Chlorflurenol

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of Chlorflurenol
Basic structural formula (stereocenter is marked with an * )
General
Surname Chlorflurenol
other names
  • ( RS ) -2-chloro-9-hydroxyfluorene-9-carboxylic acid methyl ester
  • Methyl 2-chloro-9-hydroxyfluorene-9-carboxylate
  • CFL
  • Chlorflurecol
  • Chlorflurenol-methyl
  • Chlorofurenol methyl ester
  • Curbiset
  • IT 3456
  • Maintain
  • Multiprop
Molecular formula C 15 H 11 ClO 3
External identifiers / databases
CAS number 2536-31-4 (chlorofuranol)
EC number 219-800-8
ECHA InfoCard 100.018.001
PubChem 17334
ChemSpider 16404
Wikidata Q15632720
properties
Molar mass 274.7 g mol −1
Physical state

firmly

density

1.496

Melting point

152 ° C

solubility

practically insoluble in water (0.021 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlorflurenol is a growth regulator from the morphactin family .

Stereoisomers

The Chlorflurenol is a racemate (1: 1 mixture) of the ( R ) - and ( S ) -form, which can be named as follows:

  • ( R ) -2-chloro-9-hydroxyfluorene-9-carboxylic acid methyl ester
  • ( S ) -2-chloro-9-hydroxyfluorene-9-carboxylic acid methyl ester
Chlorflurenol
(2 stereoisomers)
(R) -chlorofluorol
( R ) configuration 		(S) -chlorofuranol
( S ) configuration

synthesis

Chlorflurenol can be prepared from fluorenone through a multi-stage reaction . This is converted to chlorine aromatic compounds with chlorine . The further reaction with hydrogen cyanide leads to cyanohydrin . This is saponified with sodium hydroxide to give α-hydroxycarboxylic acid and then reacted with methanol to give the corresponding methyl ester as the end product.

Chlorflurenol synthesis.svg

Mode of action

Chlorflurenol is an auxin transport inhibitor. It ensures a bushier growth by inhibiting the growth in length and removing the apical dominance . Morphactins disrupt mitotic activity in meristematic tissues and thus change the orientation of the mitotic spindles . Used together with herbicides , it enhances the herbicidal effect as a synergist.

Admission

Chlorflurenol was approved in Germany from 1971 to 2002. In 2004 the EU Commission decided not to include Chlorflurenol in the list of permitted active ingredients in plant protection products in Annex I of Directive 91/414 / EEC.

No pesticides containing this active ingredient are permitted in Switzerland, Germany or Austria.

Individual evidence

  1. ↑ a b c d e Entry on Chlorflurenol in the GESTIS substance database of the IFA , accessed on November 28, 2013(JavaScript required) .
  2. ↑ a b data sheet Chlorflurenol-methyl, PESTANAL at Sigma-Aldrich , accessed on November 1, 2016 ( PDF ).
  3. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 746 (English, limited preview in Google Book search).
  4. ↑ Marian Saniewski, Hiroshi Okubo, Jerzy Puchalski: Effect of morphactin on stem growth in relation to auxin in precooled rooted tulip bulbs . In: Acta Physiologiae Plantarum . tape 21 , no. 2 , 1999, p. 167-174 , doi : 10.1007 / s11738-999-0072-2 (English).
  5. ↑ Botany online : Synthetic growth regulators and inhibitors
  6. ↑ Decision of the Commission of January 30, 2004 on the non-inclusion of certain active substances in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with these active substances (2004/129 / EC)
  7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Chlorflurenol (chlorflurecol) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.