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Molecules 2015, 20(12), 21023-21036; doi:10.3390/molecules201219743

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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Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 10 October 2015 / Revised: 17 November 2015 / Accepted: 17 November 2015 / Published: 25 November 2015
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [710 KB, uploaded 25 November 2015]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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