the scope of the Directive; already banned, 79/117/EEC as amended by
91/188/EEC.
IARC Class 3
Oral Acute oral LD
50
for rats 18 mg/kg. Extremely poisonous orally to all animals.
Toxicity Class WHO (a.i.) Ib EPA (formulation) I ECClassifcation Not specifed, but
inorganic mercury generally is assigned T+; R26/27/28| R33| N; R50, R53, concentration-
dependent. PIC Yes.
ECOTOXICOLOGY:
Fish Toxic to fsh.
mercurous chloride
NOMENCLATURE:
Common name chlorure mercureux (F-ISO, accepted in lieu of a common name);
mercurous chloride (E-ISO, accepted in lieu of a common name)
IUPAC name mercury(I) chloride; dimercury dichloride
Chemical Abstracts name mercury chloride (Hg2Cl
2
) Other names
calomel CAS RN [10112911] Hg2Cl
2
; [7546307] HgCl EC no 2333075
Smiles code Cl[Hg][Hg]Cl
PHYSICAL CHEMISTRY:
Mol. wt. 472.1 M.f. Cl
2
Hg
2
Form White powder. M.p. Sublimes at 400500 C
S.g./density 7.15 Solubility In water 2 mg/l (25 C). Soluble in most organic solvents,
and also in cold dilute acids. Stability Decomposes slowly in sunlight. Under aqueous
conditions, slowly decomposes to mercury and mercuric chloride (more rapid
decomposition in the presence of alkali).
COMMERCIALISATION:
History Has long been used as an insecticide and, having a lower toxicity to mammals,
largely replaced mercuric chloride, as recommended by H. Glasgow (J. Econ. Entomol., 1929,
22, 335).
APPLICATIONS: Uses Soil application for control of Delia spp. and Plasmodiophora
brassicae in brassicas; and Sclerotium cepivorum in onions. Control of dollar spot and
Fusarium patch on turf. Phytotoxicity Phytotoxic to many crops.
Formulation types DP; TC.
Hg
2
Cl
2
mesoprazine 359
PRODUCTS:
Discontinued products Cyclosan* (Rhne-Poulenc).
ANALYSIS:
Product analysis by colorimetry (CIPAC Handbook, 1970, 1, 514), by titration
(AOAC Methods, 18th Ed., 971.04) or by gravimetry (ibid., 922.05). Mercury impurities
determined (CIPAC Handbook, 1994, F, 264). Residues determined by atomic absorption
spectrophotometry (AOAC Methods, 14th Ed., 25.13125.135) or by colorimetry (ibid.,
25.13825.145).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds. ICSC.984
(2000). CICAD 50 (2003). EU Status (1107/2009) Considered to be outside the scope of
the Directive; already banned, 79/117/EEC as amended by 91/188/EEC.
IARC Class Inorganic mercury compounds classifed 3
Oral Acute oral LD
50
for rats 210 mg/kg. Toxicity Class WHO (a.i.) II EPA (formulation)
II ECClassifcation Xn; R22| Xi; R36/37/38| N; R50, R53 PIC Yes.
ECOTOXICOLOGY:
Fish Toxic to fsh.
mesoprazine
Herbicide
NOMENCLATURE:
Common name mesoprazine (BSI, E-ISO, (f) F-ISO)
2
-isopropyl-N4-(3-methoxypropyl)-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-chloro-N-(3-methoxypropyl)-N-(1-methylethyl)-1,3,5-
triazine-2,4-diamine CAS RN [1824095] Development codes G 34 698; CGA 4999
Smiles code COCCCNc1nc(Cl)nc(NC(C)C)n1
10
H
18
ClN
5
O
COMMERCIALISATION:
360
metamifop
mesulfenfos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name m(sulfenfos) ((m) F-ISO); mesulfenfos (BSI, E-ISO)
IUPAC name O,O-dimethyl O-4-methylsulfnyl-m-tolyl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-[3-methyl-4-(methylsulfnyl)phenyl]
phosphorothioate CAS RN [3761419] Development codes BAY S 2281
Smiles code COP(=S)(OC)Oc1ccc(S(=O)C)c(C)c1
10
H
15
O
4
PS
2
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Baycid SO* (Bayer).
metamifop
Herbicide
NOMENCLATURE:
Common name m(tamifop) ((m) F-ISO); metamifop (BSI, E-ISO)
IUPAC name (R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]-2-fuoro-N-
methylpropionanilide
Chemical Abstracts name (R)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]
phenoxy]-N-(2-fuorophenyl)-N-methylpropanamide CAS RN [256412
892] Development codes DBH-129; K-12974 (both Dongbu Hannong)
P
O
O
O
S
S
O
O,O-dimethyl O-4-methylsulfinyl-m-tolyl phosphorothioate
CH
3
O
N
CH
3
F
O
O
O
N
Cl
metamifop 361
Smiles code C[C@@H](Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1)C(=O)N(C)
c4ccccc4F;without stereochemistry:CC(Oc1ccc(Oc2nc3ccc(Cl)cc3o2)cc1)C(=O)N(C)
c4ccccc4F
PHYSICAL CHEMISTRY:
Composition 96%. Mol. wt. 440.9 M.f. C
23
H
18
ClFN
2
O
4
Form Light brown, odourless,
fne granular powder. M.p. 77.078.5 C B.p. Decomposes V.p. 1.51 10
1
mPa (25 C)
K
ow
logP = 5.45 (pH 7, 20 C) Henry 6.35 10-2 Pa m
3
mol
1
(20 C) S.g./density
1.39 Solubility In water 6.87 10
4
g/l (pH 7, 20 C). In acetone, 1,2-dichloroethane,
ethyl acetate, methanol and xylene >250, n-heptane 2.32, n-octanol 41.9 (all in g/l, 20 C).
Stability Stable at 54 C.
COMMERCIALISATION:
History Reported by T. J. Kim et al. (Proc. BCPC Int. Congr., Glasgow, 2003, 1, 81).
Discovered by Korean Research Institute of Chemical Technology (KRICT) and developed
by Dongbu Hannong Chemical Co. Ltd (now Dongbu HiTek).
Manufacturers Dongbu HiTek
APPLICATIONS:
Biochemistry Acetyl-CoA carboxylase (ACCase) inhibitor. Rice/Echinochloa selectivity
is mainly due to differential sensitivity to ACCase, and may also be due to differential
foliar uptake. The (S)- isomer is less active than the (R)- isomer. Mode of action Causes
chlorosis in developing leaves, with growth inhibition. Uses Post-emergence control
of annual and perennial grass weeds (including Echinochloa spp., Leptochloa chinensis,
Digitaria spp. and Eleusine indica) in various crops, including rice; applied at 90200 g/ha for
upland crops (wheat, soya beans, cotton, turf, etc.). Formulation types EC; GR; ME; WG .
PRODUCTS:
Other products Pizero (Dongbu HiTek).
EU Status (1107/2009) Never notifed and authorised in the EU.
Oral Acute oral LD
50
50
for
rats >2000 mg/kg. Not a skin irritant; slightly irritating to eyes. May cause sensitisation
by skin contact. Inhalation LC
50
(4 h) for rats >2.61 mg/l. Other Non-mutagenic in the
Ames, chromosome aberration, cell mutation and micronucleus tests.
ECOTOXICOLOGY:
Fish LC
50
(96 h) for rainbow trout 0.307 mg/l. Daphnia EC
50
(48 h) 0.288 mg/l.
Algae EC
50
(48 h) >2.03 mg/l. Bees LD
50
(contact and oral) >100 g/bee. Worms LC
50

for earthworms >1000 ppm.
ENVIRONMENTAL FATE:
Soil/Environment Soil degradation is both chemical and microbial; DT
50
4060 d (25 C).
Aqueous photolysis produces seven detectable metabolites; DT
50
18120 d, depending on
conditions.
362
metfurazon
metazoxolon
Fungicide
NOMENCLATURE:
Common name metazoxolon (BSI, E-ISO, (m) F-ISO)
IUPAC name 4-(3-chlorophenylhydrazono)-3-methyl-1,2-oxazol-5(4H)-one;
4-(3-chlorophenylhydrazono)-3-methylisoxazol-5(4H)-one
Chemical Abstracts name 3-methyl-4,5-isoxazoledione 4-[(3-chlorophenyl)hydrazone]
CAS RN [5707733] Development codes PP395
Smiles code CC1=NOC(=O)C1=NNc2cccc(Cl)c2
10
H
8
ClN
3
O
2
COMMERCIALISATION:
History Fungicide reported by T. J. Purnell (Proc. Br. Crop Prot. Conf., 7th, 1973, 2, 603).
Evaluated by ICI Agrochemicals.
APPLICATIONS: Uses Control of Pythium spp. on ornamentals, peanuts and peas,
Rhizoctonia solani on cotton, Phytophthora capsici on peppers, Fusarium nivale on rye, and
Fusarium nivale on wheat, when applied as a seed or soil treatment.
Oral Acute oral LD
50
for female rats 3340 mg/kg. Skin and eye Acute percutaneous LD
50

for rats >1000 mg/kg Not a skin or eye irritant.
metfurazon
Herbicide
NOMENCLATURE:
Common name metfurazon (BSI (from 1984), E-ISO); metfurazone (BSI (before 1984),
(f) F-ISO)
IUPAC name 4-chloro-5-dimethylamino-2-(,,-trifuoro-m-tolyl)pyridazin-3(2H)-one
Chemical Abstracts name 4-chloro-5-(dimethylamino)-2-[(3-trifuoromethyl)
phenyl]-3(2H)-pyridazinone CAS RN [23576230] Development codes SAN 6706H
Smiles code CN(C)c1cnn(c2cccc(c2)C(F)(F)F)c(=O)c1Cl
13
H
11
ClF
3
N
3
O
COMMERCIALISATION:
History Herbicide evaluated by Sandoz AG.
methacrifos 363
methacrifos
IRAC 1B
NOMENCLATURE:
Common name methacrifos (BSI, E-ISO, (m) F-ISO)
IUPAC name methyl (E)-3-(dimethoxyphosphinothioyloxy)-2-methacrylate; (E)-O-2-
methoxycarbonylprop-1-enyl O,O-dimethyl phosphorothioate
Chemical Abstracts name (E)-methyl 3-[(dimethoxyphosphinothioyl)oxy]-2-methyl-2-
propenoate CAS RN [62610779] (E)- isomer; [30864289] unstated stereochemistry
EC no 2503662 Development codes CGA 20 168 Smiles code COC(=O)
C(=COP(=S)(OC)OC)C
PHYSICAL CHEMISTRY:
Mol. wt. 240.2 M.f. C
7
H
13
O
5
PS Form Colourless liquid. B.p. 90 C /0.01 mmHg
V.p. 160 mPa (20 C) K
ow
logP 3.0 Henry 9.61 10-2 Pa m
3
mol
1
1.225 (20 C) Solubility In water 400 mg/l (20 C). Miscible with many organic solvents,
e.g. methanol, benzene, hexane, and dichloromethane. Stability Relatively unstable in
alkaline conditions; on hydrolysis DT
50
(calc.) (20 C) 66 d (pH 1), 29 d (pH 7), 9.5 d (pH
9). Decomposes atc. 200 C. F.p. 6973 C
COMMERCIALISATION:
History Insecticide reported by R. Wyniger et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1977,
3, 1033). Introduced by Ciba-Geigy AG (later Novartis Crop Protection AG).
Patents BE 766000; GB 1342630 Manufacturers Novartis
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Insecticide and acaricide
with respiratory, contact, and stomach action. Gives rapid knockdown, and has long
residual activity. Uses Mainly used for control of arthropod pests in stored products by
incorporation or by surface treatment. Phytotoxicity Should not be used on plant foliage.
Formulation types DP; EC. Compatibility Incompatible with strongly acidic or alkaline
materials.
PRODUCTS:
Discontinued products Damfn* (Novartis).
ANALYSIS:
Product analysis by glc. Residues in grain determined by glc with FPD or TID (J.
Desmarchelier et al., Pestic. Sci., 1977, 8, 473).
O
P(OCH
3
)
2
S
C
C
CH
3
H
C
O
CH
3
O
364
methanesulfonyl fuoride
EHC 63 (1986) is a general review of organophosphorus insecticides. JMPR Mtg. 65 (1992);
JMPR Evaln. I 66 (1992); JMPR Evaln. II 61 (1990). EU Status (1107/2009) Not approved,
Oral Acute oral LD
50
50
for rats
>3100 mg/kg. Mild skin irritant; non-irritating to eyes (rabbits). Inhalation LC
50
(6 h) for
rats 2.2 mg/l air. NOEL (2 y) for rats 0.6 mg/kg b.w. daily. ADI/RfD (JMPR) 0.006 mg/kg
b.w. [1990]. Toxicity Class WHO (a.i.) IIECClassifcation Xn; R22| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail 116 mg/kg. Fish LC
50
(96 h) for carp 30.0,
rainbow trout 0.4 mg/l.
ENVIRONMENTAL FATE:
Animals Rapid excretion; metabolism via hydrolysis of the methyl esters as well as
cleavage of the phosphoric and vinyl ester bonds, followed by mineralisation to CO
2
.
methalpropalin
Herbicide
NOMENCLATURE:
Common name methalpropalin (BSI, E-ISO); m(thalpropaline) ((f) F-ISO)
IUPAC name ,,-trifuoro-N-(2-methylallyl)-2,6-dinitro-N-propyl-p-toluidine
Chemical Abstracts name N-(2-methyl-2-propenyl)-2,6-dinitro-N-propyl-4-
(trifuoromethyl)benzenamine CAS RN [57801464]
Smiles code CCCN(CC(=C)C)c1c(cc(cc1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
14
H
16
F
3
N
3
O
4
COMMERCIALISATION:
History Herbicide evaluated by Eli Lilly & Co.
methanesulfonyl fuoride
Insecticide
NOMENCLATURE:
IUPAC name methanesulfonyl fuoride (I)
Chemical Abstracts name (I) Other names MSF CAS RN [558258]
Smiles code CS(=O)(=O)F
PHYSICAL CHEMISTRY: Mol. wt. 98.10 M.f. CH
3
FO
2
S
COMMERCIALISATION:
History Fumigant insecticide marketed by Bayer AG.
methasulfocarb 365
APPLICATIONS:
PRODUCTS:
Discontinued products Fumette* (Bayer).
methasulfocarb
Fungicide, plant growth regulator
FRAC 42, U; thiocarbamate fungicide
NOMENCLATURE:
Common name m(thasulfocarb) ((m) F-ISO); methasulfocarb (BSI, E-ISO)
IUPAC name S-4-methylsulfonyloxyphenyl methylthiocarbamate
Chemical Abstracts name S-[4-[(methylsulfonyl)oxy]phenyl] methylcarbamothioate
CAS RN [66952496] Development codes NK-191 (Nippon Kayaku)
Smiles code CNC(=O)Sc1ccc(OS(=O)(=O)C)cc1
9
H
11
NO
4
S
2
M.p. 137.5138.5 C Solubility In water 480 mg/l. Soluble in acetone, alcohols, and
benzene. Stability Stable to light.
COMMERCIALISATION:
History Fungicide and plant growth regulator reported by K. Ohmori (Jpn. Pestic. Inf.,
1985, No. 46, p. 17). Introduced in Japan (1984) by Nippon Kayaku Co., Ltd.
Patents US 4126696; DE 2745229; JP 5347527 Manufacturers Nippon Kayaku
APPLICATIONS: Uses Soil fungicide for control of Corticium, Fusarium, Mucor,
Pseudomonas, Pythium, Rhizopus, Rhizoctonia, and Trichoderma spp. in rice. Application rate
0.61 g/rice nursery tray. Formulation types DP .
PRODUCTS:
Discontinued products Kayabest* (Nippon Kayaku).
ANALYSIS:
Product and residue analysis by glc.
Oral Acute oral LD
50
50
for rats and mice >5000 mg/kg. Inhalation LC
50

(4 h) for rats >0.44 mg/l air. Other Non-mutagenic to mice. Non-teratogenic to rats.
ECOTOXICOLOGY:
Fish LC
50
CH
3
NHCOS OSO
2
CH
3
366
methazole
methazole
Herbicide
NOMENCLATURE:
Common name methazole (BSI, ANSI, Australia, WSSA)
IUPAC name 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione
Chemical Abstracts name 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-
3,5-dione CAS RN [20354261] EC no 2437616 Development codes VCS-438
(Sandoz) Smiles code Cn1c(=O)on(c2ccc(Cl)c(Cl)c2)c1=O
PHYSICAL CHEMISTRY:
9
H
6
Cl
2
N
2
O
3
Form Colourless crystals;
(tech. a light tan solid). M.p. 123124 C V.p. 0.133 mPa (25 C) K
ow
logP = 2.590.04
(25 C) Henry 2.32 10-2 Pa m
3
mol
1
(calc.) S.g./density 1.24 (25 C) Solubility In
water 1.5 mg/l (25 C). In DMF 323, dichloromethane 255, cyclohexanone 171, acetone
40, xylene 55, methanol 6.5 (all in g/l, 25 C). Stability Solutions in methanol undergo
photodecomposition when exposed to uv light. Suspensions in water, when exposed to
sunlight, are more stable (G. W. Ivie et al., J. Agric. Food Chem., 1973, 21, 386). Hydrolysed in
strongly acidic and alkaline media. Decomposes below the b.p.
COMMERCIALISATION:
History Herbicide reported by W. Furness (Proc. Int. Congr. Plant Prot., 7th, Paris, 1970,
p. 314). Introduced by Velsicol Chemical Corp. and later manufactured and marketed by
Sandoz AG. Patents US 3437664
APPLICATIONS:
Mode of action Selective systemic herbicide, absorbed by the roots and leaves, with
translocation. Uses Used to control certain grasses and many broad-leaved weeds: pre-
emergence in garlic and potatoes (12 kg/ha); as a directed spray on to soil or emerged
weeds in citrus, stone-fruit, nuts, tea and established vines (6 kg/ha) and on cotton 15 cm
tall (12 kg/ha), onions (>2 leaves) (2.5 kg/ha), newly seeded or winter-dormant alfalfa
(>1 y old) (2.25 kg/ha). Preferably applied to moist soil; lower rates were applicable to light
sandy soils. Formulation types WP; GR; WG . Compatibility Incompatible with some
ester-type hormone herbicides.
PRODUCTS:
Discontinued products Probe* (Sandoz); Tunic* (Sandoz).
ANALYSIS:
Product analysis by lc and i.r. spectrophotometry (AOAC Methods, 18th Ed., 992.02, 982.03;
N
O
N
Cl
Cl
CH
3
O
O
methfuroxam 367
D. M. Whiteacre et al., Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 367). Residues
determined by glc with ECD (idem, ibid.) or by hplc (idem, ibid.).
Oral Acute oral LD
50
50

for rabbits >12 500 mg/kg. Mild irritant to skin and eyes (rabbits). No skin sensitisation
(guinea pigs). Chloracne observed in rabbit-ear studies and among certain workers at
manufacturing plants. Inhalation LC
50
(4 h) for rats >200 mg/l air (dust). NOEL In 2-year
feeding trials in rats and mice, a yellow-brown pigment occurred in the spleen or liver at
>100 mg/kg diet. Non-mutagenic and non-teratogenic in rabbits (at up to 60 mg/kg daily),
but foetal toxicity observed at 30 mg/kg daily. In a 3-generation study in rats, NOEL
was 50 mg/kg diet (cataracts were observed at 100 mg/kg diet, but no other ill-effects).
Toxicity Class WHO (a.i.) IIIECClassifcation Xn; R21/22| Xi; R36/38| N; R51, R53
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks 11 200, bobwhite quail 1825 mg/kg diet. In
1-generation study NOEL for bobwhite quail and mallard ducks 3 mg/kg diet. Fish LC
50

(96 h) for bluegill sunfsh 4.47, rainbow trout 4.09 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, methazole undergoes decarboxylation to 1-(3,4-dichlorophenyl)-3-
methylurea, which is further degraded by N-demethylation to 3,4-dichlorophenylurea, and
then to 3,4-dichloroaniline. Degradation is almost complete within 3 d.
Soil/Environment Microbially degraded in soil by the same route as in plants. Soil DT
50

<30 d.
methfuroxam
Fungicide
NOMENCLATURE:
Common name methfuroxam (BSI, E-ISO, ANSI); m(thfuroxame) ((m) F-ISO)
IUPAC name 2,4,5-trimethyl-3-furanilide
Chemical Abstracts name 2,4,5-trimethyl-N-phenyl-3-furancarboxamide
CAS RN [28730178] Development codes H719 (Uniroyal)
Smiles code Cc1oc(C)c(C(=O)Nc2ccccc2)c1C
14
H
15
NO
2
Form Colourless crystals
with a faint odour. M.p. 138142 C V.p. <13 Pa (20 C) Solubility In water
10 mg/l (25 C). In DMF 412, acetone 125, methanol 64, benzene 36 (all in g/kg).
Stability Hydrolysed by strong acids and alkalis.
368
methiobencarb
COMMERCIALISATION:
History Fungicide reported by K. T. Alcock (Plant Dis. Reptr., 1978, 62, 854). Introduced in
Germany by Uniroyal Chemical Co., Inc. Patents DE 2006471
APPLICATIONS:
Biochemistry Inhibitor of succinate dehydrogenase complex, in the respiratory electron
transport chain. Mode of action Systemic fungicide. Uses Seed treatment for control of
Tilletia and Ustilago spp. in cereals applied at up to 50 g/100 kg seed.
Formulation types DS; FS; LS; WS .
PRODUCTS:
Discontinued products Trivax* (Uniroyal).
ANALYSIS:
Product analysis by gc.
Oral Acute oral LD
50
for male rats 4300, female rats 1470, mice 620880, dogs 10 000
50
for rabbits 3160 mg/kg. No skin irritation
(rabbits); slight irritation of mucous membranes. Inhalation LC
50
for rats 17.39 mg/l air.
NOEL In 90 d feeding trials, no ill-effects were observed in rats at 300 mg/kg diet or in
dogs at 1000 mg/kg diet.
ECOTOXICOLOGY:
Fish LC
50
for bluegill sunfsh 0.18, rainbow trout 0.26 mg/l. Bees Combinations with
imazalil and thiabendazole are not hazardous to bees when used as recommended.
ENVIRONMENTAL FATE:
Plants After application of 30 g methfuroxam per 100 kg seed, the residue levels in unripe
and ripe maize are 0.020.13 and 00.01 mg/kg, respectively.
methiobencarb
Herbicide
NOMENCLATURE:
Common name methiobencarb (BSI, E-ISO); m(thiobencarbe) ((m) F-ISO)
IUPAC name S-4-methoxybenzyl diethylthiocarbamate
Chemical Abstracts name S-[(4-methoxyphenyl)methyl] diethylcarbamothioate
CAS RN [18357783] Development codes NTN 5810
Smiles code CCN(CC)C(=O)SCc1ccc(OC)cc1
13
H
19
NO
2
S
COMMERCIALISATION:
methocrotophos 369
methiuron
Herbicide
NOMENCLATURE:
Common name methiuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,1-dimethyl-3-m-tolyl-2-thiourea
Chemical Abstracts name N,N-dimethyl-N-(3-methylphenyl)thiourea
CAS RN [21540352] Development codes MH 090
Smiles code CN(C)C(=S)Nc1cccc(C)c1
10
H
14
N
2
M.p. 145 C Solubility In water 400 mg/l (25 C). In methanol 70, pyridine 470 (both g/l,
25 C). Stability Hydrolysed by concentrated acids; stable to light.
COMMERCIALISATION:
History Herbicide introduced by Yorkshire Tar Distillers Ltd.
APPLICATIONS:
Mode of action Selective herbicide. Uses Used at 1.122.24 kg/ha for selective pre-em.
control of weeds in onions, potatoes and sugar beet, and at 2.24 kg/ha post-em. in brassicas
and onions when the weeds are at the seedling stage. Formulation types EC; GR .
ANALYSIS:
Product analysis is by hydrolysis with acid, distillation of the m-toluidine released which
is measured by titration. Residues may be determined by colorimetry of a derivative of
m-toluidine, which has been formed by hydrolysis.
Oral Acute oral LD
50
for ratsc. 2200 mg/kg. Toxicity Class WHO (a.i.) O
ENVIRONMENTAL FATE:
Soil/Environment Persists in soilc. 50 d at 15 C.
methocrotophos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name methocrotophos (BSI, E-ISO); m(tocrotophos) ((m) F-ISO)
IUPAC name (E)-2-(N-methoxy-N-methylcarbamoyl)-1-methylvinyl dimethyl phosphate;
3-dimethoxyphosphinoyloxy-N-methoxy-N-methylisocrotonamide
Chemical Abstracts name (E)-3-(methoxymethylamino)-1-methyl-3-oxo-1-
propenyl dimethyl phosphate CAS RN [25601847] Development codes C 2307
Smiles code COCNC(=O)C=C(C)OP(=O)(OC)OC
8
H
16
NO
6
P
370
methoprotryne
COMMERCIALISATION:
History Insecticide evaluated by Ciba AG (later Ciba-Geigy AG).
APPLICATIONS:
methometon
Herbicide
NOMENCLATURE:
Common name methometon (BSI, E-ISO); m(tom) ((m) F-ISO)
IUPAC name 6-methoxy-N
2
,N4-bis(3-methoxypropyl)-1,3,5-triazine-2,4-diamine
Chemical Abstracts name 6-methoxy-N,N-bis(3-methoxypropyl)-1,3,5-
triazine-2,4-diamine CAS RN [1771079] Development codes G 34 690
Smiles code COCCCNc1nc(NCCCOC)nc(OC)n1
12
H
23
N
5
O
3
COMMERCIALISATION:
methoprotryne
Herbicide
NOMENCLATURE:
Common name methoprotryn (WSSA); methoprotryne (BSI, E-ISO); m(toprotryne) ((f)
F-ISO)
IUPAC name N
2
-isopropyl-N4-(3-methoxypropyl)-6-methylthio-1,3,5-triazine-2,4-
diamine
Chemical Abstracts name N-(3-methoxypropyl)-N-(1-methylethyl)-6-(methylthio)-
1,3,5-triazine-2,4-diamine CAS RN [841065] Development codes G 36 393
Smiles code COCCCNc1nc(NC(C)C)nc(SC)n1
11
H
21
N
5
OS Form Colourless powder.
M.p. 6870 C V.p. 0.038 mPa (20 C) Henry 3.22 10
5
Pa m
3
mol
1
1.186 (20 C) Solubility In water 320 mg/l (20 C). In acetone 450, dichloromethane 650,
hexane 5, methanol 400, octanol 150, toluene 380 (all in g/l, 20 C). Stability Hydrolysed
N N
N
NH(CH
2
)
3
OCH
3
CH
3
S NHCH(CH
3
)
2
methoprotryne 371
in aqueous alkaline and acidic media to the inactive 2-hydroxytriazine. pKa Basic, 4.0
(21 C)
COMMERCIALISATION:
History Herbicide reported by A. Gast et al. (Z. Pfanzenkr. Pfanzenpathol. Pfanzenschutz,
1965, 72, 325). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents BE 584306;
GB 927348
APPLICATIONS:
site. Mode of action Selective herbicide, absorbed by the leaves and roots. Uses Selective
post-emergence control of annual broad-leaved weeds and grasses in winter-sown cereals
at 1.52.0 kg/ha. Formulation types WP.
PRODUCTS:
Discontinued products Gesaran* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc (CIPAC Handbook, 1983, 1B, 1864; 1980, 1A, 1302). Residues
determined by glc (K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192).
Oral Acute oral LD
50
for rats >5000, mice 2400 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats >150 mg/kg. Not a skin irritant (rats). NOEL (90 d) for rats 3750 mg a.i./kg
diet (c 250 mg a.i./kg daily); for dogs 11 250 mg/kg diet (c. 375 mg/kg daily).
ECOTOXICOLOGY:
Fish LC
50
(96 h) for bluegill sunfsh 9.8, rainbow trout 8, and crucian carp 31 mg/l.
Bees Non-toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, the thiomethyl group is replaced by hydroxyl, presumably after oxidation
of the sulfur to sulfoxide and sulfone. Demethylation of the amino groups at C4 and C6
occurs, with cleavage of the amine moieties and their replacement by hydroxyl, presumably
followed by ring opening. Soil/Environment In soil, the thiomethyl group is replaced by
hydroxyl, presumably after oxidation of the sulfur to sulfoxide and sulfone. Demethylation
of the amino groups at C4 and C6 occurs, with cleavage of the amine moieties and their
replacement by hydroxyl, presumably followed by ring opening.
372
methoxychlor
methoquin-butyl
Insecticide
NOMENCLATURE:
Common name m(thoquine-butyl) ((m) F-ISO); methoquin-butyl (BSI, E-ISO)
IUPAC name butyl 3-methylquinoline-4-carboxylate
Chemical Abstracts name butyl 3-methyl-4-quinolinecarboxylate Other names BMC
CAS RN [19764433] Smiles code CCCCOC(=O)c1c(C)cnc2ccccc12
15
H
17
NO
2
COMMERCIALISATION:
methoxychlor
Insecticide
IRAC 3B
NOMENCLATURE:
Common name methoxychlor (BSI, E-ISO, ESA, JMAF); m(thoxychlore) ((m) F-ISO)
IUPAC name 1,1,1-trichloro-2,2-bis(4-methoxyphenyl)ethane
Chemical Abstracts name 1,1-(2,2,2-trichloroethylidene)bis[4-methoxybenzene]
Other names DMDT CAS RN [72435] Offcial codes OMS 466; ENT 1716
Smiles code COc1ccc(cc1)C(c2ccc(OC)cc2)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade contains 88% methoxychlor and 12% related isomers.
Mol. wt. 345.7 M.f. C
16
H
15
Cl
3
O
2
Form Colourless crystals; (tech., grey powder).
M.p. 89 C; (tech., 77 C) V.p. Very low S.g./density 1.41 (25 C) Solubility In water
0.1 mg/l (25 C). Readily soluble in aromatic, chlorinated and ketonic solvents, and
vegetable oils. In chloroform and xylene 440, methanol 50 (all in g/kg, 22 C).
Stability Stable to oxidising agents and to uv irradiation. Reacts with alkalis, especially in
the presence of catalytically-active metals, with loss of hydrogen chloride, but more slowly
than DDT. Colour turns to pink or tan on exposure to light.
COMMERCIALISATION:
History Insecticide reported by P. Luger et al. (Helv. Chim. Acta, 1944, 27, 892). Introduced
by J. R. Geigy AG (now Syngenta AG) and by E. I. du Pont de Nemours & Co. (neither
company now manufactures or markets it). Patents CH 226180; GB 547871 (to Ciba-
Geigy); US 2420928; US 2477655; GB 624561 (to DuPont)
CH
3
O CH
CCl
3
OCH
3
methoxychlor 373
APPLICATIONS:
Biochemistry Acts on the nervous system of insects and disturbs the function of
neurons by interaction with the sodium channel. Mode of action Insecticide with contact
and stomach action. Uses Control of a wide range of insect pests (particularly chewing
insects) in feld crops, forage crops, fruit, vines, fowers, vegetables, and in forestry. Used
also for control of insect pests in animal houses, dairies, and in household and industrial
premises. Formulation types AE; DP; EC; GR; WP. Compatibility Incompatible with
highly alkaline materials.
PRODUCTS:
Discontinued products Marlate* (Kincaid); Sixanol* (Quinta).
ANALYSIS:
Product analysis by total chlorine content (H. L. Pease, J. Assoc. Off. Anal. Chem., 1976, 58, 40).
Residues determined by glc, tlc or paper chromatography (AOAC Methods, 18th Ed., 970.52;
J. Solomon & W. L. Lockhart, J. Assoc. Off. Anal. Chem., 1978, 60, 690; Anal. Methods Pestic.
Plant Growth Regul., 1972, 6, 441) or colorimetrically (AOAC Methods, 18th Ed., 954.09; ibid.
10th Ed., 24.14824.152). See also Pestic. Anal. Man., I, 208, 303, 304, 502; ibid., II, 180.120. In
drinking water by glc with ECD (AOAC Methods, 18th Ed., 990.06).
JMPR Evaln. 29 (1977). PDS 28 (1977). ICSC.306 (1999). IARC 20 (1979).
IARC Class 3
Oral Acute oral LD
50
50

for rabbits >2000 mg/kg. Not a skin irritant. NOEL In 1 y feeding trials, no toxic effect
observed in dogs receiving 300 mg/kg daily; in 2 y trials in rats, no effect at 200 mg/kg diet,
but some reduction in growth occurred at 1600 mg/kg diet. ADI/RfD (JMPR) 0.1 mg/kg
b.w. [1977]; (EPA) cRfD 0.005 mg/kg b.w. [1991]. Water GV 0.02 mg/l
Toxicity Class WHO (a.i.) U.
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(8 d) for bobwhite
quail and ring-necked pheasants >5000 mg/kg diet. Fish LC
50
0.052, bluegill sunfsh 0.067 mg/l. Daphnia LC
50
(48 h) 0.00078 mg/l.
ENVIRONMENTAL FATE:
Animals Degradation in animals is principally by O-dealkylation to the corresponding
phenol and diphenol, and by dehydrochlorination to 4,4-dihydroxybenzophenone (K. S.
Kapoor, J. Agric. Food Chem., 1970, 18, 11451152; J. Pestic. Sci., 1989, 14, 85; M. D. Corbett et
al., Chem. Res. Toxicol., 1990, 3, 8). Soil/Environment DT
50
in waterc. 46 d.
374
2-methoxyethylmercury silicate
2-methoxyethylmercury acetate
Fungicide
NOMENCLATURE:
IUPAC name 2-methoxyethylmercury acetate
Chemical Abstracts name (acetato-O)(2-methoxyethyl)mercury CAS RN [151382]
EC no 2057902 Smiles code COCC[Hg]OC(=O)C
5
H
10
HgO
3
COMMERCIALISATION:
History Fungicide introduced by Kenogard VT AB.
APPLICATIONS: Uses A fungicide used to protect seeds of cereals, cotton, fax, oilseed
rape and sugar beet from infection by Alternaria, Botrytis, Drechslera, Fusarium, Phoma,
Pythium, Rhizoctonia, Septoria and Tilletia spp. and Ustilago hordei. Formulation types LS .
PRODUCTS:
Discontinued products Panogen* (Kenogard AB).
ANALYSIS:
Product analysis by titration (AOAC Methods, 18th Ed., 971.04) or gravimetrically (ibid.,
973.11).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds. JMPR Evaln.
9 (1967) EU Status (1107/2009) Alkoxyalkyl mercury compounds considered to be
outside the scope of the Directive; already banned, 79/117/EEC.
IARC Class Methylmercury compounds are classifed 2B
2-methoxyethylmercury silicate
Fungicide
NOMENCLATURE:
IUPAC name The compound is an organomercury silicate but there is some doubt about
whether it is an orthosilicate or a metasilicate and therefore about its true molecular
structure
Chemical Abstracts name hydrogen [metasilicato(2)-O](2-methoxyethyl)
mercurate(1) CAS RN [64491925]
PHYSICAL CHEMISTRY:
Form Colourless crystalline powder. V.p. 440 mPa (35 C) Solubility Practically insoluble
methoxyphenone 375
in water. Stability 2-Methoxyethylmercury salts are stable to alkali but are decomposed
by halogen acids (J. Chatt, Chem. Rev. 1951 48, 7).
COMMERCIALISATION:
History Fungicide introduced by I. G. Farbenindustrie AG (later Bayer AG).
APPLICATIONS: Uses In seed treatments, against various seed-borne diseases of
cereals. Formulation types DS .
PRODUCTS:
Discontinued products Ceresan Universal Dry Seed Treatment* (Bayer); Soprasan*
(Sopra).
ANALYSIS:
Product analysis by titration (CIPAC Handbook, 1970, 1, 503; AOAC Methods, 18th Ed., 971.04)
or gravimetry (ibid., 973.11).
JMPR Evaln. 9 (1967)
Oral Acute oral LD
50
for rats 1140 mg formulated product/kg. Toxicity Class WHO (a.i.)
IIIPIC Not specifcally listed in the relevant DGD, but all mercury compounds are included
in the PIC procedure.
methoxyphenone
Herbicide
NOMENCLATURE:
Common name methoxyphenone (JMAF)
IUPAC name 4-methoxy-3,3-dimethylbenzophenone
Chemical Abstracts name (4-methoxy-3-methylphenyl)(3-methylphenyl)
methanone CAS RN [41295287] Development codes NK-049 (Nippon Kayaku)
Smiles code COc1ccc(cc1C)C(=O)c2cccc(C)c2
PHYSICAL CHEMISTRY:
Mol. wt. 240.3 M.f. C
16
H
16
O
2
Form Colourless crystals. M.p. 62.062.5 C
Solubility In water 2 mg/l (20 C). Soluble in most organic solvents. Stability Stable
under acid and alkaline conditions, but slowly decomposed by sunlight.
COMMERCIALISATION:
History Herbicide reported (Proc. Asian-Pacifc Weed Sci. Soc. Conf., 4th, 1973, p. 215).
Introduced by Nippon Kayaku Co., Ltd. Patents JP 51005446; GB 1355926; US 3873304
APPLICATIONS:
Biochemistry Inhibits photosynthesis. Mode of action Selective herbicide, inducing
chlorosis. Uses A selective pre-em. herbicide effective against annual grasses and broad-
leaved weeds in paddy rice and vegetable crops at 35 kg/ha; also used in rice pre-em. in
376
2-methyl(prop-2-ynyl)aminophenyl methylcarbamate
combination with bensulide, at 3050 kg granules/ha. Formulation types WP.
PRODUCTS:
Discontinued products Kayametone* (Nippon Kayaku).
ANALYSIS:
Oral Acute oral LD
50
for rats and mice >4000 mg/kg. NOEL (90 d) for rats 1500 mg/kg
diet, for mice 1000 mg/kg diet. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
Soil/Environment It is biodegradable, leaving no residue problems.
4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate
Chemical Abstracts name 3,5-dimethyl-4-(methyl-2-propynylamino)phenyl
methylcarbamate CAS RN [23623496] Development codes C 20 132
Smiles code CNC(=O)Oc1cc(C)c(N(C)CC#C)c(C)c1
14
H
18
N
2
O
2
COMMERCIALISATION:
APPLICATIONS:
insecticide.
Oral Acute oral LD
50
for rats 30 mg/kg.
2-methyl(prop-2-ynyl)aminophenyl methylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate
Chemical Abstracts name 2-(methyl-2-propynylamino)phenyl methylcarbamate
CAS RN [23504076] Development codes C 17 018
Smiles code CNC(=O)Oc1ccccc1N(C)CC#C
12
H
14
N
2
O
2
methylarsenic sulfde 377
COMMERCIALISATION:
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Contact insecticide.
Oral Acute oral LD
50
for rats 60 mg/kg.
5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid
Fungicide, herbicide, nematicide
NOMENCLATURE:
IUPAC name 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid; tetrahydro-5-methyl-6-
thioxo-2H-1,3,5-thiadiazin-3-ylacetic acid
Chemical Abstracts name dihydro-5-methyl-6-thioxo-2H-1,3,5-thiadiazine-
3(4H)-acetic acid Other names thiadiazinthion CAS RN [3655887]
Smiles code CN1CN(CC(=O)O)CSC1=S
6
H
10
N
2
O
2
S
2
COMMERCIALISATION:
History Nematicide introduced by Bayer AG.
PRODUCTS:
Discontinued products Terracur* (Bayer).
methylarsenic sulfde
Fungicide
NOMENCLATURE:
IUPAC name methylarsenic sulfde
Chemical Abstracts name methylthioxoarsine Other names MAS
CAS RN [2533826] Smiles code C[As]=S
PHYSICAL CHEMISTRY: Mol. wt. 122.0 M.f. CH
3
AsS Form Colourless fakes with
an unpleasant odour. M.p. 110 C Solubility Practically insoluble in water. Readily soluble
in carbon disulfde; less soluble in chlorinated hydrocarbons, DMF, diethyl ether, ethanol,
pyridine.
COMMERCIALISATION:
History Fungicidal properties of this chemical, which was reported in 1858 (von Bayer,
Ann. Chem. Pharm., 1858, 107, 279), described in 1931. Introduced by Bayer AG (1958).
Patents DE 1079886
APPLICATIONS: Uses Used as a seed or soil treatment to control Rhizoctonia solani
and other soil fungi.
378
methyldymron
PRODUCTS:
Discontinued products Rhizoctol* (Bayer); Urbasulf * (Bayer);
Discontinued mixtures Rhizoctol combi* (+ benquinox) (Bayer); Rhizoctol slurry*
(+ benquinox) (Bayer).
ANALYSIS:
Product analysis is by conversion to arsine which was measured by titration with bromine.
Residues may be determined by a colorimetric method after conversion to arsenate (H.
Frehse & H.Tietz, J. Agric. Food Chem., 1959, 7, 553).
Oral Acute oral LD
50
50
for
rabbits 1400 mg/kg. Skin irritation occurred to 6 persons after a 4-h exposure of a
moistened formulation (equivalent to 48 g arsenic/kg). ECClassifcation Not specifed,
but arsenic compounds in general (with exceptions) are assigned T; R23/25| N; R50, R53|
concn. dep.
methyldymron
Herbicide
HRAC Z
NOMENCLATURE:
Common name methyldymron (JMAF)
IUPAC name 1-methyl-3-(1-methyl-1-phenylethyl)-1-phenylurea; 3-(,-dimethylbenzyl)-
1-methyl-1-phenylurea
Chemical Abstracts name N-methyl-N-(1-methyl-1-phenylethyl)-N-phenylurea
CAS RN [42609734] Development codes K-1441; SK-41 (SDS Biotech KK)
Smiles code CN(C(=O)NC(C)(C)c1ccccc1)c2ccccc2
17
H
20
N
2
O Form Colourless, odourless
crystals. M.p. 72 C K
ow
logP = 3.01 S.g./density 1.11.2 Solubility In water 120 mg/l
(20 C). In acetone 913, hexane 8.2, methanol 637 (all in g/l, 20 C).
Stability Stable to heat and uv light.
COMMERCIALISATION:
History Herbicide reported by T. Takematsu et al. (Proc. 5th Asian-Pacifc Weed Sci. Soc.
Conf., 1975, 121). Introduced in Japan (1978) by Showa Denko (agrochemical interests
later SDS Biotech K.K.). Patents JP 7242493
NHCON
CH
3
C
CH
3
CH
3
methyl isothiocyanate 379
APPLICATIONS:
Biochemistry Cell division inhibitor. Mode of action Selective herbicide, absorbed
principally by the roots, with translocation to the meristem. Uses Pre- and early post-
emergence control of cyperaceous and some annual grass weeds in turf, at 210 kg/ha.
PRODUCTS:
Discontinued products Stacker* (SDS Biotech K.K.).
ANALYSIS:
Product and residue analysis by glc and hplc; details available from SDS Biotech.
Oral Acute oral LD
50
for male mice 5000, female mice 5269, male rats 5852, female rats
50
Inhalation LC
50
(14 d) for rats >4.85 mg/l. NOEL (90 d) for male rats 26.4, female rats
25.6 mg/kg diet. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp 14 mg/l. Daphnia LC
50
(3 h) for D. pulex >40 ppm.
ENVIRONMENTAL FATE:
Plants Rapidly metabolised in plants.
methyl isothiocyanate
Fungicide, herbicide, insecticide, nematicide
NOMENCLATURE:
Common name isothiocyanate de m(thyle) (F-ISO, accepted in lieu of a common
name); methyl isothiocyanate (BSI, E-ISO, JMAF, accepted in lieu of a common name)
IUPAC name methyl isothiocyanate
Chemical Abstracts name isothiocyanatomethane Other names MIT; MITC
CAS RN [556616] EC no 2091325 Smiles code CN=C=S
PHYSICAL CHEMISTRY:
Composition Tech. is 94.5% pure. Mol. wt. 73.1 M.f. C
2
H
3
NS Form Colourless
crystals, with a horseradish-like odour. M.p. 3536 C; (tech., 25.327.6 C)
B.p. 118119 C V.p. 2.13 kPa (25 C) K
ow
logP = 1.37 (calc.) S.g./density 1.069 (37 C);
(tech., 1.0537 (40 C)) Solubility In water 8.2 g/l (20 C). Readily soluble in common
organic solvents, such as ethanol, methanol, acetone, cyclohexanone, dichloromethane,
chloroform, carbon tetrachloride, benzene, xylene, petroleum ether and mineral oils.
Stability Unstable and reactive. Rapidly hydrolysed by alkalis, more slowly in acidic and
neutral solutions, DT
50
85 h (pH 5), 490 h (pH 7), 110 h (pH 9) (25 C). Sensitive to oxygen
and to light. Stable up to 200 C. pKa 12.3 F.p. 26.9 C
CH
3
NCS
380
methyl isothiocyanate
COMMERCIALISATION:
History Nematicidal activity reported by E. A. Pieroh et al. (Anz. Schdlingsskd., 1959, 32,
183). Introduced by Schering AG (now Bayer AG). Patents US 3113908
Manufacturers Bayer CropScience
APPLICATIONS: Uses Multi-purpose soil fumigant for control of nematodes, soil fungi,
soil insects, and weed seeds. Phytotoxicity Phytotoxic to all green plants.
PRODUCTS:
Discontinued products Trapex* (Aventis); Trapexide* (Aventis).
ANALYSIS:
Product analysis by glc or by hplc. Residues determined by glc with FPD (M. Ottnad et
al., Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 563). Details available from Bayer
CropScience.
Oral Acute oral LD
50
percutaneous LD
50
for rats 2780, male mice 1870, rabbits 263 mg/kg. Strongly irritating to
eyes and skin (rabbits). Inhalation LC
50
(1 h) for rats 1.9 mg/l air. NOEL (2 y) for rats
10 mg/l drinking water (0.370.56 mg/kg b.w. daily); (2 y) for mice 20 mg/l drinking water
(3.48 mg/kg b.w. daily); (1 y) for dogs 0.4 mg/kg b.w.. daily (by gavage). ADI/RfD (BfR)
0.004 mg/kg b.w. [2005]. Other Not carcinogenic. Toxicity Class WHO (a.i.) II.
ECClassifcation T; R23/25| C; R34| R43| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks 136 mg/kg. Dietary LC
50
10 936, pheasants >5000 mg/kg diet. Fish LC
50
(96 h) for bluegill sunfsh 0.14, rainbow
trout 0.09, mirror carp 0.370.57 mg/l. Daphnia LC
50
(48 h) 0.055mg/l. Algae EC
50
(96 h)
0.248 mg/l; NOEC (96 h) 0.125 mg/l. Bees Not hazardous to bees when used as directed.
ENVIRONMENTAL FATE:
Soil/Environment In damp soil, degradation and evaporation of the bulk of the substance
occurs within 3 weeks at 1820 C soil temperature, 4 weeks at 612 C, and 8 weeks at
06 C. At the lower temperatures, leaching is more signifcant and is dependent on soil
moisture. The potential for groundwater contamination is small, due to low leaching and
fast degradation.
3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate 381
methylmercury dicyandiamide
Fungicide
NOMENCLATURE:
Common name methylmercury dicyandiamide (BSI, accepted in lieu of a common
name.)
IUPAC name 1-cyano-3-(methylmercurio)guanidine; (methylmercurio)
guanidinocarbonitrile
Chemical Abstracts name (cyanoguanidinato-N)methylmercury CAS RN [502396]
Smiles code C[Hg]NC(=N)NC#N
3
H
6
HgN
4
COMMERCIALISATION:
History Fungicide introduced in Sweden in 1938, and in USA by Panogen Inc.
PRODUCTS:
Discontinued products Panogen* (Panogen).
IARC Class methylmercury compounds are classifed 2B.
Toxicity Class WHO (a.i.) OECClassifcation Not specifed, but organic mercury
generally is assigned T+; R26/27/28| R33| N; R50, R53 (concentration-dependent). PIC Yes.
3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate
Insecticide
NOMENCLATURE:
IUPAC name 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate
Chemical Abstracts name 3-methyl-1-phenyl-1H-pyrazol-5-yl dimethylcarbamate
Smiles code CN(C)C(=O)Oc1cc(C)nn1c2ccccc2
13
H
15
N
3
O
2
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Pyrolan* (Ciba-Geigy).
382
metobenzuron
metobenzuron
Herbicide
NOMENCLATURE:
Common name m(tobenzuron) ((m) F-ISO); metobenzuron (BSI, E-ISO)
IUPAC name ()-1-methoxy-3-[4-(2-methoxy-2,4,4-trimethylchroman-7-yloxy)phenyl]-1-
methylurea
Chemical Abstracts name ()-N-[4-[(3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-
1-benzopyran-7-yl)oxy]phenyl]-N-methoxy-N-methylurea CAS RN [111578326]
Development codes UMP-488 (Mitsui Petrochemical)
Smiles code CON(C)C(=O)Nc1ccc(Oc2ccc3c(OC(C)(CC3(C)C)OC)c2)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 400.5 M.f. C
22
H
28
N
2
O
5
Form White powder. M.p. 101.0102.5 C
Solubility In water 0.4 mg/l (25 C).
COMMERCIALISATION:
History Reported by T. Morimoto et al. (Proc. Br. Crop Prot. Conf. Weeds, 1993, 1, 67).
Introduced by Mitsui Petrochemical Industries Ltd (became Mitsui Chemicals Inc.).
APPLICATIONS:
Biochemistry Inhibitor of photosynthesis. Uses Selective post-emergence herbicide for
control of a wide range of broad-leaved weeds, including triazine-resistant weeds, in maize.
Application rates 125250 g/ha.
Compatibility Combination with 2,4-D increases effcacy and widens the weed spectrum.
Oral Acute oral LD
50
LD
50
for rabbits >2000 mg/kg. Non-irritating to skin and slightly irritating to eyes (rabbits).
NOEL (2 y) for rats 75 ppm (4.4 mg/kg b.w.) (EPA Tracking). ADI/RfD (EPA) 0.04 mg/kg
b.w. [1993]. Other Non-mutagenic in the Ames Test.
ENVIRONMENTAL FATE:
Soil/Environment DT
50
in soil 4 h (under irradiation), 8 h (in the dark). Low mobility in
sandy loam soil.
NHCON
CH
3
OCH
3
O
CH
3
CH
3
CH
3
CH
3
O
O
metolcarb 383
metolcarb
Insecticide
IRAC 1A; carbamate
NOMENCLATURE:
Common name metolcarb (BSI, E-ISO); m(tolcarb) ((m) F-ISO); MTMC (JMAF)
IUPAC name m-tolyl methylcarbamate
Chemical Abstracts name 3-methylphenyl methylcarbamate CAS RN [1129415]
EC no 2144460 Development codes C-3 (Nihon Nohyaku)
Smiles code CNC(=O)Oc1cccc(C)c1
9
H
11
NO
2
Form Tech. is a colourless
solid. M.p. 7677 C; 7475 C (tech.) V.p. 145 mPa (20 C) Solubility In water 2.6 g/l
(30 C). Soluble in polar organic solvents e.g. in cyclohexanone 790, xylene 100 (both in g/
kg, 30 C), methanol 880 g/kg (room temperature). Sparingly soluble in non-polar solvents.
COMMERCIALISATION:
History Insecticide introduced by Nihon Nohyaku Co., Ltd and by Sumitomo Chemical
Co., Ltd.
Manufacturers Hunan Haili; Saeryung
APPLICATIONS:
contact and respiratory action. Uses Control of planthoppers, leafhoppers, and
other sucking insects on rice. Also used for control of citrus mealybugs, onion thrips,
Mediterranean fruit fies, pink bollWorms and cotton aphids. Formulation types DP; EC;
MG; WP. Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Metacrate* (Sumitomo Chemical); Tsumacide* (Nihon
Nohyaku); Discontinued mixtures Ofunack M* (+ pyridaphenthion) (Mitsui Chemicals
Agro).
ANALYSIS:
Product analysis by glc or by hplc (S. Sakaue et al., Nippon Nogei Kagaku Kaishi, 1981, 55,
1237). Residues determined by glc of a derivative with ECD (J. Miyamoto et al., Nihon
Noyaku Gakkaishi, 1978, 3, 119).
CH
3
O
C
O
NHCH
3
384
metsulfovax
Oral Acute oral LD
50
for male rats 580, female rats 498, mice 109 mg/kg.
50
for rats >2000 mg/kg. Inhalation LC
50
for rats
0.475 mg/l air. Toxicity Class WHO (a.i.) IIECClassifcation Xn; R22| N; R51, R53
ECOTOXICOLOGY:
Fish Low toxicity to fsh.
ENVIRONMENTAL FATE:
Animals Metabolism of carbamate insecticides is reviewed (M. Cool & C. K. Jankowski in
Insecticides).
metsulfovax
Fungicide
NOMENCLATURE:
Common name metsulfovax (BSI, ANSI, E-ISO, (m) F-ISO)
IUPAC name 2,4-dimethyl-1,3-thiazole-5-carboxanilide; 2,4-dimethylthiazole-5-
carboxanilide
Chemical Abstracts name 2,4-dimethyl-N-phenyl-5-thiazolecarboxamide
CAS RN [21452186] Development codes G696
Smiles code Cc1nc(C)c(s1)C(=O)Nc2ccccc2
12
H
12
N
2
OS Form Crystals.
M.p. 140142 C V.p. 0.0017 mPa (25 C) S.g./density 1.27 Solubility In water
342 mg/l. In hexane 0.32, methanol 171, toluene 12.9 (all in g/l). pKa 2.05
COMMERCIALISATION:
History Fungicide evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
Biochemistry Inhibitor of succinate dehydrogenase complex, in the respiratory electron
transport chain. Mode of action Systemic fungicide. Uses Control of Puccinia, Ustilago,
Rhizoctonia solani, Tilletia spp., and other Basidiomycetes in cereals, cotton, potatoes, and
ornamentals. Applied to foliage or as a seed treatment at 2080 g/100 kg seed or up to
1 kg/ha foliar application. Formulation types FS; SC. WS .
PRODUCTS:
Discontinued products Provax* (Uniroyal).
Oral Acute oral LD
50
50
for
rabbits >2000 mg/kg. Inhalation LC
50
(4 h) for rats >5.7 mg/l air. NOEL (2 y) for female
rats 50 mg/kg diet, for male rats 400 mg/kg diet. ADI/RfD (BfR) 0.025 mg/kg b.w. [1991].
mexacarbate 385
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks >5620 mg/kg diet. Fish LC
50
(96 h) for bluegill
sunfsh 34 mg/l. Daphnia LC
50
(48 h) >97 mg/l.
ENVIRONMENTAL FATE:
50
c. 7 d.
mexacarbate
NOMENCLATURE:
Common name mexacarbate (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name 4-dimethylamino-3,5-xylyl methylcarbamate
Chemical Abstracts name 4-(dimethylamino)-3,5-dimethylphenyl methylcarbamate
CAS RN [315184] EC no 2062493 Development codes Dowco 139
Smiles code CNC(=O)Oc1cc(C)c(N(C)C)c(C)c1
12
H
18
N
2
O
2
M.p. 85 C V.p. 1.33
10
4
mPa Solubility In water 1000 ppm (25 C). In xylene 5.1 10
4
, benzene 1.02 10
5
,
ethanol 1.16 10
5
, acetone 1.16 10
5
(all in ppm, 25 C).
COMMERCIALISATION:
History Insecticide introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
PRODUCTS:
Discontinued products Zectran* (DowElanco).
EHC 64 (1986; a review of carbamate pesticides in general). IARC 12 (1976).
IARC Class 3
Toxicity Class WHO (a.i.) OECClassifcation T+; R28| Xn; R21| N; R50, R53
386
milneb
MG 191
Herbicide safener
NOMENCLATURE:
IUPAC name 2-dichloromethyl-2-methyl-1,3-dioxolane
CAS RN [22052637] Development codes MG 191 Smiles code CC1(OCCO1)
C(Cl)Cl
5
H
8
Cl
2
O
2
B.p. 9192 C /4 kPa
K
ow
logP = 1.24 Solubility In water 9.75 g/l. Soluble in protic and aprotic organic solvents.
Stability Stable 24 w at 54 C; stable 40 w at 10 klux (25 C). Stable to hydrolysis at pH 4,
6 and 8.
COMMERCIALISATION:
History Reported by F. Dutka et al. (Proc. Br. Crop Prot. Conf. Weeds, 1987, 1, 7784).
Herbicide safener developed by Nitrokmia Ipartelepek.
APPLICATIONS:
Biochemistry Increases glutathione synthesis and glutathione-related enzyme activity
in protected plants. Mode of action Readily absorbed by maize roots and translocated.
Uses A safener for thiocarbamate herbicides.
Oral Acute oral LD
50
for male rats 465, female rats 492, male and female mice 653 mg/kg.
milneb
Fungicide
NOMENCLATURE:
Common name milneb (BSI, ANSI); thiadiazine (JMAF)
IUPAC name 4,4,6,6-tetramethyl-3,3-ethylenedi-1,3,5-thiadiazinane-2-thione
Chemical Abstracts name 3,3-(1,2-ethanediyl)bis[tetrahydro-4,6-dimethyl-2H-
1,3,5-thiadiazine-2-thione] CAS RN [3773497] Development codes Experimental
Fungicide 328 Smiles code CC1NC(C)N(CCN
2
C(C)NC(C)SC2=S)C(=S)S1
12
H
22
N
4
S
4
COMMERCIALISATION:
History Fungicide evaluated by E. I. du Pont de Nemours & Co.
PRODUCTS:
Discontinued products Banlate* (DuPont).
O O
CH
3
CHCl
2
mirex 387
mipafox
NOMENCLATURE:
Common name mipafox (BSI, E-ISO, (m) F-ISO)
IUPAC name N,N-diisopropylphosphorodiamidic fuoride
Chemical Abstracts name N,N-bis(1-methylethyl)phosphorodiamidic fuoride
CAS RN [371868] EC no 2067423 Development codes Pestox 15
Smiles code CC(C)NP(=O)(F)NC(C)C
6
H
16
FN
2
OP
COMMERCIALISATION:
History Insecticide and acaricide introduced by Pest Control Ltd (later Schering
Agrochemicals).
PRODUCTS:
Discontinued products Isopestox* (Schering).
Toxicity Class WHO (a.i.) OECClassifcation T+; R39/26/27/28
mirex
Insecticide
NOMENCLATURE:
Common name mirex (ESA)
IUPAC name dodecachloropentacyclo[5.3.0.02,6.03,9.04,8]
decane; perchloropentacyclo[5.3.0.02,6.03,9.04,8]decane;
dodecachloropentacyclo[5.2.1.02,6.03,9.05,8]decane
Chemical Abstracts name 1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-1,3,4-
metheno-1H-cyclobuta[cd]pentalene Other names perchlordcone
CAS RN [2385855] EC no 2191966 Development codes GC 1283 (Allied)
Smiles code ClC1(C2(Cl)C3(Cl)C4(Cl)C5(Cl)C1(Cl)C3(Cl)Cl)C5(Cl)C(Cl)(Cl)C24Cl
10
Cl
12
V.p. 0.1 mPa (Residue Reviews,
103, 1 (1988)) Solubility In water 7 10
5
ppm (22 C) (Residue Reviews, 103, 1 (1988)).
In dioxane 1.53 10
5
, benzene 1.22 10
5
, carbon tetrachloride 7.2 10
4
, methyl ethyl
ketone 5.6 10
4
(all in ppm, room temperature).
COMMERCIALISATION:
History Insecticide introduced by Allied Chemical Corp., Agricultural Div. (later Hopkins
Ltd).
APPLICATIONS:
Mode of action Ingested insecticide.
388
monalide
PRODUCTS:
Discontinued products Dechlorane* (Allied); Mirex* (Seppic).
ANALYSIS:
Residues determined by glc with ECD, tlc or paper chromatography (AOAC Methods, 18th
Ed., 977.19, 980.22, 970.52). See also Pestic. Anal. Man., I, 303.
EHC 44 (1984). HSG 39 (1990). IARC 20 (1979). EU Status (1107/2009) Considered
to be outside the scope of the Directive; already banned, 79/117/EEEC, as amended by
IARC Class 2B
NOEL NOAEL for rats 1 ppm (0.07 mg/kg b.w.) (EPA IRIS). ADI/RfD (EPA) cRfD 0.0002
mg/kg b.w. [1992]. Water GV Excluded from GV derivation (U). Toxicity Class WHO
(a.i.) OECClassifcation R40| R62, R63| R64| Xn; R21/22| N; R50, R53
MNFA
Acaricide
NOMENCLATURE:
Common name MNFA (JMAF)
IUPAC name 2-fuoro-N-methyl-N-1-naphthylacetamide
Chemical Abstracts name 2-fuoro-N-methyl-N-(1-naphthalenyl)acetamide
CAS RN [5903139] Development codes NA-26
Smiles code CN(C(=O)CF)c1cccc2ccccc12
13
H
12
FNO
COMMERCIALISATION:
History Acaricide introduced by Nippon Soda Co., Ltd.
PRODUCTS:
Discontinued products Nissol* (Nippon Soda).
monalide
Herbicide
NOMENCLATURE:
Common name monalide (BSI, E-ISO, (f) F-ISO)
IUPAC name 4-chloro-2,2-dimethylvaleranilide; 4-chloro-,-dimethylvaleranilide
Chemical Abstracts name N-(4-chlorophenyl)-2,2-dimethylpentanamide
CAS RN [7287367] Development codes Schering 35 830 (AgrEvo)
monisouron 389
Smiles code CCCC(C)(C)C(=O)Nc1ccc(Cl)cc1
13
H
18
ClNO Form Colourless crystals.
M.p. 8788 C V.p. 0.24 mPa (25 C) Henryc. 2.52 10
3
Pa m
3
mol
1
(calc.)
Solubility In water 22.8 mg/l (23 C). In cyclohexanonec. 500, xylene 100, petroleum
ether <10 (all in g/l, 23 C). Stability Stable to at least 50 C and to hydrolysis (room
temperature) at pH 7; DT
50
154 d (pH 5), 116 d (pH 8.95).
COMMERCIALISATION:
History Herbicide reported by F. Arndt (Z. Pfanzenkr. Pfanzenpathol. Pfanzenschutz, 1965,
Sonderheft III, p. 277). Introduced by Schering AG (later AgrEvo GmbH).
Patents GB 971819
APPLICATIONS:
Mode of action Selective, systemic herbicide, absorbed by the leaves and roots.
Uses Post-emergence control of broad-leaved weeds in umbelliferous crops, such as
carrots, parsley, celery, and dill at 4 kg /ha . Formulation types EC.
PRODUCTS:
Discontinued products Potablan* (AgrEvo).
ANALYSIS:
Product analysis by hplc. Residues determined by glc after hydrolysis to 4-chloroaniline and
bromination.
Oral Acute oral LD
50
for rats and mice >4000 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats and rabbits >800 mg a.i. (as EC)/kg. NOEL (28 d) for rats 150 mg/kg daily.
ECOTOXICOLOGY:
Fish LC
50
for guppies >100 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment In soil (laboratory conditions) DT
50
30 d (pH 4.85), 48 d (pH 5.2), 59
d (pH 10.8). Degradation is presumably by ring hydroxylation, degradation to the aniline
derivative, and ring opening. Duration of residual activity in soil isc. 68 weeks.
monisouron
Herbicide
NOMENCLATURE:
Common name monisouron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-methylurea; 1-(5-tert-butylisoxazol-3-yl)-
3-methylurea
390
monuron; monuron-TCA
Chemical Abstracts name N-[5-(1,1-dimethylethyl)-3-isoxazolyl]-N-methylurea
CAS RN [55807460] Development codes SSH-41
Smiles code CNC(=O)Nc1cc(on1)C(C)(C)C
9
H
15
N
3
O
2
COMMERCIALISATION:
History Herbicide introduced by Shionogi & Co., Ltd.
monuron; monuron-TCA
Herbicide
NOMENCLATURE:
Common name monuron (BSI, E-ISO, F-ISO, ANSI, WSSA); monuron-TCA (WSSA for
the trichloroacetate salt (ii)); chlorfenidim* (former exception, USSR); CMU (JMAF)
IUPAC name 3-(4-chlorophenyl)-1,1-dimethylurea (i); 3-(4-chlorophenyl)-1,1-
dimethyluronium trichloroacetate (ii)
Chemical Abstracts name N-(4-chlorophenyl)-N,N-dimethylurea (i); trichloroacetic
acid compound with N-(4-chlorophenyl)-N,N-dimethylurea (1:1) (ii); 3-(p-chlorophenyl)-
1,1-dimethylurea (i) CAS RN [150685] monuron (i); [140410] monuron-
TCA (ii) EC no 2057661 (i) Development codes GC-2996 (Allied) (for (ii))
Smiles code monuron:CN(C)C(=O)Nc1ccc(Cl)cc1
PHYSICAL CHEMISTRY: Mol. wt. 198.7; (monuron-TCA 362.0) M.f. C
9
H
11
ClN
2
O
(monuron); C11H
12
Cl4N
2
O3 (monuron-TCA) Form Monuron and monuron-TCA are
crystalline solids. M.p. 174175 C; (monuron-TCA 7881 C) V.p. 0.067 mPa (25 C)
(monuron) K
ow
logP = 1.46, 2.12 (Agchem. Desk Ref.) Henry 5.79 10
5
Pa m
3
mol
1

