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Discovery of Novel Cinnamic Acid Derivatives as Fungicide Candidates
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-01-25 , DOI: 10.1021/acs.jafc.3c05655 Hanru Liu 1 , Chonglin Cai 1 , Xingjia Zhang 1 , Wenkui Li 1, 2 , Zhiqing Ma 1, 2 , Juntao Feng 1, 2 , Xili Liu 1, 3 , Peng Lei 1, 2
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-01-25 , DOI: 10.1021/acs.jafc.3c05655 Hanru Liu 1 , Chonglin Cai 1 , Xingjia Zhang 1 , Wenkui Li 1, 2 , Zhiqing Ma 1, 2 , Juntao Feng 1, 2 , Xili Liu 1, 3 , Peng Lei 1, 2
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Structural diversity derivatization from natural products is an important and effective method of discovering novel green pesticides. Cinnamic acids are abundant in plants, and their unparalleled structures endow them with various excellent biological activities. A series of novel cinnamic oxime esters were designed and synthesized to develop high antifungal agrochemicals. The antifungal activity, structure–activity relationship, and action mechanism were systematically studied. Compounds 7i, 7u, 7v, and 7x exhibited satisfactory activity against Gaeumannomyces graminis var. tritici, with inhibition rates of ≥90% at 50 μg/mL. Compounds 7z and 7n demonstrated excellent activities against Valsa mali and Botrytis cinerea, with median effective concentration (EC50) values of 0.71 and 1.41 μg/mL, respectively. Compound 7z exhibited 100% protective and curative activities against apple Valsa canker at 200 μg/mL. The control effects of 7n against gray mold on tomato fruits and leaves were all >96%, exhibiting superior or similar effects to those of the commercial fungicide boscalid. Furthermore, the quantitative structure–activity relationship was established to guide the further design of higher-activity compounds. The preliminary results on the action mechanism revealed that 7n treatment could disrupt the function of the nucleus and mitochondria, leading to reactive oxygen species accumulation and cell membrane damage. Its primary biochemical mechanism may be inhibiting fungal ergosterol biosynthesis. The novel structure, simple synthesis, and excellent activity of cinnamic oxime esters render them promising potential fungicides.
中文翻译：
新型肉桂酸衍生物作为候选杀菌剂的发现
天然产物的结构多样性衍生是发现新型绿色农药的重要而有效的方法。肉桂酸在植物中含量丰富，其无与伦比的结构赋予其各种优异的生物活性。设计合成了一系列新型肉桂肟酯，用于开发高抗真菌农药。系统研究了其抗真菌活性、构效关系和作用机制。化合物7i 、 7u 、 7v和7x表现出令人满意的对抗全芽孢杆菌变种的活性。小麦，50 μg/mL 时抑制率≥90%。化合物7z和7n表现出优异的抗苹果腐烂病和灰葡萄孢的活性，中位有效浓度(EC 50 )值分别为0.71和1.41 μg/mL。 200 μg/mL 的化合物7z对苹果腐烂病表现出 100% 的保护和治疗活性。 7n对番茄果实和叶片灰霉病的防效均>96%，优于市售杀菌剂啶酰菌胺或相似效果。此外，还建立了定量构效关系，以指导进一步设计更高活性的化合物。作用机制的初步结果表明， 7n处理会破坏细胞核和线粒体的功能，导致活性氧积累和细胞膜损伤。其主要生化机制可能是抑制真菌麦角甾醇的生物合成。 肉桂肟酯结构新颖、合成简单、活性优异，是一种很有前景的潜在杀菌剂。
更新日期：2024-01-25
中文翻译：
新型肉桂酸衍生物作为候选杀菌剂的发现
天然产物的结构多样性衍生是发现新型绿色农药的重要而有效的方法。肉桂酸在植物中含量丰富，其无与伦比的结构赋予其各种优异的生物活性。设计合成了一系列新型肉桂肟酯，用于开发高抗真菌农药。系统研究了其抗真菌活性、构效关系和作用机制。化合物7i 、 7u 、 7v和7x表现出令人满意的对抗全芽孢杆菌变种的活性。小麦，50 μg/mL 时抑制率≥90%。化合物7z和7n表现出优异的抗苹果腐烂病和灰葡萄孢的活性，中位有效浓度(EC 50 )值分别为0.71和1.41 μg/mL。 200 μg/mL 的化合物7z对苹果腐烂病表现出 100% 的保护和治疗活性。 7n对番茄果实和叶片灰霉病的防效均>96%，优于市售杀菌剂啶酰菌胺或相似效果。此外，还建立了定量构效关系，以指导进一步设计更高活性的化合物。作用机制的初步结果表明， 7n处理会破坏细胞核和线粒体的功能，导致活性氧积累和细胞膜损伤。其主要生化机制可能是抑制真菌麦角甾醇的生物合成。 肉桂肟酯结构新颖、合成简单、活性优异，是一种很有前景的潜在杀菌剂。
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