Regioselective Synthesis of Multisubstituted 2,3-Dihydrooxazoles by 1,3-Dithiane Umpolung.

Herein, we report a novel strategy for the regioselective synthesis of aromatic and heteroaromatic 2,3-dihydrooxazoles from 2-alkynyl-1,3-dithianes and nitrones. This method exploits the 1,3-dithiane umpolung, nucleophilic cycloaddition, and rearrangement processes to achieve the rapid assembly of dihydrooxazole molecules. The regioselective method is extremely mild, achieving complete conversion within one min under air at 25 °C with high efficiency.

Dual RNA sequencing during Trichoderma harzianum-Phytophthora capsici interaction reveals multiple biological processes involved in the inhibition and highlights the cell wall as a potential target.

BACKGROUND: Phytophthora capsici is a destructive oomycete pathogen, causing huge economic losses for agricultural production. The genus Trichoderma represents one of the most extensively researched categories of biocontrol agents, encompassing a diverse array of effective strains. The commercial biocontrol agent Trichoderma harzianum strain T-22 exhibits pronounced biocontrol effects against many plant pathogens, but its activity against P. capsici is not known. RESULTS: T. harzianum T-22 significantly inhibited the growth of P. capsici mycelia and the culture filtrate of T-22 induced lysis of P. capsici zoospores. Electron microscopic analyses indicated that T-22 significantly modulated the ultrastructural composition of P. capsici, with a severe impact on the cell wall integrity. Dual RNA sequencing revealed multiple biological processes involved in the inhibition during the interaction between these two microorganisms. In particular, a marked upregulation of genes was identified in T. harzianum that are implicated in cell wall degradation or disruption. Concurrently, the presence of T. harzianum appeared to potentiate the susceptibility of P. capsici to cell wall biosynthesis inhibitors such as mandipropamid and dimethomorph. Further investigations showed that mandipropamid and dimethomorph could strongly inhibit the growth and development of P. capsici but had no impact on T. harzianum even at high concentrations, demonstrating the feasibility of combining T. harzianum and these cell wall synthesis inhibitors to combat P. capsici. CONCLUSION: These findings provided enhanced insights into the biocontrol mechanisms against P. capsici with T. harzianum and evidenced compatibility between specific biological and chemical control strategies. © 2024 Society of Chemical Industry.