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Chlordane

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Chlordane
Chlordane
Chlordane
Names
Systematic IUPAC name
1,2,4,5,6,7,8,8-Octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methanoindene
Other names
Chlordan; Ortho; Octachloro-4,7-methanohydroindane
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.000.317 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H6Cl8/c11-3-1-2-4(5(3)12)9(16)7(14)6(13)8(2,15)10(9,17)18/h2-5H,1H2
  • ClC1CC2C(C1Cl)[C@@]3(Cl)C(=C(Cl)[C@@]2(Cl)C3(Cl)Cl)Cl
Properties
C10H6Cl8
Molar mass 409.76 g·mol−1
Appearance Colorless, viscous liquid
Odor Slightly pungent, chlorine-like
Density 1.60 g/cm3
Melting point 106 °C (223 °F; 379 K)
Boiling point 175 °C (347 °F; 448 K)
5.6 g/100 mL
1.565
Hazards
Flash point 107 °C (225 °F; 380 K)
Explosive limits 0.7-5%
Lethal dose or concentration (LD, LC):
590 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chlordane, or chlordan, is an organochlorine compound used as a pesticide. This white solid was sold in the U.S. until 1983 as an insecticide for crops like corn and citrus, and on lawns and domestic gardens.[1] Technical grade chlordane is a complex mixture of over 120 structurally related chemical compounds.[2]

Production and uses

Chlordane is one so-called cyclodiene pesticide, meaning that it is derived from hexachlorocyclopentadiene. Hexachlorocyclopentadiene forms an adduct with cyclopentadiene, and chlorination of this adduct gives two isomers, α and β. The beta-isomer is popularly known as gamma. The mixture is called chlordane. The β isomer is more bioactive.[1] It was sold in the United States from 1948 to 1988, both as a dust and an emulsified solution.

Because of concern about damage to the environment and harm to human health, the United States Environmental Protection Agency (EPA) banned all uses of chlordane in 1983, except termite control. The EPA banned all uses of chlordane in 1988.[3] The EPA recommends that children should not drink water with more than 60 parts of chlordane per billion parts of drinking water (60 ppb) for longer than 1 day. EPA has set a limit in drinking water of 2 ppb.

Chlordane is very persistent in the environment because it does not break down easily. It has an environmental half-life of 10 to 20 years.[4]

Origin, pathways of exposure, and processes of excretion

In the years 1948–1988 chlordane was a common pesticide for corn and citrus crops, as well as a method of home termite control.[5] Pathways of exposure to chlordane include ingestion of crops grown in chlordane-contaminated soil, inhalation of air near chlordane-treated homes and landfills, and ingestion of high-fat foods such as meat, fish, and dairy, as Chlordane builds up in fatty tissue.[6] The United States Environmental Protection Agency reported that over 30 million homes were treated with technical chlordane or technical chlordane with heptachlor. Depending on the site of home treatment, the indoor air levels of chlordane can still exceed the Minimal Risks Levels (MRLs) for both cancer and chronic disease by orders of magnitude.[7] Chlordane is excreted slowly through feces and urine elimination, as well as through breast milk in nursing mothers, and is able to cross the placenta and become absorbed by developing fetuses in pregnant women.[8] The breakdown products of chlordane, metabolite, oxychlordane accumulates in American's blood and adipose tissue with age [9]

Environmental impact

Being hydrophobic, chlordane adheres to soil particles and enters groundwater only slowly, owing to its low solubility (0.009 ppm). It degrades only over the course of years.[10] Chlordane bioaccumulates in animals. It is highly toxic to fish, with an LD50 of 0.022–0.095 mg/kg (oral).

Two components of the chlordane mixture, cis-nonachlor and trans-nonachlor, are the main bioaccumulating constituents.[2] trans-Nonachlor is more toxic than technical chlordane and cis-nonachlor is less toxic.[2] Oxychlordane (C10H4Cl8O) is the primary metabolite of chlordane.[2]

Chlordane is a known persistent organic pollutants (POP), classified among the "dirty dozen" and banned by the 2001 [[Stockholm Convention on Persistent Organic Pollutants].

