engleski

The fungicidal effect of nicotinamide-based compounds

The nicotinamide derivates represent the promising candidate in the field of pesticides due to significant fungicidal activity, insecticidal activity, herbicidal activity, plant growth regulator activity and bactericidal activity. The series of nicotinamide-bromides with various alkyl chain lengths (from ethyl to octadecyl) were synthesized, and the toxicity of aqueous solutions towards Fusarium graminearum, Sclerotinia sclerotiorum, and Botrytis cinerea was examined. The obtained data were compared with DFT calculations results to understand the structural origin of fungicidal behavior and correlate it with the structural properties of investigated molecules. A significant correlation was established between the lipophilicity of the molecules (obtained from DFT calculations) and the growth rate of the examined phytopathogenic fungi. The results had suggested that Sclerotinia sclerotiorum is most sensitive to nicotinamide compounds exposure, while F. graminearum is most resistant to the change of lipophilicity of compounds. For all investigated compounds, the growth rate was decreased with the increase of carbon atoms in the side-chain until [C14Nic] [Br]. Further prolongation increased the growth rate of fungus, as it was noted for [C16Nic] [Br] and [C18Nic][Br]. This behavior was explained by the distinguished hydrophobic and hydrophilic surfaces in [C14Nic][Br] due to interactions between keto oxygen and bromide anion absent in the case of nicotinamides with a longer chain.

nicotinamide ; DFT calculations ; Fusarium graminearum ; Sclerotinia sclerotiorum ; Botrytis cinerea

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