Synthesis and Biological Activities of Novel 1,2,4-Triazole Derivatives Containing 1,2,3-Thiadiazole Ring

doi:10.1007/s40242-014-3491-6

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (3): 390-395.doi: 10.1007/s40242-014-3491-6

Previous Articles Next Articles

Synthesis and Biological Activities of Novel 1,2,4-Triazole Derivatives Containing 1,2,3-Thiadiazole Ring

LI Yuedong¹, MAO Wutao^1,2, FAN Zhijin^1,3, LI Juanjuan¹, FANG Zhen¹, JI Xiaotian¹, ZONG Guangning¹, LI Fengyun¹

1. State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, P. R. China;
2. College of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang 473061, P. R. China;
3. Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Nankai University, Tianjin 300071, P. R. China

Received:2013-11-13 Revised:2014-01-06 Online:2014-06-01 Published:2014-02-25
Contact: FAN Zhijin E-mail:fanzj@nankai.edu.cn
Supported by:
Supported by the National Key Technology Research and Development Program of China(No.2011BAE06B02).

Abstract

Abstract:

A series of novel 1,2,4-triazole derivatives containing 1,2,3-thiadiazole ring was designed and synthesized. Their structures were confirmed by IR, ¹H NMR, high resolution mass spectrometer(HRMS) and electrospray ionization-mass spectrometer(ESI-MS) combined with melting points and elemental analysis. Preliminary bioassays indicate that these compounds exhibit good insecticidal activity against Aphis laburni at 100 μg/mL, especially compound 6b shows mortality of no less than 95%. Most of the compounds show good activities against tobacco mosaic virus(TMV) with different modes in vivo at 100 μg/mL. Compound 6d standed out, showing a good insecticidal activity and very high induction effects against TMV in vivo. Collectively, our data demonstrate a new strategy for insect and virus control.

Key words: 1,2,3-Thiadiazole, 1,2,4-Triazole, Insecticidal activity, Anti-tobacco mosaic virus(TMV) activity

LI Yuedong, MAO Wutao, FAN Zhijin, LI Juanjuan, FANG Zhen, JI Xiaotian, ZONG Guangning, LI Fengyun. Synthesis and Biological Activities of Novel 1,2,4-Triazole Derivatives Containing 1,2,3-Thiadiazole Ring[J]. Chemical Research in Chinese Universities, 2014, 30(3): 390-395.

References

[1] Liu T. X., Sparks A. N., Yue B. S., J. Entomol. Sci., 2001, 36, 244
[2] Jacobson R. M., Ramsay J. R., Aller H. E., Thirugnanam M., 1-Dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles, EP 0213718A2, 1987
[3] Howatt K. A., Weed Technol., 2005, 19, 777
[4] Shang J., Wang W. M., Li Y. H., J. Agric. Food Chem., 2012, 60, 8286
[5] Fan Z. J., Yang Z. K., Zhang H. K., Mi N., Wang H., Cai F., Zuo X., Zheng Q. X., Song H. B., J. Agric. Food Chem., 2010, 58(5), 2630
[6] Zhang P. Z., Zhou S. F., Li T. R., Jiang L., Chin. Chem. Lett., 2012, 23, 1381
[7] Xu L. Z., Li W. H., Yu G. P., Qin Y. Q., Yang S. H., Hou B. R., Chem. Res. Chinese Universities, 2005, 21(5), 528
[8] Wang B. L., Liu X. H., Zhang X. L, Chem. Biol. Drug Des., 2011, 78, 42
[9] Yang B., He Q. J., Zhu D. Y., Cancer Chem. Other. Pharm., 2006, 57, 268
[10] Zhao X., Liu J. R., Xin H. W., Lu B. W., Bao X. R., Li J. F., Liu Y., Yang X. Y., Yuan L., Chem. Res. Chinese Universities, 2012, 28(3), 424
[11] Tang H., Zheng C. H., Ren X. H., Liu J., Liu N., Lü J. G., Zhu L., Zhou Y. J., Chin. Chem. Lett., 2013, 24, 219
[12] Chang J. J., Wang Y., Zhang H. Z., Chem. J. Chinese Universities, 2011, 32(8), 1970
[13] Simon P. A., William M. B., Frontiers. Biosci., 2000, 5, 124
[14] Du Q. S., Zhu W. P., Zhao Z. J., Qian X. H., Xu Y. F., J. Agric. Food. Chem., 2012, 60, 346
[15] Fan Z. J., Ai Y. W., Chen J. Y., Wang H. Y., Liu F. L., Bao L. L., Shi Z. G., J. Sichuan Normal Univ.(Nat. Sci.), 2005, 28, 608
[16] Yasuda M., Kusajima M., Nakajima M., Akutsu K., Kudo T., Yoshida S., Nakashita H., J. Pestic. Sci., 2006, 31, 329
[17] Fan Z. J., Shi Z. G., Zhang H. K., Liu X. F., Bao L. L., Ma L., Zuo X., Zheng Q. X., Mi N., J. Agric. Food. Chem., 2009, 57, 4279
[18] Mao W. T., Zhao H., Fan Z. J., Ji X. T., Hua X. W., Kalinina T., Yury Y. M., Vasiliy A. B., Chin. Chem. Lett., 2012, 23, 1233
[19] Luo Y. P., Gong Q., Chen Q., Yang G. F., Chin. J. Org. Chem., 2008, 28, 1561
[20] Liu X. H., Wang J. Q., Tan C. X., Asian J. Chem., 2011, 23, 4064
[21] Wang H., Yang Z. K., Fan Z. J., Wu Q. J., Zhang Y. J., Mi N., Wang S. X., Zhang Z. C., Song H. B., Liu F., J. Agric. Food Chem., 2011, 59, 628
[22] Babcock J. M., Gerwick C. B., Huang J. X., Pest Manag. Sci., 2011, 67, 328

