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Anthranilic diamide compound with trifluoromethyl substituted N-arylpyrazole structures, method for preparing anthranilic diamide compound and application

A technology of formamidobenzamide and trifluoromethylphenyl, applied in the field of o-formamidobenzamide compounds and their preparation

Inactive Publication Date: 2017-11-21
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] It can be seen from the above that the current mainstream research methods often retain the main structure of N-pyridine-pyrazole and perform a large number of structural replacements on the 3-position substituent of pyrazole. Although some highly active compounds with development prospects have been found, but In the long run, traditional methods still need to be improved in order to obtain new compounds with novel structures

Method used

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  • Anthranilic diamide compound with trifluoromethyl substituted N-arylpyrazole structures, method for preparing anthranilic diamide compound and application
  • Anthranilic diamide compound with trifluoromethyl substituted N-arylpyrazole structures, method for preparing anthranilic diamide compound and application
  • Anthranilic diamide compound with trifluoromethyl substituted N-arylpyrazole structures, method for preparing anthranilic diamide compound and application

Examples

Experimental program
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Effect test

example 1

[0043] Example 1: N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(4-trifluoromethyl-2-thiazolyl)-3-trifluoromethyl- 1H-pyrazole-5-carboxamide

[0044] 3-trifluoromethyl-1-(4-trifluoromethyl-2-thiazolyl)-1H-pyrazole-5-carboxylic acid (6mmol) was placed in a 100 mL two-necked flask, and 50 mL of anhydrous dichloro Methane and 2 drops of DMF. Afterwards, the reaction was placed in an ice bath, and oxalyl chloride (15 mmol) was slowly added dropwise at 0° C. After 20 min, the addition was completed, and stirred at room temperature for 2 h. After TLC confirmed that the reaction was complete, the solvent was removed under reduced pressure to obtain 3-trifluoromethyl-1-(4-trifluoromethyl-2-thiazolyl)-1H-pyrazole-5-yl chloride, which was sealed and stored.

[0045] In a 100 mL three-necked flask, the acid chloride (6 mmol) prepared above was dissolved in a mixed solution of 45 mL of anhydrous N,N-dimethylformamide and 15 mL of anhydrous pyridine, and stirred at 70° C. for 30 min....

example 2

[0047] Example 2: N-(4-chloro-2-methyl-6-(isopropylcarbamoyl)phenyl)-1-(4-trifluoromethyl-2-thiazolyl)-3-trifluoromethyl -1H-pyrazole-5-carboxamide

[0048] The above preparation of 6-chloro-8-methyl-2-(3-trifluoromethyl-1-(4-trifluoromethyl-2-thiazolyl)-1H-pyrazol-5-yl)-4H- 1,3-Benzoxazinone (2.0mmol) was placed in a 50mL two-necked reaction flask, 25mL N,N-dimethylacetamide was added, and then isopropylamine (6.0mmol) was slowly added dropwise, stirred at room temperature for 2h, filtered, The filter cake was dried to obtain the target product N-(4-chloro-2-methyl-6-(isopropylcarbamoyl)phenyl)-1-(4-trifluoromethyl-2-thiazolyl)-3-tri Fluoromethyl-1H-pyrazole-5-carboxamide, the yield is 89.1%.

example 3

[0049] Example 3: N-(4-chloro-2-methyl-6-(cyclopropylcarbamoyl)phenyl)-1-(4-trifluoromethyl-2-thiazolyl)-3-trifluoromethyl -1H-pyrazole-5-carboxamide

[0050] The above preparation of 6-chloro-8-methyl-2-(3-trifluoromethyl-1-(4-trifluoromethyl-2-thiazolyl)-1H-pyrazol-5-yl)-4H- 1,3-Benzoxazinone (2.0mmol) was placed in a 50mL two-necked reaction flask, 25mL of acetone was added, and cyclopropylamine (6.0mmol) was slowly added dropwise, stirred at room temperature for 2h, filtered, and the filter cake was dried to obtain the target product N- (4-Chloro-2-methyl-6-(cyclopropylcarbamoyl)phenyl)-1-(4-trifluoromethyl-2-thiazolyl)-3-trifluoromethyl-1H-pyrazole -5-formamide, the yield is 81.1%.

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Abstract

The invention discloses an anthranilic diamide compound with trifluoromethyl substituted N-arylpyrazole structures, a method for preparing the anthranilic diamide compound and application. The anthranilic diamide compound is shown as a formula I. An X in the formula independently represents hydrogen, halogen, trifluoromethyl and cyan; an R1 in the formula independently represents 2, 6-dichloro-4-trifluoromethyl-phenyl, 4-trifluoromethyl-2-thiazolyl, 3-5-di (trifluoromethyl) phenyl, 2-chlorine-6-trifluoromethyl-phenyl, 2-trifluoromethyl-4-chlorphenyl and 2-trifluoromethyl-4-fluorophenyl; an R2 in the formula independently represents methyl, ethyl, isopropyl, cyclopropyl and tert-butyl. The anthranilic diamide compound, the method and the application have the advantages that excellent effects of preventing Lepidoptera pests can be realized by the anthranilic diamide compound, and the anthranilic diamide compound can be applied to preventing and treating diseases and insect pests of diversified crops, is high in efficiency and low in toxicity and is environmentally friendly.

Description

technical field [0001] The invention belongs to the field of pesticides and insecticides, and relates to an o-carboxamidobenzamide compound containing a trifluoromethyl-substituted N-arylpyrazole structure and a preparation method and application thereof. technical background [0002] With the wide application of pesticides, people's understanding of pesticides is getting deeper and deeper. The continuous progress and development of society has prompted profound changes in the concept of pesticides. The traditional pesticides in the past can no longer meet the development needs of today's society, and the discovery of new broad-spectrum pesticides with high efficiency, low toxicity, low residue, and environmental friendliness is an urgent task for scientific researchers. [0003] O-carboxamidobenzamide compounds are effective insecticides developed in recent years against Lepidoptera pests. A new type of compound that targets ryanodine receptors was developed by DuPont in ...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D231/14A01N43/78A01N43/56A01P7/04
CPCA01N43/56A01N43/78C07D231/14C07D417/04
Inventor 朱红军刘琪高尚朱瑞刁亚梅徐涛田磊
Owner NANJING UNIV OF TECH