Dehalogenation of the herbicides bromoxynil (3,5-dibromo-4- hydroxybenzonitrile) and ioxynil (3,5-diiodino-4-hydroxybenzonitrile) by Desulfitobacterium chlororespirans

Applied and Environmental Microbiology

Volumn 71, Issue 7, 2005, Pages 3741-3746

  Cupples, Alison M ^a   Sanford, Robert A ^b   Sims, Gerald K ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; BIOMASS; BROMINE COMPOUNDS; HERBICIDES; METABOLITES; OXIDATION; PHENOLS; STOICHIOMETRY;

DEIODINATION; DESULFITOBACTERIUM CHLORORESPIRANS; ELECTRON ACCEPTORS; STOICHIOMETRIC CONVERSION;

DEHALOGENATION;

BENZOIC ACID DERIVATIVE; BROMOXYNIL; CARBON 14; CHLORINE; HERBICIDE; IOXYNIL; LACTIC ACID; PESTICIDE; PYRUVIC ACID; UNCLASSIFIED DRUG;

BIODEGRADATION; HERBICIDE; OXIDATION;

ARTICLE; BACTERIAL GROWTH; BACTERIUM CULTURE; BIOREMEDIATION; BIOTRANSFORMATION; CHEMICAL STRUCTURE; DEBROMINATION; DEHALOGENATION; DEIODINATION; DESULFITOBACTERIUM; DESULFITOBACTERIUM CHLORORESPIRANS; ENZYME SPECIFICITY; ENZYME SUBSTRATE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; NONHUMAN; PEST CONTROL; SOIL POLLUTION; STOICHIOMETRY;

ANAEROBIOSIS; BIODEGRADATION, ENVIRONMENTAL; CULTURE MEDIA; DESULFITOBACTERIUM; HERBICIDES; IODOBENZENES; NITRILES;

DESULFITOBACTERIUM; DESULFITOBACTERIUM CHLORORESPIRANS;

EID: 22144480319     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.71.7.3741-3746.2005     Document Type: Article

References (50)

