Soil Adsorption Coefficients of s-Triazines Estimated with a New Gradient HPLC Method

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 1, 1998, Pages 335-343

  Kaune, A ^a,b   Bruggemann R ^b,c   Sharma, M ^b   Kettrup, A ^a,b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b INSTITUTE OF EPIDEMIOLOGY   (Germany)

^c LEIBNIZ INSTITUTE OF FRESHWATER ECOLOGY AND INLAND FISHERIES   (Germany)

Author keywords

Keto enol tautomerism; Octanol water partition coefficient; Pesticides; Sorption; Symmetrical triazines

Indexed keywords

EID: 0345170252     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9704930     Document Type: Article

References (52)

1. Armstrong, D. E.; Chesters, G.; Harris, R. F. Atrazine hydrolysis in soil. Soil Sci. Soc. Am. Proc. 1967, 31, 61-66.
2. Bailey, G. W.; White, J. L.; Rothberg, T. Adsorption of organic herbicides by montmorillonite: role of pH and chemical character of adsorbate. Soil Sci. Soc. Am. Proc. 1968, 32, 222-234.
3. Bottoni, P.; Keizer, J.; Funari, E. Leaching indices of some major triazine metabolites. Chemosphere 1996, 32, 1401-1411.
4. Bowman, B. T. Mobility and dissipation studies of metribuzin, atrazine and their metabolites in plainfield sand using field lysimeters. Environ. Toxicol. Chem. 1991, 10, 573-579.
5. Briggs, G. G. Theoretical and experimental relationships between soil adsorption, octanol-water partition coefficients, water solubilities, bioconcentration factors, and the parachor. J. Agric. Food Chem. 1981, 29, 1050-1059.
6. Brouwer, W. W. M.; Boesten, J. J. T. I.; Siegers, W. G. Adsorption of transformation products of atrazine by soil. Weed Res. 1990, 30, 123-128.
7. Chung, K. H.; Ro, K. S.; Ondrus, M. G. Adsorption and extraction of hydroxyatrazine from wetland sediment. J. Environ. Sci. Health A 1994, 29, 1577-1586.
8. Clay, S. A.; Allmara, R. R.; Koskinen, W. C.; Wyse, D. L. Desorption of atrazine and cyanazine from soil. J. Environ. Qual. 1988, 17, 719-723.
9. Dieckmann, H.; Kreuzig, R.; Bahadir, M. Significance of ketoenol-tautomery in the analysis of 1,2,4-triazinone metabolites. Fresenius' J. Anal. Chem. 1994, 348, 749-753.
10. oc estimation of deethylatrazine, deisopropylatrazine, hexazinone and terbuthylazine by reversed phase chromatography and sorption isotherms. Toxicol. Environ. Chem. 1994, 44, 1-10.
11. Engelhardt, H.; Ahr, G. Properties of chemically bonded phases. Chromatographia 1981, 14, 227-233.
12. Erickson, L. E.; Lee, K. H. Degradation of atrazine and related s-triazines. Crit. Rev. Environ. Control 1989, 19, 1-14.
13. Ernst, C.; Rehm, H.-J. Utilization of chlorinated s-triazines by a new strain of Klebsiella pneumoniae. Appl. Microbiol. Biotechnol. 1995, 42, 763-768.
14. Gerstl, Z. Estimation of organic chemical sorption by soils. J. Contam. Hydrol. 1990, 6, 357-375.
15. Goss, K.-U.; Schramm, K.-W. Determination of effective diffusion coefficients for gaseous and dissolved organic substances in soil material using a "stopped elution" method with HPLC and GC. J. Soil Sci. 1991, 42, 47-58.
16. Green, R. E.; Davidson, J. M.; Biggar, J. W. An assessment of methods for determining adsorption-desorption of organic chemicals. In Agrochemicals in Soils; Banin, A., Kafkafi, V., Eds.; Pergamon Press: New York, 1980; pp 73-82.
17. Grossenbacher, H.; Horn, C.; Cook, A. M.; Hütter, R. 2-Chloro-4-amino-1,3,5-triazine-6(5H)-one: a new intermediate in the biodegradation of chlorinated s-triazines. Appl. Environ. Microbiol. 1984, 48, 451-453.
18. oc) for soils by high performance liquid chromatography. Chemosphere 1988, 17, 67-77.
19. oc) for aromatic compounds by HPLC retention factors (k′). Chemosphere 1996, 32, 343-351.
20. Karickhoff, S. W. Semi-empirical estimation of sorption of hydrophobic pollutants on natural sediments and soils. Chemosphere 1981, 10, 833-846.
21. Kaune, A. Quantitative Struktur-Wirkungsbeziehungen zur Modellierung der Mineralisierung ausgewählter Triazine im Boden. Ph.D. Thesis, Technische Universität München, Munich, Germany, 1997.
22. Kördel, W.; Stutte, J.; Kotthoff, G. HPLC screening method for the determination of the adsorption-coefficient on soil - comparison of different stationary phases. Chemosphere 1993, 27, 2341-2352.
23. Kördel, W.; Kotthoff, G.; Müller, J. HPLC-screening method for the determination of the adsorption-coefficient on soil - results of a ring test. Chemosphere 1995, 30, 1373-1384.
24. Kruger, E. L.; Zhu, B. L.; Coats, J. R. Relative mobilities of atrazine, five atrazine degradates, metolachlor, and simazine in soils of Iowa. Environ. Toxicol. Chem. 1996, 15, 691-695.
