Degradation of alachlor in natural and sludge-amended soils, studied by gas and liquid chromatography coupled to mass spectrometry (GC-MS and HPLC-MS)

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 24, 2005, Pages 9571-9577

  Rodríguez Cruz, Sonia ^a,b   Lacorte, Silvia ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b INSTITUTO DE RECURSOS NATURALES Y AGROBIOLOGÍA DE SALAMANCA   (Spain)

Author keywords

Alachlor; Alachlor ESA; Degradation; GC MS; HPLC MS; Soil

Indexed keywords

ACETAMIDE DERIVATIVE; ALACHLOR; ALKANESULFONIC ACID; ETHANE SULFONATE; HERBICIDE;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; POLLUTION; SEWAGE; SOIL; STEREOISOMERISM;

ACETAMIDES; ALKANESULFONATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENVIRONMENTAL POLLUTION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HERBICIDES; KINETICS; MASS SPECTROMETRY; SEWAGE; SOIL; STEREOISOMERISM;

EID: 28944436817     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf051920+     Document Type: Article

References (35)

1. Barceló, D.; Chiron, S.; Fernández-Alba, A.; Valverde, A.; Alpendurada, M. F. Monitoring pesticides and metabolites in surface water and groundwater in Spain. Herbicide metabolites in surface water and groundwater. ACS Symp. Ser. 1996, 630, 237-253.
2. Spalding, R. F.; Exner, M. E.; Snow, D. D.; Casada, D. A.; Burbach, M. E.; Monson, S. J. Herbicides in ground water beneath Nebraska's management systems evaluation area. J. Environ. Qual. 2003, 32, 92-99.
3. Sánchez-Brunete, C.; Martínez, L.; Tadeo, J. L. Determination of corn herbicides by GC-MS and GC-NPD in environmental samples. J. Agric. Food Chem. 1994, 42, 2210-2214.
4. Carabias Martínez, R.; Rodríguez Gonzalo, E., Fernández Laespada, M. E.; Sánchez San Román, F. J. Evaluation of surface- and ground-water pollution due to herbicides in agricultural areas of Zamora and Salamanca (Spain). J. Chromatogr., A 2000, 869, 471-480.
5. Sánchez-Camazano, M.; Lorenzo, L. F.; Sánchez- Martín, M. J. Atrazine and alachlor inputs to surface and ground waters in irrigated corn cultivation areas of Castilla-Leon region, Spain. Environ. Monit. Assess. 2005, 105, 11-24.
6. Guo, L.; Bicki, T. J.; Felsot, A.; Hinesly, T. D. Sorption and movement of alachlor in soil modified by carbon-rich wastes. J. Environ. Qual. 1993, 22, 186-194.
7. Senesi, N.; Brunetti, G.; La Cava, P.; Miano, T. M. Adsorption of alachlor by humic acids from sewage sludge and amended and non-amended soils. Soil Sci. 1994, 157, 176-184.
8. Wang, Q. Q.; Lemley, A. T. Kinetic effect of humic acid on alachlor degradation by anodic fenton treatment. J. Environ. Qual. 2004, 33, 2342-2352.
9. Aga, D. S.; Thurman, E. M. Formation and transport of the sulfonic acid metabolites of alachlor and metolachlor in soil. Environ. Sci. Technol. 2001, 35, 2455-2460.
10. Müller, M. D.; Buser, H.-R. Environmental behaviour of acetamide pesticide stereoisomers. 2. Stereo- and enantioselective degradation in sewage sludge and soil. Environ. Sci. Technol. 1995, 29, 2031-2037.
11. Fava, L.; Bottoni, P.; Crobe, A.; Funari, E. Leaching properties of some degradation products of alachlor and metolachlor. Chemosphere 2000, 41, 1503-1508.
12. Al-Khatib, K.; Braumgartner Unland, J.; Olson, B. L. S.; Graham, D. W. Alachlor and metolachlor transformation pattern in corn and soil. Weed Sci. 2002, 50, 581-586.
13. Stamper, D. M.; Tuovinen, O. H. Biodegradation of the acetanilide herbicides alachlor, metolachlor, and propachlor. Crit. Rev. Microb. 1998, 24, 1-22.
14. Walker, A.; Moon, Y. H.; Welch, S. J. Influence of temperature, soil-moisture, and soil characteristics on the persistence of alachlor. Pestic. Sci. 1992, 35, 109-116.
15. Júrado-Expósito, M.; Walker, A. Degradation of isoproturon, propyzamide, and alachlor in soil with constant and variable incubation conditions. Weed Res. 1998, 38, 309-318.
16. Clay, S. A.; Clay, D. E.; Moorman, T. B. Comparison of atrazine and alachlor sorption, mineralization, and degradation potential in surface and aquifer sediments. Pesticide decontamination and detoxification. ACS Symp. Ser. 2004, 863, 199-212.
