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

Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
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Academic Editor: Jean Jacques Vanden Eynde
Molecules 2015, 20(12), 21023-21036; https://doi.org/10.3390/molecules201219743
Received: 10 October 2015 / Revised: 17 November 2015 / Accepted: 17 November 2015 / Published: 25 November 2015
(This article belongs to the Section Organic Chemistry)
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. View Full-Text
Keywords: 3,7-dimethyl-2,6-octadienamide; 3,7-dmethyl-6,7-epoxy-2-octadienamide; synthesis; fungicidal activity 3,7-dimethyl-2,6-octadienamide; 3,7-dmethyl-6,7-epoxy-2-octadienamide; synthesis; fungicidal activity
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Yang, M.; Dong, H.; Jiang, J.; Wang, M. Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues. Molecules 2015, 20, 21023-21036.

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