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Protocol guidelines for the investigations of photochemical fate of pesticides in water, air, and soils

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Part of the book series: Residue Reviews ((RECT,volume 96))

Abstract

Pesticides represent an increasingly important sort of synthetic chemical introduced into the environment through human activity. A compound is important in environmental chemistry provided it has (or shows evidence of having) the following characteristics (Choudhry et al. 1979a):

  • produced or distributed in large quantity

  • high likelihood of entry into the environment — dispersion tendency (transport)

  • persistence (lack of degradation under biotic and abiotic conditions)

  • bio-accumulation (concentration effects, e.g., in the food chain or by other mechanisms)

  • significant toxicity and related biological effects

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References

  • Abdel-Malik, M. M., and P De Mayo, Surface photochemistry, The amide Photo-Fries rearrangement. Can. J. Chem. 62, 1275 (1984).

    Article  CAS  Google Scholar 

  • Benson, S. W., Thermochemical Kinetics, Second Edition. New York, Wiley-Interscience (1976)

    Google Scholar 

  • Blazejowski, J., and J. Szychlinski, 1,4-Dioxane as a solvent in spectroscopy and photochemistry. Anal. Chim. Acta 159, 369 (1984).

    Article  CAS  Google Scholar 

  • Buch, R. R., T. H. Land, R. B. Annelin, and C. L. Frye, Photolytic oxidative demethylation of aqueous dimethylsiloxanols. Environ. Toxicol. Chem. 3, 215 (1984).

    Article  CAS  Google Scholar 

  • Bunce, N. J., Photolysis of 2-chlorobiphenyl in aqueous acetonitrile. Chemosphere 8, 653 (1978).

    Article  Google Scholar 

  • Burkhard, N., and J. A. Guth, Photolysis of organophosphorus insecticides on soil surfaces. Pestic. Sci. 10, 313 (1979).

    Article  CAS  Google Scholar 

  • Calvert, J. G., and J. N. Pitts, Photochemistry. New York, Wiley (1966).

    Google Scholar 

  • Chen, Z. M., M. J. Zabik, and R. A. Leavitt, Comparative study of thin film photodegradative rates for 36 pesticides. Ind. Eng. Chem. Prod. Res. Dev. 23, 5 (1984).

    Article  CAS  Google Scholar 

  • Choudhry, G. G., Humic substances. Part II. Photophysical, photochemical and free radical characteristics. Toxicol. Environ. Chem. 4, 261 (1981).

    Article  CAS  Google Scholar 

  • Choudhry, G. G., Humic Substances, Structural, Photophysical, Photochemical and Free Radical Aspects and Interactions with Environmental Chemicals (pp. 158–159 ). New York, Gordon and Breach Sci. Publ. (1984a).

    Google Scholar 

  • Choudhry, G. G., Photophysical and photochemical properties of soil and aquatic humic materials. Residue Rev. 92, 59 (1984b).

    CAS  Google Scholar 

  • Choudhry, G. G., Humic Substances, Structural Aspects and Photophysical, Photochemical and Free Radical Characteristics. In O. Hutzinger (ed.): The Handbook of Environmental Chemistry, Vol. 1, Part C., pp. 1–24. Berlin, Springer-Verlag (1984 c).

    Google Scholar 

  • Choudhry, G. G., and O. Hutzinger, Acetone sensitized and non-sensitized photolysis of tetra-, penta-, and hexachlorobenzenes in acetonitrile-water mixtures, Photoisomerization and formation of several products including polychlorobiophenyls. Environ. Sci. Technol. 18, 235 (1984).

    Article  CAS  Google Scholar 

  • Choudhry, G. G., and G. R. B. Webster, Environmental photochemistry of PCDDs. Part I. Kinetics and quantum yields of the photodegradation of 1,2,3,4,7-penta- and 1,2,3,4,7,8-hexachlorodibenzo p-dioxin in aqueous acetonitrile. Chemosphere 14, 9 (1985).

