Novel Naphthyl and Phenyl Maleimide Derivatives: Molecular Design, Systematic Optimization, Antifungal Evaluation, and Action Mechanism

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

Опубликована: Апрель 29, 2025

A systematic optimization strategy, as an effective screening approach for new antifungal compounds, was implemented to rationally construct novel naphthyl and phenyl maleimide derivatives. The structures of molecules A32 B6 were further confirmed by single-crystal X-ray diffraction. in vitro activity evaluation showed that the target compound obtained structure exhibited excellent inhibition (EC50 = 0.59 μg/mL) against Rhizoctonia solani, which better than control agent dimethachlone (1.21 μg/mL). Further vivo experiments on rice leaves potted plants R. solani at 200 μg/mL possessed outstanding protective efficiency compared dimethachlone. mycelium morphology observation SEM indicated (25 severely damaged surface mycelium, accordance with increased result cell membrane permeability assay. MD simulations molecular docking analysis revealed compounds A1 have a similar binding mode active pocket plasma H+-ATPases (PMA1) reference fungicide fluoroimide. In particular, there more hydrogen bonds protein complex complexes This research constructing derivatives strategy provides practical way find leads, thereby developing fungicides.

Язык: Английский

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Citral‐based amide derivatives improve the antifungal activity of Kresoxim‐methyl against Rhizoctonia solani

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Май 26, 2025

Abstract BACKGROUND Rhizoctonia solani , the fungal pathogen causing rice sheath blight, threatens global food security. Prolonged use of Kresoxim‐methyl (KM), a common fungicide, has led to resistance and reduced effectiveness. This study investigates synergistic effects citral‐based amide derivatives with KM explains underlying mechanisms. RESULT Among tested derivatives, compound d25 exhibited most pronounced effect, achieving peak ratio (SR = 2.66 ± 0.67) at molar 25% in mixture. At 10%, mixture (Mix) demonstrated significant antifungal activity both vitro vivo effectively reducing mycelial dry weight enhancing leaf protection. Mechanistic studies revealed that Mix disrupted tricarboxylic acid (TCA) cycle, thereby inhibiting energy metabolism. Additionally, interfered arachidonic metabolism, impairing cell membrane repair mechanisms fungicidal efficacy KM. Toxicity assessments minimal cytotoxicity against human lines low acute toxicity toward Apis mellifera L. zebrafish. CONCLUSION The findings elucidate Mix, underscoring their potential as effective fungicide synergists. establishes robust theoretical practical foundation for chemical control strategies R. providing new insights into development safe efficient formulations. © 2025 Society Chemical Industry.

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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Discovery of novel 4‐sulfur‐substituted pyrazol‐5‐yl‐benzamide derivatives containing amide/hydrazide/ester moieties as potential succinate dehydrogenase inhibitors

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Июнь 2, 2025

Abstract BACKGROUND Succinate dehydrogenase inhibitor (SDHI) fungicides have been widely utilized in the combat of plant pathogenic fungi due to their potent, broad‐spectrum antifungal activity and unique mode action. In this study, a series novel 4‐sulfur‐substituted pyrazol‐5‐yl‐benzamide derivatives containing amide, hydrazide, or ester moieties were synthesized develop innovative SDH inhibitors. RESULTS The bioassay studies indicated that several compounds exhibited potent vitro fungicidal against various fungi. Particularly, compound 4d demonstrated efficacy, with EC 50 values 0.21, 0.95, 0.64, 1.33, 0.66 mg L −1 Valsa mali , Botrytis cinerea Rhizoctonia solani Fusarium graminearum Gaeumannomyces graminis respectively. vivo effectively prevented V. infection apples at showing superior protective curative effects (93.4% 85.5%) compared lead A27 (68.7% 57.0%) commercial fungicide fluxapyroxad (55.4% 43.6%). Enzymatic inhibition assays molecular docking analysis suggested could serve as potential inhibitor. CONCLUSION This study offers valuable insights for expanding spectrum further developing them © 2025 Society Chemical Industry.

Язык: Английский

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