Trinexapac

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Structural formula
Trinexapac basic structure V4-Seite001.svg
Basic structural formula
General
Surname Trinexapac
other names
  • ( RS ) -4-Cyclopropyl (hydroxy) methylene-3,5-dioxocyclohexanecarboxylic acid
  • Mode
  • Primo
  • Cimectacarb
Molecular formula C 11 H 12 O 5
External identifiers / databases
CAS number
  • 104273-73-6 (keto form)
  • 143294-89-7 (enol form)
EC number 806-797-9
ECHA InfoCard 100.234.106
PubChem 14371531
ChemSpider 10469309
Wikidata Q15632713
properties
Molar mass 224.41 g mol −1
Physical state

firmly

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trinexapac is a growth regulator from the carboxylic acid family . Trinexapac inhibits the biosynthesis of gibberellins . It works to shorten the internodes and is used as a stalk stabilizer in cereals, rice and sunflowers.

Trinexapac refers to the free carboxylic acid, its ethyl ester is also used in commercial products and is referred to as trinexapac-ethyl ( molecular formula C 13 H 16 O 5 , molar mass 252.26 g · mol −1 , melting point 36–39 ° C).

synthesis

Trinexapac can be prepared from 3,5-dihydroxybenzoic acid by a multi-stage reaction . This is hydrogenated, then it reacts with ethanol and cyclopropyl chloride . In the last step, the ethane group is split off again with hydrogen chloride .

Admission

Trinexapac has been approved in Germany since 1995. In the European Union trinexapac was in the list of allowed applications as plant growth regulator, effective May 1, 2007 pesticide active ingredients added. Plant protection products with this active ingredient are approved in a number of EU countries, including Germany, Austria and Switzerland.

Individual evidence

  1. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. Trinexapac-ethyl data sheet from Sigma-Aldrich , accessed on November 28, 2013 ( PDF ).
  3. External identifiers of or database links for Trinexapac-ethyl : CAS number: 95266-40-3, EC number: 680-302-2, ECHA InfoCard: 100.205.281 , ChemSpider : 83439 , Wikidata : Q27155616 .
  4. Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 797 ( limited preview in Google Book search).
  5. Directive 2006/64 / EC of the Commission of July 18, 2006 (PDF) amending Council Directive 91/414 / EEC to include the active substances clopyralid, cyprodinil, fosetyl and trinexapac.
  6. General Directorate Health and Food Safety of the European Commission: Entry on Trinexapac (aka cimetacarb ethyl) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.