新型甲氧基丙烯酸酯类衍生物的合成及杀菌活性研究
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摘要
甲氧基丙烯酸酯类杀菌剂是以天然产物Strobilurin A和Oudemansin A为先导而开发的新型细胞色素bcl复合物Q_0抑制剂，是一类高效、广谱及环境友好的新型杀菌剂，目前它已成为世界杀菌剂市场上最主要的品种，占据了市场份额的20％以上。随着抗性的产生，研究结构新颖的新一代反抗性的甲氧基丙烯酸酯类杀菌剂成为该领域内一个具有挑战性的课题。
为了寻求高活性的先导结构，结合本课题组前期的工作基础，本文以商品化品种和文献报道的高活性化合物作为先导结构，根据活性亚结构拼接、生物等排取代等方法对甲氧基丙烯酸酯类衍生物的侧链部分以及药效团部分开展深入的结构优化研究。具体研究内容如下：
1、对甲氧基丙烯酸酯类杀菌剂的天然产物结构、开发历程、结构修饰、合成、作用机制和抗性等方面的研究进展进行了系统总结。
2、设计合成了三类共53个侧链结构新颖的甲氧基丙烯酸酯类衍生物。采用~1H NMR、MS、元素分析对所合成的化合物进行了系统的结构表征，同时还测定了部分代表性化合物的晶体结构。
3、设计合成了一类共48个药效团为呋喃酮的新型类甲氧基丙烯酸酯类衍生物。采用~1HNMR、MS、元素分析对所合成的化合物进行了系统的结构表征，同时还测定了代表性化合物的晶体结构。
4、设计合成了一类共12个药效团为1,3,4-(?)二唑的新型类甲氧基丙烯酸酯类衍生物。采用~1H NMR、MS、元素分析对所合成的化合物进行了系统的结构表征。
5、测试了所有化合物的除草、杀虫和杀菌活性，发现部分化合物具有较好的杀菌活性。在200 mg．L~(-1)浓度下，测定了所有化合物对黄瓜霜霉病、黄瓜白粉病、黄瓜灰霉病和水稻纹枯病的杀菌活性。其中化合物Ⅰv对黄瓜白粉病菌的抑制活性达90％，ⅡI、Ⅱr、Ⅲd和Ⅲe对黄瓜白粉病的抑制活性为81％，Ⅰn、Ⅰu、Ⅳ3k对黄瓜白粉病菌的抑制活性均高于60％，Ⅳ1a和Ⅳ3k对黄瓜霜霉病的抑制活性为67％，Ⅲd对水稻纹枯病的抑制活性为62％。
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 compoundⅠv showed 90% fungicidal activity against Sphaerotheca fidiginea, the compoundsⅡ1,Ⅱr,Ⅲd andⅢe showed 81% fungicidal activity against Sphaerotheca fuliginea, the compoundsⅠn,Ⅰu,Ⅳ3k showed more than 60% fungicidal activity against Sphaerotheca fuliginea, the compoundsⅣ1a andⅣ3k showed 67% fungicidal activity against Pseudoperonospora cubensis, the compoundⅢd showed 62% fungicidal activity against Rhizoctonia solani.
为了寻求高活性的先导结构，结合本课题组前期的工作基础，本文以商品化品种和文献报道的高活性化合物作为先导结构，根据活性亚结构拼接、生物等排取代等方法对甲氧基丙烯酸酯类衍生物的侧链部分以及药效团部分开展深入的结构优化研究。具体研究内容如下：
1、对甲氧基丙烯酸酯类杀菌剂的天然产物结构、开发历程、结构修饰、合成、作用机制和抗性等方面的研究进展进行了系统总结。
2、设计合成了三类共53个侧链结构新颖的甲氧基丙烯酸酯类衍生物。采用~1H NMR、MS、元素分析对所合成的化合物进行了系统的结构表征，同时还测定了部分代表性化合物的晶体结构。
3、设计合成了一类共48个药效团为呋喃酮的新型类甲氧基丙烯酸酯类衍生物。采用~1HNMR、MS、元素分析对所合成的化合物进行了系统的结构表征，同时还测定了代表性化合物的晶体结构。
4、设计合成了一类共12个药效团为1,3,4-(?)二唑的新型类甲氧基丙烯酸酯类衍生物。采用~1H NMR、MS、元素分析对所合成的化合物进行了系统的结构表征。
5、测试了所有化合物的除草、杀虫和杀菌活性，发现部分化合物具有较好的杀菌活性。在200 mg．L~(-1)浓度下，测定了所有化合物对黄瓜霜霉病、黄瓜白粉病、黄瓜灰霉病和水稻纹枯病的杀菌活性。其中化合物Ⅰv对黄瓜白粉病菌的抑制活性达90％，ⅡI、Ⅱr、Ⅲd和Ⅲe对黄瓜白粉病的抑制活性为81％，Ⅰn、Ⅰu、Ⅳ3k对黄瓜白粉病菌的抑制活性均高于60％，Ⅳ1a和Ⅳ3k对黄瓜霜霉病的抑制活性为67％，Ⅲd对水稻纹枯病的抑制活性为62％。
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 compoundⅠv showed 90% fungicidal activity against Sphaerotheca fidiginea, the compoundsⅡ1,Ⅱr,Ⅲd andⅢe showed 81% fungicidal activity against Sphaerotheca fuliginea, the compoundsⅠn,Ⅰu,Ⅳ3k showed more than 60% fungicidal activity against Sphaerotheca fuliginea, the compoundsⅣ1a andⅣ3k showed 67% fungicidal activity against Pseudoperonospora cubensis, the compoundⅢd showed 62% fungicidal activity against Rhizoctonia solani.
引文
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