Reactions of hydrated electrons with triazine derivatives in aqueous medium

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 21, 2006, Pages 8171-8176

  Varghese, Rani ^a   Mohan, Hari ^b   Manoj, P ^a   Manoj, V M ^a   Aravind, Usha K ^a   Vandana, K ^a   Aravindakumar, C T ^a  

^a MAHATMA GANDHI UNIVERSITY   (India)

^b BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Degradation; Electron adducts; Pulse radiolysis; Second order rate constants; Steady state radiolysis

Indexed keywords

HERBICIDE; TRIAZINE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; ELECTRON; KINETICS; PULSE RADIOLYSIS; SPECTROSCOPY;

ELECTRONS; HERBICIDES; KINETICS; PULSE RADIOLYSIS; SPECTRUM ANALYSIS; TRIAZINES; WATER;

EID: 33751218023     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061916d     Document Type: Article

References (42)

1. Hassall, K. A. In The Biochemistry and Use of Pesticides: Structure, Metabolism, Mode of Action and Uses in Crop Protection, 2nd ed.; Macmillian Publishers: Hampshire, United Kingdom, 1990; pp 440-445.
2. Pellzzetti, E.; Maurino, V.; Minero, C.; Carlin, V.; Pramauro, E.; Zerbinati O.; Tosato, M. L. Photocatalytic degradation of atrazine and other s-triazine herbicides. Environ. Sci. Technol. 1990, 24, 1559-1565.
3. D'Itri, F. M.; Wolfson, L.G. Rural Ground Water Contamination; Lewis: Chelsea, MI, 1988.
4. Stein, M. W.; Sansone, E.B. Degradation of Chemical Carcinogens; Van Nostrand Reinhold: New York, 1980.
5. Mullar, K. R., Ed. Chemical Waste: Handling and Treatment; Springer-Verlag: Berlin, 1986.
6. Burkhard, N.; Guth, V. Photodegradation of atrazine, atratone and ametryne in aqueous solutions with acetone as photosensitizer. Pestic. Sci. 1976, 7, 65-71.
7. Pape, B. E.; Zabic, M. J. Photohemistry of bioactive compounds. Photohemistry of selected 2-chloro- and 2-methylthio-4,6-di-(alkylamino)-s- triazine herbicides. J. Agric. Food Chem. 1970, 18 (2), 202-207.
8. Ruzo, L. O.; Zabik, M. J.; Schuetz, R. D. Photohemistry of bioactive compounds. Kinetics of selected s-triazines in solution. J. Agric. Food Chem. 1973, 21, 1047-1049.
9. Higuera, M. J.; Montoya, M. R.; Mellado, J. M. R. On the Electroreduction of 4-chloro-2,6-diisopropylamino-s-triazine (propazine) on mercury electrodes. Electrochem. Commun. 1999, 1, 184-189.
10. Skopalova, J.; Lemr, K.; Kotoucek, M.; Cap L Ondra, P. Electrochemical reduction of prometryne and the other 2-methylthio-4,6-dialkylamino-s-triazine herbicides at mercury electrodes. Electroanalysis 1998, 10 (5), 331-335.
11. Galvin, R. M; Mellado, J. M. R.; Higuera, M. J.; Montoya, M. R. Reductive detoxification of the s-triazine herbicides simazine and propazine at laboratory scale. Bull. Electrochem. 2001, 17 (2), 49-55.
12. 2 oxidation of atrazine first degradation products: Deethylatrazine and deisopropylatrazine. Environ. Toxicol. Chem. 1996, 15, 868-872.
13. Arantegui, J.; Prado, J.; Chamarro, E.; Esplugas, S. Kinetics of the UV degradation of atrazine in aqueous solution in the presence of hydrogen peroxide. J. Photochem. Photobiol. A: Chem. 1995, 88, 65-74.
14. Adams, C. D.; Randtke, S. J. Ozonation byproducts of atrazine in synthetic and natural waters. Environ. Sci. Technol. 1992, 26, 2218-2227.
15. Petrier, C.; David, B.; Laguian, S. Ultrasonic degradation at 20 kHz and 500 kHz of atrazine and pentachlorophenol in aqueous solution: Preliminary results. Chemosphere 1996, 32, 1709-1718.
16. 3+-catalyzed degradation of chlorophenoxy herbicides by hydrogen peroxide. Environ. Sci. Technol. 1992, 26, 944-951.
17. Pratap, K.; Lemley, A. T. Fenton electrochemical Treatment of Aqueous Atrazine and Metolachlor. J. Agric. Food. Chem. 1998, 46, 3285-3291.
18. Bier, E. L.; Singh, J.; Li, Z.; Comfort, S. D.; Shea, P. J. Remediating hexahydro-1,3,5-trinitro-1,2,5-triazine-contaminated water and soil by Fenton oxidation. Environ. Toxicol. Chem. 1999, 18 (6), 1078-1084.
