Design, synthesis, X‐ray crystal structure, and antifungal evaluation of new acetohydrazide derivatives containing a 4‐thioquinazoline moiety DOI

Guangmin Tian,

Mingyan Yi,

T F Yan

et al.

Pest Management Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Abstract BACKGROUND To find efficient agricultural fungicides, 29 new 4‐thioquinazoline‐containing acetohydrazide derivatives were prepared and tested for their fungicidal properties. RESULTS All of the target compounds characterized by 1 H 13 C nuclear magnetic resonance high‐resolution mass spectrometry techniques, molecular structure compound A2 was verified single‐crystal X‐ray diffraction measurement. The experimental results revealed that many from this series had impressive inhibition efficacies in vitro against fungi. For example, A25 identified as best agent Rhizoctonia solani with an EC 50 (half‐maximal effective concentration) value 0.66 μg mL −1 , superior to those commercial fungicides chlorothalonil, carbendazim boscalid. Additionally, displayed favorable protection curative activities vivo rice sheath blight caused R . Antifungal mechanistic studies on indicated exerted its strong anti ‐R effects probably through fungal succinate dehydrogenase activity [half‐maximal inhibitory concentration (IC ) = 4.88 μ m ] impairment cell membrane integrity, based enzymatic bioassays, docking studies, scanning transmission electron microscopy observations. CONCLUSION Acetohydrazide containing 4‐thioquinazoline moiety potential be employed lead developing more near future. © 2024 Society Chemical Industry.

Language: Английский

Design, Synthesis, and 3D-QASR of 2-Ar-1,2,3-triazole Derivatives Containing Hydrazide as Potential Fungicides DOI

Xue Yin,

Xiaofeng Liu, Xia Wu

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(22), P. 12415 - 12424

Published: May 23, 2024

A series of novel 2-Ar-1,2,3-triazole derivatives were designed and synthesized based on our previously discovered active compound 6d against Rhizoctonia solani. Most these compounds exhibited good antifungal activity R. solani at a concentration 25 μg/mL. Based the results biological activity, we established three-dimensional quantitative structure–activity relationship (3D-QSAR) model that guided synthesis 7y. Compound 7y superior (EC50 = 0.47 μg/mL) compared to positive controls hymexazol 12.80 tebuconazole 0.87 μg/mL). Furthermore, demonstrated better protective than aforementioned two commercial fungicides in both detached leaf assays greenhouse experiments, achieving 56.21% 65.75% efficacy, respectively, 100 The ergosterol content was determined molecular docking performed explore mechanism molecules. DFT calculation MEP analysis illustrate this study. These suggest could serve as lead for controlling

Language: Английский

Citations

9

Design, bioactivity and mechanism of N′-phenyl pyridylcarbohydrazides with broad-spectrum antifungal activity DOI
Yuhao Zhang,

Bohang Zhou,

Pengan Wei

et al.

Molecular Diversity, Journal Year: 2024, Volume and Issue: unknown

Published: June 26, 2024

Language: Английский

Citations

7

Discovery of Novel Quinazolinone-2-carbohydrazide Derivatives as Effective Succinate Dehydrogenase Inhibitors and Biosafety Assessment on Rice and Zebrafish DOI

Taisen Yan,

Hong Li, Sha Li

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: 73(9), P. 5054 - 5066

Published: Feb. 18, 2025

To develop potent and safe antifungal agents in agriculture, a total of 48 novel quinazolinone-2-carbohydrazide derivatives were designed synthesized based on the pharmacophore hybridization method. The bioassay results demonstrated that many compounds exhibited powerful broad-spectrum inhibition activities vitro against tested fungi. For instance, E23 F23 possessed EC50 (half-maximal effective concentration) values 0.41 0.47 μg/mL Rhizoctonia solani, comparable to commercial fungicide Boscalid (EC50 = 0.49 μg/mL). Additionally, compound also pronounced effects Verticillium dahliae, Alternaria Colletotrichum gloeosporioides with 0.27, 1.15, 0.27 μg/mL, respectively. In vivo assays rice plants revealed this at 200 nearly equipotent curative protective R. as compared positive controls Carbendazim. Moreover, had an obvious activity fungal succinate dehydrogenase (SDH) from solani half-maximal concentration (IC50) 11.76 μM, interactions between SDH enzyme further confirmed by molecular docking studies. Furthermore, presence triggered morphological changes mycelia increased conductivity permeability cell membranes. Interestingly, built three-dimensional quantitative structure-activity relationship (3D-QSAR) models showed electrostatic effect played more important role maintaining anti-R. target than other effects. Finally, biosafety assessment its safety toward zebrafish.

