Heptachlor and Heptachlor Epoxide

  • George W. Ware
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 104)

Abstract

Heptachlor (1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methanoindene) is an insecticide that was used on corn, alfalfa, hay, and vegetables, and as a termiticide. During the mid-1970s, use of heptachlor on food crops was phased out due to the persistence of the chemical and its epoxide. Currently, heptachlor is used only as a termiticide on a very limited number of crops. Its structure and properties are shown in Table 1.

Keywords

Corn Ozone Hydrocarbon Anemia Epoxide 

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References

  1. Abbott DC, Collins GB, Goulding R (1972) Organochloride pesticide residues in human fat in the United Kingdom 1969–1971. Brit Med J 2: 553–556.PubMedCrossRefGoogle Scholar
  2. Abbott DC, Collins GB, Goulding R, Hoodless RA (1981) Organochlorine pesticide residues in human fat in the United Kingdom 1976–1977. Brit Med J 283 (6304): 1425–1428.CrossRefGoogle Scholar
  3. ACGIH (1983) American Conference of Governmental Industrial Hygienists. TLVs: Threshold limit values for chemical substances and physical agents in the work environment with intended changes for 1983–1984. Cincinnati, OH. pp 14, 21.Google Scholar
  4. Ahmed FE, Hart RW, Lewis NJ (1977) Pesticide-induced DNA damage and its repair in cultured human cells. Mutat Res 42: 161–174.PubMedCrossRefGoogle Scholar
  5. Arnold DW, Kennedy GL Jr, Keplinger ML, Calandra JC, Calo CJ (1977) Dominant lethal studies with technical chlordane, HCS-3260 and heptachlor: heptachlor epoxide. J Toxicol Environ Hlth 2: 547–555.CrossRefGoogle Scholar
  6. Bakken AF, Sepi M (1976) Insecticides in human breast milk. Acta Paediatr Scand 65: 535–539.PubMedCrossRefGoogle Scholar
  7. Ben-Dyke R, Sanderson DM, Noakes DN (1970) Acute toxicity data for pesticides. Wildl Rev Pestic Control. 9: 119.Google Scholar
  8. Benes V, Sram R (1969) Mutagenic activity of some pesticides in Drosophila melanogaster. Ind Med 38: 50–52.Google Scholar
  9. Burns JE (1974) Organochlorine pesticide and polychlorinated biphenyl residues in biopsied human adipose tissue Texas, 1969–1972. Pestic Monit J 7: 122.Google Scholar
  10. Cerey K, Izakovic V, Ruttkay-Nedecka J (1973) Effects of heptachlor on dominant lethality and bone marrow in rats. Mutat Res 21: 26.CrossRefGoogle Scholar
  11. Curley A, Copeland MF, Kimbrough RK (1969) Chlorinated hydrocarbon insecticides in organs of stillborn and blood of newborn babies. Arch Environ Hlth 19: 628–632.Google Scholar
  12. Curley A, Burse VW, Jennings RW, Villaneuva EC, Tomatis L, Akazaki K (1973) Chlorinated hydrocarbon pesticides and related compounds in adipose tissue from people of Japan. Nature 242: 338–340.PubMedCrossRefGoogle Scholar
  13. Dadey JL, Kammer AG (1953) Chlordane intoxication. J Am Med Assoc 153: 723.PubMedGoogle Scholar
  14. Davis HJ (1965) Pathology report on mice fed aldrin, dieldrin, heptachlor or heptachlor epoxide for two years. Internal U.S. Food and Drug Administration memorandum to Dr. A. J. Lehman, July 19. (Cited in Epstein 1976 ).Google Scholar
  15. Den Tonkelaar EM, Van Esch GJ (1974) No-effect levels of organochlorine pesticides based on induction of microsomal liver enzymes in short-term toxicity experiments. Toxicology 2: 371.CrossRefGoogle Scholar
  16. Derbes VJ, Dent JH, Forrest WW, Johnson MF (1955) Fatal chlordane poisoning. J Am Med Assoc 158: 1367–1369.PubMedGoogle Scholar
