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Environmental and metabolic transformations of primary aromatic amines and related compounds

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Residue Reviews

Part of the book series: Residue Reviews ((RECT,volume 76))

Abstract

Nitrogen forms a variety of functional groups in combinations with carbon, hydrogen, and oxygen (Table I). These functional groups have been particularly useful for adapting and activating aromatic compounds for use as chemical intermediates in synthetic processes. In addition, many final products contain nitrogen functionalities including pesticides, explosives, drugs, dyes, antioxidants, and antiozonants (Meylan et al. 1976, Mason and Sweeney 1976).

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References

  • Anagnostopoulos, E., I. Scheunert, W. Klein, and F. Korte: Conversion of Pchloroaniline-14C in green algae and water. Chemosphere 4, 351 (1978).

    Google Scholar 

  • Bailey, G. W., and J. L. White: Factors influencing the adsorption, desorption, and movement of pesticides in soil. Residue Reviews 32, 29 (1970).

    PubMed  CAS  Google Scholar 

  • Baisas, G. J.: The reaction of azidoquinones with nucleophiles and the chemistry of primary aminoquinones, Ph.D. thesis, order number 74–19, 241 (1974).

    Google Scholar 

  • Balba, H. M., G. G., Still, and E. ‘R. Mansager,Pyrolytic method for estimation of bound residues of chloroaniline compounds in plants. J. Assoc. Official Anal. Chemists 62, 237 (1979).

    CAS  Google Scholar 

  • Banjerjee, S., H. C. Sikka, R. Gray, and C. M. Kelly: Photodegradation of 3,3’dichlorobenzidine. Environ. Sci. Technol, 12, 1425 (1978).

    Google Scholar 

  • Banks, B. E. C.: Biological formation and reactions of the amino group, pp. 517–519. In S. Patai (ed.): The chemistry of the amino group. New York: WileyInterscience (1968).

    Google Scholar 

  • Barrow, G. M.: Physical Chemistry, 2nd Ed., pp. 544–545. New York: McGraw-Hill, (1966).

    Google Scholar 

  • Barry, E. J., D. Malejka-Gigant, and H. R. Gutmann: Interaction of aromatic amines with rat liver proteins in vivo. Chem-Biol. Interactions 1, 139 (1969).

    CAS  Google Scholar 

  • Bartha, R.: Biochemical transformations of anilide herbicides in soil. J. Agr. Food Chem. 16, 602 (1968).

    CAS  Google Scholar 

  • Bartha, R, Altered propanil biodegradation in temporarily air-dried soil. J. Agr. Food Chem. 19, 394 (1971).

    CAS  Google Scholar 

  • Bartha, R, and D. Pramer: Pesticide transformation to aniline and azo compounds in soil. Science 156, 1617 (1967).

    PubMed  CAS  Google Scholar 

  • Biederbeck, V. O., and E. A. Paul: Fractionation of soil humate with phenolic solvents and purification of the nitrigen-rich portion with polyvinylpyrrolidone. Soil Sci. 115, 357 (1973).

    CAS  Google Scholar 

  • Biggar, J. W., U. Mingelgrin, and M. W. Cheung: Equilibrium and kinetics of adsorption of picloram and parathion with soils. J. Agr. Food Chem. 26, 1306 (1978).

    CAS  Google Scholar 

  • Bollag, J-M., P. Blattmann, and T. Laanio: Adsorption and transformation of four substituted anilines in soil. J. Agr. Food Chem. 26, 1302 (1978).

    CAS  Google Scholar 

  • Bollag, J-M., P. Blattmann, and T. Laanio, and S. Russel: Aerobic versus anaerobic metabolism of halogenated anilines by a Paracoccus sp. Microbial Ecol. 3, 65 (1976).

    CAS  Google Scholar 

  • Bordeleau, L. M., J. D. Rosen, and R. Bartha: Herbicide-derived chlorobenzene residues: Pathway of formation. J. Agr. Food Chem. 20, 573 (1972).

