School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China.
Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Nanning 530004, China.
Int J Mol Sci. 2024 Apr 23;25(9):4595. doi: 10.3390/ijms25094595.
The development of novel natural product-derived nano-pesticide systems with loading capacity and sustained releasing performance of bioactive compounds is considered an effective and promising plant protection strategy. In this work, 25 -carvone-based thiazolinone-hydrazone compounds ~ were synthesized by the multi-step modification of -carvone and structurally confirmed. Compound was found to show favorable and broad-spectrum antifungal activity through the in vitro antifungal activity evaluation of compounds ~ against eight phytopathogenic fungi. Thus, it could serve as a leading compound for new antifungal agents in agriculture. Moreover, the -carvone-based nanochitosan carrier bearing the 1,3,4-thiadiazole-amide group was rationally designed for the loading and sustained releasing applications of compound , synthesized, and characterized. It was proven that carrier had good thermal stability below 200 °C, dispersed well in the aqueous phase to form numerous nanoparticles with a size of~20 nm, and exhibited an unconsolidated and multi-aperture micro-structure. Finally, -carvone-based thiazolinone-hydrazone/nanochitosan complexes were fabricated and investigated for their sustained releasing behaviors. Among them, complex with a well-distributed, compact, and columnar micro-structure displayed the highest encapsulation efficiency and desirable sustained releasing property for compound and thus showed great potential as an antifungal nano-pesticide for further studies.
开发具有生物活性化合物负载能力和持续释放性能的新型天然产物衍生的纳米农药系统被认为是一种有效且有前途的植物保护策略。在这项工作中,通过对香芹酮的多步修饰和结构确证,合成了 25 种基于香芹酮的噻唑啉酮腙类化合物。通过对化合物 ~ 对 8 种植物病原真菌的体外抗真菌活性评价,发现化合物 表现出良好的广谱抗真菌活性。因此,它可以作为农业中新型抗真菌剂的先导化合物。此外,为了实现化合物 的负载和持续释放应用,合理设计了带有 1,3,4-噻二唑酰胺基团的基于香芹酮的纳米壳聚糖载体 ,并对其进行了合成和表征。结果表明,载体 在 200°C 以下具有良好的热稳定性,在水相中分散良好,形成尺寸约为~20nm 的众多纳米颗粒,并具有非固结和多孔的微结构。最后,制备了基于香芹酮的噻唑啉酮腙/纳米壳聚糖复合物,并研究了其持续释放行为。其中,具有均匀分布、紧密和柱状微结构的复合物 显示出最高的包封效率和对化合物 的理想持续释放性能,因此作为一种有前途的抗真菌纳米农药,具有进一步研究的潜力。