Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing, China.
College of Agronomy and Biotechnology, China Agricultural University, Beijing, China.
Pest Manag Sci. 2021 May;77(5):2252-2263. doi: 10.1002/ps.6250. Epub 2021 Jan 21.
Picolinate/picolinic acid compounds are an important class of synthetic auxin herbicides. To explore the herbicidal activity of 6-pyrazolyl picolinate compounds, a series of 3-chloro-6-pyrazolyl-picolinate derivatives was designed and synthesized.
Twenty-five 3-chloro-6-pyrazolyl-picolinate derivatives synthesized were tested for herbicidal activity and the IC value of compound c5 to the growth of Arabidopsis thaliana root was 27 times lower than that of the commercial herbicide clopyralid. Compound c5 displayed better post-emergence herbicidal activity and broader (Picloram, Clopyralid, Aminopyralid) herbicidal spectrum at a dosage of 400 g ha in comparison with clopyralid; it also was safe to wheat and maize at this dosage. Arabidopsis thaliana phenotypes and expression of auxin-response genes demonstrated that compound c5 might be a novel auxin-type herbicide. Molecular docking analyses revealed that compound c5 had stronger binding ability to receptor AFB5 (auxin signaling F-box protein 5) than clopyralid.
These 6-pyrazolyl picolinate compounds could be used as potential lead structures for the discovery of a novel synthetic auxin herbicide. © 2021 Society of Chemical Industry.
吡啶酸/烟酸化合物是一类重要的合成生长素除草剂。为了探索 6-吡唑基吡啶酸化合物的除草活性，设计并合成了一系列 3-氯-6-吡唑基吡啶酸衍生物。
测试了 25 种 3-氯-6-吡唑基吡啶酸衍生物的除草活性，化合物 c5 对拟南芥根生长的 IC 值比商业除草剂氯吡嘧磺隆低 27 倍。与氯吡嘧磺隆相比，化合物 c5 在 400 g/ha 的剂量下具有更好的苗后除草活性和更宽的（Picloram、Clopyralid、Aminopyralid）除草谱；在该剂量下对小麦和玉米也安全。拟南芥表型和生长素反应基因的表达表明，化合物 c5 可能是一种新型的生长素型除草剂。分子对接分析表明，化合物 c5 与受体 AFB5（生长素信号 F-box 蛋白 5）的结合能力强于氯吡嘧磺隆。
这些 6-吡唑基吡啶酸化合物可作为发现新型合成生长素除草剂的潜在先导结构。 © 2021 英国化学学会。
