Summary
Hexachlorobenzene (HCB) is today known as an environmental pollutant of ubiquitous occurrence. Its physical properties favor its global distribution and its accumulation in sediments and biota. Its chemical properties result in only slow abiotic and biotic degradation. HCB was earlier used in some industrial connections but above all as a fungicide. However, after a severe disaster in Turkey in the 1950’s - delayed outbreak of liver porphyria in persons eating HCB-treated seed grains - most applications gradually ceased. Since the input into the environment continues, other sources must exist and these are discussed in the present survey.
The analysis of HCB presents some problems and methods to overcome these are briefly mentioned. Analysis of samples of air, water, sediment and fish point to a fairly even distribution within the western hemisphere; industrialized areas may show increased levels.
Among the persistent xenobiotics HCB displays extreme physical properties, the influence of which on uptake and bioconcentration in aquatic organisms is briefly discussed. The lack of detailed investigations covering the metabolism of HCB in e. g., fish has rendered necessary a brief account of its far better known biotransformation in rats and mice. This is initially very slow but the rate increases gradually during a chronic exposure, possibly reflecting the pronounced enzyme-inducing properties of HCB. Apart from the main metabolite - pentachlorophenol - numerous other products containing oxygen or sulfur have been identified. Mechanistic studies have revealed a route directly from HCB to sulfur-containing conjugates via microsomally bound glutathione S-transferases. It is today well established that oxidative transformation of HCB via a P-450-dependent MFO-system is a prerequisite for outbreak of porphyria e.g., in the rat. However, experiments using carbon-14-labeled compounds indicate that HCB-metabolites as such are not directly involved in the porphyria-induction process. These results are supported by tests where pentachlorobenzene - forming the same phenolic metabolites as HCB - is reported not to induce porphyria in the rat. Alternative mechanisms involving, e. g., oxygen radicals are now being discussed.
The acute toxicity of HCB to aquatic organisms as studied in laboratory experiments is low. Effects, if observed, occur at levels far above those found in the environment. It is, however, noteworthy that long-term tests comparable to those on rats and mice have apparently not been performed. Exposure of a protozoan to HCB is reported to give disturbed porphyrin metabolism. Field studies indicate similar effects in pike exposed to HCB, PCB and DDT. An acceptable advanced hazard assessment of HCB would require extended tests to comprise potential porphyrinogenic capacity of HCB and also effects on reproduction capacity. To permit comparison with fish caught in the field it is essential that laboratory exposure is expressed as content in fish, preferably on a lipid base.
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
Abernethy S, Bobra AM, Shiu WY, Wells PG, Mackay D (1986) Acute lethal toxicity of hydrocarbons and chlorinated hydrocarbons to two planktonic crustaceans: The key role of organism-water partitioning. Aquat Toxicol 8:163–174
Åkermark B, Backström P, Eklund-Westlin U, Göthe R, Wachtmeister CA (1976) Photochemical dechlorination of 1,2,4-trichlorobenzene. Acta Chem Scand B30: 49–52
Alleman MA, Koster JF, Wilson JM, Edixhoven-Bosdijk A, Slee RG, Kroos MJ, Eijk HG van (1985) The involvement of iron and lipid peroxidation in the pathogenesis of HCB induced porphyria. Biochem Pharmacol 34:101–116
Anderson RS, Giam CS, Ray LE, Tripp MR (1981) Effects of environmental pollutants on immunological competency of the clam Mercenaria mercenaria: Impaired bacterial clearance. Aquat Toxicol 1:187–195
Bakke JE (1986) Catabolism of glutathione conjugates. In: Paulson GD, Caldwell J, Hudson DH, Menn JJ (eds) Xenobiotic conjugation chemistry. ACS Symp Ser 299. Am Chem Soc, Washington D C, pp 301–321
Ballschmiter K, Zell M (1980) Baseline studies of the global pollution I. Occurrence of organo- halogens in pristine European and Antarctic aquatic environment. Intern J Environ Anal Chem 8:15–35