(25 C, calc.) S.g./density 1.27 (20 C) Solubility Monuron: In water 230 mg/l (25 C).
In acetone 52 g/kg (27 C); sparingly soluble in petroleum oils and in polar organic
solvents. Monuron-TCA: In water 918 mg/l (room temperature). In 1,2-dichloroethane
400, methanol 177, xylene 91 (all in g/kg, room temperature). Stability Decomposes at
185200 C; rate of hydrolysis at room temperature and pH 7 negligible, but increases at
elevated temperatures and under acidic or alkaline conditions.
COMMERCIALISATION:
History Herbicidal activity of monuron reported by H. C. Bucha & C. W. Todd (Science,
1951, 114, 493). Introduced by E. I. du Pont de Nemours & Co. and, as the trichloroacetate,
by Allied Chemical Corp., Agricultural Division (later Hopkins Agricultural Chemical Co.).
Patents US 2655445; GB 691403; GB 692589; US 2782112; US 2801911
Manufacturers Hermania
APPLICATIONS:
Biochemistry Photosynthesis inhibitor. Mode of action Total herbicide, absorbed via
the roots. Uses It was recommended at 1030 kg/ha for total weed control in non-crop
areas; 510 kg/ha for annual maintenance. Monuron-TCA was used at 1015 kg/ha for total
morfamquat dichloride; morfamquat 391
weed control of uncropped areas. Formulation types WP (monuron).
Compatibility Acidic in reaction and incompatible with alkaline materials.
PRODUCTS:
Discontinued products Telvar* ((i)) (DuPont); Urox* ((ii)) (Allied).
ANALYSIS:
Product analysis of monuron by hydrolysis and titration of the liberated amine
(CIPAC Handbook, 1980, 1A, 1310) and of monuron-TCA by i.r. spectrometry. Impurities
determined by tlc (ibid., 1994, F, 336). Residues of monuron determined by glc (Anal.
Methods Pestic. Plant Growth Regul., 1972, 6, 664) or by hplc.
IARC 53 (1991). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
IARC Class 3
Oral Monuron: Acute oral LD
50
for rats 3600 mg/kg. Monuron-TCA: Acute oral LD
50

for rats 23003700 mg (in corn oil)/kg. Skin and eye Application of monuron to intact
or abraded skin of guinea-pigs produced no irritation or sensitisation. Monuron-TCA is
irritating to skin and mucous membranes. NOEL for rats and dogs 250500 mg/kg diet
(M C. Hodge et al., AMA Arch. Ind. Health, 1958, 17, 45). Toxicity Class WHO (a.i.) U (also
for monuron-TCA)ECClassifcation R40| Xn; R22| N; R50, R53 (i): R40| Xi; R36/38| N;
R50, R53 (ii)
ENVIRONMENTAL FATE:
Soil/Environment Slowly decomposed in moist soils.
morfamquat dichloride; morfamquat
Herbicide
NOMENCLATURE:
Common name morfamquat (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,1-bis(3,5-dimethylmorpholinocarbonylmethyl)-4,4-bipyridinium
Chemical Abstracts name 1,1-bis[2-(3,5-dimethyl-4-morpholinyl)-2-oxoethyl]-
4,4-bipyridinium CAS RN [4636833] morfamquat dichloride EC no 2250628
morfamquat dichloride Development codes PP745
PHYSICAL CHEMISTRY:
Mol. wt. 468.6; (morfamquat dichloride 539.5) M.f. C
26
H
36
N
4
O
4
; (morfamquat dichloride
C26H36Cl
2
N4O4)
COMMERCIALISATION:
History Dichloride introduced as herbicide (H. M. Fox, Proc. Br. Weed Control Conf., 7th,
1964, 29; H. M. Fox & C. R. Beech, ibid., p. 108) by ICI Plant Protection Div. (later ICI
Agrochemicals).
392
mucochloric anhydride
APPLICATIONS:
Mode of action Systemic herbicide.
PRODUCTS:
Discontinued products Morfoxone* (ICI).
Toxicity Class WHO (a.i.) OECClassifcation Xn; R22| Xi; R36/37/38| R52, R53
(assigned to morfamquat and to its dichloride)
morphothion
IRAC 1B
NOMENCLATURE:
Common name morphothion (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name O,O-dimethyl S-morpholinocarbonylmethyl phosphorodithioate
Chemical Abstracts name O,O-dimethyl S-[2-(4-morpholinyl)-2-oxoethyl]
phosphorodithioate CAS RN [144412] EC no 2056280
Smiles code COP(=S)(OC)SCC(=O)N1CCOCC1
PHYSICAL CHEMISTRY:
Mol. wt. 285.3 M.f. C
8
H
16
NO
4
PS
2
COMMERCIALISATION:
History Systemic insecticide introduced by Sandoz AG.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide.
PRODUCTS:
Discontinued products Ekatin M* (Sandoz).
ECClassifcation T; R23/24/25| N; R50, R53
mucochloric anhydride
Fungicide
NOMENCLATURE:
IUPAC name 2,2,3,3-tetrachloro-4,4-oxydibut-2-en-4-olide; 5,5-oxybis(3,4-dichloro-
5H-furan-2-one) Chemical Abstracts name 5,5-oxybis[3,4-dichloro-2(5H)-furanone]
myclozolin 393
Other names mucochloric anhydride CAS RN [4412093]
Development codes GC 2466
Smiles code ClC1=C(Cl)C(=O)OC1OC2OC(=O)C(=C2Cl)Cl
8
H
2
Cl
4
O
5
COMMERCIALISATION:
History Fungicide reported by A. E. Rich (Plant Dis. Rep., 1960, 44, 306). Evaluated by Allied
Chemical Corp., Agrochemical Div. (later Hopkins Ltd).
myclozolin
Fungicide
NOMENCLATURE:
Common name myclozoline ((f) F-ISO); myclozolin (BSI, E-ISO)
IUPAC name (RS)-3-(3,5-dichlorophenyl)-5-methoxymethyl-5-methyl-1,3-oxazolidine-
2,4-dione
Chemical Abstracts name 3-(3,5-dichlorophenyl)-5-(methoxymethyl)-5-methyl-2,4-
oxazolidinedione CAS RN [54864618] Development codes BAS 436F (BASF)
Smiles code COCC1(C)OC(=O)N(C1=O)c2cc(Cl)cc(Cl)c2
12
H
11
Cl
2
NO
4
Form Colourless
crystalline solid. M.p. 111 C V.p. 0.059 mPa (20 C) Henry 2.68 10
3
Pa m
3
mol
1
(calc.)
Solubility In water 6.7 mg/kg (20 C). In chloroform 400, ethanol 20 (both g/kg, 20 C).
Stability Hydrolysed under alkaline conditions.
COMMERCIALISATION:
History Fungicide reported by E-H. Pommer & B. Zeeh (Meded. Fac. Landbouwwet. Rijksuniv.
Gent, 1982, 47, 935). Introduced by BASF AG. Patents DE 2324591
APPLICATIONS:
Mode of action Contact fungicide. Uses Diseases caused by Botrytis, monilia, sclerotinia
spp. are controlled on beans, cucumbers, grapes, groundnuts, lettuce, oilseed rape,
ornamentals, stone fruit, strawberries, sunfowers, tomatoes. Formulation types SC. WP.
ANALYSIS:
Product analysis is by glc with FID. Residues may be determined by glc with ECD.
Oral Acute oral LD
50
50
for
rats >2000 mg/kg. Toxicity Class WHO (a.i.) U
394
naphthalic anhydride
naphthalene
NOMENCLATURE:
Common name naphtal(ne) (F-ISO); naphthalene (BSI, E-ISO, accepted in lieu of a
common name)
IUPAC name naphthalene (I)
Chemical Abstracts name (I) CAS RN [91203] Smiles code c1ccc2ccccc2c1
10
H
8
Form Colourless faky crystals.
M.p. 80 C B.p. 218 C V.p. 6500 mPa (20 C) Henry 2.78 101 Pa m
3
mol
1
(calc.)
S.g./density 1.517 (15 C) Solubility In water 30 mg/l (room temperature). In benzene,
toluene 285, carbon tetrachloride, chloroform 500, ethanol, methanol 77 (all in g/l). Very
soluble in 1,2-dichloroethane, diethyl ether. F.p. 79 C (open cup), 88 C (closed cup)
COMMERCIALISATION:
History Has long been used as a household fumigant against clothes moths.
APPLICATIONS:
Mode of action Fumigant insecticide. Uses Its effectiveness as a household fumigant
against clothes moths has been questioned (W. S. Abbott & S. C. Billings, J. Econ. Entomol.,
1935, 28, 493). Has been used as a fumigant against soil fungi, but is rapidly decomposed by
soil micro-organisms.
ANALYSIS:
Product analysis by distillation from mixtures in the presence of ethanol and precipitation
as the picrate (D. S. Binnington & W. F. Giddes, Ind. Eng. Chem. Anal. Ed., 1934, 6, 461; W. L.
Millar, J. Assoc. Off. Agric. Chem., 1934, 17, 308).
ICSC.667 (2005). IARC 82 (2002). EU Status (1107/2009) Not approved, 2004/129/EC.
IARC Class 2B
Oral Acute oral LD
50
for rats 2200 mg/kg. NOEL NOAEL for rats 71 mg/kg daily (EPA
IRIS). ADI/RfD (EPA) aRfD 0.4 mg/kg b.w., cRfD 0.1 mg/kg b.w. [2008].
Toxicity Class WHO (a.i.) U; (WHO Recommended Classifcation gives O)
ECClassifcation R40| Xn; R22| N; R50, R53
naphthalic anhydride
Herbicide safener
NOMENCLATURE:
Common name naphthalic anhydride (draft E-ISO, is used in lieu of common name)
IUPAC name naphthalene-1,8-dicarboxylic anhydride
Chemical Abstracts name 1H,3H-naphtho[1,8-cd]pyran-1,3-dione CAS RN [81845]
naphthalic anhydride 395
Smiles code O=C1OC(=O)c2cccc3cccc1c23
PHYSICAL CHEMISTRY:
12
H
6
O
3
Form Light tan crystalline
solid. M.p. 270274 C Solubility Relatively insoluble in water and most non-polar
solvents; in DMF 13.9 g/l. Stability Stable under normal storage conditions; non-
hygroscopic.
COMMERCIALISATION:
History Enhancement of the selectivity of thiocarbamate herbicides to maize reported by
O. L. Hoffman (Weed Sci. Soc. Am., Abstr., 1969, No. 12) and reviewed by G. R. Stephenson
& F. Y. Chang (in Chem. Action Herbic. Antid., p. 35). Introduced by Gulf Oil Corp.
Patents US 3131509; US 3564768
APPLICATIONS:
55(11) 10431058). Uses Used as a seed coating, at 5 g/kg seed, prior to planting and
protects maize from damage by EPTC, vernolate and related thiocarbamate herbicides.
Germination of maize seed planted 2 y after treatment was not affected.
Formulation types TC.
PRODUCTS:
Discontinued products Protect* (Gulf).
ANALYSIS:
Residues in crops determined by glc with ECD (J. R. Riden, Anal. Methods Pestic. Plant Growth
Regul., 1976, 8, 483).
Oral Acute oral LD
50
for rats 12 300 mg/kg. Skin and eye Acute percutaneous LD
50
for
rabbits >2025 mg/kg. Moderate irritant to eyes of albino rabbits. Inhalation Inhalation
of the dust by rats for 4 h at 820 mg/m
3
air revealed no toxic symptom. NOEL In 90 d
feeding trials, no ill-effect noted for rats and dogs receiving 500 mg/kg diet.
396
naproanilide
naproanilide
Herbicide
HRAC K3 WSSA 15; alkanamide (acetamide)
NOMENCLATURE:
Common name naproanilide (JMAF)
IUPAC name 2-(2-naphthyloxy)-N-phenylpropionamide
Chemical Abstracts name 2-(2-naphthalenyloxy)-N-phenylpropanamide
CAS RN [52570168] unstated stereochemistry Development codes MT-101 (Mitsui
Toatsu) Smiles code CC(Oc1ccc2ccccc2c1)C(=O)Nc3ccccc3
19
H
17
NO
2
Form Whitish crystals.
M.p. 128 C V.p. 2.8 10
6
mPa (20 C) S.g./density 1.256 (25 C) Solubility In water
0.75 mg/l (27 C). In acetone 171, toluene 42, ethanol 17, benzene 46 (all in g/l, 27 C).
Stability Dilute aqueous solutions slowly degraded by uv light; solid stable to light.
F.p. 110 C
COMMERCIALISATION:
History Herbicide reported by S. Fujisawa (Jpn. Pestic. Inf., 1981, No. 39, p. 19). Introduced
by Mitsui Toatsu Chemicals, Inc. (later Mitsui Chemicals, Inc.).
APPLICATIONS:
Biochemistry The active principle is thought to be the corresponding carboxylic acid.
Mode of action Selective herbicide, absorbed through stems and roots. Uses Controls
annual and some perennial weeds, but not Echinochloa crus-galli, in paddy rice, at
23 kg/ha. Gives good control of young Sagittaria pygmaea. Phytotoxicity Phytotoxic to
direct seeding rice at high dosages. Formulation types GR .
PRODUCTS:
Discontinued products Uribest* (Mitsui Chemicals Agro).
ANALYSIS:
Product and residue analysis by hplc (Gotoh, J. Pestic. Sci., 1977, (4), p. 2).
Oral Acute oral LD
50
for rats >15 000, mice >20 000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >3000, mice >5000 mg/kg. Toxicity Class EPA (formulation) IV
ECOTOXICOLOGY:
Fish TLm (72 h) >100 ppm. Daphnia LC
50
(6 h) 40 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment DT
50
in soil 27 d.
CH C
NH
O
O
CH
3
naptalam 397
naptalam
Herbicide
HRAC P WSSA 19; phthalamate
NOMENCLATURE:
naptalam
Common name NPA (JMAF, for sodium salt); alanap* (former exception, Turkey);
naptalame ((m) F-ISO); naptalam (BSI, E-ISO, WSSA)
IUPAC name N-1-naphthylphthalamic acid
Chemical Abstracts name 2-[(1-naphthalenylamino)carbonyl]benzoic acid
CAS RN [132661] naptalam; [132672] naptalam-sodium EC no 2050734
(naptalam-sodium) Smiles code OC(=O)c1ccccc1C(=O)Nc2cccc3ccccc23
PHYSICAL CHEMISTRY:
naptalam Mol. wt. 291.3 (naptalam); 313.3 (naptalam-sodium) M.f. C
18
H
13
NO
3
; sodium
salt C18H
12
NNaO3 Form Crystalline solid. M.p. 185 C V.p. <133 Pa (20 C) K
ow
logP
= 0.104 (pH 5), 0.004 (pH 7), 0.036 (pH 9); logP = 0.006 (naptalam-sodium, Uniroyal,
via USDA ARS PPD) Henry <1.94 10
2
Pa m
3
mol
1
Solubility In water 200 mg/l (20 C). In acetone 5, DMF 39, DMSO 43, methyl ethyl
ketone 4, isopropanol 2, carbon tetrachloride 0.1 (all in g/kg). Practically insoluble in
benzene, hexane, and xylene. Sodium salt: In water 300 g/kg (20 C). In acetone 17, DMF
50, methyl ethyl ketone 6, isopropanol 21, benzene 0.5, xylene 0.4 (all in g/kg). Stability
Hydrolysis DT
50
7.1 d (pH 5), 2.4 y (pH 7), stable (pH 9) (all 20 C); a second study shows
DT
50
2.9 d (pH 5, 25 C). pKa 4.6
COMMERCIALISATION:
History Plant growth-regulating activity of N-arylphthalamic acids reported by O. L.
Hoffman & A. E. Smith (Science, 1949, 109, 588). Naptalam-sodium introduced by Uniroyal
Chemical Co., Inc. (became Chemtura Corp.) in 1955. Patents US 2556664; US 2556665
Manufacturers Chemtura
APPLICATIONS:
Biochemistry Inhibits indolylacetic acid transport. Mode of action Selective herbicide,
absorbed predominantly by the roots, but also, to some extent, by the foliage, with
accumulation in meristematic tissue. Inhibits seed germination. Uses Pre-emergence
control of many broad-leaved weeds and some grasses in cucurbits, asparagus, peanuts,
soya beans, and established woody ornamentals, at 2.05.5 kg/ha. Phytotoxicity
Phytotoxic to beet, tomatoes, spinach, and lettuce. Formulation types GR; SL; WP.
CO
2
H
C
NH
O
398
naptalam
Compatibility Incompatible with pesticides which may cause amine transfer or
replacement.
PRODUCTS:
naptalam
Discontinued products Aksol* (DuPont); Alanap* (sodium salt) (Chemtura);
Alanap-L* (sodium salt) (Chemtura); Naptro* (Crystal).
ANALYSIS:
Product analysis by uv spectrometry; details from Chemtura. Residues determined by
hydrolysis to 1-naphthylamine, a derivative of which is measured by colorimetry (A. E.
Smith & G. M. Stone, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 4, 1). See also
Pestic. Anal. Man., II, 180.297. In soil, by hplc/ELCD (Environ. Chem. Methods).
naptalam
Oral Acute oral LD
50
50
for
rabbits >5000 mg/kg. Severe eye irritant; mild skin irritant (rabbits). Inhalation LC
50
(4 h)
for rats >2.07 mg/l air. NOEL In chronic feeding trials, NOEL for rats 30, dogs 5 mg/kg
b.w. daily. ADI/RfD (EPA) cRfD 0.258 mg/kg b.w. [2004]. Other Not a bacterial mutagen.
Toxicity Class WHO (a.i.) U EPA (formulation) II (Alanap-L) ECClassifcation Xn; R22
ECOTOXICOLOGY:
naptalam
Birds LD
50
50
(8 d) for mallard ducks and
bobwhite quail >10 000 ppm. Fish LC
50
(96 h) for rainbow trout 76.1, bluegill sunfsh 354
ppm. Daphnia LC
50
(48 h) 118.5 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Plants In plants, naptalam rapidly breaks down into phthalic acid and 1-naphthylamine.
Soil/Environment Duration of residual activity isc. 38 w, depending on soil type
and moisture content (E. Smith et al., J. Agric. Food Chem., 1957, 5, 748). For sandy loam,
adsorption Kd 14.98, K
oc
2152.
natamycin 399
natamycin
Fungicide
NOMENCLATURE:
Common name natamycin (BAN); pimaricin (traditional name); tennecetin (traditional
name)
IUPAC name (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-
3,6-dideoxy--D-mannopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-
trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
Chemical Abstracts name [1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*
25R*,26S*)]-22-[(3-amino-3,6-dideoxy--D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-
methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-
carboxylic acid Other names myprozine CAS RN [7681938] EC no 2316835
Smiles code CC1OC(OC2CC3OC(O)(CC(O)C3C(=O)O)CC(O)CC4OC4C=CC(=O)
OC(C)CC=CC=CC=CC=C2)C(O)C(N)C1O
PHYSICAL CHEMISTRY:
Composition Exists as a trihydrate. Tech. is >87%. Mol. wt. 665.7 (anhydrous)
M.f. C
33
H
47
NO
13
Form White crystals. M.p. 280300 C (decomp.) Solubility In water
4.1 g/l (2022 C). In DMSO >200, methanol 97, ethanol 5.5, acetone 0.85, petroleum spirit
0.1, benzene 0.05 (all in g/l, 2022 C) (J. R. Marsh & P. J. Weiss, J. Assoc. Off. Anal. Chem., 1967,
50, 457). Stability Stable when dry, but sensitive to light. Forms water-soluble salts with
acids or alkalis.
COMMERCIALISATION:
Production By fermentation of Streptomyces natalensis and S. chattanoogensis.
History Structure established by B. T. Golding et al. (Tetrahedron Lett., 1966, p. 3551), W.
E. Meyer (Chem. Commun., 1968, p. 470) and G. Gaudiano et al. (Chem. Ind. (Milan), 1966,
48, 1327). Stereochemistry revised (J. M. Lancelin & J. M. Beau, J. Am. Chem. Soc., 1990, 112,
4060, 6749; A. J. Duplantier & S. Masamune, ibid., p. 7079). Introduced as a fungicide by
Gist-Brocades N.V. Patents GB 712547; GB 844289; US 3892850 Manufacturers Gist-
Brocades
O
O
O
HO
HO
O
OH
CO
2
H
CH
3
O O
HO
NH
2
OH
CH
3
400
NC-170
APPLICATIONS:
Uses Control of diseases of bulbs, especially basal rot (Fusarium oxysporum) of daffodils,
preferably combined with a hot-water treatment. Formulation types WP.
PRODUCTS:
Discontinued products Delvolan* (Gist-Brocades).
ANALYSIS:
Product analysis is either by bioassay with a suitable micro-organism, and confrmed by the
effect of the enzyme pimaricinase, or by uv spectrometry. Residues may be determined by
bioassay.
Oral Acute oral LD
50
for rats 27304670 mg/kg (G. J. Levinskas, Toxicol. Appl. Pharmacol.,
1966, 8, 97). Skin and eye No acute toxicity, even at high doses. Not a skin or eye irritant
(rabbits). Not a skin sensitiser. Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Fish Not toxic to fsh.
ENVIRONMENTAL FATE:
Readily biodegradable.
NC-170
Insecticide
NOMENCLATURE:
IUPAC name 4-chloro-5-(6-chloro-3-pyridylmethoxy)-2-(3,4-dichlorophenyl)pyridazin-
3(2H)-one
Chemical Abstracts name 4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-
dichlorophenyl)-3(2H)-pyridazinone CAS RN [107360349]
Development codes NC-170
Smiles code Clc1ccc(COc2cnn(c3ccc(Cl)c(Cl)c3)c(=O)c2Cl)cn1
16
H
9
Cl
4
N
3
O
2
M.p. 180181 C
COMMERCIALISATION:
History Insect growth regulator reported by T. Miyake et al. (Proc. 1988 Br. Crop Prot. Conf. -
Pests Dis., 2, 535). Evaluated by Nissan Chemical Industries Ltd.
APPLICATIONS: Uses Evaluated for control of hoppers in rice.
Oral Acute oral LD
50
LD
50
for rabbits >2000 mg/kg. Not irritating to skin or eyes (rabbits).
ECOTOXICOLOGY:
Daphnia LC
50
>1 mg/l.
NC-330 401
NC-196
Insecticide
NOMENCLATURE:
IUPAC name 2-benzyl-5-[2-(ethoxycarbonylamino)ethoxy]-pyridazin-3(2H)-one
Chemical Abstracts name ethyl [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]
oxy]ethyl]carbamate CAS RN [133456867] Development codes NC-196
16
H
19
N
3
O
4
M.p. 73.578.0 C
COMMERCIALISATION:
History Reported by T. Miyake et al. (Proc. Br. Crop Prot. Conf., Pests Dis. - 1994, 1, 59).
Manufacturers Nissan
APPLICATIONS:
Mode of action Juvenile hormone mimic, also with ovicidal properties. Active by contact
and as a soil drench. Uses Evaluated for control of Brown planthopper (Nilaparvata
lugens) and diamond-back moth (Plutella xylostella) in rice. Formulation types GR .
Oral Acute oral LD
50
50
for female rabbits >5000 mg/kg. Slight
eye irritant, not a skin irritant (rabbits). Other Negative in Ames, micronucleus and Rec
tests.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp and rainbow trout >40 mg/l. Daphnia LC
50
(48 h) >40 mg/l.
NC-330
Herbicide
NOMENCLATURE:
IUPAC name methyl 5-(4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl)-1-(2-pyridyl)
pyrazole-4-carboxylate
CAS RN [104770298] Development codes NC-330; NCI-851013 (both Nissan)
Smiles code COC(=O)c1cnn(c1S(=O)ONC(=O)Nc2nc(C)cc(C)n2)c3ccccn3
17
H
17
N
7
O
5
S Form Pale brownish solid.
M.p. 159160 C Solubility In water 849 mg/l (25 C).
SO
2
NHCONH
N
N
CH
3
CH
3
N
N
CO
2
Me
N
402
nickel bis(dimethyldithiocarbamate)
COMMERCIALISATION:
History Herbicide reported by T. Nawamaki et al. (Proc. Br. Crop Prot. Conf. Weeds, 1991, 1,
45). Developed by Nissan Chemical Industries Ltd.
Manufacturers Nissan
APPLICATIONS:
Biochemistry Branched chain amino acid synthesis (ALS or AHAS) inhibitor. Acts by
inhibiting biosynthesis of the essential amino acids valine and isoleucine, hence stopping
cell division and plant growth. Selectivity derives from rapid metabolism in the crop.
Metabolic basis of selectivity in sulfonylureas reviewed (M. K. Koeppe & H. M. Brown, Agro-
Food-Industry, 1995, 6, 914). Mode of action Systemic herbicide, absorbed mainly by
the foliage and translocated to meristem tissues. Uses Control of grass and broad-leaved
weeds post-emergence in winter wheat, at 100150 g/ha. Phytotoxicity Phytotoxic to
winter barley.
ANALYSIS:
Residues of sulfonylureas in soil and water may be determined by immunoassay (Environ.
Chem. Methods). Methods for sulfonylurea residues in crops, soil and water reviewed (A. C.
Barefoot et al., Proc. Br. Crop Prot. Conf. Weeds, 1995, 2, 707).
Oral Acute oral LD
50
for rats and mice >5000 mg/kg. Skin and eye Non-irritating to skin;
mild eye irritant (rabbits). Other Non-mutagenic in the Ames test.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp >5 mg/l.
nickel bis(dimethyldithiocarbamate)
NOMENCLATURE:
IUPAC name nickel bis(dimethyldithiocarbamate)
Chemical Abstracts name nickel dimethylcarbamodithioate Other names
organic nickel (JMAF) CAS RN [15521650] Development codes M-1; DDC-Ni
Smiles code [Ni+2].CN(C)C(=S)[S-].CN(C)C(=S)[S-]
PHYSICAL CHEMISTRY:
6
H
12
N
2
NiS
4
Form Green, amorphous
powder. M.p. Decomposes above 250 C Solubility Practically insoluble in water. In
(CH
3
)
2
N C
S
S
Ni
2
nifuridide 403
chloroform 287, DMF 560, tetrahydrofuran 475 (all in mg/l, 20 C). Stability Stable in
acidic and alkaline media at room temperature.
COMMERCIALISATION:
History Fungicide introduced by Mikasa Chemical Co. (who merged with Yashima
Chemical Industry Co. Ltd in 1996) and frst registered in Japan in 1968.
Manufacturers Yashima
APPLICATIONS:
Mode of action Foliar fungicide and bactericide with protective action. Uses Control of
bacterial leaf blight and bacterial grain rot in paddy rice, at 18002400 g/ha.
Formulation types DP; WP.
PRODUCTS:
Discontinued products Sankel* (Yashima).
EHC 78 (1988) is a general review of dithiocarbamates and their degradation products.
Oral Acute oral LD
50
for rats >36 000, mice >30 000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >5000 mg/kg. NOEL (2 y) for rats 200 mg/kg diet.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp 360 mg/l.
nifuridide
Insecticide
NOMENCLATURE:
Common name nifuridide (BSI, ANSI, E-ISO, (m) F-ISO)
IUPAC name 6-amino-,,,2,2,3,3-heptafuoro-5-nitropropion-m-toluidide
Chemical Abstracts name N-[2-amino-3-nitro-5-(trifuoromethyl)phenyl]-2,2,3,3-
tetrafuoropropanamide CAS RN [61444620] Development codes EL-468
Smiles code Nc1c(NC(=O)C(F)(F)C(F)F)cc(cc1[N+](=O)[O-])C(F)(F)F
10
H
6
F
7
N
3
O
3
COMMERCIALISATION:
History Insecticide evaluated by Eli Lilly & Co.
PRODUCTS:
Discontinued products Bant* (Lilly).
404
nithiazine
nipyraclofen
Herbicide
NOMENCLATURE:
Common name nipyraclof(ne) ((m) F-ISO); nipyraclofen (BSI, E-ISO)
IUPAC name 1-(2,6-dichloro-,,-trifuoro-p-tolyl)-4-nitropyrazol-5-ylamine
Chemical Abstracts name 1-[2,6-dichloro-4-(trifuoromethyl)phenyl]-4-nitro-1H-
pyrazol-5-ylamine CAS RN [99662110] Development codes SLA 3992 (Bayer)
Smiles code Nc1c(cnn1c2c(Cl)cc(cc2Cl)C(F)(F)F)[N+](=O)[O-]
10
H
5
Cl
2
F
3
N
4
O
2
COMMERCIALISATION:
History Herbicide discovered by Bayer AG.
APPLICATIONS:
nithiazine
Insecticide
IRAC 4A
NOMENCLATURE:
Common name nithiazine (BSI, E-ISO, (m) F-ISO, ANSI, not Japan)
IUPAC name 2-nitromethylene-1,3-thiazinane
Chemical Abstracts name tetrahydro-2-(nitromethylene)-2H-1,3-thiazine
CAS RN [58842209] Development codes IN-A0159 (DuPont); SD 35651 (Shell,
DuPont) Smiles code [O-][N+](=O)C=C1NCCCS1
5
H
8
N
2
O
2
S Solubility In water 200 g/l
(23 C).
COMMERCIALISATION:
History Insecticide reported by S. B. Soloway et al. (Pestic. Venom Toxici. (Selected Papers
Internat. Congr. Entomol., 15th, 1976), 1978, p. 153). Notable as original member of
nitromethylene group of insecticides. Evaluated originally by Shell Research Ltd, later E. I.
du Pont de Nemours & Co.
APPLICATIONS:
Biochemistry Agonist of the nicotinic acetylcholine receptor, affecting the synapses in the
insect central nervous system.
NH
S
NO
2
CH
nitralin 405
nitralin
Herbicide
NOMENCLATURE:
Common name nitralin (BSI, E-ISO, (m) F-ISO, WSSA, JMAF)
IUPAC name 4-methylsulfonyl-2,6-dinitro-N,N-dipropylaniline
Chemical Abstracts name 4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylbenzenamine
CAS RN [4726141] Development codes SD 11 831
Smiles code CCCN(CCC)c1c(cc(cc1[N+](=O)[O-])S(=O)(=O)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
13
H
19
N
3
O
6
S Form Tech. is a yellow
powder. M.p. 151152 C (tech.) V.p. 0.002 mPa (25 C) S.g./density 1.39 (20 C, tech.)
Solubility In water 0.6 mg/l (22 C). In acetone 360, DMSO 330, 2-nitropropane 250 (all
in g/l, 22 C); sparingly soluble in common hydrocarbon and aromatic solvents and alcohols.
Stability Contact of nitralin with concentrated bases, or temperatures >200 C, should
be avoided.
COMMERCIALISATION:
History Herbicide reported by J. B. Regan et al. (Proc. Northeast. Weed Control Conf.,
1966, p. 36). Introduced by Shell Research Ltd. Patents BE 672199
APPLICATIONS:
Mode of action Selective herbicide. Uses Used pre-em. to control annual grasses and
many broad-leaved weeds in cotton, groundnuts, rape, soya beans and transplanted crops
such as brassicas, tobacco, tomatoes at 0.50.75 kg/ha on light soils, 1.01.5 kg/ha on
heavier soils (<5% o.m.); not used in highly organic or peat soils. Formulation types WP.
PRODUCTS:
Discontinued products Planavin* (Shell).
ANALYSIS:
Product analysis by i.r. spectrometry or by glc (Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 625). Residues determined by glc with ECD (ibid.).
Oral Acute oral LD
50
LD
50
for rabbits >2000 mg/kg. NOEL (2 y) for rats and dogs 2000 mg/kg diet.
ENVIRONMENTAL FATE:
Soil/Environment Relatively immobile in soil; DT
50
c. 3050 d.
406
nitrilacarb; nitrilacarb 1:1 zinc chloride complex
nitrilacarb; nitrilacarb 1:1 zinc chloride complex
NOMENCLATURE:
Common name nitrilacarb (BSI, E-ISO, ANSI, ESA); nitrilacarbe ((m) F-ISO)
IUPAC name 4,4-dimethyl-5-(methylcarbamoyloxyimino)valeronitrile; 4,4-dimethyl-5-
(methylcarbamoyloxyimino)pentanenitrile
Chemical Abstracts name 4,4-dimethyl-5-[[[(methylamino)carbonyl]oxy]imino]
pentanenitrile CAS RN [29672193] nitrilacarb; [58270089] 1:1 complex with zinc
chloride, formerly [61332329] Development codes AC 82 258 (zinc complex); CL 72
613 (nitrilacarb)
PHYSICAL CHEMISTRY:
Mol. wt. 197.2; (zinc chloride complex 333.5)
M.f. C
9
H
15
N
3
O
2
; (zinc chloride complex C
9
H15Cl
2
N3O
2
Zn) Form The tech. zinc chloride
complex is an almost colourless powder. M.p. 120125 C (zinc chloride complex) S.g./
density 0.5 (zinc chloride complex) Solubility The zinc chloride complex is soluble in
water, acetone, acetonitrile, alcohols; slightly soluble in chloroform; practically insoluble in
benzene, diethyl ether, hexane, toluene, xylene. Stability The zinc chloride complex is very
hygroscopic; stable 1.5 y (25 C) when stored in original, unopened containers.
COMMERCIALISATION:
History Insecticide reported by W. K. Whitney & J. L. Aston (Proc. Br. Insectic. Fungic. Conf.,
8th, 1975, 2, 633). The 1:1 complex with zinc chloride introduced by American Cyanamid
Co. Patents US 3681505, US 3621049.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Nitrilacarb was used against a range of
phytophagous mites and aphids, also whitefies, thrips, leafhoppers at 2575 g/100 l, and
Leptinotarsa decemlineata, at 0.5 kg/ha.
PRODUCTS:
Discontinued products Accotril* (1:1 zinc chloride complex.) (Cyanamid); Cyanotril*
(Cyanamid).
ANALYSIS:
Residues are determined by glc.
nitrofen 407
nitrofen
Herbicide
NOMENCLATURE:
Common name NIP (JMAF); nitrofen (BSI, E-ISO, WSSA); nitrof(ne) ((m) F-ISO);
niclofen (Canada)
IUPAC name 2,4-dichlorophenyl 4-nitrophenyl ether
Chemical Abstracts name 2,4-dichloro-1-(4-nitrophenoxy)benzene
CAS RN [1836755] EC no 2174060 Development codes FW-925
Smiles code [O-][N+](=O)c1ccc(Oc2ccc(Cl)cc2Cl)cc1
12
H
7
Cl
2
NO
3
Form Crystalline solid.
M.p. 7071 C V.p. 1.06 mPa (40 C) Solubility In water 0.71.2 mg/l (22 C).
COMMERCIALISATION:
History Herbicide introduced by Rohm & Haas Co. Patents GB 974475; US 3080225
APPLICATIONS:
Mode of action Selective herbicide. Uses Toxic to a number of broad-leaved and
grass weeds, and effective when left as a thin layer on the soil surface; activity is rapidly
lost on incorporation in soil. It was used for weed control in cereals pre-em. at 2 kg/
ha. Many vegetable crops tolerate applications pre-em. 3 kg/ha and post-em. 1 kg/ha.
PRODUCTS:
Discontinued products Tok* (Rohm & Haas); Tokkorn* (Rohm & Haas).
ANALYSIS:
Product analysis by glc with FID (I. L. Adler & B. M. Jones, Anal. Methods Pestic. Plant Growth
Regul., 1978, 10, 403). Residues determined by glc with ECD of a derivative (idem, ibid.).
JMPR Evaln. 41 (1983). PDS 84 (1996). ICSC.929 (1999). IARC 30 (1983).
banned, 79/117/EEC as amended by 87/181/EEC.
IARC Class tech. is 2B
Oral Acute oral LD
50
for rats 638888, rabbits 300510 (both as mg a.i. (as EC)/kg).
Skin and eye Neither the a.i. nor the formulations caused irritation to skin of rabbits or
visible toxic effects. ADI/RfD (JMPR) No ADI [1983]. Other Women of child-bearing age
should not be exposed to the product. Carcinogenic in rats and mice and is teratogenic
in several species tested. Toxicity Class WHO (a.i.) IaECClassifcation R45| R61| Xn;
R22| N; R50, R53
408
4-(2-nitroprop-1-enyl)phenyl thiocyanate
nitrofuorfen
Herbicide
NOMENCLATURE:
Common name nitrofuorfen (BSI, E-ISO, ANSI, WSSA); nitrofuorf(ne) ((m) F-ISO)
IUPAC name 2-chloro-,,-trifuoro-p-tolyl 4-nitrophenyl ether
Chemical Abstracts name 2-chloro-1-(4-nitrophenoxy)-4-(trifuoromethyl)benzene
CAS RN [42874011] Development codes RH-2512
Smiles code [O-][N+](=O)c1ccc(Oc2ccc(cc2Cl)C(F)(F)F)cc1
13
H
7
ClF
3
NO
3
COMMERCIALISATION:
History Herbicide evaluated by Rohm & Haas Co.
APPLICATIONS:
N-3-nitrophenylitaconimide
Fungicide
NOMENCLATURE:
IUPAC name N-3-nitrophenylitaconimide
Chemical Abstracts name 3-methylene-N-(3-nitrophenyl)pyrrolidine-2,5-dione
CAS RN [4137126] Development codes B 720
Smiles code [O-][N+](=O)c1cccc(c1)N
2
C(=O)CC(=C)C2=O
PHYSICAL CHEMISTRY:
Mol. wt. 232.2 M.f. C
11
H
8
N
2
O
4
COMMERCIALISATION:
History Fungicide reported by B. von Schmeling (Phytopathology, 1962, 52, 819). Evaluated
by Uniroyal Chemical Co., Inc.
4-(2-nitroprop-1-enyl)phenyl thiocyanate
Fungicide
NOMENCLATURE:
Common name nitrostyrene (JMAF)
IUPAC name 4-(2-nitroprop-1-enyl)phenyl thiocyanate
Chemical Abstracts name 4-(2-nitro-1-propenyl)phenyl thiocyanate
CAS RN [950005] Smiles code CC(=Cc1ccc(SC#N)cc1)[N+](=O)[O-]
10
H
8
N
2
O
2
S
norbormide 409
COMMERCIALISATION:
History Fungicide introduced by Nippon Kayaku Co., Ltd.
PRODUCTS:
Discontinued products Styrocide* (Nippon Kayaku).
norbormide
Rodenticide
NOMENCLATURE:
Common name nobormide ((f) F-ISO); norbormide (BSI, E-ISO, ANSI)
IUPAC name 5-(-hydroxy--2-pyridylbenzyl)-7-(-2-pyridylbenzylidene)-8,9,10-
trinorborn-5-ene-2,3-dicarboximide
Chemical Abstracts name 3a,4,7,7a-tetrahydro-5-(hydroxyphenyl-2-pyridinylmethyl)-
8-(phenyl-2-pyridinylmethylene)-4,7-methano-1H-isoindole-1,3(2H)-dione
CAS RN [991424] EC no 2135896 Development codes McN-1025 (McNeil)
Smiles code OC(C1=CC2C3C(C1C2=C(c4ccccc4)c5ccccn5)C(=O)NC3=O)(c6ccccc6)
c7ccccn7
PHYSICAL CHEMISTRY:
Composition Mixture of stereoisomers. Mol. wt. 511.6 M.f. C
33
H
25
N
3
O
3

