Bis(4-fluorophenylmethylsulfanyldiketones): synthesis, structure and fungicidal properties

A series of bis(4-fluorophenylmethylsulfanyldiketones) were synthesized by multicomponent thiomethylation reaction between 2,4-pentanedione, α,ω-alkanedithiols, and 4-fluorobenzaldehyde in the presence of an organocatalyst. It was found that the developed α-monosubstituted β-diketones mainly exist in the keto form. Considering the green chemistry metrics, the prospects for industrial implementation of the synthesis of target molecules were evaluated. Among the prepared bis-sulfanyl diketones, the highest fungicidal activity against the plant pathogenic fungi Bipolaris sorokiniana, Fusarium oxysporum, and Rhizoctonia solani was found for the compound containing a 4,4′-thiodibenzene spacer between the sulfur atoms in the bis(4-fluorophenylmethylsulfanyldiketone) molecule.