Design,Synthesis, and Fungicidal Activities of Indole-Modified Cinnamamide Derivatives |
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Authors: | Xinwei Zhang Jun Fang Chenjie Li Jie Zhang Shuwen Yang Bin Deng Song Tu |
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Institution: | Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005 P. R. China |
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Abstract: | Dimethomorph is a kind of cinnamamide fungicide with high fungicidal activities for oomycete diseases. The commercially available dimethomorph is a mixture of two isomers, in which (Z)-dimethomorph possessing higher activity and (E)-dimethomorph possessing lower activity. Herein, we reported the design, synthesis and fungicidal activities of a series of novel indole-modified cinnamamide derivatives, which used the indole group to ‘fix’ the cis-styrene group in (Z)-dimethomorph. The modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. Tested the fungicidal activities, it was found that compounds 8j , 9a , 9e , 9i and 9j showed excellent in vivo fungicidal activities (80–100 %) against Pseudoperonospora cubensis at a concentration of 100 mg L−1, while dimethomorph and flumorph were noneffective. Moreover, parts of synthesized indole-modified cinnamamide derivatives 8 ( 8a , 8c , 8d and 8j ) and 9 ( 9c and 9j ) exhibited the same in vivo fungicidal activities against Phytophthora infestans with dimethomorph or flumorph at a concentration of 50 mg L−1 with 100 % inhibition. The biological assay results indicated that indole-modified cinnamamide derivatives have promising applications in the prevention and treatment of Phytophthora infestans. |
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Keywords: | cinnamamide fungicide dimethomorph indole synthesis fungicidal activities |
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