Chlordecone: Difference between revisions

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			{{Use dmy dates\|date=February 2020}}
	{{About\|the pesticide\|the indie rock band\|Kepone (band)}}		{{About\|the pesticide\|the indie rock band\|Kepone (band)}}
	{{chembox		{{chembox
			\| Verifiedfields = changed
	\| verifiedrevid = 402193161
			\| Watchedfields = changed
			\| verifiedrevid = 415672056
	\| ImageFile = Chlordecone.png		\| ImageFile = Chlordecone.png
	\| ImageSize = 120px		\| ImageSize = 120px
			\| ImageClass = skin-invert
	\| ImageFile2 = Chlordecone Kepone 3D.png		\| ImageFile2 = Chlordecone Kepone 3D.png
	\| ImageSize2 = 120px		\| ImageSize2 = 120px
			\| IUPACName = decachloropentacyclodecan-5-one<ref></ref>
	\| IUPACName = 1,1a,3,3a,4,5,5,5a,5b,6-Decachlorooctahydro-2''H''-1,3,4-(methanetriyl)cyclobutapentalen-2-one
	\| OtherNames = Chlordecone<br>Clordecone<br>Merex		\| OtherNames = Chlordecone<br>Clordecone<br>Merex<br />
			CAS name: <small>1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobutapentalen-2-one</small>
	\| Section1 = {{Chembox Identifiers
			\|Section1={{Chembox Identifiers
	\| KEGG = C01792
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| KEGG = C01792
	\| 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		\| 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
	\| InChIKey = LHHGDZSESBACKH-UHFFFAOYAM		\| InChIKey = LHHGDZSESBACKH-UHFFFAOYAM
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 462576		\| ChEMBL = 462576
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
Line 19:		Line 26:
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 143-50-0		\| CASNo = 143-50-0
	\| PubChem = 299		\| PubChem = 299
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 293		\| ChemSpiderID = 293
			\| UNII_Ref = {{fdacite\|changed\|FDA}}
	\| SMILES = ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl
			\| UNII = RG5XJ88UDF
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 16548
			\| EINECS = 205-601-3
			\| SMILES = ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| C = 10 \| Cl = 10 \| O= 1		\| C=10 \| Cl=10 \| O=1
	\| MolarMass = 490.633 g/mol		\| MolarMass = 490.633 g/mol
	\| Appearance =		\| Appearance = tan to white crystalline solid
	\| Density = 1.6 g/cm<sup>3</sup>		\| Odor = odorless
			\| Density = 1.6 g/cm<sup>3</sup>
	\| ~~MeltingPt~~ =		\| MeltingPtC = 349
			\| MeltingPt_notes = (decomposes)
	\| BoilingPt =
	\| ~~Solubility~~ =		\| BoilingPt =
			\| Solubility = 0.27 g/100 mL
			\| SolubleOther = soluble in ], ], ] <br> slightly soluble in ], ]
			\| LogP = 5.41
			\| VaporPressure = 3.10<sup>−7</sup> kPa
	}}		}}
	\| ~~Section3~~ = {{Chembox ~~Hazards~~		\|Section4={{Chembox Thermochemistry
			\| DeltaHf = -225.9 kJ/mol
	\| MainHazards =
	\| ~~FlashPt~~ =		\| Entropy = 764 J/K mol
			}}
	\| Autoignition =
			\|Section7={{Chembox Hazards
			\| MainHazards = carcinogen<ref name=PGCH/>
			\| FlashPt_notes = Non-flammable<ref name=PGCH/>
			\| AutoignitionPtC =
			\| LD50 = 95 mg/kg (rat, oral)
			\| PEL = none<ref name=PGCH>{{PGCH\|0365}}</ref>
			\| IDLH = N.D.<ref name=PGCH/>
			\| REL = Ca TWA 0.001 mg/m<sup>3</sup><ref name=PGCH/>
	}}		}}
	}}		}}

			'''Chlordecone''', better known in the United States under the brand name '''Kepone''', is an ] and a colourless solid. It is an obsolete ], now prohibited in the western world, but only after many thousands of tonnes had been produced and used.<ref name=Ullmann2>Robert L. Metcalf "Insect Control" in ''Ullmann's Encyclopedia of Industrial Chemistry'' Wiley-VCH, Wienheim, 2002. {{doi\|10.1002/14356007.a14_263}}</ref> Chlordecone is a known ] that was banned globally by the ] in 2009.<ref name="COP4, 2009 Press release">, 2009.</ref>
	'''Kepone''', also known as '''chlordecone''', is a ]ic<ref></ref> ] related to ], used between 1966 and 1975 in the USA for ant and ]s.

