Abstract
The mutagenicity of 19 herbicide-derived chlorinated azobenzenes and structurally related chlorinated anilines and nitrobenzenes was assayed towards several strains ofS. typhimurium, using the plate incorporation method and the fluctuation test, in the presence or in the absence of liver post-mitochondrial fractions, in aerobic and anaerobic conditions.
Positive results were obtained with 4,4′-dichloroazobenzene, 4,4′-dichloroazoxybenzene, 3,4-dichloronitrobenzene and, to a much lesser extent, with 3,4,3′,4′-tetrachloroazobenzene. No mutagenic effect was observed with 2,3,7,8-tetrachlorodibenzo-p-dioxin in any condition.
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References
Ames, B. N., J. McCann, and E. Yamasaki: Methods for detecting carcinogens and mutagens with the Salmonella/mammalian microsome mutagenicity test. Mutation Res.31, 347 (1975).
Bartha, R., and D. Pramer: Pesticide transformation to aniline and azo compounds in soil. Science156, 1617 (1967).
Bartha, R., H. A. B. Linke, and D. Pramer: Pesticide transformations: Production ofchloroazobenzenes from chloroanilines. Science161, 582 (1968).
Bartha, R., and D. Pramer: Metabolism of acylanilide herbicides. Adv. Appl. Microbiol.13, 317 (1970).
Bartsch, H.: Predictive value of mutagenicity tests in chemical carcinogenesis. Mutation Res.38, 177 (1976).
Bordeleau, L. M., J. D. Rosen, and R. Bartha: Herbicide-derived chloroazobenzene residues: Pathway of formation. J. Agric. Food Chem.20, 573 (1972).
Buu-Hoï, N. P., G. Saint-Ruf, P. Bigot, and M. Mangane: Preparation, propriétés et identification de la “dioxine” (tetrachloro-2,3,7,8-dibenzo-p-dioxine) dans les pyrolysats de défoliants à base d'acide trichloro-2,4,5-phenoxyacétique et de ses esters et des végétaux contaminés. Comptes rendus Acad. Sci.273, série D, 708 (1971).
Chisaka, H., and D. C. Kearney: Metabolism of propanil in soils. J. Agric. Food Chem.18, 854 (1970).
Corbett, J. F., and P. F. Holt: Dehalogenation during the reduction of halogenonitroarenes with lithium aluminium hydride. J. Chem. Soc. 2385 (1963).
Curley, A., V. W. Burse, R. W. Jennings, E. C. Villanueva, and R. D. Kimbrough: Evidence of tetrachlorodibenzofuran (TCDF) in Aroclor 1254® and the urine of rats following dietary exposure to Aroclor 1254®. Bull. Environ. Contam. Toxicol.14, 153 (1975).
Green, M. H. L., B. A. Bridges, A. M. Rogers, G. Horspool, W. J. Muriel, J. W. Bridges, and J. R. Fry: Mutagen screening by a simplified bacterial fluctuation test: Use of microsomal preparations and whole liver cells for metabolic activation. Mutation Res.48, 287 (1977).
Hsia, M. T. S., F. V. Z. Bairstow, L. C. T. Shih, J. C. Pounds, and J. R. Allen: 3,4,3′,4′-tetrachloroazobenzene: a potential environmental toxicant. Res. Commun. Chem. Pathol. Pharmacol.17, 225 (1977).
Hussain, S., L. Ehrenberg, C. Löfroth, and T. Gejvall: Mutagenic effects of TCDD on bacterial systems. Ambio1, 32 (1972).
Kaufman, D. D., J. R. Plimmer, J. Iwan, and V. I. Klingbiel: 3,3′,4,4′-tetrachloroazoxybenzene from 3,4-dichloroaniline in microbial culture. J. Agric. Food Chem.20, 916 (1972).
Kimbrough, R. D.: The toxicity of polychlorinated polycyclic compounds and related chemicals. Chem. Rubber Co. Crit. Rev. Toxicol.8, 445 (1974).
Poland, A., E. Glover, A. S. Kende, M. Decamp, and C. M. Giandomerrico: 3,4,3′,4′-tetrachloroazoxybenzene and azobenzene: potent inducers of aryl hydrocarbon hydroxylase. Science194, 627 (1976).
Prasad, I.: Mutagenic effects of the herbicide 3′,4′-dichloropropionanilide and its degradation products. Can. J. Microbiol.16 (5) 369 (1970).
Purchase, I. F. H., E. Longstaff, J. Ashby, J. A. Styles, D. Anderson, P. A. Lefevre, and F. R. Westwood: Evaluation of six short tests for detecting organic chemical carcinogens and recommendations for their use. Nature264, 624 (1976).
Rosenkranz, H. S., W. T. Speck, and B. Gutter: Microbiol assay procedures: experience with two systems, in “In vitro metabolic activation in mutagenesis testing” (de Serres, Fouts, Bend and Philpot, p. 337).
Saint-Ruf, G., Do Phuoc Hien and M. Mercier: Effects of 3,4,3′,4′-tetrachloroazobenzene and 3,4,3′,4′-tetrachloroazoxybenzene in rat liver microsomes. Bull. Environ. Contam. Toxicol.22, 638 (1979).
Speck, W. T., and H. S. Rosenkranz: Mutagenicity of azathioprine. Cancer Res.36, 108 (1976).
Still, G. G.: 3,4,3′,4′-tetrachloroazobenzene: its translocation and metabolism in rice plants. Weed Res.9, 211 (1969).
Taylor, J. S., R. C. Nuthrich, K. M. Lloyd, and A. Poland: Chloracne from manufacture of a new herbicide. Arch. Dermatol.113, 616 (1977).
Wheeler, O. H., and D. Gonzales: Oxidation of primary aromatic amines with manganese dioxide. Tetrahedron20, 189 (1964).
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Gilbert, P., Saint-Ruf, G., Poncelet, F. et al. Genetic effects of chlorinated anilines and azobenzenes onSalmonella typhimurium . Arch. Environ. Contam. Toxicol. 9, 533–541 (1980). https://doi.org/10.1007/BF01056933
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DOI: https://doi.org/10.1007/BF01056933