Nucleophilic substitution of phosphorothionate ester pesticides with bisulfide (HS-) and polysulfides (Sn2-)

Environmental Science and Technology

Volumn 40, Issue 17, 2006, Pages 5428-5434

  Wu, Tong ^a   Gan, Qiu ^a   Jans, Urs ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ABIOTIC DEGRADATION; NUCLEOPHILIC SUBSTITUTIONS; ORGANOPHOSPHORUS INSECTICIDES;

CONCENTRATION (PROCESS); ESTERS; PH EFFECTS; POLYSULFIDES; SOLUTIONS; SUBSTITUTION REACTIONS;

PESTICIDES;

CHLORPYRIFOS; FENCLOFOS; ORGANOPHOSPHORUS COMPOUND; PARATHION; PESTICIDE; PHOSPHOROTHIOIC ACID DERIVATIVE; SULFIDE;

CONCENTRATION (PROCESS); ESTERS; PESTICIDES; PH EFFECTS; POLYSULFIDES; SOLUTIONS; SUBSTITUTION REACTIONS;

ANOXIC CONDITIONS; AQUEOUS SOLUTION; CARBON; COMPARATIVE STUDY; DEGRADATION; ESTER; EXPERIMENTAL STUDY; HALF LIFE; HYDROLYSIS; INSECTICIDE; MICROBIAL ACTIVITY; ORGANIC COMPOUND; ORGANOPHOSPHATE; PESTICIDE; POREWATER; SALTMARSH; SEDIMENT; SULFIDE; SULFUR; TEMPERATURE EFFECT;

ANOXIA; AQUEOUS SOLUTION; ARTICLE; ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL IMPACT; HYDROLYSIS; INSECTICIDAL ACTIVITY; MICROBIAL DEGRADATION; PESTICIDE SPRAYING; REACTION ANALYSIS; SEDIMENT; WATER ANALYSIS;

CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; KINETICS; ORGANOTHIOPHOSPHORUS COMPOUNDS; PESTICIDES; SULFIDES;

EID: 33748529971     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es060711i     Document Type: Article

References (44)

