Tetrachlorvinphos

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

Tetrachlorvinphos
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
3D model (JSmol)
Beilstein Reference
 1890909
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.040.772
EC Number
  • 244-865-4
KEGG
PubChem CID
RTECS number
  • TB9100000
UNII
UN number 2783
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
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

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
  1. Tetrachlorvinphos, alanwood.net
  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".
  7. "TETRACHLORVINPHOS | CAMEO Chemicals | NOAA".

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

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