Farinomalein is a natural

maleimide Maleimide is a chemical compound with the formula H2C2(CO)2NH (see diagram). This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group. Malei ...

with formula C₁₀H₁₃NO₄ - was first isolated from the

entomopathogenic fungus An entomopathogenic fungus is a fungus that can kill or seriously disable insects. Typical life cycle These fungi usually attach to the external body surface of insects in the form of microscopic spores (usually asexual, mitosporic spores also ...

'' 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'' 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 z ...

''.Sastia Prama Putri, Hiroshi Kinoshita, Masayasu Kato and Takuya Nihira. ''Antimicrobial and antioomycete activities of the novel antibiotic farinomalein''. Poster Presentation 2P-2124, Annual Conference, The Society for Bioscience and Bioengineering, Japan, 28 October 2010. These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of

Phytophthora ''Phytophthora'' (from Greek language, Greek (''phytón''), "plant" and (), "destruction"; "the plant-destroyer") is a genus of plant-damaging oomycetes (water molds), whose member species are capable of causing enormous economic losses on cro ...

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, the furanone is oxidized to 3-isopropylfuran-2,5-dione by

Dess–Martin periodinane Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. This periodinane has several advantages over chromium- and DMSO-based oxidants ...

, followed by acetic acid reflux with beta-alanine. The white powdered product has a melting point of 75-77 °C.

References

{{reflist Maleimides Phytophthora Carboxylic acids Pesticides Isopropyl compounds