    CAS  Google Scholar 

  • Boyland, E., D. Manson, and S. F. D. Orr: The biochemistry of aromatic amines. Biochem. J. 65, 417 (1957).

    PubMed  CAS  Google Scholar 

  • Brauns, F. E., and D. A. Brauns: The chemistry of lignin, supplement volume 19491958, pp. 587–589. New York: Academic Press (1960).

    Google Scholar 

  • Bray, H. G., S. P. James, and W. V. Thorpe: Metabolism of the monochloronitrobenzenes in the rabbit. Biochem. J. 64, 38 (1956).

    PubMed  CAS  Google Scholar 

  • Brown, J. P., G. W. Roehm, and R. J. Brown: Mutagenicity testing of certified food colors and related azo, xanthene and triphenylmethane dyes with the Samonella/ microsome system. Mutation Res. 56, 249 (1978).

    PubMed  CAS  Google Scholar 

  • Buser, H-R., and H.P. Bossiiardt: Studies on the possible formation of polychloroazobenzenes in quintozene treated soil. Pest. Sci. 6, 35 (1975).

    CAS  Google Scholar 

  • Cantarow, A., and B. Schepartz: Biochemistry, pp. 347–365. Philadelphia: W. B. Saunders Co. (1967 a).

    Google Scholar 

  • Cantarow, A., and B. Schepartz, Biochemisty, pp. 280–281. Philadelphia: W. B. Saunders Co. (1967 b).

    Google Scholar 

  • Cerniglia, C. E., and D. T. Gibson: Metabolism of naphthalene by Cunninghamella elegans. Applied Environ. Microbiol. 34, 363 (1977).

    CAS  Google Scholar 

  • Challis, B. C., and A. R. Butler: Substitution at amino nitrogen, pp. 306–308. In S. Patai (ed.): The chemistry of the amino group. New York: Wiley-Interscience (1968).

    Google Scholar 

  • Cheshire, M. V., P. A. Cranwell, C. P. Falshaw, A. J. Floyd, and R. D. Haworth: Humic acid-II structure of humic acids. Tetrahedron 23, 1869 (1967).

    Google Scholar 

  • Chisaka, H., and P. C. Kearney: Metabolism of propanil in soils. J. Agr. Food Chem. 18, 854 (1970).

    CAS  Google Scholar 

  • Chung, K-T., G. E. Fulk, and M. Egan: Reduction of azo dyes by intestinal anaerobes. Applied Environ. Microbiol. 35, 558 (1978).

    CAS  Google Scholar 

  • Clayson, D. B., and R. C. Garner: Carcinogenic aromatic amines and related compounds, pp. 366–461. In C. E. Searle (ed.): Chemical carcinogens. Washington, D. C.: American Chemical Society (1976).

    Google Scholar 

  • Conant, J. B., and W. D. Peterson: The rate of coupling of diazonium salts with phenols in buffer solutions. J. Amer. Chem. Soc. 52, 1220 (1930).

    CAS  Google Scholar 

  • Conant, J. B., and W. D. Peterson, R. E. Lurz, and B. B. Corson: 1,4-Aminonaphthol hydrochloride. Org. Syn. Collective Vol. I, 49 (1964).

    Google Scholar 

  • Corbett, J. F.: Benzoquinone imines. Part II. Hydrolysis of p-benzoquinone monoimine and p-benzoquinone diimine. J. Chem. Soc. B 1969, p. 213.

    Google Scholar 

  • Corberr, M. D., B. R. Chipko, and D. G. Baden: Chloroperoxidase-catalysed oxidations of 4-chloroaniline to 4-chloronitrosobenzene. Biochem. J. 175, 353 (1978).

    Google Scholar 

  • Corberr, M. D., B. R. Chipko, and D. G. Baden, D. G. Baden, and B. R. Chipko: Arylamine oxidations by chloroperoxidase. Bioorg. Chem. 8, 91 (1979 a).

