title: Mutagenicity of diallate, sulfallate, and triallate and relationship between structure and mutagenic effects of carbamates used widely in agriculture.
abstract: In an investigation of the mutagenic properties of 20 carbamate herbicides and fungicides by use of the Salmonella/microsome mutagenicity test as developed by Ames et al. (Mutation Res., 31: 347-364, 1975), we have found that three thiocarbamate compounds, diallate, sulfallate and triallate, are mutagenic in the presence of a liver microsomal fraction on strains TA1535 and TA100. This indicates that the metabolic products of these thiocarbamates are causing base-pair substitutions. Since the 2-chloro-allyl group is common to the three mutagenic compounds but is not common to the 17 nonmutagenic compounds, a metabolic derivative of this group is probably responsible for the mutagenic activity.
mesh_terms: D000818:Animals; D004050:Ditiocarb / Q000031:analogs & derivatives; D004353:Drug Evaluation, Preclinical; D005659:Fungicides, Industrial / Q000494:pharmacology*; D006540:Herbicides / Q000494:pharmacology*; D066298:In Vitro Techniques; D008862:Microsomes, Liver / Q000378:metabolism; D009153:Mutagens; D051381:Rats; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship; D013859:Thiocarbamates / Q000494:pharmacology*; D014214:Triallate / Q000494:pharmacology*
chemical_list: D005659:Fungicides, Industrial; D006540:Herbicides; D009153:Mutagens; D013859:Thiocarbamates; C016122:CDEC; D004050:Ditiocarb; D014214:Triallate