1209. Bifenthrin

Nomenclature

CAS number: 82657-04-3
[1α,3α(Z)]-(±)-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid (2-methyl[1,1′-biphenyl]-3-yl)methyl ester; 2-methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate; biphenate; biphenthrin; biphentrin; FMC-54800; Brigade (FMC); Talstar (FMC); Capture (FMC); Wisdom (Amvac).
C23H22ClF3O2; mol wt 422.87.
C 65.33%, H 5.24%, Cl 8.38%, F 13.48%, O 7.57%.

Description and references

Third generation synthetic pyrethroid. Prepn: J. F. Engel, EP 3336; idem, US 4238505 (1979, 1980 both to FMC); E. L. Plummer et al., Pestic. Sci. 14, 560 (1983). Physical properties, toxicology and review of field studies: H. J. H. Doel et al., Meded. Fac. Landbouwwet. Rijksuniv. Gent 49, 929 (1984). Insecticidal activity: M. S. Mulla, H. A. Darwazeh, Bull. Soc. Vector Ecol. 10, 1 (1985); M. S. Hamed, C. O. Knowles, J. Econ. Entomol. 81, 1295 (1988). Field studies: Y. Antignus et al., Ann. Appl. Biol. 110, 557 (1987); J. T. Trumble et al., J. Econ. Entomol. 81, 608 (1988). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.

Chemical structure

Properties

Light brown viscous oil, mp 51-66°. d25 1.212 g/ml. Vapor pressure at 25°: 1.81 × 10-7 Torr. Sol in methylene chloride, chloroform, acetone, ether, toluene. Slightly sol in heptane, methanol. Soly in water: <0.1 ppb. LD50 orally in rats: 54.5 mg/kg; LD50 dermally in rabbits: >2000 mg/kg (Doel).

Use

Insecticide, acaricide.