Ballschmiter K, Niemczyk R, Schäfer W, Zoller W (1987) Isomer-specific identification of polychlorinated benzenes and biphenyls in effluents of municipal waste incineration. Fresenius Z Anal Chem 328: 583–587
Bidleman T (1984) Estimation of vapor pressures for nonpolar organic compounds by capillary gas chromatography. Anal Chem 56: 2490–2496
Bidleman T, Wideqvist U, Jansson B, Söderlund R (1987) Organochlorine pesticides and polychlorinated biphenyls in the atmosphere of southern Sweden. Atmos Environ 21: 641–654
Bjerk JE, Brevik EM (1980) Organochlorine compounds in aquatic environments. Arch Environ Contam Toxicol 9: 743–750
Blackwood TR, Sipes TG (1979) Status assessment of toxic chemicals. US Environ Prot Ag EPA-600/2–79-210g: 1–20
Bleavins MR, Aulerich RJ, Ringer R (1983) Hexachlorobenzene induced effects on the lymphocyte blastogenic response to concanavalin in the mink. Environ Toxicol Chem 2: 411–416
Bøckman OC (1981) HCB og andere halogenerte organiske forbindelser 17. Nordiske Symposium om Vattenforskning. Nordforsk Miljövårdsser 1981:1:119–130 (In Norwegian)
Brandt J, Bergman A (1987) PCB methyl sulphones and related compounds: Identification of target cells and tissues in different species. Chemosphere 16:1671–1676
Brevik EM (1981) Organochlorine residues in fish from Lake Mjøsa in Norway. Bull Environ Contam Toxicol 26: 679–680
Bro-Rasmussen F (1986) Hexachlorobenzene: An ecotoxicological profile of an organochlorine compound. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 231–242
Calamari D, Galassi S, Setti F, Vighi M (1983) Toxicity of selected chlorobenzenes to aquatic organisms. Chemosphere 12: 253–262
Caron G, Suffet IH, Belton T (1985) Effect of dissolved organic carbon on the environmental distribution of nonpolar organic compounds. Chemosphere 14: 993–1000.
Choudhry GG, Huzinger O (1984) Acetone-sensitized and nonsensitized photolyses of tetra-, penta- and hexachlorobenzenes in acetonitrile-water mixtures. Environ Sci Technol 18: 235–241
Courtney KD (1979) Hexachlorobenzene - a review. Environ Res 20: 225–266
Debets FMH, Hamers WJHMB, Strik JJTWA (1980) Metabolism as a prerequisite for the porphyrinogenic action of polyhalogenated aromatics, with special reference to hexachlorobenzene and polybrominated biphenyls (Firemaster BP-6). Int J Biochem 12: 1019- 1025
Debets FMH, Reinders JH, Debets AJM, Lössbrock TG, Strik JJTWA, Koss G (1981) Biotransformation and porphyrinogenic action of hexachlorobenzene and its metabolites in a primary liver cell culture. Toxicology 19:185–196
De Matteis F (1986) Experimental hepatic porphyria caused by hexachlorobenzene: Mechanism of the metabolic block. In: Morris CR, Cabral JPR (eds) Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 427–431
Doucette WY, Andren AW (1988) Estimation of octanol/water partition coefficients: Evaluation of six methods for highly hydrophobic aromatic hydrocarbons. Chemosphere 17: 345–359
Ekelund R, Granmo Å, Berggren M, Renberg L, Wahlberg C (1987) Influence of suspended solids on bioavailability of hexachlorobenzene and lindane to the deposit-feeding bivalve Abra nitida (Müller). Bull Environ Contam Toxicol 38: 500–508
Ernst W (1986) Hexachlorobenzene in the Marine Environment: Distribution, fate and ecotoxicological aspects. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 211–222
Falandysz J (1982) Chlorinated hydrocarbons in salmon netted in Gdansk Bay, Baltic Sea (Poland). Meeresforschung 29: 219–224
Fowler SW, Villeneuve JP, Burns, KA (1986) Vertical flux of hexachlorobenzene in coastal waters of the North-west Mediterranean Sea. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 67–73
Geike F, Parasher, CD (1976 a) Effect of hexachlorobenzene (HCB) on growth of Tetrahy- mena pyriformis . Bull Environ Contam Toxicol 16: 347–354
Geike F, Parasher CD (1976b) Effect of hexachlorobenzene on some growth parameters of Chlorella pyrenoidosa. Bull Environ Contam Toxicol 15: 670–677
Gluth G, Hanke W (1984) A comparison of physiological changes in carp,Cyprinus carpio induced by several pollutants at sublethal concentration - II. The dependency on the temperature. Comp Biochem Physiol 79C: 39–45
