Degradation of fumigant pesticides: 1,3-dichloropropene, methyl isothiocyanate, chloropicrin, and methyl bromide

Vadose Zone Journal

Volumn 2, Issue 3, 2003, Pages 279-286

  Dungan, Robert S ^a   Yates, Scott R ^b  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

^b U S SALINITY LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMMONIA; BACTERIA; CARBON INORGANIC COMPOUNDS; DEHALOGENATION; FUMIGATION; INSECTICIDES; ISOMERS; METHANE; MICROORGANISMS; PESTICIDES; SOILS;

AMMONIA OXIDIZING BACTERIA; CHEMICAL AND BIOLOGICALS; METHYL ISOTHIOCYANATE; MICROBIOLOGICAL DEGRADATION; NUCLEOPHILIC SUBSTITUTIONS; OXIDATION OF METHANE; REPEATED APPLICATION; SOIL ORGANIC MATTERS;

BIODEGRADATION;

EID: 4544339417     PISSN: None     EISSN: 15391663     Source Type: Journal    
DOI: 10.2113/2.3.279     Document Type: Article

References (62)

1. Baker, L.W., D.L. Fitzell, J.N. Seiber, T.R. Parker, T. Shibamoto, M.W. Poore, K.E. Longley, R.P. Tomlin, R. Propper, and D.W. Duncan. 1996. Ambient air concentrations of pesticides in California. Environ. Sci. Technol. 30:1365-1368.
2. Basile, M., N. Senesi, and F. Lamberti. 1986. A study of some factors affecting volatilization losses of 1,3-dichloropropene (1,3-D) from soil. Agric. Ecosyst. Environ. 17:269-279.
3. Belser, N.O., and C.E. Castro. 1971. Biodehalogenation-The metabolism of the nematicides cis- and trans-3-chloroallyl alcohol by a bacterium isolated from soil. J. Agric. Food Chem. 19:23-26.
4. Boesten, J.J.T.I., L.J.T. Van der Pas, J.H. Smelt, and M. Leistra. 1991. Transformation rate of methyl isothiocyanate and 1,3-dichloro-propene in water-saturated sandy subsoils. Neth. J. Agric. Sci. 39: 179-190.
5. Castro, C.E., and N.O. Belser. 1966. Hydrolysis of cis- and trans-1,3-dichloropropene in wet soil. J. Agric. Food Chem. 14:69-70.
6. Castro, C.E., R.S. Wade, and N.O. Belser. 1983. Biodehalogenation. The metabolism of chloropicrin by Pseudomonas sp. J. Agric. Food Chem. 31:1184-1187.
7. Chung, K.Y., D.W. Dickson, and L.-T. Ou. 1999. Differential enhanced degradation of cis- and trans-1,3-D in soil with a history of repeated field applications of 1,3-D. J. Environ. Sci. Health B34:749-768.
8. Dungan, R.S., J. Gan, and S.R. Yates. 2001. Effect of temperature, organic amendment rate, and moisture content on the degradation of 1,3-dichloropropene in soil. Pest Manage. Sci. 57:1107-1113.
9. Dungan, R.S., J. Gan, and S.R. Yates. 2002. Accelerated degradation of methyl isothiocyanate in soil. Water Air Soil Pollut. 142:299-310.
10. Dungan, R.S., A.M. Ibekwe, and S.R. Yates. 2003. Effect of propargyl bromide and 1,3-dichloropropene on microbial communities in an organically amended soil. FEMS Microbiol. Ecol. 43:75-87.
11. Ellicott, M.L., and E.A. Des Jardin. 2001. Fumigation effects on bacterial populations in new golf course bermudagrass putting greens. Soil Biol. Biochem. 33:1841-1849.
12. Felsot, A., J.V. Maddox, and W. Bruce. 1981. Enhanced microbial degradation of carbofuran in soils with histories of Furadan use. Bull. Environ. Contam. Chem. 26:781-788.
13. Gan, J., J.O. Becker, F.F. Ernst, C. Hutchinson, J.A. Knuteson, and S.R. Yates. 2000b. Surface application of ammonia thiosulfate fertilizer to reduce volatilization of 1,3-dichloropropene from soil. Pest Manage. Sci. 56:264-270.
14. Gan, J., S.K. Papiernik, S.R. Yates, and W.A. Jury. 1999. Temperature and moisture effects on fumigant degradation in soil. J. Environ. Qual. 28:1436-1441.
15. Gan, J., and S.R. Yates. 1996. Degradation and phase partition of methyl iodide in soil. J. Agric. Food Chem. 44:4001-4008.
16. Gan, J., S.R. Yates, M.A. Anderson, W.F. Spencer, F.F. Ernst, and M.V. Yates. 1994. Effect of soil properties on degradation and sorption of methyl bromide in soil. Chemosphere 29:2685-2700.
17. Gan, J., S.R. Yates, D. Crowley, and J.O. Becker. 1998a. Acceleration of 1,3-dichloropropene degradation by organic amendments and potential application for emissions reduction. J. Environ. Qual. 27:408-414.
