Furmecyclox

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Structural formula
Structural formula of Furmecyclox
General
Surname Furmecyclox
other names

N -Cyclohexyl- N -methoxy-2,5-dimethyl-3-furamide

Molecular formula C 14 H 21 NO 3
External identifiers / databases
CAS number 60568-05-0
EC number 262-302-0
ECHA InfoCard 100.056.620
PubChem 43359
Wikidata Q15632815
properties
Molar mass 251.32 g mol −1
Physical state

firmly

Melting point

33 ° C

solubility

practically insoluble in water (0.0013 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: 351-410
P: 273-281-501
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Furmecyclox is a chemical compound from the group of furans and carboxamides . It was used as a fungicidal active ingredient in pesticides ( Campogran ) and wood preservatives . From 1980 pentachlorophenol (PCP) was replaced by the less toxic wood preservative Xyligen B with furmecyclox as the active ingredient, until this was also banned in 1988.

Extraction and presentation

Furmecyclox is presented in a multi-step reaction. First, acetoacetic acid and acetyloxypropanal react with one another to form 2,5-dimethylfuran-3-carboxylic acid, which reacts with thionyl chloride . The intermediate product reacts further with N -cyclohexylhydroxylamine and dimethyl sulfate to form the end product.

Synthesis of Furmecyclox.svg

Admission

The active ingredient furmecyclox is not approved for use in plant protection products in the European Union . In Germany, Austria and Switzerland, Furmecyclox is not contained in any approved pesticides.

Individual evidence

  1. ↑ a b c d Entry on Furmecyclox in the GESTIS substance database of the IFA , accessed on August 29, 2013 (JavaScript required)
  2. ↑ a b Furmecyclox data sheet , PESTANAL at Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
  3. ↑ Entry on N-cyclohexyl-N-methoxy-2,5-dimethyl-3-furamide 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 .
  4. ↑ Information on harmful substances on Furmecyclox .
  5. ↑ Entry on PCP on naturheilkundelexikon.de.
  6. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 890 . Preview ( Memento from May 30, 2014 in the Internet Archive )
  7. ↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.
  8. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Furmecyclox in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.