This study aimed to synthesize some
new sulfone derivatives containing
a 1,3,4-oxadiazole moiety and investigate their in vitro antibacterial
activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), the pathogens
of rice bacterial leaf blight and citrus canker, respectively, by
performing turbidimeter tests. Antibacterial bioassay results showed
that compound 6d revealed excellent bioactivities against Xoo and Xac, with the 50% effective concentration
(EC50) values of 0.17 and 1.98 μg/mL, respectively,
compared with thiodiazole copper (121.82 and 77.04 μg/mL, respectively)
and bismerthiazol (92.61 and 58.21 μg/mL, respectively). Meanwhile,
greenhouse-condition trials indicated that, compared with thiodiazole
copper and bismerthiazol, compound 6d more effectively
reduced rice bacterial leaf blight.
2-Cyanoacrylate is an important kind of herbicide targeted in photosystem II. Starting from cyano ethyl acetate, the chiral title compounds were synthesized under microwave irradiation, which has the advantages of shorter reaction time, higher yield, and simpler procedure. A half-leaf method was used to determine the inhibition and curative efficacies of the eight chiral products against tobacco mosaic virus in vivo. It was found that chiral compound IIc-R possesses moderate inhibition and curative effect in vivo with rates of 89.1 and 43.1%, respectively. In the MTT test, these new chiral compounds were found to possess weak antiproliferation activities to PC3 and A431 cells.
Target compounds 4a- n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaldoximes (3) with chloromethylated heterocyclic compounds (ClCH 2-R 3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a- e with KMnO 4 in HOAc at room temperature afforded eight new compounds, 5a- h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, (1)H NMR, (13)C NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC 50 = 58.7 and 65.3 microg/mL) as the commercial product Ningnanmycin (EC 50 = 52.7 microg/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.
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