Abstract：
BACKGROUND: Utilizing fungicides to protect crops from diseases is an effective method, and novel eco-friendly plant-derived fungicides with high efficiency and low toxicity are urgent requirements for sustainable crop protection.
RESULTS: Two series of rosin-based fungicides (totally 35) were designed and synthesized. In vitro fungicidal activity revealed that Compound 6a (Co. 6a) effectively inhibited the growth of Valsa mali [median effective concentration (EC50) = 0.627 μg mL-1], and in vivo fungicidal activity suggested a significant protective efficacy of Co. 6a in protecting both apple branches (35.12% to 75.20%) and apples (75.86% to 90.82%). Quantum chemical calculations (via density functional theory) results indicated that the primary active site of Co. 6a lies in its amide structure. Mycelial morphology and physiology were investigated to elucidate the mode-of-action of Co. 6a, and suggested that Co. 6a produced significant cell membrane damage, accelerated electrolyte leakage, decreased succinate dehydrogenase (SDH) protein activity, and impaired physiological and biochemical functions, culminating in mycelial mortality. Molecular docking analysis revealed a robust binding energy (ΔE = -7.29 kcal mol-1) between Co. 6a and SDH. Subsequently, biosafety evaluations confirmed the environmentally-friendly nature of Co. 6a via the zebrafish model, yet toxicological results indicated that Co. 6a at median lethal concentration [LC50(96)] damaged the gills, liver and intestines of zebrafish.
CONCLUSIONS: The above research offers a theoretical foundation for exploiting eco-friendly rosin-based fungicidal candidates in sustainable crop protection. © 2024 Society of Chemical Industry.
RESULTS: Two series of rosin-based fungicides (totally 35) were designed and synthesized. In vitro fungicidal activity revealed that Compound 6a (Co. 6a) effectively inhibited the growth of Valsa mali [median effective concentration (EC50) = 0.627 μg mL-1], and in vivo fungicidal activity suggested a significant protective efficacy of Co. 6a in protecting both apple branches (35.12% to 75.20%) and apples (75.86% to 90.82%). Quantum chemical calculations (via density functional theory) results indicated that the primary active site of Co. 6a lies in its amide structure. Mycelial morphology and physiology were investigated to elucidate the mode-of-action of Co. 6a, and suggested that Co. 6a produced significant cell membrane damage, accelerated electrolyte leakage, decreased succinate dehydrogenase (SDH) protein activity, and impaired physiological and biochemical functions, culminating in mycelial mortality. Molecular docking analysis revealed a robust binding energy (ΔE = -7.29 kcal mol-1) between Co. 6a and SDH. Subsequently, biosafety evaluations confirmed the environmentally-friendly nature of Co. 6a via the zebrafish model, yet toxicological results indicated that Co. 6a at median lethal concentration [LC50(96)] damaged the gills, liver and intestines of zebrafish.
CONCLUSIONS: The above research offers a theoretical foundation for exploiting eco-friendly rosin-based fungicidal candidates in sustainable crop protection. © 2024 Society of Chemical Industry.
摘要：
背景：利用杀菌剂保护农作物免受疾病侵害是一种有效的方法，高效低毒的新型生态友好型植物源杀菌剂是可持续作物保护的迫切需求。
结果：设计并合成了两个系列的松香基杀菌剂（共35种）。体外杀真菌活性表明，化合物6a（Co。6a）有效抑制了Valsamali的生长[中位有效浓度（EC50）=0.627μgmL-1]，和体内杀菌活性表明Co.6a在保护苹果树枝（35.12％至75.20％）和苹果（75.86％至90.82%）方面具有显着的保护作用。量子化学计算（通过密度泛函理论）结果表明，Co。6a的主要活性位点位于其酰胺结构中。研究了菌丝体形态和生理学，以阐明Co的作用方式。6a，并表明Co。6a产生了显着的细胞膜损伤，加速电解液泄漏，琥珀酸脱氢酶（SDH）蛋白活性降低，生理和生化功能受损，最终导致菌丝死亡。分子对接分析显示，Co.6a和SDH之间具有强大的结合能（ΔE=-7.29kcalmol-1）。随后，生物安全评估通过斑马鱼模型证实了Co.6a的环境友好性质，然而，毒理学结果表明，Co。6a在中位致死浓度[LC50（96）]损害了g，斑马鱼的肝脏和肠道。
结论：上述研究为在可持续作物保护中开发生态友好型松香基杀菌剂提供了理论基础。©2024化学工业学会。
结果：设计并合成了两个系列的松香基杀菌剂（共35种）。体外杀真菌活性表明，化合物6a（Co。6a）有效抑制了Valsamali的生长[中位有效浓度（EC50）=0.627μgmL-1]，和体内杀菌活性表明Co.6a在保护苹果树枝（35.12％至75.20％）和苹果（75.86％至90.82%）方面具有显着的保护作用。量子化学计算（通过密度泛函理论）结果表明，Co。6a的主要活性位点位于其酰胺结构中。研究了菌丝体形态和生理学，以阐明Co的作用方式。6a，并表明Co。6a产生了显着的细胞膜损伤，加速电解液泄漏，琥珀酸脱氢酶（SDH）蛋白活性降低，生理和生化功能受损，最终导致菌丝死亡。分子对接分析显示，Co.6a和SDH之间具有强大的结合能（ΔE=-7.29kcalmol-1）。随后，生物安全评估通过斑马鱼模型证实了Co.6a的环境友好性质，然而，毒理学结果表明，Co。6a在中位致死浓度[LC50（96）]损害了g，斑马鱼的肝脏和肠道。
结论：上述研究为在可持续作物保护中开发生态友好型松香基杀菌剂提供了理论基础。©2024化学工业学会。
