Degradation of flumioxazin in illuminated water-sediment systems

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 20, 2011, Pages 11186-11195

  Shibata, Atsushi ^a   Kodaka, Rika ^a   Fujisawa, Takuo ^a   Katagi, Toshiyuki ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

flumioxazin; hydrolysis; natural water; photodegradation; water sediment system

Indexed keywords

BOTTOM SEDIMENTS; CYCLIC IMIDES; DEGRADATION PROFILES; FLUMIOXAZIN; HALF LIVES; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; MICROBIAL DEGRADATION; NATURAL WATERS; OVERLYING WATER; PHENYL RINGS; PHOTO-INDUCED; UNIFORM DISTRIBUTION; WATER LAYERS; WATER-SEDIMENT SYSTEM;

BIODEGRADATION; DEGRADATION; HYDROLYSIS; IRRADIATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTODEGRADATION; PHOTOLYSIS; RESONANCE; SEDIMENTOLOGY; SULFUR COMPOUNDS;

ANOXIC SEDIMENTS;

BENZOXAZINE DERIVATIVE; FLUMIOXAZIN; HERBICIDE; PHTHALIMIDE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; LIGHT; PHOTOLYSIS; POLLUTION; SEDIMENT;

BENZOXAZINES; ENVIRONMENTAL POLLUTION; GEOLOGIC SEDIMENTS; HERBICIDES; LIGHT; PHOTOLYSIS; PHTHALIMIDES; WATER;

EID: 80055009313     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf202542v     Document Type: Article

References (33)