    Google Scholar 

  • Corberr, M. D., B. R. Chipko, and D. G. Baden, The nonmicrosomal production of N- (4-chlorophenyl) glycohydroxamic acid from 4-chloronitrosobenzene by rat liver homogenate. Bioorg. Chem. 8, 1 (1979 b).

    Google Scholar 

  • Corks, G. T., N. J. Bunce, A. L. Beaumont, and R. L. Merrick: Diazonium cations as intermediates in the microbial transformation of chloroanilines to chlorinated biphenyls, azo compounds, and triazenes. J. Agr. Food Chem. 27, 644 (1979).

    Google Scholar 

  • Cranwell, P. A., and R. D. Hawortii: Humic acid-IV the reaction of alpha-amino acid esters with quinones. Tetrahedron 27, 1831 (1971).

    CAS  Google Scholar 

  • Crawford, D. L., and R. L. Crawford: Microbial degradation of lignin. Presented Amer. Chem. Soc. Meeting, Sept. 12, Washington, D. C. (1979).

    Google Scholar 

  • Daniel, J. W.: The excretion and metabolism of edible food colours. Toxicol. Applied Pharmacol. 4, 572 (1962).

    CAS  Google Scholar 

  • Daniels, D G H, and B. C. Saunders: Studies in peroxidase action. Part VIII. The oxidation of p-chloroaniline. A reaction involving dechlorination. J. Chem. Soc. 1953, 822.

    Google Scholar 

  • Diaciienko, G. W.: Determination of several industrial aromatic amines in fish. Environ. Sci. Technol. 13, 329 (1979).

    Google Scholar 

  • Doneson, K. S., and F. A. Rose: Sulfoconjugation and sulfohydrolysis, pp. 239–325. In W. H. Fishman (ed.): Metabolic conjugation and metabolic hydrolysis, Vol. I. New York: Academic Press (1970).

    Google Scholar 

  • Dubin, P., and K. L. Wright: Reduction of azo food dyes in cultures of Protens vulgaris. Xenobiotica 5, 563 (1975).

    PubMed  CAS  Google Scholar 

  • Dutton, G. J.: The biosynthesis of glucuronides, pp. 185–300. In G. J. Dutton (ed.): Glucuronic acid free and combined. New York: Academic Press (1966).

    Google Scholar 

  • Engelhardt, G., P. Wallnofer, G. Fuchsbichler, and W. Baumeister: Bacterial transformations of 4-chloroaniline. Chemosphere 2/3, 85 (1977).

    Google Scholar 

  • Erickson, M. D., and E. D. Pellizzari• Identification and analysis of polychlorinated biphenyls and other related chemicals in municipal sewage sludge samples. Washington, D. C.: Environmental Protection Agency 560/6–77–021 (1977).

    Google Scholar 

  • Ewing, B. B., E. S. K. Chian, J. C. Cook, C. A. Evans, P. K. Hopke, and E. G. Perkins: Monitoring to detect previously unrecognized pollutants in surface waters. Washington, D. C.: Environmental Protection Agency 560/7–77–001 (1977).

    Google Scholar 

  • Fletcher, C. L., and D. D. Kaufman: Hydroxylation of monochloroaniline pesticide residues by Fusarium oxysporum schlecht. J. Agr. Food Chem. 27, 1127 (1979).

    CAS  Google Scholar 

  • Foussereau, J.: Allergic eczema from disperse yellow 3 in nylon stockings and socks. Trans. St. Johns Hospital Dermatol. Soc. 58, 75 (1972).

    CAS  Google Scholar 

  • Freund, W.: A new synthesis of arsonic acids, part I. Coupling of a, p-unsaturated carbonyl compounds with diazotized p-arsonilic acid. J. Chem. Soc. 1951, 1943.

    Google Scholar 

  • Frobisher, M., R. D. Hinsdill, K. T. Crabtree, and C. R. Goodheart: Fundamentals of microbiology, pp. 669–673. Philadelphia: W. B. Saunders Co. (1974).

    Google Scholar 

  • Fuchsbichler, G., and A. Süss: Desorption and austausch von sorbiertem 4-chloranilin. Chemosphere 4, 345 (1978).

