Mutagenic activities of a chlorination by-product of butamifos, its structural isomer, and their related compounds

• Published in: Chemosphere (Oxford) 2010, Vol.78 (4), p.482-487
• Main Authors: Kamoshita, Masahiro, Kosaka, Koji, Endo, Osamu, Asami, Mari, Aizawa, Takako
• Format: Article
• Language: English
• Subjects: 2-methyl-5-nitrophenol; 5-methyl-2-nitrophenol; 6-chloro-2-methyl-5-nitrophenol; Ames assay; Ames test; Animals; Butamifos; Carcinogens - metabolism; Chlorination; chlorination byproducts; Chloromethylnitrophenol; DNA, Bacterial - drug effects; genotoxicity; Halogenation; Hydrogen-Ion Concentration; Methylnitrophenol; methylnitrophenols; Microsomes, Liver - metabolism; mutagenicity; Mutagenicity Tests; Mutagens - pharmacology; Nitrophenols - metabolism; Organothiophosphorus Compounds - metabolism; Organothiophosphorus Compounds - pharmacology; Rats; Salmonella typhimurium; Salmonella typhimurium - metabolism; Structure-Activity Relationship; toxicity testing; YG1029 strain
• ISSN: 0045-6535; 1879-1298
• DOI: 10.1016/j.chemosphere.2009.10.002

The mutagenic activities of 5-methyl-2-nitrophenol (5M2NP), a chlorination by-product of butamifos, its structural isomer 2-methyl-5-nitrophenol (2M5NP), and related compounds were evaluated by the Ames assay. The mutagenic activities of 5M2NP and 2M5NP were negative or not particularly high. However, those of their chlorinated derivatives were increased in Salmonella typhimurium strain TA100 and the overproducer strains YG1026, and YG1029 in the absence and/or presence of a rat liver metabolic activation system (S9 mix), particularly for YG1029. The mutagenic activities of 6-chloro-2-methyl-5-nitrophenol (6C2M5NP) in YG1029 in the absence and presence of S9 mix were 70 000 and 110 000 revertants mg −1, respectively. When nitro functions of 6C2M5NP and 4-chloro-5-methyl-2-nitrophenol (4C5M2NP) were reduced to amino functions, their mutagenic activities were markedly decreased. The mutagenic activities of 5M2NP and 4C5M2NP were lower than those of 2M5NP and 6C2M5NP, respectively. Thus, it was shown that substituent position is a key factor for the mutagenic activities of methylnitrophenols (MNPs) and related compounds. The mutagenic activities of the extracts of 2M5NP in chlorination increased early during the reaction time and then decreased. The main chlorination by-product contributing to the mutagenic activities of the extracts of 2M5NP in chlorination was 6C2M5NP. The results of chlorination of 2M5NP suggested that MNPs were present as their dichlorinated derivatives or further chlorination by-products in drinking water.