Citation: Yue-Dong Li, Wu-Tao Mao, Zhi-Jin Fan, Juan-Juan Li, Zhen Fang, Xiao-Tian Ji, Xue-Wen Hua, Guang-Ning Zong, Feng-Yun Li, Chao-Lun Liu, Jian-Hua Yu. Synthesis and biological evaluation of novel 1,2,4-triazole containing 1,2,3-thiadiazole derivatives[J]. Chinese Chemical Letters, ;2013, 24(12): 1134-1136. shu

Synthesis and biological evaluation of novel 1,2,4-triazole containing 1,2,3-thiadiazole derivatives

1.
a State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China;
2.
b Division of Hematology, College of Medicine and School of Public Health, The Ohio State University, Columbus, OH 43210, United States

Corresponding author: Zhi-Jin Fan, Jian-Hua Yu,
Received Date: 3 May 2013
Available Online: 4 June 2013

A series of novel 1,2,4-triazoles containing 1,2,3-thiadiazole derivatives were designed and synthesized. Their structures were confirmed by melting points, IR, ¹H NMR, and elemental analysis and ESI-MS or HRMS. Preliminary bioassays indicated that these compounds exhibited very good insecticidal activity against Aphis laburni at 100 mg/mL, with mortality no less than 95%. Compounds 6a, 6c, 6f, 6l showed higher curative activity against TMV and compound 6h showed a higher induction effects against TMV in vivo at 100 μg/mL. Collectively, our data demonstrate a new strategy for control of insects and viruses.
- 1,2,3-Thiadiazole,
- 1,2,4-Triazole,
- Insecticidal activity,
- Anti-TMV activity
1. [1]
  [1] T.X. Liu, A.N. Sparks, B.S. Yue, Toxicity and efficacy of triazamate against turnip aphid (Homoptera: Aphididae) on cabbage, J. Entomol. Sci. 36 (2001) 244-250.
2. [2]
  [2] Rohm, Haas Company, 1-Dimethylcarbamoyl-3-substituted-5-substituted -1H- 1,2,4-triazoles: EP 0213718A2, 1987.
3. [3]
  [3] K.A. Howatt, Carfentrazone ethyl injury to spring wheat (Triticum aestivum) is minimized by some ALS2 inhibiting herbicides, Weed Technol. 19 (2005) 777-783.
4. [4]
  [4] J. Shang, W.M. Wang, Y.H. Li, et al., Synthesis, crystal structure, in vitro acetohydroxyacid synthase inhibition, in vivo herbicidal activity, and 3D-QSAR of new asymmetric aryl disulfides, J. Agric. Food Chem. 60 (2012) 8286-8293.
5. [5]
  [5] X.H. Liu, J.Q. Weng, C.X. Tan, Synthesis, crystal structure, and fungicidal activity of 5-(4-cyclopropyl-5-((3-fluorobenzyl)thio)-4H-1,2,4-triazol-3-yl)-4-methyl- 1,2,3-thiadiazole, J. Chem. 2013 (2013) 1-5.
6. [6]
  [6] P.Z. Zhang, S.F. Zhou, T.R. Li, L. Jiang, Efficient synthesis and in vitro antifungal activity of 1H-benzimidazol-1-yl acetates/propionates containing 1H-1,2,4-triazole moiety, Chin. Chem. Lett. 23 (2012) 1381-1384.
7. [7]
  [7] B.L. Wang, X.H. Liu, X.L. Zhang, et al., Synthesis, structure and biological activity of novel 1,2,4-triazole mannich bases containing a substituted benzylpiperazine moiety, Chem Biol. Drug Des. 78 (2011) 42-49.
8. [8]
  [8] B. Yang, Q.J. He, D.Y. Zhu, Antiproliferative activity of contragestazol (DL1112IT) in murine and human tumor models in vitro and in vivo, Cancer Chemoth. Pharm. 57 (2006) 268-273.
9. [9]
  [9] L. Xia, Z.J. Fan, J.H. Yao, Discovery of bitriazolyl compounds as novel antiviral candidates for combating the tobacco mosaic virus, Bioorg. Med. Chem. Lett. 16 (2006) 2693-3268.
10. [10]
  [10] X.F. Cao, W.J. Chu, Y.B. Cao, Y.S. Yang, Design and synthesis of novel antifungal triazole derivatives with good activity and water solubility, Chin. Chem. Lett. 24 (2013) 303-306.
11. [11]
  [11] Y. Liu, X.F. Cao, X. Liu, et al., Synthesis, pharmacokinetics and in vivo antifungal activity of the novel water-soluble prodrugs of itraconazole analogue YL-24, Chin. Chem. Lett. 24 (2013) 321-324.
12. [12]
  [12] H. Tang, C.H. Zheng, X.H. Ren, et al., Synthesis and biological evaluation of novel triazole derivatives as antifungal agents, Chin. Chem. Lett. 24 (2013) 219-222.
13. [13]
