Citation: Chen Xiulei, Jia Haowu, Li Zhong, Xu Xiaoyong. Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita[J]. Chinese Chemical Letters, ;2019, 30(6): 1207-1213. doi: 10.1016/j.cclet.2019.02.033 shu

Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita

Chen Xiulei ^a ,
Jia Haowu ^a ,
Li Zhong ^a,b ,
Xu Xiaoyong ^a,b,*,

a.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
Shanghai Collaborative Innovation Center for Biomanufacturing Technology, Shanghai 200237, China

E-mail address:

xyxu@ecust.edu.cn

Received Date: 4 January 2019
Revised Date: 25 February 2019
Accepted Date: 28 February 2019
Available Online: 1 June 2019

Figures(3)

To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.
- 1,2,3-Benzotriazin-4-one,
- Heterocycle,
- M. incognita,
- Nematicidal activity,
- Fragment
1. [1]
  P.P.J. Haydock, S.R. Woods, I.G. Grove, et al., Chemical Control of Nematodes, CABI Publishing, Wallingford, 2006, pp. 392-410.
2. [2]
  P. Abad, J. Gouzy, J.M. Aury, et al., Nat. Biotechnol. 26(2008) 909-915. doi: 10.1038/nbt.1482
3. [3]
  M.D. Whorton, D.E. Foliart, Mutat. Res., Rev. Genet. Toxicol. 123(1983) 13-30. doi: 10.1016/0165-1110(83)90044-1
4. [4]
  H.C. Meher, V.T. Gajbhiye, G. Chawla, et al., Pest Manage. Sci. 65(2009) 1201-1207. doi: 10.1002/ps.v65:11
5. [5]
  G.P. Lahm, J. Desaeger, B.K. Smith, et al., Bioorg. Med. Chem. Lett. 27(2017) 1572-1575. doi: 10.1016/j.bmcl.2017.02.029
6. [6]
  T.R. Faske, K. Hurd, J. Nematol. 47(2015) 316-321.
7. [7]
  Y. Oka, S. Shuker, N. Tkachi, Pest Manage. Sci. 68(2012) 268-275. doi: 10.1002/ps.v68.2
8. [8]
  L.L. Gan, B. Fang, C. He, Bull. Korean Chem. Soc. 31(2010) 3684-3692. doi: 10.5012/bkcs.2010.31.12.3684
9. [9]
  J. Kossakowski, M. Krawiecka, B. Kuran, Molecules 11(2006) 615-626. doi: 10.3390/11080615
10. [10]
  J.B. Acri, B.K. Siedleck, J.M. Witkin, J. Pharmacol. Exp. Ther. 277(1996) 198-206.
11. [11]
  J.C. Lien, L.J. Huang, J.P. Wang, et al., Bioorg. Med. Chem. 5(1997) 2111-2120. doi: 10.1016/S0968-0896(97)00133-8
12. [12]
  M. Kimura, T. Masuda, K. Yamada, et al., Bioorg. Med. Chem. Lett. 14(2004) 4287-4290. doi: 10.1016/j.bmcl.2004.05.091
13. [13]
  G. Le Bihan, F. Rondu, A. Pele-Tounian, et al., J. Med. Chem. 42(1999) 1587-1603. doi: 10.1021/jm981099b
14. [14]
  C.S. Ananda Kumar, S.B. Benaka Prasad, K. Vinaya, et al., Eur. J. Med. Chem. 44(2009) 1223-1229. doi: 10.1016/j.ejmech.2008.09.025
15. [15]
  B.C. Sasse, U.R. Mach, J. Leppaenen, etal., Bioorg. Med. Chem. 15(2007)7258-7273. doi: 10.1016/j.bmc.2007.08.034
16. [16]
  Y. Zhang, Y.Z. Zhan, Y. Ma, et al., Chin. Chem. Lett. 29(2018) 441-446. doi: 10.1016/j.cclet.2017.08.035
17. [17]
  L.Y. Zhang, B.L. Wang, Y.Z. Zhan, et al., Chin. Chem. Lett. 27(2016) 163-167. doi: 10.1016/j.cclet.2015.09.015
18. [18]
  B.L. Wang, L.Y. Zhang, X.H. Liu, et al., Bioorg. Med. Chem. Lett. 27(2017) 5457-5462. doi: 10.1016/j.bmcl.2017.10.065
19. [19]
  H. Sun, H. Li, J. Wang, et al., Chin. Chem. Lett. 29(2018) 977-980. doi: 10.1016/j.cclet.2017.10.015
20. [20]
  L. Pan, X.Z. Li, D.A. Sun, et al., Chin. Chem. Lett. 27(2016) 375-379. doi: 10.1016/j.cclet.2016.01.029
21. [21]
  G.L. Wang, X.L. Chen, Y.Y. Deng, et al., J. Agric. Food Chem. 63(2015) 6883-6889. doi: 10.1021/acs.jafc.5b01762
22. [22]
  G.L. Wang, X. Chen, Y.N. Chang, et al., Chin. Chem. Lett. 26(2015) 1502-1506. doi: 10.1016/j.cclet.2015.10.024
23. [23]
  Y.N. Chang, J.W. Zhang, X.L. Chen, et al., Bioorg. Med. Chem. Lett. 27(2017) 2641-2644. doi: 10.1016/j.bmcl.2016.12.065
24. [24]
  K.L. Kirk, J. Fluorine Chem. 127(2006) 1013-1029. doi: 10.1016/j.jfluchem.2006.06.007
1. [1]
  Xinyu Tian , Jiaxiang Guo , Zeyi Li , Shihou Sheng , Tianyu Zhang , Xianfei Li , Chuandong Dou . Control over electronic structures of organic diradicaloids via precise B/O-heterocycle fusion. Chinese Chemical Letters, 2025, 36(1): 110174-. doi: 10.1016/j.cclet.2024.110174
2. [2]
  Hailang Deng , Abebe Reda Woldu , Abdul Qayum , Zanling Huang , Weiwei Zhu , Xiang Peng , Paul K. Chu , Liangsheng Hu . Killing two birds with one stone: Enhancing the photoelectrochemical water splitting activity and stability of BiVO₄ by Fe ions association. Chinese Chemical Letters, 2024, 35(12): 109892-. doi: 10.1016/j.cclet.2024.109892
3. [3]
  Chuyu Huang , Zhishan Liu , Linping Zhao , Zuxiao Chen , Rongrong Zheng , Xiaona Rao , Yuxuan Wei , Xin Chen , Shiying Li . Metal-coordinated oxidative stress amplifier to suppress tumor growth combined with M2 macrophage elimination. Chinese Chemical Letters, 2024, 35(12): 109696-. doi: 10.1016/j.cclet.2024.109696
4. [4]
  Jun-Jie Fang , Zheng Liu , Yun-Peng Xie , Xing Lu . Superatomic Ag₅₈ nanoclusters incorporating a [MS₄@Ag₁₂]²⁺ (M = Mo or W) kernel show aggregation-induced emission. Chinese Chemical Letters, 2024, 35(10): 109345-. doi: 10.1016/j.cclet.2023.109345
5. [5]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
13. [13]
  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
14. [14]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2023.100332
15. [15]
  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
16. [16]
  Yong-Fang Shi , Sheng-Hua Zhou , Zuju Ma , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . From [Ba3S][GeS4] to [Ba3CO3][MS4] (M = Ge, Sn): Enhancing optical anisotropy in IR birefringent crystals via functional group implantation. Chinese Journal of Structural Chemistry, 2025, 44(1): 100455-100455. doi: 10.1016/j.cjsc.2024.100455
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(603)
HTML views(6)

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