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Science 7 September 1979:
Vol. 205. no. 4410, pp. 1013 - 1015
DOI: 10.1126/science.472719
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Articles

Science, Vol 205, Issue 4410, 1013-1015
Copyright © 1979 by American Association for the Advancement of Science

articles

Novel activation mechanism for the promutagenic herbicide diallate

I Schuphan, JD Rosen, and JE Casida

The potent bacterial mutagen 2-chloroacrolein is formed from the carcinogenic herbicide S-2,3-dichloroallyl diisopropylthiocarbamate (diallate) on incubation with hepatic microsomal monooxygenases or on reaction with m-chloroperbenzoic acid. A proposed activation mechanism for this promutagen involves sulfoxidation followed by [2,3] sigmatropic rearrangement and 1,2-elimination reactions. A portion of the highly reactive intermediate, diallate sulfoxide (proximate mutagens), is attacked by glutathione in a reaction which competes with its transformation to the ultimate mutagen, 2-chloroacrolein.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Two Recessive Gene Inheritance for Triallate Resistance in Avena fatua L..
A. J. Kern, T. M. Myers, M. Jasieniuk, B. G. Murray, B. D. Maxwell, and W. E. Dyer (2002)
J. Hered. 93, 48-50
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