2088. Chlorfenapyr

Nomenclature

CAS number: 122453-73-0
4-Bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile; AC-303630; CL-303630; Pirate (BASF); Stalker.
C15H11BrClF3N2O; mol wt 407.61.
C 44.20%, H 2.72%, Br 19.60%, Cl 8.70%, F 13.98%, N 6.87%, O 3.93%.

Description and references

Halogenated pyrrole mitochondrial uncoupler. Prepn: D. G. Brown et al., BR 8803788; eidem, US 5010098 (1988, 1991 both to Am. Cyanamid). Chemical and biological properties: J. B. Lovell et al., Brighton Crop Prot. Conf. - Pests Dis. 1990, 37. Summary of field trials: T. P. Miller et al., ibid. 43. Field trials on apples: Y.-J. Ahn et al., Appl. Entomol. Zool. 31, 67 (1996). Mechanism of action: B. C. Black et al., Pestic. Biochem. Physiol. 50, 115 (1994).

Chemical structure

Properties

White solid, mp 91-92°. Sol in acetone, diethyl ether, DMSO, THF, acetonitrile, alcohols. Insol in water. Log P ≈5. LD50 (single dose) in male, female rats (mg/kg): 223, 459 orally; in rabbits: >2000 dermally (Lovell). LC50 in Japanese carp: 0.5 ppm (Lovell).

Use

Insecticide. Acaricide.