Language: Английский

Citations

1

Synthesis, antibacterial evaluation and preliminary mechanism study of novel isoquinoline‐3‐carboxylic acid derivatives containing an acylhydrazone disulfone moiety DOI Open Access
Shangde Sun, Ping Fang, Zhiyuan Xu

et al.

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

Published: Feb. 24, 2025

Limitations in the use and availability of copper-based fungicides antibiotics has led to a scarcity bactericidal agents. It is urgent develop green bactericides with new modes-of-action effective chemotypes. A bioactive substructure splicing approach was applied optimize structure natural product isoquinolin-3-carboxylic acid (IQ3CA). The structure-activity relationship analysis showed that increase sulfur atomic oxidation state small groups on sulfone will be beneficial for antibacterial activities. difulone compound SF2 most potent activity against Xanthomonas oryzae pv. (Xoo), Ralstonia solanacearum (Rs) Acidovorax citrulli (Ac), median lethal concentration values 2.52, 2.62 1.12 μg mL-1, respectively, which were superior those IQ3CA kasugamycin. protective curative effects Ac 69.31% 55.64%, better than thiodiazole copper (58.37% 43.08%). Furthermore, preliminary mechanistic investigations indicated could membrane permeability, reduce exopolysaccharide content, inhibit both bacterial motility biofilm formation. series novel isoquinoline-3-acylhydrazone derivatives incorporating thioether/disulfone moieties synthesized, bioassay results demonstrated remarkable by disrupting membranes. © 2025 Society Chemical Industry.

Language: Английский

Citations

1

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

Jianqi Chai,

Xiaobin Wang, Kai Yue

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(20), P. 11308 - 11320

Published: May 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.

Language: Английский

Citations

5

Current status and future trends of microbial and nematode-based biopesticides for biocontrol of crop pathogens DOI
Rayhane Hamrouni,

Flor Regus,

Anne‐Marie Farnet

et al.

Critical Reviews in Biotechnology, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 20

Published: July 10, 2024

The increasing public demand to avoid the use of synthetic pesticides and fertilizers in agricultural production systems, causing serious environmental damages, has challenged industry develop new effective solutions manage control phytopathogens. Biopesticides, particularly microbial-based biopesticides, are a promising alternative with high biodegradability, specificity, suitability for incorporation into integrated pest management practices, low likelihood resistance development, practically no known human health risks. However: expensive methods, narrow action spectra, susceptibility conditions, short shelf life, poor storage stability, legislation registry constraints, general lack knowledge slowing down their adoption. In addition regulatory framework revisions improved training initiatives, preservation thoughtfully designed formulations, field test validations needed offer microbial- nematode-based biopesticides efficacy increased shelf-life. During last several years, substantial advancements biopesticide have been developed. novelty part this review written 2023 is summarize (i) mechanisms beneficial microorganisms used increase crop performance (ii) successful formulation including commercial products biological phytopathogens based on microorganisms, nematode and/or metabolites.

