Synthesis and Biological Activities of 3‐Substituted Analogues of Tenuazonic Acid

Liu, Yuxiu; Cui, Zhipeng; Zhao, Huihui; Li, Yonghong; Gu, Yu‐Cheng; Wang, Qingmin

doi:10.1002/jhet.1878

Cited by 6 publications

(2 citation statements)

References 20 publications

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“…The previous modification at C-5 position with alkyl groups showed positive effect for improving the bioactivity. [4,5] Especially, the introduction of 5,5-spirocyclo moieties at the skeleton of tetronic acid led to the discovery of new classes of insecticides such as spirodiclofen, spiromesifen and spirotetramat (Figure 1), which indicated that the 5,5-spirotetramic and 5,5-spirotetronic acid derivatives changed the mode of action with the greatly improved activities. [6][7][8] In the past decades, the synthesis and biological activity evaluation of 5-akyltetronic acid derivatives have also attracted enormous attentions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives

Zhao¹,

Guan²,

Li³

et al. 2019

Chin. J. Org. Chem.

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A series of novel 3-acetyl-4-hydrazinyl-5,5-disubstitutedtetronic acid and (E/Z)-3-(1-hydrazinylethyli-dene)-5,5disubstitutedfuran-2,4-dione derivatives were designed and synthesized, and four methyl 5-methyl pyrazole-4-carboxylate were obtained unexpectedly. Their structures were confirmed by high-resolution mass spectrum (HR-ESI-MS), 1 H NMR, 13 C NMR spectral data and X-ray diffraction. The bioassay results of the hydrazinyl compounds along with the amino analogues indicated that some compounds exhibited moderate to excellent fungicidal activities against phytopathagens. For example, compounds 5G, 5H, 5I and 5i showed 100% in vivo control efficacy against Colletotrichum lagenarium, and compound 5G also exhibited 100% in vivo control efficacy against Erysiphe graminis, Puccinia polysora and Colletotrichum lagenarium at 400 μg/mL. Compounds 5b, 5E and 6F showed 100% mortality against Plutella xylostella, compounds 6A, 6g and 6H exhibited 100% mortality against Myzus persicae, and compound 6b showed 100% mortality against Tetranychus cinnabarinus at 600 μg/mL. The 5,5-spiro cyclohexyl moiety significantly improved the fungicidal activity of the tetronic acid derivatives, and the introduction of the substituted hydrazino group to the furan-2,4-dione skeleton led to higher insecticidal and acaricidal activities. 5G and 5i were found to have the most potential to be further modified for searching new fungicide as the lead compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives

Zhao¹,

Guan²,

Li³

et al. 2019

Chin. J. Org. Chem.

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“…Butenolide scaffold is widely found in the natural products [ 20 , 21 ], such as stypolactone [ 22 ], lambertellol A [ 23 ], yaoshanenolides A, yaoshanenolides B [ 24 , 25 ] and others. These natural products have insecticidal [ 26 , 27 , 28 ], bactericidal [ 29 , 30 , 31 ], antifungal [ 32 , 33 ], antitumor and other excellent biological activities. The commercially available butenolide pesticides include spirodiclofen [ 34 ], spiromesifen [ 35 ], spirotetramat [ 36 ], spiropidion [ 37 ] and flupyradifurone [ 38 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of New butenolide Containing Methoxyacrylate Scaffold

Zhang

Zhao

et al. 2022

Molecules

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In order to improve the antifungal activity of new butenolides containing oxime ether moiety, a series of new butenolide compounds containing methoxyacrylate scaffold were designed and synthesized, based on the previous reports. Their structures were characterized by 1H NMR, 13C NMR, HR-MS spectra, and X-ray diffraction analysis. The in vitro antifungal activities were evaluated by the mycelium growth rate method. The results showed that the inhibitory activities of these new compounds against Sclerotinia sclerotiorum were significantly improved, in comparison with that of the lead compound 3–8; the EC50 values of V-6 and VI-7 against S. sclerotiorum were 1.51 and 1.81 mg/L, nearly seven times that of 3–8 (EC50 10.62 mg/L). Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observation indicated that compound VI-3 had a significant impact on the structure and function of the hyphal cell of S. sclerotiorum mycelium and the positive control trifloxystrobin. Molecular simulation docking results indicated that the introduction of methoxyacrylate scaffold is beneficial to improving the antifungal activity of these compounds against S. sclerotiorum, which can be used as the lead for further structure optimization.

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Studies on the Synthesis and Bioactivities of 4‐Amino Derivatives of Tetramic Acid

Liu

Zhao

Song

et al. 2014

Journal of Heterocyclic Chem

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Synthesis and Biological Activities of 3‐Substituted Analogues of Tenuazonic Acid

Cited by 6 publications

References 20 publications

Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives

Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives

Synthesis and Antifungal Activity of New butenolide Containing Methoxyacrylate Scaffold

Studies on the Synthesis and Bioactivities of 4‐Amino Derivatives of Tetramic Acid

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