    Article  CAS  Google Scholar 

  • Choudhry, G. G., J. A. van den Broeck, and O. Hutzinger, Formation of polychlorodibenzofurans (PCDFs) by the photolysis of polychlorobenzenes (PCBZs) in aqueous acetonitrile containing phenols. Chemosphere 12, 487 (1983).

    Article  CAS  Google Scholar 

  • Choudhry, G. G., J. A. van den Broeck, G. R. B. Webster, and O. Hutzinger, Photochemical incorporations of polychlorobenzenes into some humic model monomers. Submitted to Environ. Toxicol Chem. (1985).

    Google Scholar 

  • Choudhry, G. G., A. A. M. Roof, and O. Hutzinger, Mechanisms in sensitized photochemistry of environmental chemicals. Toxicol. Environ. Chem. 2, 259 (1979 a).

    Article  CAS  Google Scholar 

  • Choudhry, G. G., A. A. M. Roof, and O. Hutzinger, Photochemistry of halogenated benzenes derivatives. I. Trichlorobenzenes, Reductive dechlorination, isomerization and formation of polychlorobiphenyls. Tetrahedron Lett. 2059 (1979 b).

    Google Scholar 

  • Choudhry, G. G., A. A. M. Roof, and O. Hutzinger, Photochemistry of halogenated benzene derivatives. Part 2. Photoreactions of α-substituted p-chlorotoluenes. J. Chem. Soc. Perkin Trans. I, 2957 (1982).

    Google Scholar 

  • Choudhry, G. G., G. Sundstrom, L. O. Ruzo, and O. Hutzinger, Photochemistry of chlorinated diphenyl ethers. J. Agric. Food Chem. 25, 1371 (1977 a).

    Article  Google Scholar 

  • Choudhry, G. G., G. Sundstrom, F W. M. van der Wielen, and O. Hutzinger, Synthesis of dibenzofurans by photolysis of chlorinated diphenyl ethers in acetone solution. Chemosphere 6, 327 (1977 b).

    Article  CAS  Google Scholar 

  • Cooper, W. J., and R. G. Zika, Photochemical formation of hydrogen peroxide in surface and ground waters exposed to sunlight. Science 220, 711 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Cox, R. A., R. G. Derwent, and M. R. Williams, Atmospheric photooxidation reactions. Rates, reactivity and mechanism for reaction of organic compounds with hydroxyl radicals. Environ. Sci. Technol. 14, 57 (1980).

    Article  CAS  Google Scholar 

  • Crosby, D. G., Experimental approaches to pesticide photodecomposition. Residue Rev. 25, 1 (1969).

    PubMed  CAS  Google Scholar 

  • Crosby, D. G., and K. W. Moilanen, Vapor-phase photodecomposition of aldrin and dieldrin. Arch. Environ. Contamin. Toxicol. 2, 62 (1974).

    Article  CAS  Google Scholar 

  • Crosby, D. G., and A. S. Wong, Environmental degradation of 2,3,7,8-tetrachlorodibenzo p-dioxin (TCDD). Science 195, 1337 (1977).

    Article  PubMed  CAS  Google Scholar 

  • Demayo, P., and H. Shizuka, In W. R. Ware (ed.): Creation and detection of the excited state, Vol. 4, Chapt. 4. New York, Marcel Dekker (1976).

    Google Scholar 

  • Dilling, W. L., C. J. Bredeweg, and N. B. Tefertiller, Simulated atmospheric photodecomposition rates of methylene chloride, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethylene, and other compounds. Environ. Sci. Technol. 10, 351 (1976).

    Article  CAS  Google Scholar 

  • Dilling, W. L., L. C. Lickly, T. D. Lickly, and P. G. Murphy, Organic photochemistry. 19. Quantum yields for o,o-diethyl-0-(3,5,6-Trichloro-2-pyridinyl) phosphorothioate (Chlorpyrifos) and 3,5,6-trichloro-2-pyridinol in dilute aqueous solutions and their environmental phototransformation rates. Environ. Sci. Technol. 18, 540 (1984).

