Martinho Luan A, de Lima Daniel M, Praciano Victor H J G, Oliveira Sarah Christina C, Kleber Z Andrade Carlos
Instituto de Química, Laboratório de Química Metodológica e Orgânica Sintética (LaQMOS), Universidade de Brasília, 70904-970 Brasília, DF, Brazil.
Instituto de Ciências Biológicas, Departamento de Botânica, Laboratório de Alelopatia Alfredo Gui Ferreira, Universidade de Brasília, 70910-900 Brasília, DF, Brazil.
J Agric Food Chem. 2025 Jan 8;73(1):298-317. doi: 10.1021/acs.jafc.4c09477. Epub 2024 Dec 28.
In this work, several imidazo[1,2-]pyridines were synthesized through the Groebke-Blackburn-Bienaymé three-component reaction (GBB-3CR), and their phytotoxicity was evaluated by the influence on the growth of wheat coleoptiles and three important agricultural seeds (, , and ) at test concentrations of 1000, 300, 100, 30, and 10 μM. A structure-activity relationship was established, showing the importance of halogen groups at the position of the attached aromatic ring and the presence of a cyclohexylamine group for greater activity. Post-modification of some GBB-3CR adducts was carried out, leading to imidazo[1,2-]pyridine-tetrazole hybrids, which were also evaluated in these bioassays. The phytotoxicity on seed germination and growth bioassays demonstrated that was the most susceptible seed, and the most affected parameters were the root and shoot lengths. The most active compound was also evaluated against , , and weeds under hydroponic conditions to assess its phytotoxic potential at a more advanced level of bioassays. Promising results were also achieved, in which the most affected growth factor by inhibition was the root growth, and a stimulus to shoot growth was noted, making it a promising hit in the search for new herbicides.
在本研究中，通过格罗布克-布莱克本-比内梅三组分反应（GBB-3CR）合成了几种咪唑并[1,2 -]吡啶，并在1000、300、100、30和10 μM的测试浓度下，通过对小麦胚芽鞘以及三种重要农作物种子（，，和）生长的影响来评估它们的植物毒性。建立了构效关系，表明连接芳环位置上的卤素基团以及环己胺基团的存在对于提高活性的重要性。对一些GBB-3CR加合物进行了后修饰，得到了咪唑并[1,2 -]吡啶-四唑杂化物，这些杂化物也在这些生物测定中进行了评估。种子萌发和生长生物测定中的植物毒性表明，是最敏感的种子，受影响最大的参数是根长和芽长。还在水培条件下对活性最高的化合物针对，，和杂草进行了评估，以在更高水平的生物测定中评估其植物毒性潜力。也取得了有前景的结果，其中受抑制影响最大的生长因子是根生长，并且注意到对芽生长有刺激作用，这使其成为寻找新型除草剂的一个有前景的候选物。