19. Arnold, S. M.; Mickey, W. J.; Harris, R. F. Degradation of atrazine by Fenton's reagent: Condition optimization and product quantification. Environ. Sci. Technol. 1995, 29, 2083-2089.
20. Lancas, F. M.; Queiroz, M. E. C. Behavior of triazines upon γ-irradiation. J. Radioanal. Nucl. Chem., Lett. 1995, 199, 395-403.
21. Tauber, A.; von Sonntag, C. Products and kinetics of the OH-radical-induced dealkylation of atrazine. Acta Hydrochim. Hydrobiol. 2000, 28, 15-23.
22. Joseph, J. M.; Jacob, T. A.; Manoj, V. M.; Aravindakumar, C. T.; Mohan, H.; Mittal, J. P. Oxidative degradation of triazine derivatives in aqueous medium: A radiation and photochemical study. J. Agric. Food Chem. 2000, 48, 3704-3709.
23. Getoff, N. Radiation chemistry and environment. Radiat. Phys. Chem. 1999, 54, 377-384.
24. Spinks, J. W. T.; Woods, R. J. Water and inorganic aqueous systems. In An Introduction to Radiation Chemistry, 3rd ed.; John Wiley and Sons, Inc.: New York, 1990; pp 243-313.
25. •-) in aqueous solution. J. Phys. Chem. Ref. Data 1988, 17, 513-886.
26. Zacheis, G. A.; Gray, K. A.; Kamat, P. V. Radiolytic reduction of hexachlorobenzene in surfactant solutions: A steady-state and pulse radiolysis study. Environ. Sci. Technol. 2000, 34, 3401-3407.
27. Flyunt, R.; Makogon, O.; Schoneich, C.; Asmus, K. D. Radiolytically induced reductive degradation of halothane in air-saturated aqueous solutions in the presence of methionine. Nukleonika 2000, 45, 45-50.
28. Chaychian, M.; Silverman, J.; Al-Sheikhly, M.; Poster, D. L.; Neta, P. Ionizing radiation induced degradation of tetrachlorobiphenyl in transformer oil. Environ. Sci. Technol. 1999, 33, 2461-2464.
29. Gilchrist, T. L. Six-membered ring compounds with two or more heteroatoms. In Heterocyclic Chemistry, 3rd ed.; Longmann Publishers: Essex, England, 1997; pp 257-294.
30. (a) Guha, S. N.; Moorthy, P. N.; Kishore, K.; Naik, D. B.; Rao, K. N. One-electron reduction of thionine studied by pulse radiolysis. Proc. Indian Acad. Sci. (Chem. Sci.) 1987, 99, 261.
31. (b) Priyadarsini, K. I.; Naik, D. B.; Moorthy, P. N.; Mittal, J. P. Tihany Symp. Radiat. Chem. Hungarian Chem. Soc. 1995, 205.
32. (c) Panajkar, M. S.; Moorthy, P. N.; Shirke, N. D. BARC Rep. 1988, 1410.
33. Buxton, G. V.; Stuart, C. R. Re-evaluation of the thiocyanate dosimeter for pulse radiolysis. J. Chem. Soc. Faraday Trans. 1995, 91, 279-281.
34. Fielden, E. M. In The Study of Fast Processes and Transient Species by Electron Pulse Radiolysis; Baxendale, J. H., Busi, F., Eds.; 1982; p 49.
35. Candeias, L. P.; Steenken, S. Electron adducts of adenine nucleosides nucleotides in aqueous solution: Protonation at two carbon sites (C2 and C8) and intra- and intermolecular catalysis by phosphate. J. Phys. Chem. 1992, 96, 937-944.
36. von Sonntag, C. Radiation chemistry of aqueous solutions and peroxyl radicals. The Chemical Basis of Radiation Biology, Taylor & Francis: London, 1987; pp 31-77.
37. aq and H atoms to hypoxanthine and inosine and the reactions of α-hydroxyalkyl radicals with purines. A pulse radiolysis and product analysis study. Int. J. Radiat. Biol. 1994, 66, 351-365.
38. Rao, R. R.; Aravindakumar, C. T.; Rao, B. S. M.; Mohan, H.; Mittal, J. P. Kinetics and spectral properties of electron adducts of 2′-deoxyinosine: A comparison with other purine nucleosides. J. Chem Soc., Perkin Trans 2 1996, 1077-1080.
39. - and OH adducts. Chem. Rev. 1989, 89, 503-520.
40. Hayon, E. Optical absorption spectra of ketyl radicals and radical anions of some pyrimidines. J. Chem. Phys. 1969, 51, 4881-4892.
41. Das, S.; Deeble, D. J.; Schuchmann, M.-N.; von Sonntag, C. Pulse radiolytic studies on uracil and uracil derivatives. Protonation of their electron adducts at oxygen and carbon. Int. J. Radiat. Biol. 1984, 46, 7-9.
42. Deeble, D. J.; Das, S.; Schuchmann, M.-N.; von Sonntag, C. Uracil derivatives: Sites and kinetics of protonation of the radical anions and UV of C(5) and C(6) H-atom adducts. J. Phys. Chem. : 1985, 89, 5784-5788.