Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety

doi:10.6023/cjoc201802015

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1755-1762.DOI: 10.6023/cjoc201802015 Previous Articles Next Articles

Articles

新型含取代噁二唑结构的吡唑肟类化合物的合成与生物活性研究

戴红^a, 丁颖^a, 杜显超^a, 姚炜^a, 陈庆文^a, 王祥龙^a, 仲苏林^b, 曹雄飞^b, 石玉军^a

a 南通大学化学化工学院南通 226019;
b 联合国南通农药剂型开发中心南通 226006

收稿日期:2018-02-08 修回日期:2018-03-01 发布日期:2018-03-29
通讯作者: 石玉军 E-mail:yjshi2015@163.com
基金资助:
南通市科技计划（No.MS22015020）和江苏省大学生创新训练计划（No.201710304048）资助项目.

Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety

Dai Hong^a, Ding Ying^a, Du Xianchao^a, Yao Wei^a, Chen Qingwen^a, Wang Xianglong^a, Zhong Sulin^b, Cao Xiongfei^b, Shi Yujun^a

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b United Nations Nantong Pesticide Forulation Development Centre, Nantong 226006

Received:2018-02-08 Revised:2018-03-01 Published:2018-03-29
Contact: 10.6023/cjoc201802015 E-mail:yjshi2015@163.com
Supported by:
Project supported by the Science and Technology Project Fund of Nantong City (No. MS22015020) and the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No. 201710304048).

1. Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety.PDF(915KB)

Abstract

In order to find novel pyrazole oximes with good bioactivities, a series of novel pyrazole oxime derivatives containing substituted oxadiazole moiety were designed and synthesized according to the method of active substructure combination. Their structures were confirmed by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay data indicated that some title compounds showed good insecticidal activities. At the concentration of 500 μg/mL, 9 compounds possessed insecticidal activity against Oriental armyworm with 80%~100%. When the concentration was lowered to 100 μg/mL, 3 compounds still displayed significant insecticidal activity against Oriental armyworm with 70%, 60% and 70%. Additionally, one compound had 60% insecticidal activity against Aphis medicaginis at 500 μg/mL.

Key words: oxadiazole, pyrazole oxime, synthesis, biological activity

Cite this article

Dai Hong, Ding Ying, Du Xianchao, Yao Wei, Chen Qingwen, Wang Xianglong, Zhong Sulin, Cao Xiongfei, Shi Yujun. Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety[J]. Chin. J. Org. Chem., 2018, 38(7): 1755-1762.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[2] Dai, H.; Zhuang. H. Y.; Shi, L.; Li, G.; Zhang, H. J.; Fang, Y.; Dai, B. J. Chin. J. Org. Chem. 2015, 35, 2399 (in Chinese).
(戴红, 庄辉阳, 施磊, 李刚, 张海军, 方源, 戴宝江, 有机化学, 2015, 35, 2399.)
[3] Dai, H.; Li, H.; Jin. Z. C.; Liu, W. Y.; Xiao, Y.; He, H. B.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 185 (in Chinese).
(戴红, 李宏, 金智超, 刘文永, 肖瑶, 何海兵, 汪清民, 石玉军, 有机化学, 2016, 36, 185.)
[4] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[5] Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[6] Chen, L.; Ou, X. M.; Mao, C. H.; Shang, J.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Bioorg. Med. Chem. 2007, 15, 3678.
[7] Ouyang, G. P.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699.
[8] Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672.
[9] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[10] Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest Manage. Sci. 2014, 70, 1207.
[11] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[12] Dai, H.; Chen, J.; Li, H.; Dai, B. J.; He, H. B.; Fang, Y.; Shi, Y. J. Molecules 2016, 21, 276.
[13] Huang, Q. C.; Qian, X. H.; Song, G. H.; Cao, S. Pest Manage. Sci. 2003, 59, 933.
[14] Formagio, A. S. N.; Tonin, L. T. D.; Foglio, M. A.; Madjarof, C.; Carvalho. J. E. D.; Costa, W. F. D.; Cardoso, F. P.; Sarragiotto, M. H. Bioorg. Med. Chem. 2008, 16, 9660.
[15] Ruan, L. L.; Fan, R. J.; Liu, X. H.; Chen, J.; Weng, J. Q. Chin. J. Org. Chem. 2015, 35, 1166 (in Chinese).
(阮铃莉, 范人杰, 刘幸海, 陈杰, 翁建全, 有机化学, 2015, 35, 1166.)
[16] Shi, Y. J.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Dai, H.; Hong, Y.; Li, C. J.; Shi, J.; Wu, J. M. Chin. J. Org. Chem. 2017, 37, 1844 (in Chinese).
(石玉军, 叶林玉, 仲苏林, 曹雄飞, 戴红, 洪宇, 李春建, 石健, 吴锦明, 有机化学, 2017, 37, 1844.)
[17] Suzuki, J.; Okamura, D.; Gushikawa, T.; Hirai, K.; Ando, T. J. Pestic. Sci. 2011, 36, 392.
[18] Liu, A. C.; Feng, J. L.; He, X. L.; Chen, L.; Zou, X. D. Chin. J. Pestic. 2014, 53, 561 (in Chinese).
(刘安昌, 冯佳丽, 贺晓露, 陈露, 邹晓东, 农药, 2014, 53, 561.)
[19] Li, Y. H.; Zhu, H. J.; Chen, K.; Liu, R.; Khallaf, A.; Zhang, X. N.; Ni, J. P. Org. Biomol. Chem. 2013, 11, 3979.
[20] Liu, Q.; Zhu, R.; Gao, S.; Ma, S. H.; Tang, H. J.; Yang, J. J.; Diao, Y. M.; Wang, H. L.; Zhu, H. J. Pest Manage. Sci. 2017, 73, 917.
[21] Zhao, Q. Q.; Liu, S. H.; Li, Y. H.; Wang, Q. M. J. Agric. Food Chem. 2009, 57, 2849.
[22] Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541.
[23] Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504.
[24] Dai, H.; Ye, L. Y.; Zhuang, H. Y.; Dai, B. J.; Fang, Y.; Shi, Y. J. Molecules 2015, 20, 21870.

新型含取代噁二唑结构的吡唑肟类化合物的合成与生物活性研究

Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Oxadiazole Moiety

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[14]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.