    Google Scholar 

  • Fuhremann, T. W., and E. P. Lichtenstein: Release of soil-bound methyl [14C] parathion residues and their uptake by earthworms and oat plants. J. Agr. Food Chem. 26, 605 (1978).

    CAS  Google Scholar 

  • Games, L. M., and R. A. Hites: Composition, treatment efficiency, and environmental significance of dye manufacturing plant effluents. Anal. Chem. 49, 1433 (1977).

    CAS  Google Scholar 

  • Golab, T., W. A. Althans, and H. L. Wooten: Fate of [14C] trífluralin in soil. J. Agr. Food Chem. 27, 163 (1979).

    CAS  Google Scholar 

  • Gorrod, D. W.: Differentiation of various types of biological oxidation of nitrogen in organic compounds. Chem.-Biol. Interactions 7, 289 (1973).

    CAS  Google Scholar 

  • Hauser, C. R., and D. S. Breslow: Condensations. XV. The electronic mechanism of the diazo coupling reaction. J. Amer. Chem. Soc. 63, 418 (1941).

    CAS  Google Scholar 

  • Helling, C. S., and A. E. Krivonak: Physiochemical characteristics of bound dinitroaniline herbicides in soil. J. Agr. Food Chem. 26, 1156 (1978 a).

    Google Scholar 

  • Helling, C. S., and A. E. Krivonak, Biological characteristics of bound dinitroaniline herbicides in soils. J. Agr. Food Chem. 26, 1164 (1978 b).

    Google Scholar 

  • Hlcxibo’rrom, W. J.: Reactions of organic compounds, 3rd Ed., pp. 284–287. New York: Wiley (1957).

    Google Scholar 

  • Hill, D. L., T.W. Siiiir, and R. F. Struck: Macromolecular binding and metabolism of the carcinogen 4-chloro-2-methylaniline Cancer Res. 39, 2528 (1979).

    PubMed  CAS  Google Scholar 

  • Hsu, T-S., and R. Bartha: Interaction of pesticide-derived chloroaniline residues with soil organic matter. Soil Sci. 116 444 (1974 a).

    Google Scholar 

  • Hsu, T-S., and R. Bartha, Biodegradation of chloroaniline-humus complexes in soil and in culture solution. Soil Sci. 118 213 (1974 b).

    CAS  Google Scholar 

  • Hughes, E. D., C. K. Incold, and J. H. Ridd: Nitrosation, diazotisation, and deamination. Part I. Principles, background, and method for the kinetic study of diazotisation. J. Chem. Soc. 1958 a, 58.

    Google Scholar 

  • Hughes, E. D., C. K. Incold, and J. H. Ridd,Part II. Second and third order diazotisation of aniline in dilute perchloric acid. J. Chem. Soc. 1958 b 65.

    Google Scholar 

  • Hughes, E. D., C. K. Incold, and J. H. Ridd, and J. H. Ridd: Part III. Zeroth order diazotisation of aromatic amines in carboxylic acid buffers. J. Chem. Soc. 1958 c 70.

    Google Scholar 

  • Hughes, E. D., C. K. Incold, and J. H. Ridd, C. K. Ingold, and J. H. Ridd: Part IV. Hydrogen ion catalysis in the diazotisa-tion of o-chloroaniline in dilute perchloric acid. J. Chem. Soc. 1958 d 77.

    Google Scholar 

  • Hughes, E. D., C. K. Incold, and J. H. Ridd, and J. H. Ridd: Part V. Catalysis by anions of strong acids in the diazotisation of aniline and of o-chloroaniline in dilute perchloric acid. J. Chem. Soc. 1958 e, 82.

    Google Scholar 

  • Hughes, E. D., C. K. Incold, and J. H. Ridd, C. K. Incold, and J. H. Ridd: Part VI. Comparative discussion of mechanisms of N- and 0-nitrosation with special reference to diazotisation. J. Chem. Soc. 1958 f 88.

