Fenvalerate

Fenvalerate is a synthetic pyrethroid insecticide. It is a mixture of four optical isomers which have different insecticidal activities. The 2-S alpha (or SS) configuration, known as esfenvalerate, is the most insecticidally active isomer. Fenvalerate consists of about 23% of this isomer.

Fenvalerate
structural formula of fenvalerate with an unknown stereochemistry
Fenvalerate molecule
Names
IUPAC name
(RS)-alpha-Cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.052.098
KEGG
RTECS number
  • CY 1576350
UNII
  • InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3 checkY
    Key: NYPJDWWKZLNGGM-UHFFFAOYSA-N checkY
  • InChI=1/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3
    Key: NYPJDWWKZLNGGM-UHFFFAOYAU
  • Clc1ccc(cc1)C(C(=O)OC(C#N)c3cccc(Oc2ccccc2)c3)C(C)C
Properties
C25H22ClNO3
Molar mass 419.91 g·mol−1
Appearance Yellow-brown viscous liquid
Density 1.175 g/cm3
2 μg/L
Pharmacology
QP53AC14 (WHO) QP53AX02 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Fenvalerate is an insecticide of moderate mammalian toxicity. In laboratory animals, central nervous system toxicity is observed following acute or short-term exposure. Fenvalerate has applications against a wide range of pests including some of the more destructive such as the Helicoverpa assulta.[1] Residue levels are minimized by low application rates. Fenvalerate is most toxic to bees and fish. It is found in some emulsifiable concentrates, ULV, wettable powders, slow release formulations, insecticidal fogs, and granules. It is most commonly used to control insects in food, feed, and cotton products, and for the control of flies and ticks in barns and stables. Fenvalerate does not affect plants, but is active for an extended period of time.

Fenvalerate may irritate the skin and eyes on contact, and is also harmful if swallowed.

References
  1. Wang, Kai-Yun; Zhang, Yong; Wang, Hong-Yan; Xia, Xiao-Ming; Liu, Tong-Xian (2010-01-01). "Influence of three diets on susceptibility of selected insecticides and activities of detoxification esterases of Helicoverpa assulta (Lepidoptera: Noctuidae)". Pesticide Biochemistry and Physiology. 96 (1): 51–55. doi:10.1016/j.pestbp.2009.09.003.
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