Benalaxyl

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of benalaxyl
Structural formula without stereochemistry
General
Surname Benalaxyl
other names
  • Methyl N - (2,6-dimethylphenyl) - N - (phenylacetyl) - DL -alaninate
  • ( RS ) -Methyl- N - (2,6-dimethylphenyl) - N - (phenylacetyl) alaninate
  • Gallows
  • Tairel
Molecular formula C 20 H 23 NO 3
Brief description

white, crystalline solid

External identifiers / databases
CAS number 71626-11-4
EC number 275-728-7
ECHA InfoCard 100,068,822
PubChem 51369
Wikidata Q2795787
properties
Molar mass 325.40 g mol −1
Physical state

firmly

density

1.181 g cm −3

Melting point

78-80 ° C

Vapor pressure

0.572 mPa (20 ° C)

solubility

practically insoluble in water (0.0286 g l −1 )

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

Caution

H and P phrases H: 410
P: 273-501
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benalaxyl is a chemical compound from the group of acetylalanines . Benalaxyl occurs as a racemic mixture of the ( R ) - and the ( S ) - enantiomer . ( R ) -Benalaxyl is the more potent compound (the eutomer ) and is also known as Benalaxyl-M . Benalaxyl was launched as a systemic fungicide in 1983 ; it works by inhibiting RNA polymerase I.

Extraction and presentation

Benalaxyl can be obtained by esterification of ( RS ) -2-chloropropionic acid [(±) -2-chloropropionic acid] with methanol , subsequent aminolysis of the methyl ester with 2,6-dimethylaniline and amidation with phenylacetyl chloride.

Synthesis of benalaxyl

use

Benalaxyl is used in potato cultivation against late blight and tuber blight and Alternaria as well as against downy mildew of the grapevine . There is a partial effect against Botrytis and Roter Brenner .

Admission

In 2004 the EU Commission decided to include benalaxyl for use as a fungicide in the list of substances permitted as active ingredients in pesticides.

The active ingredient Benalaxyl-M was added to the list of permitted active ingredients in 2013.

In Germany, Switzerland and Austria pesticides with the active ingredient Benalaxyl-M are approved, in Austria also pesticides with Benalaxyl.

Individual evidence

  1. ↑ a b data sheet Benalaxyl of the FAO (PDF; 580 kB)
  2. ↑ a b c d e Entry on Benalaxyl in the GESTIS substance database of the IFA , accessed on August 24, 2016(JavaScript required) .
  3. ↑ a b Benalaxyl data sheet from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
  4. ↑ Entry on Methyl N- (2,6-dimethylphenyl) -N- (phenylacetyl) -DL-alaninate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and expand labeling .
  5. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 10 ( limited preview in Google Book search).
  6. ↑ Directive 2004/58 / EC of the Commission of April 23, 2004 (PDF) amending Council Directive 91/414 / EEC to include the active substances alpha-cypermethrin, benalaxyl, bromoxynil, desmedipham, ioxynil and phenmedipham.
  7. ↑ Implementing Regulation (EU) No. 1175/2013 of November 20, 2013 (PDF)
  8. ↑ Directorate-General for Health and Food Safety of the European Commission: Entry on Benalaxyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.