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Design, Synthesis and Biological Activity Study of Novel N-Phenylpyrazole Anthranilic Diamides Containing Heptafluoroisopropyl Moieties

  • Weibin Xie ,
  • Huangong Li ,
  • Xiangde Meng ,
  • Zhengming Li ,
  • Sha Zhou
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  • 1 State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 30071
* Corresponding author. E-mail: ;

Received date: 2020-12-09

  Revised date: 2020-12-31

  Online published: 2021-02-07

Supported by

National Key Research and Development Plan(2018YFD0200100); National Natural Science Foundation of China(21602118)

Abstract

In order to develop new green pesticides with high efficiency and low toxicity, N-phenylpyrazole anthranilic diamides containing heptafluoroisopropyl moieties were designed, synthesized and evaluated for their insecticidal activity against Oriental armyworm. Their structures were confirmed by NMR and HRMS analysis. Preliminary biological activity showed that most of the compounds exhibited good insecticidal activity. In particular, compound Ic againstOriental armywormwas 20% at 2.5 mg/L. This result laid a certain foundation for the innovation of ryanodine receptor insecticides in the future.

Cite this article

Weibin Xie , Huangong Li , Xiangde Meng , Zhengming Li , Sha Zhou . Design, Synthesis and Biological Activity Study of Novel N-Phenylpyrazole Anthranilic Diamides Containing Heptafluoroisopropyl Moieties[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1722 -1727 . DOI: 10.6023/cjoc202012017

