Metabolism of permethrin isomers in American cockroach adults,house fly adults,and cabbage looper larvae |
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| Authors: | Toshio Shono Tadaaki Unai John E Casida |
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| Institution: | Pesticide Chemistry and Toxicology Laboratory, Department of Entomological Sciences, University of California, Berkeley, California 94720 USA |
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| Abstract: | Forty-two insect metabolites of 1RS,trans]-and 1RS,cis]-permethrin are tentatively identified in studies with Periplaneta americana adults, Musca domestica adults, and Trichoplusia ni larvae involving administration of 14C preparations labeled in either the alcohol or acid moieties. The less-insecticidal trans isomer is generally metabolized more rapidly than the more-insecticidal cis isomer, particularly in cabbage looper larvae, and metabolites retaining the ester linkage appear in larger amount with cis-permethrin. Although the dichlorovinyl group effectively blocks oxidation in the acid side chain, the permethrin isomers are metabolized by hydrolysis and hydroxylation at the geminal-dimethyl group (either trans- or cis-methyl substituent) and the phenoxybenzyl group (predominantly at the 4′-position in all species but also at the 6-position in house flies). The alcoholic and phenolic metabolites are excreted as glucosides, and the carboxylic acids are excreted as glucosides and amino conjugates (glycine, glutamic acid, glutamine, and serine) with considerable species variation in the preferred conjugating moiety. |
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