Triasulfuron

Structural formula
General
Surname	Triasulfuron
other names	1- [2- (2-chloroethoxy) phenylsulfonyl] -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea; Amber; Logran;
Molecular formula	C 14 H 16 ClN 5 O 5 S
External identifiers / databases
EC number	617-298-9
ECHA InfoCard	100.119.228
PubChem	73282
ChemSpider	66025
Wikidata	Q2384787
properties
Molar mass	401.83 g mol −1
Physical state	firmly
density	1.47 g cm −3
Melting point	178.1 ° C (decomposition); 188.6 ° C (decomposition);
Vapor pressure	0.0021 mPa (25 ° C)
solubility	very sparingly soluble in water (0.815 g l −1 at 20 ° C); slightly soluble in acetone (14 g l −1 at 20 ° C);
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 410
	P: 273-501
Toxicological data	> 5050 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Triasulfuron is a chemical compound from the group of sulfonylureas , which was introduced by Ciba-Geigy in 1985 .

Extraction and presentation

Triasulfuron can be prepared by a multi-stage reaction starting from o -aminophenol . This reacts with sodium nitrite to form the diazonium salt , which further reacts with sulfur dioxide in the presence of copper (I) chloride , with ammonium hydroxide , 2-chloroethyl p -toluenesulfonate and phosgene . With 2-amino-4-methoxy-6-methyl-1,3,5-triazine, the end product is now formed.

use

Triasulfuron is used as a selective post-emergence herbicide in grain cultivation. The effect is based on the inhibition of acetolactate synthase .

Admission

The approval of plant protection products with this active ingredient was revoked in Germany on September 30, 2016. After the revocation, there was a sell-off period for stocks until March 30, 2017 and a use-by period until September 30, 2017.

In the other EU countries and Switzerland, there is no approval for plant protection products with this active ingredient.

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on Triasulfuron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 4, 2014.
↑ ^a ^b Entry on Triasulfuron. In: Römpp Online . Georg Thieme Verlag, accessed on March 4, 2014.
↑ ^a ^b Data sheet Triasulfuron at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ Entry on 1- [2- (2-chloroethoxy) phenylsulfonyl] -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea Template: Linktext-Check / Escaped 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 .
↑ ^a ^b Entry on triasulfuron in the GESTIS substance database of the IFA , accessed on March 4, 2014 (JavaScript required)
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 202 ( limited preview in Google Book search).
↑ Gerrit Hogrefe: Important building blocks in the herbicide range are missing . Ed .: agrarzeitung. July 15, 2016, p. 18 .
↑ bvl.bund.de: BVL - Fachmachrichten - Approvals of pesticides with isoproturon and triasulfuron will be revoked on September 30, 2016 , accessed on July 23, 2016.
↑ General Directorate Health and Food Safety of the European Commission: Entry on triasulfuron in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[ppdb-1] Entry on Triasulfuron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 4, 2014.

[roempp-2] Entry on Triasulfuron. In: Römpp Online . Georg Thieme Verlag, accessed on March 4, 2014.

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

[CLP_100.119.228-4] Entry on 1- [2- (2-chloroethoxy) phenylsulfonyl] -3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) urea Template: Linktext-Check / Escaped 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 .

[GESTIS-5] Entry on triasulfuron in the GESTIS substance database of the IFA , accessed on March 4, 2014 (JavaScript required)

[unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 202 ( limited preview in Google Book search).

[7] Gerrit Hogrefe: Important building blocks in the herbicide range are missing . Ed .: agrarzeitung. July 15, 2016, p. 18 .

[bvl.bund.de-8] vl.bund.de: BVL - Fachmachrichten - Approvals of pesticides with isoproturon and triasulfuron will be revoked on September 30, 2016 , accessed on July 23, 2016.

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on triasulfuron in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.