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Peer-reviewedCC BY 4.0Chemistry & Biodiversity

Design, Synthesis, and Antifungal Structure‐Activity Relationship of Hydrazide Derivatives Containing a Cyclopropyl Group Against Phytopathogenic Fungi

  • Shanshan Yang1
  • Xinyuan Wang1
  • Bixi Yin2
  • Weiting Yan1
  • Lei Wang1
  • Yunying Sha1
  • Lizhong Wang1
  • Zhuyun Liu1
  1. 1College of Intelligent Pharmaceutical and Chemical New Materials Taizhou Polytechnic College Taizhou P. R. China
  2. 2Yangtze River Pharmaceutical Group Taizhou P. R. China
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Abstract

To discover novel antifungal agents with unique scaffolds for crop protection, a series of 23 hydrazide derivatives containing a cyclopropyl group, including 14 new chemical entities, were designed, synthesized, and evaluated for their antifungal activity against eight phytopathogenic fungi. The in vitro bioassay results at 50 µg/mL revealed that most target compounds exhibited moderate to excellent antifungal activities. Notably, three compounds (4, 6, 7) displayed the most potent broad‐spectrum activity with inhibition rates of 95.0%–100.0% against all eight tested fungi. Their EC50 values were below 10 µg/mL against most fungi. SEM analysis revealed that the parent compound 1 caused pronounced morphological alterations in A. alternata mycelia, including shrinkage, collapse, and irregular distortion, providing a preliminary indication of the cellular effect of the series. Molecular docking of compound 1 with succinate dehydrogenase (SDH) generated a plausible binding model, suggesting SDH as a potential target candidate for this series, pending direct enzymatic validation. SAR analysis demonstrated that the phenyl ring was consistently associated with high activity, and para‐substitution with halogen atoms is favorable for enhancing antifungal activity. These findings suggest that cyclopropyl‐containing hydrazide derivatives, particularly compounds 4, 6, and 7, represent promising lead candidates for the development of novel antifungal agents.

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Cite

BibTeXRIS
BibTeX
@article{yang2026design,
  title = {{Design, Synthesis, and Antifungal Structure‐Activity Relationship of Hydrazide Derivatives Containing a Cyclopropyl Group Against Phytopathogenic Fungi}},
  author = {Shanshan Yang and Xinyuan Wang and Bixi Yin and Weiting Yan and Lei Wang and Yunying Sha and Lizhong Wang and Zhuyun Liu},
  journal = {Chemistry \& Biodiversity},
  year = {2026},
  month = oct,
  doi = {10.1002/cbdv.71820},
  url = {https://doi.org/10.1002/cbdv.71820},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Design, Synthesis, and Antifungal Structure‐Activity Relationship of Hydrazide Derivatives Containing a Cyclopropyl Group Against Phytopathogenic Fungi
AU  - Shanshan Yang
AU  - Xinyuan Wang
AU  - Bixi Yin
AU  - Weiting Yan
AU  - Lei Wang
AU  - Yunying Sha
AU  - Lizhong Wang
AU  - Zhuyun Liu
PY  - 2026
DA  - 2026/10/01
JO  - Chemistry & Biodiversity
DO  - 10.1002/cbdv.71820
UR  - https://doi.org/10.1002/cbdv.71820
AB  - To discover novel antifungal agents with unique scaffolds for crop protection, a series of 23 hydrazide derivatives containing a cyclopropyl group, including 14 new chemical entities, were designed, synthesized, and evaluated for their antifungal activity against eight phytopathogenic fungi. The in vitro bioassay results at 50 µg/mL revealed that most target compounds exhibited moderate to excellent antifungal activities. Notably, three compounds (4, 6, 7) displayed the most potent broad‐spectrum activity with inhibition rates of 95.0%–100.0% against all eight tested fungi. Their EC50 values were below 10 µg/mL against most fungi. SEM analysis revealed that the parent compound 1 caused pronounced morphological alterations in A. alternata mycelia, including shrinkage, collapse, and irregular distortion, providing a preliminary indication of the cellular effect of the series. Molecular docking of compound 1 with succinate dehydrogenase (SDH) generated a plausible binding model, suggesting SDH as a potential target candidate for this series, pending direct enzymatic validation. SAR analysis demonstrated that the phenyl ring was consistently associated with high activity, and para‐substitution with halogen atoms is favorable for enhancing antifungal activity. These findings suggest that cyclopropyl‐containing hydrazide derivatives, particularly compounds 4, 6, and 7, represent promising lead candidates for the development of novel antifungal agents.
SN  - 1612-1872
SN  - 1612-1880
ER  -