Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi
A compound, C1-C6- technology, applied in the direction of chemicals for biological control, plant growth regulators, botanical equipment and methods, etc., can solve the problems of narrow application spectrum, no fungicidal activity, etc.
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Embodiment 1
[0332] Example 1: 2-(2-chloro-5-methylphenoxy)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzene base) preparation of ethyl-1-one (compound 33):
[0333] a) Step-1:-4-(2-Methyl-1,3-dioxolan-2-yl)benzonitrile
[0334]To a stirred solution of 4-acetylbenzonitrile (10 g, 69 mmol) and ethylene glycol (80 mL, 1.4 mol) was added trimethyl orthoformate (50 mL, 0.9 mol) and N-bromosuccinyl at 25 °C Amine (1.2 g, 7 mmol). The resulting reaction mixture was stirred at 65°C for 12 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (120 mL) and washed with water (80 mL). The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (12 g, 92% yield).
[0335] b) Step-2:-N'-Hydroxy-4-(2-methyl-1,3-dioxolan-2-yl)benzamidine
[0336] To a stirred solution of 4-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (12 g, 63 mmol) and ethanol (80 mL) was added...
Embodiment 2
[0350] Example 2: -2-((4-methoxyphenyl)thio)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl) The preparation of phenyl) ethyl-1-ketone (compound 23):
[0351] At 0°C, 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.3g , 0.9 mmol) and acetonitrile (8 mL) were added potassium carbonate (0.27 g, 2 mmol) and 4-methoxythiophenol (0.13 g, 0.9 mmol). The resulting reaction mixture was stirred at 25°C for 1 hour. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 mL) and washed with water (10 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 20% ethyl acetate in hexane as eluent to give 2-((4-methoxyphenyl)thio)-1-(4-(5- (Trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.19 g, 54% yield).
[0352] Table 2: The following compounds were prepared using similar procedures...
Embodiment 3
[0357] Example 3: -2-((3,4-difluorophenyl)amino)-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl) The preparation of phenyl) ethyl-1-ketone (compound 27):
[0358] To a stirred solution of 3,4-difluoroaniline (0.1 g, 0.8 mmol) and N,N-dimethylformamide (8 mL) at 0 °C was added sodium bicarbonate (0.11 g, 1.3 mmol) and potassium iodide (0.02 g, 0.1 mmol). The mixture was stirred at 25°C for 15 minutes. Then 2-bromo-1-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)ethan-1-one (0.22g , 0.7 mmol), and the resulting reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (10 mL) and washed with water (10 mL). The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel using 20% ethyl acetate in hexane as eluent to give 2-((3,4-difluorophenyl)amino)-1-(4-(5- (Trifluoromethyl)-1,2,4-...
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