Metosulam

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Structural formula
Structural formula of metosulam
General
Surname Metosulam
other names
  • N - (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy- [1,2,4] triazolo [1,5- a ] pyrimidine-2-sulfonamide
  • Pronto
Molecular formula C 14 H 13 Cl 2 N 5 O 4 S
Brief description

light to dark yellow crystalline powder

External identifiers / databases
CAS number 139528-85-1
EC number 604-145-6
ECHA InfoCard 100.124.036
PubChem 86422
ChemSpider 77938
Wikidata Q17124753
properties
Molar mass 418.26 g mol −1
Physical state

firmly

density

1.49 g cm −3

Melting point

210-211.5 ° C

boiling point

decomposes

Vapor pressure

negligibly small

solubility

very sparingly soluble in water (0.7 g l −1 at 20 ° C)

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

Caution

H and P phrases H: 351-373-410
P: 273
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 .

Metosulam is a chemical compound from the group of sulfonamides , triazoles and pyrimidines (triazolopyrimidines), which was introduced in 1994 by DowElanco (now Dow AgroSciences ) as a sulfonylurea herbicide.

Extraction and presentation

Metosulam can be obtained by reacting 5-amino-3-mercapto-1,2,4-triazole with chlorine , 4-bromo-3-methylaniline, malonyl chloride , phosphorus oxychloride , again chlorine and sodium methoxide .

use

Metosulam is used as a selective pre-emergence herbicide against weeds in grain and maize.

Admission

Metosulam is not approved in Austria or Switzerland, in Germany only together with Flufenacet .

Individual evidence

  1. ↑ a b c d e f Entry on Metosulam. In: Römpp Online . Georg Thieme Verlag, accessed on May 26, 2014.
  2. ↑ a b c Entry on Metosulam in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 26, 2014.
  3. ↑ entry to metosulam in the GESTIS Bank of IFA , accessed on July 23, 2016(JavaScript required) .
  4. ↑ Entry on 2 ′, 6′-dichloro-5,7-dimethoxy-3′-methyl [1,2,4] triazolo [1,5-a] pyrimidine-2-sulfonanilide 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 .
  5. ↑ Metosulam data sheet from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
  6. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 979 ( limited preview in Google Book Search).
  7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Metosulam in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 7, 2019.