    Google Scholar 

  • Irving, C. C.: Conjugates of N-hydroxy compounds, pp. 53–119. In W. H. Fishman (ed.): Metabolic conjugation and metabolic hydrolysis, Vol. I. New York: Academic Press (1970).

    Google Scholar 

  • Iwan, J., G-A. Hoyer, D. Rosenberg, and D. Coller’ Transformations of 4-chloroo-toluidine in soils: Generation of coupling products by one-electron oxidation. Pest. Sci. 7, 621 (1976).

    CAS  Google Scholar 

  • Jenkins, R. L., J. E. Haskins, L. G. Carmona, and R. B. Baird: Chlorination of benzidine and other aromatic amines in aqueous environments. Arch. Environ. Contam. Toxicol. 7, 301 (1978).

    PubMed  CAS  Google Scholar 

  • Kadlubar, F. F., J. A. Miller, and E. C. Miller: Guanyl 06-arylamination and O’-arylation of DNA by the carcinogen N-hydroxy-l-naphthylamine. Cancer Res. 38, 3628 (1978).

    PubMed  CAS  Google Scholar 

  • Kao, J., J. Faulkner, and J. W. Bridges: Metabolism of aniline in rats, pigs and sheep. Drug Metab. Distrib. 6, 549 (1978).

    CAS  Google Scholar 

  • Katan, J., and E. P. Lichtenstein: Mechanisms of production of soil-bound residues of [’4C] parathion by microorganisms. J. Agr. Food Chem. 25, 1404 (1977).

    CAS  Google Scholar 

  • Kaubisca, N., J. W. Daly, and D. M. Jerina: Arene oxides as intermediates in the oxidative metabolism of aromatic compounds. Isomerization of methyl-substituted arene oxides. Biochem. 11, 3080 (1972).

    Google Scholar 

  • Kaufman, D. D., J. R. Plimmer, and U. I. Klingbiel• Microbial oxidation of 4-chloroaniline. J. Agr. Food Chem. 21, 127 (1973).

    CAS  Google Scholar 

  • Kearney, P., and J. R. Plimmer: Metabolism of 3,4-dichloroaniline in soils. J. Agr. Food Chem. 20, 584 (1972).

    CAS  Google Scholar 

  • Khan, S. U.: Adsorption of pesticide by humic substances. A review. Environ. Letters 3, 1 (1972).

    CAS  Google Scholar 

  • Kriek, E.: On the mechanism of action of carcinogenic aromatic amines, I. Binding of 2-acetylaminofluorene and N-hydroxy-2-acetylaminofluorene to rat-liver nucleic acids in vivo. Chem.-Biol. Interactions 1, 3 (1969).

    CAS  Google Scholar 

  • Kriek, E, J. A. Miller, and E. C. Miller: 8-(N-2-Fluorenylacetamido) guanosine, an arylamidation reaction product of guanosine and the carcinogen N-acetoxy-N-2fiuorenylacetamide in neutral solution. Biochem. 6, 177 (1967).

    CAS  Google Scholar 

  • Land, E. J.: Electronic spectra and kinetics of aromatic free radicals. In G. Porter (ed): Progress in reaction kinetics, vol. 3, pp. 394–399. New York: Pergamon (1965).

    Google Scholar 

  • Land, E. J, and G. Porter: Primary photochemical processes in aromatic molecules, part 8. Absorption spectra and acidity constants of anilio radicals. Trans. Faraday Soc. 59, 2027 (1963).

    CAS  Google Scholar 

  • Lichtenstein, E. P., J. Katan, and B. N. Anderecg: Binding of “persistent” and “nonpersistent” 14C-labeled pesticides in an agricultural soil. J. Agr. Food Chem. 25, 43 (1977).

    CAS  Google Scholar 

  • Lu, P-Y., R. L. Metcalf, N. Plummer, and D. Mandel: The environmental fate of three carcinogens: Benzo-(a)-pyrene, benzidine, and vinyl chloride evaluated in laboratory model ecosystems. Arch. Environ. Contam. Toxicol. 6, 129 (1977).