Health effects

Exposure to chlordane metabolites may be associated with testicular cancer. The incidence of seminoma in men with the highest blood levels of cis-nonachlor was almost double that of men with the lowest levels.[11] Prostate cancer has been associated with trans-nonachlor levels, a component of chlordane.[12] Japanese workers who used chlordane over a long period of time had minor changes in liver function.[13]

Heptachlor and chlordane are some of the most potent carcinogens tested in animal models. No human epidemiological study has been conducted to determine the relationship between levels of chlordane/heptachlor in indoor air and rates of cancer in inhabitants. However, studies have linked chlordane/heptachlor in human tissues with cancers of the breast, prostate, brain, and cancer of blood cells—leukemia and lymphoma.[14][15] Breathing chlordane in indoor air is the main route of exposure for these levels in human tissues. Currently, USEPA has defined a concentration of 24 nanogram per cubic meter of air (ng/M3) for chlordane compounds over a 20-year exposure period as the concentration that will increase the probability of cancer by 1 in 1,000,000 persons. This probability of developing cancer increases to 10 in 1,000,000 persons with an exposure of 100 ng/M3 and 100 in 1,000,000 with an exposure of 1000 ng/M3.[16]

The non-cancer health effects of chlordane compounds, which include diabetes, insulin resistance, migraines, respiratory infections, diabetes, immune-system activation, anxiety, depression, blurry vision, confusion, intractable seizures as well as permanent neurological damage,[17] probably affect more people than cancer. The Agency for Toxic Substances and Disease Registry (ATSDR) has defined a concentration of chlordane compounds of 20 ng/M3 as the Minimal Risk Level (MRLs). ATSDR defines Minimal Risk Level as an estimate of daily human exposure to a dose of a chemical that is likely to be without an appreciable risk of adverse non-cancerous effects over a specific duration of exposure.[18] Recent results from 8 large epidemiological studies in the United States, using CDC's NHANES data, have consistently shown of all the chemicals found in the blood of Americans, heptachlor epoxides and oxychlordane have the highest associated risk with insulin resistance and diabetes.[19][20][21]

Remediation

Chlordane was applied under the home/building during treatment for termites and the half-life can be up to 30 years. Chlordane has a low vapor pressure and volitizes slowly into the air of home/building above. To remove chlordane from indoor air requires either ventilation (Heat Exchange Ventilation) or activated carbon filtration. Chemical remediation of chlordane in soils was attempted by the US Army Corps of Engineers by mixing chlordane with aqueous lime and persulfate. In a phytoremediation study, Kentucky bluegrass and Perennial ryegrass were found to be minimally affected by chlordane, and both were found to take it up into their roots and shoots.[22] Mycoremediation of chlordane in soil have found that contamination levels were reduced.[22] The fungi species Phanerochaete chrysosporium has been studied, and were found to reduce concentrations by 21% in water in 30 days and in solids in 60 days.[23]

