| Compound Name |
Chlordecone |
| Stockholm Annex code | I, IV |
| Key |
Annex I to the regulation are subject to prohibition (with specific exemptions) on manufacturing, placing on the market and use; Annex II to the regulation are subject to restriction on manufacturing, placing on the market and use; Annex III to the regulation are subject to release reduction provisions; and Annex IV to the regulation are subject to waste management provisions. Note that for some substances listed in Annex I, specific exemptions on the prohibition of their use, manufacturing and placing on the market may apply. |
| Classification |
Intentional |
| Category |
A - (Elimination) Parties have put in place measures to eliminate the production and use of the chem |
| Year of Listing Decision |
2009 |
| Persistence |
12 years |
| Specific exemptions associated with its use |
Production: None |
| Acceptable purposes associated with its use |
None Used as a pesticide. |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Chlordecone |
| Synonyms |
Kepone Merex Clordecone Decachloroketone GC 1189 Decachlorotetracyclodecanone Kepone-2-one, decachlorooctahydro-CCRIS 128 Decachlorotetrahydro-4,7-methanoindeneone AI3-16391 |
| Structure | C2(C3(C4(C1(C5(C2(C3(C(C45Cl)(Cl)Cl)Cl)Cl)Cl)Cl)Cl)Cl)Cl.png)
Molecular Formula:
C10Cl10O
|
| CAS Number | 143-50-0 |
| European Community (EC) Number | 205-601-3 |
| European Chemicals Agency (ECHA) | 205-601-3 |
| PubChem ID | 299 |
| DSSTOX Substance ID | DTXSID1020770 |
| KEGG | C01792 |
| ChemSpider |
293 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| 1.0 | 1,1a,3,3a,4,5,5,5a-Octachlorooctahydro-2H-1,3,4-(methanetriyl)cyclobuta[cd]pentalen-2-one | DTXSID60989261 | 69417-78-3 | 421 g/mol | C10H2Cl8O |
| 1.0 | 1,1a,3a,4,5,5,5a,6-Octachlorooctahydro-2H-1,3,4-(methanetriyl)cyclobuta[cd]pentalen-2-one | DTXSID80997767 | 76391-90-7 | 421 g/mol | C10H2Cl8O |
| 1.0 | 1,1a,3,3a,4,5,5,5a,5b-Nonachlorooctahydro-2H-1,3,4-(methanetriyl)cyclobuta[cd]pentalen-2-one | DTXSID80967900 | 53308-47-7 | 456 g/mol | C10HCl9O |
| 0.9 | 2,2,6-Trichloro-6-(1-chloro-2-methylpropyl)cyclohexan-1-one | DTXSID20575260 | 89110-96-3 | 292 g/mol | C10H14Cl4O |
| 0.9 | Endrin ketone | DTXSID00872845 | 53494-70-5 | 380 g/mol | C12H8Cl6O |
| 0.87 | NSC314544 | DTXSID70330806 | 67277-93-4 | 326 g/mol | C13H12Cl4O |
| Description | Reference | Article Link |
|---|---|---|
| Chlordecone (Kepone®, C10Cl10O) is an organochlorine pesticide formerly used worldwide. Its rare perchlorinated bishomocubane structure, present in only two other insecticides, Kelevan and Mirex (used also as fire-retardant), originates from the dimerization of hexachlorocyclopentadiene which is a key intermediate in the synthesis of many other organochlorine pesticides (e.g., aldrin, dieldrin, heptachlor, or endosulfan). Mirex (C12Cl12) differs from chlordecone, as it possesses a dichloromethylene group in place of carbonyl moiety. Kelevan (C17H12Cl10O4) used in Europe to fight against the Colorado potato beetle is made from chlordecone by addition of ethyl levulinate onto the ketone function. Both compounds are known to generate chlordecone among other degradative metabolites in environmental conditions. Chlordecone persists in the environment. In humans, recent epidemiological and toxicological studies have demonstrated that chlordecone is a reproductive and developmental toxicant, an endocrine-disrupting chemical and a neurotoxic. It is also consistently associated with an increase in the risk of prostate cancer. In human and some mammals, chlordecone is metabolized in liver: after reduction into chlordecol, a chlordecol-glucuronide is formed and excreted. | Chaussonneri et al. 2016. Microbial Degradation of a Recalcitrant Pesticide: Chlordecone. | Link |
| Chlordecone (CLD) was used to control insect pests (mainly the banana weevil) in banana plantations in the Caribbean, particularly in Guadeloupe and Martinique from 1971 to 1993, despite being banned in the United States since 1974. This pesticide was also used in the USA, as well as in some countries of Africa (Cameroon, Ivory Coast), latin America (Panama, Honduras, Equator, Nicaragua) and Asia. Chlordecone (C10Cl10O) is a bis-homocubane, comprising a cage structure with 10 chlorine atoms and a ketone functionality. It was commercialized under the brand names Kepone® and Curlone® and was spread at the foot of each banana plant as a solution delivering 1.5 grams of chlordecone per plant. With 800 banana plants per hectare and 2.5 applications per year, the resulting dosage was a significant 3 kg chlordecone per hectare per year. As a consequence of such intensive application, 8–9% of the cultivated areas of Guadeloupe have CLD concentrations higher than 1 mg/kg in topsoil, and some banana fields have concentrations higher than 9 mg/kg. CLD adsorbs strongly to soils rich in organic matter, and