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Concept
Cyhalothrine
Résumé
Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide.
It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.
Gamma-cyhalothrin and lambda-cyhalothrin are the active ingredients in the current commercial products based on cyhalothrin. Both are cyanohydrin esters of cis-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylic acid. All of the insecticidal activity is due to the proportion of absolute stereochemistry (1R) in the mixture. The active isomer of deltamethrin, (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid, has the same stereochemistry.
γ-cyhalothrin (a single chiral isomer) is indeed twice as active as λ-cyhalothrin on a weight-for-weight basis. The latter is racemic and contains the (1R) and inactive (1S) isomers in equal amounts.
By 1974, a team of Rothamsted Research scientists had discovered three pyrethroids (MoA 3a), suitable for use in agriculture, namely permethrin, cypermethrin and deltamethrin. These compounds were subsequently licensed by the NRDC, as NRDC 143, 149 and 161 respectively, to companies which could then develop them for sale in defined territories. Imperial Chemical Industries (ICI) obtained licenses to permethrin and cypermethrin but their agreement with the NRDC did not allow worldwide sales. Also, it was clear to ICI's own researchers at Jealott's Hill that future competition in the marketplace might be difficult owing to the greater potency of deltamethrin compared to the other compounds.
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