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Fate of polynuclear aromatic compounds (PNAs) in soil-plant systems

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Residue Reviews

Part of the book series: Residue Reviews ((RECT,volume 88))

Abstract

Polycyclic aromatic hydrocarbons (PAH) consist of three or more fused benzene rings in linear, angular, or cluster arrangements. Substitution of carbon in the benzene ring with nitrogen, sulfur, oxygen, or other elements creates heterocyclic aromatic compounds (Blumer 1976). Excluding diphenyl types there are some 70 possible isomers of 4-6 fused rings. Additionally these isomers may be substituted by a variety of substituents (Erskine and Whitehead 1975). The aromatic hydrocarbons and heterocycles, unsubstituted and substituted, are referred to alternatively as polynuclear aromatics (PNAs), polycyclic aromatic compounds (PCAs), and polycyclic organic matter (POM) (NAS 1972, U.S. EPA 1975 b).

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References

  • Ahokas, J., R. Paakkonen, K. Ronnholm, V. Raunio, and O. Pelkonen: Oxidative metabolism of carcinogens by trout liver resulting in binding and mutagenicity. Hoppe-Seyler’s Z. Physiol. Chem. Bd. 357, S: 1019 (1976).

    Google Scholar 

  • Akhtar, M. N., D. R. Boyd, N. J. Thompson, D. T. Gibson, V. Mahadevan, and D. M. Jerina: Absolute stereochemistry of the dihydroanthracene-cis-and trans-1,2-diols produced from anthracene by mammals and bacteria. J. Chem. Soc. 1506 (1975).

    Google Scholar 

  • Alexander, M.: Introduction to soil microbiology, 2nd ed. New York: Wiley (1977).

    Google Scholar 

  • Ames, B. N., P. Sims, and P. L. Grover: Epoxides of polycyclic hydrocarbons are frameshift mutagens. Science 176, 47 (1972)

    PubMed  CAS  Google Scholar 

  • Andleman, J. B., and M. J. Suess: The photodecomposition of 3,4-benz-pyrene sorbed on calcium carbonate. In Foust S. J., and J. U. Hunter (eds.): Organic compounds in aquatic environments. New York: Marcel Dekker, pp. 439–468 (1971).

    Google Scholar 

  • Arffman, E., and B. C. Christensen: Studies on the newt test for carcinogenicity. I. Benzo(a)pyrene, dibenz(a,h)anthracene, and 3-methylcholanthrene. Acta Pathol. Microbiol. Scand. 52, 330 (1961).

    Google Scholar 

  • Bailey, E. J., and N. Dungal: Polycyclic hydrocarbons in icelandic smoked food. Brit. J. Cancer. 12, 348 (1958).

    PubMed  CAS  PubMed Central  Google Scholar 

  • Bailey, G. W., and J. L. White: Review of adsorption and desorption of organic pesticides by soil colloids, with implications concerning pesticide bioactivity. J. Agr. Food Chem. 12, 324 (1964).

    CAS  Google Scholar 

  • Balls, M.: Benzpyrene-induced tumors in the clawed toad, Xenopus laevis. Experientia 20(3), 143 (1964).

    CAS  Google Scholar 

  • Bartle, K. D., M. L. Lee, and M. Novotny: An integrated approach to the analysis of air-pollutant polynuclear aromatic hydrocarbons. Proc. Anal. Div. Amer. Chem. Soc, Oct., pp. 304–307 (1976).

    Google Scholar 

  • Bazin, M. J., P. T. Saunders, and J. I. Prosser: Models of microbial interactions in the soil. CRC Critical Reviews in Microbiology, pp. 463-498 (1976).

    Google Scholar 

  • Bigger, C. A. H., J. E. Tomaszewski, A. W. Andrews, and A. Dipple: Evaluation of metabolic activation of 7, 12-dimethylbenz (a) anthracene in vitro by Araclor 1254-induced rat liver S-9 fraction. Cancer Res. 40, 655 (1980).

    PubMed  CAS  Google Scholar 

  • Binet, L., and L. Mallet: Diffusion of pH in the animated environment. Gaz. Hop. (Paris) 135, 1142 (1963).

    CAS  Google Scholar 

  • Blum, S. C., and R. E. Swarbrick: Hydroponic growth of crops in solutions saturated with 14C-benzo(a)pyrene. J. Agr. Food Chem. 25, 1093 (1977).

    CAS  Google Scholar 

  • Blumer, M.: Curtisite, idrialite, and pendletonite, polycyclic aromatic hydrocarbon minerals: Their composition and origin. Chem. Geol. 16, 245 (1975).

    CAS  Google Scholar 

  • — Polycyclic aromatic compounds in nature. Sci. American 234(3), 35 (1976).

    CAS  Google Scholar 

  • —, and W. W. Youngblood: Polycyclic aromatic hydrocarbons in soils and recent sediments. Science 188, 53 (1975).

    PubMed  CAS  Google Scholar 

  • Borneff, J., and R. Knerr: Carcinogenic substances in water and soil. II. Stability of 3,4-benzpyrene in light. Arch. Hyg. 143, 405 (1959).

    CAS  Google Scholar 

  • —, and H. Kunte: Carcinogenic substances in water and soil. XIV. Further investigations concerning polycyclic aromatic hydrocarbons in soil samples. Arch. Hyg. 147,401 (1963).

    CAS  Google Scholar 

  • —, G. Farkazdi, H. Glathe, and H. Kunte: The behavior of polycyclic aromate hydrocarbons in experiments with garbage-sewage sludge composts as fertilizers. Zlb. Bakt. Hyg. I. Abt. Orig. B, 157:151 (1973).

    CAS  Google Scholar 

  • —, F. Selenka, H. Kunte, and A. Maximos: Experimental studies on the formation of polycyclic aromatic hydrocarbons in plants. Env. Res. 2, 22 (1968a).

