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==Uses== ==Uses==
Endosulfan has been used in agriculture around the world to control insect pests including ]s, ], ]s, ]s, ]s. It has also seen use in wood preservation, home gardening, and ] control, though it is not currently used for public health purposes. The ] estimated world wide annual production to be about 9,000 ]s (t) in the early 1980s.<ref name="EHC">World Health Organization, , 1984.</ref> From 1980–89, worldwide consumption averaged 10,500 t per year, and for the 1990s use increased to 12,800 t per year. India is the world's largest consumer of endosulfan.<ref name=Canada/> Because of its unique mode of action, it is useful in resistance management; however, because it is non-specific, it can negatively impact populations of beneficial insects.<ref>{{cite web|url=http://edis.ifas.ufl.edu/pdffiles/PI/PI03900.pdf|title=Florida Crop/Pest Management Profiles: Tomatoes. CIR 1238.|last=Mossler|first=Mark|coauthors=Michael J. Aerts and O. Norman Nesheim|date=March 2006|publisher=University of Florida, IFAS Extension|accessdate=2009-01-27}}</ref> Endosulfan has been used in agriculture around the world to control insect pests including ]s, ], ]s, ]s, ]s. It has also seen use in wood preservation, home gardening, and ] control, though it is not currently used for public health purposes. The ] estimated world wide annual production to be about 9,000 ]s (t) in the early 1980s.<ref name="EHC">World Health Organization, , 1984.</ref> From 1980–89, worldwide consumption averaged 10,500 t per year, and for the 1990s use increased to 12,800 t per year. India is the world's largest consumer of endosulfan.<ref name=Canada/> Because of its unique mode of action, it is useful in resistance management; however, because it is non-specific, it can negatively impact populations of beneficial insects.<ref>{{cite web|url=http://edis.ifas.ufl.edu/pdffiles/PI/PI03900.pdf|title=Florida Crop/Pest Management Profiles: Tomatoes. CIR 1238.|last=Mossler|first=Mark|coauthors=Michael J. Aerts and O. Norman Nesheim|date=March 2006|publisher=University of Florida, IFAS Extension|accessdate=2009-01-27}}</ref> It is, however, considered to be only moderately toxic to honey bees,<ref>{{cite journal|last=Extension Toxicology Network |date=June 1996|title=Pesticide Information Profile: Endosulfan|publisher=Oregon State University}}</ref> and it is less toxic to bees than ] insecticides.<ref name="RED"/>


==Chemistry== ==Chemistry==

Revision as of 20:32, 23 February 2009

Endosulfan
File:Endosulfan.png
Names
IUPAC names 6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-
6,9-methano-2,4,3-benzodioxathiepine-3-oxide
Other names Benzoepin, Endocel, Parrysulfan, Phaser, Thiodan, Thionex
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.003.709 Edit this at Wikidata
CompTox Dashboard (EPA)
SMILES
  • ClC1(C(Cl)2Cl)C(COS(OC3)=O)C3C2(Cl)C(Cl)=C1Cl
Properties
Molar mass 406.95
Density 1.745 g/cm³
Melting point 70-100 °C
Solubility in water 0.33 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards T, Xi, N
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Endosulfan is a neurotoxic organochlorine insecticide. It is an endocrine disruptor and is highly acutely toxic. Banned in more than 50 countries, including the European Union and several Asian and West African nations, it is still used extensively in many other countries including India, Brazil, and Australia. It is produced by Bayer CropScience, Makhteshim Agan, and government-of-India-owned Hindustan Insecticides Limited among others, and sold under the tradenames Thionex, Endocil, Phaser, and Benzoepin. Because of its high toxicity and high potential for bioaccumulation and environmental contamination, a global ban on the use and manufacture of endosulfan is being considered under the Stockholm Convention.