  [13] P.A. Simon, M.B. William, Treatment of epilepsy: existing therapies and future developments, Front. Biosci. 5 (2000) 124-152.
14. [14]
  [14] Q.S. Du, W.P. Zhu, Z.J. Zhao, X.H. Qian, Y.F. Xu, Novel benzo-1,2,3-thiadiazole-7- carboxylate derivatives as plant activators and the development of their agricultural applications, J. Agric. Food Chem. 60 (2012) 346-353.
15. [15]
  [15] Z.J. Fan, Y.W. Ai, J.Y. Chen, et al., Preparation of BTH standard and HPLC analysis of Bion 50%WG, J. Sichuan Normal Univ. (Nat. Sci.) 28 (2005) 608-610.
16. [16]
  [16] M. Yasuda, M. Kusajima, M. Nakajima, et al., Thiadiazole carboxylic acid moiety of tiadinil, SV-03, induces systemic acquired resistance in tobacco without salicylic acid accumulation, J. Pestic. Sci. 31 (2006) 329-334.
17. [17]
  [17] Z.J. Fan, Z.G. Shi, H.K. Zhang, et al., Synthesis and biological activity evaluation of 1,2,3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance, J. Agric. Food Chem. 57 (2009) 4279-4286.
18. [18]
  [18] W.T. Mao, H. Zhao, Z.J. Fan, et al., Synthesis and bioactivity of N-tert-butyl-N0-acyl- 5-methyl-1,2,3-thiadiazole-4-carbohydrazides, Chin. Chem. Lett. 23 (2012) 1233-1236.
19. [19]
  [19] Y.P. Luo, Q. Gong, Q. Chen, G.F. Yang, Synthesis and herbicidal activities of tetrazolinone derivatives containing oxime ether, Chin. J. Org. Chem. 28 (2008) 1561-1565.
20. [20]
  [20] X.H. Liu, J.Q. Wang, C.X. Tan, Microwave synthesis and biological activity of hydrazone derivatives containing 1,2,3-thiadiazole, Asian J. Chem. 23 (2011) 4064-4066.
21. [21]
  [21] W.T. Mao, D.D. Guo, Z.J. Fan, et al., Synthesis, crystal structure and biological activity of 1,5-bis(4-methoxyphenyl)-3-(4-methyl-1,2,3-thiadiazol-5-yl)pentane- 1,5-dione, Chin. J. Struct. Chem. 32 (2013) 357-362.
22. [22]
  [22] H. Wang, Z.K. Yang, Z.J. Fan, Synthesis and insecticidal activity of N-tert-butyl- N,N'-diacylhydrazines containing 1,2,3-thiadiazoles, J. Agric. Food Chem. 59 (2011) 628-634.
1. [1]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
2. [2]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
3. [3]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
4. [4]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
5. [5]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
6. [6]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
7. [7]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
8. [8]
  Peng Zhang , Yitao Yang , Tian Qin , Xueqiu Wu , Yuechang Wei , Jing Xiong , Xi Liu , Yu Wang , Zhen Zhao , Jinqing Jiao , Liwei Chen . Interface engineering of Pt/CeO₂-{100} catalysts for enhancing catalytic activity in auto-exhaust carbon particles oxidation. Chinese Chemical Letters, 2025, 36(2): 110396-. doi: 10.1016/j.cclet.2024.110396
9. [9]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
10. [10]
  Maosen Xu , Pengfei Zhu , Qinghong Cai , Meichun Bu , Chenghua Zhang , Hong Wu , Youzhou He , Min Fu , Siqi Li , Xingyan Liu . In-situ fabrication of TiO₂/NH₂−MIL-125(Ti) via MOF-driven strategy to promote efficient interfacial effects for enhancing photocatalytic NO removal activity. Chinese Chemical Letters, 2024, 35(10): 109524-. doi: 10.1016/j.cclet.2024.109524
11. [11]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
12. [12]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
13. [13]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
14. [14]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
15. [15]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
16. [16]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
17. [17]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
18. [18]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
19. [19]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
20. [20]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(697)
HTML views(25)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142