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).
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).
Alexander, M.: Introduction to soil microbiology, 2nd ed. New York: Wiley (1977).
Ames, B. N., P. Sims, and P. L. Grover: Epoxides of polycyclic hydrocarbons are frameshift mutagens. Science 176, 47 (1972)
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).
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).
Bailey, E. J., and N. Dungal: Polycyclic hydrocarbons in icelandic smoked food. Brit. J. Cancer. 12, 348 (1958).
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).
Balls, M.: Benzpyrene-induced tumors in the clawed toad, Xenopus laevis. Experientia 20(3), 143 (1964).
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).
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).
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).
Binet, L., and L. Mallet: Diffusion of pH in the animated environment. Gaz. Hop. (Paris) 135, 1142 (1963).
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).
Blumer, M.: Curtisite, idrialite, and pendletonite, polycyclic aromatic hydrocarbon minerals: Their composition and origin. Chem. Geol. 16, 245 (1975).
— Polycyclic aromatic compounds in nature. Sci. American 234(3), 35 (1976).
—, and W. W. Youngblood: Polycyclic aromatic hydrocarbons in soils and recent sediments. Science 188, 53 (1975).
Borneff, J., and R. Knerr: Carcinogenic substances in water and soil. II. Stability of 3,4-benzpyrene in light. Arch. Hyg. 143, 405 (1959).
—, and H. Kunte: Carcinogenic substances in water and soil. XIV. Further investigations concerning polycyclic aromatic hydrocarbons in soil samples. Arch. Hyg. 147,401 (1963).
—, 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).
—, F. Selenka, H. Kunte, and A. Maximos: Experimental studies on the formation of polycyclic aromatic hydrocarbons in plants. Env. Res. 2, 22 (1968a).
— The synthesis of 3,4-benzopyrene and other polycyclic aromatic hydrocarbons in plants. Arch. Hyg. 152, 279 (1968b).
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).
Boyland, E.: Studies in tissue metabolism. II. The inhibition of lactic dehydrogenase by derivatives of carcinogenic compounds. Biochem. J. 27, 791 (1933).
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).
—, E. D. Copenhaver, and H. A. Pfruderer (eds.): Environmental, health, and control aspects of coal conversion: an information overview. ORNL/ EIS-94 (1977).
Brisou, J.: Biosynthesis of 3,4-benzpyrene and anaerobiosis. C. R. Soc. Biol. 163, 772 (1969).
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).
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).
Cerneglia, C. E., and D. T. Gibson: Metabolism of naphthalene by cell extracts of Cunninghamella elegans. Arch. Biochem. Biophys. 186, 121 (1978).
— Oxidation of benzo(a)pyrene by the filamentous fungus Cunninghamella elegans. J. Biol. Chem. 254, 12174 (1979).
—, 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).
Colucci, J. M., and C. R. Begeman: Carcinogenic air pollutants in relation to automotive traffic in New York. Environ. Sci. Tech. 5, 145 (1971).
Dagley, S.: Microbial degradation of organic compounds in the biosphere. Amer. Scientist 63, 681 (1975).
—, W. C. Evans, and D. W. Ribbons: Polycyclic aromatic compounds. Nature 188, 560 (1960).
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).
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).
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).
Diehl, E. K., F. du Brevil, and R. A. Glenn: Polynuclear emission from coalfired installations. J. Eng. Power. 89, 276 (1967).
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).
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).
—, and D. S. H. Ugrekhlidze: Degradation of benzene in tea plants. Doklady Academii Nauk SSSR 184, 228 (1969).
—, 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).
Eglinton, G. T., and M. T. Murphy: Organic geochemistry. New York: Pergamon (1968).
Ershova, K. P.: Studies of the content of polycyclic hydrocarbons in effluents of petro-chemical industry and surface waters. Hyg. Sanit. 36, 474 (1971).
Erskine, R. L., and E. V. Whitehead: Composition and analysis of marine pollutants. Iranian J. Sci. Tech. 3, 221 (1975).