Form Colourless to off-white crystalline powder. M.p. >160 C Solubility In water
60 mg/l (room temperature). In ethanol 14, chloroform >150, diethyl ether 1, 0.1M
hydrochloric acid 29 (all in mg/l, 30 C). Stability Stable at room temperature when dry,
and to boiling water; hydrolysed by alkali.
COMMERCIALISATION:
History Rodenticide reported by A. P. Roszkowski et al. (Science, 1964, 144, 412).
Introduced by the McNeil Laboratories Inc. Patents GB 1059405
APPLICATIONS: Uses A selective rodenticide lethal to all members of the genus
Rattus that have been tested. It is relatively non-lethal to other rodents.
Formulation types CB .
PRODUCTS:
Discontinued products Raticate* (McNeil); Shoxin* (McNeil).
ANALYSIS:
Product analysis by uv spectrometry (C. A. Janick et al., J. Pharm. Sci., 1966, 55, 1077).
Oral Acute oral LD
50
for Rattus rattus 52, R. norvegicus, R. hawaiiensisc. 10, mice
2250, hamsters 140, prairie dogs >1000 mg/kg; a single oral dose of 1000 mg/kg had
no effect on cats, dogs, monkeys, nor was it lethal to any of 40 other animal species
tested (P. Roszkowski, J. Pharmacol. Exp. Ther., 1965, 149, 288). NOEL Three adult male
410
noruron
volunteers received 15 mg/kg daily for 3 d without ill-effect. Toxicity Class WHO (a.i.) II
nornicotine
Insecticide
NOMENCLATURE:
Common name nornicotine (traditional name)
IUPAC name (S)-3-(pyrrolidin-2-yl)pyridine
Chemical Abstracts name (S)-3-(2-pyrrolidinyl)pyridine CAS RN [494973]
Smiles code C1CNC(C1)c2cccnc2
PHYSICAL CHEMISTRY:
Mol. wt. 148.2 M.f. C
9
H
12
N
2
COMMERCIALISATION:
noruron
Herbicide
For stereochemistry, see W. R. Diveley et al., J. Org. Chem., 34, 616 (1969).
NOMENCLATURE:
Common name norea (ANSI, WSSA); noruron (BSI, E-ISO, (m) F-ISO)
IUPAC name (3aRS,4SR,5RS,7SR,7aRS)-1,1-dimethyl-3-(perhydro-4,7-methanoinden-5-yl)
urea; (3aRS,4SR,5RS,7SR,7aRS)-3-(hexahydro-4,7-methanoindan-5-yl)-1,1-dimethylurea
Chemical Abstracts name 3a,4,5,7,7a-N,N-dimethyl-N-(octahydro-4,7-methano-
1H-inden-5-yl)urea CAS RN [18530568] 3a,4,5,7,7a- isomer; [2163793]
unstated stereochemistry Development codes Hercules 7531
Smiles code CN(C)C(=O)NC1CC2CC1C3CCCC23
PHYSICAL CHEMISTRY:
Mol. wt. 222.3 M.f. C
13
H
22
N
2
O
COMMERCIALISATION:
History Herbicide reported by G. A. Buntin et al. (Abstr. Am. Chem. Soc. Meeting, Los
Angeles, 1963). Introduced by Hercules Inc., Agrochemical Div. (and later Nor-Am.).
APPLICATIONS:
Mode of action Selective herbicide.
PRODUCTS:
Discontinued products Herban* (Hercules).
nuarimol 411
nuarimol
Fungicide
FRAC 3, G1; SBI Class I, DMI: pyrimidine
NOMENCLATURE:
Common name nuarimol (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name ()-2-chloro-4-fuoro--(pyrimidin-5-yl)benzhydryl alcohol
Chemical Abstracts name ()--(2-chlorophenyl)--(4-fuorophenyl)-5-
pyrimidinemethanol CAS RN [63284719] unstated stereochemistry EC no 2640711
Development codes EL-228 (Lilly) Smiles code OC(c1ccc(F)cc1)(c2cncnc2)c3ccccc3Cl
PHYSICAL CHEMISTRY:
Mol. wt. 314.7 M.f. C
17
H
12
ClFN
2
O Form Colourless crystals. M.p. 126127 C V.p.
<0.0027 mPa (25 C) K
ow
logP = 3.18 (pH 7)
Henry 6.73 10
8
Pa m
3
mol
1
(calc.) S.g./density 0.60.8 (bulk) Solubility In water 26
mg/l (pH 7, 25 C). In acetone 170, methanol 55, xylene 20 (all in g/l, 25 C). Readily soluble
in acetonitrile, benzene, and chloroform. Slightly soluble in hexane. Stability Decomposed
rapidly by uv light. Stable at 52 C.
COMMERCIALISATION:
History Fungicide introduced in Greece (1980) by Eli Lilly & Co. (agrochemical interests
later Dow AgroSciences). Rights sold to Gowan Co. Patents GB 1218623
APPLICATIONS:
Biochemistry Sterol demethylation (ergosterol biosynthesis) inhibitor.
Mode of action Systemic foliar fungicide with curative and protective action. Interferes
with the completion of division of sporids. Uses Control of a wide range of pathogenic
fungi, such as Pseudocercosporella spp., Septoria spp., Ustilago spp., powdery mildew, leaf
spot, etc., in cereals, both as a foliar spray and as a seed treatment; powdery mildews
on pome fruit, stone fruit, vines, hops, cucurbits, and other crops; scab on apples; etc.
Formulation types EC; SC. SL; WP; Seed treatment.
F C
OH
N
N
Cl
412
OCH
PRODUCTS:
Discontinued products Cidorel* (BASF Espaola); Gandural* (Dow AgroSciences);
Gauntlet* (Shell); Tridal* (Dow AgroSciences); Trimidal* (Dow AgroSciences); Triminol*
(DowElanco); Discontinued mixtures Gandural S* (+ sulfur) (Dow AgroSciences).
ANALYSIS:
Product analysis by glc with FID (E. W. Day & O. D. Decker, Anal. Methods Pestic. Plant Growth
Regul., 1984, 13, 183). Residues in soil and plant tissue determined by glc with ECD (idem,
ibid.). Details available from Dow AgroSciences.
Oral Acute oral LD
50
3000, beagle dogs 500 mg/kg. Skin and eye Acute percutaneous LD
50
for rabbits >2000
mg/kg. No skin irritation; slight eye irritant (rabbits). Not a skin sensitiser (guinea pigs).
Inhalation Rats essentially unaffected after 1 h by 0.37 mg tech./l air. NOEL (2 y) for rats
and mice 50 mg/kg diet. Toxicity Class WHO (a.i.) III EPA (formulation) III
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 200 mg/kg. Fish LC
50
(96 h) for bluegill
sunfshc. 12.1 mg/l. Daphnia LC
50
(48 h) >25 mg/l. Algae EC
50
(96 h) for Selenastrum
capricornutum 2.5 mg/l. Bees Not toxic to bees; LC
50
(contact) >11 g/l. Worms NOEC
(14 d) for earthworms 100 g/kg soil.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, elimination is rapid. Plants Numerous
photodegradation products are formed. Soil/Environment Microbial degradation is
accelerated by light; DT
50
(lab.) 344 d, (feld)c. 150 d. K
oc
26, depending on soil type.
OCH
Fungicide, herbicide
NOMENCLATURE:
Common name OCH (WSSA)
IUPAC name octachlorocyclohex-2-enone
Chemical Abstracts name 2,3,4,4,5,5,6,6-octachloro-2-cyclohexen-1-one
CAS RN [4024811] Smiles code ClC1=C(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C1=O
PHYSICAL CHEMISTRY:
Mol. wt. 371.7 M.f. C
6
Cl
8
O
COMMERCIALISATION:
History Herbicide and fungicide introduced by Goodrich Chemical Co.
2-(octylthio)ethanol 413
PRODUCTS:
Discontinued products Oktone* (Goodrich).
OCS 21693
Herbicide
NOMENCLATURE:
IUPAC name methyl 2,3,5,6-tetrachloro-N-methoxy-N-methylterephthalamate
Chemical Abstracts name methyl 2,3,5,6-tetrachloro-4-[[methoxy(methyl)amino]
carbonyl]benzoate CAS RN [14419013] Development codes OCS 21693
Smiles code CON(C)C(=O)c1c(Cl)c(Cl)c(C(=O)OC)c(Cl)c1Cl
11
H
9
Cl
4
NO
4
COMMERCIALISATION:
History Herbicidal activity reported by W. Furness (Symp. New Herbic., 3rd, 1969, p. 261).
Introduced by Velsicol Corp. (later Sandoz AG).
2-(octylthio)ethanol
Insect repellent
NOMENCLATURE:
IUPAC name 2-(octylthio)ethanol
Chemical Abstracts name 2-(octylthio)ethanol Other names 2-hydroxyethyl octyl
sulfde CAS RN [3547339] EC no 2225984 Development codes Phillips R-874
Smiles code CCCCCCCCSCCO
10
H
22
OS Form Pale amber liquid,
with a mild, mercaptan-like odour. M.p. 0 C B.p. 98 C /0.1 mmHg V.p. 79 mPa (25 C)
K
ow
logP = 0.561 S.g./density 0.9250.935 (24 C) Solubility Slightly soluble in water;
miscible with most organic solvents including refned kerosene, though a co-solvent
such as isopropanol is required with the latter to maintain solution at low temperatures.
Stability Stable at pH 68, and to heat and light.
COMMERCIALISATION:
History Insect-repelling properties reported by L. D. Goodhue (J. Econ. Entomol., 1960,
53, 805). Introduced by Phillips Petroleum Co. and by the McLaughlin Gormley King Co.
Patents US 2863799 (to Phillips Petroleum Co., 1958) Manufacturers MGK
APPLICATIONS: Uses Its chief use is as a repellent to Blattodea, at 1 g/m{2}. Also as
a repellent using pressurised patio foggers against Formicidae, Muscidae and crawling
insects. Formulation types EC; OL .
CH
3
(CH
2
)
7
SCH
2
CH
2
OH
414
oxapyrazon; oxapyrazon-sodium; oxapyrazon-(2-hydroxyethyldimethylammonium)
ANALYSIS:
Details of a glc method available from McLaughlin Gormley King Co.
Oral Acute oral LD
50
50
for
albino rabbits 13 590 mg/kg. Application of 0.05 mg to the cornea of albino rats produced
corneal necrosis in 2 of the 5 eyes tested, but they healed without opacities.
Inhalation LC
50
(4 h) for rats 6.12 mg/l. NOEL In 90 d feeding trials, rats receiving 20 000
mg/kg diet showed no adverse effect. Toxicity Class WHO (a.i.) U.
ECClassifcation Xi; R41
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and bobwhite quail >8000 mg/kg diet.
Fish LC
50
(96 h) for rainbow trout 2.9, bluegill sunfsh 2.7 mg/l. Daphnia LC
50
(48 h)
0.38 mg/l.
oxapyrazon; oxapyrazon-sodium;
oxapyrazon-(2-hydroxyethyldimethylammonium)
Herbicide
NOMENCLATURE:
Common name oxapyrazon* (BSI (19841990), E-ISO (pre-1990), for
2-hydroxyethyldimethylammonium salt); oxapyrazone ((f) F-ISO); oxapyrazon (Canada,
since 1990 BSI, E-ISO)
IUPAC name 5-bromo-1,6-dihydro-6-oxo-1-phenylpyridazin-4-yloxamic acid
Chemical Abstracts name [(5-bromo-1,6-dihydro-6-oxo-1-phenyl-4-pyridazinyl)
amino]oxoacetic acid CAS RN [4489310] oxapyrazon; [25316567]
oxapyrazon-sodium; [25316578] oxapyrazon-(2-hydroxyethyldimethylammonium)
Development codes BAS 3380H (oxapyrazon-sodium); BAS 350H (oxapyrazon-(2-
hydroxyethyldimethylammonium)) (both BASF)
Smiles code oxapyrazon-sodium:[Na+].[O-]C(=O)C(=O)Nc1cnn(c2ccccc2)c(=O)c1Br
PHYSICAL CHEMISTRY:
Mol. wt. 338.1; (sodium salt 360.1; 2-hydroxyethyldimethylammonium salt 427.3)
M.f. C
12
H
8
BrN
3
O
4
; (sodium salt C
12
H
7
BrN
3
NaO
4
; 2-hydroxyethyldimethylammonium salt
C
16
H
19
BrN
4
O
5
)
COMMERCIALISATION:
History Herbicide developed by BASF AG.
oxydeprofos 415
oxathiapiprolin
Fungicide
NOMENCLATURE:
Common name oxathiapiprolin (pa ISO)
IUPAC name 1-(4-{4-[(5RS)-5-(2,6-difuorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-
thiazol-2-yl}-1-piperidyl)-2-[5-methyl-3-(trifuoromethyl)-1H-pyrazol-1-yl]ethanone
Chemical Abstracts name 1-[4-[4-[5-(2,6-difuorophenyl)-4,5-dihydro-3-
isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifuoromethyl)-1H-pyrazol-
1-yl]ethanone CAS RN [1003318679] Development codes DPXQGU42
Smiles code Cc1cc(nn1CC(=O)N
2
CCC(CC2)c3nc(cs3)C4=NOC(C4)c5c(cccc5F)F)C(F)(F)F
PHYSICAL CHEMISTRY:
Mol. wt. 539.52 M.f. C
24
H
22
F
5
N
5
O
2
S
oxydeprofos
IRAC 1B
NOMENCLATURE:
Common name oxyd(profos) ((m) F-ISO); oxydeprofos (BSI, E-ISO); ESP (JMAF)
IUPAC name S-2-ethylsulfnyl-1-methylethyl O,O-dimethyl phosphorothioate
Chemical Abstracts name S-[2-(ethylsulfnyl)-1-methylethyl] O,O-dimethyl
phosphorothioate CAS RN [2674911] Development codes Bayer 23 655; S 410
Smiles code CCS(=O)CC(C)SP(=O)(OC)OC
7
H
17
O
4
PS
2
Form Yellow oil.
B.p. 115 C /0.02 mmHg V.p. 0.625 mPa (20 C) S.g./density 1.257 (20 C)
Solubility Soluble in water, alcohols, chlorinated hydrocarbons, ketones; sparingly soluble
in light petroleum.
COMMERCIALISATION:
History Insecticide described by G. Schrader (Phosphorsure-Ester). Introduced by Bayer
AG. Patents DE 1035958; US 2952700
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic and contact
insecticide and acaricide. Uses Effective against sap-feeding insects and mites at 25 g/100 l.
CF
3
S
N
N
O
F
F
N
O
N
N
CH
3
416
oxydisulfoton
PRODUCTS:
Discontinued products Estox* (Bayer); Metasystox S* (Bayer).
ANALYSIS:
Product analysis is by titration after reduction by titanium disulfate. Residues may be
determined by glc.
Oral Acute oral LD
50
50
for male
rats 800 mg/kg. NOEL In 50 d feeding trials, the growth of rats receiving 10 mg/kg daily
was not affected. Other I.p. LD
50
for guinea-pigs 100 mg/kg. Toxicity Class WHO (a.i.) Ib
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp and Japanese killifsh >40 mg/l.
oxydisulfoton
IRAC 1B
NOMENCLATURE:
Common name oxydisulfoton (BSI, E-ISO, (m) F-ISO)
IUPAC name O,O-diethyl S-2-ethylsulfnylethyl phosphorodithioate
Chemical Abstracts name O,O-diethyl S-[2-(ethylsulfnyl)ethyl] phosphorodithioate
CAS RN [2497076] EC no 2196791
Development codes Bayer 23 323; S 309; L 16/184
Smiles code CCOP(=S)(OCC)SCCS(=O)CC
8
H
19
O
3
PS
3
COMMERCIALISATION:
History Insecticide and acaricide introduced by Bayer AG.
APPLICATIONS:
acaricide.
PRODUCTS:
Discontinued products Disyston S* (Bayer).
Toxicity Class WHO (a.i.) OECClassifcation T+; R28| T; R24| N; R50, R53| concn.
dep.
pebulate 417
parafuron
Herbicide
NOMENCLATURE:
Common name parafuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,1-dimethyl-3-(,,-trifuoro-p-tolyl)urea
Chemical Abstracts name N,N-dimethyl-N-[4-(trifuoromethyl)phenyl]urea
CAS RN [7159991] Development codes C 15 935
Smiles code CN(C)C(=O)Nc1ccc(cc1)C(F)(F)F
10
H
11
F3N
2
O
COMMERCIALISATION:
History Herbicide introduced by Ciba AG (later Ciba-Geigy AG).
pebulate
Herbicide
HRAC N WSSA 8; thiocarbamate
NOMENCLATURE:
Common name pebulate (BSI, E-ISO, (m) F-ISO, WSSA, JMAF)
IUPAC name S-propyl butyl(ethyl)thiocarbamate
Chemical Abstracts name S-propyl butylethylcarbamothioate CAS RN [1114712]
EC no 2142154 Development codes R-2061 (Stauffer)
Smiles code CCCCN(CC)C(=O)SCCC
PHYSICAL CHEMISTRY:
10
H
21
NOS
Form Colourless or yellow liquid, with an aromatic odour. B.p. 142 C /21 mmHg
V.p. 9 Pa (30 C); 4.7 Pa (25 C) K
ow
logP = 3.83 Henry 20 Pa m
3
mol
1
(20 C, calc.)
S.g./density 0.956 (20 C) Solubility In water 60 mg/l (20 C). Miscible with most
organic solvents, e.g. acetone, benzene, toluene, xylene, methanol, isopropanol and
kerosene. Stability Stable up to 200 C. In water, DT
50
(40 C) 11 d (pH 4 and pH 10),
12 d (pH 7). F.p. 124 C
COMMERCIALISATION:
History Herbicide reported by E. O. Burt (Proc. South. Weed Conf., 12th, 1959, p. 19).
C N
O
S
CH
3
(CH
2
)
3
CH
3
CH
2
(CH
2
)
2
CH
3
418
pebulate
Introduced by Stauffer Chemical Co. (now Syngenta AG). Divested to Cedar Chemical
Corp. in 2001. Patents US 3175897
APPLICATIONS:
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). The sulfoxide may be the
active form (P. B. Barrett & J. L. Harwood, Proc. Br. Crop Prot. Conf. Weeds, 1993, 1, 183).
Mode of action Selective systemic herbicide, absorbed by the roots, with translocation
throughout the plant. Acts by inhibition of germination. Uses Control of annual grasses
(including nutgrasses) and some broad-leaved weeds in sugar beet, tomatoes and tobacco.
Applied pre-emergence, at 46 kg/ha with soil incorporation. Formulation types EC; GR.
PRODUCTS:
Discontinued products Tillam* (Tri-Ag); Discontinued mixtures Edge* (+ fonofos)
(Zeneca).
ANALYSIS:
Product analysis by glc with FID (AOAC Methods, 18th Ed., 974.05; CIPAC Handbook, 1983,
1B, 1887). Residues in crops and soils determined by glc (G. G. Patchett et al., Anal. Methods
Pestic., Plant Growth Regul. Food Addit., 1964, 4, 343; W. Y. Ja et al., Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 698). See also Pestic. Anal. Man., II, 180.238. In soil or water by glc
with NPD (AOAC Methods, 18th Ed., 991.07; Environ. Chem. Methods). Analytical methods
available from Syngenta.
EHC 76 (1988); a general review of thiocarbamates. EU Status (1107/2009) Not
Oral Acute oral LD
50
LD
50
for rabbits 4640 mg/kg. Slight irritation of skin, eyes and mucous membranes (rabbits).
Not a skin sensitiser (guinea pigs). Inhalation LC
50
(4 h) for female rats >3.5 mg/l.
NOEL (2 y) for rats 0.74 mg/kg b.w. daily (EPA RED). Not carcinogenic or teratogenic.
ADI/RfD (EPA) aRfD 0.5, cRfD 0.007 mg/kg b.w. [1999]. Toxicity Class WHO (a.i.) II EPA
(formulation) III ECClassifcation Xn; R22| N; R51, R53
ECOTOXICOLOGY:
Birds Dietary LC
50
(7 d) for bobwhite quail 8400 mg/kg diet. Fish LC
50
(96 h) for rainbow
trout and bluegill sunfshc. 7.4 mg/l; (48 h) for silver mullet 6.25, killifsh 7.78 mg/l.
Daphnia LC
50
(48 h) 5.9 mg/l. Bees Non-toxic to bees at 0.011 mg/bee.
ENVIRONMENTAL FATE:
Animals In animals, pebulate is rapidly metabolised. In rats, following oral
administration,c. 50% was expired as CO
2
, 25% excreted in the urine, and 5% excreted
in the faeces, within 3 days. Plants In plants, pebulate is rapidly metabolised to CO
2
and
naturally-occurring plant constituents. Soil/Environment In soil, pebulate disappears
mainly by microbial degradation to the mercaptan, ethylbutylamine and CO
2
. DT
50
in soil
23 w.
pentanochlor 419
penfuron
Insecticide
benzoylurea
NOMENCLATURE:
IUPAC name 1-(2,6-difuorobenzoyl)-3-(,,-trifuoro-p-tolyl)urea
Chemical Abstracts name 2,6-difuoro-N-[[[4-(trifuoromethyl)phenyl]amino]carbonyl]
benzamide CAS RN [35367318] Development codes PH-60-44 (Duphar); TH-60-44
(Thompson-Hayward)
15
H
9
F
5
N
2
O
2
COMMERCIALISATION:
History Evaluated by Duphar B.V. and Thompson-Hayward Chemical Co.; EUP granted in
1983 (Shibuya).
APPLICATIONS: Uses Evaluated against spruce budworm. Effective against pests of
stored products, such as Tribolium castaneum and Trogoderma granarium.
pentanochlor
Herbicide
HRAC C2 WSSA 7; anilide
NOMENCLATURE:
Common name pentanochlor (BSI, E-ISO); CMMP (JMAF); pentanochlore ((f) F-ISO);
solan (WSSA, Canada, ex ANSI)
IUPAC name 3-chloro-2-methylvalero-p-toluidide
Chemical Abstracts name N-(3-chloro-4-methylphenyl)-2-methylpentanamide
Smiles code CCCC(C)C(=O)Nc1ccc(C)c(Cl)c1
13
H
18
ClNO Form Colourless solid;
(tech., colourless to pale cream powder). M.p. 8586 C (pure); 8286 C (tech.)
V.p. Very low at room temperature S.g./density 1.106 (20 C) Solubility In water
89 mg/l (20 C). In diisobutyl ketone 460, isophorone 550, methyl isobutyl ketone 520,
xylene 200300, pine oil 410 (all in g/kg, 20 C). Stability Stable to hydrolysis in neutral
media at room temperature.
CH
3
Cl
NHCOCH(CH
2
)
2
CH
3
CH
3
420
perfuidone
COMMERCIALISATION:
History Herbicide reported by D. H. Moore (Proc. Northeast. Weed Control Conf., 1960,
p. 86). Introduced by FMC Corp. Patents GB 869169; US 3020142
APPLICATIONS:
site. Mode of action Selective, contact herbicide with absorption via the leaves.
Uses Selective pre- and post-emergence herbicidal control in carrots, celeriac, celery,
fennel, parsley, and parsnips, at <4 kg/ha. Used pre-sowing on tomatoes and some fower
crops, and as a contact spray in carnations, chrysanthemums, fruit trees, ornamental trees
and shrubs, roses, sweet peas, and tomatoes. With chlorpropham, used as above, though
also on narcissi and tulips. Formulation types EC.
PRODUCTS:
Discontinued products Croptex Bronze* (Certis UK); Solan* (Nufarm UK);
Discontinued mixtures Atlas Brown* (+ chlorpropham) (Nufarm UK).
ANALYSIS:
Residues determined by hydrolysis to 3-chloro-p-toluidine which is estimated by glc.
Oral Acute oral LD
50
for rats >10 000 mg/kg. Skin and eye Slight irritation of skin and
mucous membranes. NOEL In 140 d feeding trials, rats receiving 20 000 mg/kg diet
suffered no effect on body weight or survival, but histopathological changes were found in
the liver; these effects were not observed at 2000 mg/kg diet. Toxicity Class WHO (a.i.)
U EPA (formulation) IV
ECOTOXICOLOGY:
Bees Not very toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Similar to 3,4-dichloroaniline-based acylanilide herbicides; converted
to 3-chloro-4-methylaniline. This does not accumulate but is converted to 3,3-dichloro-
4,4-dimethylazobenzene.
perfuidone
Herbicide
NOMENCLATURE:
Common name perfuidone (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 1,1,1-trifuoro-N-(4-phenylsulfonyl-o-tolyl)methanesulfonamide;
1,1,1-trifuoro-2-methyl-4-(phenylsulfonyl)methanesulfonanilide
Chemical Abstracts name 1,1,1-trifuoro-N-[2-methyl-4-(phenylsulfonyl)
perfuidone 421
phenyl]methanesulfonamide CAS RN [37924133] EC no 2537183
Development codes MBR-8251
Smiles code Cc1cc(ccc1NS(=O)(=O)C(F)(F)F)S(=O)(=O)c2ccccc2
PHYSICAL CHEMISTRY:
Mol. wt. 379.4 M.f. C
14
H
12
F
3
NO
4
S
2
Form Colourless crystals. M.p. 142144 C V.p.
<1.3 mPa (25 C) Solubility In water 60 mg/l (22 C). In acetone 750, methanol 595,
acetonitrile 560, chloroform 175, dichloromethane 162, diethyl ether 93, benzene 11,
hexane 0.03 (all in g/l, 22 C). Stability Stable to both acid and alkaline hydrolysis, and to
heat. Susceptible to slow degradation in aqueous solution under uv irradiation. pKa 2.5
COMMERCIALISATION:
History Herbicide reported by W. A. Gentner (Agric. Res. (Wash., D.C.), 1971, 20(2), 5).
Introduced by 3M Company. Patents GB 1306564; BE 765558
APPLICATIONS:
Biochemistry Interferes with protein biosynthesis and with cellular respiration.
Mode of action Selective herbicide which acts by contact and by root absorption.
Uses Pre-emergence herbicide for control of Cyperus esculentus, many
monocotyledonous weeds, and certain broad-leaved weeds in cotton, transplanted
tobacco, rice, sugar cane, and established turf at 1.14.5 kg/ha. Phytotoxicity Phytotoxic
to carrots, oats, sugar beet, soya beans, and spinach. Formulation types WP; GR; SL .
Compatibility Incompatible with liquid nitrogen fertilisers and acidic fertilisers.
PRODUCTS:
Other mixtures Destun* (+ benazolin) (3M).
ANALYSIS:
Product analysis by glc of a derivative with FID (C. D. Green, Anal. Methods Pestic. Plant
Growth Regul., 1978, 10, 437). Residues determined by glc of a derivative with ECD (idem,
ibid.).
Oral Acute oral LD
50
LD
50
for rabbits >4000 mg/kg. Severe eye irritant; mild skin irritant (rabbits).
Inhalation LC
50
(4 h) for rats 3.2 mg/l air. NOEL In 90 d feeding trials, rats receivingc. 800
mg/kg diet and dogs receivingc. 200 mg/kg showed no ill effects. ADI/RfD (EPA) 0.01 mg/
kg b.w. [1989]. Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassifcation Xn;
R22| Xi; R36
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for quail 7144, ducks >10 000 mg/kg (for WP formulation).
Fish LC
50
(96 h) for rainbow trout 312, bluegill sunfsh 318 mg/l.
ENVIRONMENTAL FATE:
Soil/Environment In wet, neutral or alkaline soils, leaching occurs, particularly in soils
422
PH 60-38
having low clay or organic matter content. Leaching occurs to a much lesser extent
in acidic soils. Microbial action accounts for the breakdown of a signifcant portion of
perfuidone in the soil, although photodecomposition and volatilisation also occur to some
extent. Soil DT
50
c. 1 month.
PH 60-38
Insecticide
IRAC 15
NOMENCLATURE:
IUPAC name 1-(4-chlorophenyl)-3-(2,6-dichlorobenzoyl)urea
Chemical Abstracts name 2,6-dichloro-N-[[(4-chlorophenyl)amino]carbonyl]benzamide
CAS RN [35409973] Development codes PH 60-38
Smiles code Clc1ccc(NC(=O)NC(=O)c2c(Cl)cccc2Cl)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 343.6 M.f. C
14
H
9
Cl
3
N
2
O
2
COMMERCIALISATION:
History Insect growth regulator evaluated by Philips Duphar (later Uniroyal Chemical Co.,
Inc.).
APPLICATIONS:
Biochemistry Chitin synthesis inhibitor. Mode of action Insect growth regulator
phenisopham
Herbicide
NOMENCLATURE:
Common name ph(nisophame) ((m) F-ISO); phenisopham (BSI, E-ISO)
IUPAC name isopropyl 3-[ethyl(phenyl)carbamoyloxy]carbanilate;
3-(isopropoxycarbonylamino)phenyl N-ethylcarbanilate
Chemical Abstracts name 3-[[(1-methylethoxy)carbonyl]amino]phenyl
ethylphenylcarbamate CAS RN [57375630] Development codes SN 58 132
(Schering) Smiles code CCN(C(=O)Oc1cccc(NC(=O)OC(C)C)c1)c2ccccc2
19
H
22
N
2
O
4
M.p. 109110 C V.p. 6.65 10
4
mPa (25 C) Henry 7.59 10
5
Pa m
3
mol
1
(calc.)
Solubility In water 3 mg/l (25 C). In dichloromethane 300, ethanol 98, methanol 60,
isopropanol 26, toluene 35 (all in g/l, 25 C). Stability Unstable under alkaline conditions,
DT
50
35 d (pH 9), 29 d (pH 12), 2 d (pH 13), 7 h (pH 14).
COMMERCIALISATION:
History Herbicide reported in Schering AG Tech. Inf. 1977. Introduced by Schering AG.
Patents DE 2413933
phenkapton 423
APPLICATIONS:
Mode of action Selective and contact herbicide. It acts mainly by contact but there also
appears to be some activity through the soil. Uses Mainly used to control broad-leaved
weeds in cotton; applied at 12 kg/ha. Formulation types EC.
PRODUCTS:
Discontinued products Diconal* (Schering); Verdinal* (Schering).
ANALYSIS:
Product analysis by tlc. Residues determined by hydrolysis to N-ethylaniline a derivative
being measured by glc with ECD.
Oral Acute oral LD
50
for rats >4000, mice >5000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rabbits >1000 mg/kg. NOEL (90 d) for rats 1 mg/kg daily; (182 d)
for dogs 3 mg/kg daily. Toxicity Class WHO (a.i.) U
phenkapton
IRAC 1B
NOMENCLATURE:
Common name phenkapton (BSI, E-ISO, (m) F-ISO); CMP (JMAF)
IUPAC name S-2,5-dichlorophenylthiomethyl O,O-diethyl phosphorodithioate
Chemical Abstracts name S-[[(2,5-dichlorophenyl)thio]methyl] O,O-diethyl
phosphorodithioate CAS RN [2275141] EC no 2188927
Development codes G 28 029 Smiles code CCOP(=S)(OCC)SCSc1cc(Cl)ccc1Cl
11
H
15
Cl
2
O
2
PS
3
COMMERCIALISATION:
History Insecticide and acaricide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
Toxicity Class WHO (a.i.) OECClassifcation T; R23/24/25| N; R50, R53
424
phenobenzuron
phenmedipham-ethyl
Herbicide
NOMENCLATURE:
Common name phenm(diphame-) ((m) F-ISO); phenmedipham-ethyl (BSI, E-ISO)
IUPAC name 3-ethoxycarbonylaminophenyl 3-methylcarbanilate; ethyl
3-(3-methylcarbaniloyloxy)carbanilate
Chemical Abstracts name 3-[(ethoxycarbonyl)amino]phenyl (3-methylphenyl)
carbamate CAS RN [13684441] Development codes SN 38 574
Smiles code CCOC(=O)Nc1cccc(OC(=O)Nc2cccc(C)c2)c1
PHYSICAL CHEMISTRY:
Mol. wt. 314.3 M.f. C
17
H
18
N
2
O
4
COMMERCIALISATION:
History Superseded ethyl homologue of phenmedipham. Herbicide evaluated by Schering
AG.
APPLICATIONS:
site.
phenobenzuron
Herbicide
NOMENCLATURE:
Common name phenobenzuron (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-benzoyl-1-(3,4-dichlorophenyl)-3,3-dimethylurea
Chemical Abstracts name N-(3,4-dichlorophenyl)-N-[(dimethylamino)carbonyl]
benzamide CAS RN [3134121] Development codes PP 6525
Smiles code CN(C)C(=O)N(C(=O)c1ccccc1)c2ccc(Cl)c(Cl)c2
16
H
14
Cl
2
N
2
O
2
COMMERCIALISATION:
History Herbicidal activity reported by P. Poignant et al. (Symp. New Herbic., 2nd, 1965, p.
1). Introduced by Pechiney-Progil (later Rhne-Poulenc Agrochimie).
PRODUCTS:
Discontinued products Benzomarc* (Rhne-Poulenc).
phenylmercury chloride 425
2-phenyl-4H-3,1-benzoxazin-4-one
Herbicide
NOMENCLATURE:
IUPAC name 2-phenyl-4H-3,1-benzoxazin-4-one (I)
Chemical Abstracts name (I) CAS RN [1022464] Development codes H-170
Smiles code O=c1oc(nc2ccccc12)c3ccccc3
14
H
9
NO
2
COMMERCIALISATION:
History Herbicide reported by A. Fischer (Meded. Landbouwhogesch. Opzoekingsstn. Staat
Gent, 1965, 30, 163). Introduced by BASF AG.
PRODUCTS:
Discontinued products Linurotox* (BASF).
phenylmercury chloride
Fungicide
NOMENCLATURE:
IUPAC name phenylmercury chloride
Chemical Abstracts name chlorophenylmercury CAS RN [100561]
PHYSICAL CHEMISTRY:
Mol. wt. 313.1 M.f. C
6
H
5
ClHg Form Colourless crystals. M.p. 250 C V.p. 1.3 10-2
mPa (0 C); 1.3 mPa (45 C) Solubility In water 0.003%. Readily soluble in acetone,
cyclohexanone, methyl ethyl ketone, tetrahydrofuran, DMF. Slightly soluble in benzene,
toluene, xylene, chloroform, methanol, ethanol (room temperature). Sparingly soluble in
carbon tetrachloride, diethyl ether, petroleum ether and mineral oils. Stability Stable
under neutral conditions. Weak alkalis convert it to phenylmercury hydroxide, strong
alkalis to the oxide. Stable in acidic media at room temperature.
COMMERCIALISATION:
Manufacturers Arco Chemie; Bayer; ICI; Steetley
APPLICATIONS:
Mode of action Curative fungicide. Uses Dry fungicidal treatment for the protection of
seed (wheat, rye, barley, and oats) against Stinking smut, snow mould and barley leaf stripe.
PRODUCTS:
Discontinued products Agronal* (Spolana); Discontinued mixtures Tillantox*
(+ benquinox) (Bayer).
426
phenylmercury dimethyldithiocarbamate
ANALYSIS:
973.11). Mercury impurities determined (CIPAC Handbook, 1994, F, 264).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds. JMPR Evaln.
9 (1967). EU Status (1107/2009) Aryl mercury compounds considered to be outside the
scope of the Directive; already banned, 79/117/EEC.
Oral Acute oral LD
50
for highly soluble organic mercury compounds 50100 mg/kg.
Skin and eye Causes irritation of skin, mucous membranes and respiratory organs.
ADI/RfD (JMPR) No ADI [1967]. PIC Yes.
phenylmercury dimethyldithiocarbamate
Fungicide
NOMENCLATURE:
IUPAC name phenylmercury dimethyldithiocarbamate
Chemical Abstracts name (dimethylcarbamodithioato-S,S)phenylmercury
CAS RN [32407991] Smiles code CN(C)C(=S)[S-].[Hg+]c1ccccc1
9
H
11
HgNS
2
Form Fine colourless
to grey-white powder. M.p. 175 C V.p. 1.1 10
1
mPa (35 C) Solubility In water
6 mg/l (20 C). In aniline 150, cyclohexanone 50, pyridine 50 (all in g/l); readily soluble
in chloroform; sparingly soluble in acetic acid, alcohols, diethyl ether, tetrahydrofuran.
Stability Stable at 180 C and in water at pH 12.
COMMERCIALISATION:
History Fungicide introduced by Berk Chemicals (later Steetley Chemicals Ltd).
APPLICATIONS:
Mode of action Fungicide with low volatility and high stability. Uses Used to eradicate
Venturia spp. on most varieties of apples and pears at 1.53.0 g (as mercury)/100 l.
Phytotoxicity A few varieties of apple and pear are damaged by mercury compounds.
PRODUCTS:
Discontinued products Phelam* (Steetley).
ANALYSIS:
Mercury impurities determined (CIPAC Handbook, 1994, F, 264).
JMPR Evaln. 9 (1967) EU Status (1107/2009) Aryl mercury compounds considered to be
outside the scope of the Directive; already banned, 79/117/EEC.
phenylmercury nitrate 427
Toxicity Class WHO (a.i.) OECClassifcation Not specifed, but organic mercury
generally is assigned T+; R26/27/28| R33| N; R50, R53 (concentration-dependent) PIC Yes.
phenylmercury nitrate
NOMENCLATURE:
Common name phenylmercury nitrate (BSI, E-ISO, chemical name, used in lieu of
common name, although the material used commercially is the basic nitrate with formula
as given); nitrate de ph(nylmercure) (draft F-ISO)
IUPAC name phenylmercury hydroxide with phenylmercury nitrate; phenylmercury
nitrate (basic)
Chemical Abstracts name hydroxy(nitrato)diphenyldimercury CAS RN [8003052]
Smiles code O[Hg]c1ccccc1.[O-][N+](=O)O[Hg]c1ccccc1
PHYSICAL CHEMISTRY:
Composition See notes under Common name. Tech. has a mercury content of 63.4%
m/m. Mol. wt. 634.4 M.f. C
12
H
11
Hg
2
NO
4
Form Colourless powder. M.p. c. 188 C
(decomp.) Solubility In water 600 mg/kg (20 C). In acetone 5, benzene 3, ethanol 1,
methanol 9 (g/kg, 20 C).
COMMERCIALISATION:
History Fungicide introduced by Steetley Ltd.
APPLICATIONS: Uses Used against Venturia spp. on apples and pears,at 1.53.0 g (as
mercury)/100 l. Seed dressings, usually combined with an insecticide or another fungicide,
are used for cereals, sugar beet, fodder beet and mangolds. Phytotoxicity A few varieties
of apple and pear are damaged by mercury compounds.
PRODUCTS:
Discontinued mixtures Harvesan Plus* (+ gamma-HCH) (Steetley); Murcicide*
(+ captan) (Steetley).
ANALYSIS:
973.11). Mercury impurities determined (CIPAC Handbook, 1994, F, 264).
EHC 1 (1976), 86 (1989), both general reviews of mercury and its compounds.
EU Status (1107/2009) Aryl mercury compounds considered to be outside the scope of
the Directive; already banned, 79/117/EEC.
Other I.v. LD
50
for rats 27 mg/kg. Toxicity Class WHO (a.i.) IbECClassifcation T;
R25, R48/24/25| C; R34| Xi; R37| R44 PIC Yes.
428
phosdiphen
phosacetim
Rodenticide
IRAC 1B
NOMENCLATURE:
Common name phosac(time) ((f) F-ISO); phosacetim (BSI, E-ISO)
IUPAC name O,O-bis(4-chlorophenyl) N-acetimidoylphosphoramidothioate
Chemical Abstracts name O,O-bis(4-chlorophenyl) (1-iminoethyl)phosphoramidothioate
CAS RN [4104147] EC no 2238747 Development codes Bayer 38 819
Smiles code CC(=N)NP(=S)(Oc1ccc(Cl)cc1)Oc2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 375.2 M.f. C
14
H
13
Cl
2
N
2
O
2
PS
COMMERCIALISATION:
History Rodenticide reported by V. B. Richens (Pest Control, 1967, 35(9), 28). Introduced
by Bayer AG.
APPLICATIONS:
PRODUCTS:
Discontinued products Gophacide* (Bayer).
Toxicity Class WHO (a.i.) OECClassifcation T+; R27/28| N; R50, R53
phosdiphen
Fungicide
NOMENCLATURE:
Common name phosdiphen (JMAF)
IUPAC name bis(2,4-dichlorophenyl) ethyl phosphate
Chemical Abstracts name bis(2,4-dichlorophenyl) ethyl phosphate CAS RN [36519
003] Development codes MTO-460 (Mitsui Toatsu) Smiles code CCOP(=O)
(Oc1ccc(Cl)cc1Cl)Oc2ccc(Cl)cc2Cl
PHYSICAL CHEMISTRY:
14
H
11
Cl
4
O
4
P Form Pale yellow liquid
Cl O
Cl
P
OCH
2
CH
3
O
O
Cl
Cl
phosfolan 429
(tech.). B.p. 175 C /0.2 mmHg (tech.) V.p. 66 mPa (20 C) (tech.) Henry 3.92 10
1
Pa
m
3
mol
1
(calc.) S.g./density 1.405 (25 C, tech.) Solubility In water 0.7 mg/l (20 C).
Soluble in acetone, xylene and hexane. Stability Stable in acidic media, but unstable in
alkaline media. Hydrolysis DT
50
(25 C) 7 d (pH 7), 4 d (pH 9). Thermally stable up to
200 C.
COMMERCIALISATION:
History Fungicide reported by M. Hamada et al. (Ann. Phytopathol. Soc. Japan, 1971, 37,
365). Introduced by Hokko Chemical Industry Co., Ltd and Mitsui Toatsu Chemicals Inc.
(later Mitsui Chemicals Inc.). Patents JP 634549 (to Hokko) Manufacturers Hokko;
Mitsui Toatsu
APPLICATIONS: Uses Control of rice blast (Pyricularia oryzae).
ANALYSIS:
Oral Acute oral LD
50
for male rats 6200, mice 5300 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >5000, mice 90009600 mg/kg.
APPLICATIONS:
(24 h) of tech. to skin and eyes of rabbits produced no irritation. NOEL (90 d) for
rats and mice 200 mg/kg diet; (2 y) for rats and mice 30 mg/kg diet. No reproductive,
teratogenic or mutagenic effects observed in rats. Toxicity Class WHO (a.i.) U EPA
(formulation) III
ECOTOXICOLOGY:
Fish LC
50
phosfolan
IRAC 1B
NOMENCLATURE:
Common name phospholan ((m) F-ISO); phosfolan (BSI, E-ISO)
IUPAC name diethyl 1,3-dithiolan-2-ylidenephosphoramidate;
2-(diethoxyphosphinylimino)-1,3-dithiolane
Chemical Abstracts name diethyl 1,3-dithiolan-2-ylidenephosphoramidate
CAS RN [947024] EC no 2134232 Development codes EI 47 031 (Cyanamid)
Smiles code CCOP(=O)(OCC)N=C1SCCS1
7
H
14
NO
3
PS
2
Form Pale yellow solid.
M.p. 36.5 C; (tech., 3745 C) B.p. 115118 C /0.001 mmHg V.p. 0.031 mPa (20 C)
Solubility In water 650 g/l. Soluble in acetone, benzene, cyclohexane, ethanol, and toluene.
430
phosnichlor
Slightly soluble in diethyl ether. Sparingly soluble in hexane. Stability Stable under neutral
and slightly acidic conditions but hydrolysed at 2>pH>9.
COMMERCIALISATION:
History Insecticide introduced by American Cyanamid Co. Patents GB 974138; FR
1327386
APPLICATIONS:
Biochemistry Cholinesterase inhibitor Mode of action Systemic insecticide and
acaricide with contact and stomach action. Uses Control of lepidopterous larvae
(particularly Spodoptera spp.), sucking insects, and mites on cotton, cabbage, onions,
tobacco, and other crops. Formulation types EC; GR .
PRODUCTS:
Discontinued products Cyalane* (Cyanamid); Cylan* (Cyanamid); Cyolan*
(Cyanamid); Cyolane* (Cyanamid).
ANALYSIS:
Residues determined by glc (N. R. Pasarela & E. J. Orloski, Anal. Methods Pestic. Plant Growth
Regul., 1973, 7, 231).
EHC 63 (1986), a general review of organophosphorus insecticides.
Oral Acute oral LD
50
for male rats 8.9, male mice 12.1 mg/kg. Skin and eye Acute
percutaneous LD
50
for male rabbits 23, male guinea pigs 54 mg/kg. NOEL In 90 d feeding
trials dogs receiving 1 mg/kg daily showed no clinical symptom. Toxicity Class WHO (a.i.)
IaECClassifcation T+; R27/28
ENVIRONMENTAL FATE:
Plants In plants, phosfolan is metabolised at the nitrogen-phosphorus bond to less toxic,
water-soluble compounds.
phosnichlor
Insecticide
IRAC 1B
NOMENCLATURE:
Common name nichlorfos ((m) France); phosnichlor (BSI, E-ISO, (m) F-ISO)
CAS RN [5826766] Smiles code COP(=S)(OC)Oc1ccc(Cl)c(c1)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 297.7 M.f. C
8
H
9
ClNO
5
PS
pindone 431
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Isochlorthion* (Chemagro).
phoxim-methyl
Insecticide
IRAC 1B
NOMENCLATURE:
Common name phoxime-m(thyl) ((f) F-ISO); phoxim-methyl (BSI, E-ISO)
IUPAC name O,O-dimethyl -cyanobenzylideneamino-oxyphosphonothioate; dimethoxyp
hosphinothioyloxyimino(phenyl)acetonitrile
Chemical Abstracts name 3-methoxy-6-phenyl-2,4-dioxa-5-aza-3-phosphapept-5-
ene-7-nitrile 3-sulfde; -[[(dimethoxyphosphinothioyl)oxy]imino]benzeneacetonitrile
CAS RN [14816161] Development codes SRA 7760
Smiles code COP(=S)(OC)ON=C(C#N)c1ccccc1
10
H
11
N
2
O
3
PS
COMMERCIALISATION:
History Superseded dimethyl analogue of phoxim (q.v.). Insecticide evaluated by Bayer AG.
APPLICATIONS:
pindone
Rodenticide
NOMENCLATURE:
Common name no name (Portugal); pival* (former exception, Turkey); pivaldione
(France); pindone (BSI, E-ISO, (f) F-ISO)
IUPAC name 2-pivaloylindan-1,3-dione
O
COC(CH
3
)
3
O
432
piproctanyl bromide
Chemical Abstracts name 2-(2,2-dimethyl-1-oxopropyl)-1H-indene-1,3(2H)-dione
CAS RN [83261] EC no 2014628
Smiles code CC(C)(C)C(=O)C1C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY:
Mol. wt. 230.3 M.f. C
14
H
14
O
3
Form Yellow crystals. M.p. 108.5110.5 C V.p. Very low
Solubility In water 18 mg/l (25 C). Soluble in most organic solvents. Readily soluble in
aqueous alkalis or ammonia to give bright yellow salts. Stability Very stable.
COMMERCIALISATION:
History Insecticidal properties reported by L. B. Kilgore et al. (Ind. Eng. Chem., 1942, 34,
494). Introduced by Kilgore Chemical Co. Patents US 2310949
APPLICATIONS:
Biochemistry Anticoagulant; inhibits blood coagulation by blocking prothrombin
formation. Uses Control of rats and mice, in baits containing 250 mg/kg. Bait shyness
does not occur after feeding. Renders cereal bait resistant to insect infestation and fungal
infection. Formulation types AB; CB; CP; RB . Compatibility Compatible with other
rodenticides.
PRODUCTS:
Discontinued products Pival* (Marman, Motomco); Pivalyn* (sodium salt) (Motomco).
ANALYSIS:
ANALYSIS: by colorimetry (J. B. La Clair, J. Assoc. Off. Agric. Chem., 1955, 38, 299).
EHC 175 (1995). ICSC.515 (2004).
Oral Acute oral LD
50
for rats 280, rabbits 150170, dogs 75100 mg/kg. Chronic oral LD
50

