Farinomalein
Encyclopedia
Farinomalein - a natural maleimide
Maleimide
Maleimide is the chemical compound with the formula H2C22NH . This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -CNHC- functional group...

 with formula C10H13NO4 - was first isolated from the entomopathogenic fungus
Entomopathogenic fungus
An entomopathogenic fungus is a fungus that can act as a parasite of insects and kills or seriously disables them.-Typical life cycle:These fungi usually attach to the external body surface of insects in the form of microscopic spores...

 Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).

Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae
Phytophthora sojae
Phytophthora sojae is an oomycete and a soil-borne plant pathogen that causes stem and root rot of soybean. This is a prevalent disease in most soybean growing regions, and a major cause of crop loss . In wet conditions the pathogen produces zoospores that move in water and are attracted to soybean...

. These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora
Phytophthora
Phytophthora is a genus of plant-damaging Oomycetes , whose member species are capable of causing enormous economic losses on crops worldwide, as well as environmental damage in natural ecosystems. The genus was first described by Heinrich Anton de Bary in 1875...

 stem rot in soybean.

Synthesis

A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported. Firstly, 5-hydroxy-4-methyl-2-5(H)-furanone is oxidised to 3-isopropylfuran-2,5-dione by Dess–Martin periodinane, followed by acetic acid reflux with beta-alanine
Beta-alanine
β-Alanine is a naturally occurring beta amino acid, which are amino acids in which the amino group is at the β-position from the carboxylate group . The IUPAC name for β-alanine would be 3-aminopropanoic acid...

. The white powdered product has a melting point of 75-77°C.

External links

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