Design, Synthesis, and Biological Evaluation of Novel Aryl Sulfonamide Derivatives as Potential Succinate Dehydrogenase Inhibitors Targeting Phytopathogenic Fungi

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

In our pursuit of novel succinate dehydrogenase inhibitor (SDHI) fungicides for agriculture, we replaced the traditional amide structure with a sulfonamide framework and introduced various heterocyclic aromatic rings at sulfonamide's termini. This strategy yielded 30 synthesized compounds, which were screened antifungal activity against eight phytopathogenic fungi. The biological assay results demonstrated that several target compounds exhibited significant in vitro activity. Notably, compound 2f showed remarkable Valsa mali an EC50 value 0.56 mg/L, outperforming Boscalid (EC50 = 1.79 mg/L). vivo experiments revealed provided protection to apple fruits, comparable Boscalid. SEM analysis 3e disrupted morphology fungal hypha analysis, suggested terminal polyhalogen-substituted pyridine moieties might be pivotal regions influencing their efficacy. Molecular docking binding mode SDH. Furthermore, detailed SDH inhibition assays confirmed potential (IC50 2.51 μM) as prospective inhibitors. RNA transcriptomic indicated application could influence gene expression fungi, thereby exerting defensive effect plant pathogenic Consequently, shows promise developing efficient agrochemical fungicide.

Language: Английский

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Design and Syntheses of Proherbicides Targeting 4-Hydroxyphenylpyruvate Dioxygenase

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) is regarded as a crucial target in the domain of herbicide discovery. Herein, we adopted proherbicides concept, based on initially discovered lead compound II-aa. Our group has designed four derivatives by incorporating alkyl, carbonyl ester, sulfonyl and phosphate ester fragments. Although these did not exhibit very strong inhibitory activity against HPPD vitro, vivo studies demonstrated their efficacy suppressing activity. This was reduction protein levels emergence significant bleaching symptoms treated plants. Among derivatives, acetyl (III-ag), cyclopropyl (III-ak), pyridine-sulfonyl (III-bm) substituted herbicidal that surpassed II-aa, exhibiting complete control over nine weed species at concentration 120 g active ingredient per hectare (g ai/ha). It worth noting dose 30 ai/ha sufficient to achieve seven species. one compound, III-ay (diethylamino carbonyl), exhibited selective inhibition growth six 90% while demonstrating no adverse effects normal crops such corn, wheat, peanuts. A structure–activity relationship study reduced relative counterparts yet enhanced crop tolerance. The results our research indicate proherbicide approach potential significantly enhance selectivity herbicides. strategy poised play pivotal role advancement next-generation

Language: Английский

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Synthesis and Herbicidal Activity of 3-Phenyl-5-oxy-benzothiazole-2-one Derivatives

ACS Agricultural Science & Technology, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

Language: Английский

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Novel Diphenyl Ether Carbonyl Ester Fragment as a Promising Skeleton Targeting Succinate Dehydrogenase

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

Succinate dehydrogenase (SDH) is a globally recognized critical target for fungicides. Our research mainly focuses on discovering novel molecular skeletons targeting SDH. We designed series of diphenyl ether ester derivatives that exhibit potential efficacy against Rhizoctonia solani by utilizing bioisosteric approach. These results indicate compounds with shorter linkers significantly enhance the antifungal activity. Furthermore, an ester-linked compound was superior to its amide and N-(alkoxy) counterparts. Specifically, ba achieved remarkable 92% in controlling R. at dosage 50 μg/mL EC50 value 0.44 μg/mL, thus outperforming boscalid without negatively impacting rice growth. Moreover, caused significant damage mycelium demonstrated IC50 1.69 μM SDH, exhibiting comparable boscalid. unveil promising avenue replacing traditional heterocyclic amide-based inhibitors, potentially heralding new generation SDH-targeting

Language: Английский

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Synthesis and Activity of Novel Pyrazole/Pyrrole Carboxamides Containing a Dinitrogen Six-Membered Heterocyclic as Succinate Dehydrogenase and Ergosterol Biosynthesis Inhibitors against Colletotrichum camelliae

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 23, 2025

Pyrazole carboxamide derivatives were initially extensively studied as succinate dehydrogenase inhibitors (SDHIs). In the present study, a series of pyrazole/pyrrole carboxamides containing dinitrogen six-membered heterocyclic designed based on our reported active skeletons with dual mode action. Bioactivity results showed that target compound Q18 demonstrated superior antifungal efficacy against Colletotrichum camelliae (C. camelliae) an EC50 value 6.0 mg/L. The in vivo protective activity was 74.7% at 100 Scanning electron microscopy and transmission could disrupt surface morphology mycelia cause lipid peroxidation cell membrane, which further verified by determination relative conductivity malondialdehyde contents. Combined ergosterol content, docking between SDH CYP51, IC50 for (9.7 mg/L), it is concluded potential SDHI biosynthesis inhibitor. Thus, study provides fresh insight into amides.

