Advertisement

Chlorophenols in the Terrestrial Environment

  • John Jensen
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 146)

Abstract

Chlorination of naturally occurring phenols has taken place perpetually, but since the introduction of pentachlorophenol (PCP) as a commercial antiseptic in 1936, the worldwide production of chlorophenols has rapidly increased with an elevated environmental burden as a result. Today, chlorophenols (CP) are widespread in the environment. Even in the most remote natural environments, analyses have shown the presence of chlorophenols in both aquatic and terrestrial food chains. Previously reported reviews on chlorophenols have mainly focused on the aquatic environment or on the toxicological aspects of chlorophenols (e.g., Ahlborg and Thunberg 1980; Bevenue and Beckman 1967; WHO 1987, 1989) mainly due to the preponderance of information in these areas. However, partitioning models have shown that more than 95% of the load of pentachlorophenol is associated with the soil (Hattemer-Frey and Travis 1989; Shiu et al. 1994; Wild et al. 1992). This review is solely committed to the fate and ecotoxicological effects of chlorophenols in the terrestrial environment. After a short review of the fate and bioavailability of chlorophenols in soil, the major parts of this paper present ecotoxicological data [no-effect concentration/effect concentration (NOEC/EC) values] of chlorophenols relating to soil flora and fauna. The data were collected from laboratory and field experiments published in international papers. Finally, a short evaluation of the ecological risk of chlorophenols in the terrestrial environment and the risk assessment in a few countries are presented.

Keywords

Sewage Sludge Soil Respiration Terrestrial Environment Soil Concentration Ecotoxicological Effect 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Adema DMM, Henzen L (1989) A comparison of plant toxicities of some industrial chemicals in soil culture and soilless culture. Ecotoxicol Environ Saf 18: 219–229.PubMedCrossRefGoogle Scholar
  2. Ahlborg UG, Thunberg TM (1980) Chlorinated phenols: occurence, toxicity, metabolism, and environmental impact. CRC Crit Rev Toxicol 7: 1–36.CrossRefGoogle Scholar
  3. Baker MD, Mayfield CI (1980) Microbial and non-biological decomposition of chlorophenols and phenol in soil. Water Air Soil Pollut 13: 411–424.CrossRefGoogle Scholar
  4. Bellin CA, O’Connor GA (1990) Plant uptake of pentachlorophenol from sludgeamended soils. J Environ Qual 19: 298–302.Google Scholar
  5. Bevenue A, Beckman H (1967) Pentachlorophenol: a discussion of its properties and its occurence as a residue in human and animal tissues. Residue Rev 19: 83–134.PubMedGoogle Scholar
  6. Bornkamm R, Meyer G (1985) Die wirkung chemischer belastung auf die stadtvege- tationen. Specielle Berichte Berlin Kern Forschung Anlage Jülich 296: 130–145.Google Scholar
  7. Boyde SA, Mikesell MD, Lee J (1989) Chlorophenols in soils. In: Sawhney BL, Brown K (eds) Reactions and movement of organic chemicals in soils. Spec Pub 22. Soil Science Society of America, Madison, WI, pp 209–228.Google Scholar
  8. Bryant SE, Schultz TW (1994) Toxicological assessment of biotransformation products of pentachlorophenol: Tetrahymena population growth impairment. Arch Environ Contam Toxicol 26: 299–303.PubMedCrossRefGoogle Scholar
  9. Butte W, Denker J, Kirsch M, Höpner T (1985) Pentachlorophenol and tetrachlorophenol in Wadden sediment and clams Mya arenaria of the Jadebusen after a 14-year period of wastewater discharge containing pentachlorophenol. Environ Pollut (Ser B) 9: 29–39.CrossRefGoogle Scholar
