Two series of allyl sulfonamides, prepared from Morita-Baylis-Hillman adducts and primary aromatic sulfonamides, were fully characterized. The Z configuration for the products derived from 2-[hydroxy(phenyl)methyl]acrylonitrile (1) and E configuration for those derived from methyl 2-[hydroxy(phenyl)methyl]acrylate (2) were confirmed by X-ray diffraction for one compound of each series (1e, 2f). Density functional theory calculations for all allyl sulfonamides agreed with the X-ray crystallographic data. X-ray diffraction studies indicate that these compounds form dimers in their crystal structures. Fingerprint plots show that compound 1e is stabilized by H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N interactions, while the compound 2f has no N⋯H/H⋯N contacts. Hirshfeld surface analyses were performed to gain insight into the behavior of these interactions. Calculated frontier orbitals showed that their highest occupied and lowest unoccupied molecular orbitals are antibonding orbitals. The allyl sulfonamides 1e and 2f are among the most active compounds in each series, inhibiting approximately 60% of the mycelial growth of Botrytiscinerea at 3 mmol L-1.

Twelve tetraphenylphosphonium allyldithiocarbimates were synthesized and fully characterized by high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), infrared and nuclear magnetic resonance (NMR) spectroscopies. The spectroscopic data indicated that the allyldithiocarbimate anions present Z configuration, as confirmed by X-ray crystallography. These new compounds inhibited the germination of Phakopsora pachyrhizi and Hemileia vastatrix at very low doses, with IC50 (concentration to achieve 50% of inhibition of spore germination) values ranging from 0.028 to 0.166 mmol L-1, and IC90 (concentration to achieve 90% of inhibition of spore germination) values varying from 0.156 to 0.528 mmol L-1. Allyldithiocarbimate salts are lead compounds for the development of new antifungals for coffee leaf rust and Asian soybean rust, devastating plant diseases with limited control options.

Here we describe the total syntheses and characterization by elemental analyses, infrared and NMR spectroscopy of three new compounds analogous to avenaciolide, a bis-γ-lactone isolated from Aspergillus avenaceus that possesses antifungal activity, where the octyl group of the natural product was replaced by aromatic groups containing chlorine and fluorine atoms. The effects of the avenaciolide, the novel compounds and their synthetic precursors on mycelia development and conidia germination of Colletotrichum gloeosporioides and Fusarium solani were evaluated in vitro. The title compounds were almost as active as avenaciolide. The absolute structures of the chlorinated analogs were determined by X-ray diffraction analysis.

O ácido 6alfa,7beta-di-hidroxivouacapan-17beta-óico (1) e o 6alfa,7beta-di-hidroxivouacapan-17beta-oato de metila (2) são produtos naturais isolados do extrato hexânico de frutos de Pterodon polygalaeflorus Benth. Este trabalho descreve a preparação e caracterização por espectroscopias no infravermelho, de ressonância magnética nuclear e por análise elementar do derivado inédito 6alfa,7beta-tiocarbonildioxivouacapan-17beta-oato de metila (5), a partir do éster 2. A estrutura do composto 5 foi determinada por difração de raios-X. Na concentração de 100 ppm, este composto inibiu o crescimento radicular de Sorgum bicolor L. (-28%) e não mostrou efeitos significantes sobre Cucumis sativus L..

The 6alpha,7beta-dihydroxyvouacapan-17beta-oic acid (1) and methyl 6alpha,7beta-dihydroxyvouacapan-17beta-oate (2) are natural products isolated from the hexane extract of Pterodon polygalaeflorus Benth fruits. Here we describe the preparation and characterization by infrared and nuclear magnetic resonance spectroscopy, and by elemental analysis of the novel derivative methyl 6alpha,7beta-thiocarbonyldioxyvouacapan-17beta-oate (5), from the ester 2. The structure of compound 5 was determined by X-ray diffraction. At the concentration of 100 ppm, this compound inhibited the radicle growth of Sorgum bicolor L. (-28%) and showed no significant effect on Cucumis sativus L..