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Chlordecone

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This article is about the pesticide. For the indie rock band, see Kepone (band).
Chlordecone
Names
IUPAC name
decachloropentacyclo[5.3.0.02.6.03.9.04.8]decan-5-one[1]
Other names
Chlordecone
Clordecone
Merex
CAS name: 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalen-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.093 Edit this at Wikidata
EC Number
  • 205-601-3
KEGG
UNII
  • InChI=1S/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20 checkY
    Key: LHHGDZSESBACKH-UHFFFAOYSA-N checkY
  • InChI=1/C10Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20
    Key: LHHGDZSESBACKH-UHFFFAOYAM
  • ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl
Properties
C10Cl10O
Molar mass 490.633 g/mol
Appearance tan to white crystalline solid
Odor odorless
Density 1.6 g/cm3
Melting point 349 °C (660 °F; 622 K) (decomposes)
0.27 g/100 mL
Solubility soluble in acetone, ketone, acetic acid
slightly soluble in benzene, hexane
log P 5.41
Vapor pressure 3.10−7 kPa
Thermochemistry
764 J/K mol
-225.9 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 carcinogen[2]
Flash point Non-flammable[2]
Lethal dose or concentration (LD, LC):
95 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 Ca TWA 0.001 mg/m3[2]
IDLH (Immediate danger)
 N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Kepone, also known as chlordecone, is an organochlorine compound and a colourless solid. This compound is an obsolete insecticide related to Mirex and DDT. Its use was so disastrous that it is now prohibited in the western world, but only after many thousands of tonnes had been produced.[3] Kepone is a known persistent organic pollutant (POP) that was banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.[4]

Toxicology

The LC50 (LC = lethal concentration) is 35 μg/ L for Etroplus maculatus,[5] 22–95 μg/kg for blue gill and trout. Kepone bioaccumulates in animals by factors up to a million-fold.

Workers with repeated exposure suffer severe convulsions resulting from degradation of the synaptic junctions.[3]

Chronic low level exposure appears to cause prostate cancer,[6] and "significant excesses of deaths were observed for stomach cancer in women and pancreatic cancer in women".[7]

Kepone has been found to act as an agonist of the GPER (GPR30), which interacts strongly with the estrogen sex hormone estradiol.[8]

History

In the US, kepone was produced by Allied Signal Company and LifeSciences Product Company in Hopewell, Virginia. The improper handling and dumping of the substance into the nearby James River (U.S.) in the 1960s and 1970s drew national attention to its toxic effects on humans and wildlife. The product is similar to DDT and is a degradation product of Mirex.[3] Kepone was not federally regulated until after the Hopewell disaster, in which 29 factory workers were hospitalized with various ailments, including neurological.[9] Kepone is cited amongst a handful of other noxious substances as the driver for Gerald Ford's half-hearted approval in 1976 of the Toxic Substances Control Act, which "remains one of the most controversial regulatory bills ever passed".[10]

The history of Kepone incidents are reviewed in Who's Poisoning America?: Corporate Polluters and Their Victims in the Chemical Age (1982).

In 2009, Kepone was included in the Stockholm Convention on Persistent Organic Pollutants, which bans its production and use worldwide.[4]

Case studies

James River estuary

In July 1975,[11] Virginia Governor Mills Godwin Jr. shut down the James River to fishing for 100 miles, from Richmond to the Chesapeake Bay.[9] This ban remained in effect for 13 years, until efforts to clean up the river began to show results.[12]

Due to the pollution risks, many fishermen, marinas, seafood businesses, and restaurants, along with their employees along the river suffered economic losses. In 1981, a large group of these entities sued Allied Chemical in federal district court (Eastern District of Virginia), claiming special economic damages from Allied's negligent damage to the fish and wildlife.[13] In a case that sometimes appears in law school courses on Remedies, the court rejected the traditional "economic-loss rule", which requires physical impact causing personal injury or property damage to receive economic damages, and instead allowed a limited group of the plaintiffs—the fishing boat owners, the marinas, and the bait and tackle shops—to recover economic damages from Allied Chemical.

