Discovery of Trifluorobutene Amide Derivatives as Potential Nematicides: Design, Synthesis, Nematicidal Activity Evaluation, SAR, and Mode of Action Study

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(3), С. 1429 - 1443

Опубликована: Янв. 8, 2024

Plant-parasitic nematodes are one of the major threats to crop protection. However, only limited nematicides currently available and confronted with a growing resistance problem, which necessitates development novel nematicides. In this study, series trifluorobutene amide derivatives was synthesized through strategy bond reversal, their nematicidal activity against Meloidogyne incognita evaluated. The bioassay showed that compounds C2, C10, C18 some analogues thereof exhibited good activity. Among them, compound C2 containing benzene ring [C26 (R = 2-CH3) C33 2-Cl)] excellent bioactivity M. in vitro. LC50/72h values reached 14.13 14.71 mg·L–1, respectively. Moreover, C10 thiophene [C43 5-CH3), C44 4-CH3), C50 5-Cl)] significant vivo inhibition rates 68.8, 65.5, 69.8% at 2.5 mg·L–1 matrix, Meanwhile, also control effects both cups microplots. structure–activity relationship (SAR) discussed detail. Comparative molecular field analysis (CoMFA) conducted develop SAR profile. preliminary mode action investigation strong on egg hatching, motility, feeding behavior, growth Caenorhabditis elegans. At same time, impact active biochemical indicators related oxidative stress influenced production ROS (reactive oxygen species), accumulation lipofuscin lipids C.

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 and development of pyrazol‐5‐ylbenzamide derivatives containing chiral oxazoline moiety as fungicides based on molecular docking

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 16, 2025

Development of novel chiral antifungal agents for effective control plant pathogens is urgently needed. In this study, a series pyrazol-5-yl-benzamide derivatives containing oxazoline moiety were rationally designed and developed based on molecular docking. The in vitro assay results indicated that compounds (rac)-4h (R1 = Et), (S)-4 h S-Et) (R)-4 R-Et) exhibited remarkable activities against Valsa mali with median concentration (EC50) values 0.24, 0.06 1.08 mg/L, respectively. Preliminary structure-activity relationships (SARs) revealed the modification substituent group at significantly affected target compounds. Furthermore, (S)-4h (87.5%) (R)-4h (84.3%) vivo protective comparable to tebuconazole V. mali. Subsequent docking analysis, succinate dehydrogenase (SDH) enzyme inhibition assays dynamic (MD) simulations verified potential class could be SDH helped explain large difference (R)-4h. Confocal laser scanning microscopy (CLSM) electron (SEM) observations confirmed these two severely disrupted mycelial morphology Theoretical calculation studies provided some insight into subsequent such derivatives. Resistance frequency showed treatments less likely produce resistant fungal strains than tebuconazole. Meanwhile, no apparent toxicity Apis mellifera L. Therefore, are candidates development fungicides crop protection. © 2025 Society Chemical Industry.

Язык: Английский

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Tailoring curcumin ternary complex nanocrystals via microfluidic mediated assembly: Stability, solubility, bioaccessibility and formation mechanism

Food Chemistry, Год журнала: 2025, Номер unknown, С. 143920 - 143920

Опубликована: Март 1, 2025

Язык: Английский

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Hit to lead optimization of carbothioate derivatives as novel succinate dehydrogenase inhibitors using a multistep virtual screening approach

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Март 26, 2025

Succinate dehydrogenase inhibitors (SDHIs) represent one of the most important fungicide subclasses for chemical control plant diseases. The identification novel SDHIs with innovative scaffolds through virtual screening is crucial pathogenic fungi management and food security. A carbothioate hit compound was identified a hierarchical protocol β-ketonitrile fungicidal as query structure. structural optimization resulted optimal A12 showed good in vitro broad-spectrum activities against Rhizoctonia solani, Sclerotiorum sclerotiorum, Botrytis cinerea Fusarium graminearum, EC50 values 4.38, 10.76, 7.69, 10.28 μg/mL, respectively. also exhibited promising vivo protective efficacy rice sheath blight. Scanning electron microscopy (SEM) observation SDH enzymatic assays revealed that served potent inhibitor, an IC50 value 4.53 μM. Computational binding mode research demonstrated formed H-bonds, cation-π T-π interaction SDH. lead further potential agricultural SDHI fungicides. © 2025 Society Chemical Industry.

