Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing 1,3,4-Oxadiazole Group

Abstract

In order to explore new pyrazole oxime compounds possessing satisfactory bioactivities, sixteen pyrazole oxime derivatives containing 1,3,4-oxadiazole group were prepared with fenpyroximate selected as lead structure. Their insecticidal activities were determined. Preliminary bioassay demonstrated that all the target compounds displayed 100% insecticidal activities towards Mythimna separata at 500 μg/mL, of which 5 target compounds possessed 80%～100% insecticidal activities against Mythimna separata at 100 μg/mL. Moreover, at concentration of 500 μg/mL, mortality rates against Aphis medicaginis of 9 target compounds were 100%, those of 3 compounds were 70%～100% at 100 μg/mL. Additionally, 4 target compounds exhibited more than 80% mortality rates against Tetranychus cinnabarinus at 500 μg/mL. Keywords 1,3,4-oxadiazole; pyrazole oxime; synthesis; bioactivity 近年来, 含氮杂环衍生物因其具有多种生物活性而 引起人们广泛的关注 [1][2][3][4][5][6][7][8][9][10] . 吡唑肟化合物是含氮杂环体 系中的重要分支之一, 在植物保护及生物医药等领域起 到至关重要的作用, 常被用于杀菌 [11] 、杀虫 [12] 、抗植物 病毒 [13] 和抗癌 [14][15] 等活性分子创制中. Kraus 等合成的 唑螨酯(Fenpyroximate)常常用于瘘螨或附线螨等害虫的 防治, 而且该化合物持效期较长 [16] ; Fu 等 [17] 研制的化合 物 A 表现出较优的杀虫活性, 在 200 μg/mL 浓度下对蚜 虫的致死率为 93%, 在 100 μg/mL 浓度下对朱砂叶螨的 致死率达 100%; He 等 [18] 报道的化合物 B 对蚜虫、小菜 蛾及螨虫展现出优异的防治效果, 该化合物在 200 μg/mL 浓度下对蚜虫的防效为 100%, 在 50 μg/mL 浓度 下对小菜蛾的防效为 86.42%, 在 10 μg/mL 浓度下对螨 虫的致死率为 100%; Ling 等 [19] 合成的化合物 C 对人肝 癌细胞 SMMC-7721 和人肺癌细胞 H1299 显示出较好的 抗肿瘤作用, 其 IC 50 值分别是 3.09 和 6.18 μmol/L. 同时, 1,3,4-噁二唑衍生物也是一类重要的氮杂环类化合物, 因其具备优异的杀虫 [20] 、杀菌 [21][22] 、除草 [23] 、抗病毒 [24] 及抗癌 [25][26] 等生物活性, 在农业生产及医疗保健等方面 应用广泛 [27][28][29] . 目前已有多种具有广谱生物活性的 1,3,

Design, Synthesis and Bioactivities of Novel Pyridyl Containing Pyrazole Oxime Ether Derivatives

“…Recently, Wang et al found that oxazole-containing pyrazole oxime ether derivative A ( Figure 1 ) had a broad spectrum of insecticidal and fungicidal properties [ 28 ]. Sun et al reported pyrazole oxime ether B ( Figure 1 ) with an aryloxy-linked 1,3,4-oxadiazole moiety displaying satisfactory insecticidal effects [ 29 ]. This greatly promoted the development of bioactive pyrazole oxime ether molecules.…”