Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(17), С. 9599 - 9610

Опубликована: Апрель 22, 2024

In the search for novel succinate dehydrogenase inhibitor (SDHI) fungicides to control Rhizoctonia solani, thirty-five pyrazole-4-carboxamides bearing either an oxime ether or ester group were designed and prepared based on strategy of molecular hybridization, their antifungal activities against five plant pathogenic fungi also investigated. The results indicated that majority compounds containing demonstrated outstanding in vitro activity R. some displayed pronounced Sclerotinia sclerotiorum Botrytis cinerea. Particularly, compound 5e exhibited most promising solani with EC50 value 0.039 μg/mL, which was about 20-fold better than boscalid (EC50 = 0.799 μg/mL) 4-fold more potent fluxapyroxad 0.131 μg/mL). Moreover, detached leaf assay showed could suppress growth rice leaves significant protective efficacies (86.8%) at 100 superior (68.1%) (80.6%), indicating application prospects. addition, (SDH) enzymatic inhibition revealed generated remarkable SDH (IC50 2.04 μM), obviously those 7.92 μM) 6.15 μM). Furthermore, SEM analysis caused a disruption characteristic structure morphology hyphae, resulting damage. docking fit into identical binding pocket through hydrogen bond interactions as well fluxapyroxad, they had similar mechanism. density functional theory electrostatic potential calculations provided useful information regarding electron distribution transfer, contributed understanding structural features mechanism lead compound. These findings suggested be candidate SDHI warranting further investigation.

Язык: Английский

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Design, Synthesis, and Antifungal Activities of Novel Potent Fluoroalkenyl Succinate Dehydrogenase Inhibitors

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(26), С. 14535 - 14546

Опубликована: Июнь 21, 2024

The development of new fungicide molecules is a crucial task for agricultural chemists to enhance the effectiveness fungicides in production. In this study, series novel fluoroalkenyl modified succinate dehydrogenase inhibitors were synthesized and evaluated their antifungal activities against eight fungi. results from

Язык: Английский

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Design, Synthesis, and Biological Evaluation of Novel Pyrazol-5-yl-benzamide Derivatives Containing Oxazole Group as Potential Succinate Dehydrogenase Inhibitors

Journal of Agricultural and Food Chemistry, Год журнала: 2022, Номер 70(43), С. 13839 - 13848

Опубликована: Окт. 21, 2022

A series of pyrazol-5-yl-benzamide derivatives containing the oxazole group were designed and synthesized as potential SDH inhibitors. According to results bioassays, most target compounds displayed moderate-to-excellent in vitro antifungal activities against Valsa mali, Sclerotinia scleotiorum, Alternaria alternata, Botrytis cinerea. Among them, C13, C14, C16 exhibited more excellently inhibitory S. sclerotiorum than boscalid (EC50 = 0.96 mg/L), with EC50 values 0.69, 0.26, 0.95 mg/L, respectively. In vivo experiments on rape leaves cucumber showed that C13 C14 considerable protective effects boscalid. SEM analysis indicated significantly destroyed typical structure morphology scleotiorum hyphae. respiratory inhibition effect assays, (28.0%) (33.9%) a strong respiration rate mycelia, which was close (30.6%). The molecular docking could form interactions key residues TRP O:173, ARG P:43, TYR Q:58, MET P:43 SDH. Furthermore, mechanism these demonstrated by enzymatic assay. These demonstrate can be developed into novel inhibitors for crop protection.

