Quinoline 4-hydroxypicolinate compound and application thereof in prevention and treatment of magnaporthe oryzae
A technology of hydroxypicolinic acid and rice blast fungus, applied in application, fungicide, organic chemistry and other directions, can solve the problem of no research and development report on the activity of rice blast fungus, and achieve the effect of improving comprehensive performance and good environmental compatibility
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Embodiment 1
[0030] Preparation of 6-(trifluoromethyl)-quinolin-4-yl(2-fluoropyridine)carboxylate (I-a)
[0031] 2-Fluoropyridine-3-carboxylic acid (1.1 mol) and intermediate 6-trifluoromethyl-4-quinolinol (1.0 mmol) were dissolved in 3 mLofCH 2 Cl 2 The solvent was stirred and cooled down to 0°C, and EDCI (1.2 mmol) and DMAP (1.2 mmol) were added to the above system. The reaction was carried out at 40°C under nitrogen protection for 15h-20h. After the reaction was completed, the reaction solution was washed with saturated brine (2×2mL), and washed with water (2×2mL), dried over sodium sulfate, filtered with suction, and the crude product was obtained by flash column chromatography (petroleum ether / ethyl acetate, v / v=10 :1–1:1) to obtain compound 6-(trifluoromethyl)-quinolin-4-yl(2-fluoropyridine)carboxylate, white powder, yield 51%, 1 H NMR (400MHz, CDCl 3 )δ: 9.08 (d, J = 4.8Hz, 1H), 8.62–8.67 (m, 1H), 8.58 (d, J = 4.4Hz, 1H), 8.45 (s, 1H), 8.29 (d, J 1 =8.8Hz,1H),7.95(dd,J 1 =8.8Hz...
Embodiment 2
[0033] Preparation of 6-(trifluoromethyl)-quinolin-4-yl(2-chloropyridine)carboxylate (I-b)
[0034] White powder, yield 37%, 1 H NMR (400MHz, CDCl 3 )δ: 9.11(d,J=4.8Hz,1H), 8.70(dd,J 1 =4.8Hz,J 2 =2.0Hz,1H),8.51(dd,J 1 =8.0Hz,J 2 =2.0Hz,1H),8.41(s,1H),8.31(d,J 1 =8.8Hz,1H),7.96(dd,J 1 =8.8Hz,J 1 =1.5Hz,1H),7.64(d,J=4.8Hz,1H),7.53(dd,J 1 =8.0Hz,J 2 = 4.8Hz, 1H).
Embodiment 3
[0036] Preparation of 6-(trifluoromethyl)-quinolin-4-yl(2-methoxypyridine)carboxylate (I-c)
[0037] White powder, yield 26%, 1 H NMR (400MHz, CDCl 3 )δ:9.07(d,J=4.6Hz,1H), 8.63(s,1H),8.48(dd,J 1 =4.8Hz,J 2 =1.7Hz,1H),8.44(dd,J 1 =7.5Hz,J 2 1.7 Hz, 1H), 8.28(d, J=8.8Hz, 1H), 7.95(d, J=8.8Hz, 1H), 7.72(d, J=4.9Hz, 1H), 7.11 (dd, J 1 =7.5Hz,J 2 =4.9Hz, 1H), 4.19(s, 3H).
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