A kind of piperic acid derivative and its preparation and application
A derivative, piperic acid technology, applied in the fields of insecticides, acaricides and fungicides, can solve the problems that insecticides, acaricides and fungicides have not been reported, so as to improve the chance of interaction and combination, Effects of overall biological properties
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Embodiment 1
[0124] Example 1: Preparation of Compound 1-45
[0125] 1) Preparation of N-(2-bromo-6-trifluoromethyl-4-heptafluoroisopropylphenyl)-2-fluoro-3-nitrobenzamide
[0126]
[0127] 2-Fluoro-3-nitrobenzoic acid (9.72g, 52.4mmol), thionyl chloride (40.05g) and DMF (0.40g) were added to the reaction flask, and the temperature was raised to 80°C for 8 hours, and then evaporated under reduced pressure. Thionyl chloride was added to obtain acid chloride, 1,3-dimethyl-2-imidazolidinone (160 mL), 2-bromo-6-trifluoromethyl-4-heptafluoroisopropylaniline (16.40 g, 40.0 mmol) and potassium iodide (1.68 g), the temperature was raised to 100° C. and reacted for 48 hours. The reaction solution was cooled to room temperature, filtered to remove insoluble matter, dissolved in ethyl acetate (100 mL), washed with saturated aqueous sodium bicarbonate solution and saturated brine successively, the organic phase was separated, the organic phase was dried over anhydrous magnesium sulfate, and filter...
Embodiment 2
[0141] Example 2: Preparation of Compound 1-2
[0142]
[0143] To the reaction flask was added 2,2-difluoro-1,3-benzodioxin-5-carboxylic acid (0.21 g, 1.0 mmol), thionyl chloride (1.08 g), toluene (10 mL) and DMF (1 drop), the temperature was raised to 80 °C for 4 hours, the thionyl chloride was evaporated under reduced pressure, the obtained acid chloride was dissolved in toluene (20 mL), and N-(2-bromo-6-trifluoromethyl-4-heptafluoro) was added. Isopropylphenyl)-2-fluoro-3-aminobenzamide (0.50 g, 0.9 mmol) was heated to 110° C. to react, and TLC was monitored until the reaction was complete. The reaction solution was cooled to room temperature, stirred well, a solid was gradually precipitated, filtered, and the filter cake was separated and purified by column chromatography to obtain the title compound, 0.55 g of white solid, the yield was 83% (as N-(2-bromo-6-trifluoromethane). (base-4-heptafluoroisopropylphenyl)-2-fluoro-3-aminobenzamide).
[0144] 1 H NMR (300MHz, ...
Embodiment 3
[0145] Example 3: Preparation of Compound 1-51
[0146] 1) Preparation of N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-nitrobenzamide
[0147]
[0148] 2-Fluoro-3-nitrobenzoic acid (3.71g, 20.0mmol), thionyl chloride (16.05g) and DMF (0.20g) were added to the reaction flask, the temperature was raised to 80°C and reacted for 6 hours, and evaporated under reduced pressure. Thionyl chloride was obtained to obtain acid chloride, acetonitrile (40 mL), 2,6-dibromo-4-heptafluoroisopropylaniline (4.23 g, 10.0 mmol), potassium iodide (0.42 g) were added, and the temperature was raised to 100 ° C for reaction, TLC Monitor until the reaction is complete, about 8 hours. The reaction solution was cooled to room temperature, filtered to remove insolubles, acetonitrile was evaporated under reduced pressure, ethyl acetate (30 mL) was added to dissolve, washed with saturated aqueous sodium bicarbonate solution and saturated brine successively, the organic phase was separated, a...
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