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Synthesis and crystal structure of phosphonic acid and bisphosphoramidate derivatives: QSAR studies of their anti-fungal potential on Macrophomina Phaseolina (Tassi) Goid

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Abstract

A series of phosphonic acid and bisphosphoramidate derivatives were synthesized and characterized. The bioactivities against the fungal pathogen Macrophomina phaseolina and human acetylcholinesterase AChE enzyme were studied using QSAR based on multiple linear regression. L17, with (p-Cl–C6H4–NH) (p-Cl–C6H4)C(H)P(O)(OC2H5)2 skeleton, demonstrated a great mortality on the M. phaseolina mycelial growth by 83% inhibition at 150 mg/L; the other tested derivative showed moderate to weak antifungal activity against the fungus. QSAR model based on the GA-MLR method revealed the importance of 3D descriptors (De, Mor18e, H8m, and Mor30p) on the antifungal activity. It showed good capability in predicting the fungicidal activity of the studied molecules. Another derivative, L5, with (m-CH3–NC5H4–NH)(m-CH3–C6H4)C(H)P(O)(OCH3)2 skeleton displays the most potent anti-AChE activity. The electronic parameters, ΔEL-H, and ELUMO, have the highest contribution of human AChE. The authors suggest that these models could be usefully employed in designing more effective crop protection compounds without side effects on non-target organisms.

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Acknowledgements

Financial support of this work by Iran National Science Foundation: INSF and Tarbiat Modares University is gratefully acknowledged.

Funding

This work was supported by Tarbiat Modares University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Basic Sciences, Tarbiat Modares University, P.O.Box: 14115-175, Tehran, Iran

    Khodayar Gholivand, Omolbanin Barzegar, Hadis Nasrollah Tabar, Rouhollah Yaghoubi, Mahdieh Hosseini, Maryam Rahimzadeh Dashtaki & Ahmad Mani-Varnosfaderani

  2. Department of Plant Pathology, Faculty of Agriculture, Tarbiat Modares University, Tehran, Iran

    Mohsen Abbod & Naser Safaie

  3. Department of Advanced Materials, Technical Engineering Faculty, Imam Hossein University, Tehran, Iran

    Ali Asghar Ebrahimi Valmoozi

  4. Institute of Physics of the ASCR, v.v.i., Na Slovance 2, 182 21, Praha 8, Czech Republic

    Michal Dusek

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  1. Khodayar Gholivand
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  2. Mohsen Abbod
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  3. Ali Asghar Ebrahimi Valmoozi
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Contributions

Gholivand, Valmoozi, Hosseini, Barzegar, Nasrollah Tabar, and Yaghoubi participated in the synthesis of the compounds and crystal structure analysis, Abbod provided the antifungal assay and the GA-MLR QSAR study of the fungicidal activity and wrote the related sections. Valmoozi were the major contributors in writing the manuscript, Safaie participated in the antifungal assay, Valmoozi provided the anti-AChE assay and related QSAR study. All authors read and approved the final manuscript.

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Correspondence to Khodayar Gholivand.

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Gholivand, K., Abbod, M., Ebrahimi Valmoozi, A.A. et al. Synthesis and crystal structure of phosphonic acid and bisphosphoramidate derivatives: QSAR studies of their anti-fungal potential on Macrophomina Phaseolina (Tassi) Goid. J IRAN CHEM SOC 18, 1591–1606 (2021). https://doi.org/10.1007/s13738-020-02133-4

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