Design, synthesis, and biological evaluation of oxime ether derivatives containing 1,5‐dimethyl‐6‐thioxo‐1,3,5‐triazinane‐2,4‐dione as protoporphyrinogen IX oxidase inhibitors

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

Abstract BACKGROUND Herbicides based on protoporphyrinogen IX oxidase (PPO; EC 1.3.3.4) are widely used for weeding control in agricultural fields to safeguard food security. PPO herbicides, because of their low dosage, rapid action weeds, slow accumulation the environment and toxicity mammals, have become an important field research development new herbicides. This study presents a novel molecular scaffold with remarkably potent herbicidal activity. RESULTS A series oxime ether derivatives containing 1,5‐dimethyl‐6‐thioxo‐1,3,5‐triazinane‐2,4‐dione 6a–6z were designed synthesized bioisosterism substructure splicing, characterized by 1 H 13 C nuclear magnetic resonance spectroscopies, high‐resolution mass spectrometry. The configuration compound 6u was confirmed single‐crystal X‐ray diffraction. Compound 6r displayed excellent activity >95% against Echinochloa crus‐galli , Digitaria sanguinalis Medicago sativa Conyza canadensis at dosage 37.5 g hm–2 glasshouse. At 75 hm–2, safe application rice showed (>200 μg g–1) towards Apis mellifera . Transcriptomics analysis E. treated using oxadiazon as positive control, revealed compound's mode‐of‐action. There eight metabolic biosynthetic pathways DEGs ‘photosynthesis’, ‘porphyrin metabolism’, ‘carotenoid biosynthesis’ so between same. Scaffold94.443 (coproporphyrinogen‐III oxidase) upstream changes downregulated quantitative reverse transcription PCR combined chlorophyll biosynthesis. target may be Nt inhibitory effects, represented K i, 30.34 n m vitro Molecular docking that could form two hydrogen bonds Arg98. CONCLUSION Through we successfully developed lead exhibiting activity, no harm honeybees. Further herbicides this is warranted. © 2025 Society Chemical Industry.

Язык: Английский

Discovery of N-Phenylphthalimides Containing Ether Moiety as Potential Protoporphyrinogen IX Oxidase Inhibitors

Journal of Agricultural and Food Chemistry, Год журнала: 2025, Номер 73(11), С. 6599 - 6609

Опубликована: Март 5, 2025

The discovery of novel protoporphyrinogen IX oxidase (PPO) inhibitors has become a key focus in herbicide development. To explore new PPO inhibitors, series N-phenylphthalimide derivatives with ether moieties were designed and successfully synthesized. Among these, compound B18 (Ki = 10.3 nM) exhibited strong inhibitory effect on NtPPO, outperforming flumiclorac-pentyl 46.3 flumioxazin 52.0 nM). It is noted that compounds A3, B18, B19, B20 showed broad-spectrum herbicidal activity against the tested weeds at 75 g a.i./ha. In addition, results molecular simulation density functional theory (DFT) calculations indicated possessed not only robust hydrogen bond Arg98 NtPPO but also superior chemical reactivity, electrostatic field, polarity. Therefore, may be regarded as promising lead for development high-efficiency inhibitors.

Язык: Английский

A doubly Phenoxyacetate-bridged dinuclear manganese(II) complex with 1,10-Phenanthroline: Synthesis, 1-D supramolecular structure, Hirshfeld surface analysis, magnetic and theoretical studies

Polyhedron, Год журнала: 2024, Номер 267, С. 117337 - 117337

Опубликована: Дек. 4, 2024

Язык: Английский