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Metabolism of fenpyroximate in rats


, : Metabolism of fenpyroximate in rats. Journal of Pesticide Science 18(1): 59-66

Metabolism of fenpyroximate, tert-butyl (E)-alpha-(1,3-dimethyl-5-phenoxypyrazol-4-yl-methyleneaminooxyl)-p-toluate in rats was studied. After a single oral administration of (pyrazole-3-14C), (phenyl-14C(U)) or (benzene ring-14C (U))fenpyroximate, the radiocarbon level in the blood increased to reach the maximum level of 0.18, 0.16 or 0.18 mu-g fenpyroximate eq./ml at 12, 12 or 9 hr, respectively, and then decreased at a half-life, of 11.3, 10.6 or 9 hr, respectively. The radiocarbons in 14C-fenpyroximate were rapidly and almost completely excreted into the urine and feces within 72 hr. The excretion rates of radiocarbon into the urine and feces were 26.2 and 65.5% for (pyrazole-3-14C), 26.1 and 63.9% for (phenyl-14C (U)) and 6.4 and 86.9% for (benzene ring-14C(U))fenpyroximate, respectively. Urinary metabolites identified were 1,3-dimethyl-5-phenoxypyrazole-4-carboxylic acid, 4-cyano-1-methyl-5-phenoxypyrazole-3-carboxylic acid and terephthalic acid. Major metabolites in the feces were (E)-4-((1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl)benzoic acid, (E)-2-(4-((1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl)benzoyloxy)-2-methylpropionic acid, (E)-2-(4-((1,3-dimethyl-5-(4-hydroxy)phenoxypyrazol-4-yl)methylene-aminooxymethyl)benzoyloxy)-2-methylpropionic acid,(E)-2-(4-((1-hydroxymethyl-3-methyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl) benzoyloxy)-2-methylpropionic acid and 4-hydroxymethylbenzoic acid. Fenpyroximate seemed to be metabolized via oxidation of the t-butyl group and methyl group at 3-position in the pyrazole ring, p-hydroxylation in the phenoxy moiety, N-demethylation, hydrolysis of the t-butyl ester, cleavage of the oxime ether bond and/or E/Z isomerization.

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