Transformation of the fungicide chlorothalonil by Fenton reagent

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 26, 2002, Pages 7570-7575

  Park, Jong Woo ^a   Lee, Sung Eun ^a   Rhee, In Koo ^a   Kim, Jang Eok ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Chlorothalonil; Fenton reagent; Transformation; UV irradiation

Indexed keywords

CHLORINE; CHLOROTHALONIL; FENTON'S REAGENT; FERRIC CHLORIDE; FERRIC ION; FERRIC NITRATE; FERRIC SULFATE; FERROUS GLUCONATE; FUNGICIDE; HYDROGEN PEROXIDE; IRON; NITRATE; NITRILE; REAGENT; WATER;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; COMPARATIVE STUDY; DECHLORINATION; FUNGICIDAL ACTIVITY; FUNGUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; MASS FRAGMENTOGRAPHY; NONHUMAN; PH; SOLUTION AND SOLUBILITY; TIME; ULTRAVIOLET IRRADIATION; ULTRAVIOLET RADIATION;

CHLORINE; FERRIC COMPOUNDS; FUNGICIDES, INDUSTRIAL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; IRON; KINETICS; NITRATES; NITRILES; SOLUTIONS; TIME FACTORS; ULTRAVIOLET RAYS; WATER;

FUNGI;

EID: 0037132514     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf025772o     Document Type: Article

References (44)

