Chlordecone, better known in the United States under the brand name Kepone, is an

organochlorine compound An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalent bond, covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens subst ...

and a colourless solid. It is an obsolete

insecticide Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...

, now prohibited in the western world, but only after many thousands of tonnes had been produced and used.Robert L. Metcalf "Insect Control" in ''Ullmann's Encyclopedia of Industrial Chemistry'' Wiley-VCH, Wienheim, 2002. Chlordecone is a known

persistent organic pollutant Persistent organic pollutants (POPs), sometimes known as "forever chemicals", are organic compounds that are resistant to environmental degradation through chemical, biological, and photolytic processes. They are toxic chemicals that adversely ...

(POP) that was banned globally by the

Stockholm Convention on Persistent Organic Pollutants Stockholm Convention on Persistent Organic Pollutants is an international environmental treaty, signed on 22 May 2001 in Stockholm and effective from 17 May 2004, that aims to eliminate or restrict the production and use of persistent organic ...

in 2009.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.

Synthesis

Chlordecone is made by dimerizing

hexachlorocyclopentadiene Hexachlorocyclopentadiene (HCCPD), also known as C-56, Graphlox, and HRS 1655, is an organochlorine compound with the formula C5Cl6. It is a precursor to pesticides, flame retardants, and dyes. It is a colourless liquid, although commercial sample ...

and

hydrolyzing Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...

to a

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

. It is also the main degradation product of

Mirex Mirex was an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants b ...

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 Hopewell is an independent city surrounded by Prince George County and the Appomattox River in the Commonwealth of Virginia. At the 2020 census, the population was 23,033. The Bureau of Economic Analysis combines the city of Hopewell with Prin ...

. The improper handling and dumping of the substance (including the waste materials generated in its manufacturing process) into the nearby

James River The James River is a river in the U.S. state of Virginia that begins in the Appalachian Mountains and flows U.S. Geological Survey. National Hydrography Dataset high-resolution flowline dataThe National Map , accessed April 1, 2011 to Chesapea ...

(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. "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 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 Chlordane, or chlordan, is an organochlorine compound that was used as a pesticide. It is a white solid. In the United States, chlordane was used for termite-treatment of approximately 30 million homes until it was banned in 1988. Chlordane was b ...

and

Endosulfan Endosulfan is an off-patent organochlorine insecticide and acaricide that is being phased out globally. It became a highly controversial agrichemical due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. ...

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

neurological Neurology (from el, νεῦρον (neûron), "string, nerve" and the suffix -logia, "study of") is the branch of medicine dealing with the diagnosis and treatment of all categories of conditions and disease involving the brain, the spinal ...

.Richard Foster
Kepone: The 'Flour' Factory
''Richmond Magazine'' (July 8, 2005). Chlordecone is cited amongst a handful of other noxious substances as the driver for

Gerald Ford Gerald Rudolph Ford Jr. ( ; born Leslie Lynch King Jr.; July 14, 1913December 26, 2006) was an American politician who served as the 38th president of the United States from 1974 to 1977. He was the only president never to have been elected ...

's half-hearted approval in 1976 of the

Toxic Substances Control Act The Toxic Substances Control Act (TSCA) is a United States law, passed by the 94th United States Congress in 1976 and administered by the United States Environmental Protection Agency (EPA), that regulates chemicals not regulated by other U.S. ...

, which "remains one of the most controversial regulatory bills ever passed". In 2009, chlordecone was included in the

, which bans its production and use worldwide.

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 A lipoprotein is a biochemical assembly whose primary function is to transport hydrophobic lipid (also known as fat) molecules in water, as in blood plasma or other extracellular fluids. They consist of a triglyceride and cholesterol center, su ...

LDL Low-density lipoprotein (LDL) is one of the five major groups of lipoprotein that transport all fat molecules around the body in extracellular water. These groups, from least dense to most dense, are chylomicrons (aka ULDL by the overall densit ...

and HDL. The LC₅₀ (LC = lethal concentration) is 35 μg/ L for ''

Etroplus maculatus The orange chromide (''Pseudetroplus maculatus'') is a species of cichlid fish that is Endemism, endemic to freshwater and brackish water, brackish streams, lagoons and estuary, estuaries in southern India and Sri Lanka.Pethiyagoda, R., Maduwage, ...

'', 22–95 μg/kg for

blue gill The bluegill (''Lepomis macrochirus''), sometimes referred to as "bream", "brim", "sunny", or "copper nose" as is common in Texas, is a species of North American freshwater fish, native to and commonly found in streams, rivers, lakes, ponds and ...

and

trout Trout are species of freshwater fish belonging to the genera '' Oncorhynchus'', ''Salmo'' and ''Salvelinus'', all of the subfamily Salmoninae of the family Salmonidae. The word ''trout'' is also used as part of the name of some non-salmoni ...

