Novel Insecticidal Benzo[4,5]imidazo[1,2‐b]pyrazole Derivatives Identified through Ring‐Closure Scaffold Hopping on Fipronil DOI Open Access
Cong Zhou, Guanglong Li, Sihui Wang

et al.

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract A series of innovative benzo[4,5]imidazo[1,2‐ b ]pyrazole scaffold containing compounds were rationally designed through a ring‐closure hopping strategy and synthetized with an intermediate derivatization approach. Physicochemical properties analysis indicated the potential pesticide‐likeness target compounds. The optimal compound A14 showed relatively good insecticidal activity against P. xylostella , LC 50 value 37.58 mg/L, demonstrated lower acute fish toxicity compared to fipronil. Docking binding mode that bound GABAR H‐bond between amide group residue 6’Thr. differences in modes fipronil may be key factor for reduced activities. elucidated SAR profile lay foundation further structural optimization derivatives.

Language: Английский

The role of silicon in drug discovery: a review DOI Creative Commons
Jenny‐Lee Panayides, Darren L. Riley, Felix Hasenmaile

et al.

RSC Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 15(10), P. 3286 - 3344

Published: Jan. 1, 2024

This review aims to highlight the role of silicon in drug discovery.

Language: Английский

Citations

10
Design, Synthesis, and Fungicidal Activities of Novel N-(Pyrazol-5-yl)benzamide Derivatives Containing a Diphenylamine Moiety DOI

Yidan Ma,

Huan Zhou,

Guo‐Tai Lin

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(12), P. 6691 - 6701

Published: March 18, 2024

To accelerate the development of novel fungicides, a variety

Language: Английский

Citations

6
3D‐QSAR model‐oriented optimization of Pyrazole β‐Ketonitrile derivatives with diphenyl ether moiety as novel potent succinate dehydrogenase inhibitors DOI
Liangliang Cheng, Cong Zhou,

Qinglong Yuan

et al.

Pest Management Science, Journal Year: 2024, Volume and Issue: 80(10), P. 5299 - 5306

Published: June 28, 2024

Abstract BACKGROUND Succinate dehydrogenase inhibitor (SDHI) fungicides play important roles in the control of plant fungal diseases. However, they are facing serious challenges from issues with resistance and cross‐resistance, primarily attributed to their frequent application structural similarities. There is an urgent need design develop SDHI novel structures. RESULTS Aiming discover potent fungicides, 31 innovative pyrazole β ‐ketonitrile derivatives diphenyl ether moiety were rationally designed synthesized, which guided by a 3D‐QSAR model our previous study. The optimal target compound A23 exhibited not only outstanding vitro inhibitory activities against Rhizoctonia solani half‐maximal effective concentration (EC 50 ) value 0.0398 μg mL −1 comparable that for fluxapyroxad = 0.0375 ), but also moderate protective efficacy vivo rice sheath blight. Porcine succinate (SDH) enzymatic assay revealed SDH, 0.0425 μ m . Docking study within R. SDH indicated effectively binds into ubiquinone site mainly through hydrogen‐bonds, cation–π π–π interactions. CONCLUSION identified containing inhibitor, might be good lead fungicide research optimization. © 2024 Society Chemical Industry.

Language: Английский

Citations

6
Recent Advances in Design and Development of Diazole and Diazine Based Fungicides (2014–2023) DOI
Ebrahim Saeedian Moghadam,

Fahimeh Bonyasi,

Bahareh Bayati

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(28), P. 15427 - 15448

Published: July 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.

Language: Английский

Citations

6
Design, Synthesis, and Antifungal Activity of Acrylamide Derivatives Containing Trifluoromethylpyridine and Piperazine DOI
Jinli Chen, Meng Zhang,

Chunmei Yuan

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(20), P. 11360 - 11368

Published: May 9, 2024

In this study, a series of acrylamide derivatives containing trifluoromethylpyridine or piperazine fragments were rationally designed and synthesized. Subsequently, the in vitro antifungal activities all synthesized compounds evaluated. The findings revealed that 6b, 6c, 7e exhibited >80% activity against Phomopsis sp. (Ps) at concentration 50 μg/mL. Furthermore, EC50 values for Ps determined to be 4.49, 6.47, 8.68 μg/mL, respectively, which better than positive control with azoxystrobin (24.83 μg/mL). At 200 protective compound 6b reached 65%, was comparable (60.9%). Comprehensive mechanistic studies, including morphological studies fluorescence microscopy (FM), cytoplasmic leakage, enzyme assays, indicated disrupts cell membrane integrity induces accumulation defense activity, thereby inhibiting mycelial growth. Therefore, serves as valuable candidate development novel fungicides plant protection.

