Aqueous oxidation of phenylurea herbicides by triplet aromatic ketones

Environmental Science and Technology

Volumn 40, Issue 21, 2006, Pages 6636-6641

  Canonica, Silvio ^a   Hellrung, Bruno ^b   Müller, Pavel ^b   Wirz, Jakob ^b  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS; HERBICIDES; IMPURITIES; KETONES; OXIDATION; REACTION KINETICS;

DISSOLVED NATURAL ORGANIC MATTER (DDM); ORGANIC CONTAMINANTS; PHENYLUREA HERBICIDES;

UREA;

2 ACETONAPHTHONE; 3' METHOXYACETOPHENONE; AROMATIC COMPOUND; BENZOPHENONE; CARBANILAMIDE; DISSOLVED ORGANIC MATTER; HERBICIDE; KETONE; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ELECTRON TRANSITIONS; HERBICIDES; IMPURITIES; KETONES; OXIDATION; REACTION KINETICS; UREA;

DISSOLVED ORGANIC MATTER; HERBICIDE; IRRADIATION; KETONE; ORGANIC POLLUTANT; OXIDATION; REACTION KINETICS; TRANSFORMATION; WATER POLLUTION;

AQUEOUS SOLUTION; ARTICLE; DIFFUSION; ELECTRON TRANSPORT; IRRADIATION; KINETICS; LASER; MEASUREMENT; OXIDATION; PHOTOLYSIS; POLLUTANT; STEADY STATE;

CHEMISTRY; ENVIRONMENTAL MONITORING; ESTERS; HERBICIDES; HYDROGEN-ION CONCENTRATION; KETONES; KINETICS; LASERS; LIGHT; MODELS, CHEMICAL; ORGANIC CHEMICALS; PHENOLS; PHENYLUREA COMPOUNDS; PHOTOLYSIS; SPECTROPHOTOMETRY;

EID: 33750852442     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es0611238     Document Type: Article

References (28)

