Citation: Wu Ningjie, Cheng Long, Wang Jian, Yu Jiping, Xing Jiahua, Xu Tianming, Wei Youchang. Synthesis and Insecticidal Activity of Novel 4-Arylamino Pyrimidine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 852-860. doi: 10.6023/cjoc201807044 shu

Synthesis and Insecticidal Activity of Novel 4-Arylamino Pyrimidine Derivatives

Wu Ningjie ^a ,
Cheng Long ^b ,
Wang Jian ^b ,
Yu Jiping ^a ,
Xing Jiahua ^a ,
Xu Tianming ^a ,
Wei Youchang ^a,b,,

a.
Sinochem Lantian Zhejiang Research Institute of Chemical Industry Co. Ltd., Hangzhou 310023
b.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Wei Youchang, weiyouchang@sinochem.com
Received Date: 24 July 2018
Revised Date: 22 October 2018
Available Online: 25 March 2018
Fund Project: the China Postdoctoral Science Foundation 2016M601971Project supported by the China Postdoctoral Science Foundation (No. 2016M601971)

Figures(3)

A series of novel 4-arylamino pyrimidine derivatives were synthesized using substituted aniline as starting material via diazotization, Meerwein arylation, isothiocyanation, addition, methylation and cyclization. The preliminary results of insecticidal activities indicated that most of the compounds exhibited 100% insecticidal activitiy against Mythimna separata Walker at 500 mg/L. At 20 mg/L, N-(2-chloro-4-fluorophenyl) -2, 6-dimethyl-5-(4-phenoxy-2-(trifluoromethyl) phenyl) -pyrimidin-4-amine (6h) exhibited 80% and 60% mortality against Mythimna separata Walker and Plutella xylostella Linnaeus, respectively.
- 4-arylamino pyrimidine,
- pyrimidinamine,
- synthesis,
- insecticidal
1. [1]
  Oerke, E. C. J. Agric. Sci. 2006, 144, 31. doi: 10.1017/S0021859605005708
2. [2]
  Wang, B. L.; Zhu, H. W.; Ma, Yi.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483. doi: 10.1021/jf4012467
3. [3]
  Keen, N.; Taylor, S. Nat. Rev. Cancer 2004, 4, 927. doi: 10.1038/nrc1502
4. [4]
  Chu, X.-J.; DePinto, W.; Bartkovitz, D.; So, S.-S.; Vu, B. T.; Packman, K.; Lukacs, C.; Ding, Q.; Jiang, N.; Wang, K.; Goelzer, P.; Yin, X.; Smith, M. A.; Higgins, B. X.; Chen, Y.; Xiang, Q.; Moliterni, J.; Kaplan, G.; Graves, B.; Lovey, A.; Fotouhi, N. J. Med. Chem. 2006, 49, 6549. doi: 10.1021/jm0606138
5. [5]
  Cha, M. Y.; Lee, K.-O.; Kang, S.-J.; Jung, Y. H.; Song, J. Y.; Choi, K. J.; Byun, J. Y.; Lee, H.-J.; Lee, G. S.; Park, S. B.; Kim, M. S. J. Med. Chem. 2012, 55, 2846. doi: 10.1021/jm201758g
6. [6]
  Odell, L. R.; Abdel-Hamid, M. K.; Hill, T. A.; Chau, N.; Young, K. A.; Deane, F. M.; Sakoff, J. A.; Andersson, S.; Daniel, J. A.; Robinson, P. J.; McCluskey, A. J. Med. Chem. 2017, 60, 349. doi: 10.1021/acs.jmedchem.6b01422
7. [7]
  Xu, Y.; Yang, J. C.; Ren, L. H.; Hao, S. L.; Liu, C. L. Agrochemicals 2011, 50, 474(in Chinese). doi: 10.3969/j.issn.1006-0413.2011.07.002
8. [8]
  Chen, M. H.; Wu, W. N.; Chen, L. J.; Shu, H. Agrochemicals 2017, 56, 474(in Chinese).
9. [9]
  Wang, B.-L.; Shi, Y.-X.; Ma, Y.; Liu, X.-H.; Li, Y.-H.; Song, H.-B.; Li, B.-J.; Li, Z.-M. J. Agric. Food Chem. 2010, 58, 5515. doi: 10.1021/jf100300a
10. [10]
  Zhang, Y.; Zhan, Y.-Z.; Ma, Y.; Hua, X.-W.; Wei, W.; Zhang, X.; Song, H.-B.; Li, Z.-M.; Wang, B.-L. Chin. Chem. Lett. 2018, 29, 441. doi: 10.1016/j.cclet.2017.08.035
