Synthesis and fungicidal activity of pyrazole derivatives containing 1,2,3,4-tetrahydroquinoline.
Synthesis and fungicidal activity of pyrazole derivatives containing 1,2,3,4-tetrahydroquinoline.
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1,2,3,4-四氢喹啉吡唑衍生物的合成及其杀菌活性
DOI：
10.1186/s13065-016-0186-8
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发表时间：
2016
影响因子：
--
通讯作者：
Ling Y
中科院分区：
文献类型：
--
作者：
Lei P;Zhang X;Xu Y;Xu G;Liu X;Yang X;Zhang X;Ling Y
小麦全蚀病是由小麦全蚀病菌（Gaeumannomycesgraminisvar.）小麦白粉病是小麦最重要和最普遍的根病之一。鉴于全蚀病仍然难以控制，有必要开发新的有效的农用化学品。吡唑类化合物因其良好的生物活性而被广泛报道。为了寻找结构简单、杀菌活性高的化合物，将天然产物中的生物活性基团1，2，3，4-四氢喹啉引入吡唑结构中。合成了一系列含1，2，3，4-四氢喹啉的吡唑类化合物，并对其杀菌活性进行了评价。sclerotiorum和G.禾谷变种三个月。化合物10 d、10 e、10 h、10 i和10 j对G.禾谷变种三聚体均在90%以上。即使在16.7 μg/mL的较低浓度下，化合物10 d和10 e也分别表现出100%和94.0%的满意活性。结论合成了一系列含1，2，3，4-四氢喹啉的吡唑衍生物，其结构经1H NMR、13 C NMR、IR、HRMS或元素分析确证。化合物10 g的晶体结构通过X射线衍射证实。生物活性测定结果表明，所有目标化合物均具有明显的杀菌活性。特别是化合物10 d和10 e显示出相当的抗G.禾谷变种设计并合成了一系列含1，2，3，4-四氢喹啉的吡唑衍生物。生物活性测定结果表明，所有化合物均具有明显的杀菌活性。
BackgroundTake-all of wheat, caused by the soil-borne fungus Gaeumannomyces graminis var. tritici, is one of the most important and widespread root diseases. Given that take-all is still hard to control, it is necessary to develop new effective agrochemicals. Pyrazole derivatives have been often reported for their favorable bioactivities. In order to discover compounds with high fungicidal activity and simple structures, 1,2,3,4-tetrahydroquinoline, a biologically active group of natural products, was introduced to pyrazole structure. A series of pyrazole derivatives containing 1,2,3,4-tetrahydroquinoline were synthesized, and their fungicidal activities were evaluated.ResultsThe bioassay results demonstrated that the title compounds displayed obvious fungicidal activities at a concentration of 50 μg/mL, especially against V. mali, S. sclerotiorum and G. graminis var. tritici. The inhibition rates of compounds 10d, 10e, 10h, 10i and 10j against G. graminis var. tritici were all above 90 %. Even at a lower concentration of 16.7 μg/mL, compounds 10d and 10e exhibited satisfied activities of 100 % and 94.0 %, respectively. It is comparable to that of the positive control pyraclostrobin with 100 % inhibition rate.ConclusionA series of pyrazole derivatives containing 1,2,3,4-tetrahydroquinoline were synthesized and their structures were confirmed by 1H NMR, 13C NMR, IR spectrum and HRMS or elemental analysis. The crystal structure of compound 10g was confirmed by X-ray diffraction. Bioassay results indicated that all title compounds exhibited obvious fungicidal activities. In particular, compounds 10d and 10e showed comparable activities against G. graminis var. tritici with the commercial fungicide pyraclostrobin at the concentration of 16.7 μg/mL.Graphical abstractA series of pyrazole derivatives containing 1,2,3,4-tetrahydroquinoline were designed and synthesized. Bioassay results indicated that all these compounds exhibited obvious fungicidal activities.