Design and synthesis of novel cinnamamide derivatives‐based lansiumamide B as potent fungicidal candidates,Pest Management Science

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Design and synthesis of novel cinnamamide derivatives‐based lansiumamide B as potent fungicidal candidates
Pest Management Science ( IF 3.8 ) Pub Date : 2025-05-27 , DOI: 10.1002/ps.8858
Yizhou Yang _{1,

2} , Jianrong Tang _{1,

2} , Tianrun Zhao _{1,

2} , Qi Li _{1,

2} , Jiuhui Ye _{1,

2} , Jing Zhang _{1,

2} , Zhiqing Ma _{1,

2} , Xili Liu ₁ , Xiaojun Chen ₃ , He Yan _{1,

2}

Affiliation

BACKGROUNDNatural products have been and continue to be a significant resource for developing environmentally friendly pesticides with distinctive structures and mechanisms. Lansiumamide B (LB), a cinnamamide compound extracted from Clausena lansium seeds, has served as the lead compound for the design and synthesis of a series of cinnamamide derivatives. The fungicidal activity of these derivatives has been evaluated.RESULTSThe majority of the proposed compounds displayed moderate to considerable antifungal efficacy against the tested pathogenic fungi and oomycetes, with some exhibiting broad‐spectrum fungicidal activities. Compound B26 showed excellent activity against Colletotrichum orbiculare in vitro, with a median effective concentration (EC50) value of 0.36 μg/mL, better than positive control boscalid (0.95 μg/mL) and the lead compound LB (60.18 μg/mL). In vivo, B26 also exhibited greater fungicidal activity against C. orbiculare than boscalid and LB. Furthermore, the study found that the mycelium cell wall was damaged after treatment with compound B26 through observation of the mycelial morphology and ultrastructure of C. orbiculare. Consequently, mycelial growth was inhibited.CONCLUSIONThe results indicated that cinnamamide compounds containing a 1,2,3,4‐tetrahydroisoquinoline moiety represent a novel class of antifungal active scaffold, and compound B26 has the potential to be developed into a new type of fungicide. © 2025 Society of Chemical Industry.

中文翻译：

基于新型肉桂酰胺衍生物的镭酰胺 B 的设计与合成作为有效的杀真菌候选物

背景自然产品一直是并将继续成为开发具有独特结构和机制的环保型杀虫剂的重要资源。Lansiumamide B （LB）是一种从 Clausena lansium 种子中提取的肉桂酰胺化合物，已作为一系列肉桂酰胺衍生物设计和合成的先导化合物。已经评估了这些衍生物的杀菌活性。结果大多数拟议化合物对测试的病原真菌和卵菌表现出中等到相当的抗真菌功效，其中一些表现出广谱杀真菌活性。化合物 B26 在体外对环炭疽菌表现出优异的活性，中位有效浓度（EC50）值为 0.36 μg/mL，优于阳性对照啶酰菌胺（0.95 μg/mL）和先导化合物 LB （60.18 μg/mL）。在体内，B26 对 C. orbiculare 的杀菌活性也高于啶酰菌和 LB。此外，通过观察环状蚜的菌丝形态和超微结构，研究发现化合物 B26 处理后菌丝体细胞壁受损。因此，菌丝生长受到抑制。结论结果表明，含有 1,2,3,4-四氢异喹啉部分的肉桂酰胺化合物是一类新型的抗真菌活性支架，化合物 B26 有可能开发成一种新型杀菌剂。© 2025 化工学会.

更新日期：2025-05-27

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