    CAS  Google Scholar 

  • — The synthesis of 3,4-benzopyrene and other polycyclic aromatic hydrocarbons in plants. Arch. Hyg. 152, 279 (1968b).

    CAS  Google Scholar 

  • Bourcart, J., and L. Mallet: Marine pollution of the shores of the central region of the Tyrrhenian Sea (Bay of Naples) by BP-type, pH. C. R. Acad. Sci. (Paris) 260, 3729 (1965).

    CAS  Google Scholar 

  • Boyland, E.: Studies in tissue metabolism. II. The inhibition of lactic dehydrogenase by derivatives of carcinogenic compounds. Biochem. J. 27, 791 (1933).

    PubMed  CAS  PubMed Central  Google Scholar 

  • Braunstein, H. M.: Environmental, health, and control aspects of coal conversion: An information overview. Oak Ridge National Laboratory. Prepared for Energy Research and Development Administration. ORNL/E15-94 (1977).

    Google Scholar 

  • —, E. D. Copenhaver, and H. A. Pfruderer (eds.): Environmental, health, and control aspects of coal conversion: an information overview. ORNL/ EIS-94 (1977).

    Google Scholar 

  • Brisou, J.: Biosynthesis of 3,4-benzpyrene and anaerobiosis. C. R. Soc. Biol. 163, 772 (1969).

    CAS  Google Scholar 

  • Brown, E. R., J. J. Hazdra, L. Keith, F. Greenspan, J. B. Kwapinski, and P. Beamer: Frequency of fish tumors found in a polluted watershed as compared to nonpolluted Canadian waters. Cancer Res. 33, 189 (1973).

    PubMed  CAS  Google Scholar 

  • Calder, J. A., and J. H. Lader: Effect of dissolved aromatic hydrocarbons on the growth of marine bacteria in batch culture. Applied Environ. Microbiol. 32, 95 (1976).

    CAS  Google Scholar 

  • Cerneglia, C. E., and D. T. Gibson: Metabolism of naphthalene by cell extracts of Cunninghamella elegans. Arch. Biochem. Biophys. 186, 121 (1978).

    Google Scholar 

  • — Oxidation of benzo(a)pyrene by the filamentous fungus Cunninghamella elegans. J. Biol. Chem. 254, 12174 (1979).

    Google Scholar 

  • —, R. L. Herbert, R. H. Dodge, P. J. Szaniszlo, and D. T. Gibson: Some approaches to studies on the degradation of aromatic hydrocarbons by fungi. In A. L. Bourquin and H. Pritshard (eds.); Microbial degradation of pollutants in marine environments. EPA-600/9-79-012:360-369 (1979).

    Google Scholar 

  • Colucci, J. M., and C. R. Begeman: Carcinogenic air pollutants in relation to automotive traffic in New York. Environ. Sci. Tech. 5, 145 (1971).

    CAS  Google Scholar 

  • Dagley, S.: Microbial degradation of organic compounds in the biosphere. Amer. Scientist 63, 681 (1975).

    CAS  Google Scholar 

  • —, W. C. Evans, and D. W. Ribbons: Polycyclic aromatic compounds. Nature 188, 560 (1960).

    PubMed  CAS  Google Scholar 

  • Dao, T. L., C. King, and T. Tominaga: Isolation, identification, and biological study of compounds derived from 3-methylcholanthrene by irradiation in dimethyl sulfoxide. Cancer Res. 31, 1492 (1971).

    PubMed  CAS  Google Scholar 

  • Davies, I. W., R. M. Harrison, R. Perry, D. Ratnayake, and R. A. Wellings: Municipal incinerator as source of polynuclear aromatic hydrocarbons in environment. Environ. Sci. Tech. 10, 451 (1976).

    CAS  Google Scholar 

  • Dean-Raymond, D., and R. Bartha: Biodegradation of some polynuclear aromatic petroleum components of marine bacteria. Chapter 9, Vol. 16 of Development in industrial microbiology. Society for Industrial Microbiology. Amer. Inst. Biol. Sciences, Washington, D.C., pp. 97-109 (1975).

    Google Scholar 

  • Diehl, E. K., F. du Brevil, and R. A. Glenn: Polynuclear emission from coalfired installations. J. Eng. Power. 89, 276 (1967).

    CAS  Google Scholar 

  • Dobbs, R. A., and J. M. Cohen: Carbon adsorption isotherms for toxic organics, U.S. Environmental Protection Agency 600/8-80-023, 321 p. (1980).

    Google Scholar 

  • Durmishidze, S. V., T. V. Devadariani, L. K. Kavtaradze, and L. S. H. Krartskhava: Assimilation and conversion of 3,4-benzypyrene by plants under sterile conditions. Doklady Academii Nauk SSSR 218, 1468 (1974).

    CAS  Google Scholar 

  • —, and D. S. H. Ugrekhlidze: Degradation of benzene in tea plants. Doklady Academii Nauk SSSR 184, 228 (1969).

    CAS  Google Scholar 

  • —, T. V. Devadariani, and L. K. Kavtaradze: Cleavage of 3,4-benzpyrene-l,2-14C by higher plants. Bull. Acad. Sci. Georgian SSR 70, 460 (1973).

    Google Scholar 

  • Eglinton, G. T., and M. T. Murphy: Organic geochemistry. New York: Pergamon (1968).

    Google Scholar 

  • Ershova, K. P.: Studies of the content of polycyclic hydrocarbons in effluents of petro-chemical industry and surface waters. Hyg. Sanit. 36, 474 (1971).

    Google Scholar 

  • Erskine, R. L., and E. V. Whitehead: Composition and analysis of marine pollutants. Iranian J. Sci. Tech. 3, 221 (1975).

