Tetrachlorvinphos

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Tetrachlorvinphos
File:(Z)-Tetrachlorvinphos structure.svg
Names
Preferred IUPAC name
(Z)-2-Chloro-1-(2,4,5-trichlorophenyl)ethen-1-yl dimethyl phosphate
Other names
  • Stirofos
  • CVMP[1]
  • TCVP[2]
  • Benzyl alcohol, 2,4,5-trichloro-α-(chloromethylene)-, dimethyl phosphate
  • 2-Chloro-1-(2,4,5-trichlorophenyl) vinyl dimethyl phosphate
  • Gardona
  • IPO 8
  • NCI C00168
  • Rabon
  • Tetrachlorvinphos[3]
Identifiers
3D model (JSmol)
1890909
ChEBI
ChEMBL
ChemSpider
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EC Number
  • 244-865-4
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KEGG
RTECS number
  • TB9100000
UNII
UN number 2783
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  • 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
  • COP(=O)(OC)O/C(=C\Cl)/c1cc(c(cc1Cl)Cl)Cl
Properties
C10H9Cl4O4P
Molar mass 365.95 g·mol−1
Melting point 97 to 98 °C (207 to 208 °F; 370 to 371 K)[4]
Pharmacology
QP53AF14 (WHO) QP53BB04 (WHO)
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H332, H410
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).

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

History

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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.[5] 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.[6][7]

Human health hazards

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Symptoms of exposure to this material include increased perspiration, nausea, lachrymation, salivation, blurred vision, diarrhea, pulmonary edema, respiratory depression 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.[3]

Chemical properties

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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.[3]

References

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

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