A study of fungicidal and anti-phenol oxidase activity of some \u03b1-amino phosphonate derivatives

Mohsen Abbod,Ali Asghar Ebrahimi Valmoozi,Naser Safaie,Khodayar Gholivand,Mahyar Bonsaii,Mohammad Mehrabadi

doi:10.1186/s40538-021-00246-3

Abstract

BackgroundDeveloping new pesticides with multi-function may be a suitable strategy to save time and cost and reduce the emergence of resistant strains of pests and pathogens. The organophosphorus derivatives have not been widely used in agriculture as fungicides. In this work, a series of six α-amino phosphonate derivatives were prepared and tested for their fungicidal and anti-phenol oxidase activities.ResultsThe prepared compounds revealed a promising anti-fungal activity against Macrophomina phaseolina and Pythium aphanidermatum, especially M4, with MIC of 62 mg/L for M. phaseolina. M4 did not affect the fungus permeability rate of the cell membrane; however, it displayed a significant efficiency on mycelial soluble protein content. M4 and M3 with a hydroxyl group on the aniline moiety exhibited an observed anti-phenol oxidase activity. M4 inhibited the enzyme at 1 mg/mL. The DFT theoretical study revealed a significant correlation between the substituents of aniline moiety and the bioactivity of the studied compounds. The negative charge conspicuously influenced the anti-phenol oxidase activity.ConclusionsOur findings suggest the studied compounds as bases to design more effective α-amino phosphonate fungicides with additional anti-phenol oxidase activity.Graphic abstract

Highlights

Developing new pesticides with multi-function may be a suitable strategy to save time and cost and reduce the emergence of resistant strains of pests and pathogens
Anti‐fungal activity The synthesized compounds were evaluated for their fungicidal activity against two important plant pathogens, including Macrophomina phaseolina from the true fungi and Pythium aphanidermatum from the Oomycetes
M4 inhibited the growth of P. aphanidermatum at any of the tested concentrations; we have tested these compounds at lower doses (Table 1)

Summary

Introduction

Developing new pesticides with multi-function may be a suitable strategy to save time and cost and reduce the emergence of resistant strains of pests and pathogens. The organophosphorus derivatives have not been widely used in agriculture as fungicides. A series of six α-amino phosphonate derivatives were prepared and tested for their fungicidal and anti-phenol oxidase activities. Most organophosphorus derivatives have been limited to use in agriculture as insecticides, and nowadays, increasing attention is paid to develop new organophosphorus derivatives as fungicides [4]. Kitazin, and Pyrazophos are examples of the few organophosphorus compounds which are used as fungicides [4]. Phenol oxidase (PO) interferes with several biological pathways in insects like melanization and sclerotization cascades [5,6,7,8,9]; it is considered a critical defense tool against pathogens attack [6]. Inhibition of PO may serve as a good strategy for insects control by making their immune system feeble against pathogens [10]

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