Goldstein JA, Friesen M, Scotti TM, Hickman P, Hass JR, Bergman H (1978) Assessment of the contribution of chlorinated dibenzo-p-dioxins and dibenzofurans to HCB-induced toxicity, porphyria, changes in mixed function oxygenases and histopathological changes. Toxicol Appl Pharmacol 46: 633–649
Goldstein JA, Linko P, Hahn ME, Gasiewicz TA, Yeowell HN (1986) Structure-activity relationships of chlorinated benzenes as inducers of hepatic cytochrome P-450 isozymes in the rat. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 519–526
Hawker DW, Connell DW (1985) Relationships between partition coefficient, uptake rate constant, clearance rate constant and time to equilibrium for bioaccumulation. Chemo- sphere 14:1205–1219
Heinish E (1978) Biogeochemische Kreisläufe persistenter organisher Verbindungen, dargestellt am Hexachlorbenzol. Sitzungsber Akad Wiss DDR 20N: 3–67
IARC (1979) Monographs on the evaluation of the carcinogenic risk of chemicals to humans. Int Ag Res Cancer, Lyon 20:155–177
Ingebrigtsen K, Skaare SU (1983) Distribution and elimination of 14C-hexachlorobenzene after single oral exposure in the rainbow trout (Salmo gairdneri). J Toxicol Environ Health 12: 309–316
Ingebrigtsen K, Solbakken JE (1985) Distribution and elimination of 14C-hexachlorobenzene after single oral exposure in cod (Gadus morhua) and flounder (Platichthys flesus). J Toxicol Environ Health 16:197–205
Jensen S, Johnels A G, Olsson M, Otterlind G (1972) DDT and PCB in herring and cod from the Baltic, the Kattegatt and the Skagerak. Ambio Spec Rep No 1: 71–85
Jensen S, Renberg L, Reutergårdh (1977) Residue analysis of sediment a nd sewage sludge for organochlorines in the presence of elemental sulfur. Anal Chem 49: 77–79
Jensen S, Reutergårdh L, Jansson B (1983) Analytical methods for measuring organochlorines and methyl mercury by gas chromatography. FAO/SIDA Manual of methods in aquatic environment research. Part 9. Analysis of metals and organochlorines in fish. FAO Fish Tech Pap 212: 21–33
Johnsen RE, Munsell Y (1977) Facile elimination of sulfur interference in pesticide analysis by gas chromatography. Bull Environ Contam Toxicol 17: 573–576
Kobayanski H (1982) Microbiological removal of hazardous organic compounds. Environ Sci Technol 16:170A-183A
Koss G, Koransky W (1978) Pentachlorophenol in different species of vertebrates after administration of hexachlorobenzene and pentachlorobenzene. In: Ranga Rao K (ed) Pentachlorophenol. Plenum, New York, London, pp 131–137
Koss G, Seubert S, Seubert A, Koransky W, Ippen H (1978) Studies on the toxicology of hexachlorobenzene III Observations in a long-term experiment. Arch Toxicol 40: 285–294
Koss G, Schüler E, Arndt B, Seidel Y, Seubert S, Seubert A (1986) A comparative toxicologi- cal study on pike (Esox lucius L) from the river Rhine and river Lahn. Aquat Toxicol 8:1–9
Krämer W, Ballschmiter K (1988) Global baseline pollution studies XII. Content and pattern of polychloro-cyclohexanes (HCH) and -biphenyls (PCB), and content of hexachlorobenzene in the water column of the Atlantic Ocean. Fresenius Z Anal Chem 330: 524–526
Krämer W, Buchert H, Reuter V, Biscoito M, Maul DG, Le Grand G, Ballschmiter K (1984) Global Baseline Pollution Studies IX C6-C14 organochlorine compounds in surface-water and deep-sea fish from the eastern North Atlantic. Chemosphere 13:1255–1267
Laake M (1978) En sammenligning av dyrkingsmetoder for alger ved forsök med heksaklor-bensen. Fjortonde nordiska symp om vattenforskning. Ålborg, Denmark 25–27 April 1978, Nordforsk Miljövårdssekr Publ 1978: 2, pp 179–190 (In Norwegian)
Laake M (1981) Heksaklorbensen - en okotoxikologisk vurdering. Sjutconde nordiska symp. om vattenforskning. Porsgrunn, Norway 4–7 maj 1981. Nordforsk Miljövårdssekr Publ 1981:1, pp 233–262 (In Norwegian)
Linder R, Scotti T, Goldstein J, McElroy K, Walsh D (1980) Acute and subchronic toxicity of pentachlorobenzene. J Environ Pathol Toxicol 4:183–196
Lund BO, Bergman Å, Brandt I (1988) Metabolic activation and toxicity of a DDT-metabolite, 3-methylsulphonyl-DDE, in the adrenal zona fasciculata in mice. Chem Biol Interact 65: 25–40