1. Ahn, Y.-B., S.-K. Rhee, D. E. Fennell, L. J. Kerkhof, U. Hentschel, and M. M. Häggblom. 2003. Reductive dehalogenation of brominated phenolic compounds by microorganisms associated with the marine sponge Aplysina aerophoba. Appl. Environ. Microbiol. 69:4159-4166.
2. Arbeli, Z., and Z. Ronen. 2003. Enrichment of a microbial culture capable of reductive denomination of the flame retardant tetrabromobisphenol-A, and identification of the intermediate metabolites produced in the process. Biodegradation 14:385-395.
3. Bedard, D. L., and H. M. Van Dort. 1998. Complete reductive dehalogenation of brominated biphenyls by anaerobic microorganisms in sediment. Appl. Environ. Microbiol. 64:940-947.
4. Bouchard, B., R. Beaudet, R. Villemur, G. McSween, F. Lépine, and J.-G. Bisaillon. 1996. Isolation and characterization of Desulfitobacterium frappieri sp. nov., an anaerobic bacterium which reductively dechlorinates pentachlorophenol to 3-chlorophenol. Int. J. Syst. Bacteriol. 46:1010-1015.
5. Boulanger, B., J. Vargo, J. L. Schnoor, and K. C. Hornbuckle. 2004. Detection of perfluorooctane surfactants in Great Lakes water. Environ. Sci. Technol. 38:4064-4070.
6. Boyle, A. W., C. D. Phelps, and L. Y. Young. 1999. Isolation from estuarine sediments of a Desulfovibrio strain which can grow on lactate coupled to the reductive dehalogenation of 2,4,6-tribromophenol. Appl. Environ. Microbiol. 65:1133-1140.
7. Breitenstein, A., A. Saano, M. Salkinoja-Salonen, J. R. Andreesen, and U. Lechner. 2001. Analysis of a 2,4,6-trichlorophenol-dehalogenating enrichment culture and isolation of the dehalogenating member Desulfitobacterium frappieri strain TCP-A. Arch. Microbiol. 175:133-142.
8. 14C]dimethenamid under anaerobic conditions in flooded soil microcosms. J. Agric. Food Chem. 50:1483-1491.
9. David, M. B., L. E. Gentry, K. M. Starks, and R. A. Cooke. 2003. Stream transport of herbicides and metabolites in a tile-drained, agricultural watershed. J. Environ. Qual. 32:1790-1801.
10. Dennie, D., I. Gladu, F. Lépine, R. Villemur, J.-G. Bisaillon, and R. Beaudet. 1998. Spectrum of the reductive dehalogenation activity of Desulfitobacterium frappieri PCP-1. Appl. Environ. Microbiol. 64:4603-4606.
11. DeWeerd, K. A., and J. M. Suflita. 1990. Anaerobic aryl reductive dehalogenation of halobenzoates by cell extracts of "Desulfomonile tiedjei." Appl. Environ. Microbiol. 56:2999-3005.
12. Dolfing, J., and B. K. Harrison. 1992. Gibbs free energy of formation of halogenated aromatic compounds and their potential role as electron acceptors in anaerobic environments. Environ. Sci. Technol. 26:2213-2218.
13. Dolfing, J. 2003. Thermodynamic considerations for dehalogenation, p. 89-114. In M. M. Häggblom and I. D. Bossert (ed.), Dehalogenation: microbial processes and environmental applications. Kluwer Academic Publishers, Norwell, Mass.
14. Gerritse, J., V. Renard, T. M. Pedro Gomes, P. A. Lawson, M. D. Collins, and J. C. Gottschal. 1996. Desulfitobacterium sp. strain PCE1, an anaerobic bacterium that can grow by reductive dechlorination of tetrachloroethene or ortho-chlorinated phenols. Arch. Microbiol. 165:132-140.
15. Golovleva, L. A., R. N. Pertsova, F. Kunc, and M. Vokounová. 1988. Decomposition of the herbicide bromoxynil in soil and in bacterial cultures. Folia Microbiol. 33:491-499.
16. Graß, B., H. Mayer, J. Nolte, G. Preuß, and N. Zullei-Seibert. 2000. Studies on the metabolism of hydroxybenzonitrile herbicides: I. Mass spectrometric identification. Pest Manag. Sci. 56:49-59.
17. Grover, R., D. T. Waite, A. J. Cessna, W. Nicholaichuk, D. G. Irvin, L. A. Kerr, and K. Best. 1997. Magnitude and persistence of herbicide residues in farm dugouts and ponds in the Canadian prairies. Environ. Toxicol. Chem. 16:638-643.
18. Gu, A. Z., H. D. Stensel, J. M. H. Pietari, and S. E. Strand. 2003. Vinyl bromide as a surrogate for determining vinyl chloride reductive dechlorination potential. Environ. Sci. Technol. 37:4410-4416.
19. Häggblom, M. M., M. D. Rivera, and L. Y. Young. 1996. Anaerobic degradation of halogenated benzoic acids coupled to denitrification observed in a variety of sediment and soil samples. FEMS Microbiol. Lett. 144:213-219.
20. Hale, R. C., M. J. La Guardia, E. P. Harvey, M. O. Gaylor, T. M. Mainor, and W. H. Duff. 2001. Persistent pollutants in land-applied sludges. Nature 412:140-141.
21. He, Q., and R. A. Sanford. 2003. Characterization of Fe(III) reduction by chlororespiring Anaeromyxobacter dehalogenans. Appl. Environ. Microbiol. 69:2712-2718.
22. Knight, V. K., M. H. Berman, and M. M. Häggblom. 2003. Biotransformation of 3,5-dibromo-4-hydroxybenzonitrile under denitrifying, Fe(III)-reducing, sulfidogenic, and methanogenic conditions. Environ. Toxicol. Chem. 22:540-544.
23. Larney, F. J., A. J. Cessna, and M. S. Bullock. 1999. Herbicide transport on wind-eroded sediment. J. Environ. Qual. 28:1412-1421.
24. Lecouturier, D., J. J. Godon, and J. M. Lebeault. 2003. Phylogenetic analysis of an anaerobic microbial consortium deiodinating 5-amino-2,4,6- triiodoisophthalic acid. Appl. Microbiol. Biotechnol. 62:400-406.
