Indirect photodegradation of clethodim in aqueous media. byproduct identification by quadrupole time-of-flight mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 5, 2010, Pages 3068-3076

  Sevilla Morán, Beatriz ^a   Alonso Prados, José L ^a   García Baudín, José M ^a   Sandín España, Pilar ^a  

^a INIA   (Spain)

Author keywords

Clethodim herbicide; Natural substances; Photodegradation products; Photolysis; QTOF

Indexed keywords

CLETHODIM; CYCLOHEXANONE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; SOLUTION AND SOLUBILITY;

CHROMATOGRAPHY, LIQUID; CYCLOHEXANONES; MASS SPECTROMETRY; OXIDATION-REDUCTION; PHOTOCHEMISTRY; SOLUTIONS; WATER;

EID: 77949396021     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf9034173     Document Type: Article

References (30)

1. Konstantinou, I. K.; Hela, D. G.; Albanis, T. A. The status of pesticide pollution in surface waters (rivers and lakes) of Greece. Part I. Review on occurrence and levels. Environ. Pollut. 2006, 141 (3), 555-570.
2. Rebich, R. A.; Coupe, R. H.; Thurman, E. M. Herbicide concentrations in the Mississippi River Basin: The importance of chloroacetanilide herbicide degradates. Sci. Total Environ. 2004, 321, 189-199.
3. Marín, J. M.; Sancho, J. V.; Pozo, O. J.; López, F. J.; Hernández, F. Quantification and confirmation of anionic, cationic and neutral pesticides and transformation products in water by on-line solid phase extraction-liquid chromatography-tandem mass spectrometry. J. Chromatogr., A 2006, 1133, 204-214.
4. Iwataki, I. Cyclohexanedione herbicides: Their activities and properties; CRC Press: Boca Raton, FL, 1992; Vol. XVI, pp 397-426.
5. Mazellier, P.; Jirkovsky, J.; Bolte, M. Degradation of diuron photoinduced by iron(III) in aqueous solution. Pestic. Sci. 1997, 49 (3), 259-267.
6. Quivet, E.; Faure, R.; Georges, J.; Païssé, J. O.; Herbreteau, B.; Lantéri, P. Photochemical degradation of imazamox in aqueous solution: Influence of metal ions and anionic species on the ultraviolet photolysis. J. Agric. Food Chem. 2006, 54 (10), 3641-3645.
7. Sevilla-Morán, B.; Sandín-España, P.; Vicente-Arana, M. J.; Alonso-Prados, J. L.; García-Baudín, J. M. Study of alloxydim photodegradation in the presence of natural substances: Elucidation of transformation products. J. Photochem. Photobiol., A 2008, 198 (2-3), 162-168.
8. Somasundaram, L.; Coats, J. R. Pesticide transformation products. Fate and significance in the environment; ACS Symposium Series; American Chemical Society: Washington, DC, 1991; Vol. 459, p 305.
9. European Commission Report. Council Directive 98/83/EC of 3 November 1998 on the quality of water intended for human consumption, 1998, pp 32-54.
10. Sandín-España, P.; Magrans, J. O.; García- Baudín, J. M. Study of clethodim degradation and by-product formation in chlorinated water by HPLC. Chromatographia 2005, 62 (3-4), 133-137.
11. Marek, L. J.; Koskinen, W. C.; Bresnahan, G. A. LC/MS analysis of cyclohexanedione oxime herbicides in water. J. Agric. Food Chem. 2000, 48 (7), 2797-2801.
12. Ibáñez, M.; Sancho, J. V.; Pozo, O. J.; Hernández, F. Use of quadrupole time-of-flight mass spectrometry in environmental analysis: Elucidation of transformation products of triazine herbicides in water after UV exposure. Anal. Chem. 2004, 76 (5), 1328-1335.