			==Synthesis==
	== Chemistry and toxicology ==
			Chlordecone is made by dimerizing ] and ] to a ].<ref>Survey of Industrial Chemistry by Philip J. Chenier (2002), p. 484.</ref>
	Chemically, kepone is a ] polycyclic ] insecticide and ] with the chemical formula {{Carbon}}<sub>10</sub>{{Chlorine}}<sub>10</sub>{{Oxygen}}. The dry powder is readily absorbed through the skin and respiratory tract. Some unprotected production workers exposed to kepone powder suffered tremors, jerky eye movements, memory loss, headaches, slurred speech, unsteadiness, lack of coordination, loss of weight, rash, enlarged liver, decreased libido, sterility, chest pain, arthralgia, and the increased risk of developing cancer.{{Citation needed\|date=October 2009}} Kepone persists in the environment, with a half-life of about 30 years.

			It is also the main degradation product of ].<ref name=Ullmann2/>

	== History ==		== History ==
			In the U.S., chlordecone, commercialized under the brand name "Kepone", was produced by ] and LifeSciences Product Company in ]. The improper handling and dumping of the substance (including the waste materials generated in its manufacturing process) into the nearby ] (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 July 4, 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. <ref name=McAllister>"Two young doctors stopped the spread of Kepone poisoning", by Bill McAllister, L.A. Times-Washington Post Service, reprinted in ''Courier-Journal'' (Louisville KY), January 5, 1976, p. 1</ref> At least 29 people in the area were hospitalized as a result of their exposure to Kepone. <ref name=McAllister/>
	Kepone was produced by ] in ] and caused a nationwide pollution controversy due to improper handling and dumping of the substance into the nearby ].<ref></ref> In the United States, its use was banned in 1975. In 2009, kepone was included in the ], which bans its production and use worldwide.<ref>]: , respekt.cz, 10.5.2009</ref>

			The product is made in a ] reaction shared with pesticides like ] and ].<ref name=Ullmann2/> Chlordecone is cited amongst a handful of other noxious substances as the driver for ]'s half-hearted approval in 1976 of the ], which "remains one of the most controversial regulatory bills ever passed".<ref name="hanson07">{{cite journal \|last1=Hanson \|first1=David J. \|title=Those Were The Days \|journal=Chemical & Engineering News \|date=15 January 2007 \|volume=85 \|issue=3 \|url=https://cen.acs.org/articles/85/i3/Those-Days.html \|publisher=American Chemical Society\|doi=10.1021/cen-v085n003.p044 }}</ref>
	In July 2003, a ''Richmond Magazine'' article chronicled the effects on Allied Signal employees and described how ] and CBS's ] brought nationwide attention to the problem.<ref></ref>

			==Regulation==
	Due to the pollution scare, many businesses and restaurants along the river suffered, and then-Governor ] shut down the James River to fishing from ] to the ].
			In the US, Chlordecone was not federally regulated until after the Hopewell disaster, in which 29 factory workers were hospitalized with various ailments, including ].<ref name=foster05>Richard Foster, , ''Richmond Magazine'' (July 8, 2005).</ref>

			In France it was banned on the mainland only, in 1993.<ref name="rapport"/>
	== French Antilles ==

			In 2009, chlordecone was included in the ], which bans its production and use worldwide.<ref name= "COP4, 2009 Press release"/>
	The French island of ] is heavily contaminated with kepone,<ref></ref> following years of unrestricted (including spray planes) use on ] plantations. Despite a 1990 ban of the substance by France, the island was, after intensive lobbying by the economically powerful ] community, allowed to continue using kepone until 1993, under the since disputed argument that no alternative pesticide was available. Similarly, the nearby island of ] is also contaminated, but to a lesser extent. Since 2003, the local authorities restricted cultivation of crops because the soil has been seriously contaminated by kepone. That may correlate with the fact that Guadeloupe has one of the highest prostate cancer rates in the world.<ref>European Journal, ], 26 May, 2010.</ref>