    CAS  Google Scholar 

  • Flaig, W.: Chemistry of humic substances in relation to coalification. In R. F. Gould (ed.): Coal science, Advances In Chemistry Series 55, 58 (1965).

    Google Scholar 

  • Gardner, W. S., R. F. Lee, K. R. Tenore, and L. W. Smith: Degradation of selected polycyclic aromatic hydrocarbons in coastal sediments: Importance of microbes and polychaete worms. Water, Air, and Soil Pollution II, 339 (1979).

    Google Scholar 

  • Geissman, T. A., K. Y. Sim, and J. Murdoch: Organic minerals, picene, and chrysene as constituents of the mineral curtisite (idrialite). Experientia 23, 793 (1967).

    CAS  Google Scholar 

  • Gibson, D. T.: Microbial degradation of aromatic compounds. Science 161, 1093 (1968).

    CAS  Google Scholar 

  • — The microbial oxidation of aromatic hydrocarbons. CRC Critical Rev. Microbiol. 1, 199 (1971).

    CAS  Google Scholar 

  • — Microbial degradation of carcinogenic hydrocarbons and related compounds. Proc. Symp. Sources, Effects, and Sinks of Hydrocarbons in Aquatic Environment. Aug. 9-11, pp. 225-237 (1976).

    Google Scholar 

  • —, D. M. Jerina, H. Yagi, and H. J. C. Yeh]: Oxidation of the carcinogens benzo(a)pyrene and benzo(a)anthracene to dihydrodiols by a bacterium. Science 189, 295 (19

    PubMed  CAS  Google Scholar 

  • —, G. E. Cardini, F. C. Maseies, and R. E. Kallio: Incorporation of oxygen-18 into benzene by Pseudomonas putida. Biochem. 9, 1631 (1970).

    CAS  Google Scholar 

  • —, J. R. Koch, and R. E. Kallio: Oxidative degradation of aromatic hydrocarbons by microorganisms. I. Enzymatic formation of catechol from benzene. Biochem. 7, 2653 (1968).

    CAS  Google Scholar 

  • Giger, W., and M. Blumer: Polycyclic aromatic hydrocarbons in the environment: Isolation and characterization by chromatography, visible, ultraviolet, and mass spectrometry. Anal. Chem. 46, 1663 (1974).

    PubMed  CAS  Google Scholar 

  • Graf, W.: On the natural occurrence and importance of carcinogenic polycyclic aromatic hydrocarbons. Mediainische Klinik 60, 561 (1965).

    Google Scholar 

  • —, and H. Diehl: Concerning the naturally caused normal level of carcinogenic polycyclic aromatics and its cause. Arch. Hyg. 150, 49 (1966).

    CAS  Google Scholar 

  • —, and A. G. Hallen The phototoxic activity of carcinogenic polycyclic hydrocarbons and their degradation products in the biological test. Zentralbl. Bakteriol. Parasitenko. Infektionskr. Hyg. Abt. l: Orig., Reihe B 164, 250 (1977).

    CAS  Google Scholar 

  • —, and W. Nowak: Growth stimulation in lower and higher plants by carcinogenic polycyclic aromatic compounds. Arch. Hyg. Bakt. 150, 513, ORNL/tr-4111 (1966).

    PubMed  CAS  Google Scholar 

  • —, and C. Winter: 3:4 Benzypyren in erdol. Arch. Hyg. 152, 289 (1968).

    CAS  Google Scholar 

  • Griest, W. H., and S. E. Herbes: Characterization of environmental distribution of polycyclic aromatic hydrocarbons in sediment and water in the vicinity of a coal coking plant. Amer. Chem. Soc. Meeting, Div. Environ. Chem., Anaheim, CA, Mar. 18-22 (1978).

    Google Scholar 

  • Grigorenko, L. T., P. P. Dikun, I. A. Kalinina, A. N. Mironova, and V. P. Rzhekhin: 3,4-Benzpyrene content in sunflower and cotton seed oils. Prikl. Biokhim. Microbiol. 6, 142 (1970).

    CAS  Google Scholar 

  • Grimmer, G., and D. Duvel: Endogenous formation of polycyclic hydrocarbons in higher plants. 8. Carcinogenic hydrocarbons in the environment of humans. Aeitschrift Naturforsch Teil B. 256, 1171 (1970).

    Google Scholar 

  • —, and A. Hildebrand: Content of polycyclic hydrocarbons in various types of vegetables and lettuce. Deutsche Lebensmittel-Rundschau. Heft 8, 237 (1965).

    Google Scholar 

  • Groenewegen, D., and H. Stolp: Microbial breakdown of polycyclic aromatic hydrocarbons. Tbl. Bakt. Hyg. I. Abt: Orig. B162, 225 (1976).

    Google Scholar 

  • Gubergrits, M., L. Paalme, and R. Kirso: Degradation of benzo(a)pyrene and phenol by physicochemical agents during self-purification of reservoirs, Vapr. Profil Zagryazeniya Vnesh Sreds, Chastnosti Vodoemor, Kentseragen Veshchestvami, pp. 49-53 (1972).

    Google Scholar 

  • Hakama, M., and E. A. Saxen: Cereal consumption and gastric cancer. Int. J. Cancer 2, 265 (1967).

    PubMed  CAS  Google Scholar 

  • Hancock, J. L., H. G. Applegate, and J. D. Dodd: Polynuclear aromatic hydrocarbons on leaves. Atmos. Environ. 4, 363 (1970).

    CAS  Google Scholar 

  • Hangebrauck, R. P., D. J. Von Lehmden, and J. E. Meeker: Emissions of polynuclear hydrocarbons and other pollutants from heat generation and incineration processes. J. Air. Pollut. Control Assoc. 14, 267 (1964).

