Li Huiting, Wei Wei, Shi Rongchuan, Gou Yunhan, Li Xiaofei, Li Chengyang, Li Yiqun, Cao Yiming, Liu Shangzhong
Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China.
Key Laboratory of National Forestry and Grassland Administration on Pest Chemical Control, China Agricultural University, Beijing 100193, China.
Molecules. 2025 Feb 23;30(5):1022. doi: 10.3390/molecules30051022.
6-Aryl-2-picolinic acid herbicides are an important subclass of auxin herbicides, characterized by their good absorption and conductivity, broad weed control spectrum, and excellent herbicidal activity against some resistant weeds. Based on previous studies from our group and the distinct characteristics of physico-chemical properties and biological activities of active skeleton structure containing fluorine atoms, this paper introduces the design and synthesis of 41 novel 4-amino-6-(5-aryl-substituted-1-pyrazolyl)-3-chloro-5-fluoro-2-picolinic acid compounds. The test of inhibiting roots growth showed that most of the -series compounds exhibited superior inhibitory effects compared to picloram, with six compounds demonstrated even better inhibitory capability than the new herbicidal molecule florpyrauxifen. For example, compound , at a concentration of 0.5 µmol/L, exhibited a 78.4% inhibition of root growth, whereas florpyrauxifen showed only a 33.8% inhibition. Root growth inhibition tests on weeds showed that 28 compounds, at a concentration of 250 µM, demonstrated a greater than 80% inhibition of (BN) root growth. Post-emergence herbicidal activity tests showed that most compounds exhibited good inhibitory effects on broadleaf weeds, with 10 compounds achieving a 100% inhibition of the growth of (AL). These results demonstrate that some of the 4-amino-6-(5-aryl-substituted-1-pyrazolyl)-3-chloro-5-fluoro-2-picolinic acid compounds could be used as potential lead structures in the discovery of novel synthetic auxin herbicides.
6-芳基-2-吡啶甲酸类除草剂是生长素类除草剂的一个重要亚类，其特点是吸收性和传导性良好、杂草防治谱广，且对一些抗性杂草具有优异的除草活性。基于本课题组之前的研究以及含氟原子活性骨架结构独特的理化性质和生物活性特点，本文介绍了41种新型4-氨基-6-(5-芳基取代-1-吡唑基)-3-氯-5-氟-2-吡啶甲酸化合物的设计与合成。抑制根系生长试验表明，与毒莠定相比，该系列大多数化合物表现出更优异的抑制效果，其中有6种化合物的抑制能力甚至优于新型除草分子双唑草腈。例如，化合物在浓度为0.5 μmol/L时，对根系生长的抑制率为78.4%，而双唑草腈仅为33.8%。对杂草的根系生长抑制试验表明，28种化合物在浓度为250 μM时，对（BN）根系生长的抑制率大于80%。苗后除草活性试验表明，大多数化合物对阔叶杂草表现出良好的抑制效果，其中有10种化合物对（AL）生长的抑制率达到100%。这些结果表明，部分4-氨基-6-(5-芳基取代-1-吡唑基)-3-氯-5-氟-2-吡啶甲酸化合物可作为发现新型合成生长素类除草剂的潜在先导结构。