    Article  CAS  Google Scholar 

  • Draper, W. M., and D. G. Crosby, Hydrogen peroxide and hydroxyl radical, Intermediates in indirect photolysis reactions in water. J. Agric. Food Chem. 29, 699 (1981).

    Article  CAS  Google Scholar 

  • Draper, W. M., and D. G. Crosby, The photochemical generation of hydrogen peroxide in natural waters. Arch. Environ. Contam. Toxicol. 12, 121 (1983).

    Article  CAS  Google Scholar 

  • Draper, W. M., and D. G. Crosby, Solar photooxidation of pesticides in dilute hydrogen peroxide. J. Agric. Food Chem. 32, 231 (1984).

    Article  CAS  Google Scholar 

  • Dulin, D., and T. Mill, Development and evaluation of sunlight actinometers. Environ. Sci. Technol. 16, 815 (1982).

    Article  CAS  Google Scholar 

  • Fisher, G. J., J. C. Leblanc, and H. E. Johns, A calorimetric determination of the quantum yield for the ionization of malachite green cyanide by ultraviolet radiation. Photochem. Photobiol. 6, 757 (1967).

    Article  CAS  Google Scholar 

  • Gab, S., S. Nitz, H. Parlar, and F Korte, Photomineralisation of certain aromatic xenobiotica, Chemosphere 5, 251 (1975).

    Article  Google Scholar 

  • Gebefugi, I., R. Baumann, and F Korte, Photochemischer abbau von 2,3,7,8-tetrachlorodibenzo p-dioxin (TODD) unter simulierten unweltbedingungen. Naturwissenschaften 64, 486 (1977).

    Article  Google Scholar 

  • Gohre, K., and G. C. Miller, Singlet oxygen generation on soil surfaces. J. Agric. Food Chem. 31, 1104 (1983).

    Article  CAS  Google Scholar 

  • Guth, J. A., Experimental approaches to studying the fate of pesticides in soil. In D. H. Hutson and T. R. Roberts (eds.): Progress in Pesticide Biochemistry, Chapt. 2, pp. 85–114. New York, Wiley.

    Google Scholar 

  • Hanst, P. L., and B. W. Gay Jr., Photochemical reactions among formaldehyde, chlorine and nitrogen dioxide in air. Environ. Sci. Technol. 11, 1105 (1977).

    Article  CAS  Google Scholar 

  • Helling, L. S., and B. C. Turner, Pesticide mobility, Determination by soil thin layer chromatography. Science 162, 562 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Hendry, D. G., Atmospheric Chemistry. In laboratory protocols for evaluating the fate of organic chemicals in air and water, by T. Mill, W. R. Mabey, D. C. Bomberger, D. C. Chou, and J. H. Smith. EPA-600/3-82-022, Chapter 5, pp. 139–209 (1982).

    Google Scholar 

  • Holmes, J. R., R. J. O’Brien, J. H. Crabtree, T. A. Hecht, and J. H. Seinfeld, Measurement of ultraviolet radiation intensity in photochemical smog studies. Environ. Sci. Technol. 7, 519 (1973).

    Article  CAS  Google Scholar 

  • Howard, C. J., and K. M. Evenson, Rate constants for the reactions of OH with CH4 and fluorine, chlorine, and bromine substitued methane at 296 K. J. Chem. Phys. 64, 197 (1976 a).

    Article  CAS  Google Scholar 

  • Howard, C. J., and K. M. Evenson, Rate constants for the reactions of OH with ethane and some halogen substituted ethanes at 296 K. J. Chem. Phys. 64, 4303 (1976 b).

    Article  CAS  Google Scholar 

  • Howard, P H., J. Saxena, and H. Sikka, Determining the fate of chemicals. Environ. Sci. Technol. 12, 398 (1978).

    Article  CAS  Google Scholar 

  • Ivie, G. W., and J. E. Casida, Enhancement of photoalteration of cyclodiene insecticide chemical residues by rotenone. Science 167, 1620 (1970).

