Metabolism of metolachlor by the fungus Cunninghamella elegans

The metabolism of metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide] by the fungus Cunninghamella elegans ATCC 36112 was determined. The six metabolites identified comprised 81% of the total [C-14]-metolachlor metabolized by C. elegans. These metabolites were separated by reversed-phase high-performance liquid chromatography and identified by H-1 nuclear magnetic resonance, UV, and atmospheric pressure chemical ionization (APCT) mass spectral techniques. Metabolites I and II were identified as stereoismers of 2-chloro-N-[2-ethyl-6-hydroxymethylphenyl)]-N-(2-hydroxy-1-methylethyl)acetamide. Metabolites III and IV have been tentatively identified as stereoismers of 2-chloro-N-[2-(1-hydroxyethyl)-6-methylphenyl]-N-(2-methoxy-1-methylethyl)acetatamide. Metabolites V and VI were identified as stereoismers of 2-chloro-N-(2-ethyl-6-hydroxy-methylphenyl)-N-(2-methoxy-1-methylethyl) acetamide and 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-hydroxy-1-methylethyl)acetamide, respectively. The fungus Cunninghamella elegans was able to biotransform metolachlor. Multiple site oxidation of metolachlor by C. elegans occurred predominantly by O-demethylation of the N-alkyl side chain and benzylic hydroxylation of the arylalkyl side chain.