  17. Dobbs RA, Cohen JM (1980) Carbon adsorption isotherms for toxic organics. Report no. EPA 600/8–80–023. USEPA Office of Research and Development, Washington, DC.Google Scholar
  18. Enan EE, El-Sebae AH, Enan OH (1982) Effects of some chlorinated hydrocarbon insecticides on liver function in white rats. Meded Fac Landbouwwet, Rijksuniv Gent 47 (1): 447–457.Google Scholar
  19. Epstein SS (1976) Carcinogenicity of heptachlor and chlordane. Sci Total Environ 6: 103.PubMedCrossRefGoogle Scholar
  20. FAO/WHO (1978) Food and Agricultural Organization/World Health Organization. FAO plant production and protection paper 10 Rev. Pesticides Residues in Food-1977. Rep Joint Meet FAO Panel of Experts on Pesticide Residues and Environment and the WHO Expert Committee on Pesticide Residues, Rome.Google Scholar
  21. Furie B, Trubowitz S (1976) Insecticides and blood dyscrasias: Chlordane exposure and self-limited refractory megaloblastic anemia. J Am Med Assoc 235: 1720–1722.CrossRefGoogle Scholar
  22. Gaines TB (1960) The acute toxicity of pesticides to rats. Toxicol Appl Pharmacol 2: 88.PubMedCrossRefGoogle Scholar
  23. Gentile JM, Gentile GJ, Bultman J, Sechriest R, Wagner ED, Plewa MJ (1982) An evaluation of the genotoxic properties of insecticides following plant and animal activation. Mutat Res 101 (1): 19–29.PubMedCrossRefGoogle Scholar
  24. Greer ES, Miller DJ, Bruscato FN, Holt RL (1980) Investigation of pesticide residues in human adipose tissue in the northeast Louisiana area. J Agric Food Chem 28 (1): 76–78.PubMedCrossRefGoogle Scholar
  25. Hadina PD, Singh RL, Peters DAV (1974) Changes in brain biogenic amines and body temperature after cyclodiene insecticides. Toxicol Appl Pharmacol 29: 119.Google Scholar
  26. IARC (1979) International Agency for Research on Cancer. Heptachlor and heptachlor epoxide. In: Some halogenated hydrocarbons. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 20. IARC, Lyon, France. pp 129–154.Google Scholar
  27. Infante PF, Epstein SS, Newton WA Jr (1978) Blood dyscrasias and childhood tumors and exposure to chlordane and heptachlor. Scand J Work Environ Hlth 4: 137–150.Google Scholar
  28. IRDC (1973) International Research and Development Corporation. Unpublished report to Velsicol Chemical Corporation, Eighteen Month Oral Carcinogenic Study in Mice, September 26. (Cited in Epstein 1976).Google Scholar
  29. Jolley WP, Stemmer HL, Pfitzer EA (1966) The effects of feeding diets containing a mixture of heptachlor and heptachlor epoxide to female rats for 2 years. Unpublished report from the Kettering Laboratory to Velsicol Corporation, January 28. (Cited in Epstein 1976).Google Scholar
  30. Klemmer KW, Budy AM, Takahasdhi W, Haley TJ (1977) Human tissue distribution of cyclodiene pesticides Hawaii 1964–1973. Clin Toxicol 11 (1): 71–82.PubMedCrossRefGoogle Scholar
  31. Krampl V (1971) Relationship between serum enzymes and histological changes in liver after administration of heptachlor in the rat. Bull Environ Contam Toxicol 5: 529.CrossRefGoogle Scholar
  32. Kroger M (1972) Insecticide residues in human milk. J Pediatr 80: 401–405.PubMedCrossRefGoogle Scholar
  33. Kutz FW, Strassman SC, Sperling JF (1979) Survey of selected organochlorine pesticides in the general population of the United States: Fiscal years 1970–1975. Ann NY Acad Sci 320: 60–68.PubMedGoogle Scholar
  34. Marshall TC, Dorough W, Swim HE (1976) Screening of pesticides for mutagenic potential using Salmonella typhimuriummutants. J Agric Food Chem 24: 560.PubMedCrossRefGoogle Scholar
