Design and Synthesis of Novel 4‑Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha–1. Moreove...

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Published inJournal of agricultural and food chemistry Vol. 67; no. 37; pp. 10489 - 10497
Main Authors Lei, Kang, Li, Pan, Yang, Xue-Fang, Wang, Shi-Ben, Wang, Xue-Kun, Hua, Xue-Wen, Sun, Bin, Ji, Lu-Sha, Xu, Xiao-Hua
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.09.2019
Amer Chemical Soc
Subjects
Agriculture
Agriculture, Multidisciplinary
Chemistry
Chemistry, Applied
Food Science & Technology
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
synthesis
4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one
auxin herbicide
β-triketone
herbicidal activity
beta-triketone
ACID-DERIVATIVES
CRYSTAL-STRUCTURE
4-hydroxyl-3-(2-phenoxyacety)-pyran-2-one
ARABIDOPSIS
INHIBITORS
TRIKETONE
ANTIMICROBIAL ACTIVITY
DISCOVERY
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Summary:In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha–1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha–1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.
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ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.9b03109