MacLeod KE, Hanish R, Lewis R (1982) Evaluation of gel permeation chromatography for GC/MS analysis of pesticides and other chemicals. J Anal Toxicol 6: 38–40
McKim J, Schneider P, Veith G (1985) Absorption dynamics of organic chemical transport across trout gills as related to octanol-water partition coefficient. Toxicol Appl Pharmacol 77:1–10
Mehendale HM, Fields M, Matthews HB (1975) Metabolism and effects of hexachlorobenzene on hepatic microsomes in the rat. J Agric Food Chem 23: 261–265
Metealf RL, Kapoor JP, Lu PY, Schuth CK, Sherman P (1973) Model ecosystems studies of the environmental fate of six organochlorine pesticides. Environ Health Perspect 4: 27-34
Miller MM, Waslk SP, Huang GL, Shiu WY, Mackay D (1985) Relationships between octa- nol- water partition coefficient and aqueous solubility. Environ Sci Technol 19: 522–529
Morgenstern R, DePierre JW (1985) Microsomal glutathione S-transferase. In: Hodgson E, Bend JR, Philpot RM (eds) Reviews in biochemical toxicology, vol 7. Elsevier, Amsterdam, New York, pp 67–104
Morita M (1977) Chlorinated benzenes in the environment. Ecotoxicol Environ Safety 1:1–6
Müller MD (1982) Hexachlorbenzol in der Schweiz - Ausmass und Hintergründe der Umweltkontamination. Chimia 36: 437–445
Niimi AJ (1983) Biological and toxicological effects of environmental contaminants in fish and their eggs. Can J Fish Aquat Sci 40: 306–312
Nijhuis H, Heeschen W (1986) Hexachlorobenzene contamination of milk and human samples. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. I ARC Sci Publ No 77, Lyon, pp 133–137
Norén K (1988) Changes in the levels of organochlorine pesticides, polychlorinated biphenyls, dibenzo-p-dioxins and dibenzofurans in human milk from Stockholm, 1972–1985. Chemo- sphere 17: 39–48
Oliver BG, Charlton MN (1984) Chlorinated organic contaminants on settling particulates in the Niagara River vicinity of Lake Ontario. Environ Sci Technol 18: 903–908
Oliver BG, Nicol KD (1982) Chlorobenzenes in sediments, water and selected fish from Lakes Superior, Huron, Erie and Ontario. Environ Sci Technol 16: 532–536
Olsson M, Jensen S (1975) Pike as the Test Organism for Mercury, DDT and PCB Pollution. A Study of the contamination in the Stockholm archipelago. Inst Freshwater Res, Drott- ningholm, Sweden, Rep No 54: 83–106
Ommen van B, Bladeren PJ van, Temmink JHM, Müller F (1985) Formation of pentachloro- phenol as the major product of microsomal oxidation of hexachlorobenzene. Biochem Bio- phys Res Commun 126: 25–32
Ommen van B, Adang AEP, Brader L, Posthumus MA, Müller F, Bladeren PJ van (1986 a) The microsomal metabolism of hexachlorobenzene - origin of the covalent binding to protein. Biochem Pharmacol 35: 3233–3238
Ommen van B, Adang AEP, Müller F, Bladeren PJ van (1986 b) The microsomal metabolism of pentachlorophenol and its covalent binding to protein and DNA. Chem Biol Interact 60: 1–11
Ommen van B, Bladeren PJ van, Adang AEP, Bessems JGM, Koeman JH (1987) Biotransformation of 14C-hexachlorobenzene and its major oxidative metabolites by primary cultures of chick embryo hepatocytes. In: Ommen B van. Thesis, Dep Toxicol, Agric Univ, Wageningen, The Netherlands, pp 107–119
Ommen van B, Voncken JW, Müller F, Bladeren PJ van (1988) The oxidation of tetrachloro- 1,4-hydroquinone by microsomes and purified cytochrome P-450b. Implications for covalent binding to protein and involvement of reactive oxygen species. Chem Biol Interact 65: 247–259
Opperhuizen A, Velde EW v d, Gobas FAPC, Liem PAK, Steen JMD v d (1985) Relation between bioconcentration in fish and steric factors of hydrophobic chemicals. Chemo- sphere 14:1871–1896
Perttila M, Tervo V, Parmanne R (1982) Age dependence of the concentration of harmful substances in Baltic herring Clupea harengus . Chemosphere 11: 1019–1026
Phelps DK, Pruell RS, Lake J (1986) Hexachlorobenzene in selected marine samples: an environmental perspective. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 121–130
Quinlivan SC, Ghassemi M, Leshendok TV (1975/77) Sources, characteristics and treatment and disposal of industrial wastes containing hexachlorobenzene. J Hazardous Materials 1:343–359
