Thiometone

Structural formula
General
Surname	Thiometone
other names	S - [2- (ethylthio) ethyl] O , O -dimethyldithiophosphate; O , O -dimethyl- S - (3-thiapentyl) dithiophosphate;
Molecular formula	C 6 H 15 O 2 PS 3
Brief description	colorless liquid with a characteristic odor
External identifiers / databases
EC number	211-362-6
ECHA InfoCard	100.010.330
PubChem	12541
ChemSpider	12024
Wikidata	Q426304
properties
Molar mass	246.36 g mol −1
Physical state	liquid
density	1.209 g cm −3
boiling point	110 ° C (13.3 Pa)
Vapor pressure	negligible
solubility	poorly soluble in water (200 mg l −1 at 25 ° C); soluble in most organic solvents;
Refractive index	1.5515 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 301-312
	P: 280-301 + 310-331
Toxicological data	40 mg kg −1 ( LD 50 , rat , oral ) ; 179 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

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

Extraction and presentation

Thiometone can be obtained by reacting 2-ethylthioethyl chloride or 2-ethylthioethanol [in the presence of p -toluenesulfonic acid chloride (TosCl)] with dimethyldithiophosphate .

properties

Thiometone is a colorless oily liquid with a characteristic odor that is poorly soluble in water. It metabolizes rapidly in animals and plants to the water-soluble sulfoxide and sulfone derivative . Some of the metabolites of thiometone are more powerful inhibitors of cholinesterase and thus more toxic than thiometone itself.

use

Thiometone is used as an insecticide and acaricide .

Admission

Thiometon was approved in the FRG between 1971 and 1981 and in the GDR until 1967.

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

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on thiometone in the GESTIS substance database of the IFA , accessed on September 3, 2012(JavaScript required) .
↑ ^a ^b ^c ^d ^e WHO / FAO Data Sheet on Pesticides (PDS) for Thiometon ( Memento from August 11, 2014 in the Internet Archive )
↑ Entry on thiometon 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 Thiometon in Shellsol at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 369 ( limited preview in Google Book search).
↑ Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ... Springer DE, 2010, ISBN 3-0348-0028-2 , p. 27 ( 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 thiometone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on thiometone in the GESTIS substance database of the IFA , accessed on September 3, 2012(JavaScript required) .

[inchem.org-2] WHO / FAO Data Sheet on Pesticides (PDS) for Thiometon ( Memento from August 11, 2014 in the Internet Archive )

[CLP_100.010.330-3] Entry on thiometon 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 Thiometon in Shellsol at 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. 369 ( limited preview in Google Book search).

[Peter_Brandt-6] Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ... Springer DE, 2010, ISBN 3-0348-0028-2 , p. 27 ( limited preview in Google Book search).

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

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on thiometone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.