Tetrachlorvinphos

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−1
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 [77 °F], 100 kPa). Infobox references

Tetrachlorvinphos is an organophosphate insecticide used to kill fleas and ticks.^[2]

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.^[4] 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.^[5]^[6]

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.^[7]

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.^[7]

Alternative Chemical Names

This is a listing of alternate names for this chemical, including trade names and synonyms.^[7]

BENZYL ALCOHOL, 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)-, DIMETHYL PHOSPHATE
2-CHLORO-1-(2,4,5-TRICHLOROPHENYL)VINYL DIMETHYL PHOSPHATE
2-CHLORO-1-(2,4,5-TRICHLOROPHENYL)VINYL PHOSPHORIC ACID DIMETHYL ESTER
DIMETHYL 2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL PHOSPHATE
GARDONA
IPO 8
NCI C00168
PHOSPHORIC ACID, 2-CHLORO-1-(2,3,5-TRICHLOROPHENYL) ETHENYL DIMETHYL ESTER
PHOSPHORIC ACID, 2-CHLORO-1-(2,4,5-TRICHLOROPHENYL)VINYL DIMETHYL ESTER
RABON
RABOND
TETRACHLORVINPHOS
2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL ALCOHOL DIMETHYL PHOSPHATE
2,4,5-TRICHLORO-ALPHA-(CHLOROMETHYLENE)BENZYL PHOSPHATE

References

^ Tetrachlorvinphos, alanwood.net
^ ^a ^b "Tetrachlorvinphos (TCVP)". Natural Resources Defense Council.
^ "Tetrachlorvinphos". Sigma-Aldrich.
^ "Archived copy" (PDF). Archived from the original (PDF) on 2014-08-09. Retrieved 2013-07-28.{{cite web}}: CS1 maint: archived copy as title (link)
^ "EPA Sued Over Toxic Pesticides in Pet Flea Collars | EcoWatch". ecowatch.com. Archived from the original on 2014-02-09.
^ "NRDC Sues EPA to Ban Two Toxic Pesticides in Pet Flea Collars".
^ ^a ^b ^c "TETRACHLORVINPHOS | CAMEO Chemicals | NOAA".

This article contains public domain text from the EPA and the NOAA .

External links

Tetrachlorvinphos (TCVP), Environmental Protection Agency

[alanwood-1] Tetrachlorvinphos, alanwood.net

[nrdc-2] "Tetrachlorvinphos (TCVP)". Natural Resources Defense Council.

[3] "Tetrachlorvinphos". Sigma-Aldrich.

[4] "Archived copy" (PDF). Archived from the original (PDF) on 2014-08-09. Retrieved 2013-07-28.{{cite web}}: CS1 maint: archived copy as title (link)

[5] "EPA Sued Over Toxic Pesticides in Pet Flea Collars | EcoWatch". ecowatch.com. Archived from the original on 2014-02-09.

[6] "NRDC Sues EPA to Ban Two Toxic Pesticides in Pet Flea Collars".

[cameochemicals.noaa.gov-7] "TETRACHLORVINPHOS | CAMEO Chemicals | NOAA".

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Names

Preferred IUPAC name (Z)-2-Chloro-1-(2,4,5-trichlorophenyl)ethen-1-yl dimethyl phosphate
Other names Stirofos; CVMP;^[1] TCVP^[2]
Identifiers
CAS Number	22248-79-9^Y
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^Y
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⁻¹
Melting point	97 to 98 °C (207 to 208 °F; 370 to 371 K)^[3]
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 [77 °F], 100 kPa). Infobox references