【 Technological Breakthrough; Product Innovation 】 Nankai University Develops New Difluorovinylsilane Compounds With Excellent Antifungal Activity

Professor Wang Qingmin's research group at Nankai University has developed a novel difluorovinylsilane compound, which exhibits excellent antifungal activity against plant pathogens such as Botrytis cinerea, Colletotrichum macrophylla, and Fusarium graminearum. By using amine radical cleavage to replace silanol boronic acid esters, breaking through their high oxidation potential limitations, the synthesis method is environmentally friendly and scalable. Research has shown that some compounds have an inhibition rate of over 60% against Botrytis cinerea at a concentration of 50 μ g/mL, with EC50 values better than or equivalent to commercial fungicides, providing a new direction for the development of fungicides.

According to the Chinese website of World Agrochemical Network, plant pathogenic fungi pose a significant threat to global food security, ecosystems, and human livelihoods. Green chemical control is the most mainstream and effective method for fungal prevention and control. The scarcity of new lead compounds for fungicides is the main bottleneck problem in current development, therefore, discovering efficient new lead compounds and targets is particularly important.

Core parameters: Antibacterial rate>60% at 50 μ g/mL, EC50 value better than commercial fungicides
Fluorine atoms have a small radius, high electronegativity, and strong binding ability with carbon atoms. Introducing fluorine elements into bioactive molecules can significantly improve their acidity, lipophilicity, and stability, thereby enhancing their binding ability to target receptors or enzymes, improving molecular transport efficiency, and preventing metabolic inactivation, thereby enhancing biological activity.

Silicon derivatives are crucial as key raw materials in related fields, but the high oxidation potential of silanol esters of silicon boronic acid limits their application in photocatalytic silanization. Traditional methods rely on nucleophilic reagents to lower the potential, while amine radicals, as an innovative strategy, demonstrate the potential to activate Si-B bonds, providing a new pathway for green synthesis. However, currently silicon containing and difluoroene based fragments exist independently in most compounds, and introducing both into the same molecule will provide a new research perspective for medicinal chemistry.

In response to the bottleneck problem of the scarcity of new lead compounds for fungicides, Professor Wang Qingmin's research group at Nankai University used silicon-based boronic acid pinal ester as the raw material and broke through its high oxidation potential limitation through free radical transfer strategy to synthesize a series of difluorovinylsilane compounds. Further biological experiments have confirmed that multiple target compounds exhibit excellent antifungal activity against plant pathogens such as Botrytis cinerea, Colletotrichum macrophylla, and Fusarium graminearum.

The relevant research results were published in Chinese Chemical Letters (DOI: 10.1016/j.clet. 2025.111940). This method has a simple, green, and mild synthetic approach, strong substrate universality, compatibility with multiple functional groups and natural product structures, and can be scaled up at the gram level.

Some compounds showed good antibacterial activity against Botrytis cinerea (Table 1), and DFT and MEP analysis revealed the correlation between structure and activity (Figure 2).

DFT and MEP analysis revealed that highly active compounds have unique electronic properties. Scanning electron microscopy confirmed its effective inhibition of hyphal growth.

The author developed a method for efficiently generating silicon-based free radicals and introducing difluoroene based fragments through the homolytic substitution reaction of silanol boronic acid esters using amine free radicals. This method can synthesize silicon containing difluoroalkenes on a large scale under mild conditions and exhibits excellent antifungal activity: the inhibition rate against pathogenic bacteria such as gray mold is>60% at 50 μ g/mL, and the EC50 value is better than or equivalent to commercial fungicides. Theoretical calculations (DFT/MEP) reveal the unique electronic properties of highly active compounds, and scanning electron microscopy confirms their effective inhibition of hyphal growth. This work provides innovative lead compounds for the development of structurally optimized and novel fungicides.