    Article  PubMed  CAS  Google Scholar 

  • Ivie, G. W., and J. E. Casida, Sensitized photodecomposition and photosensitizer activity of pesticide chemicals exposed to sunlight on silica gel chromatoplates. J. Agric. Food Chem. 19, 405 (1971 a).

    Article  CAS  Google Scholar 

  • Ivie, G. W., and J. E. Casida, Photosensitizers for the accelerated degradation of chlorinated cyclodienes and other insecticide chemicals exposed to sunlight on bean leaves. J. Agric. Food chem. 19, 410 (1971 b).

    Article  CAS  Google Scholar 

  • Kramer, H. E. A., and A. Maute, Sensitized photooxygenation, Change from type I (radical) to type II (singlet oxygen). Photochem. Photobiol. 17, 413 (1973).

    Article  CAS  Google Scholar 

  • Klehr, M., J. Iwan, and J. Riemann, An experimental approach to the photolysis of pesticides adsorbed on soil, Thidiazuron-Pestic. Sci. 14, 359 (1983).

    CAS  Google Scholar 

  • Koller, L. R., Ultraviolet Radiation. 2nd ed., p. 105. New York, Wiley (1965).

    Google Scholar 

  • Lamola, A. A., and G. S. Hammond, Intersystem crossing efficiencies. J. Chem. Phys. 41, 2129 (1965).

    Article  Google Scholar 

  • Leermaker, L. A., H. T. Thomas, L. D. Weis, and F. C. James, Spectra and photochemistry of molecules adsorbed on silica gel. IV. J. Am. Chem. Soc. 88, 5075 (1966).

    Article  Google Scholar 

  • Leighton, P. A., Photochemistry of Air Pollution. New York, Academic Press. (1961).

    Google Scholar 

  • Lemaire, J., I. Campbell, H. Hulpke, J. A. Guth, W. Merz, J. Philp, and C. von Waldow An assessment of test methods for photodegradation of chemicals in the environment. Chemosphere 11, 119 (1982).

    Article  CAS  Google Scholar 

  • Liang, T. T., and E. P. Lichtenstein, Effects of soil and leaf surfaces on the photodecomposition of [14C] azinphosmethyl. J. Agric. Food Chem. 24, 1205 (1976).

    Article  PubMed  CAS  Google Scholar 

  • Mabey, W. R., T. Mill, and D. G. Hendry, Photolysis in water. In Laboratory Protocols for Evaluating the Fate of Organic Chemicals in Air and Water, by T. Mill, W. R. Mabey, D. C. Bomberger, D. C. Chou, and J. H. Smith. EPA-600/3-8-022, Chapter 3, pp. 49–102 (1982).

    Google Scholar 

  • McCall, P. J., D. A. Laskowski, R. L. Swann, and H. J. Dishburger, Measurement of sorption coefficient of organic chemicals and their use in environmental fate analysis. In Test Protocols for Environmental Fate and Movement of Toxicants. AOAC. Arlington, VA 22209, pp. 89–109 (1981).

    Google Scholar 

  • Mill, T., D. Dulin, and J. Davenport, Development and evaluation of sunlight actinometers. EPA Report (Draft) EPA Contract 68-01-6325 (1981 b).

    Google Scholar 

  • Mill, T., W. R. Mabey, D. G. Hendry, J. Winterle, J. Davenport, V. Barich, D. Dulin, and D. Tse, Design and validation of screening and detailed methods for environmental processes EPA (1982). Cited in Photolysis in Aqueous Solution in Sunlight, Office of Toxic Substances, Office of Pesticides and Toxic Substances, U.S. Environmental Protection Agency, Washington, DC, CS-6000, October 1983.

    Google Scholar 

  • Mill, T., W. R. Mabey, B. Y. Lan, and A. Baraze, Chemosphere 10, 1281 (1981 a).

    Article  CAS  Google Scholar 

  • Miller, G. C., Unpublished work, University of Nevada, Reno (1981); cited in Miller and Zepp, 1983.

    Google Scholar 

  • Miller, G. C., and R. G. Zepp, Extrapolating photolysis rates from the laboratory to the environment. Residue Rev. 85, 89 (1983).