    PubMed  CAS  Google Scholar 

  • Harrison, R. M., R. Perry, and R. A. Wellings: Polynuclear aromatic hydrocarbons in raw, potable, and waste waters. Water Res. 9, 331 (1975).

    CAS  Google Scholar 

  • Hase, A., and R. A. Hites: On the origin of polycyclic aromatic hydrocarbons in recent sediments: Biosynthesis of anaerobic bacteria. Geochim. et.Cosmochim. Acta 40, 1141 (1976).

    CAS  Google Scholar 

  • Hass, B. S., and H. G. Applegate: The effects of unsubstituted polycyclic aromatic hydrocarbons on the growth of Escherichia coli. Chem. Biol. 10, 265 (1975).

    CAS  Google Scholar 

  • Hassett, J. J., J. C. Means, W. L. Banwart, S. G. Wood, A. Khan, and S. Ali: Sorption of dibenzothiophene by soils and sediments. J. Environ. Qual. 9, 184 (1980).

    CAS  Google Scholar 

  • Hattori, T., and R. Hattori: The physical environment in soil microbiology: an attempt to extend principles of microbiology to soil microorganisms. CRC Critical Rev. Microbiol., pp. 423-461 (1976).

    Google Scholar 

  • Hayaishi, O., and M. Nozaki: Nature and mechanisms of oxygenases. Science 164, 389 (1969).

    PubMed  CAS  Google Scholar 

  • Hayatsu, R., R. G. Scott, L. P. Moore, and M. H. Studier: Aromatic units in coal. Nature 257, 378 (1975).

    CAS  Google Scholar 

  • Herbes, S. E.: Partitioning of polycyclic aromatic hydrocarbons between dissolved and participate phases in natural waters. Water Res. 11, 493 (1977).

    CAS  Google Scholar 

  • — Rates of microbial transformations of polycyclic aromatic hydrocarbons in waters and sediments in the vicinity of a coal-coking wastewater discharge. Applied Environ. Microbiol. 41, 20 (1981).

    CAS  Google Scholar 

  • —, and L. R. Schwall: Microbial transformations of polycyclic aromatic hydrocarbons in pristine and petroleum-contaminated sediments. Applied Environ. Microbiol. 35, 306 (1978).

    CAS  Google Scholar 

  • —, G. R. Southworth, and C. W. Gehrs: Organic contaminants in aqueous coal conversion effluents: environmental consequences and research priorities. Trace substances in environmental health-X. A Symposium D. D. Hemphdll (ed.), Univ. Missouri, Columbia (1976).

    Google Scholar 

  • Hites, R. A., R. E. La Flamme, and J. W. Farrington: Sedimentary polycyclic aromatic hydrocarbons: The historical record. Science 19, 829 (1977).

    Google Scholar 

  • Hodgson, E., and F. E. Guthrie: Introduction to biochemical toxicology. New York: Elsevier (1980).

    Google Scholar 

  • Hodgson, G. W., B. Hitshon, K. Taguchi, B. L. Baker, and E. Peake: Geochemistry of porphyrins, chlorins, and polycyclic aromatics in soils, sediments, and sedimentary rocks. Geochim. Cosmochim. Acta. 32, 737 (1968).

    CAS  Google Scholar 

  • Horton, A. W., M. J. Burton, R. Tye, and E. L. Bingham: Composition and contaminants of distillate oils. Amer. Chem. Soc. Div. Petrol. Chem. Preprint 8, 59 (1963).

    Google Scholar 

  • Hussien, Y. A., M. S. Tewfik, and Y. A. Hamdi: Degradation of certain aromatic compounds by rhizobia. Soil Bio. Biochem. 6, 377 (1974).

    CAS  Google Scholar 

  • Il’nitskii, A. P.: Control of the pollution of water basins by carcinogenic hydrocarbons. Hyg. Sanit. 31, 389 (1966).

    Google Scholar 

  • —, and J. P. Cohan: Prophylaxis of food contamination with carcinogens. Voprosy Onhologii 18, 106 (1972).

    CAS  Google Scholar 

  • —, R. P. Ershova, A. Ya. Khesina, L. G. Rozhkova, V. G. Klubkov, and A. A. Korolev: Stability of carcinogenic substances in water and the efficacy of methods of decontamination. Gig. Sanit. 36, 8 (1971).

    CAS  Google Scholar 

  • —, L. G. Solenova, and V. V. Ignatova: Sanitary and oncological assessment of agricultural use of sewage containing carcinogenic hydrocarbons. Kazanskii Meditsinskii Zh. 2:80. ORNL/tr-2959 (1974).

    Google Scholar 

  • —, V. Yu Gvil’dis, U. S. Muschenko, and L. M. Shabad: Role of volcanoes in the formation of the natural level of carcinogens. Doklady Akademii Nauk SSSR 234, 717 (1977).

    CAS  Google Scholar 

  • Ishio, S., H. Nakagawa, and T. Tomiyama: Algal cancer and its causes. IL Separation of carcinogenic compounds from sea bottom mud polluted by wastes from the coal chemical industry. Bull. Japan Soc. Sci. Fish. 38, 571, ORNL/tr-2848 (1972).

    CAS  Google Scholar 

  • Jackson, H. M.: Synthetic fuels from coal: status and outlook of coal gasification and liquefaction. Committee on Energy and Natural Resources, U.S. Senate, Pub. No. 96-17, 1-196 (1979).

    Google Scholar 

  • Jamison, V. W., R. L. Raymond, and J. O. Hudson: Microbial hydrocarbon cooxidation. III. Isolation and characterization of an α,α′,dimethyl-cis, cismuconic acid-producing strain of Nor cardia corallina. Applied Microbiol. 17, 853 (1969).

