Biodegradation of the Acetanilide Herbicides Alachlor, Metolachlor, and Propachlor

Critical Reviews in Microbiology

Volumn 24, Issue 1, 1998, Pages 1-22

  Stamper, David M ^a   Tuovinen, Olli H ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Alachlor; biodegradation; chloroacetanilides; glutathione conjugation; herbicide biodegradation; metolachlor; propachlor

Indexed keywords

EID: 0003104502     PISSN: 1040841X     EISSN: 15497828     Source Type: Journal    
DOI: 10.1080/10408419891294163     Document Type: Article

References (64)

1. Humburg, N. E, Colby, S. R., Hill, E. R., Kitchen, L. M., Lym, R. G., McAvoy, W. J., and Prasad, R., Herbicide Handbook of the Weed Science Society of America, 6th ed., Weed Science Society of America, Champaign, IL. 1989.
2. Thurman, E. M., Goolsby, D. A., Aga D.S., Pomes, N. L., and Meyer, M. T., Occurrence of alachlor and its sulfonated metabolite in rivers and reservoirs in the midwestern United States: the importance of sulfonation in the transport of chloroacetanilide herbicides, Environ. Sci. Technol., 30, 569, 1996.
3. Aga, D. S., Thurman, E. M., Yockel, M. E., Zimmerman, L. R., and Williams, T. D., Identification of a new sulfonic acid metabolite of metolachlor in soil, Environ. Sci. Technol., 30, 592, 1996.
4. Kolpin, D. W., Thurman, E. M., and Goolsby, D. A., Occurrence of selected pesticides and their metabolites in near-surface aquifers of the midwestern United States, Environ. Sci. Technol., 30, 335, 1996.
5. Chesters, G., Simsiman, G. V., Levy, J., Alhajjar, B. J., Fathulla, R. N., and Harkin, J. M., Environmental fate of alachlor and metolachlor, Rev. Environ. Contam. Toxicol., 110, 1, 1989.
6. Galassi, S., Provini, A., Mangiapan, S., and Benfenati, E., Alachlor and its metabolites in surface water, Chemosphere, 32, 229, 1996.
7. Gustafson, D. I., Pesticides In Drinking Water, Van Nostrand Reinhold, New York. 1993.
8. Potter, T. L. and Carpenter, T. L., Occurrence of alachlor environmental degradation products in groundwater, Environ. Sci. Technol., 29, 1557, 1995.
9. Richards, R. P., Baker, D. B., Creamer, N. L., Kramer, J. K., Ewing, D. E., Merryfield, B. J., and Wallrabenstein, L. K., Well water quality, well vulnerability, and agricultural contamination in the midwestern United States, J. Environ. Qual., 25, 389, 1996.
10. Chiron, S., Abian, J., Ferrer, M., Sanchez-Baeza, F., Messeguer, A., and Barceló, D., Comparative photodegradation rates of alachlor and bentazone in natural water and determination of breakdown products, Environ. Toxicol. Chem., 14, 1287, 1995.
11. Kochany, J. and Maguire, R. J., Sunlight photodegradation of metolachlor in water, J. Agric. Food Chem., 42, 406, 1994.
12. Rejtö, M., Saltzman, S., and Acher, A. J., Photodecomposition of propachlor, J. Agric. Food Chem., 32, 226, 1984.
13. Somich, C. L., Kearney, P. C., Muldoon, M. T., and Elsasser, S., Enhanced soil degradation of alachlor by treatment with ultraviolet light and ozone, J. Agric. Food Chem., 36, 1322, 1988.
14. Field, J. A. and Thurman, E. M., Glutathione conjugation and contaminant transformation, Environ. Sci. Technol., 30, 1413, 1996.
15. Leavitt, J. R. C. and Penner, D., In vitro conjugation of glutathione and other thiols with acetanilide herbicides and EPTC sul-foxide and the action of the herbicide antidote R-25788, J. Agric. Food Chem., 27, 533, 1979.
16. Stamper, D. M., Traina, S. J., and Tuovinen, O. H., Anaerobic transformation of alachlor, propachlor, and metolachlor with sulfide, J. Environ. Qual., 26, 488, 1997.
17. Rossini, L., Jepson, I., Greenland, A. J., and Gorla, M. S., Characterization of glu-tathione S-transferase isoforms in three maize inbred lines exhibiting differential sensitivity to alachlor, Pest. Physiol., 112, 1595, 1996.
18. Scarponi, L., Perucci, P., and Martinetti, L., Conjugation of 2-chloroacetanilide herbicides with glutathione: role of molecular structures and of glutathione S-transferase enzymes, J. Agric. Food Chem., 39, 2010, 1991.