25. Lecouturier, D., A. Rochex, and J. M. Lebeault. 2003. Enrichment and properties of an anaerobic mixed culture that reductively deiodinates 5-amino-2,4,6-triiodoisophthalic acid, an X-ray contrast agent precursor. Appl. Microbiol. Biotechnol. 62:550-556.
26. Lerch, R. N., and P. E. Blanchard. 2003. Watershed vulnerability to herbicide transport in northern Missouri and southern Iowa streams. Environ. Sci. Technol. 37:5518-5527.
27. McBride, K. E., J. W. Kenny, and D. M. Stalker. 1986. Metabolism of the herbicide bromoxynil by Klebsiella pneumoniae subsp. ozaenae. Appl. Environ. Microbiol. 52:325-330.
28. Miller, J. J., B. D. Hill, C. Chang, and C. W. Lindwall. 1995. Residue detections in soil and shallow groundwater after long-term herbicide applications in southern Alberta. Can. J. Soil Sci. 75:349-356.
29. Monserrate, E., and M. M. Häggblom. 1997. Dehalogenation and biodegradation of brominated phenols and benzoic acids under iron-reducing, sulfidogenic, and methanogenic conditions. Appl. Environ. Microbiol. 63:3911-3915.
30. Morris, P. J., J. F. Quensen III, J. M. Tiedje, and S. A. Boyd. 1992. Reductive denomination of the commercial polybrominated biphenyl mixture Firemaster BP6 by anaerobic microorganisms from sediments. Appl. Environ. Microbiol. 58:3249-3256.
31. Muir, D. C. G., and N. P. Grift. 1987. Herbicide levels in rivers draining two prairie agricultural watersheds (1984). J. Environ. Sci. Health B 22:259-284.
32. Plewa, M. J., E. D. Wagner, S. D. Richardson, A. D. Thruston, Jr., Y.-T. Woo, and A. B. McKague. 2004. Chemical and biological characterization of newly discovered iodoacid drinking water disinfection byproducts. Environ. Sci. Technol. 38:4713-4722.
33. Putschew, A., S. Wischnack, and M. Jekel. 2000. Occurrence of triiodinated X-ray contrast agents in the aquatic environment. Sci. Total Environ. 255:129-134.
34. Rittmann, B. E., and P. L. McCarty. 2001. Environmental biotechnology: principles and applications. McGraw-Hill, Inc., New York, N.Y.
35. Roberts, T. R., D. H. Hutson, P. W. Lee, P. H. Nicholls, and J. R. Plimmer (ed.). 1998. Metabolic pathways of agrochemicals. Part 1, Herbicides and plant growth regulators. The Royal Society of Chemistry, Cambridge, United Kingdom.
36. Ronen, Z., and A. Abeliovich. 2000. Anaerobic-aerobic process for microbial degradation of tetrabromobisphenol A. Appl. Environ. Microbiol. 66:2372-2377.
37. Rosenbrock, P., J. C. Munch, I. Scheunert, and U. Dörfler. 2004. Biodegradation of the herbicide bromoxynil and its plant cell wall bound residues in an agricultural soil. Pestic. Biochem. Physiol. 78:49-57.
38. Sanford, R. A., J. R. Cole, F. E. Löffler, and J. M. Tiedje. 1996. Characterization of Desulfitobacterium chlororespirans sp. nov., which grows by coupling the oxidation of lactate to the reductive dechlorination of 3-chloro-4-hydroxybenzoate. Appl. Environ. Microbiol. 62:3800-3808.
39. Sanford, R. A., J. R. Cole, and J. M. Tiedje. 2002. Characterization and description of Anaeromyxobacter dehalogenans gen. nov., sp. nov., an aryl-halorespiring facultative anaerobic myxobacterium. Appl. Environ. Microbiol. 68:893-900.
40. Semchuk, K. M., H. H. McDuffie, A. Senthilselvan, J. A. Dosman, A. J. Cessna, and D. G. Irvine. 2003. Factors associated with detection of bromoxynil in a sample of rural residents. J. Toxicol. Environ. Health Part A 66:103-132.
41. Sexstone, A. J., N. P. Revsbech, T. B. Parkin, and J. M. Tiedje. 1985. Direct measurement of oxygen profiles and denitrification rates in soil aggregrates. Soil Sci. Soc. Am. J. 49:645-651.
42. Smith, A. E. 1971. Degradation of bromoxynil in Regina heavy clay. Weed Res. 11:276-282.
43. Smith, A. E., and D. R. Cullimore. 1974. The in vitro degradation of the herbicide bromoxynil. Can. J. Microbiol. 20:773-776.
44. Ternes, T. A., and R. Hirsch. 2000. Occurrence and behavior of X-ray contrast media in sewage facilities and the aquatic environment. Environ. Sci. Technol. 34:2741-2748.
45. Topp, E., L. Xun, and C. S. Orser. 1992. Biodegradation of the herbicide bromoxynil (3,5-dibromo-4-hydroxybenzonitrile) by purified pentachlorophenol hydroxylase and whole cells of Flavobacterium sp. strain ATCC 39723 is accompanied by cyanogenesis. Appl. Environ. Microbiol. 58:502-506.
46. U.S. Environmental Protection Agency. 1998. Reregistration eligibility decision (RED): bromoxynil. EPA-738-R-98-013. U.S. Environmental Protection Agency, Washington, D.C.
47. Věková, J., L. Pavlù, J. Vosáhlo, and J. Gabriel. 1995. Degradation of bromoxynil by resting and immobilized cells of Agrobacterium radiobacter 8/4 strain. Biotechnol. Lett. 17:449-452.
48. Vokounová, M., O. Vacek, and F. Kunc. 1992. Degradation of the herbicide bromoxynil in Pseudomonas putida. Folia Microbiol. 37:122-127.
49. Vosáhlová, J., L. Pavlù, J. Vosáhlo, and V. Brenner. 1999. Degradation of bromoxynil, ioxynil, dichlobenil and their mixtures by Agrobacterium radiobacter 8/4. Pestic. Sci. 49:303-306. (Letter.)
50. Yang, Y., and P. L. McCarty. 1998. Competition for hydrogen within a chlorinated solvent dehalogenating anaerobic mixed culture. Environ. Sci. Technol. 32:3591-3597.