Mutagenicity of tetranitroazoxytoluenes: a preliminary screening in Salmonella typhimurium strains TA100 and TA100NR.

Tetranitroazoxytoluenes are polynitroaromatic compounds that can be produced during the microbial reduction of the explosive, 2,4,6-trinitrotoluene (TNT). The three major tetranitroazoxytoluenes were synthesized and tested in Salmonella typhimurium strains TA100 and TA100NR. All compounds were mutagenic in TA100 but not in TA100NR, indicating the need for nitroreductase activity to induce mutagenicity. The most active chemical was 4,4',6,6'-tetranitro-2,2'-azoxytoluene (2735 rev/mumol) followed by 2',4,6,6'-tetranitro-2',4-azoxytoluene (929 rev/mumol) and 2,2'-6,6'-tetranitro-4,4'-azoxytoluene (320 rev/mumol). These chemicals were more active than the aminodinitrotoluenes (298 rev/mumol for 2-amino-4,6-dinitrotoluene and 115 rev/mumol for 4-amino-2,6-dinitrotoluene) and only 4,4',6,6'-tetranitro-2,2'-azoxytoluene was more active than the parent compound, TNT (1022 rev/mumol).