  10. Cascorbi I, Ahlers J (1989) Correlation between the lipophilicity of substituted phenols and their inhibition of the Na+/K+-ATPase of chinese hamster ovary cells. Toxicology 58: 197–210.PubMedCrossRefGoogle Scholar
  11. Cascorbi I, Forêt M (1991) Interaction of xenobiotics on the glycose-transport system and the Na+/K+-ATPase of human skin fibroblasts. Ecotoxicol Environ Saf 21: 38–46.PubMedCrossRefGoogle Scholar
  12. Casterline JL, Barnett NM, Ku Y (1985) Uptake, translocation and transformation of pentachlorophenol in soyabean and spinach plants. Environ Res 37: 101–118.PubMedCrossRefGoogle Scholar
  13. Cirelli DP (1978) Patterns of pentachlorophenol usage in the United States of America—an overview. The environmental fate of 14C-Pentachlorophenol in laboratory model ecosystems. In: Rao KR (ed) Pentachlorophenol. Chemistry, Pharmacology, and Environmental Toxicology. Plenum Press, New York, pp 13–18.Google Scholar
  14. Cohen E, Gamliel A, Katan J (1988) The fungitoxicity of chlorophenols to the pathogenic fungi Fusarium oxysporum and Rhizoctonia solani: a SAR study. Pestic Sci 24: 139–146.CrossRefGoogle Scholar
  15. Drong K, Lamprecht I (1993) Toxicological studies of energy flows in ecological systems. Pure Appl Chem 65: 1967–1972.CrossRefGoogle Scholar
  16. Fahrig R, Nilsson C-A, Rappe C (1978) Genetic activity of chlorophenols and chlorophenol impurities. In: Kao KR (ed) Pentachlorophenol. Chemistry, Pharmacology and Environmental Toxicology. Plenum Press, New York, pp 325–338.Google Scholar
  17. Ferro AM, Sims RC, Bugbee B (1994) Hycrest crested wheatgrass accelerates the degradation of pentachlorophenol in soil. J Environ Qual 23: 272–279.PubMedCrossRefGoogle Scholar
  18. Fisher SW, Wadleigh RW (1986) Effects of pH on the acute toxicity and uptake of 14C pentachlorophenol in the midge Chironomus riparius. Ecotoxicol Environ Saf 11: 1–8.PubMedCrossRefGoogle Scholar
  19. Ghoshal S, Banerji SK, Bajpai RK (1992) Role of photodegradation in pentachlorophenol decontamination in soils. Ann NY Acad Sci 665: 412–422.CrossRefGoogle Scholar
  20. Goats GC, Edwards CA (1988) The prediction of field toxicity of chemicals to earthworms by laboratory methods. In: Edwards CA, Neuhauser EF (eds) Earthworms in Waste and Environmental Management. SPB Academic, The Hague, Netherlands, pp 283–294.Google Scholar
  21. Gruttke H, Kratz W, Weigmann G, Haque A (1988) Terrestrial model food chain and Environmental Chemicals. I. Transfer of 14C pentachlorophenate between springtails and carabids. Ecotoxicol Environ Saf 15: 253–259.PubMedCrossRefGoogle Scholar
  22. Haimi J, Salminen J, Huhta V, Knuutinen J, Palm H (1992) Bioaccumulation of organochlorine compounds in earthworms. Soil Biol Biochem 24: 1699–1703.CrossRefGoogle Scholar
  23. Haimi J, Molin S (1994) Responses of two earthworm populations with different exposure histories to chlorophenolic contamination. Poster presentation, Third European Conference on Ecotoxicology, August 28–31, 1994, Zürich, Switzerland.Google Scholar
  24. Haque A, Scheunert I, Korte F (1978) Isolation and identification of a metabolite of pentachlorophenol 14C in rice plants. Chemosphere 1: 65–69.CrossRefGoogle Scholar
  25. Haque A, Gruttke H, Kratz W, Kielhorn U, Weigman G, Meyer G, Bornkamm R, Schuphan I, Ebing W (1988) Environmental fate and distribution of sodium-14Cpentachlorophenate in a section of urban wasteland ecosystem. Sci Total Environ 68: 127–139.PubMedCrossRefGoogle Scholar
  26. Harvey WA, Crafts AS (1950) Toxicity of pentachlorophenol and its sodium salt in three Yolo soils. Hilgardia 21: 487–498.Google Scholar