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. 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: Washington, DC, http://www.epa.gov/oppbead1/pestsales/01pestsales/ market_estimates2001.pdf; (accessed Jan. 14, 2005).
4. Cavalier, T. C.; Lavy, T. L.; Mattice, J. D. Persistence of selected pesticides in groundwater samples. Groundwater 1991, 29, 225-231.
5. Cerejeira, M. J.; Viana, P.; Batista, S.; Pereira, T.; Silva, E.; Valério, M. J.; Silva, A.; Ferreira, M.; Silva-Fernandes, A. M., Pesticides in Portuguese surface and ground waters. Water Res. 2003, 37, 1055-1063.
6. 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 [online]: http://www.cdpr.ca.gov/ docs/rifa/rep1129.pdf; (accessed Jan. 30, 2005)
7. 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.
8. Kolpin, D. W.; Thurman, E. M.; Linhart, S. M. The environmental occurrence of herbicides: The importance of degradates in groundwater. Arch. Environ. Contam. Toxicol. 1998, 35, 385-390.
9. Lee, C. C.; Green, R. E.; Apt, W. J. Transformation and adsorption of fenamiphos, fenamiphos sulfoxide and fenamiphos sulfone in molokai soil and simulated movement with irrigation. J. Contam. Hydrol. 1986, 1, 211-225.
10. Ou, L. T.; Rao, P. S. C. Degradation and metabolism of oxamyl and phenamiphos in soils. J. Environ. Sci. Health 1986, B21, 25-33.
11. Singh, R. P.; Brindle, I. D.; Hall, C. D.; Chiba, M. Kinetic study of the decomposition of methyl [1-(butylcarbamoyl)-1H-benimidazol-2-yl] carbamate (benomyl) to methyl-1H-benzimidazol-2-yl carbamate (MBC). J. Agric. Food Chem. 1990, 38, 1758-1762.
12. Hallberg, G. R. Pesticides pollution of groundwater in the humid United States. Agric. Ecosyst. Environ. 1989, 26, 299-367.
13. 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.
14. Faust, S. D.; Gomaa, H. M. Chemical hydrolysis of some organic phosphorus and carbamate pesticides in aquatic environments. Environ. Lett. 1972, 3, 171-201.
15. Holden, A. J.; Chen, L.; Shaw, I. C. Thermal stability of organophosphorus pesticide triazophos and its relevance in the assessment of risk to the consumer of triazophos residues in food. J. Agric. Food Chem. 2001, 49, 103-106.
16. Hong, F.; Pehkonen, S. Hydrolysis of phorate using simulated environmental conditions: rates, mechanisms and product analysis. J. Agric. Food Chem. 1998, 46, 1192-1199.
17. Liu, B.; McConnell, L. L.; Torrents, A. Hydrolysis of chlorpyrifos in natural waters of the Chesapeake Bay. Chemosphere 2001, 44, 1315-1323.
18. Meikle, R. W.; Youngson, C. R. The hydrolysis rate of chlorpyrifos, O,O-diethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioate, and its dimethyl analog, chlorpyrifos-methyl, in dilute aqueous solution. Arch. Environ. Contam. Toxicol. 1978, 7, 13-22.
19. 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.
20. 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.
21. Kamiya, M.; Kameyama, K. Effects of selected metal ions on photodegradation of organophosphorus pesticides sensitized by humic acids. Chemosphere 2001, 45, 231-235.
22. Noblet, J. A.; Smith, L. A.; Suffet, I. H. M. Influence of natural dissolved organic matter, temperature, and mixing on the abiotic hydrolysis of triazine and organophosphate pesticides. J. Agric. Food Chem. 1996, 44, 3685-3693.
23. 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.
24. Haag, W.; Mill, T. Some reactions of naturally occurring nucleophiles with haloalkanes in water. Environ. Toxicol. Chem. 1988, 7, 917-924.
25. 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.
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. Miller, P. L.; Vasudevan, D.; Gschwend, P. M.; Roberts, A. L. Transformation of hexachloroethane in a sulfidic natural water. Environ. Sci. Technol. 1998, 32, 1269-1275.
28. Edwards, J.; Pearson, R. G. The factors determining nucleophilic reactivity. J. Am. Chem. Soc. 1962, 84, 16-24.
29. Edwards, J. O. Correlation of relative rates and equilibria with a double basicity scale. J. Am. Chem. Soc. 1954, 76, 1540-1547.
30. 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.; American Chemical Society: Washington, DC, 1989; pp 101-138.
31. 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.
32. Wu, T.; Jans, U. Nucleophilic substitution reactions of chlorpyrifos-methyl with sulfur species. Environ. Sci. Technol. 2006, 40, 784-790.
33. Jans, U.; Miah, M. H. Reaction of chlorpyrifos-methyl in aqueous hydrogen sulfide/bisulfide solutions. J. Agric. Food Chem. 2003, 51, 1956-1960.
34. Skoog, D. A.; West, D. M.; Holler, F. J.; Crouch, S. R. Analytical Chemistry: An Introduction; Saunders College Publishing: Fort Worth, TX, 1999.
35. Millero, F. J. The thermodynamics and kinetics of the hydrogen sulfide system in natural waters. Mar. Chem. 1986, 18, 121-147.
36. Giggenbach, W. Optical spectra of highly alkaline sulfide solutions and the second dissociation constant of hydrogen sulfide. Inorg. Chem. 1971, 10, 1333-1338.
37. Meyer, B.; Ward, K.; Koshlap, K.; Peter, L. Second dissociation constant of hydrogen sulfide. Inorg. Chem. 1983, 22, 2345-2346.
38. Giggenbach, W. Optical spectra and equilibrium distribution of polysulfide ions in aqueous solution at 20°C. Inorg. Chem. 1972, 11, 1201-1207.
39. Pearson, R. G. Hard and soft acids and bases. J. Am. Chem. Soc. 1963, 85, 3533-3539.
40. Meyer, B.; Peter, L.; Spitzer, K. Trends in the charge distribution in sulfanes, sulfanesulfonic acids, sulfanedisulfonic acids, and sulfurous acid. Inorg. Chem. 1977, 16, 27-33.
41. Pickerling, T. L.; Tobolsky, A. V. Inorganic and organic polysulfides. In Sulfur in Organic and Inorganic Chemistry; Senning, A., Ed.; Marcel Dekker: New York, 1972; pp 19-38.
42. Luther, G. W., III The frontier-molecular orbital theory approach in geochemical processes. In Aquatic Chemical Kinetics: Reaction Rates of Processes in Natural Waters; Stumm, W., Ed.; John Wiley: New York, 1990; pp 173-198.
43. 2-). Environ. Sci. Technol. 2002, 36, 2008-2018.
44. Wu, T. Role of reduced sulfur species in promoting the transformation of insecticide in the environment. Ph.D. Dissertation, The City University of New York, New York, 2006.