    CAS  Google Scholar 

  • Jeffrey, A. M., H. J. C. Yeh, D. M. Jerina, T. R. Patel, J. F. Davey, and D. T. Gibson: Initial reactions in the oxidation of naphthalene by Pseudomonas putida. Biochem. 14, 575 (1975).

    CAS  Google Scholar 

  • Jerina, D. M., J. W. Daly, A. M. Jeffrey, and D. T. Gibson: Cis-l,2-dihydroxy-1,2-dihydronaphthalene: a bacterial metabolite from naphthalene. Arch. Biochem. Biophys. 142, 394 (1971).

    PubMed  CAS  Google Scholar 

  • Jones, J. R. E.: Fish and river pollution. London: Butterworths (1964).

    Google Scholar 

  • Junk, G. A., and C. S. Ford: A review of organic emissions from selected combustion processes. Chemosphere 9, 187 (1980).

    CAS  Google Scholar 

  • Karickhoff, S. W., D. S. Brown, and T. A. Scott: Sorption of hydrophobic pollutants of natural sediments. Water Res. 13, 241 (1979).

    CAS  Google Scholar 

  • Karu, T., U. Kirse, and M. Gubergrits: Kinetics of the photoinduced cooxidation of benzo(a)pyrene and phenols. Eesti NSV Tead Akad. Toim, Keem, Geol. 22, 217 (1973).

    CAS  Google Scholar 

  • Khesina, A. Ya, N. P. Shcherback, L. M. Shabad, and I. S. Vostrov: Benzpyrene breakdown by the soil microflora. Byulleten Eksperimental’noi Biologii i Meditsiny 68, 70 (1969).

    CAS  Google Scholar 

  • Kingsbury, G. L., R. C. Sims, and J. B. White: Multimedia goals for environmental assessment. EPA-600/7-79-176b (1979).

    Google Scholar 

  • Kolar, L., R. Ledvina, J. Ticha, and R. Hanus: Contamination of soil, agricultural crops, and vegetables by 3,4-benzpyrene in the vicinity of Ceska Budejovice. Ceskosolvenska Hygiena 20, 135 (1975).

    CAS  Google Scholar 

  • Lane, D. A., and M. Katz: The photomodification of benzo(a)pyrene, benzo(b)-fluoranthene, and benzo(k)fluoranthene under simulated atmospheric conditions. In Suffet I. H. (ed.): Fate of pollutants in the air and water environments. Part 2, pp. 135–154. New York: Wiley (1977).

    Google Scholar 

  • Lee, R., W. S. Gardner, J. W. Anderson, J. W. Blaylock, and J. B. Clarke: Fate of polycyclic aromatic hydrocarbons in controlled ecosystem enclosures. Environ. Sci. Tech. 12, 832 (1978).

    CAS  Google Scholar 

  • Lijinsky, W., and J. H. Quastel: Metabolism of carcinogenic hydrocarbons by soil microorganisms. Arch. Biochem. Biophys. 63, 160 (1956).

    PubMed  CAS  Google Scholar 

  • Lopp, A., L. Paalme, and M. Gubergrits: Kinetics of photoinduced oxidation of 7,12-dimethylbenz(a)anthracene in various solvents. Eesti NSV Tead Akad. Toim, Keem, Geol. 25, 22 (1976).

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  • Mackay, D., and P. J. Leinonen: Rate of evaporation of low-solubility contaminants from water bodies to atmosphere. Environ. Sci. Tech. 9, 1178 (1975).

    CAS  Google Scholar 

  • —, and A. W. Wolkoff: Rate of evaporation of low-solubility contaminants from water bodies to atmosphere. Environ. Sci. Tech. 7, 611 (1973).

    CAS  Google Scholar 

  • Macphee, C, and R. Ruelle: Lethal effects of 1888 chemicals upon four species of fish from western North America. Univ. Idaho, Coll. Forestry, Wildlife and Range Sciences, Bull. No. 3 (1969).

    Google Scholar 

  • Mailath, F. P., F. Medve, and J. Morik: Photolysis of 3,4-benzypyrene by ultraviolet radiation and sunlight. Egeszsgtudomany 13, 333 (1974).

    Google Scholar 

  • Mair, B. J., and J. L. Martinez Pico: Diagenesis of plant sterols. Proc. Amer. Petrol. Inst. 42, 173 (1962).

    CAS  Google Scholar 

  • Malaney, G. W., P. A. Lutin, J. J. Chibulka, and L. H. Hickerson: Resistance of carcinogenic organic compounds to oxidation by activated sludge. J. Water Pollut. Control Fed. 39, 20202 (1967).

    Google Scholar 

  • Mallet, L., A. Perdriau, and J. Perdriau: The extent of pollution by BP-type PH in the North Sea and Glacial Arctic Ocean. Bull. Acad. Nat. Med. (Paris) 147, 320 (1963).

    CAS  Google Scholar 

  • —, J. Zanghi, and J. Brisou: Investigations of the possibilities of biosynthesis of a polybenzene hydrocarbons of the benzo-3,4-pyrene type by a Clostridium putride in the presence of marine plankton lipids. Acad. Sci., Paris Ser. D. 264, 1534 (1967).

    CAS  Google Scholar 

  • McBride, M. B., T. J. Pinnavaia, and M. M. Mortland: Adsorption of aromatic molecules by clays in aqueous suspensions. Ithaca, New York: N.Y. State College of Agriculture and Life Sci., Cornell University (1975).

    Google Scholar 

  • McCann, J., and B. N. Ames: A simple method for detecting environmental carcinogens as mutagens. Ann. N.Y. Acad. Sci. 271, 5 (1975).

    Google Scholar 

  • McGinnes, P. R., and V. L. Snoeynik: Determination of the fate of polynuclear aromatic hydrocarbons in natural water systems. WRC Res. Rep. 80. Urbana, Illinois: University of Illinois Water Resources Center (1974).

