Hostname: page-component-745bb68f8f-f46jp Total loading time: 0 Render date: 2025-01-09T21:37:03.424Z Has data issue: false hasContentIssue false
  • English
  • Français

Disappearance of s-Triazines as Affected by Soil pH Using a Balance-Sheet Approach

Published online by Cambridge University Press:  12 June 2017

J. A. Best  and
J. B. Weber
J. A. Best
Affiliation:
Velsicol Chemical Corp., W. Des Moines, IA
J. B. Weber
Affiliation:
Crop Sci. Dept., North Carolina State University, Raleigh, NC 27607
Get access Rights & Permissions [Opens in a new window]

Abstract

The effect of soil pH on the disappearance of 14C ring-labeled atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine], hydroxyatrazine [2-hydroxy-4-(ethylamino)-6-(isopropylamino)-s-triazine], and prometryne [2,4-bis(isopropylamino)-6-(methylthio)-s-triazine] were studied over a 5-month period in a Bladen silt loam soil under greenhouse conditions. Employment of an integrated system allowed simultaneous monitoring of degradation, volatilization, respiration, plant uptake, and leaching processes. A resulting balance-sheet indicated that a range of 87 to 99% of the 14C added could be accounted for after 5 months. Degradation was found to be the primary mode of dissipation. The pattern of atrazine degradation was characteristic of nonbiological processes, while prometryne degradation was probably by microbial action. Hydroxyatrazine was the major metabolite from the atrazine treatments while prometryne yielded an unknown and hydroxypropazine [2-hydroxy-4,6-bis(isopropylamino)-s-triazine]. Ex-tractable atrazine after 5 months amounted to 35% of the initial amount added in the pH 7.5 soil and 11% in the pH 5.5 soil, while prometryne occurred as 10% in the pH 7.5 soil and 42% in the pH 5.5 soil. Plant uptake and leaching occurred to a greater extent in the more alkaline soil with each chemical, but these pathways along with volatilization and respiration were minor contributors toward the disappearance of these herbicides.

Type
Research Article
Information
Weed Science , Volume 22 , Issue 4 , July 1974 , pp. 364 - 373
Copyright
Copyright © 1974 by the Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

