Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents,Journal of Agricultural and Food Chemistry

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Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-03 , DOI: 10.1021/acs.jafc.4c04811
Simon Backx ₁ , Jelle Van Vooren _{1,

2} , Jasper Geerts _{1,

2} , Cédric Hyde _{1,

2} , Owen Van Hecke _{1,

2} , Hanne Pappaert _{1,

2} , Kevin Dewitte ₃ , Maarten Ameye _{2,

4} , Kris Audenaert ₂ , Willem Desmedt _{2,

5} , Sven Mangelinckx ₁

Affiliation

The growing problem of herbicide resistance necessitates the development of novel herbicidal active ingredients, together with other integrated weed management approaches. Natural products are a major source of inspiration for novel actives. In previous research, we identified a 3-acyltetramic acid of microbial origin that inhibited algal growth in marine biofilms, at least in part through inhibition of photosystem II. In this work, we demonstrate the herbicidal effect of this lead compound and construct multiple libraries to test the impact of the different substituents of the central scaffold in order to study the structure–activity relationships. Among these analogues, the highest activities were found for medium- to long-chain acyl groups and apolar secondary amino acid residues. Finally, we provide first insights into the herbicidal mechanisms and present preliminary field-trial and ecotoxicological results for TA12-Pro, the most active analogue in our library. Together, this research shows the potential of 3-acyltetramic acids for herbicide development.

中文翻译：

氨基酸衍生的3-酰基特四酸作为除草剂的研究

日益严重的除草剂抗性问题需要开发新型除草活性成分以及其他综合杂草治理方法。天然产品是新型活性物质的主要灵感来源。在之前的研究中，我们发现了一种微生物来源的 3-酰基四胺酸，它至少部分通过抑制光系统 II 来抑制海洋生物膜中的藻类生长。在这项工作中，我们展示了该先导化合物的除草作用，并构建了多个文库来测试中心支架不同取代基的影响，以研究构效关系。在这些类似物中，发现中链至长链酰基和非极性仲氨基酸残基的活性最高。最后，我们提供了对除草机制的初步见解，并展示了 TA12-Pro（我们库中最活跃的类似物）的初步田间试验和生态毒理学结果。总之，这项研究显示了 3-酰基四胺酸用于除草剂开发的潜力。

更新日期：2024-09-03

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