Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide
Received date: 2021-02-03
Revised date: 2021-04-30
Online published: 2021-06-29
Supported by
National Natural Science Foundation of China(21762012); National Natural Science Foundation of China(32072445); National Natural Science Foundation of China(21562012); Program of Introducing Talents to Chinese Universities (111 Program(D20023(D20023)); S &T Planning Project of Guizhou Province(黔科合[2017]1402); S &T Planning Project of Guizhou Province(黔科合[2017]5788)
A series of novel N-cyano sulfonyimide derivatives containing trifluoromethyl pyridinamide were designed and synthesized by combination method of active substructure, and their structures were identified by 1H NMR, 13C NMR, 19F NMR and HRMS. Their antibacterial activity against Xanthomonas axonopodis pv. citri (Xac), Ralstonia solanacearum (R solanacearum), Xanthomonas oryzae pv. oryzae (Xoo) and insecticidal activity on Plutella xylostella (P. xylostella) were investigated. Some of the compounds were tested to display good antibacterial and moderate insecticidal activities. Among them, 3-chloro-N-(2-(N-cyano-S-(3,4-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G10) showed 67%, 53% and 48% activities against Xac, R. Solanacearum and Xoo at 200 mg/L, respectively. The antibacterial activity of 3-chloro-N- (2-(N-cyano-S-(2,5-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G17) against Xac was 69% and the inhibition rate of N-(2-(S-(2-bromo-4-fluorobenzyl)-N-cyanosulfonimidoyl)ethyl)-3-chloro-5-(trifluoromethyl)picolinamide (G14) on Xoo was 49%. N-(2-(S-(4-Bromo-2-fluorobenzyl)-N-cyanosulfonimidoyl)ethyl)-3-chloro-5-(trifluoromethyl)picolinamide (G1), 3-chloro-N-(2-(N-cyano-S-(3-fluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G7), 3-chloro- N-(2-(N-cyano-S-(2,4-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G8) and G10 also had moderate bactericidal activity at 100 mg/L, which are slightly higher than or comparable to that of the positive controls at the corresponding concentration. Moreover, compounds G10 and 3-chloro-N-(2-(N-cyano-S-(4-isopropylbenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G11) also showed moderate insecticidal activity against P. xvlostella of 77% and 70% at 500 mg/L.
Ali Dai , Renfeng Zhang , Chuanhui Li , Lijiao Yu , Ya Wang , Jian Wu . Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3633 -3642 . DOI: 10.6023/cjoc202102017
| [1] | Hu, Q.; Min, L.; Yang, X. Y.; Jin, S. X.; Zhang, L.; Li, Y. Y.; Ma, Y. Z.; Qi, X. W.; Li, D. Q.; Liu, H. B.; Zhu, L. F.; Zhang, X. L. Plant Physiol. 2018, 176, 1808. |
| [2] | Ferrarezi, J. H.; Dos Santos, J. A.; Sette, L. D.; Ferreira, H.; Sass, D. C. Afr. J. Biotechnol. 2019, 18, 713. |
| [3] | Chen, S.; Wang, C. Y.; Yang, J. Y.; Chen, B.; Wang, W. J.; Su, J.; Feng, A. Q.; Zeng, L. X.; Zhu, X. Y. Sci. Rep. 2020, 10, 12642. |