French Antilles

The French islands of Martinique and Guadeloupe are heavily contaminated with kepone,[14] following years of its massive and unrestricted use on banana plantations.[15][16] Despite a 1990 ban of the substance by France, the economically powerful banana planters lobbied intensively to obtain a derogation to use kepone until 1993, arguing that no alternative pesticide was available, which has since been disputed. Following the 1993 ban, the banana planters were discreetly granted derogations to use their remaining stocks, and a 2005 report prepared by the French National Assembly stated that it seemed likely that the chemical, under the name Curlone, continued to be illegally imported and used for years, including on sweet potato crops.[17] Since 2003, local authorities have restricted cultivation of crops because the soil has been seriously contaminated by kepone. A large-scale study by the public health agency Santé publique France published in 2018 showed that 95% of the inhabitants of Guadeloupe and 92% of those of Martinique are contaminated by the chemical.[18] Guadeloupe has one of the highest prostate cancer diagnosis rates in the world.[19]

  • Kepone was the name of an American indie rock band from Richmond, Virginia formed in 1991.
  • The Dead Kennedys recorded a song named "Kepone Factory", a satire of the controversy surrounding Allied Signal and their negligence regarding employee safety, for their 1981 album In God We Trust, Inc..

Synthesis

Kepone is made by dimerizing hexachlorocyclopentadiene and hydrolyzing to a ketone.[20]

References

  1. ^ IUPAC Agrochemical information.
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0365". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b c Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
  4. ^ a b Press Release – COP4 – Geneva, 8 May 2009: Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty, 2009.
  5. ^ Asifa KP, Chitra KC. (2015). Determination of Median Lethal Concentration (LC50) and Behavioral Effects of Chlordecone in the Cichlid fish, Etroplus maculatus. Int J. Sci.Res.4 (3):1473–75
  6. ^ Brureau, L.; Emeville, E.; Ferdinand, S.; Thome, J.; Romana, M.; Blanchet, P.; Multigner, L. (2015). "Exposition au chlordécone et cancer de la prostate. Interactions avec les gènes codants pour les œstrogènes". Progrès en Urologie. 25 (13): 755. doi:10.1016/j.purol.2015.08.080. PMID 26544275.
  7. ^ Luce, Danièle; Dugas, Julien; Vaidie, Amandine; Michineau, Léah; El-Yamani, Mounia; Multigner, Luc (2020). "A cohort study of banana plantation workers in the French West Indies: First mortality analysis (2000–2015)" (PDF). Environmental Science and Pollution Research. 27 (33): 41014–41022. doi:10.1007/s11356-019-06481-4. PMID 31621027. S2CID 204707528.
  8. ^ Prossnitz, Eric R.; Barton, Matthias (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.
  9. ^ a b Richard Foster, Kepone: The 'Flour' Factory, Richmond Magazine (July 8, 2005).
  10. ^ Hanson, David J. (15 January 2007). "Those Were The Days". Chemical & Engineering News. 85 (3). American Chemical Society.
  11. ^ SUGAWARA, SANDRA (25 October 1985). "Virginia's James River Still Is Choked With Pesticide Contamination". Los Angeles Times. Washington Post.
  12. ^ Jack Cooksey, "What's in the Water?", Richmond Magazine, June 2007. Retrieved 13 June 2012.
  13. ^ Pruitt v. Allied Chemical Corp., 523 F. Supp. 975 (E.D. Va. 1981).
  14. ^ Durimel A.; et al. (2013). "pH dependence of chlordecone adsorption on activated carbons and role of adsorbent physico-chemical properties". Chemical Engineering Journal. 229: 239–349. doi:10.1016/j.cej.2013.03.036.
  15. ^ Wong, Alfred; Ribero, Christine (26 March 2014). "Alternative Agricultural Cropping Options for Chlordecone-Polluted Martinique". Études Caribéennes (26). doi:10.4000/etudescaribeennes.6710.Open access icon
  16. ^ Agard-Jones, Vanessa (1 November 2013). "Bodies in the System". Small Axe. 17 (3(42)): 182–192. doi:10.1215/07990537-2378991. ISSN 0799-0537. S2CID 145642259.
  17. ^ Rapport d'information (...) sur l'utilisation du chlordécone et des autres pesticides dans l'agriculture martiniquaise et guadeloupéenne.
  18. ^ Chlordécone : les Antilles empoisonnées pour des générations, Le Monde, 6 June 2018.
  19. ^ "France: Island Paradise With Contaminated Drinking Water". European Journal. Deutsche Welle. 26 May 2010. Archived from the original on 27 May 2010.
  20. ^ Survey of Industrial Chemistry by Philip J. Chenier (2002), p. 484.
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