含芳基三氮唑结构的3-乙砜基吡啶类化合物的合成及杀虫活性研究
收稿日期: 2020-09-18
修回日期: 2020-12-14
网络出版日期: 2021-02-22
基金资助
2011绿色农药协同创新中心(KYY-ZX-20170007)
Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds
Received date: 2020-09-18
Revised date: 2020-12-14
Online published: 2021-02-22
Supported by
Collaborative Innovation Center of 2011 Green Pesticide(KYY-ZX-20170007)
以3,6-二氯吡啶-2-羧酸为起始原料, 依据活性亚结构拼接原理, 设计合成了结构新颖的含芳基三氮唑结构的3-乙砜基吡啶类化合物, 所有目标化合物均经1H NMR, 13C NMR和HRMS结构表征. 初步杀虫活性测试结果表明, 在500 mg/L浓度下, 目标化合物均对玉米粘虫(Mythimna separata walker)表现出良好的致死活性, 2-(3-(2,6-二氟苯基)-1-甲基-1H-1,2,4-三唑-5-基)-3-(乙基磺酰基)-6-(吡咯烷-1-基)吡啶(9c), N-(仲丁基)-6-(3-(2,6-二氟苯基)-1-甲基- 1H-1,2,4-三唑-5-基)-5-(乙基磺酰基)吡啶-2-胺(9g), 6-(3-(2,6-二氟苯基)-1-甲基-1H-1,2,4-三唑-5-基)-5-(乙基磺酰基)-N-异丁基吡啶-2-胺(9h)在100 mg/L时, 致死率仍达到80%.
姚阳意 , 任朝丽 , 陈丽 , 钟良坤 , 许天明 , 谭成侠 . 含芳基三氮唑结构的3-乙砜基吡啶类化合物的合成及杀虫活性研究[J]. 有机化学, 2021 , 41(5) : 2055 -2062 . DOI: 10.6023/cjoc202009042
According to the principle of active substructure splicing, novel 3-ethyl sulfone pyridine substituted aryl triazole compounds were designed and synthesized using 3,6-dichloropyridine-2-carboxylic acid as primary material. All the compounds were characterized by 1H NMR, 13C NMR and HRMS spectra. The preliminary bioassay indicated that most title compounds exhibited relatively high insecticidal activity against Mythimna separata walker at 500 mg/L. Especially 2-(3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl)-3-(ethylsulfonyl)-6-(pyrrolidin-1-yl)pyridine (9c), N-(sec-butyl)-6- (3-(2,6-difluorophenyl)-1-methyl-1H-1,2,4-triazol-5-yl)-5-(ethylsulfonyl)pyridin-2-amine (9g), 6-(3-(2,6-difluorophenyl)-1- methyl-1H-1,2,4-triazol-5-yl)-5-(ethylsulfonyl)-N-isobutylpyridin-2-amine (9h) exhibited mortality 80% against M. separate at 100 mg/L.
Key words： ethylsulfone; triazole; pyridine; synthesis; insecticidal activity
| [1] | Monicka, J.; James, C. J. Mol. Struct. 2014, 1075, 335. |
| [2] | Zan, N.-N.; Wan, F.-X.; Wang, S.-C.; Zhang, J.-H.; Jiang, L. Chin. J. Org. Chem. 2017, 37, 1537. (in Chinese). |
| [2] | (昝宁宁, 万福贤, 王士春, 张君辉, 姜林, 有机化学, 2017, 37, 1537.) |
| [3] | Shelke, S.; Mhaske, P.; Kasam, S. Bobade, V. D. J. Heterocycl. Chem. 2015, 51, 1893. |
| [4] | Shao, X.-S.; Xu, Z.-P.; Zhao, X.-F.; Xu, X.-Y.; Tao, L.-M.; Li, Z.; Qian, X.-H. J. Agric. Food Chem. 2010, 58, 2690. |
| [5] | Refaat, H. Eur. J. Med. Chem. 2010, 45, 2949. |
| [6] | Prosenjit, D.; Yehoshoa, B.; David, M. ACS Catal. 2017, 7, 7456. |
| [7] | Liu, Z.-X.; Yuan, J.; Zhang, Z.-F.; Yan, D.-Y.; Zhang, W.-B. Chin. J. Org. Chem. 2018, 38, 3302. (in Chinese). |
| [7] | (刘战雄, 袁晶, 张振锋, 颜德岳, 张万斌, 有机化学, 2018, 38, 3302). |
| [8] | Suresh, L.; Sagar, V.; Poornachandra, Y.; Ganesh, K.; Chandramouli, G. Bioorg. Med. Chem. Lett. 2017, 27, 1451. |
| [9] | Ma, H.-J.; Li, Y.-H.; Zhao, Q.-F.; Zhang, T.; Xie, R.-L.; Mei, X.-D.; Ning, J. J. Agric. Food Chem. 2010, 58, 4356. |
| [10] | Dai, H.; Huang, M.-L.; Ge, S.-S.; Sun, S.-Y.; Shen, A.-B.; Cheng, X.-Y.; Li, C.-J.; Shi, J. Chin. J. Org. Chem. 2017, 37, 3289. (in Chinese). |
