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Methyl arylpyrazole fluorouracil compounds, and preparation method and application thereof

A compound, pyridine technology, applied in the field of pesticides, achieves the effects of simple synthesis process, less residue in the body, and fast metabolism

Inactive Publication Date: 2014-12-10
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, foreign drug resistance monitoring has found that the field populations of Homoptera insects Bemisia tabaci, Silverleaf whitefly, etc. have developed resistance or resistance to mainstream insecticides such as imidacloprid to varying degrees, which is a sound for the control of agricultural pests. alarm bell

Method used

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  • Methyl arylpyrazole fluorouracil compounds, and preparation method and application thereof
  • Methyl arylpyrazole fluorouracil compounds, and preparation method and application thereof
  • Methyl arylpyrazole fluorouracil compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] This example illustrates the synthesis of 5-fluorouracil acetic acid

[0059] Add KOH1.12g (20mmol), H 2 O15mL, after dissolving, add 2.6g (20mmol) of 5-fluorouracil (20mmol) and 1.82g (22mmol) of chloroacetic acid in 10mL aqueous solution, and continue the reaction for 6h after completion. After the reaction, the pH was adjusted to 2 with concentrated hydrochloric acid, a large amount of white solid precipitated, filtered, washed with water, and recrystallized with water to obtain 3.0 g of the product with a yield of 80%. Product melting point: 289-291°C.

Embodiment 2

[0061] This example illustrates the synthesis of 5-fluorouracil amidoalcohol

[0062] Add 3.76 g (20 mmol) of 5-fluorouracil acetic acid into a three-necked flask, dissolve it in 50 mL of DMF, and stir for 1 h. At room temperature, 1.6 g (24 mmol) of ethanolamine was slowly added dropwise, and the reaction was refluxed for 24 h. After the reaction was completed, 100 mL of water was added after concentrating the solvent, a large amount of solids precipitated, filtered, washed with water, and recrystallized with ethanol to obtain 3.18 g of the product, with a yield of 69%. Product melting point: 253-256°C.

Embodiment 3

[0064] This example illustrates the synthesis of 3-methyl-1-phenyl-1H-pyrazole-5-carboxylic acid

[0065] Add 10mmol of phenylhydrazine and 15ml of ethanol to a four-neck flask, dissolve and add 1.58g (10mmol) of ethyl acetylacetonate, react at room temperature for 2h, filter, and recrystallize from ethanol to obtain 5-hydroxy-3-methyl-1-phenyl -4,5-Dihydro-1H-pyrazole-5-carboxylic acid ethyl ester.

[0066] Add the above product and 8ml of concentrated hydrochloric acid into a four-necked flask, and heat to reflux for 2h. After the reaction, the solvent was spin-dried to obtain ethyl 3-methyl-1-phenyl-1H-pyrazole-5-carboxylate.

[0067] Add the above product and 20ml of 50% NaOH into a four-necked flask, and heat to reflux for 2h. After the reaction, cool to room temperature, adjust the pH to 2-3 with concentrated hydrochloric acid, extract with ethyl acetate, take the organic phase, dry, rotary evaporate, and recrystallize to obtain a white solid. The yield is 58.2%, and ...

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Abstract

The invention discloses methyl arylpyrazole fluorouracil compounds, and a preparation method and an application thereof. The compounds are compounds represented by the structural general formula (I) and pharmaceutically acceptable salts thereof. The compounds provided by the invention have the advantages of low dose, good insecticidal effect, simple process method, low cost, and wide market prospect.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a methylarylpyrazole-fluorouracil compound, a preparation method and an application as an insecticide. Background technique [0002] With the continuous growth of the world's population and the relative reduction of arable land, the issue of food has attracted more and more attention. Diseases, insects, and pests will cause serious losses to agricultural production every year. The average loss caused by them during plant growth is about 10-20%, which will cause huge losses to food production. Pesticides have become indispensable in agricultural production. Indispensable safeguards. [0003] At present, the hot insecticides in the market include fipronil and chlorantraniliprole. However, foreign drug resistance monitoring has found that the field populations of Homoptera insects Bemisia tabaci, Silverleaf whitefly, etc. have developed resistance or resistance to mainstream ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12C07D401/14A01N43/56A01P7/04
Inventor 万嵘穆海萍陈月杨阳傅晓东秦小飞沈陈
Owner NANJING TECH UNIV