Xia Zhi, Zhou Qing, Zhang Yu, Zhang Tao, Xue Wei
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China; College of Chemistry and Chemical Engineering, Guizhou University of Engineering Science, Bijie 551700, China.
National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China.
J Adv Res. 2025 May;71:55-65. doi: 10.1016/j.jare.2024.05.029. Epub 2024 May 31.
INTRODUCTION: Traditional pesticides have poor-water solubility, high toxicity and low bioavailability. Therefore, it is of great significance for the sustainable and healthy development of the pesticide industry to develop efficient and ecofriendly new chemical pesticide products and formulations. OBJECTIVES: This study aims to synthesize a series of derivatives based on chalcone structure (HPPO), and then use the amphiphilic and self-assembly characteristics of N-succinyl-chitosan (NSCS) to prepare HPPO@NSCS nanoparticles (HPPO@NSCS NPs) in order to realize the green application of HPPO, and investigate the antifungal activity and mechanisms of HPPO@NSCS NPs. METHODS: NSCS was synthesized by structural modification using chitosan as the carrier. Based on its amphiphilic and self-assembly characteristics, HPPO-16@NSCS NPs were reasonably prepared by combining with active small molecule HPPO-16. Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM), dynamic light scattering (DLS), fluorescence spectroscopy (FS) and high-performance liquid chromatography (HPLC) were used to characterize the physicochemical properties of NSCS and HPPO-16@NSCS NPs. The inhibitory activity of nanopesticides against Rhizoctonia solani (R. solani) was tested in vivo and in vitro. The mechanism of antifungal action was discussed from the observation of pathogen morphology, fluorescence staining and enzyme activity determination. RESULTS: 28 small molecules based on chalcone structure (HPPO-1-28), NSCS and HPPO-16@NSCS were successfully synthesized. The application of HPPO-16@NSCS could impair the development, cell structure, cellular energy utilization, and metabolism pathways of the fungi. The protective effects of HPPO-16@NSCS NPs on rice leaves and leaf sheaths were 80.9 and 76.1 %, respectively, which were better than those of azoxystrobin. CONCLUSION: This study reveals that these simple chalcone derivatives can be further explored as viable antibacterial alternatives and NSCS as a novel pesticide matrix can be used for the delivery of more insoluble pesticides.
引言：传统农药水溶性差、毒性高且生物利用度低。因此，开发高效、生态友好的新型化学农药产品和制剂对农药行业的可持续健康发展具有重要意义。 目的：本研究旨在合成一系列基于查尔酮结构的衍生物（HPPO），然后利用N-琥珀酰壳聚糖（NSCS）的两亲性和自组装特性制备HPPO@NSCS纳米颗粒（HPPO@NSCS NPs），以实现HPPO的绿色应用，并研究HPPO@NSCS NPs的抗真菌活性及作用机制。 方法：以壳聚糖为载体，通过结构修饰合成NSCS。基于其两亲性和自组装特性，与活性小分子HPPO-16合理制备HPPO-16@NSCS NPs。采用傅里叶变换红外光谱（FTIR）、透射电子显微镜（TEM）、动态光散射（DLS）、荧光光谱（FS）和高效液相色谱（HPLC）对NSCS和HPPO-16@NSCS NPs的理化性质进行表征。在体内和体外测试纳米农药对立枯丝核菌（R. solani）的抑制活性。从病原菌形态观察、荧光染色和酶活性测定等方面探讨抗真菌作用机制。 结果：成功合成了28种基于查尔酮结构的小分子（HPPO-1-28）、NSCS和HPPO-16@NSCS。HPPO-16@NSCS的应用可损害真菌的发育、细胞结构、细胞能量利用和代谢途径。HPPO-16@NSCS NPs对水稻叶片和叶鞘的保护效果分别为80.9%和76.1%，优于嘧菌酯。 结论：本研究表明，这些简单的查尔酮衍生物可作为可行的抗菌替代品进一步探索，NSCS作为一种新型农药基质可用于递送更多难溶性农药。
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