Synthesis And Fungicidal Activity Of Novel Methoxyacrylate Derivatives

Theβ-methoxyacrylate fungicides are an outstanding new class of cytochrome bcl complex Qo site inhibitors, and this class of fungicides is based on a group of natural lead derivatives of (E)-methylβ-methoxyacrylate, such as strobilurin A and oudemansin A. With their broad spectrum of activity, high activity at low rates of application and outstanding environmental friendly, the strobilurins have been one of the most important classes of agricultural fungicides and might in the near future assume the number one position in the market, represent more than 20 percent of the world fungicide market. However, as we all know that the resistance appeared after the long term use of fungicides, discovering new generation of fighting resistence with novel frame construction has become a challenged poject in pesticidal field.In order to search for novel lead-structure with high activities, according to the early work of our research group, the side chain and pharmacophore of the strobilurins derivatives were optimized from the commercialized strobilurins and high bioactive compounds the literature reported, by the means of the active structural stitching and the bioisosterism, This dissertation including as follows:1. The strobilurins derivatives are summarized in the paper, and the review describes in detail their structure of natural structure , history of develoment, structure optimization, synthesis methods, biochemical mode of action and resistance risk.2. Fifty-three strobilurin derivatives with novel side chains were designed and synthesized by a multiple step synthetic procedures. Their structures were characterized by ¹H NMR, MS spectroscopies, element quantitative analysis and X-Ray analysis. The structures are shown as follows:3. Fourty-eight strobilurin derivatives with the furan-2(5H)-one pharmacophore were designed and synthesized by a multiple step synthetic procedures. Their structures were characterized by ¹H NMR, MS spectroscopies, element quantitative analysis and X-Ray analysis. The structures are shown as follows: 4. Twelve strobilurin derivatives with the 1,3,4-Oxazole pharmacophore were designed and synthesized by a multiple step synthetic procedures. Their structures were characterized by ¹H NMR, MS spectroscopies and element quantitative analysis. The structure is shown as follows:5. The bioactivity of all the target compounds were tested. The result of test indicated that many compounds displayed excellent fungicidal activity against tested fungi at the concentration of 200 mg.L^-1.For example, the compoundâ… v showed 90% fungicidal activity against Sphaerotheca fidiginea, the compoundsâ…¡1,â…¡r,â…¢d andâ…¢e showed 81% fungicidal activity against Sphaerotheca fuliginea, the compoundsâ… n,â… u,â…£3k showed more than 60% fungicidal activity against Sphaerotheca fuliginea, the compoundsâ…£1a andâ…£3k showed 67% fungicidal activity against Pseudoperonospora cubensis, the compoundâ…¢d showed 62% fungicidal activity against Rhizoctonia solani.