Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones

doi:10.6023/cjoc201808033

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 861-866.DOI: 10.6023/cjoc201808033 Previous Articles Next Articles

Notes

3-(((3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)亚甲基)氨基)取代苯并[d][1,2,3]三嗪-4(3H)-酮类化合物的合成及生物活性

张燕, 朱洪伟, 尚俊峰, 王宝雷, 李正名

南开大学化学学院元素有机化学国家重点实验室化学化工协同创新中心(天津) 天津 300071

收稿日期:2018-08-28 修回日期:2018-10-22 发布日期:2018-11-12
通讯作者: 王宝雷, 李正名 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
基金资助:
天津市自然科学基金（No.17JCYBJC19900）、国家重点研发计划（No.2017YFD0200505）和国家自然科学基金（No.21772103）资助项目.

Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones

Zhang Yan, Zhu Hongwei, Shang Junfeng, Wang Baolei, Li Zhengming

Collaborative Innovation Center of Chemical Science and Enginneering(Tianjin), State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Received:2018-08-28 Revised:2018-10-22 Published:2018-11-12
Contact: 10.6023/cjoc201808033 E-mail:nkwbl@nankai.edu.cn;nkzml@vip.163.com
Supported by:
Project supported by the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900), the National Key Research and Development Program of China (No. 2017YFD0200505), and the National Natural Science Foundation of China (No. 21772103).

1. Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones.PDF(3783KB)

Abstract

A series of 3-(((3-bromo-1-(3-chloropyridin-2-yl) -1H-pyrazol-5-yl) methylene) amino) substituted-benzo[d] [1,2,3]-triazin-4(3H) -ones were synthesized successfully with ethyl N-pyridylpyrazole carboxylate and substituted aminobenzoic acids as starting materials, via multi-step reactions of reduction, oxidation, nucleophilic addition, condensation and diazotization. The preliminary bioassay tests indicated that most of these compounds have certain insecticidal activities, among which one compound showed a mortality rate of 70% towards Mythimna separata Walker at the test concentration of 200 mg·L^-1, some compounds exhibited favorable fungicidal activities at 50 mg·L^-1, particularly two compounds which possessed 92.3% growth inhibitory rate against Physalospora piricola, could be used as new fungicidal leading structures for further investigations on this type of compounds.

Key words: N-pyridylpyrazole derivatives, benzotriazinone, insecticidal activity, fungicidal activity, structure-activity relationship

Cite this article

Zhang Yan, Zhu Hongwei, Shang Junfeng, Wang Baolei, Li Zhengming. Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones[J]. Chin. J. Org. Chem., 2019, 39(3): 861-866.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Oerke, E. C.; Dehne, H. W. Crop Prot. 2004, 23, 275.
[2] Liu, X.-H.; Fang, Y.-M.; Xie, F.; Zhang, R.-R.; Shen, Z.-H.; Tan, C.-X.; Weng, J.-Q.; Xu, T.-M.; Huang, H.-Y. Pest Manage. Sci. 2017, 73, 1900.
[3] Dai, H.; Ding, Y.; Du, X.; Yao, W.; Chen, Q.; Wang, X.; Zhong, S.; Cao, X.; Shi, Y. Chin. J. Org. Chem. 2018, 38, 1755(in Chinese). (戴红, 丁颖, 杜显超, 姚炜, 陈庆文, 王祥龙, 仲苏林, 曹雄飞, 石玉军, 有机化学, 2018, 38, 1755.)
[4] Lamberth, C.; Dinges, J. In Bioactive Heterocyclic Compound Classes-Agrochemicals, Eds.:Lamberth, C.; Dinges, J., Wiley-VCH, Weinheim, 2012, pp. 3~20.
[5] Lahm, G. P.; Cordova, D.; Barry, J. D. Bioorg. Med. Chem. 2009, 17, 4127.
[6] Wu, Z.-B.; Zhou, X.; Ye, Y.-Q.; Wang, P.-Y.; Yang, S. Chin. Chem. Lett. 2017, 28, 121.
[7] Selby, T. P.; Lahm, G. P.; Stevenson, T. M. Pest Manage. Sci. 2017, 73, 658.
[8] Wu, J.; Song, B.-A.; Hu, D.-Y.; Yue, M.; Yang, S. Pest Manage. Sci. 2012, 68, 801.
[9] Zhang, J.-F.; Xu, J.-Y.; Wang, B.-L.; Li, Y.-X.; Xiong, L.-X.; Li, Y.-Q.; Ma, Y.; Li, Z.-M. J. Agric. Food Chem. 2012, 60, 7565.
[10] Wang, B.; Ma, Y.; Xiong, L.; Li, Z. Chin. J. Chem. 2012, 30, 815.
[11] Wang, B.-L.; Zhu, H.-W.; Ma, Y.; Xiong, L.-X.; Li, Y.-Q.; Zhao, Y.; Zhang, J.-F.; Chen, Y.-W.; Zhou, S.; Li, Z.-M. J. Agric. Food Chem. 2013, 61, 5483.
[12] Yan, T.; Yu, S.; Liu, P.; Liu, Z.; Wang, B.; Xiong, L.; Li, Z. Chin. J. Chem. 2012, 30, 919.
[13] Wang, B.-L.; Zhu, H.-W.; Li, Z.-M.; Wang, L.-Z.; Zhang, X.; Xiong, L.-X.; Song, H.-B. Pest Manage. Sci. 2018, 74, 726.
[14] Wang, G. L.; Chen, X.; Chang, Y. N.; Du, D.; Li, Z.; Xu, X. Y. Chin. Chem. Lett. 2015, 26, 1502.
[15] Ibrahim, T. S.; Rashad, A. A.; Abdel-Samii, Z. K.; El-Feky, S. A.; Abdel-Hamid, M. K.; Barakat, W. Med. Chem. Res. 2012, 21, 4369.
[16] Zhang, J.; Li, P.; Wang, Y.; Zhang, C.; Chen, L.; Tang, X.; He, M.; Xue, W. Chem. J. Chin. Univ. 2018, 39, 1455(in Chinese). (张菊平, 李普, 王一会, 张橙, 陈丽娟, 汤旭, 贺鸣, 薛伟, 高等学校化学学报, 2018, 39, 1455.)
[17] Dong, W.; Xu, J.; Xiong, L.; Liu, X.; Li, Z. Chin. J. Chem. 2009, 27, 579.
[18] Leiby, R. W. J. Heterocycl. Chem. 1984, 21, 1825.
[19] Zhou, Y.; Wang, B.; Di, F.; Xiong, L.; Yang, N.; Li, Y.; Li, Y.; Li, Z. Bioorg. Med. Chem. Lett. 2014, 24, 2295.
[20] Sircar, J. C.; Capiris, T.; Kesten, S. J.; Herzig, D. J. J. Med. Chem. 1981, 24, 735.
[21] Benhammadi, S.; Iraten, S.; Othman, A. A. Orient. J. Chem. 2016, 32, 2567.
[22] Sun, N.; Shen, Z.; Zhai, Z.; Han, L.; Weng, J.; Tan, C.; Liu, X. Chin. J. Org. Chem. 2017, 37, 2705(in Chinese). (孙娜波, 沈钟华, 翟志文, 韩亮, 翁建全, 谭成侠, 刘幸海, 有机化学, 2017, 37, 2705.)

