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Longifolene-Derived Primary Amine Carboxylates for Sustainable Weed Management: Synthesis and Herbicidal Activity
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-07-25 , DOI: 10.1021/acs.jafc.4c02329 Yanqun Huang 1 , Pingping Lu 2 , Hongyun Lan 2 , Daozhan Huang 2 , Beiyang Liu 2 , Qiaozhen Wei 2 , Lanjie Huang 2 , Yuehong Gan 2
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-07-25 , DOI: 10.1021/acs.jafc.4c02329 Yanqun Huang 1 , Pingping Lu 2 , Hongyun Lan 2 , Daozhan Huang 2 , Beiyang Liu 2 , Qiaozhen Wei 2 , Lanjie Huang 2 , Yuehong Gan 2
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Twelve novel longifolene-derived primary amine carboxylates were synthesized and evaluated for herbicidal activity. The structures of title compounds were confirmed by Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance (NMR), 13C NMR, and high-resolution mass spectrometry. The results showed that all the synthesized compounds exhibited higher herbicidal activity than the corresponding carboxylic acids involved in the reaction and the commercial herbicide glyphosate; some of them even possessed inhibition rates of 100% against Lolium multiflorum Lam. and Brassica campestris at low concentrations (0.039–0.313 mmol/L). Moreover, structural factors, including types of carboxylates and carbon chain length, had a great influence on the herbicidal performance. The herbicidal activity of dicarboxylates was similar to or much higher than that of corresponding monocarboxylates and glyphosate. Furthermore, compound 5l was found to be the most active candidate against the root and shoot growth of L. multiflorum Lam. and B. campestris with half maximal inhibitory concentrations (IC50) of around 0.010 and 0.023 mmol/L. The present work indicated that those prepared compounds have great potential to serve as high-performance botanical herbicides used at low doses.
中文翻译：
用于可持续杂草管理的长叶烯衍生伯胺羧酸盐：合成和除草活性
合成了十二种新型长叶烯衍生的伯胺羧酸盐并评估了除草活性。标题化合物的结构通过傅里叶变换红外光谱、 1H核磁共振(NMR)、 13CNMR和高分辨率质谱确认。结果表明，所有合成的化合物均表现出比参与反应的相应羧酸和商业除草剂草甘膦更高的除草活性；其中一些对黑麦草的抑制率甚至达到100%。和低浓度的甘蓝(0.039–0.313 mmol/L)。此外，结构因素，包括羧酸盐的类型和碳链长度，对除草性能有很大影响。二羧酸盐的除草活性与相应的单羧酸盐和草甘膦相似或远高于相应的单羧酸盐和草甘膦。此外，发现化合物5l是对抗何首乌根和芽生长最有效的候选化合物。 B. Campestris的半数最大抑制浓度 (IC 50 ) 约为 0.010 和 0.023 mmol/L。目前的工作表明，所制备的化合物具有作为低剂量使用的高性能植物除草剂的巨大潜力。
更新日期：2024-07-25
中文翻译：
用于可持续杂草管理的长叶烯衍生伯胺羧酸盐：合成和除草活性
合成了十二种新型长叶烯衍生的伯胺羧酸盐并评估了除草活性。标题化合物的结构通过傅里叶变换红外光谱、 1H核磁共振(NMR)、 13CNMR和高分辨率质谱确认。结果表明，所有合成的化合物均表现出比参与反应的相应羧酸和商业除草剂草甘膦更高的除草活性；其中一些对黑麦草的抑制率甚至达到100%。和低浓度的甘蓝(0.039–0.313 mmol/L)。此外，结构因素，包括羧酸盐的类型和碳链长度，对除草性能有很大影响。二羧酸盐的除草活性与相应的单羧酸盐和草甘膦相似或远高于相应的单羧酸盐和草甘膦。此外，发现化合物5l是对抗何首乌根和芽生长最有效的候选化合物。 B. Campestris的半数最大抑制浓度 (IC 50 ) 约为 0.010 和 0.023 mmol/L。目前的工作表明，所制备的化合物具有作为低剂量使用的高性能植物除草剂的巨大潜力。
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