Language: Английский

Citations

5

Design, Synthesis, Antifungal Activity, and Mechanism of Action of New Piperidine-4-carbohydrazide Derivatives Bearing a Quinazolinyl Moiety DOI

Yehui Yang,

Songsong Liu,

Taisen Yan

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(31), P. 17283 - 17294

Published: July 29, 2024

A series of new piperidine-4-carbohydrazide derivatives bearing a quinazolinyl moiety were prepared and evaluated for their fungicidal activities against agriculturally important fungi. Among these derivatives, the chemical structure compound A45 was clearly verified by X-ray crystallographic analysis. The antifungal bioassays revealed that many compounds in this possessed good to excellent inhibition effects toward tested For example, A13 A41 had EC50 values 0.83 0.88 μg/mL Rhizoctonia solani vitro, respectively, superior those positive controls Chlorothalonil Boscalid (1.64 0.96 μg/mL, respectively). Additionally, above two also exhibited notable inhibitory Verticillium dahliae (with 1.12 3.20 respectively), far better than Carbendazim (19.3 11.0 More importantly, could potently inhibit proliferation R. potted rice plants, showing vivo curative protective efficiencies 76.9% 76.6% at 200 respectively. Furthermore, demonstrated an effective succinate dehydrogenase (SDH) activity vitro with IC50 value 6.07 μM. Finally, molecular docking study be well embedded into active pocket SDH via multiple noncovalent interactions, involving residues like SER39, ARG43, GLY46.

Language: Английский

Citations

5

Environmental Evaluation on Toxicity, Toxic Mechanism, and Hydrolysis Behavior of Potential Acethydrazide Fungicide Candidates DOI
Zhanfang Chen, Jing Chang, Shuo Wang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(11), P. 5636 - 5644

Published: March 8, 2024

The evaluation of toxicity and environmental behavior bioactive lead molecules is helpful in providing theoretical support for the development agrochemicals, line with sustainable ecological environment. In previous work, some acethydrazide structures have been demonstrated to exhibit excellent broad-spectrum fungicidal activity; however, its compatibility needs be further elucidated if it identified as a potential fungicide. this project, compounds F51, F58, F72, F75 zebrafish was determined at 10 μg mL–1 1 mL–1. Subsequently, toxic mechanism compound F58 preliminarily explored by histologic section TEM observations, which revealed that gallbladder volume common carp treated increased, accompanied deepened bile color, damaged plasma membrane, atrophied mitochondria cells. Approximately, F58-treated hepatocytes exhibited cytoplasmic heterogeneity, partial cellular vacuolation mitochondrial membrane rupture. Metabolomics analysis indicated differential metabolites were enriched formation-associated steroid biosynthesis, primary acid taurine hypotaurine metabolism pathways, well function-related glycerophospholipid metabolism, linolenic α-linolenic arachidonic suggesting may acute liver carp. Finally, hydrolysis dynamics investigated, obtained half-life 5.82 days. above results provide important guiding significance new green fungicides.

Language: Английский

Citations

4

4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops DOI Creative Commons
Halina Maniak, Konrad Matyja, Elżbieta Pląskowska

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(10), P. 2212 - 2212

Published: May 8, 2024

The research on new compounds against plant pathogens is still socially and economically important. It results from the increasing resistance of pests to protection products need maintain high yields crops, particularly oilseed crops used manufacture edible industrial oils biofuels. We tested thirty-five semi-synthetic hydrazide–hydrazones with aromatic fragments natural origin phytopathogenic laccase-producing fungi such as Botrytis cinerea, Sclerotinia sclerotiorum, Cerrena unicolor. Among investigated molecules previously identified potent laccase inhibitors were also strong antifungal agents fungal species tested. highest activity showed derivatives 4-hydroxybenzoic acid salicylic aldehydes 3-tert-butyl, phenyl, or isopropyl substituents. S. sclerotiorum appeared be most susceptible compounds, lowest IC50 values between 0.5 1.8 µg/mL. applied two variants phytotoxicity tests for representative crop seeds selected hydrazide–hydrazones. Most show no low phytotoxic effect flax sunflower seeds. Moreover, a positive impact seed germination infected was observed. With potential application, cytotoxicity choice toward MCF-10A BALB/3T3 cell lines lower than that azoxystrobin fungicide

Language: Английский

Citations

4

Ibuprofen-furo[2,3-d]pyrimidine-based Hybrid Bearing Triazole, Hydrazide and Oxadiazole as Potent Antitumor Agents: Design and Synthesis and Activity Evaluation DOI

Chujie Liao,

Chun Feng, Li Li

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1319, P. 139481 - 139481

Published: Aug. 2, 2024

Language: Английский

Citations

3