Organic synthesis and fungicidal activity of oxylipin-based compounds

摘要: Previous research has shown that the naturally occurring reactive electrophilic species (RES), 12-oxophytodienoic acid (OPDA), not only serves as a precursor for jasmonic but is also potent antifungal compound. However, both low amount present in plants and multistep synthesis required to produce this compound on scale viable agrochemical use currently limits its practical value. The aim of was generate range molecular mimics OPDA with minimum number synthetic steps screen activity. Synthetic 4-octyl-cyclopentenone containing cyclopentenone ring an eight carbon alkyl chain found show highest vitro activity against C. herbarum B. cinerea inhibition concentration (MIC) 100-200µM. This indicates structurally simplified can be successfully synthesised mimic specific fungal strains. Application could act surfactant by disrupting disorganising lipid membrane non-specifically, resulting leakage potassium ions, which proposed mode action sensitivity fungi correlated composition spores. (E)-2-alkenals were studied their antimicrobial (E)-2-undecenal have pathogens. hydrophilic moiety (the a,s-unsaturated carbonyl group), common 4-octyl-cyclentenone essential bioactivity, hydrophobic plays important role activities. 4-Octyl-cyclopentenone showed no visible toxicity test plant, Arabidopsis thaliana, suggesting high Botrytis Cladosporium exploited commercialisation new generation agrochemical.