Язык: Английский

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Synthesis, Antifungal Evaluation, 3D-QSAR, and Preliminarily Mechanism Study of Novel Chiral Mandelic Acid Derivatives

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(20), С. 7631 - 7641

Опубликована: Май 14, 2023

To investigate the effect of spatial configuration on biological activity compounds, a series chiral mandelic acid derivatives with moiety 1,3,4-oxadiazole thioether have been designed and synthesized. Bioassay results demonstrated that most title compounds S-configuration exhibited better in vitro antifungal against three plant fungi, such as H3' (EC50 = 19.3 μg/mL) Gibberella saubinetii, which was approximately 16 times higher than H3 317.0 μg/mL). CoMFA CoMSIA models were established for 3D-QSAR analysis provided an important support further optimization this compounds. Comparing preliminary mechanism studies between enantiomers (H3 H3') found compound (H3') stronger ability to destroy surface structure G. saubinetii mycelia, causing leakage intracellular substances accelerate growth hyphae be inhibited. The novel view active deep study pesticides.

Язык: Английский

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Discovery of Novel Pyrazol-5-yl-benzamide Derivatives Containing a Thiocyanato Group as Broad-Spectrum Fungicidal Candidates

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(46), С. 17700 - 17712

Опубликована: Ноя. 8, 2023

In an effort to promote the development of new fungicides, a series 48 novel N-(1-methyl-4-thiocyanato-1H-pyrazol-5-yl)-benzamide derivatives A1-A36 and B1-B12 were designed synthesized by incorporating thiocyanato group into pyrazole ring, their fungicidal activities evaluated against Sclerotinia sclerotiorum, Valsa mali, Botrytis cinerea, Rhizoctonia solani, Phytophthora capsici. in vitro antifungal/antioomycete assay, many target compounds exhibited good broad-spectrum activities. Among them, compound A36 displayed best antifungal activity V. mali with EC50 value 0.37 mg/L, which was significantly higher than that positive controls fluxapyroxad (13.3 mg/L) dimethomorph (10.3 mg/L). Meanwhile, B6 antioomycete P. capsici 0.41 azoxystrobin (29.2 but lower (0.13 Notably, A27 inhibitory B. R. S. respective values 0.71, 1.44, 1.78, 0.87, 1.61 mg/L. The vivo experiments revealed presented excellent protective curative efficacies capsici, similar control dimethomorph. Scanning electron microscopy (SEM) transmission (TEM) analyses showed could change mycelial morphology severely damage ultrastructure results SDH enzymatic inhibition indicated effectively inhibit (PcSDH). Furthermore, molecular docking analysis demonstrated significant hydrogen bonds Pi-S bonding between key amino acid residues PcSDH, explain probable mechanism action. Collectively, these studies provide valuable approach expanding spectrum pyrazol-5-yl-benzamide derivatives.

Язык: Английский

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Design, Synthesis, and Herbicidal Activity of Pyrazole Amide Derivatives as Potential Transketolase Inhibitors

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(7), С. 3334 - 3341

Опубликована: Фев. 12, 2024

The design and synthesis of new herbicidal active compounds based on a target are great significance for the development herbicides. Transketolase (TK) plays key role in Calvin cycle plant photosynthesis has been confirmed as potential candidate to develop discover To obtain with ultraefficient targeting TK, series pyrazole amide derivatives were designed synthesized through structural optimization lead compound 4u TK target. bioassay results showed that 6ba 6bj displayed highly inhibitory effect root inhibition about 90% against Digitaria sanguinalis (DS) 80% Amaranthus retroflexus (AR) Setaria viridis (SV) by small cup method, which was better than positive control mesotrione nicosulfuron. Furthermore, exhibited an excellent (against DS) over SV) at dosage 150 g ingredient/ha foliar spray method. enzyme activity test consistent activities. Also, molecular docking analysis went deep into cavity bound strong interaction, might act TK. Above all, promising herbicide Hence, they could be developed more efficient herbicides further optimization.

