Citation: Luo Chunyan, Ma Wenjing, Lv Liang, Pang Huailin, Xiang Juncheng, Zhou Liqi, Yin Dulin, Liu Jiyong. Synthesis and Insecticidal Activity of Novel meta-Diamide Compounds Containing Cyclopropyl Group[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2963-2970. doi: 10.6023/cjoc202003025 shu

Synthesis and Insecticidal Activity of Novel meta-Diamide Compounds Containing Cyclopropyl Group

Luo Chunyan ^a ,
Ma Wenjing ^b ,
Lv Liang ^b ,
Pang Huailin ^b ,
Xiang Juncheng ^c ,
Zhou Liqi ^c ,
Yin Dulin ^a,, ,
Liu Jiyong ^b,,

a.
National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081
b.
CAC Shanghai International Trading Co., Ltd., Shanghai 200335
c.
Greentech Laboratory Co., Ltd., Shanghai 200335

Corresponding author: Yin Dulin, dulinyin@126.com Liu Jiyong, jiyong_liu@cacch.com
Received Date: 9 March 2020
Revised Date: 26 May 2020
Available Online: 15 July 2020

Figures(3)

To discover novel insecticide with improved activity, a series of meta-diamide compounds containing cyclopropyl moiety were synthesized on the principle of biologically active factor splicing. The structures of synthetic derivatives were characterized by ¹H NMR, ¹³C NMR and HRMS. Preliminary bioassay data showed that some of the title compounds exhibited good insecticidal activities against Plutella xylostella and Chilo suppressalis. Among them, the mortality of N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(N-(cyclopropylmethyl)benzamido)-2-fluorobenzamide (6d) and 3-(N-(cyclopropylmethyl)benzamido)-N-(2, 6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzamide (6e) was 100% against Plute-lla xylostella at 1 mg/L, and the mortality of compound 6d was 100% against Chilo suppressalis at 5 mg/L.
- synthesis,
- cyclopropyl,
- meta-diamide,
- inseticidal activity
1. [1]
  Zhou, S.; Gu, Y. C.; Liu, M.; Wu, C. C.; Zhou, S.; Zhao, Y.; Jia, Z. H.; Wang, B. L.; Xiong, L. X.; Yang, N.; Li, Z. M. J. Agric. Food Chem. 2014, 62, 11054. doi: 10.1021/jf503513n
2. [2]
  Zhou, S.; Yan, T.; Li, Y. X.; Jia, Z. H.; Wang, B. L.; Zhao, Y.; Qiao, Y. Y.; Xiong, L. X.; Li, Y. Q.; Li, Z. M. Org. Biomol. Chem. 2014, 12, 6643. doi: 10.1039/C4OB00716F
3. [3]
  Li, Y. H.; Zhu, H. J; Chen, K.; Liu, R.; Khallaf, A; Zhang, X. J; Ni, J. P. Org. Biomol. Chem. 2013, 11, 3979. doi: 10.1039/c3ob40345a
4. [4]
  Meng, X. D.; Zhou, S.; Xie, Y. T.; Zhao, Y.; Xiong, L. X.; Zhou, S.; Li, Z. M. Chin. J. Org. Chem. 2017, 37, 908(in Chinese).
5. [5]
  Li, Y.; Li, M.; Chai, B. S; Liu, C. L. Agrochemicals 2005, 45, 697(in Chinese).
6. [6]
  Qu, J. J.; Zhu, X. K; Wang, L.; Xu, C.; Liu, F.; Ren, L.; Xu, X. B.; Xiong, L. X.; Wang, Y.; Rui, C. H.; Liu, S. D. J. Agric. Food Chem. 2012, 60, 10942. doi: 10.1021/jf303376t
7. [7]
  Zhou, Y. Y.; Wang, B. L; Di, F. J; Xu, C.; Xiong, L. X.; Yang, N.; Li, Y. Q; Li, Y. X.; Li, Z. M. Bioorg. Med. Chem. Lett. 2014, 24, 2295. doi: 10.1016/j.bmcl.2014.03.077
8. [8]
  Kang, S. H.; Song, B. A; Wu, J; He, M.; Hu, D. Y.; Jin, L. H; Zeng, S; Xue, W.; Yang, S. Eur. J. Med. Chem. 2014, 67, 14.
9. [9]
  Guo, L.; Wang, Y.; Zhou, X. G.; Li, Z. Y.; Liu, S. Z.; Liang, P.; Gao, X. W. Pest Manage. Sci. 2014, 70, 1083. doi: 10.1002/ps.3651
10. [10]
  Guo, L.; Liang, P.; Zhou, X. G.; Gao, X. W. Sci. Rep. 2014, 4, 6924.
11. [11]
  Hu, Z. D.; Chen, H. Y.; Li, Z. Y.; Zhang, D. Y.; Yin, F.; Lin, Q. S.; Bao, H. L.; Zhou, X. M.; Feng, X. Guangdong Agric. Sci. 2012, (1), 79(in Chinese). doi: 10.3969/j.issn.1004-874X.2012.01.030
