Novel Pyrazole Acyl(thio)urea Derivatives Containing a Biphenyl Scaffold as Potential Succinate Dehydrogenase Inhibitors: Design, Synthesis, Fungicidal Activity, and SAR

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(5), P. 2512 - 2525

Published: Jan. 29, 2024

As part of a program to discover novel succinate dehydrogenase inhibitor fungicides, series new pyrazole acyl(thio)urea compounds containing diphenyl motif were designed and synthesized. Their structures confirmed by

Language: Английский

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Discovery of Highly Efficient Novel Antifungal Lead Compounds Targeting Succinate Dehydrogenase: Pyrazole-4-carboxamide Derivatives with an N-Phenyl Substituted Amide Fragment

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(49), P. 19312 - 19323

Published: Nov. 29, 2023

Developing environmentally friendly fungicides is crucial to tackle the issue of rising pesticide resistance. In this study, a series novel pyrazole-4-carboxamide derivatives containing N-phenyl substituted amide fragments were designed and synthesized. The structures target compounds confirmed by 1H NMR, 13C HRMS, crystal structure most active compound N-(1-(4-(4-(tert-butyl)benzamido)phenyl)propan-2-yl)-3-(difluoromethyl)-N-methoxy-1-methyl-1H-pyrazole-4-carboxamide (U22) was further determined X-ray single-crystal diffraction. bioassay results indicated that 26 possessed good in vitro antifungal activity against Sclerotinia sclerotiorum with EC50 values for U12, U13, U15, U16, U18, U22, U23 being 4.17 ± 0.46, 8.04 0.71, 7.01 12.77 1.00, 8.11 0.70, 0.94 0.11, 9.48 0.83 μg·mL–1, respectively, which similar controls bixafen (6.70 0.47 μg·mL–1), fluxapyroxad (0.71 0.14 pydiflumetofen (0.06 0.01 μg·mL–1). Furthermore, vivo S. U12 (80.6%) U22 (89.9%) excellent preventative efficacy at 200 same as control (82.4%). Scanning electron microscopy transmission studies found could destroy hyphal morphology damage mitochondria, cell membranes, vacuoles. molecular docking succinate dehydrogenase (SDH) they interact well site SDH. This study validated our approach design strategy produce an enhanced biological compared parent structure.

Language: Английский

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Pyrazole derivatives: Recent advances in discovery and development of pesticides

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110912 - 110912

Published: Feb. 1, 2025

Language: Английский

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Novel 5-(Trifluoromethyl)-1,2,4-oxadiazole-Based Pyrimidin-4-ether Histone Deacetylase Inhibitors for Controlling Rust Disease: Design, Synthesis, Activity, and Structure–Activity Relationship

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

Published: Feb. 12, 2025

Rust disease, an important plant pathogen, can lead to reduced crop or fruit production. Trifluoromethyloxadiazole (TFMO) is a class of histone deacetylase inhibitors (HDACs). Herein, series 5-(trifluoromethyl)-1,2,4-oxadiazole (TFMO)-based pyrimidin-4-ether derivatives were designed and synthesized. Antirust bioassay results TFMOs showed that some them possessed excellent activities against rust pathogens, such as Puccinia sorghi, Phakopsora pachyrhizi, rubigo. The most active compound, 3-(5-(((6-(difluoromethyl)pyrimidin-4-yl)oxy)methyl)thiophen-2-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole (XII6), exhibited 50% control P. pachyrhizi at 0.780 mg/L, which was significantly better than the commercial fungicide azoxystrobin (0%) same concentration. field trial indicated compound effect rubigo 116 g a.i./ha. acute toxic XII6 has low toxicity. Furthermore, enzyme activity strong, nonselective HDAC inhibitor. Finally, structure–activity relationship established, XII6-HDAC binding mode carried out based on crystal structure hHDAC1, hHDAC4, hHDAC6. This work provided for further optimization.

Language: Английский

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Synthesis and Biological Activities of Novel Pyrazole Carboxamides Containing an Aryloxypyridyl Ethylamine Module

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(7), P. 3342 - 3353

Published: Feb. 9, 2024

Pyrazole carboxamide is widely utilized in agricultural crop protection. In this research, we synthesized two classes of compounds, namely, pyrazole-5-carboxamide (4a) and pyrazole-4-carboxamide (4b), which are distinguished by the inclusion N-1-(6-aryloxypyridin-3-yl) ethylamine skeleton. This design was inspired frequent occurrence diaryl ether modules pesticide molecules. The bioassay results revealed that some compounds 4a exhibit higher insecticidal activity (IA) than 4b, while 4b display stronger fungicidal compared to 4a. suggests pyrazolyl plays a crucial role determining selectivity these toward different biological species. Notably, compound 4a-14 not only retains potent tolfenpyrad, exact lead 4a, against Lepidoptera pest Plutella xylostella Thysanoptera Frankliniella occidentalis but also shows excellent IA pests with piercing-sucking mouthparts, such as Aphis craccivora Koch Nilaparvata lugens. research has important implications for control mouthparts development new insecticides fungicides. findings highlight potential inhibitory complex I an effective target pests, particularly those have developed resistance traditional insecticides. Additionally, it sheds light on binding mode 4b-11 II, serves negative reference SDHI study emphasizes significance species identifies avenues future enhancing amino modules. discovery (S)-4a-14 presents promising candidate provides valuable insights into effect respiratory chain insect pests. These both theory practice, offering directions strategies fungicide development.

