Nomenclature
CAS number: 51630-58-1
4-Chloro-α-(1-methylethyl)benzeneacetic acid cyano(3-phenoxyphenyl)methyl
ester; α-cyano-3-phenoxybenzyl α-(4-chlorophenyl)isovalerate; cyano(3-phenoxyphenyl)methyl 4-chloro-α-(1-methylethyl)benzeneacetate; α-cyano-3-phenoxybenzyl-2-(4-chlorophenyl)-3-methylbutyrate; phenvalerate; S-5602; SD-43775; WL-43775; Belmark (Shell); Pydrin (Shell); Pyridin (DuPont); Sumicidin (Sumitomo); Tirade (Sumitomo).
C
25H
22ClNO
3; mol wt 419.90.
C 71.51%, H 5.28%, Cl 8.44%, N 3.34%, O 11.43%.
Description and 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° = 1.1×108 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.Derivative
(S,S)-Isomer.
Nomenclature
CAS number: 66230-04-4
Esfenvalerate; Aα; OMS-3023; S-1844; S-5602α; Sumi-alpha (Sumitomo).
Properties
White crystalline solid, mp 59-60.2°. [α]D25 15.0° (c = 2.0 in CH3OH). d2323 1.163. Vapor pressure at 20°: 2.63×107 mm Hg; at 25°: 5.00×107 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, α-methylnaphthalene
50-60, xylene >60.Caution
Eye, skin irritant.Use
Insecticide.
Therapeutic Category (Veterinary)
Ectoparasiticide.