12. [12]
  Hu, Z. D.; Feng, X.; Li, Z. Y.; Zhang, D. Y.; Chen, H, Y. Agrochem. Res. Appl. 2010, 14, 25(in Chinese).
13. [13]
  Li, X. X.; Liang, P.; Gao, X. W. J. Plant Protect. 2015, 42, 481(in Chinese). doi: 10.13802/j.cnki.zwbhxb.2015.04.001
14. [14]
  Yang, J. C.; Wu, Q.; Wang, X. L. Agrochemicals 2014, 53, 215(in Chinese).
15. [15]
  Nakao, T.; Banba, S. Bioorg. Med. Chem. 2016, 24, 372. doi: 10.1016/j.bmc.2015.08.008
16. [16]
  Nakao, T.; Banba, S.; Nomura, M.; Hirase, K. Insect Biochem. Mol. Biol. 2013, 43, 366. doi: 10.1016/j.ibmb.2013.02.002
17. [17]
  Ozoe, Y.; Kita, T.; Ozoe, F.; Nakao, T.; Sato, K.; Hirase, K. Pestic. Biochem. Physiol. 2013, 107, 285. doi: 10.1016/j.pestbp.2013.09.005
18. [18]
  Katsuta, H.; Nomura, M.; Wakita, T.; Daido, H.; Kobayashi, Y.; Kawahara, A.; Banba, S. J. Pestic. Sci. 2019, 44, 120. doi: 10.1584/jpestics.D18-088
19. [19]
  Qi, H. L.; Cui, L.; Wang, Q. Q.; Liu, F.; Bing, C. H. Plant Protect. 2017, 43, 112(in Chinese). doi: 10.3969/j.issn.0529-1542.2017.01.018
20. [20]
  Muriel, B.; Gagnebin, A.; Waser, J. Chem. Sci. 2019, 10, 10716. doi: 10.1039/C9SC03790J
21. [21]
  Menear, K. A.; Adcock, C.; Boulter, R.; Cockcroft, X.; Copsey, L.; Cranston, A.; Dillon, K. J.; Drzewiecki, J.; Garman, S.; Gomez, S.; Javaid, H.; Kerrigan, F.; Knights, C.; Lau, A.; Vincent, M.; Jr, Moore, S.; Smith, J. C.; Martin, N. M. J. Med. Chem. 2008, 51, 6581. doi: 10.1021/jm8001263
22. [22]
  Chang, F.; Dutta, S.; Becnel, J. J.; Estep, A. S.; Mascal, M. J. Agric. Food Chem. 2014, 62, 476. doi: 10.1021/jf4045843
23. [23]
  Liu, A. C.; He, X. L.; Feng, J. L.; Yu, C. H.; Zhang, S. K. Agrochemicals 2015, 54, 790(in Chinese).
24. [24]
  Dai, H.; Hong, Y.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Shi, Y. J.; Li, C. J.; Shi, J.; Shi, L. Chin. J. Org. Chem. 2017, 37, 3006(in Chinese).
25. [25]
  Zhu, B. C.; Xu, T. M.; Kong, X. L.; Wei, W.; Li, X. N. Agrochemicals 2009, 48, 712(in Chinese). doi: 10.3969/j.issn.1006-0413.2009.10.003
26. [26]
  Zhang, H. M.; Feng, Q; Weng, J. Q.; Kong, X. L.; Wei, Y. C.; Yuan, J.; Xing, J. H. Chin. J. Org. Chem. 2013, 33, 32(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]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
5. [5]
  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
6. [6]
  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
7. [7]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
8. [8]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 100010-. doi: 10.3866/PKU.WHXB202309041
9. [9]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
10. [10]
  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
11. [11]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
12. [12]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
13. [13]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
14. [14]
  Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe₂O₄@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187
15. [15]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
16. [16]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
17. [17]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
18. [18]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
19. [19]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
20. [20]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1293)
HTML views(184)

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