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

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 ant...

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Main Authors: Yan Wei, Kai-Long Miao, Shuang-Hong Hao
Format: Article
Language:English
Published: MDPI AG 2018-01-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/23/1/122
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spelling doaj-297d4becdcac4b28b5f23414b0ab06ff2020-11-24T23:54:16ZengMDPI AGMolecules1420-30492018-01-0123112210.3390/molecules23010122molecules23010122Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal ActivitiesYan Wei0Kai-Long Miao1Shuang-Hong Hao2Research Center of Agro-Bionic Engineering & Technology of Shandong Province, College of Chemistry & Pharm., Qingdao Agricultural University, Qingdao 266109, ChinaResearch Center of Agro-Bionic Engineering & Technology of Shandong Province, College of Chemistry & Pharm., Qingdao Agricultural University, Qingdao 266109, ChinaResearch Center of Agro-Bionic Engineering & Technology of Shandong Province, College of Chemistry & Pharm., Qingdao Agricultural University, Qingdao 266109, ChinaA 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.http://www.mdpi.com/1420-3049/23/1/1224-methylumbelliferonesynthesisacaricidal activityherbicidal activityantifungal activity
collection DOAJ
language English
format Article
sources DOAJ
author Yan Wei
Kai-Long Miao
Shuang-Hong Hao
spellingShingle Yan Wei
Kai-Long Miao
Shuang-Hong Hao
Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
Molecules
4-methylumbelliferone
synthesis
acaricidal activity
herbicidal activity
antifungal activity
author_facet Yan Wei
Kai-Long Miao
Shuang-Hong Hao
author_sort Yan Wei
title Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
title_short Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
title_full Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
title_fullStr Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
title_full_unstemmed Novel 4-Methylumbelliferone Amide Derivatives: Synthesis, Characterization and Pesticidal Activities
title_sort novel 4-methylumbelliferone amide derivatives: synthesis, characterization and pesticidal activities
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2018-01-01
description 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.
topic 4-methylumbelliferone
synthesis
acaricidal activity
herbicidal activity
antifungal activity
url http://www.mdpi.com/1420-3049/23/1/122
work_keys_str_mv AT yanwei novel4methylumbelliferoneamidederivativessynthesischaracterizationandpesticidalactivities
AT kailongmiao novel4methylumbelliferoneamidederivativessynthesischaracterizationandpesticidalactivities
AT shuanghonghao novel4methylumbelliferoneamidederivativessynthesischaracterizationandpesticidalactivities
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