Nucleophilic substitution reactions of chlorpyrifos-methyl with sulfur species

Environmental Science and Technology

Volumn 40, Issue 3, 2006, Pages 784-790

  Wu, Tong ^a   Jans, Urs ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHLORINE COMPOUNDS; COASTAL ZONES; DEGRADATION; GRAIN (AGRICULTURAL PRODUCT); HYDROLYSIS; INSECT CONTROL; INSECTICIDES; PH EFFECTS; RATE CONSTANTS; REACTION KINETICS; SOLUTIONS; SULFIDE MINERALS; SULFUR COMPOUNDS;

CHLORPYRIFOS-METHYL; METHOXY GROUP; THIOPHENOLATE; TRICHLOROPYRIDINOL;

SUBSTITUTION REACTIONS;

CARBON; CHLORPYRIFOS METHYL; HYDROGEN BISULFIDE; HYDROGEN SULFIDE; NORCHLORPYRIFOS METHYL; POLYSULFIDE; PYRIDINOL; SULFUR DERIVATIVE; THIOPHENOL DERIVATIVE; THIOPHENOLATE; THIOSULFATE; TRICHLOROPYRIDINOL; UNCLASSIFIED DRUG;

CARBON; CHLORINE COMPOUNDS; COASTAL ZONES; DEGRADATION; GRAIN (AGRICULTURAL PRODUCT); HYDROLYSIS; INSECT CONTROL; INSECTICIDES; PH EFFECTS; RATE CONSTANTS; REACTION KINETICS; SOLUTIONS; SUBSTITUTION REACTIONS; SULFIDE MINERALS; SULFUR COMPOUNDS;

CHEMICAL CONTROL;

AQUEOUS SOLUTION; ARTICLE; CALCULATION; CHEMICAL SINK; CHEMICAL STRUCTURE; COASTAL WATERS; HALF LIFE TIME; HYDROLYSIS; MARINE ENVIRONMENT; NUCLEOPHILIC SUBSTITUTION REACTION; PREDICTION AND FORECASTING; REACTION ANALYSIS; REACTION TIME; SALT MARSH; SUBSTITUTION REACTION;

CHLORPYRIFOS; GEOLOGIC SEDIMENTS; HALF-LIFE; HYDROGEN-ION CONCENTRATION; INSECTICIDES; KINETICS; SULFUR; WATER POLLUTANTS, CHEMICAL;

AVENA; HEXAPODA; HORDEUM VULGARE SUBSP. VULGARE; INSECTA; TRITICUM AESTIVUM;

EID: 32344451797     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es051468a     Document Type: Article

References (42)