Язык: Английский

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Design, Synthesis, Antifungal Activity, and Action Mechanism of Pyrazole-4-carboxamide Derivatives Containing Oxime Ether Active Fragment As Succinate Dehydrogenase Inhibitors

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(20), С. 11308 - 11320

Опубликована: Май 9, 2024

The dearomatization at the hydrophobic tail of boscalid was carried out to construct a series novel pyrazole-4-carboxamide derivatives containing an oxime ether fragment. By using fungicide-likeness analyses and virtual screening, 24 target compounds with theoretical strong inhibitory effects against fungal succinate dehydrogenase (SDH) were designed synthesized. Antifungal bioassays showed that compound E1 could selectively inhibit in vitro growth R. solani, EC50 value 1.1 μg/mL superior agricultural fungicide (2.2 μg/mL). observations by scanning electron microscopy (SEM) transmission (TEM) demonstrated reduce mycelial density significantly increase mitochondrial number mycelia cytoplasm, which similar phenomenon treated boscalid. Enzyme activity assay had significant effect SDH from IC50 3.3 μM (7.9 μM). mode action further analyzed molecular docking dynamics simulation studies. Among them, hydrogen bonds more SDH-E1 complex than SDH-boscalid complex. This research on strategy benzene ring for constructing pyrazole-4-carboxamides fragment provides unique thought design new antifungal drugs targeting SDH.

Язык: Английский

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1,3,4-Oxadiazole Sulfonamide Derivatives Containing Pyrazole Structures: Design, Synthesis, Biological Activity Studies, and Mechanism Study

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

Опубликована: Янв. 29, 2025

Sulfonamide derivatives have been widely used for pesticide research in recent years. Herein, 1,3,4-oxadiazole sulfonamide containing a pyrazole structure were synthesized, and their structure-activity relationship was studied. Bioactivity tests showed the remarkable efficacy of most synthesized compounds. Especially Xanthomonas oryzae pv oryzae, A23 exhibited 100% inhibition at 100 mg/L, surpassing bismerthiazol (99.3%), 90% 50 outperforming thiodiazole copper (84.5%), with an EC50 5.0 markedly more active than (23.9 mg/L) (63.5 mg/L). Initial investigations into antimicrobial mechanisms involved series biochemical analyses, including bacterial growth rate analysis, scanning electron microscopy, biofilm formation experiments, molecular docking analyses. Notably, considerably inhibited Xoo biofilms, disrupting integrity cell membranes. Co-analysis transcriptomics proteomics revealed capability to regulate pathways such as tryptophan metabolism phenylpropanoid biosynthesis, enhancing innate immunity rice activating its disease resistance. Thus, emerges potential immunoinducible lead compound discovery highly immune-inducing agents.

Язык: Английский

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

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

Опубликована: Фев. 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.

Язык: Английский

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Discovery of α-Methylene-γ-Butyrolactone Derivatives with Hydrazide Moieties as Novel Fungicidal Agents

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

Опубликована: Апрель 10, 2025

To discover novel fungicides with unique structures, a series of α-methylene-γ-butyrolactone derivatives were designed and synthesized by incorporating flexible amide or hydrazide chain through active substructure splicing linker modification strategies. Bioassay assessments demonstrated that certain hydrazide-containing compounds have potent fungicidal efficacy. Notably, compound 7IIj exhibited broad-spectrum antifungal activity, EC50 values as low 0.179, 0.301, 0.647, 0.549, 0.789 mg/L against Rhizoctonia solani, Physalospora piricola, Botrytis cinerea, Gaeumanomyces graminis, Valsa mali, respectively. In vivo experiments confirmed the effective activity 7IIj, showing an inhibitory rate 69.7% V. mali on apple twigs at 200 mg/L. Additionally, concentration 100 mg/L, significant protective curative effects R. solani rice plants. Research mechanism action revealed could disrupt hyphal morphology, induce reactive oxygen species (ROS) accumulation, affect mitochondrial membrane potential (MMP), interfere respiratory metabolism binding to complex II. Molecular docking analysis showed interactions TRP 173, TYR 58, ARG 43 in succinate dehydrogenase (SDH) site, resembling mode fluxapyroxad. These findings suggest holds SDH inhibitor for agricultural disease control.

Язык: Английский

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