Structural Formula Vector Image
Title: Permethrin
CAS Registry Number: 52645-53-1
CAS Name: 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester
Additional Names: 3-(phenoxyphenyl)methyl (±)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; m-phenoxybenzyl (±)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Manufacturers' Codes: FMC-33297; NIA-33297; NRDC-143; PP-557; SBP-1513; S-3151
Trademarks: Ambush (Syngenta); Coopex (Bayer CropSci.); Dragnet (FMC); Ectiban (Schering-Plough); Eksmin (Sumitomo); Elimite (Allergan); Nix (Pharmygi^e-Scat); Perigen (Bayer CropSci.); Pounce (FMC); Permasect (Mitchell Cotts); Ridect (Pfizer)
Molecular Formula: C21H20Cl2O3
Molecular Weight: 391.29
Percent Composition: C 64.46%, H 5.15%, Cl 18.12%, O 12.27%
Literature References: Synthetic pyrethroid insecticide, more stable to light and at least as active as the natural pyrethrins and with low mammalian toxicity: M. Elliott et al., Nature 246, 169 (1973). Of the four possible isomers, the (1R,trans)- and the (1R,cis)-isomers are the two esters primarily responsible for insecticidal activity: P. E. Burt et al., Pestic. Sci. 5, 791 (1974). Prepn of the racemic mixture: T. Mizutani et al., DE 2437882 (1975 to Sumitomo); F. Mori et al., DE 2544150; eidem, US 4113968 (1976, 1978, both to Kuraray). Metabolism: M. Elliott et al., J. Agric. Food Chem. 24, 270 (1976); L. C. Gaughan et al., ibid. 26, 613 (1978). Photodecompn: R. L. Holmstead et al., ibid. 590. Analysis: H. Swaine, M. J. Tandy, Anal. Methods Pestic. Plant Growth Regul. 13, 103-120 (1984). Field evaluation to control flies and ticks in cows: S. S. Quisenberry, D. R. Strohbehn, J. Econ. Entomol. 77, 422 (1984); R. B. Davey, E. H. Ahrens, Am. J. Vet. Res. 45, 1008 (1984). Clinical trial in pediatric pediculosis: E. Ares Mazas et al., Int. J. Dermatol. 24, 603 (1985). Toxicity studies in mammals: L. Metker et al., U.S. NTIS AD Rep. 1977, AD-AO47284, 70 pp; F. Cantalamessa, Arch. Toxicol. 67, 510 (1993). Review: C. N. E. Ruscoe, Pestic. Sci. 8, 236 (1977). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.
Properties: Technical material is a mixture of ~60% trans- and 40% cis-isomers: Colorless crystals to a pale yellow viscous liquid, mp ~35°. bp0.05 220°. d20 1.190-1.272. Vapor pressure at 50° <1 ´ 10-6 mm Hg. Soly in water: <1 ppm. Sol or miscible with org solvents except ethylene glycol. LD50 orally in female rats: 3801 mg/kg (Metker). LD50 in 8 day old rats, male adult rats (mg/kg): 340.5, 1500.0 orally (Cantalamessa). Toxic to bees and fish.
Melting point: mp ~35°
Boiling point: bp0.05 220°
Density: d20 1.190-1.272
Toxicity data: LD50 orally in female rats: 3801 mg/kg (Metker); LD50 in 8 day old rats, male adult rats (mg/kg): 340.5, 1500.0 orally (Cantalamessa)
CAUTION: Mild irritant to skin and eyes (Metker).
Use: Insecticide.
Therap-Cat: Ectoparasiticide.
Therap-Cat-Vet: Ectoparasiticide.
Keywords: Ectoparasiticide.

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