| Revision as of 13:37, 1 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1 InChIKey1 SMILES.← Previous edit |
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{{Use dmy dates|date=February 2020}} |
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{{About|the pesticide|the indie rock band|Kepone (band)}} |
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{{About|the pesticide|the indie rock band|Kepone (band)}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 290070010 |
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| Watchedfields = changed |
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| verifiedrevid = 415672056 |
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| ImageFile = Chlordecone.png |
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| ImageFile = Chlordecone.png |
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| ImageSize = 120px |
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| ImageSize = 120px |
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| ImageClass = skin-invert |
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| ImageFile2 = Chlordecone Kepone 3D.png |
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| ImageFile2 = Chlordecone Kepone 3D.png |
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| ImageSize2 = 120px |
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| ImageSize2 = 120px |
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| IUPACName = decachloropentacyclodecan-5-one<ref></ref> |
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| IUPACName = 1,1a,3,3a,4,5,5,5a,5b,6-Decachlorooctahydro-2''H''-1,3,4-(methanetriyl)cyclobutapentalen-2-one |
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| OtherNames = Chlordecone<br>Clordecone<br>Merex |
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| OtherNames = Chlordecone<br>Clordecone<br>Merex<br /> |
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CAS name: <small>1,1a,3,3a,4,5,5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2H-cyclobutapentalen-2-one</small> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| InChI1 = 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 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChIKey1 = LHHGDZSESBACKH-UHFFFAOYAM |
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| KEGG = C01792 |
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| 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 |
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| InChIKey = LHHGDZSESBACKH-UHFFFAOYAM |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 462576 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LHHGDZSESBACKH-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 143-50-0 |
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| CASNo = 143-50-0 |
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| PubChem = 299 |
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| PubChem = 299 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 293 |
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| ChemSpiderID = 293 |
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| SMILES = ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = RG5XJ88UDF |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 16548 |
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| EINECS = 205-601-3 |
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| SMILES = ClC54C(=O)C1(Cl)C2(Cl)C5(Cl)C3(Cl)C4(Cl)C1(Cl)C2(Cl)C3(Cl)Cl |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 10 | Cl = 10 | O= 1 |
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| C=10 | Cl=10 | O=1 |
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| MolarMass = 490.633 g/mol |
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| MolarMass = 490.633 g/mol |
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| Appearance = |
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| Appearance = tan to white crystalline solid |
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| Density = 1.6 g/cm<sup>3</sup> |
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| Odor = odorless |
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| Density = 1.6 g/cm<sup>3</sup> |
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| MeltingPt = |
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| MeltingPtC = 349 |
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| MeltingPt_notes = (decomposes) |
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| BoilingPt = |
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| Solubility = |
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| BoilingPt = |
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| Solubility = 0.27 g/100 mL |
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| SolubleOther = soluble in ], ], ] <br> slightly soluble in ], ] |
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| LogP = 5.41 |
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| VaporPressure = 3.10<sup>−7</sup> kPa |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section4={{Chembox Thermochemistry |
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| DeltaHf = -225.9 kJ/mol |
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| MainHazards = |
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| FlashPt = |
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| Entropy = 764 J/K mol |
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}} |
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| Autoignition = |
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|Section7={{Chembox Hazards |
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| MainHazards = carcinogen<ref name=PGCH/> |
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| FlashPt_notes = Non-flammable<ref name=PGCH/> |
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| AutoignitionPtC = |
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| LD50 = 95 mg/kg (rat, oral) |
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| PEL = none<ref name=PGCH>{{PGCH|0365}}</ref> |
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| IDLH = N.D.<ref name=PGCH/> |
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| REL = Ca TWA 0.001 mg/m<sup>3</sup><ref name=PGCH/> |
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}} |
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'''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> |
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'''Kepone''', also known as '''chlordecone''', is a ]ic<ref></ref> ] related to ], used between 1966 and 1975 in the USA for ant and ]s. |
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==Synthesis== |
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== Chemistry and toxicology == |
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Chlordecone is made by dimerizing ] and ] to a ].<ref>Survey of Industrial Chemistry by Philip J. Chenier (2002), p. 484.</ref> |
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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. |
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It is also the main degradation product of ].<ref name=Ullmann2/> |
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== History == |
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== History == |
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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/> |
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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> |
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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> |
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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> |
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==Regulation== |
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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 ]. |
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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> |
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In France it was banned on the mainland only, in 1993.<ref name="rapport"/> |
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== French Antilles == |
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In 2009, chlordecone was included in the ], which bans its production and use worldwide.<ref name= "COP4, 2009 Press release"/> |
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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> |
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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> |
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== In popular culture == |
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== Toxicology == |
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* ] 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 ]. |
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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. |
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Workers with repeated exposure suffer severe ] resulting from degradation of the ].<ref name=Ullmann2/> |
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* 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. |
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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> |
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* 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 |
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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> |
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==Incidents== |
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The history of chlordecone incidents are reviewed in ''Who's Poisoning America?: Corporate Polluters and Their Victims in the Chemical Age'' (1982). |
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=== James River estuary === |
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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> |
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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. |
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=== French Antilles === |
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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> |
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== In popular culture == |
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* ] was the name of an American indie rock band from ] formed in 1991. |
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* 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 '']''. |
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==References== |
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