新型Strobilurins衍生物的设计、合成及生物活性研究
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摘要
Strobilurins类杀菌剂是人们以天然产物为先导化合物设计合成的一类新型高效、广谱、安全性高的杀菌剂,现已成为当今世界杀菌剂市场最活跃、最有发展潜力的新一代杀菌剂。由于长期施用,该类杀菌剂也产生了抗性。因此针对抗性的产生,要求不断改造更新杀菌剂品种的骨架结构。
为了寻求高活性的结构骨架或先导结构,本文采用电子等排原理、活性亚结构拼接方法,对Strobilurins类杀菌剂的侧链进行了结构改造和修饰,设计合成了四种结构类型十个系列共155个未见文献报道的化合物。并研究了所合成化合物的生物活性、构效关系及波谱性质,寻找到一批具有优良杀菌活性的新型化合物。具体研究内容如下:
1、系统总结了具有杀菌活性的Strobilurins衍生物的分类、合成方法、作用机制及其抗性等方面的研究进展。
2、设计合成了四大类十个系列共155个新型Strobilurins衍生物。所有合成化合物都采用~1H NMR、MS、元素分析进行了结构表征,同时也获得了部分代表性化合物的晶体,进一步确证了化合物的结构。
3、按照《农药生物活性测定标准操作规范(SOP)》,采用活体盆栽法,测试了所有化合物的除草、杀虫和杀菌活性(部分化合物的生物活性测试正在进行中)。发现了一批具有优良杀菌活性的化合物,其中化合物Ⅳ1k已成功申请国内专利和国际PCT专利保护,其开发工作正在进行中。这将为我国开发具有自主知识产权的新型农药做出贡献。
杀菌活性方面: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、水稻纹枯病的杀菌活性。发现了一批具有优良杀菌活性的化合物,其中化合物Ⅰ1a、Ⅰ1c、Ⅰ1m、Ⅰ1w、Ⅰ1x、Ⅰ3j、Ⅰ3l、Ⅳ1b、Ⅱ1a、Ⅱ1g、Ⅱ1i、Ⅱ1j、Ⅱ1k、Ⅱ1l、Ⅱ1p、Ⅱ1q、Ⅱ1r、Ⅱ3b、Ⅱ3c、Ⅱ3d、Ⅲ1a、Ⅲ1d、Ⅲ2d、Ⅲ2f、Ⅲ3a、Ⅲ3b、Ⅲ3c、Ⅲ3d、Ⅲ3e、Ⅲ3h、Ⅲ3j、Ⅲ3k、Ⅳ1f、Ⅳ1g、Ⅳ1k、Ⅳ1l、Ⅳ2g在该浓度下对黄瓜霜霉病的抑制活性达到100%,Ⅰ1a、Ⅰ1c、Ⅰ1e、Ⅰ1l、Ⅰ1m、Ⅰ3q、Ⅱ1b、Ⅱ1d、Ⅱ1h、Ⅲ1e、Ⅲ1f、Ⅲ2e、Ⅲ3f、Ⅲ3i、Ⅲ3I、Ⅳ1a、Ⅳ1d、Ⅳ1e、Ⅳ1h、Ⅳ1i、Ⅳ1j、Ⅳ1m、Ⅳ2b的抑制率也超过80%。同时化合物Ⅲ1a、Ⅲ2f、Ⅳ1e、Ⅳ1k、Ⅳ1l对黄瓜白粉病菌的抑制率为100%,化合物Ⅱ1b、Ⅱ1h、Ⅳ2b、Ⅳg、Ⅳ1a、Ⅳ1b、Ⅳ1c、Ⅳ1d、Ⅳ1h、Ⅳ1j、Ⅳ1m对黄瓜白粉病也表现出超过80%的抑菌率。进一步的杀菌复筛表明,化合物Ⅳ1k对黄瓜霜霉病、黄瓜白粉病的防效优于同类商品化对照药剂醚菌酯。
杀虫活性方面:试验结果表明,Ⅱ1d、Ⅱ1e、Ⅱ1h、Ⅱ1k、Ⅱ1l在500 mg.L~(-1)下对粘虫的抑制率为100%,而且化合物Ⅱ1d还表现出较好的杀螨活性,对朱砂叶螨的抑制率达到98%。当浓度降至100 mg.L~(-1)时,化合物Ⅱ1h对粘虫的抑制率仍为100%,在浓度降为20 mg.L~(-1)时,化合物Ⅱ1h的抑制率为55%,这说明该化合物的杀虫活性达到了一定的水平,体现出进一步研究的价值。
除草活性方面:以稗草、马唐、狗尾草、早熟禾、芥菜、反枝苋及小藜等六种杂草为试验靶标,在用量为150 g/hm~2条件下,对所合成的化合物进行了盆栽普筛试验。试验结果显示,未发现有除草活性的化合物。
4、以细胞色素bcl复合物为靶标,对部分目标化合物进行了酶活性试验。结果表明,系列化合物Ⅲ1a-1f、Ⅲ2a-2i、Ⅲ3a-3l的酶活性远优于同类商品化对照药剂。其中化合物Ⅲ1e的IC_(50)为1.2nM,比同类商品化对照药剂醚菌酯高出120多倍,比嘧菌酯高300多倍,体现出了进一步研究的价值。
5、初步总结了Strobilurins衍生物的结构与活性关系,为进一步研究该类化合物、创制新型杀菌剂提供了重要的理论依据。
The strobilurins are an outstanding new class of agricultural fungicides,and this class of fungicides is based on a group of natural lead derivatives of(E)-methylβ-methoxyacrylate,such as strobilurin A,oudemansin A and myxothiazol A.With their broad spectrum of activity,high activity at low rates of application and outstanding environmental tolerability,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.However,as we all know that the resistance appeared after the long term use of fungicides,new frame construction are needed to be found to keep or improve the biological activity.
