Acrylamidoaryl pyrazole compounds, and one-pot synthesis method and application thereof

An acrylamide-based compound technology, used in applications, animal repellants, plant growth regulators, etc.

Active Publication Date: 2016-07-06
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

Method used

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  • Acrylamidoaryl pyrazole compounds, and one-pot synthesis method and application thereof
  • Acrylamidoaryl pyrazole compounds, and one-pot synthesis method and application thereof
  • Acrylamidoaryl pyrazole compounds, and one-pot synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1, 3-cyano-4-trifluoromethylsulfinyl-5-acrylamido-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole ((II ) Synthesis of 1)

[0050]

[0051] Add 25mL tetrahydrofuran and 4.5g 1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole into a 100mL reactor , 1g of sodium hydroxide, 0.96g of acryloyl chloride, after mixing evenly, put the reactor into an 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 neutral, extracted, dried over anhydrous magnesium sulfate, and passed through the column with petroleum ether and ethyl acetate (4:1) to obtain 4.42 g of (II) 1 as a light yellow solid. Yield is 88.2%.mp:180.1~183.6℃.IRν(cm -1 ): 3197 (N—H), 3073 (C—H), 2251 (—CN), 1716 (—C=O), 1631 (pyrazole ring skeleton vibration), 1535 and 1405 (benzene ring skeleton vibration), 1315 (C—F), 882 (aromatic ring C...

Embodiment 2

[0052] Example 2, 3-cyano-4-trifluoromethylsulfinyl-5-(2-methylacryl)amido-1-(2,6-dichloro-4-trifluoromethylphenyl) -Synthesis of pyrazole ((Ⅱ)2)

[0053]

[0054] Add 25mL dioxane, 4.5g 1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-4-trifluoromethylsulfinyl-5- Aminopyrazole, 2.65g of sodium carbonate, 1.13g of 2-methacryloyl chloride, after mixing evenly, put the reactor 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 neutral, extracted, dried over anhydrous magnesium sulfate, and passed through the column with petroleum ether and ethyl acetate (4:1) to obtain 4.28 g of (II) 2 as a light yellow solid. Yield is 82.3%.mp:162.4~166.4℃.IRν(cm -1 ): 3364 (N—H), 3073 (C—H), 2255 (—CN), 1702 (—C=O), 1633 (pyrazole ring skeleton vibration), 1550 and 1409 (benzene ring skeleton vibration), 1316 (C—F), 877 (aromatic ring C—H). 1 HNMR (...

Embodiment 3

[0055] Example 3, 3-cyano-4-trifluoromethylsulfinyl-5-(3-methylacryl)amido-1-(2,6-dichloro-4-trifluoromethylphenyl) -Synthesis of pyrazole ((Ⅱ)3)

[0056]

[0057] Add 25mL of toluene and 4.5g of 1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole into a 100mL reactor , 1.7g sodium ethoxide, and 1.15g 3-methacryloyl chloride, 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 4.32 g of (II) 3 as a yellow solid. The rate is 85.5%.mp:172.4~175℃.IRν(cm -1 ): 3416 (N—H), 3084 (C—H), 2252 (—CN), 1710 (—C=O), 1647 (pyrazole ring skeleton vibration), 1540 and 1382 (benzene ring skeleton vibration), 1312 (C—F), 880 (aromatic ring C—H). 1 HNMR (CD...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly discloses 3-cyano-5-acrylamido-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole compounds, and a solvothermal one-pot synthesis method thereof and application thereof. The solvothermal one-pot synthesis method for preparing the target substances has the advantage of short reaction time; and the solvent can not be easily volatilized in the closed system, and can be recycled, thereby effectively lowering the production cost. The method has the advantages of energy saving, environment friendliness and higher, and is simple to operate. The 3-cyano-5-acrylamido-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole derivatives (II) have favorable bioactivity, especially have high activity in the aspects of agriculture, horticulture, flowers and sanitary insect pest control, can be self-degraded under the irradiation of sunlight, are green low-residue compounds with insecticidal activity, and thus, have great development and application values.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a 3-cyano-5-acrylamido-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole compound and its solvent The thermal one-pot synthesis method also relates to the application of this type of compound. Background technique [0002] In the past ten years, heterocyclic compounds have attracted the attention of people in the field of pesticides due to their high-efficiency biological activity, and have become a hot spot in the research and development of pesticides today. Among various heterocyclic compounds, arylpyrazole compounds have a wide range of biological activities, and are one of the main structures of compounds with insecticidal activity in recent years. Due to the high efficiency, low toxicity and structural diversity shown by arylpyrazole compounds, they have very broad research and development prospects. Arylpyrazole insecticides are a class of γ-aminobutyric acid-r...

Claims

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Application Information

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IPC IPC(8): C07D231/44C07D403/12C07D405/12C07D231/40A01N47/02A01N43/56A01P7/04
CPCA01N43/56A01N47/02C07D231/40C07D231/44C07D403/12C07D405/12
Inventor 陈连清周泉牛雄雷
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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