1. Armstrong, D.E. and Chester, G. 1967. Atrazine hydrolysis in soil. Soil Sci. Soc. Amer. Proc. 31:61–66.Google Scholar
2. Ashton, F.M. and Crafts, A.S. 1973. Triazines, pages 310–346, in Mode of Action of herbicides. Wiley and Sons, Inc., New York.Google Scholar
3. Bailey, G.W., White, J.L., and Rothberg, T. 1968. Adsorption of organic herbicides by montmorillonite: Role of pH and chemical character of adsorbate. Soil Sci. Soc. Amer. Proc. 32:222–234.Google Scholar
4. Birk, L.A. and Roadhouse, F.E.B. 1964. Penetration of and persistance in soil of the herbicide atrazine. Can. J. Plant Sci. 44:21–27.Google Scholar
5. Broadbent, F.E. and Bradford, G.R. 1952. Cation-exchange groupings in the soil organic fraction. Soil Sci. 74:447–457.Google Scholar
6. Burnside, O.C., Fenster, C.R., and Wicks, G.A. 1971. Soil persistence of repeated annual application of atrazine. Weed Sci. 19:290–293.Google Scholar
7. Burnside, O.C., Fenster, C.R., Wicks, G.A., and Drew, J.V. 1969. Effect of soil and climate on herbicide dissipation. Weed Sci. 17:241–245.CrossRefGoogle Scholar
8. Burnside, O.C., Wicks, G.A., and Fenster, C.R. 1965. Herbicide longevity in Nebraska soils. Weeds 13:277–278.Google Scholar
9. Davis, D.E., Gramlich, J.V., and Funderburk, H.H. Jr. 1965. Atrazine absorption and degradation by corn, cotton, and soybeans. Weeds 13:252–255.Google Scholar
10. Gysin, H. 1962. Triazine herbicides, their chemistry, biological properties and mode of action. Chem. Ind. (London), 1393–1400.Google Scholar
11. Harris, C.I. 1967. Fate of 2-chloro-s-triazines in soil. J. Agr. Food Chem. 15:157–162.Google Scholar
12. Harris, C.I., Kaufman, D.D., Sheets, T.J., Nash, R.G., and Kearney, P.C. 1968. Behavior and fate of s-triazines in soils. Adv. Pest. Contr. Res. 8:1–56.Google Scholar
13. Hauck, R.D. and Stephenson, F.F. 1964. Nitrification of triazine nitrogen. J. Agr. Food Chem. 12:147–150.CrossRefGoogle Scholar
14. Hayes, M.H.B. 1970. Adsorption of triazine herbicides on soil organic matter, including a short review on soil organic matter chemistry. Res. Rev. 32:131–176.Google Scholar
15. Horrobin, S. 1963. The hydrolysis of some 1,3,5-triazines: Mechanism, structure and reactivity. J. Chem. Soc. 4130–4135.Google Scholar
16. Kamprath, E.J. and Welch, C.D. 1962. Retention and cation-exchange properties of organic matter in Coastal Plain soils. Soil Sci. Soc. Amer. Proc. 26:263–265.Google Scholar
17. Kaufman, D.D. and Kearney, P.C. 1970. Microbial degradation of triazine herbicides. Res. Rev. 32:234–266.Google Scholar
18. Kearney, P.C. and Plimmer, J.R. 1969. Prometryne degradation in soils and light. Abstracts, 158th Amer. Chem. Soc. Meetings, New York., Sept. 8–12.Google Scholar
19. Knusli, E., Berrer, D., Dupuis, G., and Esser, H. 1969. s-Triazines. Pages 51–78 in Kearney, P.C. and Kaufman, D.D. (ed.), Degradation of herbicides. Marcel Dekker, Inc., New York.Google Scholar
20. Kononova, M.M. 1966. Soil organic matter. 2nd Ed. Pergamon Press, Inc., New York. 450 pp.Google Scholar
21. Baron, H.M. Le 1970. Ways and means to influence the activity and the persistence of triazine herbicides in soils. Res. Rev. 32:311–353.Google Scholar
22. Montgomery, M.L. and Freed, V.H. 1964. Metabolism of triazine herbicides by plants. J. Agr. Food Chem. 12:11–14.Google Scholar
23. Morrison, R.T. and Boyd, R.N. 1972. Organic chemistry. 2nd ed., Allyn and Bacon, Inc., Boston, Mass. 1204 pp.Google Scholar
24. Nearpass, D.C. 1965. Effects of soil acidity on the adsorption penetration, and persistence of simazine. Weeds 13:341–346.Google Scholar
25. Negi, N.S., Funderburk, H.H. Jr., and Davis, D.E. 1964. Metabolism of atrazine by susceptible and resistant plants. Weeds 12:53–57.Google Scholar
26. Sheets, T.J. 1970. Persistence of triazine herbicides in soils. Res. Rev. 32:287–310.Google Scholar
27. Sheets, T.J. and Shaw, W.C. 1963. Herbicidal properties and persistence in soils of s-triazines. Weeds 11:15–21.Google Scholar
28. Shimabukuro, R.H., Frear, D.S., Swanson, H.R., and Walsh, W.C. 1971. Glutathione conjugation, an enzymatic basis for atrazine resistance in corn. Plant Physiol. 47:10–14.Google Scholar
29. Sikka, H.C. and Davis, D.E. 1966. Dissipation of atrazine from soil by corn, sorghum and johnsongrass. Weeds 14:289–293.CrossRefGoogle Scholar
30. Skipper, H.D., Gilmour, C.M., and Furtick, W.R. 1967. Microbial versus chemical degradation of atrazine in soils. Soil Sci. Soc. Amer. Proc. 31:653–656.Google Scholar
31. Skipper, H.D. and Volk, V.V. 1972. Biological and chemical degradation of atrazine in three Oregon soils. Weed Sci. 20:344–347.Google Scholar
32. Stevenson, F.J. and Butler, J.H.A. 1969. Chemistry and humic acids and related pigments. Pages 534–557 in Eglinton, G. and Murphy, M.J.T., eds. Organic geochemistry. Springer-Verlag, New York.CrossRefGoogle Scholar
33. Weber, J.B. 1967. Spectrophotometrically determined ionization constants of 13-alkylamino-s-triazines and the relationships of molecular structure and basicity. Spectrochimica Acta 23A:458–461.CrossRefGoogle Scholar
34. Weber, J.B. 1970. Mechanisms of adsorption of s-triazines by clay colloids and factors affecting plant availability. Res. Rev. 32:93–130.Google Scholar
35. Weber, J.B. 1972. Interaction of organic pesticides with particulate matter in aquatic and soil systems. Adv. Chem. Ser. 111:55–120.Google Scholar
36. Weber, J.B. and Best, J.A. 1972. Activity and movement of 13 soil-applied herbicides as influenced by soil reaction. Proc. S. Weed Sci. Soc. 25:403–413.Google Scholar
37. Weber, J.B., Perry, P.W., and Ibaraki, K. 1968. Effect of pH on the phytotoxicity of prometryne applied to synthetic soil media. Weed Sci. 16:134–136.Google Scholar
38. Weber, J.B., Weed, S.B., and Ward, T.M. 1969. Adsorption of s-triazines by soil organic matter. Weed Sci. 17:417–421.Google Scholar
39. Wershaw, R.L. and Goldberg, M.C. 1972. Interaction of organic pesticides with natural organic polyelectrolytes. Adv. Chem. Ser. 111:149–158.Google Scholar
40. White, J.L. and Cruz, M. 1971. The role of soil colloids in the behavior and fate of pesticides in soils. Pest. Chem. 6:23–45.Google Scholar
41. Whittenburg, D.C. 1965. Fate of prometryne in cotton plants. Weeds 13:68–71.CrossRefGoogle Scholar
42. Worsham, A.D. 1967. Safe use of herbicides. Proc. W. Weed Control Conf. 21:20–22.Google Scholar