Bridging type arylpyrazole amide compound as well as solvent heat one-pot synthesis method and application thereof

A kind of technology of aryl pyrazole amide and compound, applied in the field of organic synthesis

Active Publication Date: 2016-06-22
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the solvothermal method is widely used in the synthesis of inorganic materials, but there are few reports on the application in organic synthesis. Experiments have proved that the solvothermal one-pot synthesis method has the advantages of high yield, short time, simple operation, energy saving and environmental protection. , it is expected to become a new method for efficiently preparing bridged arylpyrazole-type amide compounds, and the application prospect will be very broad

Method used

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  • Bridging type arylpyrazole amide compound as well as solvent heat one-pot synthesis method and application thereof
  • Bridging type arylpyrazole amide compound as well as solvent heat one-pot synthesis method and application thereof
  • Bridging type arylpyrazole amide compound as well as solvent heat one-pot synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1, N,N-bis[3-cyano-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole]ethanedi Synthesis of Amide ((Ⅱ)1)

[0049]

[0050] Add 30mL tetrahydrofuran and 9.1g 1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole into a 100mL reaction kettle , 1g sodium hydroxide, 1.27g oxalyl chloride, after mixing evenly, put the reaction kettle into the oven, the reaction temperature is 90°C, and the reaction time is 720 minutes. After the reaction was completed, the solvent was removed by rotary evaporation, the pH was adjusted to neutrality, extracted, dried over anhydrous magnesium sulfate, and passed through the column with petroleum ether and ethyl acetate (4:1) to obtain 7.91 g of (II) 1 as a light yellow solid. Yield is 85.2%.mp:183.1~183.8℃.IRν(cm -1 ): 3204 (N—H), 3056 (C—H), 2247 (—CN), 1713 (—C=O), 1628 (pyrazole ring skeleton vibration), 1528 and 1395 (benzene ring skeleton vibration), 1308 (C—F), 8...

Embodiment 2

[0051] Example 2, N,N-bis[3-cyano-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole]ethanedi Synthesis of Amide ((Ⅱ)2)

[0052]

[0053] Add 30mL of dioxane and 9g of 1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-4-trifluoromethylsulfinyl-5-amino in a 100mL reactor Pyrazole, 2.65g of sodium carbonate, 1.23g of methyl oxalyl chloride, after mixing evenly, put the reaction kettle into an oven, the reaction temperature is 110°C, and the reaction time is 720 minutes. After the reaction was completed, the solvent was removed by rotary evaporation, the pH was adjusted to neutrality, extracted, dried over anhydrous magnesium sulfate, and passed through the column with petroleum ether and ethyl acetate (4:1) to obtain 7.58 g of (II) 2 as a light yellow solid. Yield is 81.7%.mp:182.6.4~183.4℃.IRν(cm -1 ): 3218 (N—H), 3068 (C—H), 2251 (—CN), 1709 (—C=O), 1631 (pyrazole ring skeleton vibration), 1534 and 1403 (benzene ring skeleton vibration), 1314 (C—F...

Embodiment 3

[0054] Example 3, N,N-bis[3-cyano-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole]ethanedi Synthesis of Amide ((Ⅱ)3)

[0055]

[0056] Add 30mL of toluene, 9g of 1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole, 1.7g of sodium ethoxide and 1.18g of dimethyl oxalate, after mixing evenly, put the reaction kettle into an oven, the reaction temperature is 120°C, and the reaction time is 720 minutes. After the reaction, remove the solvent by rotary evaporation, adjust the pH to neutral, extract, dry over anhydrous magnesium sulfate, and pass through the column with petroleum ether and ethyl acetate (4:1) to obtain 8.03 g of (II) 3 as a yellow solid. The rate is 86.5%.mp:182.4~183.7℃.IRν(cm -1 ): 3237 (N—H), 3071 (C—H), 2248 (—CN), 1706 (—C=O), 1651 (pyrazole ring skeleton vibration), 1533 and 1391 (benzene ring skeleton vibration), 1308 (C—F), 875 (aromatic ring C—H). 1 HNMR (CDCl 3 , 400MHz) δ (ppm): 10....

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Abstract

The invention belongs to the technical field of organic synthesis, and concretely discloses a bridging type arylpyrazole amide compound as well as a solvent heat one-pot synthesis method and application thereof. The solvent heat one-pot synthesis method is used for preparing a target object; the reaction time is short; a solvent cannot be volatilized in a sealed system and can be recycled; the production cost is effectively reduced; the advantages of energy saving and environment protection are realized; in addition, the operation is simple; the yield is higher. The prepared bridging type arylpyrazole amide compound (II) has good biological activity, has high activity particularly in the aspects of agriculture, gardening, flowers and sanitation insect prevention and controlling, and belongs to an efficient, low-toxicity, broad-spectrum, environment-friendly and green insecticide, so that great development and application values are realized.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a bridged arylpyrazole amide compound and a solvothermal one-pot synthesis method thereof, and also relates to the application of the compound. Background technique [0002] The development direction of new pesticides in the 21st century is high efficiency, low toxicity, broad spectrum, and environmental friendliness. Phthalamide insecticides are a kind of green insecticides, which have the following characteristics: (1) high efficiency; (2) wide insecticidal spectrum; (3) high retention activity; (4) low toxicity, selectable Good sex, safe to arthropod beneficial insects, safe to mammals, fish, and birds; (5) less dosage; (6) no interaction with traditional insecticides, and can be used for integrated pest control. Among them, flubendiamide is a representative of phthalamide insecticides, and flubendiamide is a new type of insecticide jointly developed by Japanese pes...

Claims

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Application Information

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IPC IPC(8): C07D231/44A01N43/56A01P7/04
CPCA01N43/56C07D231/44
Inventor 陈连清周泉牛雄雷
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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