A new series of acylhydrazones derived from metribuzin with modulated herbicidal activity

• DOI: 10.1016/j.heliyon.2023.e21313
• Publication Date: 2023-10-28T02:53:07Z
• Authors: David Peña; Antonio López-Piñ...; Damian Fernández; Mark E. Light; Juan Manuel Prieto; Lucía Santisteban; Richardo Xhavier ...; Pedro Cintas; Reyes Babiano
• Keywords: Metribuzin; Hydrazone; Lipophilicity; Chloroformate

This paper reports the preparation and herbicidal evaluation of a small library acylhydrazones based on synthetic herbicide metribuzin. The hydrazone linkage easily obtained by reaction metribuzin with aliphatic aromatic aldehydes, masks efficiently exocyclic amino group, thereby altering significantly H-bonding receptor increasing lipophilicity relative to parent herbicide. structures all compounds, including key stereochemical issues conformation E/Z configuration around CN bond were thoroughly elucidated spectroscopic methods, unambiguously corroborated X-ray diffraction analysis. assays using an acylhydrazone performed tomato rapeseed plants grown in greenhouse. Our results demonstrate, regardless rate application, that such formulations do not alter selectivity Moreover, activity was even higher alkyl derivative than achieved commercial metribuzin, thus suggesting this substance can be applied no need combination chemical coadjuvants, unlike most commercially available herbicides. Therefore, study shows promising effect derivatization common as improve without compromising selectivity, allowing farmers its use crop protection safely effectively.