References

[1]
Pengfei, L.; Sha, Z.; Lixia, X.; Shujing, Y.; Xiao, Z.; Zhengming, L. Chem. J. Chin. Univ. 2012, 33,738. (in Chinese)
[1]
( 李鹏飞, 周莎, 熊丽霞, 于淑晶, 张晓, 李正名, 高等学校化学学报, 2012, 33,738.)
[2]
Xuhong, Q.; Xiaoyong, X.; Gonghua, S.; Zhong, L. J. Guizhou Univ. 2003, 20,83. (in Chinese)
[2]
( 钱旭红, 徐晓勇, 宋恭华, 李忠, 贵州大学学报, 2003, 20,83.)
[3]
Yibin, Z. World Pestic. 2007, 29,1. (in Chinese)
[3]
( 张一宾, 世界农药, 2007, 29,1.)
[4]
George, P.L.; Daniel, C.; James, D.B. Bioorg. Med. Chem. 2009, 17,4127.
[5]
Rogers, E.F.; Koniuszy, F.R. J. Am. Chem. Soc. 1948, 70,3086.
[6]
Ruest, L.; Deslongchamps, P. Can. J. Chem. 1993, 71,634.
[7]
Nagatomo, M.; Koshimizu, M.; Masuda, K.; Tabuchi, T.; Urabe, D.; Inoue, M. J. Am. Chem. Soc. 2014, 136,5916.
[8]
Changlin, L. Chin. J. Pest. 2005, 44,522. (in Chinese)
[8]
( 刘长令, 农药, 2005, 44,522.)
[9]
Lehmberg, E.; Casida, J.E. Pestic. Biochem. Physiol. 1994, 48,145.
[10]
Masanori, T.; Hayami, N.; Takashi, F.; Akiral, S.; Hiroki, K.; Kenji, T.; Shinsuke, F.; Hiroshi, K.; Takashi, H.; Tetsuyoshi, N. J. Pestic. Sci. 2005, 30,354.
[11]
Zhu, Y.; Loso, M. US 7709649, 2010.
[12]
Xiulan, Z.; Yuxin, L.; Jinlong, M.; Hongwei, Z.; Baolei, W.; Mingzhen, M.; Lixia, X.; Yongqiang, L.; Zhengming, L. Bioorg. Med. Chem. 2013, 22,186.
[13]
Jingbo, L.; Yuxin, L.; Xiulan, Z.; Xuewen, H.; Changchun, W.; Wei, W.; Yingying, W.; Dandan, C.; Lixia, X.; Na, Y.; Haibin, S.; Zhengming, L. J. Agric. Food. Chem. 2016, 64,3697.
[14]
Jingbo, L.; Yuxin, L.; Xiulan, Z.; Dandan, C.; Wei, W.; Changchun, W.; Yongtao, X.; Lixia, X.; Zhengming, L. Chin. J. Chem. 2017, 35,368.
[15]
Jingbo, L.; Fengyun, L.; Jingyue, D.; Yuxin, L.; Xiulan, Z.; Yuanhong, W.; Lixia, X.; Zhengming, L. Bioorg. Med. Chem. 2018, 26,3541.
[16]
Jingbo, L.; Fengyun, L.; Yuxin, L.; Xiulan, Z.; Xuewen, H.; Lixia, X.; Zhengming, L. Pest. Manage. Sci. 2019, 75,1034.
[17]
Yangyang, Z.; Li, G.; Huangong, L.; Pengwei, S.; Fanfei, M.; Yan, Z.; Yongtao, X.; Binqiao, S.; Sha, Z.; Y, M.; Lixia, X.; Na, Y.; Yuxin, L.; Zheng-Ming, L. J. Agric. Food Chem. 2020, 68,11282.
[18]
Yangyang, Z.; Huangong, L.; Pengwei, S.; Li, G.; Jingbo, L.; Sha, Z.; Lixia, X.; Na, Y.; Yuxin, L.; Zhengming, L. Bioorg. Med. Chem. Lett. 2020, 30,1.
[19]
Lin, L.; Liu, C.; Qin, J.; Wang, J.; Dong, S.; Chen, W.; He, W.; Gao, Q.; You, M.; Yuchi, Z. Insect. Biochem. Mol. Biol. 2018, 92,73.
[20]
Jian, Z.; Xiuhong, T.; Isaac, I.; Song, C.; Jingjing, W.; Jinlong, Y.; Hui, L.; Xuhong, Q. J. Agric. Food Chem. 2010, 58,2736.
[21]
Gribkov, D.; EL Qacemi, M.; Stoller, A.; Jeanguenat, A.; Bigot, A. WO 2019/30357, 2019.
[22]
Jifeng, Z.; Junying, X.; Baolei, W.; Yuxin, L.; Lixia, X.; Yongqiang, L.; Y, M.; Zhengming, L. J. Agric. Food Chem. 2012, 60,7565.
[23]
Weili, D.; Junying, X.; Lixia, X.; Xinghai, L.; Zhengming, L. Chin. J. Chem. 2009, 27,579.
[24]
Christian, G.; André, J.; Ana, C. D.; Christoph, G.; Daniel, P.K.; Andrew, J.C. Bioorg. Med. Chem. Lett. 2012, 22,3800.
[25]
Xuewen, H.; Wutao, M.; Zhijin, F.; Xiaotian, J.; Fengyun, L.; Guangning, Z.; Haibin, S.; Juanjuan, L.; Like, Z.; Lifeng, Z.; Xiaowen, L.; Genhao, W.; Xiaoyan, C. Aust. J. Chem. 2014, 67,1491.
[26]
Mingzhen, M.; Yuxin, L.; Yunyun, Z.; Xiulan, Z.; Qiaoxia, L.; Fengjuan, D.; Haibin, S.; Lixia, X.; Yongqiang, L.; Zhengming, L. J. Agric. Food. Chem. 2014, 62,1536.
[27]
Shapiro, R.; Taylor, E.G.; Zimmerman, W.T. WO 2006062978, 2006.
[28]
Sha, Z.; Yucheng, G.; Ming, L.; Changchun, W.; Sha, Z.; Yu, Z.; Zhehui, J.; Baolei, W.; Lixia, X.; Na, Y.; Zhengming, L. J. Agric. Food Chem. 2014, 62,11054.
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