tetrachlorvinphos

{{Chembox

| ImageFile = (Z)-Tetrachlorvinphos structure.svg

| ImageSize =

| PIN = (Z)-2-Chloro-1-(2,4,5-trichlorophenyl)ethen-1-yl dimethyl phosphate

| OtherNames = Stirofos; CVMP;[http://www.alanwood.net/pesticides/tetrachlorvinphos.html Tetrachlorvinphos], alanwood.net TCVP{{cite web | url = http://www.nrdc.org/living/chemicalindex/tetrachlorvinphos.asp | publisher = Natural Resources Defense Council | title = Tetrachlorvinphos (TCVP) }}

|Section1={{Chembox Identifiers

| CASNo = 22248-79-9

| CASNo_Ref = {{Cascite|correct|CAS}}

| Beilstein = 1890909

| ChEBI = 35005

| ChEMBL = 1452359

| ChemSpiderID = 4447527

| EINECS = 244-865-4

| KEGG = C14513

| KEGG1 = D05929

| PubChem = 5284462

| RTECS = TB9100000

| UNNumber = 2783

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

| UNII = DM33MW89QU

| SMILES = COP(=O)(OC)O/C(=C\Cl)/c1cc(c(cc1Cl)Cl)Cl

| 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

}}

|Section2={{Chembox Properties

| C=10 | H=9 | Cl=4 | O=4 | P=1

| Appearance =

| Density =

| MeltingPtC = 97 to 98

| MeltingPt_ref = {{cite web | url = https://www.sigmaaldrich.com/US/en/product/sial/43677 | title = Tetrachlorvinphos | publisher = Sigma-Aldrich}}

| BoilingPt =

| Solubility =

}}

|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 =

| FlashPt =

| AutoignitionPt =

}}

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.{{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 }} 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.{{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}} {{Cite web|url=http://www.nrdc.org/media/2014/140206.asp|title = NRDC Sues EPA to Ban Two Toxic Pesticides in Pet Flea Collars}}

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.{{Cite web|url=http://cameochemicals.noaa.gov/chemical/16121|title=TETRACHLORVINPHOS | CAMEO Chemicals | NOAA}}

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.

Alternative Chemical Names

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

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

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

External links

[https://web.archive.org/web/20141112003549/http://www.epa.gov/oppsrrd1/reregistration/tcvp/ Tetrachlorvinphos (TCVP)], Environmental Protection Agency

Category:Acetylcholinesterase inhibitors

Category:Organophosphate insecticides

Category:Chloroarenes

Category:IARC Group 2B carcinogens

Category:Methoxy compounds