Fenvalerate

Fenvalerate
Names
	IUPAC name (RS)-alpha-Cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate
Identifiers
CAS Number	51630-58-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5014 ;
ChEMBL	ChEMBL492491 ;
ChemSpider	3230 ;
ECHA InfoCard	100.052.098
KEGG	C10988 ;
PubChem CID	3347;
RTECS number	CY 1576350;
UNII	Z6MXZ39302 ;
CompTox Dashboard (EPA)	DTXSID3020621 ;
	InChI 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 Key: NYPJDWWKZLNGGM-UHFFFAOYSA-N ; 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;
	SMILES Clc1ccc(cc1)C(C(=O)OC(C#N)c3cccc(Oc2ccccc2)c3)C(C)C;
Properties
Chemical formula	C25H22ClNO3
Molar mass	419.91 g·mol−1
Appearance	Yellow-brown viscous liquid
Density	1.175 g/cm3
Solubility in water	2 μg/L
Pharmacology
ATCvet code	QP53AC14 (WHO) QP53AX02 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 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

^ 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.

External links

Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center
Esfenvalerate Pesticide Information Profile - Extension Toxicology Network
Fenvalerate in the Pesticide Properties DataBase (PPDB)
WHO fenvalerate fact page

[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.

[1]

Names


IUPAC name (RS)-alpha-Cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate
Identifiers
CAS Number	51630-58-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5014
ChEMBL	ChEMBL492491
ChemSpider	3230
ECHA InfoCard	100.052.098
KEGG	C10988
PubChem CID	3347
RTECS number	CY 1576350
UNII	Z6MXZ39302
CompTox Dashboard (EPA)	DTXSID3020621
InChI 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 Key: NYPJDWWKZLNGGM-UHFFFAOYSA-N 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
SMILES Clc1ccc(cc1)C(C(=O)OC(C#N)c3cccc(Oc2ccccc2)c3)C(C)C
Properties
Chemical formula	C₂₅H₂₂ClNO₃
Molar mass	419.91 g·mol⁻¹
Appearance	Yellow-brown viscous liquid
Density	1.175 g/cm³
Solubility in water	2 μg/L
Pharmacology
ATCvet code	QP53AC14 (WHO) QP53AX02 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).