Fenvalerate
Title: Fenvalerate
CAS Registry Number: 51630-58-1
CAS Name: 4-Chloro-a-(1-methylethyl)benzeneacetic acid cyano(3-phenoxyphenyl)methyl ester
Additional Names: a-cyano-3-phenoxybenzyl a-(4-chlorophenyl)isovalerate; cyano(3-phenoxyphenyl)methyl 4-chloro-a-(1-methylethyl)benzeneacetate; a-cyano-3-phenoxybenzyl-2-(4-chlorophenyl)-3-methylbutyrate; phenvalerate
Manufacturers' Codes: S-5602; SD-43775; WL-43775
Trademarks: Belmark (Shell); Pydrin (Shell); Pyridin (DuPont); Sumicidin (Sumitomo); Tirade (Sumitomo)
Molecular Formula: C25H22ClNO3
Molecular Weight: 419.90
Percent Composition: C 71.51%, H 5.28%, Cl 8.44%, N 3.34%, O 11.43%
Literature References: Synthetic pyrethroid insecticide without the usual cyclopropane ring. Prepn: DE 2335347; K. Fujimoto et al., US 3996244 (1974, 1976, both to Sumitomo); D. A. Wood, DE 2651341; idem, US 4061664 (1977, both to Shell). Has two chiral centers giving four possible optical isomers; prepn and comparative insecticidal activity of isomers: M. Hirano et al., DE 2737297; eidem, US 4503071 (1978, 1985 both to Sumitomo). Absolute configuration of most active isomer, esfenvalerate: K. Aketa et al., Agric. Biol. Chem. 42, 895 (1978). GC separation of isomers: G. R. Cayley, B. W. Simpson, J. Chromatogr. 356, 123 (1986); determn of esfenvalerate in technical prepn: S. Sakaue et al., Agric. Biol. Chem. 51, 1671 (1987). Comprehensive description of activity and physical properties of esfenvalerate: H. Oo'uchi, Jpn. Pestic. Inf. 1985, 21-24. Comparative soil metabolism of isomers: P.W. Lee et al., J. Agric. Food Chem. 35, 384 (1987). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.
Properties: Clear yellow viscous liquid at 23°. d23 1.17. nD20 1.5533. Vapor press at 25° = 1.1´10-8 mm Hg. Soly at 20° (g/l): acetone, >450; chloroform, >450; methanol, >450; hexane, 77. Insol in water. More stable in acidic soln than in alk soln. Dec gradually between 150-300°. No significant breakdown after 100 hrs at 75°. LD50 orally in rats: 451 mg/kg (DMSO); >3200 mg/kg (aqueous suspension), Shell Technical Data Bulletin. Highly toxic to fish and bees.
Index of refraction: nD20 1.5533
Density: d23 1.17
Toxicity data: LD50 orally in rats: 451 mg/kg (DMSO); >3200 mg/kg (aqueous suspension), Shell Technical Data Bulletin
 
Derivative Type: (S,S)-Isomer
CAS Registry Number: 66230-04-4
Additional Names: Esfenvalerate; Aa
Manufacturers' Codes: OMS-3023; S-1844; S-5602a
Trademarks: Sumi-alpha (Sumitomo)
Properties: White crystalline solid, mp 59-60.2°. [a]D25 -15.0° (c = 2.0 in CH3OH). d2323 1.163. Vapor pressure at 20°: 2.63´10-7 mm Hg; at 25°: 5.00´10-7 mm Hg. Soly (1%): acetonitrile >60, chloroform >60, DMF >60, DMSO >60, ethyl acetate >60, acetone >60, ethyl cellosolve 40-50, n-hexane 1-5, kerosene <1, methanol 7-10, a-methylnaphthalene 50-60, xylene >60.
Melting point: mp 59-60.2°
Optical Rotation: [a]D25 -15.0° (c = 2.0 in CH3OH)
Density: d2323 1.163
 
CAUTION: Eye, skin irritant.
Use: Insecticide.
Therap-Cat-Vet: Ectoparasiticide.

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