Investigation of the Heterogeneously Catalyzed Hydrolysis of Organophosphorus Pesticides

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 1, 1998, Pages 325-334

  Dannenberg, Andrea ^a   Pehkonen, Simo O ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

Hydrolysis; Organophosphorus; Oxides; Pesticides; Products

Indexed keywords

EID: 0001138523     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970368o     Document Type: Article

References (37)

1. Baldwin, D. S.; Beattie, J. K.; Coleman, L. M.; Jones, D. R. Phosphate Ester Hydrolysis Facilitated by Mineral Phases. Environ. Sci. Technol. 1995, 29, 1706-1709.
2. Brown, M. A.; Petreas, M. X.; Okamoto, H. S.; Mischke, T. M.; Stephens, R. D. Monitoring of Malathion and Its Impurities and Environmental Transformation Products on Surfaces and in Air Following an Aerial Application. Environ. Sci. Technol. 1993, 27, 388-397.
3. Carey, F. A.; Sundberg, F. A. Advanced Organic Chemistry, 2nd ed.; Plenum Press: New York, 1984; p 176.
4. Carter, D. L.; Mortland, M. M.; Kemper, W. D. Specific Surface. In Methods of Soil Analysis, Part I: Physical and Mineralogical Methods, 2nd ed.; Klute, A., Ed.; American Society of Agronomy, Soil Science Society of America: Madison, WI, 1986; pp 413-423.
5. Exner, O. On the Enthalpy-Entropy Relationship. Collect. Czech. Commun. 1964, 29, 1094.
6. Faust, S. D.; Gomaa, H. M. Chemical Hydrolysis of Some Organic Phosphorus and Carbamate Pesticides in Aquatic Environments. Environ. Lett. 1972, 3, 171-201.
7. Good, W.; Ingham, D. B.; Stone, J. On Establishing the Validity of Enthalpy-Entropy Relationships. Tetrahedron 1975, 31, 257.
8. Grassetti, D. R.; Murray, J. F., Jr. Determination of Sulfhydryl Groups with 2,2′-or 4,4′-dithiodipyridine. Arch. Biochem. Biophys. 1987, 119, 41-49.
9. Hendry, P.; Sargeson, A. M. Base Hydrolysis of Coordinated Trimethyl Phosphate. Aust. J. Chem. 1986, 39, 1177-1186.
10. Hendry, P.; Sargeson, A. M. Metal Ion Promoted Reactions of Phosphate Derivatives. In Progress in Inorganic Chemistry: Bioinorganic Chemistry; Lippard, S. J., Ed.; WileyInterscience: New York, 1990; Vol. 38, pp 201-258.
11. Howard, P. H. Handbook of Environmental Fate and Exposure Data for Organic Chemicals; Lewis Publishers: Chelsea, MI, 1991; pp 209, 309.
12. Humphrey, R. E.; Ward, M. H.; Hinze, W. Spectrophotometric Determination of Sulfite with 4,4′-dithiodipyridine and 5,5′-dithiobis-(2-nitrobenzoic acid). Anal. Chem. 1970, 42, 698-702.
13. James, R. O.; Parks, G. A. Characterization of Aqueous Colloids by Their Electrical Double-Layer and Intrinsic Suface Chemical Properties in Surface and Colloid Science; Matijevic, E., Ed.; Plenum: New York, 1982; p 185.
14. Jones, D.; Lindoy, L.; Sargeson, A. Enhanced Base Hydrolysis of Coordinated Phosphate Esters: The Reactivity of an Unusual Co(III) Amine Dimer. J. Am. Chem. Soc. 1984. 106, 7807-7819.
15. Ketelaar, J. A. A.; Gersmann, H. R.; Beck, M. M. Metal-Catalyzed Hydrolysis of Thiophosphoric Esters. Nature 1956, 177, 392-393.
16. Khan, S. U. Pesticides in the Soil Environment; Elsevier: Amsterdam, 1980; p 240.
17. Lacorte, S.; Barceló, D. Rapid Degradation of Fenitrothion in Estuarine Waters. Environ. Sci. Technol. 1994, 28, 1159-1163.
18. Lacorte, S.; Molina, C.; Barceló, D. Screening of Organophosphorus Pesticides in Environmental Matrices by Various Gas Chromatographic Techniques. Anal. Chim. Acta 1993, 281, 71-84.
