新型4-芳氨基嘧啶类衍生物的合成及其杀虫活性
收稿日期: 2018-07-24
修回日期: 2018-10-22
网络出版日期: 2018-11-26
基金资助
中国博士后科学基金（No.2016M601971）资助项目.
Synthesis and Insecticidal Activity of Novel 4-Arylamino Pyrimidine Derivatives
Received date: 2018-07-24
Revised date: 2018-10-22
Online published: 2018-11-26
Supported by
Project supported by the China Postdoctoral Science Foundation (No. 2016M601971).
吴宁捷 , 程龙 , 王剑 , 郁季平 , 邢家华 , 许天明 , 魏优昌 . 新型4-芳氨基嘧啶类衍生物的合成及其杀虫活性[J]. 有机化学, 2019 , 39(3) : 852 -860 . DOI: 10.6023/cjoc201807044
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.
Key words： 4-arylamino pyrimidine; pyrimidinamine; synthesis; insecticidal
[1] Oerke, E. C. J. Agric. Sci. 2006, 144, 31.
[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.
[3] Keen, N.; Taylor, S. Nat. Rev. Cancer 2004, 4, 927.
[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.
[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.
[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.
[7] Xu, Y.; Yang, J. C.; Ren, L. H.; Hao, S. L.; Liu, C. L. Agrochemicals 2011, 50, 474(in Chinese). (徐英, 杨吉春, 任兰会, 郝树林, 刘长令, 农药, 2011, 50, 474.)
[8] Chen, M. H.; Wu, W. N.; Chen, L. J.; Shu, H. Agrochemicals 2017, 56, 474(in Chinese). (陈美航, 吴文能, 陈丽娟, 舒华, 农药, 2017, 56, 474.)
[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.
[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.
[11] Zhang, Y.; Li, Z.; Song, H.; Wang, B. Chin. J. Chem. 2018, 36, 635.
[12] Dai, H.; Ye, L.; Li, Y.; Fang, Y.; Shi, Y.; Liang, Z.; Shi, J. Chin. J. Org. Chem. 2017, 37, 1020(in Chinese). (戴红, 叶林玉, 李阳, 方源, 石玉军, 梁志鹏, 石健, 有机化学, 2017, 37, 1020.)
[13] Matsumoto, K.; Yokoi, S.; Fujii, K.; Akiyoshi, Y. EP 0196524, 1987[Chem. Abstr. 1987, 106, 14736].
[14] Obata, T.; Fujii, K.; Ooka, A.; Yamanaka, Y. EP 0665225, 1995[Chem. Abstr. 1995, 123, 314007].
[15] Fujii, K.; Tanaka, T.; Fukuda, Y. EP 0370704, 1990[Chem. Abstr. 1990, 113, 212005].
[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] 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] 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] Liu, Q.; Huang, F.; Yuan, X.; Wang, K.; Zou, Y.; Shen, J.; Xu, Y. J. Med. Chem. 2017, 60, 10231.
[20] Li, L.; Liu, Z. P.; Lin, Y. B. Chin. J. Org. Chem. 2007, 27, 1244(in Chinese). (李丽, 刘展鹏, 林原斌, 有机化学, 2007, 27, 1244.)
[21] Gharat, L. A.; Muthukaman, N.; Narayana, L.; Khairatkar-Joshi, N.; Kattige, V. G. WO 2012055995, 2012[Chem. Abstr. 2012, 156, 613397].
[22] Long, J. K.; Gregory, V.; Gutteridge, S.; Taggi, A. E.; Bereznak, J. F. WO 2012031061, 2012[Chem. Abstr. 2012, 156, 378885].
[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). (李琴, 于海波, 关爱莹, 梁松军, 宋玉泉, 李斌, 有机化学, 2012, 32, 1736.)
/
| 〈 |
|
〉 |
