Please use this identifier to cite or link to this item: http://hdl.handle.net/10662/23139
Title: A new series of acylhydrazones derived from metribuzin with modulated herbicidal activity
Authors: Peña Abades, David
López Piñeiro, Antonio
Fernández Rodríguez, Damián
Light, Mark E.
Prieto, Juan Manuel
Santisteban, Lucía
Valladares, Richardo Xhavier
Cintas Moreno, Pedro
Babiano Caballero, Reyes
Keywords: Acilhidrazona;Metribuzina;Actividad herbicida;Plantas de tomate;Colzas;Acylhydrazone;Metribuzin;Herbicidal activity;Tomato plants;Rapeseeds
Issue Date: 2023
Publisher: Elsevier
Abstract: This paper reports the preparation and herbicidal evaluation of a small library of acylhydrazones based on the synthetic herbicide metribuzin. The hydrazone linkage easily obtained by reaction of metribuzin with aliphatic and aromatic aldehydes, masks efficiently the exocyclic amino group, thereby altering significantly H-bonding with the receptor and increasing the lipophilicity relative to the parent herbicide. The structures of all compounds, including key stereochemical issues on conformation and E/Z configuration around the C––N bond were thoroughly elucidated by spectroscopic methods, and unambiguously corroborated by X-ray diffraction analysis. The herbicidal assays using an aliphatic and an aromatic acylhydrazone were performed on tomato and rapeseed plants grown in greenhouse. Our results demonstrate, regardless of rate application, that such acylhydrazone formulations do not alter the selectivity of metribuzin. Moreover, the herbicide activity was even higher in the alkyl derivative than that achieved by commercial metribuzin, thus suggesting that this substance can be applied with no need of combination with chemical coadjuvants, unlike most formulations of commercially available herbicides. Therefore, the study shows the promising effect of chemical derivatization of a common herbicide as metribuzin, to improve the herbicide activity without compromising selectivity, and allowing the farmers its use in crop protection safely and effectively.
URI: http://hdl.handle.net/10662/23139
DOI: 10.1016/j.heliyon.2023.e21313
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