    Google Scholar 

  • McKee, J. E., and H. W. Wolf (eds.): Water quality criteria, 2nd ed., Calif. State Water Resources Control Board (1963).

    Google Scholar 

  • McKenna, E. J.: Bio degradation of polynuclear aromatic hydrocarbon pollutants: By soil and water microorganisms. Amer. Inst. Chem. Eng. 70th Ann. Meet. Nov. 13-17, New York, NY (1977).

    Google Scholar 

  • Means, J. C., J. J. Hassett, S. G. Wood, and W. L. Banwart: Sorption properties of energy-related pollutants and sediments. 327–340. In P. W. Jones and P. Leber (eds.): Polynuclear aromatic hydrocarbons. Ann Arbor, Mich.: Ann Arbor Sci. Publ., Inc. (1979).

    Google Scholar 

  • Means, J. C. —, G. S. Wood, J. J. Hassett, and W. L. Banwart: Sorption of polynuclear aromatic hydrocarbons by sediments and soils. Environ. Sci. Tech. 14, 1524 (1980).

    CAS  Google Scholar 

  • Medvedev, V. A., and V. D. Davidov: Transformation of individual organic products of the coke industry in chernozemic soils. Pochvovedenie 11, 22 (1972).

    Google Scholar 

  • Murdock, J., and T. A. Geissman: Pendletonite, a new hydrocarbon mineral from California. Amer. Mineral 52, 611 (1967).

    Google Scholar 

  • National Academy of Sciences, National Research Council: Particulate polycyclic organic matter. Washington, D.C.: National Academy of Sciences (1972).

    Google Scholar 

  • Niaussat, P., C. Auger, and L. Mallet: Appearance of carcinogenic hydrocarbons in pure Bacillus hadius cultures relative to the presence of certain compounds in the medium. Compt. Rend. 270D, 1042 (1970).

    Google Scholar 

  • —, L. Mallet, and J. Ottenwaelder: Appearance of 3,4-benzpyrene in various strains of marine phytoplankton raised in vitro. Compt. Rend. Acad. Sci. Paris, t. 268, 1109 (1969).

    CAS  Google Scholar 

  • Nozaki, M., H. Kagamiyama, and O. Hayaishi: Metapyrochatechase. I. Purification, crystallization and some properties. Biochem. Z. 338, 582 (1963).

    PubMed  CAS  Google Scholar 

  • Paalme, L., and M. Gubergrits: Kinetics of photodecomposition of 1,2-benzpyrene. Eesti NSV Tead Akad. Toim, Keem, Geol. 21, 48 (1972).

    CAS  Google Scholar 

  • — Kinetics of cooxidation of 1,2-and 3,4-benzpyrene activated by UV radiation. In N. M. Emanuel (ed.): Tear Prakt Zhidkofazn Okieleniya, pp. 12–122, Nauka, Moscow, U.S.S.R. (1974).

    Google Scholar 

  • — Kinetics of the separate and combined photo degradation of benzo(a)pyrene, pyrene, and 3-methylcholanthrene. Eesti NSV Tead Akad. Toim, Keem, Geol. 25, 271 (1976).

    CAS  Google Scholar 

  • —, A. Lopp, and M. Gubergrits: Kinetics of cooxidative photodegradation of benzo(a)pyrene and 7,12-dimethylbenz(a)anthracene. Eesti NGV Tead Akadd. Toim, Keem, Geol. 25, 247 (1976).

    CAS  Google Scholar 

  • —, R. Priiman, M. I. Gloshko, and M. Gubergrits: Simultaneous photoinduced oxidation of 3,4-benzpyrene and alkyl arylsulfonates. Vodn. Resur.,pp. 174–178 (1975).

    Google Scholar 

  • Panalaks, T.: Determination and identification of polycyclic aromatic hydrocarbons in smoked and charcoal-broiled food products by high pressure liquid chromatography. J. Environ. Sci. Health B 11, 299 (1976).

    Google Scholar 

  • Perry, J. J.: Microbial cooxidations involving hydrocarbons. Microbiol. Rev. 45, 59 (1979).

    Google Scholar 

  • Poglazova, M. N., G. E. Fedoseeva, A. J. Khesina, M. N. Meissel, and L. M. Shabad: Destruction of benzo (a)pyrene by soil bacteria. Life Sciences 6, 1053 (1967a).

    PubMed  CAS  Google Scholar 

  • A. J. Khesina, M. N. Meissel, and L. M. Shabad — Further investigations of the decomposition of benz(a) pyrene by soil bacteria. Doklady Akademii Nauk SSSR. 176, 1165 (1967b).

    PubMed  CAS  Google Scholar 

  • A. J. Khesina, M. N. Meissel, and L. M. Shabad — The oxidation of benz (a) pyrene by microorganisms in relation to its concentration in the medium. Doklady Akademii Nauk SSSR 179, 1460 (1968).

    PubMed  CAS  Google Scholar 

  • Radding, S. B., T. Mill, C. W. Gould, D. H. Liu, H. L. Johnson, D. C. Bomberger, and C. V. Fojo: The environmental fate of selected polynuclear aromatic compounds. U.S. Environmental Protection Agency, 122 p. EPA-560/5-75-009 (1976).

    Google Scholar 

  • Raymond, R. L., V. W. Jamison, and J. O. Hudson: Microbial hydrocarbon cooxidation. I. Oxidation of mono-and dicyclic hydrocarbons by soil isolates. Applied Microbiol. 15, 857 (1967).

    CAS  Google Scholar 

  • Reinbold, K. A., J. J. Hassett, J. C. Means, and W. L. Banwart: Adsorption of energy-related organic pollutants: a literature review. Inst. Environ. Sci., Dept. Agron., Univ. EL, Urbana, Champaign, for U.S. EPA Office for Research and Development, Athens, GA, 130 p. (1978).

