Recent Advances in Design and Development of Diazole and Diazine Based Fungicides (2014–2023)

Journal of Agricultural and Food Chemistry, Год журнала: 2024, Номер 72(28), С. 15427 - 15448

Опубликована: Июль 5, 2024

With fungal diseases posing a major threat to agricultural production, the application of fungicides control related is often considered necessary ensure world's food supply. The search for new bioactive agents has long been priority in crop protection due continuous development resistance against currently used types active compounds. Heterocyclic compounds are an inseparable part core structures numerous lead compounds, these rings constitute pharmacophores significant number developed over past decade by agrochemists. Among heterocycles, nitrogen-based play essential role. To date, diazole (imidazole and pyrazole) diazine (pyrimidine, pyridazine, pyrazine) derivatives make up important series synthetic fungicides. In recent years, many reports have published on design, synthesis, study fungicidal activity scaffolds, but there was lack comprehensive classified review nitrogen-containing scaffolds. Regarding this issue, here we reviewed articles families. current review, molecules synthesized so far based size ring.

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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Design, selective synthesis and biological activities evaluation of novel thiazol-2-ylbenzamide and thiazole-2-ylbenzimidoyl chloride derivatives

Bioorganic Chemistry, Год журнала: 2024, Номер 147, С. 107333 - 107333

Опубликована: Апрель 6, 2024

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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Asymmetric Synthesis and Bioactivity Evaluation of Chiral Oxazoline Skeleton Molecules

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

Опубликована: Фев. 6, 2025

The utilization of novel organic synthesis methods is increasingly critical in the development innovative agrochemicals. In this study, we designed and synthesized a series chiral oxazoline derivatives using one-pot method. This method involved first catalyzing asymmetric aldol addition reaction oxazolinyl esters with paraformaldehyde, followed by esterification various pharmacophore-containing carboxylic acids. Unexpectedly, many target compounds exhibited promising antifungal antioomycete activities, their absolute configurations showing pronounced enantioselective activities. Notably, compound (R)-5c demonstrated significant biological activities against Valsa mali Phytophthora capsica (EC50 = 1.023 mg/L EC50 0.149 mg/L, respectively), which were markedly superior to its enantiomer (S)-5c 9.565 0.924 respectively). vivo experiments confirmed that both curative protective effects V. P. capsici. CLSM SEM analyses further indicated 5c had distinct physiological on capsici hyphae. Moreover, acute toxicity tests zebrafish (Danio rerio) revealed significantly lower compared control drugs tebuconazole dimethomorph. Consequently, study provides valuable insights for analogues as potential

Язык: Английский

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Discovery of Novel Pyrazole/Thiazole Derivatives Containing Cyano/Thiocyanato Groups as Fungicide Candidates

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

Опубликована: Март 3, 2025

The introduction of groups with high drug activity is an effective strategy for discovering novel succinate dehydrogenase inhibitor (SDHI) fungicides, providing insights the future design SDHI fungicides higher efficacy and resistance. In this study, we designed synthesized a series pyrazole/thiazole derivatives containing cyano/thiocyanato evaluated them antifungal activity. Some compounds exhibited promising activities against tested fungi, among them, B31 B35 displayed excellent in vitro Rhizoctonia solani EC50 values 1.83 1.08 μg/mL, which were close proximity to commercial fungicide boscalid (EC50 = 0.87 μg/mL). For Altemaria solani, compound (11.14 μg/mL) showed good below (15.31 SAR studies further reveal that induced conjugated interactions between target receptor facilitate electron transport process, contributing its preliminary mechanistic studies, mycelium cells irregular abnormal state under SEM TEM observation caused production accumulation ROS. Molecular docking results SDH enzyme assays indicate has potential be fungicide.

