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

Published Date
15 February 2016, Vol.1106:130–140, doi:10.1016/j.molstruc.2015.10.097

Author 

Eder C. Tavares ^a,,1,

Mayura M.M. Rubinger ^a

Eclair V. Filho ^a

Marcelo R.L. Oliveira ^a

Dorila Piló-Veloso ^b

Javier Ellena ^c

Silvana Guilardi ^d

Rafael A.C. Souza ^d

Laércio Zambolim ^e

• aDepartamento de Química, Universidade Federal de Viçosa, 36570-900 Viçosa, MG, Brazil
• bDepartamento de Química – ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil
• cInstituto de Física de São Carlos, Universidade de São Paulo, 13560-970 São Carlos, SP, Brazil
• dInstituto de Química, Universidade Federal de Uberlândia, 38408-100 Uberlândia, MG, Brazil
• eDepartamento de Fitopatologia – CCA, Universidade Federal de Viçosa, 36570-900 Viçosa, MG, Brazil

Received 13 July 2015. Revised 27 October 2015. Accepted 28 October 2015. Available online 2 November 2015. 

Highlights

• 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.

Abstract

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).

Graphical abstract

Keywords

• Dithiocarbimates
• Morita-Baylis-Hillman adducts
• Antifungal activity
• Botrytis cinerea
• Crystal structure of allyldithiocarbimates

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• ∗ 
  Corresponding author.
  
  

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