Archives of Environmental Contamination and Toxicology

, Volume 32, Issue 2, pp 117–125

Metabolism of Metolachlor by the Fungus Cunninghamella elegans

  • J. V.  Pothuluri
  • F. E.  Evans
  • D. R.  Doerge
  • M. I.  Churchwell
  • C. E.  Cerniglia

DOI: 10.1007/s002449900163

Cite this article as:
Pothuluri, J., Evans, F., Doerge, D. et al. Arch. Environ. Contam. Toxicol. (1997) 32: 117. doi:10.1007/s002449900163

Abstract.

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 [14C]-metolachlor metabolized by C. elegans. These metabolites were separated by reversed-phase high-performance liquid chromatography and identified by 1H nuclear magnetic resonance, UV, and atmospheric pressure chemical ionization (APCI) 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)acetamide. 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.

Copyright information

© Springer-Verlag New York Inc. 1997

Authors and Affiliations

  • J. V.  Pothuluri
    • 1
  • F. E.  Evans
    • 1
  • D. R.  Doerge
    • 1
  • M. I.  Churchwell
    • 1
  • C. E.  Cerniglia
    • 1
  1. 1.Division of Microbiology, National Center for Toxicological Research, Food and Drug Administration, 3900 NCTR Road, Jefferson, Arkansas 72079, USA US