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endosulfan

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endosulfan

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Also known as Benzoepin, Endosulphan, 6,7,8,9,10-Hexachloro-1,5,5a,6,9,9a-hexachloro-6,9-methano-2,4,3-benzo-dioxathiepin-3-oxide, Thiodan, 1,9,10,11,12,12-hexachloro-4,6-dioxa-5-thiatricyclo[7.2.1.0(2,8)]dodec-10-ene 5-oxide, 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dimethanol cyclic sulfite, 1,4,5,6,7,7-Hexachloro-8,9,10-trinorborn-5-en-2,3-ylenedimethyl sulphite, alpha,beta-1,2,3,4,7,7-Hexachlorobicyclo(2.2.1)-2-heptene-5,6-bisoxymethylene sulfite

Endosulfan is an organochlorine insecticide and acaricide, which acts by blocking the GABA-gated chloride channel of the insect (IRAC group 2A). It became highly controversial due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention in April 2011. The ban took effect in mid-2012, with certain uses exempted for five additional years. More than 80 countries, including the European Union, Australia, New

Chemical data

Formula
C9H6Cl6O3S
Molecular weight
406.9 g/mol
IUPAC name
1,9,10,11,12,12-hexachloro-4,6-dioxa-5lambda4-thiatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide
SMILES
C1C2C(COS(=O)O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl
InChIKey
RDYMFSUJUZBWLH-UHFFFAOYSA-N
XLogP
3.8
Polar surface area
54.7 Ų
H-bond donors
0
H-bond acceptors
4
Formal charge
0

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Research

2,968 papers

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Wikidata facts

Mass
403.8168811319999
Show 9 more facts
chemical formula
C₉H₆Cl₆O₃S
melting point
223
Commons category
Endosulfan
NIOSH Pocket Guide ID
0251
density
1.74
canonical SMILES
C1C2C(COS(=O)O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl
vapor pressure
0.00001
solubility
0.00001
time-weighted average exposure limit
0.1
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Article

19 sections
Contents
  • Uses
  • Production
  • History of commercialization and regulation
  • Health effects
  • Toxicity
  • Endocrine disruption
  • Reproductive and developmental effects
  • Cancer
  • Environmental fate
  • Status by region
  • India
  • New Zealand
  • Philippines
  • United States
  • Australia
  • Taiwan
  • Brazil
  • References
  • External links

Endosulfan is an organochlorine insecticide and acaricide, which acts by blocking the GABA-gated chloride channel of the insect (IRAC group 2A). It became highly controversial due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Because of its threats to human health and the environment, a global ban on the manufacture and use of endosulfan was negotiated under the Stockholm Convention in April 2011. The ban took effect in mid-2012, with certain uses exempted for five additional years. More than 80 countries, including the European Union, Australia, New Zealand, several West African nations, the United States, Brazil, and Canada had already banned it or announced phase-outs by the time the Stockholm Convention ban was agreed upon. It is still used extensively in India and China despite laws against its use. It is also used in a few other countries. It is produced by the Israeli firm Makhteshim Agan and several manufacturers in India and China. On May 13, 2011, the India Supreme Court ordered a ban on the production and sale of endosulfan in India, pending further notice.

==Uses== Endosulfan has been used in agriculture around the world to control insect pests including whiteflies, aphids, leafhoppers, Colorado potato beetles and cabbage worms. Due to its unique mode of action, it is useful in resistance management; however, as it is not specific, it can negatively impact populations of beneficial insects. It is, however, considered to be moderately toxic to honey bees, and it is less toxic to bees than organophosphate insecticides.

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