for rabbits 0.52, dogs 2.5, sheep >12 mg/kg daily. Other Acute LD
50
by injection for rats
isc. 50 mg/kg, but it is more toxic when given in small daily doses of 1535 mg/kg. Dogs are
killed by daily doses of 2.5 mg/kg (J. R. Beauregard et al., J. Agric. Food Chem., 1955, 3, 124;
J. P. Saunders et al., ibid., p. 762). Toxicity Class WHO (a.i.) IbECClassifcation T; R25,
R48/25| N; R50, R53
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks 250, bobwhite quail 1560 mg/kg. Fish LC
50
(96
h) for bluegill sunfsh 1.6, rainbow trout 0.21 mg/l.
piproctanyl bromide
NOMENCLATURE:
Common name piproctanyl (for cation) (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-allyl-1-(3,7-dimethyloctyl)piperidinium bromide
piproctanyl bromide 433
Chemical Abstracts name 1-(3,7-dimethyloctyl)-1-(2-propenyl)piperidinium
bromide CAS RN [56717114] piproctanyl bromide; [69309473] piproctanyl
Development codes Ro 060761/000 (Dr Maag); ACR-1222
Smiles code [Br-].CC(C)CCCC(C)CC[N+]1(CC=C)CCCCC1
PHYSICAL CHEMISTRY: Mol. wt. 346.4; (piproctanyl 266.5) M.f. piproctanyl bromide
C
18
H
36
BrN; piproctanyl C
18
H
36
N Form Pale yellow wax. M.p. 75 C
V.p. <5 10
5
mPa (20 C) Solubility Very soluble in water. In methanol >2400, ethanol
2100, acetone 1400 (all in g/l). Practically insoluble in hexane and cyclohexane. Stability In
aqueous solutions, stable for up to 3 years under normal conditions. Stable to hydrolysis at
50 C (pH 3 to pH 13). Stable to light, and up to 100 C.
COMMERCIALISATION:
History Plant growth regulator reported by G. A. Hppi et al. (Experientia, 1976, 32,
37). The bromide introduced by Dr R. Maag Ltd. Patents DE 2459129 (to Hoffmann-La
Roche)
APPLICATIONS:
Mode of action Plant growth regulator, absorbed by the leaves and roots, but not readily
translocated between shoots. Inhibits elongation of internodes, and shortens and stiffens
stems and peduncles. Uses Inhibition of longitudinal growth (to produce more compact
and sturdier plants) in ornamentals, especially chrysanthemums, but also azaleas, fuchsias,
petunias, and calceolarias. Formulation types SL .
PRODUCTS:
Discontinued products Alden* (Dr Maag); Stemtrol* (Dr Maag).
ANALYSIS:
Product analysis by reaction with sodium phenylsulfde to form allyl phenyl sulfde which is
determined by glc. Residues determined in the same way.
Oral Acute oral LD
50
percutaneous LD
50
for rats 115240 mg/kg. Non-irritating to skin (guinea pigs) and eyes
(rabbits). Inhalation LC
50
for rats 1.5 mg/l air. NOEL In 90 d feeding trials, rats receiving
150 mg/kg daily and dogs receiving 25 mg/kg daily showed no signifcant ill-effects.
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and bobwhite quail >10 000 mg/kg diet.
Fish LC
50
(96 h) for rainbow trout 12.7, bluegill sunfsh 62 mg/l. Bees Not toxic to bees.
434
pirimetaphos
piprotal
NOMENCLATURE:
Common name piprotal (ESA)
IUPAC name 5-[bis[2-(2-butoxyethoxy)ethoxy]methyl]-1,3-benzodioxole (I); 1-bis[2-(2-
butoxyethoxy)ethoxy]methyl-3,4-methylenedioxybenzene
Smiles code CCCCOCCOCCOC(OCCOCCOCCCC)c1ccc2OCOc2c1
PHYSICAL CHEMISTRY:
Mol. wt. 456.6 M.f. C
24
H
40
O
8
COMMERCIALISATION:
History Synergist for pyrethrum reported by L. O. Hopkins & D. R. Maciver (Pyrethrum
Post, 1965, 8(2), 3). Introduced by McLaughlin Gormley King Co.
PRODUCTS:
Discontinued products Tropital* (MGK).
pirimetaphos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name pirimetaphos (BSI, E-ISO, (m) F-ISO); pyrim(taphos) (France)
IUPAC name 2-diethylamino-6-methylpyrimidin-4-yl methyl methylphosphoramidate
Chemical Abstracts name 2-(diethylamino)-6-methyl-4-pyrimidinyl methyl
methylphosphoramidate CAS RN [31377692] Development codes SAN I 52 135
Smiles code CCN(CC)c1nc(C)cc(OP(=O)(NC)OC)n1
11
H
21
N
4
O
3
P
COMMERCIALISATION:
History Insecticide evaluated by Sandoz AG.
APPLICATIONS:
pirimiphos-ethyl 435
pirimiphos-ethyl
Insecticide
IRAC 1B
NOMENCLATURE:
Common name pirimiphos-ethyl (BSI, E-ISO, ANSI, BAN, ESA); pyrimiphos-(thyl) ((m)
F-ISO)
IUPAC name O,O-diethyl O-2-diethylamino-6-methylpyrimidin-4-yl phosphorothioate
Chemical Abstracts name O-[2-(diethylamino)-6-methyl-4-pyrimidinyl]
O,O-diethyl phosphorothioate CAS RN [23505411] EC no 2457040
Development codes PP211 Smiles code CCOP(=S)(OCC)Oc1cc(C)nc(n1)N(CC)CC
PHYSICAL CHEMISTRY:
Composition Tech. is 95% pure. Mol. wt. 333.4 M.f. C
13
H
24
N
3
O
3
PS Form Straw-
coloured liquid; (tech. is a clear red-brown liquid with a mercaptan-like odour).
M.p. 1518 C (tech.) B.p. Decomposes abovec. 194 C V.p. 0.68 mPa (20 C); 39 mPa
(25 C) K
ow
logP = 5.0 (unionised) S.g./density 1.14 (20 C) Solubility In water 2.3 mg/l
(pH 7.2). Miscible with most organic solvents. Stability Stable for at least 1 year at room
temperature, and for at least 5 days at 80 C. Hydrolysed by acid and base; DT
50
(25 C)
521200 d (pH range 5.58.5), most stable pH 78. F.p. >60 C
COMMERCIALISATION:
History Superseded diethyl homologue of pirimiphos-methyl (q.v.). Insecticide introduced
by ICI Plant Protection Division (later Zeneca Agrochemicals). Patents GB 1019227; GB
1205000 Manufacturers Hunan Haili
APPLICATIONS:
respiratory action. Uses Broad-spectrum control of Diptera and Coleoptera soil pests
and some foliar pests on bananas and other fruit, feld crops, ornamentals, turf, vegetables,
etc. Also used as a seed treatment, and in compost to control sciarid and phorid fies on
mushrooms. Phytotoxicity Phytotoxic at high rates of seed dressing.
Formulation types DS; EC; GR; CG.
PRODUCTS:
Discontinued products Fernex* (Zeneca); Primicid* (Zeneca); Solgard* (Zeneca).
ANALYSIS:
Product analysis by glc with FID (CIPAC Handbook, 1988, D, 146). Identity also by glc, tlc, i.r.
O
P(OCH
2
CH
3
)
2
S
N
N
(CH
3
CH
2
)
2
N
CH
3
436
polychloroterpenes
or nmr (CIPAC Handbook, 1994, F, 406). Residues determined by glc with FPD or FTD (D. J.
W. Bullock, Anal. Methods Pestic. Plant Growth Regul., 1976, 8, 171).
Oral Acute oral LD
50
for rats 140200, guinea pigs 50100, cats 2550 mg/kg.
50
for male rats 10002000 mg/kg. Non-irritating to
skin; may cause eye irritation (rabbits). Not a skin sensitiser (guinea pigs).
Inhalation LC
50
(6 h) for rats >5 ppm (no toxic effects over 3 w). NOEL (90 d) for rats
1.6 mg/kg diet (0.08 mg/kg daily); for dogs 0.2 mg/kg daily. For rats receiving 27 mg/kg diet
(1.6 mg/kg daily) and dogs 2 mg/kg daily, the only effect was on the cholinesterase levels.
Toxicity Class WHO (a.i.) Ib EPA (formulation) II ECClassifcation T; R25| Xn; R21| N;
R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks 2.5, bobwhite quail 1020 mg/kg. Fish LC
50
(96 h)
for common carp 0.22, brown trout 0.02 mg/l. Daphnia LC
50
(48 h) 0.3 g/l. Bees Toxic
to bees.
ENVIRONMENTAL FATE:
50
2170 d (non-sterile, aerobic, o.m. 1.86.3%, pH 6.07.5).
For details of persistence in soil, see D. L. Suett, Pestic. Sci., 1975, 6, 385.
polychlorodicyclopentadiene isomers
NOMENCLATURE:
IUPAC name polychlorodicyclopentadiene isomers
CAS RN [8029296]
COMMERCIALISATION:
History Insecticide and herbicide introduced by Velsicol Chemical Corp.
PRODUCTS:
Discontinued products Bandane* (Velsicol).
polychloroterpenes
NOMENCLATURE:
IUPAC name heptachloro-2,2-dimethyl-3-methylene-8,9,10-trinorbornane
polynactins 437
Chemical Abstracts name chlorinated mixed terpenes Other names terpene
polychlorinates CAS RN [8001501] Development codes Compound 3961
PHYSICAL CHEMISTRY:
Mol. wt. 379.4 M.f. C
10
H
11
Cl
7
(65% Cl)
COMMERCIALISATION:
History Insecticidal and acaricidal activity of this reaction mixture described by D. L. Kent
et al. (Soap Chem. Spec., 1953, 19(6), 157). Introduced by Goodrich Chemical Co.
PRODUCTS:
Discontinued products Strobane* (Goodrich).
ANALYSIS:
Product analysis by tlc (AOAC Methods 18th Ed., 972.05).
IARC Monographs Programme on the Evaluation of Carcinogenic Risks (1974) 5. IARC 5
(1974).
IARC Class 3
polynactins
Acaricide
NOMENCLATURE:
IUPAC name [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28
S*,29S*,32S*,34S*)]-5,14,23,32-tetraethyl-2,11,20,29-tetramethyl-4,13,22,31,37,38,3-
9,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
(tetranactin); [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S
*,29S*,32S*,34S*)]-5,14,23-triethyl-2,11,20,29,32-pentamethyl-4,13,22,31,37,38,39,-
40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
(trinactin); [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,
O
CH
3
O
O
R
4
O
O
CH
3
O
O
R
2
O
O
CH
3
O
R
1
O
CH
3
O
R
3
dinactin: R
1
, R
3
= CH
3
- ; R
2
, R
4
= CH
3
CH
2
-
tetranactin: R
1
, R
2
, R
3
, R
4
= CH
3
CH
2
-
trinactin: R
1
= CH
3
- ; R
2
, R
3
, R
4
= CH
3
CH
2
-
438
potassium cyanate
29S*,32S*,34S*)]-5,23-diethyl-2,11,14,20,29,32-hexamethyl-4,13,22,31,37,38,39,40-
-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone (dinactin)
Chemical Abstracts name [1R(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,2
5R*,28S*,29S*,32S*,34S*)]-5,14,23,32-tetraethyl-2,11,20,29-tetramethyl-4,13,22,31,37,38,3-
9,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
(tetranactin) Other names tetranactin; trinactin; dinactin CAS RN [33956615]
tetranactin; [7561719] trinactin; [20261852] dinactin; [39285046] polynactin,
formerly [56485451] and [56573638] Smiles code tetranactin, without
stereochemistry:CCC1CC2CCC(O
2
)C(C)C(=O)OC(CC)CC3CCC(O3)C(C)C(=O)
OC(CC)CC4CCC(O4)C(C)C(=O)OC(CC)CC5CCC(O5)C(C)C(=O)O1
PHYSICAL CHEMISTRY:
Composition A mixture of tetranactin, trinactin and dinactin. Mol. wt. 793.1
(tetranactin); 779.0 (trinactin); 765.0 (dinactin) M.f. C
44
H
72
O
12
(tetranactin); C
43
H
70
O
12

(trinactin); C
42
H
68
O
12
(dinactin) M.p. 111112 C Solubility In water 0.02 g/l (25 C).
In acetone 56, methanol 17, benzene 387, xylene 243, hexane 8 (all in g/l, 25 C).
COMMERCIALISATION:
Production By fermentation of Streptomyces aureus S-3466.
APPLICATIONS:
Biochemistry Thought to act through leakage of cations through the lipid layer of the
mitochondrial membrane. Uses For control of spider mites in fruit trees.
PRODUCTS:
Discontinued mixtures Mitecidin* (+ fenobucarb) (Eiko Kasei); Mitedown*
(+ fenbutatin oxide) (Eiko Kasei).
Oral Acute oral LD
50
for mice >15 000 mg/kg. Skin and eye Acute percutaneous LD
50
for
mice >10 000 mg/kg. Mild skin and eye irritant. Toxicity Class EPA (formulation) IV
ECOTOXICOLOGY:
Fish TLm for carp 0.003 ppm.
potassium cyanate
Herbicide
NOMENCLATURE:
IUPAC name potassium cyanate (I)
Smiles code [K+].[O-]C#N
PHYSICAL CHEMISTRY:
Mol. wt. 81.12 M.f. CKNO Form Colourless crystals. S.g./density 2.056 (20 C)
Solubility In water 630 g/l (10 C), 720 g/l (70 C).
potassium phosphates 439
Stability Slowly hydrolysed in aqueous solution to form ammonia and potassium
bicarbonate.
COMMERCIALISATION:
History Introduced as herbicide by American Cyanamid Co.
APPLICATIONS:
Mode of action Total herbicide. Formulation types SP.
PRODUCTS:
Discontinued products Aerocyanate* (Cyanamid).
ANALYSIS:
Product analysis by conversion to an insoluble derivative which is weighed
(CIPAC Handbook, 1985, 1C, 2200; AOAC Methods, 18th Ed., 952.01).
potassium phosphates
Fungicide
NOMENCLATURE:
Chemical Abstracts name monopotassium phosphate
Other names potassium dihydrogen phosphate; potassium monophosphate; dipotassium
phosphate; dipotassium hydrogen phosphate CAS RN [7778770] monopotassium salt;
[7758114] dipotassium salt
PHYSICAL CHEMISTRY:
Mol. wt. 136.1 (monopotassium salt); 174.2 (dipotassium salt) M.f. H
2
KO
4
P; HK
2
O
4
P
Form Crystalline powder. M.p. >465 C (dipotassium salt) Solubility In water 150 g/100
g. (dipotassium salt)
COMMERCIALISATION:
History The dipotassium salt was frst registered in USA in 2002.
Manufacturers Lidochem
APPLICATIONS:
Mode of action The dipotassium salt may act both by direct toxicity to the pathogen and
also, through its fertiliser action, by stimulating the plants natural defences.
Uses The monopotassium salt is for control of powdery mildew in fruit and vegetables.
Also used as a fertiliser, and as a buffering agent in pesticide formulations. The dipotassium
salt is for control of powdery mildews, Downy mildews, leaf spot, root rot, etc in woody
ornamentals, turf, grapes, and fruit and nut trees which are not yet bearing.
PRODUCTS:
Other products Nutrol (dihydrogen phosphate) (Lidochem);
Discontinued products eKsPunge* (dihydrogen phosphate) (Lidochem).
440
proclonol
ICSC.608 (potassium dihydrogen phosphate; 2005).
Oral Acute oral LD
50
for male rats >5000, female rats >500 mg/kg (dihydrogen phosphate).
50
for rabbits >2000 mg/kg. Not a skin irritant; a mild
eye irritant (dihydrogen phosphate).
primidophos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name prymidophos ((m) France); primidophos (BSI, E-ISO, (m) F-ISO)
IUPAC name O,O-diethyl O-(2-N-ethylacetamido-6-methylpyrimidin-4-yl)
phosphorothioate; N-(4-diethoxyphosphinothioyloxy-6-methylpyrimidin-2-yl)-N-
ethylacetamide
Chemical Abstracts name O-[2-(acetylethylamino)-6-methyl-4-pyrimidinyl] O,O-
diethyl phosphorothioate CAS RN [39247966] Development codes PP484
Smiles code CCOP(=S)(OCC)Oc1cc(C)nc(n1)N(CC)C(=O)C
PHYSICAL CHEMISTRY:
Mol. wt. 347.4 M.f. C
13
H
22
N
3
O
4
PS
COMMERCIALISATION:
History Insecticide evaluated by ICI Plant Protection Division (later ICI Agrochemicals).
APPLICATIONS:
proclonol
Acaricide
NOMENCLATURE:
Common name proclonol (BAN, JMAF)
IUPAC name 4,4-dichloro--cyclopropylbenzhydrol
Chemical Abstracts name 4-chloro--(4-chlorophenyl)--cyclopropylbenzenemethanol
CAS RN [14088712] Development codes R-8284 (Janssen)
Smiles code OC(C1CC1)(c2ccc(Cl)cc2)c3ccc(Cl)cc3
PHYSICAL CHEMISTRY:
Mol. wt. 293.2 M.f. C
16
H
14
Cl
2
O
profuazol 441
COMMERCIALISATION:
History Acaricide introduced by Janssen Pharmaceutica, N.V.
PRODUCTS:
Discontinued products Kilacar* (Asepta).
procyazine
Herbicide
NOMENCLATURE:
Common name procyazine (BSI, E-ISO, (f) F-ISO, ANSI)
IUPAC name 2-(4-chloro-6-cyclopropylamino-1,3,5-triazin-2-ylamino)-2-
methylpropiononitrile
Chemical Abstracts name 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-triazin-2-yl]amino]-
2-methylpropanenitrile CAS RN [32889488] Development codes CGA 18 762
Smiles code CC(C)(Nc1nc(Cl)nc(NC2CC2)n1)C#N
PHYSICAL CHEMISTRY:
Mol. wt. 252.7 M.f. C
10
H
13
ClN
6
COMMERCIALISATION:
History Herbicide introduced by Ciba-Geigy AG.
ANALYSIS:
See Pestic. Anal. Man., I, 302.
profuazol
Herbicide
HRAC E WSSA 14
NOMENCLATURE:
Common name profuazol (BSI, E-ISO, (m) F-ISO)
IUPAC name 1,2-dichloro-4-fuoro-5-[(6S,7aR)-6-fuoro-2,3,5,6,7,7a-hexahydro-1,3-
dioxo-1H-pyrrolo[1,2-c]imidazol-2-yl]methanesulfonanilide
Chemical Abstracts name 1-chloro-N-[2-chloro-4-fuoro-5-[(6S,7aR)-
6-fuorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]phenyl]
methanesulfonamide CAS RN [190314433] Development codes IN-TY029; DPX-
TY029 (DuPont)
PHYSICAL CHEMISTRY:
Mol. wt. 414.2 M.f. C
13
H
11
Cl
2
F
2
N
3
O
4
S
COMMERCIALISATION:
History Herbicide developed by E. I. du Pont de Nemours & Co.
442
profuralin
APPLICATIONS:
Biochemistry Inhibitor of protoporphyrinogen oxidase.
profuralin
Herbicide
NOMENCLATURE:
Common name profuralin (BSI, E-ISO, ANSI, WSSA); profuraline ((f) F-ISO)
IUPAC name N-(cyclopropylmethyl)-,,-trifuoro-2,6-dinitro-N-propyl-p-toluidine;
N-cyclopropylmethyl-2,6-dinitro-N-propyl-4-trifuoromethylaniline
Chemical Abstracts name N-(cyclopropylmethyl)-2,6-dinitro-N-propyl-4-
(trifuoromethyl)benzenamine CAS RN [26399360] EC no 2476566
Development codes CGA 10 832
Smiles code CCCN(CC1CC1)c2c(cc(cc2[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 347.3 M.f. C
14
H
16
F
3
N
3
O
4
Form Yellow-orange crystals. M.p. 32.132.5 C
V.p. 8.4 mPa (20 C) Henry 2.92 101 Pa m
3
mol
1
Solubility In water 0.1 mg/l (20 C). In n-octanol 220 g/l (20 C); readily soluble in most
organic solvents, e.g. ethanol, acetone, xylene, and n-hexane. Stability Stable for at least
3 years under normal storage conditions. Solutions are slowly hydrolysed at 100 C; DT
50

6 h (pH 3, pH 7 and pH 10). Decomposed by uv light. Decomposes atc. 180 C.
COMMERCIALISATION:
History Herbicide reported by T. D. Taylor et al. (Annu. Meet. Weed Sci. Soc. Am., 1973,
Abstr. 169). Introduced by Ciba-Geigy AG. Patents US 3546295
APPLICATIONS:
Mode of action Selective herbicide, absorbed by the roots and shoots. Uses Control
of annual and perennial broad-leaved and grass weeds in cotton, soya beans, brassicas,
capsicums, tomatoes, and other crops. Applied pre-planting by soil incorporation at
0.751.5 kg/ha. Phytotoxicity Small grains, sorghum, maize, beet and direct-seeded
tomatoes are sensitive. Formulation types EC.
PRODUCTS:
Discontinued products Pregard* (Ciba-Geigy); Tolban* (Ciba-Geigy).
ANALYSIS:
Product analysis by glc with FID (R. A. Kahrs, Anal. Methods Pestic. Plant Growth Regul., 1978,
10, 451). Residues determined by glc with ECD or MCD (idem, ibid.).
F
3
C
NO
2
NO
2
N
CH
2
CH
2
CH
2
CH
3
proglinazine-ethyl; proglinazine 443
Oral Acute oral LD
50
for ratsc. 10 000 mg/kg. Skin and eye Acute percutaneous LD
50
for
rabbits >4000, rats >3170 mg/kg. Non-irritating to skin; moderate eye irritant (rabbits).
Inhalation LC
50
(4 h) for rats >3.97 mg/l air. NOEL (90 d) for rats 200 mg/kg diet (c.
13 mg/kg daily); for dogs 600 mg/kg diet (c. 20 mg/kg daily). Toxicity Class WHO (a.i.) U
ECClassifcation Xi; R36| N; R50, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail and mallard ducks 1000 mg/kg. Fish LC
50
(96 h)
for bluegill sunfsh 0.023, trout 0.015 mg/l. Bees Toxic to honeybees.
ENVIRONMENTAL FATE:
Animals For details of metabolites see A. R. Jacobson and J. T. Gerig (Chem Res. Toxicol.
1988, 1, 304). Plants Minute quantities of polar metabolites are produced in cotton and
soya beans. Soil/Environment Degraded by soil micro-organisms. No signifcant leaching
through the soil.
proglinazine-ethyl; proglinazine
Herbicide
NOMENCLATURE:
Common name proglinazine (for the acid) (BSI, E-ISO, (f) F-ISO, WSSA)
IUPAC name N-(4-chloro-6-isopropylamino-1,3,5-triazin-2-yl)glycine (for the acid)
Chemical Abstracts name N-[4-chloro-6-[(1-methylethyl)amino]-1,3,5-triazin-
2-yl]glycine (for the acid) CAS RN [68228182] ester; [68228206] acid
Development codes MG-07 (acid) (Nitrokmia)
PHYSICAL CHEMISTRY:
Composition Tech. isc. 94%. Mol. wt. 273.3 (ester); 245.7 (acid) M.f. ester C
10
H
16
ClN
5
O
2
;
acid C
8
H
12
ClN
5
O
2
Form Colourless crystals (ester). M.p. 110112 C (ester)
V.p. 0.27 mPa (20 C) (ester) Solubility In water 750 mg/l (25 C, ester). In acetone 500,
hexane 35, xylene 100 (all in g/l, 25 C, ester). Stability Decomposes at 160 C; stable to
light. Stable at room temperature (pH 58), but on heating is hydrolysed by acid or alkali to
the corresponding herbicidally-inactive hydroxytriazine.
COMMERCIALISATION:
History The ethyl ester introduced as a herbicide by Nitrokmia Ipartelepek.
N N
N Cl NHCH
2
CO
2
H
(CH
3
)
2
CHNH
444
promacyl
APPLICATIONS:
site. Mode of action Selective herbicide. Uses Pre-emergence control of seedling weeds
(particularly broad-leaved) in maize at 4 kg/ha. Formulation types WP
ANALYSIS:
Oral Acute oral LD
50
for rats and mice >8000, rabbits >3000, guinea pigs 857923 mg/
kg. Skin and eye Acute percutaneous LD
50
for rabbits >4000, rats >1500 mg/kg. Non-
irritating to skin and eyes (rabbits). Moderate skin sensitisation (guinea pigs). Other Acute
i.p. LD
50
for rats 829891, mice 7201080 mg/kg. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
Soil/Environment Degraded in soil, DT
50
5670 d.
promacyl
IRAC 1A
NOMENCLATURE:
Common name promacyl (Australia)
IUPAC name 5-methyl-m-cumenyl butyryl(methyl)carbamate
Chemical Abstracts name 3-methyl-5-(1-methylethyl)phenyl methyl(1-
oxobutyl)carbamate Other names promecarb A CAS RN [34264249]
Development codes CRC 7320
Smiles code CCCC(=O)N(C)C(=O)Oc1cc(C)cc(c1)C(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 277.4 M.f. C
16
H
23
NO
3
Form Tech. is a clear amber to dark brown liquid.
B.p. 158 C /5 mmHg V.p. 400 Pa (149 C) S.g./density 0.996 (20 C)
Solubility Sparingly soluble in water. Miscible with aliphatic and aromatic hydrocarbons,
alcohols, esters, ethers, ketones. Stability Stable 200 C; also unchanged after 300 d at
50 C.
COMMERCIALISATION:
History Insecticide and ixodicide introduced by ICI Australia (later Crop Care Australasia
Pty Ltd). Patents AU 441004; AU 454280
OCONCOCH
2
CH
2
CH
3
CH
3
CH(CH
3
)
2
CH
3
promecarb 445
APPLICATIONS:
Biochemistry Cholinesterase inhibitor Uses Effective for controlling Boophilus
microplus on cattle by sprays or plunge dips. Also controls Haemaphysalis longicornis,
Haematobia irritans exigua and Ixodes holocyclus on cattle and horses.
PRODUCTS:
Discontinued products Promicide* (ICI Australia).
ANALYSIS:
Product analysis by glc (D. Gunew, Anal. Methods Pestic. Plant Growth Regul., 1980, 11, 139).
Residues in cattle determined by glc (D. E. Clegg & P. R. Martin, Pestic. Sci., 1973, 4, 447).
Oral Acute oral LD
50
for female rats 1220, female mice 20004000, female guinea pigs 250,
female rabbits 8000 mg/kg. Skin and eye Acute percutaneous LD
50
for female rats >4000
mg/kg. Slight irritant to skin (rats). Inhalation No toxic sign in rats exposed to saturated
atmosphere for 6 h/d each 5 d/w for 3 w. NOEL (2 y) for rats 500 mg/kg diet.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hens 40008000 mg/kg.
promecarb
Insecticide
IRAC 1A
NOMENCLATURE:
Common name promecarb (BSI, E-ISO, ESA, JMAF); prom(carbe) ((m) F-ISO)
IUPAC name 5-methyl m-cumenyl methylcarbamate; 3-isopropyl-5-methylphenyl
methylcarbamate
Chemical Abstracts name 3-methyl-5-(1-methylethyl)phenyl methylcarbamate
CAS RN [2631370] EC no 2201130 Development codes SN 34 615; SSI 0792
Smiles code CNC(=O)Oc1cc(C)cc(c1)C(C)C
PHYSICAL CHEMISTRY:
12
H
17
NO
2
CH
3
CH(CH
3
)
2
OCONHCH
3
446
promecarb
M.p. 8787.5 C B.p. 117 C /0.01 mmHg V.p. 1.4 mPa (25 C) K
ow
logP = 3.189 (pH 4)
Henry 3.19 10
3
Pa m
3
mol
1
(calc.) Solubility In water 91 mg/l (pH 45, 25 C). Readily
soluble in organic solvents, e.g. in acetone, DMF, dichloroethane 400600, cyclohexanol,
cyclohexanone, isopropanol, isobutanol, methanol 200400, carbon tetrachloride, xylene
100200 (all in g/l, 25 C). Stability Hydrolysed by strong acids and alkalis, DT
50
(22 C)
103 d (pH 7), 36 h (pH 9), stable at pH 5. Stable 250 C, and >140 h at 50 C.
COMMERCIALISATION:
History Insecticide reported by A. Formigoni & G. P. Bellini (Congr. Int. Antiparassitari,
Naples, 1965) and by A. Jger (Z. Angew. Entomol., 1966, 58, 188). Introduced by Schering
AG (later AgrEvo GmbH). Patents DE 1156272
APPLICATIONS:
with contact and stomach action; has good initial knockdown of insects. Uses Control of
sucking and chewing insects (Colorado Beetles and other Coleoptera, aphids, Lepidoptera
larvae, leaf miners, etc.) in potatoes, maize, pome fruit, stone fruit, and citrus fruit.
Formulation types EC; WP. Compatibility Incompatible with alkaline materials.
PRODUCTS:
Discontinued products Carbamult* (AgrEvo).
ANALYSIS:
Product analysis by hplc Residues determined by glc with ECD of a derivative.
Oral Acute oral LD
50
percutaneous LD
50
for rabbits >2025 mg/kg; (50% WP formulation) for rats and rabbits
>1000 mg/kg. Inhalation LC
50
(4 h) for rats >0.16 mg/l air. NOEL (1.5 y) for rats >20 mg/
kg. Toxicity Class WHO (a.i.) II EPA (formulation) II ECClassifcation T; R25| N; R50,
R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 78, mallard ducks 3.5 mg/kg. Fish LC
50
(96 h) for
rainbow trout 0.3, bluegill sunfsh 0.64 mg/l; (72 h) for carp 4.3 mg/l; (120 h) for European
trout 1.2 mg/l. Bees Toxic to bees; LD
50
0.0011 mg/bee.
ENVIRONMENTAL FATE:
Animals In mammals, the substituted phenol moiety is eliminated after condensation
with glucuronic acid. Metabolism of carbamate insecticides is reviewed (M. Cool & C.
K. Jankowski in Insecticides). Soil/Environment Presumably, as for other carbamates,
cleavage of the N-methylcarbamate moiety and decomposition into CO
2
and methylamine.
Soil DT
50
<28 d (lab. and feld studies). Soil adsorption Kd 1.72 (2.64% o.c., pH 6.0), 1.63
(1.01% o.c., pH 6.7).
propaphos 447
propaphos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name propaphos (BSI, JMAF, E-ISO); propafos ((m) F-ISO)
IUPAC name 4-(methylthio)phenyl dipropyl phosphate
Chemical Abstracts name 4-(methylthio)phenyl dipropyl phosphate
Other names DPMP CAS RN [7292162] Development codes NK-1158 (Nippon
Kayaku) Smiles code CCCOP(=O)(OCCC)Oc1ccc(SC)cc1
13
H
21
O
4
PS Form Colourless liquid.
B.p. 175177 C /0.85 mmHg V.p. 0.12 mPa (25 C) K
ow
logP = 3.67
Henry 2.92 10
4
Pa m
3
mol
1
125 mg/l (25 C). Soluble in most organic solvents. Stability Stable <230 C; stable in
neutral and acidic media, but is slowly decomposed in alkaline media.
COMMERCIALISATION:
History Insecticide reported (Jpn. Pestic. Inf., 1970, No. 4, p. 7). Introduced by Nippon
Kayaku Co., Ltd and frst marketed in Japan in 1973. Patents JP 482500; JP 462729
Manufacturers Nippon Kayaku
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic insecticide
with contact and stomach action. Uses Control of Chilo suppressalis, Laodelphax
striatella, Nephotettix cincticeps, Oulema oryzae (including strains resistant to other
organophosphorus and carbamate insecticides) in paddy rice. Applied at 35 g/rice nursery
tray. Formulation types DP; GR .
PRODUCTS:
Discontinued products Kayaphos* (Nippon Kayaku); Discontinued mixtures Fuji-
One Kayaphos Oncol* (+ benfuracarb + isoprothiolane) (Nihon Nohyaku).
ANALYSIS:
Product and residue analysis by glc (S. Asaka et al., Noyaku Kagayu, 1975, 3, 36).
EHC 63 (1986) is a general review of organophosphorus insecticides. J. Pestic. Sci., 1989, 14,
511515. EU Status (1107/2009) Never notifed to the EU.
Oral Acute oral LD
50
for rats 70, mice 90, rabbits 82.5 mg/kg. Skin and eye Acute
O
P(OCH
2
CH
2
CH
3
)
2
O
CH
3
S
448
propyl 3-tert-butylphenoxyacetate
percutaneous LD
50
for rats 88.5 mg/kg. Inhalation LC
50
for rats 39.2 mg/m
3
. NOEL (2 y)
for rats 0.08, mice 0.05 mg/kg b.w. Toxicity Class WHO (a.i.) Ib
ECOTOXICOLOGY:
Birds LD
50
for chickens 2.55.0 mg/kg. Fish LC
50
(48 h) for carp 4.8 mg/l. Daphnia Toxic.
Bees Toxic to bees.
ENVIRONMENTAL FATE:
Plants For metabolism in plants, see Y. Fujii et al., J. Pestic. Sci., 1980, 5(1), 5562.
propyl 3-tert-butylphenoxyacetate
NOMENCLATURE:
IUPAC name propyl 3-tert-butylphenoxyacetate
Chemical Abstracts name propyl [3-(1,1-dimethylethyl)phenoxy]acetate
CAS RN [66227096] Development codes M&B 25 105
Smiles code CCCOC(=O)COc1cccc(c1)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 250.3 M.f. C
15
H
22
O
3
Form Colourless liquid with a characteristic odour. B.p.
162 C /20 mmHg Solubility Sparingly soluble in water.
COMMERCIALISATION:
History Plant growth-regulating properties reported by C. J. Hibbitt & J. A. Hardisty
(Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1979, 44, 835). Introduced by May & Baker Ltd
(later Rhne-Poulenc Agrochimie). Patents GB 1524320
APPLICATIONS: Uses Promotes lateral branching in maiden and young non-cropping
apple and pear trees by temporarily inhibiting the growth of the apical meristem.
PRODUCTS:
Discontinued products M&B 25105* (Hortichem).
ANALYSIS:
Oral Acute oral LD
50
50
for rats
>2000 mg/kg. Moderate irritant to skin and eyes (rabbits).
prothidathion 449
propyl isome
NOMENCLATURE:
Common name propyl isome (ESA)
IUPAC name dipropyl 5,6,7,8-tetrahydro-7-methylnaphtho[2,3-d]-1,3-dioxole-5,6-
dicarboxylate (I); dipropyl 1,2,3,4-tetrahydro-3-methyl-6,7-methylenedioxynaphthalene-1,2-
dicarboxylate
Chemical Abstracts name (I) Other names dipropyl maleate isosafrole condensate
CAS RN [83590] Smiles code CCCOC(=O)C1C(C)Cc2cc3OCOc3cc2C1C(=O)
OCCC
20
H
26
O
6
COMMERCIALISATION:
History Synergist for pyrethrum reported by M. E. Synerholm & A. Hartzell (Contr. Boyce
Thompson Inst., 1945, 14, 79). Introduced by S. B. Penick & Co.
Toxicity Class WHO (a.i.) OECClassifcation T; R24| Xn; R22| N; R50, R53
prosulfalin
Herbicide
NOMENCLATURE:
Common name prosulfaline ((m) F-ISO); prosulfalin (BSI, E-ISO, ANSI, WSSA)
IUPAC name N-(4-dipropylamino-3,5-dinitrophenylsulfonyl)-S,S-dimethylsulfmide
Chemical Abstracts name N-[[4-(dipropylamino)-3,5-dinitrophenyl]sulfonyl]-S,S-
dimethylsulflimine CAS RN [51528031]
Smiles code CCCN(CCC)c1c(cc(cc1[N+](=O)[O-])S(=O)(=O)N=S(C)C)[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 406.5 M.f. C
14
H
22
N
4
O
6
S
2
COMMERCIALISATION:
History Herbicide evaluated by Eli Lilly & Co.
prothidathion
Acaricide
IRAC 1B
NOMENCLATURE:
Common name prothidathion (BSI, E-ISO, (m) F-ISO)
IUPAC name S-2,3-dihydro-5-isopropoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-diethyl
450
prothiocarb; prothiocarb hydrochloride
phosphorodithioate; 3-diethoxyphosphinothioylthiomethyl-5-isopropoxy-1,3,4-thiadiazol-
2(3H)-one
Chemical Abstracts name O,O-diethyl S-[[5-(1-methylethoxy)-2-oxo-1,3,4-thiadiazol-
3(2H)-yl]methyl] phosphorodithioate CAS RN [20276839]
Development codes GS 13 010
Smiles code CCOP(=S)(OCC)SCn1nc(OC(C)C)sc1=O
10
H
19
N
2
O
4
PS
3
COMMERCIALISATION:
History Acaricide evaluated by J. R. Geigy S.A. (later Ciba-Geigy AG).
APPLICATIONS:
prothiocarb; prothiocarb hydrochloride
Fungicide
FRAC 28, F4; carbamate fungicide
NOMENCLATURE:
Common name prothiocarbe ((m) F-ISO); prothiocarb (BSI, E-ISO)
IUPAC name S-ethyl (3-dimethylaminopropyl)thiocarbamate
Chemical Abstracts name S-ethyl [3-(dimethylamino)propyl]carbamothioate
CAS RN [19622083] prothiocarb; [19622196] hydrochloride EC no 2431939
hydrochloride Development codes SN 41 703 (Schering)
PHYSICAL CHEMISTRY:
Composition Tech. is 95%. Mol. wt. 190.3; (hydrochloride 226.8) M.f. C
8
H
18
N
2
OS;
(hydrochloride C8H19ClN
2
OS) Form Prothiocarb hydrochloride is a hygroscopic,
colourless, odourless crystalline solid; (tech. has a strong odour). M.p. 120121 C
(hydrochloride) V.p. 0.0019 mPa (25 C, hydrochloride) Henry hydrochloride: 4 10
1
0
Pa m
3
mol
1
(calc.) Solubility Hydrochloride: In water 890 g/l (23 C). In benzene, hexane
<0.15, chloroform 100, methanol 680 (all in g/l, 23 C).
COMMERCIALISATION:
History Fungicide reported by M. G. Bastiaansen et al. (Meded. Fac. Landbouwwet. Rijksuniv.
Gent, 1974, 39, 1019). The hydrochloride introduced by Schering AG. Patents DE 1567169.
APPLICATIONS:
Biochemistry Proposed mode of action is affecting cell membrane permeability, by
inhibiting fatty acid biosynthesis. Mode of action Systemic fungicide, taken up by the
roots and translocated to the aerial parts. Uses Prothiocarb hydrochloride is a soil-applied
fungicide with a specifc action against Phycomycetes, e.g. Phytophthora, Pythium spp. It was
only recommended for ornamental crops, mainly as a protective fungicide.
Formulation types SL (hydrochloride).
prothoate 451
PRODUCTS:
Discontinued products Dynone* (Schering); Previcur* (hydrochloride) (Schering).
ANALYSIS:
Product analysis by argentometric titration of the ethanethiol liberated by hydrolysis.
Residues determined by the fuorimetric measurement of the N,N-dimethylpropane-1,3-
diamine liberated by alkaline hydrolysis.
EHC 76 (1988) is a general review of thiocarbamates. EU Status (1107/2009) Not
Oral Hydrochloride: Acute oral LD
50
for rats 1300, mice 6601200 mg/kg.
50
for rats >1470, rabbits >980 (both as mg a.i. as
formulation/kg). NOEL (90 d) for rats 0.5 mg/kg diet, for dogs 1.8 mg/kg diet.
Toxicity Class WHO (a.i.) OECClassifcation Xn; R22| N; R51, R53 (hydrochloride)
prothoate
IRAC 1B
NOMENCLATURE:
Common name prothoate (BSI, E-ISO, (m) F-ISO)
IUPAC name O,O-diethyl S-isopropylcarbamoylmethyl phosphorodithioate;
2-diethoxyphosphinothioylthio-N-isopropylacetamide
Chemical Abstracts name O,O-diethyl S-[2-[(1-methylethyl)amino]-2-oxoethyl]
phosphorodithioate Other names trimethoate CAS RN [2275185]
EC no 2188932 Development codes E.I. 18 682 (Cyanamid); L 343 (Montedison)
Smiles code CCOP(=S)(OCC)SCC(=O)NC(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 285.4 M.f. C
9
H
20
NO
3
PS
2
Form Colourless crystals with a camphor-like odour;
(tech. is an amber to yellow semi-solid). M.p. 28.5 C; (tech.: 2124 C) V.p. 13 mPa
(40 C) S.g./density 1.151 (32 C) Solubility In water 2.5 g/l (20 C, tech.). Miscible
with most organic solvents e.g. hexane, cyclohexane, higher petroleum FRACtions <30,
light petroleum <20, glycerol <10 (all in g/kg, 20 C). Stability Stable at 4.0<pH<8.2, but
decomposed at 50 C inc. 48 h at pH 9.2. Tech. is stable to light and at 60 C. F.p. 160 C
S
P(OCH
2
CH
3
)
2
S
CH
2
C
(CH
3
)
2
CHNH
O
452
proxan; proxan-sodium
COMMERCIALISATION:
History Insecticide reported (Ital. Agric., 1955, 99, 747). Discovered by American
Cyanamid Co. and later introduced by Montecatini S.p.A. (later Agrimont S.p.A.).
Patents US 2494283 (to Cyanamid); GB 791824 (to Montedison)
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic acaricide and
insecticide with contact and stomach action. Uses Control of mites, aphids, thrips, Lace
bugs, and other sucking insect pests on a range of crops, including fruit trees, citrus,
vegetables, cotton, ornamentals, sugar beet, sugar cane, tobacco, and vines.
Formulation types EC; WP; SL; DP; GR . Compatibility Not compatible with highly
alkaline materials.
PRODUCTS:
Discontinued products Fac* (Agrimont); Discontinued mixtures Erysit Super*
(+ chlorfenson) (Schering); Fac Super* (+ chlorfenson) (Sopra).
ANALYSIS:
Product analysis by glc (B. Bazzi, Anal. Methods Pestic. Plant Growth Regul., 1976, 8, 213).
Residues on crops are determined by glc (B. Bazzi, loc. cit.; B. Bazzi et al., Pestic. Sci., 1974, 5,
511).
Oral Acute oral LD
50
for male rats 8.0, female rats 8.9, mice 19.820.3 mg/kg.
50
for rats 655, rabbits 100200 mg/kg.
Inhalation LC
50
(4 h) for rats 0.0029 mg/l air. NOEL (90 d) for rats 0.5 mg/kg daily, for
mice 1 mg/kg daily. Toxicity Class WHO (a.i.) Ia EPA (formulation) I
ECClassifcation T+; R27/28| R52, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for bobwhite quail 22.5 mg/kg, pheasants 18.8 mg/kg, wild ducks
11.9 mg/kg. Fish LC
50
(96 h) for goldfsh 33, trout 20, guppies 14 mg/l. Bees Dangerous to
bees.
proxan; proxan-sodium
Herbicide
NOMENCLATURE:
Common name proxan (E-ISO from 1990, BSI, Canada, New Zealand); proxane ((m)
F-ISO from 1990); IPX (WSSA)
IUPAC name O-isopropyl hydrogen dithiocarbonate
proximpham 453
Chemical Abstracts name O-(1-methylethyl) hydrogen carbonodithioate
CAS RN [108258] proxan; [140932] proxan-sodium EC no 2054435 sodium salt
PHYSICAL CHEMISTRY:
Mol. wt. 136.2; (sodium salt 158.2) M.f. C
4
H
8
OS
2
; (sodium salt C
4
H
7
NaOS
2
)
COMMERCIALISATION:
History Herbicide reported by L. L. Baumgartner & B. Wolf (Contrib. Boyce Thompson
Inst., 1949, 15, 403). Introduced by Goodrich Chemical Co.
PRODUCTS:
Discontinued products Goodriten.i.x.* (Goodrich).
Toxicity Class WHO (a.i.) OECClassifcation Xn; R22| Xi; R38| N; R51, R53 (sodium
salt)
proximpham
Herbicide
NOMENCLATURE:
Chemical Abstracts name 2-propanone O-[(phenylamino)carbonyl]oxime
CAS RN [2828424] Smiles code CC(=NOC(=O)Nc1ccccc1)C
10
H
12
N
2
O
2
M.p. 109.5 C V.p. 6.7 10
1
mPa (20 C) Henry 2.58 10
4
Pa m
3
mol
1
(20 C, calc.)
S.g./density 1.02 Solubility In water 500 mg/l (20 C). Readily soluble in common
organic solvents, e.g. in methanol 43, DMF 41, ethanol 36, acetone 35, benzene 34, toluene
9, diethyl ether 5 (g/100g). Practically insoluble in hexane. Stability Stable up toc. 90 C.
In acidic media, hydrolysed to aniline and diphenylurea; in alkaline media, hydrolysed to
diphenyl urea and acetone oxime; in neutral aqueous solution, DT
50
13 d.
COMMERCIALISATION:
APPLICATIONS: Uses Selective pre-emergence or pre-planting control of annual
weeds in beet crops,corn salad, lettuce and spinach as well as in the seeding of Scots pine
and spruce. Only used in mixed formulations.
ANALYSIS:
PRODUCTS: determined by gc with FID (D. Spengler & A. Jumar, Arch. Pfanzenschutz
1969, 5, 445) or titration of the iodine liberated by acid hydrolysis in the presence of
N
O
O
N
H
454
PT807
iodide. Residues in soil by extraction with acetone, isolation and separation from other
herbicides by tlc, saponifcation with semi-concentrated sulfuric acid, diazotisation,
coupling with N-(1-naphthyl)ethylenediamine dihydrochloride, and spectrophotometric
measurement of the extinction at 550 nm (D. Spengler & A. Jumar, J. Chromatogr. 1970, 49,
329).
Oral Acute oral LD
50
for rats 1540, mice 1300 mg/kg. NOEL (90 d) for rats 100 mg/kg.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for guppies 93 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment In soil, there is partly microbial, partly hydrolytic degradation; DT
50

