METABOLISM OF ALACHLOR BY THE FUNGUS CUNNINGHAMELLA-ELEGANS

The fungus Cunninghamella elegans ATCC 36112 transformed 98.6% of [C-14]alachlor [2-chloro-N-methoxymethyl-N-(2,6-diethylphenyl)acetamide] added to Sabouraud's dextrose broth to four metabolites within 96 h. Metabolism occurred predominantly by benzylic hydroxylation of one of the arylethyl side chains. Metabolites were separated by reversed-phase high-performance liquid chromatography and identified by H-1 nuclear magnetic resonance, UV, and mass spectral techniques. Two major metabolites were isomers of 2-chloro-N-(methoxymethyl)-N-[2-ethyl-6-(l-hydroxyethyl)-phenyl]acetamide and another was 2-chloro-N-(2,6-diethylphenyl)acetamide; the minor metabolite was 2-chloro-N-(methoxymethyl)-N-(2-vinyl-6-ethylphenyl)acetamide. The fungal transformations appear to be similar to those of mammalian microsomal oxidation since C. elegans oxidized alachlor at the benzylic positions and N-dealkylation occurred.