Tetraphenylphosphonium allyldithiocarbimates derived from Morita-Baylis-Hillman adducts: Synthesis, characterization, crystal structure and antifungal activity

• Twelve tetraphenylphosphonium allyldithiocarbimates derived from Morita-Baylis-Hillman adducts were prepared.
• The highly stereoselective reactions yielded Z-isomers, as confirmed by X-ray diffraction.
• The allyldithiocarbimates were active against Botrytis cinerea.
• The most active compound presented IC50 of 38 μM.

Botrytis blight is a very destructive disease caused by Botrytis spp., infecting flowers, trees, vegetables and fruits. Twelve new compounds were prepared by the reaction of potassium N-aryl-sulfonyldithiocarbimates with Morita-Baylis-Hillman derivatives bearing phenyl and furyl groups. These are the first examples of allyldithiocarbimate anions and were isolated as tetraphenylphosphonium salts. The new compounds were characterized by HRMS, NMR and Infrared spectroscopy. Further, the structures of three allyldithiocarbimates were determined by single crystal X-ray diffraction. The compounds are isostructural and crystallize in the space group P21/c of the monoclinic system, and the allyldithiocarbimate anions present Z configuration. All the compounds were active against Botrytis cinerea. The best results were achieved with the tetraphenylphosphonium (Z)-3-(furan-2-yl)-2-(methoxycarbonyl)allyl-(4-chlorophenylsulfonyl)dithiocarbimate (IC50 38 μM).

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