Structure via PubChem · Public domain (PubChem)
endosulfan
Sign in to saveAlso 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
via PubChem
Research
2,968 papers- Endosulfan poisoning: An overview.Journal of forensic and legal medicine · 2017
- Endosulfan, a global pesticide: a review of its fate in the environment and occurrence in the Arctic.The Science of the total environment · 2010
- Postnatal exposure to endosulfan affects uterine development and fertility.Molecular and cellular endocrinology · 2020
- Endosulfan affects embryonic development synergistically under elevated ambient temperature.Environmental science and pollution research international · 2023
- Molecular mechanism of Endosulfan action in mammals.Journal of biosciences · 2017
via PubMed
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
via Wikidata · CC0
~25 min read
Article
19 sectionsContents
- 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.