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Endosulfan

Tags: Endosulfan
Endosulfan
endosulfan


Endosulfan is an off-patent organochlorine insecticide and acaricide. This colourless solid has emerged as a highly controversial agrichemical[1] due to its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. Banned in more than 63 countries, including the European Union, Australia and New Zealand, and other Asian and West African nations,[2] and being phased out in the United States,[3][4] and Brazil[5] it is still used extensively in many other countries including India and China. It is produced by Bayer CropScience, Makhteshim Agan, and Government-of-India–owned Hindustan Insecticides Limited among others. Because of its threats to the environment, a global ban on the use and manufacture of endosulfan is being considered under the Stockholm Convention.

Endosulfan
Identifiers
CAS number115-29-7 YesY
ChemSpider21117730 YesY
KEGGC11090 N
Properties
Molecular formulaC9H6Cl6O3S
Molar mass406.95
Density1.745 g/cm³
Melting point

70–100 °C

Solubility in water0.33 mg/L
Hazards
EU classificationYes (T, Xi, N)
R-phrasesR24/25 R36 R50/53
NFPA 704
NFPA 704.svg
1
2
0
 N(what is this?)  (verify)
Except where noted otherwise, data are given for materials in their
standard state (at 25 °C, 100 kPa)
Infobox references

Endosulfan has been used in agriculture around the world to control insect pests including whiteflys, aphids, leafhoppers, Colorado potato beetles and cabbage worms.[7] 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.[8] It is, however, considered to be moderately toxic to honey bees,[9] and it is less toxic to bees than organophosphate insecticides

The World Health Organization estimated world wide annual production to be about 9,000 metric tonnes (t) in the early 1980s.[11] From 1980–89, worldwide consumption averaged 10,500 t per year, and for the 1990s use increased to 12,800 t per year.

Endosulfan is a derivative of hexachlorocyclopentadiene and is chemically similar to aldrin, chlordane, and heptachlor. Specifically, it is produced by the Diels-Alder reaction of hexachlorocyclopentadiene with cis-butene-1,4-diol and subsequent reaction of the adduct with thionyl chloride. Technical endosulfan is a 7:3 mixture of stereoisomers, designated α and β. α- and β-endosulfan are conformational isomers arising from the pyramidal stereochemistry of sulfur. α-Endosulfan is the more thermodynamically stable of the two, thus β-endosulfan irreversibly converts to the α form, although the conversion is slow

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