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

Authors :
David Peña
Antonio López-Piñeiro
Damian Fernández
Mark E. Light
Juan Manuel Prieto
Lucía Santisteban
Richardo Xhavier Valladares
Pedro Cintas
Reyes Babiano
Source :
Heliyon, Vol 9, Iss 11, Pp e21313- (2023)
Publication Year :
2023
Publisher :
Elsevier, 2023.

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.

Details

Language :
English
ISSN :
24058440
Volume :
9
Issue :
11
Database :
Directory of Open Access Journals
Journal :
Heliyon
Publication Type :
Academic Journal
Accession number :
edsdoj.7f2d72ff47f995d4ab5b927e6202
Document Type :
article
Full Text :
https://doi.org/10.1016/j.heliyon.2023.e21313