Chinese Journal of Organic Chemistry >
Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety
Received date: 2022-11-16
Revised date: 2022-12-23
Online published: 2023-01-05
Supported by
National Natural Science Foundation of China(22177057); Science and Technology Project Fund of Nantong City(MS2202024)
Sixteen novel pyrazole amide compounds containing an isoxazole unit were synthesized through introducing an isoxazole moiety to pyrazole amide molecules based on the structure of chlorantraniliprole. The structures of the designed compounds were characterized with 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay showed that most of the target compounds exhibited 100% insecticidal activities against Mythimna separata at the dosage of 500 μg/mL. Three compounds had 80%~100% mortality rate towards M. separata at the dosage of 100 μg/mL, and three compounds still possessed 40%~50% mortality rate against M. separata when the dosage was lowered to 20 μg/mL. Three compounds displayed 100% insecticidal activities towards Aphis medicaginis at 500 μg/mL, and still showed good insecticidal activities against A. medicaginis with 70%~100% at 100 μg/mL. In addition, two compounds demonstrated 90%~100% mortality rates towards Tetranychus cinnabarinus at 500 μg/mL.
Key words： isoxazole; pyrazole amide; synthesis; insecticidal activity
Zichan Zhang , Yang Sun , Sheng Hua , Baolin Xu , Min Zhang , Qin Zhao , Dandan Zheng , Yang Wang , Jianfeng Ju , Yujun Shi , Hong Dai . Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety[J]. Chinese Journal of Organic Chemistry, 2023 , 43(4) : 1435 -1443 . DOI: 10.6023/cjoc202211021
| [1] | Wang, Y. Y.; Xu, F. Z.; Zhu, Y. Y.; Song, B. A.; Liu, D. X.; Yu, G.; Chen, S. H.; Xue, W.; Wu, J. Bioorg. Med. Chem. Lett. 2018, 28, 2979. |
| [2] | Zhou, Y. H.; Sun, W.; Peng, J. L.; Yan, H.; Zhang, L.; Liu, X. Y.; Zuo, Z. L. Bioorg. Chem. 2019, 93, 103322. |
| [3] | Mekky, A. E. M.; Sanad, S. M. H.; Said, A. Y.; Elneairy, M. A. A. Synth. Commun. 2020, 50, 2376. |
| [4] | Wang, J. L.; Zhou, Y. Q.; Wang, X. W.; Duan, L. X.; Duan, J.; Li, W. G.; Zhang, A. D. J. Agric. Food Chem. 2020, 68, 3071. |
| [5] | He, B.; Wu, F. X.; Yu, L. K.; Wu, L.; Chen, Q.; Hao, G. F.; Yang, W. C.; Lin, H. Y.; Yang, G. F. J. Agric. Food Chem. 2020, 68, 5059. |
| [6] | Eryilmaz, S.; Celikoglu, E. T.; Idil, O.; Inkaya, E.; Kozak, Z.; Misir, E.; Gul, M. Bioorg. Chem. 2020, 95, 103476. |
| [7] | Tu, M. T.; Shao, Y. Y.; Yang, S.; Sun, B. L.; Wang, Y. Y.; Tan, C. X.; Wang, X. D. Molecules 2022, 27, 4692. |
| [8] | Zheng, Z. G.; Dai, A. L.; Jin, Z. C.; Chi. Y. R.; Wu, J. J. Agric. Food Chem. 2022, 70, 11019. |
| [9] | Kiyani, H.; Mosallanezhad, A. Curr. Org. Synth. 2018, 15, 715. |
| [10] | Soliman, N. N.; Salam, M. A.; Fadda, A. A.; Abdel-Motaal, M. J. Agric. Food Chem. 2020, 68, 5790. |
| [11] | Lin, X. D.; Li, Y.; Zhong, W. Q.; Hong, T.; Li, L. H.; Song, S. Y.; He, D. H. J. Agric. Food Chem. 2021, 69, 9520. |
| [12] | Yuan, Y.; Subedi, L.; Lim, D.; Jung, J. K.; Kim, S. Y. Bioorg. Med. Chem. Lett. 2018, 29, 329. |
