Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues

Molecules

Mingyan Yang²  Hongbo Dong²  Jiazhen Jiang²  Mingan Wang¹ 

[1] Department of Applied Chemistry, China Agricultural University, Beijing 100193, China

关键词: 3;    7-dimethyl-2;    6-octadienamide;    3;    7-dmethyl-6;    7-epoxy-2-octadienamide;    synthesis;    fungicidal activity;   

DOI  :  10.3390/molecules201219743

来源: mdpi

【 摘 要 】

In order to find new lead compounds with high fungicidal activity, (Z/E)-3,7-dimethyl-2,6-octadienoic acids were synthesized via selective two-step oxidation using the commercially available geraniol/nerol as raw materials. Twenty-eight different (Z/E)-3,7-dimethyl-2,6-octadienamide derivatives were prepared by reactions of (Z/E)-carboxylic acid with various aromatic and aliphatic amines, followed by oxidation of peroxyacetic acid to afford their 6,7-epoxy analogues. All of the compounds were characterized by HR-ESI-MS and ¹H-NMR spectral data. The preliminary bioassays showed that some of these compounds exhibited good fungicidal activities against Rhizoctonia solani (R. solani) at a concentration of 50 µg/mL. For example, 5C, 5I and 6b had 94.0%, 93.4% and 91.5% inhibition rates against R. solani, respectively. Compound 5f displayed EC₅₀ values of 4.3 and 9.7 µM against Fusahum graminearum and R. Solani, respectively.

【 授权许可】

CC BY   
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