13. Aguera, A.; Estrada, L. A. P.; Ferrer, I.; Thurman, E. M.; Malato, S.; Fernandez-Alba, A. R. Application of time-of-flight mass spectrometry to the analysis of phototransformation products of diclofenac in water under natural sunlight. J. Mass Spectrom. 2005, 40 (7), 908-915.
14. Falb, L. N.; Bridges, D. C.; Smith, A. E. Separation of clethodim herbicide from acid and photodegradation products by liquid chromatography. J- Assoc. Off. Anal. Chem. 1991, 74 (6), 999-1002.
15. Falb, L. N.; Bridges, D. C.; Smith, A. E. Effects of pH and adjuvants on clethodim photodegradation. J. Agric. Food Chem. 1990, 38 (3), 875-878.
16. European Commission Report. Commission Directive 94/37/EC of 22 July 1994 amending Council Directive 91/414/EEC concerning the placing of plant protection products on the market, 1994, pp 0065-0081.
17. Dimou, A. D.; Sakkas, V. A.; Albanis, T. A. Trifluralin photolysis in natural waters and under the presence of isolated organic matter and nitrate ions: Kinetics and photoproduct analysis. J. Photochem. Photobiol., A 2004, 163 (3), 473-480.
18. Machado, F.; Boule, P. Photonitration and photonitrosation of phenolic derivatives induced in aqueous-solution by excitation of nitrite and nitrate ions. J. Photochem. Photobiol., A 1995, 86 (1-3), 73-80.
19. Andreozzi, R.; Raffaele, M.; Nicklas, P. Pharmaceuticals in STP effluents and their solar photodegradation in aquatic environment. Chemosphere 2003, 50 (10), 1319-1330.
20. Chaabane, H.; Vulliet, E.; Joux, F.; Lantoine, F.; Conan, P.; Cooper, J.-F.; Coste, C.-M. Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms. Water Res. 2007, 41, 1781-1789.
21. Galichet, F.; Mailhot, G.; Bonnemoy, F.; Bohatier, J.; Boite, M. Iron(III) photo-induced degradation of isoproturon: Correlation between degradation and toxicity. Pest Manage. Sci. 2002, 58 (7), 707-712.
22. Boule, P. The handbook of environmental chemistry, Vol. II, Part L: Reactions and processes: Environmental photochemistry; SpringerVerlag: Berlin, 1999; p 359.
23. Sandín-España, P.; González-Blázquez, J. J.; Magrans, J. O.; García-Baudín, J. M. Determination of herbicide tepraloxydim and main metabolites in drinking water by solid-phase extraction and liquid chromatography with UV detection. Chromatographia 2002, 55(11/12), 681-686.
24. Curtin, D. Y.; Grubbs, E. J.; McCarty, C. G. Uncatalysed syn-anti isomerization of imines, oxime ethers, and haloimines. J. Am. Chem. Soc. 1966, 88 (12), 2775-2786.
25. Khmel'nitskii, R. A.; Efremov, Yu. A. Rearrangements in sulphoxides and sulphones induced by electron impact. Russ. Chem. Rev. 1977, 46 (1), 83-111.
26. Ono, S.; Shiotani, H.; Ishihara, K.; Tokieda, M.; Soeda, Y. Degradation of the herbicide alloxydim-sodium in soil. J. Pestic. Sci. 1984, 9 (3), 471-480.
27. Hashimoto, Y.; Ishihara, K.; Soeda, Y. Fate of alloxydim-sodium on or in soybean plants. J. Pestic. Sci. 1979, 4 (3), 299-304.
28. 14C-alloxydim-sodium in sugar beets. J. Pestic. Sci. 1979, 4 (2), 121-128.
29. Pasto, D. J.; Cottard, F.; Jumelle, L. Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative C-S bond cleavage and rearrangement reactions. J. Am. Chem. Soc. 1994, 116 (20), 8978-8984.
30. Sheu, C.; Foote, C. S.; Gu, C.-L. Photooxidation of 1,5- dithiacyclooctane. A novel carbon-sulfur bond cleavage. J. Am. Chem. Soc. 1992, 114 (8), 3015-3021.