    Google Scholar 

  • Rogoff, M. H., and I. Wender: The microbiology of coal. I. Bacterial oxidation of phenanthrene. J. Bacteriol. 73, 264 (1957).

    PubMed  CAS  PubMed Central  Google Scholar 

  • Rohrlich, M., and P. Suckow: Oxidative modification of 3,4-benzpyrene on cereals and in pastry. Chem. Mikrobiol. Technol. Lebensm. 2, 137 (1973).

    CAS  Google Scholar 

  • Rondia, D., and S. S. Epstein: Effect of antioxidants on photodecomposition of benzo(a)pyrene. Life Sci. 7, 513 (1968).

    CAS  Google Scholar 

  • Ryan, P. W., and C. K. McMahon: Some chemical and physical characteristics of emissions from forest firest. Paper 76-2.3, 69th Annual Meeting Air Pollution Control Assoc, Portland, OR, June 27-July 1 (1976).

    Google Scholar 

  • Sawicki, E., J. E. Meeker, and M. J. Morgan: Polynuclear aza compounds in automotive exhaust. Arch. Environ. Health 11, 773 (1965).

    PubMed  CAS  Google Scholar 

  • Selander, H., H. Yagi, D. M. Jerina, M. C. Wells, J. F. Davey, V. Mahadevan, and D. T. Gibson: Dihydrodiols from anthracene and phenanthrene. J. Amer. Chem. Soc. 129, 67 (1971).

    Google Scholar 

  • Shabad, L. M.: Studies in the U.S.S.R. on the distribution, circulation, and fate of carcinogenic hydrocarbons in the human environment and the role of their disposition in tissues in carcinogenesis. A Review. Cancer Res. 27, 1132 (1967).

    PubMed  CAS  Google Scholar 

  • — Circulation of carcinogenic substances in the environment: From laboratory experiments to field investigations. GANN Monograph on Cancer Research 17, 179 (1975).

    CAS  Google Scholar 

  • —, and Y. L. Cohan: The contents of benzo(a)pyrene in some crops. Arch. Geschwultsforsch 40, 237 (1972).

    CAS  Google Scholar 

  • —, A. Ya Khesina, H. P. Schubak, and G. A. Smirnov: The carcinogenic hydrocarbon benzo(a)pyrene in the soil. J. Nat. Cancer Inst. 47, 1179 (1969).

    Google Scholar 

  • Shamsuzzaman, K. M., and E. A. Barnsley: The regulation of naphthalene metabolism in pseudomonas. Biochem. Biophys. Res. 60, 592 (1974). 1179 (1969).

    Google Scholar 

  • Shamsuzzaman, K. M., and E. A. Barnsley: The regulation of naphthalene metabolism in pseudomonas. Biochm. Biophys. Res. 60, 592 (1974).

    Google Scholar 

  • Shcherbak, N. P.: Some results of a study of the fate of benz(a)pyrene in soil. Vapr. Onkel. 15, 75 (1969).

    CAS  Google Scholar 

  • Sherrill, T. W., and G. S. Sayler: Phenanthrene biodegradation in freshwater environments. Applied Environ. Microbiol. 39, 172 (1980).

    CAS  Google Scholar 

  • Shiraishi, Y.: Determination of polycyclic aromatic hydrocarbons in food. IV. 3,4-Benzpyrene in fish and shellfish. J. Food. Hyg. Soc. Japan 16, 178 (1975).

    CAS  Google Scholar 

  • —, and E. Takabatake: Determination of polycyclic aromatic hydrocarbons in foods. 3. 3,4-Benzopyrene in vegetables. Shokuhin Eiseigaku Zasshi 15, 18, ORNL/tr-4125 (1974).

    CAS  Google Scholar 

  • Siddiqi, I., and K. H. Wagner: Determination of 3,4-benzpyrene and 3,4-benzfluoranthene in rain water, ground water, and wheat. Chemosphere 1, 83 (1972).

    CAS  Google Scholar 

  • Siegfried, R.: Effect of garbage compost on the 3,4-benzpyrene content of carrots and head lettuce. Naturwissenschaften 62, 300, ORNL/tr-4124 (1975).

    Google Scholar 

  • Sims, R. C: Land treatment of polynuclear aromatic compounds. PhD disserta’tion. Dept. Biol. Agr. Eng., No. Carolina State Univ., Raleigh, NC (1982).

    Google Scholar 

  • Simmon, V., and J. M. Baden: Mutagenic activity of vinyl compounds and derived epoxides. Mut. Res. 78, 227 (1980).

    CAS  Google Scholar 

  • Sisler, F. D., and C. E. Zobell: Microbial utilization of carcinogenic hydrocarbons. Science 106, 521 (1947).

    PubMed  CAS  Google Scholar 

  • Skrigan, A. L: Diagenesis of α-pinene in pine stumps. Doklady Akad. Nauk. SSSR 80, 607 (1951).

    CAS  Google Scholar 

  • — Diagenesis of abietic acid in buried pine trees. Through Chem. Abstr. 62, 10664 (1965).

    Google Scholar 

  • Smirnov, G. A.: The study of the benz(alpha)pyrene content in the soil and vegetation in the airfield region. Vop. Onkol. 16, 83 (1970).

    CAS  Google Scholar 

  • Smith, J., W. R. Mabey, N. Bohomos, B. R. Holt, S. S. Lee, T. W. Chou, D. C. Bomberger, and T. Hill: Environmental pathways of selected chemicals in freshwater systems. U.S. EPA (Office of Research and Development), Athens, GA. EPA-600/7-78-074 (1978).