In order to search for novel strobilurin derivatives with high activities,according to the bioisosterism and the connecting principle of actively biological groups,nineteen series and seven kinds of two hundred and twenty-nine strobilurin derivatives were designed and synthesized in good to excellent yields.Their bioactivities,structure-activity relationship and spectral properties were studied,and many of them were found to show excellent fungicidal activities.This dissertation may be summarized as follows:
The strobilurin derivatives are summarized in the paper,and the review describes in detail their main categorizationp,synthesis methods,biochemical mode of action and resistance risk.
Two hundred and twenty-nine strobilurin derivatives were designed and synthesized by a multiple step synthetic procedures.Their structures were characterized by ~ⅠH NMR,MS spectroscopies, element quantitative analysis and X-Ray analysis.The results of bioactivity assay indicated that many compounds displayed excellent fungicidal activity against tested fungi at the concentration of 200 mg.L~(-1),such asⅠ1a,Ⅰ1c,Ⅰ1m,Ⅰ1w,Ⅰ1x,Ⅰ3j,Ⅰ3l,Ⅳ1b,Ⅱ1a,Ⅱ1g,Ⅱ1i,Ⅱ1j,Ⅱ1k,Ⅱ1l,Ⅱ1p,Ⅱ1q,Ⅱ1r,Ⅱ3b,Ⅱ3c,Ⅱ3d,Ⅲ1a,Ⅲ1d,Ⅲ2d,Ⅲ2f,Ⅲ3a,Ⅲ3b,Ⅲ3c,Ⅲ3d,Ⅲ3e,Ⅲ3h,Ⅲ3j,Ⅲ3k,Ⅳ1f,Ⅳ1g,Ⅳ1k,Ⅳ1l,Ⅳ2g they showed 100%fungicidal activity against Pseudoperonospora cubensis,and the compoundsⅠ1a,Ⅰ1c,Ⅰ1e,Ⅰ1l,Ⅰ1m,Ⅰ3q,Ⅱ1b,Ⅱ1d,Ⅱ1h,Ⅲ1e,Ⅲ1f,Ⅲ2e,Ⅲ3f,Ⅲ3i,Ⅲ31,Ⅳ1a,Ⅳ1d,Ⅳ1e,Ⅳ1h,Ⅳ1i,Ⅳ1j,Ⅳ1m,Ⅳ2b also showed more than 80%fungicidal activity.Meanwhile,the compoundsⅢ1a,Ⅲ2f,Ⅳ1e,Ⅳ1k,Ⅳ1l showed 100%fungicidal activity against Sphaerotheca fuliginea at the concentration of 200 mg.L~(-1), and the compoundsⅡ1b,Ⅱ1h,Ⅳ2b,Ⅳg,Ⅳ1a,Ⅳ1b,Ⅳ1c,Ⅳ1d,Ⅳ1h,Ⅳ1j,Ⅳ1m also showed more than 80%fungicidal activity.Especially the compoundsⅣ1k were more excellent against Pseudoperonospora cubensis and Sphaerotheca fuliginea than the commercial Kresoxim-methyl.
The results of test indicated that all the target compounds did not displayed good herbicidal activity,however,some of them exhibited excellent in vivo insecticidal activity against Tetranychus cinnabarnus,Mythima separate,Aphis medicagini at the concentration of 250 mg.L~(-1)and 500 mg.L~(-1), such asⅡ1d,Ⅱ1e,Ⅱ1h,Ⅱ1k,Ⅱ1l,they showed 100%insecticidal activity against Mythima separate at the concentration of 500 mg.L~(-1),Especially the compoundsⅡ1h was more excellent with the 55%inhibition activity against Mythima separate at the concentration of 20 mg.L~(-1),which indicated that the strobilurins scaffold could be identified as a novel insecticidal lead structure.
