Insecticidal action and mitochondrial uncoupling activity of AC-303,630 and related halogenated pyrroles
1994
Black, B.C. | Hollingworth, R.M. | Ahammadsahib, K.I. | Kukel, C.D. | Donovan, S.
The mode of action of the experimental insecticide/acaricide, AC-303,630 (14-bromo-2-(4-chlorophenyl)-1 (ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile); Pirate, Stalker, CAS No. [122453-73-0]), and its halogenated pyrrole analogs was studied. AC-303,630 caused greatly increased respiratory activity in German cockroaches but was virtually inactive as an uncoupler against isolated mitochondria. However, its N-dealkylated analog, AC-303,268, was a potent uncoupler with notable activity in the range of 10-100 nM against rat, fish, and insect mitochondria. Both respiratory stimulation and toxicity were antagonized in insects by pretreatment with the monooxygenase inhibitor piperonyl butoxide. Structure-activity studies with a range of halogenated pyrroles also supported a relationship between uncoupling and toxicity. Based on these results it is concluded that AC-303,630 is a propesticide that is activated by the oxidative removal of the N-ethoxymethyl group. This releases a lipophilic, weakly acidic pyrrole metabolite which exerts its toxicity through mitochondrial uncoupling.
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