METABOLISM OF METOLACHLOR BY THE FUNGUS CUNNINGHAMELLA-ELEGANS

The metabolism of metolachlor ethylphenyl)-N-(2-methoxy-1-methylethyl) acetamide] by the fungus Cunninghamella elegans ATCC 36112 was determi ned. The six metabolites identified comprised 81% of the total [C-14]- metolachlor metabolized by C. elegans. These metabolites were separate d by reversed-phase high-performance liquid chromatography and identif ied by H-1 nuclear magnetic resonance, UV, and atmospheric pressure ch emical ionization (APCT) mass spectral techniques. Metabolites I and I I were identified as stereoismers of thylphenyl)]-N-(2-hydroxy-1-methy lethyl)acetamide. Metabolites III and IV have been tentatively identif ied as stereoismers of hylphenyl]-N-(2-methoxy-1-methylethyl)acetatami de. Metabolites V and VI were identified as stereoismers of -hydroxy-m ethylphenyl)-N-(2-methoxy-1-methylethyl) acetamide and ethylphenyl)-N- (2-hydroxy-1-methylethyl)acetamide, respectively. The fungus Cunningha mella elegans was able to biotransform metolachlor. Multiple site oxid ation of metolachlor by C. elegans occurred predominantly by O-demethy lation of the N-alkyl side chain and benzylic hydroxylation of the ary lalkyl side chain.