Язык: Английский

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Quality control strategy for postharvest fragrant pears: pathogenesis of brown rot caused by Monilinia fructicola and protective mechanism of carvacrol

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Май 10, 2025

Abstract BACKGROUND Brown rot, triggered by Monilinia fructicola , causes substantial postharvest losses. However, the widespread application of chemical fungicides has development resistance in pathogenic fungi and accumulation hazardous residues. Plant‐derived offer an eco‐friendly alternative to owing their low toxicity broad‐spectrum activity. RESULTS secreted acidic substances that reduced pH while increasing pectinase (PG) cellulase (Cx) activities 230.6% 59.8%, respectively, leading increase 85.9% hydrogen peroxide (H 2 O ), slight increases superoxide dismutase (SOD; 15.1%), catalase (CAT; 5.8%) peroxidase (POD; 9.2%), elevations malondialdehyde (MDA content conductivity 48.8% 49.4%. Meanwhile, it defense enzyme activity [phenylalanine ammonialyase (PAL), β‐1,3‐glucanase (GLU), Chitinase (CHI)] secondary metabolite secretion (lignin, total phenol, flavonoids). By contrast, carvacrol treatment inhibited M . vitro [median effective concentration (EC 50 ) 24.2 mg L −1 ] lesion diameter expansion vivo Additionally, controls values decreases Cx PG activity, reduces H MDA enhancing antioxidant enzymes. CVR restores system promoting enzymes secretion, thus achieving a protective effect against invasion. CONCLUSION This study demonstrated can pears protect them from pathogens, prolonging storage period. research provides novel approach controlling brown rot fruit caused M. which profound implications for global industry is great economic environmental significance. © 2025 Society Chemical Industry.

Язык: Английский

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Design and synthesis of novel cinnamamide derivatives‐based lansiumamide B as potent fungicidal candidates

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Май 10, 2025

Abstract BACKGROUND Natural products have been and continue to be a significant resource for developing environmentally friendly pesticides with distinctive structures mechanisms. Lansiumamide B (LB), cinnamamide compound extracted from Clausena lansium seeds, has served as the lead design synthesis of series derivatives. The fungicidal activity these derivatives evaluated. RESULTS majority proposed compounds displayed moderate considerable antifungal efficacy against tested pathogenic fungi oomycetes, some exhibiting broad‐spectrum activities. Compound 26 showed excellent Colletotrichum orbiculare in vitro , median effective concentration (EC 50 ) value 0.36 μg/mL, better than positive control boscalid (0.95 μg/mL) LB (60.18 μg/mL). In vivo also exhibited greater C. LB. Furthermore, study found that mycelium cell wall was damaged after treatment through observation mycelial morphology ultrastructure . Consequently, growth inhibited. CONCLUSION results indicated containing 1,2,3,4‐tetrahydroisoquinoline moiety represent novel class active scaffold, potential developed into new type fungicide. © 2025 Society Chemical Industry.

Язык: Английский

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Exploring 2,6-DibromoBODIPYs as Potential Photosensitizers for Photodynamic Inactivation of Phytopathogenic Fungi

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

Опубликована: Июнь 4, 2025

Antimicrobial photodynamic therapy (aPDT) is a promising alternative strategy to overcoming fungal resistance. It based on the generation of reactive oxygen species (ROS) upon irradiation suitable photosensitizer (PS) with abundant natural sunlight. Currently, further application aPDT in controlling plant diseases has been hampered by limited access PSs. In this work, we designed and synthesized set 2,6-dibromoBODIPYs investigated their performance as novel PSs for against eight highly destructive pathogenic fungi. Most these target compounds showed excellent broad-spectrum antifungal activities, demonstrated bioassay results, entering into interior hyphal cells situ generating ROS destroy subcellular organelles. Among those, compound 17a exhibits highest singlet (1O2) efficiency, an EC50 value each five common pathogens (0.955, 0.883, 0.281, 1.09, 1.05 mg/L Valsa mali, Sclerotinia sclerotiorum, Rhizoctonia solani, Fusarium graminearum, Trichoderma viride, respectively). These values are comparable or even slightly better than those achieved commercial PS Rose Bengal (RB) fungicide thifluzamide. capable inhibiting growth R. solani detached leaves rice provides effective protection curative activities at 50 mg/L. addition, also features compatibility low toxicity nontargeted organisms including Apis mellifera L. results indicate that may be used potential killing phytopathogenic

Язык: Английский

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Evaluation of the antifungal activity of novel bis-pyrazole carboxamide derivatives and preliminary investigation of the mechanism

Bioorganic Chemistry, Год журнала: 2024, Номер 153, С. 107779 - 107779

Опубликована: Сен. 1, 2024

Язык: Английский

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