Novel activation mechanism for the promutagenic herbicide diallate.
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.
D000171:Acrolein / Q000494:pharmacology; D000818:Animals; D001711:Biotransformation; D006540:Herbicides / Q000378:metabolism* / Q000494:pharmacology; D051379:Mice; D008862:Microsomes, Liver / Q000378:metabolism; D009153:Mutagens; D009154:Mutation / Q000187:drug effects; D051381:Rats; D013859:Thiocarbamates / Q000378:metabolism* / Q000494:pharmacology
D006540:Herbicides; D009153:Mutagens; D013859:Thiocarbamates; D000171:Acrolein