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Effect of Moisture on Chlorimuron Degradation in Soil

Published online by Cambridge University Press:  12 June 2017

Thomas P. Fuesler  and
Michael K. Hanafey
Thomas P. Fuesler
Affiliation:
Section Res. Biol., Agric. Products Dep., E. I. du Pont de Nemours & Co., Inc., Wilmington, DE 19880-0402
Michael K. Hanafey
Affiliation:
Sen. Res. Chem., Agric. Products Dep., E. I. du Pont de Nemours & Co., Inc., Newark, DE 19714
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Abstract

The overall degradation of chlorimuron was very similar at −0.1 and −1.5 MPa and slightly less in air-dry soil. Degradation rates increased with increasing temperature. The primary 14C-labeled compounds observed in moist-soil extracts were desmethyl chlorimuron and saccharin, while the primary 14C-labeled compound observed in air-dry soil extracts was saccharin. Saccharin is formed quantitatively from ethyl 2-(aminosulfonyl)benzoate (phenylsulfonamide) during extraction and therefore represents phenylsulfonamide formed in the soil as a result of chemical hydrolysis of the sulfonylurea bridge. These degradation products suggest that chemical hydrolysis of the sulfonylurea bridge is the primary mode of degradation in air-dry soil, while microbial degradation and chemical hydrolysis both occur in moist soil. These laboratory results demonstrate that chlorimuron will degrade in air-dry soil at a temperature-dependent rate by chemical hydrolysis.

Keywords

Chlorimuron, ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic aciddesmethyl chlorimuron, ethyl 2-[[[[(4-chloro-6-hydroxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] benzoatephenylsulfonamide, ethyl 2-(aminosulfonyl)benzoatesaccharin, 1,2-benzisothiazol-3(2H)-one 1,1-dioxideDegradationdissipationdroughtmoisturesoilsulfonylureatemperaturetwo-compartment model
Type
Soil, Air, and Water
Information
Weed Science , Volume 38 , Issue 3 , May 1990 , pp. 256 - 261
Copyright
Copyright © 1990 by the Weed Science Society of America 

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References

Literature Cited

1. Anderson, R. L. 1985. Environmental effects on metsulfuron and chlorsulfuron bioactivity in soil. J. Environ. Qual. 14:517–521.Google Scholar
2. Anderson, R. L. and Barrett, M. R. 1985. Residual phytotoxicity of chlorsulfuron in two soils. J. Environ. Qual. 14:111–114.Google Scholar
3. Beyer, E. M., Duffy, M. J., Hay, J. V., and Schlueter, D. D. 1988. Sulfonylureas. Pages 117–189 in Kearney, P. C. and Kaufman, D. D., eds. Herbicides: Chemistry, Degradation, and Mode of Action. Vol 3. Marcel-Dekker, New York.Google Scholar
4. Beyer, E. M., Brown, H. M., and Duffy, M. J. 1987. Sulfonylurea herbicide soil relations. Proc. Br. Crop Prot. Conf.–Weeds. 531–540.Google Scholar
5. Breitenbeck, G. A. and Bremner, J. M. 1984. Use of a flat-surface combination pH electrode for measurement of soil pH. Commun. Soil Sci. Plant Anal. 15:87–98.Google Scholar
6. Brown, H. M. 1990. Mode of action, crop selectivity, and soil relations of the sulfonylurea herbicides. Pestic. Sci. (in press).Google Scholar
7. Brown, H. M. and Neighbors, S. M. 1987. Soybean metabolism of chlorimuron ethyl: Physiological basis for soybean selectivity. Pestic. Biochem Physiol. 29:112–120.Google Scholar
8. Duffy, M. J., Hanafey, M. K., Linn, D. M., Russell, M. H., and Peter, C. J. 1987. Predicting sulfonylurea herbicide behavior under field conditions. Proc. Br. Crop Prot. Conf.-Weeds. 2:541–547.Google Scholar
9. Day, P. R. 1965. Particle fractionation and particle-size analysis. Pages 545–567 in Black, C. A., ed. Methods of Soil Analysis. Part 1. Am. Soc. Agron., Inc., Madison.Google Scholar
10. E. I. du Pont de Nemours & Co., Inc. 1988. Technical Aspects of Herbicides Containing Chlorimuron Ethyl. Bull. No. H-02996.Google Scholar
11. Gray, T.R.G., Jones, J. G., and Wright, S.J.L. 1978. Microbial aspects of the soil, plant, aquatic, air and animal environments. Pages 17–77 in Hill, I. R. and Wright, S.J.L., eds. Pesticide Microbiology: Microbiological Aspects of Pesticide Behavior in the Environment Academic Press, London.Google Scholar
12. Hamaker, J. W. and Goring, C.A.I. 1976. Turnover of pesticide residues in soil. Pages 219–243 in Kaufman, D. D., Still, G. G., Paulson, G. D., and Bandal, S. K., eds. Bound and Conjugated Pesticide Residues. ACS Symp. Ser. 29. ACS, Washington, DC.Google Scholar
13. Hurle, K. and Walker, A. 1980. Persistence and its prediction. Pages 83–122 in Hance, R. J., ed. Interactions Between Herbicides and the Soil. Academic Press, London.Google Scholar
14. Joshi, M. M., Brown, H. M., and Romesser, J. A. 1985. Degradation of chlorsulfuron by soil microorganisms. Weed Sci. 33:888–893.Google Scholar
15. Richards, L. A. 1965. Physical condition of water in soil. Pages 128–152 in Black, C. A., ed. Methods of Soil Analysis. Part 1. Am. Soc. Agron., Inc., Madison.Google Scholar
16. Schulte, E. E. 1980. Recommended soil organic matter tests: Routine colorimetric determination of soil organic matter. Page 30 in Recommended Soil Test Procedures for the North Central Region. North Dakota State Univ. Bull. No. 499.Google Scholar
17. Thirunarayanan, K., Zimdahl, R. L., and Smika, D. E. 1985. Chlorsulfuron adsorption and degradation in soil. Weed Sci. 33:558–563.Google Scholar
18. Walker, A. and Brown, P. A. 1983. Measurement and prediction of chlorsulfuron persistence in soil. Bull. Environ. Contam. Toxicol. 30:365–372.Google Scholar