			On March 14, 2024, the ] assumed responsibility for the chlordecone contamination affecting populations in Martinique and Guadeloupe.<ref>{{Cite journal \|last=Resiere \|first=Dabor \|last2=Lapostolle \|first2=Fréderic \|last3=Florentin \|first3=Jonathan \|last4=Banydeen \|first4=Rishika \|last5=Gueye \|first5=Papa \|last6=Pujo \|first6=Jean \|last7=Mégarbane \|first7=Bruno \|last8=Kallel \|first8=Hatem \|last9=Névière \|first9=Rémi \|date=June 2024 \|title=A health strategy for chlordecone (Kepone) exposure in the French Territories of America \|url=https://doi.org/10.1016/S0140-6736(24)00883-3 \|journal=The Lancet \|volume=403 \|issue=10443 \|pages=2481–2482 \|doi=10.1016/s0140-6736(24)00883-3 \|issn=0140-6736}}</ref>
	== In popular culture ==

			== Toxicology ==
	* ] was the name of an American indie rock band from Richmond, Virginia. Formed in 1991, the band's name is derived from the kepone crisis that occurred in the Richmond area in the 1970s. It was originally formed as a sideproject of Michael Bishop, ex-bassist of ].
			Chlordecone can accumulate in the liver and the distribution in the human body is regulated by binding of the pollutant or its metabolites to ] like ] and ].<ref>{{cite journal \|last1=Delannoy \|first1=Matthieu \|last2=Girardet \|first2=Jean-Michel \|last3=Djelti \|first3=Fathia \|last4=Yen \|first4=Frances T. \|last5=Cakir-Kiefer \|first5=Céline \|title=Affinity of chlordecone and chlordecol for human serum lipoproteins \|journal=Environmental Toxicology and Pharmacology \|date=1 November 2020 \|volume=80 \|pages=103486 \|doi=10.1016/j.etap.2020.103486 \|pmid=32891758 \|s2cid=221523766 \|url=https://hal.univ-lorraine.fr/hal-02925906/file/Delannoy%20et%20al.%20draft%20sent%20to%20editorial%20preprint%281%29.pdf }}</ref> The LC<sub>50</sub> (LC = lethal concentration) is 35 μg/ L for '']'',<ref>{{cite journal \|last1=Asifa \|first1=K. P. \|last2=Chitra \|first2=K. C. \|year=2013 \|title=Determination of median lethal concentration (LC50) and behavioral effects of chlordecone in the cichlid fish, Etroplus maculatus \|journal=International Journal of Science and Research \|volume=4 \|issue=3 \|pages=1473–1475 \|url=https://www.ijsr.net/archive/v4i3/SUB152402.pdf }}</ref> 22–95 μg/kg for ] and ]. Chlordecone ]s in animals by factors up to a million-fold.

			Workers with repeated exposure suffer severe ] resulting from degradation of the ].<ref name=Ullmann2/>
	* The ] recorded a song named "Kepone Factory", deliberately referring to the chemical compound kepone, for their 1981 album '']''. The song was written in 1978 and was performed live despite not appearing on any recording until 1981.

