Furalaxyl

Structural formula
1: 1 mixture of the ( S ) -form (left) and the ( R ) -form (right)
General
Surname	Furalaxyl
other names	Methyl N - (2,6-dimethylphenyl) N -2-furoylalaninate ( RS ) -Methyl- N - (2,6-dimethylphenyl) - N -2-furoylalaninate (±) -Methyl- N - (2,6-dimethylphenyl) - N -2-furoylalaninate Methyl N - (2,6-dimethylphenyl) - N - (2-furylcarbonyl) - DL -alaninate Fungarid Fonganil
Molecular formula	C 17 H 19 NO 4
Brief description	white crystals
External identifiers / databases
CAS number 57646-30-7 EC number 260-875-1 ECHA InfoCard 100.055.323 PubChem 42504 ChemSpider 38763 Wikidata Q19280071
properties
Molar mass	301.34 g mol −1
Physical state	firmly
density	1.22 g cm −3
Melting point	70 ° C and 84 ° C (two forms of crystallization)
solubility	very heavy in water (0.23 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302-412 P: 273
Toxicological data	940 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Furalaxyl is an active ingredient in pesticides from the acylalanine group , a systemic fungicide introduced by Ciba-Geigy in 1977 .

Manufacturing

Furalaxyl can be obtained starting from 2,6-dimethylaniline and methyl 2-bromopropionate , the product of which reacts further with furan-2-carboxylic acid chloride . The synthesis produces a 1: 1 mixture ( racemate ) of the ( S ) form and the ( R ) form of the active ingredient.

use

Furalaxyl has both protective and curative effects and is mainly used in growing ornamental plants under glass. There it is used to combat soil fungi ( Pythium , Phytophthora ) and Oomycetes such as downy mildew .

The active ingredient inhibits the synthesis of ribosomal RNA .

Admission

Furalaxyl was approved in the FRG from 1979 to 1989.

No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Individual evidence

1. ↑ ^{a b c d e f} Entry on furalaxyl. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.
2. ↑ ^{a b c} Entry on furalaxyl in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .
3. ↑ Entry on Methyl N- (2,6-dimethylphenyl) -N- (2-furylcarbonyl) -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 expand harmonized classification and labeling .
4. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 29 ( limited preview in Google Book search).
5. ↑ David J. Fisher, Ann L. Hayes: Mode of action of the systemic fungicides furalaxyl, metalaxyl and ofurace . In: Pesticide Science . tape 13 , no. 3 , June 1982, pp. 330–339 , doi : 10.1002 / ps.2780130316 ( PDF ).
6. ↑ approval history of the BVL .
7. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on furalaxyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.