Synthesis and Characterization of Slow-Release Chitosan Oligosaccharide Pyridine Schiff Base Copper Complexes with Antifungal Activity

Herein, a series of chitosan oligosaccharide copper complexes modified with pyridine groups (CPSx-Cu complexes) were successfully prepared via the Schiff base reaction and ion complexation reaction for slow-release fungicide. The structures of the synthesized derivatives were characterized via Fourier transform infrared spectroscopy and 1H and 13C nuclear magnetic resonance spectroscopy, and the unit configuration of the complexes was calculated using Gaussian software. The slow-release performance experiment demonstrated that the cumulative copper ion release rate of CPSx-Cu complexes was dependent on the type of substituents on the pyridine ring. Furthermore, the in vitro and in vivo antifungal activities of the CPSx-Cu complexes were investigated. At a concentration of 0.4 mg/mL, CPSx-Cu complexes completely inhibited the growth of Pythium vexans and Phytophthora capsici. Results indicated that CPSx-Cu complexes with slow-release ability exhibited better antifungal activity than thiodiazole-copper and copper sulfate basic. This study confirmed that combining chitosan oligosaccharide with bioactive pyridine groups and copper ions is an effective approach to further developing slow-release copper fungicides, providing new possibilities for the application of copper fungicides in green agriculture. This study lays the foundation for further studies on biogreen copper fungicides.