Citation: Zhong Liangkun, Jiang Tao, Zhang Fan, Fu Qing, Liu Xinghai, Xu Tianming, Ding Chengrong, Chen Jie, Yuan Jing, Tan Chengxia. Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2655-2662. doi: 10.6023/cjoc201903056 shu

Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives

Zhong Liangkun ^a,b ,
Jiang Tao ^a ,
Zhang Fan ^b ,
Fu Qing ^a ,
Liu Xinghai ^a ,
Xu Tianming ^b ,
Ding Chengrong ^a ,
Chen Jie ^c ,
Yuan Jing ^c,, ,
Tan Chengxia ^a,,

a.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
b.
Zhejiang Research Institute of Chemical Industry. Ltd., Hangzhou 310023
c.
School of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou 311300

Corresponding author: Yuan Jing, 1015251265@qq.com Tan Chengxia, tanchengxia@zjut.edu.cn
Received Date: 26 March 2019
Revised Date: 19 April 2019
Available Online: 15 September 2019
Fund Project: the National Key Research and Development Plan 2017YFD0200507Project supported by the National Key Research and Development Plan (No. 2017YFD0200507)

Figures(3)

A series of 3-arylisoxazoline-pyrazole-5-carboxamide derivatives derived from ethyl 5, 5-dimethoxy-2, 4-dioxopentanoate were designed, synthesized, and characterized by ¹H NMR, ¹³C NMR and HRMS. The preliminary bioassay indicated that most title compounds exhibited positive potency against Mythimna separate (Walker) at 500 mg/L. At the concentration of 100 mg/L, three compounds were still moderately active against Mythimna separate (Walker) (lethal rate≈60%). At 500 mg/L, four compounds were also active against Aphis craccivora. The results indicated that the potential of these 3-arylisoxazoline-pyrazole-5-carboxamide derivatives can be utilized in insecticide research with further optimization.
- arylisoxazoline,
- pyrazole-5-carboxamide,
- synthesis,
- insecticidal activity
1. [1]
  Pirol, S.-C.; Caliskan, B.; Durmaz, I.; Atalay, R.; Banoglu, E. Eur. J. Med. Chem. 2014, 87, 140. doi: 10.1016/j.ejmech.2014.09.056
2. [2]
  Gong, C.-C.; Tan, H.-Y.; Zhang, Q. Chin. J. Org. Chem. 2018, 38, 3086 (in Chinese).
3. [3]
  He, B.; Wang, D.-W.; Yang, W.-C.; Chen, Q.; Yang, G.-F. Chin. J. Org. Chem. 2017, 37, 2895 (in Chinese).
4. [4]
  Li, Y.-X.; Liu, S.-H.; Li, Y.-H.; Song, H.-B.; Wang, Q.-M. Bioorg. Med. Chem. Lett. 2009, 19, 2953. doi: 10.1016/j.bmcl.2009.04.048
5. [5]
  Bizikova, P.; Linder, K.; Olivry, T. Vet. Dermatol. 2014, 25, 103. doi: 10.1111/vde.12117
6. [6]
  Aloisi, A.; Franchet, A.; Ferrandon, D.; Bianco, A.; Moyon, C. Bioorg. Med. Chem. Lett. 2018, 28, 2631. doi: 10.1016/j.bmcl.2018.06.036
7. [7]
  Xiong, L.; Li, H.; Jiang, L.-N.; Ge, J.-M.; Yang, W.-C.; Zhu, X.-L.; Yang, G.-F. J. Agric. Food Chem. 2017, 65, 1021. doi: 10.1021/acs.jafc.6b05134
8. [8]
  Sun, N.-B.; Shen, Z.-H.; Zhai, Z.-W.; Han, L.; Weng, J.-Q.; Tan, C.-X.; Liu, X.-H. Chin. J. Org. Chem. 2017, 37, 2705 (in Chinese).
9. [9]
  Li, X.-H.; Zhi, L.-P.; Song, B.-A.; Xu, H.-L. Chem. Res. Chin. Univ. 2008, 24, 454. doi: 10.1016/S1005-9040(08)60095-1
10. [10]
  Shi, Y.-J.; Zhou, Q.; Wang, Y.; Qian, H.-W.; Ye, L.-Y.; Feng, X.; Chen, H.; Li, Y.-T.; Dai, H.; Wei, Z.-H.; Wu, J.-M. Chin. J. Org. Chem. 2018, 38, 2450 (in Chinese).
11. [11]
  Zhang, X.-L.; Wang, B.-L.; Mao, M.-Z.; Xiong, L.-X.; Yu, S.-J.; Li, Z.-M. Chem. J. Chin. Univ. 2013, 34, 96 (in Chinese).
12. [12]
  Song, H.-J.; Liu, Y.-X.; Xiong, L.-X.; Li, Y.-Q.; Yang, N.; Wang, Q.-M. J. Agric. Food Chem., 2013, 61, 8730. doi: 10.1021/jf402719z
13. [13]
