Transformation of organophosphorus pesticides in the presence of aqueous chlorine: Kinetics, pathways, and structure - Activity relationships

Environmental Science and Technology

Volumn 43, Issue 7, 2009, Pages 2335-2340

  Duirk, Stephen E ^a   Desetto, Lisa M ^a,b   Davis, Gary M ^a,b  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

^b Student Services Authority

Author keywords

[No Author keywords available]

Indexed keywords

DRINKING WATER TREATMENTS; HYDROLYSIS RATES; HYPOCHLORITE IONS; HYPOCHLOROUS ACIDS; INTRINSIC RATES; MOLECULAR DESCRIPTORS; NEAR-NEUTRAL PH; ORGANOPHOSPHORUS PESTICIDES; STRUCTURE-ACTIVITY RELATIONSHIPS; TRANSFORMATION PRODUCTS;

ACIDS; AGRICULTURAL CHEMICALS; BIOCHEMISTRY; CHEMICALS REMOVAL (WATER TREATMENT); CHLORINE; HYDROLYSIS; POTABLE WATER;

PESTICIDES;

CHLORETHOXYFOS; CHLORINE; CHLORPYRIFOS; DIMPYLATE; DRINKING WATER; HYPOCHLORITE; HYPOCHLOROUS ACID; MALATHION; METHIDATHION; NUCLEOPHILE; ORGANOPHOSPHORUS COMPOUND; PARATHION; PESTICIDE; PHOSMET; PHOSPHORODITHIOIC ACID; PHOSPHOROTHIOIC ACID; TEBUPIRIMFOS; UNCLASSIFIED DRUG;

CHLORINE; DRINKING WATER; ENVIRONMENTAL FATE; HYDROLYSIS; KINETICS; ORGANOPHOSPHATE; PESTICIDE; TRANSFORMATION; WATER TREATMENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHLORINATION; CONTROLLED STUDY; DEGRADATION KINETICS; HYDROLYSIS; PH MEASUREMENT; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION; WATER TREATMENT;

CHLORINE; HYDROLYSIS; KINETICS; ORGANOPHOSPHORUS COMPOUNDS; PESTICIDES; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

EID: 64349102564     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es802868y     Document Type: Article

References (30)