25. oct from Structures. Chem. Rev. (Washington, D.C.) 1993, 93, 1281-1306.
26. Liu, J.; Qian, C. Hydrophobic coefficients of s-triazine and phenylurea herbicides. Chemosphere 1995, 31, 3951-3959.
27. Mandelbaum, R. T.; Wackett, L. P.; Allan, D. L. Rapid hydrolysis of atrazine to hydroxyatrazine by soil bacteria. Environ. Sci. Technol. 1993, 27, 1943-1946.
28. Mersie, W.; Seybold, C. Adsorption and desorption of atrazine, deethylatrazine, deisopropylatrazine, and hydroxyatrazine on Levy wetland soil. J. Agric. Food Chem. 1996, 44, 1925-1929.
29. Meylan, W.; Howard, P. H.; Boethling, R. S. Molecular topology/fragment contribution method for predicting soil sorption coefficients. Environ. Sci. Technol. 1992, 26, 1560-1567.
30. Mills, M. S.; Thurman, E. M. Reduction of nonpoint source contamination of surface water and groundwater by starch encapsulation of herbicides. Environ. Sci. Technol. 1994, 28, 73-79.
31. Müller, M.; Kördel, W. Comparison of screening methods for the estimation of adsorption coefficients on soil. Chemosphere 1996, 32, 2493-2504.
32. Nearpass, D. C. Effects of soil acidity on the adsorption, penetration and persistence of simazine. Weeds 1965, 13, 341-346.
33. OECD. OECD guidelines for testing of chemicals, test guideline 106 adsorption-desorption in soils; Paris, 1981.
34. Pote, D. H.; Daniel, T. C.; Edwards, D. R.; Mattice, J. D.; Wickliff, D. B. Effect of drying and rainfall intensity on cyromazine loss from surface-applied caged-layer manure. J. Environ. Qual. 1994, 23, 101-104.
35. oc of 14 triazole fungicides using a "humic acid" HPLC column. In Humic Substances in the Global Environment and Implications on Human Health; Senesi, N., Miano, T. M., Eds.; Elsevier: Amsterdam, 1994; pp 1037-1042.
36. oc) of substituted phenylureas: QSAR models. Chemosphere 1994, 28, 1929-1941.
37. Rippen, G. Handbuch Umweltchemikalien: Stoffdaten, Prüfund Nachweisverfahren, Vorschriften, Richtlinien, 2nd ed.; ecomed Verlag: Landsberg/Lech, Germany, 1987.
38. Roda, A.; Minutello, A.; Angellotti, M. A.; Fini, A. Bile acid structure-activity relationship: evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. J. Lipid Res. 1990, 31, 1433-1443.
39. Roy, W. R.; Krapac, I. G. Adsorption and desorption of atrazine and deethylatrazine by low organic carbon geologic materials. J. Environ. Qual. 1994, 23, 549-556.
40. Russel, J. D.; Cruz, M.; White, J. L.; Bailey, G. W.; Payne, W. R.; Pope, J. D.; Teasley, J. I. Mode of chemical degradation of s-triazines by montmorillonite. Science 1968, 160, 1340-1342.
41. Sabljic, A. On the prediction of soil sorption coefficients of organic pollutants from molecular structure: application of molecular topology model. Environ. Sci. Technol. 1987, 21, 358-366.
42. ow correlations. Chemosphere 1995, 31, 4489-4514; correction published in Chemosphere 1996, 32, 805.
43. Singh, G.; Spencer, W. F.; Cliath, M. M.; van Genuchten, M. Th. Sorption behaviour of s-triazine and thiocarbamate herbicides on soils. J. Environ. Qual. 1990, 19, 520-525.
44. Smolin, E. M.; Rapoport, L. s-Triazines and Derivatives; Interscience Publishers: New York, 1959.
45. Solomon, K. R.; Baker, D. B.; Richards, P.; Dixon, K. R.; Klaine, S. J.; La Point, T. W.; Kendall, R. J.; Weisskopf, C. P.; Giddings, J. M.; Giesy, J. P.; Hall, L. W.; Williams, W. M. Ecological risk assessment of atrazine in North American surface waters. Environ. Taxicol. Chem. 1996, 15, 31-76.
46. Somasundaram, L.; Coats, J. R.; Racke, K. D. Mobility of pesticides and their hydrolysis metabolites in soil. Environ. Toxicol. Chem. 1991, 10, 185-194.
47. Szabó, G.; Guczi, J.; Bulman, R. A. Examination of silicasalicylic acid and silica-8-hydroxyquinoline HPLC stationary phases for estimation of the adsorption coefficient of soil for some aromatic hydrocarbons. Chemosphere 1995, 30, 1717-1727.
48. Wang, Y.; Pittman, C. U.; Saebo, S. Investigation of the structure and the properties of ammeline, melamine, and 2,4-diamino-1,3,5-triazine by ab initio calculations. J. Org. Chem. 1993, 58, 3085-3090.
49. Wang, Z.; Gamble, D. S.; Langford, C. H. Interaction of atrazine with Laurentian soil. Environ. Sci. Technol. 1992, 26, 560-565.
50. Weber, J. B. Molecular structure and pH effects on the adsorption of 13 s-triazine compounds on montmorillonite clay. Am. Mineral. 1966, 51, 1657-1670.
51. Weber, J. B. Adsorption of s-triazines by montmorillonite as a function of pH and molecular structure. Soil Sci. Soc. Am. Proc. 1970, 34, 401-404.
52. Worthing, C. R., Ed. The Pesticide Manual. A World Compendium, 8th ed.; British Crop Protection Council: Bracknell, U.K., 1987.