  27. Hattemer-Frey HA, Travis CC (1989) Pentachlorophenol: environmental partitioning and human exposure. Arch Environ Contam Toxicol 18: 482–489.PubMedCrossRefGoogle Scholar
  28. Heimbach F (1984) Correlation between three methods for determining the toxicity of chemicals to earthworms. Pestic Sci 15: 605–611.CrossRefGoogle Scholar
  29. Howard PH (1989) Handbook of Environmental Fate and Exposure Data for Organic Chemicals, Vol 1. Large Production and Priority Pollutants. Lewis Publishers, Chelsea, MI.Google Scholar
  30. Hulzebos EM, Adema DMM, Dirven-van Breemen EM, Henzen L, van Dis WA, Herbold HA, Hoekstra JA, Baerselman R, van Gestel CAM (1993) Phytotoxicity studies with Lactuca sativa in soil and nutrient solution. Environ Toxicol Chem 12: 1079–1094.Google Scholar
  31. Ide A, Niki Y, Sakamoto F, Watanabe I, Watanabe H (1972) Decomposition of pentachiorphenol in paddy soil. Agric Biol Chem 36: 1937–1944.CrossRefGoogle Scholar
  32. Ishizawa S, Toyoda H, Matsugushi T (1961a) Effects of DD, EDB and PCP upon microorganisms and their activities in soil. Part I. Effects on microflora. Soil Plant Food 6: 145–155.Google Scholar
  33. Ishizawa S, Tanabe I, Matsuguchi T (1961b) Effects of DD, EDB and PCP upon microorganisms and their activities in soil. Part II. Effects om microbial activity. Soil Plant Food 6: 156–163.Google Scholar
  34. Jensen J, Folker-Hansen P (1995) Soil quality criteria for selected organic compounds. Working Report (Arbejdsrapport) no. 47, Danish Environmental Protecting Agency, Copenhagen, Denmark.Google Scholar
  35. Kappers FI, van Eijk JAAMW (1987) Effects on free-living soil nematodes of long-term exposure to chlorinated phenols in laboratory microcosms. Pharma Weekbl 9: 353.Google Scholar
  36. Kaufman DD (1978) Degradation of pentachlorophenol in soil and soil microorganisms. In: Rao KR (ed) Pentachlorophenol. Chemistry, Pharmacology, and Environmental Toxicology. Plenum Press, New York, pp 27–39.Google Scholar
  37. Kitunen VH, Valo RJ, Salkinoja-Salonen MS (1987) Contamination of soil around wood-preserving facilities by polychlorinated aromatic compounds. Environ Sci Technol 21: 96–101.CrossRefGoogle Scholar
  38. Knuutinen J, Palm H, Hakala H, Haimi J, Huhta V, Salminen J (1990) Polychlorinated phenols and their metabolites in soil and earthworms of sawmill environment. Chemosphere 20: 609–623.CrossRefGoogle Scholar
  39. Kuwatsuka S, Igarashi M (1975) Degradation of PCP in soils. II. Relationship between the degradation of PCP and the properties of soils, and the identification of the degradation products of PCP. Soil Sci Plant Nutr 21: 405–414.Google Scholar
  40. Lagas P (1988) Sorption of chlorophenols in the soil. Chemosphere 17: 205–216.CrossRefGoogle Scholar
  41. Li S, Paeologou M, Purdy WC (1991) Determination of the acidity constants of chlorinated phenolic compounds by liquid chromatography. J Chromatogr Sci 29: 66–69.Google Scholar
  42. Lu P-Y, Metcalf RL, Cole LK (1978) The environmental fate of 14Cpentachlorophenol in laboratory model ecosystems. In: Rao KR (ed) Pentachlorophenol. Chemistry, Pharmacology, and Environmental Toxicology. Plenum Press, New York, pp 53–63.Google Scholar
  43. Ma K-C, Shiu W-Y, Mackay D (1993) Aqueous solubilities of chlorinated phenols at 25 °C. J Chem Eng Data 38: 364–366.CrossRefGoogle Scholar
  44. Miljostyrelsen (Danish EPA) (1995) Toksikologiske kvalitetskriterier for jord og vand (Toxicological quality criteria for soil and drinkingwater) (in Danish). Projekt om jord og grundvand no. 12, fra Miljostyrelsen, Copenhagen, Denmark.Google Scholar
