Coumaphos

Coumaphos
Skeletal formula of coumaphos
Space-filling model of the coumaphos molecule
Names
Preferred IUPAC name
O-(3-Chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl phosphorothioate
Other names
3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone
Coumaphos, Meldane, Asuntol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.260 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: BXNANOICGRISHX-UHFFFAOYSA-N checkY
  • 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
  • S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2
Properties
C14H16ClO5PS
Molar mass 362.77 g/mol
Pharmacology
QP53AF08 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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. Archived from the original on 2017-02-26. Retrieved 2008-08-28.
  3. ^ Johnson, Reed M.; Ellis, Marion D.; Mullin, Christopher A.; Frazier, Maryann (2010). "Pesticides and honey bee toxicity – USA" (PDF). Apidologie. 41 (3): 312. doi:10.1051/apido/2010018. S2CID 12927448.
  4. ^ "Coumaphos Review". www.apvma.gov.au. Archived from the original on August 29, 2008.
  5. ^ "Neonicotinoid pesticides 'damage brains of bees'". BBC News. 27 March 2013.
  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, archived from the original (PDF) on February 25, 2012, retrieved October 29, 2011
  • Coumaphos, US Environmental Protection Agency


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