    PubMed  CAS  Google Scholar 

  • Macdonald, J. C., A. M. Plescia, E. C. Miller, and J. A. Miller: The metabolism of methylated aminoazo dyes. III. The demethylation of various N-methyl-C14aminoazo dyes in vivo. Cancer Res. 13, 292 (1953).

    PubMed  CAS  Google Scholar 

  • March, J.: Advanced organic chemistry: Reactions, mechanisms, and structure, p. 555. New York: McGraw-Hill (1968 a).

    Google Scholar 

  • March, J.:, Advanced organic chemistry: Reactions, mechanisms, and structure, pp. 281–302. New York: McGraw-Hill (1968 b).

    Google Scholar 

  • Marsh, C. A.: Chemistry of D-glucuronic acid and its glycosides, pp. 3–136. In G. J. Dutton (ed.): Glucuronic acid free and combined. New York: Academic Press (1966).

    Google Scholar 

  • Mason, R., and S. C. Sweeney: A literature survey oriented towards adverse environmental effects resultant from the use of azo compounds, brominated hydrocarbons, EDTA, formaldehyde resins and o–nitrochlorobenzene. Washington, D. C.: Environmental Protection Agency 560/2–76–005 (1976).

    Google Scholar 

  • Mccormicx, N. G., J. H. Cornell, and A. M. Kaplan: Identification of biotransformation products from 2,4-dinitrotoluene. Applied Environ. Microbiol. 35, 945 (1978).

    Google Scholar 

  • Mccormicx, N. G., J. H. Cornell, and A. M. Kaplan, F. E. F.Eherry, and H. S. Levinson: Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds. Applied Environ. Microbiol. 31, 949 (1976).

    Google Scholar 

  • Meylan, W. M., P. H. Howard, and M. Sack: Chemical market input/output analysis of selected chemical substances to assess sources of environmental contamination: Task I. Naphthylamines. Washington, D. C.: Environmental Protection Agency 560/6–77–002 (1976).

    Google Scholar 

  • Michaelis, L., and E. S. Hill: Potentiometric studies on semiquinones. J. Amer. Chem. Soc. 55, 1481 (1933).

    CAS  Google Scholar 

  • Miller, E. C., F. F. Kadlubar, J. A. Miller, H. C. Pitot, and N. R. Drinkwater: The N-hydroxy metabolites of N-methyl-4-aminoazobenzene and related dyes as proximate carcinogens in the rat and mouse. Cancer Res. 39, 3411 (1979).

    PubMed  CAS  Google Scholar 

  • Minard, R. D., S. Russel, and J-M. Bollag: Chemical transformations of 4-chloroaniline to a triazene in a bacterial culture medium. J. Agr. Food Chem. 25, 841 (1977).

    CAS  Google Scholar 

  • Moreale, A., and R. van Bladel: Soil interactions of herbicide-derived aniline residues: A thermodynamic approach. Soil Sci. 127, 1 (1979).

    CAS  Google Scholar 

  • Morton, K. C., C. M. King, and K. P. Baetcke: Metabolism of benzidine to Nhydroxy-N,N’-diacetylbenzidine and subsequent nucleic acid binding and mutagenicity. Cancer Rec. 39, 3107 (1979).

    CAS  Google Scholar 

  • Neumann, H-G.: Ultimate electrophilic carcinogens and cellular nucleophilic reactants. Arch. Toxikol. 32, 27 (1974).

    CAS  Google Scholar 

  • Oesch, F.: Mammalian epoxide hydiases: Inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. Xenobiotica 3, 305 (1972).

    Google Scholar 

  • Ogata, Y., and Y. Takagi: Kinetics of the condensation of anilines wtih nitrosobenzenes to form azobenzenes. J. Amer. Chem. Soc. 80, 3591 (1958).

    CAS  Google Scholar 

  • Paris, D. F., W. C. Steen, and G. L. Baughman: Kinetics of microbial transformations of pollutants in natural waters. Presented Amer. Chem. Soc. Meeting, Sept. 10, Washington, D. C. (1979).

