Permethrin の植物における代謝 Metabolism of Permethrin in Bean Plants

Permethrin [3-phenoxybenzyl 3-(2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate]の(+)-transおよび(+)-cis体をおのおのインゲンマメの葉面に処理すると, 両者とも速やかに代謝される.trans体とcis体の半減期はおのおの約7日と9日であった.両異性体ともエステル結合の開裂, アルコール側のフェノキシ基とおそらく酸側のジメチル基の酸化, ならびに生成するカルボン酸とアルコール類の抱合などの代謝反応を受ける.おもな代謝物はアルコール側からphenoxybenzyl alcohol, 2'-hydroxyphenoxybenzyl alcohol, 4'-hydroxyphenoxybenzyl alcoholのグルコシド, 酸側からはdichlorovinyl chrysanthemic acidとおそらくその水酸化体のグルコシドであった.permethrinの両異性体およびそれらの代謝物は植物体中でほとんど移行しなかった.

When applied to the leaf surface of bean plants, (+)-trans and (+)-cis permethrin[3-phenoxybenzyl 3-(2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylate] were readily metabolized in bean plants. The half-life was about 7 days and 9 days, respectively, for trans and cis permethrin. Both isomers of permethrin underwent ester cleavage, oxidation at the phenoxy group of the alcohol and probably at the geminal dimethyl group in the acid, and conjugation of the resulting carboxylic acids and alcohols. The major metabolites derived from the alcohol moiety were glucosides of 3-phenoxybenzyl alcohol, 3-(2'-hydroxyphenoxy)benzyl alcohol and 3-(4'-hydroxyphenoxy)benzyl alcohol, and those derived from the acid moiety were glucosides of 3-(2, 2-dichlorovinyl)-2, 2-dimethylcyclopropanecarboxylic acid and probably its hydroxylated derivatives. Both permethrin isomers and their metabolites hardly moved from the application site to the other parts of the plants.