710 d. Aniline is not found.
prynachlor
Herbicide
NOMENCLATURE:
Common name prynachlore ((m) F-ISO); prynachlor (BSI, E-ISO, ANSI, WSSA)
IUPAC name 2-chloro-N-(1-methylprop-2-ynyl)acetanilide
Chemical Abstracts name 2-chloro-N-(1-methyl-2-propynyl)-N-
phenylacetamide CAS RN [21267721] Development codes BAS 290H (BASF)
Smiles code CC(C#C)N(C(=O)CCl)c1ccccc1
PHYSICAL CHEMISTRY:
Mol. wt. 221.7 M.f. C
12
H
12
ClNO
COMMERCIALISATION:
History Herbicide developed by BASF AG.
PRODUCTS:
Discontinued products Basamaize* (BASF).
PT807
Most data here are taken from the EPA Fact Sheet.
NOMENCLATURE:
Chemical Abstracts name N,N-diethyl-2-(4-methylbenzyloxy)ethylamine hydrochloride
Other names MBTA CAS RN [274671613] Development codes PT807
PHYSICAL CHEMISTRY:
Composition Except where stated otherwise, data are for the hydrochloride salt.
PT807 455
Mol. wt. 221.3 M.f. C
14
H
23
NO (free base) Form Colourless slightly viscous liquid.
B.p. 105.91.5 C V.p. 1.19 10-2 mPa (EPA Fact Sheet) K
ow
logP <0 (pH 5 and 7),
2.02.4 (pH 9) (EPA Fact Sheet) S.g./density 1.0596 Solubility Miscible with water (pH
59). Miscible with acetonitrile, methanol, dichloromethane and octanol (25 C).
Stability Stable to hydrolysis. pKa 9.55
COMMERCIALISATION:
History Plant growth regulator. First registered in USA in 1999; registration cancelled in
2004.
Manufacturers GMJA
APPLICATIONS:
Mode of action Systemic. Uses Promotes sugar accumulation in processing oranges and
shortens the time to maturation; applied at 0.013 lb/a. Formulation types SC.
PRODUCTS:
Discontinued products Ecolyst* (GMJA).
EPA Fact Sheet, Jan. 2000.
Oral Acute oral LD
50
for rats 531 mg/kg. Skin and eye Slight to moderate eye irritant;
not a skin irritant. Not a skin sensitiser. NOEL Acute neurotoxicity NOAEL for rats 50
mg/kg daily. Reproductive NOAEL for rats 14 mg/kg daily. (EPA Fact Sheet).
ADI/RfD (EPA) aRfD 0.5, cRfD 0.14 mg/kg b.w. [2000].
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(8 d) for bobwhite
quail and mallard ducks >5600 ppm. Fish LC
50
(96 h) for rainbow trout 6.7, bluegill sunfsh
>12.6, sheepshead minnows 16 mg/l. Daphnia LC
50
(24 h) 24 mg/l. Algae IC50 (96 h) for
Pseudokirchneriella subcapitata 0.40, Skeletonema costatum 0.119, Navicula pelliculosa
0.88 mg/l. Other aquatic spp. EC
50
(96 h) for eastern oysters 7.0, mysid shrimps 20 mg/l.
IC50 (96 h) for Lemma gibba >116 mg/l. Bees LD
50
for honeybees >25 g/bee.
ENVIRONMENTAL FATE:
Animals After administration to rats, rapidly metabolised and excreted, primarily in the
urine; only minor amounts of parent were identifed in urine and faeces. The primary
metabolite was a carboxylic acid metabolite, which then undergoes conjugation to
glucuronic acid, or hydroxylation on the alkyl portion of the molecule.
Soil/Environment Stable to photolysis. Soil DT
50
(aerobic metabolism) 335 d; the
primary degradation pathway is aerobic degradation to CO
2
. Persistent, moderately mobile
to immobile; K
oc
28511 000.
456
pyfubmide
pydanon
NOMENCLATURE:
Common name pydanon (BSI, E-ISO, (m) F-ISO)
IUPAC name ()-hexahydro-4-hydroxy-3,6-dioxopyridazin-4-ylacetic acid
Chemical Abstracts name hexahydro-4-hydroxy-3,6-dioxo-4-pyridazineacetic acid
CAS RN [22571079] unstated stereochemistry Development codes H 1244
Smiles code OC(=O)CC1(O)CC(=O)NNC1=O
PHYSICAL CHEMISTRY:
Mol. wt. 188.1 M.f. C
6
H
8
N
2
O
5
M.p. 98 C V.p. Negligible (room temperature) Solubility
Readily soluble in water.
COMMERCIALISATION:
History Plant growth regulator developed by C. F. Spiess & Sohn.
APPLICATIONS:
Mode of action Plant growth regulator. rapidly absorbed by leaves and roots and
translocated acropetally and basipetally. Uses Applied to young plants to delay general
development for 13 w. Applied before bud break, causing retardation of blossom for
12 w. Also prevents chlorosis of seedlings inside containers.
Oral Oral LD
50
for mice 1000 mg/kg. Toxicity Class WHO (a.i.) O
pyfubmide
NOMENCLATURE:
Common name pyfubumide (pa ISO)
IUPAC name 3-isobutyl-N-isobutyryl-1,3,5-trimethyl-4-[2,2,2-trifuoro-1-methoxy-1-
(trifuoromethyl)ethyl]pyrazole-4-carboxanilide
O
OH
HN
H
N
O
O
OH
CF
3
F
3
C
O
N
O
N
N
CH
3
C H
3
CH
3
O
CH
3
C H
3
C H
3
CH
3
CH
3
pyracarbolid 457
Chemical Abstracts name 1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-
methylpropyl)-4-[2,2,2-trifuoro-1-methoxy-1-(trifuoromethyl)ethyl]phenyl]-1H-
pyrazole-4-carboxamide CAS RN [926914558] Development codes NNI0711
Smiles code Cc1c(c(n(n1)C)C)C(=O)N(c2ccc(c(c2)CC(C)C)C(C(F)(F)F)(C(F)(F)F)OC)
C(=O)C(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 535.52 M.f. C
25
H
31
F
6
N
3
O
3
pyracarbolid
Fungicide
NOMENCLATURE:
Common name pyracarbolide ((m) F-ISO); pyracarbolid (BSI, E-ISO)
IUPAC name 3,4-dihydro-6-methyl-2H-pyran-5-carboxanilide
Chemical Abstracts name 3,4-dihydro-6-methyl-N-phenyl-2H-pyran-5-carboxamide
CAS RN [24691767] EC no 2464194 Development codes Hoe 13 764; Hoe 02
989 *; Hoe 6052 *; Hoe 6053 * Smiles code CC1=C(CCCO1)C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY:
13
H
15
NO
2
Form Colourless
solid. M.p. 110111 C V.p. 0.016 mPa (25 C) Solubility In water 0.6 g/l (40 C). In
chloroform 366, ethanol 89, ethyl acetate 86, hexane 0.1, xylene 13 (all in g/l, 25 C).
Stability Stable to light and heat and in alkaline media, but decomposed by acids.
COMMERCIALISATION:
History Fungicide reported by H. Stingle et al. (Int. Congr. Plant Prot., 7th, Paris, 1970, p.
205 (Abstr.)) and B. Jank & F. Grossman (Pestic. Sci., 1971, 2, 43). Introduced by Hoechst AG.
Patents DE 1668899; GB 1194526
APPLICATIONS:
Mode of action Systemic fungicide, absorbed by plants via roots and leaves.
Uses Effective against Basidiomycetes. It controls Rusts (Uredinales), Smuts (Ustilaginales),
and Damping-off disease caused by Thanatephorus cucumeris (Rhizoctonia solani). It is
used in bean, cereal, coffee, and tea crops. Rates and concentrations vary considerably
depending on disease/crop combination and formulation. Formulation types SC. WP;
Seed treatment.
PRODUCTS:
Discontinued products Sicarol* (Hoechst).
ANALYSIS:
Product analysis is by titration. Residues may be determined by colorimetric methods.
458
pyriclor
Oral Acute oral LD
50
for female rats >15 000 mg (in starch mucilage)/kg.
50
for female rats >1000 mg/kg. NOEL (2 y) for rats
400, dogs 1600 mg/kg diet. Other Acute i.p. LD
50
for female rats 1600 mg/kg.
Toxicity Class WHO (a.i.) UECClassifcation R52, R53
ECOTOXICOLOGY:
Fish LC
50
(96 h) for carp 42.3, rainbow trout 45.5 mg/l.
pyresmethrin
Insecticide
IRAC 3
NOMENCLATURE:
Common name pyresm(thrine) ((f) F-ISO); pyresmethrin (BSI, E-ISO)
IUPAC name 5-benzyl-3-furylmethyl (E)-(1R)-trans-3-(2-methoxycarbonylprop-1-
enyl)-2,2-dimethylcyclopropanecarboxylate; 5-benzyl-3-furylmethyl (E)-(1R,3R)-3-(2-
methoxycarbonylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate
Chemical Abstracts name [1R-[1,3(E)]]-[5-(phenylmethyl)-3-furanyl]methyl
3-(3-methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
CAS RN [24624586], formerly [56194684] and [20425392]
Development codes NRDC 106; RU-12061
Smiles code COC(=O)C(=CC1C(C(=O)OCc2coc(Cc3ccccc3)c2)C1(C)C)C
23
H
26
O
5
COMMERCIALISATION:
History Insecticide discovered by M. Elliott et al.
APPLICATIONS:
pyriclor
Herbicide
NOMENCLATURE:
Common name pyriclor (WSSA)
IUPAC name 2,3,5-trichloropyridin-4-ol
Chemical Abstracts name 2,3,5-trichloro-4-pyridinol CAS RN [1970407]
Smiles code Oc1c(Cl)cnc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 198.4 M.f. C
5
H
2
Cl
3
NO
pyridafol 459
COMMERCIALISATION:
History Herbicide reported by M. J. Huraux & H. M. Lawson (Symp. New Herbic., 2nd, 1965,
p. 269). Introduced by Dow Chemical Co. (later DowElanco).
APPLICATIONS:
Mode of action Translocated herbicide.
PRODUCTS:
Discontinued products Daxtron* (Dow).
pyridafol
Herbicide
HRAC C3; phenylpyridazine
NOMENCLATURE:
Common name pyridafol (BSI, E-ISO, (m) F-ISO)
IUPAC name 6-chloro-3-phenylpyridazin-4-ol
Chemical Abstracts name 6-chloro-3-phenyl-4-pyridazinol CAS RN [40020017]
EC no 2547521 Development codes NOA 402 989; SAN 1367H
PHYSICAL CHEMISTRY:
Mol. wt. 206.6 M.f. C
10
H
7
ClN
2
O
COMMERCIALISATION:
History Herbicide evaluated by Novartis Crop Protection AG.
APPLICATIONS:
receptor site.
EU Status (1107/2009) Not approved, application withdrawn.
ENVIRONMENTAL FATE:
Soil/Environment In soil, formed as a degradate of pyridate, q.v. for details.
N
N Cl
OH
460
pyrifenox
pyridinitril
Fungicide
NOMENCLATURE:
Common name pyridinitril (BSI, E-ISO); DDPP (JMAF); pyridinitrile ((m) F-ISO)
IUPAC name 2,6-dichloro-4-phenylpyridine-3,5-dicarbonitrile
Chemical Abstracts name 2,6-dichloro-4-phenyl-3,5-pyridinedicarbonitrile
CAS RN [1086028] Development codes IT 3296
Smiles code Clc1nc(Cl)c(C#N)c(c1C#N)c2ccccc2
13
H
5
Cl
2
N
3
COMMERCIALISATION:
History Fungicide reported by G. Mohr et al. (Meded. Rijksfac. Landbouwwet. Gent, 1968,
33, 1293). Introduced by E. Merck (later Shell Agrar GmbH).
APPLICATIONS:
PRODUCTS:
Discontinued mixtures Ciluan* (+ captan) (E. Merck).
pyrifenox
Fungicide
FRAC 3, G1; SBI Class I, DMI: pyridine
NOMENCLATURE:
Common name pyrif(nox) ((m) F-ISO); pyrifenox (BSI, ANSI, E-ISO)
IUPAC name 2,4-dichloro-2-(3-pyridyl)acetophenone (E,Z)-O-methyloxime
Chemical Abstracts name 1-(2,4-dichlorophenyl)-2-(3-pyridinyl)ethanone
O-methyloxime CAS RN [88283414] Development codes Ro 151297;
ACR 3651 A (both Dr Maag); CGA 179945 (Ciba); NRK-297 (Nippon Kayaku)
Smiles code CON=C(Cc1cccnc1)c2ccc(Cl)cc2Cl
PHYSICAL CHEMISTRY:
Composition A mixture of (E)- and (Z)- isomers. Mol. wt. 295.2 M.f. C
14
H
12
Cl
2
N
2
O
N
CH
2
C
N
CH
3
O
Cl
Cl
pyrifenox 461
Form Pale yellow, viscous liquid, with a slightly sweet odour. B.p. 212.1 C V.p. 1.7 mPa
(25 C) K
ow
logP = 3.4 (pH 5.0), 3.7 (pH 7.0), 3.7 (pH 9.0) (all 25 C) S.g./density 1.28
(20 C) Solubility In water 300 (pH 5.0), 150 (pH 6.7), 130 (pH 9.0) (all in mg/l, 25 C).
In n-hexane 210 g/l (25 C). Completely miscible with ethanol, acetone, toluene and
n-octanol. Stability Stable for >3 years in a closed container at room temperature. Stable
to uv light and to hydrolysis in water (pH 3, 7, 9; 50 C). pKa 4.61, weak base F.p. 106 C
(1013 mbar)
COMMERCIALISATION:
History Fungicide reported by P. Zobrist et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1986,
1, 47). Introduced by Dr R Maag Ltd and frst marketed in 1986. Patents EP 49854
Manufacturers Syngenta
APPLICATIONS:
Biochemistry Ergosterol biosynthesis inhibitor. Mode of action Systemic fungicide
with protective and curative action. Absorbed by the leaves and roots, and translocated
acropetally. Uses Systemic Fungicide used, at 40150 g/ha, for the control of powdery
mildew, scab and other pathogenic Ascomycetes, Basidiomycetes and Deuteromycetes on
grapes, cucurbits, pome fruit, stone fruit, peanuts, sugar beet, ornamentals and vegetables.
Formulation types EC; WG; WP.
PRODUCTS:
Discontinued products Corado* (Ciba); Corona* (Syngenta); Curado* (Ciba);
Dorado* (Syngenta); Podigrol* (Syngenta); Discontinued mixtures Furado*
(+ mancozeb) (Ciba); Rondo* (+ captan) (Syngenta).
ANALYSIS:
Product analysis by tlc, glc, or hplc; glc with FID is recommended. Residues determined
by lc, glc or hplc. See R. P. Hanni & A. J. Schuler, in Comp. Anal. Profles, Chapt. 3. Details also
available from Syngenta.
J. Pestic. Sci., 1991, 16, 355359. EU Status (1107/2009) Not approved, Commission
Oral Acute oral LD
50
for rats 2912, mice >2000 mg/kg. Skin and eye Acute percutaneous
LD
50
for rats >5000 mg/kg. Weak irritant to skin (humans); non-irritant to eyes (rabbits).
Not a skin sensitiser (guinea pigs). Inhalation LC
50
3
air.
NOEL (2 y) for rats 15 mg/kg b.w. daily; (1.5 y) for mice 45 mg/kg b.w. daily; (1 y) for dogs
10 mg/kg b.w.. daily. ADI/RfD (BfR) 0.09 mg/kg b.w. [1991]; (EPA) 0.01 mg/kg b.w. [1987].
Other Not mutagenic, not teratogenic, and not oncogenic. Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Birds Acute oral LD
50
(14 d) for mallard ducks and bobwhite quail >2000 mg/kg.
Fish LC
50
(96 h) for rainbow trout 7.1, mirror carp 12.2, bluegill sunfsh 6.6 mg/l.
Daphnia EC
50
50
(96 h) for Scenedesmus subspicatus 0.095
mg/l. Bees LD
50
(48 h) (oral) 59 g/bee; (contact) 70 g/bee. Worms LC
50
(14 d)
462
pyriminostrobin
for earthworms 733 mg/kg. Otherbenefcial 200 g/l EC formulation harmless to
Typhlodromus pyri and Orius insidiosus; slightly toxic to Coccinella septempunctata and
Trichogramma cacoeciae (IOBC).
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, pyrifenox is rapidly absorbed, metabolised
and excreted in the urine and faeces. There are no indications of bioretention in tissue
or organs. Plants Relatively rapid degradation in plants. DT
50
in peanut leaves 4 d, apple
leaves 3 d, apple fruit 9 d. The main degradation pathway is by hydrolysis and elimination
of the oxime group. Soil/Environment Moderate soil mobility, no tendency toward
bioaccumulation, little potential for environmental persistence, and fairly rapid dissipation
in plants, soil, water and animals. See R. P. Hanni & A. J. Schuler, in Comp. Anal. Profles,
Chapt. 3. DT
50
in soil 50120 d, K
oc
980 ml/g soil.
pyriminostrobin
Acaricide
NOMENCLATURE:
Common name pyriminostrobin (pa ISO)
IUPAC name methyl (E)-2-{-[2-(2,4-dichloroanilino)-6-(trifuoromethyl)pyrimidin-4-
yloxy]-o-tolyl}-3-methoxyacrylate
Chemical Abstracts name methyl (E)-2-[[[2-[(2,4-dichlorophenyl)amino]-6-
(trifuoromethyl)-4-pyrimidinyl]oxy]methyl]--(methoxymethylene)benzeneacetate
Smiles code InChI=1S/C23H18Cl
2
F3N3O4/c1-33-12-16(21(32)34-2)15-6-4-3-5-
13(15)11-35-20-10
1
9(23(26,27)28)30-22(31-20)29-18-8-7-14(24)9-17(18)25/h3-
10,12H,11H2,1-2H3,(H,29,30,31)/b16-12+
PHYSICAL CHEMISTRY:
Mol. wt. 528.31 M.f. C
23
H
18
Cl
2
F
3
N
3
O
4
CF
3
H
O
C H
3
O
CH
3
O
O N
NH
N
Cl
Cl
pyrinuron 463
pyrimitate
IRAC 1B
NOMENCLATURE:
Common name pyrimitate (BSI, E-ISO, (m) F-ISO, BAN (from 1985)); pyrimithate* (BAN
before 1985)
IUPAC name O-2-dimethylamino-6-methylpyrimidin-4-yl O,O-diethyl phosphorothioate
Chemical Abstracts name O-[2-(dimethylamino)-6-methyl-4-pyrimidinyl] O,O-
diethyl phosphorothioate CAS RN [5221498] Development codes ICI 29 661
Smiles code CCOP(=S)(OCC)Oc1cc(C)nc(n1)N(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 305.3 M.f. C
11
H
20
N
3
O
3
PS
COMMERCIALISATION:
History Veterinary insecticide and acaricide introduced by ICI Pharmaceuticals Division.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses For veterinary use.
PRODUCTS:
Discontinued products Diothyl* (ICI).
pyrinuron
Rodenticide
NOMENCLATURE:
Common name pyrinuron (BSI, E-ISO, (m) F-ISO, ANSI); piriminil (JMAF)
IUPAC name 1-(4-nitrophenyl)-3-(3-pyridylmethyl)urea
Chemical Abstracts name N-(4-nitrophenyl)-N-(3-pyridinylmethyl)urea
CAS RN [53558251] Development codes RH-787
Smiles code [O-][N+](=O)c1ccc(NC(=O)NCc2cccnc2)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 272.3 M.f. C
13
H
12
N
4
O
3
COMMERCIALISATION:
History Rodenticide evaluated by Rohm & Haas Co.
PRODUCTS:
Discontinued products Vacor* (Rohm & Haas).
464
pyrisoxazole
pyriprole
Insecticide
NOMENCLATURE:
Common name pyriprole (BSI, E-ISO, (m) F-ISO)
IUPAC name 1-(2,6-dichloro-,,-trifuoro-p-tolyl)-4-(difuoromethylthio)-5-[(2-
pyridylmethyl)amino]pyrazole-3-carbonitrile
Chemical Abstracts name 1-[2,6-dichloro-4-(trifuoromethyl)phenyl]-
4-[(difuoromethyl)thio]-5-[(2-pyridinylmethyl)amino]-1H-pyrazole-3-
carbonitrile CAS RN [394730713] Development codes V3086
Smiles code N#CC1=NN(C2=C(Cl)C=C(C(F)(F)F)C=C2Cl)
C(NCC3=NC=CC=C3)=C1SC(F)F
PHYSICAL CHEMISTRY:
Mol. wt. 494.3 M.f. C
18
H
10
Cl
2
F
5
N
5
S
COMMERCIALISATION:
History Under development as an insecticide. Patents EP 1310497; US 7371768.
APPLICATIONS: Uses Control of Lepidoptera and Coleoptera.
pyrisoxazole
Fungicide
FRAC 3, G1; SBI Class I, DMI: pyridine
NOMENCLATURE:
Common name pyrisoxazole (pa ISO)
N
N
N
N
H
N
S
F
F
F
F
F
Cl
Cl
C H
3
C H
3
Cl
N
N
O
pyroxyfur 465
IUPAC name 3-[(3R,5RS)-5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine
Chemical Abstracts name 3-[(3R)-5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]
pyridine CAS RN [291771998] (3R,5R)- isomer; [291771830] (3R,5S)- isomer
Development codes SYP-48
Smiles code C[C@@]1(CC(ON1C)c2ccc(cc2)Cl)c3cccnc3
PHYSICAL CHEMISTRY:
Mol. wt. 288.77 M.f. C
16
H
17
ClN
2
O
pyroxychlor
Fungicide
NOMENCLATURE:
Common name pyroxychlor (BSI, E-ISO, ANSI); pyroxychlore ((m) F-ISO)
IUPAC name 2-chloro-6-methoxy-4-trichloromethylpyridine; 6-chloro-4-trichloromethyl-
2-pyridyl methyl ether
Chemical Abstracts name 2-chloro-6-methoxy-4-(trichloromethyl)pyridine
Smiles code COc1cc(cc(Cl)n1)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 260.9 M.f. C
7
H
5
Cl
4
NO
COMMERCIALISATION:
History Fungicide evaluated by Dow Chemical Co. (later DowElanco).
PRODUCTS:
Discontinued products Lorvek* (Dow); Nurelle* (Dow).
pyroxyfur
Fungicide
NOMENCLATURE:
Common name pyroxyfur (BSI, ANSI, E-ISO, (m) F-ISO)
IUPAC name 6-chloro-4-trichloromethyl-2-pyridyl furfuryl ether
Chemical Abstracts name 2-chloro-6-(2-furanylmethoxy)-4-(trichloromethyl)
pyridine CAS RN [70166482] Development codes Dowco 444
Smiles code Clc1cc(cc(OCc2ccco2)n1)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 327.0 M.f. C
11
H
7
Cl
4
NO
2
COMMERCIALISATION:
History Fungicide evaluated by Dow Chemical Co. (later DowElanco).
466
quinalphos-methyl
PRODUCTS:
Discontinued products Grandstand* (Dow).
N-pyrrolidinosuccinamic acid
NOMENCLATURE:
IUPAC name N-pyrrolidinosuccinamic acid
Chemical Abstracts name 4-oxo-4-(1-pyrrolidinylamino)butanoic acid
CAS RN [23744050] Development codes F 529
Smiles code OC(=O)CCC(=O)NN1CCCC1
PHYSICAL CHEMISTRY:
Mol. wt. 186.2 M.f. C
8
H
14
N
2
O
3
COMMERCIALISATION:
History Plant growth regulator evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
Mode of action Plant growth retardant.
PRODUCTS:
Discontinued products FFive* (Uniroyal).
quinalphos-methyl
Insecticide
IRAC 1B
NOMENCLATURE:
Common name quinalphos-methyl (BSI, E-ISO, (m) F-ISO); chinalphos-m(thyl) ((m)
France)
IUPAC name O,O-dimethyl O-quinoxalin-2-yl phosphorothioate
Chemical Abstracts name O,O-dimethyl O-2-quinoxalinyl phosphorothioate
CAS RN [13593083] Development codes SAN 52 056I
Smiles code COP(=S)(OC)Oc1cnc2ccccc2n1
PHYSICAL CHEMISTRY:
Mol. wt. 270.2 M.f. C
10
H
11
N
2
O
3
PS
COMMERCIALISATION:
History Insecticide evaluated by Sandoz AG. For quinalphos, see Main entries.
APPLICATIONS:
quinonamid 467
quinazamid
Fungicide
NOMENCLATURE:
Common name quinazamid (BSI, E-ISO); quinazamide ((m) F-ISO)
IUPAC name p-benzoquinone monosemicarbazone
Chemical Abstracts name 2-(4-oxo-2,5-cyclohexadien-1-ylidene)hydrazinecarboxamide
CAS RN [61566210] Development codes RD 8684; BTS 8684
Smiles code NC(=O)NN=C1C=CC(=O)C=C1
PHYSICAL CHEMISTRY:
Mol. wt. 165.2 M.f. C
7
H
7
N
3
O
2
COMMERCIALISATION:
History Fungicide evaluated by Boots Co., Ltd (later Schering Agrochemicals).
quinconazole
Fungicide
NOMENCLATURE:
Common name quinconazole (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one
Chemical Abstracts name 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-
4(3H)-quinazolinone CAS RN [103970758] Development codes SN 539 865
Smiles code Clc1ccc(c(Cl)c1)n2c(nc3ccccc3c2=O)n4cncn4
PHYSICAL CHEMISTRY:
Mol. wt. 358.2 M.f. C
16
H
9
Cl
2
N
5
O
COMMERCIALISATION:
History Fungicide reported by C. R. Leake (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 1,
343). Evaluated by Schering AG.
APPLICATIONS:
Biochemistry Sterol demethylation inhibitor.
quinonamid
Algicide
NOMENCLATURE:
Common name quinonamid (BSI, E-ISO); quinonamide ((m) F-ISO)
IUPAC name 2,2-dichloro-N-(3-chloro-1,4-naphthoquinon-2-yl)acetamide
Chemical Abstracts name 2,2-dichloro-N-(3-chloro-1,4-dihydro-1,4-dioxo-2-
468
quinothion
naphthalenyl)acetamide CAS RN [27541884] Development codes Hoe 02 997
Smiles code ClC(Cl)C(=O)NC1=C(Cl)C(=O)c2ccccc2C1=O
PHYSICAL CHEMISTRY:
12
H
6
Cl
3
NO
3
Form Yellow needles.
M.p. 214216 C V.p. 0.011 mPa (20 C) Solubility In water 3.0 (pH 4.6), 60 (pH 7)
(both mg/l, 23 C). In acetonec. 7, ethanolc. 3, hexane 0.04, xylene 8 (all in g/l, 20 C).
Stability Decomposed by acid or alkali.
COMMERCIALISATION:
History Algicide reported by P. Hartz et al. (Meded. Fac. Landbouwwet. Rijksuniv. Gent, 1972,
37, 699). Introduced by Hoechst AG. Patents DE 1768447; GB 1263625
APPLICATIONS: Uses Effective against algae in the open as well as algae and mosses
under glass. It could be used as a seed treatment or spray for control of algae in paddies, as
a dip for clay pots, and for treating benches, etc., in greenhouses.
PRODUCTS:
Discontinued products Alginex* (Hoechst); Nosprasit* (Hoechst).
ANALYSIS:
Product and residue analysis is by glc.
Oral Acute oral LD
50
for rats 11 70015 000 mg/kg. NOEL (90 d) for rats 2000 mg/kg
diet. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Japanese quail 11 13615 542 mg/kg (depending on carrier and
sex). Fish LC
50
(96 h) for rainbow trout 0.45 mg/l.
quinothion
Insecticide
IRAC 1B
NOMENCLATURE:
Common name quinothion (BSI)
IUPAC name O,O-diethyl O-2-methyl-4-quinolyl phosphorothioate
Chemical Abstracts name O,O-diethyl O-(2-methyl-4-quinolinyl) phosphorothioate
CAS RN [22439403] Smiles code CCOP(=S)(OCC)Oc1cc(C)nc2ccccc12
PHYSICAL CHEMISTRY:
Mol. wt. 311.3 M.f. C
14
H
18
NO
3
PS
COMMERCIALISATION:
R-1492 469
APPLICATIONS:
quintiofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name quintiofos (BSI, E-ISO, (m) F-ISO, BAN)
IUPAC name O-ethyl O-8-quinolyl phenylphosphonothioate
Chemical Abstracts name O-ethyl O-8-quinolinyl phenylphosphonothioate
CAS RN [1776836] Development codes BAY 9037
Smiles code CCOP(=S)(Oc1cccc2cccnc12)c3ccccc3
PHYSICAL CHEMISTRY:
Mol. wt. 329.4 M.f. C
17
H
16
NO
2
PS
COMMERCIALISATION:
APPLICATIONS:
PRODUCTS:
Discontinued products Bacdip* (Bayer).
R-1492
IRAC 1B
NOMENCLATURE:
IUPAC name S-4-chlorophenylthiomethyl O,O-dimethyl phosphorodithioate
Chemical Abstracts name S-[[(4-chlorophenyl)thio]methyl] O,O-dimethyl
phosphorodithioate Other names methylcarbophenothione; methyl carbophenothion
CAS RN [953173] Development codes R-1492 (Stauffer); G-29288 (Geigy)
Smiles code COP(=S)(OC)SCSc1ccc(Cl)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 314.8 M.f. C
9
H
12
ClO
2
PS
3
Form Light yellow to amber liquid with a moderate
mercaptan odour. M.p. c. 18 C V.p. 400 mPa (25 C) S.g./density 1.341.35 (20 C)
Solubility In water c. 1 mg/l (room temperature). Miscible with most organic solvents.
Stability Moderately stable to heat and resistant to hydrolysis.
470
RA-17
COMMERCIALISATION:
History Insecticide and acaricide reported by J. A. Harding (J. Econ. Entomol., 1959, 52,
1219). Introduced by Stauffer Chemical Co. (later ICI Americas). Patents US 2793224.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic. Uses Acaricide
similar in spectrum of activity to its analogue carbophenothion (q.v.), but more effective
against cotton boll weevil; applied at 50100 g/100 l.
PRODUCTS:
Discontinued products Methyl Trithion* (Stauffer); TriMe* (Stauffer).
ANALYSIS:
Product analysis by uv absorption methods, or by glc. For residues, see G. H. Batchelder et
al., Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1964, 2, 313; Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 443.
ECClassifcation T; R24/25| N; R50, R53| concn. dep.
RA-17
Acaricide
IRAC 1B
NOMENCLATURE:
IUPAC name N
2
-diethoxyphosphinothioyl-N
2
-ethyl-N1,N1-dipropylglycinamide
Chemical Abstracts name O,O-diethyl [2-(dipropylamino)-2-oxoethyl]
ethylphosphororamidothioate Other names phosglycin CAS RN [105084660]
Development codes RA-17 (MV)
Smiles code CCCN(CCC)C(=O)CN(CC)P(=S)(OCC)OCC
PHYSICAL CHEMISTRY:
Mol. wt. 338.4 M.f. C
14
H
31
N
2
O
3
PS Form Solid. M.p. 34 C V.p. 1.8 mPa (25 C) K
ow

logP = 3.9 Solubility In water 140 mg/l (20 C). In acetone, benzene, chloroform,
dichloromethane, ethanol, hexane >200 mg/l (20 C).
Stability Stable up to 180 C. Degraded photochemically on silica gel plate (DT
50
18 h).
COMMERCIALISATION:
History Acaricide reported by K. Balogh & G. Tarpai (6th Int. Congr. Pestic. Chem., 1986).
Introduced in Hungary (1987) by szakmagyarorszgi Vegyimvek. Patents BE 903304; HU
2164940
N
P(OCH
2
CH
3
)
2
S
CH
2
CON(CH
2
CH
2
CH
3
)
2
CH
3
CH
2
rabenzazole 471
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Effective against adults and larvae of
phytophagous mites in apples (2.5 kg/ha), citrus (12 hg/ha) and grapes (23 kg/ha).
PRODUCTS:
Discontinued products Alkatox* (Sagrochem).
ANALYSIS:
Oral Acute oral LD
50
50
for rats >5000 mg/kg. Inhalation Non-toxic to
rats at 0.59 mg/l air.
ECOTOXICOLOGY:
Fish LC
50
for carp 9.47, grass carp 12.5 mg/l, for sheat fsh 12 mg a.i. (as EC)/l.
rabenzazole
Fungicide
NOMENCLATURE:
Common name rabenzazole (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-(3,5-dimethylpyrazol-1-yl)benzimidazole
Chemical Abstracts name 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1H-benzimidazole
CAS RN [40341046] Smiles code Cc1cc(C)n(n1)c2nc3ccccc3[nH]2
PHYSICAL CHEMISTRY:
Mol. wt. 212.3 M.f. C
12
H
12
N
4
COMMERCIALISATION:
History Fungicide reported by W. Specht & M. Tillkes (Pfanz.-Nachr. Bayer (Engl. Ed.), 1980,
33, 61). Introduced by Bayer AG.
PRODUCTS:
Discontinued products Ciriom* (Bayer); Discontinued mixtures Ciriom F*
(+ fuberidazole) (Bayer).
472
RH 5849
rescalure
Attractant
NOMENCLATURE:
Common name rescalure (pa ISO)
IUPAC name (3RS,6RS;3RS,6SR)-6-isopropenyl-3-methyldec-9-en-1-yl acetate
Chemical Abstracts name 3-methyl-6-(1-methylethenyl)-9-decen-1-yl acetate
CAS RN [64309031] Smiles code CC(CCC(CCC=C)C(=C)C)CCOC(=O)C
PHYSICAL CHEMISTRY:
Mol. wt. 252.39 M.f. C
16
H
28
O
2
RH 5849
Insecticide
NOMENCLATURE:
IUPAC name 2-benzoyl-1-tert-butylbenzohydrazide
Chemical Abstracts name benzoic acid 2-benzoyl-1-(1,1-dimethylethyl)hydrazide
CAS RN [112225873] Development codes RH-5849 (Rohm & Haas)
PHYSICAL CHEMISTRY:
Mol. wt. 296.4 M.f. C
18
H
20
N
2
O
2
Form Colourless crystals. M.p. 174176 C
V.p. 0.24 mPa (25 C) K
ow
logP = 2.326 Solubility In water c. 50 mg/l. In
cyclohexanonec. 50, mesityl oxidec. 150 g/l. Stability Stable under normal storage
conditions.
COMMERCIALISATION:
History Insect growth regulator, of interest as the frst non-steroidal ecdysone agonist,
reported by K. D. Wing (Science, 1988, 241, 467), K. D. Wing et al. (ibid., p. 470). Introduced
by Rohm & Haas Co. Patents EP 236618 Manufacturers Rohm & Haas; Zhejiang Heyi
O
O
CH
3
C H
3
CH
2
CH
2
CH
3
HN N
O
O
C(CH
3
)
3
RU 25475 473
APPLICATIONS:
Biochemistry Non-steroidal ecdysone agonist. Mode of action Induces premature
moulting at any point in larval development. Inhibits feeding and oviposition. Uses Control
of colorado beetles on potatoes, pear leaf blister moths, leaf miners on apples and other
crops, gypsy moths, codling moths, Mexican bean beetles, cutWorms, rice stem borers,
ArmyWorms, boll weevils and housefies. Formulation types SC. GR .
Oral Acute oral LD
50
50
for rats
>5000 mg/kg. Not irritant to skin or eyes of rabbits. Other Not mutagenic in Ames assay.
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and quail >5000 mg/kg diet. Fish LC
50
(96 h)
for bluegill sunfsh and trout >100 mg/l. Daphnia LC
50
(48 h) 7 mg/l; for life cycle 0.50.7
mg/l. Bees LD
50
(contact) >0.1 g/bee.
ENVIRONMENTAL FATE:
Soil/Environment In silt loam DT
50
27 d (23 C).
rhodethanil
Herbicide
NOMENCLATURE:
Common name rhodethanil (BSI, E-ISO); rod(thanil) ((m) F-ISO)
IUPAC name 3-chloro-4-ethylaminophenyl thiocyanate
Chemical Abstracts name 3-chloro-4-(ethylamino)phenyl thiocyanate
CAS RN [3703466] Development codes BAY 5396 b H; BAY 53 427
Smiles code CCNc1ccc(SC#N)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 212.7 M.f. C
9
H
9
ClN
2
S
COMMERCIALISATION:
RU 25475
Insecticide
IRAC 3
NOMENCLATURE:
IUPAC name (S)--cyano-3-phenoxybenzyl (1R,3S)-[(RS)-1,2-dibromo-2,2-
dichloroethyl]-2,2-dimethylcyclopropanecarboxylate; Roth: (S)--cyano-3-phenoxybenzyl
(1R)-trans-3-((RS)-1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropanecarboxylate
474
ryanodine
Chemical Abstracts name cyano(3-phenoxyphenyl)methyl 3-(1,2-dibromo-2,2-
dichloroethyl)-2,2-dimethylcyclopropanecarboxylate Other names tralocythrin*
(unaccepted common name) CAS RN [66841267] unstated stereochemistry
Development codes RU 25475; HAG 106
Smiles code CC1(C)C(C(Br)C(Cl)(Cl)Br)C1C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2
PHYSICAL CHEMISTRY:
Mol. wt. 576.1 M.f. C
22
H
19
Br
2
Cl
2
NO
3
COMMERCIALISATION:
History Insecticide evaluated by Roussel Uclaf for use in cotton.
APPLICATIONS:
ryanodine
Insecticide
NOMENCLATURE:
Chemical Abstracts name (3S,4R,4aR,6S,6aS,7S,8R,8aS,8bR,9S,9aS)-dodecahydro-
4,6,7,8a,8b,9a-hexahydroxy-3,6a,9-trimethyl-7-(1-methylethyl)-6,9-methanobenzo[1,2]
pentaleno[1,6-bc]furan-8-yl 1H-pyrrole-2-carboxylate Other names ryania extract
CAS RN [15662336] ryanodine, formerly [1361019], [1580069], [25800571]
and [15800609]; [94513550] 9,21-dehydroryanodine; [8047130] formerly ryania,
now a deleted number for ryanodine EC no 2397322
Smiles code CC(C)C1(O)C(OC(=O)c2ccc[nH]2)C3(O)C4(O)C1(C)C5(O)CC3(C)
C6(O)CCC(C)C(O)C46O5
PHYSICAL CHEMISTRY:
Composition The main toxicant of ryania, the ground stemwood of the shrub Ryania
speciosa; 9,21-dehydroryanodine and other ryanoids are also present in the crude plant
extract. Mol. wt. 493.6 M.f. C
25
H
35
NO
9
M.p. 219220 C (decomp.) Solubility Soluble
in water, ethanol, acetone, diethyl ether, chloroform; almost insoluble in benzene, light
O
CH
3
CH
3
OH
OH
CH
3
HO
OH
OH
HO
CH
3
CH
3
O
H
O
NH
salicylanilide 475
petroleum. Stability Relatively stable on exposure to light and air. Specifc rotation []D25
+26
COMMERCIALISATION:
Production Extracted from the powdered stem of the tropical shrub Ryania speciosa.
History Insecticidal activity of ryania reported by B. E. Pepper & L. A. Carruth (J.
Econ. Entomol., 1945, 38, 59). Introduced by S. B. Penick & Co. Patents US 2400295
Manufacturers Dunhill
APPLICATIONS:
Biochemistry Thought to cause a release of calcium from the sarcoplasmic reticulum in
skeletal muscles fbers which in turn leads to sustained muscle contraction and paralysis.
Mode of action Active by ingestion and by contact. Uses Ryania was used for control of
codling moth, European corn borer and citrus thrips in fruit and maize. Applied at 1072 kg
ryania/ha (20145 g alkaloid/ha). Formulation types WP.
PRODUCTS:
Discontinued products Natur-Gro R-50* (AgriSystems International); Natur-Gro
Triple Plus* (AgriSystems International); Ryan 50* (Dunhill); Ryania* (Penick); Rynotox*
(Penick).
ANALYSIS:
Product analysis by uv spectroscopy after extraction by liquid-liquid partition.
Oral Acute oral LD
50
of ryania for rats 1200, mice 650 mg/kg. Lethal dose of ryanodine in
dogs 0.4 mg/kg. NOEL In 150 d feeding trials, guinea-pigs and chickens receiving
10 g/kg diet suffered no toxic symptom. Toxicity Class WHO (a.i.) III EPA (formulation)
III ECClassifcation Xn; R21/22| N; R50, R53
ECOTOXICOLOGY:
Fish Toxic to fsh.
salicylanilide
Fungicide
NOMENCLATURE:
Common name salicylanilide (BSI, E-ISO, F-ISO, JMAF, accepted in lieu of a common
name.)
IUPAC name salicylanilide
Chemical Abstracts name 2-hydroxy-N-phenylbenzamide CAS RN [87172]
Smiles code Oc1ccccc1C(=O)Nc2ccccc2
PHYSICAL CHEMISTRY:
Mol. wt. 213.2 M.f. C
13
H
11
NO
2
476
schradan
COMMERCIALISATION:
History Fungicide reported by R. G. Fargher et al. (Mem. Shirley Inst., 1930, 9, 37).
Introduced by ICI Limited.
APPLICATIONS:
PRODUCTS:
Discontinued products Shirlan* (ICI).
schradan
IRAC 1B
NOMENCLATURE:
Common name schradan (BSI, E-ISO, ESA, JMAF); schradane ((m) F-ISO)
IUPAC name octamethylpyrophosphoric tetra-amide
Chemical Abstracts name octamethyldiphosphoramide Other names OMPA
CAS RN [152169] EC no 2058010
Smiles code CN(C)P(=O)(OP(=O)(N(C)C)N(C)C)N(C)C
PHYSICAL CHEMISTRY:
Composition Tech. contains decamethyltriphosphoric triamide, ((CH3)2N)2PO.OPO.
(N(CH3)2)OPO(N(CH3)2)2, (2550%), which is also insecticidal, and other amides of
higher phosphoric acids. Mol. wt. 286.3 M.f. C
8
H
24
N
4
O
3
P
2
Form Colourless, viscous
liquid. M.p. 1420 C B.p. 118122 C /0.3 mmHg V.p.c. 100 mPa (25 C)
S.g./density 1.1343 (25 C) Solubility Miscible with water and most organic solvents;
slightly soluble in petroleum oils. Stability Stable to water and alkali, but hydrolysed under
acid conditions to dimethylamine and orthophosphoric acid.
COMMERCIALISATION:
History Systemic insecticide discovered by G. Schrader & H. Kenthal (cited by G.
Schrader, Phosphorsure-Ester, p. 88). Introduced by Pest Control Ltd (later Schering
Agriculture). Patents GB 631549, GB 652981.
APPLICATIONS:
acaricide. Relatively inert as a contact insecticide. Uses Effective against sap-feeding insects
and mites. Used as a soil drench for transplanted trees.
PRODUCTS:
Discontinued products Pestox3* (FBC); PestoxIII* (FBC);
Discontinued mixtures Sytam* (+ dimefox) (with tris(dimethylamino)phosphine oxide)
scilliroside 477
(Murphy, Wacker); Terra Sytam* (+ dimefox) (with tris(dimethylamino)phosphine oxide)
(Murphy, Wacker).
ANALYSIS:
Product analysis CIPAC Handbook, 1983, 1B, 1795; mixture with dimefox, 1980, 1A, 334.
Oral Acute oral LD
50
for male rats 9.1, female rats 42 mg/kg. Toxicity Class WHO (a.i.) Ia
scilliroside
Rodenticide
NOMENCLATURE:
Common name scilliroside (JMAF)
IUPAC name 3-(-D-glucopyranosyloxy)-17-(2-oxo-2H-pyran-5-yl)-14-androst-4-
ene-6,8,14-triol 6-acetate
Chemical Abstracts name (3,6)-6-acetyloxy-3-(-D-glucopyranosyloxy)-8,14-
dihydroxybufa-4,20,22-trienolide Other names red squill CAS RN [507608]
EC no 2080774 Smiles code CC(=O)OC1CC2(O)C(CCC3(C)C(CCC32O)
c4ccc(=O)oc4)C5(C)CC(CC=C15)OC6OC(CO)C(O)C(O)C6O
PHYSICAL CHEMISTRY:
Composition The name scilliroside applies to a glycoside contained in the extract of the
powdered bulbs of the red squill, Urginea (Scilla) maritima. Mol. wt. 620.7
M.f. C
32
H
44
O
12
Form Hydrated prisms (from aqueous methanol) which losec. 8% m/m in
vacuo, giving a hemihydrate. M.p. 168170 C (hemihydrate) V.p. Very low
Solubility Slightly soluble in water. Readily soluble in alcohols, ethylene glycol, dioxane
and glacial acetic acid. Slightly soluble in ethyl acetate, acetone and chloroform. Practically
insoluble in diethyl ether and petroleum ether. Stability Decomposes at 200 C; bulbs
should be dried at temperatures below 80 C. Dried red squill powder loses its scilliroside
O
OH
OH
CH
2
OH
O
CH
3
OCOCH
3
OH
CH
3
OH
O
O
OH
H
H
478
sebuthylazine
content on storage and when exposed to the atmosphere. Specifc rotation []D20 59
to 60 (methanol)
COMMERCIALISATION:
History Rodenticide. Red squill has been used since the 13th century. Scilliroside, the
toxic principle, was isolated and identifed by A. Stoll & J. Renz (Helv. Chim. Acta, 1942, 25,
377; 1943, 26, 648). Chemistry and toxicology of cardiac glycosides reviewed by A. Stoll
(Experientia, 1954, 10, 282). The two varieties of U. maritima, red squill and white squill,
contain glycosides, but only the former was used against rats.
APPLICATIONS:
Biochemistry Activity may be due to metabolism to the aglycone, scillirosidin. Causes
emesis, and affects the cardiovascular and central nervous systems. Its specifc toxicity to
rats may be due to the inability of the rodent to vomit, a reaction squill induces in other
animals. Mode of action Selective rodenticide with stomach action. Uses Control of
most species of rodents, e.g. brown rats (Rattus norvegicus), black rats (Rattus rattus), house
mice (Mus musculus), long-tailed feld mice (Apodemus sylvaticus), and Field voles (Microtus
agrestis). Formulation types RB; GB.
ANALYSIS:
Product analysis by tlc, or by chromatographic separation on paper and, after elution,
photometric assay (M. Wichtl & L. Fuchs, Arch. Pharm., 1962, 295, 361).
Oral Acute oral LD
50
for male rats 0.7, female rats 0.43 mg/kg (A. Stoll & J. Renz Helv. Chim.
Acta, 1942, 25, 377; 1943, 26, 648). Dogs, cats, and pigs survived 16 mg/kg (S. A. Barnett et
al., J. Hyg. 1949, 47, 431). In most mammals, with the exception of rodents, scilliroside is an
emetic. Toxicity Class WHO (a.i.) Ia EPA (formulation) I ECClassifcation T+; R28
ECOTOXICOLOGY:
Birds Fowls survived 400 mg/kg.
sebuthylazine
Herbicide
NOMENCLATURE:
Common name sebuthylazine (BSI, E-ISO, (f) F-ISO)
N
N
N
NH
Cl
NH
2-sec-butylamino-4-chloro-6-ethylamino-1,3,5-triazine
secbumeton 479
IUPAC name N
2
-sec-butyl-6-chloro-N4-ethyl-1,3,5-triazine-2,4-diamine; 2-sec-
butylamino-4-chloro-6-ethylamino-1,3,5-triazine
Chemical Abstracts name 6-chloro-N-ethyl-N-(1-methylpropyl)-1,3,5-
triazine-2,4-diamine CAS RN [7286693] Development codes GS 13 528
Smiles code CCCCNc1nc(Cl)nc(NCC)n1
PHYSICAL CHEMISTRY:
Mol. wt. 229.7 M.f. C
9
H
16
ClN
5
Form Colourless powder. M.p. 159161 C
Solubility Sparingly soluble in water. Soluble in acetone, benzene, dioxane; very soluble in
chloroform; slightly soluble in diethyl ether, ethanol.
COMMERCIALISATION:
History Herbicide introduced by J. R. Geigy S.A. (later Ciba-Geigy AG).
PRODUCTS:
Discontinued mixtures Vorox(i)Granulat 371* (+ amitrole + atrazine) (Spiess).
secbumeton
Herbicide
NOMENCLATURE:
Common name secbumeton (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name N
2
-sec-butyl-N4-ethyl-6-methoxy-1,3,5-triazine-2,4-diamine
Chemical Abstracts name N-ethyl-6-methoxy-N-(1-methylpropyl)-1,3,5-triazine-2,4-
diamine CAS RN [26259450] EC no 2475541 Development codes GS 14 254
(Geigy) Smiles code CCNc1nc(NC(C)CC)nc(OC)n1
10
H
19
N
5
M.p. 8688 C V.p. 0.97 mPa (20 C) Henry 3.64 10
4
Pa m
3
mol
1
(calc.)
dichloromethane 600, hexane 22, methanol 500, n-octanol 200, toluene 350 (all in g/l,
20 C). Stability DT
50
(calc.) 30 d (pH 1), 175 d (pH 13) (20 C). pKa 4.4
COMMERCIALISATION:
History Herbicide reported by A. Gast & E. Fankhauser (Proc. Br. Weed Control Conf., 8th,
1966, p. 485). Introduced by J. R. Geigy S.A. (later Ciba-Geigy AG). Patents CH 337019; GB
814948
APPLICATIONS:
Mode of action Total and selective herbicide, taken up by leaves and roots.
Uses Controls mono- and di-cotyledonous weeds both annual and perennial. It was used
in established lucerne either at 13 kg/ha or in combination with simazine. In combination
with terbuthylazine it was suitable for non-cropped land. Formulation types WP.
480
sesamex
PRODUCTS:
Discontinued products Etazine* (Ciba-Geigy); Etazine 3585* (Ciba-Geigy); Sumitol*
(Ciba-Geigy); Discontinued mixtures Etazine 3947* (+ simazine) (Ciba-Geigy);
Primatol 3588* (+ terbuthylazine) (Ciba-Geigy).
ANALYSIS:
Product analysis by glc or by acidimetric titration. Residues determined by glc with MCD
or FPD (K. Ramsteiner et al., J. Assoc. Off. Anal. Chem., 1974, 57, 192; E. Knsli, Anal. Methods
Pestic., Plant Growth Regul. Food Addit., 1964, 4, 13).
Oral Acute oral LD
50
for rats 2680 mg tech./kg. NOEL (90 d) for rats 640 mg/kg diet (c
43 mg/kg daily), for dogs 1600 mg/kg diet (40 mg/kg daily). Toxicity Class WHO (a.i.) U
ECClassifcation Xn; R22| Xi; R36| N; R50, R53
sesamex
NOMENCLATURE:
Common name sesamex (ESA)
IUPAC name 5-[1-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-1,3-benzodioxole (I);
2-(1,3-benzodioxol-5-yloxy)-3,6,9-trioxaundecane
Smiles code CCOCCOCCOC(C)Oc1ccc2OCOc2c1
PHYSICAL CHEMISTRY:
Mol. wt. 298.3 M.f. C
15
H
22
O
6
Form Straw-coloured liquid with a faint odour.
B.p. 137141 C /0.08 mmHg Solubility Readily soluble in kerosine and
dichlorodifuoromethane. Stability Unstable in sunlight and on powdered carriers.
COMMERCIALISATION:
History Synergist for pyrethroid insecticides reported by M. Beroza (J. Agric. Food Chem.,
1956, 4, 49). Introduced by Shulton Inc.
PRODUCTS:
Discontinued products Sesoxane* (Shulton).
Oral Acute oral LD
50
simeton 481
sesasmolin
NOMENCLATURE:
Common name sesasmolin (ESA)
IUPAC name 1,3-benzodioxol-5-yl (1R,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)
perhydrofuro[3,4-c]furan-1-yl ether; 1-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-yloxy)
tetrahydrofuro[3,4-c]furan; 2-(1,3-benzodioxol-5-yl)-6-(1,3-benzodioxol-5-yloxy)-3,7-
dioxabicyclo[3.3.0]octane
Chemical Abstracts name [1S-(1,3a,4,6a)]-5-[4-(1,3-benzodioxol-5-yloxy)
tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole CAS RN [526078]
Smiles code C1Oc2ccc(OC3OCC4C(OCC34)c5ccc6OCOc6c5)cc2O1
PHYSICAL CHEMISTRY:
Mol. wt. 370.4 M.f. C
20
H
18
O
7
COMMERCIALISATION:
History Synergistic activity with pyrethrum of sesame oil (from Sesamum indicum)
reported by C. Eagleson (Soap Chem. Spec., 1942, 18(12), 125) and traced to sesasmolin by
H. L. Haller et al. (J. Org. Chem., 1942, 7, 183; J. Econ. Entomol., 1942, 35, 247).
simeton
Herbicide
NOMENCLATURE:
Common name simeton (BSI, WSSA)
IUPAC name N
2
,N4-diethyl-6-methoxy-1,3,5-triazine-2,4-diamine; 2,4-bis(ethylamino)-6-
methoxy-1,3,5-triazine
Chemical Abstracts name N,N-diethyl-6-methoxy-1,3,5-triazine-2,4-diamine
Smiles code CCNc1nc(NCC)nc(OC)n1
PHYSICAL CHEMISTRY:
Mol. wt. 197.2 M.f. C
8
H
15
N
5
O
COMMERCIALISATION:
History Herbicide developed by J. R. Geigy S.A. (later Ciba-Geigy AG).
482
SMY 1500
SMY 1500
Herbicide
NOMENCLATURE:
IUPAC name 4-amino-6-tert-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one
Chemical Abstracts name 4-amino-6-(1,1-dimethylethyl)-3-(ethylthio)-
1,2,4-triazin-5(4H)-one Other names ethiozin * (rejected common name
proposal) CAS RN [64529562] Development codes SMY 1500 (Bayer)
Smiles code CCSc1nnc(c(=O)n1N)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 228.3 M.f. C
9
H
16
N
4
OS Form Colourless crystals. M.p. 96.4 C
V.p. 7.5 10
3
mPa (20 C) K
ow
logP = 2.08 Henry 5.04 10
3
Pa m
3
mol
1
(calc.)
Solubility In water 0.34 mg/l (20 C). In dichloromethane >200, isopropanol 100200,
toluene 100200 g/kg.
COMMERCIALISATION:
History Herbicide reported by H. Hack & L. Eue (Proc. 1985 Br. Crop Prot. Conf. - Weeds,
1, 35). Introduced in Israel (1989) by Bayer AG.
APPLICATIONS:
site. Uses Pre-emergence control of grasses (particularly Bromus spp.) and some broad-
leaved weeds in cereals (mainly wheat) and tomatoes at 0.551.7 kg/ha.
Formulation types WG .
PRODUCTS:
Discontinued products Lektan* (Bayer); Tycor* (Bayer).
Oral Acute oral LD
50
for ratsc. 2000 mg/kg, micec. 1000, dogs >5000 mg/kg.
50
for rats >5000 mg/kg. NOEL (2 y) for rats 25
mg/kg diet. ADI/RfD (EPA) 0.05 mg/kg b.w. [1990].
N
N N
O
SCH
2
CH
3
(CH
3
)
3
C
NH
2
SN 106 279 483
SN 106 279
Herbicide
NOMENCLATURE:
IUPAC name methyl (R)-2-(7-(2-chloro-,,-trifuoro-p-tolyloxy)-2-naphthyloxy)
propionate
Chemical Abstracts name methyl (R)-2-[[7-[2-chloro-4-(trifuoromethyl)phenoxy]-2-
naphthalenyl]oxy]propanoate CAS RN [103055614]
Development codes SN 106 279
PHYSICAL CHEMISTRY:
Mol. wt. 424.8 M.f. C
21
H
16
ClF
3
O
4
Form Tech. is a yellow liquid. V.p. 2.39 10
3
mPa
(25 C) Solubility In water 0.7 mg/l. In ethanol and acetone 870, methanol 850 (g/l,
20 C).
COMMERCIALISATION:
History Herbicide evaluated by Schering AG. Reported by F. Arndt et al. (Proc. Br. Crop Prot.
Conf. Weeds, 1989, 1, 35).
APPLICATIONS:
Mode of action Taken up principally by plant leaves. Treated plants display diphenyl ether
symptoms of root and shoot necrosis of meristems. Uses Post-emergence herbicide for
control of broad-leaved weeds, such as Veronica spp., Viola spp., Lamium spp., in winter
cereals, at 100200 g/ha.
Oral Acute oral LD
50
for male rats >400 mg/kg. Skin and eye Acute percutaneous LD
50