19. Lacorte, S.; Lartiges, S. B.; Garrigues, P.; Barcelo, D. Degradation of Organophosphorus Pesticides and Their Transformation Products in Estuarine Waters. Environ. Sci. Technol. 1995, 29, 431-438.
20. Lartiges, S. B.; Garrigues, P. P. Degradation Kinetics of Organophosphorus and Organonitrogen Pesticides in Different Waters under Various Environmental Conditions. Environ. Sci. Technol. 1995, 29, 1246-1254.
21. Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions; Wiley: New York, 1963.
22. Lores, E. M.; Moore, C. J.; Moody, P.; Clark, J.; Forester, J.; Knight, J. Temephos Residues in Stagnant Ponds after Mosquito Larvicide Applications by Helicopter. Bull. Environ. Contam. Toxicol. 1985, 35, 308-313.
23. Mabey, W.; Mill, T. Critical Review of Hydrolysis of Organic Compounds in Water under Environmental Conditions. J. Phys. Ref. Data 1978, 7, 383.
24. Mortland, M. M.; Raman, K. V. Catalytic Hydrolysis of Some Organic Phosphate Pesticides by Copper(II). J. Agric. Food Chem. 1967, 15, 163-167.
25. Muhlmann, R.; Schrader, A. Hydrolyse der Insektiziden Phophoräurester. Z. Naturforsch. 1957, 12B, 196-208.
26. Pehkonen, S. O.; Siefert, R. L.; Erel, Y.; Webb, S.; Hoffmann, M. R. Photoreduction of Iron Oxyhydroxides in the Presence of Important Atmospheric Organic Compounds. Environ. Sci. Technol. 1993, 27, 2056-2062.
27. Premdas, P. D.; Kendrick, B. A New System to Bioassay Pesticides in the Surface Microlayer using Floating Propagules of an Aero-Aquatic Hyphomycetous Fungus Pseudoaegerita Matsushimae. Environ. Monit. Assess. 1992, 22, 169-180.
28. Schimmel, S. C.; Garnas, R. L.; Patrick, J. M., Jr.; Moore, J. C. Acute Toxicity, Bioconcen-tration, and Persistence of AC 222, 705, Benthiocarb, Chlorpyrifos, Fenvakrate, Methyl Para-thion, and Permethrin in the Estuarine Environment. J. Agric. Food Chem. 1983, 31, 104-113.
29. Schwarzenbach, R. P.; Giger, W.; Schaffner, C.; Wanner, O. Groundwater Contamination by Volatile Halogenated Alkanes: Abiotic Formation of Volatile Sulfur Compounds under Anerobic Conditions. Environ. Sci. Technol. 1985, 19, 322-327.
30. Schwertmann, U.; Cornell, R. M. Iron Oxides in the Laboratory, 1st ed.; VCH: Weinheim, Germany, 1991; pp 14-18.
31. Sulzberger, B.; Laubscher, H. A Comparative Study of the Kinetics of the Photochemical Reductive Dissolution of Various Iron(III) Hydr(oxides). Proceedings from the 188th National Meeting of the American Chemical Society, San Francisco, CA; American Chemical Society; Washington, DC, 1992; p 203, ENVR-6.
32. Tetas, M.; Lowenstein, L. The Effect of Bivalent Metal Ions on the Hydrolysis of Adenosine Di- and Triphosphate. Biochemistry 1963, 2, 350-357.
33. Torrents, A.; Stone, A. T. Oxide Surface-Catalyzed Hydrolysis of Carboxylate Esters and Phosphorothioate Esters. Soil Sci. Soc. Am. J. 1994, 58, 738-745.
34. Von Westernhagen, H.; Landolt, M.; Kocan, R.; Fuerstenberg, G.; Janssen, D.; Kremling, K. Toxicity of Sea-Surface Microlayer; Effects on Herring and Turbot Embryos. Mar. Environ. Res. 1987, 23, 273-290.
35. Wang, T. C.; Lenahan, R. A.; Tucker, J. W., Jr. Deposition and Persistence of Aerially-Applied Fenthion in a Florida Estuary. Bull. Environ. Contam. Toxicol. 1987, 38, 226-231.
36. 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.
37. Weber, K. Degradation of Parathion in Seawater. Water Res. 1976, 10, 237-241.