Microbial Metabolism of N-Methylcarbamate Insecticide. I. Metabolism of o-sec-Butylphenyl N-Methylcarbamate by Aspergillus niger van Tieghem

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In order to understand the metabolic fate of N-methylcarbamate in soil, the metabolism of o-sec-butylphenyl N-methylcarbamate (BPMC) (I) in a fungus, Aspergillus niger van Tieghem, was investigated. The following ten metabolites were detected in addition to unchanged BPMC ; o-sec-butylphenol (M-1), o-sec-butylphenylcarbamate (M-2), o-(1-methylacetonyl) phenyl N-methylcarbamate (M-3), o-sec-butylphenyl N-hydroxymethylcarbamate (M-4), o-(1-hydroxy-1-methylpropyl) phenyl N-methylcarbamate (M-5), threo-o-(2-hydroxy-1-methylpropyl) phenyl N-methylcarbamate (M-6), erythro-o-(2-hydroxy-1-methylpropyl) phenyl N-methylcarbamate (M-7), o-(1-hydroxymethylpropyl) phenyl N-methylcarbamate (M-8), o-(3-hydroxy-1-methylpropyl) phenyl N-methylcarbamate (M-9) and one unidentified product (UK-1). Both thin-layer chromatography (TLC) and gas-liquid chromatography (GLC) were used for detection and isolation of these metabolites, and the structures of these materials were characterized by ultraviolet, infrared, nuclear magnetic resonance and mass spectral analyses. Some major metabolites were identified by comparison of their chemical and physicochemical properties with those of synthesized materials.
社団法人日本薬学会の論文
1976-09-25