NMR investigation of the behavior of an organothiophosphate pesticide, chlorpyrifos, sorted on soil components

Environmental Science and Technology

Volumn 40, Issue 3, 2006, Pages 791-796

  Seger, Mark R ^a   Maciel, Gary E ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ADSORPTION; DECOMPOSITION; HYDROLYSIS; ISOMERIZATION; KAOLIN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SOILS;

CROSS POLARIZATION; HUMIC ACID; MAGIC-ANGLE SPINNING; MONTMORILLONITE;

PESTICIDES;

ACETONE; ALUMINUM; CALCIUM ION; CARBON 13; CHLORPYRIFOS; DIMETHYL SULFOXIDE; HUMIC ACID; KAOLIN; MONTMORILLONITE; ORGANOPHOSPHATE PESTICIDE; PHOSPHOROTHIOIC ACID DERIVATIVE;

ACETONE; ADSORPTION; DECOMPOSITION; HYDROLYSIS; ISOMERIZATION; KAOLIN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PESTICIDES; SOILS;

NUCLEAR MAGNETIC RESONANCE; ORGANOPHOSPHATE; PESTICIDE; SOIL CHEMISTRY;

ADSORPTION; ALUMINUM NUCLEAR MAGNETIC RESONANCE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CLAY; DECOMPOSITION; DEVICE; HYDRATION; HYDROLYSIS; INTERMETHOD COMPARISON; ISOMERIZATION; MINERALIZATION; MOTION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SIGNAL DETECTION; SOLID STATE; SPECTROPHOTOMETER;

ADSORPTION; ALUMINUM SILICATES; BENTONITE; CHLORPYRIFOS; HYDROLYSIS; KAOLIN; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PHOSPHORUS ISOTOPES; SOIL POLLUTANTS;

EID: 32344431937     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es051703p     Document Type: Article

References (37)