its partitioning coefficient (log Koc) has been reported in the range of 3.3–3.41. CLD is only slightly soluble in water (2.7 mg/L at pH 7 and 25°C) and tends to bioaccumulate in fatty tissues of living organisms. CLD is also neurotoxic, immunotoxic, hepatotoxic and spermatotoxic to most living organisms. In 2009, CLD was added to the list of persistent organic pollutants in the Stockholm Convention, banning its production and use worldwide. Studies suggest exposure to CLD may be linked to higher occurrence of prostate cancer and to impaired cognitive and motor development in young children. Watershed modelling predicts that CLD will remain in soils for decades or even centuries because of its stability and affinity for soil organic matter, providing a long term source of contamination to the aquatic environment. Surface water, ground water, sediments and receiving coastal wasters have all been impacted. CLD has also been found to accumulate in animals and plants used for food, including tubers and other vegetables grown in soil as well as in marine fauna. Effective methods to decontaminate soil and protect downgradient environments, food and water supply are clearly needed. | Lomheim et al., 2020. Evidence for extensive anaerobic dechlorination and transformation of the pesticide chlordecone (C10Cl10O) by indigenous microbes in microcosms from Guadeloupe soil. | Link |
| Chlordecone, commonly referred to as Kepone, is a highly chlorinated cyclodiene pesticide which bioaccumulates in the food chain. In the French West Indies, Guadeloupe and Martinique, it was intensively applied to banana fields from 1973 to 1993 to control root borers. This pesticide undergoes no significant biotic or abiotic degradation in the environment and is still present in soils where it was applied.In 1980, a detailed report showed that chlordecone was the chlorinated chemical most frequently detected and at the highest concentrations in wild birds, mammals, fish, and shellfish living in areas of banana cultivation or at the coast near outlets of contaminated rivers. It was only in 1999 that health and environmental authorities became aware of the extent of the chlordecone pollution of environmental media, including soils, waterways, and the food chain. Earlier observations and toxicological studies have demonstrated that chlordecone is a reproductive and developmental toxicant, neurotoxic and carcinogenic in rodents, and is an endocrine-disrupting chemical because of its estrogenic properties both in vitro and in vivo. Several surveys have confirmed that the French West Indian population continues to be exposed to this chemical though consumption of contaminated foodstuffs and tap water. | Multigner et al., 2016. Chlordecone exposure and adverse effects in French West Indies populations. | Link |
| The cyclodiene insecticide chlordecone (CLD) (1,1a,3,3a,4,5, 5,5a,5b,6-decachlorooctahydro-1,3,4-metheno-2Hcyclobuta[cd]pentalen-2-one) is one of the persistent organic pollutants (POPs) listed on Annex A of the Stockholm convention. It was classified as a persistent organic pollutant (POP) in 2009, but unfortunately, it had been used for 2 decades to control the development of the banana weevil, Cosmopolites sordidus, in banana plantations of the French West Indies. Over that period (1972–1978 under the trademark Kepone® and 1981–1993 under the trademark Curlone®), approximatively 300 t of CLD was applied in banana plantations and contained approximately 20,000 ha representing 25 % of agricultural soils in the FWI. Soils of banana plantations directly exposed to this insecticide are contaminated with CLD concentrations ranging between 0.1 and 37.4 mg kg?1. In addition, although CLD displays high affinity for soil organic matter, its residues leach from agricultural soils to water resources and pollute drinking water in the FWI but also contaminate aquatic biota, including fish and giant shrimp locally called ouassou. Moreover, due to its biomagnification potential, CLD can be transferred to crops (tuber vegetables; cucurbits) and accumulate in poultry or cattle fed with CLD-contaminated resources. Monitoring contamination revealed the presence of CLD not only in soils but also in rivers, springs, drinking water, and food crop products such as tuber vegetables, cucurbits, food fishing products (shrimp, fish), and food breeding products too (ducks, hens). Consequently, contamination of the environment and of the food chain by CLD chronically exposes FWI populations, with consequences on human health such as higher prevalence of prostate cancer in FWI populations exposed to CLD, or delays in cognitive, visual, and motor development in young children exposed to CLD. | Merlin et al., 2015. Evaluation of the ecotoxicological impact of the organochlorine chlordecone on soil microbial community structure, abundance, and function. | Link |