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Application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases

A technology for trifluoromethylpyrazoles and fungal diseases, applied in the field of pesticides, can solve problems such as no reports of antifungal drugs, and achieve the effects of broad-spectrum, high-efficiency bactericidal activity and unique structure

Active Publication Date: 2018-11-23
INST OF PLANT PROTECTION HENAN ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, in the prior art, the above-mentioned 1,5-diaryl-3-trifluoromethylpyrazole compounds have not been reported as antifungal drugs in the field of pesticides

Method used

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  • Application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases
  • Application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases
  • Application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation of embodiment 1 compound (1)

[0029] a. Add 4.5 grams of sodium metal to 70 ml of anhydrous methanol, cool to room temperature after the reaction is complete, slowly add 14 g of p-fluoroacetophenone and 17 g of ethyl trifluoroacetate (120 mmol), after the dropwise addition, heat up Reflux for 24 hours, concentrate to a yellow viscous liquid, add 2mol / L hydrochloric acid to adjust the pH to 2-3, extract with ethyl acetate, dry over magnesium sulfate, and evaporate the solvent to obtain a yellow oil 1-p-fluoro-4,4 , 4-trifluorobutanol-1,3 dione 21g, yield 90%.

[0030] b. Add 23.4g 1-p-fluoro-4,4,4-trifluorobutane-1,3dione and 19.g (mmol) p-carboxyphenylhydrazine hydrochloride to a round bottom flask filled with absolute ethanol , stirred and refluxed for 24 hours, solids were precipitated, filtered, and recrystallized from ethanol to obtain 28 g of the target compound, with a yield of 80%.

Embodiment 2

[0031] The preparation of embodiment 2 compound (2)

[0032] a. Add 4.5 grams of sodium metal to 70 ml of anhydrous methanol, cool to room temperature after the reaction is complete, slowly add 13.5 g (100 mmol) of p-methylacetophenone and 17 g (120 mmol) of ethyl trifluoroacetate, drop After the addition, heat up and reflux for 24 hours, concentrate to a yellow viscous liquid, add 2mol / L hydrochloric acid to adjust the pH value to 2-3, extract with ethyl acetate, dry over magnesium sulfate, and evaporate the solvent to obtain a yellow oily substance 1-p Tolyl-4,4,4-trifluorobutan-1,3dione 20g, yield 86%.

[0033] b. Add 23g (100mmol) 1-p-tolyl-4,4,4-trifluorobutane-1,3-dione and 19g (100mmol) p-carboxyphenylhydrazine hydrochloride to a round-bottomed flask filled with absolute ethanol Salt, stirred and refluxed for 24 hours, a solid precipitated out, filtered, and recrystallized from ethanol to obtain 25.9 g of the target compound, with a yield of 75%.

Embodiment 3

[0034] The preparation of embodiment 3 compound (3)

[0035] a. Add 4.5 grams of sodium metal to 70 ml of anhydrous methanol, cool to room temperature after the reaction is complete, slowly add 15 g of p-methoxyacetophenone and 17 g (120 mmol) of ethyl trifluoroacetate, after the addition is complete , heated and refluxed for 24 hours, concentrated to a yellow viscous liquid, added 2mol / L hydrochloric acid to adjust the pH value to 2-3, extracted with ethyl acetate, dried over magnesium sulfate, and obtained yellow oily 1-p-methoxybenzene after distilling off the solvent 22.6 g of 4,4,4-trifluorobutan-1,3-dione, yield 92%.

[0036] b. Add 18.514g 1-p-methoxyphenyl-4,4,4-trifluorobutane-1,3-dione and 24.6g (100mmol) p-carboxyphenylhydrazine salt to a round bottom flask filled with absolute ethanol Salt 19g (100mmol), stirred and refluxed for 24 hours, a solid precipitated out, filtered, and recrystallized from ethanol to obtain 31.4g of the target compound, with a yield of 87%...

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Abstract

The invention belongs to the technical field of pesticides, and particularly relates to application of 1,5-diaryl-3-pyrazole compound in prevention and control of agricultural fungal diseases. The general structural formula of the 1,5-diaryl-3-pyrazole compound is as shown in the description, wherein R1 is selected from fluorine, methoxyl or methyl; and R2 is selected from -CHOOH, -SO2NH2, -NO2, -F,-C1 or -Br. Compared with a traditional agricultural fungicide, the 1,5-diaryl-3-pyrazole compound provided by the invention is unique in structure, adopts an action mechanism different from that ofa traditional fungicide, and has no cross resistance risks on resistance strains generated by an existing fungicide.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to the application of 1,5-diaryl-3-trifluoromethylpyrazole compounds in the prevention and treatment of agricultural fungal diseases. Background technique [0002] There have been many reports and literatures on the preparation and application of 1,5-diaryl-3-trifluoromethylpyrazoles as cyclooxygenase (COX-2) inhibitors. Literature (J.Med.Chem.40,9,1347-1365) reported a class of 1,5-diarylpyrazole compounds [0003] [0004] When X is selected from methyl, Y is selected from -CF 3 , Z selected from -SO 2 NH 2 It is the antipyretic and analgesic drug celecoxib, and its structural formula is as follows: [0005] [0006] However, in the prior art, the above-mentioned 1,5-diaryl-3-trifluoromethylpyrazole compounds have not been reported as antifungal drugs in the field of pesticides. Contents of the invention [0007] The invention provides the application o...

Claims

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Application Information

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IPC IPC(8): A01N43/56A01P3/00
CPCA01N43/56
Inventor 马毅辉王振宇孙祥龙杨党伟杨军秦光宇贾刚民李巍
Owner INST OF PLANT PROTECTION HENAN ACAD OF AGRI SCI
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