Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives

Qiao, Lili; Yan, Wei; Hao, Shu

doi:10.6023/cjoc201708004

Cited by 6 publications

(4 citation statements)

References 3 publications

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“…Yield 70%, m.p. 179–180 °C (as reported) [ 53 ]. The compound is unstable and needs to be used as soon as possible for the next step.…”

Section: Methodsmentioning

confidence: 77%

“…However, the literature about CF 3 -substituted coumarins is limited, and the reports about these compounds are mainly focused on their use as substrate probes to detect the physiology [ 50 , 51 , 52 ]. Also, in view of these observations and in continuation of our research program on the synthesis of fluorinated coumarins [ 53 ], we herein report the synthesis and characterization of some novel 4-trifluoromethyl-6-substituted-ureido-7-methoxylcoumarins, whose fluorescent properties and antifungal and herbicidal activities are also evaluated.…”

Section: Introductionmentioning

confidence: 99%

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Novel Trifluoromethylcoumarinyl Urea Derivatives: Synthesis, Characterization, Fluorescence, and Bioactivity

Qiao

Hao

2018

Molecules

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A series of novel trifluoromethylcoumarinyl urea derivatives were designed, synthesized, and characterized by 1H-NMR, 13C-NMR, and HR-ESI-MS. The fluorescence spectra of the target compounds were recorded. The spectra show that most of the title compounds glow green with λmaxem of 500–517 nm, while compounds 5r, 5s, 5u, and 5l (compounds named by authors) glow violet with λmaxem of 381–443 nm. Moreover, the herbicidal and antifungal activities of the synthesized compounds were evaluated for their potential use as pesticides. The results indicate that compound 5f against the caulis of Amaranthus retroflexus and compounds 5j and 5l against the taproot of Digitaria sanguinalis are equivalent to the commercial herbicide Acetochlor. Nine of the title compounds are more antifungal than commercial fungicide Carbendazim against Botrytis cinerea.

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“…Yield 70%, m.p. 179–180 °C (as reported) [ 53 ]. The compound is unstable and needs to be used as soon as possible for the next step.…”

Section: Methodsmentioning

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Novel Trifluoromethylcoumarinyl Urea Derivatives: Synthesis, Characterization, Fluorescence, and Bioactivity

Qiao

Hao

2018

Molecules

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“…The coumarin derivatives 45 – 48 − designed and synthesized by introducing the amide moiety, showed excellent herbicidal activity (Figure a). For example, the compound 45 significantly inhibited the growth of D. sanguinalis and A. retroflexus stems at a concentration of 20 mg/L, and exhibited comparable herbicidal activity as that of acetochlor, while the compound 47 showed better herbicidal activity (>70%) at 20 mg/L and performed better than acetochlor.…”

Section: Benzopyran Active Compounds For Agricultural Applicationmentioning

confidence: 99%

Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals

Liu,

Zhang,

Zou

et al. 2024

J. Agric. Food Chem.

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Scaffold structures, new mechanisms of action, and targets present enormous challenges in the discovery of novel pesticides. The discovery of new scaffolds is the basis for the continuous development of modern agrochemicals. Identification of a good scaffold such as triazole, carbamate, methoxy acrylate, pyrazolamide, pyrido-pyrimidinone mesoionic, and bisamide often leads to the development of a new series of pesticides. In addition, pesticides with the same target, including the inhibitors of succinate dehydrogenase (SDH), oxysterol-binding-protein, and p-hydroxyphenyl pyruvate dioxygenase (HPPD), may have the same or similar scaffold structure. Recent years have witnessed significant progress in the discovery of new pesticides using natural products as scaffolds or bridges. In recent years, there have been increasing reports on the application of natural benzopyran compounds in the discovery of new pesticides, especially osthole and coumarin. A systematic and comprehensive review of benzopyran active compounds in the discovery of new agricultural chemicals is helpful to promote the discussion and development of benzopyran active compounds. Therefore, this work systematically reviewed the research and application of benzopyran derivatives in the discovery of agricultural chemicals, summarized the antiviral, herbicidal, antibacterial, fungicidal, insecticidal, nematicidal and acaricidal activities of benzopyran active compounds, and discussed the structural−activity relationship and mechanism of action. In addition, some active fragments were recommended to further optimize the chemical structure of benzopyran active compounds based on reference information.

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“…Many commercial pesticidal compounds have acylamino group in the molecule, for example carbamates and benzoylphenyl urea insecticides, anilide fungicides, ureas, amides and carbamates herbicides [ 34 ]. As a continuous study on the development of novel pesticides based on the coumarin scaffold [ 35 , 36 ], by introducing amides to 4-methylumbelliferone, a series of novel 4-methylumbelliferone amide derivatives were designed and synthesized through the principle of bioactive substructure combination. The acaricidal, herbicidal and antifungal activities of these new compounds were tested.…”

Section: Introductionmentioning

confidence: 99%

Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities

2018

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A series of novel 4-methylumbelliferone amide derivatives were designed, synthesized and characterized by 1H NMR, 13C NMR and HR-ESI-MS. The structures of compounds 4bd and 4be (compounds named by authors) were further confirmed by X-ray single crystal diffraction. The acaricidal, herbicidal and antifungal activities of the synthesized compounds were assayed for their potential use as pesticide. The results indicated that compounds 4bi, 4ac and 4bd were strong acaricidals against Tetranychus cinnabarinus, with 72h corrected mortalities of greater than 80% at 1000 mg/L. Meanwhile, compounds 4bh and 4bf exhibit the strongest inhibition against the taproot development of Digitaria sanguinalis and Chenopodium glaucum, and were even more potent than the commercial herbicide Acetochlor against D. sanguinalis. In addition, compounds 4bk, 4bh and 4bp showed the highest antifungal activity against the mycelium growth of Valsa mali, which makes them more effective than commercial fungicide Carbendazim.

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Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives

Cited by 6 publications

References 3 publications

Novel Trifluoromethylcoumarinyl Urea Derivatives: Synthesis, Characterization, Fluorescence, and Bioactivity

Novel Trifluoromethylcoumarinyl Urea Derivatives: Synthesis, Characterization, Fluorescence, and Bioactivity

Recent Advances and Outlook of Benzopyran Derivatives in the Discovery of Agricultural Chemicals

Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities

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