1. Donaldson, D.; Kiely, T.; Grube, A. Pesticides Industry Sales and Usage, 2000 and 2001 market estimates; EPA 733-R-04-001. EPA Office of Pesticide Programs: http://www.epa.gov/oppbead1/pestsales/01pestsales/ market·estimates2001.pdf (accessed Jan. 14, 2005).
2. Hallberg, G. R. Pesticides pollution of groundwater in the humid United States. Agric. Ecosyst. Environ. 1989, 26, 299-367.
3. 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.
4. Khan, S. U. Pesticides in the Soil Environment, Elsevier: Amsterdam, The Netherlands, 1980.
5. EPA. Office of pesticide programs, overview on the chlorpyrifosmethyl revised risk; 〈http://www.epa.gov/oppsrrd1/op/chlorpyrifos-methyl. htm〉, http://www.epa.gov/pesticide/op/chlorpyrifos-methyl/overview〉 (accessed April 19, 2004).
6. Smolen, J. M.; Stone, A. T. Divalent metal ion-catalyzed hydrolysis of phosphorothionate ester pesticides and their corresponding oxonates. Environ. Sci. Technol. 1997, 31, 1664-1673.
7. Mabey, W.; Mill, T. Critical review of hydrolysis of organic compounds in water under environmental conditions. J. Phys. Chem. Ref. Data 1978, 7, 383-415.
8. Pehkonen, S.O.; Zhang, Q. The degradation of organophophorus pesticides in natural waters: a critical review. Crit. Rev. Environ. Sci. Technol. 2002, 32, 17-72.
9. Weber, K. Degradation of parathion in seawater. Water Res. 1976, 10, 237-241.
10. Wolfe, N. L.; Zepp, R. G.; Gordon, J. A.; Baughman, G. L.; Cline, D. M. Kinetics of chemical degradation of malathion in water. Environ. Sci. Technol. 1977, 11, 88-93.
11. Wan, H. B.; Wong, M. K.; Mok, C. Y. Mercury(II) ion-promoted hydrolysis of some organophosphorus pesticides. Pestic. Chem. 1994, 42, 93-99.
12. Mortland, M. M.; Raman, K. V. Catalytic hydrolysis of some organic phosphate pesticides by copper(II). J. Agric. Food Chem. 1967, 15, 163-167.
13. Dannenberg, A.; Pehkonen, S. O. Investigation of the heterogeneously catalyzed hydrolysis of organophosphorus pesticides. J. Agric. Food Chem. 1998, 46, 325-334.
14. Racke, K. D.; Steele, K. P.; Yoder, R. N.; Dick, W. A.; Avidov, E. Factors affecting the hydrolytic degradation of chlorpyrifos in soil. J. Agric. Food Chem. 1996, 44, 1582-1592.
15. Wanner, O.; Egli, T.; Fleischmann, T.; Lanz, K.; Reichert, P.; Schwarzenbach, R. P. Behavior of the insecticides disulfoton and thiometon in the Rhine River: a chemodynamic study. Environ. Sci. Technol. 1989, 23, 1232-1242.
16. Landis, W. G. Distribution and nature of the aquatic organophosphorus acid anhydrases-enzymes for organophosphate detoxification. Rev. Aquat. Sci. 1991, 5, 267-285.
17. Bakke, J. E.; Price, C. E. Metabolism of O,O-dimethyl-O-(3,5,6-trichloro- 2-pyridyl)phosphorothionate in sheep and rats. J. Environ. Sci. Health 1976, B11, 9-22.
18. Howarth, R. W.; Teal, J. M. Sulfate reduction in a New England salt marsh. Limnol. Oceanogr. 1979, 24, 999-1013.
19. Trudinger, P. A.; Loughlin, R. E. Metabolism of simple sulfur compounds. In Comprehensive Biochemistry, Neuberger, A., Deenen, L. v., Eds.; Elsevier: New York, 1981; pp 165-256.
20. Gun, J.; Goifman, A.; Shkrob, I.; Kamyshny, A.; Ginzburg, B.; Hadas, O.; Dor, I.; Modestov, A. D.; Lev, O. Formation of polysulfides in an oxygen rich freshwater lake and their role in the production of volatile sulfur compounds in aquatic systems. Environ. Sci. Technol. 2000, 34, 4741-4746.
21. MacCrehan, W.; Shea, D. Temporal relationship of thiols to inorganic sulfur compounds in anoxic Chesapeake Bay sediment porewater. In Geochemical Transformations of Sedimentary Sulfur, Vairavamurthy, M. A., Schoonen, M. A. A., Eds.; ACS Symposium Series 612; American Chemical Society: Washington, DC, 1995; pp 294-310.
22. Barbash, J. E.; Reinhard, M. Reactivity of sulfur nucleophiles toward halogenated organic compounds in natural waters. In Biogenic Sulfur in the Environment; Saltzman, E. S., Cooper, W. J., Eds.; ACS: Washington, DC, 1989; pp 101-138.
23. Lippa, K. A.; Demel, S.; Lau, I. H.; Roberts, A. L. Kinetics and mechanism of the nucleophilic displacement reactions of chloroacetanilide herbicides: investigation of α-substituent effects. J. Agric. Food Chem. 2004, 52, 3010-3021.
24. 2-). Environ. Sci. Technol. 2002, 36, 2008-2018.
25. 2-). Environ. Sci. Technol. 2002, 36, 4065-4073.
26. Roberts, A. L.; Sanborn, P. N.; Gschwend, P. M. Nucleophilic substitution reactions of dihalomethanes with hydrogen sulfide species. Environ. Sci. Technol. 1992, 26, 2263-2274.
27. Edwards, J.; Pearson, R. G. The factors determining nucleophilic reactivity. J. Am. Chem. Soc. 1962, 84, 16-24.
28. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2nd ed.; John Wiley: Hoboken, NJ, 2003.
29. Hartley, D.; Kidd, H. The Agrochemicals Handbook, 2nd ed.; The Royal Society of Chemistry: Nottingham, England, 1987.
30. Eskenazi, B.; Bradman, A.; Castorina, R. Exposures of children to organophosphate pesticides and their potential adverse health effects. Environ. Health Perspect. 1999, 107, 409-419.
31. Pico, Y.; Rodriguez, R.; Manes, J. Capillary electrophoresis for the determination of pesticide residues. Trends Anal. Chem. 2003, 22, 133-151.
32. Cox, J. R.; Ramsay, O. B. Mechanisms of nucleophilic substitution in phosphate esters. Chem. Rev. 1964, 64, 317-352.
33. Faust, S. D.; Gomaa, H. M. Chemical hydrolysis of some organic phosphorus and carbamate pesticides in aquatic environments. Environ. Lett. 1972, 3, 171-201.
34. Jans, U.; Miah, M. H. Reaction of chlorpyrifos-methylin aqueous hydrogen sulfide/bisulfide solutions. J. Agric. Food Chem. 2003, 51, 1956-1960.
35. Perlinger, J.A.; Kalluri, V. M.; Venkatathy, R.; Angst, W. Addition of hydrogen sulfide to juglone. Environ. Sci. Technol. 2002, 36, 2663-2669.
36. Skoog, D. A.; West, D. M.; Holler, F. J.; Crouch, S. R. Analytical Chemistry: An Introduction; Saunders College Publishing: Fort Worth, TX, 1999.
37. Millero, F. J. The thermodynamics and kinetics of the hydrogen sulfide system in natural waters. Mar. Chem. 1986, 18, 121-147.
38. Giggenbach, W. Optical spectra and equilibrium distribution of polysulfide ions in aqueous solution at 20°. Inorg. Chem. 1972, 11, 1201-1207.
39. Kabachnik, M. I.; Mastrukova, T. A.; Shipov, A. E.; Melentyeva, T. A. The application of the hammett equation to the theory of tautomeric equilibrium': Thione-thiol equilibrium, acidity, and structure of phosphorus thio-acids. Tetrahedron 1960, 9, 10-28.
40. Swain, C. G.; Scott, C. 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. Boulegue, J.; Lord, C. J., III; Church, T. M. Sulfur speciation and associated trace metals (Fe, Cu) in the pore waters of Great Marsh, Delaware. Geochim. Cosmochim. Acta 1982, 46, 453-464.
42. Kohn, G.K., Baker, D. R., Eds. The agrochemical industry. Riegel's Handbook of Industrial Chemistry, Van Nostrand Reinhold: New York, 1992.