1. Somasundaram, L., Coats, J. R., Eds. Pesticide Transformation Products, ACS Symposium Series 459; American Chemical Society: Washington, DC, 1991; pp 2-29.
2. 13C NMR Analysis of Sequence Distributions in Poly(ethylene-co-1-hexene). Ph.D. Dissertation, Colorado State University, 2006.
3. (b) Seger, M. R.; Maciel, G. E. NMR Investigation of an Organothiophosphate Pesticide, Chlorpyrifos, Sorbed on Montmorillonite Clays. Environ. Sci. Technol. 2006, 40, 797-802.
4. Yaron, B. Some aspects of surface interactions of clays with organophosphorus pesticides. Soil Sci. 1978, 125, 210-216.
5. Kamiya, M.; Mitsuhashi, S.; Makino, M. Catalytic properties of cyclodextrins on the hydrolysis of parathion and paraoxon in aquatic medium containing humic acids. Chemosphere 1992, 25, 1783-1796.
6. Mingelgrin, U.; Saltzman, S.; Yaron, B. A possible model for the surface-induced hydrolysis of organophosphorus pesticides on kaolinite clays. Soil Sci. Soc. Am. J. 1977, 41, 519-523.
7. Fukuto, T. R.; Hornig, E. O.; Metcalf, R. L. Insecticide decomposition - nuclear magnetic resonance in examination of thermal decomposition of O,O-dimethyl O-(4I)methylthio-3-toly phosphorothioate. J. Agric. Food Chem. 1964, 12, 169-171.
8. (b) Rengasamy, S.; Parmar, B. S. Investigation of some factors influencing isomalathion formation in malathion products. J. Agric. Food Chem. 1988 136, 1025-1030.
9. Greenhalgh, R.; Blackwell, B. A.; Preston, C. M.; Murray, W. J. Phosphorus-31 nuclear magnetic resonance analysis of technical organophosphorus insecticides for toxic contaminants. J. Agric. Food Chem. 1983, 31, 710-713.
10. Brzak, K. A.; Harms, D. W.; Bartels, M. J.; Nolan, R. J. Determination of Chlorpyrifos, Chlorpyrifos oxon, and 3,5,6-trichloro-2-pyridinol in rat and human blood. J. Anal. Toxicol. 1998, 22, 203-210.
11. Racke, K. D.; Steele, K. P.; Yoder, R. N.; Dick, W. A.; Avidov, E. Factors affecting the hydrolytic degradation of Chlorpyrifos. J. Agric. Food Chem. 1996, 44, 1582-1592.
12. Awasthi, M. D.; Prakash, N. B. Persistence of Chlorpyrifos in soils under different moisture regimes. Pestic. Sci. 1997, 50, 1-4.
13. Macalady, D. L.; Wolfe, N. L. New perspectives on the hydrolytic degradation of the Organothiophosphate insecticide Chlorpyrifos. J. Agric. Food Chem. 1983, 31, 1139-1147.
14. Sanchez-Camazano, M.; Sanchez-Martin, M. J. Trimethyl phosphate induced decomposition of kaolinite. Clay Clay Miner. 1994, 42, 221-225.
15. Shainberg, I. Rate and mechanism of Na-montmorillonite hydrolysis in suspensions. Soil Sci. Soc. Am. Proc. 1973, 37, 689-694.
16. Worthing, C. R.; Walker, S. B., Eds. The Pesticide Manual, 8th ed.; British Crop Protection Council: UK, 1987.
17. Andrew, E. R. Magic angle spinning in solid-state NMR-spectroscopy. Philos. Trans R. Soc. London, Ser. A 1981, 299, 505-520.
18. (b) Andew, E. R.; Bradbury, A.; Eades, R. G. Nuclear magnetic resonance spectra from a crystal rotated at high speed. Nature 1958, 182, 1659-1659.
19. (c) Kessmeier, H.; Norberg, R. E. Pulsed nuclear magnetic resonance in rotating solids. Phys. Rev. 1967, 155, 321-337.
20. Gay, I. D. A magic-angle spinner for vacuum-sealed samples. J. Magn. Reson. 1984, 50, 413-420.
21. Pines, A.; Gibby, M. G.; Waugh, J. S. Proton-enhanced nuclear induction spectroscopy - method for high-resolution NMR of dilute spins in solids. J. Chem. Phys. 1972, 56, 1776-1777.
22. (b) Schaefer, J.; Stejskal, E. O. Carbon-13 nuclear magnetic resonance of polymers spinning at the magic angle. J. Am. Chem. Soc. 1976, 90, 1031-1032.
23. Herzfeld, J.; Berger, A. E. Sideband intensities in NMR spectra of samples spinning at the magic angle. J. Chem. Phys. 1980, 73, 6021-6030.
24. Herzfeld, J.; Berger, A. E. Sideband intensities for NMR-spectra of samples spun at the magic angle. Biophys. J. 1979, 25, A164.
25. 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.
26. 31P NMR for the analysis of organophosphorus insecticide residues in cole crops. J. Agric. Food Chem. 1991, 39, 911-916.
27. Krolski, M. E.; Bosnak, L. L.; Murphy, J. J. Application of nuclear magnetic resonance spectroscopy to the identification and quantification of pesticide residues in soil. J. Agric. Food Chem. 1992, 40, 458-461.
28. 13C DP- and CP-MAS solid-state NMR methods. Ph.D. Dissertation, Colorado State University, 2001.
29. 13C NMR of soil and organic soil fractions. Anal. Chem. 2003, 75, 2421-2432.
30. 13C NMR spectral editing of humic material. J. Mol. Struct. 2000, 550-551, 297-305.
31. Sanchez-Camazano, M.; Sanchez-Martin, M. J. Montmorillonite-catalyzed hydrolysis of phosmet. Soil Sci. 1983, 136, 89-93.
32. Bielawski, J.; Casida, J. E. Phosphorylating intermediates in the peracid oxidation of phosphorothionates, phosphorothiolates, and Phosphorodithioates. J. Agric. Food Chem. 1988, 36, 610-615.
33. Kowalska, M.; Güler, H.; Cocke, D. Interactions of clay minerals with organic pollutants. Sci. Total Environ. 1994, 141, 223-240.
34. Duer, M. J.; Rocha, J.; Klinowski, J. Solid-state NMR studies of the molecular motion in the kaolinite:DMSO intercalate. J. Am. Chem. Soc. 1992, 114, 6867-6874.
35. Maderia, M.; Hunsicker, L. M.; DeRose, V. J. Metal-phosphate interactions in the hammerhead ribozyme observed by P-31 NMR and phosphorothioate substitutions. Biochemistry 2000, 39, 12113-12120.
36. Olah, G. A.; McFarland, C. W. Organophosphorus Compounds. XIII. Protonation, cleavage, and alkylation of thiophosphates and thiophosphites. J. Org. Chem. 1975, 40, 2582-2587.
37. VanWazer, J. R.; Callis, C. F.; Shoolery, J. N.; Jones, R. C. Principles of phosphorus chemistry. II. Nuclear magnetic resonance measurements. J. Am. Chem. Soc. 1956, 70, 5715-5726.