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Coumaphos

From Wikipedia, the free encyclopedia
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 InfoCard100.000.260Edit 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 mass362.77 g/mol
Pharmacology
QP53AF08 (WHO)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Coumaphos is a nonvolatile, fat-solublephosphorothioate withectoparasiticide properties: it killsinsects andmites. 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 controlVarroa mites inhoney bee colonies, though in many areas it is falling out of favor as the mites developresistance and as the residual toxicity effects are becoming better understood.[2][3]

InAustralia, its registration as suited to homeveterinary use was cancelled by theAustralian 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 anextremely 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

[edit]
  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 fromthe original on 2017-02-26. Retrieved2008-08-28.
  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 fromthe 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 fromthe original(PDF) on February 25, 2012, retrievedOctober 29, 2011

External links

[edit]
  • Coumaphos, US Environmental Protection Agency
Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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