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| {{chembox | {{chembox | ||
| ⚫ | | verifiedrevid = 443542165 | ||
| | Watchedfields = changed | |||
| ⚫ | | ImageFile = Coumaphos-Structural Formula V.1.svg | ||
| ⚫ | | verifiedrevid = |
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| ⚫ | | ImageSize = 220px | ||
| ⚫ | |ImageFile=Coumaphos. |
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| | ImageAlt = Skeletal formula of coumaphos | |||
| ⚫ | |ImageSize= |
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| | ImageFile1 = Coumaphos 3D spacefill.png | |||
| ⚫ | | |
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| | ImageSize1 = 220 | |||
| ⚫ | |OtherNames=3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone<br> |
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| | ImageAlt1 = Space-filling model of the coumaphos molecule | |||
| ⚫ | | PIN=''O''-(3-Chloro-4-methyl-2-oxo-2''H''-1-benzopyran-7-yl) ''O'',''O''-diethyl phosphorothioate | ||
| ⚫ | | OtherNames=3-Chloro-7-diethoxyphosphinothioyloxy-4-methyl-2-chromenone<br /> Coumaphos, Meldane, Asuntol, Azunthol, Muscatox, Agridip, Asuntol, Meldone, Resitox, Baymix | ||
| |Section1={{Chembox Identifiers | |Section1={{Chembox Identifiers | ||
| | |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| | ChemSpiderID = 2768 | | ChemSpiderID = 2768 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | | UNII_Ref = {{fdacite|correct|FDA}} | ||
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| | CASNo_Ref = {{cascite|correct|CAS}} | | CASNo_Ref = {{cascite|correct|CAS}} | ||
| | CASNo=56-72-4 | | CASNo=56-72-4 | ||
| | |
| PubChem=2871 | ||
| | ChEBI_Ref = {{ebicite|correct|EBI}} | |||
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| ChEBI = 3903 | ||
| ⚫ | | |
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| | ChEBI = 3903 | |||
| | SMILES = S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2 | | SMILES = S=P(OCC)(OCC)Oc2ccc\1c(OC(=O)C(/Cl)=C/1C)c2 | ||
| }} | }} | ||
| |Section2={{Chembox Properties | |Section2={{Chembox Properties | ||
| | |
| Formula=C<sub>14</sub>H<sub>16</sub>ClO<sub>5</sub>PS | ||
| | |
| MolarMass=362.77 g/mol | ||
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| Appearance= | ||
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| Density= | ||
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| MeltingPt= | ||
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| BoilingPt= | ||
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| Solubility= | ||
| }} | }} | ||
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|Section6={{Chembox Pharmacology | ||
| ⚫ | | ATCvet = yes | ||
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| | ATCCode_prefix = P53 | |||
| ⚫ | | |
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| ⚫ | | ATCCode_suffix = AF08 | ||
| | Autoignition= | |||
| }} | |||
| |Section7={{Chembox Hazards | |||
| ⚫ | | MainHazards= | ||
| ⚫ | | FlashPt= | ||
| | AutoignitionPt = | |||
| }} | }} | ||
| }} | }} | ||
| '''Coumaphos''' is a |
'''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> | ||
| It is also used to control ] in ] colonies, though in many areas it is falling out of favor as the |
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> | ||
| In ], its registration as suited to home ] use was cancelled by the ] in June 2004 after the manufacturer failed to show |
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> | ||
| 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> | |||
| ⚫ | ==References== | ||
| * | |||
| ⚫ | * , US Environmental Protection Agency | ||
| 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> | |||
| {{insecticides}} | |||
| {{Cholinergics}} | |||
| ⚫ | ==References== | ||
| ⚫ | ] | ||
| {{reflist}} | |||
| ⚫ | ] | ||
| ⚫ | ] | ||
| ⚫ | ] | ||
| ==External links== | |||
| ⚫ | * , US Environmental Protection Agency | ||
| {{Insecticides}} | |||
| {{organic-compound-stub}} | |||
| {{Acetylcholine metabolism and transport modulators}} | |||
| ] | |||
| ] | |||
| ⚫ | ] | ||
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Latest revision as of 16:07, 3 December 2024
 | |
 | |
| 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 | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.260 
|
| KEGG | |
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C14H16ClO5PS |
| Molar mass | 362.77 g/mol |
| Pharmacology | |
| ATCvet code | QP53AF08 (WHO) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
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.
References
- "Asuntol - Cattle, Goat, Sheep - anti lice, fleas, sucking flies and mite". vetcontact.com.
- "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.
- 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.
- "Coumaphos Review". www.apvma.gov.au. Archived from the original on August 29, 2008.
- "Neonicotinoid pesticides 'damage brains of bees'". BBC News. 27 March 2013.
- 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
External links
- Coumaphos, US Environmental Protection Agency