1. Canonica, S.; Jans, U.; Stemmler, K.; Hoigné, J. Transformation kinetics of phenols in water: Photosensitization by dissolved natural organic material and aromatic ketones. Environ. Sci. Technol. 1995, 29, 1822-1831.
2. Aguer, J. P.; Richard, C. Transformation of fenuron induced by photochemical excitation of humic acids. Pestic. Sci. 1996, 46, 151-155.
3. Gerecke, A. C.; Canonica, S.; Müller, S. R.; Schärer, M.; Schwarzenbach, R. P. Quantification of dissolved natural organic matter (DOM) mediated phototransformation of phenylurea herbicides in lakes. Environ. Sci. Technol. 2001, 35, 3915-3923.
4. Werner, J. J.; McNeill, K.; Arnold, W. A. Environmental photodegradation of mefenamic acid. Chemosphere 2005, 58, 1339-1346.
5. 2 extrusion photoproduct. Environ. Sci. Technol. 2005, 39, 3630-3638.
6. Chin, Y. P.; Miller, P. L.; Zeng, L. K.; Cawley, K.; Weavers, L. K. Photosensitized degradation of bisphenol A by dissolved organic matter. Environ. Sci. Technol. 2004, 38, 5888-5894.
7. Canonica, S.; Hellrung, B.; Wirz, J. Oxidation of phenols by triplet aromatic ketones in aqueous solution. J. Phys. Chem. A 2000, 104, 1226-1232.
8. Cohen, S. G.; Parola, A.; Parsons, G. H. Photoreduction by amines. Chem. Rev. 1973, 73, 141-161.
9. Das, P. K.; Encinas, M. V.; Scaiano, J. C. Laser flash photolysis study of the reactions of carbonyl triplets with phenols and photochemistry of p-hydroxypropiophenone. J. Am. Chem. Soc. 1981, 103, 4154-4162.
10. Das, P. K.; Bobrowski, K. Charge transfer reactions of methoxybenzenes with aromatic carbonyl triplets. A laser flash photolytic study. J. Chem. Soc.-Faraday Trans. II 1981, 77, 1009-1027.
11. Bhattacharyya, S. N.; Das, P. K. Photoreduction of benzophenone by amino acids, aminopolycarboxylic acids and their metal complexes. A laser flash photolysis study. J. Chem. Soc.-Faraday Trans. II 1984, 80, 1107-1116.
12. Encinas, M. V.; Lissi, E. A.; Olea, A. F. Quenching of triplet benzophenone by vitamins E and C and by sulfur-containing amino acids and peptides. Photochem. Photobiol. 1985, 42, 347-352.
13. Marciniak, B.; Bobrowski, K.; Hug, G. L. Quenching of triplet states of aromatic ketones by sulfur-containing amino acids in solution. Evidence for electron transfer. J. Phys. Chem. 1993, 97, 11937-11943.
14. Loeff, I.; Rabani, J.; Treinin, A.; Linschitz, H. Charge-transfer and reactivity of nπ* and ππ* organic triplets, including anthraquinonesulfonates, in interactions with inorganic anions: A comparative study based on classical Marcus theory. J. Am. Chem. Soc. 1993, 115, 8933-8942.
15. Encinas, M. V.; Lissi, E. A.; Vasquez, M.; Olea, A. F.; Silva, E. Photointeraction of benzophenone triplet with lysozyme. Photochem. Photobiol. 1989, 49, 557-563.
16. Bonneau, R.; Wirz, J.; Zuberbühler, A. D. Methods for the analysis of transient absorbance data. Pure Appl. Chem. 1997, 69, 979-992.
17. Wegelin, M.; Canonica, S.; Mechsner, K.; Fleischmann, T.; Pesaro, F.; Metzler, A. Solar water disinfection: Scope of the process and analysis of radiation experiments. J. Water Supply Res. Technol. - Aqua 1994, 43, 154-169.
18. Dulin, D.; Mill, T. Development and evaluation of sunlight actinometers. Environ. Sci. Technol. 1982, 16, 815-820.
19. Canonica, S.; Freiburghaus, M. Electron-rich phenols for probing the photochemical reactivity of freshwaters. Environ. Sci. Technol. 2001, 35, 690-695.
20. Canonica, S.; Kohn, T.; Mac, M.; Real, F. J.; Wirz, J.; Von Gunten, U. Photosensitizer method to determine rate constants for the reaction of carbonate radical with organic compounds. Environ. Sci. Technol. 2005, 39, 9182-9188.
21. Hayon, E.; Ibata, T.; Lichtin, N. N.; Simic, M. Electron and hydrogen atom attachment to aromatic carbonyl compounds in aqueous solution. Absorption spectra and dissociation constants of ketyl radicals. J. Phys. Chem. 1972, 76, 2072-2078.
22. 2- photocatalysed UV degradation of phenylurea herbicides. ChemPhysChem 2005, 6, 2064-2074.
23. Das, P. K.; Bhattacharyya, S. N. Laser flash photolysis study of electron transfer reactions of phenolate ions with aromatic carbonyl triplets. J. Phys. Chem. 1981, 85, 1391-1395.
24. Bhattacharyya, K.; Das, P. K. Nanosecond transient processes in the triethylamine quenching of benzophenone triplets in aqueous alkaline media. Substituent effect, ketyl radical deprotonation, and secondary photoreduction kinetics. J. Phys. Chem. 1986, 90, 3987-3993.
25. Hansch, C.; Leo, A.; Taft, R. W. A survey of Hammett substituent constants and resonance and field parameters. Chem. Rev. 1991, 91, 165-195.
26. Mansch, C.; Gao, H. Comparative QSAR: Radical reactions of benzene derivatives in chemistry and biology. Chem. Rev. 1997, 97, 2995-3059.
27. Canle, M.; Rodriguez, S.; Vazquez, L. F. R.; Santaballa, J. A.; Steenken, S. First stages of photodegradation of the urea herbicides Fenuron, Monuron and Diuron. J. Mol. Struct. 2001, 565, 133-139.
28. De Laat, J.; Maouala Makata, P.; Doré, M. Rate constants for reactions of ozone and hydroxyl radicals with several phenylureas and acetamides. Environ. Technol. 1996, 17, 707-716.