    Google Scholar 

  • Pierce, R. H., JR., C. E. Olney, and G. T. Felbace, JR.: Pesticide adsorption in soils and sediments. Environ. Letters 1, 157 (1971).

    CAS  Google Scholar 

  • Pierce, R. H., JR., C. E. Olney, and G. T. Felbace, -DDT adsorption to suspended particulate matter in sea water. Geochim. Cosmochim. Acta 38, 1061 (1974).

    CAS  Google Scholar 

  • Plimmer, J. R., P. C. Kearney, H. Chisaka, J. B. Yount, and U. I. Klingebiel: 1,3-Bis (3,4-dichlorophenyl) triazene from propanil in soils. J. Agr. Food Chem. 18, 859 (1970).

    CAS  Google Scholar 

  • Poland, A., and E. Glover: 3,4,3’,4’-Tetrachloro-azoxybenzene and -azobenzene: Potent inducers of aryl hydrocarbon hydroxylase. Science 194, 627 (1976).

    PubMed  CAS  Google Scholar 

  • Riffaldi, R., and M. Schnitzer. Effect of 6N HCl hydrolysis on the analytical characteristics and chemical structure of humic acids. Soil Sci. 115, 349 (1973).

    CAS  Google Scholar 

  • Roberts, J. D. and M. C. Caserio: Basic principles of organic chemistry, pp. 915–916. New York: W. A. Benjamin (1965 a).

    Google Scholar 

  • Roberts, J. D. and M. C. Caserio, Basic principles of organic chemistry, pp. 892–895. New York: W. A. Benjamin (1965 b).

    Google Scholar 

  • Rondestvedt, C. S., JR.: Arylation of unsaturated compounds by diazonium salts. Organic Reactions 11, 189 (1960).

    CAS  Google Scholar 

  • Saunders, B. C., A. G. Holmes-Siedle, and B. P. Stark: Peroxidase. Washington, D. C.: Butterworths (1964).

    Google Scholar 

  • Schnitzer, M., and S. U. Khan: Humic substances in the environment. New York: Marcel Dekker (1972).

    Google Scholar 

  • Shafer, N., and R. Shafer: Potential of carcinogenic effects of hair dyes. N. Y. State J. Med. 76, 394 (1976).

    PubMed  CAS  Google Scholar 

  • Sjoblad, R. D., and J-M. Bollag: Oxidative coupling of aromatic pesticide intermediates by a fungal phenol oxidase. Applied Environ. Microbiol. 33, 906 (1977).

    CAS  Google Scholar 

  • Smith, R. L., and R. T. Williams: Implications of the conjugation of drugs and other exogenous compounds, pp. 457–491. In G. J. Dutton (ed.): Glucuronic acid free and combined. New York: Academic Press (1966).

    Google Scholar 

  • Sollenberger, P. Y., and R. B. Martin: Carbon-nitrogen and nitrogen-nitrogen double bond condensation reactions, pp. 349–406. In S. Patai (ed.): Chemistry of the amino group. New York: Wiley-Interscience (1968).

    Google Scholar 

  • Sorensen, J.: Occurrence of nitric and nitrous oxides in a coastal marine sediment. Applied Environ. Microbiol. 36, 809 (1978).

    CAS  Google Scholar 

  • Sprott, G. D., and C. T. Corke: Formation of 3,3’,4,4’-tetrachloroazobenzene from 3,4-dichloroaniline in Ontario soils. Can. J. Microbiol. 17, 235 (1971).

    CAS  Google Scholar 

  • Stevenson, F. J., and K. M. Col: Infrared spectra of humic acids and related substances. Geochim Cosmochim. Acta 35, 471 (1971).

    CAS  Google Scholar 

  • Still, G. G.: Metabolism of 3,4-dichloropropionanilide in plants: the metabolic fate of the 3,4-dichloroaniline moiety. Science 159, 992 (1968).

