Tetrachlorvinphos: Difference between revisions

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	{{Chembox		{{Chembox
	\| ImageFile = Tetrachlorvinphos structure.~~png~~		\| ImageFile = (Z)-Tetrachlorvinphos structure.svg
	\| ImageSize =		\| ImageSize =
	\| ~~SystematicName~~ = ~~dimethoxy~~ phosphate		\| PIN = (''Z'')-2-Chloro-1-(2,4,5-trichlorophenyl)ethen-1-yl dimethyl phosphate
	\| OtherNames = Stirofos;<ref name=alanwood>, alanwood.net</ref~~> CVMP;<ref name=alanwood/~~> TCVP<ref name=nrdc>{{cite web \| url = http://www.nrdc.org/living/chemicalindex/tetrachlorvinphos.asp \| publisher = ] \| title = Tetrachlorvinphos (TCVP) }}</ref>		\| OtherNames = Stirofos; CVMP;<ref name=alanwood>, alanwood.net</ref> TCVP<ref name=nrdc>{{cite web \| url = http://www.nrdc.org/living/chemicalindex/tetrachlorvinphos.asp \| publisher = ] \| title = Tetrachlorvinphos (TCVP) }}</ref>
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 22248-79-9		\| CASNo = 22248-79-9
			\| CASNo_Ref = {{Cascite\|correct\|CAS}}
⚫	\| PubChem =
			\| Beilstein = 1890909
⚫	\| ChemSpiderID = ~~25077200~~
	\| ~~ATCvet~~ = ~~yes~~		\| ChEBI = 35005
			\| ChEMBL = 1452359
⚫	\| ATCCode_prefix = P53
		⚫	\| ChemSpiderID = 4447527
⚫	\| ATCCode_suffix = AF14
			\| EINECS = 244-865-4
⚫	\| ATC_Supplemental = {{ATCvet\|P53\|BB04}}
			\| KEGG = C14513
			\| KEGG1 = D05929
		⚫	\| PubChem = 5284462
			\| RTECS = TB9100000
			\| UNNumber = 2783
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = DM33MW89QU		\| UNII = DM33MW89QU
	\| SMILES = ~~COOP~~(=O)(O/C(=C\Cl)/c1cc(c(cc1Cl)Cl)Cl~~)OOC~~		\| SMILES = COP(=O)(OC)O/C(=C\Cl)/c1cc(c(cc1Cl)Cl)Cl
	\| ~~InChI~~ = 1/~~C10H9Cl4O6P~~/c1-16-19~~-21~~(15,~~20-~~17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5-		\| StdInChI = InChI=1S/C10H9Cl4O4P/c1-16-19(15,17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5-
		⚫	\| StdInChIKey = UBCKGWBNUIFUST-YHYXMXQVSA-N
	\| InChIKey = ZKERVNBIQYEUTA-YHYXMXQVBE
	\| StdInChI = 1S/C10H9Cl4O6P/c1-16-19-21(15,20-17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5-
⚫	\| StdInChIKey = ~~ZKERVNBIQYEUTA~~-YHYXMXQVSA-N
	}}		}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| C =10\|H=9\|Cl=4\|O=6\|P=1		\| C=10 \| H=9 \| Cl=4 \| O=4 \| P=1
	\| Appearance =		\| Appearance =
	\| Density =		\| Density =
	\| MeltingPtC = 97 to 98		\| MeltingPtC = 97 to 98
	\| ~~Melting_ref~~ = <ref>{{cite web \| url = ~~http~~://www.sigmaaldrich.com/~~catalog~~/product/~~fluka~~/~~45679?lang=en~~ \| title = Tetrachlorvinphos \| publisher = ]}}</ref>		\| MeltingPt_ref = <ref>{{cite web \| url = https://www.sigmaaldrich.com/US/en/product/sial/43677 \| title = Tetrachlorvinphos \| publisher = ]}}</ref>
