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Study of amino acid-derived 3-acyltetramic acids as herbicidal agents

Simon Backx (UGent) , Jelle Van Vooren (UGent) , Jasper Geerts, Cédric Hyde, Owen Van Hecke (UGent) , Hanne Pappaert (UGent) , Kevin Dewitte (UGent) , Maarten Ameye (UGent) , Kris Audenaert (UGent) , Willem Desmedt (UGent) , et al.
(2024) JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 72(36). p.19644-19656
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Abstract
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.
Keywords
herbicides, agrochemistry, tetramic acids, chemical synthesis

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Citation

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MLA
Backx, Simon, et al. “Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 72, no. 36, 2024, pp. 19644–56, doi:10.1021/acs.jafc.4c04811.
APA
Backx, S., Van Vooren, J., Geerts, J., Hyde, C., Van Hecke, O., Pappaert, H., … Mangelinckx, S. (2024). Study of amino acid-derived 3-acyltetramic acids as herbicidal agents. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 72(36), 19644–19656. https://doi.org/10.1021/acs.jafc.4c04811
Chicago author-date
Backx, Simon, Jelle Van Vooren, Jasper Geerts, Cédric Hyde, Owen Van Hecke, Hanne Pappaert, Kevin Dewitte, et al. 2024. “Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 72 (36): 19644–56. https://doi.org/10.1021/acs.jafc.4c04811.
Chicago author-date (all authors)
Backx, Simon, Jelle Van Vooren, Jasper Geerts, Cédric Hyde, Owen Van Hecke, Hanne Pappaert, Kevin Dewitte, Maarten Ameye, Kris Audenaert, Willem Desmedt, and Sven Mangelinckx. 2024. “Study of Amino Acid-Derived 3-Acyltetramic Acids as Herbicidal Agents.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 72 (36): 19644–19656. doi:10.1021/acs.jafc.4c04811.
Vancouver
1.
Backx S, Van Vooren J, Geerts J, Hyde C, Van Hecke O, Pappaert H, et al. Study of amino acid-derived 3-acyltetramic acids as herbicidal agents. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 2024;72(36):19644–56.
IEEE
[1]
S. Backx et al., “Study of amino acid-derived 3-acyltetramic acids as herbicidal agents,” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 72, no. 36, pp. 19644–19656, 2024.
@article{01J6Y33JEC8VQA4706E3PCGZTR,
  abstract     = {{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.}},
  author       = {{Backx, Simon and Van Vooren, Jelle and Geerts, Jasper and Hyde, Cédric and Van Hecke, Owen and Pappaert, Hanne and Dewitte, Kevin and Ameye, Maarten and Audenaert, Kris and Desmedt, Willem and Mangelinckx, Sven}},
  issn         = {{0021-8561}},
  journal      = {{JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY}},
  keywords     = {{herbicides,agrochemistry,tetramic acids,chemical synthesis}},
  language     = {{eng}},
  number       = {{36}},
  pages        = {{19644--19656}},
  title        = {{Study of amino acid-derived 3-acyltetramic acids as herbicidal agents}},
  url          = {{http://doi.org/10.1021/acs.jafc.4c04811}},
  volume       = {{72}},
  year         = {{2024}},
}
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