Design, Synthesis, and Bioactivity of Eighteen Novel 2H-1,4-Benzoxazin-3(4H)-one Containing a Propanolamine Moiety
Jia-Rui Rao
Guizhou Tea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorCorresponding Author
Yu-Feng Zhou
Guizhou Tea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorXin Zhang
Institute of Biotechnology, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorXing-Li Zhao
Institute of Biotechnology, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorJia-Rui Rao
Guizhou Tea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorCorresponding Author
Yu-Feng Zhou
Guizhou Tea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorXin Zhang
Institute of Biotechnology, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorXing-Li Zhao
Institute of Biotechnology, Guizhou Academy of Agricultural Sciences, Guiyang, 550006 China
Search for more papers by this authorAbstract
To develop a novel skeleton for broad-spectrum pesticides with high-efficiency against tea tree diseases, a series of aniline 2H-1,4-benzoxazin-3(4H)-one derivatives containing a propanolamine structure was synthesized and confirmed by 1H-NMR, 13C-NMR, 19F-NMR, HRMS, and single-crystal diffraction analysis. Bioactivities were evaluated against tobacco mosaic virus (TMV, the model virus), three kinds of bacteria, and five typical plant fungi. Bioassay results showed that compound 2i (EC50=395.05 μg/mL) had the best curative activity against TMV, 3d (EC50=45.70 μg/mL) had the best inhibitory activity against Pseudomonas syringae pv. Actinidiae, and 3a (EC50=13.53 μg/mL) had the best inhibitory activity against Pestalotiopsis trachicarpicola. Scanning electron microscope morphological observation of P. trachicarpicola treated with 0, 100, and 200 μg/mL 3a revealed dried, flattened and folded outer walls of the hyphae at higher concentrations, leading to inhibition of fungal growth. The broad-spectrum bioactivities (against viruses, bacteria and fungi) of this series of target compounds indicate that these 2H-1,4-benzoxazin-3(4H)-one derivatives containing a propanolamine moiety are potential skeletons for developing pesticides with wide-ranging activities against various tea tree diseases.
Graphical Abstract
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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