Genotoxic activity of important nitrobenzenes and nitroanilines in the Ames test and their structure-activity relationship

The most important commercially available nitro-and aminobenzenes and the explosive trinitrobenzene were tested for mutagenicity in the Salmonella typhymurium TA 98 and TA 100 both in the absence and presence of S 9. Ten of the 14 compounds tested (71%) were mutagenic. All the substances showed positive results in TA 98 and 4 substances were also mutagenic in TA 100. The three diaminobenzenes and 4-nitroaniline were mutagenic only with metabolic activation. All other compounds did not require the addition of S 9. Only nitrobenzene, 1,2-dinitrobenzene, aniline and 2-nitroaniline were negative in both strains. In summary, all substances that are derived from nitrobenzene or aniline by addition of a nitro group in the meta- or para-position were mutagenic, whereas nitrobenzene and aniline themselves and their ortho-derivates were nonmutagenic. The possible relationships between the position of the substituents and the mutagenicity are discussed. (C) 1997 Elsevier Science B.V.