1. Gilliom, R. J.; Barbasg, J. E.; Crawford, C. G.; Hamilton, P. A.; Martin, J. D.; Nakagaki, N.; NowellL. H.; Scott, J. C.; Stackelberg, P. E.; Thelin, G. P.; Wolock, D. M. Pesticides in the Nation's Streams and Ground Water, 1992-2001; U.S. Geological Survey: Reston, VA, 2006.
2. Duirk, S. E.; Collette, T. W. Degradation of chlorpyrifos in aqueous chlorine solutions: pathways, kinetics, and modeling. Environ. Sci. Technol. 2006, 40 (2), 546-551.
3. Coupe, R. H.; Blomquist, J. D. Water-soluble pesticides in finished water of community water supplies. J. Am. Water Works Assoc. 2004, 96 (10), 56-68.
4. Kolpin, D. W.; Barbash, J. E.; Gilliom, R. J. Pesticides in ground water of the United States, 1992-1996. Ground Water 2000, 38 (6), 858-863.
5. Pehkonen, S. O.; Zhang, Q. The degradation of organophos-phorus pesticides in natural waters: A. critical review. Crit. Rev. Env. Sci. Technol. 2002, 32 (1), 17-72.
6. Community Water System Survey, EPA815-R-97-011a; United States Environmental Protection Agency: Washington, DC, 1997; Vol. 1.
7. Lopez, A.; Mascolo, G.; Tiravanti, G.; Santori, M.; Passino, R. Oxidation of sulfur-containing s-triazines during groundwater hypochlorination. Water Sci. Technol. 1994, 30 (7), 53-59.
8. Mascolo, G.; Lopez, A.; Passino, R.; Ricco, G.; Tiravanti, G. Degradation of sulfur-containing s-triazines during water chlorination. Water Res. 1994, 28 (12), 2499-2506.
9. Adams, C. D.; Randtke, S. J. Removal of atrazine from drinking-water by ozonation. J. Amer. Water Works Assoc. 1992, 84 (9), 91-102.
10. Verstraeten, I. M.; Thurman, E. M.; Lindsey, M. E.; Lee, E. C.; Smith, R. D. Changes in concentrations of triazine and acetamide herbicides by bank filtration, ozonation, and chlorination in a public water supply. J. Hydrol. 2003, 276 (1-4), 287-288.
11. Miles, C. J. Degradation of aldicarb, aldicarb sulfoxide, and aldicarb sulfone in chlorinated water. Environ. Sci. Technol. 1991, 25 (10), 1774-1779.
12. Mason, Y. Z.; Choshen, E.; Ravacha, C. Carbamate insecticides-Removal from water by chlorination and ozonation. Water Res. 1990, 24 (1), 11-21.
13. Kodama, S.; Yamamoto, A.; Matsunaga, A. S-Oxygenation of thiobencarb in tap water processed by chlorination. J. Agric. Food. Chem. 1997, 45 (3), 990-994.
14. Zhang, Q.; Pehkonen, S. O. Oxidation of diazinon by aqueous chlorine: Kinetics, mechanisms, and product studies. J. Agric. Food. Chem. 1999, 47 (4), 1760-1766.
15. Magara, Y.; Aizawa, T.; Matumoto, N.; Souna, F. Degradation of pesticides by chlorination during water-purification. Water Sci. Technol. 1994, 30 (7), 119-128.
16. Wu, J. G.; Laird, D. A. Abiotic transformation of chlorpyrifos to chlorpyrifos oxon in chlorinated water. Environ. Toxicol. Chem. 2003, 22 (2), 261-264.
17. Duirk, S. E.; Tarr, J. C.; Collette, T. W. Chlorpyrifos transformation by aqueous chlorine in the presence of bromide and natural organic matter. J. Agric. Food. Chem. 2008, 56 (4), 1328-1335.
18. Snoeyink, V. L.; Jenkins, D. A. Water Chemistry; John Wiley & Sons: New York, NY, 1980.
19. Dodd, M. C.; Huang, C. H. Aqueous chlorination of the antibacterial agent trimethoprim: Reaction kinetics and pathways. Water Res. 2007, 41 (3), 647-655.
20. Acero, J. L.; Benitez, F. J.; Real, F. J.; Gonzalez, M. Chlorination of organophosphorus pesticides in natural waters. J. Hazard. Mater. 2008, 153 (1-2), 320-328.
21. Edwards, J. O.; Pearson, R. G. Factors determining nucleophilic reactivities. J. Am. Chem. Soc. 1962, 84 (1), 16-24.
22. England, W. B.; Kovacic, P.; Hanrahan, S. M.; Jones, M. B. Molecular-orbital theory of supernucleophiles - Complementary criteria and supporting evidence. J. Org. Chem. 1980, 45 (11), 2057-2063.
23. Faust, S. D.; Gomaa, H. M. Chemical hydrolysis of some organic phosphorus and carbamate pesticides in aquatic environments. Environ. Lett, 1972, 3, (3), 171-201,
24. Fogelman, K. D.; Walker, D. M.; Margerum, D. W. Non-metal redox kinetics - hypochlorite and hypochlorous acid reactions with sulfite. Inorg. Chem. 1989, 28 (6), 986-993.
25. Deborde, M.; von Gunten, U. Reactions of chlorine with inorganic and organic compounds during water treatment -Kinetics and mechanisms: A. critical review. Water Res. 2008, 42 (1-2), 13-51.
26. Cherney, D. P.; Duirk, S. E.; Tarr, J. C.; Collette, T. W. Monitoring the speciation of aqueous free chlorine from pH 1 to 12 with Raman spectroscopy to determine the identity of the potent low-pH oxidant. Appl. Spectrosc. 2006, 60 (7), 764-772.
27. Hu, J. Y.; Morita, T.; Magara, Y.; Aizawa, T. Evaluation of reactivity of pesticides with ozone in water using the energies of frontier molecular orbitals. Water Res. 2000, 34 (8), 2215-2222.
28. Canonica, S.; Tratnyek, P. G. Quantitative structure-activity relationships for oxidation reactions of organic chemicals in water. Environ. Toxicol. Chem. 2003, 22 (8), 1743-1754.
29. Macalady, D. L.; Wolfe, N. L. Newperspectives on the hydrolytic degradation of the organophosphorothioate insecticide chlorpyrifos. J. Agric. Food. Chem. 1983, 31 (6), 1139-1147.
30. Wolfe, N. L.; Zepp, R. G.; Baughman, G. L.; Gordon, J. A. Kinetic investifation of malathion degradation in water. Bull. Environ. Contam. Toxicol. 1975, 13 (6), 707-713.