| [4] | Chen, J. X.; Luo, Y. Q.; Wei, C. Q.; Wu, S. K.; Wu, R.; Wang, S. B.; Hu, D. Y.; Song, B. A. Pest Manage. Sci. 2020, 76, 3188. |
| [5] | Chen, X. J.; Li, L. C.; Wang, H. C.; Huang, Y. F.; Wang, M. S.; Zhang, C. Q. Plant Pathol. J. 2016, 15, 102. |
| [6] | Isokar, S. S.; Bramhankar, S. B.; Das, A. K.; Thakur, K. D.; Pillai, Tini.; Dinkwar, G. T.; Kharat, V. M. Int. J. Chem. Stud. 2020, 8, 62. |
| [7] | Kemmitt, G.; Sparks, T. C.; Hunter, J. E.; Lorsbach, B. A.; Hanger, G.; Gast, R. E.; Bryant, R. J. J. Agric. Food Chem. 2018, 66, 10337. |
| [8] | Zhang, Y.; Pan, X. Y.; Duan, Y. B.; Zhu, X. F.; Ma, X. W.; Huang, T. T.; Gao, T. C.; Zhou, M. G. Australas. Plant Pathol. 2015, 44, 541. |
| [9] | Dannenberg, C. A.; Fritze, L.; Krauskopf, F.; Bolm, C. Org. Biomol. Chem. 2017, 15, 1086. |
| [10] | Hu, W. M.; Teng, F.; Peng, H. B.; Yu, J. T.; Sun, S.; Cheng, J.; Shao, Y. Tetrahedron Lett. 2015, 56, 7056. |
| [11] | Hua, X. W.; Mao, W. T.; Fan, Z. J.; Ji, X. T.; Li, F. Y.; Zong, G. N.; Song, H. B.; Li, J. J.; Zhou, L. K.; Zhou, L. F.; Liang, X. W.; Wang, G. H.; Chen, X. Y. Aust. J. Chem. 2014, 67, 1491. |
| [12] | Longhurst, C.; Babcock, J. M.; Denholm, I.; Gorman, K.; Thomas, J. D.; Sparks, T. C. Pest. Manage. Sci. 2013, 69, 809. |
| [13] | Yu, H. B.; Qin, Z. F.; Dai, H.; Zhang, X.; Qin, X.; Wang, T. T.; Fang, J. X. ARKIVOC 2008, 16, 99. |
| [14] | Wang, Z. Y.; Guo, W.; Zhu, J. D. US 20190152932, 2019 |
| [14] | [Chem. Abstr. 2019, 164, 519677] |
| [15] | Hua, X. W.; Mao, W. T.; Fan, Z. J.; J, X. T.; Li, F. Y.; Zong, G. G.; Song, H. B.; Li, J. J.; Zhou, L. K.; Zhou, L. F.; Liang, X. W.; Wang, G. H.; Chen, X. Y. Aust. J. Chem. 2014, 67, 1491. |
| [16] | Mao, W. T.; Zong, G. N.; Fan, Z. J.; Li, F. Y.; Song, H. B.; Li, J. J.; Tatiana, K. A.; Inna, K.; Ksenia, L.; Yury, M. Y.; Nataliya, B. P. J. Struct. Chem. 2015, 34, 1428. |
| [17] | Pasteris, R. J.; Bereznak, J. F.; Chittaboina, S.WO 2018080859, 2018 |
| [17] | [Chem. Abstr. 2018, 168, 488871] |
| [18] | Hartmut, A.; Simon, D. R.; Stefan, L.; Hansjoerg, D.; Elmar, G.; Christopher, H.; Schmutzler, D.WO 2013124230, 2013 |
| [18] | [Chem. Abstr. 2013, 159, 399083] |
| [19] | Thorsten, O.; Dennis, F.; Christian, G.US 20140057926, 2014 |
| [19] | [Chem. Abstr. 2014, 160, 398991] |
| [20] | Christian, G.; Oost, Thorsten, O. US 20150239875A1, 2015 |
| [20] | [Chem. Abstr. 2015, 163, 363329] |
| [21] | Andreas, B.; Dirk, G.; Armin, H.; Joerg, P. H.; Bernhard, S.; Dieter, W.US 9708274, 2017 |
| [21] | [Chem. Abstr. 2017, 162, 137891] |
| [22] | Cumming, J. N.; Scott, J. D. US 20170260181, 2017 |
| [22] | [Chem. Abstr. 2017, 164, 406699] |
| [23] | Khan, T. A.; Scott, J. D.; Cumming, J. N. US 9422255, 2016 |
| [23] | [Chem. Abstr. 2016, 161, 535595] |
