Discovery of novel herbicidal cyclic keto‐enol derivatives containing a pyridazinone moiety and their structure–activity relationship studies on weeds,Pest Management Science

当前位置： X-MOL 学术 › Pest Manag. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Discovery of novel herbicidal cyclic keto‐enol derivatives containing a pyridazinone moiety and their structure–activity relationship studies on weeds
Pest Management Science ( IF 3.8 ) Pub Date : 2025-05-27 , DOI: 10.1002/ps.8925
Yoshinobu Jin ₁ , Toshiyuki Kiji ₁ , Seiji Yamato ₁

Affiliation

BACKGROUNDAcetyl‐coenzyme A carboxylase (ACCase) is one of the most important enzymes involved in the biosynthesis of fatty acids in both plants and animals, and its inhibitors are widely used to control gramineous plants or sucking pests in crop fields. Phenyl‐substituted cyclic keto‐enols (CKEs) are known as a chemical class inhibiting ACCase, and several compounds are commercially available as herbicides or insecticides.RESULTSWe synthesized a new series of phenyl‐substituted CKEs containing a pyridazinone moiety and examined the structure–activity relationship (SAR) based on herbicidal activity. We found that the methyl group at the 2 position of the pyridazinone ring significantly contributes to herbicidal efficacy. Similarly, we revealed that a methyl group at the 6 position of the pyridazinone ring is critical for exerting high herbicidal activity on both grass weeds and broadleaf weeds. Additionally, compounds with ethyl groups at the ortho position of the phenyl ring showed improved herbicidal activity, especially against grass weeds. The ACCase inhibition assay results showed good correlations with the SAR of the pot tests. Several optimized compounds, based on herbicidal activity, demonstrated high herbicidal efficacy against not only grass weeds but also broadleaf weeds, causing characteristic bleaching symptoms.CONCLUSIONPhenyl‐substituted CKE derivatives containing a pyridazinone moiety have a broad weed control spectrum and likely possess multiple modes of action. These features make these compounds useful as tools for effectively controlling a variety of weeds, including resistant weeds. © 2025 Society of Chemical Industry.

中文翻译：

含有吡哒嗪酮部分的新型除草剂环状酮烯醇衍生物的发现及其对杂草的构效关系研究

背景乙酰辅酶 A 羧化酶（ACCase）是植物和动物体内参与脂肪酸生物合成的最重要酶之一，其抑制剂广泛用于防治禾本科植物或农田吸食害虫。苯取代的环酮烯醇（CKE）被称为抑制 ACCase 的化学类别，有几种化合物可作为除草剂或杀虫剂在市场上买到。结果我们合成了一系列新的苯基取代的 CKEs，其中包含哒嗪酮部分，并检查了基于除草活性的结构-活性关系（SAR）。我们发现吡哒嗪酮环 2 位的甲基对除草效果有显着贡献。同样，我们揭示了吡哒嗪酮环 6 位的甲基对于对禾本科杂草和阔叶杂草发挥高除草活性至关重要。此外，在苯环邻位具有乙基的化合物显示出更好的除草活性，尤其是对禾本科杂草。ACCase 抑制试验结果显示与 pot 试验的 SAR 具有良好的相关性。几种基于除草活性的优化化合物不仅对禾本科生杂草而且对阔叶杂草表现出很高的除草功效，从而导致典型的白化症状。结论含有哆嗪酮部分的苯基取代的 CKE 衍生物具有广泛的杂草控制谱，并且可能具有多种作用模式。这些特性使这些化合物可用作有效控制各种杂草（包括抗性杂草）的工具。© 2025 化工学会.

更新日期：2025-05-27

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南