Design, Synthesis, Insecticidal Activity, and SAR of Aryl Isoxazoline Derivatives Containing Pyrazole-5-carboxamide Motif

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(40), С. 14458 - 14470

Опубликована: Окт. 2, 2023

It is important to develop new insecticides with a mode of action because increasing pesticide resistance. In this study, series novel aryl isoxazoline derivatives containing the pyrazole-5-carboxamide motif were designed and synthesized. Their structures confirmed by 1H NMR, 13C HRMS. Bioassays indicated that 24 compounds synthesized possessed excellent insecticidal activity against Mythimna separate no Aphis craccivora Tetranychus cinnabarinus. Among these derivatives, 3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydrozol-3-yl)-N-(4-fluorophenyl)-1-methyl-1H-pyrazole-5-carboxamide (IA-8) had best M. separate, which comparable positive control fluralaner. The molecular docking results compound IA-8 fluralaner GABA model demonstrated same between in active site GABA. Molecular structure comparisons ADMET analysis can potentially be used design more compounds. structure–activity relationships are also discussed. This work provided an insecticide for further optimization.

Язык: Английский

---

A Comprehensive Investigation of Hydrazide and Its Derived Structures in the Agricultural Fungicidal Field

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(22), С. 8297 - 8316

Опубликована: Май 30, 2023

Hydrazides are present in many bioactive molecules and exhibit a variety of biological activities, such as insecticidal, herbicidal, antifungal, antitumor, antiviral effects. In this Review, we review the application hydrazide its derived structures agricultural fungicidal field, including monohydrazides, diacylhydrazines, hydrazide-hydrazones, sulfonyl hydrazides. addition, antifungal mechanism action derivatives was analyzed summarized, mainly involving succinate dehydrogenase inhibitors, laccase targeting plasma membranes. Finally, based on structural analysis novel lead compounds, structure–activity relationship constructed development trend applications prospected. It is hoped that Review can provide some significant guidance for new fungicides future.

Язык: Английский

---

Deeper Insights on the Nonlinear Optical Properties of O-acylated Pyrazoles

Journal of Electronic Materials, Год журнала: 2024, Номер 53(4), С. 1868 - 1883

Опубликована: Фев. 16, 2024

Язык: Английский

---

Novel Flavonol Derivatives Containing 1,3,4-Thiadiazole as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

ACS Omega, Год журнала: 2024, Номер unknown

Опубликована: Апрель 5, 2024

In order to discover novel compounds with excellent agricultural activities, flavonol derivatives containing 1,3,4-thiadiazole were synthesized and evaluated for their antifungal activities. The bioassay results showed that some of the target had good activities against Botrytis cinerea, Phomopsis sp. Sclerotinia sclerotiorum in vitro. It is worth noting half-effective concentration (EC50) value Y18 B. cinerea was 2.4 μg/mL, which obviously superior azoxystrobin (21.7 μg/mL). curative activity at 200 μg/mL (79.9%) better than (59.1%), its protective (90.9%) (83.9%). Morphological studies by using scanning electron microscopy fluorescence revealed could affect normal growth mycelium. addition, mechanism action indicated integrity cell membranes inducing production endogenous reactive oxygen species release malondialdehyde content, leading membrane lipid peroxidation contents. inhibitory on plant fungi notable, offering significant potential development new agents.

Язык: Английский

---

Pyrazole derivatives: Recent advances in discovery and development of pesticides

Chinese Chemical Letters, Год журнала: 2025, Номер unknown, С. 110912 - 110912

Опубликована: Фев. 1, 2025

Язык: Английский

---

Targeting tubulin protein to combat fungal disease: Design, synthesis, and its new mechanistic insights of benzimidazole hydrazone derivatives

International Journal of Biological Macromolecules, Год журнала: 2025, Номер unknown, С. 140226 - 140226

Опубликована: Янв. 1, 2025

Язык: Английский

---

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

Deleted Journal, Год журнала: 2025, Номер 7(2)

Опубликована: Фев. 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

Язык: Английский

---

Exploring the potential in postharvest preservation of sweet potato: 2-methylbutanoic acid, isobutyric acid, perillaldehyde and salicylaldehyde, to control Rhizopus stolonifer

Postharvest Biology and Technology, Год журнала: 2024, Номер 210, С. 112785 - 112785

Опубликована: Янв. 17, 2024

Язык: Английский

---

Synthesis and Antifungal Activity of Chalcone Derivatives Containing 1,3,4‐Thiadiazole

Chemistry & Biodiversity, Год журнала: 2024, Номер 21(8)

Опубликована: Май 21, 2024

Abstract 24 chalcone derivatives containing 1,3,4‐thiadiazole were synthesized. The results of bioactivity tests indicated that some the target compounds exhibited superior antifungal activities in vitro . Notably, EC 50 value D4 was 14.4 μg/mL against Phomopsis sp , which significantly better than azoxystrobin (32.2 μg/mL) and fluopyram (54.2 μg/mL). vivo protective activity on kiwifruit (71.2 %) to (62.8 at 200 μg/mL. 74.4 57.6 % Rhizoctonia solani rice leaf sheaths leaves, respectively, slightly those (72.1 49.2 Scanning electron microscopy (SEM) showed mycelial surface collapsed, contracted grew abnormally after treatment. Finally, further verified by assay, fluorescence (FM) observation, determination relative conductivity, membrane lipid peroxidation degree cytoplasmic content leakage. Molecular docking suggested could be a potential SDHI.

Язык: Английский

---

Discovery of Benzothiazolylpyrazole-4-Carboxamides as Potent Succinate Dehydrogenase Inhibitors through Active Fragment Exchange and Link Approach

Journal of Agricultural and Food Chemistry, Год журнала: 2023, Номер 71(40), С. 14471 - 14482

Опубликована: Сен. 29, 2023

Succinate dehydrogenase (SDH) is an attractive target for developing green fungicides to manage agricultural pathogens in modern agriculture research. Herein, this work, we report the discovery of benzothiazolylpyrazole-4-carboxamides I-III as potent SDH inhibitors using active fragment exchange and link approach. The results fungicidal activity assays showed that some synthesized compounds exhibited excellent inhibition against tested fungi. Systematic structure-activity relationship studies led compound Ip, N-(1-((4,6-difluorobenzo[d]thiazol-2-yl)thio)propan-2-yl)-3-(difluoromethyl)-N-methoxy-1-methyl-1H-pyrazole-4-carboxamide, which higher Fusarium graminearum Schw (EC50 = 0.93 μg/mL) than commercial thifluzamide > 50 boscalid μg/mL). molecular simulation suggested hydrophobic interactions were primary driving forces between ligands SDH. Promisingly, found Ip could stimulate growth wheat seedlings Arabidopsis thaliana increase biomass treated plants. Preliminary on plant promoter mechanism indicated it nitrate reductase planta, that, turn, stimulates

Язык: Английский

---