Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon-Silicon Bioisosteric Replacement Strategy.

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 which possesses outstanding acaricidal activity. With an LC value of 0.062 mg/L, compound 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 of compound possesses an IC value of 2.32 μM against SDH, which was about twofold superior compared to the active metabolites of cyenopyrafen (IC = 4.72 μM). Molecular docking study showed that the active metabolites and and their corresponding silicon counterparts form H-bonds and cation-π interaction with the residues of Trp165, Tyr433, and Arg279.