Citation: Yu Fuqiang, Guan Aiying, Li Mengru, Hu Lan, Li Xiaowu. Design, synthesis, and fungicidal activity of novel 1, 3, 4-oxadiazole derivatives[J]. Chinese Chemical Letters, ;2018, 29(6): 915-918. doi: 10.1016/j.cclet.2018.01.050 shu

Design, synthesis, and fungicidal activity of novel 1, 3, 4-oxadiazole derivatives

Yu Fuqiang ^a,b ,
Guan Aiying ^b,, ,
Li Mengru ^b ,
Hu Lan ^b ,
Li Xiaowu ^a,,

a.
Department of Materials Physics and Chemistry, School of Material Science and Engineering, and Key Laboratory for Anisotropy and Texture of Materials, Ministry of Education, Northeastern University, Shenyang 110819, China
b.
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R & D Co., Ltd., Shenyang 110021, China

Corresponding author: Guan Aiying, guanaiying@sinochem.com Li Xiaowu, xwli@mail.neu.edu.cn
Received Date: 4 December 2017
Revised Date: 22 January 2018
Accepted Date: 24 January 2018
Available Online: 7 June 2018

Figures(3)

Employing the intermediate derivatization method (IDM), twenty novel 1, 3, 4-oxadiazole derivatives containing arylpyrazoloxyl moiety were designed and synthesized. The structures of the title compounds were identified by ¹H NMR, ¹³C NMR, MS and elemental analyses, compound 4 was further identified by single-crystal X-ray diffraction. Antifungal activities against rice sheath blight (RSB) and sorghum anthracnose (SA) were evaluated by the mycelium linear growth rate method. Compounds 4, 16 and 20 displayed significant activities against RSB (EC₅₀=0.88 mg/L, 0.91 mg/L and 0.85 mg/L, respectively), higher than the reference tebuconazole; While compound 3 exhibited higher activity against SA (EC₅₀=1.03 mg/L), equal to commercial pyraclostrobin (EC₅₀=1.06 mg/L). The study showed that compound 20 is a promising fungicide for further development.
- 1, 3, 4-Oxadiazole derivatives,
- Intermediate derivatization method,
- Rice sheath blight,
- Sorghum anthracnose,
- Structure-activity relationship
1. [1]
  L. Meng, Chemical Control of Rice Sheath Blight and Effect Evaluation of Several Pharmaceutical Compounds (Dissertation), Nanjing Agricultural University, Nanjing, 2013 p. 1.
2. [2]
  L.P. Teng, L. Yu, J. Gao, J. Henan Agric. Sci. 41(2012) 80-83.
3. [3]
  FRAC (Fungicide Resistance Action Committee) Code List 2017, Fungicides Sorted by Mode of Action (Including FRAC Code Numbering); www. frac. info (Accessed December 01, 2017).
4. [4]
  M.S. Gibson, Tetrahedron 18(1962) 1377-1380. doi: 10.1016/S0040-4020(01)99292-0
5. [5]
  A.U. Rehman, S. Ahtzaz, M.A. Abbasi, et al., J. Chil. Chem. Soc. 62(2017) 3370-3375. doi: 10.4067/S0717-97072017000100013
6. [6]
  D. Szulczyk, P. Tomaszewski, M. Jozwiak, et al., Molecules 22(2017) 409.
7. [7]
  D. Kerzare, R. Chikhale, R. Bansode, et al., J. Braz. Chem. Soc. 27(2016) 1998-2010.
8. [8]
  M.U. Islam, M. Albratty, J. Chem. Bio. Phys. Sci. Sec. A 6(2016) 624-633.
9. [9]
  M.S.Y. Khan, G. Chawla, M.A. Mueed, Indian J. Chem. Sec. B 43(2004) 1302-1305.
10. [10]
  B.A. Song, J.X. Chen, D.Y. Hu, et al., CN Patent 106432125, 2017.
11. [11]
  T.T. Zhang, P.Y. Wang, J. Zhou, et al., J. Heterocycl. Chem. 54(2017) 2319-2325. doi: 10.1002/jhet.2820
12. [12]
  Y. Zhang, X.H. Liu, Y.Z. Zhan, et al., Bioorg. Med. Chem. Lett. 26(2016) 4661-4665. doi: 10.1016/j.bmcl.2016.08.059
13. [13]
  X.M. Zheng, Z. Li, Y.L. Wang, et al., J. Fluorine Chem. 123(2003) 163-169. doi: 10.1016/S0022-1139(03)00168-4
14. [14]
  J.C. Liu, W.D. Wang, H.W. He, Chin. J. Org. Chem. 34(2014) 1447-1451. doi: 10.6023/cjoc201403013
15. [15]
  R.Sven, P. Josef, S. Thorsten, et al., WO Patent 2011092187, 2011.
16. [16]
  J.F.Lu., CN Patent 102558058, 2012.
17. [17]
  X.F. Sun, J.F. Tian, M.N. Zhu, B.S. Chai, C.L. Liu, Chin. J. Pestic. 50(2011) 781-789.
18. [18]
  X.F. Cao, J.L. Liu, Z.N. Li, M.S. Ji, Chin. J. Pestic. 49(2010) 323-325343.
19. [19]
  C. MacBean, The pesticide manual, 16th ed., BCPC, Alton, UK, 2012 p. 966.
20. [20]
  C. MacBean, The pesticide manual, 16th ed., BCPC, Alton, UK, 2012 p. 967.
21. [21]
  C. MacBean, The pesticide manual, 16th ed., BCPC, Alton, UK, 2012pp. 963-964.
22. [22]
  P. Mcdougall, AgriService/AgriReference/Products (Pyraclostrobin), Phillips McDougall AgriService, 2015 http://www.phillipsmcdougall.co.uk/. (accessed Dec. 02, 2017) p. 220.
