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Quinoline compound and synthetic method and application thereof

A technology of compounds and quinolines, which is applied in the field of quinolines and their synthesis, can solve the problems of complex synthesis process, few types, and insignificant weed effect, and achieve good weeding effect, good effect, and simple and easy synthesis method line effect

Active Publication Date: 2019-08-20
HUNAN AGRI BIOTECH RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in order to slow down the resistance of weeds to it, it is generally used in combination with other herbicides to slow down its resistance. For example, in patent 201811297362.6 "A herbicidal composition containing quinclorac and its application", dichloroquine is used Phenolic acids, aryloxyphenoxypropionates and sulfonylureas, as herbicidal compositions, can improve the herbicidal effect to a certain extent, and can also slow down the resistance of weeds, but for weeds that have developed resistance The effect is not significant
In order to completely solve the problem of weed resistance, it is the best way to develop new quinoline herbicides, but currently there are few new types of quinoline herbicides, and some of them are not effective against resistant weeds. Some synthetic processes are complex

Method used

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  • Quinoline compound and synthetic method and application thereof
  • Quinoline compound and synthetic method and application thereof
  • Quinoline compound and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 10mmol substituent R 1 Be the compound N (its structural formula is as follows) of Cl atom and the acid chloride SOCl of 80mmol 2 Reagent, dissolved in 150mL of toluene solvent, reacted for 12h, cooled, and the solvent and excess SOCl were evaporated under reduced pressure 2 , to get the substituent R 1 The intermediate M (its structural formula is as follows) of Cl is ready for use.

[0030] 10 mmol of substituent R 2 The compound L (its structural formula is as follows) that is ethyl, the calcium hydroxide of 17mmol, the calcium oxide of 3mmol are added in the 250mL two-necked flask, after adding the acetonitrile of 80mL, heating and stirring and refluxing for 0.5h, will be dissolved in the acetonitrile solvent of 20mL 10 mmol of intermediate M was added dropwise to the reaction system, and the reaction was continued under reflux for 12 hours. After the reaction was completed, it was cooled and poured into 200 mL of ice water, adjusted to pH=4-5 with hydrochloric a...

Embodiment 2

[0039] 10mmol substituent R 1 Be the compound N of nitro (its structural formula is as follows) and the acid chloride POCl of 80mmol 3 Reagent, dissolved in 150mL of toluene solvent, reacted for 12h, cooled, and the solvent and excess SOCl were evaporated under reduced pressure 2 , to get the substituent R 1 The intermediate M (its structural formula is as follows) of Cl is ready for use.

[0040] 12 mmol of substituent R2 Phenyl compound L (its structural formula is as follows), 17mmol of magnesium hydroxide, and 3mmol of magnesium oxide were added to a 250mL two-necked flask, and 80mL of 1,4-dioxane was added, heated and stirred under reflux for 1 hour, and the dissolved 10mmol of intermediate M in 20mL of 1,4-dioxane solvent was added dropwise to the reaction system, and after reflux reaction for 24h (the disappearance of the raw material point was monitored by thin-layer chromatography), it was cooled and poured into 200mL of ice water, and used Sulfuric acid was used t...

Embodiment 3

[0049] 10mmol substituent R 1 Be the compound N (its structural formula is as follows) of Cl atom and the acid chloride SOCl of 80mmol 2 Reagents, dissolved in 150mL of tetrahydrofuran solvent, reacted for 12h, cooled, and the solvent and excess SOCl were evaporated under reduced pressure 2 , to get the substituent R 1 The intermediate M (its structural formula is as follows) of Cl is ready for use.

[0050] 15mmol substituent is R 2 Benzyl compound L (its structural formula is as follows), 17mmol of calcium hydroxide and 3mmol of magnesium oxide were added to a 250mL two-necked flask, and 100mL of acetonitrile was added, heated and stirred under reflux for 0.5h, and then dissolved in 20mL of acetonitrile solvent 10mmol of intermediate M was added dropwise to the reaction system, and refluxed for 24h. Cool and pour into 200 mL of ice water, adjust the pH to 4-5 with sulfuric acid, and filter to obtain a solid.

[0051] Dissolve the solid in chloroform, add water for extra...

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Abstract

The invention discloses a quinoline compound and a synthetic method and application thereof. The structure is as follows: on the basis of a traditional quinolinic acid structure, a pyrazol structure is introduced to form a new quinolinic acid derivative. The synthetic method of the quinoline compound in the invention is simple and feasible, and mass production is easy to implement. The quinoline compound of the invention has a good weed control effect and has a good effect on weeds having resistance.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and pesticides, in particular to a quinoline compound and its synthesis method and application. Background technique [0002] The chemical name of quinclorac is: 3,7-dichloro-8-quinolinic acid. It is a characteristic selective herbicide for controlling barnyardgrass in rice fields and belongs to the hormone-type quinolinic acid herbicide. The agent can be quickly absorbed by the germinated seeds, roots, stems and leaves, and quickly conduct to the stems and tops, causing them to be poisoned and dead. It has developed drug resistance. Since quinclorac was registered in my country in 1993, it can control barnyardgrass, black brome, foxtail, crabgrass, etc. It can also effectively control duckweed, cress, saponin and morning glory weeds, etc. . It has been used continuously for more than 20 years. Recently, barnyardgrass has developed resistance to it in major rice producing areas in my ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06A01N43/56A01N43/50A01P13/00
CPCA01N43/50A01N43/56C07D401/06
Inventor 柏连阳李祖任罗丁峰邬腊梅彭琼
Owner HUNAN AGRI BIOTECH RES CENT
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