1230. Bioresmethrin

Nomenclature

CAS number: 28434-01-7
(1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid [5-(phenylmethyl)-3-furanyl]methyl ester; trans-(+)-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid (5-benzyl-3-furyl)methyl ester; 5-benzyl-3-furylmethyl-(+)-trans-chrysanthemate; d-trans-[(5-benzyl-3-furyl)methyl]chrysanthemumate; (+)-trans-resmethrin; NRDC-107; NIA-18739; SBP-1390; Resbuthrin (Wellcome); Biobenzyfuroline (Sumitomo).
C22H26O3; mol wt 338.44.
C 78.07%, H 7.74%, O 14.18%.

Description and references

Synthetic pyrethroid insecticide. Prepn: M. Elliott, N. F. Janes, FR 1503260; eidem, US 3465007 and US 3542928 (1967, 1969, 1970, all to Nat. Res. Dev. Corp.). Insecticidal activity: M. Elliott et al., Nature 213, 493 (1967); idem, et al., Pestic. Sci. 2, 243 (1971). Mammalian metabolism: C. O. Abernathy, J. E. Casida, Science 179, 1235 (1973). Control of cockroaches: P. R. Chadwick et al., J. Med. Entomol. 13, 625 (1977). Acute toxicity: T. B. Gaines, R. E. Linder, Fundam. Appl. Toxicol. 7, 299 (1986). Brief review: D. S. Gunew, Anal. Methods Pestic. Plant Growth Regul. 10, 19-29 (1978). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.

Chemical structure

Properties

bp0.0008 174°. nD20 1.5346. [α]D20 -7.8° (c = 5 in acetone). Sol in most organic solvents. Insol in water. LD50 in adult male, female rats (mg/kg): 1244, 1721 orally (Gaines, Linder).

Use

Insecticide.