for male rats >>400 mg/kg.
CH
CH
3
O O
F
3
C Cl
CO
2
CH
3
484
sodium (Z)-3-chloroacrylate
SN 72129
Insecticide
NOMENCLATURE:
IUPAC name (E)-2-chlorobenzoyl(2,3-dihydro-4-phenyl-1,3-thiazol-2-ylidene)acetonitrile
Chemical Abstracts name (E)-2-chloro--oxo--(4-phenyl-2(3H)-thiazolylidene)
benzenepropanenitrile Other names thiapronil* (unadopted proposed common name)
CAS RN [77768582] unstated stereochemistry Development codes SN 72129
Smiles code Clc1ccccc1C(=O)C(=C2NC(=CS2)c3ccccc3)C#N
PHYSICAL CHEMISTRY:
Mol. wt. 338.8 M.f. C
18
H
11
ClN
2
OS Form Colourless crystals. M.p. 182183 C
V.p. <1.3 10
5
mPa (25 C) Solubility In water 69 mg/l (room temperature). In acetone
0.015, methanol 4.2, isopropanol 1.9 (all in g/l). Stability Stable in acid and alkali.
COMMERCIALISATION:
History Insecticide reported by H. Joppien et al. (Proc. 10th Int. Congr. Plant Prot., 1983, 1,
Oral Acute oral LD
50
50
for
rabbits >2000 mg/kg.
sodium (Z)-3-chloroacrylate
NOMENCLATURE:
IUPAC name sodium (Z)-3-chloroacrylate
Chemical Abstracts name sodium (Z)-3-chloro-2-propenoate
Other names sodium cis-3-chloroacrylate CAS RN [4312974]
Development codes UC 20 299 Smiles code [Na+].[O-]C(=O)/C=C\Cl; without
stereochemistry:[Na+].[O-]C(=O)C=CCl
PHYSICAL CHEMISTRY:
Mol. wt. 128.5 M.f. C
3
H
2
ClNaO
2
COMMERCIALISATION:
History Herbicide reported by R. A. Herrett & A. N. Kurtz (Science, 1963, 141, 1192).
Introduced as a defoliant by Union Carbide Corp. (later Rhne-Poulenc Ag.).
C
N
S
NH
O
Cl
sodium fuoride 485
PRODUCTS:
Discontinued products Prep* (Union Carbide).
ECClassifcation Xn; R21/22
sodium fuoride
Insecticide
NOMENCLATURE:
Common name fuorure de sodium (F-ISO, used in lieu of a common name); sodium
fuoride (E-ISO, used in lieu of a common name)
IUPAC name sodium fuoride
Chemical Abstracts name sodium fuoride CAS RN [7681494] EC no 2316678
Smiles code [F-].[Na+]
PHYSICAL CHEMISTRY:
Mol. wt. 42.0 M.f. FNa Form Colourless powder. M.p. 993 C V.p. Negligible (room
temperature) S.g./density 2.8 Solubility In water 42.2 g/l (18 C). Slightly soluble in
ethanol.
COMMERCIALISATION:
History Introduced in baits against insects in stores.
APPLICATIONS:
Mode of action Insecticide with stomach and contact action. Uses Used in insect baits
and as a timber preservative. Phytotoxicity Highly phytotoxic.
PRODUCTS:
Discontinued products Florocid* (Allied).
ANALYSIS:
Product analysis is by determination of the fuorine content by titrimetric methods
(AOAC Methods, 18th Ed., 921.04, 929.04, 933.03).
ICSC.951 (2003).
Oral Highly toxic, the lowest oral lethal dose being 28100 mg/kg for a range of
vertebrates. Acute oral LD
50
for rats 180 mg/kg (Am. Ind. Hyg. Assoc. J., 1969, 30, 470).
Toxicity Class WHO (a.i.) IIECClassifcation T; R25| Xi; R36/38| R32
NaF
486
sodium fuoroacetate
sodium fuoroacetate
Rodenticide
IRAC 26
NOMENCLATURE:
Common name sodium fuoroacetate (E-ISO, accepted in lieu of a common name);
fuoroac(tate de sodium) (F-ISO, accepted in lieu of a common name); fuoroacetic acid
(BSI, for parent acid)
IUPAC name sodium fuoroacetate
Chemical Abstracts name sodium fuoroacetate Other names Compound 1080
CAS RN [62748] EC no 2005482 Smiles code [Na+].[O-]C(=O)CF
PHYSICAL CHEMISTRY:
Mol. wt. 100.0 M.f. C
2
H
2
FNaO
2
Form Colourless, hygroscopic powder.
M.p. Decomposesc. 200 C V.p. Non-volatile Solubility Very soluble in water. Almost
insoluble in ethanol, acetone and petroleum oils.
COMMERCIALISATION:
History Rodenticidal properties reported by E. R. Kalmbeck (Science, 1945, 102, 232).
APPLICATIONS:
Biochemistry Inhibits aconitase in the tricarboxylic acid cycle. Uses Used in baits for
control of rodents. In Australia, also used for control of wild rabbits, wild dogs and wild
pigs. Formulation types CB .
ANALYSIS:
Product analysis is by conversion to lead chloride fuoride (AOAC Methods, 14th Ed.,
6.0196.062); sodium fuoride is a usual contaminant. For a qualitative determination
of fuoroacetic acid in residues, see AOAC Methods, 18th Ed., 949.09; for quantitive
determination by extraction, see ibid., 949.10, followed by fuorine determination, ibid.,
944.08.
PDS 16 (1975). ICSC.484 (1997).
Oral Acute oral LD
50
for Rattus norvegicus 0.22 mg/kg (S. H. Dieke & C. P. Richter, U.S.
Public Health Rep., 1946, 61, 672). Highly toxic to all other mammals (see Sodium
monofuoroacetate). NOEL NOAEL (13 w) for rats 0.05 mg/kg b.w. daily (EPA RED).
ADI/RfD (EPA) cRfD 0.00002 mg/kg b.w. [1993, 1995]. Toxicity Class WHO (a.i.) Ia.
ECClassifcation T+; R26/27/28| N; R50
FCH
2
CO
2
Na
sophamide 487
sodium selenate
Insecticide
NOMENCLATURE:
IUPAC name sodium selenate
Chemical Abstracts name disodium selenate CAS RN [13410010]
Smiles code [Na+].[Na+].[O-][Se](=O)(=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 188.9 M.f. Na
2
O
4
Se
COMMERCIALISATION:
History Introduced as an insecticide.
sophamide
Insecticide
IRAC 1B
NOMENCLATURE:
Common name sophamide (BSI, E-ISO, (m) F-ISO)
IUPAC name S-methoxymethylcarbamoylmethyl O,O-dimethyl phosphorodithioate;
2-dimethoxyphosphinothioylthio-N-methoxymethylacetamide
Chemical Abstracts name S-[2-[(methoxymethyl)amino]-2-oxoethyl] O,O-
dimethyl phosphorodithioate CAS RN [37032158] Development codes MC-62
Smiles code COCNC(=O)CSP(=S)(OC)OC
PHYSICAL CHEMISTRY:
Mol. wt. 259.3 M.f. C
6
H
14
NO
4
PS
2
COMMERCIALISATION:
History Insecticide evaluated by Murphy Chemical Co.
APPLICATIONS:
PRODUCTS:
Discontinued products Formocarbam* (Murphy).
488
SSF-109
SSF-109
Fungicide
NOMENCLATURE:
Chemical Abstracts name ()-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)
cycloheptanol CAS RN [129586329] Development codes SSF-109 (Shionogi)
Smiles code OC1(CCCCCC1n2cncn2)c3ccc(Cl)cc3
PHYSICAL CHEMISTRY:
Mol. wt. 291.8 M.f. C
15
H
18
ClN
3
O Form Colourless crystals. M.p. 128129 C
K
ow
logP = 0.481 Solubility In water 125 mg/l (25 C).
COMMERCIALISATION:
History Broad-spectrum fungicide introduced by Shionogi and Co. Ltd (whose
agrochemical interests became Aventis CropScience Shionogi K.K. in 2001, became part of
Bayer AG).
APPLICATIONS:
Biochemistry Inhibits ergosterol biosynthesis. Mode of action Systemic fungicide with
preventive and curative action. Uses Broad-spectrum fungicide for control of Ascomycetes,
Phycomycetes, Basidiomycetes, and Fungi Imperfecti on lettuce, cucumbers, wheat, oats,
and rice. Particularly active against grey mould (Botrytis cinerea), including benzimidazole-
resistant strains.
ANALYSIS:
Product by tlc or hplc.
Oral Acute oral LD
50
for rats 153214, mice 273 mg/kg. Other Negative in the Ames test
and micronucleus test.
ECOTOXICOLOGY:
Fish LC
50
(48 h) for carp 22.5, killifsh 10.9 mg/l. Daphnia LC
50
(3 h) for Daphnia pulex
100.5 mg/l.
N N
N
HO
Cl H
N N
N
HO
Cl H
(1S,2S)- isomer (1R,2R)- isomer
SSI-121 489
SSH-108
NOMENCLATURE:
IUPAC name 2-difuoromethylthio-4,6-bis(isopropylamino)-1,3,5-triazine
Chemical Abstracts name 6-[(difuoromethyl)thio]-N,N-bis(1-methylethyl)-1,3,5-
triazine-2,4-diamine CAS RN [103427732] Development codes SSH-108
PHYSICAL CHEMISTRY:
Mol. wt. 277.3 M.f. C
10
H
17
F
2
N
5
S
APPLICATIONS: Uses In mixture with acetochlor for use in maize and other crops.
SSI-121
Acaricide
NOMENCLATURE:
IUPAC name ((chlorobis(2-methyl-2-phenylpropyl)stannyl)methyl)trimethylsilane
Chemical Abstracts name [[chlorobis(2-methyl-2-phenylpropyl)stannyl]methyl]
trimethylsilane Other names bis(2-methyl-2-phenylpropyl)trimethylsilylmethyl stannyl
chloride(II) CAS RN [108307079] Development codes SSI-121 (Shionogi)
Smiles code CC(C)(c1ccccc1)[Sn](Cl)(C[Si](C)(C)C)C(C)(C)c2ccccc2
PHYSICAL CHEMISTRY:
Mol. wt. 507.8 M.f. C
24
H
37
ClSiSn
COMMERCIALISATION:
History Acaricide evaluated by Shionogi and Co., Ltd; discontinued in 1994.
APPLICATIONS:
Mode of action Contact acaricide. Uses Control of all stages of spider mites (including
cyhexatin- and fenbutatin oxide-resistant strains) on apples, citrus fruit, tea, and other
crops. Formulation types WP.
EHC 15 (1980) is a general review of tin and tin compounds.
N N
N NHCH(CH
3
)
2
(CH
3
)
2
CHNH
SCHF
2
(CH
3
)
2
C
Sn
CH
2
Si(CH
3
)
3
Cl
C(CH
3
)
2
CH
2
CH
2
490
strychnine
Oral Acute oral LD
50
for rats 2000 mg/kg (Shibuya). Skin and eye Acute percutaneous
LD
50
for rats >1000 mg/kg (Shibuya).
strychnine
Rodenticide
NOMENCLATURE:
Common name strychnine (BSI, E-ISO, F-ISO, accepted in lieu of a common name)
IUPAC name strychnidin-10-one
Chemical Abstracts name strychnidin-10-one CAS RN [57249] EC no 2003197
Smiles code O=C1C[C@@H]2OCC=C3CN4CC[C@]56[C@@H]4C[C@@H]3[C@
@H]2[C@@H]6N1c7ccccc75;without stereochemistry:O=C1CC2OCC=C3CN4CCC56
C4CC3C2C6N1c7ccccc75
PHYSICAL CHEMISTRY:
Mol. wt. 334.4 M.f. C
21
H
22
N
2
O
2
Form Colourless crystals. M.p. 270280 C (decomp.);
>199 C (sulfate) K
ow
logP = 4.0 (pH 7) Solubility In water 143 mg/l. In benzene 5.6,
ethanol 6.7, chloroform 200 (all in g/l). Sparingly soluble in diethyl ether and petroleum
spirit. Sulfate solubility in water 30 g/l (15 C); soluble in ethanol. Stability Stable to
light, and at pH 59. Strychnine is a base, and forms water-soluble salts with acids: the
hydrochloride, with 1.52.0 moles of water of crystallisation which are lost at 110 C; the
sulfate, as pentahydrate, becoming anhydrous at 100 C. Specifc rotation []D18 139
(chloroform) pKa 8.26
COMMERCIALISATION:
Production Produced by extracting seeds of Strychnos or Loganiaceae spp. History The
physiological properties of the alkaloids in extracts of Strychnos (Loganiaceae) species
have long been known, strychnine being the most important. Seeds of Strychnos nux-
vomica were used as a rat poison in Germany in the late 17th century. Strychnine was
frst isolated in pure form from St. Ignatius beans (Strychnos ignatii) in 1818 (Pest Control
Agents from Natural Products).
APPLICATIONS:
Biochemistry Antagonist to the neurotransmitter glycine, acting principally on the
spinal cord. Mode of action Rodenticide absorbed mainly by the intestine. Uses Used
N
O
O
N
H
H
H
H
H
sulfallate 491
(as strychnine sulfate) for control of moles, squirrels, rabbits, gophers, mice and other
small mammals, and also for control of sparrows, pigeons and other bird pests. Rats are
somewhat resistant, as they normally avoid the bait. Formulation types CB; RB .
ANALYSIS:
Product analysis by acid-base titration (AOAC Methods, 18th Ed., 920.211) or by
spectrophotometry (ibid., 962.22).
ICSC.197 (2000). EU Status (1107/2009) Not approved, 2004/129/EC.
50
for rabbits >2000 mg/kg. ADI/RfD (EPA) cRfD
0.0003 mg/kg b.w. [1988]. Other Lethal dose: for rats 130 mg/kg; for bearsc. 0.5 mg/kg;
for man 3060 mg/kg. Toxicity Class WHO (a.i.) Ib.ECClassifcation T+; R27/28| N;
R50, R53 (base): T+; R26/28| N; R50, R53 (salts)
ECOTOXICOLOGY:
Birds Acute oral LD
50
for starlings <5.0 mg sulfate/kg. Dietary LC
50
for bobwhite
quailc. 4000, mallard ducksc. 200 ppm.
ENVIRONMENTAL FATE:
Animals Rapidly absorbed by gastro-intestinal tract but not through the skin. Distribution,
metabolism to several non-toxic polar products, and excretion, are rapid. Only 520% of
unchanged alkaloid is excreted in the urine; the major metabolites were the 21,22-epoxide
and strychnine N-oxide. Soil/Environment Immobile in soil; degraded microbially.
sulfallate
Herbicide
NOMENCLATURE:
Common name CDEC (WSSA); sulfallate (BSI, E-ISO, (m) F-ISO)
IUPAC name 2-chloroallyl diethyldithiocarbamate
Chemical Abstracts name 2-chloro-2-propenyl diethylcarbamodithioate
CAS RN [95067] EC no 2023889 Development codes CP 4742 (Monsanto)
Smiles code CCN(CC)C(=S)SCC(=C)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 223.8 M.f. C
8
H
14
ClNS
2
Form Amber oil.
B.p. 128 C /1 mmHg V.p. 293 mPa (20 C) S.g./density 1.088 (25 C) Solubility In
water 92 mg/l (25 C). Soluble in most organic solvents. Stability Hydrolysed by alkali;
DT
50
47 d (pH 5), 30 d (pH 8).
COMMERCIALISATION:
History Herbicide introduced by the Monsanto Co. Patents US 2744898, US 2919182.
492
sulfoxide
APPLICATIONS:
Biochemistry Inhibits lipid metabolism. Mode of action Systemic, selective herbicide,
readily absorbed by plant roots but not by foliage. Uses As a pre-em. herbicide
(36 kg/ha) on a wide range of vegetable crops controlling annual weeds, but not
established or vegetatively propagating perennials. Formulation types EC; GR .
PRODUCTS:
Discontinued products Vegadex* (Monsanto).
ANALYSIS:
Product analysis is by glc. Residues may be determined by glc (Anal. Methods Pestic. Plant
Growth Regul., 1972, 6, 704; see also Pestic. Anal. Man., I, 302).
IARC 30 (1983).
IARC Class 2B
Oral Acute oral LD
50
for rats 850 mg/kg. Skin and eye It is somewhat irritant to skin and
eyes. Toxicity Class WHO (a.i.) IIECClassifcation R45| Xn; R22| N; R50, R53
ENVIRONMENTAL FATE:
Soil/Environment Persists in soil for 2142 d.
sulfoxide
NOMENCLATURE:
Common name sulfoxide (ESA)
IUPAC name 2-(1,3-benzodioxol-5-yl)-1-methylethyl octyl sulfoxide; 1-methyl-2-(3,4-
methylenedioxyphenyl)ethyl octyl sulfoxide
Chemical Abstracts name 5-[2-(octylsulfnyl)propyl]-1,3-benzodioxole
CAS RN [120627] Smiles code CCCCCCCCS(=O)C(C)Cc1ccc2OCOc2c1
PHYSICAL CHEMISTRY:
18
H
28
O
3
S Form Tech. is a brown liquid
with a mild odour. B.p. Decomposes without boiling. S.g./density 1.061.09 (25 C, tech.)
Solubility Practically insoluble in water. Miscible with most organic solvents; in petroleum
oils 2025 g/kg.
COMMERCIALISATION:
History Synergist for pyrethroid insecticides reported by M. E. Synerholm et al. (Contrib.
Boyce Thompson Inst., 1947, 15, 35). Introduced by S. B. Penick & Co. Patents US 2486445
(to Boyce Thompson Institute).
PRODUCTS:
Discontinued products Sulfocide* (Penick).
sulprofos 493
ANALYSIS:
Product analysis is by uv spectroscopy at 288 nm, after isolation by steam distilllation
(WHO Insecticides, 30 Rev. 1,p. 170).
Oral Acute oral LD
50
sulglycapin
Herbicide
NOMENCLATURE:
Common name sulglycapin (BSI, E-ISO, (m) F-ISO)
IUPAC name azepan-1-ylcarbonylmethyl methylsulfamate
Chemical Abstracts name 2-(hexahydro-1H-azepin-1-yl)-2-oxoethyl methylsulfamate
CAS RN [51068601] Development codes BAS 461H; BAS 46 100H (both BASF)
Smiles code CNS(=O)(=O)OCC(=O)N1CCCCCC1
PHYSICAL CHEMISTRY:
Mol. wt. 250.3 M.f. C
9
H
18
N
2
O
4
S
COMMERCIALISATION:
History Herbicide reported by E. Eysell et al. (Proc. Br. Crop Prot. Conf. Weeds, 1976, 2,
709). Evaluated by BASF AG.
sulprofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name sulprofos (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate
Chemical Abstracts name O-ethyl O-[4-(methylthio)phenyl] S-propyl
phosphorodithioate CAS RN [35400432] Development codes NTN 9306;
BAY 123234 (both Bayer) Smiles code CCCSP(=S)(OCC)Oc1ccc(SC)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 322.4 M.f. C
12
H
19
O
2
PS
3
Form Colourless oil, with a mercaptan-like odour; (tech.,
tan liquid). M.p. 15 C (tech.) B.p. 125 C /1 Pa V.p. 0.084 mPa (20 C); 0.16 mPa (25 C)
O
P
S OCH
2
CH
3
SCH
2
CH
2
CH
3 CH
3
S
494
sulprofos
K
ow
logP = 5.48 Henry 8.74 10-2 Pa m
3
mol
1
Solubility In water 0.31 mg/l (20 C). In isopropanol 400600, dichloromethane, hexane,
toluene >1200 (all in g/l, 20 C). Stability Hydrolysis in buffer systems, DT
50
(22 C) 26 d
(pH 4), 151 d (pH 7), 51 d (pH 9). Photodegraded in water and on soil surfaces. For flms in
sunlight, 50% decomposition occurs in <2 days. F.p. 64 C
COMMERCIALISATION:
History Insecticide reported by G. Zoebelein (Proc. Conf. Pest Control, 4th, Cairo, 1978,
p. 456). Introduced by Bayer AG. Patents NL 6508899 (1965) (to Bayer)
Manufacturers Bayer Corp.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic insecticide with
contact and stomach action. Uses Control of Lepidoptera, Thysanoptera, Heliothis spp., and
other insects in cotton, soya beans, tobacco, vegetables, and tomatoes.
Formulation types EC; UL .
PRODUCTS:
Discontinued products Bolstar* (Bayer CropScience); Helothion* (Bayer).
ANALYSIS:
Product analysis by glc with FID (AOAC Methods, 18th Ed., 980.12).
EHC 63 (1986; a general review of organophosphorus insecticides). ICSC.248 (1995).
Oral Acute oral LD
50
for male rats 304, female rats 176, male and female micec. 1700 mg/
kg. Skin and eye Acute percutaneous LD
50
for male rats 5491, female rats 1064 mg/kg.
Not irritating to skin; mild irritant to eyes (rabbits). Not a skin sensitiser. Inhalation LC
50

(4 h) for male and female rats >4130 g/l air. NOEL (2 y) for dogs 10 mg/kg diet (0.25 mg/
kg b.w.), rats 6, mice 2.5. ADI/RfD (EPA) 0.003 mg/kg b.w. [1986]. Toxicity Class WHO
(a.i.) II EPA (formulation) II ECClassifcation (T; R25| Xn; R21)
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(5 d) for bobwhite
quail 99 mg/kg diet. Fish LC
50
(96 h) for bluegill sunfsh 1114, rainbow trout 2338 mg/l.
Daphnia LC
50
(48 h) 0.831 g/l. Algae ErC50 for Selenastrum capricornutum 64 mg/l.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration,c. 92% is eliminated within 24 h. The main
degradation products are the oxygen-analogue, phenol, sulprofos sulfoxide and sulprofos
sulfone, and the corresponding oxygen-analogues and phenols. Plants The major
metabolites are sulprofos sulfoxide and sulprofos sulfone. The corresponding phenols and
oxygen-analogues are minor degradation products. Soil/Environment The adsorption
of sulprofos in various soil types occurred rapidly; the compound is highly adsorbed.
DT
50
in the range of some days to several weeks, depending on the soil types. The major
metabolites are sulprofos sulfoxide and sulprofos sulfone.
swep 495
sultropen
Fungicide
NOMENCLATURE:
Common name sultrop(ne) ((m) F-ISO); sultropen (BSI, E-ISO)
IUPAC name 2,4-dinitrophenyl pentyl sulfone
Chemical Abstracts name 2,4-dinitro-1-(pentylsulfonyl)benzene
CAS RN [963224] Development codes RD 7901; BTS 7901
Smiles code CCCCCS(=O)(=O)c1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 302.3 M.f. C
11
H
14
N
2
O
6
S
COMMERCIALISATION:
History Fungicide evaluated by Boots Co., Ltd (later Schering Agrochemicals).
swep
Herbicide
NOMENCLATURE:
Common name swep (ANSI, WSSA); MCC (JMAF)
IUPAC name methyl 3,4-dichlorocarbanilate
Chemical Abstracts name methyl (3,4-dichlorophenyl)carbamate
Smiles code COC(=O)Nc1ccc(Cl)c(Cl)c1
PHYSICAL CHEMISTRY:
Mol. wt. 220.1 M.f. C
8
H
7
Cl
2
NO
2
COMMERCIALISATION:
History Herbicide reported by H. R. Hudgins (Proc. South. Weed Control Conf., 1963, 16,
118). Introduced by FMC Corp.
ANALYSIS:
In water, by lc with uv detection, see AOAC Methods, 18th Ed., 992.14.
496
SYP-Z048
SYP-Z048
Fungicide
NOMENCLATURE:
Chemical Abstracts name 3-[5-(4-chlorophenyl)-2,3-dimethyl-3-isoxazolidinyl]pyridine
Other names dingjunezuo CAS RN [847749375] Development codes SYP-Z048
(Shenyang Research)
PHYSICAL CHEMISTRY:
Mol. wt. 288.8 M.f. C
16
H
17
ClN
2
O Form Light yellow sticky oil. Solubility Insoluble in
water. Very soluble in acetone, ethyl acetate and chloroform.
COMMERCIALISATION:
History Discovered by Shenyang Research Institute of Chemical Industry in 1996 and
registered in China in 2002.
APPLICATIONS:
Mode of action Broad spectrum systemic fungicide with protective and curative
properties. Uses For control of tomato grey mould, apple spot leaf drop, peanut brown
spot, cucumber scab, wheat root rot and grape white rot. Formulation types EC.
PRODUCTS:
Other products Jun Si Qi (Shenyang Research).
Oral Acute oral LD
50
dermal LD
50
for rabbits >2000 mg/kg. Other Negative in Ames test.
O N
CH
3
CH
3
N
Cl
SYP-Z071 497
SYP-Z071
Fungicide
FRAC 11, C3; QoI; strobilurin type: methoxyacrylate
NOMENCLATURE:
IUPAC name methyl 2-{2-[3-(4-chlorophenyl)-1-methylallylideneaminooxymethyl]
phenyl}-3-methoxyacrylate
Other names enestroburin; enestrobin CAS RN [750643573]
Development codes SYP-Z071
Smiles code COC=C(C(=O)OC)c1ccccc1CON=C(C)C=Cc2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 399.9 M.f. C
22
H
22
ClNO
4
Form White crystals; (tech. is a pale yellow oil).
Solubility Insoluble in water. Very soluble in acetone, ether and chloroform.
COMMERCIALISATION:
History Discovered by Shenyang Research Institute of Chemical Industry in 1997 and
reported by L. X. Zhang et al. (Proc. BCPC. Int. Congr., Glasgow, 2003, 1, 93).
APPLICATIONS:
Biochemistry Quinone outside Inhibitor. Respiratory electron transport inhibitor. Acts
by inhibiting cytochrome pathway (Complex III) between cytochrome b and cytochrome
c1, at the ubiquinol oxidising site. Mode of action Protective, curative translaminar and
systemic fungicide, with secondary insecticidal activity. Uses Provides broad-spectrum
disease control, for example of cucumber downy mildew (Pseudoperonospora cubensis),
cucumber powdery mildew (Sphaerotheca fuliginea), cucumber grey mould (Botrytis
cinerea) and wheat powdery mildew (Blumeria graminis). Also active against Lepidoptera.
Oral Acute oral LD
50
percutaneous LD
50
for male and female rabbits >2000 mg/kg. Slight eye irritation; no skin
irritation (rabbits). Other Negative in Ames test.
Cl
N
CH
3
O
O
CH
3
O
O
CH
3
498
2,4,5-T
2,4,5-T
Herbicide
Esters include: 2,4,5-T-butotyl (the 2-butoxyethyl), 2,4,5-T-butyl, 2,4,5-T-isoctyl (the iso-
octyl), and 2,4,5-T-butometyl (the 2-butoxy-1-methylethyl).
NOMENCLATURE:
Common name 2,4,5-T (BSI, E-ISO, (m) F-ISO, WSSA, JMAF); 2,4,5-T (also used by JMAF
for the butotyl ester)
IUPAC name (2,4,5-trichlorophenoxy)acetic acid
Chemical Abstracts name (2,4,5-trichlorophenoxy)acetic acid CAS RN [93765]
2,4,5-T; [3813147] 2,4,5-T-trolamine; [2008460] 2,4,5-T-triethylammonium; [25168
154] 2,4,5-T-isoctyl EC no 2022733 Smiles code OC(=O)COc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Composition Tech. is 94%. Mol. wt. 255.5; 367.7 (2,4,5-T-isoctyl) M.f. C
8
H
5
Cl
3
O
3
;
C16H21Cl3O3 (2,4,5-T-isoctyl) Form Colourless crystals. M.p. 154-155 C; 113-115 C
(tris(2-hydroxyethyl)ammonium salt); solidifes 20 C (tech., butyl ester) V.p. 7 10
4
mPa
(25 C) K
ow
logP = 2.0 (ARS PPD, unstated pH) Henry 1.19 10
6
Pa m
3
mol
1
(calc.)
S.g./density 1.80 (20 C) Solubility In water 150 mg/l (25 C). In methanol 496, ethanol
548.2, diethyl ether 234.3, toluene 7.32, xylene 6.08, heptane 0.4 (all in g/l, 25 C). The
alkali-metal and amine salts are readily soluble in water, but insoluble in petroleum oils. The
esters are practically insoluble in water, but soluble in petroleum oils. Stability Stable in
aqueous solution at pH 59. pKa 2.85 (J. Agr. & Food Chem., 26, 189 (1978))
COMMERCIALISATION:
Production Manufactured by condensation of sodium chloroacetate with sodium
2,4,5-trichlorophenoxide. At high temperatures the action of alkali on 2,4,5-trichlorophenol
can produce some 2,3,7,8-tetrachlorodibenzo-p-dioxin. History Herbicide reported by
C. L. Hamner & H. B. Tukey (Science, 1944, 100, 154). Introduced by Amchem Products Inc.
(later Rhne-Poulenc Agrochimie).
APPLICATIONS:
Biochemistry Similar to that of 2,4-D. Mode of action Selective systemic herbicide with
hormone-like action, absorbed by the roots, bark, and foliage, and translocated through the
phloem. Uses Control of woody weeds, brush, and undergrowth in grassland and non-crop
land. Control of tree shoots and undergrowth in forestry. Treatment of tree stumps to
prevent regrowth. Amine formulations were used for weed control in rice.
Phytotoxicity Phytotoxic to almost all broad-leaved crops, and particularly
cotton, tomatoes, ornamentals, grapes, and fruit trees. Formulation types EC; SL .
Compatibility Mixing with solutions of heavy-metal salts, e.g. copper sulfate, can lead to
focculation.
Cl
Cl
Cl
OCH
2
CO
2
H
2,4,5-T 499
PRODUCTS:
Discontinued products Sylvoxone 850* (isoctyl ester) (Sopra); Weedone* (Rhne-
Poulenc).
ANALYSIS:
Product analysis by hplc (AOAC Methods, 18th Ed., 980.08; J. Assoc. Off. Anal. Chem., 1980,
63, 379), by hplc, or glc or titration (CIPAC Handbook, 1985, 1C, 2220), by glc of a suitable
ester (CIPAC Handbook, 1985, 1C, 2072, 2257; 1994, F, 292319), or by an epinasty
determination (AOAC Methods, 18th Ed., 960.10). Free phenol impurity determined by hplc
(CIPAC Handbook, 1994, F, 362). Estimation of 2,3,7,8-tetrachlorodibenzo-p-dioxin content
has been studied (J. W. Edmunds et al., Pestic. Sci., 1973, 4, 101; P. G. Baker et al., ibid., 1981,
12, 297; CIPAC Handbook, 1994, F, 352; ibid., 1985, C, 2284). Residues determined by glc
of a suitable ester (Pestic. Anal. Man., 1979, 1, 201-D; W. Specht & M. Tillkes, Fresenius Z.
Anal. Chem., 1980, 301, 300; 1981, 4307, 257; Anal. Methods Pestic. Plant Growth Regul., 1972,
6, 702; H. Lkke & P. Odgaard, Pestic. Sci., 1981, 12, 375; H. E. Munro, ibid., 1977, 8, 157).
In drinking water by conversion to methyl ester with diazomethane, then glc with ECD
(AOAC Methods, 18th Ed., 992.32).
JMPR Evaln. 33 (1979), 37 (1981). PDS 13 (1975). IARC 41 (1986); Suppl. 7 (1987).
IARC Class 2B
Oral Acute oral LD
50
for rats 3001700 mg/kg (depending on vehicle and rat strain);
for mice 3891380, dogs 100 mg/kg. Skin and eye Acute percutaneous LD
50
for rats
>5000 mg/kg. NOEL In 2-y feeding trials no effect observed in rats receiving 30 mg/kg
diet; nor in 90 d trials in beagle dogs at 60 mg/kg diet. ADI/RfD (JMPR) 0.03 mg/kg b.w.
[1981], for 2,4,5-T containing not more than 0.01 mg tetrachlorodibenzodioxin (TCDD)/
kg; (EPA) cRfD 0.01 mg/kg b.w. [1989]. Water GV 0.009 mg/l. Other A contaminant,
2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), produced foetal deaths in hamsters at 0.0091
mg/kg and it causes serious acne in man. Later methods of manufacture of 2,4,5-T limited
the amount of the contaminant to <0.01 mg/kg 2,4,5-T. Toxicity Class WHO (a.i.) II
ECClassifcation Xn; R22| Xi; R36/37/38| N; R50, R53 (for acid, salts or esters) PIC Yes.
ECOTOXICOLOGY:
Birds Acute oral LC
50
(8 d) for bobwhite quail 2776 mg/kg diet; for ducks >4650 mg/kg
diet. Fish LC
50
(96 h) for rainbow trout 350, carp 355 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Animals In mammals, following oral administration, 50% is eliminated in the urine
within 23 h. There is no accumulation. Plants Degradation in plants is similar to that
for 2,4-D. This involves cleavage of the acetic acid moiety, ring hydroxylation of the
2,4,5-trichlorophenol so formed, and presumably ring opening and degradation. Soil/
Environment In soil, degradation occurs more slowly than for 2,4-D.
500
tar oils
tar oils
Fungicide, herbicide, insecticide
NOMENCLATURE:
CAS RN [65996829], coal tar oils; [8002297] tar oils (naphthalene oils, derived from
wood tar); different numbers apply to tar oils from other sources
PHYSICAL CHEMISTRY:
Composition Tar oils consist mainly of aromatic hydrocarbons, but contain components
soluble in aqueous alkali: the phenols or tar acids; and nitrogenous bases soluble in dilute
mineral acids: tar bases. They are produced by the distillation of tars resulting from the
high-temperature carbonisation of coal and of coke oven and blast furnace tars.
Form Brown to black liquids. B.p. Tar oils are the FRACtion boiling from 230 C
upwards. S.g./density 1.051.11 (15 C) Solubility Insoluble in water. Soluble in most
organic solvents and in dimethyl sulfate.
COMMERCIALISATION:
Production Tar oils are produced by the distillation of tars resulting from the high-
temperature carbonisation of coal and of coke oven and blast furnace tars.
History Although they have been used for wood preservation since 1890, the
introduction of the formulated products known as tar oil washes for crop protection, using
the heavy creosote and anthracene oil ranges, dates fromc. 1920.
APPLICATIONS: Uses Control of overwintering stages (particularly eggs) of many
insects, e.g. aphids, suckers, moths, Mealybugs and scale insects, and overwintering diseases
on dormant pome, stone, cane and bush fruit, and grape vines. Moss and lichen are also
controlled. Also used as a hop defoliant, and as a game repellent in forestry.
Phytotoxicity Extremely phytotoxic, and so must only be used during the dormant
season. Formulation types EC; Emulsion.
PRODUCTS:
Discontinued products Clean-Up* (Miracle).
ANALYSIS:
Product analysis is by standard methods (MAFF Ref. Bk., 1958, No. 1, p. 81).
Skin and eye Irritating to skin, eyes and respiratory system. May cause dermatitis,
especially in sunlight. ECClassifcation Tar oils are classifed as R45
ECOTOXICOLOGY:
Fish Toxic to fsh.
2,4,5-TB 501
tazimcarb
Insecticide, molluscicide
NOMENCLATURE:
Common name tazimcarbe ((m) F-ISO); tazimcarb (BSI, E-ISO)
IUPAC name N-methyl-1-(3,5,5-trimethyl-4-oxo-1,3-thiazolidin-2-ylideneamino-oxy)
formamide; 3,5,5-trimethyl-2-methylcarbamoyloxyimino-1,3-thiazolidin-4-one
Chemical Abstracts name 3,5,5-trimethyl-2,4-thiazolidinedione 2-[O-[(methylamino)
carbonyl]oxime]; formerly 2-[[[(aminocarbonyl)oxy]methyl]imino]-3,5,5-
trimethyl-4-thiazolidinone CAS RN [40085572], formerly [62113035]
Development codes PP505 Smiles code CNC(=O)ON=C1SC(C)(C)C(=O)N1C
PHYSICAL CHEMISTRY:
Mol. wt. 231.3 M.f. C
8
H
13
N
3
O
3
S
COMMERCIALISATION:
History Insecticide and molluscicide evaluated by ICI Agrochemicals.
APPLICATIONS:
2,4,5-TB
Herbicide
NOMENCLATURE:
Common name 2,4,5-TB (BSI, E-ISO, (m) F-ISO, WSSA)
IUPAC name 4-(2,4,5-trichlorophenoxy)butyric acid
Chemical Abstracts name 4-(2,4,5-trichlorophenoxy)butanoic acid
CAS RN [93801] Smiles code OC(=O)CCCOc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 283.5 M.f. C
10
H
9
Cl
3
O
3
COMMERCIALISATION:
History Herbicide.
502
2,3,6-TBA
2,3,6-TBA
Herbicide
HRAC O WSSA 4; benzoic acid (auxin)
NOMENCLATURE:
Common name 2,3,6-TBA (BSI, E-ISO, (m) F-ISO, WSSA); acide trichlorobenzoique
(optional alternative in France); TCBA (JMAF)
IUPAC name 2,3,6-trichlorobenzoic acid
Chemical Abstracts name 2,3,6-trichlorobenzoic acid CAS RN [50317]; [2078
424] 2,3,6-TBA-sodium EC no 2000264 Development codes HC-1281 (Heyden)
Smiles code OC(=O)c1c(Cl)ccc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade isc. 60% 2,3,6-TBA. Mol. wt. 225.5 M.f. C
7
H
3
Cl
3
O
2

Form Colourless crystals; (tech., colourless to buff, crystalline powder). M.p. 125126 C
(pure acid);c. 80100 C (tech.) B.p. Decomposes on distillation V.p. Very low at room
temperature; 3.2 Pa (100 C) Solubility In water 7.7 g/l (22 C). Readily soluble in
common organic solvents, e.g. acetone 60.7, benzene 23.8, chloroform 23.7, ethanol
63.7, methanol 71.7, xylene 21.0 (all in g/100 ml). Sodium salt, in water 440 g/kg (25 C).
Stability Stable to light, and to temperatures up to 60 C.
COMMERCIALISATION:
History Herbicide reported by H. J. Miller (Weeds, 1952, 1, 185). Introduced by the
Heyden Chemical Corp. and later by E. I. du Pont de Nemours & Co. (who now neither
manufacture nor market it), and currently available in mixtures with other herbicides.
Patents US 2848470 (1958); US 3081162 (1963)
APPLICATIONS:
Biochemistry Auxin type. Mode of action Systemic growth-regulator herbicide with
hormone-like action, absorbed by the leaves and roots. Uses Used post-emergence, in
combinations with other growth regulator herbicides, in cereals and grass seed crops to
control broad-leaved annual and perennial weeds, including Bilderdykia convolvulus, Galium
aparine, Polygonum aviculare, P. persicaria, Chamomilla and Matricaria spp.
Compatibility Mixtures with fertilisers are not recommended.
PRODUCTS:
Discontinued products Trysben* (dimethylammonium salt) (DuPont);
Discontinued mixtures Benzabor* (+ borax) (US Borax).
Cl
CO
2
H
Cl
Cl
TDE 503
ANALYSIS:
Product and salt analysis by titration or by glc (CIPAC Handbook, 1985, 1C, 2225; ibid., 2257;
ibid., 1994, F, 292319); in mixture with MCPA, by titration or by glc of a derivative (ibid.,
1985, 1C, 2148). Residues determined by glc of a suitable derivative (J. J. Kirkland & H. L.
Pease, J. Agric. Food Chem., 1964, 12, 468).
Oral Acute oral LD
50
for rats 1500, mice 1000, guinea pigs >1500, rabbits 600 mg/kg.
50
for rats >1000 mg/kg. NOEL In 6469 d feeding
trials, rats receiving 10 000 mg/kg diet suffered a minor disturbance of water metabolism,
no trace of which was apparent at 1000 mg/kg diet. It is largely excreted unchanged in the
urine. Toxicity Class WHO (a.i.) III EPA (formulation) III ECClassifcation Xn; R22| N;
R51, R53
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hens >1500 mg/kg. Fish Threshold value for toxic activity
100150 mg/l for perch and 300 mg/l for roach. One of several determining factors is the
content of the second, more toxic, 2,4,5- isomer in the active ingredient. Bees Not toxic
to bees.
ENVIRONMENTAL FATE:
Animals In mammals, excretion is mainly as the unchanged form in the urine.
Soil/Environment Very slow degradation in soil. A stable protein complex may possibly
be formed.
TDE
Insecticide
NOMENCLATURE:
Common name TDE (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane
Chemical Abstracts name 1,1-(2,2-dichloroethylidene)bis[4-chlorobenzene]
Other names DDD CAS RN [72548] Development codes Me-1700
Smiles code ClC(Cl)C(c1ccc(Cl)cc1)c2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 320.0 M.f. C
14
H
10
Cl
4
B.p. 193 C (Agchem. Desk Ref.) Solubility In water 0.05
ppm (25 C) (Residue Reviews, 103, 1 (1988))
Stability Stable to hydrolysis; DT
50
28 y (pH 7, 25 C) (Agchem. Desk Ref.)
COMMERCIALISATION:
History Insecticide reported by P. Luger et al. (Helv. Chim. Acta, 1944, 27, 892). Introduced
by Rohm & Haas Co. (found in nature as a degradation product of DDT).
504
tebutam
APPLICATIONS:
Mode of action Contact, ingested insecticide.
PRODUCTS:
Discontinued products Rhothane* (Rohm & Haas).
ANALYSIS:
See Pestic. Anal. Man., I, 303, 502.
tebutam
Herbicide
HRAC K1 WSSA 3; benzamide (mi)
NOMENCLATURE:
Common name tebutam (BSI, E-ISO); t(butame) ((m) F-ISO); butam (ANSI, WSSA); no
name (Japan)
IUPAC name N-benzyl-N-isopropylpivalamide
Chemical Abstracts name 2,2-dimethyl-N-(1-methylethyl)-N-(phenylmethyl)
propanamide CAS RN [35256850] EC no 2524703
Development codes GPC-5544 (Gulf); Ro 149480/000 (Roche); CGA 39625 (Ciba-
Geigy)
Smiles code CC(C)N(Cc1ccccc1)C(=O)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 233.4 M.f. C
15
H
23
NO Form Light brown liquid. B.p. 9597 C /0.1 mmHg
V.p.c. 89 mPa (25 C) K
ow
logP = 3 Henry 1.5 10-2 Pa m
3
mol
1
(calc.)
S.g./density 0.975 (20 C) Solubility In water 0.79 g/l (pH 7, 20 C). Readily soluble
in organic solvents, e.g. acetone, hexane, methanol, toluene, chloroform >500 g/l (25 C).
Stability Chemically stable under normal storage conditions. Thermally stable at
temperatures below the boiling point. Stable to light. Stable to hydrolysis at pH 5, 7 and 9
(all at 25 C). F.p. >80 C (with 2% toluene)
COMMERCIALISATION:
History Herbicide reported by R. A. Schwartzbeck (Proc. Br. Crop Prot. Conf. Weeds,
1976, 2, 739). Introduced by Gulf Oil Chemicals Co. and later acquired by Dr R. Maag Ltd
(became Syngenta AG). Patents US 3974218; US 3707366 (to Gulf)
Manufacturers Syngenta
CH
2
N CH(CH
3
)
2
C
C(CH
3
)
3
O
tecoram 505
APPLICATIONS:
Biochemistry Microtubule assembly inhibition. Mode of action Selective herbicide,
acting by inhibition of weed germination and also through root uptake. Uses Pre-
emergence control of annual grasses, volunteer cereals and broad-leaved weeds in
oilseed rape and brassicas, at 2.83.6 kg/ha. Phytotoxicity A large number of crops are
susceptible, including cereals, maize, carrots, fax, onions, garlic, lettuce, melons, sorghum,
spinach, and sugar beet. Formulation types EC.
PRODUCTS:
Discontinued products Colzor* (Novartis); Comodor* (Novartis).
ANALYSIS:
Product analysis by hplc. Residues determined by glc with FID or by hplc.
Oral Acute oral LD
50
for albino rats 6210, guinea pigs 2025 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats and albino rabbits >2000 mg/kg. A slight irritant to the eyes and
skin of rabbits. Inhalation LC
50
for rats >2.18 mg/l air. There was no adverse effect when
albino rats were exposed to an aerosol (66% vol. mixture of tech. product and acetone).
NOEL (2 y) for rats 600, mice 3000 ppm. ADI/RfD (BfR) 0.3 mg/kg b.w. [1990].
ECOTOXICOLOGY:
Birds Dietary LC
50
(8 d) for mallard ducks and bobwhite quail >5000 mg/kg. Fish LC
50