Flaig, W.: Chemistry of humic substances in relation to coalification. In R. F. Gould (ed.): Coal science, Advances In Chemistry Series 55, 58 (1965).
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).
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).
Gibson, D. T.: Microbial degradation of aromatic compounds. Science 161, 1093 (1968).
— The microbial oxidation of aromatic hydrocarbons. CRC Critical Rev. Microbiol. 1, 199 (1971).
— 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).
—, 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
—, G. E. Cardini, F. C. Maseies, and R. E. Kallio: Incorporation of oxygen-18 into benzene by Pseudomonas putida. Biochem. 9, 1631 (1970).
—, 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).
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).
Graf, W.: On the natural occurrence and importance of carcinogenic polycyclic aromatic hydrocarbons. Mediainische Klinik 60, 561 (1965).
—, and H. Diehl: Concerning the naturally caused normal level of carcinogenic polycyclic aromatics and its cause. Arch. Hyg. 150, 49 (1966).
—, 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).
—, and W. Nowak: Growth stimulation in lower and higher plants by carcinogenic polycyclic aromatic compounds. Arch. Hyg. Bakt. 150, 513, ORNL/tr-4111 (1966).
—, and C. Winter: 3:4 Benzypyren in erdol. Arch. Hyg. 152, 289 (1968).
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).
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).
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).
—, and A. Hildebrand: Content of polycyclic hydrocarbons in various types of vegetables and lettuce. Deutsche Lebensmittel-Rundschau. Heft 8, 237 (1965).
Groenewegen, D., and H. Stolp: Microbial breakdown of polycyclic aromatic hydrocarbons. Tbl. Bakt. Hyg. I. Abt: Orig. B162, 225 (1976).
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).
Hakama, M., and E. A. Saxen: Cereal consumption and gastric cancer. Int. J. Cancer 2, 265 (1967).
Hancock, J. L., H. G. Applegate, and J. D. Dodd: Polynuclear aromatic hydrocarbons on leaves. Atmos. Environ. 4, 363 (1970).
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).
Harrison, R. M., R. Perry, and R. A. Wellings: Polynuclear aromatic hydrocarbons in raw, potable, and waste waters. Water Res. 9, 331 (1975).
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).
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).
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).
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).
Hayaishi, O., and M. Nozaki: Nature and mechanisms of oxygenases. Science 164, 389 (1969).
Hayatsu, R., R. G. Scott, L. P. Moore, and M. H. Studier: Aromatic units in coal. Nature 257, 378 (1975).
Herbes, S. E.: Partitioning of polycyclic aromatic hydrocarbons between dissolved and participate phases in natural waters. Water Res. 11, 493 (1977).
— 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).
—, and L. R. Schwall: Microbial transformations of polycyclic aromatic hydrocarbons in pristine and petroleum-contaminated sediments. Applied Environ. Microbiol. 35, 306 (1978).
—, 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).
Hites, R. A., R. E. La Flamme, and J. W. Farrington: Sedimentary polycyclic aromatic hydrocarbons: The historical record. Science 19, 829 (1977).
Hodgson, E., and F. E. Guthrie: Introduction to biochemical toxicology. New York: Elsevier (1980).
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).
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).
Hussien, Y. A., M. S. Tewfik, and Y. A. Hamdi: Degradation of certain aromatic compounds by rhizobia. Soil Bio. Biochem. 6, 377 (1974).
Il’nitskii, A. P.: Control of the pollution of water basins by carcinogenic hydrocarbons. Hyg. Sanit. 31, 389 (1966).
—, and J. P. Cohan: Prophylaxis of food contamination with carcinogens. Voprosy Onhologii 18, 106 (1972).
—, 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).
—, 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).
—, 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).
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).
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).
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).
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).
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).
Jones, J. R. E.: Fish and river pollution. London: Butterworths (1964).
Junk, G. A., and C. S. Ford: A review of organic emissions from selected combustion processes. Chemosphere 9, 187 (1980).
