title: Metabolism of metolachlor by the fungus Cunninghamella elegans.
abstract: The metabolism of metolachlor[2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-met hyl ethyl)acetamide]by the fungus Cunninghamella elegans ATCC 36112 was determined. Thesix metabolites identified comprised 81% of the total[14C]-metolachlor metabolized by C. elegans. Thesemetabolites were separated by reversed-phase high-performance liquidchromatography and identified by 1H nuclear magnetic resonance, UV, and atmospheric pressure chemical ionization (APCI) mass spectraltechniques. Metabolites I and II were identified as stereoismers of2-chloro-N-[2-ethyl-6-hydroxymethylphenyl)]-N-(2-hydroxy-1-me thylet hyl)acetamide. Metabolites III and IV have been tentatively identified as stereoismers of2-chloro-N-[2-(1-hydroxyethyl)-6-methylphenyl]-N-(2-methoxy-1-++ +methy lethyl)acetamide. Metabolites V and VI were identified as stereoismers of2-chloro-N-(2-ethyl-6-hydroxy-methylphenyl)-N-(2-methoxy-1-me thylet hyl)acetamideand 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-hydroxy-1-methylethyl)acetam ide, respectively. The fungus Cunninghamellaelegans was able to biotransform metolachlor. Multiple site oxidation ofmetolachlor by C. elegans occurred predominantly byO-demethylation of the N-alkyl side chain and benzylichydroxylation of the arylalkyl side chain.
authors.affiliation: Division of Microbiology, National Center for Toxicological Research, Food and Drug Administration, 3900 NCTR Road, Jefferson, Arkansas 72079, USA.
authors.forename: J V
authors.initials: JV
authors.lastname: Pothuluri
authors.forename: F E
authors.initials: FE
authors.lastname: Evans
authors.forename: D R
authors.initials: DR
authors.lastname: Doerge
authors.forename: M I
authors.initials: MI
authors.lastname: Churchwell
authors.forename: C E
authors.initials: CE
authors.lastname: Cerniglia
mesh_terms: D000081:Acetamides / Q000378:metabolism*; D020093:Cunninghamella / Q000378:metabolism*; D006540:Herbicides / Q000378:metabolism*
chemical_list: D000081:Acetamides; D006540:Herbicides; C051786:metolachlor