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The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae
Long Cheng, Ruirui Zhang, Hongke Wu, Xinghai Liu, Tianming Xu
Front. Chem. Sci. Eng. ›› 2019, Vol. 13 ›› Issue (2) : 369-376.
The synthesis of 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives and their antifungal activity against Pyricularia oryzae
A series of novel 6-(tert-butyl)-8-fluoro-2,3-dimethylquinoline carbonate derivatives were designed and synthesized. Bioassay results showed that some of them exhibited good activity against Pyricularia oryzae (P. oryzae). It was found that the compound 5q (benzyl (6-(tert-butyl)-8-fluoro-2,3-dimethylquinolin-4-yl) carbonate) possessed good activity against P. oryzae whatever protective activity (10 mg·L−1) or curative activity (25 mg·L−1), which was better than that of control tebufloquin. In addition, the frontier molecular orbit results revealed that the compound held higher activity against P. oryzae when the total energy was low and the ClogP was high, which may provide useful information for further design novel fungicides.
quinoline / synthesis / antifungal activity / rice blast / SAR
Fig.1 (a) Schematics of a Pickering emulsion. (b) Asymmetric Janus Pickering emulsions through particle jamming of coalesced emulsions. The scale bar is 500 μm. Reproduced with permission from Ref. [15], copyright 2014, Springer Nature. (c) The deformation and stability of Pickering emulsions in an electric field. The scale bar is 300 μm. Reproduced with permission from Ref. [11], copyright 2013, The American Association for the Advancement of Science. (d) Schematics of an armored bubble. (e) Optic images of a spherical armored bubble. The scale bar is 400 μm. Reproduced with permission from Ref. [18], copyright 2006, American Chemical Society. (f) Two floating armored bubbles do not coalesce due to particle stabilization. The scale bar is 200 μm. Reproduced with permission from Ref. [37], copyright 2020 Elsevier. (g) Nonspherical armored bubbles with various shapes [18]. The scale bar is 200 μm. (h) Schematics of a liquid marble. (i) Photographs of liquid marbles encapsulating various chemical solutions. The scale bar is 2 mm. Reproduced with permission from Ref. [38], copyright 2019, Wiley-VCH. (j) SEM image of a dried polyhedral liquid marble stabilized by hexagonal fluorinated PET plates. The scale bar is 200 μm. Reproduced with permission from Ref. [39], copyright 2019, Wiley-VCH. (k) Complex particle-stabilized liquid/air surfaces forming a complex structure representing a Chinese dragon symbol. The scale bar is 10 cm. Reproduced with permission from Ref. [40], copyright 2018, Wiley-VCH. |
Fig.2 (a) Schematic of a gas marble. Insert illustrating the cross-section of the gas marble shell and the layout of particles on the marble surface. (b) Optical image of a gas marble. The fluorescent picture demonstrates the enlargement of the particle layout. (c) Comparison of mechanical stability among gas marbles, liquid marbles and armored marbles at different sizes of bubbles and drops (Db). Both the critical overpressures (ΔP+) and underpressures (ΔP+) are normalized by capillary pressure (ΔPcap) to make a fair comparison. Reproduced with permission from Ref. [45], copyright 2017, American Physicsal Society. |
Fig.3 (a) Morphology and lifetimes of different marbles: soap water bubble, water gas marble and water/glycerol gas marble. The water/glycerol gas marble has the longest lifetime, which maintains its morphology after 9 months. (b) Phase diagram of different regimes of gas marble depending on the initial glycerol mass ratio and the relative humidity. Reproduced with permission from Ref. [8], copyright 2022, American Physical Society. |
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