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Chlordecone

From Wikipedia, the free encyclopedia
(Redirected fromKepone)
This article is about the pesticide. For the indie rock band, seeKepone (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 InfoCard100.005.093Edit 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 mass490.633 g/mol
Appearancetan to white crystalline solid
Odorodorless
Density1.6 g/cm3
Melting point349 °C (660 °F; 622 K) (decomposes)
0.27 g/100 mL
Solubilitysoluble inacetone,ketone,acetic acid
slightly soluble inbenzene,hexane
logP5.41
Vapor pressure3.10−7 kPa
Thermochemistry
764 J/K mol
−225.9 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
carcinogen[2]
Flash pointNon-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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Chlordecone, better known in the United States under the brand nameKepone, is anorganochlorine compound and a colourless solid. It is an obsoleteinsecticide, now prohibited in the Western world, but only after many thousands of tonnes had been produced and used.[3] Chlordecone is a knownpersistent organic pollutant that was banned globally by theStockholm Convention on Persistent Organic Pollutants in 2009.[4]

Synthesis

[edit]

Chlordecone is made by dimerizinghexachlorocyclopentadiene andhydrolyzing to aketone.[5]

It is also the main degradation product ofmirex.[3]

History

[edit]

In the U.S., chlordecone, commercialized under the brand name "Kepone", was produced byAllied Signal Company and LifeSciences Product Company inHopewell, Virginia. The improper handling and dumping of the substance (including the waste materials generated in its manufacturing process) into the nearbyJames River (U.S.) in the 1960s and 1970s drew national attention to its toxic effects on humans and wildlife. After two physicians, Dr. Yi-nan Chou and Dr. Robert S. Jackson of the Virginia Health Department, notified the Centers for Disease Control that employees of the company had been found to have toxic chemical poisoning, LifeSciences voluntarily closed its plant on 4 July 1975, and cleanup of the contamination began and a 100-mile section of the James River was closed to fishing while state health officials looked for other persons who might have been injured.[6] At least 29 people in the area were hospitalized as a result of their exposure to Kepone.[6]

The product is made in aDiels-Alder reaction shared with pesticides likechlordane andendosulfan.[3] Chlordecone is cited amongst a handful of other noxious substances as the driver forGerald Ford's approval of theToxic Substances Control Act in 1976, a United States regulatory bill that was controversial due to the financial burden it put on chemical production companies to get approval for new compounds.[7]

Regulation

[edit]

In the US, Chlordecone was not federally regulated until after the Hopewell disaster, in which 29 factory workers were hospitalized with various ailments, includingneurological.[8]

In France it was banned on the mainland only, in 1993.[9]

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

On 14 March 2024, theFrench National Assembly assumed responsibility for the chlordecone contamination affecting populations in Martinique and Guadeloupe.[10]

Toxicology

[edit]

Chlordecone can accumulate in the liver and the distribution in the human body is regulated by binding of the pollutant or its metabolites tolipoproteins likeLDL andHDL.[11] The LC50 (LC = lethal concentration) is 35 μg/ L forEtroplus maculatus,[12] 22–95 μg/kg forblue gill andtrout. Chlordeconebioaccumulates in animals by factors up to a million-fold.

Workers with repeated exposure suffer severeconvulsions resulting from degradation of thesynaptic junctions.[3]

Chronic low level exposure appears to causeprostate cancer in men,[13] and "significant excesses of deaths were observed forstomach cancer in women andpancreatic cancer in women".[14]

Chlordecone has been found to act as anagonist of theGPER (GPR30), which interacts strongly with theestrogen sex hormoneestradiol.[15]

Incidents

[edit]

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

James River estuary

[edit]

In July 1975,[16]Virginia GovernorMills Godwin Jr. shut down theJames River to fishing for 100 miles, fromRichmond to theChesapeake Bay.[8] This ban remained in effect for 13 years, until efforts to clean up the river began to show results.[17]

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 suedAllied Chemical in federal district court (Eastern District of Virginia), claiming special economic damages from Allied's negligent damage to the fish and wildlife.[18] 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

[edit]

