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Interactions of Buthidazole with Clay Minerals and Soils

Published online by Cambridge University Press:  12 June 2017

Song-Wu Li  and
Max M. Mortland
Song-Wu Li
Affiliation:
Dep. Crop Soil Sci., Michigan State Univ., East Lansing, MI 48824
Max M. Mortland
Affiliation:
Dep. Crop Soil Sci., Michigan State Univ., East Lansing, MI 48824
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Abstract

The newly developed herbicide buthidazole {3-[5-(1,1-dimethylethyl)-1,3,4-thiadizol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone} was studied with respect to its interaction with soils and homoionic clay minerals and its response to irradiation with ultraviolet light. Results showed that it could enter the interlamellar spaces of swelling clays such as smectite. Isothermic adsorption studies indicated that Cu+2-smectite adsorbed more buthidazole than Cu+2-kaolinite. The Cu+2-clay adsorption isotherm fitted the Langmuir model. The effect of exchangeable cations on adsorption was not significant in soils of high organic matter content. Bioassay studies indicated that buthidazole's phytotoxicity was not decreased in either clays or in organic soils. Infrared spectroscopic studies showed the coordination of buthidazole with Cu+2 through C=O Cu interaction with buthidazole resulted in a ligand-to-metal ratio to 1:1. Protonation of buthidazole occurred in Al+3-and H+-smectite. The herbicide was labile to UV-light irradiation at 254 nm but not at 366 nm. The photoconversion indicated a first-order reaction. The photolytic product(s) included the –N=C=O structure. Copper(II) ions, which form complexes, retarded photolysis of buthidazole in UV-light, but the Ca+2 ion, which is unable to form complexes, did not.

Keywords

Adsorptionphotolysisherbicidekaolinite
Type
Research Article
Information
Weed Science , Volume 29 , Issue 6 , November 1981 , pp. 667 - 671
Copyright
Copyright © 1981 by the Weed Science Society of America 

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References

Literature Cited

1. Bailey, G. W. and White, J. L. 1970. Factors influencing the adsorption, desorption, and movement of pesticides in soil. Residue Rev. 32:29–92.Google Scholar
2. Crosby, D. G. 1969. Experimental approaches to pesticide photo-decomposition. Residue Rev. 25:1–12.Google Scholar
3. Day, B. E., Jordan, L. S., and Jolliffe, V. A. 1968. The influence of soil characteristics on the adsorption and phytotoxicity of simazine. Weed Sci. 16:209–212.CrossRefGoogle Scholar
4. Doner, H. E. and Mortland, M. M. 1969. Benzene complexes with copper(II)-montmorillonite. Science 166:1406–1407.CrossRefGoogle ScholarPubMed
5. Freed, V. H., Vernetti, J., and Montgomery, M. 1962. The soil behavior of herbicides as influenced by their physical properties. Proc. West. Weed Control Conf. 19:21.Google Scholar
6. Harris, C. M. and Warren, G. F. 1964. Adsorption and desorption of herbicides by soil. Weeds 12:120–126.CrossRefGoogle Scholar
7. Hurle, K. 1977. Biotests for the detection of herbicides in the soil. Pages 285–306 in McFarlane, N. R., ed. Crop Protection Agents. Academic Press, New York.Google Scholar
8. Joschek, H. H. and Miller, S. I. 1966. Photocleavage of phenoxyphenols and bromophenols. J. Am. Chem. Soc. 88:3269–3272.Google Scholar
9. Joschek, H. H. and Miller, S. I. 1966. Photooxidation of phenol cresols, and dihydroxybenzens. J. Am. Chem. Soc. 88:3273.CrossRefGoogle Scholar
10. Krantz, A. and Laureni, J. 1977. A methodology for the preparation and characterization of three-membered, potentially anti-aromatic molecules. Preparation of matrix-isolated thiirene and selenirene. J. Am. Chem. Soc. 99:4842–4844.CrossRefGoogle Scholar
11. Krantz, A. and Laureni, J. 1977. Preparation of matrix-isolated thiirene. Ber. Bunsenges. Phys. Chem. 82:14–24.Google Scholar
12. McGlamery, M. D. and Slife, F. W. 1966. The adsorption and desorption of atrazine as affected by pH, temperature, and concentration. Weeds 14:237–239.Google Scholar
13. Mills, A. C. and Biggar, J. W. 1969. Solubility-temperature effect on the adsorption of gamma- and beta-BHC aqueous and hexane solutions by soil materials. Soil Sci. Soc. Am. Proc. 33:210.Google Scholar
14. Mortland, M. M. 1966. Urea complexes with montmorillonite: an infrared absorption study. Clay Miner. 6:143–156.Google Scholar
15. Mortland, M. M. 1970. day-organic complexes and interactions. Adv. Agron. 22:75–119.CrossRefGoogle Scholar
16. Mortland, M. M. and Meggitt, W. F. 1966. Interaction of ethyl N,N-di-n-propylthiocarbamate (EPTC) with montmorillonite. J. Agric. Food Chem. 14:126–129.Google Scholar
17. Munakta, K. and Kuwahara, M. 1969. Photochemical degradation products of pentachlorophenol. Residue Rev. 25:13–23.Google Scholar
18. Parfitt, R. L. and Mortland, M. M. 1968. Ketone adsorption on montmorillonite. Soil Sci. Soc. Am. Proc. 32:355–363.CrossRefGoogle Scholar
19. Plimmer, J. R. 1970. The photochemistry of halogenated herbicides. Residue Rev. 33:47–74.Google Scholar
20. Rossotti, F. J. C. 1960. The thermodynamics of metal ion complex formation in solution. Pages 5–67 in Lewis, J. and Wilkins, R. G., eds. Modern Coordination Chemistry. Interscience Pub., New York.Google Scholar
21. Russell, J. D., Cruz, M. I., and White, J. L. 1968. The adsorption of 3-aminotriazole by montmorillonite. J. Agric. Food Chem. 16:21–24.Google Scholar
22. Skipper, H. D., Volk, V. V., Mortland, M. M., and Raman, K. V. 1978. Hydrolysis of atrazine on soil colloids. Weed Sci. 26:44–51.Google Scholar
23. Upchurch, R. P. and Kamprath, E. J. 1966. The correlation of herbicidal activity with soil and climatic factors. Weeds 14:42–49.Google Scholar
24. Zeller, K. P., Meier, H., and Mueller, E. 1972. Photolysis of 1,2,3-thiadiazole. Justus Liebigs Ann. Chem. 766:32–44.Google Scholar