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

doi:10.6023/cjoc202012017

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1722-1727.DOI: 10.6023/cjoc202012017 Previous Articles Next Articles

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新型含N-七氟异丙基苯基吡唑的邻甲酰氨基苯甲酰胺类化合物的设计合成以及生物活性研究

谢伟彬¹, 李焕功¹, 孟祥德¹, 李正名¹^,^* nkzml@vip.163.com, 周莎¹^,^*()

1 南开大学元素有机化学研究所元素有机化学国家重点实验室天津 300071

收稿日期:2020-12-09 修回日期:2020-12-31 发布日期:2021-02-07
通讯作者: 李正名, 周莎
基金资助:
国家重点研究开发计划(2018YFD0200100); 国家自然科学基金(21602118)

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

Weibin Xie¹, Huangong Li¹, Xiangde Meng¹, Zhengming Li¹^,^* nkzml@vip.163.com, Sha Zhou¹^,^*()

1 State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 30071

Received:2020-12-09 Revised:2020-12-31 Published:2021-02-07
Contact: Zhengming Li, Sha Zhou
About author:
* Corresponding author. E-mail: zhousha@nankai.edu.cn;
E-mail: nkzml@vip.163.com
Supported by:
National Key Research and Development Plan(2018YFD0200100); National Natural Science Foundation of China(21602118)

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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.

Key words: heptafluoroisopropyl, anthranilic diamide, synthesis, insecticidal activity

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.

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Fig. & Tab. 6

Figure 1. The Structure of Ryanodine, Flubendiamide and Chlorantraniliprole

Figure 2. Design of target compounds

Scheme 1. Synthesis route of compound I

Compd.	larvicidal activity/%
Compd.	200 mg/L	100 mg/L	50 mg/L	25 mg/L	10 mg/L	5 mg/L	2.5 mg/L
Ia	100	100	20
Ib	100	50
Ic	100	100	100	100	100	100	20
Id	100	100	5
Ie	100	100	5
If	100	100	25
Chlorantraniliprole		100	100	100	100	100	100

Table 1. Insecticidal activity of target compound I against Oriental armyworm

Figure 3. Autodock of chlorantraniliprole

Figure 4. Autodock of compound Ic

References 28

[1]	Pengfei, L.; Sha, Z.; Lixia, X.; Shujing, Y.; Xiao, Z.; Zhengming, L. Chem. J. Chin. Univ. 2012, 33,738. (in Chinese)
	( 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)
	( 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)
	( 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)
	( 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. pmid: 29191465
[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. pmid: 22812664
[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. pmid: 24433133
[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.

新型含N-七氟异丙基苯基吡唑的邻甲酰氨基苯甲酰胺类化合物的设计合成以及生物活性研究

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

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