为发现结构新颖、活性优异、环境友好的新型杀虫剂,本文采用活性亚结构拼接策略,以环丙氟虫胺为先导化合物,设计并合成了两个系列共计20个未见文献报道的新型双酰胺化合物, 其结构经过1H NMR、13C NMR和HRMS 确证。初步的生物活性测试结果表明, 目标化合物虽未显著提升对鳞翅目害虫小菜蛾和粘虫的杀虫活性,但在半翅目害虫防治方面取得了一定进展。部分化合物对苜蓿蚜和褐飞虱表现出良好的杀虫活性,特别是化合物N-(3-((2-溴-6-(二氟甲氧基)-4-(全氟丙烷)苯基)氨甲酰基)-2-氟苯基)-N-(1,1-二氧化四氢噻吩-3-基)-6-(三氟甲基)烟酰胺(8e)表现尤为突出,在10 mg/L测试浓度下对苜蓿蚜的杀虫活性为100.0%,在40 mg/L下对褐飞虱的杀虫活性为97.6%,显著优于对照药剂环丙氟虫胺。本研究为开发新型双酰胺杀虫剂提供了候选先导分子,也为防治半翅目害虫提供了新的解决方案。
To discover novel, highly active, and eco-friendly insecticides, 20 unreported diamide compounds were designed via active substructure splicing strategy using cyproflanilide as the lead. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Preliminary bioassays showed that although the target compounds did not significantly improve activity against lepidopteran pests including Plutella xylostella and Mythimna separata, progress was made against hemipteran pests. Some compounds exhibited good activity against Aphis craccivora and Nilaparvata lugens. Notably, compound N-(3-((2-bromo-6-(difluoromethoxy)-4-(perfluoropropan-2-yl)phenyl)carbamoyl)-2-fluorophenyl)-N-(1,1-dioxidotetrahydrothiophen-3-yl)-6-(trifluoromethyl)nicotinamide(8e) showed outstanding efficacy, with 100.0% insecticidal activity against Aphis craccivora at 10 mg/L and 97.6% against Nilaparvata lugens at 40 mg/L, significantly outperforming the control cyproflanilide. This study provides lead candidates for developing novel diamide insecticides and offers new solutions for managing hemipteran pests.
[1] Colin-Duchevet, L.; Sangely, A.; Charnet, P.; Sandoz, J.-C.J. Hazard. Mater. 2026, 507, 141739.
[2] Wu J.; Liu X.; Peng Y.; Zheng W.; Yang L.; Li X.; Zhang Y. Int.J. Mol. Sci. 2026, 27, 2897.
[3] Sun Z.; Xu H.Mini-Rev.Med. Chem. 2018, 18, 1.
[4] Lin L.; Jiang H.; Hadiatullah H.; Ma R.; Korza H.; Gu Y.; Yuchi Z.Biomolecules 2025, 15, 259.
[5] Xu Q. B.; Liang P. B.; Lu H.Z.; Xu C. L.; Wang M. A.; Zhang J. Chin.J. Org. Chem. 2021, 41, 3116 (in Chinese).
(许庆博, 梁培博, 路慧哲, 徐灿烂, 王明安, 张建军. 有机化学, 2021, 41, 3116.)
[6] Tohnishi M,Nishimatsu T,Motoba K,Hirooka T, Seo A.J. Pestic.Sci. 2010,35(4):490-491.
[7] Huang P. M.; Wu M. H.; Lv L.; Zhou L. Q.; Liu X. W.; Liu J. Y.Tetrahedron Lett. 2022, 96, 153743.
[8] Bastian M, Alec G, Jerome W. Chemical science. 2019, 10(46):10716-10722.
[9] Nakao T.; Banba S. Bioorg.Med. Chem. 2016, 24, 372.
[10] Yanbing W,Ru Y,Qiaoling Z, Liya Q,Guonian Z,Mengli C,J. Econ. Entomol. 2019,112(3):1348-1353.
[11] Jia Z. Q.; Zhang Y. C.; Huang Q. T.; Jones A. K.; Han Z. J.; Zhao C. Q.J. Hazard. Mater. 2020, 394, 122521.
[12] Nakao T.; Naoi A.; Hama M.; Kawahara N.; Hirase K.J. Econ. Entomol. 2012, 105, 1781.
[13] Zhang X.C.Ph.D. Dissertation, Shenyang Agricultural University, Shenyang, 2023(in Chinese).
(张鑫忱, 博士论文, 沈阳农业大学, 沈阳, 2023).
[14] Du W.; Awolola T. S.; Howell P.; Koekemoer L. L.; Brooke B. D.; Benedict M. Q.; Coetzee M.; Zheng L.Insect Mol. Biol. 2005, 14, 179.
[15] Xun X.; Ni Y. D.; Li J. F.; Ding Y.; Zhang M.; Wang Y.; Hu L. P.; Zhou H. Y.; Yang B.; Shi J.; Gao L.; Dai H. Chin.J. Org. Chem. 2020, 40, 1638(in Chinese).
(荀校, 倪亚丹, 李金峰, 丁颖, 张敏, 王杨, 胡兰萍, 周环宇, 杨冰, 石健, 高磊, 戴红, 有机化学, 2020, 40, 1638.)
[16] Tan H. J.World Pesticides., 2026, 1314.002(in Chinese).
(谭海军, 世界农药,2026, 1314.002.)
[17] Ge W. C.; Chen G. H.; Dong B. B.; Li H. S.; Wang M. Z.; Yang F. X.; Wu S. F.; Gao C. F.Pestic. Biochem. Physiol. 2025, 218, 106756.
[18] Zempleni J.; Wijeratne S. S.K.; Hassan, Y. I.BioFactors. 2009, 35, 36.
[19] Tanabe G.; Otani T.; Cong W.; Minematsu T.; Ninomiya K.; Yoshikawa M.; Muraoka O.Bioorg. Med. Chem. Lett. 2011, 21, 3159.
[20] Volkmann R. A.; Kelbaugh P. R.; Nason D. M.; Jasys V. J.J. Org. Chem. 1992, 57, 4352.
[21] W J J,P D E,E M S,G L,R T R,A A,J N T,I G D.J. Org. Chem. 2008,73(18):6970-82.
[22] Liang J. J.; Pan J. Y.; Xu D. C.; Xie J. W.Tetrahedron Lett. 2014, 55, 6335.
[23] Hu Y. J.; Wang X. B.; Li S. Y.; Xie S. S.; Wang D. G.K.; Kong, L. Y.Tetrahedron Lett. 2015, 56, 105.
[24] Jain A.; Maji S.; Shukla K.; Kumari A.; Garg S.; Metre R. K.; Bhattacharyya S.; Rana N. K.Org. Biomol. Chem. 2022, 20, 3124.
[25] Liu J. Y.; Wu M. H.; Xiang J. C.; Pang H. L.; Li B.; Lv L.J. Org.Chem. 2024,44(05):1584-1591(in Chinses).
(刘吉永, 吴明慧, 相君成, 庞怀林, 李斌, 吕亮. 有机化学, 2024, 44(05):1584-1591.)
[26] Luo C. Y.; Ma W. J.; Lv L.; Pang H. L.;Xiang J. C.; Zhou L. Q.; Yin D. L.; Liu J. Y.J. Org.Chem. 2020,40(09):2963-2970(in Chinses).
(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(09):2963-2970.)
[27] 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.
[28] Fratamico P. M.; Bagi L. K.[J].Ind. Microbiol. Biotechnol. 2001, 27, 129.