The French islands ofMartinique andGuadeloupe are heavily contaminated with chlordecone,[19] following years of its massive and unrestricted use on banana plantations: primarily againstCosmopolites sordidus.[20][21] Despite a 1990 ban on the substance in mainland France, the economically powerful banana planters lobbied intensively to obtain a waiver to keep using Kepone until 1993. They argued that no alternative pesticide was available, which has since been disputed. After 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 states that after the 1993 ban was imposed, the chemical was illegally imported to the islands under the name Curlone, and continued to be used for many years.[9] Since 2003, local authorities in the two islands have restricted the cultivation of various food crops because thesoil is badly contaminated by chlordecone. A 2018 large-scale study by the French public health agency,Santé publique France, shows that 95% of the inhabitants of Guadeloupe and 92% of those of Martinique are contaminated by the chemical.[22] Guadeloupe has one of the highestprostate cancer diagnosis rates in the world.[23]

References

[edit]
  1. ^IUPAC Agrochemical information.
  2. ^abcdeNIOSH Pocket Guide to Chemical Hazards."#0365".National Institute for Occupational Safety and Health (NIOSH).
  3. ^abcdRobert L. Metcalf "Insect Control" inUllmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Wienheim, 2002.doi:10.1002/14356007.a14_263
  4. ^abPress 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. ^Survey of Industrial Chemistry by Philip J. Chenier (2002), p. 484.
  6. ^ab"Two young doctors stopped the spread of Kepone poisoning", by Bill McAllister, L.A. Times-Washington Post Service, reprinted inCourier-Journal (Louisville KY), 5 January 1976, p. 1
  7. ^Hanson, David J. (15 January 2007)."Those Were The Days".Chemical & Engineering News.85 (3). American Chemical Society.doi:10.1021/cen-v085n003.p044.
  8. ^abRichard Foster,Kepone: The 'Flour' Factory,Richmond Magazine (8 July 2005).
  9. ^ab"N° 2430 – Rapport d'information sur l'utilisation du chlordécone et des autres pesticides dans l'agriculture martiniquaise et guadeloupéenne (M. Philippe-Edmond Mariette, Président, et M. Joël Beaugendre, Rapporteur)".assemblee-nationale.fr. Retrieved7 June 2024.Rapport d'information (...) sur l'utilisation du chlordécone et des autres pesticides dans l'agriculture martiniquaise et guadeloupéenne.
  10. ^Resiere, Dabor; Lapostolle, Fréderic; Florentin, Jonathan; Banydeen, Rishika; Gueye, Papa; Pujo, Jean; Mégarbane, Bruno; Kallel, Hatem; Névière, Rémi (June 2024)."A health strategy for chlordecone (Kepone) exposure in the French Territories of America".The Lancet.403 (10443):2481–2482.doi:10.1016/s0140-6736(24)00883-3.ISSN 0140-6736.
  11. ^Delannoy, Matthieu; Girardet, Jean-Michel; Djelti, Fathia; Yen, Frances T.; Cakir-Kiefer, Céline (1 November 2020)."Affinity of chlordecone and chlordecol for human serum lipoproteins"(PDF).Environmental Toxicology and Pharmacology.80 103486.Bibcode:2020EnvTP..8003486D.doi:10.1016/j.etap.2020.103486.PMID 32891758.S2CID 221523766.
  12. ^Asifa, K. P.; Chitra, K. C. (2013)."Determination of median lethal concentration (LC50) and behavioral effects of chlordecone in the cichlid fish, Etroplus maculatus"(PDF).International Journal of Science and Research.4 (3):1473–1475.
  13. ^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.
  14. ^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.Bibcode:2020ESPR...2741014L.doi:10.1007/s11356-019-06481-4.PMID 31621027.S2CID 204707528.
  15. ^Prossnitz, Eric R.; Barton, Matthias (May 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.PMC 4040308.PMID 24530924.
  16. ^SUGAWARA, SANDRA (25 October 1985)."Virginia's James River Still Is Choked With Pesticide Contamination".Los Angeles Times. The Washington Post.
  17. ^Jack Cooksey, "What's in the Water?",Richmond Magazine, June 2007. Retrieved 13 June 2012.
  18. ^Pruitt v. Allied Chemical Corp.,523 F. Supp. 975 (E.D. Va. 1981).
  19. ^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.Bibcode:2013ChEnJ.229..239D.doi:10.1016/j.cej.2013.03.036.
  20. ^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
  21. ^Agard-Jones, Vanessa (1 November 2013). "Bodies in the System".Small Axe.17 (3(42)):182–192.doi:10.1215/07990537-2378991.S2CID 145642259.
  22. ^Chlordécone : les Antilles empoisonnées pour des générations, Le Monde, 6 June 2018.
  23. ^"France: Island Paradise With Contaminated Drinking Water".European Journal.Deutsche Welle. 26 May 2010. Archived fromthe original on 27 May 2010.

External links

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