Naturally Occuring Insectcides

Abhay R. Vishwakarma
Msc part- ll Sem-IV
Mithibai college
Paper : III
 Contents

 Pesticide

 Introduction

 Pyrathrum

 Synthesis of pyrethrin – I

 Rotenoids

 Azadirachitin
 What is Pesticide???

• A chemical used for the control of….

– Insects
– Plant Pathogens
– Weeds
 PESTICIDES: TYPES & USES
Herbicides:
Used to control unwanted
plants or weeds.
Insecticides:
Used to control insects.
Fungicides:
Used to control fungal
diseases.
Miticides:
Used to control ticks & mites
(Spider-like animals).
History of insecticide: DDT
Naturally Ooccurring Insecticide : Introduction

• Many insecticidal compounds are known from plants.

• Most plants make defensive compounds called allomones.
Only a few are important commercially.
• Plant-derived insecticides have largely been replaced by
synthetic materials, but there are some advantages to the
naturally occurring materials. For example, these substances
are biodegradable.
• Selectivity is needed. Compounds that are toxic to insects,
but not toxic to mammals, are preferable, of course.
 Pyrethrum (pyrathrin – I )
Chrysanthemum cinerariifolium, Asteraceae
Structure
 Biological properties
 The biological active chemicals are ester which occur in
flower head.

 Pyrethrins acts as contact poisons affecting the insects nervous system

which paralyses the insect within in 90sec

 Pyrethrins contains a synergist (piperonyl butoxide) ,synergist work by

restricting an enzyme that insect use to detoxify the pyrethrins

 Acute toxicity in mammals is relatively low because the pyrethrins ester

are converted into nontoxic compounds

 Action of pyrethrin on cold blooded animal such as cockroach, house

flies , mosquito
 Rotenoids (Rotenone)
Rabo molle,
Derris elliptica, Lonchocarpus Legume root,
Fabaceae muehlenbergianus, Fabaceae
Fabaceae
Structure
 Biological properties
 Inhabit a cellular process, prevent insects of oxygen in their tissue
cells.

Their biological action is because rotenoids contain flavonoids

derivative which strongly inhabit mitochondrial respiration

Some mammalian toxicity – limits is used.

When exposed to sunlight it is easily biodegardes to form carbon

dioxide and water.

A non – polar molecule acts as acts toxic towards cold – blooded

animals but harmless to the man and enviorments

Uses: soft bodied insects, red spider, greenfly, cater pillar, wasps
 Synthesis of pyrethrin - I
Synthetic of trans – chrysanthemic acid methyl ester

Br + SO2Na

1-bromo-3-methyl p toluenesulfinate
2-butene DMF

SO2

allyl sulfone
 SO
2

NaOMe

1,3 COOMe
eliminatiom

trans – chrysanthemic acid methyl ester

Mechanism
OMe
H

SO2

COOMe
Synthesis of alcohol moiety
OH
OH
CH2OH CH2Br

Dibial- Witting
H
Pph3, reaction
CBr4 HBr

O
Lactol H

OH
Condensation of ester and alcohol

OH

OH

1 Oxd of OH- group

2 isomerisation of exo
methylene group
Pyrethrin
Reference :
The perethrum of flowers C. B. Gndinger

The insect P. J. Gullan, P. S. Cranston

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