Coumaphos

Coumaphos

Names
IUPAC name O,O-Diethyl O-3-chloro-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate
Other names 3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone Coumafos, Meldane, Asunthol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix
Identifiers
CAS Number	56-72-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:3903
ChEMBL	ChEMBL251680
ChemSpider	2768
ECHA InfoCard	100.000.260
KEGG	D07750
PubChem	2871
UNII	L08SZ5Z5JC
InChI InChI=1S/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3 Key: BXNANOICGRISHX-UHFFFAOYSA-N InChI=1/C14H16ClO5PS/c1-4-17-21(22,18-5-2)20-10-6-7-11-9(3)13(15)14(16)19-12(11)8-10/h6-8H,4-5H2,1-3H3 Key: BXNANOICGRISHX-UHFFFAOYAO
SMILES S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2
Properties
Chemical formula	C14H16ClO5PS
Molar mass	362.77 g/mol
Pharmacology
ATCvet code	QP53AF08 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Coumaphos is a nonvolatile, fat-soluble phosphorothioate with ectoparasiticide properties: it kills insects and mites. It is well known by a variety of brand names as a dip or wash, used on farm and domestic animals to control ticks, mites, flies and fleas.^[1]

It is also used to control Varroa mites in honey bee colonies, though in many areas it is falling out of favor as the mites develop resistance and as the residual toxicity effects are becoming better understood.^[2][3]

In Australia, its registration as suited to home veterinary use was cancelled by the Australian Pesticides and Veterinary Medicines Authority in June 2004 after the manufacturer failed to show it was safe for use on pets.^[4]

The compound has been linked to neurological problems in bees, and may be a factor in colony collapse.^[5]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[6]

References

1. "Asuntol - Cattle, Goat, Sheep - anti lice, fleas, sucking flies and mite". vetcontact.com.
2. "A Review of Treatment Options for Control of Varroa Mite in New Zealand". biosecurity.govt.nz.
3. Johnson, Reed M.; Ellis, Marion D.; Mullin, Christopher A.; Frazier, Maryann (2010). "Pesticides and honey bee toxicity – USA". Apidologie. 41 (3): 312. doi:10.1051/apido/2010018.
4. http://www.apvma.gov.au/chemrev/coumaphos.shtml Archived August 29, 2008, at the Wayback Machine.
5. http://www.bbc.co.uk/news/science-environment-21958547
6. "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011.

External links

• Coumaphos, US Environmental Protection Agency