:Coumaphos

{{chembox

| verifiedrevid = 443542165

| ImageFile = Coumaphos-Structural Formula V.1.svg

| ImageSize = 220px

| ImageAlt = Skeletal formula of coumaphos

| ImageFile1 = Coumaphos 3D spacefill.png

| ImageSize1 = 220

| ImageAlt1 = Space-filling model of the coumaphos molecule

| PIN=O-(3-Chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl phosphorothioate

| OtherNames=3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone
Coumaphos, Meldane, Asuntol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2768

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = L08SZ5Z5JC

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07750

| 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

| InChIKey = BXNANOICGRISHX-UHFFFAOYAO

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 251680

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BXNANOICGRISHX-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=56-72-4

| PubChem=2871

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 3903

| SMILES = S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2

}}

|Section2={{Chembox Properties

| Formula=C₁₄H₁₆ClO₅PS

| MolarMass=362.77 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section6={{Chembox Pharmacology

| ATCvet = yes

| ATCCode_prefix = P53

| ATCCode_suffix = AF08

}}

|Section7={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

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.{{cite web | url = http://www.vetcontact.com/en/art.php?a=52&t= | title = Asuntol - Cattle, Goat, Sheep - anti lice, fleas, sucking flies and mite | publisher = vetcontact.com}}

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.{{Cite web | url = http://www.biosecurity.govt.nz/pests-diseases/animals/varroa/paper/varroa-treatment-options.htm#8 | title = A Review of Treatment Options for Control of Varroa Mite in New Zealand | publisher = biosecurity.govt.nz | access-date = 2008-08-28 | archive-url = https://web.archive.org/web/20170226141153/http://www.biosecurity.govt.nz/pests-diseases/animals/varroa/paper/varroa-treatment-options.htm#8 | archive-date = 2017-02-26 | url-status = dead }}{{cite journal | doi = 10.1051/apido/2010018 | title = Pesticides and honey bee toxicity – USA | year = 2010 | last1 = Johnson | first1 = Reed M. | last2 = Ellis | first2 = Marion D. | last3 = Mullin | first3 = Christopher A. | last4 = Frazier | first4 = Maryann | journal = Apidologie | volume = 41 | issue = 3 | pages = 312| s2cid = 12927448 | url = https://hal.archives-ouvertes.fr/hal-00892096/file/hal-00892096.pdf }}

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.{{cite web |url=http://www.apvma.gov.au/chemrev/coumaphos.shtml |title= Coumaphos Review|website=www.apvma.gov.au |archive-url=https://web.archive.org/web/20080829185148/http://www.apvma.gov.au/chemrev/coumaphos.shtml |archive-date=August 29, 2008}}

The compound has been linked to neurological problems in bees, and may be a factor in colony collapse.{{Cite news|url=https://www.bbc.co.uk/news/science-environment-21958547|title = Neonicotinoid pesticides 'damage brains of bees'|work = BBC News|date = 27 March 2013}}

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 ({{UnitedStatesCode|42|11002}}), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.{{Citation| publisher = Government Printing Office | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = July 1, 2008 | access-date = October 29, 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = February 25, 2012 | url-status = dead }}