Methidathione

Structural formula
General
Surname	Methidathione
other names	O , O -Dimethyl- S - (2-methoxy-1,3,4 (4 H ) -thiadiazol-5-on-4-yl) methyldithiophosphate ( IUPAC )
Molecular formula	C 6 H 11 N 2 O 4 PS 3
Brief description	colorless solid
External identifiers / databases
EC number	213-449-4
ECHA InfoCard	100.012.227
PubChem	13709
ChemSpider	13115
Wikidata	Q411730
properties
Molar mass	302.34 g mol −1
Physical state	firmly
density	1.51 g cm −3
Melting point	39 - 40 ° C
solubility	slightly soluble in water (240 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 300 + 310 + 330-318-410
	P: 262-280-301 + 310 + 330-302 + 352 + 310-304 + 340 + 310-305 + 351 + 338 + 310
Toxicological data	20 mg kg −1 ( LD 50 , rat , oral ) ; 196 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 .

Methidathione is a chemical compound from the group of thiophosphoric acid esters .

Extraction and presentation

Methidathione can be obtained by a multistage reaction based on a reaction between methanol , carbon disulfide and hydrazine and a further reaction of the intermediate product methyl thiocarbamic acid with phosgene , formaldehyde , thionyl chloride and O , O -dimethyl hydrogen dithiophosphate .

properties

Methidathione is a colorless solid that is sparingly soluble in water. It is stable under neutral and slightly acidic conditions, but hydrolyzes rapidly under alkaline conditions.

use

Methidathione is a non-systemic organophosphate - insecticide and acaricide with feeding and contact effects. It is used to control insects and mites in fruits, vegetables, tobacco, alfalfa and sunflowers and is particularly effective against scale insects . It is sold, for example, under the trade names Ultrazid and Supracid and works by inhibiting acetylcholinesterase .

Admission

Methidathione has not been approved as an active ingredient in pesticides in the European Union since 2004. Some EU states have been given a transition period until June 30, 2007 for certain applications (for Germany in oilseed rape). In Switzerland, too, no pesticides containing this active ingredient are permitted. Its manufacture and export is legal (as of 2019).

Individual evidence

↑ Methidathion data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on methidathione in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .

↑ Entry on methidathione 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 .

↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 617 (English, limited preview in Google Book search).

^ ^A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 377 (English, limited preview in Google Book search).

↑ entry methidathion at Extoxnet.

↑ Decision of the Commission of January 30, 2004 on the non-inclusion of certain active substances in Annex I of Directive 91/414 / EEC of the Council as well as the revocation of the authorizations for plant protection products with these active substances

^ Directorate-General for Health and Food Safety of the European Commission: Entry on methidathione in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

↑ Stefan Häne: Too toxic for Switzerland - but exportable anyway. In: derbund.ch . March 15, 2019, accessed March 16, 2019 .

[Sigma-1] Methidathion data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on methidathione in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .

[CLP_100.012.227-3] Entry on methidathione 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 .

[Unger-4] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 617 (English, limited preview in Google Book search).

[Roberts-5] A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 377 (English, limited preview in Google Book search).

[6] try methidathion at Extoxnet.

[7] Decision of the Commission of January 30, 2004 on the non-inclusion of certain active substances in Annex I of Directive 91/414 / EEC of the Council as well as the revocation of the authorizations for plant protection products with these active substances

[PSM-8] Directorate-General for Health and Food Safety of the European Commission: Entry on methidathione in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[9] Stefan Häne: Too toxic for Switzerland - but exportable anyway. In: derbund.ch . March 15, 2019, accessed March 16, 2019 .