Synthesis and Biological Activities of Novel 1,2,4-Triazole Derivatives Containing 1,2,3-Thiadiazole Ring

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	ZHAO Yangyang, LI Huangong, SUN Pengwei, GAO Li, ZHOU Sha, XIONG Lixia, YANG Na, LI Yuxin, LI Zhengming. Design, Synthesis, Biological Evaluation and SARs of Anthranilic Diamide Derivatives Containing Pyrrole Moieties [J]. Chemical Research in Chinese Universities, 2020, 36(6): 1168-1173.
[2]	ZHANG Xiulan, ZHANG Huan, LIU Jingbo, XIONG Lixia, LI Zhengming. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole [J]. Chemical Research in Chinese Universities, 2020, 36(5): 829-834.
[3]	ZHAO Yang, CHENG Jingli, XIE Zhengang, FANG Shaowei, ZHAO Jinhao. Syntheses and Insecticidal Activity of Spirocyclic Tetronic Acid Derivatives Containing Oxime Ether Moiety [J]. Chemical Research in Chinese Universities, 2020, 36(5): 810-815.
[4]	WANG Xianhao, LI Jianguo, WANG Guangjian, HAN Xianzheng, LI Dongmei, TIAN Zhongzhen. Design, Synthesis and Insecticidal Activities of Novel 5-Alkoxyfuran-2(5H)-one Derivatives [J]. Chemical Research in Chinese Universities, 2019, 35(5): 799-805.
[5]	LI Ling, ZOU Jiyong, XIA Qing, CUI Hongmin, YOU Shengyong, LIU Yuxiu, WANG Qingmin. Anti-TMV and Insecticidal Potential of Four Iridoid Glycosides from Gardenia Jasminoides Fruit [J]. Chemical Research in Chinese Universities, 2018, 34(5): 697-699.
[6]	HUA Xuewen, LIU Chen, ZHOU Sha, CHEN Minggui, XIONG Lixia, LI Yongqiang, LI Zhengming. Design, Synthesis and Insecticidal Evaluation of Novel N-Pyridylpyrazolecarboxamide Derivatives Containing Isoxazole, Isoxazoline and 1,3,4-Thiadiazole Rings [J]. Chemical Research in Chinese Universities, 2017, 33(6): 882-889.
[7]	FANG Ting, SUN Chuanwen, XU Yiyi, YUAN Jing, WANG Yuanfeng, XING Jiahua. Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring [J]. Chemical Research in Chinese Universities, 2014, 30(6): 931-936.
[8]	ZHU Hongwei, WANG Baolei, ZHANG Xiulan, XIONG Lixia, YU Shujing, LI Zhengming. Syntheses and Biological Activities of Novel 3-Bromo-1-(3-chloropy-ridin-2-yl)-N-hydroxy-N-aryl-1H-pyrazole-5-carboxamides [J]. Chemical Research in Chinese Universities, 2014, 30(3): 409-414.
[9]	LIU Chen, ZHANG Jifeng, ZHOU Yunyun, WANG Baolei, XIONG Lixia, LI Zhengming. Design, Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Oxime Ester and Diacylhydrazine Moieties [J]. Chemical Research in Chinese Universities, 2014, 30(2): 228-234.
[10]	CHEN Youwei, WANG Baolei, GUO Yanjun, ZHOU Yunyun, PAN Li, XIONG Lixia, YU Shujing, LI Zhengming. Synthesis and Biological Activities of Novel Methyl Xanthine Derivatives [J]. Chemical Research in Chinese Universities, 2014, 30(1): 98-102.
[11]	ZHANG Xiu-lan, LIU Ai-lin, ZHAO Yu, XIONG Li-xia, LI Zheng-ming. Synthesis and Biological Activity of Novel Anthranilic Diamides Containing N-Substituted Arylmethylene Moieties [J]. Chemical Research in Chinese Universities, 2013, 29(6): 1134-1139.
[12]	ZHANG Ji-feng, LIU Chen, LIU Peng-fei, YAN Tao, WANG Bao-lei, XIONG Li-xia, LI Zheng-ming. Synthesis and Biological Activities of Novel Anthranilic Diamides Analogues Containing Benzo[b]thiophene [J]. Chemical Research in Chinese Universities, 2013, 29(4): 714-720.
[13]	SUN Chuan-wen, WU Ying, CHEN Yan-xia, NAN Shi-bin, ZHANG Wang-geng. cis-Nitenpyram Analogues Bearing Acyloxy Segments Anchored on the Tetrahydropyrimidine Ring: Synthesis,Insecticidal Activities and Molecular Docking Studies [J]. Chemical Research in Chinese Universities, 2013, 29(3): 477-482.
[14]	ZHOU Yun-yun, LI Yu-xin, LI Yi-ming, YANG Xiao-ping, MAO Ming-zhen, LI Zheng-ming. Design, Synthesis and Structure-activity of N-Glycosyl-1-pyridyl-1H-pyrazole-5-carboxamide as Inhibitors of Calcium Channels [J]. Chemical Research in Chinese Universities, 2013, 29(2): 249-255.
[15]	ZHAO Yu, LI Yong-qiang, XIONG Li-xia, XU Li-ping, PENG Li-na, LI Fang, LI Zheng-ming. Design, Syntheses and Biological Activities of Novel Anthranilic Diamide Insecticides Containing N-Pyridylpyrazole [J]. Chemical Research in Chinese Universities, 2013, 29(1): 51-56.