References

  1. ^ a b Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263
  2. ^ a b c d Bondy, G. S.; Newsome, WH; Armstrong, CL; Suzuki, CA; Doucet, J; Fernie, S; Hierlihy, SL; Feeley, MM; Barker, MG (2000). "Trans-Nonachlor and cis-Nonachlor Toxicity in Sprague-Dawley Rats: Comparison with Technical Chlordane". Toxicological Sciences. 58 (2): 386–98. doi:10.1093/toxsci/58.2.386. PMID 11099650. {{cite journal}}: Invalid |display-authors=9 (help)
  3. ^ Pesticides and Breast Cancer Risk: Chlordane, Fact Sheet #11, March 1998, Program on Breast Cancer and Environmental Risk Factors Cornell University
  4. ^ Bennett, G. W., Ballee, D. L., Hall, R. C., Fahey, J. F., Butts, W. L., and Osmun, J. V. (1974). "Persistence and distribution of chlordane and dieldrin applied as termiticides". Bull. Environ. Contam. Toxicol. 11 (1): 64–9. doi:10.1007/BF01685030. PMID 4433785.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Agency for Toxic Substances & Disease Registry (ATSDR). Toxic Substances Portal: Chlordane. Last updated September, 2010 [online]. Available at URL: http://www.atsdr.cdc.gov/substances/toxsubstance.asp?toxid=62
  6. ^ Agency for Toxic Substances & Disease Registry (ATSDR). ToxFaqs: September, 1995. Available at URL: http://www.atsdr.cdc.gov/toxfaqs/tfacts31.pdf
  7. ^ R. W. Whitmore, et al. (1994). Non-occupational exposures to pesticides for residents of two U.S. cities. Archives of Environmental Contamination and Toxicology. 26: 47-59.
  8. ^ Center for Disease Control and Prevention (CDC). National Report on Human Exposure to Environmental Chemicals: Chemical Information: Chlordane. Last updated November, 2010 [online].
  9. ^ D. Lee, et al. (2007). Association between serum concentrations of persistent organic pollutants and insulin resistance among nondiabetic adults: Results from the National Health and Nutrition Examination Survey. Diabetic Care. 30:622-628.
  10. ^ http://organic.com.au/pesticides/Chlorodane/
  11. ^ McGlynn, Katherine A.; Quraishi, Sabah M.; Weber, JP; Rubertone, MV; Erickson, RL; et al. (April 29, 2008). "Persistent Organochlorine Pesticides and Risk of Testicular Germ Cell Tumors". Journal of the National Cancer Institute. 100 (9): 663–71. doi:10.1093/jnci/djn101. PMID 18445826Template:Inconsistent citations {{cite journal}}: Explicit use of et al. in: |last3= (help)CS1 maint: postscript (link).
  12. ^ http://www.ehponline.org/members/2009/0900919/0900919.pdf doi:10.1289/ehp.0900919
  13. ^ http://www.atsdr.cdc.gov/tfacts31.html
  14. ^ Cassidy, R.A., et al, (2005). The Link Between the Insecticide Heptachlor Epoxide, Estradiol, and Breast Cancer. Breast Cancer Research and Treatment. 90:55-64
  15. ^ Richard A. Cassidy. 2010. Cancer and chlordane-treated homes: a pinch of prevention is worth a pound of cure. Leukemia & Lymphoma. 51:1368-1369
  16. ^ http://www.epa.gov/iris/subst/0142.htm
  17. ^ http://www.atsdr.cdc.gov/mmg/mmg.asp?id=349&tid=62
  18. ^ http://www.atsdr.cdc.gov/toxprofiles/tp31.html
  19. ^ D. Lee, et al. (2006). A strong dose-response relation between serum concentrations of persistent organic pollutants and diabetes. Diabetes Care. 29:1638-1644.
  20. ^ C. J. Patel, et al. (2010). An Environment-Wide Association Study (EWAS) on type 2 diabetes mellitus. Plos One 5(5);e10746. doi:10137.
  21. ^ C. J. Everett, et al. (2010). Biomarkers of pesticide exposure and diabetes in the 1999-2004 National Health and Nutrition Examination Survey. Environment International. 36:398-401
  22. ^ a b Medina, Victor F. "Legacy Chlordane in Soils from Housing Areas Treated with Organochlorine Pesticides" (PDF). US Army Corps of Engineers. Retrieved 10 October 2012. {{cite web}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  23. ^ Kennedy, D.W. (1990). "Comparative biodegradation of alkyl halide insecticides by the White Rot fungus, Phanerochaete chrysosporium". Appl. Environ. Microbiol. 56:2347–2353. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

External links

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