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 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.

[1]  Y. Wei,et al.  New angular oxazole-fused coumarin derivatives: synthesis and biological activities , 2018, Natural product research.

[2]  Y. Wei,et al.  Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives , 2018 .

[3]  Akshata R. Pahelkar,et al.  Preparative-scale synthesis of amino coumarins through new sequential nitration and reduction protocol , 2017 .

[4]  Renuka Nagamallu,et al.  Synthesis of Coumarin Appended 1,3-Oxazines as Potent Antimicrobial and Antioxidant Agents , 2017, Pharmaceutical Chemistry Journal.

[5]  Young Hwan Park,et al.  Suppression of IgE‐mediated mast cell activation and mouse anaphylaxis via inhibition of Syk activation by 8‐formyl‐7‐hydroxy‐4‐methylcoumarin, 4&mgr;8C , 2017, Toxicology and applied pharmacology.

[6]  A. Gryboś,et al.  Synthesis of a new series of aryl/heteroarylpiperazinyl derivatives of 8-acetyl-7-hydroxy-4-methylcoumarin with low nanomolar 5-HT1A affinities. , 2017, European journal of medicinal chemistry.

[7]  Hongwei Zhou,et al.  Coumarin-based Hg2+ fluorescent probe: Synthesis and turn-on fluorescence detection in neat aqueous solution , 2017 .

[8]  Le Pan,et al.  Antifungal activity of umbelliferone derivatives: Synthesis and structure-activity relationships. , 2017, Microbial pathogenesis.

[9]  Virendra R. Mishra,et al.  Photostability of Coumarin Laser Dyes - a Mechanistic Study Using Global and Local Reactivity Descriptors , 2017, Journal of Fluorescence.

[10]  Zhaojun Han,et al.  Evaluation of antifungal activities and structure-activity relationships of coumarin derivatives. , 2017, Pest management science.

[11]  Yong Wang,et al.  A highly selective and sensitive fluorescence probe for rapid detection of hypochlorite in tap water and cancer cells , 2016 .

[12]  Gaoxue Wang,et al.  Synthesis and anthelmintic activity of coumarin-imidazole hybrid derivatives against Dactylogyrus intermedius in goldfish. , 2016, Bioorganic & medicinal chemistry letters.

[13]  V. Vyas,et al.  Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives. , 2016, Bioorganic chemistry.

[14]  Guanghua Zhang,et al.  Synthesis of polymeric fluorescent brightener based on coumarin and its performances on paper as light stabilizer, fluorescent brightener and surface sizing agent , 2016 .

[15]  Xiu-Zhuang Li,et al.  Phytotoxicity of umbelliferone and its analogs: Structure-activity relationships and action mechanisms. , 2015, Plant physiology and biochemistry : PPB.

[16]  Yang Zhang,et al.  Coumarin derivatives from Ainsliaea fragrans and their anticoagulant activity , 2015, Scientific Reports.

[17]  Hengshan Wang,et al.  Novel Coumarin-Containing Aminophosphonatesas Antitumor Agent: Synthesis, Cytotoxicity, DNA-Binding and Apoptosis Evaluation , 2015, Molecules.

[18]  A. Kulkarni,et al.  Synthesis, spectral, thermal, fluorescence, antimicrobial, anthelmintic and DNA cleavage studies of mononuclear metal chelates of bi-dentate 2H-chromene-2-one Schiff base. , 2015, Journal of photochemistry and photobiology. B, Biology.

[19]  王栋,et al.  N -酰基- N -间氟苄基-6-氨基香豆素的合成及除草活性 , 2015 .

[20]  Radwan S. El-Haggar,et al.  Anti-Inflammatory Screening and Molecular Modeling of Some Novel Coumarin Derivatives , 2015, Molecules.

[21]  J. Bollyky,et al.  4-Methylumbelliferone Treatment and Hyaluronan Inhibition as a Therapeutic Strategy in Inflammation, Autoimmunity, and Cancer , 2015, Front. Immunol..

[22]  Dominik Koszelewski,et al.  Mixed Carbonates as Useful Substrates for a Fluorogenic Assay for Lipases and Esterases , 2015, Chembiochem : a European journal of chemical biology.

[23]  K. Racke.  Pesticide Chemistry , 2015 .

[24]  P. Kuo,et al.  Synthesis and Antibacterial Activity of Analogs of 5-Arylidene-3-(4-methylcoumarin-7-yloxyacetylamino)-2-thioxo-1,3-thiazoli-din-4-one , 2014, Molecules.

[25]  A. García-Argáez,et al.  Vasodilation and radical-scavenging activity of imperatorin and selected coumarinic and flavonoid compounds from genus Casimiroa. , 2014, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[26]  Z. Liao,et al.  Coumarin-containing aminophosphonates bridged with chiral side chain: synthesis and influence of chirality on cytotoxicity and DNA binding , 2013, Medicinal Chemistry Research.

[27]  L. Gille,et al.  4-Methyl-7-hydroxycoumarin antifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties. , 2013, Food chemistry.

[28]  V. Lokeshwar,et al.  Dietary supplement hymecromone and sorafenib: a novel combination for the control of renal cell carcinoma. , 2013, The Journal of urology.

[29]  Xiaobing Wang,et al.  α-Glucosidase inhibitors via green pathway: biotransformation for bicoumarins catalyzed by Momordica charantia peroxidase. , 2013, Journal of agricultural and food chemistry.

[30]  B. Hammock,et al.  Development of pyrethroid-like fluorescent substrates for glutathione S-transferase. , 2012, Analytical biochemistry.

[31]  P. Arora,et al.  Synthesis and Screening of Some Novel Coumarin Derivatives for Antipsychotic Activity , 2012 .

[32]  Hong Liang,et al.  Synthesis and antioxidant activities of novel 4-Schiff base-7-benzyloxy-coumarin derivatives. , 2011, Bioorganic & medicinal chemistry letters.

[33]  K. Bhat,et al.  Isolation, characterisation and antibacterial activity studies of coumarins from Rhododendron lepidotum Wall. ex G. Don, Ericaceae , 2010 .

[34]  U. Phalgune,et al.  Efficacy of 4-methyl-7-hydroxy coumarin derivatives against vectors Aedes aegypti and Culex quinquefasciatus. , 2008, Indian journal of experimental biology.

[35]  G. Leclercq,et al.  Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells. , 2007, Bioorganic & medicinal chemistry.

[36]  Y. Tyagi,et al.  Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity. , 2005, European journal of medicinal chemistry.

[37]  M. Ramana,et al.  Guanidinium Nitrate: A Novel Reagent for Aryl Nitrations. , 2005 .

[38]  R. Khanna,et al.  Regioselective Mononitration of Coumarins Using Chromium Nitrate as Nitrating Agent. , 2002 .

[39]  N. Ganguly,et al.  CERIUM(IV) AMMONIUM NITRATE MEDIATED NITRATION OF COUMARINS , 2001 .

[40]  T. Dennehy,et al.  The microimmersion bioassay: A novel method for the topical application of pesticides to spider mites , 1993 .

[41]  K. Shin,et al.  Effects of psoralen and angelicin on hepatic drug-metabolizing enzyme activities , 1988 .

[42]  I. Kozlova.  Synthesis of o-acylamino-4-methyl-7-hydroxycoumarins (4-methylumbelliferones) , 1985 .

[43]  S. Banerjee,et al.  Coumarins of Heracleum canescens and Heracleum pinnatum. Sources for dermal photosensitizing agents. , 1976, Planta medica.