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Phenylpyrazole Insecticide Photochemistry, Metabolism, and GABAergic Action:  Ethiprole Compared with Fipronil

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Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy and Management, University of California, Berkeley, California 94720-3112
Cite this: J. Agric. Food Chem. 2003, 51, 24, 7055–7061
Publication Date (Web):October 15, 2003
https://doi.org/10.1021/jf030439l
Copyright © 2003 American Chemical Society

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    Abstract

    Ethiprole differs from fipronil, the major phenylpyrazole insecticide, only in an ethylsulfinyl substituent replacing the trifluoromethylsulfinyl moiety. This study compares their photochemistry, metabolism, action at the γ-aminobutyric acid (GABA) receptor, and insecticidal potency. On exposure to sunlight as a thin film, ethiprole undergoes oxidation (major), reduction, and desethylsulfinylation but not desulfinylation whereas the major photoreaction for fipronil is desulfinylation. Metabolic sulfone formation is more rapid with ethiprole than fipronil in human expressed CYP3A4 in vitro and mouse brain and liver in vivo. High biological activity is observed for the sulfide, sulfoxide, sulfone, and desulfinyl derivatives in both the ethiprole and the fipronil series in GABA receptor assays (human recombinant β3 homomer and house fly head membranes) with [3H]EBOB and in topical toxicity to house flies with and without the P450-inhibiting synergist piperonyl butoxide. On an overall basis, the ethiprole series is very similar in potency to the fipronil series.

    Keywords: Ethiprole; fipronil; GABA receptor; metabolism; phenylpyrazole insecticide; photochemistry

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