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Antiinfective agent stubs
Coumaphos
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Coumaphos

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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
KEGG
PubChem CID
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.

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.

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.

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

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.

External links

  • Coumaphos, US Environmental Protection Agency



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