Uses

Endosulfan has been used in agriculture around the world to control insect pests including whiteflys, aphids, leafhoppers, Colorado potato beetles, cabbage worms. It has also seen use in wood preservation, home gardening, and tse-tse fly control, though it is not currently used for public health purposes. The World Health Organization estimated world wide annual production to be about 9,000 metric tonnes (t) in the early 1980s. From 1980–89, worldwide consumption averaged 10,500 t per year, and for the 1990s use increased to 12,800 t per year. India is the world's largest consumer of endosulfan. Because of its unique mode of action, it is useful in resistance management; however, because it is non-specific, it can negatively impact populations of beneficial insects. It is, however, considered to be only moderately toxic to honey bees, and it is less toxic to bees than organophosphate insecticides.

Chemistry

The IUPAC name for endosulfan is 6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine-3-oxide. It is a cyclodiene insecticide, chemically similar to aldrin, chlordane, and heptachlor. Like these "cousins" it is synthesized from hexachlorocyclopentadiene. Specifically, it is produced by the Diels-Alder reaction of hexachlorocyclopentadiene with cis-butene-1,4-diol and subsequent reaction with thionyl chloride. Technical endosulfan is a mixture of steroisomers, designated "α" and "β," in a 7:3 ratio. The technical material may also contain small amounts endosulfan sulfate and related chemicals. α- and β-endosulfan are conformational isomers, and can be interconverted without breaking bonds. α-Endosulfan is the more thermodynamically stable of the two, and β-endosulfan slowly and irreversibly converts to the α form over time.

History

  • Early 1950s Endosulfan developed.
  • 1954 Hoechst AG (now Bayer CropScience) wins USDA's approval of endosulfan in the US.
  • 2000 Home and garden uses are terminated by agreement with the EPA.
  • 2002 The U.S. Fish and Wildlife Service recommends that endosulfan should be cancelled, and the EPA determines that endosulfan residues on food and in water pose unacceptable risks. The agency allows endosulfan to stay on the market, but imposes restrictions on its agricultural uses.
  • 2007 The international community takes steps to restrict the use and trade of endosulfan. It is recommended for inclusion in the Rotterdam Convention on Prior Informed Consent, and the European Union proposes to add it to the list of chemicals banned under the Stockholm Convention on Persistent Organic Pollutants. If approved, all use and manufacture of endosulfan would be banned globally. Meanwhile, Canada announces that endosulfan is under consideration for phase-out in that country, and Bayer CropScience voluntarily pulls its endosulfan products from the U.S. market but continues to sell them abroad.
  • 2008 In February, environmental, consumer, and farm labor groups including the Natural Resources Defense Council, Organic Consumers Association, and the United Farm Workers call on the U.S. EPA to ban endosulfan. In May, coalitions of scientists, environmental groups, and arctic tribes ask the EPA to cancel endosulfan, and in July a coalition of environmental and workers groups file a lawsuit against the EPA challenging its 2002 decision to not ban it. In October, the Review Committee of the Stockholm Convention moved endosulfan along in the procedure for listing under the treaty, while India blocked its addition to the Rotterdam Convention.
  • 2009 New Zealand bans endosulfan.

Health effects

Endosulfan is one of the more toxic pesticides on the market today, responsible for many fatal pesticide poisoning incidents around the world. Endosulfan is also a xenoestrogen—a synthetic substance that imitates or enhances the effect of estrogens—and it can act as an endocrine disruptor, causing reproductive and developmental damage in both animals and humans. Whether endosulfan can cause cancer is debated.

Toxicity

Endosulfan is acutely neurotoxic to both insects and mammals, including humans. The US EPA classifies it as Category I: "Highly Acutely Toxic" based on a LD50 value of 30 mg/kg for female rats, while the World Health Organization classifies it as Class II "Moderately Hazardous" based on a rat LD50 of 80 mg/kg. It is a GABA-gated chloride channel antagonist, and a Ca, Mg ATPase inhibitor. Both of these enzymes are involved in the transfer of nerve impulses. Symptoms of acute poisoning include include hyperactivity, tremors, convulsions, lack of coordination, staggering, difficulty breathing, nausea and vomiting, diarrhea, and in severe cases, unconsciousness. Doses as low as 35 mg/kg have been documented to cause death in humans, and many cases of sub-lethal poisoning have resulted in permanent brain damage. Farm workers with chronic endosulfan exposure are at risk of rashes and skin irritation.

