Ethyl isoxazoline derivative and application thereof
An ethyl and alkyl technology, applied in the field of isoxazoline derivatives and their preparation, can solve the problems of insufficient herbicidal action, narrow weed plant spectrum, low selectivity and the like
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Embodiment 1
[0102] Example 1: 3-(((5-chloro-3-(difluoromethyl)-1-(3-fluorophenyl)-1H-pyrazol-4-yl)methyl)sulfonyl)-5- Synthesis of Ethyl-5-methyl-4,5-dihydroisoxazole
[0103]
[0104] Step 1: Synthesis of 3-(difluoromethyl)-1-(3-fluorophenyl)-1H-pyrazol-5-ol
[0105]
[0106] Ethyl difluoroacetoacetate (5.00g, 30.1mmol) was dissolved in absolute ethanol (100mL), stirred at 0°C, and then 3-fluorophenylhydrazine (5.69g, 45.2mmol) was slowly added dropwise to the above mixture, After the dropwise addition, the temperature was raised to room temperature to react for 2 hours, and then the temperature was raised to 80° C. to react overnight, and the reaction was stopped. The ethanol was removed, the above mixed solution was washed with water (100mL), extracted three times with ethyl acetate (50mL), the organic phases were combined to remove the solvent under reduced pressure, and separated by column chromatography (eluent: Petroleum ether / EtOAc (v / v) = 10 / 1), to obtain 4.00 g of yellow...
Embodiment 2
[0129]Example 2: 3-(((5-Chloro-3-(difluoromethyl)-1-(2,4-difluorophenyl)-1H-pyrazol-4-yl)methyl)sulfonyl) -Synthesis of 5-ethyl-5-methyl-4,5-dihydroisoxazole
[0130]
[0131] Step 1: Synthesis of 3-(difluoromethyl)-1-(2,4-difluorophenyl)-1H-pyrazol-5-ol
[0132]
[0133] Dissolve ethyl difluoroacetoacetate (5.00g, 30.1mmol) in absolute ethanol (100mL), stir at 0°C, then slowly drop (2,4-difluorophenyl)hydrazine (6.51g, 45.2mmol) Add it to the above mixture, after the dropwise addition is complete, raise the temperature to room temperature to react for 2 hours, then raise the temperature to 80°C to react overnight, and stop the reaction. The ethanol was removed, the above mixed solution was washed with water (100mL), extracted three times with ethyl acetate (50mL), the organic phases were combined to remove the solvent under reduced pressure, and separated by column chromatography (eluent: Petroleum ether / EtOAc (v / v) = 10 / 1), to obtain 4.00 g of yellow solid product, y...
Embodiment 3
[0156] Example 3: 3-(((3-chloro-5-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl)methyl)sulfonyl)-5-ethyl-5- Synthesis of Methyl-4,5-Dihydroisoxazole
[0157]
[0158] Step 1: 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde and 3-chloro-5-(difluoromethyl)-1-methyl-1H- Synthesis of Pyrazole-4-Carboxaldehyde
[0159]
[0160] Ethyl difluoroacetoacetate (5.00g, 30.1mmol) was dissolved in absolute ethanol (100mL), stirred at 0°C, then hydrazine hydrate (1.45g, 45.2mmol) was slowly added dropwise to the above mixture, and the addition was completed , heated up to room temperature at 25°C and reacted for 4h, then heated up to 80°C and reacted overnight to stop the reaction. The ethanol was removed, the above mixture was washed with water (50 mL), extracted three times with ethyl acetate (50 mL), the organic phases were combined and the solvent was removed under reduced pressure to obtain a light yellow solid product.
[0161] DMF (2.20g, 30.1mmol) was stirred at ...
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