Fipronil insecticide: Novel photochemical desulfinylation with retention of neurotoxicity

Proceedings of the National Academy of Sciences of the United States of America - Tập 93 Số 23 - Trang 12764-12767 - 1996
Dominik Hainzl1, John E. Casida1
1Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy, and Management, University of California, Berkeley, CA 94720-3112

Tóm tắt

Fipronil is an outstanding new insecticide for crop protection with good selectivity between insects and mammals. The insecticidal action involves blocking the γ-aminobutyric acid-gated chloride channel with much greater sensitivity of this target in insects than in mammals. Fipronil contains a trifluoromethylsulfinyl moiety that is unique among the agrochemicals and therefore presumably important in its outstanding performance. We find that this substituent unexpectedly undergoes a novel and facile photoextrusion reaction on plants upon exposure to sunlight, yielding the corresponding trifluoromethylpyrazole, i.e., the desulfinyl derivative. The persistence of this photoproduct and its high neuroactivity, resulting from blocking the γ-aminobutyric acid-gated chloride channel, suggest that it may be a significant contributor to the effectiveness of fipronil. In addition, desulfinylfipronil is not a metabolite in mammals, so the safety evaluations must take into account not only the parent compound but also this completely new environmental product.

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Proceedings of the National Academy of Sciences of the United States of America

Tập 93 Số 23

12764-12767

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