3D-QSAR-Directed Synthesis of Halogenated Coumarin-3-Hydrazide Derivatives: Unveiling Their Potential as SDHI Antifungal Agents

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(21), С. 11938 - 11948

Опубликована: Май 16, 2024

The pursuit of new succinate dehydrogenase (SDH) inhibitors is a leading edge in fungicide research and development. use 3D quantitative structure–activity relationship (3D-QSAR) models significantly enhances the development compounds with potent antifungal properties. In this study, we leveraged natural product coumarin as molecular scaffold to synthesize 74 novel 3-coumarin hydrazide derivatives. Notably, 4ap (0.28 μg/mL), 6ae (0.32 6ah (0.48 μg/mL) exhibited exceptional vitro effectiveness against Rhizoctonia solani, outperforming commonly used boscalid (0.52 μg/mL). Furthermore, 4ak (0.88 (0.61 (0.65 6ak (1.11 showed significant activity Colletotrichum orbiculare, surpassing both SDHI (43.45 broad-spectrum carbendazim (2.15 Molecular docking studies SDH enzyme assays indicate that compound 4ah may serve promising fungicide. Our ongoing aims refine 3D-QSAR model further, enhance design, conduct additional bioactivity assays.

Язык: Английский

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Coumarin derivatives containing the 1,3,4 oxadiazole/thiadiazole moiety discovered as potential anti-tobacco mosaic virus agents

Molecular Diversity, Год журнала: 2025, Номер unknown

Опубликована: Янв. 20, 2025

Язык: Английский

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

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

Опубликована: Апрель 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

Язык: Английский

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Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(22), С. 12300 - 12318

Опубликована: Май 27, 2024

Scaffold structures, new mechanisms of action, and targets present enormous challenges in the discovery novel pesticides. The scaffolds is basis for continuous development modern agrochemicals. Identification a good scaffold such as triazole, carbamate, methoxy acrylate, pyrazolamide, pyrido-pyrimidinone mesoionic, bisamide often leads to series In addition, pesticides with same target, including inhibitors succinate dehydrogenase (SDH), oxysterol-binding-protein, p-hydroxyphenyl pyruvate dioxygenase (HPPD), may have or similar structure. Recent years witnessed significant progress using natural products bridges. recent years, there been increasing reports on application benzopyran compounds pesticides, especially osthole coumarin. A systematic comprehensive review active agricultural chemicals helpful promote discussion compounds. Therefore, this work systematically reviewed research derivatives chemicals, summarized antiviral, herbicidal, antibacterial, fungicidal, insecticidal, nematicidal acaricidal activities compounds, discussed structural–activity relationship mechanism action. some fragments were recommended further optimize chemical structure based reference information.

Язык: Английский

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Recent Advances of Coumarin-Type Compounds in Discovery of Pesticides

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

Опубликована: Ноя. 18, 2024

Coumarin, a naturally occurring active ingredient with various biological activities in pesticides, is commonly found plants belonging to the Rutaceae and Apiaceae families. Thanks its unique structural properties natural benefits, coumarin derivatives exhibit wide range of physiological activities, including insecticidal, antifungal, antibacterial, herbicidal, antiviral properties. These compounds have attracted considerable interest field pesticide development, although there lack comprehensive reviews on their use pesticides. This Review aims provide detailed overview applications covering structure–activity relationship analyses, mechanisms action. It hoped that this will offer new insights into discovery these development.