11. [11]
  Zhang, Y.; Li, Z.; Song, H.; Wang, B. Chin. J. Chem. 2018, 36, 635. doi: 10.1002/cjoc.v36.7
12. [12]
  Dai, H.; Ye, L.; Li, Y.; Fang, Y.; Shi, Y.; Liang, Z.; Shi, J. Chin. J. Org. Chem. 2017, 37, 1020(in Chinese).
13. [13]
  Matsumoto, K.; Yokoi, S.; Fujii, K.; Akiyoshi, Y. EP 0196524, 1987[Chem. Abstr. 1987, 106, 14736].
14. [14]
  Obata, T.; Fujii, K.; Ooka, A.; Yamanaka, Y. EP 0665225, 1995[Chem. Abstr. 1995, 123, 314007].
15. [15]
  Fujii, K.; Tanaka, T.; Fukuda, Y. EP 0370704, 1990[Chem. Abstr. 1990, 113, 212005].
16. [16]
  Cuccia, S. J.; Wood, W. W.; Buckwalter, B. L.; Chiarello, J. F.; Fleming, L. B. US 6281219, 2001[Chem. Abstr. 2001, 135, 195573].
17. [17]
  Schwoegler, A.; Gewehr, M.; Mueller, B.; Grote, T.; Grammenos, W.; Tormo, I.; Blasco, J.; Gypser, A.; Rheinheimer, J.; Blettner, C.; Schaefer, P.; Schieweck, F.; Wagner, O.; Stierl, R.; Schofl, U.; Strathmann, S.; Scherer, M. WO 2005012261, 2005[Chem. Abstr. 2005, 142, 198096].
18. [18]
  Mueller, M.; Schwarz, H.-G.; Wiese, W. B.; Wroblowsky, H.-J.; Arnold, C.; Dahmen, P.; Franken, E.-M.; Malsam, O.; Voerste, A. EP 2092824, 2009[Chem. Abstr. 2009, 151, 281672].
19. [19]
  Liu, Q.; Huang, F.; Yuan, X.; Wang, K.; Zou, Y.; Shen, J.; Xu, Y. J. Med. Chem. 2017, 60, 10231. doi: 10.1021/acs.jmedchem.7b01530
20. [20]
  Li, L.; Liu, Z. P.; Lin, Y. B. Chin. J. Org. Chem. 2007, 27, 1244(in Chinese).
21. [21]
  Gharat, L. A.; Muthukaman, N.; Narayana, L.; Khairatkar-Joshi, N.; Kattige, V. G. WO 2012055995, 2012[Chem. Abstr. 2012, 156, 613397].
22. [22]
  Long, J. K.; Gregory, V.; Gutteridge, S.; Taggi, A. E.; Bereznak, J. F. WO 2012031061, 2012[Chem. Abstr. 2012, 156, 378885].
23. [23]
  Li, Q.; Yu, H. B.; Guan, A. Y.; Liang, S. J.; Song, Y. Q.; Li, B. Chin. J. Org. Chem. 2012, 32, 1736(in Chinese).
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
5. [5]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
6. [6]
  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
7. [7]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
8. [8]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
9. [9]
  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
10. [10]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
11. [11]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
12. [12]
  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
13. [13]
  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
14. [14]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
15. [15]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
16. [16]
  Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H₂O₂合成：协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
17. [17]
  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
18. [18]
  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
19. [19]
  Yuxin CHEN , Yanni LING , Yuqing YAO , Keyi WANG , Linna LI , Xin ZHANG , Qin WANG , Hongdao LI , Wenmin WANG . Construction, structures, and interaction with DNA of two Sm^Ⅲ₄ complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1141-1150. doi: 10.11862/CJIC.20240258
20. [20]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1746)
HTML views(130)

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