Dimethylvinphos

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Dimethylvinphos
other names	( Z ) -2-chloro-1- (2,4-dichlorophenyl) vinyl dimethyl phosphate; Rangado;
Molecular formula	C 10 H 10 Cl 3 O 4 P
Brief description	white crystals
External identifiers / databases
EC number	607-152-2
ECHA InfoCard	100.114.978
PubChem	16769
ChemSpider	21865388
Wikidata	Q22807428
properties
Molar mass	331.52 g mol −1
Physical state	firmly
density	1.26 g cm −3
Melting point	69.5 ° C
boiling point	decomposes when heated
Vapor pressure	1.3 · 10 −3 Pa (20 ° C)
solubility	very heavy in water (0.13 g l −1 at 25 ° C); slightly in xylene 325 g l −1 at 20 ° C); easily in acetone 375 g l −1 at 20 ° C); easily in cyclohexanone 475 g l −1 at 20 ° C);
safety instructions
H and P phrases	H: 310-410
	P: 301 + 330 + 331 + 310
Toxicological data	155–210 mg kg −1 ( LD 50 , rat , oral ) ; 0.97–1.186 mg l −1 ( LC 50 , rat , inhalation 4 h ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethlyvinphos is a synthetic insecticide from the active ingredient group of organophosphates . It was launched in 1966.

Extraction and presentation

Dimethylvinphos is produced analogously to the structurally related tetrachlorvinphos . The reaction of 1,3-dichlorobenzene with dichloroacetyl chloride gives 2,2,2 ', 4', 5'- pentachloroacetophenone . This in turn reacts with trimethyl phosphite to form dimethyl vinphos.

Structure and properties

There are two diastereomers of dimethylvinphos. However, more than 95% of the ( Z ) -isomer occurs in technical products .

Dimethylvinphos is a white, crystalline solid that is very sparingly soluble in water. The substance is unstable in sunlight and hydrolyzes in neutral water with a half-life of 40 days.

Use and mode of action

In countries where Dimethylvinphos is approved, it is available as a powder under the name Rangado .

Dimethylvinphos is mainly used as an insecticide in rice cultivation. It is mainly used against curlers and stalk-boring insects. It acts both as a contact poison and as a food poison.

The effect of Dimethylvinphos is based on the inhibition of acetylcholinesterase in insects. This prevents the nervous system from transmitting signals, which can lead to paralysis, respiratory failure and even death.

Analytics

The reliable detection and quantification of dimethylvinphos can be carried out using liquid chromatographic methods. A mass spectrometer can be used for identification after the chromatographic separation .

Admission

Dimethylvinphos is not approved in the European Union or Switzerland . In the EU, the maximum residue limit in all foods is 0.01 mg / kg.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Dimethylvinphos in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 10, 2019.
↑ ^a ^b ^c ^d data sheet Dimethlyvinphos at Sigma-Aldrich , accessed on January 10, 2019 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 304 ( limited preview in Google Book Search).
↑ External identifiers of or database links to (Z) -Dimethylvinphos : CAS number: 67628-93-7, EC number: 811-278-5, ECHA -InfoCard: 100.241.577 , Wikidata : Q90008452 .
↑ ^a ^b ^c Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls, Jack R. Plimmer: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 2007, ISBN 978-1-84755-137-5 , pp. 282 ff . ( limited preview in Google Book search).
↑ ^a ^b Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).
↑ Jimi Cho, Jonghwa Lee, Chai-Uk Lim & Jongsung Ahn: Quantification of pesticides in food crops using QuEChERS approaches and GC-MS / MS . In: Food Additives & Contaminants: Part A . tape 33 , no. 12 . Taylor & Francis, 2016, pp. 1803-1816 , doi : 10.1080 / 19440049.2016.1235800 ( researchgate.net ).
^ Directorate-General for Health and Food Safety of the European Commission: Entry on dimethylvinphos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on January 10, 2019.

[PPDB-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Dimethylvinphos in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 10, 2019.

[Sigma-2] ta sheet Dimethlyvinphos at Sigma-Aldrich , accessed on January 10, 2019 ( PDF ).

[Thomas_A._Unger-3] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 304 ( limited preview in Google Book Search).

[4] External identifiers of or database links to (Z) -Dimethylvinphos : CAS number: 67628-93-7, EC number: 811-278-5, ECHA -InfoCard: 100.241.577 , Wikidata : Q90008452 .

[Roberts-5] Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls, Jack R. Plimmer: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 2007, ISBN 978-1-84755-137-5 , pp. 282 ff . ( limited preview in Google Book search).

[kalyani-6] Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).

[7] Jimi Cho, Jonghwa Lee, Chai-Uk Lim & Jongsung Ahn: Quantification of pesticides in food crops using QuEChERS approaches and GC-MS / MS . In: Food Additives & Contaminants: Part A . tape 33 , no. 12 . Taylor & Francis, 2016, pp. 1803-1816 , doi : 10.1080 / 19440049.2016.1235800 ( researchgate.net ).

[8] Directorate-General for Health and Food Safety of the European Commission: Entry on dimethylvinphos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on January 10, 2019.