Discovery of α-Methylene-γ-Butyrolactone Derivatives with Hydrazide Moieties as Novel Fungicidal Agents DOI
Feiyu Wang, Dan Xu, Hong‐Wei He

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

To discover novel fungicides with unique structures, a series of α-methylene-γ-butyrolactone derivatives were designed and synthesized by incorporating flexible amide or hydrazide chain through active substructure splicing linker modification strategies. Bioassay assessments demonstrated that certain hydrazide-containing compounds have potent fungicidal efficacy. Notably, compound 7IIj exhibited broad-spectrum antifungal activity, EC50 values as low 0.179, 0.301, 0.647, 0.549, 0.789 mg/L against Rhizoctonia solani, Physalospora piricola, Botrytis cinerea, Gaeumanomyces graminis, Valsa mali, respectively. In vivo experiments confirmed the effective activity 7IIj, showing an inhibitory rate 69.7% V. mali on apple twigs at 200 mg/L. Additionally, concentration 100 mg/L, significant protective curative effects R. solani rice plants. Research mechanism action revealed could disrupt hyphal morphology, induce reactive oxygen species (ROS) accumulation, affect mitochondrial membrane potential (MMP), interfere respiratory metabolism binding to complex II. Molecular docking analysis showed interactions TRP 173, TYR 58, ARG 43 in succinate dehydrogenase (SDH) site, resembling mode fluxapyroxad. These findings suggest holds SDH inhibitor for agricultural disease control.

Language: Английский

Comprehensive Overview of Carboxamide Derivatives as Succinate Dehydrogenase Inhibitors DOI
Bo Luo,

Yuli Ning

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 70(4), P. 957 - 975

Published: Jan. 18, 2022

Up to now, a total of 24 succinate dehydrogenase inhibitors (SDHIs) fungicides have been commercialized, and SDHIs were also one the most active developed in recent years. Carboxamide derivatives represented an important class with broad spectrum antifungal activities. In this review, development carboxamide as great significances summarized. addition, structure–activity relationships (SARs) activities was summarized based on analysis structures commercial lead compounds. Moreover, cause resistance some solutions introduced. Finally, trend prospected. We hope review will give guide for novel future.

Language: Английский

Citations

96
Synthesis of 4H-Pyrazolo[3,4-d]pyrimidin-4-one Hydrazine Derivatives as a Potential Inhibitor for the Self-Assembly of TMV Particles DOI
Ya Wang,

Shengxin Guo,

Wei Sun

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(6), P. 2879 - 2887

Published: Jan. 19, 2024

Tobacco mosaic virus coat protein (TMV-CP), as a potential target for the development of antiviral agents, can assist in long-distance movement viruses and plays an extremely important role replication propagation. This work focuses on synthesis action mechanism novel 4H-pyrazolo[3,4-d] pyrimidin-4-one hydrazine derivatives. The synthesized compounds exhibited promising activity TMV. Specifically, compound G2 high inactivating (93%) toward TMV, slightly better than commercial reagent NNM (90%). was further explored by employed molecular docking, dynamics simulation, microscale thermophoresis, qRT-PCR, transmission electron microscopy. Results indicated that had capability to interact with amino acid residues such Trp352, Tyr139, Asn73 active pocket TMV-CP, creating strong hydrophobic interactions thus obstructing virus's self-assembly.

Language: Английский

Citations

24
Design, synthesis and biological activity of chalcone derivatives containing pyridazine DOI Creative Commons
Shuai Chen, Miaohe Zhang, Shuang Feng

et al.

Arabian Journal of Chemistry, Journal Year: 2023, Volume and Issue: 16(7), P. 104852 - 104852

Published: March 27, 2023

Inspired by the application of fungicide from natural products, a series chalcone derivatives containing pyridazine were designed, synthesized, and evaluated for their antifungal activities against nine plant fungi antibacterial activity three bacteria. The results revealed that B8 showed best Xanthomonas campestris pv. citri (Xac) with an EC50 value 78.89 μg/mL, superior to Bismerthiazol (EC50 = 86.72 μg/mL). bioactivity some compounds had good fungi, such as B4 Botrytis cinerea (BC) 8.91 which was better than azoxystrobin 20.28 Compounds B4, D2 D3 biological Rhizoctonia solani (RS), 18.10, 20.18 20.60 comparable azoxystrobin. Antifungal mechanism studies BC suggest disrupts cell membrane mycelium thus inhibits growth fungus. above indicates have potential become fungicides.

Language: Английский

Citations

33
A Comprehensive Investigation of Hydrazide and Its Derived Structures in the Agricultural Fungicidal Field DOI
Jing Chang, Yang Liu, Tiancheng Zhang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(22), P. 8297 - 8316

Published: May 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.