    CAS  Google Scholar 

  • Miller, G. C., M. J. Millie, D. G. Crosby, S. Sontum, and R. G. Zepp, Photolysis of 3,4-dichloroaniline in water. Tetrahedron 33, 1797 (1979).

    Article  Google Scholar 

  • Mikami, N., K. Imanishi, H. Yamada, and J. Miyamoto, Photodegradation of the funigicide tolclofos-methyl in water and on soil surface. J. Pesticide Sci. 9, 215 (1984).

    Article  CAS  Google Scholar 

  • Moore, W. J., Physical Chemistry. First edition, pp. 334–337. New York, Longman (1972).

    Google Scholar 

  • Murov, S. L., Handbook of Photochemistsry. New York, Marcel Dekker (1973).

    Google Scholar 

  • Nestrick, T. J., L. L. Lamparski, and D. I. Townsend, Identification of tetrachlorodibenzo p-dioxin isomers at 1 ng level by photolytic degradation and pattern recognition techniques. Anal. Chem. 52, 1865 (1980).

    Article  CAS  Google Scholar 

  • Nilles, G. P, and M. J. Zabik, Photochemistry of bioactive compounds. Multiphase photodegradation of Basalin. J. Agric. Food Chem. 22, 684 (1974).

    Article  PubMed  CAS  Google Scholar 

  • OECD, Guidelines for Testing of Chemicals. Guidelines #106, Adsorption/Desorption (1981).

    Google Scholar 

  • Parlar, H., Photochemistry at surfaces and interphases. In O. Hutzinger (ed.): The Handbook of Environmental Chemistry, Vol. 2, Part A, pp. 145–159. Berlin, SpringerVerlag (1980).

    Google Scholar 

  • Perry, R. A., R. Atkinson, and J. N. Pitts, Jr., Kinetics and mechanism of the gas phase reaction of OH radicals with aromatic hydrocarbons over the temperature range 296–473 K. J. Phys. Chem. 81, 296 (1977).

    Article  CAS  Google Scholar 

  • Peterson, J. T., Calculated actinic fluxes (290-700 nm) for air pollution photochemistry applications. EPA-600/4-76-025 (1976).

    Google Scholar 

  • Pitts, J. N., Jr., J. M. Veronon, and J. K. S. Wan, A rapid actinometer for photochemical air pollution studies. Internat. J. Air Poll. 6, 757 (1975).

    Google Scholar 

  • Pitts, J. N., Jr., A. M. Winer, D. R. Fitz, A. K. Knudsen, and R. Atkinson, Experimental protocol for determining absorption cross section of organic chemicals. EPA-600/3-81-051 (1981).

    Google Scholar 

  • Plimmer, J. R., and U. I. Klingebiel, Photolysis of hexachlorobenzene. J. Agric. Food Chem. 24, 721 (1976).

    Article  PubMed  CAS  Google Scholar 

  • Plum, C. N., E. Sanhueza, R. Atkinson, W. P. L. Carter, and J. N. Pitts, Jr., OH radical rate constants and photolysis rate of α-dicarbonyls. Environ. Sci. Technol. 17, 479 (1983).

    Article  CAS  Google Scholar 

  • Ravishankra, A. R., W. Wagner, S. Fischer, G. Smiter, R. Schiff, R. T. Watson, G. Testi, and D. D. Davis, A kinetic study of the reactions of OH with several aromatic and olefinic compounds. Intern. J. Chem. Kinet. 10, 783–804 (1978).

    Article  Google Scholar 

  • Roof, A. A. M., Aquatic Photochemistry. In O. Hutzinger (ed.), The Handbook of Environmental Chemistry, Vol. 2, Part B, pp. 43–72. Berlin, Springer-Verlag (1982).

    Google Scholar 

  • Rosen, J. D., and W. F. Carey, Preparation of the photoisomers of aldrin and dieldrin. J. Agric. Food Chem. 16, 536 (1968).

