Influence of humic acid on adsorption and desorption of atrazine, hydroxyatrazine, deethylatrazine, and deisopropylatrazine onto a clay-rich soil sample

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 22, 2004, Pages 6747-6754

  Abate, Gilberto ^a   Penteado, José C ^a   Cuzzi, Jonas D ^a   Vitti, Godofredo C ^a   Lichtig, Jaim ^a   Masini, Jorge C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Adsorption; Atrazine; Atrazine metabolites; Humic acid; Soil

Indexed keywords

2 AMINO 4 CHLORO 6 ETHYLAMINO 1,3,5 TRIAZINE; ATRAZINE; DEETHYLATRAZINE; HUMIC ACID; HYDROXYATRAZINE; ORGANIC MATTER; UNCLASSIFIED DRUG;

ADSORPTION; AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CONCENTRATION RESPONSE; DESORPTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LEACHING; SAMPLING;

ADSORPTION; ALUMINUM SILICATES; ATRAZINE; HUMIC SUBSTANCES; HYDROXYLATION; SOIL; TRIAZINES;

EID: 7244234149     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf049229e     Document Type: Article

References (43)

1. Queiroz, M. E. C.; Lanças, F. M. HRGC study of sorption and desorption of atrazine, ametryn and metolachlor on Brazilian soils. J. Braz. Chem. Soc. 1997, 8, 1-6.
2. Graymore, M.; Stagnitti, F.; Allinson, G. Impacts of atrazine in aquatic ecosystems. Environ. Int. 2001, 26, 483-495.
3. Wang, Z.; Gamble, D. S.; Langford, C. H. Interaction of atrazine with Laurentian Soil. Environ. Sci. Technol. 1992, 26, 560-565.
4. Koskinen, W. C.; Rochette, E. A. Atrazine sorption-desorption in field-moist soils. Int. J. Environ. Anal. Chem. 1996, 65, 223-230.
5. Townsend, M. A.; Young, D. P. Atrazine and its metabolites as indicators of stream-aquifer interactions in Kansas, U.S.A. Int. J. Anal. Chem. 2000, 78, 9-23.
6. Laabs, V.; Amelung, W.; Pinto, A.; Altstaedt, A.; Zech, W. Leaching and degradation of corn and soybean pesticides in an Oxisol of the Brazilian Cerrados. Chemosphere 2000, 41, 1441-1449.
7. Moorman, T. B.; Jayachandran, K.; Reungsang, A. Adsorption and desorption of atrazine in soils and subsurface sediments. Soil Sci. 2001, 166, 921-929.
8. Loiseau, L.; Barriuso, E. Characterization of the atrazine's bound (nonextractable) residues using fractionation techniques for soil organic matter. Environ. Sci. Technol. 2002, 36, 683-689.
9. Kolpin, D. W.; Thurman, E. M.; Linhart, S. M. Finding minimal herbicide concentrations in groundwater? Try looking for their degradates. Sci. Total Environ. 2000, 248, 115-122.
10. Panshin, S. Y.; Carter, D. S.; Bayless, E. R. Analysis of atrazine and four degradation products in the pore water of the vadose zone, Central Indiana. Environ. Sci. Technol. 2000, 34, 2131-2137.
11. Shipitalo, M. J.; Owens, L. B. Atrazine, deethylatrazine and deisopropylatrazine in surface runoff from conservation tilled watersheds. Environ. Sci. Technol. 2003, 37, 944-950.
12. Hayes, T. B.; Collins, A.; Lee, M.; Mendoza, M.; Noriega, N.; Stuart, A. A.; Vonk, A. Hermaphroditic, demasculinized frogs after exposure to the herbicide atrazine at low ecologically relevant doses. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5476-5480.
13. Stevenson, F. J. Humus Chemistry, Genesis, Composition, Reactions, 2nd ed.; Wiley: New York, 1994.
14. Vaidyanathan, L. V.; Eagle, D. J. The influence of organic matter and clay on adsorption of atrazine by top soils. In Advances in soil organic matter research: The impact on agriculture and the environment; Wilson, W. S., Ed.; The Royal Society of Chemistry: Cambridge, U.K., 1991; pp 381-391.
15. Javaroni, R. C. A.; Landgraf, M. D.; Rezende, M. O. O. Comportamento dos Herbicidas atrazina e alaclor aplicados em solo preparado para o cultivo de cana-de-açúcar. Quim. Nova 1999, 22, 58-64.
16. Martin-Neto, L.; Vieira, E. M.; Sposito, G. Mechanism of atrazine sorption by humic acid- a spectroscopic study. Environ. Sci. Technol. 1994, 28, 1867-1873.
17. Sposito, G.; Martin-Neto, L.; Yang, A. Atrazine complexation by soil humic acid. J. Environ. Qual. 1996, 25, 1203-1209.
18. Martin-Neto, L.; Traghetta, D. G.; Vaz, C. M. P.; Crestana, S.; Sposito, G. On the interaction mechanisms of atrazine and hydroxiatrazine with humic substances. J. Environ. Qual. 2001, 30, 520-525.
19. Kulikova, N. A.; Perminova, I. V. Binding of atrazine to humic substances from soil, peat, and coal related to their structure. Environ. Sci. Technol. 2002, 36, 3720-3724.
