Chlfenvinphos

Structural formula
Mixture of ( E ) and ( Z ) isomers
General
Surname	Chlfenvinphos
other names	O - (2-chloro-1- (2,4-dichlorophenyl) vinyl) - O , O -diethyl phosphate Haptasol Haptarax Sapecron Birlane Diethyl (2-chloro-1- (2,4-dichlorophenyl)) vinyl phosphate Phosphoric acid (2-chloro-1- (2,4-dichlorophenyl) ethenyl) diethyl ester
Molecular formula	C 12 H 14 Cl 3 O 4 P
Brief description	amber liquid
External identifiers / databases
CAS number 470-90-6 [( EZ ) mixture] 18708-86-6 [( E ) -isomer] 18708-87-7 [( Z ) -isomer] EC number 207-432-0 ECHA InfoCard 100.006.758 PubChem 5377791 Wikidata Q408184
properties
Molar mass	359.57 g mol −1
Physical state	liquid
density	1.36 g cm −3
Melting point	−23 - −19 ° C
boiling point	167-170 ° C (0.66 mbar)
Vapor pressure	<0.001 hPa (20 ° C)
solubility	heavy in water (145 mg l −1 at 20 ° C) miscible with acetone, xylene, ethanol, kerosene and propylene glycol
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 300 + 330-311-410 P: 260-264-280-284-301 + 310
Toxicological data	10 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlorfenvinphos is a mixture of two isomeric chemical compounds from the group of organic phosphoric acid esters .

Extraction and presentation

Chlorfenvinphos can be obtained by reacting m - dichlorobenzene with dichloroacetyl chloride and then reacting the intermediate product with triethyl phosphite .

properties

Chlfenvinphos is a colorless liquid in its pure form, and as a technical product it is amber-colored, which is sparingly soluble in water. The technical product is a mixture of cis and trans isomers. It contains no less than 92% chlorfenvinphos, with a typical sample containing 9.7% of the cis and 83.8% trans isomers. The cis isomer is less effective as an insecticide than the trans isomer.

use

Chlfenvinphos is an insecticide that was used in the United States until 1991. Thereafter, use in the United States was banned. Commercial preparations usually contain 90% chlorfenvinphos in liquid form. Chlfenvinphos acts as a cholinesterase inhibitor and slowly hydrolyzes in solution.

Admission

In Switzerland, chlorfenvinphos was approved in some preparations against cabbage , carrot and onion fly in vegetable cultivation. In the EU states including Germany and Austria as well as in Switzerland, pesticides containing chlorfenvinphos as an active ingredient are no longer permitted.

Individual evidence

1. ↑ ^{a b c} data sheet chlorfenvinphos from Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
2. ↑ ^{a b c d e f g h} Entry on chlorfenvinphos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
3. ↑ ^{a b} Joint Meeting on Pesticide Residues (JMPR), Monograph für Chlorfenvinphos , accessed December 9, 2014.
4. ↑ Entry on chlorfenvinphos in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 293 in the Google book search).
6. ^ Agency for Toxic Substances and Disease Registry: Chlorfenvinphos
7. ^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 224 in Google book search).
8. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Chlfenvinphos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.