(96 h) for rainbow trout 23, bluegill sunfsh 19, moonfsh 18.7 mg/l. Algae LC
50
(96 h) for
Scenedesmus subspicatus 82 mg/l. Bees Acute oral LD
50
100 g/bee.
ENVIRONMENTAL FATE:
Animals In rats, following oral administration, rapidly excreted in the urine and faeces.
Plants In plants, tebutam is rapidly metabolised. Soil/Environment Bound by the organic
matter of soil; DT
50
c. 2 mo.
tecoram
Fungicide
NOMENCLATURE:
Common name tecoram (BSI)
IUPAC name N,N,N,N-tetramethyl-N,N-ethylenedi(thiuram disulfde)
Chemical Abstracts name N,N,N,N-tetramethyl-4,9-dithioxo-2,3,10,11-tetrathia-5,8-
diazadodecanedithioamide CAS RN [5836237]
Smiles code CN(C)C(=S)SSC(=S)NCCNC(=S)SSC(=S)N(C)C
506
TEPP
PHYSICAL CHEMISTRY:
Mol. wt. 450.8 M.f. C
10
H
18
N
4
S
8
COMMERCIALISATION:
History Fungicide evaluated by Aagrunol N.V.
PRODUCTS:
Discontinued products Azosan* (Aagrunol).
TEPP
IRAC 1B
NOMENCLATURE:
Common name TEPP (BSI, E-ISO, (m) F-ISO, ESA, JMAF); ethyl pyrophosphate (BAN)
IUPAC name tetraethyl pyrophosphate
Chemical Abstracts name tetraethyl diphosphate Other names TEP CAS RN [107
493] EC no 2034953 Smiles code CCOP(=O)(OCC)OP(=O)(OCC)OCC
PHYSICAL CHEMISTRY:
Mol. wt. 290.2 M.f. C
8
H
20
O
7
P
2
Form Colourless hygroscopic liquid; (tech. is a dark amber-
coloured mobile liquid). B.p. 124 C /1 mmHg V.p. 21 mPa (20 C)
S.g./density 1.185 (20 C);c. 1.2 (25 C, tech.) Solubility Miscible with water and most
organic solvents; sparingly soluble in petroleum oils. Stability Rapidly hydrolysed by water,
DT
50
6.8 h (pH 7, 25 C). Decomposes at 170 C with the formation of ethylene.
COMMERCIALISATION:
History Aphicide discovered in 1938 by G. Schrader & H. Kkenthal (cited by G. Schrader,
Phosphorsure-Ester). In 1943, I. G. Farbenindustrie AG introduced a derivative then
thought to be hexaethyl tetraphosphate (known as HETP) but since shown to contain
TEPP as the main insecticidal component.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Non-systemic acaricide and
aphicide. Uses Acaricide and aphicide with a very brief persistence.
Formulation types AE .
PRODUCTS:
Discontinued products Nifos T* (Monsanto); Vapotone* (Chevron).
ANALYSIS:
Product analysis by selective hydrolysis (CIPAC Handbook, 1970, 1, 667; AOAC Methods, 18th
Ed., 949.06). Residues determined by glc (J. Crossley, Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 471).
terallethrin 507
Oral Acute oral LD
50
for rats 1.12 mg/kg. Skin and eye Acute percutaneous LD
50
for
male rats 2.4 mg/kg. Toxicity Class WHO (a.i.) IaECClassifcation T+; R27/28| N; R50
ENVIRONMENTAL FATE:
Animals It is rapidly metabolised by animals.
terallethrin
Insecticide
IRAC 3
NOMENCLATURE:
Common name terallethrin (BSI, E-ISO); t(rall) ((f) F-ISO)
IUPAC name (RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl
2,2,3,3-tetramethylcyclopropanecarboxylate
Chemical Abstracts name ()-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-
1-yl 2,2,3,3-tetramethylcyclopropanecarboxylate CAS RN [15589318] unstated
stereochemistry Development codes M-108
Smiles code CC1=C(CC=C)C(=O)CC1OC(=O)C2C(C)(C)C2(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 276.4 M.f. C
17
H
24
O
3
Form Light yellow oily liquid. V.p. 27 mPa (20 C)
Solubility Insoluble in water. Soluble in organic solvents. Stability Unstable to light and
to alkali.
COMMERCIALISATION:
History Insecticide introduced by Sumitomo Chemical Co., Ltd.
Manufacturers Jiangsu Yangnong
APPLICATIONS:
neurons by interaction with the sodium channel. Uses Public health fumigant insecticide
used for control of housefies and cockroaches.
ANALYSIS:
Oral Acute oral LD
50
for rats 174224 mg/kg.
CH
3
CH
3
CH
3
C
CH
3
H
O
O
CH
3
CH
2
CH
CH
2
O
508
terbuchlor
terbucarb
Herbicide
NOMENCLATURE:
Common name MBPMC (JMAF); terbucarb (BSI, E-ISO); terbucarbe ((m) F-ISO);
terbutol (WSSA)
IUPAC name 2,6-di-tert-butyl-p-tolyl methylcarbamate
Chemical Abstracts name 2,6-bis(1,1-dimethylethyl)-4-methylphenyl methylcarbamate
CAS RN [1918112] Development codes Hercules 9573
Smiles code CNC(=O)Oc1c(cc(C)cc1C(C)(C)C)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 277.4 M.f. C
17
H
27
NO
2
COMMERCIALISATION:
History Herbicide reported by A. H. Haubein & J. R. Hansen (J. Agric. Food Chem., 1965, 13,
555). Introduced by Hercules Inc. (later Nor-Am.).
PRODUCTS:
Discontinued products Azak* (Hercules).
terbuchlor
Herbicide
NOMENCLATURE:
Common name terbuchlor (BSI, E-ISO, ANSI, WSSA); terbuchlore ((m) F-ISO)
IUPAC name N-butoxymethyl-6-tert-butyl-2-chloroacet-o-toluidide
Chemical Abstracts name N-(butoxymethyl)-2-chloro-N-[2-(1,1-dimethylethyl)-6-
methylphenyl]acetamide CAS RN [4212935] Development codes MON 0358; CP 46
358 Smiles code CCCCOCN(C(=O)CCl)c1c(C)cccc1C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 325.9 M.f. C
18
H
28
ClNO
2
COMMERCIALISATION:
History Herbicide evaluated by Monsanto Co.
tetcyclacis 509
tetcyclacis
NOMENCLATURE:
Common name tetcyclacis (BSI, E-ISO, (m) F-ISO)
IUPAC name rel-(1R,2R,6S,7R,8R,11S)-5-(4-chlorophenyl)-3,4,5,9,10-penta-
azatetracyclo[5.4.1.02,6.08,11]dodeca-3,9-diene
Chemical Abstracts name (3a,4,4a,6a,7,7a)-1-(4-chlorophenyl)-3a,4,4a,6a,7,7a-
hexahydro-4,7-methano-1H-[1,2]diazeto[3,4-f]benzotriazole CAS RN [77788217]
Development codes BAS 106W (BASF)
Smiles code Clc1ccc(cc1)N
2
N=NC3C4CC(C5N=NC54)C32
PHYSICAL CHEMISTRY:
Mol. wt. 273.7 M.f. C
13
H
12
ClN
5
Form Colourless crystalline solid. M.p. 190 C (decomp.)
Solubility In water 3.7 mg/kg (20 C). In chloroform 42, ethanol 2 (both in g/kg, 20 C).
Stability Decomposed by sunlight and concentrated acid.
COMMERCIALISATION:
History Plant growth regulator reported by J. Jung et al. (Z. Acker-Pfanzenbau, 1980, 149,
128). Introduced by BASF AG. Patents DE 2615878; GB 1573161; US 4189434
APPLICATIONS:
Biochemistry Gibberellin and sterol biosynthesis inhibitor. Mode of action Plant growth
retardant. Uses It was used for improvement of rice seedlings. Treated seedlings are more
compact and shorter than untreated ones and they show enhanced rooting and tillering
capacity after transplanting into the feld. Formulation types SP.
PRODUCTS:
Discontinued products Ken byo* (BASF).
ANALYSIS:
Product analysis is by hplc with uv detection. Residues may be determined by glc with ECD
of a derivative.
Oral Acute oral LD
50
50
for rats
>4640 mg/kg.
ECOTOXICOLOGY:
Algae EC
50
(cell volume) for Chlorella fusca 5.2 ;mol/l (Pestic. Sci. (1996) 47, 337).
510
tetrachlorvinphos
tetrachlorothiophene
Nematicide
NOMENCLATURE:
IUPAC name tetrachlorothiophene (I)
Chemical Abstracts name (I) Other names TCTP CAS RN [6012971]
Development codes TD-183 Smiles code Clc1sc(Cl)c(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 221.9 M.f. C
4
Cl
4
S
COMMERCIALISATION:
History Nematicide developed by Pennwalt Corp.
PRODUCTS:
Discontinued products Penphene* (Pennwalt).
tetrachlorvinphos
IRAC 1B
NOMENCLATURE:
Common name tetrachlorvinphos (BSI, E-ISO, (m) F-ISO); stirofos (ESA); CVMP (JMAF)
IUPAC name (Z)-2-chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate
Chemical Abstracts name (Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl
phosphate CAS RN [22248799] tetrachlorvinphos; [22350761] the analogous (E)-
isomer; [961115] mixed (Z)- + (E)- isomers Development codes SD 8447 (Shell)
Smiles code COP(=O)(OC)O/C(=C\Cl)/c1cc(Cl)c(Cl)cc1Cl;without
stereochemistry:COP(=O)(OC)OC(=CCl)c1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Composition Tech. grade is typically 98% pure. Mol. wt. 366.0 M.f. C
10
H
9
Cl
4
O
4
P
Form Tech. is an off-white crystalline solid. M.p. 9497 C V.p. 0.0056 mPa (20 C)
Henry 1.86 10
4
Pa m
3
mol
1
(calc.) Solubility In water 11 mg/l (20 C). In acetone
<200, chloroform, dichloromethane 400, xylene <150 (all in g/kg, 20 C). Stability Stable
<100 C; slowly hydrolysed (50 C), DT
50
54 d (pH 3), 44 d (pH 7), 80 h (pH 10.5).
O
P(OCH
3
)
2
O
Cl
Cl
C
Cl
C
Cl
H
(Z)- isomer
tetrachlorvinphos 511
COMMERCIALISATION:
History Insecticide reported by R. R. Whetsone et al. (J. Agric. Food Chem., 1966, 14,
352). Introduced by Shell Chemical Company, USA (later DuPont Agricultural Products,
who transferred rights to Fermenta Animal Health Co., which became Boehringer
Ingelheim Vetmedica, Inc., and to Hartz Mountain for pet uses). Patents US 3102842
Manufacturers Shanghai MCC
APPLICATIONS:
and acaricide with contact and stomach action. Uses A selective insecticide controlling
Lepidoptera and Diptera in fruit; and Lepidoptera in cotton, maize, rice, tobacco and
vegetables. With certain exceptions, not highly active against Hemiptera and other sucking
pests and, because of rapid breakdown, is not effective against soil-dwelling pests. It is used
against Muscidae in dairies and in livestock barns, against certain ectoparasites on poultry,
and against pests of stored products. Also used against insects that damage forests and
pasture. Phytotoxicity Russetting may occur on Golden Delicious apples under certain
conditions. Formulation types DP; EC; SC. WP. Compatibility Incompatible with
dodine and with alkaline materials.
PRODUCTS:
Discontinued products Appex* (Shionogi); Debantic* (ISK Biosciences); Gardcide*
(Cyanamid); Gardona* (crop protection use) (BASF); Rabon* (DuPont); Rabond*
(Cyanamid).
ANALYSIS:
Product analysis by glc with FID; details available from BASF. Residues of tetrachlorvinphos
and its major metabolites in plants determined by glc (Anal. Methods Pestic. Plant Growth
Regul., 1973, 7, 297; K. I. Beynon & A. N. Wright, J. Sci. Food Agric., 1969, 20, 250; K. I. Beynon
et al., Pestic. Sci., 1970, 1, 250, 254, 259). See also Pestic. Anal. Man., II, 180.252, 186.950. In
drinking water by glc with NPD (AOAC Methods, 18th Ed., 991.07).
EHC 63 (1986; a general review of organophosphorus insecticides). IARC 30 (1983).
IARC Class 3
Oral Acute oral LD
50
percutaneous LD
50
for rabbits >2500 mg/kg. NOEL NOAEL for rats 4.23 mg/kg b.w. (EPA
RED); NOEL (2 y) for rats 125 mg/kg diet, for dogs 200 mg/kg diet. Reproduction studies
on rats receiving 1000 mg/kg diet showed no adverse effects. ADI/RfD (EPA) aRfD 0.067,
cRfD 0.0423 mg/kg b.w. [2006]. Toxicity Class WHO (a.i.) U EPA (formulation) III
ECOTOXICOLOGY:
Birds Acute oral LD
50
for Chukar partridges and mallard ducks >2000 mg/kg, for various
other birds 15002600 mg/kg. Fish LC
50
(24 h) for fve different species 0.36.0 mg/l.
Bees Toxic to bees.
512
O,O,O,O-tetrapropyl dithiopyrophosphate
ENVIRONMENTAL FATE:
Animals In mammals, rapid metabolism occurs, with elimination of the metabolites
within a few days. Metabolites found in the urine of dogs and rats include
2,4,5-trichlorophenylethanediol glucuronide, further glucuronic acid derivatives,
2,4,5-trichloromandelic acid, and 2-chloro-1-(2,4,5-trichlorophenyl)vinylmethyl hydrogen
phosphate. No signifcant residues of tetrachlorvinphos or its metabolites are found in
milk or tissues of exposed animals. Soil/Environment For a review on metabolism and
breakdown in plants, animals and soil, see K. I. Beynon et al., Residue Rev., 1973, 47, 55.
tetrafuron
Herbicide
NOMENCLATURE:
Common name tetrafuron (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 1,1-dimethyl-3-[3-(1,1,2,2-tetrafuoroethoxy)phenyl]urea
Chemical Abstracts name N,N-dimethyl-N-[3-(1,1,2,2-tetrafuoroethoxy)
phenyl]urea CAS RN [27954376], formerly [34766295] and [36510948]
Development codes Hoe 2991 Smiles code CN(C)C(=O)Nc1cccc(OC(F)(F)C(F)F)c1
PHYSICAL CHEMISTRY:
Mol. wt. 280.2 M.f. C
11
H
12
F
4
N
2
O
2
COMMERCIALISATION:
O,O,O,O-tetrapropyl dithiopyrophosphate
Insecticide
IRAC 1B
NOMENCLATURE:
IUPAC name O,O,O,O-tetrapropyl dithiopyrophosphate
Chemical Abstracts name tetrapropyl thiodiphosphate; thiodiphosphoric acid
([(HO)2P(S)]2O) tetrapropyl ester Other names NPD CAS RN [3244904]
EC no 2218170 Development codes ASP-51 (Stauffer)
Smiles code CCCOP(=S)(OCCC)OP(=S)(OCCC)OCCC
PHYSICAL CHEMISTRY:
12
H
28
O
5
P
2
S
2
Form Tech. is a straw
to amber-coloured liquid, with a faint aromatic odour. B.p.c. 170 C /1 mmHg
V.p. c. 13 mPa (25 C) S.g./density 1.1191.123 (20 C) Solubility In water 30 mg/l
(20 C). Miscible with acetone, ethanol, kerosene, 4-methylpentan-2-one, xylene.
Stability Stable <100 C. DT
50
32 d (pH 7 buffer, 40 C).
tetrasul 513
COMMERCIALISATION:
History Insecticide reported by A. D. F. Toy (J. Am. Chem. Soc., 1951, 73, 4670). Introduced
by Stauffer Chemical Co. (later ICI Americas). Patents US 2663722
APPLICATIONS:
Uses Insecticide particularly effective at 8.6. kg/ha for the control of Blissus leucopterus in
turf. Formulation types EC; GR .
PRODUCTS:
Discontinued products Aspon* (Stauffer); Sod* (Chevron).
ANALYSIS:
Product analysis by glc with FID (R. D. Mills & M. Yuan, Anal. Methods Pestic. Plant Growth
Regul., 1984, 13, 149). Residues in soil and turf determined by glc (idem, ibid.).
Oral Acute oral LD
50
for male albino rats 2800, female rats 740 mg/kg.
50
for rabbits >2000 mg/kg. Mildly irritating to skin
and non-irritating to eyes (rabbits). Other In 90 d feeding trials at sublethal rates, rats
showed some depression of red blood cell cholinesterase. ECClassifcation Xn; R21/22
ENVIRONMENTAL FATE:
Soil/Environment Persistent in soil.
tetrasul
Acaricide
NOMENCLATURE:
Common name tetradisul (Canada); diphenylsulphide (JMAF); tetrasul (BSI, E-ISO, (m)
F-ISO, ESA)
IUPAC name 4-chlorophenyl 2,4,5-trichlorophenyl sulfde
Chemical Abstracts name 1,2,4-trichloro-5-[4-(chlorophenyl)thio]benzene
CAS RN [2227136] Development codes V-101 (N. V. Philips-Roxane)
Smiles code Clc1ccc(Sc2cc(Cl)c(Cl)cc2Cl)cc1
PHYSICAL CHEMISTRY:
Composition Tech. is 77.5%. Mol. wt. 324.1 M.f. C
12
H
6
Cl
4
S Form Tech. is a cream to
yellow-brown solid. M.p. 88.488.6 C; (tech., 7585 C) V.p. 0.10 mPa (20 C)
Henry 1.0
8
Pa m
3
mol
1
(calc.) Solubility In water 0.03 mg/l (20 C). In 1,2-dichloroethane
274, ethanol 20, xylene 400 (all for tech., in g/l, 20 C). Stability Stable at ambient
temperature in the dark; it is slowly oxidised via the corresponding sulphoxide to
tetradifon under prolonged exposure to sunlight. No conversion after 30 min at 90 C in
a methanolic potassium hydroxide solution; <2% decomposition after 7 d at pH 6 as a 25
mg/l suspension in water.
514
thiadifuor
COMMERCIALISATION:
History Acaricide reported by J. Meltzer & F. C. Dietvoorts (Proc. Int. Congr. Crop Prot.,
4th, 1957, 1, 669). Introduced by N.V. Philips-Roxane (later Uniroyal Chemical Co., Inc.).
Patents NL 94329; US 3054719
APPLICATIONS:
Mode of action Contact acaricide. Uses For the control of various phytophagous mites
which hibernate in the winter egg form. It is necessary to apply it when the winter eggs
were about to hatch. It was recommended for use on cucumber, bush fruit, top fruit and
grapes at 36 g/100 l. Formulation types WP.
PRODUCTS:
Discontinued products Animert V101* (DuPont).
ANALYSIS:
Product analysis by glc (L. R. Mitchell, J. Assoc. Off. Anal. Chem., 1976, 59, 209). Residues
determined by glc (idem, ibid.; AOAC Methods, 18th Ed., 976.23). See also Pestic. Anal. Man., I,
303.
Oral Acute oral LD
50
for male rats 8250, female rats 6810, male and female mice 5010,
male guinea pigs 8250, female guinea pigs 8800 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits >2000 mg/kg. NOEL (2 y) for rats 10 mg/kg diet. In 90 d feeding trials,
beagle-dogs tolerated 200 mg/kg diet. In a 3-generation study on rats, NOEL 20 mg/kg
diet Toxicity Class WHO (a.i.) U
thiadifuor
Fungicide
NOMENCLATURE:
Common name thiadifuor (BSI, E-ISO, (m) F-ISO)
IUPAC name 3-(4-chlorophenyl)-N
2
-methyl-N4,N5-bis(trifuoromethyl)-1,3-thiazolidine-
2,4,5-triylidenetriamine
Chemical Abstracts name N,N-[3-(4-chlorophenyl)-2-(methylimino)-4,5-
thiazolidinediylidene]bis[1,1,1-trifuoromethanamine] CAS RN [80228939]
Development codes SLJ 4027a
Smiles code CN=C1SC(=NC(F)(F)F)C(=NC(F)(F)F)N1c2ccc(Cl)cc2
PHYSICAL CHEMISTRY:
Mol. wt. 353.3 M.f. C
12
H
7
F
6
N
4
S
COMMERCIALISATION:
thiazafuron 515
thiazafuron
Herbicide
NOMENCLATURE:
Common name thiazafuron (BSI, E-ISO, (m) F-ISO); thiazfuron (Canada)
IUPAC name 1,3-dimethyl-1-(5-trifuoromethyl-1,3,4-thiadiazol-2-yl)urea
Chemical Abstracts name N,N-dimethyl-N-[5-(trifuoromethyl)-1,3,4-thiadiazol-2-yl]
urea CAS RN [25366238] EC no 2469014 Development codes GS 29 696
Smiles code CNC(=O)N(C)c1nnc(s1)C(F)(F)F
PHYSICAL CHEMISTRY:
Mol. wt. 240.2 M.f. C
6
H
7
F
3
N
4
OS Form Colourless crystals. M.p. 136137 C
V.p. 0.27 mPa (20 C) K
ow
logP = 1.82 Henry 3.09 10
5
Pa m
3
mol
1
(calc.)
S.g./density 1.6 (20 C) Solubility In water 2.1 g/l (20 C). In ethanol 300, methanol 257,
n-octanol 60, DMF 600, xylene <50, benzene 12, hexane dichloromethane 146 (all in g/kg,
20 C). Stability No signifcant hydrolysis in 28 d at pH 1, pH 5 or pH 7.
COMMERCIALISATION:
History Herbicide reported by G. Mller et al. (C. R. Journ. Etud. Herbic. Conf. COLUMA,
7th, 1973, p. 32). Introduced by Ciba-Geigy AG. Patents BE 725984; GB 1254468
APPLICATIONS:
Biochemistry Photosynthetic electron transport inhibitor. Mode of action Non-
selective soil-herbicide, absorbed principally by the roots. Uses Control of most annual
and perennial grasses and broad-leaved weeds, in addition to woody plants such as shrubs
and bushes, on uncultivated land, industrial land, railway tracks, etc. Applied either pre-
emergence or early post-emergence at 28 kg/ha in moist and temperate and 612 kg/ha
in warm and dry regions. Formulation types GR; WP.
PRODUCTS:
Discontinued products Erbotan* (Ciba-Geigy).
ANALYSIS:
Product analysis by hplc. Residues determined by glc with FPD.
Oral Acute oral LD
50
LD
50
for rats >2150 mg/kg. Slight irritant to eyes, but non-irritant to skin (rabbits).
Inhalation LC
50
of 80% formulation for rats >0.35 mg/l. NOEL (90 d) for rats 160 mg/kg
diet (11 mg/kg daily); (105 d) for dogs 250 mg/kg diet (8 mg/kg daily).
N N
S
F
3
C N
CH
3
CONHCH
3
516
thicyofen
Toxicity Class WHO (a.i.) IIECClassifcation Xn; R22| N; R50, R53
ECOTOXICOLOGY:
50
(96 h) for rainbow trout 82, bluegill sunfsh and
crucian carp >100 mg/l. Bees Not toxic to bees.
ENVIRONMENTAL FATE:
Soil/Environment Degraded in soils, DT
50
50200 d.
thicrofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name thicrofos (BSI, E-ISO, (m) F-ISO)
IUPAC name S-(6-chloro-3,4-dihydro-2H-1-benzothi-in-4-yl) O,O-diethyl
phosphorothioate
Chemical Abstracts name S-(6-chloro-3,4-dihydro-2H-1-benzothiopyran-4-yl)
O,O-diethyl phosphorothioate CAS RN [41219323] unstated stereochemistry
Development codes Hoe 20 906
Smiles code CCOP(=O)(OCC)SC1CCSc2ccc(Cl)cc12
PHYSICAL CHEMISTRY:
Mol. wt. 352.8 M.f. C
13
H
18
ClO
3
PS
2
COMMERCIALISATION:
History Insecticide evaluated by Hoechst AG.
APPLICATIONS:
thicyofen
Fungicide
NOMENCLATURE:
Common name thicyof(ne) ((m) F-ISO); thicyofen (BSI, E-ISO)
IUPAC name ()-3-chloro-5-ethylsulfnylthiophene-2,4-dicarbonitrile
Chemical Abstracts name ()-3-chloro-5-(ethylsulfnyl)-2,4-thiophenedicarbonitrile
CAS RN [116170300] unstated stereochemistry Development codes PH 5107; DU
S
CH
3
CH
2
S
CN
Cl
CN
O
thidiazimin 517
510 311 (Duphar) Smiles code CCS(=O)c1sc(C#N)c(Cl)c1C#N
PHYSICAL CHEMISTRY:
Mol. wt. 244.7 M.f. C
8
H
5
ClN
2
OS
2
Form Solid. M.p. 130 C V.p. <1 mPa (20 C)
K
ow
logP = 2.54 Henry <1.02 10
3
Pa m
3
mol
1
(calc.) Solubility In water 240 mg/l
(20 C).
COMMERCIALISATION:
History Fungicide reported by T. W. Hofman et al. (Proc. 1990 Br. Crop Prot. Conf. - Pests
Dis., 2, 431). Introduced by Duphar B.V. (later Uniroyal Chemical Co., Inc.).
APPLICATIONS:
Biochemistry Multi-site inhibitor. Uses Non-systemic seed treatment for control
of Fusarium and Pythium spp., Pyrenophora graminea, and Tilletia caries in cereals, maize
and cotton. Also used as a soil treatment for control of Pythium spp. in fower bulbs.
Formulation types SC.
Oral Acute oral LD
50
percutaneous LD
50
for rats >2000 mg/kg. Other Non-mutagenic in in vitro tests.
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
for bobwhite quail and
mallard ducks >5620 mg/kg.
ENVIRONMENTAL FATE:
Soil/Environment Rapidly degraded in soil, DT
50
<30 d.
thidiazimin
Herbicide
HRAC E WSSA 14; thiadiazole
NOMENCLATURE:
Common name thidiazimin (BSI, E-ISO); thidiazimine ((f) F-ISO)
IUPAC name (Z)-6-(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,1-c][1,2,4]thiadiazol-3-
ylideneamino)-7-fuoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one
Chemical Abstracts name 6-[(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo[2,1-c][1,2,4]
thiadiazol-3-ylidene)amino]-7-fuoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one
CAS RN [123249434] Development codes SN 124 085 Smiles code CC1(C)
Cc2nsc(=Nc3cc4N(CC#C)C(=O)COc4cc3F)n2C1
18
H
17
FN
4
O
2
S Form Colourless
crystals. M.p. 158 C V.p. 5.0 10-8 mPa (25 C) K
ow
logP = 3.0 (pH 7) Henry 2.82
10
9
Pa m
3
mol
1
(calc.) Solubility In water (6.6 0.5) 10
3
g/l (pH 7, 25 C).
pKa 2.60.1 (conjugate acid)
518
thiocarboxime
COMMERCIALISATION:
History Herbicide reported by R. Weiler et al. (Proc. Br. Crop Prot. Conf. Weeds, 1993, 1,
APPLICATIONS:
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Contact herbicide
with rapid action. Uses Post-emergence control of broad-leaved weeds in winter cereals,
particularly effective against Lamium purpureum, Veronica hederifolia, Veronica persica and
Viola arvensis. Application rates were 2040 g/ha. Formulation types SC.
Oral Acute oral LD
50
50
for
rats >>5000 mg/kg. No skin or eye irritancy (rabbits). Not a skin sensitiser (guinea pigs).
Inhalation LC
50
for rats >4.89 mg/l. Other Non-teratogenic and non-genotoxic.
ECOTOXICOLOGY:
Birds Low toxicity to birds.
ENVIRONMENTAL FATE:
50
3070 d, depending on soil type. Soil adsorption coeffcient
(K
oc
) 7001200 ml/g.
thiocarboxime
NOMENCLATURE:
Common name thiocarboxime (BSI, E-ISO, (f) F-ISO)
IUPAC name 3-[1-(methylcarbamoyloxyimino)ethylthio]propiononitrile
Chemical Abstracts name 2-cyanoethyl N-[[(methylamino)carbonyl]oxy]
ethanimidothioate CAS RN [25171635] Development codes WL 21 959; SD 17250
Smiles code CNC(=O)ON=C(C)SCCC#N
PHYSICAL CHEMISTRY:
Mol. wt. 201.2 M.f. C
7
H
11
N
3
O
2
S
COMMERCIALISATION:
History Insecticide and acaricide evaluated by Shell Research Ltd.
APPLICATIONS:
PRODUCTS:
Discontinued products Talcord* (Shell).
2-thiocyanatoethyl laurate 519
thiochlorfenphim
Fungicide
NOMENCLATURE:
Common name thiochlorfenphim (BSI, E-ISO); thiochlorphenphim ((f) F-ISO);
thiochlorphenphime (France)
IUPAC name N-(4-chlorophenylthiomethyl)phthalimide
Chemical Abstracts name 2-[[(4-chlorophenyl)thio]methyl]-1H-isoindole-1,3(2H)-
dione CAS RN [19378586] Development codes BAY 66 109; SRA 3208
Smiles code Clc1ccc(SCN
2
C(=O)c3ccccc3C2=O)cc1
PHYSICAL CHEMISTRY:
Mol. wt. 303.8 M.f. C
15
H
10
ClNO
2
S
COMMERCIALISATION:
History Fungicide evaluated by Bayer AG.
2-thiocyanatoethyl laurate
Insecticide
NOMENCLATURE:
IUPAC name 2-thiocyanatoethyl laurate
Chemical Abstracts name 2-thiocyanatoethyl dodecanoate CAS RN [301111]
Smiles code CCCCCCCCCCCC(=O)OCCSC#N
PHYSICAL CHEMISTRY:
Mol. wt. 285.5 M.f. C
15
H
27
NO
2
S
COMMERCIALISATION:
History Insecticide developed by Rohm & Haas Co.
PRODUCTS:
Discontinued products Lethane 60* (Rohm & Haas).
520
thiofanox
thiofanox
IRAC 1A; oxime carbamate
NOMENCLATURE:
Common name thiofanocarb (Republic of South Africa); thiofanox (BSI, E-ISO, (m) F-ISO,
ANSI, ESA)
IUPAC name 3,3-dimethyl-1-methylthiobutanone O-methylcarbamoyloxime;
1-(2,2-dimethyl-1-methylthiomethylpropylideneamino-oxy)-N-methylformamide
Chemical Abstracts name 3,3-dimethyl-1-(methylthio)-2-butanone O-[(methylamino)
carbonyl]oxime CAS RN [39196184] EC no 2543464
Development codes DS 15 647 (Diamond Shamrock)
Smiles code CNC(=O)ON=C(CSC)C(C)(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 218.3 M.f. C
9
H
18
N
2
O
2
S Form Colourless solid, with a pungent odour. M.p. 56.5
57.5 C V.p. 22.6 mPa (25 C) Solubility In water 5.2 g/l (22 C). Readily soluble in
chlorinated and aromatic hydrocarbons, ketones and non-polar solvents. Slightly soluble
in aliphatic hydrocarbons. Stability Stable to heat under normal storage conditions.
Relatively stable to hydrolysis at pH 59 (under 30 C). Decomposed by strong acids and
alkalis.
COMMERCIALISATION:
History Insecticide reported by R. L. Schauer (Proc. Br. Insectic. Fungic. Conf., 7th, 1973, 2,
713). Relationship between chemical structure and biological activity of analogues reported
by T. A. Magee & L. E. Limpel (J. Agric. Food Chem., 1977, 25, 1376). Introduced by Diamond
Shamrock Chemical Co. Later sold to Rhne-Poulenc Agrochimie (now Bayer AG).
Manufacturers Bayer CropScience
APPLICATIONS:
acaricide. Uses Soil application for control of black bean aphids, beet leaf miners, Flea
beetles and pygmy mangold beetles on beet; fea beetles on rape; aphids, capsids, fea
beetles, colorado beetle and leafhoppers on potatoes; aphids, midges, fea beetles, soil-
inhabiting larvae and spider mites on cotton; aphids and spider mites in foriculture, etc.
Applied at rates in the range 0.43 kg/ha. Formulation types GR .
PRODUCTS:
Discontinued products Benelux* (ISK Biotech); Dacamox* (Bayer CropScience).
CH
3
NH C N C
C(CH
3
)
3
CH
2
SCH
3
O
O
thionazin 521
ANALYSIS:
Residues, which are likely to include thiofanox, its sulfoxide and sulfone, are oxidised to
the sulfone, which is determined by glc (W. T. Chin, J. Agric. Food Chem., 1975, 23, 963; M. B.
Szalkowski et al., J. Chromatogr., 1976, 128, 426).
Oral Acute oral LD
50
for albino rats 8.5 mg/kg. Skin and eye Acute percutaneous LD
50

for albino rabbits 39 mg/kg. NOEL (90 d) for rats and beagle dogs 1 mg/kg daily. Clinical
symptoms of reversible cholinesterase inhibition at 4.0 mg/kg daily, lasting for 34 hours.
Weight gain of rats receiving 100 mg/kg diet was not affected. ADI/RfD (EPA) 0.0003 mg/
kg b.w. [1988]. Toxicity Class WHO (a.i.) Ib EPA (formulation) I
ECOTOXICOLOGY:
Birds Acute oral LD
50
for mallard ducks 109, bobwhite quail 43 mg/kg. Fish LC
50
(96 h)
for rainbow trout 0.13, bluegill sunfsh 0.33 mg/l. Bees Not toxic to bees when used as
directed.
ENVIRONMENTAL FATE:
Animals Metabolism of carbamate insecticides is reviewed (M. Cool & C. K. Jankowski
in Insecticides). Plants Metabolism in plants is the same as in soil. The duration of activity
following absorption through the roots is at least 8 weeks. Soil/Environment In soil, the
methylthio group is rapidly oxidised to the sulfoxide and, further, to the sulfone. Further
degradation occurs to water-soluble metabolites.
thionazin
IRAC 1B
NOMENCLATURE:
Common name thionazin (BSI, E-ISO); thionazine ((m) F-ISO)
IUPAC name O,O-diethyl O-pyrazin-2-yl phosphorothioate
Chemical Abstracts name O,O-diethyl O-pyrazinyl phosphorothioate
CAS RN [297972] EC no 2060496 Development codes Experimental Nematicide
18 133 (Cyanamid) Smiles code CCOP(=S)(OCC)Oc1cnccn1
PHYSICAL CHEMISTRY:
8
H
13
N
2
O
3
PS Form Colourless to
pale yellow liquid; (tech. is a dark brown liquid). M.p. -1.67 C V.p. 400 mPa (30 C)
Henryc. 8.71 10-2 Pa m
3
mol
1
(calc.) S.g./density 1.207 (25 C); tech. 1.2041.210
522
thiophanate
(25 C) Solubility In water 1.14 g/l (27 C). Miscible with most organic solvents.
Stability Readily hydrolysed by alkali (pH >9).
COMMERCIALISATION:
History Nematicide introduced by American Cyanamid Co. Patents US 2918468; US
2938831; US 3091614
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Uses Soil insecticide and nematicide effective
against a number of plant-parasitic as well as free-living nematodes, including those
attacking buds, bulbs, leaves and roots, as well as against soil dwelling pests such as
root maggots and symphylids and foliar insects such as aphids and leaf miners. When
incorporated in mushroom compost at spawning it is effective against mushroom fies. It is
of short persistence. Formulation types EC; GR .
PRODUCTS:
Discontinued products Bulb Dip* (Neals); Cynem* (Cyanamid); Nemafos*
(Cyanamid); Zinophos* (Cyanamid).
ANALYSIS:
Product analysis is by hydrolysis with fuorimetric determination of the sodium salt
of pyrazin-2-ol (U. Kiigemagi et al., J. Agric. Food Chem., 1963, 11, 293). Residues may be
determined by glc (D. R. Coahran, Bull. Environ. Contam. Toxicol., 1966, 1, 208).
Oral Acute oral LD
50
50