19. Wolf, A. E., Dietz, K.-J., and Schröder, P., Degradation of glutathione S-conjugates by a carboxypeptidase in the plant vacuole, FEBS Lett., 384, 31, 1996.
20. Zablotowicz, R. M., Hoagland, R. E., Locke, M. A., and Hickey, W. J., Glutathione-S-transferase activity and metabolism of glutathione conjugates by rhizosphere bacteria, Appl. Environ. Microbiol., 61, 1054, 1995.
21. Driskell, W. J. and Hill, R. H., Identification of a major human urinary metabolite of metolachlor by LC-MS/MS, Bull. Environ. Contam. Toxicol., 58, 929, 1997.
22. Driskell, W. J., Hill, R. H., Shealy, D. B., Hull, R. D., and Hines, C. J., Identification of a major human urinary metabolite of alachlor by LC-MS/MS, Bull. Environ. Contam. Toxicol., 56, 853, 1996.
23. Lebaron, H. M., McFarland, J. E., Simoneaux, B. J. and Ebert, E., Meto-lachlor, in Herbicides: Chemistry, Degradation, and Mode of Action., Vol. 3., Kearny, P. C. and Kaufman, D. D., Eds., Marcel Dekker, New York, 1988, 335.
24. Sharp, D. B., Alachlor, in Herbicides: Chemistry, Degradation, and Mode of Action., Vol. 3., Kearny, P. C. and Kaufman, D. D., Eds., Marcel Dekker, New York, 1988, 301.
25. Tiedje, J. M. and Hagedorn, M. L., Degradation of alachlor by a soil fungus, Chaetomium globosum, J. Agric. Food Chem., 23, 77, 1975.
26. Ferrey, M. L., Koskinen, W. C., Blanchette, R. A., and Burns, T. A., Mineralization of alachlor by lignin-degrading fungi, Can. J. Microbiol., 40, 795, 1994.
27. Smith, A. E. and Phillips, D. V., Degradation of alachlor by Rhizoctonia solani, Agron. J., 67, 347, 1975.
28. Shelton, D. R., Khader, S., Karns, J. S., and Pogell, B. M., Metabolism of twelve herbicides by Streptomyces, Biodegradation, 7, 129, 1996.
29. Novick, N. J. and Alexander, M., Cometab-olism of low concentrations of propachlor, alachlor, and cycloate in sewage and lake water, Appl. Environ. Microbiol., 49, 737, 1985.
30. Sun, H. L., Sheets, T. S., and Corbin, F. T., Transformation of alachlor by soil microbial communities, Weed Sci., 38, 416, 1990.
31. Novick, N. J., Mukherjee, R., and Alexander, M., Metabolism of alachlor and propachlor in suspensions of pretreated soils and in samples from ground water aquifers, J. Agric. Food Chem., 34, 721, 1986.
32. Radosevich, M., Crawford, J. J., Traina, S. J., Oh, K.-H. and Tuovinen, O. H., Biodegradation of atrazine and alachlor in subsurface sediments, in Sorption and Degradation of Pesticides and Organic Chemicals in Soils., Linn, D. M., Carski, F. H., and Brusseau, M. L., Eds., Soil Science Society of America, American Society of Agronomy, Madison, WI, 1993, 33.
33. Ostrofsky, E. B., Traina, S. J., and Tuovinen, O. H., Variation in atrazine mineralization rates in relation to agricultural management practice, J. Environ. Qual., 26, 647, 1997.
34. Ward, A. D., Hatfield, J. L., Lamb, J. A., Alberts, E. E., Logan, T. J., and Anderson, J. L., The management systems evaluation areas program: tillage and water quality research, Soil Tillage Res., 30, 49, 1994.
35. Felsot, A. S. and Dzantor, E. K., Effect of alachlor concentration and an organic amendment on soil dehydrogenase activity and pesticide degradation rate, Environ. Toxicol. Chem., 14, 23, 1995.
36. Felsot, A. S. and Dzantor, E. K., Enhancing biodegradation for detoxification of herbicide waste in soil, in Enhanced Biodegradation of Pesticides in the Environment, Racke, K. D. and Coats, J. R., Eds., ACS Symposium Series 426, American Chemical Society, Washington, D.C., 1990, 249.
37. Capri, E. and Walker, A., Biodegradation of liquid and microencapsulated formulations of alachlor in a clay loam soil, Bull. Environ. Contam. Toxicol., 50, 506, 1993.
38. Walker, A. and Brown, P., The relative persistence in soil of five acetanilide herbicides, Bull. Environ. Contam. Toxicol., 34, 143, 1985.
39. Pothuluri, J. V., Moorman, T. B., Oben-huber, D. C., and Wauchope, R. D., Aerobic and anaerobic degradation of alachlor in samples from a surface-to-groundwater profile, J. Environ. Qual., 19, 525, 1990.
40. Sahid, I. and Wei, C. C., Degradation of two acetanilide herbicides in a tropical soil, Bull. Environ. Contam. Toxicol., 50, 24, 1993.
