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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
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.
Ahlborg UG, Thunberg TM (1980) Chlorinated phenols: occurence, toxicity, metabolism, and environmental impact. CRC Crit Rev Toxicol 7: 1–36.
Baker MD, Mayfield CI (1980) Microbial and non-biological decomposition of chlorophenols and phenol in soil. Water Air Soil Pollut 13: 411–424.
Bellin CA, O’Connor GA (1990) Plant uptake of pentachlorophenol from sludgeamended soils. J Environ Qual 19: 298–302.
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.
Bornkamm R, Meyer G (1985) Die wirkung chemischer belastung auf die stadtvege- tationen. Specielle Berichte Berlin Kern Forschung Anlage Jülich 296: 130–145.
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.
Bryant SE, Schultz TW (1994) Toxicological assessment of biotransformation products of pentachlorophenol: Tetrahymena population growth impairment. Arch Environ Contam Toxicol 26: 299–303.
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.
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.
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.
Casterline JL, Barnett NM, Ku Y (1985) Uptake, translocation and transformation of pentachlorophenol in soyabean and spinach plants. Environ Res 37: 101–118.
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.
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.
Drong K, Lamprecht I (1993) Toxicological studies of energy flows in ecological systems. Pure Appl Chem 65: 1967–1972.
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.
Ferro AM, Sims RC, Bugbee B (1994) Hycrest crested wheatgrass accelerates the degradation of pentachlorophenol in soil. J Environ Qual 23: 272–279.
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.
Ghoshal S, Banerji SK, Bajpai RK (1992) Role of photodegradation in pentachlorophenol decontamination in soils. Ann NY Acad Sci 665: 412–422.
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.
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.
Haimi J, Salminen J, Huhta V, Knuutinen J, Palm H (1992) Bioaccumulation of organochlorine compounds in earthworms. Soil Biol Biochem 24: 1699–1703.
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.
Haque A, Scheunert I, Korte F (1978) Isolation and identification of a metabolite of pentachlorophenol 14C in rice plants. Chemosphere 1: 65–69.
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.
Harvey WA, Crafts AS (1950) Toxicity of pentachlorophenol and its sodium salt in three Yolo soils. Hilgardia 21: 487–498.
Hattemer-Frey HA, Travis CC (1989) Pentachlorophenol: environmental partitioning and human exposure. Arch Environ Contam Toxicol 18: 482–489.
Heimbach F (1984) Correlation between three methods for determining the toxicity of chemicals to earthworms. Pestic Sci 15: 605–611.
Howard PH (1989) Handbook of Environmental Fate and Exposure Data for Organic Chemicals, Vol 1. Large Production and Priority Pollutants. Lewis Publishers, Chelsea, MI.
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.
Ide A, Niki Y, Sakamoto F, Watanabe I, Watanabe H (1972) Decomposition of pentachiorphenol in paddy soil. Agric Biol Chem 36: 1937–1944.
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.
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.
Jensen J, Folker-Hansen P (1995) Soil quality criteria for selected organic compounds. Working Report (Arbejdsrapport) no. 47, Danish Environmental Protecting Agency, Copenhagen, Denmark.
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.
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.
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.
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.
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.
Lagas P (1988) Sorption of chlorophenols in the soil. Chemosphere 17: 205–216.
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.
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.
Ma K-C, Shiu W-Y, Mackay D (1993) Aqueous solubilities of chlorinated phenols at 25 °C. J Chem Eng Data 38: 364–366.
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.
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).
Moulton MP, Schultz TW (1986) Comparisons of several structure-toxicity relationships for chiorophenols. Aquat Toxicol 8: 121–128.
Murthy NBK, Kaufman DD, Fries GF (1979) Degradation of pentachlorophenol ( PCP) in aerobic and anaerobic soil. J Environ Sci Health B 14: 1–14.
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.
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.
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.
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.
Richards DJ, Shieh WK (1986) Biological fate of organic priority pollutants in the aquatic environment. Water Res 20: 1077–1090.
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.
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.
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.
Sato K (1987) Effect of increasing pentachlorophenol (PCP) concentrations on bacterial populations in glycine-pecolated soils. Biol Fertil Soils 5: 1–5.
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.
Schellenberg K, Leuenberger C, Schwarxenbach RP (1984) Sorption of chlorinated phe- nols by natural sediments and aquifer materials. Environ Sci Technol 18: 652–657.
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.
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.
Seiler JP (1991) Pentachlorophenol. Mutat Res 257: 27–47.
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.
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.
Smejtek P (1987) The physicochemical basis of the membrane toxicity of pentachlorophenol: an overview. J Membr Sci 33: 249–268.
Tam TY, Trevors JT (1981) Effects of pentachlorophenol on asymbiotic nitrogen fixation in soil. Water Air Soil Pollut 16: 409–414.
Trevors JT (1982a) Effect of temperature on the degradation of pentachlorophenol by Pseudomonas species. Chemosphere 11: 471–475.
Trevors JT (1982b) Differences in the sensitivity of short-term bioassays. Bull Environ Contam Toxicol 28: 655–659.
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.
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.
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.
van Gestel CAM, Ma W (1988) Toxicity and bioaccumulation of chlorophenols in earthworms, in relation to bioavailability. Ecotoxicol Environ Saf 15: 289–297.
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.
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.
van Gestel CAM, Ma W (1990) An approach to quantitative structure-activity rela- tionships (QSARs) in earthworm toxicity studies. Chemosphere 21: 1023–1033.
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.
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.
Vershueren K (1983) Handbook of Environmental Data on Organic Chemicals. Van Nostrand Reinhold, New York.
Virtanen MT, Hattula ML (1982) The fate of 2,4,6,-trichlorophenol in an aquatic continous-flow system. Chemosphere 11: 641–649.
Visser WJF (1993) Contaminated Land Policies in some Industrialized Countries. Report TCB R02, Technical Soil Protection Committee, The Hague, The Netherlands.
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.
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.
Walker N (1954) Preliminary observations on the decomposition of chlorophenols in soil. Plant Soil 5: 194–204.
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.
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.
Weinbach EC, Garbus J (1965) The interaction of uncoupling phenols with mitochondria and with mitochondrial protein. J Biol Chem 240: 1811–1819.
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.
Wild SR, Harrad SJ, Jones KC (1992) Pentachlorophenol in the UK environment. I: A budget and source inventory. Chemosphere 24: 833–845.
Wild SR, Harrad SJ, Jones KC (1993) Chlorophenols in digested U.K. sewage sludges. Water Res 27: 1527–1534.
World Health Organization (WHO) (1987) Pentachlorophenol. Environmental Health Criteria, vol 71. World Health Organization, Geneva, pp 1–236.
WHO (1989) Chlorophenols other than pentachlorophenol. Environmental Health Criteria, vol 93. World Health Organization, Geneva, pp 1–209.
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.
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.
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.
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.
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.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1996 Springer-Verlag New York, Inc.
About this chapter
Cite this chapter
Jensen, J. (1996). Chlorophenols in the Terrestrial Environment. In: Ware, G.W. (eds) Reviews of Environmental Contamination and Toxicology. Reviews of Environmental Contamination and Toxicology, vol 146. Springer, New York, NY. https://doi.org/10.1007/978-1-4613-8478-6_2
Download citation
DOI: https://doi.org/10.1007/978-1-4613-8478-6_2
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4613-8480-9
Online ISBN: 978-1-4613-8478-6
eBook Packages: Springer Book Archive