Vamidothion

Structural formula
	1: 1 mixture of two stereoisomers
General
Surname	Vamidothion
other names	O , O -Dimethyl- S -5- ( N -methyl-2-methyl-3-thiavaleramide) thiophosphate
Molecular formula	C 8 H 18 NO 4 PS 2
Brief description	white solid
External identifiers / databases
EC number	218-894-8
ECHA InfoCard	100.017.178
PubChem	560193
Wikidata	Q290452
properties
Molar mass	287.34 g mol −1
Physical state	firmly
Melting point	43 ° C
safety instructions
H and P phrases	H: 301-312-400
	P: 210-280-305 + 351 + 338
Toxicological data	64 mg kg −1 ( LD 50 , rat , oral ) ; 1160 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 .

Vamidothion is a mixture of two isomeric chemical compounds from the group of thiophosphoric acid esters . It is chiral and is used as an insecticide as a 1: 1 mixture of the mutually enantiomeric ( R ) form and the ( S ) form .

Extraction and presentation

Vamidothion can be obtained by reacting 2-chloroethanol with ethyl 2-mercaptopropionate , methylamine , thionyl chloride and dimethyl thiophosphate .

properties

Vamidothion as a pure substance is a white crystalline solid, whereas the technical product is a yellowish, waxy solid. The technical product decomposes slowly at room temperature, but is stable in organic solvents (e.g. cyclohexanone , methyl ethyl ketone ). It hydrolyzes under alkaline conditions .

use

Vamidothion is used as an acaricide . The most important application is the use in apples and pears against aphids. It is also used on other pome fruits, sugar beets and, to a lesser extent, on grapes, grains, sugar cane and hops.

Admission

Vamidothion 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.

Individual evidence

↑ ^a ^b ^c Joint Meeting on Pesticide Residues (JMPR), Monograph for Vamidothion , accessed December 9, 2014.
↑ ^a ^b ^c ^d ^e ^f Entry for CAS no. 2275-23-2 in the GESTIS substance database of the IFA , accessed on September 18, 2012(JavaScript required) .
↑ Entry on Vamidothion in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Data sheet Vamidothion solution, 100 ng / μL in acetonitrile from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 338 ( limited preview in Google Book search).
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Vamidothion in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[inchem.org-1] Joint Meeting on Pesticide Residues (JMPR), Monograph for Vamidothion , accessed December 9, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f Entry for CAS no. 2275-23-2 in the GESTIS substance database of the IFA , accessed on September 18, 2012(JavaScript required) .

[CLP_100.017.178-3] Entry on Vamidothion in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Sigma-4] Data sheet Vamidothion solution, 100 ng / μL in acetonitrile from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[Thomas_A._Unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 338 ( limited preview in Google Book search).

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

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Vamidothion in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.