Design, synthesis biological activity, and docking of novel fluopyram derivatives containing guanidine group

Liang, Peibo; Shen, Shengqiang; Xu, Qingbo; Wang, Simin; Jin, Shiying; Lu, Huizhe; Dong, Yanhong; Zhang, Jianjun

doi:10.1016/j.bmc.2020.115846

Cited by 28 publications

(25 citation statements)

References 29 publications

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“…Phytopathogenic fungi are the main causes of both the quality and yield loss of agricultural products, and the annual economic losses around the world are estimated to exceed $200 billion. , Chemical controls are both efficient and economical and have played a vital role in enhancing agricultural productivity throughout human history. , Chemical antifungal agents are the traditional approach to prevent and treat plant diseases. Unfortunately, the extensive use of a few conventional chemical antifungal agents has resulted in severe resistance to phytopathogenic fungi and negative impacts on the environment and public health. , Therefore, to respond to increasing resistance, the continuous development of novel, environmentally friendly, and low-toxicity antifungal agents is still a hot spot in pesticide research. , …”

Section: Introductionmentioning

confidence: 99%

“…1,2 Chemical controls are both efficient and economical and have played a vital role in enhancing agricultural productivity throughout human history. 3,4 Chemical antifungal agents are the traditional approach to prevent and treat plant diseases. Unfortunately, the extensive use of a few conventional chemical antifungal agents has resulted in severe resistance to phytopathogenic fungi and negative impacts on the environment and public health.…”

Section: ■ Introductionmentioning

confidence: 99%

“…5,6 Therefore, to respond to increasing resistance, the continuous development of novel, environmentally friendly, and low-toxicity antifungal agents is still a hot spot in pesticide research. 3,7 Plants are naturally rich in antifungal active substances, and plant-derived metabolites are extensively available for developing botanical fungicides. 8,9 Botanical pesticides refer to pesticides obtained from plant-based active ingredients or plant secondary metabolites to prevent pests and diseases.…”

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel Citral-thiazolyl Hydrazine Derivatives as Promising Antifungal Agents against Phytopathogenic Fungi

Zhang

Shi

Duan

et al. 2021

J. Agric. Food Chem.

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To develop new antifungal agents against phytopathogenic fungi, a series of citral-thiazolyl hydrazine derivatives were designed, synthesized, and characterized by FT-IR, 1 H NMR, 13 C NMR, and HRMS. Antifungal activity results showed that most synthetic compounds exhibited broad-spectrum antifungal activities against six phytopathogenic fungi in vitro. Notably, compounds b and c15 exhibited remarkable antifungal activity against Colletotrichum gloeosprioides, Rhizoctonia solani, Phytophthora nicotianae var. nicotianae, Diplodia pinea, Colletotrichum acutatum, and Fusarium oxysporum f. sp. niveum, which were all superior to the positive control tricyclazole. Structure−activity relationship (SAR) studies demonstrated that introducing electron-withdrawing groups such as F on the benzene ring exhibited outstanding antifungal activities against all the tested fungi. Furthermore, compound b could effectively control rice sheath blight and showed higher curative activities against R. solani than validamycin•bacillus in vivo. In addition, the in vitro cytotoxicity results indicated that compound b possessed moderate cytotoxicity activity, and all citral-thiazolyl hydrazine derivatives exhibited lower or no cytotoxicity to the LO2 and HEK293 cell lines. In addition, the acute oral toxicity test showed that compound b had moderate toxicity (level II) with an LD 50 value of 310 mg/kg bw (95% confidence limit: 175−550 mg/kg bw). Finally, a preliminary action mechanism study showed that causing obvious malformation of mycelium and increasing cell membrane permeability are two of the potential mechanisms by which compound b exerts antifungal activity. The present work indicates that some of these derivatives may serve as novel potential fungicides, and compound b is expected to be the leading structure for the development of new antifungal agents.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Novel Citral-thiazolyl Hydrazine Derivatives as Promising Antifungal Agents against Phytopathogenic Fungi

Zhang

Shi

Duan

et al. 2021

J. Agric. Food Chem.

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“…FLP has been widely used in agriculture and has toxicological effects on non-target organisms (Liu et al 2021). Bayer Crop Science developed FLP, a new broad-spectrum fungicide in the benzamide class (Matadha et al 2019;Liang et al 2021). FLP is extremely helpful in combating a wide range of pathogens in over 1970 plants, including crop plants, vegetables, vines, and some grapes, primarily by restricting the SDH, parasitic and fungal, and chain of parasitic respiratory (Liu et al 2021).…”