  45. Mitsui S, Watanabe I, Honma M, Honda S (1964) The effect of pesticides on the denitrification in paddy soil. Soil Sci Plant Nutr 10: 15–23 (107–115).Google Scholar
  46. Moulton MP, Schultz TW (1986) Comparisons of several structure-toxicity relationships for chiorophenols. Aquat Toxicol 8: 121–128.CrossRefGoogle Scholar
  47. Murthy NBK, Kaufman DD, Fries GF (1979) Degradation of pentachlorophenol ( PCP) in aerobic and anaerobic soil. J Environ Sci Health B 14: 1–14.PubMedCrossRefGoogle Scholar
  48. Neuhauser EF, Durkin PR, Malecki MR, Anatra M (1986) Comparative toxicity of ten organic chemicals to four earthworm species. Comp Biochem Physiol C 83: 197–200.PubMedCrossRefGoogle Scholar
  49. Paasivirta J, Heinola K, Humpi T, Karjalainen A, Knuutinen J, Mäntykoski K, Paukku R, Piilola T, Surma-ASho K, Tarhanen J, Welling L, Vihonen H (1985) Polychlorinated phenols, guaacols and catechols in environment. Chemosphere 14: 469–491.CrossRefGoogle Scholar
  50. Puolanne, J (1991) Strategies and means of solving the problem of soil contamination in Finland. Paper presented at the conference: “Deteccion y recuperacion de suelos contaminados,” Madrid, May, 1991.Google Scholar
  51. Ravanel P, Taillandier G, Tissut M, Benoit-Guyod JL (1985) Effect of chlorophenols on isolated plant mitochondria activities: a QSAR study. Ecotoxicol Environ Saf 9: 300–320.PubMedCrossRefGoogle Scholar
  52. Richards DJ, Shieh WK (1986) Biological fate of organic priority pollutants in the aquatic environment. Water Res 20: 1077–1090.CrossRefGoogle Scholar
  53. Römbke J, Bauer C, Marschner A (1994) Verhalten and Wirkungen von sechs umweltchemikalien in terrestrichen labortests. In: Alef K, Blum W, Schwarz S, Riss a, Fiedler H, Hutzinger O (eds) ECOINFORMA. Umweltbundesamt, 59 September 1994. 3. Fachtagung and ausstellung für umweltinformation and umweltkommunikation. Band 6: Bodenkontamination, Bodensanierung, Bodeninformationssysteme. 6: 269–281.Google Scholar
  54. Rouse JD, Sabatini DA, Suflita JM, Harwell JH (1994) Influence of surfactants on microbial degradation of organic compounds. Crit Rev Environ Sci Technol 24: 325–370.CrossRefGoogle Scholar
  55. Sato K (1985) Effect of a pesticide, pentachlorophenol (PCP), on soil microflora. II. Effect of PCP on bacterial flora in soil percolated with glycine or water. J Genet Appl Microbiol 31: 197–210.CrossRefGoogle Scholar
  56. Sato K (1987) Effect of increasing pentachlorophenol (PCP) concentrations on bacterial populations in glycine-pecolated soils. Biol Fertil Soils 5: 1–5.CrossRefGoogle Scholar
  57. Schäfer W, Sanderman H (1988) Metabolism of pentachlorophenol in cell suspension cultures of wheat (Triticum aestivum). Tetrachlorocatechol as primary metabolite: J Agric Food Chem 36: 370–377.Google Scholar
  58. Schellenberg K, Leuenberger C, Schwarxenbach RP (1984) Sorption of chlorinated phe- nols by natural sediments and aquifer materials. Environ Sci Technol 18: 652–657.CrossRefGoogle Scholar
  59. Scheunert I, Qiao Z, Korte F (1986) Comparative studies of the fate of atrazine-14C and pentachlorophenol-14C in various laboratory and outdoor soil-plant systems. J Environ Sci Health B 21: 457–485.CrossRefGoogle Scholar
  60. Schönborn W, Dumpert K (1990) Effects of pentachlorophenol and 2,4,5trichlorophenoxyacetic acid on the microflora of the soil in a beech wood. Biol Fertil Soils 9: 292–300.CrossRefGoogle Scholar
  61. Seiler JP (1991) Pentachlorophenol. Mutat Res 257: 27–47.PubMedGoogle Scholar
  62. Shiu WY, Ma KC, Varhanickova D, Mackay D (1994) Chlorophenols and alkylphenols: a review and correlation of environmental relevant properties and fate in an evaluative environment. Chemosphere 29: 1155–1224.CrossRefGoogle Scholar