Язык: Английский

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Exploring Brominated Aromatic Butenolides from Aspergillus terreus EGF7-0-1 with Their Antifungal Activities

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(36), С. 19869 - 19882

Опубликована: Сен. 2, 2024

Fungal diseases could severely harm agricultural productions. To develop new antifungal agents, based on the Global Natural Products Social Molecular Networking, typical bromine isotope peak ratios, and ultraviolet absorptions, cultivation of soft coral-derived endophytic fungi

Язык: Английский

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Design, Synthesis, Antifungal Evaluation, and Three-Dimensional Quantitative Structure–Activity Relationship of Novel 5-Sulfonyl-1,3,4-thiadiazole Flavonoids

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

Опубликована: Сен. 17, 2024

Plant pathogenic fungi frequently disrupt the normal physiological and biochemical functions of plants, leading to diseases, compromising plant health, ultimately reducing crop yield. This study aimed address this challenge by identifying antifungal agents with innovative structures novel mechanisms action. We designed synthesized a series flavonoid derivatives substituted 5-sulfonyl-1,3,4-thiadiazole evaluated their activity against five phytopathogenic fungi. Most demonstrated excellent

Язык: Английский

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Rational design and discovery of novel hydrazide derivatives as potent succinate dehydrogenase inhibitors inspired by natural d/l‐camphor

Pest Management Science, Год журнала: 2024, Номер unknown

Опубликована: Окт. 18, 2024

Abstract BACKGROUND Succinate dehydrogenase inhibitors (SDHIs) have rapidly become one of the fastest‐growing categories fungicides used against plant pathogenic fungi. Recent research advancements emphasized that structural modifications SDHIs using naturally sourced scaffolds represent an innovative strategy for developing new, highly effective, broad‐spectrum fungicides. A novel series d/l ‐camphorhydrazide derivatives potentially targeting fungal succinate (SDH) were designed, synthesized and evaluated their antifungal effects Rhizoctonia solani , Fusarium graminearum Valsa mali Botrytis cinerea . RESULTS Amongst them, compounds A1‐7 ( d ‐camphor) A2‐7 l displayed excellent in vitro activity R. with median effective concentration (EC 50 ) values 0.38 0.48 μg mL −1 which obviously superior to boscalid (0.87 ). A2‐5 ‐camphor, EC = 3.27 exhibited good V. (2.13 − 1), A2‐21 (5.2 A1‐5 (5.15 showed F. below (5.85 Preliminary mechanistic studies, scanning transmission electron microscopy, indicated compound induced disordered entanglement hyphae, shrinkage hyphal surfaces, vacuole swelling rupture, disrupted normal growth. Additionally, production accumulation reactive oxygen species, mitochondrial membrane potential, effectively inhibited germination formation sclerotia Moreover, molecular docking results SDH enzyme assays yielded promising outcomes. CONCLUSION In this study, designed optimized emerged as candidates SDH‐targeting fungicides, demonstrating strong activity. These hold potential new agents further research. © 2024 Society Chemical Industry.

Язык: Английский

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Synthesis, Molecular Electron Density Theory Study, Molecular Docking, and Pharmacological Evaluation of New Coumarin–Sulfonamide–Nitroindazolyl–Triazole Hybrids as Monoamine Oxidase Inhibitors

International Journal of Molecular Sciences, Год журнала: 2024, Номер 25(12), С. 6803 - 6803

Опубликована: Июнь 20, 2024

Inhibitors of monoamine oxidases (MAOs) are interest for the treatment neurodegenerative disorders and other human pathologies. In this frame, present work describes different synthetic strategies to obtain MAO inhibitors via coupling aminocoumarin core with arylsulfonyl chlorides followed by copper azide-alkyne cycloaddition, leading coumarin-sulfonamide-nitroindazolyl-triazole hybrids. The nitration position on coumarin moiety was confirmed through nuclear magnetic resonance spectroscopy molecular electron density theory in order elucidate mechanism selectivity electrophilic aromatic substitution reaction. derivatives were evaluated their inhibitory potency against cholinesterases. Molecular docking calculations provided a rational binding mode best compounds series A B. identified hybrids 14a-c as novel inhibitors, selective action isoform B, potential combat neurological diseases.

Язык: Английский

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Design, Synthesis and Anti-Fungal Activities of Non-Amides Coumarin Derivatives As Potential Sdh Inhibitors

Опубликована: Янв. 1, 2024

Язык: Английский

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