	\| BoilingPt =		\| BoilingPt =
	\| Solubility =		\| Solubility =
	}}		}}
	\|~~Section3~~={{Chembox ~~Hazards~~		\|Section6={{Chembox Pharmacology
			\| ATCvet = yes
		⚫	\| ATCCode_prefix = P53
		⚫	\| ATCCode_suffix = AF14
		⚫	\| ATC_Supplemental = {{ATCvet\|P53\|BB04}}
			}}
			\|Section7={{Chembox Hazards
			\| GHSPictograms = {{GHS07}}{{GHS09}}
			\| GHSSignalWord = Warning
			\| HPhrases = {{H-phrases\|302\|332\|410}}
			\| PPhrases = {{P-phrases\|261\|264\|270\|271\|273\|301+312\|304+312\|304+340\|312\|330\|391\|501}}
	\| MainHazards =		\| MainHazards =
	\| FlashPt =		\| FlashPt =
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	==History==		==History==
	Tetrachlorvinphos was initially registered for use in the United States in 1966 by the ]. Tetrachlorvinphos was originally registered for use on various food crops, livestock, pet animals, and in or around buildings. The crop uses were voluntarily canceled from product registrations in 1987. <ref> http://www.epa.gov/oppsrrd1/REDs/factsheets/0321fact.pdf </ref> In 2014, the ] (NRDC) filed a lawsuit against the ] (EPA) seeking EPA to respond to ~~NRDC’s~~ 2009 petition to ban tetrachlorvinphos in common pet flea treatment products. <ref> http://ecowatch.com/2014/02/06/epa-sued-over-pesticides-flea-collars/ </ref><ref> http://www.nrdc.org/media/2014/140206.asp </ref>		Tetrachlorvinphos was initially registered for use in the United States in 1966 by the ]. Tetrachlorvinphos was originally registered for use on various food crops, livestock, pet animals, and in or around buildings. The crop uses were voluntarily canceled from product registrations in 1987.<ref>{{cite web\|url=http://www.epa.gov/oppsrrd1/REDs/factsheets/0321fact.pdf \|title=Archived copy \|access-date=2013-07-28 \|url-status=dead \|archive-url=https://web.archive.org/web/20140809140513/http://www.epa.gov/oppsrrd1/REDs/factsheets/0321fact.pdf \|archive-date=2014-08-09 }}</ref> In 2014, the ] (NRDC) filed a lawsuit against the ] (EPA) seeking EPA to respond to NRDC's 2009 petition to ban tetrachlorvinphos in common pet flea treatment products.<ref>{{cite web \|url=http://ecowatch.com/2014/02/06/epa-sued-over-pesticides-flea-collars/ \|title=EPA Sued Over Toxic Pesticides in Pet Flea Collars {{!}} EcoWatch \|website=ecowatch.com \|url-status=dead \|archive-url=https://web.archive.org/web/20140209023439/http://ecowatch.com/2014/02/06/epa-sued-over-pesticides-flea-collars/ \|archive-date=2014-02-09}} </ref><ref>{{Cite web\|url=http://www.nrdc.org/media/2014/140206.asp\|title = NRDC Sues EPA to Ban Two Toxic Pesticides in Pet Flea Collars}}</ref>