Preliminary bioassay showed some strobilurin derivatives containing pyrazolines and benzothiazole showed excellent insecticidal or fungicidal activity,and the relationship of the biological activity and their structures were studied also.
为了寻求高活性的结构骨架或先导结构,本文采用电子等排原理、活性亚结构拼接方法,对Strobilurins类杀菌剂的侧链进行了结构改造和修饰,设计合成了四种结构类型十个系列共155个未见文献报道的化合物。并研究了所合成化合物的生物活性、构效关系及波谱性质,寻找到一批具有优良杀菌活性的新型化合物。具体研究内容如下:
1、系统总结了具有杀菌活性的Strobilurins衍生物的分类、合成方法、作用机制及其抗性等方面的研究进展。
2、设计合成了四大类十个系列共155个新型Strobilurins衍生物。所有合成化合物都采用~1H NMR、MS、元素分析进行了结构表征,同时也获得了部分代表性化合物的晶体,进一步确证了化合物的结构。
3、按照《农药生物活性测定标准操作规范(SOP)》,采用活体盆栽法,测试了所有化合物的除草、杀虫和杀菌活性(部分化合物的生物活性测试正在进行中)。发现了一批具有优良杀菌活性的化合物,其中化合物Ⅳ1k已成功申请国内专利和国际PCT专利保护,其开发工作正在进行中。这将为我国开发具有自主知识产权的新型农药做出贡献。
杀菌活性方面: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、水稻纹枯病的杀菌活性。发现了一批具有优良杀菌活性的化合物,其中化合物Ⅰ1a、Ⅰ1c、Ⅰ1m、Ⅰ1w、Ⅰ1x、Ⅰ3j、Ⅰ3l、Ⅳ1b、Ⅱ1a、Ⅱ1g、Ⅱ1i、Ⅱ1j、Ⅱ1k、Ⅱ1l、Ⅱ1p、Ⅱ1q、Ⅱ1r、Ⅱ3b、Ⅱ3c、Ⅱ3d、Ⅲ1a、Ⅲ1d、Ⅲ2d、Ⅲ2f、Ⅲ3a、Ⅲ3b、Ⅲ3c、Ⅲ3d、Ⅲ3e、Ⅲ3h、Ⅲ3j、Ⅲ3k、Ⅳ1f、Ⅳ1g、Ⅳ1k、Ⅳ1l、Ⅳ2g在该浓度下对黄瓜霜霉病的抑制活性达到100%,Ⅰ1a、Ⅰ1c、Ⅰ1e、Ⅰ1l、Ⅰ1m、Ⅰ3q、Ⅱ1b、Ⅱ1d、Ⅱ1h、Ⅲ1e、Ⅲ1f、Ⅲ2e、Ⅲ3f、Ⅲ3i、Ⅲ3I、Ⅳ1a、Ⅳ1d、Ⅳ1e、Ⅳ1h、Ⅳ1i、Ⅳ1j、Ⅳ1m、Ⅳ2b的抑制率也超过80%。同时化合物Ⅲ1a、Ⅲ2f、Ⅳ1e、Ⅳ1k、Ⅳ1l对黄瓜白粉病菌的抑制率为100%,化合物Ⅱ1b、Ⅱ1h、Ⅳ2b、Ⅳg、Ⅳ1a、Ⅳ1b、Ⅳ1c、Ⅳ1d、Ⅳ1h、Ⅳ1j、Ⅳ1m对黄瓜白粉病也表现出超过80%的抑菌率。进一步的杀菌复筛表明,化合物Ⅳ1k对黄瓜霜霉病、黄瓜白粉病的防效优于同类商品化对照药剂醚菌酯。
杀虫活性方面:试验结果表明,Ⅱ1d、Ⅱ1e、Ⅱ1h、Ⅱ1k、Ⅱ1l在500 mg.L~(-1)下对粘虫的抑制率为100%,而且化合物Ⅱ1d还表现出较好的杀螨活性,对朱砂叶螨的抑制率达到98%。当浓度降至100 mg.L~(-1)时,化合物Ⅱ1h对粘虫的抑制率仍为100%,在浓度降为20 mg.L~(-1)时,化合物Ⅱ1h的抑制率为55%,这说明该化合物的杀虫活性达到了一定的水平,体现出进一步研究的价值。
除草活性方面:以稗草、马唐、狗尾草、早熟禾、芥菜、反枝苋及小藜等六种杂草为试验靶标,在用量为150 g/hm~2条件下,对所合成的化合物进行了盆栽普筛试验。试验结果显示,未发现有除草活性的化合物。
4、以细胞色素bcl复合物为靶标,对部分目标化合物进行了酶活性试验。结果表明,系列化合物Ⅲ1a-1f、Ⅲ2a-2i、Ⅲ3a-3l的酶活性远优于同类商品化对照药剂。其中化合物Ⅲ1e的IC_(50)为1.2nM,比同类商品化对照药剂醚菌酯高出120多倍,比嘧菌酯高300多倍,体现出了进一步研究的价值。
5、初步总结了Strobilurins衍生物的结构与活性关系,为进一步研究该类化合物、创制新型杀菌剂提供了重要的理论依据。
The strobilurins are an outstanding new class of agricultural fungicides,and this class of fungicides is based on a group of natural lead derivatives of(E)-methylβ-methoxyacrylate,such as strobilurin A,oudemansin A and myxothiazol A.With their broad spectrum of activity,high activity at low rates of application and outstanding environmental tolerability,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.However,as we all know that the resistance appeared after the long term use of fungicides,new frame construction are needed to be found to keep or improve the biological activity.