Language: Английский

Citations

5
Design, Synthesis, and Antifungal Activities of Novel Potent Fluoroalkenyl Succinate Dehydrogenase Inhibitors DOI
Yu Chen,

Weilong Xu,

Mian Du

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(26), P. 14535 - 14546

Published: June 21, 2024

The development of new fungicide molecules is a crucial task for agricultural chemists to enhance the effectiveness fungicides in production. In this study, series novel fluoroalkenyl modified succinate dehydrogenase inhibitors were synthesized and evaluated their antifungal activities against eight fungi. results from

Language: Английский

Citations

5
Isolating Antipathogenic Fungal Coumarins from Coriaria nepalensis and Determining Their Primary Mechanism In Vitro DOI

Jun-you Jian,

Yi‐Min Fan, Jun Jin

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(12), P. 6711 - 6722

Published: March 16, 2024

Through bioassay-guided isolation, eight undescribed coumarins (1–8), along with six reported (9–14), were obtained from Coriaria nepalensis. The new structures determined by using IR, UV, NMR, HRESIMS, and ECD calculations. results of the biological activity assays showed that compound 9 exhibited broad spectrum antifungal activities against all tested fungi in vitro a significant inhibitory effect on Phytophthora nicotianae an EC50 value 3.00 μg/mL. Notably, demonstrated greater curative protective effects tobacco balack shank than those osthol vivo. Thus, was structurally modified to obtain promising agents, novel derivatives (17b, 17j, 17k) better Sclerotinia sclerotiorum did lead 9. Preliminary mechanistic exploration illustrated could enhance cell membrane permeability, destroy morphology ultrastructure cells, reduce exopolysaccharide content P. mycelia. Furthermore, cytotoxicity revealed relatively low HEK293 lines inhibition rate 33.54% at 30 This research is for discovery fungicides natural satisfactory ecological compatibility.

Language: Английский

Citations

4
Recent innovations in crop protection research DOI Creative Commons
Peter Maienfisch,

Karsten Koerber

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

Published: Sept. 30, 2024

Abstract As the world's population continues to grow and demand for food increases, agricultural industry faces challenge of producing higher yields while ensuring safety quality harvests, operators, consumers. The emergence resistance, pest shifts, stricter regulatory requirements also urgently calls further advances in crop protection discovery new innovative products sustainable protection. This study reviews recent highlights innovation as presented at 15th IUPAC International Congress Crop Protection Chemistry held New Delhi, 2023. following are discussed: insecticides Indazapyroxamet, Dimpropyridaz Fenmezoditiaz, fungicides Mefentrifluconazole Pyridachlomethyl, nematicide Cyclobutrifluram, herbicides Rimisoxafen, Dimesulfazet, Epyrifenacil well abiotic stress management product Anisiflupurin. In addition, latest research areas all will be presented, including insecticidal alkyl sulfones 1,3,4‐trisubstituted pyrazoles, fungicidal picolinamides, herbicidal ketoenols, trifluoromethylpyrazoles, enhancement green control research. © 2024 Author(s). Pest Management Science published by John Wiley & Sons Ltd on behalf Society Chemical Industry.

Language: Английский

Citations

4
Design, synthesis, crystal structure, fungicidal activity, and mechanism of action of novel thiazole-based hydrazide derivatives containing the 4-aminoquinazoline moiety DOI

Mingyan Yi,

Hong Li, Sha Li

et al.

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 156, P. 108237 - 108237

Published: Feb. 2, 2025

Language: Английский

Citations

0
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

0