    Google Scholar 

  • Southworth, G. R.: Transport and transformation of anthracene in natural waters: Process rate studies. Oak Ridge, Tennessee: U.S. Department of Energy (ORNL) 26 p. (1977).

    Google Scholar 

  • —, J. J. Beauchamp, and P. K. Schmieder: Bioaccumulation potential of polycyclic aromatic hydrocarbons in Daphnia pulex. Water Res. 12, 973 (1978).

    CAS  Google Scholar 

  • Stanier, R. Y., and J. L. Ingraham: Protocatechuic acid oxidase. J. Biol. Chem. 210, 799 (1954).

    PubMed  CAS  Google Scholar 

  • Stevens, B., and B. E. Algar: Photoperoxidation of unsaturated organic molecules. II. Autoperoxidation of aromatic hydrocarbons. J. Phys. Chem. 72, 3468 (1968).

    CAS  Google Scholar 

  • Stotzky, G.: Techniques to study interactions between microorganisms and clay minerals in vivo and in vitro. Bull. Ecol. Res. Comm. (Stockholm) 17, 17 (1973).

    CAS  Google Scholar 

  • Suess, M. J.: Aqueous solutions of 3,4-benzpyrene. Water Res. 6, 981 (1972a).

    CAS  Google Scholar 

  • — Polynuclear aromatic hydrocarbon pollution of the marine environment. In M. Ruivo (ed.): Marine pollution and sea life. London. Fishing New Books (1972 b).

    Google Scholar 

  • — The environmental load and cycle of polycyclic aromatic hydrocarbons. The Sci. of the Total Environ. 6: 239–250 (1976).

    CAS  Google Scholar 

  • Tausson, V. O.: In N. A. Meximov (ed.): Basic principles of plant bioenergetics. Acad. Sci, U.S.S.R. (1950).

    Google Scholar 

  • Thakker, D. R., W. Levin, H. Yagi, M. Tada, A. H. Conney, and D. M. Jerina: Comparative metabolism of dihydrodiols of polycyclic aromatic hydrocarbons to bay region diol epoxides. Fourth Internat. Symp. Polynuclear Aromatic Hydrocarbons. Columbus, OH, Oct. 2-4, 1979, U.S. EPA: Battelle Press (1980).

    Google Scholar 

  • Tye, R., M. J. Burton, E. Bingham, A. Bell, and A. W. Horton: Carcinogens in a cracked petroleum residuum. Arch. Environ. Health 13, 202 (1966).

    PubMed  CAS  Google Scholar 

  • U.S. EPA: Review and evaluation of available techniques for determining persistence and routes of degradation of chemical substances in the environment. Syracuse Univ. Res. Corp., NTIS PB-243825, 549 pp. (1975 a).

    Google Scholar 

  • — Scientific and technical assessment report on particulate polycyclic organic matter (PPOM). Star Series. Superintendent of Documents, Washington, D.C.: U.S. Government Printing Office, EPA-600/6-74-001 (1975 b).

    Google Scholar 

  • — Rationale for recommended list of priority pollutants. Memo to director of Effluent Guidelines Division. Nov. 19 (1976).

    Google Scholar 

  • — Environmental pathways of selected chemicals in freshwater systems. Part II. Laboratory studies. EPA-600/7-78-074 (1978).

    Google Scholar 

  • Versar, Inc.: Water related environmental fate of 129 priority pollutants. A literature search. V. polycyclic aromatic hydrocarbons, PCBs and related compounds. For U.S. EPA Office of Water Planning and Standards, Washington, D.C. (1979).

    Google Scholar 

  • Wagner, Van K. H., and I. Siddiqi: The metabolism of 3,4-benzpyrene and 3,4-benzfluoranthene in summer wheat. Z. Pflanzen Bodenkundle 127, 211 (1970).

    CAS  Google Scholar 

  • Wagner, K. H., and C. Vonderheid: Polycyclic aromatic hydrocarbons in technically prepared composts. Naturwissenschaften 65, 491 (1978).

    CAS  Google Scholar 

  • —, and E. Wagner-Hering: The cycle of cancer-causing substances-polycyclic aromatic hydrocarbons-in plants and humans. Protectio Vitae 6, 260 (1971).

    Google Scholar 

  • Webley, D. M., R. B. Duff, and V. C. Farmer: The metabolism of iron-, zinc-and manganese deficient bacteria. J. General Microbiol. 29, 179 (1962).

    CAS  Google Scholar 

  • Windsor, J. G., and R. A. Hites: Polycyclic aromatic hydrocarbons in Gulf of Maine sediments and Nova Scotia soils. Geochim et. Cosmochim. Acta 43, 27 (1979).

    CAS  Google Scholar 

  • Wiser, W. H.: Some chemical aspects of coal liquefication. Paper presented Short Course on Coal Characteristics and Coal Conversion Processes, Oct. 29-Nov. 2, Pennsylvania State Univ., Univ. Park, PA (1973).

    Google Scholar 

  • Wright, A. S.: The role of metabolism in chemical mutagenesis and chemical carcinogenesis. Mut. Res. 75, 215 (1980).

    CAS  Google Scholar 

  • Wynder, E. L., J. Kmet, N. Dungal, and N. Segi: An epidemiological investigation of gastric cancer. Cancer 16, 1461 (1963).

    PubMed  CAS  Google Scholar 

  • Youngblood, W. W., and M. Blumer: Polycyclic aromatic hydrocarbons in the environment: Homologous series in soils and recent marine sediments. Geochim. et Cosmochim. Acta 39, 1303 (1975).

    CAS  Google Scholar 

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Sims, R.C., Overcash, M.R. (1983). Fate of polynuclear aromatic compounds (PNAs) in soil-plant systems. In: Gunther, F.A. (eds) Residue Reviews. Residue Reviews, vol 88. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-5569-7_1

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