Triflusulfuron-methyl

Structural formula
General
Surname	Triflusulfuron-methyl
other names	Methyl-2 - {[({[4- (dimethylamino) -6- (2,2,2-trifluoroethoxy) -1,3,5-triazin-2-yl] amino} carbonyl) amino] sulfonyl} -3- methyl benzoate
Molecular formula	C 17 H 19 F 3 N 6 O 6 S
Brief description	white, crystalline solid
External identifiers / databases
EC number	603-146-9
ECHA InfoCard	100.111.127
PubChem	92434
ChemSpider	83452
Wikidata	Q18631953
properties
Molar mass	492.43 g mol −1
Physical state	firmly
Melting point	160-163 ° C ; in technical quality: 155–158 ° C;
solubility	very sparingly soluble in water (0.11 g l −1 at 25 ° C)
safety instructions
H and P phrases	H: 351-410
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triflusulfuron-methyl is a chemical compound from the group of sulfonylureas and a herbicide introduced by DuPont in the 1990s .

Extraction and presentation

Triflusulfuron-methyl can be obtained starting from 2-nitro-3-methylbenzoic acid methyl ester and benzyl mercaptan . Their product reacts further with sodium hypochlorite and t -butyldimethylsilylamine . Then o- phenyl- N [4-dimethyl-2-amino-6 (2.22-trifluoroethoxy)] - 1,3,5-triazinyl carbamate is added.

use

Triflusulfuron-methyl is used as a systemic herbicide against broad-leaved weeds and grass weeds in sugar beet cultivation . It works by inhibiting acetolactate synthase (ALS inhibitor). The resistance of the crop is based on a very rapid metabolism (half-life <1h).

Admission

In Germany, Austria and Switzerland, plant protection products with triflusulfuron-methyl as an active ingredient are approved ( Debut , Safari ).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on Triflusulfuron-methyl. In: Römpp Online . Georg Thieme Verlag, accessed on November 24, 2014.
↑ Entry on triflusulfuron-methyl in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Entry on triflusulfuron-methyl in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 205 ( limited preview in Google Book search).
^ VA Wittenbach, MK Koeppe, FT Lichtner, WT Zimmerman, RW Reiser: Basis of Selectivity of Triflusulfuron Methyl in Sugar Beets ( Beta vulgaris ) . In: Pesticide Biochemistry and Physiology . tape 49 , no. 1 , May 1994, pp. 72–81 , doi : 10.1006 / pest.1994.1035 ( PDF ).
↑ General Directorate Health and Food Safety of the European Commission: Entry on triflusulfuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 14, 2016.

[roempp-1] ↑ ^a ^b ^c ^d ^e ^f Entry on Triflusulfuron-methyl. In: Römpp Online . Georg Thieme Verlag, accessed on November 24, 2014.

[2] Entry on triflusulfuron-methyl in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[CLP_100.111.127-3] Entry on triflusulfuron-methyl in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 205 ( limited preview in Google Book search).

[5] VA Wittenbach, MK Koeppe, FT Lichtner, WT Zimmerman, RW Reiser: Basis of Selectivity of Triflusulfuron Methyl in Sugar Beets ( Beta vulgaris ) . In: Pesticide Biochemistry and Physiology . tape 49 , no. 1 , May 1994, pp. 72–81 , doi : 10.1006 / pest.1994.1035 ( PDF ).

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on triflusulfuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 14, 2016.