Pyrethroids April 11

 Synthetic Pyrethroids- Discovery, classification and structures
 Mode of action
 Application of Synthetic Pyrethroids
Discovery
 Pyrethroids insecticides are synthetic analogues of the
naturally occuring insecticidal pyrethrins found in extract of
Chrysanthemum cinerariaefolium.
 Pyrethrins-Hermann Staudinger and Leopold Ruzicka in the
1920s
 1st Generation-Schechter in 1949
First non-natural pyrethroids,Allenthrin
 2nd Generation-Further classified as
Type1-Permethrin,1973
Type2-Cypermethrin,1974
 1st generation synthetic pyrethroids-
Allenthrin Resmethrin
 2nd generation synthetic pyrethroids
Permethrin Cypermethrin
Pyrethroids Insects Crops
Bifenthrin Beetles, aphids, moths, locust,lice, Beans, cereals, corn,cotton,

house flies Melons
Cypermethrin Cockroaches, flies, moths, Cotton, onions,

mosquitoes pears,peaches
Deltamethrin Aphids, bollworms, Alfalfa ,beet, maize, cotton,
caterpillars,cicadas potatoes, soybean
Fluvalinate Leafhoppers, thrips, spider mites, Cereals,

moths cotton,tobacco,apples
Permethrin Ants, termites, lice, weevils Cotton, lettuce,

wheat,tomatoes
Households
Ornamental Pyrethroids Medical uses

plants
Veterinary
uses
 Mammalian intoxication by type I pyrethroids causes symptoms
characterized by tremor i.e., T-class, exaggerated startle response and hyper
excitability.
 Intoxication by type II pyrethroids results in burrowing and pawing
behaviour, followed by salivation and coarse tremor, which evolves into
choreoathetosis ( involuntary movement and writing). This second type of
poisoning is referrred to as CS- class.
 Some pyrethroids, such as fenproparthin and cyphenothrin can result in

symptoms from both T and CS- class, thus are called TS-class.
 Characteristics-
 Physical and chemical properties- The empirical formula is C22H19Br2NO3;
molecular weight is 505.2. Its form is a colorless crystal; its specific gravity
(bulk density) is 0.55 at 25°C; log Kow = 4.6. It is less soluble (< 0.0002 mg/l)
in water at 25°C, but it is soluble in most organic solvents.
 Mode of Action-
 Deltamethrin is effective against insects via ingestion and direct contact.
Pyrethroids, in general, interfere with normal production and conduction of
nerve signals in the nervous system.
 Uses-
 Deltamethrin is a broad-spectrum insecticide. Deltamethrin has been registered
for use on areas such as golf courses, ornamental gardens, lawns, outdoor
perimeter treatments, indoors as spot and crack and crevice treatments, and pet
collars.
 Fenvalerate appears as a clear viscious yellow liquid with a mild odor. Used as
broad spectrum insecticide. Fenvalerate is a carboxylic ester obtained by formal
condensation between 2-(4-chlorophenyl)-3-methylbutyric acid and cyano(3-
phenoxyphenyl)methanol.
 Mode of Action-
 It acts directly on nerve axons by prolonging sodium channel opening in cell
membranes. Insects exposed to fenvalerate are quickly paralyzed: exposure
causes quick insect knockdown. In small animals, type II pyrethroids cause
salivation, chewing, burrowing, choreoathetosis, and seizures.
 Uses-
 Fenvalerate is a highly active contact insecticide that is effective against a wide
range of pests, including strains resistant to organochlorine, organophosphorus
and carbamate insecticides (Worthing & Walker, 1987). It is used mainly in
agriculture, with about 90% used on cotton.
 Fenvalerate appears as a clear viscious yellow liquid with a mild odor. Used as
broad spectrum insecticide. Fenvalerate is a carboxylic ester obtained by formal
condensation between 2-(4-chlorophenyl)-3-methylbutyric acid and cyano(3-
phenoxyphenyl)methanol.
 Mode of Action-
 It acts directly on nerve axons by prolonging sodium channel opening in cell
membranes. Insects exposed to fenvalerate are quickly paralyzed: exposure causes
quick insect knockdown. In small animals, type II pyrethroids cause salivation,
chewing, burrowing, choreoathetosis, and seizures.
 Uses-
 Fenvalerate is one of the most versatile synthetic pyrethroid insecticides. It
is mostly used in agriculture and on cattle, but also in homes and gardens. It acts as
a stomach poison against a wide variety of leaf and fruit-eating insects such as
bollworm fruit and shoot borers and aphids.
 Lambdacyhalothrin is a colorless to beige solid that has a mild odor. It has a low
water solubility (5 x 10-3 mg/L) and is nonvolatile with a vapor pressure of 1.5 x
10-9 mm Hg at 20oC (2, 4).
 Mode of Action-
 Lambda-cyhalothrin kills insects by contact, ingestion and ovicidal action, and is
not locally systemic in plants. It offers rapid knockdown and residual control
while anti-feeding and repellency properties extend the biological effect against
some pests.
 Uses-
 Lambda cyhalothrin (Karate®, Syngenta) is a pyrethroid insecticide, introduced
in 1988, which allows the control of a wide variety of pests such as aphids,
Colorado beetle, and thrips.

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 Synthetic Pyrethroids- Discovery, classification and structures

Bifenthrin Beetles, aphids, moths, locust,lice, Beans, cereals, corn,cotton,

Cypermethrin Cockroaches, flies, moths, Cotton, onions,

Fluvalinate Leafhoppers, thrips, spider mites, Cereals,

Permethrin Ants, termites, lice, weevils Cotton, lettuce,

Ornamental Pyrethroids Medical uses

 Some pyrethroids, such as fenproparthin and cyphenothrin can result in

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