Fenarimol

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Structural formula
Structure of fenarimol
Simplified structural formula without stereochemistry
General
Surname Fenarimol
other names
  • ( RS ) -2,4'-dichloro-alpha- (pyrimidin-5-yl) benzhydryl alcohol
  • ( RS ) -2,4'-dichloro-α- (pyrimidin-5-yl) benzhydryl alcohol
  • (±) -2,4'-Dichloro-α- (pyrimidin-5-yl) benzhydryl alcohol
Molecular formula C 17 H 12 Cl 2 N 2 O
Brief description

colorless solid

External identifiers / databases
CAS number 60168-88-9
EC number 262-095-7
ECHA InfoCard 100.056.432
PubChem 43226
Wikidata Q906987
properties
Molar mass 331.2 g · mol -1
Physical state

firmly

Melting point

117-119 ° C

boiling point

240 ° C (decomposition)

Vapor pressure

65 µ Pa (25 ° C)

solubility
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: 361fd-362-411
P: 263-273-281
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fenarimol is an active ingredient in pesticides from the group of pyrimidines (more precisely pyrimidine carbinols ). It is used as a fungicide (e.g. against rust fungi , star soot and powdery mildew ) on ornamental plants and lawns, but also on peppers, tomatoes and cucumbers and is sold under the trade name Rubigan . The effect is based on the inhibition of enzymes such. B. C 14 demethylase .

history

Fenarimol was launched in 1975 by Eli Lilly .

Stereochemistry and isomerism

Fenarimol contains a stereocenter; it is chiral . It is used as a racemate [1: 1 mixture of the ( S ) - and ( R ) - enantiomers ].

Extraction and presentation

Fenarimol can be obtained from methylpyrimidine-5-carboxylic acid, which reacts with o - chlorophenylmagnesium bromide and in the next step with p -chlorophenylmagnesium bromide.

safety instructions

For fenarimol has been demonstrated that there estrogen - receptors can activate and thus lead to increased growth of MCF7 breast cancer cells. It is toxic to fish and must therefore not get into water.

Admission

Fenarimol was only approved for a limited period in the EU until the end of 2009. No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Individual evidence

  1. a b c Entry on fenarimol in the GESTIS substance database of the IFA , accessed on February 7, 2017(JavaScript required) .
  2. a b c Entry on fenarimol. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2017.
  3. a b c d e Review Report Fenarimol . DG SANTE of the European Commission , accessed on July 13, 2017 (PDF; 133 kB).
  4. a b Datasheet Fenarimol . FAO , accessed on July 13, 2017 (PDF; 313 kB).
  5. Entry on 2,4′-dichloro-α (pyrimidin-5-yl) benzhydryl alcohol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  6. Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 378 ( limited preview in Google Book search).
  7. Annemarie Vinggaard, Vibeke Breinholt, John Christian Larsen: Screening of selected pesticides for estrogen receptor activation in vitro . In: Food Additives and Contaminants . tape 16 , no. 12 , 1999, p. 533-542 , doi : 10.1080 / 026520399283678 .
  8. ^ JF Moltmann, M. Liebig, T. Knacker, M. Keller, M. Scheurer, T. Ternes: Water relevance endocrine substances and drugs . 2007 ( PDF ).
  9. fenarimol (Rubigan) Chemical Fact Sheet .
  10. Amendment of Council Directive 91/414 / EEC to include the active substance fenarimol .
  11. General Directorate Health and Food Safety of the European Commission: Entry on fenarimol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.