Description
Furalaxyl is a acylamino acid fungicide used control diseases caused by Peronosporales fungi especially in ornamental plants. It is moderately soluble in water, is not volatile and tends to be moderately persistent in soil systems. It has a low potential for leaching to groundwater. It has a moderate mammalian oral toxicity and may be an irritant. Biodiversity toxicity tends to be low to moderate.
Chemical Properties
Bicrystalline crystals. Melting points are 70°C and 84°C, relative density is 1.223, and vapor pressure is 7.05×10-8 kPa. Solubility at 20°C (g/kg): acetone 520, benzene 480, dichloromethane 600, methanol 500, water 0.32.
Uses
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.
Production Methods
Furalaxyl is commercially produced through a multi-step synthesis involving aromatic amines and heterocyclic intermediates. Production begins with the synthesis of N-(2,6-dimethylphenyl)-N-(2-furanylcarbonyl)-racemic amino propionic acid methyl ester. This involves the acylation of 2,6-dimethylaniline with 2-furoyl chloride to form an amide intermediate. The resulting compound is then reacted with methyl 2-bromopropionate under basic conditions to introduce the propionic acid ester moiety, forming the final furalaxyl structure.
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.
Mechanism of action
Systemic with protective and curative action. Disrupts fungal nucleic acid synthesis - RNA ploymerase 1
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).