18. Gan, J., S.R. Yates, F.F. Ernst, and W.A. Jury. 2000a. Degradation and volatilization of the fumigant chloropicrin after soil treatment. J. Environ. Qual. 29:1391-1397.
19. Gan, J., S.R. Yates, S. Papiernik, and D. Crowley. 1998b. Application of organic amendments to reduce volatile pesticides emissions from soil. Environ. Sci. Technol. 32:3094-3098.
20. Geddes, J.D., G.C. Miller, and G.E. Taylor. 1995. Gas phase photolysis of methyl isothiocyanate. Environ. Sci. Technol. 29:2590-2594.
21. Gerstl, Z., U. Mingelgrin, and B. Yaron. 1977. Behavior of vapam and methylisothiocyanate in soils. Soil Sci. Soc. Am. J. 41:545-548.
22. Hartmans, S., W. Jansen, M.J. van der Werf, and J.A.M. de Bont. 1991. Bacterial metabolism of 3-chloroacrylic acid. J. Gen. Micro-biol. 137:2025-2032.
23. Kulakova, A.N., M.J. Larkin, and L.A. Kulakov. 1997. The plasmid-located haloalkane dehalogenase gene fromRhodococcus rhodoch-rous NCIMB 13064. Microbiology 143:109-115.
24. Lebbink, G., B. Proper, and A. Nipshagen. 1989. Accelerated degradation of 1,3-dichloropropene. Acta Hortic. 255:361-371.
25. Leistra, M., A.E. Groen, S.J.H. Crum, and L.J.T. van der Pas. 1991. Transformation rate of 1,3-dichloropropene and 3-chloroallyl alcohol in topsoil and subsoil material of flower-bulb fields. Pestic. Sci. 31:197-207.
26. Lembright, H.W. 1990. Soil fumigation: Principles and application technology. Suppl. J. Nematol. 22:632-644.
27. Macalady, J.L., M.E. Fuller, and K.M. Scow. 1998. Effects of metam sodium fumigation on soil microbial activity and community structure. J. Environ. Qual. 27:54-63.
28. McCall, P.J. 1987. Hydrolysis of 1,3-dichloropropene in dilute aqueous solution. Pestic. Sci. 19:235-242.
29. Miller, L.G., T.L. Connell, J.R. Guidetti, and R.S. Oremland. 1997. Bacterial oxidation of methyl bromide in fumigated agricultural soils. Appl. Environ. Microbiol. 63:4346-4354.
30. Oremland, R.S., L.G. Miller, C.W. Culbertson, T.L. Connell, and L. Jahnke. 1994. Degradation of methyl bromide by methanotrophic bacteria in cell suspensions and soils. Appl. Environ. Microbiol. 60:3640-3646.
31. Ou, L.-T., K.-Y. Chung, J.E. Thomas, T.A. Obreza, and D.W. Dickson. 1995. Degradation of 1,3-dichloropropene (1,3-D) in soils with different histories of field applications of 1,3-D. J. Nematol. 25: 249-257.
32. Ou, L.-T., P.J. Joy, J.E. Thomas, and A.G. Hornsby. 1997. Stimulation of microbial degradation of methyl bromide in soil during oxidation of an ammonia fertilizer. Environ. Sci. Technol. 31:717-722.
33. Ou, L.-T. 1997. Accelerated degradation of methyl bromide in meth-ane-, 2,4-D-, and phenol-treated soils. Bull. Environ. Contam. Tox-icol. 59:736-743.
34. Ou, L.-T. 1998. Enhanced degradation of the volatile fumigant-nema-ticides 1,3-D and methyl bromide in soil. J. Nematol. 30:50-64.
35. Ou, L.-T., J.E. Thomas, K.-Y. Chung, and A.V. Ogram. 2001. Degradation of 1,3-dichloropropene by a soil bacterial consortium and Rhodococcus sp. AS2C isolated from the consortium. Biodegrada-tion 12:39-47.
36. Papiernik, S.K., J. Gan, and S.R. Yates. 2000. Mechanism of degradation of methyl bromide and propargyl bromide in soil. J. Environ. Qual. 29:1322-1328.
37. Poelarends, G.J., M. Wilens, M.J. Larkin, J.D. van Elsas, and D.B. Janssen. 1998. Degradation of 1,3-dichloropropene by Pseudomo-nas cichorii 170. Appl. Environ. Microbiol. 64:2931-2936.
38. Rahman, A., C. Atkinson, J.A. Douglas, and D.P. Sinclair. 1979. Eradicane causes problems. N.Z. J. Agric. 139:47-49.
39. Rasche, M., M.R. Hyman, and D.J. Arp. 1990. Biodegradation of halogenated hydrocarbon fumigants by nitrifying bacteria. Appl. Environ. Microbiol. 56:2568-2571.
40. Roberts, S.T., and G. Stoydin. 1976. The degradation of (Z)- and (E)-1,3-dichloropropenes and 1,2-dichloropropane in soil. Pestic. Sci. 7:325-335.
41. Rosario, A.D., J. Remoy, V. Soliman, J. Dhaliwal, J. Dhoot, and K. Perera. 1994. Monitoring for selected degradation products following a spill of VAPAM into the Sacramento River. J. Environ. Qual. 23:279-286.
