| Compound Name |
Technical endosulfan and its related isomers |
| Stockholm Annex code | I, IV |
| Key |
Annex I to the regulation are subject to prohibition (with specific exemptions) on manufacturing, placing on the market and use; Annex II to the regulation are subject to restriction on manufacturing, placing on the market and use; Annex III to the regulation are subject to release reduction provisions; and Annex IV to the regulation are subject to waste management provisions. Note that for some substances listed in Annex I, specific exemptions on the prohibition of their use, manufacturing and placing on the market may apply. |
| Classification |
Intentional production |
| Category |
Listed under Annex A with specific exemptions (decision SC-5/3) |
| Year of Listing Decision |
2011 |
| Persistence |
The half-life of total endosulfan and alpha and beta endosulfan is 27.5 and 157 days, respectively, under aerobic conditions (GFEA-U, 2007; US EPA, 2007a). |
| Specific exemptions associated with its use |
Production: As allowed for the parties listed in the Register |
| Acceptable purposes associated with its use |
Use: Croppest complexes as listed in accordance with theprovisions of Part VI of Annex A Was used as an insecticide since the early 1950s to control crop pests, tsetse flies and ectoparasites of cattle Also used to control a vast range of pests on a variety of crops including coffee, cotton, rice, sorghum and soy Used as a wood preservative |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Technical endosulfan and its related isomers |
| Synonyms |
6,9-Methano-2,4,3-benzodioxathiepin, 6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-, 3-oxide Benzoepin 6,7,8,9,10,10-Hexachloro-1,5,5a,6,9,9a-hexahydro-3H-6,9-methano-3lambda~4~-2,4,3lambda~4~-benzodioxathiepin-3-one Thiosulfan 6,9-Methano-2,4,3-benzodioxathiepin, 6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-, 3-oxide 5-Norbornene-2,3-dimethanol, 1,4,5,6,7,7-hexachloro-, cyclic sulfite Chlorthiepin 6,7,8,9,10,10-Hexachloro-1,5,5alpha,6,9,9alpha-hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide Thiodan Endosulphan Rasayansulfan Endosulfan 35EC Thiodan 35EC Endodhan |
| Structure | O1)C3(C(=C(C2(C3(Cl)Cl)Cl)Cl)Cl)Cl.png)
Molecular Formula:
C9H6Cl6O3S
|
| CAS Number | 115-29-7 |
| European Community (EC) Number | 204-079-4 |
| European Chemicals Agency (ECHA) | 204-079-4 |
| PubChem ID | 3224 |
| DSSTOX Substance ID | DTXSID1020560 |
| KEGG | C11090 |
| ChemSpider |
21117730 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| 1.0 | Endosulfan I | DTXSID9037539 | 959-98-8 | 406 g/mol | C9H6Cl6O3S |
| 1.0 | Endosulfan II | DTXSID8037540 | 33213-65-9 | 406 g/mol | C9H6Cl6O3S |
| 0.96 | Endosulfan sulfate | DTXSID3037541 | 1031-07-8 | 422 g/mol | C9H6Cl6O4S |
| Description | Reference | Article Link |
|---|---|---|
| Endosulfan is a cyclodiene contact insecticide/miticide that became widely used beginning in the 1950s. Currently, its uses and international trade have been curtailed or eliminated in most countries, following Annex A (elimination) listing by the Stockholm Convention and subsequent bans or phase-out programs in over 80 countries. These actions have been primarily based on the conclusion that endosulfan could not be risk managed in a sustainable way due to its persistence in the environment and potential hazard to humans and other living organisms. | Singh et al., 2014. Endosulfan | Link |
| Endosulfan has been used globally as a pesticide since the 1950s to control a variety of insects including whiteflies, aphids, leafhoppers, Colorado potato beetles, and cabbage worms. Endosulfan exists as two (alpha and beta) isomers that can be metabolized to endosulfan sulfate and endosulfan diol. Because of its unique mode of action, it is useful in insect control; however, it can also negatively impact populations of beneficial insects. In contrast to most OCPs, endosulfan has a lower affinity to lipids. Consequently, biomagnification and accumulation of endosulfan are less likely to occur. The use of endosulfan became controversial because of its acute toxicity, potential for bioaccumulation, and role as an endocrine disruptor. It was banned by the Stockholm Convention in 2011 because of its threats to human health and the environment. It is still used in India, China, and a few other countries. Endosulfan is acutely neurotoxic to both insects and mammals, including humans. Fish, in particular salmonids, are considered highly susceptible to waterborne endosulfan. In contrast, toxicity of diet-borne endosulfan shows high variability among fish species. Endosulfan is a chloride channel antagonist and inhibits calcium and magnesium ATPase, which are enzymes involved in the transfer of nerve impulses. The kidney is the target organ for toxicity. Studies have shown that endosulfan may bind to estrogen receptors and perturb the endocrine system. Doses as low as 35 mg/kg have been documented to cause mortality in humans, and many cases of sublethal poisoning have resulted in permanent brain damage. Data on endosulfan levels in food products are limited; nevertheless, available data suggest that the dietary intake of endosulfan by the general population is far below the ADI of 6 micrograms per kg b.w. established by the JMPR in 1998. | Berntssen et al., 2017. Chapter 20 - Chemical Contamination of Finfish With Organic Pollutants and Metals | Link |
| Technical grade endosulfan is commercially available as a mixture typically containing > 95% of two diastereoisomers, known as alpha-endosulfan (or I) and beta-endosulfan (or II) in ratios from 2:1 to 7:3 depending on the technical mixture (Herrmann, 2002). Market names include Thiodan®, Endox®, Thiomul®, Beosit®, Endocell®, Malix®, Thionex®, Insecto®, and Tiovel®. Endosulfan formulations include emulsifiable concentrate, wettable powder, smoke tablets and ultra-low volume liquid formulations, the latter often used under subtropical conditions to minimise volatilisation losses. In temperate regions, the pesticide is typically applied to crops using air-blast or ground boom sprayers. | Weber et al., 2010. Endosulfan, a global pesticide: A review of its fate in the environment and occurrence in the Arctic. | Link |
| Endosulfan, also known as Thiodan or Thionex, is a polychlorinated compound used as a pesticide or acaricide. It has been in use since the 1950s in China, the European Union, Australia, Mexico, the United States, and India for crops including maize, soybeans, tomatoes, and cotton. It is particularly effective in removing aphids, fruit worms, beetles, leafhoppers, moth larvae, and whiteflies. However, its highly toxic properties can potentially harm humans and wildlife. Further, due to its semi-volatility, endosulfan is often found thousands of kilometers away from its intended area of action in soil, water reservoirs, sediments, and even Arctic and Antarctic lakes. These findings prove its persistent character; indeed, it is listed as a persistent organic pollutant in the atmosphere, soil, and water by the Stockholm Convention. For this reason, it has been banned in over 80 nations. However, one of the main problems with pesticides as endosulfan is the fact that they are persistent and can be dispersed from air to water bodies. The environmental presence of endosulfan has been evaluated showing values from 0.036 micrograms per liter to 62.3 micrograms per liter in water bodies. Indeed, it is an extremely toxic and harmful compound to beneficial non-target invertebrates living in aquatic media. | Alonso-Trujillo et al., 2020. Endosulfan exposure alters transcription of genes involved in the detoxification and stress responses in Physella acuta. | Link |