for rats 11 mg/kg. NOEL In feeding trials, rats receiving 25 mg/kg diet for 30 d and then
50 mg/kg diet for 60 d showed a moderate depression in growth rate, but no abnormal
behavioural reactions. ADI/RfD (EPA) 0.00005 mg/kg b.w. [1987]. Toxicity Class WHO
(a.i.) IaECClassifcation T+; R27/28
ECOTOXICOLOGY:
Birds LC
50
(5 d) for bobwhite quail 65, pheasants 72 mg/kg diet. Fish LC
50
(48 h) for
harlequin fsh 0.09 mg (as 480 g/l EC)/l. Bees LD
50
(topical) for honeybees 42 ng/l.
thiophanate
Anthelmintic, fungicide
FRAC 1, B1
NOMENCLATURE:
Common name thiophanate (BSI, E-ISO, (m) F-ISO, JMAF, BAN); thiophanate-(thyl) ((m)
France)
thioquinox 523
IUPAC name diethyl 4,4-(o-phenylene)bis(3-thioallophanate)
Chemical Abstracts name diethyl [1,2-phenylenebis(iminocarbonothioyl)]
bis[carbamate] CAS RN [23564069] Development codes NF 35 (Nippon Soda)
Smiles code CCOC(=O)NC(=S)Nc1ccccc1NC(=S)NC(=O)OCC
14
H
18
N
4
O
4
S
2
Form Colourless
crystalline solid. M.p. 195 C (decomp.) Solubility Almost insoluble in water; sparingly
soluble in most organic solvents. Stability Forms unstable solutions of salts with aqueous
alkali and complexes with divalent transition metal ions, for example copper.
COMMERCIALISATION:
History Fungicide reported by K. Ishii (Abstr. Int. Congr. Plant Prot., 7th, Paris, 1970, p.
200); reviewed (idem, Jpn. Pestic. Inf., 1971, No. 7, p. 27). Introduced by Nippon Soda Co.,
Ltd. For thiophanate-methyl, see Main Entries. Patents DE 1930540
APPLICATIONS:
Biochemistry Carbendazim (q.v.) precursor. Mode of action Systemic fungicide.
Uses Effective against Venturia spp. on apple and pear crops, powdery mildews, Botrytis and
sclerotinia spp. on various crops. Also used as an anthelminthic. Formulation types WP.
PRODUCTS:
Discontinued products Cercobin* (Nippon Soda); Nemafax* (anthelmintic) (May &
Baker); Topsin* (Nippon Soda); Verdamax* (anthelmintic) (May & Baker).
ANALYSIS:
Product analysis by uv spectrometry.
Oral Acute oral LD
50
for male and female rats >15 000 mg/kg. Skin and eye Acute
percutaneous LD
50
for male and female rats >15 000 mg/kg. Toxicity Class WHO (a.i.) U
ENVIRONMENTAL FATE:
Plants In plants it is converted into ethyl benzimidazol-2-ylcarbamate.
thioquinox
NOMENCLATURE:
Common name thioquinox (BSI, E-ISO, (m) F-ISO, ESA)
IUPAC name 1,3-dithiolo[4,5-b]quinoxaline-2-thione (I)
Development codes Bayer 30 686; Ss 1451 Smiles code S=c1sc2nc3ccccc3nc2s1
524
tiocarbazil
PHYSICAL CHEMISTRY:
Mol. wt. 236.3 M.f. C
9
H
4
N
2
S
3
COMMERCIALISATION:
History Acaricide and fungicide reported by G. Unterstenhfer (Hoefchen-Briefe, (Engl.
Ed.), 1960, 13, 207) and by K. Sasse (ibid., p. 197). Introduced by Bayer AG.
PRODUCTS:
Discontinued products Eradex* (Bayer); Eraziton* (Bayer).
tiocarbazil
Herbicide
NOMENCLATURE:
Common name tiocarbazil (BSI, E-ISO, (m) F-ISO)
IUPAC name S-benzyl di-sec-butylthiocarbamate
Chemical Abstracts name S-(phenylmethyl) bis(1-methylpropyl)carbamothioate
CAS RN [36756793] EC no 2531904 Development codes M 3432 (Agrimont)
Smiles code CCC(C)N(C(C)CC)C(=O)SCc1ccccc1
PHYSICAL CHEMISTRY:
Mol. wt. 279.4 M.f. C
16
H
25
NOS Form Colourless liquid, with aromatic odour.
B.p. 130132 C /0.1 mmHg V.p. 93 mPa (50 C) K
ow
logP = 4.4 S.g./density 1.023
(20 C) Solubility In water 2.5 mg/l (30 C). Miscible with polar and non-polar organic
solvents. Stability Stable to hydrolysis at pH 5.68.4. Slightly decomposed after 30 days
at 40 C in aqueous ethanol at pH 1.5. Stable to storage for 60 days at 40 C, and for 100
hours in aqueous solution exposed to sunlight.
COMMERCIALISATION:
History Herbicide reported by N. Caracalli et al. (Proc. Congr. Risicultura, 8th, 1973, p.
446). Introduced by Montedison S.p.A. (later Isagro S.p.A.) in Italy (1974).
Patents IT 907710; DE 2144700
C N
O
S
CH
3
CH
2
CH
CH
3
CH
2
CH
CH
2
CH
3
CH
3
tiocarbazil 525
APPLICATIONS:
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). Mode of action Selective
herbicide, absorbed by the roots and coleoptiles. Uses Control of Echinochloa spp., Lolium
perenne, Cyperus spp., and other monocotyledonous weeds in rice paddy felds. Applied
pre- or post-emergence at 4 kg/ha, or as a seed dressing. Phytotoxicity Non-phytotoxic
to rice. Formulation types EC; GR; SL; Seed treatment.
PRODUCTS:
Discontinued products Drepamon* (Isagro).
ANALYSIS:
Product and residue analysis by tlc (R. Fabbrini & G. Galluzzi, Anal. Methods Pestic. Plant
Growth Regul., 1980, 11, 307). Product analysis also by glc method; details available from
Isagro.
EHC 76 (1988) is a general review of thiocarbamates. EU Status (1107/2009) Not
Oral Acute oral LD
50
for rats, rabbits, and guinea pigs >10 000 mg tech./kg, for mice
50
for rats and rabbits >1200 mg/kg.
Inhalation LC
50
for rats >0.18 mg/l air. NOEL In 2 y feeding trials, albino rats and beagle
dogs receiving 1000 mg tech./kg diet suffered no ill-effect except for a slight weight loss
in male dogs. No effect on reproduction in albino rats receiving 300 mg/kg diet for 3
generations. Toxicity Class WHO (a.i.) U
ECOTOXICOLOGY:
Birds Acute oral LD
50
for chickens, pheasants, quail >10 000 mg tech./kg. Fish LC
50
in
several fsh species 8 mg/l. Other aquatic spp. LC
50
for the mollusc Australorbis glabratus
>60 mg/l. Bees Not hazardous for honeybees.
ENVIRONMENTAL FATE:
Animals Tiocarbazil, when administered orally at the dose of 1 g/kg, is almost totally
eliminated 7 days after treatment, either as such in the faeces or as products deriving
from its metabolism, through the urine. In the blood and in the main organs, minimum
concentrations of the product and of its metabolites have been found 48 hours after
treatment. Plants Tiocarbazil undergoes extensive metabolism in rice: 3 compounds have
been identifed in plants (except caryopsides): N,N-di-sec-butylcarbamoylthiolglycolic acid,
N,N-di-sec-butylcarbamoyl benzylsulfoxide, and N,N-di-sec-butylcarbamoyl benzylsulfone
(the frst by oxidation of the benzene ring, the other two by oxidation of the sulfur atom).
Soil/Environment Tiocarbazil is strongly adsorbed by the soil (where it largely localises
in the uppermost layer), Kom 1711, and undergoes a rapid degradation due to the attack
of soil micro-organisms; 50% of tiocarbazil applied is no longer present in the soil/water
system of a rice feld 815 days after treatment.
526
tioxymid
tioclorim
Herbicide
NOMENCLATURE:
Common name tioclorime ((f) F-ISO); tioclorim (BSI, E-ISO)
IUPAC name 6-chloro-5-(methylthio)pyrimidine-2,4-diamine
Chemical Abstracts name 6-chloro-5-(methylthio)-2,4-pyrimidinediamine
CAS RN [68925417] Development codes UK-J 1506 (Produits Chimiques)
Smiles code CSc1c(N)nc(N)nc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 190.6 M.f. C
5
H
7
ClN
4
S
COMMERCIALISATION:
History Herbicide discovered by Produits Chimiques Ugine Kuhlmann.
tioxymid
Fungicide
NOMENCLATURE:
Common name tioxymid (BSI, E-ISO); tioxymide ((m) F-ISO)
IUPAC name 5-isothiocyanato-2-methoxy-N,N-dimethyl-m-toluamide
Chemical Abstracts name 5-isothiocyanato-2-methoxy-N,N,3-trimethylbenzamide
CAS RN [70751949] Development codes SAF-787; 710 352-S
Smiles code COc1c(C)cc(N=C=S)cc1C(=O)N(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 250.3 M.f. C
12
H
14
N
2
O
2
S
COMMERCIALISATION:
History Fungicide introduced by Shionogi & Co., Ltd.
N-m-tolylphthalamic acid 527
tolprocarb
Fungicide
NOMENCLATURE:
Common name tolprocarb (pa ISO)
IUPAC name 2,2,2-trifuoroethyl (S)-[2-methyl-1-(p-toluoylaminomethyl)propyl]
carbamate
Chemical Abstracts name 2,2,2-trifuoroethyl N-[(1S)-2-methyl-1-[[(4-methylbenzoyl)
amino]methyl]propyl]carbamate CAS RN [911499622] Development codes MTF
0301 Smiles code Cc1ccc(cc1)C(=O)NC[C@H](C(C)C)/N=C(\O)/OCC(F)(F)F
16
H
21
F
3
N
2
O
3
N-m-tolylphthalamic acid
NOMENCLATURE:
IUPAC name N-m-tolylphthalamic acid
Other names N-m-t CAS RN [85723] EC no 2016269
Smiles code Cc1cccc(NC(=O)c2ccccc2C(=O)O)c1
PHYSICAL CHEMISTRY:
Mol. wt. 255.3 M.f. C
15
H
13
NO
3
Form White powder. M.p. 152 C Solubility In water
0.1 g/l.
COMMERCIALISATION:
History Plant growth regulator.
Manufacturers Makhteshim-Agan
APPLICATIONS:
Mode of action Systemic plant growth regulator which prevents abscission of fowers
and young fruit. Uses Increases fruit set of tomatoes, aubergines and lima beans under
CH
3
CH
3
CH
3
F
F
F
NH
N
O
OH
O
H
CO
2
H
CH
3
C
NH
O
528
tralopyril
adverse conditions. Formulation types WP.
PRODUCTS:
Discontinued products Tomaset* (Makhteshim-Agan).
EU Status (1107/2009) Not approved (as tolylphtalam), Commission Regulation
2076/2002.
Oral Acute oral LD
50
50
for
rabbits >20000 mg/kg. Inhalation LC
50
for rats >5 mg/l.
tralopyril
Anti-foulant, molluscicide
See also The Manual of Biocontrol Agents entry:
NOMENCLATURE:
Common name tralopyril (BSI, E-ISO, (m) F-ISO)
IUPAC name 4-bromo-2-(4-chlorophenyl)-5-(trifuoromethyl)-1H-pyrrole-3-carbonitrile
Chemical Abstracts name 4-bromo-2-(4-chlorophenyl)-5-(trifuoromethyl)-1H-
pyrrole-3-carbonitrile CAS RN [122454299] Development codes AC 303268
Smiles code N#CC1=C(C2=CC=C(Cl)C=C2)NC(C(F)(F)F)=C1Br
PHYSICAL CHEMISTRY:
Mol. wt. 349.5 M.f. C
12
H
5
BrClF
3
N
2
N
H
N
F
F
F
Cl
Br
transpermethrin 529
transpermethrin
Insecticide
IRAC 3
An isomer pair, component of permethrin.
NOMENCLATURE:
Common name transperm(thrine) ((f) F-ISO); transpermethrin (BSI, E-ISO)
IUPAC name 3-phenoxybenzyl (1RS)-trans-3-(2,2-dichlorovinyl)-2,2-dimethyl
cyclopropanecarboxylate; 3-phenoxybenzyl (1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-
Chemical Abstracts name rel-(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-
dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; trans-()-(3-phenoxyphenyl)methyl
3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other names permethrin-G CAS RN [61949777], formerly [52341329]; [51877
748] biopermethrin (the (1R)-trans- resolved isomer) (q.v.); [54774479] (1S)-trans-
isomer Development codes NRDC 146; RU 22090
Smiles code CC1(C)C(C=C(Cl)Cl)C1C(=O)OCc2cccc(Oc3ccccc3)c2
PHYSICAL CHEMISTRY:
Mol. wt. 391.3 M.f. C
21
H
20
Cl
2
O
3
APPLICATIONS:
O
CH
2
C CH
CH
3
CH
3
Cl
C
O
O
Cl
O
CH
2
C CH
CH
3
CH
3
Cl
C
O
O
Cl
H
H
H
H
(1R)-trans- isomer (biopermethrin)
(1S)-trans- isomer
530
triamiphos
ANALYSIS:
triamiphos
Acaricide, fungicide, insecticide
IRAC 1B
NOMENCLATURE:
Common name triamiphos (BSI, E-ISO, (m) F-ISO)
IUPAC name 5-amino-3-phenyl-1H-1,2,4-triazol-1-yl-N,N,N,N-tetramethylphosphonic
diamide
Chemical Abstracts name P-(5-amino-3-phenyl-1H-1,2,4-triazol-1-yl)-N,N,N,N-
tetramethylphosphonic diamide CAS RN [1031476] Development codes WP 155
(Philips-Duphar) Smiles code CN(C)P(=O)(N(C)C)n1nc(nc1N)c2ccccc2
PHYSICAL CHEMISTRY:
12
H
19
N
6
OP Form Colourless solid.
M.p. 167168 C; (tech., 166170 C) Solubility In water 250 mg/l (20 C). Moderately
to easily soluble in most organic solvents. Stability Stable at room temperature under
neutral or slightly alkaline conditions, but is readily hydrolysed by concentrated mineral
acids.
COMMERCIALISATION:
History Acaricide, fungicide and insecticide reported by B. G. van den Bos et al. (Rec. Trav.
Chim. Pays-Bas, 1960, 79, 807). Introduced by Philips-Duphar B.V. (later Uniroyal Chemical
Co., Inc.). Patents NL 109510, US 3121090,US 3220922.
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Systemic acaricide, fungicide and
insecticide. Uses For powdery mildew control, at 25 g/100 l on apples and roses. Also has
insecticidal and acaricidal properties.
PRODUCTS:
Discontinued products Wepsyn 155* (Philips-Duphar).
ANALYSIS:
Product and residue analysis is by the colorimetric determination of 5-phenyl-1,2,4-triazol-
3-ylamine formed on acid hydrolysis.
triapenthenol 531
Oral Acute oral LD
50
for rats 20 mg/kg. Toxicity Class WHO (a.i.) IbECClassifcation
T+; R27/28
triapenthenol
NOMENCLATURE:
Common name triapenth(nol) ((m) F-ISO); triapenthenol (BSI, E-ISO)
IUPAC name (E)-(RS)-1-cyclohexyl-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
Chemical Abstracts name (E)-()--(cyclohexylmethylene)--(1,1-dimethylethyl)-1H-
1,2,4-triazole-1-ethanol CAS RN [76608883] (E)- isomer
Development codes BAY RSW 0411
Smiles code CC(C)(C)C(O)/C(=C/C1CCCCC1)/n2cncn2;
without stereochemistry: CC(C)(C)C(O)C(=CC1CCCCC1)n2cncn2
PHYSICAL CHEMISTRY:
Mol. wt. 263.4 M.f. C
15
H
25
N
3
O Form Colourless crystals. M.p. 135.5 C
V.p. 4.4 10
3
mPa (20 C) K
ow
logP = 2.274 Solubility In water 68 mg/l. In acetone 150,
dichloromethane >200, hexane 510, methanol 433, isopropanol 100200, toluene 2050
(all in g/l).
COMMERCIALISATION:
History Plant growth regulator reported at 44th Deutsche Pfanzenschutz-Tag (1984),
K. Lrssen & W. Reiser (Proc. 1985 Br. Crop Prot. Conf. - Weeds, 1, 121). Introduced in
Belgium and France (1989) by Bayer AG.
APPLICATIONS:
Biochemistry The (S)-(-)- enantiomer is an inhibitor of gibberellin biosynthesis and
a plant growth regulator; the (R)-(+)- enantiomer inhibits sterol demethylation and is
fungicidal (K. Lrssen, Pfanz.-Nachr. Bayer (Eng. Ed.), 1988, 41, p. 306; U. Kraatz & L. Born,
ibid., p. 340). Uses Plant growth regulator used to control lodging in oilseed rape and
grasses grown for seed. (The (R)-(+)- enantiomer is fungicidal). Formulation types WG .
PRODUCTS:
Discontinued products Baronet* (Bayer).
CH
OH
C
N
N
N
C(CH
3
)
3
CH
532
triarathene
ANALYSIS:
Residues determined by glc with TID (R. Brennecke, Pfanz.-Nachr. Bayer (Engl. Ed.), 1990, 43,
159).
Oral Acute oral LD
50
for rats >5000, micec. 4000, dogsc. 5000 mg/kg. Skin and eye Acute
percutaneous LD
50
for rats >5000 mg/kg. NOEL (2 y) for rats 100 mg/kg diet.
ECOTOXICOLOGY:
Birds Acute oral LD
50
(14 d) for Japanese quail and hens >5000, for canaries (7 d)
>1000 mg/kg. Fish LC
50
(96 h) for golden orfe 34.4, guppies 18.8, trout 37, and carp
18 mg/l. Daphnia LC
50
(48 h) >70 mg a.i. (as 70% WP)/l. Bees Not harmful to honeybees.
triarathene
Acaricide
NOMENCLATURE:
Common name triarath(ne) ((m) F-ISO); triarathene (BSI, E-ISO, ANSI)
IUPAC name 5-(4-chlorophenyl)-2,3-diphenylthiophene (I)
Development codes UBI-T930 Smiles code Clc1ccc(cc1)c2cc(c(s2)c3ccccc3)c4ccccc4
PHYSICAL CHEMISTRY:
Mol. wt. 346.9 M.f. C
22
H
15
ClS Form Colourless crystalline solid. M.p. 127 C
B.p. 462 C V.p. 1.3 10
6
mPa (25 C) K
ow
logP = 8 Stability It is thermally stable at
127 C; exposure to sunlight for several months causes a superfcial yellowing.
COMMERCIALISATION:
History Acaricide reported by D. I. Relyea et al. (Proc. Int. Congr. Plant Prot., 10th, 1983, 1,
355). Evaluated by Uniroyal Chemical Co., Inc.
APPLICATIONS:
Mode of action Contact acaricide. Uses Acaricide effective at 280560 g/ha against
eriophyoid mites (Aculus cornutus, Epitrimerus pyri and Phyllocoptruta oleivora) and
at 2.26 kg/ha against Eutetranychus banksi, Panonychus ulmi and Tetranychus urticae. Its
acaricidal action depends on the presence of daylight. The relationship between chemical
structure and acaricidal activity has been discussed (D. I. Relyea et al., Proc. Int. Congr. Plant
Prot., 10th, 1983, 1, 355). Formulation types WP.
PRODUCTS:
Discontinued products Micromite* (Uniroyal).
triazbutil 533
Oral Acute oral LD
50
for rats >10 000 mg tech./kg. Skin and eye Acute percutaneous
LD
50
for rabbits >2000 mg/kg. Mild eye and no skin irritation (for the WP). Inhalation for
rats >5.1 mg/l.
ECOTOXICOLOGY:
Birds LC
50
(8 d) for bobwhite quail and mallard duck >5620 mg/kg diet. Fish LC
50
(96 h)
for bluegill and rainbow trout >100 mg/l. Daphnia LC
50
(48 h) 64 mg/l.
triarimol
Fungicide
NOMENCLATURE:
Common name triarimol (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 2,4-dichloro--(pyrimidin-5-yl)benzhydryl alcohol
Chemical Abstracts name -(2,4-dichlorophenyl)--phenyl-5-pyrimidinemethanol
CAS RN [26766278] Development codes EL 273
Smiles code OC(c1ccccc1)(c2cncnc2)c3ccc(Cl)cc3Cl
PHYSICAL CHEMISTRY:
Mol. wt. 331.2 M.f. C
17
H
12
Cl
2
N
2
O
COMMERCIALISATION:
History Fungicide reported by J. V. Gramlich et al. (Proc. Br. Insectic. Fungic. Conf., 5th, 1969,
2, 576). Evaluated by Eli Lilly & Co.
PRODUCTS:
Discontinued products Trimidal* (Lilly).
triazbutil
Fungicide
NOMENCLATURE:
Common name triazbutil (BSI, E-ISO, (m) F-ISO, ANSI)
IUPAC name 4-butyl-4H-1,2,4-triazole (I)
Chemical Abstracts name (I) Other names butrizol CAS RN [16227104]
Development codes RH-124 Smiles code CCCCn1cnnc1
PHYSICAL CHEMISTRY:
Mol. wt. 125.2 M.f. C
6
H
11
N
3
534
tributyl phosphorotrithioite
COMMERCIALISATION:
PRODUCTS:
Discontinued products Indar* (Rohm & Haas).
tributyl phosphorotrithioite
NOMENCLATURE:
IUPAC name tributyl phosphorotrithioite (I)
Chemical Abstracts name (I) Other names merphos CAS RN [150505]
Smiles code CCCCSP(SCCCC)SCCCC
PHYSICAL CHEMISTRY:
12
H
27
PS
3
Form Colourless to pale
yellow liquid. B.p. 115134 C /0.08 mmHg S.g./density 0.991.01 (20 C)
Solubility Sparingly soluble in water; very soluble in most organic solvents.
COMMERCIALISATION:
History Introduced by the Mobil Chemical Co. and later by Rhne-Poulenc Agrochimie.
Patents US 2955803
APPLICATIONS: Uses At 1.22.5 kg/ha to defoliate cotton. Can induce leaf abscission
in some other plants, such as roses and hydrangeas. Formulation types AI.
PRODUCTS:
Discontinued products Folex* (Rhne-Poulenc Phytosanitaire).
ANALYSIS:
Product analysis by glc. Residues determined by glc with MCD.
Oral Acute oral LD
50
for male albino rats 1272 mg/kg. Skin and eye Acute percutaneous
LD
50
for albino rabbits >4600 mg/kg. NOEL In 90 d feeding trials, dogs and rats receiving
750 mg/kg diet showed depression of cholinesterase but no other effect on pathology or
histology. ADI/RfD (EPA) cRfD 0.00003 mg/kg b.w. [1991].
trichlamide 535
tricamba
Herbicide
NOMENCLATURE:
Common name tricamba (BSI, E-ISO, (m) F-ISO, ANSI, WSSA)
IUPAC name 3,5,6-trichloro-o-anisic acid
Chemical Abstracts name 2,3,5-trichloro-6-methoxybenzoic acid
CAS RN [2307495] Smiles code COc1c(Cl)cc(Cl)c(Cl)c1C(=O)O
PHYSICAL CHEMISTRY:
Mol. wt. 255.5 M.f. C
8
H
5
Cl
3
O
3
COMMERCIALISATION:
History Herbicide developed by Velsicol Corp. (later Sandoz AG).
PRODUCTS:
Discontinued products Banvel T* (Sandoz).
trichlamide
Fungicide
NOMENCLATURE:
Common name trichlamide (BSI, E-ISO, (m) F-ISO)
IUPAC name (RS)-N-(1-butoxy-2,2,2-trichloroethyl)salicylamide
Chemical Abstracts name ()-N-(1-butoxy-2,2,2-trichloroethyl)-2-hydroxybenzamide
CAS RN [70193214] Development codes NK-483 (Nippon Kayaku)
Smiles code CCCCOC(NC(=O)c1ccccc1O)C(Cl)(Cl)Cl
13
H
16
Cl
3
NO
3
Form Colourless
crystals. M.p. 7374 C V.p. <10 mPa (20 C) Solubility In water 6.5 mg/l. Soluble in
acetone, alcohols, and benzene. Stability Stable 70 C, and stable to light.
COMMERCIALISATION:
History Fungicide reported by T. Ohmori et al. (Plant Dis., 1986, 70, 51). Introduced in
Japan (1985) by Nippon Kayaku Co., Ltd. Patents GB 2004540; DE 2837819; US 4200632
APPLICATIONS:
Mode of action Non-systemic soil fungicide. Uses Control of diseases caused by
Aphanomyces and Streptomyces spp., and related fungal diseases (e.g. club root, Root rots,
scab, etc.) in potatoes and vegetables. Formulation types DP .
PRODUCTS:
Discontinued products Hataclean* (Nippon Kayaku).
536
2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate
ANALYSIS:
Oral Acute oral LD
50
LD
50
for rats and mice >5000 mg/kg. Non-irritating to eyes and skin (rabbits).
NOEL (2 y) for male rats 0.361 mg/kg, female rats 0.431 mg/kg daily. (2 y, gavage) for male
dogs 10 mg/kg daily, for female dogs 2 mg/kg daily. Non-teratogenic in rats and rabbits.
Other Acute i.p. LD
50
for male rats 1.54, female rats 1.14, male mice 1.59, female mice
1.66 mg/kg. Non-mutagenic in the Ames test, chromosomal aberration test, and
micronucleus test (K. Fukunaga Jpn. Pestic. Inf. 1990, 56, 1214).
ECOTOXICOLOGY:
Fish LC
50
ENVIRONMENTAL FATE:
50
6090 d.
2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate
Insecticide
NOMENCLATURE:
IUPAC name 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate
Chemical Abstracts name 3,4-dichloro--(trichloromethyl)benzenemethyl
acetate Other names benzethazet*; plifenate* (rejected common name proposals)
CAS RN [21757824] Development codes BAY MEB 6046
Smiles code CC(=O)OC(c1ccc(Cl)c(Cl)c1)C(Cl)(Cl)Cl
PHYSICAL CHEMISTRY:
Mol. wt. 336.4 M.f. C
10
H
7
Cl
5
O
2
Form Colourless crystalline solid. M.p. 84.5 C
V.p. 0.014 mPa (20 C) Henry 9.42 10
5
Pa m
3
mol
1
(calc.) Solubility In water 50 mg/
kg (20 C). In cyclohexanone >600, isopropanol <10 (both in g/kg, 20 C).
COMMERCIALISATION:
History Insecticide reported by W. Behrenz et al. (Pfanz.-Nachr. Bayer (Engl. Ed.), 1977, 30,
237). Introduced by Bayer AG. Patents DE 2110056
APPLICATIONS:
Biochemistry The (-)- isomer is more active. Mode of action Contact insecticide with
respiratory action and long residual activity. Uses It was recommended for use against
such pests as clothes moths, fies and mosquitoes. Formulation types AE; DP; UL .
PRODUCTS:
Discontinued products Baygon MEB* (Bayer); Penfenate* (Bayer).
trichlorobenzyl chloride 537
ANALYSIS:
Product and residue analysis by glc with ECD.
Oral Acute oral LD
50
50
for
rats >1000 mg/kg. Inhalation (4 h) for rats >0.7 mg/l air. NOEL (90 d) for rats
1000 mg/kg diet.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for hens >2500 mg/kg. Fish LC
50
(96 h) for orfe 0.51.0 mg/l.
ENVIRONMENTAL FATE:
Animals Following oral adminstration, there is no concentration in adipose tissue or liver,
kidney or brain. The alcohol has been isolated as a metabolite in animal tissue (W. Behrenz
et al., Pfanz.-Nachr. Bayer 1977, 30, 237).
4,5,7-trichloro-2,1,3-benzothiadiazole
Herbicide
NOMENCLATURE:
IUPAC name 4,5,7-trichloro-2,1,3-benzothiadiazole (I)
Chemical Abstracts name (I) CAS RN [1982554] Development codes PH 4021
Smiles code Clc1cc(Cl)c2nsnc2c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 239.5 M.f. C
6
HCl
3
N
2
S
COMMERCIALISATION:
History Herbicide reported by J. Dams et al. (Proc. Br. Weed Control Conf., 7th, 1964, p.
1091). Evaluated by Philips-Duphar B.V. (later Uniroyal Chemical Co., Inc.).
trichlorobenzyl chloride
Herbicide
NOMENCLATURE:
IUPAC name trichlorobenzyl chloride
Chemical Abstracts name trichloro(chloromethyl)benzene Other names TCBC
CAS RN [1344327], formerly [25429361] Smiles code ClCc1c(Cl)ccc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 229.9 M.f. C
7
H
4
Cl
4
COMMERCIALISATION:
History Herbicide introduced by Monsanto Co.
538
trichloronat
PRODUCTS:
Discontinued mixtures Randox-T* (+ allidochlor) (Monsanto).
trichloronat
Insecticide
IRAC 1B
NOMENCLATURE:
Common name trichloronate (BSI (before 1984), France); trichloronat (BSI (since 1984),
E-ISO, (m) F-ISO)
IUPAC name O-ethyl O-2,4,5-trichlorophenyl ethylphosphonothioate
Chemical Abstracts name O-ethyl O-(2,4,5-trichlorophenyl) ethylphosphonothioate
CAS RN [327980] EC no 2063261 Development codes Bayer 37 289; S 4400
Smiles code CCOP(=S)(CC)Oc1cc(Cl)c(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 333.6 M.f. C
10
H
12
Cl
3
O
2
PS Form Amber-coloured liquid. B.p. 108 C /0.01
mmHg V.p. 2 mPa (20 C) Henry 1.33 10-2 Pa m
3
mol
1
(20 C) Solubility In water 50 mg/l (20 C). In dichloromethane, isopropanol >1.2 kg/kg
(20 C). Stability Hydrolysed by alkali.
COMMERCIALISATION:
History Insecticide reported by R. O. Drummond (J. Econ. Entomol., 1963, 56, 831).
Introduced by Bayer AG. Patents DE 1099530
APPLICATIONS:
Uses It was recommended for the control of root maggots, other soil-dwelling insects and
wireworms. Formulation types EC; GR; Seed treatment.
PRODUCTS:
Discontinued products Agrisil* (Bayer); Agritox* (Bayer); Phytosol* (Bayer).
ANALYSIS:
Product analysis by uv spectroscopy after hydrolysis to 2,4,5-trichlorophenol. Residues
determined by glc (E. Mllhoff, Pfanz.-Nachr. Bayer (Engl. Ed.), 1968, 21, 331). See also Pestic.
Anal. Man., I, 302.
Oral Acute oral LD
50
for rats 1637.5, rabbits 2550 mg/kg. Skin and eye Acute
percutaneous LD
50
for male rats 135341 mg/kg. NOEL In 2 y feeding trials, rats receiving
3 mg/kg diet showed no symptom of poisoning. ADI/RfD (JMPR) No ADI [1971].
Toxicity Class WHO (a.i.) IaECClassifcation T+; R28| T; R24| N; R50, R53
tridiphane 539
triclopyricarb
Fungicide
NOMENCLATURE:
Common name triclopyricarb (pa ISO)
IUPAC name methyl N-methoxy-2-(3,5,6-trichloro-2-pyridyloxymethyl)carbanilate
Chemical Abstracts name methyl N-methoxy-N-[2-[[(3,5,6-trichloropyridin-2-yl)oxy]
methyl]phenyl]carbamate CAS RN [902760401] Development codes SYP7017
Smiles code COC(=O)N(c1ccccc1COc2c(cc(c(n2)Cl)Cl)Cl)OC
PHYSICAL CHEMISTRY:
Mol. wt. 391.63 M.f. C
15
H
13
Cl
3
N
2
O
4
tridiphane
Herbicide
NOMENCLATURE:
Common name tridiphane (BSI, ANSI, E-ISO)
IUPAC name (RS)-2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane
Chemical Abstracts name ()-2-(3,5-dichlorophenyl)-2-(2,2,2-trichloroethyl)oxirane
Smiles code Clc1cc(Cl)cc(c1)C2(CC(Cl)(Cl)Cl)CO
2
PHYSICAL CHEMISTRY:
Mol. wt. 320.4 M.f. C
10
H
7
Cl
5
O Form Colourless crystals. M.p. 42.8 C V.p. 29 mPa
(25 C) K
ow
logP = 4.34 Henry 5.16 Pa m
3
mol
1
(calc.) Solubility In water 1.8 mg/l
(25 C). In methanol 0.98, acetone 9.1, xylene 4.6, chlorobenzene 5.6, dichloromethane 7.1
(all in kg/kg, 25 C). Stability Hydrolysis DT
50
80 d (pH 59, 35 C) (ARS PPD).
F.p. 46.7 C
COMMERCIALISATION:
History Herbicide reported by E. S. Saunders et al. (Proc. North Cent. Weed Control Conf.,
1981, p. 133). Introduced by Dow Chemical Co. (later DowElanco).
Patents US 4211549; EP 81351
CH
OH
C
N
N
N
C(CH
3
)
3
CH
540
trifenmorph
APPLICATIONS:
Mode of action Selective non-systemic herbicide, absorbed by the leaves and roots.
Uses Control of annual grass seedlings and broad-leaved weeds in maize. Applied post-
emergence in combination with triazine herbicides. Formulation types EC.
PRODUCTS:
Discontinued products Nelpon* (DowElanco); Tandem* (DowElanco).
ANALYSIS:
Product analysis by hplc. Residues determined by glc/ECD (Pestic. Anal. Man., II, 180.424;
Resid. Anal. Methods).
Oral Acute oral LD
50
LD
50
for rabbits 3536 mg/kg. Moderately irritating to eyes and skin (rabbits). Potential
skin sensitiser. NOEL (2 y) for rats 3 mg/kg daily. ADI/RfD (EPA) cRfD 0.003 mg/kg b.w.
[1992]. Toxicity Class WHO (a.i.) III
ECOTOXICOLOGY:
Birds Acute oral LD
50
50
(8 d) for mallard
ducks and bobwhite quail 5620 mg/kg diet. Fish LC
50
(96 h) for rainbow trout 0.53, bluegill
sunfsh 0.37 mg/l.
ENVIRONMENTAL FATE:
50
(ave.) 26 d, under aerobic conditions.
trifenmorph
Molluscicide
NOMENCLATURE:
Common name trifenmorph (BSI, E-ISO); triphenmorphe ((m) F-ISO)
IUPAC name 4-tritylmorpholine
Chemical Abstracts name 4-(triphenylmethyl)morpholine CAS RN [1420060]
EC no 2158122 Development codes WL 8008 (Shell)
Smiles code C1CN(CCO1)C(c2ccccc2)(c3ccccc3)c4ccccc4
PHYSICAL CHEMISTRY:
23
H
23
NO Form Colourless
crystalline solid. M.p. 176178 C, resolidifying and remelting at 185187 C; (tech. melts
150170 C, and again at 170185 C) V.p. 1.9 10-2 mPa (20 C)
Henry 3.13 10
1
Pa m
3
mol
1
(calc.) Solubility In water 0.02 mg/l (20 C). In carbon
tetrachloride 300, chloroform 450, tetrachloroethylene 255 (all in g/l, 20 C). Stability
Stable to heat and alkali, but hydrolysed by mild acid to morpholine and triphenylmethanol.
Slight decomposition occurs in uv light.
trifenofos 541
COMMERCIALISATION:
History Molluscicide reported by C. B. C. Boyce et al. (Nature (London), 1966, 210, 1140).
Introduced by Shell Research Ltd.
APPLICATIONS: Uses Effective against aquatic and semi-aquatic snails. Recommended
for application to irrigation and other moving water systems, at 0.030.01 mg/l, and in
static water atc. 1.02.0 mg/l. Also recommmended for application to Lymnaea truncatula
habitats, at 500 g/ha, to control fascioliasis.
PRODUCTS:
Discontinued products Frescon* (Shell).
ANALYSIS:
Product analysis is by non-aqueous titration with a perchloric-acetic acid mixture
(Pesticides used in Public Health, p. 248) or by hplc. Residues may be determined
colorimetrically with cyclohaxane-sulfuric acid (K. I. Beynon & G. R. Thomas, Bull, WHO,
1967, 37, 47); a method suitable for use under feld conditions is available (K. I. Beynon & A.
N. Wright, Pestic. Sci., 1975, 6, 515).
PDS 64 (1985). EU Status (1107/2009) Not approved, Commission Regulation
2076/2002.
Oral Acute oral LD
50
for rats 4462200, mice 7004800 mg/kg. Toxicity Class WHO
(a.i.) IIIECClassifcation Xn; R22| N; R50, R53
ENVIRONMENTAL FATE:
Plants In plants, and in soil and water, broken down initially to triphenylmethanol (K. I.
Beynon, et al., Pestic. Sci., 1972, 3, 689). Soil/Environment See plants.
trifenofos
IRAC 1B
NOMENCLATURE:
Common name trifenofos (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name O-ethyl S-propyl O-2,4,6-trichlorophenyl phosphorothioate
Chemical Abstracts name O-ethyl S-propyl O-(2,4,6-trichlorophenyl)
phosphorothioate CAS RN [38524822] Development codes RH-218; RH-8218
Smiles code CCCSP(=O)(OCC)Oc1c(Cl)cc(Cl)cc1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 363.6 M.f. C
11
H
14
Cl
3
O
3
PS
COMMERCIALISATION:
History Acaricide and insecticide introduced by Rohm & Haas Co.
542
trifopsime
APPLICATIONS:
trifop; trifop-methyl
Herbicide
NOMENCLATURE:
Common name trifop (BSI, E-ISO, (m) F-ISO)
IUPAC name (RS)-2-[4-(,,-trifuoro-p-tolyloxy)phenoxy]propionic acid
Chemical Abstracts name ()-2-[4-[4-(trifuoromethyl)phenoxy]phenoxy]propanoic
acid CAS RN [58594744] trifop (unstated stereochemistry); [59011302] trifop
(racemate); [58594777] trifop-methyl (unstated stereochemistry); [59011335] trifop-
methyl (racemate) Development codes Hoe 29 152 (trifop-methyl)
PHYSICAL CHEMISTRY:
Mol. wt. 326.3; (methyl ester 340.3) M.f. C
16
H
13
F
3
O
4
; (methyl ester C17H15F3O4)
COMMERCIALISATION:
trifopsime
Herbicide
NOMENCLATURE:
Common name trifopsime (BSI, E-ISO, (f) F-ISO)
IUPAC name acetone (R)-O-[2-[4-(,,-trifuoro-p-tolyloxy)phenoxy]propionyl]oxime
Chemical Abstracts name (R)-2-propanone O-[1-oxo-2-[4-[4-(trifuoromethyl)
phenoxy]phenoxy]propyl]oxime CAS RN [72131761]
Development codes Ro 138895
Smiles code CC(Oc1ccc(Oc2ccc(cc2)C(F)(F)F)cc1)C(=O)ON=C(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 381.4 M.f. C
19
H
18
F
3
NO
4
COMMERCIALISATION:
History Herbicide evaluated by Hofmann-La Roche Ltd.
trimethacarb 543
trimethacarb
Insecticide, molluscicide
IRAC 1A; carbamate
NOMENCLATURE:
Common name trimethacarb (BSI, ANSI, E-ISO)
IUPAC name Reaction product comprising 3,4,5-trimethylphenyl methylcarbamate (I)
and 2,3,5-trimethylphenyl methylcarbamate (II) in a ratio between 3.5:1 and 5.0:1 m/m
Chemical Abstracts name 2,3,5(or 3,4,5)-trimethylphenyl methylcarbamate
CAS RN [12407862] trimethacarb; [2686999] (I); [2655154] (II)
Development codes UC 27 867 (Union Carbide); SD 8530 (Shell) Offcial codes OMS 597
Smiles code 2,3,5-isomer:CNC(=O)Oc1cc(C)cc(C)c1C;3,4,5-isomer:CNC(=O)
Oc1cc(C)c(C)c(C)c1
PHYSICAL CHEMISTRY:
Mol. wt. 193.2 M.f. C
11
H
15
NO
2
Form Buff to brown, crystalline solid. M.p. 105114 C
V.p. 6.8 mPa (25 C) Henry 2.27 10-2 Pa m
3
mol
1
(calc.) Solubility In water >58 mg/
kg (23 C). Not readily soluble in organic solvents. Stability Decomposed by strong acids
and alkalis. Stable to light.
COMMERCIALISATION:
History Insecticide originally introduced by Shell Development Co. (now E. I. du Pont
de Nemours & Co.) and later by Union Carbide Agrochemicals (now Bayer AG, who no
longer manufacture or market it).
APPLICATIONS:
Biochemistry Cholinesterase inhibitor Mode of action Insecticide with predominantly
stomach action, but also some contact action. Long residual activity. Uses Control of
corn rootworms larvae in maize. Also controls a wide range of insect and mollusc pests,
and acts as a mammal and bird repellent. Phytotoxicity Non-phytotoxic when used as
directed. Phytotoxic to the seeds of some crops, including maize, sorghum, wheat and rice.
PRODUCTS:
Discontinued products Broot* (Drexel); Landrin* (Shell).
CH
3
CH
3
OCONHCH
3
CH
3
CH
3
CH
3
OCONHCH
3
CH
3
3,4,5- isomer 2,3,5- isomer
544
triprene
ANALYSIS:
Residues by glc with ECD (S. C. Lau & R. L. Marxmiller, J. Agric. Food Chem., 1970, 18,
413415). See also Pestic. Anal. Man., II, 180.305. In soil by gc/NPD (Environ. Chem. Methods).
Oral Acute oral LD
50
50
for rats
>2000 mg/kg. NOEL (2 y) for rats 50 ppm (2.5 mg/kg b.w.) (EPA Tracking).
ADI/RfD (EPA) 0.0025 mg/kg b.w. [1986]. Toxicity Class WHO (a.i.) O.
ECOTOXICOLOGY:
Fish Toxic to fsh. Bees Toxic to bees, in spray formulations.
ENVIRONMENTAL FATE:
Insecticides). Plants In plants, metabolism occurs via hydroxylation of the N-methyl group
and at the 3- and 4-methyl positions. All metabolites may be conjugated as glucosides.
50
c. 60 d in sterile soil.
trimeturon
Herbicide
NOMENCLATURE:
Common name trimeturon (BSI, (m) France)
IUPAC name 3-(4-chlorophenyl)-1,1,2-trimethylisourea
Chemical Abstracts name methyl N-(4-chlorophenyl)-N,N-
dimethylcarbamimidate CAS RN [3050279] Development codes BAY 40 557
Smiles code COC(=Nc1ccc(Cl)cc1)N(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 212.7 M.f. C
10
H
13
ClN
2
O
COMMERCIALISATION:
triprene
Insecticide
NOMENCLATURE:
Common name triprene (BSI, E-ISO, (m) F-ISO, ANSI, ESA)
IUPAC name S-ethyl (E,E)-(RS)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienethioate
tritac 545
Chemical Abstracts name (2E,4E)-S-ethyl 11-methoxy-3,7,11-trimethyl-
2,4-dodecadienethioate CAS RN [40596803], formerly [53023544]
Development codes ZR 619
Smiles code CCSC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC
PHYSICAL CHEMISTRY:
Mol. wt. 312.5 M.f. C
18
H
32
O
2
S
COMMERCIALISATION:
History Insect growth regulator introduced by Zoecon Corp. (later Sandoz AG).
APPLICATIONS:
Mode of action Insect growth regulator.
PRODUCTS:
Discontinued products Altorick* (Sandoz).
tripropindan
Herbicide
NOMENCLATURE:
Common name tripropindan (BSI, E-ISO); tripropindane ((m) F-ISO)
IUPAC name 1-(6-isopropyl-1,1,4-trimethylindan-5-yl)propan-1-one
Chemical Abstracts name 1-[2,3-dihydro-1,1,4-trimethyl-6-(1-methylethyl)-1H-
inden-5-yl]-1-propanone CAS RN [6682775] Development codes Ro 70668
Smiles code CC(C)c1cc2c(CCC2(C)C)c(C)c1CC(=O)C
PHYSICAL CHEMISTRY:
Mol. wt. 258.4 M.f. C
18
H
26
O
COMMERCIALISATION:
History Herbicide evaluated by Roche.
tritac
Herbicide
NOMENCLATURE:
Common name tritac (WSSA)
IUPAC name 1-(2,3,6-trichlorobenzyloxy)propan-2-ol
Chemical Abstracts name 1-[(2,3,6-trichlorophenyl)methoxy]-2-propanol
CAS RN [1861445] Smiles code CC(O)COCc1c(Cl)ccc(Cl)c1Cl
PHYSICAL CHEMISTRY:
Mol. wt. 269.6 M.f. C
10
H
11
Cl
3
O
2
546
urbacid
COMMERCIALISATION:
History Herbicide introduced by Hooker Chemical Corp.
PRODUCTS:
Discontinued products Tritac* (Hooker).
UBI-S734
Herbicide
NOMENCLATURE:
IUPAC name 2-pyridyl 1-(2,5-xylyl)ethyl sulfone 1-oxide
Chemical Abstracts name 2-[[1-(2,5-dimethylphenyl)ethyl]sulfonyl]pyridine 1-oxide
CAS RN [60263889] Development codes UBI-S734
Smiles code CC(c1cc(C)ccc1C)S(=O)(=O)c2cccc[n+]2[O-]
PHYSICAL CHEMISTRY:
Mol. wt. 291.4 M.f. C
15
H
17
NO
3
S
COMMERCIALISATION:
History Herbicide evaluated by Uniroyal Chemical Co., Inc.
urbacid
Fungicide
NOMENCLATURE:
Common name urbacid (JMAF)
IUPAC name methylarsinediyl bis(dimethyldithiocarbamate)
Chemical Abstracts name dimethylcarbamodithioic acid bis(anhydrosulfde) with
methylarsonodithious acid CAS RN [2445070]
Smiles code CN(C)C(=S)S[As](C)SC(=S)N(C)C
PHYSICAL CHEMISTRY:
Mol. wt. 330.4 M.f. C
7
H
15
AsN
2
S
4
Form Colourless crystals. M.p. 144 C V.p. Low
volatility Solubility Insoluble in water. Soluble in most organic solvents.
COMMERCIALISATION:
History Fungicide introduced by Bayer AG. Patents US 2644005; DE 833271
APPLICATIONS:
Mode of action Protective fungicide. Uses Sprays were used at 240480 g a.i. (as 800 g/
kg WP)/ha. It showed promise against Venturia inaequalis on apples, and was mainly used as
a mixture with thiram and ziram. Formulation types WP.
vamidothion 547
PRODUCTS:
Discontinued products Monzet* (Bayer); Urbacid* (Bayer);
Discontinued mixtures Tuzet* (+ thiram + ziram) (Bayer).
ANALYSIS:
Product analysis was by a titrimetric method. Residues may be determined by a
colorimetric method after conversion to arsenate (H. Frehse & H.Tietz, J. Agric. Food Chem.,
1959, 7, 553).
Oral Acute oral LD
50
for rats 175 mg/kg. ECClassifcation Not specifed, but
arsenic compounds in general (with exceptions) are assigned T; R23/25| N; R50, R53
(concentration-dependent)
vamidothion
NOMENCLATURE:
Common name vamidothion (BSI, E-ISO, (m) F-ISO, JMAF)
IUPAC name O,O-dimethyl S-2-(1-methylcarbamoylethylthio)ethyl phosphorothioate;
2-(2-dimethoxyphosphinoylthioethylthio)-N-methylpropionamide
Chemical Abstracts name O,O-dimethyl S-[2-[[1-methyl-2-(methylamino)-2-
oxoethyl]thio]ethyl] phosphorothioate CAS RN [2275232] EC no 2188948
Development codes 10 465 RP (Rhne-Poulenc); NPH 83 Offcial codes ENT 26 613
Smiles code CNC(=O)C(C)SCCSP(=O)(OC)OC
PHYSICAL CHEMISTRY:
Mol. wt. 287.3 M.f. C
8
H
18
NO
4
PS
2
Form Colourless needles; (tech., white, waxy solid).
M.p. c. 43 C; (tech., 40 C) V.p. Negligible (20 C) Solubility Readily soluble in water
(4 kg/l), benzene, toluene, methyl ethyl ketone, ethyl acetate, acetonitrile, dichloromethane,
cyclohexanone, chloroform (allc. 1 kg/l). Almost insoluble in cyclohexane and petroleum
ether. Stability Undergoes slight decomposition at room temperature, but solutions in
organic solvents (methyl ethyl ketone, cyclohexanone) are stable. Decomposed in strong
acidic or alkaline media.
S
P(OCH
3
)
2
O
CH
2
CH
2
S
CH C
CH
3
CH
3
NH
O
548
vamidothion
COMMERCIALISATION:
History Insecticide reported by J. Desmoras et al. (Phytiatr.-Phytopharm., 1962, 11, 107).
Introduced by Rhne-Poulenc Agrochimie (later Bayer AG). Patents GB 872823; BE
575106 Manufacturers Bayer CropScience
APPLICATIONS:
acaricide. Metabolised in plants to the corresponding sulfoxide, which is of similar activity
to vamidothion but of greater persistence. Uses Systemic insecticide giving persistent
control of Eriosoma lanigerum and other piercing and sucking Homoptera in cotton, hops,
pome and stone fruit, and rice, at 3750 g/hl. Formulation types EC.
PRODUCTS:
Discontinued products Asystin Z* (Kwizda); Kilval* (Bayer CropScience); Kilvar*
(Japan) (Bayer CropScience); Trucidor* (Rhne-Poulenc); Vamidoate* (Rhne-Poulenc).
ANALYSIS:
Product analysis by hplc or glc (J. Desmoras et al., Anal. Methods Pestic. Plant Growth Regul.,
1973, 7, 479). Residues determined by glc (idem, ibid.; Man. Pestic. Residue Anal., pp. 3, 6, 13;
Anal. Methods Residues Pestic., 1988, Part I, M2, M5, M10; A. Ambrus et al., J. Assoc. Off. Anal.
Chem., 1981, 64, 733; A. R. C. Hill, Analyst (London), 1984, 109, 483).
JMPR Evaln. I 66 (1992); JMPR Evaln. II 55 (1988). ICSC.758 (2001).
Oral Acute oral LD
50
for male rats 100105, female rats 6467, mice 3437 mg/kg. For
the sulfoxide, acute oral LD
50
for male rats 160, mice 80 mg/kg. Skin and eye Acute
percutaneous LD
50
for mice 1460, rabbits 1160 mg/kg. Inhalation LC
50
(4 h) for rats
1.73 mg/l air. NOEL In 90 d feeding trials, the growth rate of rats receiving 50 mg
vamidothion/kg diet or 100 mg of its sulfoxide/kg diet was unaffected. ADI/RfD (JMPR)
0.008 mg/kg b.w. [1988]. Toxicity Class WHO (a.i.) IbECClassifcation T; R25| Xn;
R21| N; R50
ECOTOXICOLOGY:
Birds Acute oral LD
50
for pheasants 35 mg/kg. Fish LC
50
(96 h) for zebra fsh 590 mg/l. At
10 mg/l, harmless to goldfsh (14 d). Daphnia EC
50
(48 h) 0.19 mg/l. Bees Toxic to bees.
ENVIRONMENTAL FATE:
Animals Oxidised to the sulfoxide and sulfone, followed by cleavage of the P-S and
S-C bonds, to give water-soluble metabolites. Plants Metabolised in plants to the
corresponding sulfoxide, which appears within hours after treatment. Also demethylation
and hydrolysis to phosphoric acid. After 20 days, all the toxic residues in the plant are in
the form of the sulfoxide. Soil/Environment In soil, DT
50
1.01.5 d (aerobic, 22 C).
vernolate 549
vaniliprole
NOMENCLATURE:
Common name vaniliprole (BSI, E-ISO, (m) F-ISO, not Denmark)
IUPAC name (E)-1-(2,6-dichloro-,,-trifuoro-p-tolyl)-5-(4-hydroxy-3-
methoxybenzylidenamino)-4-trifuoromethylthiopyrazole-3-carbonitrile
Chemical Abstracts name 1-[2,6-dichloro-4-(trifuoromethyl)phenyl]-5-[[(E)-(4-
hydroxy-3-methoxyphenyl)methylene]amino]-4-[(trifuoromethyl)thio]-1H-pyrazole-
3-carbonitrile CAS RN [145767971] Development codes RPA-098231 (Rhne-
Poulenc)
PHYSICAL CHEMISTRY:
Mol. wt. 555.3 M.f. C
20
H
10
Cl
2
F
6
N
4
O
2
S
COMMERCIALISATION:
APPLICATIONS: Uses Foliar insecticide and acaricide for use in cotton, vines,
vegetables etc.
PRODUCTS:
Discontinued products Evaluation* (Aventis).
vernolate
Herbicide
NOMENCLATURE:
Common name vernolate (BSI, E-ISO, (m) F-ISO, WSSA, JMAF)
IUPAC name S-propyl dipropylthiocarbamate
Chemical Abstracts name S-propyl dipropylcarbamothioate CAS RN [1929777]
N
N
CN
CF
3
S
N C
CF
3
Cl
Cl
CH
3
O
HO
H
C N
O
S
CH
3
(CH
2
)
2
CH
3
(CH
2
)
2
CH
2
CH
2
CH
3
550
vernolate
EC no 2176817 Development codes R-1607 (Stauffer)
Smiles code CCCSC(=O)N(CCC)CCC
PHYSICAL CHEMISTRY:
10
H
21
NOS
Form Clear liquid, with slight aromatic odour; (tech. is a clear yellow liquid). B.p. 150 C
/30 mmHg V.p. 1.39 Pa (25 C) K
ow
logP = 3.84 (20 C) S.g./density 0.952 g/ml (20 C)
Solubility In water 90 mg/l (20 C). Miscible with common organic solvents, e.g. xylene,
methyl isobutyl ketone, kerosene, acetone, ethanol. Stability Stable in neutral media, and
relatively stable in acidic and alkaline media; DT
50
13 d (pH 7, 40 C). Stable up to 200 C.
Decomposed by sunlight. F.p. 121 C
COMMERCIALISATION:
History Herbicide introduced by Stauffer Chemical Co. (became Zeneca Agrochemicals).
First registered in USA in 1964. Patents US 2913327
APPLICATIONS:
Biochemistry Inhibits lipid synthesis (not ACCase inhibition). Mode of action Selective
herbicide, absorbed by the roots, with translocation to the stems and leaves. Germination
inhibitor. Uses Control of germinating broad-leaved and grass weeds in peanuts, soya
beans, maize, tobacco and sweet potatoes, at 1.53.0 kg/ha. Soil incorporation is necessary,
either pre-planting or pre-emergence. Formulation types EC; GR .
PRODUCTS:
Discontinued products Reward* (Zeneca); Saverit* (Chemolimpex); Savirox*
(Chemolimpex); Vernam* (Drexel).
ANALYSIS:
Product analysis by glc with FID (AOAC Methods, 18th Ed., 974.05; CIPAC Handbook, 1983,
1B, 1905); see also method for butylate, (ibid., 1983, 1B, 1744). Residues in crops and soils
determined by glc or by colorimetry after conversion to a derivative (G. G. Patchett & G.
H. Batchelder, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 337; W. J. Ja, Anal.
Methods Pestic. Plant Growth Regul., 1972, 6, 708). See also Pestic. Anal. Man., II, 180.240. In soil,
also by gc/NPD (Environ. Chem. Methods). In drinking water by glc with NPD (AOAC Methods,
18th Ed., 991.07).
Oral Acute oral LD
50
percutaneous LD
50
for rabbits >5000 mg/kg. Non-irritating to eyes and skin (rabbits). Not
a skin sensitiser (guinea pigs). Inhalation LC
50
(4 h) for rats >5 mg/l. NOEL NOAEL (2
generation) for rats 1 mg/kg b.w. (EPA RED); NOEL (90 d) for rats 32 mg/kg, for dogs 38
mg/kg daily. ADI/RfD (EPA) cRfD 0.001 mg/kg b.w. [1992, 1999, 2004]. Toxicity Class
WHO (a.i.) II EPA (formulation) III ECClassifcation Xn; R22| N; R51, R53
WL 9385 551
ECOTOXICOLOGY:
Birds Dietary LC
50
(7 d) for bobwhite quail 12 000 mg/kg. Fish LC
50
(96 h) for rainbow
trout 4.6, bluegill sunfsh 8.4 mg/l. Bees Non-toxic to bees at 0.011 mg/bee.
ENVIRONMENTAL FATE:
Plants Readily metabolised by plants to CO
2
and naturally-occurring plant constituents.
Soil/Environment In soil, microbial decomposition to mercaptan, amine, isopropanol and
CO
2
. DT
50
(27 C) 816 d; (4 C) >64 d.
WL 108 477
Insecticide
IRAC 4A
NOMENCLATURE:
IUPAC name 2-nitromethylene-1,3-thiazinan-3-ylcarbamaldehyde
Chemical Abstracts name dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-
carboxaldehyde CAS RN [94050507] Development codes WL 108 477
PHYSICAL CHEMISTRY:
Mol. wt. 188.2 M.f. C
6
H
8
N
2
O
3
S Form Pale yellow crystals. M.p. 138140 C (decomp.).
K
ow
logP = 0.23 Solubility In water 500 mg/l (20 C). In xylene 2.5 g/l.
COMMERCIALISATION:
History Insecticide reported by M. Harris et al. (Proc. 1986 Brit. Crop Prot. Conf. - Pests
Dis., 1, 115). Introduced by Shell Research Limited (became American Cyanamid Co.).
Manufacturers Cyanamid
APPLICATIONS:
Biochemistry Neurotoxic insecticide.
Oral Acute oral LD
50
for mice 10002500 mg/kg. Skin and eye Acute percutaneous LD
50

for mice >600 mg/kg.
ECOTOXICOLOGY:
Fish LD
50
(96 h) for rainbow trout >100 mg/l.
WL 9385
Herbicide
NOMENCLATURE:
IUPAC name 2-azido-4-tert-butylamino-6-ethylamino-1,3,5-triazine; 6-azido-N
2
-tert-
butyl-N4-ethyl-1,3,5-triazine-2,4-diamine
552
XMC
Chemical Abstracts name 6-azido-N-(1,1-dimethylethyl)-N-ethyl-1,3,5-
triazine-2,4-diamine CAS RN [2854708] Development codes WL 9385
Smiles code CCNc1nc(NC(C)(C)C)nc([N-][N+]#N)n1
PHYSICAL CHEMISTRY:
Mol. wt. 236.3 M.f. C
9
H
16
N
8
COMMERCIALISATION:
History Herbicide reported by R. A. Abbott & G. E. Barnsley (J. Sci. Food Agric., 1968, 19, 16).
Evaluated by Shell Research Ltd.
XMC
Insecticide
IRAC 1A; carbamate
NOMENCLATURE:
Common name XMC (JMAF)
IUPAC name 3,5-xylyl methylcarbamate
Chemical Abstracts name 3,5-dimethylphenyl methylcarbamate CAS RN [2655143]
Development codes H-69 (Hodogaya) Smiles code CNC(=O)Oc1cc(C)cc(C)c1
PHYSICAL CHEMISTRY:
Composition Tech. grade is 97% pure. Mol. wt. 179.2 M.f. C
10
H
13
NO
2
Form Colourless
crystals. M.p. 99 C (tech.) B.p. 239.7 C V.p. 6.88 mPa (25 C) K
ow
logP = 2.3 (25 C)
Henry 2.33 10
3
Pa m
3
mol
1
(25 C, calc.) S.g./density 1.16 (20 C) Solubility In
water 0.53 g/l (25 C). Soluble in most organic solvents; e.g. in acetone and ethanol >100,
xylene 67 (all in g/l, 25 C); also soluble in cyclohexanone and 3,5,5-trimethylcyclohex-
2-enone. Stability Rapidly hydrolysed in alkaline media. Relatively stable to neutral and
weakly acidic aqueous solutions. Stable to light and to temperatures up to 90 C.
COMMERCIALISATION:
History Introduced in 1968 as an insecticide by Hokko Chemical Industry Co., Ltd and
Hodogaya Chemical Co., Ltd.
Manufacturers Hodogaya; Saeryung
APPLICATIONS:
Biochemistry Cholinesterase inhibitor. Mode of action Insecticide with predominantly
contact action. Uses Control of leafhoppers and planthoppers on rice, and tea green
leafhoppers on tea, at 6001200 g/ha. Formulation types DP; EC; MG; WP.
OCONHCH
3
CH
3
CH
3
XRD-563 553
PRODUCTS:
Discontinued products Cosban* (Hodogaya); Macbal* (Hodogaya); Maqbal*
(Hodogaya).
ANALYSIS:
Product analysis by hydrolysis to 3,5-xylenol, which is measured by uv spectroscopy.
Residues determined by hydrolysis to 3,5-xylenol, a derivative of which is measured by glc.
EU Status (1107/2009) Never notifed to the EU.
Oral Acute oral LD
50
for rats 542, rabbits 445, mice 245 mg/kg. Skin and eye Not a
skin irritant (rabbits). Inhalation LC
50
for rats 1.02 mg/l. NOEL (90 d) for rats and mice
230 mg/kg b.w. daily. ADI/RfD 0.0034 mg/kg b.w. Toxicity Class WHO (a.i.) III EPA
(formulation) III ECClassifcation Xn; R22
ECOTOXICOLOGY:
Birds LD
50
(14 d) for quail 188, mallard ducks 1637 mg/kg. Fish LC
50
(48 h) for carp
>40 mg/l. Daphnia EC
50
(3 h) for Daphnia pulex 0.055 mg/l. Algae EC
50
(72 h) 12.3 mg/l.
Bees LD
50
(48 h, oral) 0.095 g/bee; (48 h, contact) 0.53 g/bee. Worms LD
50
(14 d)
45.4 mg/kg dry soil.
ENVIRONMENTAL FATE:
Animals In insects, metabolism mainly involves hydroxylation of the benzene ring and
the ring methyl substituents. Soil/Environment In soil, hydrolysed to 3,5-xylenol and
N-methylcarbamic acid.
XRD-563
Fungicide
NOMENCLATURE:
IUPAC name 2,6-dichloro-N-(4-trifuoromethylbenzyl)benzamide
Chemical Abstracts name 2,6-dichloro-N-[[4-(trifuoromethyl)phenyl]
methyl]benzamide CAS RN [124426499] Development codes XRD-563
Smiles code FC(F)(F)c1ccc(CNC(=O)c2c(Cl)cccc2Cl)cc1
15
H
10
Cl
2
F
3
NO Solubility In water 3.5
mg/l. Readily soluble in organic solvents, e.g. methanol and acetone.
O
NH
CH
2
CF
3
Cl
Cl
554
xylachlor
COMMERCIALISATION:
History Reported by W. Arnold et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 443).
Fungicide evaluated by DowElanco.
APPLICATIONS:
Mode of action Can be applied as a foliar spray and penetrates into plant tissue very
rapidly where it is transported acropetally. Shows curative, eradicant and protectant
activity. Uses Control of powdery mildew on wheat and barley. Can be mixed with azole
fungicides to give broad-spectrum control of cereal diseases. Formulation types EC.
Oral Acute oral LD
50
for rats >5000, mice >500 mg/kg. Skin and eye Acute percutaneous
LD
50
for rabbits >2000 mg/kg. Slight skin and eye irritation (rabbits). Other No evidence
of teratogenicity and negative in the Ames test.
ECOTOXICOLOGY:
Birds Acute oral LD
50
for adult bobwhite quail >2000 mg/kg. Dietary LC
50
(8 d) >5000
ppm in diet. Fish LC
50
(96 h) for bluegill sunfsh >100, rainbow trout 50100 mg/l.
Daphnia LD
50
(24 h) >100 mg/l.
xylachlor
Herbicide
NOMENCLATURE:
Common name xylachlor (WSSA)
IUPAC name 2-chloro-N-isopropylacet-2,3-xylidide
Chemical Abstracts name 2-chloro-N-(2,3-dimethylphenyl)-N-(1-methylethyl)acetamide
CAS RN [63114772] Development codes AC 206 784
Smiles code CC(C)N(C(=O)CCl)c1cccc(C)c1C
PHYSICAL CHEMISTRY:
Mol. wt. 239.7 M.f. C
13
H
18
ClNO
COMMERCIALISATION:
History Herbicide evaluated by American Cyanamid Co.
PRODUCTS:
Discontinued products Combat* (Cyanamid).
xylylcarb 555
xylylcarb
Insecticide
IRAC 1A; carbamate
NOMENCLATURE:
Common name xylylcarb (BSI, E-ISO, (m) F-ISO); MPMC (JMAF)
IUPAC name 3,4-xylyl methylcarbamate
Chemical Abstracts name 3,4-dimethylphenyl methylcarbamate CAS RN [2425107]
EC no 2193649 Development codes S-1046; S-21046 (both Sumitomo Chemical)
Smiles code CNC(=O)Oc1ccc(C)c(C)c1
PHYSICAL CHEMISTRY:
Mol. wt. 179.2 M.f. C
10
H
13
NO
2
Form Colourless solid. M.p. 7980 C; (tech.,
71.576 C) V.p. 121 mPa (25 C) Solubility In water 580 mg/l (20 C). In acetonitrile
930, cyclohexanone 770, xylene 134 (all in g/kg). Stability Hydrolysed in alkaline media.
COMMERCIALISATION:
History Insecticide reported by R. L. Metcalf et al. (J. Econ. Entomol., 1963, 56, 862).
Introduced by Sumitomo Chemical Co., Ltd.
Manufacturers Sumitomo Chemical
APPLICATIONS:
Uses Control of hoppers and other sucking insects on rice; and leafhoppers, planthoppers,
and scale insects on fruit. Formulation types DP; EC; MG; WP.
PRODUCTS:
Discontinued products Meobal* (Sumitomo Chemical).
ANALYSIS:
Product analysis by hplc (S. Sakaue et al., Nippon Nogei Kagaku Kaishi, 1981, 55, 1237) or by
uv spectrometry. Residues determined by glc of a derivative with ECD (J. Miyamoto et al.,
Nihon Hoyaku Gakkaishi, 1978, 3, 119).
Oral Acute oral LD
50
percutaneous LD
50
for rats >1000 mg/kg. Toxicity Class WHO (a.i.) II
OCONHCH
3
CH
3
CH
3
556
zolaprofos
ENVIRONMENTAL FATE:
Insecticides).
zarilamid
Fungicide
NOMENCLATURE:
Common name zarilamide ((m) F-ISO); zarilamid (BSI, E-ISO, not Brazil)
IUPAC name (RS)-4-chloro-N-[cyano(ethoxy)methyl]benzamide
Chemical Abstracts name ()-4-chloro-N-(cyanoethoxymethyl)benzamide
CAS RN [84527515] unstated stereochemistry
Development codes ICIA0001; PP001 Smiles code Clc1ccc(cc1)C(=O)NCOCCC#N
PHYSICAL CHEMISTRY:
Mol. wt. 238.7 M.f. C
11
H
11
ClN
2
O
2
Form Pale brown crystals. M.p. 111 C
V.p. 0.0047 mPa (20 C) Henry 6.72 10
6
Pa m
3
mol
1
Solubility In water 167 mg/l (pH 5.3, 20 C). In acetone >500, dichloromethane, methanol
271, ethyl acetate 336, hexane 0.12, toluene 26 (all in g/l, 20 C). Stability Stable >0.75 y
at ambient temperature; DT
50
(hydrolysis) 18 d (pH 5), 6 d (pH 7).
COMMERCIALISATION:
History Fungicide reported by S. P. Heaney et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis.,
2, 551). Evaluated by ICI Agrochemicals.
APPLICATIONS:
Mode of action Anti-microtubular fungicide.
Oral Acute oral LD
50
percutaneous LD
50
for rats >2000 mg/kg. Mild irritant to eyes.
ECOTOXICOLOGY:
Daphnia LC
50
5.65 mg/l. Bees LD
50
(contact) for honeybees >0.2 mg/bee.
zolaprofos
Insecticide
IRAC 1B
NOMENCLATURE:
Common name zolaprofos (BSI, E-ISO, (m) F-ISO)
IUPAC name O-ethyl S-3-methyl-1,2-oxazol-5-ylmethyl S-propyl phosphorodithioate;
O-ethyl S-(3-methylisoxazol-5-ylmethyl) S-propyl phosphorodithioate
zolaprofos 557
Chemical Abstracts name O-ethyl S-[(3-methyl-5-isoxazolyl)methyl] S-propyl
phosphorodithioate CAS RN [63771697] Development codes BAS 268I;
BAS 26800-I (both BASF) Smiles code CCCSP(=O)(OCC)SCc1cc(C)no1
PHYSICAL CHEMISTRY:
Mol. wt. 295.4 M.f. C
10
H
18
NO
3
PS
2
COMMERCIALISATION:
History Insecticide evaluated by BASF AG.
APPLICATIONS:

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