Synthesis of Tyrosol 1,2,3-Triazole Derivatives and Their Phytotoxic Activity against <i>Euphorbia heterophylla</i>
Cristiane Aparecida Franco, Toshik Iarley da Silva, Marlon Gomes Dias, Bruno W. Ferreira, Bianca Lana de Sousa, Guilherme Mateus Bousada, Robert W. Barreto, Boniek G. Vaz, Gesiane da Silva Lima, Marcelo Henrique dos Santos, José Antônio Saraiva Grossi, Eduardo Vinícius Vieira Varejão
Abstract
The synthesis and phytotoxic activity of a series of tyrosol 1,2,3-triazole derivatives are reported herein. Target compounds were synthesized through the copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC), known as click reaction, and these were tested for phytotoxic activity on leaves of wild poinsettia (Euphorbia heterophylla), fleabane (Conyza sumatrensis), and tropical spiderwort (Commelina benghalensis). These are three highly noxious agricultural weeds that challenge available weed control methods, including the use of chemical herbicides. Twenty-five compounds were synthesized and tested. None of the compounds showed phytotoxic activity against C. benghalensis and C. sumatrensis, but almost all of them produced yellowing, bleaching, and necrosis on leaves of E. heterophylla. Two of the tyrosol 1,2,3-triazole derivatives produced more extensive lesions than those produced by the commercial herbicide diquat, used as a positive control (p ≤ 0.05). When applied on leaves of E. heterophylla, these compounds interfered with the stomatal conductance, net photosynthesis, internal carbon concentration, transpiration rate, water-use efficiency, and chlorophyll A and B contents. The interference of such compounds on such photosynthesis-related variables indicates that tyrosol 1,2,3-triazole derivatives may be capable of lowering the competitiveness of E. heterophylla and acting as additional tools for managing this competitive weed in agricultural lands.