    Article  Google Scholar 

  • Shibuya, K., T. Nagashima, S. Imai, and H. Akimoto, Photochemical ozone formation in the irradiation of ambient air samples by using a mobile smog chamber. Environ. Sci. Technol. 15, 661 (1981).

    Article  CAS  Google Scholar 

  • Smith, C. A., Y Iwata, and F. A. Gunther, Conversion and disappearance of methidathion on thin layers of dry soil. J. Agric. Food Chem. 26, 959 (1978).

    Article  CAS  Google Scholar 

  • Smith, J. H., W. R. Mabey, N. Bohonos, B. R. Holt, S. S. Lee, T. W. Chou, D. C. Bomberger, and T. Mill, Environmental Pathways of Selected Chemicals in Freshwater Systems. Part I, Background and Experimental Procedures. U.S. EPA-600/ 7-77-113 (1977).

    Google Scholar 

  • Tuazon, E. C., W. P L. Carter, A. M. Winer, and J. N. Pitts, Jr., Reactions of hydrazines with ozone under simulated atmospheric conditions. Environ. Sci. Technol. 15, 823 (1981).

    Article  CAS  Google Scholar 

  • Veslay, G. F., Complications in measuring quantum yields using cylindrical sample cells. Mol. Photochem. 3, 193 (1971).

    Google Scholar 

  • Walling, C., Fenton’s reagent revisited. Acc. Chem. Res. 8, 125 (1975).

    Article  CAS  Google Scholar 

  • Wells, C. H. J., Introduction to Molecular Photochemistry, pp. 34–58. London, Chapman and Hall (1972).

    Google Scholar 

  • Winer, A. M., R. A. Graham, G. J. Doyle, P J. Bekowies, J. M. McAfee, and J. N. Pitts, Jr., An evacuable environmental chamber and solar simulator factility for the study of atmospheric photochemistry. Adv. Environ. Sci. Technol. 10, 461 (1980).

    CAS  Google Scholar 

  • Woodrow, J. E., D. G. Crosby, and J. N. Seiber, Vapor-phase photochemistry of pesticides. Residue Rev. 85, 111 (1983).

    CAS  Google Scholar 

  • Zafiriou, O. C., J. Joussot-Dubien, R. G. Zepp, and R. G. Zika, Photochemistry of natural waters, Many compounds and environments are affected by sunlight-induced photochemistry. Environ. Sci. Technol. 18, 358A (1984).

    Article  CAS  Google Scholar 

  • Zepp, R. G., Experimental approaches to environmental photochemistry. In O. Hutzinger (ed.), The Handbook of Environmental Chemistry, Vol. 2, Part B, pp. 19–44. Berlin, Springer-Verlag (1982).

    Google Scholar 

  • Zepp, R. G., and G. L. Baughman, Prediction of photochemical transformation of pollutants in the aquatic environment. In O. Hutzinger, I. H. von Lelyveld, and B. C. S. Zoetman (eds.): Aquatic Pollutants, Transformation and Biological Effects, p. 237. New York, Pergamon Press (1978).

    Google Scholar 

  • Zepp, R. G., and D. M. Cline, Rates of direct photolysis in aquatic environment. Environ. Sci. Technol. 11, 359 (1977).

    Article  CAS  Google Scholar 

  • Zepp, R. G., G. L. Baughman, and P F. Schlotzhauer, Comparison of photochemical behavior of various humic substances in water, II. Photosensitised oxygenations. Chemosphere 10, 119 (1981).

    Article  CAS  Google Scholar 

  • Zepp, R. G., P F. Schlotzhauer, and R. M. Sink, Photosensitized transformations involving electron energy transfer in natural waters, Rate of humic substances. Environ. Sci. Technol. 19, 74 (1985).

    Article  Google Scholar 

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Choudhry, G.G., Barrie Webster, G.R. (1985). Protocol guidelines for the investigations of photochemical fate of pesticides in water, air, and soils. In: Gunther, F.A. (eds) Residue Reviews. Residue Reviews, vol 96. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-5140-8_4

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