17. Ferrer, I.; Thurman, E. M.; Barceló, D. Identification of ionic chloroacetanilide-herbicide metabolites in surface water and groundwater by HPLC/MS using negative ion spray. Anal. Chem. 1997, 69, 4547-4553.
18. Kalkhoff, S. J.; Kolpin, D. W.; Thurman, E. M.; Ferrer, I.; Barcelo, D. Degradation of chloroacetanilide herbicides: The prevalence of sulfonic and oxanilic acid metabolites in Iowa groundwaters and surface waters. Environ. Sci. Technol. 1998, 32, 1738-1740.
19. Fuhrman, J. D.; Allan, J. M. Determination of acetanilide degradates in ground and surface waters by direct aqueous injection LC/MS/MS. Liquid chromatography/mass spectrometry, MS/MS, and time-of-flight MS. ACS Symp. Ser. 2003, 850, 256-272.
20. Chesters, G.; Simsiman, G. V.; Levy, J.; Alhajjar, B. J.; Rathulla, R. N.; Harkin, J. M. Environmental fate of alachlor and metolachlor. Rev. Environ. Contam. Toxicol. 1989, 110, 1-74.
21. Ministerio de Agricultura, Pesca, y Alimentación. Métodos Oficiales de Análisis; Dirección General de Política Alimentaria: Madrid, España, 1986.
22. Thurman, E. M.; Ferrer, I.; Parry, R. Accurate mass analysis of ethanesulfonic acid degradates of acetochlor and alachlor using high-performance liquid chromatography and time-of-flight mass spectrometry. J. Chromatogr., A 2002, 957, 3-9.
23. Mangiapan, S.; Benfenati, E.; Grasso, P.; Terreni, M.; Pregnolato, M.; Pagani, G.; Barceló, D. Metabolites of alachlor in water: Identification by mass spectrometry and chemical synthesis. Environ. Sci. Technol. 1997, 31, 3637-3646.
24. Durares Sette, L.; Mendoca Alves da Costa, L. A.; Marsaioli, A. J.; Manfio, G. P. Biodegradation of alachlor by soil streptomycetes. Appl. Microbiol. Biotechnol. 2004, 64, 712-717.
25. Gonçalves, C.; Alpendurada, M. F. Assessment of pesticide contamination in soil samples from an intensive horticulture area, using ultrasonic extraction and gas chromatography-mass spectrometry. Talanta 2005, 65, 1179-1189.
26. González, S.; Petrovic, M.; Barceló, D. Simultaneous extraction and fate of linear alkylbenzene sulfonates, coconut diethanol amides, nonylphenol ethoxylates, and their degradation products in wastewater treatment plants, receiving coastal waters, and sediments in the Catalonian area (NE Spain). J. Chromatogr., A 2004, 1052, 111-120.
27. Cardoza L. A.; Cutak, B. J.; Setter, J.; Larive, C. K. High-performance liquid chromatographic-nuclear magnetic resonance investigation of the isomerization of alachlor-ethanesulfonic acid. J. Chromatogr., A 2004, 1022, 131-137.
28. 1H NMR spectroscopy. Environ. Sci. Technol. 1999, 33, 3462-3468.
29. Vargo, J. D. Determination of chloroacetanilide and chloroacetamide herbicides and their polar degradation products in water by LC/MS/MS. Liquid chromatography/mass spectrometry, MS/MS, and time-of-flight MS. ACS Symp. Ser. 2003, 850, 238-255.
30. Dorado, J.; Lopez-Fando, C.; Zancada, M.-C.; Almendros, G. Sorption-desorption of alachlor and linuron in a semiarid soil as influenced by organic matter properties alter 16 years of periodic inputs. J. Agric. Food Chem. 2005, 53, 5359-5365.
31. Patakioutas, G.; Albanis, T. A. Adsorption-desorption studies of alachlor, metolachlor, EPTC, chlorothalonil, and pirimiphosmethyl in contrasting soils. Pest Manage. Sci. 2002, 58, 352-362.
32. Torrents, A.; Jayasundera, S.; Schmidt, W. J. Influence of the polarity of organic matter on the sorption of acetamide pesticides. J. Agric. Food Chem. 1997, 45, 3320-3325.
33. Humburg, N. E.; Colby, S. R.; Hill, E. R.; Kitchen, L. M.; Lym, R. G.; McAvoy, W. J.; Prasad, R. Herbicide Handbook of the Weed Science Society of America, 6th ed.; Weed Science Society of America: Champaign, IL, 1989.
34. Chiron, S.; Abian, J.; Ferrer, M.; Sanchez-Baeza, F.; Messeguer, A.; Barcelo, D. Comparative photodegradation rates of alachlor and bentazone in natural water and determination of breakdown products. Environ. Toxicol. Chem. 1995, 14, 1287-1298.
35. Locke, M. A.; Gaston, L. A.; Zablotowicz, R. M. Alachlor biotransformation and sorption in soil from two soybean tillage systems. J. Agric. Food Chem. 1996, 44, 1128-1134.