Language: Английский

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Design, Synthesis, and Acaricidal/Insecticidal Activities of New Phenylpyrazole Derivatives Comprising an Imide Moiety

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(27), P. 15276 - 15283

Published: June 29, 2024

Using nicofluprole as the lead compound, we designed and synthesized a series of new phenylpyrazole analogues through substituting methyl group on nitrogen atom amide with an acyl group. Bioassay results showed that compounds A12–A17 1-cyanocyclopropimide exhibited outstanding insecticidal activity. The LC50 values for against Tetranychus cinnabarinus ranged from 0.58 to 0.91 mg/L. Compound A15 value 0.29 3.10 mg/L Plutella xylostella Myzus persicae, respectively. Molecular docking indicated potential binding interactions compound gamma-aminobutyric acid receptor. Additionally, density functional theory calculations implied structure might be essential its biological Phenylpyrazole derivatives, containing fragment, have further development insecticides.

Language: Английский

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(NH₄)₂S₂O₈ promoted tandem radical cyclization of quinazolin-4(3H)-ones with oxamic acids for the construction of fused quinazolinones under metal-free conditions

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(11), P. 2241 - 2251

Published: Jan. 1, 2024

A novel cascade radical addition/cyclization reaction of non-activated olefins and oxamic acids has been proposed.

Language: Английский

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Computer‐aided design of novel anthranilic diamides containing fluorinated alkoxy groups as potential ryanodine receptor insecticides

Pest Management Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 29, 2025

Abstract BACKGROUND Increasing the diversity of lead compounds has been shown to enhance efficacy diamide insecticides. Fifty novel were precisely designed and synthesized utilizing fragment‐based assembly virtual screening coupling. RESULTS The median lethal concentration (LC 50 ) values X‐30 X‐40 against Mythimna separata 0.09 0.08 mg L −1 , respectively, which are lower than that chlorantraniliprole (CHL, 0.11 ). Notably, X‐10, X‐18, X‐25, X‐32 X‐43 had corresponding LC 2.0 × 10 −4 5.0 6.0 9.0 7.0 Plutella xylostella respectively. best compound X‐10 exhibited five‐fold greater CHL (1.0 −3 X‐21, X‐29, Spodoptera frugiperda 0.27, 0.26 0.25 slightly (0.33 In case Ostrinia furnacalis showed good with comparable those (1.38 versus 1.57 Calcium imaging experiments demonstrated X‐21 acted on S. ryanodine receptors. Furthermore, this series safety toward nontarget mammals compared CHL. CONCLUSION introduction fluorinated alkoxy groups at 3‐position pyrazole ring leads insecticidal activity improved insect selectivity. © 2025 Society Chemical Industry.

Language: Английский

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Synthetic aspects, structural insights and pharmacological potential of pyrazole derivatives: an overview

Deleted Journal, Journal Year: 2025, Volume and Issue: 7(2)

Published: Feb. 13, 2025

Abstract There is an increase in infectious diseases every year. Heterocyclic compounds have been use as drugs for a long time. Amongst many heterocyclic derivatives, the containing pyrazole core has limelight because of its relative ease synthesis and excellent biological activities. Pyrazoles are aromatic consisting ring structure where two nitrogen atoms adjacent to each other contain three carbon atoms. Over years pyrazoles explored variety pharmacological applications. Herein, this review overviews information related industrially important pyrazoline scaffolds their applications, recent literature on synthesizing providing explanation activity by focusing structural relationship hence affording ideas design scaffolds. Graphical abstract

Language: Английский

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Isoxazoline: An Emerging Scaffold in Pesticide Discovery

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

Published: April 3, 2025

Isoxazolines are five-membered heterocycle compounds with a wide range of pharmacological and pesticidal activities. Numerous marketed pesticides contain an isoxazoline motif as key skeleton. Isoxazoline have relatively simple syntheses biological activities against various weeds, bacteria, other pests. In recent years, they received increasing attention widely used in organic chemistry research, such intermediate catalyst ligands synthesis. They also excellent optoelectronic properties the field materials. Hence, exploration derivatives remains important research area pesticide discovery. This review provides up-to-date overview utilized discovery, highlighting their structure properties. It summarizes relevant publications from last 10 offering insights into advancements this research.

Language: Английский

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