| [13] | Nagaraju, B.; Shanmukhakumar, J. V.; Seelam, N.; Subbaiah, T.; Prasanna, B. Curr. Org. Synth. 2019, 16, 1161. |
| [14] | Trivedi, J.; Parveen, A.; Rozy, F.; Mitra, A.; Bal, C.; Mitra, D.; Sharon, A. Eur. J. Med. Chem. 2019, 183, 111699. |
| [15] | Warda, E. T.; Shehata, I. A.; El-Ashmawy, M. B.; El-Gohary, N. S. Bioorg. Med. Chem. 2020, 28, 115674. |
| [16] | Arya, G. C.; Kaur, K.; Jaitak, V. Eur. J. Med. Chem. 2021, 221, 113511. |
| [17] | Pascal, B.; Gopal, D.; Wolfgang, V.; Matthias, P.; Franz, J. B. WO 2016102482, 2016 |
| [17] | [Chem. Abstr. 2016, 165, 152398 ] |
| [18] | Yang, Z. B.; Zhao, Y.; Li, P.; He, Y. J. J. Heterocycl. Chem. 2019, 56, 3042. |
| [19] | Yang, Z. B.; Li, P.; He, Y. J. Molecules 2019, 24, 3766. |
| [20] | Liu, J. B.; Li, F. Y.; Hao, Z. S.; Wang, Y. H.; Hua, X. W.; Li, Y. X.; Li, Z. M. Bioorg. Med. Chem. 2020, 28, 115829. |
| [21] | Xie, W. B.; Li, H. G.; Meng, X. D.; Li, Z. M.; Zhou, S. Chin. J. Org. Chem. 2021, 41, 1722. (in Chinese) |
| [21] | (谢伟彬, 李焕功, 孟祥德, 李正名, 周莎, 有机化学, 2021, 41, 1722.) |
| [22] | Yang, D. Y.; Zhao, B.; Fan, Z. J.; Yu, B.; Zhang, N. L.; Li, Z. M.; Zhu, Y. L.; Zhou, J. H.; Kalinina, T. A.; Glukhareva, T. V. J. Agric. Food Chem. 2019, 67, 13185. |
| [23] | Zeng, H. N.; Zhang, W.; Wang, Z. X.; Geng, W.; Feng, G.; Gan, X. H. J. Agric. Food Chem. 2022, 70, 7400. |
| [24] | Nayak, N.; Ramprasad, J.; Dalimba, U. J. Heterocycl. Chem. 2017, 54, 171. |
| [25] | Iqbal, J.; Ejaz, S. A.; Saeed, A.; al-Rashida, M. Eur. J. Pharmacol. 2018, 832, 11. |
| [26] | Nithyabalaji, R.; Krishnan, H.; Sribalan, R. J. Mol. Struct. 2019, 1186, 1. |
| [27] | Wu, H. X.; Han, M. H.; Jiang, K. J. Agrochemicals 2007, 46, 707. (in Chinese) |
| [27] | (吴华新, 韩敏晖, 蒋开杰, 农药, 2007, 46, 707.) |
| [28] | Xu, S. C.; Yu, Y. F.; Wang, X. J.; Wan, Q. Mod. Agrochem. 2008, 7, 8. (in Chinese) |
| [28] | (徐尚成, 俞幼芬, 王晓军, 万琴, 现代农药, 2008, 7, 8.) |
| [29] | Zhao, Y.Y.; Gao, L.; Li, H. G.; Sun, P. W.; Meng, F. F.; Zhang, Y.; Xie, Y. T.; Sun, B. Q.; Zhou, S.; Ma, Y.; Xiong, L. X.; Yang, N.; Li, Y. X.; Li, Z. M. J. Agric. Food Chem. 2020, 68, 11282. |
| [30] | Zhang, Y.; Li, Y. X.; Li, H.; Shang, J. F.; Li, Z. M.; Wang, B. L. Chin. Chem. Lett. 2022, 33, 501. |
| [31] | Liu, J. B.; Li, Y. X.; Zhang, X. L.; Hua, X. W.; Wu, C. C.; Wei, W.; Wan, Y. Y.; Cheng, D. D.; Xiong, L. X.; Yang, N.; Song, H. B.; Li, Z. M. J. Agric. Food Chem. 2016, 64, 3697. |
| [32] | Dai, H.; Chen, J.; Li, G.; Ge, S. S.; Shi, Y. J.; Fang, Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2017, 27, 950. |
| [33] | Zhang, J. F.; Xu, J. Y.; Wang, B. L.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Ma, Y.; Li, Z. M. J. Agric. Food Chem. 2012, 60, 7565. |
| [34] | Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390. |
| [35] | Shi, Y. J.; Fang, Y.; Li, Y.; Chen, J.; Li, G.; Wang, Q. M.; Dai, H. Chem. J. Chin. Univ. 2017, 38, 421. (in Chinese) |
| [35] | (石玉军, 方源, 李阳, 陈佳, 李刚, 汪清民, 戴红, 高等学校化学学报, 2017, 38, 421.) |
/
| 〈 |
|
〉 |
