Synthesis and Insecticidal Activities of N-(tert-Butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl Hydrazide Derivatives

doi:10.6023/cjoc201510019

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1051-1059.DOI: 10.6023/cjoc201510019 Previous Articles Next Articles

ARTICLE

N-叔丁基-N'-氟代苯甲酰基-取代吡啶甲酰肼衍生物的合成与杀虫活性研究

胡崇波, 刘建华, 杜晓华

浙江工业大学催化加氢中心浙江省绿色农药清洁生产技术研究重点实验室浙江省绿色农药协同创新中心杭州 310014

收稿日期:2015-10-17 修回日期:2015-12-15 发布日期:2016-01-21
通讯作者: 杜晓华 E-mail:duxiaohua@zjut.edu.cn

Synthesis and Insecticidal Activities of N-(tert-Butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl Hydrazide Derivatives

Hu Chongbo, Liu Jianhua, Du Xiaohua

Zhejiang Key Laboratory of Green Pesticides and Cleaner Production Technology, Zhejiang Green Pesticide Collaborative Innovation Center, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014

Received:2015-10-17 Revised:2015-12-15 Published:2016-01-21

1. Synthesis and Insecticidal Activities of N-(tert-Butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl Hydrazide Derivatives.PDF(3430KB)

Abstract

In order to find novel diacylhydrazine derivatives which possessed high activities against pests, 20 novel N-(tert-butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl hydrazide derivatives were synthesized by introducing fluoro-contained phenyl and pyridine into the basic structure of diacylhydrazines. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS. The bioassay results indicated that most of the compounds exhibited more than 80% mortality against Mythimna separateat the concentration of 500 mg/L. Among these compounds, N-(tert-butyl)-N'-(2,6-difluorobenzoyl)-N-2-chloronico-tinohydrazine (6bb)andN-(tert-butyl)-N'-(2,6-difluorobenzoyl)-N-2,5-dichloronicotinohydrazine (6gb)exhibited 100% and 80% mortality against Mythimna separateat 10 mg/L, respectively. The LC₅₀ of compound 6bb against Mythimna separatawas 8.77 mg/L, and it showed about 0.51 times of toxicity against Mythimna separatethan tebufenozide and had 1.5 times of toxicity against Plutella xylostella than tebufenozide.

Key words: diacylhydrazine, pyridylcarbonyl hydraziden, synthesis, insecticidal activity

Cite this article

Hu Chongbo, Liu Jianhua, Du Xiaohua. Synthesis and Insecticidal Activities of N-(tert-Butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl Hydrazide Derivatives[J]. Chin. J. Org. Chem., 2016, 36(5): 1051-1059.