			Chronic low level exposure appears to cause ] in men,<ref name="multigner16">{{cite journal \|doi=10.1016/j.purol.2015.08.080\|title=Exposition au chlordécone et cancer de la prostate. Interactions avec les gènes codants pour les œstrogènes\|year=2015\|last1=Brureau\|first1=L.\|last2=Emeville\|first2=E.\|last3=Ferdinand\|first3=S.\|last4=Thome\|first4=J.\|last5=Romana\|first5=M.\|last6=Blanchet\|first6=P.\|last7=Multigner\|first7=L.\|journal=Progrès en Urologie\|volume=25\|issue=13\|page=755\|pmid=26544275}}</ref> and "significant excesses of deaths were observed for ] in women and ] in women".<ref name="multigner20">{{cite journal \|doi=10.1007/s11356-019-06481-4\|title=A cohort study of banana plantation workers in the French West Indies: First mortality analysis (2000–2015)\|year=2020\|last1=Luce\|first1=Danièle\|last2=Dugas\|first2=Julien\|last3=Vaidie\|first3=Amandine\|last4=Michineau\|first4=Léah\|last5=El-Yamani\|first5=Mounia\|last6=Multigner\|first6=Luc\|journal=Environmental Science and Pollution Research\|volume=27\|issue=33\|pages=41014–41022\|pmid=31621027\|s2cid=204707528\|url=https://hal-univ-rennes1.archives-ouvertes.fr/hal-02355983/file/Luce2019_ESPR.pdf}}</ref>
	* A history of kepone incidents is featured in the book "Who's Poisoning America?: Corporate Polluters and Their Victims in the Chemical Age", by Ralph Nader (Editor), Ronald Brownstein (Editor), John Richard (Editor), Publisher: Random House, Incorporated 1982. ISBN: 0871562766. ISBN-13: 9780871562760

			Chlordecone has been found to act as an ] of the ] (GPR30), which interacts strongly with the ] sex hormone ].<ref name="ProssnitzBarton2014">{{cite journal \|last1=Prossnitz \|first1=Eric R. \|last2=Barton \|first2=Matthias \|title=Estrogen biology: New insights into GPER function and clinical opportunities \|journal=Molecular and Cellular Endocrinology \|date=May 2014 \|volume=389 \|issue=1–2 \|pages=71–83 \|doi=10.1016/j.mce.2014.02.002 \|pmid=24530924 \|pmc=4040308 }}</ref>

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

			=== James River estuary ===
			In July 1975,<ref name="ssv">{{cite news \|last1=SUGAWARA \|first1=SANDRA \|title=Virginia's James River Still Is Choked With Pesticide Contamination \|url=https://www.latimes.com/archives/la-xpm-1985-10-25-mn-14199-story.html \|agency=Washington Post \|work=Los Angeles Times \|date=25 October 1985}}</ref> ] Governor ] shut down the ] to fishing for 100 miles, from ] to the ].<ref name=foster05/> This ban remained in effect for 13 years, until efforts to clean up the river began to show results.<ref name="Cooksey">, ''Richmond Magazine'', June 2007. Retrieved 13 June 2012.</ref>

			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 ] in federal district court (]), claiming special economic damages from Allied's negligent damage to the fish and wildlife.<ref>''Pruitt v. Allied Chemical Corp.'', (E.D. Va. 1981).</ref> 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 ] and ] are heavily contaminated with chlordecone,<ref>{{cite journal \| author = Durimel A.\|display-authors=etal \| year = 2013 \| title = pH dependence of chlordecone adsorption on activated carbons and role of adsorbent physico-chemical properties \| journal = Chemical Engineering Journal \| volume = 229 \| pages = 239–349 \| doi=10.1016/j.cej.2013.03.036}}</ref> following years of its massive and unrestricted use on banana plantations.<ref>{{cite journal \|last1=Wong \|first1=Alfred \|last2=Ribero \|first2=Christine \|title=Alternative Agricultural Cropping Options for Chlordecone-Polluted Martinique \|journal=Études Caribéennes \|date=26 March 2014 \|issue=26 \|doi=10.4000/etudescaribeennes.6710\|doi-access=free }}{{open access}}</ref><ref>{{Cite journal\|title = Bodies in the System\|journal =]\|date = 1 November 2013 \|pages = 182–192\|volume = 17\|issue = 3(42)\|doi = 10.1215/07990537-2378991\|first = Vanessa\|last = Agard-Jones\|s2cid =145642259}}</ref> 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.<ref name="rapport">{{Cite web \|title=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) \|url=https://www.assemblee-nationale.fr/12/rap-info/i2430.asp \|access-date=2024-06-07 \|website=www.assemblee-nationale.fr}}</ref> Since 2003, local authorities in the two islands have restricted the cultivation of various food crops because the ] 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.<ref>, Le Monde, 6 June 2018.</ref> Guadeloupe has one of the highest ] diagnosis rates in the world.<ref>{{cite news \|title=France: Island Paradise With Contaminated Drinking Water \|url=http://www.dw-world.de/dw/episode/0,,5542822,00.html \|work=European Journal \|publisher=] \|date=26 May 2010 \|archiveurl=https://web.archive.org/web/20100527120102/http://www.dw-world.de/dw/episode/0,,5542822,00.html \|archivedate=27 May 2010}}</ref>

