新型含呋喃环结构的吡唑肟酯类化合物的合成及其生物活性
收稿日期: 2015-03-01
修回日期: 2015-03-19
网络出版日期: 2015-04-13
基金资助
国家自然科学基金(No. 21202089)和江苏省“六大人才高峰”(Nos. 2011-SWYY-009, 2013-SWYY-013)资助项目.
Synthesis and Bioactivity of Novel Pyrazole Oxime Ester Derivatives Containing Furan Moiety
Received date: 2015-03-01
Revised date: 2015-03-19
Online published: 2015-04-13
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202089) and the Research Foundation of the Six People Peak of Jiangsu Province (Nos. 2011-SWYY-009, 2013-SWYY-013).
为了寻找具有较高活性的杂环农药, 通过5-取代苯基-2-呋喃甲酰氯与取代吡唑肟的缩合反应, 制备了一系列含多取代基呋喃环结构的吡唑肟酯类化合物. 利用1H NMR, 13C NMR和元素分析对目标化合物的结构进行了表征. 初步的生物试验结果表明, 某些化合物表现出一定的杀虫或杀螨活性. 其中, 5-(4-三氟甲基苯基)呋喃-2-甲酸-[1-甲基-3-甲基-5-(2,4-二氯苯氧基)吡唑-4-甲醛]肟酯(6g)在浓度为400 μg/mL时对朱砂叶螨的杀死率达到83%; 5-(4-氟苯基)呋喃-2-甲酸-[1-(4-甲基苯基)-3-甲基-5-(4-甲基苯氧基)吡唑-4-甲醛]肟酯(6m)在浓度为400 μg/mL时对小菜蛾和蚜虫表现的杀死率分别为71%和64%.
石玉军 , 王森林 , 何海兵 , 李钰 , 李阳 , 方源 , 戴红 . 新型含呋喃环结构的吡唑肟酯类化合物的合成及其生物活性[J]. 有机化学, 2015 , 35(8) : 1785 -1791 . DOI: 10.6023/cjoc201503001
In search of novel heterocyclic compounds with potent biological activities, a series of novel pyrazole oxime ester derivatives bearing substituted furan ring were prepared by the reaction of 5-substituted phenyl-2-furan carbonyl chloride with different pyrazole oximes. The structures of the target compounds were characterized by 1H NMR, 13C NMR and elemental analysis. The bioassay data exhibited that some title compounds showed certain acaricidal or insecticidal activities. For example, 5-(4-trifluoromethylphenyl)furan-2-formic acid-[1-methyl-3-methyl-5-(2,4-dichlorophenoxy)pyrazole-4-carbaldehyde]-oxime ester (6g) displayed 83% inhibition rate against Tetranychus cinnabarinus at the concentration of 400 μg/mL, and 5-(4-fluoro-phenyl)furan-2-formic acid-[1-(4-methylphenyl)-3-methyl-5-(4-methylphenoxy)pyrazole-4-carbaldehyde]oxime ester (6m) showed insecticidal activity against Plutella xylostella and Aphis craccivora with 71% and 64% mortality, respectively, at the same concentration.
Key words： furan; pyrazole oxime; synthesis; biological activity
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