Karickhoff, S. W., D. S. Brown, and T. A. Scott: Sorption of hydrophobic pollutants of natural sediments. Water Res. 13, 241 (1979).
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).
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).
Kingsbury, G. L., R. C. Sims, and J. B. White: Multimedia goals for environmental assessment. EPA-600/7-79-176b (1979).
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).
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).
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).
Lijinsky, W., and J. H. Quastel: Metabolism of carcinogenic hydrocarbons by soil microorganisms. Arch. Biochem. Biophys. 63, 160 (1956).
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).
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).
Mackay, D., and P. J. Leinonen: Rate of evaporation of low-solubility contaminants from water bodies to atmosphere. Environ. Sci. Tech. 9, 1178 (1975).
—, and A. W. Wolkoff: Rate of evaporation of low-solubility contaminants from water bodies to atmosphere. Environ. Sci. Tech. 7, 611 (1973).
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).
Mailath, F. P., F. Medve, and J. Morik: Photolysis of 3,4-benzypyrene by ultraviolet radiation and sunlight. Egeszsgtudomany 13, 333 (1974).
Mair, B. J., and J. L. Martinez Pico: Diagenesis of plant sterols. Proc. Amer. Petrol. Inst. 42, 173 (1962).
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).
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).
—, 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).
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).
McCann, J., and B. N. Ames: A simple method for detecting environmental carcinogens as mutagens. Ann. N.Y. Acad. Sci. 271, 5 (1975).
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).
McKee, J. E., and H. W. Wolf (eds.): Water quality criteria, 2nd ed., Calif. State Water Resources Control Board (1963).
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).
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).
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).
Medvedev, V. A., and V. D. Davidov: Transformation of individual organic products of the coke industry in chernozemic soils. Pochvovedenie 11, 22 (1972).
Murdock, J., and T. A. Geissman: Pendletonite, a new hydrocarbon mineral from California. Amer. Mineral 52, 611 (1967).
National Academy of Sciences, National Research Council: Particulate polycyclic organic matter. Washington, D.C.: National Academy of Sciences (1972).
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).
—, 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).
Nozaki, M., H. Kagamiyama, and O. Hayaishi: Metapyrochatechase. I. Purification, crystallization and some properties. Biochem. Z. 338, 582 (1963).
Paalme, L., and M. Gubergrits: Kinetics of photodecomposition of 1,2-benzpyrene. Eesti NSV Tead Akad. Toim, Keem, Geol. 21, 48 (1972).
— 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).
— 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).
—, 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).
—, R. Priiman, M. I. Gloshko, and M. Gubergrits: Simultaneous photoinduced oxidation of 3,4-benzpyrene and alkyl arylsulfonates. Vodn. Resur.,pp. 174–178 (1975).
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).
Perry, J. J.: Microbial cooxidations involving hydrocarbons. Microbiol. Rev. 45, 59 (1979).
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).
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).
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).
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).
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).
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).
Rogoff, M. H., and I. Wender: The microbiology of coal. I. Bacterial oxidation of phenanthrene. J. Bacteriol. 73, 264 (1957).
Rohrlich, M., and P. Suckow: Oxidative modification of 3,4-benzpyrene on cereals and in pastry. Chem. Mikrobiol. Technol. Lebensm. 2, 137 (1973).
Rondia, D., and S. S. Epstein: Effect of antioxidants on photodecomposition of benzo(a)pyrene. Life Sci. 7, 513 (1968).
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).
Sawicki, E., J. E. Meeker, and M. J. Morgan: Polynuclear aza compounds in automotive exhaust. Arch. Environ. Health 11, 773 (1965).
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).
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).
— Circulation of carcinogenic substances in the environment: From laboratory experiments to field investigations. GANN Monograph on Cancer Research 17, 179 (1975).
—, and Y. L. Cohan: The contents of benzo(a)pyrene in some crops. Arch. Geschwultsforsch 40, 237 (1972).