Section: Introductionmentioning

confidence: 99%

Lithospheric Based Eco-decontamination and Fate Elucidation of Fungicide Fluopyram Containing Benzamides Background

Naeem

Ahmad

2022

Preprint

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Fungicide Fluopyram (FLP) containing benzamides class has been scrutinized for the first time for its ecotoxicity and environmental lithosphere stationed fate from various climatic zones. Fate-decisive research inclusive of examining FLP's response in perspective of alteration via adsorption/desorption and disintegration in hydrolytic, photolytic, and bio-degradative procedures. Sorptive interactions determination was done by the batch equilibration approach and indicated its dependency on the chemico-physical properties of the soils. Fragile adsorptive interactions between soils and FLP molecules were established, as indicated by physio-sorption and a fragile exothermic response indicated by negative Gibbs free energy values (-8 to -15.3 kJ mol-1). The soil with the maximal adsorption, Kd(ads) =8.6 µg mL−1, was procured to have a significant organic matter content (1.30 %), resulting in a C-type isotherm that was scrutinized using a linear and Freundlich model. The analytical techniques, inclusive of ultraviolet-visible spectrophotometric and high-performance liquid chromatography procedures have been endeavored to examine FLP fate elucidation. Hydrolysis, photolysis, and biodegradation tests procured minimum halflives of 7.45, 1.29, and 5.77 days while the most remarkable were 10.6, 7.96, and 10.6 days, respectively. The results demonstrated that FLP displayed medium binding and thus low persistence in the tested soils while being extremely susceptible to transformative mechanisms. Current research can be embraced to include further augmentation of these degradative ways and to develop realistic methods for environmental cleanup through natural routes.

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“…These SDHIs have a similar heterocyclic acid scaffold, such as pyrazole and pyridine rings. In recent years, a majority of studies have concentrated on the modification of the amine group with retaining the core moieties of commercial SDHIs, which may lead to structural similarity and cross-resistance more easily. − Consequently, the research on structure modification and optimization of a novel carboxyl acid core moiety could be another important direction for the development of novel SDHIs.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antifungal Activity of Novel Thiophene/Furan-1,3,4-Oxadiazole Carboxamides as Potent Succinate Dehydrogenase Inhibitors

Yang

Sun

Liu

et al. 2021

J. Agric. Food Chem.

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Succinate dehydrogenase (SDH) is known as an ideal target for the investigations of fungicides. To develop novel SDH inhibitors, 30 novel thiophene/furan-1,3,4-oxadiazole carboxamide derivatives were designed and synthesized. In the in vitro antifungal assay, a majority of the target compounds demonstrated fair to potent antifungal activity against seven tested phytopathogenic fungi. Compounds 4b, 4g, 4h, 4i, and 5j showed remarkable antifungal activity against Sclerotinia sclerotiorum, affording EC50 values ranging from 0.1∼1.1 mg/L. In particular, compound 4i displayed the most potent activity against S. sclerotiorum (EC 50 = 0.140 ± 0.034 mg/L), which was superior to that of boscalid (EC 50 = 0.645 ± 0.023 mg/L). A further morphological investigation revealed the abnormal mycelia and damaged cell structures of compound 4i-treated S. sclerotiorum by scanning electron microscopy. Furthermore, the in vivo antifungal assay against S. sclerotiorum revealed that compounds 4g and 4i were effective for suppressing rape Sclerotinia rot at a dosage of 200 mg/L. In the SDH inhibition assay, compounds 4g and 4i also presented significant inhibitory activity with IC 50 values of 1.01 ± 0.21 and 4.53 ± 0.19 μM, respectively, which were superior or equivalent to that of boscalid (3.51 ± 2.02 μM). Molecular docking and molecular dynamics simulation of compound 4g with SDH revealed that compound 4g could form strong interactions with the key residues of the SDH. These results indicated that this class of derivatives could be a promising scaffold for the discovery and development of novel SDH inhibitors.

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Design, synthesis biological activity, and docking of novel fluopyram derivatives containing guanidine group

Cited by 28 publications

References 29 publications

Novel Citral-thiazolyl Hydrazine Derivatives as Promising Antifungal Agents against Phytopathogenic Fungi

Novel Citral-thiazolyl Hydrazine Derivatives as Promising Antifungal Agents against Phytopathogenic Fungi

Lithospheric Based Eco-decontamination and Fate Elucidation of Fungicide Fluopyram Containing Benzamides Background

Design, Synthesis, and Antifungal Activity of Novel Thiophene/Furan-1,3,4-Oxadiazole Carboxamides as Potent Succinate Dehydrogenase Inhibitors

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