Nucleophilic reactions of phorate and terbufos with reduced sulfur species under anoxic conditions

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 9, 2007, Pages 3546-3554

  Gan, Qiu ^a,b   Jans, Urs ^a,b  

^a CITY COLLEGE OF NEW YORK   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Bisulfide; Nucleophilic substitution; Phorate; Polysulfide; Terbufos; Thiophenolate; Thiosulfate

Indexed keywords

INSECTICIDE; OXYGEN; PHORATE; PHOSPHOROTHIOIC ACID DERIVATIVE; SULFUR DERIVATIVE; TERBUFOS;

ARTICLE; CHEMISTRY; HYDROLYSIS; KINETICS; OXIDATION REDUCTION REACTION; SOLUTION AND SOLUBILITY;

HYDROLYSIS; INSECTICIDES; KINETICS; ORGANOTHIOPHOSPHORUS COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; PHORATE; SOLUTIONS; SULFUR COMPOUNDS;

EID: 34249329616     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf063296m     Document Type: Article

References (46)

1. Coats, J. R. What happens to degradable pesticides? CHEMTECH 1993, 23, 25-29.
2. Khan, S. U. Pesticides in the Soil Environment; Elsevier: Amsterdam, The Netherlands, 1980.
3. Kim, D.; Walters, J.; Sava, R. Preliminary background results of organophosphate analysis and acute toxicity testing of surface water monitored for the red imported fire ant project in Orange County, March and April, 1999; California Department of Pesticides Regulation; available at http://www.cdpr.ca.gov/docs/rifa/rep1129.pdf, accessed Jan 30, 2006.
4. Kolpin, D. W.; Barbash, J. E.; Gilliom, R. J. Occurrence of pesticides in shallow groundwater of the United States: initial results from the national water-quality assessment program. Environ. Sci. Technol. 1998, 32, 558-566.
5. Kolpin, D. W.; Furlong, E. T.; Meyer, M. T.; Thurman, E. M.; Zaugg, S. D.; Barber, L. B.; Buxton, H. T. Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: a national reconnaissance. Environ. Sci. Technol. 2002, 36, 1202-1211.
6. Hallberg, G. R. Pesticides pollution of groundwater in the humid United States. Agric. Ecosyst. Environ. 1989, 26, 299-367.
7. MacCrehan, W.; Shea, D. Temporal relationship of inorganic sulfur compounds in anoxic Chesapeake Bay sediment porewater. In Geochemical Transformations of Sedimentary Sulfur; Vairavamurthy, M. A., Schoonen, M. A. A., Ed.; American Chemical Society: Washington, DC, 1995.
8. Roberts, A. L.; Gschwend, P. M. Interaction of abiotic and microbial processes in hexachlorediane transformation in groundwater. J. Contam. Hydrol. 1994, 16, 157-174.
9. Weber, E. J.; Wolfe, N. L. Kinetic studies of the reduction of aromatic azo compounds in anaerobic sediment/water systems. Environ. Toxicol. Chem. 1987, 6, 911-919.
10. Howarth, R. W.; Giblin, A. E.; Gale, J.; Petersen, B. J.; Luther, G. W., III. Reduced sulfur compounds in the pore waters of a New England salt marsh. Environ. Biogeochem. Ecol. Bull. 1983, 35, 135-152.
11. Luther, G. W.; Giblin, A. E.; Varsolona, R. Polarographic analysis of sulfur species in marine porewaters. Limnol Oceanogr. 1985, 20, 727-736.
12. Boulegue, J.; Lord, C. J., III; Church, T. M. Sulfur speciation and associated trace metal (Fe, Cu) in the pore waters of Great Salt Marsh, Delaware. Geochim. Cosmochim. Acta 1982, 46, 453-464.
13. Lippa, K. A.; Demel, S.; Lau, I. H.; Roberts, A. L. Kinetics and mechanism of the nucleophilic displacement reaction of chloroacetanilide herbicides: investigation of α-substituent effects. J. Agric. Food Chem. 2004, 52, 3010-3021.
14. 2-). Environ. Sci. Technol. 2002, 36, 2008-2018.
15. Gan, Q.; Singh, R. M.; Wu, T.; Jans, U. Kinetics and mechanism of degradation of dichlorvos in aqueous solutions containing reduced sulfur species. Environ. Sci. Technol. 2006, 40, 5717-5723.
16. Jans, U.; Miah, M. H. Reaction of chlorpyrifos-memyl in aqueous hydrogen sulfide/bisulfide solutions. J. Agric. Food Chem. 2003, 51, 1956-1960.
17. Gan, Q.; Singh, R. M.; Jans, U. Degradation of naled and dichlorvos promoted by reduced sulfur species in well-defined anoxic aqueous solutions. Environ. Sci. Technol. 2006, 40, 778-783.
18. 2-). Environ. Sci. Technol. 2006, 40, 5428-5434.
19. PIP-Phorate. EXOTOXNET Profile for Phorate; Extension Toxicology Network, Pesticide Information Project, Cornell University, Ithaca, NY, 1993; available at http://extoxnet.orst.edu/pips/phorate.htm, accessed Dec 15, 2005.
20. PIP-Terbufos. EXOTOXNET Profile for Terbufos; Extension Toxicology Network, Pesticide Information Project, Cornell University, Imaca, NY, 1994; available at http://extoxnet.orst.edu/ pips/terbufos.htm, accessed Dec 15, 2005.
