具有含氮杂环结构的新氰基丙烯酸酯类化合物的研究
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摘要
在除草剂的分子设计中,基于D1蛋白的PS 11电子传递抑制剂的研究一直受到极大的关注。大量研究表明,氰基丙烯酸酯是一类活性很高的光系统Ⅱ(PSⅡ)电子传递抑制剂,由于该类化合物除草作用机制特殊,选择性高,对有益生物无毒,而且具有环境相容性好的特点,因而成为近年来国内外农药研究领域的热点。氰基丙烯酸酯类化合物除具有除草活性以外,还具有杀虫、杀菌、抗癌、抗病毒等生物活性。进一步开展氰基丙烯酸酯类化合物的研究将具有广阔的发展空间和良好的发展前景。
杂环化合物在具有生物活性的化合物中占据重要的地位,在医药和农药领域都有广泛的应用,例如,中草药的有效成分生物碱大多是杂环化合物；部分维生素,抗菌素都含有杂环。而含氮杂环化合物,又是其中一个非常活跃的研究领域,动植物体内起重要生理作用的血红素、叶绿素、核酸的碱基等都是含氮杂环化合物。近年来由于人们对农药安全性要求的不断提高,许多传统农药如有机磷、有机氯类农药慢慢退出了历史舞台,而含氮杂环类农药由于其独特的作用机制、高活性、高选择性、低毒、环境友好等特点成为新农药创制领域的热点,并开创了绿色农药研究的新时代。
为了进一步研究含不同取代基的氰基丙烯酸酯类化合物的构效关系,寻找高效、绿色、新型除草剂,我们以高除草活性氰基丙烯酸酯类化合物为先导结构、根据生物电子等排原理和活性基团拼接的方法,将不同结构的含氮杂环(如1,3,4-噻二唑、1,2,3-噻二唑、噻唑甲基苯基醚、噻唑甲硫基乙胺基、吡啶甲硫基乙胺基等)引入氰基丙烯酸酯的分子结构中,设计并合成了14个系列120个氰基丙烯酸酯类化合物,还合成了17个未见文献报道的中间体。所有目标化合物的结构均经1H NMR和元素分析(或高分辨质谱分析)确证,部分化合物的结构还经质谱、13C NMR、红外吸收光谱及X-射线晶体衍射进一步确证。室内生物活性测试结果表明,大部分化合物显示出优良的除草活性及良好的选择性,部分化合物还具有一定的杀菌和植物生长调节活性。有关研究成果为进一步开展氰基丙烯酸酯类化合物的研究奠定了良好的理论和实验基础。
Cyanoacrylates have been the subject of intense interest for the past decades as one kind of herbicides. A detailed study of these compounds revealed that cyanoacrylates are inhibitors of photosystem II(PS II) electron transportation, which inhibits the growth of weeds by disrupting photosynthetic electron transportation at a common binding domain on the Dl protein (32kDa polypeptide) of the PS II reaction center. In recent years many cyanoacrylates containing heterocycles exhibited excellent herbicidal activities, insecticidal activities, fungicidal activities, anticancer activities or antivirus activities. Therefore, the research in this field have good prospects for development.
Heterocyclic compounds especially nitrogen-containing heterocyclic compounds are an important part of the biologically active compounds and are widely used in the field of medicines and pesticides, for example, the active ingredients in herbal alkaloids or some vitamins and antibiotics are mostly heterocyclic compounds. Heme, chlorophyll and nucleic acid which play an important physiological role of bases in animals and plants are nitrogen-containing heterocyclic compounds also. In recent years, due to the awareness of pesticide safety requirements, many of the traditional pesticides such as organophosphate pesticides and organochlorine pesticides gradually withdraw from the stage of pesticide, while the nitrogen-containing heterocyclic pesticides have been a hot area of pesticide and opened a new era of green pesticide research due to its advantage of high activity, high selectivity, low toxicity, and environment-friendly.
In order to further study the structure-activity relationship of different substituents in cyanoacrylates and look for new herbicides with improved prifiles, we used (Z)-ethoxyethyl-2-cyano-3-methylthio-3-(2-chloro-5-pyridyl)methanaminoacrylate as a leading compound to design and synthesize 14 series of novel cyanoacrylates with nitrogen-containing heterocyclic compounds using bioisoterism and union of active group.