| [10] | (戴红, 黄美岭, 葛书山, 孙思宇, 沈爱宝, 成晓燕, 李春建, 石健, 有机化学, 2017, 37, 3289.) |
| [11] | Fadda, A.; Abd Salam, M.; Tawfik, E.; Anwar, E.; Etmana, H. RSC Adv. 2017, 63, 39773. |
| [12] | Wang, X.; Chen, Y.-F.; Yan, W.; Cao, L.-L.; Ye, Y.-H. Molecules 2016, 21, 1574. |
| [13] | Si, W.-J.; Zhang, T.; Li, Y.-F.; She, D.-M.; Pan, W.-L.; Gao, Z.-L.; Ning, J.; Mei, X.-D. J. Pestic. Sci. 2015, 41, 15. |
| [14] | Tonelli, M.; Novelli, F.; Tasso, B.; Vazzana, I.; Sparatore, A.; Boido, V.; Sparatore, F.; Colla, P.; Sanna, G.; Giliberti, G.; Busonera, B.; Farci, P.; Ibba, C.; Loddo, B. Bioorg. Med. Chem. 2014, 22, 4893. |
| [15] | Reddy, G.; Giri, S. RSC Adv. 2016, 6, 47145. |
| [16] | Zhang, L.-Y.; Wang, B.-L.; Zhan, Y.-Z.; Zhang, Y.; Zhang, X.; Li, Z.-M. Chin. Chem. Lett. 2016, 27, 163. |
| [17] | Abdel, R.; Farghaly, A. J. Chin. Chem. Soc. 2013, 51, 147. |
| [18] | Wang, Z.-J.; Liu, B.; Li, Y.-H.; Zhao, W.-G. Chin. J. Org. Chem. 2011, 31, 317. (in Chinese). |
| [18] | (王振军, 刘斌, 李永红, 赵卫光, 有机化学, 2011, 31, 317.) |
| [19] | Gonec, T.; Kos, J.; Zadrazilova, I.; Pesko, M.; Govender, R.; Keltosova, S.; Chambel, B.; Pereira, D.; Kollar, P.; Imramovsky, A.; O'Mahony, J.; Coffey, A.; Cizek, A.; Kralova, K.; Jampilek, J. Bioorg. Med. Chem. 2013, 21, 6531. |
| [20] | Francis, E.; James, T.; Joe, R.; Perry, V.; Leonard, P.; James, M.; Timothy, P.; Maruice, Y.; Donald, H.; Mary, L. WO 0024720, 2000. |
| [21] | Xu, W.-M.; Yang, S.; Bhadury, P.; He, J.; He, M.; Gao, L.-L.; Hu, D.-Y.; Song, B. Pestic. Biochem. Physiol. 2011, 101, 6. |
| [22] | Li, P.; Yin, J.; Xu, W.-M.; Wu, J.; He, M.; Hu, D.-Y.; Yang, S.; Song, B.-A. Chem. Biol. Drug Des. 2013, 82, 546. |
| [23] | Li, P.; Shi, L.; Yang, X.; Yang, L.; Chen, X.-W.; Wu, F.; Shi, Q.-C.; Xu, W.-M.; He, M.; Hu, D.-Y.; Song, B.-A. Bioorg. Med. Chem. Lett. 2014, 24, 1677. |
| [24] | Sun, X.-Y.; Feng, J.-J.; Li, S.-B.; Feng, S.-R.; Liu, Z.-M.; Qiao, X.-Q. Chin. J. Org. Chem. 2019, 39, 1037. (in Chinese). |
| [24] | (孙晓阳, 冯佳佳, 李生彬, 冯思冉, 刘振明, 宋亚丽, 乔晓强, 有机化学, 2019, 39, 1037.) |
| [25] | Masaki, T.; Takamasa, T.; Mai, I.; Atsushi, I.; Yoshihiko, N. WO 2014104407, 2014. |
| [26] | Andrew, E.; Marcel, J.; Michel, M.; Andre, J.; Daniel, E.; Graham, H.; Vikas, S.; Jagadish, P. WO 2017055147, 2017. |
| [27] | Ishaaya, I.; Horowitz, A. In Insecticides with Novel Modes of Action: Mechanisms and Application, Eds.: Ishaaya, I.; Degheele, D.,Springer, Berlin, 1998, p. 152. |
| [28] | Dey, S.; Mal, D. Tetrahedron Lett. 2005, 46, 5483. |
| [29] | Tan, C.-X.; Tian, X.-Y.; Yang, S.; Dai, L.; Ren, C.-L. CN 111943994, 2020. |
| [30] | Yuji, N.; Yuichi, O. JP 2016102104, 2016. |
| [31] | Wang, S.; Cuesta-Seijo, J. A.; Lafont, D.; Palcic, M. M.; Vidal, S. Chem.-Eur. J. 2013, 15, 15346. |
| [32] | Xu, Y.-M.; Liang, P.-Y.; Rashid, H.; Wu, L.-C.; Xie, P.; Wang, H.-D.; Zhang, S.-Y.; Wang, L.-S.; Jiang, J. Med. Chem. Res. 2019, 28, 1617. |
| [33] | Tang, H.-W.; Lou, J.; Yu, P.-G.; Liu, L.; Zheng, A.-X.; Chen, Y.-K.; Wang, C.-D. WO 2018149359, 2018. |
/
| 〈 |
|
〉 |
