4085. Fipronil

Nomenclature

CAS number: 120068-37-3
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile; 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole; (±)-5-amino-1-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile; MB-46030; Frontline (Merial); Termidor (BASF).
C12H4Cl2F6N4OS; mol wt 437.15.
C 32.97%, H 0.92%, Cl 16.22%, F 26.08%, N 12.82%, O 3.66%, S 7.34%.

Description and references

GABA-gated chloride channel blocker. Prototype of the phenylpyrazole insecticides known as fiproles. Prepn: I. G. Buntain et al., EP 295117 (1988 to May & Baker); L. R. Hatton et al., US 5232940 (1993). Mechanism of action study: L. M. Cole et al., Pestic. Biochem. Physiol. 46, 47 (1993). Comprehensive description: F. Colliot et al., Brighton Crop Prot. Conf. - Pests Dis. 1992, 29-34.

Chemical structure

Properties

White solid, mp 200.5-201°. Vapor pressure (20°): 2.8 × 109 mm Hg. Log P (n-octanol/water): 4.0. Soly: water 2 mg/l; acetone >50%; corn oil >10,000 mg/l. LD50 in rats (mg/kg): 100 orally; >2000 dermally (Colliot); in mice (mg/kg): 32 i.p. (Cole).

Use

Pesticide.

Therapeutic Category (Veterinary)

Ectoparasiticide.