120 Novel target compounds and 17 novel intermediates were synthesied. The structures of the compounds were confirmed by NMR, IR, MS, elemental analysis(or HRMS analysis) and X-ray diffraction. The bioactivity tests showed that most of the compounds showed good herbicidal activities and excellent selectivity, some of the compounds also have fungicidal activities and plant growth regulatory activities. We have laid a solid theoretical and experimental basis on the research of cyanoacrylates in the future.
杂环化合物在具有生物活性的化合物中占据重要的地位,在医药和农药领域都有广泛的应用,例如,中草药的有效成分生物碱大多是杂环化合物；部分维生素,抗菌素都含有杂环。而含氮杂环化合物,又是其中一个非常活跃的研究领域,动植物体内起重要生理作用的血红素、叶绿素、核酸的碱基等都是含氮杂环化合物。近年来由于人们对农药安全性要求的不断提高,许多传统农药如有机磷、有机氯类农药慢慢退出了历史舞台,而含氮杂环类农药由于其独特的作用机制、高活性、高选择性、低毒、环境友好等特点成为新农药创制领域的热点,并开创了绿色农药研究的新时代。
为了进一步研究含不同取代基的氰基丙烯酸酯类化合物的构效关系,寻找高效、绿色、新型除草剂,我们以高除草活性氰基丙烯酸酯类化合物为先导结构、根据生物电子等排原理和活性基团拼接的方法,将不同结构的含氮杂环(如1,3,4-噻二唑、1,2,3-噻二唑、噻唑甲基苯基醚、噻唑甲硫基乙胺基、吡啶甲硫基乙胺基等)引入氰基丙烯酸酯的分子结构中,设计并合成了14个系列120个氰基丙烯酸酯类化合物,还合成了17个未见文献报道的中间体。所有目标化合物的结构均经1H NMR和元素分析(或高分辨质谱分析)确证,部分化合物的结构还经质谱、13C NMR、红外吸收光谱及X-射线晶体衍射进一步确证。室内生物活性测试结果表明,大部分化合物显示出优良的除草活性及良好的选择性,部分化合物还具有一定的杀菌和植物生长调节活性。有关研究成果为进一步开展氰基丙烯酸酯类化合物的研究奠定了良好的理论和实验基础。
Cyanoacrylates have been the subject of intense interest for the past decades as one kind of herbicides. A detailed study of these compounds revealed that cyanoacrylates are inhibitors of photosystem II(PS II) electron transportation, which inhibits the growth of weeds by disrupting photosynthetic electron transportation at a common binding domain on the Dl protein (32kDa polypeptide) of the PS II reaction center. In recent years many cyanoacrylates containing heterocycles exhibited excellent herbicidal activities, insecticidal activities, fungicidal activities, anticancer activities or antivirus activities. Therefore, the research in this field have good prospects for development.
Heterocyclic compounds especially nitrogen-containing heterocyclic compounds are an important part of the biologically active compounds and are widely used in the field of medicines and pesticides, for example, the active ingredients in herbal alkaloids or some vitamins and antibiotics are mostly heterocyclic compounds. Heme, chlorophyll and nucleic acid which play an important physiological role of bases in animals and plants are nitrogen-containing heterocyclic compounds also. In recent years, due to the awareness of pesticide safety requirements, many of the traditional pesticides such as organophosphate pesticides and organochlorine pesticides gradually withdraw from the stage of pesticide, while the nitrogen-containing heterocyclic pesticides have been a hot area of pesticide and opened a new era of green pesticide research due to its advantage of high activity, high selectivity, low toxicity, and environment-friendly.
In order to further study the structure-activity relationship of different substituents in cyanoacrylates and look for new herbicides with improved prifiles, we used (Z)-ethoxyethyl-2-cyano-3-methylthio-3-(2-chloro-5-pyridyl)methanaminoacrylate as a leading compound to design and synthesize 14 series of novel cyanoacrylates with nitrogen-containing heterocyclic compounds using bioisoterism and union of active group.
120 Novel target compounds and 17 novel intermediates were synthesied. The structures of the compounds were confirmed by NMR, IR, MS, elemental analysis(or HRMS analysis) and X-ray diffraction. The bioactivity tests showed that most of the compounds showed good herbicidal activities and excellent selectivity, some of the compounds also have fungicidal activities and plant growth regulatory activities. We have laid a solid theoretical and experimental basis on the research of cyanoacrylates in the future.
引文
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