41. Yen, P. Y., Koskinen, W. C., and Schweizer, E. E., Dissipation of alachlor in four soils as influenced by degradation and sorption processes, Weed Sci., 42, 233, 1994.
42. Lavy, T. L., Mattice, J. D., Massey, J. H., Skulman, B. W., Senseman, S. A., Gbur, E. E., Jr., and Barrett, M. R., Long-term in situ leaching and degradation of six herbicides aged in subsoils, J. Environ. Qual., 25, 1268, 1996.
43. Konopka, A., Anaerobic degradation of chloroacetanilide herbicides, Appl. Microbiol. Biotechnol., 42, 440, 1994.
44. Bollag, J.-M., McGahen, L. L., Minard, R. D., and Liu, S.-Y., Bioconversion of alachlor in an anaerobic stream sediment, Chemosphere, 15, 153, 1986.
45. Zimdahl, R. L. and Clark, S. K., Degradation of three acetanilide herbicides in soil, Weed Sci., 30, 545, 1982.
46. Braverman, M. P., Lavy, T. L., and Barnes, C. J., The degradation and bioactivity of metolachlor in the soil, Weed Sci., 34, 479, 1986.
47. Liu, S.-Y., Freyer, A. J., and Bollag, J.-M., Microbial dechlorination of the herbicide metolachlor, J. Agric. Food Chem., 39, 631, 1991.
48. McGahen, L. L. and Tiedje, J. M., Metabolism of two new acylanilide herbicides, Antor herbicide (H–22234) and Dual (metolachlor) by the soil fungus Chaetomium globosum, J. Agric. Food Chem., 26, 414, 1978.
49. Miller, J. L., Wollam, A. G., III, and Weber, J. B., Degradation of carbon–14-atra-zine and carbon–14-metolachlor in soil from four depths, J. Environ. Qual., 26, 633, 1997.
50. Konopka, A. and Turco, R., Biodegradation of organic compounds in vadose zone and aquifer sediments, Appl. Environ. Microbiol., 57, 2260, 1991.
51. Saxena, A., Zhang, R., and Bollag, J.-M., Microorganisms capable of metabolizing the herbicide metolachlor, Appl. Environ. Microbiol., 53, 390, 1987.
52. Bollag, J.-M. and Liu, S.-Y., Microbial transformation of the herbicide metolachlor, in Diversity of Environmental Biogeochemistry., Berthelin, J., Ed., Elsevier, Amsterdam, 1991, 89.
53. Liu, S.-Y., Lu, M.-H., and Bollag, J.-M., Transformation of metolachlor in soil inoculated with a Streptomyces sp., Biodegradation, 1, 9, 1990.
54. Liu, S.-Y., Zheng, Z., Zheng, R., and Bollag, J.-M., Sorption and metabolism of meto-lachlor by a bacterial community, Appl. Environ. Microbiol., 55, 733, 1989.
55. Lee, J.-K., Minard, R. D., and Bollag, J.-M., Microbial metabolism of propachlor (2-chloro-N-isopropylacetanilide) in soil suspension, J. Kor. Agric. Chem. Soc., 25, 44, 1982.
56. Villarreal D. T., Turco, R. F., and Konopka, A., Propachlor degradation by a soil bacterial community, Appl. Environ. Microbiol., 57, 2135, 1991.
57. Villarreal, D. T., Turco, R. F., and Konopka, A., A structure-activity study with aryl acylamidases, Appl. Environ. Microbiol., 60, 3939, 1994.
58. Konopka, A., Knight, D., and Turco, R. F., Characterization of a Pseudomonas sp. capable of aniline degradation in the presence of secondary carbon sources, Appl. Environ. Microbiol., 55, 385, 1989.
59. De, M. A., O’Connor, O. A., and Kosson, D. S., Metabolism of aniline under different anaerobic electron-accepting and nutritional conditions, Environ. Toxicol. Chem., 13, 233, 1994.
60. Lyons, C. D., Katz, S., and Bartha, R., Mechanisms and pathways of aniline elimination from aquatic environments, Appl. Environ. Microbiol., 48, 491, 1984.
61. Myers C. R., Alatalo, L. J., and Myers, J. M., Microbial potential for the anaerobic degradation of simple aromatic compounds in sediments of the Milwaukee Harbor, Green Bay and Lake Erie, Environ. Toxicol. Chem., 13, 461, 1994.
62. Paris, D. E. and Wolfe, N. L., Relationship between properties of a series of anilines and their transformation by bacteria, Appl. Environ. Microbiol., 53, 911, 1987.
63. Windham, R. C., Evolved aniline catabolism in Acinetobacter calcoaceticus during continuous culture of river water, Appl. Environ. Microbiol., 51, 781, 1986.
64. Workman, S. R., Ward, A. D., Fausey, N. R., and Nokes, S. E., Atrazine and alachlor dissipation rates from field experiments, Trans. Amer. Soc. Agric. Eng., 38, 1421, 1995.