Synthesis and Evaluation of Herbicidal Ureidopyrimidine Compounds: Focus on Sulfonamide Modifications

Journal of Agricultural and Food Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 6, 2025

In this study, 32 novel ureidopyrimidine compounds containing sulfonamide fragments were strategically designed and synthesized through active substructure combination. Postemergence herbicidal activity assays demonstrated that 13a, 14d, 15c exhibited superior efficacy against broadleaf weeds, including Zinnia elegans Abutilon theophrasti, with compound achieving a remarkable 95% control rate at 9.375 g a.i./ha, comparable to of the commercial herbicide saflufenacil. Molecular docking simulations revealed these compounds, along saflufenacil, establish hydrogen bonds protoporphyrinogen oxidase, particularly involving important amino acid residues, ARG-98, GLY-175, ASN-67. Structure-activity relationship analysis, supported by density functional theory calculations molecular electrostatic potential studies, highlighted importance negatively charged regions in activity. This comprehensive research provides valuable insights into design development potent herbicides, establishing strong foundation for future advancements agricultural chemistry.

Язык: Английский

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Discovery of a Class of Novel Succinate Dehydrogenase Inhibitors Containing a Coumarin Structure

Journal of Agricultural and Food Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 7, 2025

Succinate dehydrogenase (SDH) has emerged as a highly promising target in modern agricultural research, playing crucial role developing environmentally friendly and efficient fungicides for combating pathogens. This study presents the discovery of novel class SDH inhibitors (I-III) incorporating coumarin segments achieved through an active fragment swapping linking strategy. Fungicidal activity assays revealed that several compounds within this series demonstrate significant inhibitory effects against tested fungal strains. Through comprehensive structure-activity relationship studies, compound N-(1-((3-butyl-4-methyl-2-oxo-2H-chromen-7-yl)oxy)propan-2-yl)-3-(difluoromethyl)-N-methoxy-1-methyl-1H-pyrazole-4-carboxamide (IIk) exhibited potent various species. Notably, it demonstrated superior efficacy S. sclerotiorum with EC50 value 1.14 μg/mL, outperforming commercial control agent thifluzamide (EC50 = 4.90 μg/mL). Molecular docking simulations indicated hydrophobic interactions serve primary binding mechanism between ligand SDH. Intriguingly, IIk displayed dual functionality, not only acting effective fungicide but also promoting growth wheat seedlings Arabidopsis thaliana, resulting increased plant biomass. Preliminary investigations into its growth-promoting suggest enhances nitrate reductase activity, thereby facilitating growth.

Язык: Английский

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Structural optimization of SDH‐targeting chalcone derivatives: piperazine‐driven binding stability against Xanthomonas pathogens

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Abstract BACKGROUND Natural green pesticides have become a global research hotspot, and identifying chemical structural frameworks with excellent biological activity has the direction of numerous researchers. RESULTS Twenty chalcone derivatives incorporating 1,2,3,4‐tetrahydroquinoline scaffolds were systematically evaluated for their antibacterial against six plant pathogenic bacteria. Among tested compounds, H1–H10 exhibited superior in vitro inhibition Xanthomonas citri pv. mangiferaeindicae ( Xcm ) compared to Y1–Y10. Notably, compound H6 demonstrated exceptional potency, median effective concentration (EC 50 value 3.25 μg mL −1 , significantly surpassing commercial agent (TC, EC = 75.34 ). In vivo efficacy trials revealed that achieved 65.24% curative at 100 outperforming TC (42.81%). Scanning electron microscopy further confirmed H6's disruptive effects on bacterial membrane integrity. Mechanistic studies targeting succinate dehydrogenase (SDH), key respiratory enzyme, energetic similarities between SDH inhibitor bixafen through molecular docking dynamics simulations. CONCLUSION The moiety enhanced binding affinity, while introduced piperazine substructure improved both complex stability (root mean square deviation <1.5 Å) target engagement. These findings establish as promising lead developing next‐generation inhibitors, providing critical insights into structure–activity relationships agricultural antimicrobial design. © 2025 Society Chemical Industry.

Язык: Английский

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Fungicidal Activity of Novel 6-Isothiazol-5-ylpyrimidin-4-amine-Containing Compounds Targeting Complex I Reduced Nicotinamide Adenine Dinucleotide Oxidoreductase

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 25, 2024

To discover novel inhibitors of the complex I reduced nicotinamide adenine dinucleotide (NADH) oxidoreductase as fungicides, a series 6-isothiazol-5-ylpyrimidin-4-amine-containing compounds were designed using computer-aided pesticide design method and splicing substructures from diflumetorim isotianil. In vitro fungicidal bioassays indicated that

Язык: Английский

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Discovery of Novel (5-Mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)methyl Phenyl Carbamate as a Potent Phytoene Desaturase Inhibitor through Scaffold Hopping and Linker Modification

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(34), С. 18898 - 18908

Опубликована: Авг. 15, 2024

Phytoene desaturase (PDS) is a key rate-limiting enzyme in the carotenoid biosynthesis pathway. Although commercial PDS inhibitors have been developed for decades, it remains necessary to develop novel with higher bioactivity. In this work, we used scaffold hopping and linker modification approaches design synthesize series of compounds (

Язык: Английский

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