Language: Английский

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Synthesis, bioactivity evaluation and theoretical study of nicotinamide derivatives containing diphenyl ether fragments as potential succinate dehydrogenase inhibitors

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1308, P. 138331 - 138331

Published: April 12, 2024

Language: Английский

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Development of chitosan‐based nanoparticles encapsulating Bacillus velezensis CMRP4490 metabolites for enhanced in vitro control of Sclerotinia sclerotiorum

The Canadian Journal of Chemical Engineering, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 4, 2024

Abstract Modern agriculture seeks to control pests and diseases in the field while maintaining production, reducing use of dangerous chemical molecules, resorting more sustainable solutions. One ways achieve these objectives is biological control. Furthermore, combined with control, nanoencapsulation techniques agents materials that are bioavailable biodegradable environment has proven be an alternative non‐renewable materials. Therefore, present work aimed develop a nanoparticle system for Sclerotinia sclerotiorum . The was produced using ionotropic gelation technique chitosan (CHI) as polymer. cell‐free supernatant (CFS) microorganism Bacillus velezensis CMRP4490 used produce nanoparticles, preliminary studies show its metabolites act nanoparticles were prepared different concentrations CHI CFS their antimicrobial activity evaluated against fungus S encapsulated samples have concentration 20%–80% 0.25% 0.8% showed 100% inhibitory effect Sclerotiorum , results obtained indicate synergistic between CFS.

Language: Английский

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Targeted Hybridization: Pyrazine‐2‐Carbohydrazide Derivatives as Promising Antitubercular and Antimicrobial Leads

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(36)

Published: Sept. 19, 2024

Abstract In an attempt to identify a new pharmacological lead which should be more potent than the established drug pyrazinamide, molecular hybridization technique was applied fuse two pharmacophore moieties: pyrazine‐2‐carbohydrazide ( 1 ) and diphenyl ether/piperazinyl derivative 2 ), isolate series of hybrid molecules. The synthesized compounds were tested in vitro for their antibacterial antimycobacterial properties against E. coli S. aureus Mycobacterium TB H 37 Rv strains. comparison reference medication (pyrazinamide) these exhibited moderate antitubercular action, with MIC value 15.625–125 µg/mL. All molecules characterized through IR, NMR mass spectrometry. Docking studies carried out order have better understanding related protein ligand receptor interactions.

Language: Английский

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Development and Biological Evaluation of New Diphenyl Ether Formylhydrazide Compounds as Potent Inhibitors of Succinate Dehydrogenase

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(47), P. 26133 - 26141

Published: Nov. 14, 2024

Succinate dehydrogenase (SDH), also recognized as succinate ubiquinone oxidoreductase (SQR), is considered one of the most promising targets for fungicide development, garnering significant international interest. We have focused on development highly effective, broad-spectrum-targeted SDH inhibitors. Using an active scaffold combining strategy, we designed and synthesized a series novel diphenyl ether formylhydrazine derivatives, compounds demonstrated broad-spectrum antifungal activity. Notably, compound

Language: Английский

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Design, Synthesis, and Fungicidal Activity of α-Methylene-γ-Butyrolactone Derivatives Bearing a Diphenyl Ether Moiety

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

The γ-butyrolactone scaffold, commonly present in natural products and bioactive compounds, has played a crucial role the development of novel pesticides. In this study, series α-methylene-γ-butyrolactone derivatives containing diphenyl ether moiety were designed synthesized using scaffold splicing strategy. Bioassays revealed that several target compounds demonstrated potent fungicidal activities, particularly against Phytophthora capsici Valsa mali. Notably, compound B7 (EC50 = 0.809 mg/L) exhibited highest antioomycete activity P. capsici, outperforming famoxadone 41.0 but being less effective than dimethomorph 0.180 mg/L). Meanwhile, C22 1.47 showed strongest antifungal V. mali, which was higher those 1.80 13.6 vivo experiments confirmed satisfactory protective curative effects better famoxadone. Additionally, found to inhibit sporangia formation, zoospore release, cystospore germination at 10 mg/L. Physiological biochemical studies indicated can induce changes mycelial morphology increase cell membrane permeability, modulate respiratory metabolism. Furthermore, both vitro enzymatic inhibition assays molecular docking analysis suggested primary mechanism action may involve binding complex III on chain. This work provides valuable insights for incorporating as agricultural agents.

Language: Английский

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