3-(((3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)亚甲基)氨基)取代苯并[d][1,2,3]三嗪-4(3H)-酮类化合物的合成及生物活性

Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones

PDF

Supporting Info.

Knowledge

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]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[3]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[4]	Xin Zuo, Shinuo Xu, Zhongyang Chen, Jianfeng Yan, Yaofeng Yuan. Research Progress of Electron Transport Properties in Ferrocene- Containing Single-Molecule Junctions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2313-2322.
[5]	Jinyan He, Fuyun Tian, Qingqing Wu, Yueming Zheng, Yuting Chen, Haiyan Xu, Zhengsheng Jin, Li Zhan, Xinqiang Cheng, Yueling Gu, Zhaobing Gao, Guilong Zhao. Design, Synthesis and Bioactivity of [3.3.3]Propellane-Based Voltage-Gated Calcium Channel α2δ Subunit Ligands [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2226-2238.
[6]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[7]	Zichan Zhang, Yang Sun, Sheng Hua, Baolin Xu, Min Zhang, Qin Zhao, Dandan Zheng, Yang Wang, Jianfeng Ju, Yujun Shi, Hong Dai. Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1435-1443.
[8]	Huan Xu, Hongfei Wu, Xiaoming Zhang, Xingxing Lu, Tengda Sun, Yue Qi, Yufan Lin, Xinling Yang, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 725-733.
[9]	Changxing Sun, Fuhao Zhang, Huan Zhang, Penghui Li, Lin Jiang. Design, Synthesis, Fungicidal Activity and Molecular Docking Study of Novel 2-(1-Methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 229-235.
[10]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[11]	Wenjuan Li, Rui Zhang, Zhihua Cai, Xiaoqiang Han, Lin He, Bin Dai. Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2832-2839.
[12]	Rong Zhang, Xiang Gao, Lingling Chen, Fajun Nan. Discovery and Structure-Activity Relationship Studies of Thiazole- Oxazole Tandem Heterocyclic RNA Splicing Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2925-2939.
[13]	Qian Zhang, Yihao Li, Leichuan Xu, Haoyun Ma, Xiangdong Li, Ming'an Wang. Synthesis and Fungicidal Activity of Novel Butenolide Compounds Containing Oxime Ether Moiety [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2438-2448.
[14]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[15]	Ming Cai, Liang Shao, Fan Yang, Jihong Zhang, Fei Yu. Design, Synthesis of Pentacyclic Triterpenoid Glucose Conjugate and in vitro Activity against Influenza Virus [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1453-1462.