Cypermethrin

Title: Cypermethrin
CAS Registry Number: 52315-07-8
CAS Name: 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl ester
Additional Names: (±)-a-cyano-3-phenoxybenzyl-(±)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
Manufacturers' Codes: NRDC-149; FMC-30980; PP-383
Trademarks: Ammo (FMC); Arrivo (FMC); Barricade (BASF); Basathrin (BASF); Cymbush (Syngenta); Cynoff (FMC); Demon (Syngenta); Flectron (BASF); Ripcord (BASF)
Molecular Formula: C22H19Cl2NO3
Molecular Weight: 416.30
Percent Composition: C 63.47%, H 4.60%, Cl 17.03%, N 3.36%, O 11.53%
Literature 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.
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).
Melting point: mp 60-80°
Toxicity data: LD50 in 8 day old rats, adult male rats (mg/kg): 14.9, 250.0 orally (Cantalamessa)
Use: Insecticide.
Therap-Cat-Vet: Ectoparasiticide.
Cyphenothrin Cyprenorphine Cyproconazole Cyprodinil Cyproquinate

Cypermethrin
Alpha-cypermethrin.svg
Cypermethrin 3d.png
Identifiers
CAS number 52315-07-8 YesY
PubChem 2912
ChemSpider 2809 YesY
UNII 1TR49121NP YesY
KEGG D07763 YesY
MeSH Cypermethrin
ChEBI CHEBI:4042 YesY
ChEMBL CHEMBL373204 YesY
ATC code P03BA02,QP53AC08
Jmol-3D images Image 1
Properties
Molecular formula C22H19Cl2NO3
Molar mass 416.30 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cypermethrin is a synthetic pyrethroid used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. It behaves as a fast-acting neurotoxin in insects. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticides Telecommunications Network (NPTN). It is found in many household ant and cockroach killers, including Raid and ant chalk.