Isomerization and Beckmann rearrangement reactions in the metabolism of methomyl in rats |
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Authors: | Kurt Huhtanen HWyman Dorough |
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Institution: | Department of Entomology, University of Kentucky, Lexington, Kentucky 40506 USA |
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Abstract: | Methomyl {S-methyl-N-(methylcarbamoyl)oxy]thioacetimidate}, also known as Lannate, may exist in two geometric configurations but the more stable syn isomer is the form applied as an insecticide. In the rat, syn14CN]methomyl CH3S(CH3)CNOC(O)NHCH3] was metabolized to respiratory 14CO2 and in a ratio of about 2 to 1. Studies with the anti isomer showed that it was metabolized predominately to . These and other data are presented supporting the contention that syn methomyl is partially isomerized to the anti isomer in the animal prior to the hydrolysis of the ester linkage. After hydrolysis, the syn oxime CH3S(CH3)14CNOH] is further metabolized to 14CO2 while the anti oxime is metabolized to . Proposed immediate precursors to the carbon dioxide and acetonitrile, formed by Beckmann rearrangement of the syn and anti oximes, are CH3S14C(O)NHCH3 and , respectively. |
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