21. U.S. Environmental Protection Agency. EPA-738-F-00-014. R.E.D. Facts. Phorate; 2001; available at http://www.epa.gov/oppsrrd1/REDs/factsheets/ phorate_fs.htm, accessed Nov 11, 2005.
22. U.S. Environmental Protection Agency. EPA-738-F-01-015 R.E.D. Facts. Terbufos; 2001; available at http://www.epa.gov/REDs/factsheets/ terbufos_ired_fs.htm, accessed Nov 11, 2005.
23. Chapman, R. A.; Tu, C. M.; Harris, C. R. Biochemical and chemical transformations of phorate, phorate sulfoxide, and phorate sulfone in natural and sterile mineral and organic soil. J. Econ. Entomol. 1982, 75, 112-117.
24. Szeto, S. Y.; Price, P. M.; Mackenzie, J. R.; Vernon, R. S. Persistence and uptake of phorate in mineral and organic soils. J. Agric. Food Chem. 1990, 38, 501-504.
25. Chapman, R. A.; Harris, C. R. Insecticidal activity and persistence of terbufos, terbufos sulfoxide and terbufos sulfone in soil. J. Econ. Entomol. 1980, 73, 536-543.
26. Szeto, S. Y.; Brown, M. J.; Mackenzie, J. R.; Vernon, R. S. Degradation of terbufos in the soil and its translocation into cole crops. J. Agric. Food Chem. 1986, 34, 876-879.
27. Hong, F.; Pehkonen, S. Hydrolysis of phorate using simulated environmental condition; rates, mechanism, and product analysis. J. Agric. Food Chem. 1998, 46, 1192-1199.
28. 31P NMR and GC-MS. J. Agric. Food Chem. 2000, 48, 3013-3017.
29. Hong, F.; Win, K. Y.; Pehkonen, S. O. Hydrolysis of terbufos using simulated environmental condition; rates, mechanism, and product analysis. J. Agric. Food Chem. 2001, 49, 5866-5873.
30. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry; Wiley-Interscience: New York, 2003.
31. Gan, Q.; Jans, U. Reaction of thiometon and disulfoton with reduced sulfur species in natural simulated environments. J. Agric. Food Chem. 2006, 54, 7753-7760.
32. Damste, J. S.; Rijpstra, W. I. C.; De Leeuw, J. W.; Schenck, P. A. The occurrence and identification of series of organic sulfur compounds in oils and sediment extracts: II. Their presence in samples from hypersaline and non-hypersaline palaeoenvironments and possible application as source, palaeoenvironmental and maturity indicators. Geochim. Cosmochim. Acta 1989, 53, 1323-1341.
33. Adam, P.; Philippe, E.; Albrecht, P. Photochemical sulfurization of sedimentary organic matter: a widespread process occurring at early digenesis in natural environments? Geochim. Cosmochim. Acta 1998, 62, 265-271.
34. Millero, F. J. The thermodynamics and kinetics of hydrogen sulfide systems in natural waters. Mar. Chem. 1986, 18, 121-147.
35. Giggenbach, W. Optical spectra and equilibrium distribution of polysulfide ions in aqueous solutions at 20°C. Inorg. Chem. 1972, 11, 1201-1207.
36. Schwarzenbach, G.; Fischer, A. Die Acidität der Sulfane und die Zusammensetzung wässeriger Polysulfidelösungen. Helv. Chim. Acta 1960, 43, 1365-1388.
37. Yamada, H.; Somiya, I. The determination of carbonyl compounds in ozonated water by PFBOA method. Ozone: Sci. Eng. 1989, 11, 127-141.
38. Glaze, W. H.; Koga, M.; Cancilla, D. Ozonation byproducts. 2. Improvement of an aqueous-phase derivatization method for the detection of formaldehyde and other carbonyl compounds formed by the ozonation of drinking water. Environ. Sci. Technol. 1989, 23, 838-847.
39. Sclimenti, M. J.; Krasner, S. W.; Glaze, W. H.; Weinberg, H. S. Ozone disinfection by-products: optimization of PFBHA derivatization method for analysis of aldehydes. In Proceedings of the American Water Works Association Water Quality Technology Conference; American Water Works Association: Denver, CO, 1990.
40. Swain, C. G.; Scott, G. B. Quantitative correlation of relative rates. Comparison of hydroxide ion with other nucleophilic reagents toward alkyl halides, esters, epoxides and acyl halides. J. Am. Chem. Soc. 1953, 75, 141-147.
41. Haag, W. R.; Mill, T. Some reactions of naturally occurring nucleophiles with haloalkanes in water. Environ. Toxicol. Chem. 1988, 7, 917-924.
42. Hine, J. Physical Organic Chemistry, 2nd ed.; McGraw-Hill: New York, 1962.
43. Wu, T.; Jans, U. Nucleophilic substitution reaction of chlorpyrifos-methyl with sulfur species. Environ. Sci. Technol. 2006, 42, 784-790.
44. Pross, A. Theoretical and Physical Principles of Organic Reactivity; Wiley: New York, 1995.
45. Kohn, G. K., Baker, D. R., Eds. The agrochemical industry. In Riegel's Handbook of Industrial Chemistry; Kent, J. A., Ed.; Van Nostrand Reinhold: New York, 1992.
46. Hedderich, R.; Klimmek, O.; Kroger, A.; Dirmeier, R.; Keller, M.; Stetter, K. O. Anaerobic respiration with elemental sulfur and with disulfides. FEMS Microbiol. Rev. 1998, 22, 353-381.