	==Human health hazards==		==Human health hazards==
	Symptoms of exposure to this material include increased ], ], ], ], blurred vision, ], ], respiratory embarrassment and ]s. The chemical material may be absorbed through the skin and is a lachrymator. It is a ] and is a positive animal carcinogen. <ref> http://cameochemicals.noaa.gov/chemical/16121 </ref>		Symptoms of exposure to this material include increased ], ], ], ], blurred vision, ], ], respiratory embarrassment and ]s. The chemical material may be absorbed through the skin and is a lachrymator. It is a ] and is a positive animal ].<ref name="cameochemicals.noaa.gov">{{Cite web\|url=http://cameochemicals.noaa.gov/chemical/16121\|title=TETRACHLORVINPHOS \| CAMEO Chemicals \| NOAA}}</ref>

	==Chemical properties==		==Chemical properties==
	The substance is insoluble in water. ] data are not available for this chemical; however, it is probably combustible. Tetrachlorvinphos is slowly hydrolyzed in neutral and aqueous acidic media. Is rapidly hydrolyzed in alkaline media. <ref> ~~http://~~cameochemicals.noaa.gov/~~chemical/16121 </ref~~>		The substance is insoluble in water. ] data are not available for this chemical; however, it is probably combustible. Tetrachlorvinphos is slowly hydrolyzed in neutral and aqueous acidic media. Is rapidly hydrolyzed in alkaline media.<ref name="cameochemicals.noaa.gov"/>

	==Alternative Chemical Names==		==Alternative Chemical Names==
	This is a listing of alternate names for this chemical, including trade names and synonyms. <ref> ~~http://~~cameochemicals.noaa.gov/~~chemical/16121 </ref~~>		This is a listing of alternate names for this chemical, including trade names and synonyms.<ref name="cameochemicals.noaa.gov"/>

	* BENZYL ALCOHOL, 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)-, DIMETHYL PHOSPHATE		* BENZYL ALCOHOL, 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)-, DIMETHYL PHOSPHATE
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	* 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL ALCOHOL DIMETHYL PHOSPHATE		* 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL ALCOHOL DIMETHYL PHOSPHATE
	* 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL PHOSPHATE		* 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL PHOSPHATE


	==References==		==References==
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	==External links==		==External links==
	* , ]		* , ]

			{{Acetylcholine metabolism and transport modulators}}

			]
	]		]
	]		]
			]

			]

	{{organic-compound-stub}}

Latest revision as of 22:34, 12 June 2023

Tetrachlorvinphos
Names

Preferred IUPAC name (Z)-2-Chloro-1-(2,4,5-trichlorophenyl)ethen-1-yl dimethyl phosphate
Other names Stirofos; CVMP; TCVP
Identifiers
CAS Number	22248-79-9
3D model (JSmol)	Interactive image
Beilstein Reference	1890909
ChEBI	CHEBI:35005
ChEMBL	ChEMBL1452359
ChemSpider	4447527
ECHA InfoCard	100.040.772
EC Number	244-865-4
KEGG	C14513 D05929
PubChem CID	5284462
RTECS number	TB9100000
UNII	DM33MW89QU
UN number	2783
CompTox Dashboard (EPA)	DTXSID1032648
InChI InChI=1S/C10H9Cl4O4P/c1-16-19(15,17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5-Key: UBCKGWBNUIFUST-YHYXMXQVSA-N
SMILES COP(=O)(OC)O/C(=C\Cl)/c1cc(c(cc1Cl)Cl)Cl
Properties
Chemical formula	C₁₀H₉Cl₄O₄P
Molar mass	365.95 g·mol
Melting point	97 to 98 °C (207 to 208 °F; 370 to 371 K)
Pharmacology
ATCvet code	QP53AF14 (WHO) QP53BB04 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H332, H410
Precautionary statements	P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Tetrachlorvinphos is an organophosphate insecticide used to kill fleas and ticks.

History

Tetrachlorvinphos was initially registered for use in the United States in 1966 by the U.S. Department of Agriculture. Tetrachlorvinphos was originally registered for use on various food crops, livestock, pet animals, and in or around buildings. The crop uses were voluntarily canceled from product registrations in 1987. In 2014, the Natural Resources Defense Council (NRDC) filed a lawsuit against the United States Environmental Protection Agency (EPA) seeking EPA to respond to NRDC's 2009 petition to ban tetrachlorvinphos in common pet flea treatment products.

Human health hazards

Symptoms of exposure to this material include increased perspiration, nausea, lachrymation, salivation, blurred vision, diarrhea, pulmonary edema, respiratory embarrassment and convulsions. The chemical material may be absorbed through the skin and is a lachrymator. It is a cholinesterase inhibitor and is a positive animal carcinogen.

Chemical properties

The substance is insoluble in water. Flash point data are not available for this chemical; however, it is probably combustible. Tetrachlorvinphos is slowly hydrolyzed in neutral and aqueous acidic media. Is rapidly hydrolyzed in alkaline media.