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.
Highlights
Amide compounds were widely used in pharmaceutical and agrochemical fields due to their wide range of biological activity
A lot of novel amide derivatives have been synthesized, some of them showed good fungicidal or insecticidal activities, and the mode of action on amide fungicides has been reviewed recently [8,9,10,11,12,13,14,15,16]. 2,6-Dimethyl-6-hydroxy-2E,4E-hepta-2, 4-diene acid and (6R)-3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide were isolated from the fruit of Litsea cubeba in Tibet, and they were evaluated to have good fungicidal activities in our laboratory [17,18]
In order to find some novel derivatives with excellent fungicidal activity and explore the differences between 3,7-dimethyl-2,6-octadienoic acid and 3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide (Scheme 1) against phytopathogens, (Z/E)-3,7-dimethyl-2,6-octadienoic acids were synthesized via two-step selective oxidation with the commercial available nerol/geraniol as the starting material [19,22,23]
Summary
Amide compounds were widely used in pharmaceutical and agrochemical fields due to their wide range of biological activity. 2,6-Dimethyl-6-hydroxy-2E,4E-hepta-2, 4-diene acid and (6R)-3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide were isolated from the fruit of Litsea cubeba in Tibet, and they were evaluated to have good fungicidal activities in our laboratory [17,18]. Based on these results, some of the seven-membered lactone derivatives were synthesized and confirmed to exhibit moderate to excellent fungicidal activities [19,20,21]. In order to find some novel derivatives with excellent fungicidal activity and explore the differences between 3,7-dimethyl-2,6-octadienoic acid and 3,7-dimethyl-7-hydroxyl-2-octen-1,6-olide (Scheme 1) against phytopathogens, (Z/E)-3,7-dimethyl-2,6-octadienoic acids were synthesized via two-step selective oxidation with the commercial available nerol/geraniol as the starting material [19,22,23]. Synthetic route of (Z/E)-3,7-dimethyl-2,6-octadienamide and their 6,7-epoxy analogues
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