  35. Maslansky CJ, Williams GM (1981) Evidence for an epigenetic mode of action in organochlorine pesticide hepatocarcinogenicity: A lack of genotoxicity in rat, mouse, and hamster hepatocytes. J Toxicol Environ Hlth 8 (1–2): 121–130.Google Scholar
  36. Mizyukova IG, Kurchatov GV (1970) Metabolism of heptachlor. Farmacol Toksikol (Moscow) 33(4):496–499. (Rus.) CA 73: 86885j.Google Scholar
  37. Moriya M, Ohta T, Watanabe K, Miyazawa T, Kato K, Shirasu Y (1983) Further mutagenicity studies on pesticides in bacterial reversion assay systems. Mutat Res 116 (3–4): 185–216.PubMedCrossRefGoogle Scholar
  38. NAS (1977) National Academy of Sciences. Drinking water and health. NAS, Washington, DC. pp 564, 568, 794.Google Scholar
  39. NCI (1977) National Cancer Institute. Bioassay of heptachlor for possible carcinogenicity. NCI Carcinogenesis Technical Report Series no. 9. National Cancer Institute, Bethesda, Maryland. 111 pp. (Also published by the U.S. Department of Health Education and Welfare as Publication no. NIH 77–809.)Google Scholar
  40. Podowski AA, Benerjee BC, Feroz M, Dudek MA, Willey RL, Khan MAQ (1979) Photolysis of heptachlor and cis-chlordane and toxicity of their photoisomers to animals. Arch Environ Contam Toxicol 8 (5): 509–518.PubMedCrossRefGoogle Scholar
  41. Polishuk ZW, Ron M, Wassermann M, Cucos S, Wassermann D, Lemesch C (1977) Organochlorine compound in human blood plasma and milk Pestic Monit J 10: 121–129.PubMedGoogle Scholar
  42. Probst GS, McMahon RE, Hill LE, Thompson CZ, Epp JK, Neal SB (1981) Chemically-induced unscheduled DNA synthesis in primary rat hepatocyte cultures: A comparison with bacterial mutagenicity using 218 compounds. Environ Mutagen 3 (1): 11–32.PubMedCrossRefGoogle Scholar
  43. Radomski JL, Davidow B (1953) The metabolite of heptachlor, its estimation, storage, and toxicity. J Pharmacol Exp Therap 107: 226.Google Scholar
  44. Reuber MD (1977a) Hepatic vein thrombosis in mice ingesting chlorinated hydrocarbons. Arch Toxicol 38: 163–168.CrossRefGoogle Scholar
  45. Reuber MD (1977b) Histopathology of carcinomas of the liver in mice ingesting heptachlor or heptachlor epoxide. Exp Cell Biol 45: 147–157.Google Scholar
  46. Ritcey WR, Savary G, McCully KA (1972) Organochlorine insecticide residues in human milk, evaporated milk and some milk substitutes in Canada. Can J Publ Health 63: 125–132.Google Scholar
  47. Savage EP, Tessari JD, Malberg JW, Wheeler HW, Bagby JR (1973) Organochlorine pesticide residues and polychlorinated biphenyls in human milk, Colorado 1971–1972. Pestic Monit J 7: 1–5.PubMedGoogle Scholar
  48. Shirasu Y, Moriya M, Kato K, Furuhashi A, Kada T (1976) Mutagenicity screening of pesticides in the microbial system. Mutat Res 40: 19–30.PubMedCrossRefGoogle Scholar
  49. Sigworth E (1965) Identification and removal of herbicides. J Am Waterworks Assoc 55: 1016–1022.Google Scholar
  50. Sovocool GW, Lewis RG (1975) The identification of trace levels of organic pollutants in human tissues: Compounds related to chlordane/heptachlor exposure. Trace Subst Environ Hlth 9: 265.Google Scholar
  51. Sperling F, Ewinike H (1969) Changes in LD50 of parathion and heptachlor after turpentine pretreatment (Abstract no. 24). Toxicol Appl Pharmacol 14: 622.Google Scholar
  52. Standard Methods (1985) Method 509A. Organochlorine pesticides. In: Standard methods for the examination of water and wastewater, 16th Ed. American Public Health Association, Washington, DC.Google Scholar
  53. Strassman SC, Kutz FW (1977) Insecticide residues in human milk from Arkansas and Mississippi, 1973–1974. Pestic Monit J 10: 130–133.PubMedGoogle Scholar
