Bensulfuron-methyl

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Structural formula
Bensulfuron-methyl Structural Formula V1.svg
General
Surname Bensulfuron-methyl
other names
  • Methyl α - [(4,6-dimethoxypyrimidin-2-ylcarbamoyl) sulfamoyl] - o -toluate ( IUPAC )
  • Londax
Molecular formula C 16 H 18 N 4 O 7 S
External identifiers / databases
CAS number 83055-99-6
EC number 401-340-6
ECHA InfoCard 100.100.328
PubChem 54960
Wikidata Q2896712
properties
Molar mass 410.40 g mol −1
Physical state

firmly

Melting point
  • 185–188 ° C (white to slightly yellow solid)
  • 180 ° C (in technical quality)
solubility

very heavy in water (0.12 g l −1 at 25 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 317-411
P: 273-280
Toxicological data

> 5000 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bensulfuron-methyl is a chemical compound from the group of sulfonylureas , which was introduced by DuPont in 1984 as a herbicide .

Extraction and presentation

Bensulfuron is prepared in a multistage synthesis starting from 2-methylbenzoic acid methyl ester . This is chlorinated; in the next step the intermediate reacts with thiourea and is chlorinated again. By reacting with ammonia , phosgene and adding 2-amino-4,6-dimethoxypyrimidine , bensulfuron is now formed.

use

Bensulfuron-methyl is used as a selective, systemic herbicide in rice cultivation. It works by inhibiting acetolactate synthase .

Admission

In some EU countries, plant protection products with this active ingredient are approved, but not in Germany, Austria or Switzerland.

Individual evidence

  1. ↑ a b c d e Entry on Bensulfuron-methyl. In: Römpp Online . Georg Thieme Verlag, accessed on March 25, 2014.
  2. ↑ a b data sheet Bensulfuron-methyl, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
  3. ↑ Entry on methyl-α - ((4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl) -o-toluate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 15, 2017. Manufacturers or distributors can use the expand harmonized classification and labeling .
  4. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 168 ( limited preview in Google Book search).
  5. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Bensulfuron in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.