Renner G (1981) Biotransformation of the fungicides hexachlorobenzene and pentachloroni- trobenzene. Xenobiotica 11: 436–446
Renner G, Nguyen PT (1984) Mechanism of the reductive denitration of pentachloronitroben- zene and the reductive dechlorination of hexachlorobenzene. Xenobiotica 14: 705–710
Reutergårdh L (1988) Identification and distribution of chlorinated organic pollutants in the environment. Natl Swed Environ Protect Board, Solna Rep 3465: 29–30
Reutergårdh L, Knap AH (1987) Overview of organochlorine compound analysis in marine mammals. Int Counc Explor Sea Mar Mam 7.2.2
Rippen G, Frank R (1986) Estimation of hexachlorobenzene pathways from the technosphere into the environment. In: Morris CR, Cabral JPR (eds) Hexahlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 45–52
Sanborn, JR, Childers WF, Hansen LG (1977) Uptake and elimination of [14C]-hexachloro- benzene (HCB) by the green sunfish, Lepomis cyanellus Raf., after feeding contaminated food. J Agric Food Chem 25: 551–553
Sandermann H, Scheel D, Trenck TH v d (1984) Use of plant cell cultures to study the metabolism of environmental chemicals. Ecotoxicol Environ Safety 8:167–182
Scheunert J, Marra C, Viswanathan R, Klein W, Korte F (1983) Fate of hexachlorobenzene- 14C in wheat plants and soil under outdoor conditions. Chemosphere 12: 843–858
Södergren A, Larsson P (1982) Transport of PCBs in aquatic laboratory model ecosystems from sediment to the atmosphere via the surface microlayer. Ambio 11: 41–45
Steinwandter H (1982) Contribution to the application of gel chromatography in the residue analysis. Fresenius Z Anal Chemie 313: 536–538
Stewart FP, Smith AG (1986) Metabolism of the mixed cytochrome P-450 inducer hexachlorobenzene by rat liver microsomes. Biochem Pharmacol 35: 2163–2170
Suntio LR, Shiu WY, Mackay D (1988) A review of the nature and properties of chemicals present in pulp mill effluents. Chemosphere 17:1249–1290
Sweeney GD, Basford D, Krestynski F (1986) The role pf contaminants in hexachlorobenzene toxicity. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 363–370
Takazawa RS, Strobel HW (1986) Cytochrome P-450 mediated reductive dehalogenation of hexachlorobenzene. Biochemistry 25: 4804–4809
Testaferri I, Tingoli M, Tiecco N (1980) Reactions of polychlorobenzenes with alkane thiol anions in HMPA. A simple high yield synthesis of poly(alkylthio)benzenes. J Org Chem 45: 4376–4380
Tobin P (1986) Known and potential sources of hexachlorobenzene. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 3–12
Uhnák J, Veningerovä M, Madaric A (1986) Dynamics of hexachlorobenzene residues in the food chain. In: Morris CR, Cabral JPR (eds) Hexachlorobenzene. Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 109–113
Uyeta M, Tave S, Chikusawa K, Mazaki M (1976) Photoformation of poly chlorinated biphe- nyls from chlorinated benzenes. Nature (London) 264: 583–585
Weast RC (1977) Handbook of chemistry and physics, 58th edn. CRC, Cleveland
Wittlinger R, Ballschmiter K (1987) Global Baseline Pollution Studies XI: Congener specific determination of polychlorinated biphenyls (PCB) and occurrence of alpha- and gamma- hexachlorocyclohexane (HCH), 4,4’-DDE and 4,4’-DDT in continental air. Chemosphere 16: 2497–2513
Yesair, DW, Feder PJ, Chin E, Naber SJ, Kuiper-Goodman T, Siegel Scott C, Robinson PE (1986) Development, evaluation and use of a pharmacokinetic model for hexachlorobenzene. In: Morris CR, Cabral JPR (eds) Proc Int Symp. IARC Sci Publ No 77, Lyon, pp 297–318
Zafiriou OC, Joussot-Dubien J, Zepp RG, Zika RG (1984) Photochemistry of natural waters. Environ Sci Technol 18: 358A-371A
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1989 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Wachtmeister, C.A., Ekelund, R. (1989). A Tentative Hazard Assessment of Hexachlorobenzene in the Aquatic Environment. In: Landner, L. (eds) Chemicals in the Aquatic Environment. Springer Series on Environmental Management. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-61334-0_13
Download citation
DOI: https://doi.org/10.1007/978-3-642-61334-0_13
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-64796-3
Online ISBN: 978-3-642-61334-0
eBook Packages: Springer Book Archive