Language: Английский

Citations

25
Antifungal Activity of Novel Indole Derivatives Containing 1,3,4-Thiadiazole DOI

Bangcan He,

Yuzhi Hu,

Xing Li

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(18), P. 10227 - 10235

Published: April 26, 2024

In this study, 24 indole derivatives containing 1,3,4-thiadiazole were discovered and synthesized. The target compounds' antifungal efficacy against 14 plant pathogenic fungal pathogens was then determined in vitro. With an EC50 value of 2.7 μg/mL, Z2 demonstrated the highest level bioactivity among them Botrytis cinerea (B.c.), exceeding concentrations control prescription drugs azoxystrobin (Az) (EC50 = 14.5 μg/mL) fluopyram (Fl) 10.1 μg/mL). underwent vivo testing on blueberry leaves order to evaluate its usefulness real-world settings. A reasonable protective effect obtained with a effectiveness 93.0% at 200 which superior those Az (83.0%) Fl (52.0%). At chemical had 84.0% terms curative efficacy. These figures outperformed (69.0%) (48.0%). Scanning electron microscopy (SEM) experiments light showed that altered integrity cell wall membrane fungus B.c., led increase content malondialdehyde (MDA), cellular leakage, permeability. Enzyme activity assays molecular docking studies indicated could act as potential succinate dehydrogenase inhibitor (SDHI). It hypothesized cause disruption mycelial membranes, turn leads death. According research, expected evolve into new fungicides due their significant effects fungi.

Language: Английский

Citations

11
Novel branched Heteroaromatic Pyrazole-based Polyazomethines as anticancer agents DOI Creative Commons

Aqilah A. Hakami,

Salsabeel Al-Sodies,

Hajar S. Alorfi

et al.

Results in Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 102129 - 102129

Published: Feb. 1, 2025

Language: Английский

Citations

1
Design, synthesis and biological evaluation of thiazole and imidazo[1,2-a]pyridine derivatives containing a hydrazone substructure as potential agrochemicals DOI Creative Commons
Xiaofang Yao, Rongrong Zhang, Bo Lv

et al.

Advanced Agrochem, Journal Year: 2023, Volume and Issue: 2(2), P. 154 - 162

Published: April 18, 2023

Agricultural chemicals with multifunctional applications in crop protection have attracted increasing attention. Herein, two new series of thiazole and imidazo[1,2-a]pyridine derivatives containing a hydrazone substructure were designed synthesized via concise synthesis route. Bioassay results showed that most the exhibited broad-spectrum fungistatic activities, which exemplified by compounds 1c, 1e, 1g, 1h 1j. In particular, compound 1e displayed excellent vitro inhibitory effects EC50 values 5.00, 18.24, 6.94, 3.03 μg/mL against fungi Botrytis cinerea, Cytospora sp, Fusarium graminearum, solani, respectively. Detached fruit experiments tomato gray mold (caused B. cinerea) vivo revealed control efficiency at 10, 20 40 for 5 days was 35.05%, 54.14% 81.83%, respectively, comparable even superior to fungicide carbendazim. Additionally, title also remarkable larvicidal activity M. separata some good aphicidal activity. word, bioassay indicated certain number had multiple biological activities. Given their antifungal characteristics, these interesting based on could be served as scaffolds development pesticide applications.

Language: Английский

Citations

21
Design, Synthesis, and Antifungal Evaluation of Diverse Heterocyclic Hydrazide Derivatives as Potential Succinate Dehydrogenase Inhibitors DOI
Yiliang Chen, Hao Liu, Jiahao Wang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(23), P. 12915 - 12924

Published: May 28, 2024

Plant pathogenic fungi pose a significant threat to agricultural production, necessitating the development of new and more effective fungicides. The ring replacement strategy has emerged as highly successful approach in molecular design. In this study, we employed successfully design synthesize 32 novel hydrazide derivatives containing diverse heterocycles, such thiazole, isoxazole, pyrazole, thiadiazole, 1,3,4-oxadiazole, 1,2,4-oxadiazole, thiophene, pyridine, pyrazine. Their antifungal activities were evaluated

Language: Английский

Citations

8
Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae DOI
Xingyu Chen,

Sihui Zhuang,

Weiyao Yan

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(10), P. 109635 - 109635

Published: Feb. 15, 2024

Language: Английский

Citations

7
Expanding the Structural Diversity of Tubulin-Targeting Agents: Development of Highly Potent Benzimidazoles for Treating Fungal Diseases DOI
Shan Yang, Junrong Zhang, Mei Li

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(28), P. 15541 - 15551

Published: July 3, 2024

Benzimidazoles, the representative pharmacophore of fungicides, have excellent antifungal potency, but their simple structure and single site action hindered wider application in agriculture. In order to extend structural diversity tubulin-targeted benzimidazoles, novel benzimidazole derivatives were prepared by introducing attractive pyrimidine pharmacophore. 2-((6-(4-(trifluoromethyl)phenoxy)pyrimidin-4-yl)thio)-1H-benzo[d]imidazole (A25) exhibited optimal activity against Sclerotinia sclerotiorum (S. s.), affording an half-maximal effective concentration (EC50) 0.158 μg/mL, which was higher than that reference agent carbendazim (EC50 = 0.594 μg/mL). Pot experiments revealed compound A25 (200 μg/mL) had acceptable protective (84.7%) curative (78.1%), comparable with (protective activity: 90.8%; 69.9%). Molecular docking displayed multiple hydrogen bonds π–π interactions could be formed between β-tubulin, resulting a stronger bonding effect carbendazim. Fluorescence imaging intracellular microtubules can changed significantly after treatment. Overall, these remarkable profiles constructed facilitate microtubule-targeting agents.

Language: Английский

Citations

6