Facile synthesis, spectral characterization and antimicrobial activity of 6‐substituted‐2,4,8,10‐tetra‐t‐butyl dibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6‐oxides

Abstract

Several novel 2,4,8,10-tetra-t-butyl-6-substituted dibenzo [d , g] [1,3,6,2]dioxathiaphosphocin 6-oxides were synthesized in high yield by cyclocondensation of 2,2'-thiobis(2,4-di-t-butylphenol) with phosphorus oxychloride in the presence of triethylamine and a catalytic amount of dimethylaminopyridine (DMAP) in dry toluene followed by in situ reaction with different bulky phenols/thiophenols under the same reaction conditions. The structures of the synthesized compounds were confirmed by analytical, IR, multinuclear NMR studies. Their antibacterial and antifungal activities were evaluated against Staphylococcus aureus, Escherichia coli, Aspergillus niger and Fusarium oxysporium, respectively. Some of them showed moderate activity against these microorganisms.

Phytotoxic metabolites produced by Diaporthe eres involved in cane blight of grapevine in Italy

“…These latter were identified by TLC analysis carried out in different conditions, in comparison with the corresponding standard and also by cochromatography. Furthermore, their spectroscopic properties (essentially 1 H NMR and MS) were very similar to those previously reported for 1 (Avent et al 1992), for 2 (Venkatasubbaiah et al 1991;Zhang et al 2012), for 3 (Kasthuraiah et al 2004;Passmore et al 2018) for 4 (Kimura and Tamura 1973;Venkatasubbaiah et al 1991;Capasso et al 1992) for 5 (Zhang et al 2012;Cimmino et al 2017). For 1 we carried out a complete 1 H and 13 C NMR study for the first time using 1 D and 2 D NMR experiments (COSY, HSCQ and HMBC) ( Figures S1-S5, Supplementary materials) that allowed to unambiguously assign the chemical shifts to all the carbons and the corresponding protons as reported in Table S1 of Supplementary materials, in respect to the data previously reported using only 1 D NMR (Avent et al 1992).…”

“…p-Cresol (3): 1 H NMR, d: 7.04 (d, J ¼ 8.0 Hz, H-3 and H-5), 6.74 (d, J ¼ 8.0 Hz, H-2 and H-6), 4.83 (br s, OH), 2.28 s, Me) ESI/MS (þ), m/z: 109 [M þ H] þ . These data are in agreement with the data previously reported (Kasthuraiah et al 2004;Passmore et al 2018).…”

Phytotoxic Metabolites from Three Neofusicoccum Species Causal Agents of Botryosphaeria Dieback in Australia, Luteopyroxin, Neoanthraquinone, and Luteoxepinone, a Disubstituted Furo-α-pyrone, a Hexasubstituted Anthraquinone, and a Trisubstituted Oxepi-2-one from Neofusicoccum luteum

“…Finally, by purification of the residue of the fifth fraction of the original column separation, a further homogeneous compound was isolated and identified as p-cresol (9) by comparing its 1 H NMR and MS data to those previously reported. 27 This work represents the first complete report on the production of extracellular PMs by N. luteum and the first comparison of phytotoxins produced by three different Neofusicoccum spp. involved in BD.…”

“…Finally, by purification of the residue of the fifth fraction of the original column separation, a further homogeneous compound was isolated and identified as p -cresol ( 9 ) by comparing its 1 H NMR and MS data to those previously reported …”

“…p-Cresol ( 9): 1 H NMR and ESI/MS (+) data are in agreement with those previously reported. 27,48 Computational Section. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations were run with Gaussian 16, 52 with default grids and convergence criteria.…”