Síntese e avaliação da atividade fitotóxica de novos 1,2,3-triazóis fluorados derivados do eugenol
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2021-02-19
Autores
Paula, Wenderson Tinorio de
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Universidade Federal do Espírito Santo
Resumo
Agriculture faces major challenges, going from producing high-quality food in order to feed the world’s growing world to controlling weeds, since they may cause crop yield losses of up to 32% and economic damage, besides being susceptible to herbicide resistance. In this context, developing more efficient compounds at low doses and non-toxic to the environment may be an alternative; for that, triazole organofluorides derived from natural products may be promising, considering that about 25% of licensed herbicides are fluorinated. In this work, we sought to synthesize new organofluorinated compounds containing the 1,2,3-triazolic portion using the natural product eugenol as a starting material. The derivatives were prepared in three stages. In the first one, eugenol was treated with (±) -epichloridine, obtaining (±) -2 - ((4-allyl-2-methoxyphenoxy) methyloxirane) (1) with 90% yield. The azidolysis of (1) with sodium azide resulted in the preparation of (±) -1-(4-allyl-2- methoxyphenoxy)-3-azidopropan-2-ol (2) in 95% yield. The third stage corresponded to the CuAAC reaction (click reaction) between (2) and the alkynes for the formation of 3a-3k. The characterization was performed using spectroscopic methods, such as Infrared, 1H and 13C Nuclear Magnetic Resonance. The phytotoxic activity of monofluorinated derivatives (3b, 3c, and 3d) and difluorinated (3e) at 500 ppm and difluorinated products (3f and 3g) at 250 ppm were stood out.
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Compostos heterocíclicos , produtos naturais , ervas daninhas