    PubMed  CAS  Google Scholar 

  • Tweedy, B. G., C. Loeppky, and J. A. Ross: Metobromuron: acetylation of the aniline moiety as a detoxification mechanism. Science 168, 482 (1970).

    PubMed  CAS  Google Scholar 

  • Urushigawa, Y., and Y. Yonezawa: Chemico-biological interactions in biological purification system II. biodegradation of azo compounds by activated sludge. Bull. Environ. Contam. Toxicol. 17, 214 (1977).

    PubMed  CAS  Google Scholar 

  • van Alfen, N. K., and T. Kosuge: Metabolism of the fungicide 2,6-dichloro-4nitroaniline in soils, J. Agr. Food Chem. 24, 584 (1976).

    Google Scholar 

  • Vets, C. A.: Aromatic amines: The present status of the problem. Ann. Occupational Hyg. 15, 11 (1972).

    Google Scholar 

  • Viswanathan, R., W. Klein, and F. Korte: Separation and identification of metabolites excreted by rats after long-term oral administration of imugan 14C. Chemosphere 1, 71 (1978 a).

    Google Scholar 

  • I. Scheunert, J. Komli, W. Klein, and F. Korte: Long-term studies on the fate of 3,4-dichloroaniline -“C in a plant-soil-system under outdoor conditions. J. Environ. Sci. Health B13, 243 (1978 b).

    Google Scholar 

  • Wheeler, L A, F B Soderberg, and P. Goldman: The relationship between nitro group reduction and the intestinal microfiora. J. Pharmacol. Expt. Therap. 195, 135 (1975).

    Google Scholar 

  • Wistar, R., and P. D. Bartlett: Kinetics and mechanisms of the coupling of diazonium salts with aromatic amines in buffer solutions. J. Amer. Chem. Soc. 63, 413 (1941).

    CAS  Google Scholar 

  • Wood, J. M., R. L. Crawford, E. Münck, R. Zimmerman, J. D. Lipscomb, R. S. Stephens, J. W. Bromley, L. Que, JR., J. B. Howard, and W. H. Orme-Johnson: Structure and function of dioxygenases. One approach to lignin degradation. J. Agr. Food Chem. 25, 698 (1977).

    CAS  Google Scholar 

  • Wszolok, P. C., and M. Alexander: Effect of desorption rate on the biodegradation of n-alkylamines bound to clay. J. Agr. Food Chem. 27, 410 (1979).

    Google Scholar 

  • Yamashina, I., S. Shikata, and F. Egami: Studies on enzymatic reduction of aromatic nitro, nitroso, and hydroxylamine compounds. Bull. Chem. Soc. Japan 27, 42 (1954).

    CAS  Google Scholar 

  • Yau, R. Y., D. H. Mcrae, and H. F. Wilson: Metabolism of 3’,4’-dichloropropionanilide: 3,4-Dichloroaniline-lignin complex in rice plants. Science 161, 376 (1968).

    Google Scholar 

  • Yonezawa, Y., and Y. Urushigawa: Chemico-biological interactions in biological purification systems. I. Growth inhibition effect of azo compounds on activated sludge microorganisms. Bull. Environ. Contam. Toxicol. 17, 208 (1977).

    CAS  Google Scholar 

  • Yurawecz, M. P.: GLC and mass spectrometric determination of monochloronitrobenzene residues in Mississippi River fish. Presented AOAC meeting, Oct. 17, Washington, D. C. (1978).

    Google Scholar 

  • Zavon, M. R.: Benzidine exposure as a cause of bladder tumors. Arch. Environ. Health 27, 1 (1973).

    PubMed  CAS  Google Scholar 

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© 1980 Springer-Verlag New York Inc.

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Parris, G.E. (1980). Environmental and metabolic transformations of primary aromatic amines and related compounds. In: Gunther, F.A., Gunther, J.D. (eds) Residue Reviews. Residue Reviews, vol 76. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-6107-0_1

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  • DOI: https://doi.org/10.1007/978-1-4612-6107-0_1

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