—, 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).
Shamsuzzaman, K. M., and E. A. Barnsley: The regulation of naphthalene metabolism in pseudomonas. Biochem. Biophys. Res. 60, 592 (1974). 1179 (1969).
Shamsuzzaman, K. M., and E. A. Barnsley: The regulation of naphthalene metabolism in pseudomonas. Biochm. Biophys. Res. 60, 592 (1974).
Shcherbak, N. P.: Some results of a study of the fate of benz(a)pyrene in soil. Vapr. Onkel. 15, 75 (1969).
Sherrill, T. W., and G. S. Sayler: Phenanthrene biodegradation in freshwater environments. Applied Environ. Microbiol. 39, 172 (1980).
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).
—, 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).
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).
Siegfried, R.: Effect of garbage compost on the 3,4-benzpyrene content of carrots and head lettuce. Naturwissenschaften 62, 300, ORNL/tr-4124 (1975).
Sims, R. C: Land treatment of polynuclear aromatic compounds. PhD disserta’tion. Dept. Biol. Agr. Eng., No. Carolina State Univ., Raleigh, NC (1982).
Simmon, V., and J. M. Baden: Mutagenic activity of vinyl compounds and derived epoxides. Mut. Res. 78, 227 (1980).
Sisler, F. D., and C. E. Zobell: Microbial utilization of carcinogenic hydrocarbons. Science 106, 521 (1947).
Skrigan, A. L: Diagenesis of α-pinene in pine stumps. Doklady Akad. Nauk. SSSR 80, 607 (1951).
— Diagenesis of abietic acid in buried pine trees. Through Chem. Abstr. 62, 10664 (1965).
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).
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).
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).
—, J. J. Beauchamp, and P. K. Schmieder: Bioaccumulation potential of polycyclic aromatic hydrocarbons in Daphnia pulex. Water Res. 12, 973 (1978).
Stanier, R. Y., and J. L. Ingraham: Protocatechuic acid oxidase. J. Biol. Chem. 210, 799 (1954).
Stevens, B., and B. E. Algar: Photoperoxidation of unsaturated organic molecules. II. Autoperoxidation of aromatic hydrocarbons. J. Phys. Chem. 72, 3468 (1968).
Stotzky, G.: Techniques to study interactions between microorganisms and clay minerals in vivo and in vitro. Bull. Ecol. Res. Comm. (Stockholm) 17, 17 (1973).
Suess, M. J.: Aqueous solutions of 3,4-benzpyrene. Water Res. 6, 981 (1972a).
— Polynuclear aromatic hydrocarbon pollution of the marine environment. In M. Ruivo (ed.): Marine pollution and sea life. London. Fishing New Books (1972 b).
— The environmental load and cycle of polycyclic aromatic hydrocarbons. The Sci. of the Total Environ. 6: 239–250 (1976).
Tausson, V. O.: In N. A. Meximov (ed.): Basic principles of plant bioenergetics. Acad. Sci, U.S.S.R. (1950).
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).
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).
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).
— 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).
— Rationale for recommended list of priority pollutants. Memo to director of Effluent Guidelines Division. Nov. 19 (1976).
— Environmental pathways of selected chemicals in freshwater systems. Part II. Laboratory studies. EPA-600/7-78-074 (1978).
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).
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).
Wagner, K. H., and C. Vonderheid: Polycyclic aromatic hydrocarbons in technically prepared composts. Naturwissenschaften 65, 491 (1978).
—, and E. Wagner-Hering: The cycle of cancer-causing substances-polycyclic aromatic hydrocarbons-in plants and humans. Protectio Vitae 6, 260 (1971).
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).
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).
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).
Wright, A. S.: The role of metabolism in chemical mutagenesis and chemical carcinogenesis. Mut. Res. 75, 215 (1980).
Wynder, E. L., J. Kmet, N. Dungal, and N. Segi: An epidemiological investigation of gastric cancer. Cancer 16, 1461 (1963).
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).
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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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