23. [23]
  B.L. Wang, H.W. Zhu, Y. Ma, et al., J. Agric. Food Chem. 61(2013) 5483-5493. doi: 10.1021/jf4012467
24. [24]
  Z.B. Wu, X. Zhou, Y.Q. Ye, P.Y. Wang, S. Yang, Chin. Chem. Lett. 28(2017) 121-125. doi: 10.1016/j.cclet.2016.06.010
25. [25]
  B.L. Wang, H.W. Zhu, Z.M. Li, et al., Pest Manage. Sci. 74(2018) 726-736. doi: 10.1002/ps.2018.74.issue-3
26. [26]
  C.L. Liu, Chin. J. Pestic. 50(2011) 20-22.
27. [27]
  C.L. Liu, A.Y. Guan, J.D. Yang, et al., J. Agric. Food Chem. 64(2016) 45-51. doi: 10.1021/jf5054707
28. [28]
  A.Y. Guan, C.L. Liu, X.P. Yang, M. Dekeyser, Chem. Rev. 114(2014) 7079-7107. doi: 10.1021/cr4005605
29. [29]
  A.Y. Guan, C.L. Liu, G. Huang, et al., J. Agric. Food Chem. 61(2013) 11929-11936. doi: 10.1021/jf403739e
30. [30]
  A.Y. Guan, C.L. Liu, M. Li, et al., Pest Manage. Sci. 67(2011) 647-655. doi: 10.1002/ps.v67.6
31. [31]
  H.C. Li, A.Y. Guan, G. Huang, et al., Bioorg. Med. Chem. 24(2016) 453-461. doi: 10.1016/j.bmc.2015.09.032
32. [32]
  A.Y. Guan, C.L. Liu, W. Chen, et al., J. Agric. Food Chem. 65(2017) 1272-1280. doi: 10.1021/acs.jafc.6b05580
33. [33]
  H. König, N. Götz, U. Klein, K. Eller, US Patent 5922886, 1999.
34. [34]
  R. Yang, Z.F. Gao, J.Y. Zhao, et al., J. Agric. Food Chem. 63(2015) 1906-1914. doi: 10.1021/jf505609z
1. [1]
  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
2. [2]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
3. [3]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
4. [4]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
5. [5]
  Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
6. [6]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
7. [7]
  Ying Li , Long-Jie Wang , Yong-Kang Zhou , Jun Liang , Bin Xiao , Ji-Shen Zheng . An improved installation of 2-hydroxy-4-methoxybenzyl (iHmb) method for chemical protein synthesis. Chinese Chemical Letters, 2024, 35(5): 109033-. doi: 10.1016/j.cclet.2023.109033
8. [8]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
9. [9]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
10. [10]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
11. [11]
  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
12. [12]
  Dan Ouyang , Huan Huang , Yanting He , Jiajing Chen , Jiali Lin , Zhuling Chen , Zongwei Cai , Zian Lin . Utilization of hydralazine as a reactive matrix for enhanced detection and on-MALDI-target derivatization of saccharides. Chinese Chemical Letters, 2024, 35(5): 108885-. doi: 10.1016/j.cclet.2023.108885
13. [13]
  Yu-Qi Cao , Ying-Jie Lu , Li Zhang , Jing Zhang , Yin-Long Guo . Vacuum promoted on-tissue derivatization strategy: Unravelling spatial distribution of glycerides on tissue. Chinese Chemical Letters, 2024, 35(12): 109788-. doi: 10.1016/j.cclet.2024.109788
14. [14]
  Zhiwei Zhong , Yanbin Huang , Wantai Yang . A simple photochemical method for surface fluorination using perfluoroketones. Chinese Chemical Letters, 2024, 35(5): 109339-. doi: 10.1016/j.cclet.2023.109339
15. [15]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
16. [16]
  Haitao Yin , Liang Meng , Li Li , Jiamu Xiao , Longrui Liang , Nannan Huang , Yansong Shi , Angang Zhao , Jingwen Hou . Polydopamine-modified biochar supported polylactic acid and zero-valent iron affects the functional microbial community structure for 1,1,1-trichloroethane removal in simulated groundwater. Chinese Chemical Letters, 2025, 36(1): 110313-. doi: 10.1016/j.cclet.2024.110313
17. [17]
  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
18. [18]
  Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
19. [19]
  Changyuan Bao , Yunpeng Jiang , Haoyin Zhong , Huaizheng Ren , Junhui Wang , Binbin Liu , Qi Zhao , Fan Jin , Yan Meng Chong , Jianguo Sun , Fei Wang , Bo Wang , Ximeng Liu , Dianlong Wang , John Wang . Synergizing 3D-printed structure and sodiophilic interface enables highly efficient sodium metal anodes. Chinese Chemical Letters, 2024, 35(11): 109353-. doi: 10.1016/j.cclet.2023.109353
20. [20]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(798)
HTML views(87)

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