Tetrachlorvinphos

Structural formula
	Structural formula of ( Z ) -Tetrachlorvinphos
General
Surname	Tetrachlorvinphos
other names	Stirofox; CVMP; ( Z ) -2-chloro-1- (2,4,5-trichlorophenyl) vinyl dimethyl phosphate;
Molecular formula	C 10 H 9 Cl 4 O 4 P
Brief description	yellowish to brown solid
External identifiers / databases
EC number	244-865-4
ECHA InfoCard	100.040.772
PubChem	5284462
Wikidata	Q27887626
properties
Molar mass	365.96 g mol −1
Physical state	firmly
Melting point	97-98 ° C
Vapor pressure	5.6 10 −8 mbar (20 ° C)
solubility	very poorly soluble in water (11 mg l −1 at 20 ° C); very poorly soluble in acetone, benzene, chloroform and xylene;
safety instructions
H and P phrases	H: 302-400
	P: 273
Toxicological data	480 mg kg −1 ( LD 50 , rat , oral ) ; > 2,500 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetrachlorvinphos is a chemical compound from the group of organophosphates .

Extraction and presentation

Tetrachlorvinphos can be obtained by reacting 2,2,2 ', 4', 5'-pentachloroacetophenone with trimethyl phosphite . The former, in turn, can be obtained by reacting 1,2,4-trichlorobenzene with dichloroacetyl chloride.

properties

Tetrachlorvinphos is a yellowish to brown solid that is very sparingly soluble in water. In neutral and acidic aqueous solution, slow hydrolysis takes place, in alkaline solution rapid hydrolysis.

use

Tetrachlorvinphos [more precisely the ( Z ) -isomer of the compound] is used as an insecticide against parasites ingested on the skin and through food, as well as flies in cattle, pigs, goats and horses. It is also used against bird mites in poultry, in flea collars for adult pets (weak action against ticks) and against flies on rubbish tips and in recreational areas. It was first approved in the United States in 1966. Its use as an insecticide on crops was banned in the USA in 1987. The effect is based on the inhibition of acetylcholinesterase .

Admission

Tetrachlorvinphos is not on the list of active ingredients for pesticides permitted in the European Union . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

safety instructions

Tetrachlorvinphos is not very toxic, but is classified as potentially carcinogenic. An evaluation by the IARC from March 2015 came to the conclusion that tetrachlorvinphos was classified in Category 2B ( possibly carcinogenic to humans ) on the basis of the tests carried out on rats and mice .

Individual evidence

↑ ^a ^b EPA: tetrachlorvinphos (Rabon, Gardona) EPA Pesticide Fact Sheet 10/88 .
↑ ^a ^b ^c ^d ^e ^f data sheet Tetrachlorvinphos, PESTANAL at Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
↑ ^a ^b ^c ^d EPA: Reregistration Eligibility Decision for Tetrachlorvinphos (TCVP) (PDF; 1.2 MB), July 2006.
↑ Entry on Tetrachlorvinphos. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.
^ Entry on tetrachlorvinphos in the Hazardous Substances Data Bank , accessed on August 20, 2012.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 304 ( limited preview in Google Book Search).
↑ Sandra N. Koch, Sheila MF Torres, Donald C. Plumb: Canine and Feline Dermatology Drug Handbook . John Wiley & Sons, 2012, ISBN 1-119-94994-7 , pp. 343 ( limited preview in Google Book search).
↑ Wolfgang Löscher, Fritz Rupert Ungemach, Reinhard Kroker: Pharmacotherapy for pets and farm animals . Georg Thieme Verlag, 2006, ISBN 3-8304-4160-6 , p. 320 ( limited preview in Google Book search).
↑ Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 499 ( limited preview in Google Book search).
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on tetrachlorvinphos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland and Germany ; accessed on March 12, 2016.
^ IARC press release of March 20, 2015 IARC Monographs Volume 112: evaluation of five organophosphate inscecticides and herbicides , accessed on March 23, 2015.

[EPA_Pesticide_Fact_Sheet-1] EPA: tetrachlorvinphos (Rabon, Gardona) EPA Pesticide Fact Sheet 10/88 .

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f data sheet Tetrachlorvinphos, PESTANAL at Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).

[EPA-3] EPA: Reregistration Eligibility Decision for Tetrachlorvinphos (TCVP) (PDF; 1.2 MB), July 2006.

[Römpp-4] Entry on Tetrachlorvinphos. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.

[HSDB-5] Entry on tetrachlorvinphos in the Hazardous Substances Data Bank , accessed on August 20, 2012.

[Thomas_A._Unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 304 ( limited preview in Google Book Search).

[Sandra_N._Koch,_Sheila_M._F._Torres,_Donald_C._Plumb-7] Sandra N. Koch, Sheila MF Torres, Donald C. Plumb: Canine and Feline Dermatology Drug Handbook . John Wiley & Sons, 2012, ISBN 1-119-94994-7 , pp. 343 ( limited preview in Google Book search).

[Wolfgang_Löscher,_Fritz_Rupert_Ungemach,_Reinhard_Kroker-8] Wolfgang Löscher, Fritz Rupert Ungemach, Reinhard Kroker: Pharmacotherapy for pets and farm animals . Georg Thieme Verlag, 2006, ISBN 3-8304-4160-6 , p. 320 ( limited preview in Google Book search).

[Terry_R._Roberts,_David_H._Hutson,_Philip_W._Lee,_Peter_H._Nicholls-9] Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 499 ( limited preview in Google Book search).

[10] Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.

[PSM-11] Directorate-General for Health and Food Safety of the European Commission: Entry on tetrachlorvinphos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland and Germany ; accessed on March 12, 2016.

[12] IARC press release of March 20, 2015 IARC Monographs Volume 112: evaluation of five organophosphate inscecticides and herbicides , accessed on March 23, 2015.