			== In popular culture ==
			* ] was the name of an American indie rock band from ] formed in 1991.
			* The ] recorded a song named "Kepone Factory", a satire of the controversy surrounding Allied Signal and their negligence regarding employee safety, for their 1981 album '']''.

	==References==		==References==
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	{{~~insecticides~~}}		{{Insecticides}}
			{{Xenoestrogens}}
			{{Estrogen receptor modulators}}

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Latest revision as of 00:12, 17 December 2024

This article is about the pesticide. For the indie rock band, see Kepone (band).

Chlordecone
Names


IUPAC name decachloropentacyclodecan-5-one
Other names Chlordecone Clordecone Merex CAS name: 1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobutapentalen-2-one
Identifiers
CAS Number	143-50-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16548
ChEMBL	ChEMBL462576
ChemSpider	293
ECHA InfoCard	100.005.093
EC Number	205-601-3
KEGG	C01792
PubChem CID	299
UNII	RG5XJ88UDF
CompTox Dashboard (EPA)	DTXSID1020770
InChI 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)20Key: LHHGDZSESBACKH-UHFFFAOYSA-N 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)20Key: LHHGDZSESBACKH-UHFFFAOYAM
SMILES ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl
Properties
Chemical formula	C₁₀Cl₁₀O
Molar mass	490.633 g/mol
Appearance	tan to white crystalline solid
Odor	odorless
Density	1.6 g/cm
Melting point	349 °C (660 °F; 622 K) (decomposes)
Solubility in water	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 kPa
Thermochemistry
Std molar entropy (S₂₉₈)	764 J/K mol
Std enthalpy of formation (Δ_fH₂₉₈)	-225.9 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	carcinogen
Flash point	Non-flammable
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	95 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	Ca TWA 0.001 mg/m
IDLH (Immediate danger)	N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Chlordecone, better known in the United States under the brand name Kepone, is an organochlorine compound and a colourless solid. It is an obsolete insecticide, now prohibited in the western world, but only after many thousands of tonnes had been produced and used. Chlordecone is a known persistent organic pollutant that was banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.

Synthesis

Chlordecone is made by dimerizing hexachlorocyclopentadiene and hydrolyzing to a ketone.

It is also the main degradation product of mirex.

History

In the U.S., chlordecone, commercialized under the brand name "Kepone", was produced by Allied Signal Company and LifeSciences Product Company in Hopewell, Virginia. The improper handling and dumping of the substance (including the waste materials generated in its manufacturing process) into the nearby James 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 July 4, 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. At least 29 people in the area were hospitalized as a result of their exposure to Kepone.

The product is made in a Diels-Alder reaction shared with pesticides like chlordane and endosulfan. Chlordecone 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".

Regulation

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

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

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

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

Toxicology

Chlordecone can accumulate in the liver and the distribution in the human body is regulated by binding of the pollutant or its metabolites to lipoproteins like LDL and HDL. The LC₅₀ (LC = lethal concentration) is 35 μg/ L for Etroplus maculatus, 22–95 μg/kg for blue gill and trout. Chlordecone bioaccumulates in animals by factors up to a million-fold.

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

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

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

Incidents

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

James River estuary

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

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. 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 chlordecone, following years of its massive and unrestricted use on banana plantations. 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. Since 2003, local authorities in the two islands have restricted the cultivation of various food crops because the soil 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. Guadeloupe has one of the highest prostate cancer diagnosis rates in the world.

In popular culture

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..

