Design, synthesis and antifungal activity of arylhydrazine analogs containing diphenyl ether fragments DOI

Longjian Qiu,

Yaru Liu, Lijuan Zhang

и другие.

Pest Management Science, Год журнала: 2024, Номер unknown

Опубликована: Окт. 28, 2024

Abstract BACKGROUND Succinate dehydrogenase (SDH) represents a critical target in the development of novel fungicides. To address growing issue resistance and safeguard economic viability agricultural production, pursuit new succinate inhibitors (SDHIs) has emerged as significant focus contemporary research. RESULTS In this project, 32 arylhydrazine derivatives containing diphenyl ether structural units were synthesized evaluated for their fungicidal activities against Rhizoctonia solani , Sclerotinia sclerotiorum Alternaria alternata Gibberella zeae Colletotrichum gloeosporioides . an vitro activity assay, compound D6 showed inhibitory R. with half‐maximum effective concentration (EC 50 ) 0.09 mg L −1 The vivo demonstrated that inhibited by 95.39% rice leaves, which was significantly better than boscalid (85.76%). results SDH enzyme molecular docking simulation, mitochondrial membrane potential cytoplasmic release studies morphological observations not only had activity, but also affected integrity mycelium. CONCLUSION Bioactivity screening validation mechanism action indicated potentially unique SDHI, acting on while affecting cell permeability, deserved further study. © 2024 Society Chemical Industry.

Язык: Английский

Discovery of novel sulfonamide derivatives containing pinacolone moieties as fungicide candidates against Botrytis cinerea DOI Open Access
Wei Liu,

Chaojie Liu,

Ni An

и другие.

Pest Management Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

Abstract BACKGROUND Botrytis cinerea is one of the most serious plant diseases and severely threatens agricultural production. The rapidly intensifying resistance makes commercial chemical fungicides lose control efficacy. Developing new with novel structures modes action an effective measure to solve this problem. RESULTS In work, 29 sulfonamide compounds containing pinacolone scaffolds were designed synthesized based on active substructure splicing strategy. biological activity assay three kinds strains manifested that these exhibit moderate excellent antifungal activity. Compounds 3a‐1 3a‐11 displayed highest in vitro similar agents carbendazim, procymidone, boscalid. Compound 3c had lowest EC 50 value 1.96 μg/mL against strain PJ‐02 compared boscalid (6.90 μg/mL). Bioassay results strawberry fruits tomato pots indicated also possess superb vivo agents. electronic conductivity measurement showed compound can significantly increase membrane permeability mycelium. Scanning electron microscopy observation revealed could cause mycelium twist break, inhibit branching. Density functional theory calculation molecular electrostatic potential distribution used analyze mechanism target compounds. CONCLUSION Due their , derivatives be considered qualified fungicide candidates. Preliminary exploration suggests kind may a mode action. © 2025 Society Chemical Industry.

Язык: Английский

Процитировано

1
Novel Furazanoazepines Derivatives as Sdh Inhibitors: Design, Synthesis and Their Fungicidal Activities DOI
Xingyu Ren,

Jiangping Pu,

Haidong Fu

и другие.

Опубликована: Янв. 1, 2025

Plant diseases induced by plant pathogenic fungi are the damage caused of agriculture and food losses. The development novel fungicides is an urgent way to deal with increasing resistance environmental issues. Herein, 37 furazanoazepines derivatives were effectively synthesized their antifungal activity was investigated against four phytopathogenic fungi. result indicated that compound 4h exhibited excellent Alternaria alternata (EC50 = 17.267 μg/mL), which obviously better than positive control osthole. In addition, scanning electron microscopy (SEM) showed could cause morphological hyphae. To understand its action mode, molecular docking performed on succinate dehydrogenase (SDH). results amide bond form a hydrogen interaction Gly128 residue.The 3D-QSAR conducted reveal structure-activity relationship prepared compounds. SDH enzymatic testing revealed inhibitory effect IC50 values 3.59 μg/mL, control. It concluded in this study promising for further explore potential agricultural fungicides.

Язык: Английский

Процитировано

0
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

и другие.

Bioorganic Chemistry, Год журнала: 2025, Номер 156, С. 108237 - 108237

Опубликована: Фев. 2, 2025

Язык: Английский

Процитировано

0
Novel furazanoazepines derivatives as SDH inhibitors: Design, synthesis and their fungicidal activities DOI
Xingyu Ren,

Jiangping Pu,

Haidong Fu

и другие.

Bioorganic Chemistry, Год журнала: 2025, Номер 157, С. 108244 - 108244

Опубликована: Фев. 4, 2025

Язык: Английский

Процитировано

0
Isoflavones and Stilbenes With Antifungal Activities From the Seeds of Thermopsis lanceolata R. Br DOI

Cheng-Feng Liu,

Jianguo Tan,

Xuye Wu

и другие.

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

Опубликована: Апрель 30, 2025

In order to discover novel fungicides from natural products, the phytochemical investigation of Thermopsis lanceolata seeds was thoroughly conducted. Eight new isoflavone derivatives (1-5 and 8-10), two stilbenes (6 7), as well 21 known isoflavones (11-31) were obtained crude extract T. following a bioassay-guided method. The structures 1-31 confirmed via HRESIMS, NMR, IR, UV, quantum chemistry calculations. antifungal activities against Phytophthora nicotiana, Colletotrichum orbiculare, Rhizoctonia solani, Botrytis cinerea screened according mycelial inhibition test. Compound 6 displayed significant activity B. in vitro (EC50: 9.68 μg/mL) had an 8 5.7% prevention control effect vivo (100 μg/mL). Moreover, mechanism studies revealed that causes accumulation reactive oxygen species, increases level lipid peroxidation, decreases MDH, finally triggers molecular damage cell death vitro. Therefore, can be utilized lead compound for fungicides.

Язык: Английский

Процитировано

0
Design, synthesis and antifungal activity of arylhydrazine analogs containing diphenyl ether fragments DOI

Longjian Qiu,

Yaru Liu, Lijuan Zhang

и другие.

Pest Management Science, Год журнала: 2024, Номер unknown

Опубликована: Окт. 28, 2024

Abstract BACKGROUND Succinate dehydrogenase (SDH) represents a critical target in the development of novel fungicides. To address growing issue resistance and safeguard economic viability agricultural production, pursuit new succinate inhibitors (SDHIs) has emerged as significant focus contemporary research. RESULTS In this project, 32 arylhydrazine derivatives containing diphenyl ether structural units were synthesized evaluated for their fungicidal activities against Rhizoctonia solani , Sclerotinia sclerotiorum Alternaria alternata Gibberella zeae Colletotrichum gloeosporioides . an vitro activity assay, compound D6 showed inhibitory R. with half‐maximum effective concentration (EC 50 ) 0.09 mg L −1 The vivo demonstrated that inhibited by 95.39% rice leaves, which was significantly better than boscalid (85.76%). results SDH enzyme molecular docking simulation, mitochondrial membrane potential cytoplasmic release studies morphological observations not only had activity, but also affected integrity mycelium. CONCLUSION Bioactivity screening validation mechanism action indicated potentially unique SDHI, acting on while affecting cell permeability, deserved further study. © 2024 Society Chemical Industry.

Язык: Английский

Процитировано

0