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.

Based on the structure of lead compound of 7-hydroxy-4-methyl-coumarin, a series of novel fluorinated amide coumarin derivatives were designed and synthesized through the principle of bioactive substructure combination. Their structures were characterized by 1 H NMR, were further confirmed by X-ray single crystal diffraction. The results of herbicidal activity indicated that compounds f1, N-phenylacetyl-N-(m-fluorobenzyl)-6-amino-7-methyloxy-4-trifluoromethyl-coumarin (f13), exhibited marked inhibition against the stem growth of Digitaria sanguinalis. And f9, f7, N-(naphthalene-2-carbonyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f17) showed excellent inhibition on the stem of Chenopodium glaucum. The herbicidal activities of the compounds mentioned above were more active than the commercial herbicide acetochlor. The results of crop safety evaluation showed that compounds f1、f9 and f13 were safe to Brassica pekinensis and Brassica napus but sensitive to Triticum aestivum and Sorghum bicolor. Furthermore, N-(m-bromobenzoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f12), f7 and f9 were medium active against the mycelium of phytopathogenic fungi Botrytis cinerea. was medium active to Valsa mali.