Fosthiazate

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Fosthiazate
other names	( RS ) - S - sec -Butyl- O -ethyl-2-oxo-1,3-thiazolidin-3-yl-phosphonothioate
Molecular formula	C 9 H 18 NO 3 PS 2
Brief description	colorless to yellow liquid
External identifiers / databases
EC number	619-377-3
ECHA InfoCard	100.118.576
PubChem	91758
Wikidata	Q1266349
properties
Molar mass	283.35 g mol −1
Physical state	liquid
density	1.234 g cm −3
Vapor pressure	0.0008 hPa (25 ° C)
solubility	soluble in water (9 g l −1 at 20 ° C); miscible with methanol, acetone, ethyl acetate, xylene and isopropyl alcohol;
Refractive index	1.5334 (19.6 ° C)
safety instructions
H and P phrases	H: 301 + 311 + 331-317-318-410
	EUH: 070
	P: 280-301 + 330 + 331 + 310-302 + 352 + 312-304 + 340 + 311-305 + 351 + 338 + 310
Toxicological data	558 mg kg −1 ( LD 50 , rat , oral ) ; 861 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 . Refractive index: Na-D line , 20 ° C

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

Extraction and presentation

Fosthiazate can be obtained by reacting 2-oxo-3-thiazolidine with S - sec -butyl- O- ethyl-phosphorochlorothioate in toluene .

It is also possible to display it by reacting phosphorus trichloride with ethanol , sec- butyl mercaptan and thiazolidin-2-one .

properties

Fosthiazate is a colorless to yellow liquid that is soluble in water. It is stable to hydrolysis at pH 5 and 7, and half disintegrates in 3.2 days at pH 9.

use

Fosthiazate is used as an active ingredient in crop protection products. It is used as a nematicide in agriculture (potatoes). It is primarily effective against the cyst-forming species Globodera rostochiensis and G. pallida as well as against free- living Pratylenchus , Trichodorus and gall-forming Meloidogyne species. Since fosthiazate also has insecticidal properties, a side effect is a reduction in the infestation of potato tubers by wireworms ( Agriotes spp. ). The effect is based on the inhibition of acetylcholinesterase .

Admission

In the European Union, plant protection products containing fosthiazate have been approved for use as nematicides since 2004. Since 2011, approval has also been possible for applications as an insecticide. No pesticides containing this active ingredient are permitted in Austria or Switzerland . Fosthiazate has been approved in Germany since 2004.

Web links

EU: 97/362 / EG: Commission decision of May 21, 1997 on the fundamental recognition of the completeness of the documents required for detailed examination with regard to the possible inclusion of carfentrazone-ethyl, fosthiazate and fluthiamide in Annex I of Directive 91 / 414 / EEC of the Council on the placing of plant protection products on the market - Official Journal No. L 152 of 11/06/1997 pp. 0031–0032.
EPA: Fosthiazate

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on fosthiazate in the Hazardous Substances Data Bank , accessed December 18, 2012.
↑ ^a ^b ^c ^d Entry on fosthiazates in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b ^c Data sheet Fosthiazate from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ ^a ^b ^c ^d Federal Office for Consumer Protection and Food Safety: Fosthiazate , November 2004.
↑ Entry on (RS) -S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylphosphonothioate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturer or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 285 ( limited preview in Google Book search).
^ Horst Börner: Plant diseases and plant protection . Springer, 2009, ISBN 978-3-540-49068-5 , pp. 598 ( limited preview in Google Book search).
↑ Directive 2003/84 / EC of the Commission of September 25, 2003 amending Directive 91/414 / EEC of the Council to include the active substances Flurtamone, Flufenacet, Iodosulfuron, Dimethenamid-p, Picoxystrobin, Fosthiazate and Silthiofam (PDF)
↑ Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on Fosthiazate in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.
↑ Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance. Springer, Basel 2010, ISBN 978-3-0348-0029-7 , pp. 18 ( limited preview in Google Book search).

[HSDB-1] ↑ ^a ^b ^c ^d ^e ^f Entry on fosthiazate in the Hazardous Substances Data Bank , accessed December 18, 2012.

[GESTIS-2] Entry on fosthiazates in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Sigma-3] Data sheet Fosthiazate from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[bund-4] Federal Office for Consumer Protection and Food Safety: Fosthiazate , November 2004.

[CLP_100.118.576-5] Entry on (RS) -S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylphosphonothioate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturer or distributors can expand the harmonized classification and labeling .

[Thomas_A._Unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 285 ( limited preview in Google Book search).

[Horst_Börner-7] Horst Börner: Plant diseases and plant protection . Springer, 2009, ISBN 978-3-540-49068-5 , pp. 598 ( limited preview in Google Book search).

[8] Directive 2003/84 / EC of the Commission of September 25, 2003 amending Directive 91/414 / EEC of the Council to include the active substances Flurtamone, Flufenacet, Iodosulfuron, Dimethenamid-p, Picoxystrobin, Fosthiazate and Silthiofam (PDF)

[9] Implementing Regulation (EU) No. 540/2011 of the Commission of 25 May 2011 for the implementation of Regulation (EC) No. 1107/2009 of the European Parliament and of the Council with regard to the list of approved active substances (PDF)

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Fosthiazate in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[Peter_Brandt-11] Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance. Springer, Basel 2010, ISBN 978-3-0348-0029-7 , pp. 18 ( limited preview in Google Book search).