Abstract
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.
Highlights
The coumarin scaffold is an important structure type which exists in a wide class of natural and synthetic compounds [1]
4-methylumbelliferone (7-hydroxy-4-methylcoumarin, hymecromone) and its derivatives have been used as fluorescent probes to detect Hg2+ in neat aqueous solutions [14], and hypochlorite in tap water and cancer cells [15], as well as to assay lipases and esterases [16]. 4-Methylumbelliferone derivatives possess diverse biological properties, such as antipsychotic [17], antidepressant [18], anaphylaxis [19], hypoglycemic [20], antioxidant [21], anti-inflammatory [22], antitumor [23,24], antibacterial [25] and antifungal [26] properties
Even though some coumarins are toxic, 4-methylumbelliferone is a safe compound used as active ingredient in several approved drugs [27,28]
Summary
The coumarin scaffold is an important structure type which exists in a wide class of natural and synthetic compounds [1]. Derivatives of coumarin have broad applications in the fields of perfume, food additives, cosmetics, optical brighteners [2] and dye lasers [3]. They exhibit many bioactivities of the following categories: anticoagulant [4], vasodilator [5], sedation and hypnosis [6], analgesic and hypothermy [7], estrogenic [8], antioxidant [9], dermal photosensitization [10], antibacterial [11], antifungal [12], moluscicidal and anthelmintic [13]. 4-Methylumbelliferone and its derivatives exhibited interesting pesticidal activities as well These compounds displayed strong inhibition to weeds Setaria viridis and Amaranthus retroflexus.
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