title: Synthesis and Fungicidal Activities of (Z/E)-3,7-Dimethyl-2,6-octadienamide and Its 6,7-Epoxy Analogues.
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.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. yangmy@cau.edu.cn.
authors.forename: Mingyan
authors.initials: M
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. dhb1986115@cau.edu.cn.
authors.forename: Hongbo
authors.initials: H
authors.lastname: Dong
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. jiangjiazhen@cau.edu.cn.
authors.forename: Jiazhen
authors.initials: J
authors.lastname: Jiang
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. wangma@cau.edu.cn.
authors.forename: Mingan
authors.initials: M
authors.lastname: Wang
mesh_terms: D000577:Amides / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D004853:Epoxy Resins / Q000737:chemistry*; D005658:Fungi / Q000187:drug effects*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000935:Antifungal Agents; D004853:Epoxy Resins
keywords: 3,7-dimethyl-2,6-octadienamide; 3,7-dmethyl-6,7-epoxy-2-octadienamide; fungicidal activity; synthesis