References

IUPAC Agrochemical information.
^ NIOSH Pocket Guide to Chemical Hazards. "#0365". National Institute for Occupational Safety and Health (NIOSH).
^ Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
^ 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.
Survey of Industrial Chemistry by Philip J. Chenier (2002), p. 484.
^ "Two young doctors stopped the spread of Kepone poisoning", by Bill McAllister, L.A. Times-Washington Post Service, reprinted in Courier-Journal (Louisville KY), January 5, 1976, p. 1
Hanson, David J. (15 January 2007). "Those Were The Days". Chemical & Engineering News. 85 (3). American Chemical Society. doi:10.1021/cen-v085n003.p044.
^ Richard Foster, Kepone: The 'Flour' Factory, Richmond Magazine (July 8, 2005).
^ "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)". www.assemblee-nationale.fr. Retrieved 7 June 2024.Rapport d'information (...) sur l'utilisation du chlordécone et des autres pesticides dans l'agriculture martiniquaise et guadeloupéenne.
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.
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. doi:10.1016/j.etap.2020.103486. PMID 32891758. S2CID 221523766.
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.
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.
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.
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.
SUGAWARA, SANDRA (25 October 1985). "Virginia's James River Still Is Choked With Pesticide Contamination". Los Angeles Times. Washington Post.
Jack Cooksey, "What's in the Water?", Richmond Magazine, June 2007. Retrieved 13 June 2012.
Pruitt v. Allied Chemical Corp., 523 F. Supp. 975 (E.D. Va. 1981).
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.
Wong, Alfred; Ribero, Christine (26 March 2014). "Alternative Agricultural Cropping Options for Chlordecone-Polluted Martinique". Études Caribéennes (26). doi:10.4000/etudescaribeennes.6710.
Agard-Jones, Vanessa (1 November 2013). "Bodies in the System". Small Axe. 17 (3(42)): 182–192. doi:10.1215/07990537-2378991. S2CID 145642259.
Chlordécone : les Antilles empoisonnées pour des générations, Le Monde, 6 June 2018.
"France: Island Paradise With Contaminated Drinking Water". European Journal. Deutsche Welle. 26 May 2010. Archived from the original on 27 May 2010.

External links

v t e Pest control: Insecticides
Carbamates	Aldicarb Aminocarb Bendiocarb Butocarboxim Carbaryl Carbofuran Carbosulfan m-Cumenyl methylcarbamate Ethienocarb Fenobucarb Isoprocarb Methomyl Metolcarb Oxamyl Promecarb Propoxur
Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Cryolite Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green
Insect growth regulators	Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Noviflumuron Pyriproxyfen
Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Imidaclothiz Nitenpyram Nithiazine Paichongding Thiacloprid Thiamethoxam
Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene
Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Mipafox Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos R-16661 Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon
Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Fluvalinate Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin
Diamides	Chlorantraniliprole Cyantraniliprole Flubendiamide
Other chemicals	Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime) Pyridaben Pyriprole Sarolaner Adjuvants (Piperonyl butoxide, Sesamex) Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone Ryanodine Ryanodol
Metabolites	Oxon Malaoxon Paraoxon TCPy
Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Isaria fumosorosea Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paenibacillus popilliae Purpureocillium lilacinum Spinosad

Xenoestrogens

Phytoestrogens

Flavanones	Hesperetin Liquiritigenin Naringenin Pinocembrin
Flavones	Acacetin 7,8-Dihydroxyflavone Mirificin
Prenylflavonoids	8-Prenylnaringenin 6-Prenylnaringenin 8-Geranylnaringenin 6,8-Diprenylnaringenin Icaritin
Isoflavones	Biochanin A Daidzein Daidzin Formononetin Genistein Genistin Glycitein Ononin Prunetin Puerarin Tectorigenin
Isoflavanes	Equol (S-Equol) Glabridin
Dihydrochalcones	Phloretin Phlorizin
Isoflavenes	Glabrene
Coumestans	Coumestan Coumestrol Desmethylwedelolactone Wedelolactone
Lignans	Enterodiol Enterolactone
Flavonolignans	Silybin Cinchonain-Ib
Flavonols	Quercetin
Others	Deoxymiroestrol Miroestrol Resveratrol α-Isosparteine

Mycoestrogens

Derivatives	D-Penicillamine

Synthetic

Metalloestrogens

Aluminium
Antimony
Arsenite
Barium
Cadmium
Chromium
Cobalt
Copper
Lead
Mercury
Nickel
Selenite
Tin
Vanadate

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

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