Taking Advantage of the Renewable Forest Bioresource Turpentine to Prepare α,β-Unsaturated Compounds as Highly Efficient Fungicidal Candidates

In a continuous study on the high-value-added exploration of a renewable forest bioresource turpentine in modern organic agriculture, two series of alpha-pinene derivatives containing amide and alpha,beta-unsaturated ketone pharmacophores were prepared. Through an in-depth fungicidal activity study, the title compounds presented excellent inhibitory activity against common crop fungi, especially Sclerotinia sclerotiorum, and the notable EC50 values of alpha,beta-unsaturated compounds 3u (funan containing) and 3v (thiophene containing) were 1.657 and 1.749 mu g/mL, respectively. Further physiological and biochemical studies on S. sclerotiorum revealed that compounds 3u and 3v reduced the ergosterol content in the cell membrane and increased the permeability of the cell membrane. In combination with their effect on mycelial morphology, the title compounds might have inhibitory effects on the biosynthesis of ergosterol, which is a paramount component of the target cell membrane. Moreover, quantitative structure-activity relationship (QSAR) and SAR studies revealed that the charge distribution of alpha,beta-unsaturated carbonyl ketone derivatives played an important role in the observed fungicidal activity. In summary, this study highlights the design and development of novel highefficacy turpentine-based antifungal agents.

Automated summary

In-depth study on alpha-pinene derivatives containing pharmacophores revealed excellent inhibitory activity against common crop fungi, particularly Sclerotinia sclerotiorum. Compound 3u and 3v significantly reduced ergosterol content and increased cell membrane permeability, suggesting inhibitory effects on ergosterol biosynthesis. QSAR and SAR studies indicated that the charge distribution of alpha,beta-unsaturated carbonyl ketone derivatives played a crucial role in fungicidal activity. Overall, this study emphasizes the importance of designing novel high-efficacy turpentine-based antifungal agents.