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[1] Nakagawa, Y.; C. Henrich, V. FEBS J. 2009, 276, 6128.
[2] Xu, Z.-H.; Li, J.-K. Jiangsu Agric. Sci. 2015, 45, 5 (in Chinese).
(徐志红, 李俊凯, 江苏农业科学, 2015, 45, 5.)
[3] (a) Zhao, Q.-Q.; Shang, J.; Huang, Z.-Q.; Wang, K.-Y.; Bi, F.-C.; Huang, Y.-Q.; Wang, Q.-M. J. Agric. Food Chem. 2008, 56, 5254.
(b) Wing, K. D. Science 1988, 241, 467.
[4] (a) Oikawa, N.; Nakagawa, Y.; Nishimura, K.; Ueno, T.; Fujita, T. Pestic. Sci. 1994, 41, 139.
(b) Oikawa, N.; Nakagawa, Y.; Nishimura, K.; Ueno, T.; Fujita, T. Pestic. Biochem. Physiol. 1994, 48, 135.
(c) Nakagawa, Y.; Soya, Y.; Nakai, K.; Oikawa, N.; Nishimura, K.; Ueno, T.; Fujita, T.; Kurihara, N. Pestic. Sci. 1995, 43, 339.
[5] (a) Chen, Z.-M. World Pestic. 2007, 29, 12 (in Chinese).
(程志明, 世界农药, 2007, 29, 12.) (b) Nakagawa, Y.; Hattori, K.; Shimizu, B.; Akamatsu, M.; Miyagawa, H.; Ueno, T. Pestic. Sci. 1998, 53, 267.
(c) Soin, T.; Swevers, L.; Kotzia, G.; Iatrou, K.; Janssen, C. R.; Rouge, P.; Harada, T.; Nakagawa, Y.; Smagghe, G. Pest. Manage. Sci. 2010, 66, 1215.
(d) Hormann, R. E.; Smagghe, G.; Nakagawa, Y. QSAR Comb. Sci. 2008, 27, 1098.
[6] (a) Heller, J. J.; Mattioda, H.; Klein, E.; Sagenmuller, A. Brighton Crop Prot. Conf.-Pests Dis. 1992, 1, 59.
(b) Le, D. P.; Thirugnanam, M.; Lidert, Z.; Carlson, G. R.; Ryan, J. B. Brighton Crop Prot. Conf.-Pests Dis. 1996, 2, 481.
(c) Lidert, Z.; Hormann, R. E.; Le, D. P.; Opie, T. R. CA 2103110, 1994 [Chem. Abstr. 1994, 112, 314557].
(d) Cowles, R. S.; Villani, M. G. J. Econ. Entomol. 1996, 89, 1356.
(e) Carlson, G. R.; Aller, H. E. GB 2231268, 1990 [Chem. Abstr. 1990, 114, 180361].
(f) Yanagi, M.; Sugizaki, H.; Toya, T.; Kato, Y.; Shirakura, H.; Watanabe, T.; Yajima, Y.; Kodama, S.; Masui, A.; Yanai, T.; Tsukamoto, Y.; Sawada, Y.; Yokoi, S. EP 496342, 1992 [Chem. Abstr. 1992, 117, 212514].
(g) Yanagi, M.; Watanabe, T.; Masui. Brighton Crop Prot. Conf.-Pests Dis. 2000, 2, 27.
(h) Zhang, X.-N.; Li, Y.-F.; Ni, Y.-P.; Zhu, L.-M.; Hu, J.-B.; Jiang, M.-G. Chin. J. Pestic. 2003, 42, 18 (in Chinese).
(张湘宁, 李玉峰, 倪钰萍, 朱丽梅, 胡嘉斌, 蒋木庚, 农药, 2003, 42, 18.)
[7] Mao, C.-H.; Wang, Q.-M.; Huang, R.-Q. Chin. J. Pestic. Sci. 2004, 6, 1 (in Chinese).
(毛春晖, 汪清民, 黄润秋, 农药学学报, 2004, 6, 1.)
[8] (a) Huang, Z.-Q.; Lv, Z.-J.; Zhu, H.-L.; Liu, B.; Wei, Z.; Shang, Z.-Q.; Shi, J. Chin. J. Pestic. 2014, 53, 161 (in Chinese).
(黄治强, 吕丽娟, 朱华玲, 刘斌, 尉震, 尚志强, 石军, 农药, 2014, 53, 161.) (b) Zhao, H.-W.; Liang, C. Organo-fluorine Ind. 2010, 2, 28 (in Chinese).
(赵红伟, 梁诚, 有机氟工业, 2010, 2, 28.)
[9] Wing, K. D.; Pa, L. US 5424333, 1995[Chem. Abstr. 1995, 123, 313108].
[10] (a) Shang, E.-C.; Liu, C.-L.; Du, Y.-J. Chem. Ind. Eng. Prog. 1996, 5, 11 (in Chinese).
(尚尔才, 刘长令, 杜英娟, 化工进展, 1996, 5, 11.) (b) Yang, J.-C.; Dai, R.-H.; Liu, Y.-P.; Wu, Q.; Liu, C.-L. Chin. J. Pestic. 2011, 50, 625 (in Chinese).
(杨吉春, 戴荣华, 刘允萍, 吴峤, 刘长令, 农药, 2011, 50, 625.)
[11] (a) Hsu, A. C.; Le, D. P. US 5354762, 1994 [Chem. Abstr. 1994, 122, 314457].
(b) Hsu, A. C.; Aller, H. E.; Le, D. P.; Hamp, D. W.; Weinstein, B.; Murphy, R. A. US 6013836, 2000 [Chem. Abstr. 2000, 132, 89489].
[12] Mao, C.-H.; Wang, Q.-M.; Huang, Y.-Q.; Bi, F.-C.; Wang, K.-L. CN 1654464, 2005 [Chem. Abstr. 2005, 144, 468023].
[13] (a) Liu, J.-H. Ph.D. Dissertation, Zhejiang University of Technology, Hangzhou, 2014 (in Chinese).
(刘建华, 博士论文, 浙江工业大学, 杭州, 2014.) (b) Du, X.-H; Liu, J.-H; Hu, C.-B. CN 104744358, 2015 [Chem. Abstr. 2015, 162, 82129].
[14] (a) Huang, Z.-Q.; Cui, Q.-M.; Xiong, L.-X.; Wang, Z.-W.; Wang, K.-Y.; Zhao, Q.-Q.; Bi, F.-C.; Wang, Q.-M. J. Agric. Food Chem. 2009, 57, 2450.
[15] Chen, N.-G.; Liu, X.-Y.; Ren, Z.-P. West China J. Pharm. Sci. 2008, 23, 166 (in Chinese).
(陈年根, 刘新泳, 任兆平, 华西药学杂志, 2008, 23, 166.)
[16] Zhang, X.-N.; Li, Y.-F.; Zhu, L.-M.; Liu, L.-Y.; Sha, X.-Y.; Xu, H.; Ma, H.-J.; Wang, F.-Y.; Ni, Y.-P.; Guo, L.-P. CN 1313276, 2001 [Chem. Abstr. 2001, 137, 294865].
[17] Sawada, Y.; Yanai, T.; Nakagawa, H.; Tsukamoto, Y.; Yokoi, S.; Yanagi, M.; Toya, T.; Sugizaki, H.; Kato, Y.; Shirakura, H.; Watanabe, T.; Yajima, Y.; Kodama, S.; Masui, A. Pest Manage. Sci. 2003, 59, 26.

N-叔丁基-N'-氟代苯甲酰基-取代吡啶甲酰肼衍生物的合成与杀虫活性研究

Synthesis and Insecticidal Activities of N-(tert-Butyl)-N'-fluorobenzoyl-substitutedpyridylcarbonyl Hydrazide Derivatives

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