  54. Takahashi W, Saidin D, Takei G, Wong L (1981) Organochloride pesticide residues in human milk in Hawaii, 1979–1980. Bull Environ Contam Toxicol 27 (4): 506–511.PubMedCrossRefGoogle Scholar
  55. Tashiro S, Matsumura F (1978) Metabolism of trans-nonachlor and related chlordane components in rat and man. Arch Environ Contam Toxicol 7 (1): 113–127.PubMedCrossRefGoogle Scholar
  56. USEPA (1958) Kettering Laboratory. 60-week dog feeding study. MRID no. 0061912.Google Scholar
  57. USEPA Office of Pesticide Programs, Washington, DC.Google Scholar
  58. USEPA (1978) Method for organochlorine pesticides in drinking water. Methods for organochlorine pesticides and chlorophenoxy acid herbicides in drinking water and raw source water. Interim report July 1978. USEPA Environmental Monitoring and Support Laboratory, Cincinnati, OH.Google Scholar
  59. USEPA (1980) Ambient Water quality criteria for heptachlor. Report no. EPA 440/5–80–052. NTIS PB 81–117632. USEPA Office of Water Regulations and Standards, Washington, DC.Google Scholar
  60. USEPA (1983) Occurrence of pesticides in drinking water, food, and air. USEPA Office of Drinking Water, Washington, DC.Google Scholar
  61. USEPA (1985a) Draft drinking water criteria document for chlordane, heptachlor and heptachlor epoxide. USEPA Office of Drinking Water, Washington, DC.Google Scholar
  62. USEPA (1985b) Technologies and costs for the removal of synthetic organic chemicals from potable water supplies. USEPA Office of Drinking Water, Washington, DC.Google Scholar
  63. USEPA (1986) Guidelines for carcinogen risk assessment. Fed Regis 51(185):33992–34003. September 24.Google Scholar
  64. USEPAa (1987) Drinking water criteria document for heptachlor, heptachlor epoxide and chlordane. Report no. ECAO-CIN-406. USEPA Office of Drinking Water, Washington, DC.Google Scholar
  65. Wang HH, MacMahon B (1979) Mortality of workers employed in the manufacture of chlordane and heptachlor J Occup Med 21: 745–748.PubMedCrossRefGoogle Scholar
  66. Wassermann M, Nogueira DP, Tomatis L, et al. (1972) Storage of organochlorine insecticides in people of Sao Paulo, Brazil. Ind Med 41: 22.Google Scholar
  67. Wassermann M, Tomatis L, Wassermann D, et al. (1974) Epidemiology of organo-chlorine insecticides in the adipose tissue of Israelis. Pestic Monit J 8: 1.PubMedGoogle Scholar
  68. WHO (1984) World Health Organization. Guidelines for drinking water quality. Vol I—Recommendations. WHO, Geneva, Switzerland.Google Scholar
  69. Witherup S, Cleveland FP, Shaffer FG, Schlecht H, Musen L (1955) The physiological effects of the introduction of heptachlor into the diet of experimental animals in varying levels of concentration. Unpublished report from Kettering Laboratory to Velsicol Corporation, August 17. (Cited in Epstein 1976).Google Scholar
  70. Witherup S, Cleveland FP, Stemmer K (1959) The physiological effects of the introduction of heptachlor epoxide in the varying levels of concentration into the diet of CFN rats. Unpublished report from Kettering Laboratory to Velsicol Corporation, November 10. (Cited in Epstein 1976).Google Scholar
  71. Yamaguchi I, Matsumura F, Kadous AA (1980) Heptachlor epoxide: Effects on calcium-mediated transmitter release from brain synaptosomes in rat. Biochem Pharmacol 29 (12): 1815–1823.PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag New York Inc. 1988

Authors and Affiliations

  • George W. Ware
    • 1
  1. 1.College of AgricultureUniversity of ArizonaTucsonUSA

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