Synthesis of novel glycerol-fluorinated triazole derivatives and evaluation of their phytotoxic and cytogenotoxic activities.

The control of weeds in agriculture is mainly conducted with the use of synthetic herbicides. However, environmental and human health concerns and increased resistance of weeds to existing herbicides have increased the pressure on researchers to find new active ingredients for weed control which present low toxicity to non-target organisms, are environmentally safe, and can be applied at low concentrations. It is herein described the synthesis of glycerol-fluorinated triazole derivatives and evaluation of their phytotoxic and cytogenotoxic activities. Starting from glycerol, ten fluorinated triazole derivatives were prepared in four steps. The assessment of them on Lactuca sativa revealed that they present effects on phytotoxic and cytogenotoxic parameters with different degrees of efficiency. The compounds 4a, 4b, 4d, 4e, 4i, and 4j have pre-emergent inhibition behavior, while all the investigated compounds showed post emergent effect. Mechanism of action as clastogenic, aneugenic, and epigenetic were observed in the lettuce root meristematic cells, with alterations as stick chromosome, bridge, delay, c-metaphase, and loss. It is believed that glycerol-fluorinated triazole derivatives possess a scaffold that can be explored towards the development of new chemicals for the control of weed species.

Phytochemical screening and phytocytotoxic effects of the tropical Myrcia vittoriana (Myrtaceae).

We investigated whether essential oil and aqueous and ethanolic extracts from M. vittoriana leaves have phytotoxic effects on the germination and initial development, and cytogenotoxic effects on the cell cycle, of model plants. The essential oil and extracts of M. vittoriana were characterized and used as treatments in phytotoxicity and cytotoxicity tests. The results indicated a reduction in germinative parameters and plant growth, with the higher concentrations of extracts and essential oil having the most evident effects. The cell cycle was also affected with a reduction of the mitotic index and the presence of chromosomal and nuclear alterations. All treatments showed clastogenic and aneugenic modes of action. The results can be associated with the synergistic effects of metabolites found in the extracts and essential oil, mainly the presence of the sesquiterpene germacrene D in the essential oil and of catechins, saponins, and tannins in the extracts. These substances inhibit plant germination and growth, confirming the phytotoxic effects of M. vittoriana in plant models, which should now be tested under field conditions.

Searching an auxinic herbicide to use as positive control in toxicity assays.

Due to rising concerns for environmental and human health, many toxic compounds, such as auxin-based herbicides, have been tested in relation their toxicity effect. Especially cyto- and phytotoxic assays have been performed on a number monocot and eudicot plant species. In these approaches the toxicity level of the auxin is compared to a positive control - usually a commercial compound with known effects and chemical similarity to the target compound. However, many target compounds still lack an indication of an adequate positive control. Here, we evaluate the phytotoxic and cytotoxic effect of the auxins 2,4-dichlorophenoxyacetic acid, dicamba, and picloram in order test their potential use as positive controls. All tested auxinic herbicides showed clastogenic and aneugenic effect mechanisms. The results indicate 2,4-dichlorophenoxyacetic acid as the most phyto- and cytotoxic in the discontinuous method in Lactuca sativa L. and Allium cepa L., and also in the continuous method in A. cepa. Thus, we suggest 2,4-dichlorophenoxyacetic acid as a positive control for future mutagenesis studies involving new auxins. For studies with L. sativa in continuous method, we recommend the auxin picloram as positive control as this one was the only one which allowed the development of roots.

Bioactivity and molecular properties of Phenoxyacetic Acids Derived from Eugenol and Guaiacol compared to the herbicide 2,4-D.

Herbicides are agrochemicals applied in the control of weeds. With the frequent and repetitive use of these substances, serious problems have been reported. Compounds of natural origin and their derivatives are attractive options to obtain new compounds with herbicidal properties. By aiming to develop compounds with potentiated herbicidal activity, phenoxyacetic acids were synthesized from eugenol and guaiacol. The synthesized compounds were characterized and the herbicidal potential of phenoxyacetic acids and precursors was evaluated through bioassays regarding the germination and initial development of Lactuca sativa and Sorghum bicolor seedlings, with the induction of DNA damage. The induction of changes in the mitotic cycle of meristematic cells of roots of L. sativa was also analyzed. At the concentration of 3 mmol L-1, phenols and their respective phenoxyacetic acids presented phytotoxic and cytotoxic activities in L. sativa and S. bicolor. Eugenol and guaiacol also presented genotoxic action in L. sativa. The toxic effect of eugenoxyacetic acid was more pronounced in L. sativa than in S. bicolor, similar to the commercial 2,4-D herbicide. Molecular properties of the phenols and their derivatives phenoxyacetic acids were compared with the ones obtained for the herbicide 2,4-D, where it was found a correlation between their molecular properties and bioactivity.