  63. Short KA, Doyle JD, King RJ, Seidler RD, Stotzky G, Olsen RH (1991) Effects of 2,4-dichlorophenol, a metabolite of a genetically engineered bacterium, and 2,4-dichlorophenoxyacetate on some microorganisms—mediated ecological processes in soil. Appl Environ Microbiol 57: 412–418.PubMedGoogle Scholar
  64. Smejtek P (1987) The physicochemical basis of the membrane toxicity of pentachlorophenol: an overview. J Membr Sci 33: 249–268.CrossRefGoogle Scholar
  65. Tam TY, Trevors JT (1981) Effects of pentachlorophenol on asymbiotic nitrogen fixation in soil. Water Air Soil Pollut 16: 409–414.CrossRefGoogle Scholar
  66. Trevors JT (1982a) Effect of temperature on the degradation of pentachlorophenol by Pseudomonas species. Chemosphere 11: 471–475.CrossRefGoogle Scholar
  67. Trevors JT (1982b) Differences in the sensitivity of short-term bioassays. Bull Environ Contam Toxicol 28: 655–659.PubMedCrossRefGoogle Scholar
  68. Valo R, Kitunen V, Salkinoja-Salonen M, Räisänen S (1984) Chlorinated phenols as contaminants of soil and water in the vicinity of two Finnish sawmills. Chemosphere 13: 835–844.CrossRefGoogle Scholar
  69. van Beelen P, Fleuren-Kemilä AK, Huys MPA, van Monfort ACP, van Vlaardingen PLA (1991a) The toxic effects of pollutants on the mineralization of acetate in subsoil microcosms. Environ Toxicol Chem 10: 775–789.CrossRefGoogle Scholar
  70. van Beelen P, Fleuren-Kemilä AK, van Monfort ACP (1991b) The effect of pentachlorophenol and other pollutants on the mineralization of acetate in several soils. RIVM Rep 719102010, National Institute of Public Health and Environmental Protection, Bilthoven, The Netherlands.Google Scholar
  71. van Gestel CAM, Ma W (1988) Toxicity and bioaccumulation of chlorophenols in earthworms, in relation to bioavailability. Ecotoxicol Environ Saf 15: 289–297.PubMedCrossRefGoogle Scholar
  72. van Gestel CAM, van Dis WA (1988) The influence of soil characteristics on the toxicity of four chemicals to the earthworm Eisen is eisenia andrei (Oligochaeta). Biol Fert Soils 6: 262–265.CrossRefGoogle Scholar
  73. van Gestel CAM, van Dis WA, van Breemen EM, Sparenburg PM (1989) Development of a standardized reproduction toxicity test with the earthworm species Eisenia fetida andrei using copper, pentachlorophenol, and 2,4,-dichloroaniline. Ecotoxicol Environ Saf 18: 305–312.PubMedCrossRefGoogle Scholar
  74. van Gestel CAM, Ma W (1990) An approach to quantitative structure-activity rela- tionships (QSARs) in earthworm toxicity studies. Chemosphere 21: 1023–1033.CrossRefGoogle Scholar
  75. van Gestel CAM, van Dis WA, Dirven-van Bremen EM, Sparenburg PM, Baerselman R (1991) Influence of cadmium, copper and pentachlorophenol on growth and sexual development of Eisenia andrei (Oligochaeta: Annelida). Biol Fertil Soils 12: 117–121.CrossRefGoogle Scholar
  76. Van de Meent D, Aldenberg T, Canton JH, van Gestel CAM, Slooff W (1990) Desire for levels. Background study for the policy document “Setting Environmental Quality Standards for Water and Soil.” RIVM Rep 670101002, National Institute of Public Health and Environmental Protection, Bilthoven, The Netherlands.Google Scholar
  77. Vershueren K (1983) Handbook of Environmental Data on Organic Chemicals. Van Nostrand Reinhold, New York.Google Scholar
  78. Virtanen MT, Hattula ML (1982) The fate of 2,4,6,-trichlorophenol in an aquatic continous-flow system. Chemosphere 11: 641–649.CrossRefGoogle Scholar
