2767. Cypermethrin

Nomenclature

CAS number: 52315-07-8
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl ester; (±)-α-cyano-3-phenoxybenzyl-(±)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate; NRDC-149; FMC-30980; PP-383; Ammo (FMC); Arrivo (FMC); Barricade (BASF); Basathrin (BASF); Cymbush (Syngenta); Cynoff (FMC); Demon (Syngenta); Flectron (BASF); Ripcord (BASF).
C22H19Cl2NO3; mol wt 416.30.
C 63.47%, H 4.60%, Cl 17.03%, N 3.36%, O 11.53%.

Description and references

Synthetic pyrethroid insecticide, usually exists as a mixture of cis and trans isomers. Prepn of racemic mixture: M. Elliot et al., DE 2326077; eidem, US 4024163 (1974, 1977 to NRDC). Activity: eidem, Pestic. Sci. 6, 537 (1975); M. H. Breese, ibid. 8, 264 (1977). Soil degradation: T. R. Roberts, M. E. Standen, ibid. 305; D. D. Kaufman et al., J. Agric. Food Chem. 29, 239 (1981). Metabolism: T. Shono et al., ibid. 27, 316 (1979); M. J. Crawford et al., ibid. 29, 130 (1981). Analysis: A. Sapiets et al., Anal. Methods Pestic. Plant Growth Regul. 13, 33-51 (1984). Repellent activity against flies on cattle: J. A. Shemanchuk, Pestic. Sci. 12, 412 (1981); J. E. Hillerton et al., Br. Vet. J. 141, 160 (1985). Acute toxicity study: F. Cantalamessa, Arch. Toxicol. 67, 510 (1993). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.

Chemical structure

Properties

Commercial product is a mixture of eight isomers. Viscous semi-solid, mp 60-80°. Insol in water. Sol in methanol, acetone, xylene, methylene dichloride. LD50 in 8 day old rats, adult male rats (mg/kg): 14.9, 250.0 orally (Cantalamessa).

Use

Insecticide.

Therapeutic Category (Veterinary)

Ectoparasiticide.