Metabolism of metolachlor by the fungus Cunninghamella elegans

Autor: Cerniglia, C. E., Doerge, D. R., Churchwell, M. I., Pothuluri, J. V., Evans, F. E.
Předmět:
Zdroj: Archives of Environmental Contamination & Toxicology. Feb1997, Vol. 32 Issue 2, p117. 0p.
Abstrakt: The metabolism of metolachlor [2-chloro-N-(2-ethyl- 6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetami de] by the fungus Cunninghamella elegans ATCC 36112 was determined. The six metabolites identified comprised 81% of the total [{sup}14{end}C]-metolachlor metabolized by C. elegans. These metabolites were separated by reversed-phase high-performance liquid chromatography and identified by {sup}1{end}H nuclear magnetic resonance, UV, and atmospheric pressure chemical ionization (APCI) mass spectral techniques. Metabolites I and II were identifiedas stereoismers of 2-chloro-N-[2-ethyl-6- hydroxymethylphenyl)]-N-(2-hydroxy-1-methylethyl)a cetamide. Metabolites III and IV have been tentatively identified as stereoismers of 2-chloro-N-[2-(1-hydroxyethyl)-6-methylphenyl]-N- (2-methoxy-1-methylethyl)acetamide. MetabolitesV and VI were identified as stereoismers of 2-chloro-N-(2-ethyl-6- hydroxymethylphenyl)-N-(2-methoxy-1-methylethyl)ac etamide 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. [ABSTRACT FROM AUTHOR]
Databáze: GreenFILE
Externí odkaz: