Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy,Journal of Agricultural and Food Chemistry

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Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-09-18 , DOI: 10.1021/acs.jafc.3c03898
Cong Zhou ₁ , Zhong Li ₁ , Xuhong Qian _{1,

2} , Jiagao Cheng ₁ , Peter Maienfisch _{1,

3}

Affiliation

The identification of novel pyrazolyl acrylonitrile acaricides with improved properties is of great value for the control of phytophagous mites. A series of innovative silicon-containing pyrazolyl acrylonitriles were rationally designed by applying a bioisosteric carbon–silicon replacement strategy and prepared based on novel synthetic methodology. As a result of our research, we discovered compound A25 which possesses outstanding acaricidal activity. With an LC₅₀ value of 0.062 mg/L, compound A25 was found to be 2.3-fold and 1.9-fold more potent than the commercial acaricides cyenopyrafen and cyetpyrafen, respectively. Enzymatic inhibitory assay indicated that the active principle M1 of compound A25 possesses an IC₅₀ value of 2.32 μM against Tetranychus cinnabarinus SDH, which was about twofold superior compared to the active metabolites of cyenopyrafen (IC₅₀ = 4.72 μM). Molecular docking study showed that the active metabolites 2 and 3 and their corresponding silicon counterparts form H-bonds and cation−π interaction with the residues of Trp165, Tyr433, and Arg279.

中文翻译：

通过合理的碳硅生物等排替代策略鉴定出新型杀螨剂含硅吡唑基丙烯腈衍生物

鉴定性能改进的新型吡唑基丙烯腈杀螨剂对于防治植食性螨具有重要价值。通过应用生物电子等排碳硅置换策略，合理设计了一系列创新的含硅吡唑基丙烯腈，并基于新颖的合成方法制备。经过研究，我们发现了具有出色杀螨活性的化合物A25 。化合物A25的 LC ₅₀值为 0.062 mg/L，其效力分别是市售杀螨剂 cyenopyrafen 和 cyetpyrafen 的 2.3 倍和 1.9 倍。酶抑制试验表明，化合物A25的活性成分M1对朱砂叶螨SDH的IC ₅₀值为2.32 μM ，比氰吡芬活性代谢物（IC ₅₀ = 4.72 μM）高约两倍。分子对接研究表明，活性代谢物2和3及其相应的硅对应物与Trp165、Tyr433和Arg279残基形成氢键和阳离子-π相互作用。

更新日期：2023-09-18

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