Metabolism of nitrodiphenyl ether herbicides by dioxin-degrading bacterium Sphingomonas wittichii RW1

J Agric Food Chem. 2008 Oct 8;56(19):9146-51. doi: 10.1021/jf801362k. Epub 2008 Sep 9.


Nitrodiphenyl ether herbicides, including chlomethoxyfen, nitrofen, and oxyfluorfen are potent herbicides. Some metabolites and parent compounds are considered as possible mutagens and endocrine disruptors. Both properties pose serious hygienic and environmental risks. Sphingomonas wittichii RW1 is a well-known degrader of polychlorinated dibenzo- p-dioxins, dibenzofurans, and diphenyl ethers. However, no detailed research of its metabolic activity has been performed against pesticides with a diphenyl ether scaffold. In this study, we report S. wittichii RW1 as a very potent diphenyl ether herbicide-metabolizing bacterium with broad substrate specificity. The structures of metabolites were determined by instrumental analysis and synthetic standards. Most pesticides were rapidly removed from the culture medium in the order of nitrofen > oxyfluorfen > chlomethoxyfen. In general, herbicides were degraded through the initial reduction and N-acetylation of nitro groups, followed by ether bond cleavage. Relatively low concentrations of phenolic and catecholic metabolites throughout the study suggested that these metabolites were rapidly metabolized and incorporated into primary metabolism. These results indicate that strain RW1 has very versatile metabolic activities over a wide range of environmental contaminants.

MeSH terms

  • Dioxins / metabolism*
  • Halogenated Diphenyl Ethers / metabolism
  • Herbicides / metabolism*
  • Kinetics
  • Phenyl Ethers / metabolism*
  • Sphingomonas / growth & development
  • Sphingomonas / metabolism*


  • Dioxins
  • Halogenated Diphenyl Ethers
  • Herbicides
  • Phenyl Ethers
  • oxyfluorofen
  • nitrofen
  • chlormethoxynil