EPA's acute reference dose for dietary exposure to endosulfan is 0.015 mg/kg for adults and 0.0015 mg/kg for children. For chronic dietary expsoure, the EPA references doses are 0.006 mg/(kg·day) and 0.0006 mg/(kg·day) for adults and children, respectively.

Endocrine disruption

Theo Colborn, an expert on endocrine disruption, lists endosulfan as a known endocrine disruptor, and both the EPA and the Agency for Toxic Substances and Disease Registry consider endosulfan to be a potential endocrine disruptor. Numerous in vitro studies have documented its potential to disrupt hormones and animal studies have demonstrated its reproductive and developmental toxicity, especially among males. A number of studies have documented that it acts as an anti-androgen in animals. Environmentally relevant doses of endosulfan equal to the EPA's safe dose of 0.006 mg/kg/day have been found to affect gene expression in female rats similarly to the effects of estrogen. It is not known whether endosulfan is a human teratogen (an agent that causes birth defects), though it has significant teratogenic effects in laboratory rats.

Reproductive and developmental effects

Several studies have documented that endosulfan can also affect human development. Researchers studying children from an isolated village in Kerala, India have linked endosulfan exposure to delays in sexual maturity among boys. Endosulfan was the only pesticide applied to cashew plantations in the hills above the village for 20 years and had contaminated the village environment. The researchers compared the villagers to a control group of boys from a demographically similar village that lacked a history of endosulfan pollution. Relative to the control group, the exposed boys had high levels of endosulfan in their bodies, lower levels of testosterone, and delays in reaching sexual maturity. Birth defects of the male reproductive system including cryptorchidism were also more prevalent in the study group. The researchers concluded that "our study results suggest that endosulfan exposure in male children may delay sexual maturity and interfere with sex hormone synthesis." Increased incidences of cryptorchidism have been observed in other studies of endosulfan exposed populations.

A 2007 study by the California Department of Public Health found that women who lived near farm fields sprayed with endosulfan and the related organochloride pesticide dicofol during the first eight weeks of pregnancy are several times more likely to give birth to children with autism. This is the first study to look for an association between endosulfan and autism, and additional study is needed to confirm the connection.

Endosulfan and cancer

Endosulfan is not listed as known, probable, or possible carcinogen by the EPA, IARC, or other agencies. There are no epidemiological studies linking exposure to endosulfan specifically to cancer in humans, but in vitro assays have shown that endosulfan can promote proliferation of human breast cancer cells. Evidence of cancinogenicity in animals is mixed.

Endosulfan in the environment

Endosulfan breaks down into endosulfan sulfate and endosulfan diol, both of which, according to the EPA, have "structures similar to the parent compound and are also of toxicological concern…The estimated half-lives for the combined toxic residues (endosulfan plus endosulfan sulfate) from roughly 9 months to 6 years." The EPA concluded that, "ased on environmental fate laboratory studies, terrestrial field dissipation studies, available models, monitoring studies, and published literature, it can be concluded that endosulfan is a very persistent chemical which may stay in the environment for lengthy periods of time, particularly in acid media." The EPA also concluded that "ndosulfan has relatively high potential to bioaccumulate in fish." It is also toxic to amphibians: low levels have been found to kill tadpoles.

Endosulfan is subject to long range atmospheric transport, i.e. it can travel long distances from where it is used. For example, a 2008 report by the National Parks Service found that endosulfan commonly contaminates air, water, plants and fish of National Parks in the U.S. Most of the these parks are far from areas where endosulfan is used. Endosulfan has also been detected in dust from the Sahara Desert collected in the Caribbean after being blown across the Atlantic Ocean.

Endosufan by region

India

India the world's largest user of endosulfan, and a major producer with three companies—Excel Crop Care, H.I.L., and Coromandal Fertilizers—producing 4,500 tonnes annually for domestic use and another 4,000 tonnes for export.

