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Preparation method and application of difluoromethylpyrazoxime ester containing 3-trifluoromethyl-5-chloropyrazole structure
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A kind of technology of difluoromethyl pyrazole oxime and trifluoromethyl, which is applied in the field of preparation of difluoromethyl pyrazole oxime ester
Active Publication Date: 2021-06-29
NANTONG UNIVERSITY
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However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice
Method used
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Embodiment 1
[0031]
[0032] Add 3mmol IIa, 20mmol triethylamine and 30mL dichloromethane into a reaction flask. Under stirring in an ice bath, a mixture of 6 mmol III and 3 mL of dichloromethane was added dropwise thereto. After the dropwise addition, stirring was continued at room temperature for 13 hours. After removing the solvent, the resulting residue was separated by column chromatography to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 )δ:8.08(s,1H, CH=N),6.80~7.24(m,5H,Ar-H and CHF 2 ),3.94(s,3H,CH 3 ),3.84(s,3H,CH 3 ).
Embodiment 2
[0034]
[0035] Add 4mmol IIb, 30mmol sodium acetate and 20mL chloroform into a reaction flask. Under stirring in an ice bath, a mixture of 6 mmol of III and 3 mL of chloroform was added thereto. After the addition was complete, the reaction was stirred at room temperature for 18 hours. After removing the solvent, the resulting residue was separated by column chromatography to obtain the target Ib; 1 H NMR (400MHz, CDCl 3 )δ:8.18(s,1H,CH=N), 7.31~7.37(m,1H,Ar-H),6.74~7.07(m,4H,Ar-H and CHF 2 ),3.94(s,3H,CH 3 ),3.77(s,3H,CH 3 ).
Embodiment 3
[0037]
[0038] Add 5mmol IIc, 20mmol 4-dimethylaminopyridine (DMAP) and 30mL acetone into a reaction flask. Under stirring at room temperature, a mixed solution of 7 mmol of Intermediate III and 6 mL of acetone was added thereto. After the addition was completed, the reaction was continued under reflux for 20 hours. The solvent was removed under reduced pressure, and the resulting residue was separated by column chromatography to obtain the target Ic; 1 H NMR (400MHz, CDCl 3 ) δ: 8.11(s, 1H, CH=N), 6.79~7.09(m, 5H, Ar-H and CHF 2 ),3.94(s,3H,CH 3 ),3.79(s,3H,CH 3 ).
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Abstract
The present invention relates to the preparation method and application of difluoromethylpyrazoxime ester (I) containing 3-trifluoromethyl-5-chloropyrazole structure. Obtained by reacting difluoromethylpyrazole oxime (II) with 3‑trifluoromethylpyrazoleformyl chloride (III). The difluoromethylpyrazole oxime ester containing 3-trifluoromethyl-5-chloropyrazole structure has effective control effects on harmful insects, and the compound can be used to prepare pesticides in fields such as agriculture and gardening.
Description
technical field [0001] The invention relates to the field of chemical pesticides, in particular to a preparation method and application of difluoromethylpyrazoxime ester containing a 3-trifluoromethyl-5-chloropyrazole structure. Background technique [0002] Pest control has always been the core field of pesticide scientific research, and the widespread use of insecticides has enabled most pests to be effectively controlled. However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice. [0003] Pyrazoleoxime compounds are important nitrogen-containing heterocyclic compounds, which play an important role in agriculture, and the representative compound is pyraclofen. [0004] [0005] The substituted pyrazole ring is also...
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