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N-methyl-N-o-benzoyl aminobenzene formamide compounds as well as preparation and application thereof

A technology of o-benzamidobenzamide and benzamide, which is applied in the preparation of organic compounds, carboxylic acid amide preparation, botanical equipment and methods, etc., can solve the problems of low selectivity, restrictions on popularization and application, and direct treatment of mammals. Sexual paralysis and other problems, to achieve the effect of simple treatment process, short reaction route and high yield

Inactive Publication Date: 2010-05-05
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the selectivity of the natural product ryanodine preparation is not high, it is highly toxic to mammals and can cause straight paralysis in mammals, which limits its popularization and application.

Method used

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  • N-methyl-N-o-benzoyl aminobenzene formamide compounds as well as preparation and application thereof
  • N-methyl-N-o-benzoyl aminobenzene formamide compounds as well as preparation and application thereof
  • N-methyl-N-o-benzoyl aminobenzene formamide compounds as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of N-(2-pyridyl)-2-(N-methyl-2-methyl-4-ethylpyrazolecarboxamido)benzamide (1g)

[0022] The synthetic route of the present invention is as follows:

[0023]

[0024] where R 1 For 2-methyl-4-ethylpyrazolyl, R 2 For pyridyl.

[0025] 1) Synthesis of intermediate 2-methylamino-methyl benzoate (1d):

[0026] Add 3g (0.02mol) of methyl anthranilate and 20mL of dimethyl sulfate into a 50mL flask, react at room temperature for 12h, pour into 40mL of 1mol / L NaOH solution, and wash the water layer with ethyl acetate (30mL×3 ) extraction, combined organic layers, washed with saturated brine, anhydrous Na 2 SO 4 Drying, filtration, and precipitation under reduced pressure gave a colorless liquid, and column chromatography gave 1.69 g of colorless liquid methyl 2-methylaminobenzoate, yield: 51%;

[0027] 2) Synthesis of intermediate 2-(N-methyl-2-methyl-4-ethylpyrazole carboxamido)methyl benzoate (1e)

[0028] Add 924mg (6mmol) of 1-methyl-3-ethyl-pyrazole-5...

Embodiment 2

[0034] N-(4-trifluoromethylphenyl)-2-(N-methyl-2-methyl-4-ethylpyrazolecarboxamido)benzamide (2g):

[0035] The intermediate is synthesized with reference to the method of Example 1:

[0036] Add 5mL of anhydrous dichloromethane and 250mg (0.87mmol) 2-(N-methyl-2-methyl-4-ethylpyrazolecarboxamido)benzoic acid to a 25mL single-necked flask, and dissolve 185mg (0.9mmol) DCC and 25mg (0.2mmol) DMAP anhydrous dichloromethane solution was slowly added dropwise in a three-necked flask, after stirring at room temperature for 30min, 233mg (0.83mmol) 4-trifluoromethylaniline anhydrous dichloromethane solution was added to the flask , stirred at room temperature for 2 hours, TLC followed the reaction, and after the reaction was completed, the insoluble matter was removed by filtration under reduced pressure, and the filtrate was decomposed with 1.2mol / L NaHCO 3 After washing, desolvation under reduced pressure to obtain a light yellow solid, 132 mg of a light yellow solid was obtained ...

Embodiment 3

[0038] N-(2,6-pyrimidinyl)-2-(N-methylbenzamido)benzamide (3 g):

[0039] The intermediate is synthesized with reference to the method of Example 1:

[0040] Add 5 mL of anhydrous dichloromethane and 218 mg (0.87 mmol) of 2-(N-methyl-2-benzamido) benzoic acid in a 25 mL one-necked flask, and mix 185 mg (0.9 mmol) of DCC and 25 mg ( Slowly add 0.2mmol) DMAP anhydrous dichloromethane solution dropwise into a three-necked flask, stir at room temperature for 30min, then add 78mg (0.83mmol) 2,6-pyrimidinamine anhydrous dichloromethane solution into the flask, stir at room temperature for 2h, follow the reaction by TLC , after the reaction is finished, filter under reduced pressure to remove insoluble matter, and use 1.2mol / L NaHCO for the filtrate 3 After washing, desolvation under reduced pressure, 166 mg colloidal solid was obtained by column chromatography, yield: 37% white solid, yield: 50.1%, m.p.172~174°C, 1 H NMR (CDCl 3 , 400MHz) δ: 3.51(s, 3H), 7.09~7.77(10H), 8.66(m, 2...

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PUM

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Abstract

The invention relates to N-methyl-N-benzoyl aminobenzene formamide compounds which have a structural formula presented by the general formula I, wherein R1 and R2 are substituted by aryl groups. The N-methyl-N-benzoyl aminobenzene formamide compounds are prepared by N methylation, amidation and hydrolysis, and reacting with corresponding arylamine under the action of DCC / DMAP . The applications of the N-methyl-N-benzoyl aminobenzene formamide compounds as pesticides for preventing and curing aphids, cotton bollworms and spodoptera exigua indicate that all the compounds have certain insecticidal activities on the aphids, the cotton bollworms, armyworms, the spodoptera exigua, and the like.

Description

technical field [0001] The invention belongs to N-methyl-N-phthalamido benzamide compounds and their preparation and application. Background technique [0002] The ryanodine receptor (RyR), which acts on the calcium channel in insect cells, is a novel insecticide target. Calcium ion is one of the most important second messengers in cells. The balance of calcium ion concentration in the body is closely related to the normal physiological activities of the body. Studies have found that calcium ions, as an important cell signaling substance, can participate in the release of synaptic neurotransmitters, the synthesis, distribution and metabolism of protein hormones, the activation of various enzymes inside and outside cells, the transmembrane transmission of biological signals, and the maintenance of nerve, Normal muscle excitability, regulation of glandular secretion and a series of physiological activities. Under normal circumstances, the concentration of calcium ions in cel...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D231/14C07D239/42C07C237/42C07C231/14A01N43/50A01N43/54A01N37/46A01N43/40A01P7/04
Inventor 巨修练刘志强
Owner WUHAN INSTITUTE OF TECHNOLOGY
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