Síntese de novos triazóis derivados do (3aR)-(+)-esclareolídeo com potencial atividade fungicida

Abstract

Agribusiness in Brazil is one of the main contributors to the country's Gross Domestic Product, with soybeans acting as a driving force for agricultural development since the 1970s. Soybean production can be affected by several factors, such as water shortages and challenges such as diseases, management, and pests. Among the diseases that affect soybeans, anthracnose, caused by the fungus Colletotrichum truncatum (Schwein.) Andrus & WD Moore, has attracted attention due to the emergence of parasites resistant to commonly used fungicides. In this sense, the development of new fungicidal agents is urgently needed. Structural modification of natural products continues to be a promising strategy for the development of new fungicidal agents, as evidenced by the derivatives of the natural product (+)-sclareolide against Sclerotinia sclerotiorum and Botrytis cinerea. In view of this, the present work aims to synthesize new derivatives of (3aR)-(+)-sclareolide with potential antifungal activity against the pathogen that causes soybean anthracnose. For this purpose, the 1,3-dipolar cycloaddition catalyzed by Cu(I) between aromatic azides and alkynes obtained from (3aR)-(+)-sclareolide was used, resulting in 38 novel triazole derivatives (S42-S79) with overall yields ranging from 48% to 91%.