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. 1993 Jul;59(7):2251–2256. doi: 10.1128/aem.59.7.2251-2256.1993

Reductive Dechlorination of the Nitrogen Heterocyclic Herbicide Picloram

K Ramanand 1,†, A Nagarajan 1,‡, Joseph M Suflita 1,*
PMCID: PMC182265  PMID: 16348997

Abstract

The anaerobic biodegradation of picloram (3,5,6-trichloro-4-amino-2-pyridinecarboxylic acid) in freshwater sediment was favored under methanogenic conditions but not when sulfate or nitrate was available as a terminal electron acceptor. Under the former conditions, more than 85% of the parent substrate (340 μM) was removed from nonsterile incubations in 30 days, following a 50-day acclimation period. Concomitant with substrate decay, an intermediate transiently accumulated in the sediment slurries. By liquid chromatography-mass spectrometry, the intermediate was identified as an isomer of dichloro-4-amino-2-pyridinecarboxylic acid. Proton nuclear magnetic resonance evidence suggested that a chlorine was reductively removed from the parent substrate at the position meta to the nitrogen heteroatom. Upon continued incubation, the dechlorinated product was transformed into an unidentified compound which accumulated and resisted further decay. The addition of sulfate or bromoethanesulfonic acid to sediment slurries inhibited picloram dehalogenation, but molybdate reversed the inhibitory effect of sulfate on pesticide metabolism. These findings help clarify the fate of a halogenated nitrogen heterocyclic herbicide in anaerobic environments.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Adrian N. R., Suflita J. M. Reductive dehalogenation of a nitrogen heterocyclic herbicide in anoxic aquifer slurries. Appl Environ Microbiol. 1990 Jan;56(1):292–294. doi: 10.1128/aem.56.1.292-294.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Berry D. F., Francis A. J., Bollag J. M. Microbial metabolism of homocyclic and heterocyclic aromatic compounds under anaerobic conditions. Microbiol Rev. 1987 Mar;51(1):43–59. doi: 10.1128/mr.51.1.43-59.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. DiStefano T. D., Gossett J. M., Zinder S. H. Reductive dechlorination of high concentrations of tetrachloroethene to ethene by an anaerobic enrichment culture in the absence of methanogenesis. Appl Environ Microbiol. 1991 Aug;57(8):2287–2292. doi: 10.1128/aem.57.8.2287-2292.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Genthner B. R., Price W. A., Pritchard P. H. Anaerobic Degradation of Chloroaromatic Compounds in Aquatic Sediments under a Variety of Enrichment Conditions. Appl Environ Microbiol. 1989 Jun;55(6):1466–1471. doi: 10.1128/aem.55.6.1466-1471.1989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Gibson S. A., Suflita J. M. Anaerobic biodegradation of 2,4,5-trichlorophenoxyacetic Acid in samples from a methanogenic aquifer: stimulation by short-chain organic acids and alcohols. Appl Environ Microbiol. 1990 Jun;56(6):1825–1832. doi: 10.1128/aem.56.6.1825-1832.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Gibson S. A., Suflita J. M. Extrapolation of biodegradation results to groundwater aquifers: reductive dehalogenation of aromatic compounds. Appl Environ Microbiol. 1986 Oct;52(4):681–688. doi: 10.1128/aem.52.4.681-688.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Horowitz A., Suflita J. M., Tiedje J. M. Reductive dehalogenations of halobenzoates by anaerobic lake sediment microorganisms. Appl Environ Microbiol. 1983 May;45(5):1459–1465. doi: 10.1128/aem.45.5.1459-1465.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Mohn W. W., Tiedje J. M. Microbial reductive dehalogenation. Microbiol Rev. 1992 Sep;56(3):482–507. doi: 10.1128/mr.56.3.482-507.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Ramanand K., Suflita J. M. Anaerobic degradation of m-cresol in anoxic aquifer slurries: carboxylation reactions in a sulfate-reducing bacterial enrichment. Appl Environ Microbiol. 1991 Jun;57(6):1689–1695. doi: 10.1128/aem.57.6.1689-1695.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Shelton D. R., Tiedje J. M. Isolation and partial characterization of bacteria in an anaerobic consortium that mineralizes 3-chlorobenzoic Acid. Appl Environ Microbiol. 1984 Oct;48(4):840–848. doi: 10.1128/aem.48.4.840-848.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Suflita J. M., Horowitz A., Shelton D. R., Tiedje J. M. Dehalogenation: a novel pathway for the anaerobic biodegradation of haloaromatic compounds. Science. 1982 Dec 10;218(4577):1115–1117. doi: 10.1126/science.218.4577.1115. [DOI] [PubMed] [Google Scholar]

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