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{{chembox |
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| verifiedrevid = 443542165 |
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| ImageFile = Coumaphos-Structural Formula V.1.svg |
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| verifiedrevid = 414085572 |
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| ImageSize = 220px |
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|ImageFile=Coumaphos.png |
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| ImageAlt = Skeletal formula of coumaphos |
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|ImageSize=200px |
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| ImageFile1 = Coumaphos 3D spacefill.png |
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|IUPACName=''O'',''O''-Diethyl ''O''-3-chloro-4-methyl-2-oxo-2''H''-chromen-7-yl phosphorothioate |
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| ImageSize1 = 220 |
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|OtherNames=3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone<br>Coumafos, Meldane, Asunthol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix |
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| ImageAlt1 = Space-filling model of the coumaphos molecule |
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| PIN=''O''-(3-Chloro-4-methyl-2-oxo-2''H''-1-benzopyran-7-yl) ''O'',''O''-diethyl phosphorothioate |
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| OtherNames=3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone<br /> Coumaphos, Meldane, Asuntol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2768 |
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| ChemSpiderID = 2768 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=56-72-4 |
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| CASNo=56-72-4 |
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| PubChem=2871 |
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| PubChem=2871 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ATCvet = yes |
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| ATCCode_prefix = P53 |
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| ChEBI = 3903 |
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| ATCCode_suffix = AF08 |
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| ChEBI = 3903 |
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| SMILES = S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2 |
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| SMILES = S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>14</sub>H<sub>16</sub>ClO<sub>5</sub>PS |
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| Formula=C<sub>14</sub>H<sub>16</sub>ClO<sub>5</sub>PS |
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| MolarMass=362.77 g/mol |
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| MolarMass=362.77 g/mol |
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|Section3={{Chembox Hazards |
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|Section6={{Chembox Pharmacology |
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| ATCvet = yes |
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| MainHazards= |
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| ATCCode_prefix = P53 |
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| ATCCode_suffix = AF08 |
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|Section7={{Chembox Hazards |
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'''Coumaphos''' is a non-volatile, fat-soluble ] with ] properties: it kills insects and mites. It is well known under manufacturer brand-names as a dip or wash, used on farm and domestic animals to control ticks, mites, flies and fleas. |
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'''Coumaphos''' is a nonvolatile, fat-soluble ] with ] properties: it kills ] and ]. 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.<ref>{{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}}</ref> |
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It is also used to control ] in ] colonies, though in many areas it is falling out of favor as the varroa develop ] and as the residual toxicity effects are becoming better understood. |
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It is also used to control ] in ] colonies, though in many areas it is falling out of favor as the mites develop ] and as the residual toxicity effects are becoming better understood.<ref>{{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 }}</ref><ref>{{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 }}</ref> |
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In ], its registration as suited to home ] use was cancelled by the ] in June 2004 after the manufacturer failed to show that it was safe for use on pets. |
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In ], its registration as suited to home ] use was cancelled by the ] in June 2004 after the manufacturer failed to show it was safe for use on pets.<ref>{{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}}</ref> |
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The compound has been linked to neurological problems in bees, and may be a factor in colony collapse.<ref>{{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}}</ref> |
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==References== |
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* , US Environmental Protection Agency |
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It is classified as an ] in the United States as defined in Section 302 of the U.S. ] ({{UnitedStatesCode|42|11002}}), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Citation| publisher = ] | 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 }}</ref> |
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{{insecticides}} |
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{{Cholinergics}} |
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==References== |
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{{reflist}} |
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==External links== |
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* , US Environmental Protection Agency |
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{{Insecticides}} |
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{{organic-compound-stub}} |
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{{Acetylcholine metabolism and transport modulators}} |
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