Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group

doi:10.6023/cjoc201506004

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2399-2404.DOI: 10.6023/cjoc201506004 Previous Articles Next Articles

Notes

新型含取代吡啶环的取代吡唑甲醛肟的合成及生物活性测定

戴红^a, 庄辉阳^b, 施磊^a, 李刚^a, 张海军^a, 方源^a, 戴宝江^b,c

a 南通大学化学化工学院南通 226019;
b 南通南沈植保科技开发有限公司南通 226017;
c 南通职业大学化学与生物工程学院南通 226007

收稿日期:2015-06-03 修回日期:2015-06-30 发布日期:2015-07-10
通讯作者: 张海军, 戴宝江 E-mail:zhanghj2801@163.com;daibj2001@163.com
基金资助:
国家自然科学基金(Nos. 21202089, 21372135)和南通市科技计划(No. AS2013002)资助项目.

Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group

Dai Hong^a, Zhuang Huiyang^b, Shi Lei^a, Li Gang^a, Zhang Haijun^a, Fang Yuan^a, Dai Baojiang^b,c

a College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019;
b Nantong Nanshen Plant Protection Science and Technology Development Co. Ltd, Nantong 226017;
c School of Chemical and Biological Engineering, Nantong Vocational University, Nantong 226007

Received:2015-06-03 Revised:2015-06-30 Published:2015-07-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21202089, 21372135), and the Science and Technology Project Fund of Nantong City (No. AS2013002).

1. Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group.PDF(806KB)

Abstract

In order to explore novel potent pesticide from pyrazole oxime derivatives, a series of new pyrazole oxime ester compounds bearing substituted pyridine moiety were synthesized by the introduction of pyridyl backbone into the molecules of pyrazole oxime. Their structures were confirmed by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay results showed that some of the title compounds displayed certain insecticidal and acaricidal activities. For example, compound 5i exhibited insecticidal activity against Aphis craccivora with 90% mortality at the concentration of 400 μg/mL.

Key words: substituted pyridine, pyrazole oxime, synthesis, bioactivity

Cite this article

Dai Hong, Zhuang Huiyang, Shi Lei, Li Gang, Zhang Haijun, Fang Yuan, Dai Baojiang. Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group[J]. Chin. J. Org. Chem., 2015, 35(11): 2399-2404.

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.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[3] 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.
[4] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[5] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[6] Dai, H.; Yu, H. B.; Liu, J. B.; Qin, X.; Wang, T. T.; Zhang, X.; Qin, Z. F.; Fang, J. X. Chin. J. Org. Chem. 2013, 33, 1104 (in Chinese). (戴红, 于海波, 刘建兵, 秦雪, 王婷婷, 张欣, 秦振芳, 方建新, 有机化学, 2013, 33, 1104.)
[7] 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.
[8] Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160.
[9] Dai, H.; Xiao, Y. S.; Li, Z.; Xu, X. Y.; Qian, X. H. Chin. Chem. Lett. 2014, 25, 1014.
[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] Liu, J. B.; Tao, W. F.; Hu, Y.; Dai, H.; Fang, J. X. Chin. J. Org. Chem. 2006, 26, 1566 (in Chinese). (刘建兵, 陶伟峰, 胡燕, 戴红, 方建新, 有机化学, 2006, 26, 1566.)
[12] Ye, Z. J.; Shi, L. N.; Shao, X. S.; Xu, X. Y.; Xu, Z. P.; Li, Z. J. Agric. Food Chem. 2013, 61, 312.
[13] Lu, S. Y.; Zhuang, Y. Y.; Wu, N. B.; Feng, Y.; Cheng, J. G.; Li, Z.; Chen, J.; Yuan, J.; Xu, X. Y. J. Agric. Food Chem. 2013, 61, 10858.
[14] Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92 (in Chinese). (王鑫, 王朝强, 傅翠蓉, 邹小毛, 有机化学, 2015, 35, 92.)
[15] Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Simth, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[16] Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288.
[17] Lu, S. Y.; Shao, X. S.; Li, Z.; Xu, Z. P.; Zhao, S. S.; Wu, Y. L.; Xu, X. Y. J. Agric. Food Chem. 2012, 60, 322.
[18] Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E. A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341.
[19] Xu, R. B.; Xia, R.; Luo, M.; Xu, X. Y.; Cheng, J. G.; Shao, X. S.; Li, Z. J. Agric. Food Chem. 2014, 62, 381.
[20] Mu, C.-W.; Qin, Z.-H. Modern Agrochem. 2003, 2, 1 (in Chinese). (慕长伟, 覃兆海, 现代农药, 2003, 2, 1.)
[21] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 秦雪, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1662.)
[22] Dai, H.; Shi, L.; Zhang, H. J.; Li, Y. Q.; Fang, J. X.; Shi, Y. J. Chin. J. Org. Chem. 2012, 32, 1060 (in Chinese).(戴红, 施磊, 张海军, 李永强, 方建新, 石玉军, 有机化学, 2012, 32, 1060.)
[23] Cativiela, C.; Serrano, J. L.; Zurbano, M. M. J. Org. Chem. 1995, 60, 3074. Park, M. S.; Park, H. J.; Park, K. H.; Lee, K. I. Synth. Commun. 2004, 34, 1541.

新型含取代吡啶环的取代吡唑甲醛肟的合成及生物活性测定

Synthesis and Biological Activities of Novel Substituted Pyrazole Oximes Containing Substituted Pyridine Group

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[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]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[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.