3991. Fenpropathrin

Nomenclature

CAS number: 39515-41-8
2,2,3,3-Tetramethylcyclopropane carboxylic acid cyano(3-phenoxyphenyl)methyl ester; α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate; fenpropanate; S-3206; SD-41706; WL-41706; Danitol (Sumitomo); Meothrin (Shell); Rody (Sumitomo).
C22H23NO3; mol wt 349.42.
C 75.62%, H 6.63%, N 4.01%, O 13.74%.

Description and references

Synthetic pyrethroid insecticide with repellant and contact activity. Prepn: T. Matsuo et al., DE 2231312; eidem, US 3835176 (1973, 1974 to Sumitomo). Commercial product is mixture of stereoisomers, the (S)-isomer primarily responsible for the bioactivity. Separation of enantiomers by chiral phase HPLC: R. A. Chapman, J. Chromatogr. 258, 175 (1983). Pesticidal activity: M. H. Breese, Pestic. Sci. 8, 264 (1977). Metabolism: M. J. Crawford, D. H. Hutson, ibid. 579. Degradn in soil: T. R. Roberts, M. E. Standen, ibid. 600; R. A. Chapman, Bull. Environ. Contam. Toxicol. 26, 513 (1981). Fish toxicity: J. R. Coats, ibid. 23, 250 (1979). Mammalian toxicity study: R. D. Verschoyle, W. N. Aldridge, Arch. Toxicol. 45, 325 (1980). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.

Chemical structure

Properties

Pale yellow oil, nD26 1.5283. LC50 (24 hr) in rainbow trout: 76.7 ppb (Coats). LD50 in rats (mg/kg): 2.5 i.v. (Verschoyle); in male, female rats (mg/kg): 24-36, 18-24 orally (Crawford).

Use

Insecticide, acaricide.