1. Yoshida, R.; Sakaki, M.; Sato, R.; Haga, T.; Nagano, E.; Oshio, H.; Kamoshita, K. S-53482 - a new N -phenyl phthalimide herbicide Brighton Crop Prot. Conf.-Weeds 1991, 1, 69-75
2. Vencil, W. K. Herbicide Handbook, 8 th ed.; Weed Science Society of America: Lawrence, KS, 2002; pp 200-201.
3. Katagi, T. Hydrolysis of N -phenylimide herbicide flumioxazin and its anilic acid derivative in aqueous solutions J. Pestic. Sci. 2003, 28, 44-50 (Pubitemid 36614987)
4. Kwon, J. W.; Armbrust, K. L.; Grey, T. L. Hydrolysis and photolysis of flumioxazin in aqueous buffer solutions Pest Manag. Sci. 2004, 60, 939-943 (Pubitemid 39120772)
5. Ferrell, J. A.; Vencill, W. K. Flumioxazin soil persistence and mineralization in laboratory experiments J. Agric. Food Chem. 2003, 51, 4719-4721
6. Alister, C.; Rojas, S.; Gómez, P.; Kogan, M. Dissipation and movement of flumioxazin in soil at four field sites in Chile Pest Manag. Sci. 2008, 64, 579-583 (Pubitemid 351588964)
7. Ferrell, J. A.; Vencill, W. K.; Xia, K.; Grey, T. L. Sorption and desorption of flumioxazin to soil, clay minerals and ion-exchange resin Pest Manag. Sci. 2005, 61, 40-46 (Pubitemid 40065146)
8. Tomigahara, Y.; Matsui, M.; Matsunaga, H.; Isobe, N.; Kaneko, H.; Nakatsuka, I.; Yoshitake, A.; Yamada, H. Metabolism of 7-fluoro-6-(3,4,5,6- tetrahydrophthalimido)-4-(2-propynyl)-2 H -1,4-benzoxazin-3(4 H)-one (S-53482) in rat: 1. Identification of a sulphonic acid type conjugate J. Agric. Food Chem. 1999, 47, 305-312 (Pubitemid 29179664)
9. Tomigahara, Y.; Onogi, M.; Kaneko, H.; Nakatsuka, I.; Yamane, S. Metabolism of 7-fluoro-6-(3,4,5,6-tetrahydrophthalimido)-4- (2-propynyl)-2 H -1,4-benzoxazin-3(4 H)-one (S-53482, flumioxazin) in the rat: II. Identification of reduced metabolites J. Agric. Food Chem. 1999, 47, 2429-38
10. European Commission. Working document, Guidance document on aquatic ecotoxicology Sanco/3268/2001.rev.4; European Commission, Brussels, Belgium, 2002.
11. OECD guideline for the testing of chemicals 308. Aerobic and anaerobic transformation in aquatic sediment systems; April 2002.
12. European Commission. Pyriproxifen, Existing active substance (3rd stage), Draft assessment report; European Commission, Brussels, Belgium, 2006; http://dar.efsa.europa.eu/dar-web/provision (accessed March 2011).
13. European Commission. Bensulfuron Methyl, Existing active substance (3rd stage), Draft assessment report; European Commission, Brussels, Belgium, 2007; http://dar.efsa.europa.eu/dar-web/provision (accessed March 2011).
14. Katagi, T. Behavior of pesticides in water-sediment systems Rev. Environ. Contam. Toxicol. 2006, 187, 133-251 (Pubitemid 44489859)
15. Kodaka, R.; Sugano, T.; Katagi, T.; Takimoto, Y. Aerobic aquatic metabolism of fenitrothion and its oxon analog in water-sediment systems J. Pestic. Sci. 2002, 27, 235-241 (Pubitemid 35343550)
16. Kodaka, R.; Sugano, T.; Katagi, T.; Takimoto, Y. Comparative metabolism of organophosphorus pesticides in water-sediment systems J. Pestic. Sci. 2003, 28, 175-182 (Pubitemid 37027616)
17. Aajoud, A.; Ravanel, P.; Tissut, M. Fipronil metabolism and dissipation in a simplified aquatic ecosystem J. Agric. Food Chem. 2003, 51, 1347-1352
18. Rice, P. J.; Anderson, T. A.; Coats, J. R. Effects of sediment on the fate of metolachlor and atrazine in surface water Environ. Toxicol. Chem. 2004, 23, 1145-1155 (Pubitemid 38621019)
19. Kodaka, R.; Sugano, T.; Katagi, T. Metabolism of uniconazole-P in water-sediment systems under illumination Environ. Toxicol. Chem. 2006, 25, 310-316 (Pubitemid 43134231)
20. Kwon, J. W.; Armbrust, K. L. Degradation of chlorothalonil in irradiated water/sediment systems J. Agric. Food Chem. 2006, 54, 3651-3657 (Pubitemid 43844195)
21. Kwon, J. W.; Armbrust, K. L. Laboratory persistence and fate of fluoxetine in aquatic environments Environ. Toxicol. Chem. 2006, 25, 2561-2568 (Pubitemid 44898418)
22. Kodaka, R.; Sugano, T.; Katagi, T. Degradation of esfenvalerate in illuminated water-sediment system J. Pestic. Sci. 2009, 34, 27-36
23. Kodaka, R.; Swales, S. E.; Lewis, C.; Katagi, T. Effect of illumination on degradation of pyriproxyfen in water-sediment system J. Pestic. Sci. 2011, 36, 33-40
24. van der Kolka, J. W. H.; Crum, S. J. H. Laboratory micro-ecosystems as physical models for predicting the fate of pesticides in aquatic systems Sci. Total Environ. 1993, 134, 1429-1437
25. Carton, P. R.; Allen, R. The use of a compartment model for evaluating the fate of pesticides in sediment/water system. Brighton Crop Prot. Conf.-Pest Dis. 1994, 1349-1354.
26. FOCUS Degradation Kinetics Workgroup. Degradation Kinetics Spreadsheet V2, Degradation Kinetics Software; European Commission, Brussels, Belgium; http://focus.jrc.ec.europa.eu/dk/software.html (accessed March 2011).
27. Burrows, H. D.; Canle, M.; Santaballa, J. A.; Steenken, S. Reaction pathways and mechanisms of photodegradation of pesticides J. Photochem. Photobiol. B: Biol. 2002, 67, 71-108 (Pubitemid 34746524)
28. Katagi, T. Photodegradation of pesticides on plant and soil surfaces Rev. Environ. Contam. Toxicol. 2004, 182, 1-195
29. Rayne, S.; Forest, K.; Friesen, K. J. Mechanistic aspects regarding the direct aqueous environmental photochemistry of phenol and its simple halogenated derivatives. A review Environ. Int. 2009, 35, 425-37
30. Katagi, T. Photodegradation of esfenvalerate in clay suspensions J. Agric. Food Chem. 1993, 41, 2178-2183 (Pubitemid 2007067)
31. 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 Photochem. Photobiol. A 2004, 163, 473-480
32. Estimation Programs Interface Suite for Microsoft® Windows, v 4.00; U.S. Environmental Protection Agency, Washington, DC; http://www.epa.gov/oppt/ exposure/pubs/episuite.htm (accessed March 2011).
33. Parris, G. E. Environmental and metabolic transformations of primary aromatic amines and related compounds Residue Rev. 1980, 76, 1-30