In 2001, in Kerala, India, endosulfan spraying became suspect when linked to a series of abnormalities noted in local children. Initially endosulfan was banned, yet under pressure from the pesticide industry this ban was largely revoked. Achyuthan A studied the effects of the spraying. The situation there has been called "next in magnitude only to the Bhopal gas tragedy." In 2006, in Kerala, compensation of Rs 50,000 was paid to the next kin of each of 135 people who were identified as having died as a result of endosulfan use. Chief Minister V S Achutanandan also gave an assurance to people affected by poisoning, "that the government would chalk out a plan to take care of treatment, food and other needs of the affected persons and that its promise of rehabilitation of victims would be honoured."

India is strongly opposed to adding endosulfan to the Rotterdam and Stockholm Conventions.

New Zealand

Endosulfan was banned in New Zealand by the Environmental Risk Management Authority effective January 2009 after a concerted campaign by environmental groups and the Green Party.

See also: Pesticides in New Zealand

Philippines

A shipment of about 10 tonnes of endosulfan was illegally stowed on the ill-fated MV Princess of the Stars, a ferry that sank off the waters of Romblon (Sibuyan Island), Philippines during a storm in June 2008. Search, rescue, and salvage efforts were suspended when the endosulfan shipment was discovered, and blood samples from divers at the scene were sent to Malaysia for analysis. The Department of Health of the Philippines has temporarily banned the consumption of fish caught in the area. Endosulfan is classified as a "Severe Marine Pollutant" by the International Maritime Dangerous Goods Code.

United States

Endosulfan use in the US in pounds per square mile by county in 2002. (From USGS Pesticide Use Maps)

In the United States, endosulfan is only registered for agricultural use. The companies registered to sell endousulfan in the U.S. are Makhteshim Agan, Drexel, and until recently Bayer CropScience. It has been used extensively on cotton, potatoes, tomatoes, and apples according to the Environmental Protection Agency (EPA). The EPA estimates that 1.38 million lb of endosulfan were used annually from 1987 to 1997. In California, annual use of endosulfan dropped from 230,000 lb (104 t) in 1995 to just 83,000 lb (38 t) in 2005. The US exported more than 300,000 lbs of endosulfan from 2001-2003, mostly to Latin America, but production and export has since stopped.

In California, endosulfan contamination from the San Joaquin Valley has been implicated in the extirpation of the mountain yellow-legged frog from parts of the nearby Sierra Nevada Mountains. In Florida, levels of contamination the Everglades and Biscayne Bay are high enough to pose a threat to some aquatic organisms.

In 2007, the EPA announced it was rereviewing the safety of endosulfan. The following year, Pesticide Action Network and NRDC petitioned the EPA to ban endosulfan, and a coalition of environmental and labor groups sued the EPA seeking to overturn its 2002 decision to not ban endosulfan. As of January 2009, the EPA has yet announce the conclusions of its rereview or whether it will grant the ban requested by the petitions. The lawsuit also remains unresolved.

Australia

In 2008, Australia announced that the use of endosulfan would not be banned in the country. Environmentalist have protested the decision, citing New Zealand's recent ban, with Greeens calling for a ban on its use and for "zero tolerance" for endosulfan residues on food. Endosulfan contamination from nearby farm is suspected as a possible cause for a recent spate of two-headed fish at fish farm in the Noosa River.

References

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  49. Dan B. Kimball, Superintendent National Park Service (October 29, 2008). "Letter to EPA re: Petitions to Revoke All Tolerances Established for Endosulfan; Federal Register: August 20, 2008 (Volume 73, Number 162). Docket ID No. EPA-HQ-OPP-2008-0615-0041.1". Retrieved 2009-01-27.
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  52. BURKE, KELLY (January 7, 2009). "Australia refuses to join ban on pesticide". Harden Murrumburrah Express,. Retrieved 2009-01-08.{{cite news}}: CS1 maint: extra punctuation (link)
  53. Williams, Brian (January 12, 2009). "Two-headed fish larvae blamed on farm chemicals in Noosa River". Courier Mail. Retrieved 2009-01-13. {{cite news}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

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