  79. Visser WJF (1993) Contaminated Land Policies in some Industrialized Countries. Report TCB R02, Technical Soil Protection Committee, The Hague, The Netherlands.Google Scholar
  80. Vonk JW, Adema DMM, Barug D (1986) Comparison of the effects of several chemicals on microorganisms, higher plants and earthworms. In: Assink JW, van den Brink JW (eds) Contaminated Soil 1986. Nijhoff, Dordrecht pp 191–202.Google Scholar
  81. VROM (1994) Environmental quality objectives in the Netherlands. A review of environmental quality objectives and their policy framework in the Netherlands. Risk Assessment and Environmental Quality Division, Directorate for Chemicals, External Safety and Radiation Protection, Ministry of Housing, Spatial Planning and the Environment, The Hague, The Netherlands.Google Scholar
  82. Walker N (1954) Preliminary observations on the decomposition of chlorophenols in soil. Plant Soil 5: 194–204.CrossRefGoogle Scholar
  83. Wedding RT, Hansch C, Fukuto TR (1967) Inhibition of malate dehydrogenase by phenols and the influence of ring substituents on their inhibitory effectiveness. Arch Biochem Biophys 121: 9–21.PubMedCrossRefGoogle Scholar
  84. Weigmann G, Papenhausen U, Kratz W, Gruttke H (1985) Die wirkung chemisscher belastnungen auf tier-and pflanzengesellschaften städtischer brachflächen. Specielle Berichte Berlin Kern Forschung Anlage Jülich 296: 121–129.Google Scholar
  85. Weinbach EC, Garbus J (1965) The interaction of uncoupling phenols with mitochondria and with mitochondrial protein. J Biol Chem 240: 1811–1819.PubMedGoogle Scholar
  86. Weiss UM, Moza P, Scheunert I, Hague A, Korte F (1982) Fate of pentachlorophenol-14C in rice plants under controlled conditions. J Agric Food Chem 30: 1186–1190.CrossRefGoogle Scholar
  87. Wild SR, Harrad SJ, Jones KC (1992) Pentachlorophenol in the UK environment. I: A budget and source inventory. Chemosphere 24: 833–845.CrossRefGoogle Scholar
  88. Wild SR, Harrad SJ, Jones KC (1993) Chlorophenols in digested U.K. sewage sludges. Water Res 27: 1527–1534.CrossRefGoogle Scholar
  89. World Health Organization (WHO) (1987) Pentachlorophenol. Environmental Health Criteria, vol 71. World Health Organization, Geneva, pp 1–236.Google Scholar
  90. WHO (1989) Chlorophenols other than pentachlorophenol. Environmental Health Criteria, vol 93. World Health Organization, Geneva, pp 1–209.Google Scholar
  91. Yasuda Y, Tochikubo K, Hachisuka Y, Tomida H, Ikeda K (1982) Quantitative structure-inhibitory activity relationships of phenols and fatty acids for Bacillus subtilis spore germination. J Med Chem 25: 315–320.PubMedCrossRefGoogle Scholar
  92. Zelles L, Scheuneret I, Korte F (1985). Side effects of some pesticides on non-target soil microorganisms. J Environ Sci Health B 205: 457–488.CrossRefGoogle Scholar
  93. Zelles L, El-Kabbany S, Scheunert I, Korte F (1989) Effects of pentachlorophenol 14C and HgC12 on the microflora of various soils in comparison to biodegradation and volatilization. Chemosphere 19: 1721–1727.CrossRefGoogle Scholar
  94. Zelles L, El-Kabbany S, Scheunert I (1991) The interrelationship between biological effects and the persistence of pentachlorophenol and HgC12 in various soils. Toxicol Environ Chem 30: 177–181.CrossRefGoogle Scholar
  95. Zietz E, Dumpert K, Römbke J (1987) Effects of pentachlorophenol and 2,4,5trichlorophenol on a soil ecosystem. I. Application and residue analysis. Sci Total Environ 61: 153–165.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag New York, Inc. 1996

Authors and Affiliations

  • John Jensen
    • 1
  1. 1.Department of Terrestrial EcologyDanish National Environmental Research InstituteSilkeborgDenmark

Personalised recommendations