. Chlordecone

bioaccumulate Bioaccumulation is the gradual accumulation of substances, such as pesticides or other chemicals, in an organism. Bioaccumulation occurs when an organism absorbs a substance at a rate faster than that at which the substance is lost or eliminated ...

s in animals by factors up to a million-fold. Workers with repeated exposure suffer severe

convulsions A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a s ...

resulting from degradation of the synaptic junctions. Chronic low level exposure appears to cause

prostate cancer Prostate cancer is cancer of the prostate. Prostate cancer is the second most common cancerous tumor worldwide and is the fifth leading cause of cancer-related mortality among men. The prostate is a gland in the male reproductive system that sur ...

in men, and "significant excesses of deaths were observed for

stomach cancer Stomach cancer, also known as gastric cancer, is a cancer that develops from the lining of the stomach. Most cases of stomach cancers are gastric carcinomas, which can be divided into a number of subtypes, including gastric adenocarcinomas. Lymph ...

in women and

pancreatic cancer Pancreatic cancer arises when cell (biology), cells in the pancreas, a glandular organ behind the stomach, begin to multiply out of control and form a Neoplasm, mass. These cancerous cells have the malignant, ability to invade other parts of t ...

in women". Chlordecone has been found to act as an

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

of the

GPER G protein-coupled estrogen receptor 1 (GPER), also known as G protein-coupled receptor 30 (GPR30), is a protein that in humans is encoded by the ''GPER'' gene. GPER binds to and is activated by the female sex hormone estradiol and is responsible ...

(GPR30), which interacts strongly with the

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...

sex hormone Sex hormones, also known as sex steroids, gonadocorticoids and gonadal steroids, are steroid hormones that interact with vertebrate steroid hormone receptors. The sex hormones include the androgens, estrogens, and progestogens. Their effects ar ...

estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development of f ...

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 Virginia, officially the Commonwealth of Virginia, is a state in the Mid-Atlantic and Southeastern regions of the United States, between the Atlantic Coast and the Appalachian Mountains. The geography and climate of the Commonwealth ar ...

Governor

Mills Godwin Jr. Mills Edwin Godwin Jr. (November 19, 1914January 30, 1999) was an American politician who was the 60th and 62nd governor of Virginia for two non-consecutive terms, from 1966 to 1970 and from 1974 to 1978. In his first term, he was a member of ...

shut down the

to fishing for 100 miles, from

Richmond Richmond most often refers to: * Richmond, Virginia, the capital of Virginia, United States * Richmond, London, a part of London * Richmond, North Yorkshire, a town in England * Richmond, British Columbia, a city in Canada * Richmond, California, ...

to the

Chesapeake Bay The Chesapeake Bay ( ) is the largest estuary in the United States. The Bay is located in the Mid-Atlantic (United States), Mid-Atlantic region and is primarily separated from the Atlantic Ocean by the Delmarva Peninsula (including the parts: the ...

. This ban remained in effect for 13 years, until efforts to clean up the river began to show results.Jack Cooksey, "What's in the Water?"
''Richmond Magazine'', June 2007. Retrieved 13 June 2012. 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 Allied Corp. was a major American company with operations in the chemical, aerospace, automotive, oil and gas industries. It was initially formed in 1920 as the Allied Chemical and Dye Corporation as an amalgamation of five chemical companies. In ...

in federal district court (

Eastern District of Virginia The United States District Court for the Eastern District of Virginia (in case citations, E.D. Va.) is one of two United States district courts serving the Virginia, Commonwealth of Virginia. It has jurisdiction over the Northern Virginia, H ...

), 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 Martinique ( , ; gcf, label=Martinican Creole, Matinik or ; Kalinago: or ) is an island and an overseas department/region and single territorial collectivity of France. An integral part of the French Republic, Martinique is located in th ...

and

Guadeloupe Guadeloupe (; ; gcf, label=Antillean Creole, Gwadloup, ) is an archipelago and overseas department and region of France in the Caribbean. It consists of six inhabited islands—Basse-Terre, Grande-Terre, Marie-Galante, La Désirade, and the ...

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 the chemical, under the name Curlone, most likely continued to be illegally imported and was used for many more years. Since 2003, local authorities in the two islands have restricted cultivation of many 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

diagnosis rates in the world.

In popular culture

Kepone 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 bee ...

was the name of an American indie rock band from

Richmond, Virginia (Thus do we reach the stars) , image_map = , mapsize = 250 px , map_caption = Location within Virginia , pushpin_map = Virginia#USA , pushpin_label = Richmond , pushpin_m ...

formed in 1991. * The

Dead Kennedys Dead Kennedys are an American punk rock band that formed in San Francisco, California, in 1978. The band was one of the defining punk rock, punk bands during its initial eight-year run. Dead Kennedys' lyrics were usually political in nature, sa ...

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. ''In God We Trust, Inc.'' is an EP by hardcore punk band Dead Kennedys and the first of the group's releases with drummer D.H. Peligro. The record is a screed against things ranging from organized religion and Neo-Nazism, Neo-Nazis, to the pesti ...

''.

References

External links

Terradaily: Pesticide blamed for 'health disaster' in French CaribbeanEPA releases a Toxicological Review of Kepone (External Review Draft) for public comment – 01/2008
{{Estrogen receptor modulators Obsolete pesticides Carcinogens GPER agonists Ketones Organochloride insecticides James River (Virginia) Endocrine disruptors IARC Group 2B carcinogens Persistent organic pollutants under the Stockholm Convention Male reproductive toxicants Persistent organic pollutants under the Convention on Long-Range Transboundary Air Pollution Xenoestrogens Cyclobutanes 1975 disasters in the United States 1975 in the environment Neurotoxins Presidency of Gerald Ford