| [24] | Dai, A. L.; Guo, S. X.; Li, C. H.; Zhang, R. F.; Wu, J. Mod. Agrochem. 2020, 19, 21. (in Chinese). |
| [24] | ( 代阿丽, 郭声鑫, 李传会, 张仁凤, 吴剑, 现代农药, 2020, 19, 21.) |
| [25] | Cao, X. F.; Zhang, R. F. World Pestic. 2018, 40, 7. (in Chinese). |
| [25] | ( 曹晓峰, 张瑞峰, 世界农药, 2018, 40, 7.) |
| [26] | Deng, H. X. Zhejiang Chem. Ind. 2011, 42, 1. (in Chinese). |
| [26] | ( 邓红霞, 浙江化工, 2011, 42, 1.) |
| [27] | Luo, D. X.; Guo, S. X.; He, F.; Wang, H. Y.; Xu, F. Z.; Dai, A. L.; Zhang, R. F.; Wu, J. Bioorg. Med. Chem. Lett. 2020, 30, 126902. |
| [28] | Hong, Y.; Dai, H.; 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). |
| [28] | ( 洪宇, 戴红, 叶林玉, 仲苏林, 曹熊飞, 石玉军, 李春建, 石健, 施磊, 有机化学, 2017, 37, 3006.) |
| [29] | Wang, Y. Y.; Xu, F. Z.; Luo, D. X.; Guo, S. X.; He, F.; Dai, A. L.; Song, B. A.; Wu, J. J. Agric. Food Chem. 2019, 67, 13344. |
| [30] | Xie, Y.; Chi, H. W.; Guan, A. Y.; Liu, C. L.; Ma, H. J.; Cui, D. L. J. Agric. Food Chem. 2014, 62, 12491. |
| [31] | Ji, X. X.; Li, J. J.; Meng, Z.; Zhang, S. A.; Dong, B.; Qiao, K. Plant Dis. 2019, 103, 1991. |
| [32] | Chen, J. X.; Yi, C. F.; Wang, S. B.; Wu, S. K.; Li, S. Y.; Hu, D. Y.; Song, B. A. Bioorg. Med. Chem. Lett. 2019, 29, 1203. |
| [33] | Xu, F. Z.; Wang, Y. Y.; Luo, D. X.; Yu, G.; Guo, S. X.; Fu, H.; Zhao, Y. H.; Wu, J. RSC Adv. 2018, 8, 6306. |
| [34] | Xu, F. Z.; Wang, Y. Y.; Luo, D. X.; Yu, G.; Wu, Y. K.; Dai, A. L.; Zhao, Y. H.; Wu, J. ChemistrySelect 2018, 3, 2795. |
| [35] | Guo, S. X.; He, F.; Dai, A. L.; Zhang, R. F.; Chen, S. H.; Wu, J. RSC Adv. 2020, 10, 35658. |
| [36] | Wu, J.; Hu, D. Y.; Yang, S. J. Guizhou Univ. (Nat. Sci.) 2006, 6, 622. (in Chinese). |
| [36] | ( 吴剑, 胡德禹杨松, 贵州大学学报(自然科学版), 2006, 6, 622.) |
| [37] | Christine, M. M. H.; Philip, L.; Julien, E.; Carsten, B. Adv. Synth. Catal. 2013, 355, 3363. |
| [38] | Shi, J.; Luo, N.; Ding, M. H.; Li, C. H.; Wan, S. R.; Li, P. J.; Li, J. H.; Bao, X. P. Chin. J. Org. Chem. 2021, 41, 738. (in Chinese). |
| [38] | ( 石军, 罗娜, 丁慕晗, 李传会, 万苏然, 李培甲, 李君荭, 鲍小平, 有机化学, 2021, 41, 738.) |
| [39] | Du, H.; Fan, Z. j.; Yang, L.; Bao, X. P. Chin. J. Org. Chem. 2018, 38, 531. (in Chinese). |
| [39] | ( 杜欢, 范治江, 杨岚, 鲍小平, 有机化学, 2018, 38, 531.) |
| [40] | Chen, Y.; Li, P.; Chen, M.; Su, S. J.; He, J.; Zhang, M. Liu, L. W.; Xue, W. Chin. J. Org. Chem. 2019, 39, 2813. (in Chinese). |
| [40] | ( 陈英, 李普, 陈梅, 苏时军, 贺军, 张敏, 柳立伟, 薛伟, 有机化学, 2019, 39, 2813.) |
| [41] | Shao, L. H.; Gan, Y. Y.; Hou, M.; Tao, S. L.; Zhang, L. Q.; Wang, Z. C.; Ouyang, G. P. Chin. J. Org. Chem. 2020, 40, 1975. (in Chinese). |
| [41] | ( 邵利辉, 甘宜远, 侯迷, 陶世林, 张丽琼, 王贞超, 欧阳贵平, 有机化学, 2020, 40, 1975.) |
| [42] | Luo, C. Y.; Ma, W. J.; Lv, L.; Pang, H. L.; Xiang, J. C.; Zhou, L. Q.; Yin, D. L.; Liu, J. Y. Chin. J. Org. Chem. 2020 40, 2963. (in Chinese). |
| [42] | ( 罗春艳, 马文静, 吕亮, 庞怀林, 相君成, 周丽琪, 尹笃林, 刘吉永, 有机化学, 2020 40, 2963.) |
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