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A class of N-phenylpyrazole-containing bisamide derivatives, preparation method and applications thereof

A technology of phenylpyrazole and bisamide, which is applied in the field of synthesis of agricultural chemical insecticides, can solve problems such as insect resistance, and achieve the effects of low production cost, improved insecticidal activity, and simple preparation methods

Inactive Publication Date: 2019-06-25
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, chemical insecticides are one of the effective means to prevent and control agricultural pests. However, with the widespread and irrational use of traditional insecticides, it has caused increasingly serious insect resistance and environmental problems. It is necessary to continuously develop green, efficient, low-toxic, and A new type of insecticide with low cost and unique mechanism of action

Method used

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  • A class of N-phenylpyrazole-containing bisamide derivatives, preparation method and applications thereof
  • A class of N-phenylpyrazole-containing bisamide derivatives, preparation method and applications thereof
  • A class of N-phenylpyrazole-containing bisamide derivatives, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] N-[4-chloro-2-methyl-6-[(methylcarbamoyl)phenyl]-1-(52,6-dichloro-4-nitrophenyl)-3-(trifluoromethyl base)-1H-pyrazole-5-carboxamide (derivative 08) synthesis

[0037] 1) Step A: N-[4-chloro-2-methyl-6-[(methylcarbamoyl)phenyl]-1-(2,6-dichloro-4-nitrophenyl)-3 -(Trifluoromethyl)-1H-pyrazole-5-carboxamide

[0038]Dissolve 11.76g (30mmol) of 3-trifluoromethyl-1-((2,6-dichloro-4-nitro)phenyl)-5-(furan-2-yl)-1H-pyrazole in 50mL In the mixed solution of acetone and water, add 9.48g (60mmol) potassium permanganate in batches, raise the temperature to reflux, react for 0.5h, TLC detects that the reaction is complete; Potassium oxide solution was fully basified to pH 12, and then the organic impurities were extracted with ethyl acetate, and the aqueous phase was acidified to pH 1 with a concentration of 2mol / L hydrochloric acid solution, and a solid was precipitated, dried by suction filtration to obtain 3-trifluoromethyl-1-( (2,6-Dichloro-4-nitro)phenyl)-1H-pyrazole-5-carbox...

Embodiment 2

[0042] N-[4-chloro-2-methyl-6-[(methylcarbamoyl)phenyl]-1-(2-chloro-5-nitrophenyl)-3-(trifluoromethyl)- Synthesis of 1H-pyrazole-5-carboxamide (derivative 176)

[0043] 1) Step A: Preparation of 3-trifluoromethyl-1-((2-chloro-5-nitro)phenyl)-1H-pyrazole-5-carboxylic acid

[0044] Dissolve 10.71 g (30 mmol) of 3-trifluoromethyl-1-((2-chloro-5-nitro)phenyl)-5-(furan-2-yl)-1H-pyrazole in 50 mL of acetone and water Add 9.48g (60mmol) of potassium permanganate in batches to the mixed solution, raise the temperature to reflux, react for 0.5h, and TLC detects that the reaction is complete; Fully basified to pH 12, then extracted organic impurities with ethyl acetate, acidified the aqueous phase to pH 1 with a 2mol / L hydrochloric acid solution, precipitated a solid, and dried by suction to obtain 3-trifluoromethyl-1-((2- Chloro-5-nitro)phenyl)-1H-pyrazole-5-carboxylic acid, pale yellow solid, yield 76.6%, m.p.121-122°C

[0045] 2) Step B: Preparation of N-[4-chloro-2-methyl-6-[(met...

Embodiment 3

[0048] N-[4-chloro-2-methyl-6-[(methylcarbamoyl)phenyl]-1-(2-chloro-4,5-difluorophenyl)-3-(trifluoromethyl )-1H-pyrazole-5-carboxamide (derivative 624) synthesis

[0049] 1) Step A: Preparation of 3-trifluoromethyl-1-((2-chloro-4,5-difluoro)phenyl)-1H-pyrazole-5-carboxylic acid

[0050] Dissolve 10.44g (30mmol) 3-trifluoromethyl-1-((2-chloro-4,5-difluoro)phenyl)-5-(furan-2-yl)-1H-pyrazole in 50mL acetone In the mixed solution of water and water, add 9.48g (60mmol) potassium permanganate in batches, raise the temperature to reflux, and react for 0.5h; TLC detects that the reaction is complete; filter, the filtrate is decompressed to remove acetone, and oxidized with 2mol / L hydroxide Fully alkalinize the potassium solution to pH 12, then extract organic impurities with ethyl acetate, acidify the aqueous phase with 2mol / L hydrochloric acid solution to pH 1, extract with ethyl acetate, wash with saturated saline, combine the organic layers, dry, and remove the solvent Column chr...

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Abstract

The present invention relates to a class of N-phenylpyrazole-containing bisamide derivatives having insecticidal activity and represented by a general formula (I), preparation and applications thereof, wherein based on the existing bisamide compounds, different substituted benzene rings are introduced into the site 1 of a pyrazole ring, and R1, R2, R3, R4, R5, R6, R7, R8 and R9 are defined in thespecification. According to the present invention, the drug resistance of the original compound is improved, the insecticidal activity is improved, the production cost is lowered, and particularly theproduct has effects on Mythimna separata, Plutella xylostella and other lepidopteran pests, and is the insecticide with broad application prospects.

Description

technical field [0001] The invention relates to the synthesis technology of agricultural chemical insecticides, in particular to a kind of bisamide derivatives containing N-phenylpyrazole structure and its preparation method and application. Background technique [0002] At present, chemical insecticides are one of the effective means to control agricultural pests. However, with the widespread and irrational use of traditional insecticides, it has caused increasingly serious insect resistance and environmental problems. It is necessary to continuously develop green, efficient, low-toxic, A new type of insecticide with low cost and unique mechanism of action. [0003] O-carboxamidobenzamide compounds are effective insecticides developed in recent years to control Lepidoptera pests. Japan Pesticide Company, DuPont Company of the United States, Bayer Agriscience of Germany, and many domestic universities and scientific research institutions have applied for a large number of p...

Claims

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Application Information

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IPC IPC(8): C07D231/14C07D231/16C07D231/22A01P7/04
Inventor 李正名刘敬波张秀兰
Owner NANKAI UNIV