Synthesis of cube-2,4-D, cube-3,4-D and cube-4-D, and their herbicidal assessment against Cryptostegia grandiflora (rubber vine)

Dichlorophenoxyacetic acid (2,4-D) is a widely used broad-spectrum herbicide that is effective against several Australian Weeds of National Significance (WoNS). As part of efforts to apply the bioisostere concept to reinvigorate established agrichemical templates, the benzene ring in 2,4-D was replaced with cubane to generate cube-2,4-D and related derivatives, cube-3,4-D and cube-4-D. These cubane derivatives were screened for post-emergence activity against Cryptostegia grandiflora (rubber vine), a WoNS species. Although none of the cubane derivatives outperformed 2,4-D, cube-3,4-D significantly reduced plant height growth in vitro relative to the control, suggesting greater biological activity than cube-2,4-D. In silico docking showed that cube-3,4-D closely matched the docking pose of 2,4-D within the active site, providing a possible rationale for its observed biological activity.

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Publication Details

Journal
Australian Journal of Chemistry
Published
2025-11-26
DOI
https://doi.org/10.1071/ch25127
Citations
1
Primary Topic
Weed Control and Herbicide Applications
Type
article
Field-Weighted Citation Impact
1.75
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article

Synthesis of cube-2,4-D, cube-3,4-D and cube-4-D, and their herbicidal assessment against Cryptostegia grandiflora (rubber vine)

Gimme H. Walter, Thierry Lonhienne, Isobella S. J. Stone, Hui Xing et al.
1 citations
Australian Journal of Chemistry
Weed Control and Herbicide Applications
1.75
article

Synthesis of cube-2,4-D, cube-3,4-D and cube-4-D, and their herbicidal assessment against Cryptostegia grandiflora (rubber vine)

Gimme H. Walter, Thierry Lonhienne, Isobella S. J. Stone, Hui Xing, Chuyi Su, Cody-Ellen Murray, Xin Lin, Craig M. Williams, G. Paul Savage, Paul V. Bernhardt, Sevan D. Houston, Michelle A. Rafter, Bruna Durante Batista, Sarah K. M. McGregor, Cassidy Whitefield, Luke W. Guddat, Rebecca M. Hurst
article en
1 citations

Abstract

Dichlorophenoxyacetic acid (2,4-D) is a widely used broad-spectrum herbicide that is effective against several Australian Weeds of National Significance (WoNS). As part of efforts to apply the bioisostere concept to reinvigorate established agrichemical templates, the benzene ring in 2,4-D was replaced with cubane to generate cube-2,4-D and related derivatives, cube-3,4-D and cube-4-D. These cubane derivatives were screened for post-emergence activity against Cryptostegia grandiflora (rubber vine), a WoNS species. Although none of the cubane derivatives outperformed 2,4-D, cube-3,4-D significantly reduced plant height growth in vitro relative to the control, suggesting greater biological activity than cube-2,4-D. In silico docking showed that cube-3,4-D closely matched the docking pose of 2,4-D within the active site, providing a possible rationale for its observed biological activity.

Australian Journal of ChemistryVol. 78(12)
The University of Queensland (AU), Queensland Department of Environment and Science (AU), CSIRO Health and Biosecurity (AU), CSIRO Manufacturing (AU)
Openalex Percentile: Top 11%
Weed Control and Herbicide Applications
1.75
DOISourceOpenAlex
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