42. Sinha, A.P., V.P. Agnihotri, and K. Singh. 1979. Effect of soil fumigation with vapam on the dynamics of soil microflora and their related biochemical activity. Plant Soil 53:89-98.
43. Smelt, J.H., S.J.H. Crum, and W. Teunissen. 1989b. Accelerated transformation of the fumigant methyl isothiocyanate in soil after repeated application of metam-sodium. Environ. Sci. Health. B24: 437-455.
44. Smelt, J.H., and M. Leistra. 1974. Conversion of metam-sodium to methyl isothiocyanate and basic data on behavior in soil. Pestic. Sci. 5:401-407.
45. Smelt, J.H., W. Teunissen, S.J.H. Crum, and M. Leistra. 1989a. Accelerated transformation of 1,3-dichloropropene in loamy soils. Neth. J. Agric. Sci. 37:173-183.
46. Sparks, S.E., G.B. Quistad, and J.E. Casida. 1997. Chloropicrin: Reactions with biological thiols and metabolism in mice. Chem. Res. Toxicol. 10:1001-1007.
47. Toyota, K., K. Ritz, S. Kuninaga, and M. Kimura. 1999. Impact of fumigation with metam sodium upon soil microbial community structure in two Japanese soils. Soil Sci. Plant Nutr. 45:207-223.
48. Trout, T. 2001. California regulatory impacts on adoption of methyl bromide alternative fumigants. Methyl Bromide Altern. 7(3):4-7.
49. Turner, N.J., and M.E. Corden. 1963. Decomposition of sodium-N-methyldithiocarbamate in soil. Phytophathol. 53:1388-1394.
50. van der Pas, L.J.T., and M. Leistra. 1987. Movement and transformation of 1,3-dichloropropene in the soil of flower-bulb fields. Arch. Environ. Contam. Toxicol. 16:417-422.
51. van der Waarde, J.J., R. Kok, and D.B. Janssen. 1993. Degradation of 2-chloroallyalcohol by Pseudomonas sp. Appl. Environ. Micro-biol. 59:528-535.
52. van Dijk, H. 1980. Dissipation rates in soil of 1,2-dichloroporpane and 1,3- and 2,3-dichloropropenes. Pestic. Sci. 11:625-632.
53. van Hylckama Vlieg, J.E.T., and D.B. Janssen. 1992. Bacterial degradation of 3-chloroacrylic acid and the characterization of cis- and trans-specific dehalogenases. Biodegradation 2:139-150.
54. Verhagen, C., G. Lebbink, and J. Bloem. 1996. Enhanced biodegrada-tion of the nematicides 1,3-dichloropropene and methyl isothiocya-nate in a variety of soils. Soil Biol. Biochem. 28:1753-1756.
55. Verhagen C., E. Smit, D.B. Janssen and J.D. van Elsas. 1995. Bacterial dichloropropene degradation in soil: Screening of soils and involvement of plasmids carrying the dhlA gene. Soil Biol. Biochem. 27: 1547-1557.
56. Wang, D., S.R. Yates, F.F. Ernst, J.A. Knuteson, and G.E. Brown, Jr. 2001. Volatilization of 1,3-dichloropropene under different application methods. Water Air Soil Pollut. 127:109-123.
57. Warton, B., J.N. Matthiessen, and M.M. Roper. 2001. The soil organisms responsible for the enhanced degradation of metham sodium. Biol. Fertil. Soils 34:264-269.
58. Warton, B., J.N. Matthiessen, and M.A. Shackleton. 2002. Cross-degradation-Enhanced biodegradation of isothiocyanates in soils previously treated with metham sodium. Topics 5-6, Vol. 2. p. 40. In IUPAC International Congress on the Chemistry of Crop Protection, 10th, Basel, Switzerland. August 4-9. C.H.I.P.S., Weimar, TX.
59. Wilhelm, S.N., K. Shepler, L.J. Lawrence, and H. Lee. 1996. Environmental fate of chloropicrin. p. 79-93. In J.N. Seiber et al. (ed.) Fumigants: Environmental fate, exposure, and analysis. ACS Symp. Ser. 652. American Chemical Society, Washington, DC.
60. Yagi, K.J., J. Williams, N.Y. Wang, and R.J. Cicerone. 1993. Agricultural soil fumigation as a source of atmospheric methyl bromide. Proc. Natl. Acad. Sci. USA 90:8420-8423.
61. Yagi, K.J., J. Williams, N.Y. Wang, and R.J. Cicerone. 1995. Atmospheric methyl bromide (CH3Br) from agricultural soil fumigations. Science 267:1979-1981.
62. Yates, S.R., D. Wang, F.F. Ernst, and J. Gan. 1997. Methyl bromide emissions from agricultural fields: Bare-soil deep injection. Environ. Sci. Technol. 31:1136-1143.