Язык: Английский

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Design, Synthesis, and Bioactivity Evaluation of Novel Indene Amino Acid Derivatives as Succinate Dehydrogenase Inhibitors

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

Опубликована: Апрель 21, 2025

Succinate dehydrogenase inhibitors (SDHIs) represent one of the three predominant fungicide categories in contemporary agricultural markets, garnering an increasing level research interest. Building upon our prior work utilizing aminocyclobutanecarboxylic acid as a linker, we designed and synthesized novel series indene amino derivatives to optimize hydrophobic interactions with SDH enzyme. These demonstrated potent vitro antifungal activity against Rhizoctonia solani, Botrytis cinerea, Sclerotinia sclerotiorum, compound i19 exhibiting efficacy comparable boscalid all pathogens. Structure-activity relationship analysis coupled 3D-QSAR modeling revealed significant enzymatic inhibition enhancement, particularly i18, which showed 7.4-fold improvement porcine heart (IC50 = 0.5026 μM) versus parent structure 3.7257 μM). Lipophilicity mapping molecular docking simulations attribute this enhancement fragment-induced optimization pocket interactions. Scanning electron microscopy analogous mycelial deformation patterns between i19-treated fluxapyroxad-treated samples. Complementary DFT calculations electrostatic potential further corroborated proposed binding mode, establishing scaffold promising lead for next-generation SDHI development.

Язык: Английский

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Design, Synthesis, Nematicidal Activity Evaluation, and Mode of Action Study of Novel Trifluorobutene Ester Derivatives as Potential Nematicides

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

Опубликована: Апрель 23, 2025

Crop protection globally is under threat from infections caused by plant-parasitic nematodes (PPNs). PPNs can wreak havoc on agricultural production. However, only limited nematicides are currently available, and the growing resistance problem a concern; therefore, novel urgently needed. Thirty-three trifluorobutene ester derivatives were synthesized, then their biological activity against Meloidogyne incognita was tested in this study. Among them, nine compounds exhibited excellent vitro bioactivity M. incognita; LC50/72h values reached 1.77-3.95 mg/L. In addition, derivative of active compound above containing piperazine ring significant vivo with an inhibition rate 77.3% at 1.25 mg/L matrix. The structure-activity relationships (SARs) all synthesized analyzed, further comparative molecular field analysis (CoMFA) calculated to discuss SAR profile. preliminary mechanisms action study suggested that some had great inhibitory effect egg hatching, motility, feeding ability, growth Caenorhabditis elegans. Meanwhile, effects biochemical indices related oxidative stress indicated two could significantly promote induce toxicity through damage.

Язык: Английский

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Design, synthesis and antifungal activity of novel α‐methylene‐γ‐butyrolactone derivatives containing benzothiophene moiety

Pest Management Science, Год журнала: 2024, Номер 80(8), С. 3776 - 3785

Опубликована: Март 14, 2024

The discovery of agricultural fungicide candidates from natural products is one the key strategies for developing environment friendly fungicides with high efficiency, selectivity and unique modes-of-action. Based on previous work, a series novel α-methylene-γ-butyrolactone (MBL) derivatives containing benzothiophene moiety were designed synthesized.

Язык: Английский

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Design, Bioactivity, and Action Mechanism of Pyridinecarbaldehyde Phenylhydrazone Derivatives with Broad-Spectrum Antifungal Activity

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

Опубликована: Сен. 17, 2024

Replacing old pesticides with new pesticide varieties has been the main means to solve resistance. Therefore, it is necessary research and develop antifungal agents for plant protection. In this study, a series of pyridinecarbaldehyde phenylhydrazone derivatives were designed evaluated their inhibition activity on pathogenic fungi search novel fungicide candidates. Picolinaldehyde (

Язык: Английский

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Comprehensive Overview of the Amide Linker Modification in the Succinate Dehydrogenase Inhibitors

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(47), С. 26027 - 26039

Опубликована: Ноя. 14, 2024

Succinate dehydrogenase inhibitors (SDHIs) have become one of the most important classes agrochemical fungicides. According to data from FRAC, resistance risk for SDHIs had reached up medium and even high. In general, chemical structure mainly contained three fragments: an acid core, a hydrophobic tail, amide linker, corresponding modification directions each fragment. Among them, linker (ALM) has research hotspot design novel fungicides in recent years. We presented here detailed review on ALM strategy past decade, some them entered market. their structures, were classified into four parts: (1) linked aliphatic chain between bond (2) introducing substituents replacing hydrogen atom bond, (3) reverse extending (4) changed with other bioisosteres. Moreover, structure–activity relationship interaction mechanism ALM-SDHI SDH discussed. This aims provide global perspective development SDHIs, as well suggestions food safety management.

Язык: Английский

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