20. McBride, M. B. Environmental Chemistry of Soils; Oxford University Press: New York, 1994.
21. Mersie, W.; Seybold, C. Adsorption and desorption of atrazine, deethylatrazine, deisopropilatrazine and hydroxyatrazine on Levy Wetland Soil. J. Agric. Food Chem. 1996, 44, 1925-1929.
22. Moreau-Kervevan, C.; Mouvet, C. Adsorption and desorption of atrazine deethylatrazine and hydroxyatrazine by soil components. J. Environ. Qual. 1998, 27, 46-53.
23. Krutz, J. L.; Senseman, S. A.; McInnes, K. J.; Zuberer, D. A.; Tierney, D. P. Adsorption and desorption of atrazine, desethylatrazine, deisopropylatrazine, and hydroxyatrazine in vegetated filter strip and cultivated soil. J. Agric. Food Chem. 2003, 51, 7379-7384.
24. Runes, H. B.; Jenkins, J. J.; Moore J. A.; Bottomley, P. J.; Wilson, B. D. Treatment of atrazine in nursery irrigation runoff by constructed wetland. Water Res. 2003, 37, 539-550.
25. Steinheimer, T. R. HPLC Determination of atrazine and principal degradates in agricultural soils and associated surface and groundwater. J. Agric. Food Chem. 1993, 41, 588-595.
26. Berg, M.; Müller, S. R.; Schwarzenbach, R. P. Simultaneous determination of triazines including atrazine and their major metabolites hydroxyatrazine, deethylatrazine, and deisopropylatrazine in Natural Waters. Anal. Chem. 1995, 67, 1860-1865.
27. Melfi, J. A.; Montes, C. R.; Carvalho, A. Use of pedological maps in the identification of the sensitivity of soils to acidic deposition: application to Brazilian soils. An. Acad. Bras. Cienc. 2004, 76, 139-145.
28. OECD. OECD guidelines for testing of chemicals, test guideline 106 adsorption-desorption in soils; OECD: Paris, France, 1981.
29. Vermeulen, N. M. J.; Apostolides, Z.; Potgieter, D. J. J. Separation of atrazine and some of its degradation products by high-performance liquid chromatography. J. Chromatogr. 1982, 240, 247-253.
30. Xing, B.; Pignatello, J. J.; Gigliotti, B. Competitive sorption between atrazine and other compounds in soils and model sorbents. Environ. Sci. Technol. 1996, 30, 2432-2440.
31. Pignatello, J. J.; Xing, B. Mechanisms of slow sorption of organic chemicals to natural particles. Environ. Sci. Technol. 1996, 30, 1-11.
32. Lesan, H. M.; Bhandari, A. Atrazine adsorption on surface soils: time dependent phase distribution and apparent desorption hysteresis. Water Res. 2003, 37, 1644-1654.
33. Laird, D. A.; Barriuso, E.; Dowdy, R. H.; Koskinen, W. C. Adsorption of atrazine on smectites. Soil Sci. Soc. Am. J. 1992, 56, 62-67.
34. Sheng, G.; Johnston, C. T.; Teppen, B. J.; Boyd, S. A. Potential contributions of smectite clays and organic matter to pesticide retentions in soils. J. Agric. Food Chem. 2001, 49, 2899-2907.
35. Gilchrist, G. F. R.; Gamble, D. S.; Kodama, H. Khan, S. U. Atrazine interactions with clay minerals: kinetics and equilibria of sorption. J. Agric. Food Chem. 1993, 41, 1748-1755.
36. Herwig, U.; Klumpp, E.; Narres, H.; Schwger, M. J. Physicochemical interactions between atrazine and clay minerals. Appl. Clay Sci. 2001, 18, 211-222.
37. Melo, V. F.; Singh, B.; Schaefer, C. E. G. R.; Novais, R. F.; Fontes, M. P. F. Chemical and mineralogical properties of kaolinite-rich Brazilian soils. Soil Sci. Soc. Am. J. 2001, 65, 1324-1333.
38. Mortland, M. M.; Raman, K. V. Surface acidity of smectites in relation to hydration, exchangeable cation, and structure. Clays Clay Miner. 1968, 16, 393-398.
39. Clapp, C. E.; Mingelgrin, U.; Liu, R.; Zhang, H.; Hayes, M. H. B. A quantitative estimation of the complexation of small organic molecules with soluble humic acids. J. Environ. Qual. 1997, 26, 1277-1281.
40. Liu, W.; Can, J.; Yates, S. R. Influence of herbicide structure, clay acidity, and humic acid coating on acetanilide herbicide adsorption on homoionic clays. J. Agric. Food Chem. 2002, 50, 4003-4008.
41. Wang, Z.; Gamble, D. S.; Langford, C. H. Interaction of atrazine with Laurentian fulvic acid: binding and hydrolysis. Anal. Chim. Acta 1990, 232, 181-188.
42. Lerch, R. N.; Li, Y. Analysis of hydroxylated atrazine degradation products in soils. Int. J. Environ. Anal. Chem. 2001, 79, 167-183.
43. 14C atrazine degradation products in a sandy loam soil under field conditions. Weed Sci. 1993, 41, 239-245.