1. The Pesticide Manual, 11th Ed.; Tomlin, C. D. S., Ed.; British Crop Protection Council: Farnham, U.K., 1997; pp 227-229.
2. Cox, C. Chlorothalonil. J. Pest. Reform. 1997, 17, 14-20.
3. Agrochemical Year Book; Agricultural Chemical Industrial Association: Seoul, Korea, 2002; pp 212-213.
4. 14C-TCIN in S. gairdneri. Aquat. Toxicol. 1985, 7, 93-105.
5. 14C-chlorothalonil in tropical soils. Arch. Environ. Contam. Toxicol. 2001, 40, 295-302.
6. Robert, T.; Hudson, D. Metabolic Pathways of Agrochemicals. Part 2: Insecticides and Fungicides; The Royal Society of Chemistry: Cambridge, U.K., 1999; pp 1380-1384.
7. Penuela, G. A.; Barcelo, D. Photodderadation and stability of chlorothalonil in water studied by solid-phase disk extraction, followed by gas chromatographic techniques. J. Chromatogr., A 1998, 823, 81-90.
8. Sakkas, V. A.; Lambropoulou, D. A.; Albanis, T. A. Study of chlorothalonil photodegradation in natural waters and in the presence of humic substances. Chemosphere 2002, 48, 939-945.
9. Kim, J.-E.; Fernandes, E.; Bollag, J.-M. Enzymatic coupling of the herbicide bentazon with humus monomer and characterization of reaction products. Environ. Sci. Technol. 1997, 31, 2392-2398.
10. Lee, J.-E.; Park, J.-W.; Kim, J.-E. Use of plant materials for decontamination of wastewater polluted with 2,4-dichlorophenol. Korean J. Environ. Agric. 1999, 18, 292-297.
11. Lee, J.-E.; Park, J.-W.; Kim, J.-E. Decontamination of wastewater polluted with phenolic and anilinic compounds using plant materials. Korean J. Environ. Agric. 2000, 19, 228-233.
12. Behki, R.; Topp, E.; Dick, W.; Germon, P. Metabolism of the herbicide atrazine by Rhodococcus strains. Appl. Environ. Microbiol. 1993, 59, 1955-1959.
13. Kilbane, J. J.; Chatterjee, D. K.; Karns, J. S.; Kellogg, S. T.; Chakrabarty, A. M. Biodegradation of 2,4,5-trichlorophenoxy-acetic acid by a pure culture of Pseudomonas cepacia. Appl. Environ. Microbiol. 1982, 44, 72-78.
14. Levanon, D. Roles of fungi and bacteria in the mineralization of the pesticides atrazine, alachlor, malathion and carbofuran in soil. Soil Biol. Biochem. 1993, 25, 1097-1105.
15. Alexander, M. Research needs in bioremediation. Environ. Sci. Technol. 1991, 25, 1972-1973.
16. Steinberg, S. M.; Pignatello, J. J.; Sawhney, B. L. Persistence of 1,2-dibromoethane in soils; entrapment in intraparticle micropores. Environ. Sci. Technol. 1987, 21, 1201-1208.
17. Ollis, D. F. Comparative aspects of advanced oxidation processes. In Emerging Technologies in Hazardous Waste Management III; Tedder, D. W., Pohland, F. G., Eds.; ACS Symposium Series 518; American Chemical Society: Washington, DC, 1993; pp 18-34.
18. Haag, W. R.; Yao, C. C. D. Rate constants for reaction of hydroxyl radicals with several drinking water contaminants. Environ. Sci. Technol. 1992, 26, 1005-1013.
19. Legrini, O.; Oliveros, E.; Braun, A. M. Photochemical processes for water treatment. Chem. Rev. 1983, 93, 671-698.
20. Hapeman-Somich, C. J.; Zong, G.-M.; Lusby, W. R.; Muldoon, M. T.; Waters, R. Aqueous ozonation of atrazine. Product identification and description of the degradation pathway. J. Agric. Food Chem. 1992, 40, 2294-2298.
21. Hapeman, C. J.; Anderson, B. G.; Torrents, A.; Acher, A. Mechanistic investigations concerning the aqueous ozonolysis of bromacil. J. Agric. Food Chem. 1997, 45, 1006-1011.
22. Hoigne, J.; Bader, H. Rate constants of reactions of ozone with organic and inorganic compounds in water. 2. Dissociating organic compounds. Water Res. 1983, 17, 185-194.
23. Staehelin, S.; Hoigne, J. Decomposition of ozone in water. Rate of initiation by hydroxide ions and hydrogen peroxide. Environ. Sci. Technol. 1982, 16, 676-681.
24. Adams, C. D.; Scanlan, P. A.; Secrist, N. S. Oxidation and biodegradability enhancement of 1,4-dioxane using hydrogen peroxide and ozone. Environ. Sci. Technol. 1994, 28, 1812-1818.
25. Mokrini, A.; Oussi, D.; Esplugas, S. Oxidation of aromatic compounds with UV radiation/ozone/hydrogen peroxide. Water Sci. Technol. 35, 95-102.
26. Pignatello, J. J.; Sun, Y. Complete oxidation of metolachlor and methyl parathion in water by the photoassisted fenton reaction. Water Res. 1995, 29, 1837-1844.
27. Pignatello, J. J.; Jiu, D.; Huston, P. Evidence for an additional oxidant in the photoassisted fenton reaction. Environ. Sci. Technol. 1999, 33, 1832-1839.
28. Li, Z. M.; Comfort, S. D.; Shea, P. J. Destruction of 2,4,6-trinitrotoluene by fenton oxidation. J. Environ. Qual. 26, 480-487.
29. 3+-catalyzed degradation of chlorophenoxy herbicides by hydrogen peroxide. Environ. Sci. Technol. 1992, 26, 944-951.
30. Huston, P. L.; Pignatello, J. J. Degradation of selected pesticide active ingredients and commercial formulations in water by the photoassisted fenton reaction. Water Res. 33, 1238-1246.
31. Engwall, M. A.; Pignatello, J. J.; Grasso, D. Degradation and detoxification of the wood preservatives creosote and pentachlorophenol in water by the photofenton reaction. Water Res. 1999, 33, 1151-1158.
32. 2/UV. Environ. Sci. Technol. 1993, 27, 304-310.
33. Fallmann, H.; Krutzler, T.; Bauer, R.; Malato, S.; Blanco, J. Applicability of the photofenton method for treating water containing pesticides. Catal. Today 1999, 54, 309-319.
34. Howsawkeng, J.; Watts, G. J.; Washington, D. L.; Teel, A. L.; Hess, T. F.; Crawford, R. L. Evidence for simultaneous abioticbiotic oxidations in a microbial-Fenton's system. Environ. Sci. Technol. 2001, 35, 2961-2966.
35. Pratap, K.; Lemley, A. T. Fenton electrochemical treatment of aqueous atrazine and metolachlor. J. Agric. Food Chem. 1998, 46, 3285-3291.
36. Pignatello, J. J.; Baehr, K. Ferric complexes as catalysts for "Fenton" degradation of 2,4-D and metolachlor in soil. J. Environ. Qual. 1994, 23, 365-370.
37. 2/ UV. J. Agric. Food Chem. 1993, 41, 1139-1142.
38. Gimenez, J.; Curco, D.; Marco, P. Reactor modeling in the photocatalytic oxidation of wastewater. Water Sci. Technol. 1997, 35, 207-213.
39. x; M=Fe, Cu, Co, Mn]/hydroperoxide-induced activation of dioxygen for the oxygenation of hydrocarbons; Oxygenated fenton chemistry. Acc. Chem. Res. 1996, 29, 409-416.
40. Walling, C. Fenton's reagent revisited. Acc. Chem. Res. 1975, 8, 125-131.
41. Vaughan, P. P.; Blough, N. V. Photochemical formation of hydroxyl radical by constituents of natural waters. Environ. Sci. Technol. 1998, 32, 2947-2953.
42. Larson, R. A.; Schlauch, M. B.; Marley, K. A. Ferric ion promoted photodecomposition of triazines. J. Agric. Food Chem. 1991, 39, 2057-2062.
43. Moon, D.-K.; Maruyama, T.; Osakada, K.; Yamamoto, T. Chemical oxidation of polyaniline by radical generating reagent. Chem. Lett. 1991, 1633-1636.
44. Walling, C. Intermediates in the reactions of fenton type reagents. Acc. Chem. Res. 1998, 31, 155-157.