FURALAXYL

The Uses of FURALAXYL

Furalaxyl is used for the control of soil-borne diseases caused by Phytophthora and Pythium species and other Oomycetes on ornamentals.

Definition

ChEBI: Methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate is an alanine derivative that is the N-furoyl derivative of methyl N-(2,6-dimethylphenyl)alaninate It is an alanine derivative, an aromatic amide, a carboxamide, a member of furans and a methyl ester.

Origin

Furalaxyl is a condensation product of furan-2-carboxylic acid and 2,6-dimethylaniline which is subsequently coupled with methyl 2-chloropropionate. The compound was introduced in 1984.

Metabolic pathway

Incorporation of furalaxyl into the refreshed nutrient solution is made several times at different plant growth stages, and fulalaxyl is decomposed in the nutrient solution into N-(2,6-dimethylphenyl-N-(2- furanylcarbonyl)-DL-alanine and N-(2,6- dimethylphenyl)-DL-alanine by an enzymatic process.

Degradation

Furalaxyl is a stable compound which is hydrolysed only at extreme pH values. Its calculated DT₅₀ values (20 °C) are, at pH 1, >200 days and at pH 10,22 days (PM).
Furalaxyl was degraded when irradiated in aqueous solution with UV light (254 nm) with a half-life of 86 minutes. This study used non-labelled furalaxyl but the products of amide bond fission (2) and subsequent N-dealkylation, 2,6-dimethylaniline (3) were identified (see Scheme 1). The product mixture was therefore simpler than that obtained for metalaxyl under similar conditions. Under simulated sunlight conditions degradation was slower with a half-life of 391 days (Pirisi et al., 1996).