In order to search for novel strobilurin derivatives with high activities,according to the bioisosterism and the connecting principle of actively biological groups,nineteen series and seven kinds of two hundred and twenty-nine strobilurin derivatives were designed and synthesized in good to excellent yields.Their bioactivities,structure-activity relationship and spectral properties were studied,and many of them were found to show excellent fungicidal activities.This dissertation may be summarized as follows:
The strobilurin derivatives are summarized in the paper,and the review describes in detail their main categorizationp,synthesis methods,biochemical mode of action and resistance risk.
Two hundred and twenty-nine strobilurin derivatives were designed and synthesized by a multiple step synthetic procedures.Their structures were characterized by ~ⅠH NMR,MS spectroscopies, element quantitative analysis and X-Ray analysis.The results of bioactivity assay indicated that many compounds displayed excellent fungicidal activity against tested fungi at the concentration of 200 mg.L~(-1),such asⅠ1a,Ⅰ1c,Ⅰ1m,Ⅰ1w,Ⅰ1x,Ⅰ3j,Ⅰ3l,Ⅳ1b,Ⅱ1a,Ⅱ1g,Ⅱ1i,Ⅱ1j,Ⅱ1k,Ⅱ1l,Ⅱ1p,Ⅱ1q,Ⅱ1r,Ⅱ3b,Ⅱ3c,Ⅱ3d,Ⅲ1a,Ⅲ1d,Ⅲ2d,Ⅲ2f,Ⅲ3a,Ⅲ3b,Ⅲ3c,Ⅲ3d,Ⅲ3e,Ⅲ3h,Ⅲ3j,Ⅲ3k,Ⅳ1f,Ⅳ1g,Ⅳ1k,Ⅳ1l,Ⅳ2g they showed 100%fungicidal activity against Pseudoperonospora cubensis,and the compoundsⅠ1a,Ⅰ1c,Ⅰ1e,Ⅰ1l,Ⅰ1m,Ⅰ3q,Ⅱ1b,Ⅱ1d,Ⅱ1h,Ⅲ1e,Ⅲ1f,Ⅲ2e,Ⅲ3f,Ⅲ3i,Ⅲ31,Ⅳ1a,Ⅳ1d,Ⅳ1e,Ⅳ1h,Ⅳ1i,Ⅳ1j,Ⅳ1m,Ⅳ2b also showed more than 80%fungicidal activity.Meanwhile,the compoundsⅢ1a,Ⅲ2f,Ⅳ1e,Ⅳ1k,Ⅳ1l showed 100%fungicidal activity against Sphaerotheca fuliginea at the concentration of 200 mg.L~(-1), and the compoundsⅡ1b,Ⅱ1h,Ⅳ2b,Ⅳg,Ⅳ1a,Ⅳ1b,Ⅳ1c,Ⅳ1d,Ⅳ1h,Ⅳ1j,Ⅳ1m also showed more than 80%fungicidal activity.Especially the compoundsⅣ1k were more excellent against Pseudoperonospora cubensis and Sphaerotheca fuliginea than the commercial Kresoxim-methyl.
The results of test indicated that all the target compounds did not displayed good herbicidal activity,however,some of them exhibited excellent in vivo insecticidal activity against Tetranychus cinnabarnus,Mythima separate,Aphis medicagini at the concentration of 250 mg.L~(-1)and 500 mg.L~(-1), such asⅡ1d,Ⅱ1e,Ⅱ1h,Ⅱ1k,Ⅱ1l,they showed 100%insecticidal activity against Mythima separate at the concentration of 500 mg.L~(-1),Especially the compoundsⅡ1h was more excellent with the 55%inhibition activity against Mythima separate at the concentration of 20 mg.L~(-1),which indicated that the strobilurins scaffold could be identified as a novel insecticidal lead structure.
Preliminary bioassay showed some strobilurin derivatives containing pyrazolines and benzothiazole showed excellent insecticidal or fungicidal activity,and the relationship of the biological activity and their structures were studied also.
引文
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