  Zhao, Y.; Li, Y.-Q.; Xiong, Li.-X.; Xu, L.-P.; Peng, L.-N.; Li, F.; Li, Z.-M. Chem. Res. Chin. Univ. 2013, 29, 51. doi: 10.1007/s40242-013-2167-y
14. [14]
  Grossmann, K.; Ehrhardt, T. Pest. Manage. Sci. 2007, 63, 429. doi: 10.1002/ps.1341
15. [15]
  Yang, S.-G.; Hao, G.-F.; Dayan, F.-E.; Tranel, P.; Yang, G.-F. Chin. J. Chem. 2013, 31, 1153. doi: 10.1002/cjoc.201300449
16. [16]
  Monicka, J.; James, C. J. Mol. Struct. 2014, 1075, 335. doi: 10.1016/j.molstruc.2014.07.002
17. [17]
  Chen, X.-L.; Xiao, Y.-X.; Wang, G.-L.; Li, Z.; Xu, X.-Y. Res. Chem. Intermed. 2016, 42, 5495. doi: 10.1007/s11164-015-2381-y
18. [18]
  Meanwell, N. J. Med. Chem. 2011, 54, 2529. doi: 10.1021/jm1013693
19. [19]
  Lingaraju, G.; Balaji, K.; Jayarama, S.; Anil, S.; Kiran, K.; Sadashiva, M. Bioorg. Med. Chem. Lett. 2018, 28, 3606. doi: 10.1016/j.bmcl.2018.10.046
20. [20]
  Loh, B.; Vozzolo, L.; Mok, B.; Lee, C.-C.; Fitzmaurice, R.; Caddick, S.; Fassati, A. Chem. Biol. Drug. Des. 2010, 75, 461. doi: 10.1111/j.1747-0285.2010.00956.x
21. [21]
  Talley, J.; Brown, D.; Carter, J.; Graneto, M.; Koboldt, C.; Masferrer, J.; Perkins, W.; Rogers, R.; Shaffer, A.; Zhang, Y.-Y.; Zweifel, B.; Seibert, K. J. Med. Chem. 2000, 43, 775. doi: 10.1021/jm990577v
22. [22]
  Brahmayya, M.; Venkateswararao, B.; Krishnarao, D.; Durgarao, S.; Prasad, U.; Damodharam, T.; Mishra, R. J. Pharm. Res. 2013, 7, 516.
23. [23]
  Fang, F. Ph. D. Dissertation, Guangxi University, Nanning, 2016 (in Chinese).
24. [24]
  Pascal, B.; Gopal, D.; Wolfgang, V.; Matthias, P.; Franz, J. B. WO 2016102482, 2016 [Chem. Abstr. 2016, 165, 152398].
25. [25]
  Shoop, W.; Hartline, E.; Gould, B.; Waddell, M.; McDowell, R.; Kinney, J.; Lahm, G.; Long, J.; Xu, M.; Wagerle, T.; Jones, G.; Dietrich, R.; Cordova, D.; Schroeder, M.; Rhoades, D.; Benner, E.; Confalone, P. Vet. Parasitol. 2014, 201, 179. doi: 10.1016/j.vetpar.2014.02.020
26. [26]
  Ishaaya, I.; Horowitz, A. R. In Insecticides with Novel Modes of Action: Mechanisms and Application, Eds.: Ishaaya, I.; Degheele, D., Springer, Berlin, 1998, p. 152.
27. [27]
  Semple, G.; Gharbaoui, T.; Shin, Y.; Decaire, M.; Averbuj, C.; Skinner, P. US 20070032537, 2007 [Chem. Abstr. 2007, 142, 219276].
28. [28]
  Martins, M.; Sinhorin, A.; Frizzo, C.; Buriol, L.; Scapin, E.; Zanatta, N.; Bonacorso, H. J. Heterocycl. Chem. 2013, 50, 71. doi: 10.1002/jhet.996
29. [29]
  Jagannath, M.; Madhavan, G.; Shanmugam, P. WO 2014202580, 2014[Chem. Abstr. 2014, 162, 137571].
30. [30]
  Liu, T.-T.; Ni, Y.; Zhong, L.-K.; Huang, H.-Y.; Hu, W.-Q.; Xu, T.-M.; Tan, C.-X. Chin. J. Org. Chem. 2015, 35, 422 (in Chinese).
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
3. [3]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
4. [4]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
7. [7]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
10. [10]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
11. [11]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
12. [12]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
13. [13]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
14. [14]
  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
15. [15]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
16. [16]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
18. [18]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
19. [19]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
20. [20]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1242)
HTML views(155)

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