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Quinoline carboxylic acid ester compound and preparation method and application thereof

An ester compound, quinoline carboxylic acid technology, applied in the field of agricultural bactericides, can solve the problems of small promotion area, limited resistance and control effect, pollution, etc.

Inactive Publication Date: 2019-06-28
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, copper preparations have low control efficiency, and a large amount of heavy metals are sprayed into the environment, polluting soil, water and food, causing environmental and food safety concerns; on the other hand, the extensive use of antibiotics may cause human Pathogenic bacteria develop resistance to medical antibiotics
There are only a small number of other varieties that can be used for agricultural bacterial treatment, and the actual production is limited by the double restrictions of resistance and control effect, and the promotion area is small

Method used

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  • Quinoline carboxylic acid ester compound and preparation method and application thereof
  • Quinoline carboxylic acid ester compound and preparation method and application thereof
  • Quinoline carboxylic acid ester compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143] Example 1: Methoxymethyl 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (compound 1)

[0144]

[0145] The first step reaction: Potassium 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

[0146] At room temperature, 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (12.3g, 0.05mol), 30% aqueous potassium hydroxide solution (12ml) was added to In a three-neck bottle. Heated to 60°C and reacted for 2 hours. Heating was stopped, and the product was dehydrated under reduced pressure to obtain 13.6 g of the product with a yield of 96%.

[0147] The second step reaction: Methoxymethyl 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

[0148] At room temperature, potassium 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (2.85g, 0.01mol), chloromethyl methyl ether (0.96g, 0.012 mol) were successively dissolved in N,N-dimethylformamide (15ml). Heated to 100°C and reacted for 6 hours. Heati...

Embodiment 2

[0150] Example 2: 2-methoxyethyl 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (compound 10)

[0151]

[0152] The first step reaction: 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-oyl chloride

[0153] At room temperature, mix 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (14.9g, 0.06mol), dichloroethane (90ml) and N,N - Dimethylformamide (0.2g) was added into a three-necked flask, and thionyl chloride (14.6g, 0.12mol) was added dropwise to the above mixture. Heat to reflux for 5 hours. Heating was stopped, and the solvent and residual thionyl chloride were removed under reduced pressure to obtain 14.6 g of the product with a yield of 92%.

[0154] The second step reaction: 2-methoxyethyl 1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

[0155] At room temperature, 2-methoxyethanol (0.76g, 0.01mol) and triethylamine (2.02g, 0.02mol) were successively dissolved in dichloromethane (20ml). Cool to 0°C in a cry...

Embodiment 3

[0157] Example 3: 2-methoxyethyl 6-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (compound 45)

[0158]

[0159] The first step reaction: 6-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-acid chloride

[0160] At room temperature, mix 6-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (15.8g, 0.06mol), dichloroethane (90ml) and N,N - Dimethylformamide (0.2g) was added into a three-necked flask, and thionyl chloride (14.6g, 0.12mol) was added dropwise to the above mixture. Heat to reflux for 5 hours. Heating was stopped, and the solvent and residual thionyl chloride were removed under reduced pressure to obtain 16.2 g of the product with a yield of 96%.

[0161] The second step reaction: 2-methoxyethyl 6-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

[0162] At room temperature, 2-methoxyethanol (0.76g, 0.01mol) and triethylamine (2.02g, 0.02mol) were successively dissolved in dichloromethane (20ml). Cool to 0°C in a cr...

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Abstract

The invention belongs to the technical field of bactericides, and particularly relates to a quinoline carboxylic acid ester compound shown in the formula (I), and the compound in the formula (I) showsvery good activity for various bacteria in the agricultural field. In addition, due to the fact that the compounds have very high bioactivity, the good effect can be achieved at very low dosage, andthe compound can be used for preparing the bactericides in the agricultural field.

Description

technical field [0001] The invention belongs to the technical field of agricultural bactericides, and in particular relates to a quinoline carboxylic acid compound and a preparation method and application thereof. Background technique [0002] Bacterial crop disease is a common disease in agricultural production in my country, and its damage degree has surpassed that of viruses, becoming the second largest pathogen after fungi. Due to the various transmission modes of bacterial diseases, the lack of control agents, and the long-term continuous cropping, the difficulty of prevention and control is increasing. According to incomplete statistics, the current occurrence area of ​​bacterial diseases in my country is 120 million mu, and the market capacity of bacterial disease prevention and treatment exceeds 2 billion yuan. [0003] In current agricultural production, the medicaments for preventing and controlling bacterial diseases mainly include copper preparations (including ...

Claims

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Application Information

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IPC IPC(8): C07D215/56A01N43/42A01N43/84A01P1/00
CPCC07D215/56A01N43/42A01N43/84A01N43/40C07D401/04C07D413/04
Inventor 许辉唐剑峰迟会伟吴建挺韩君刘莹赵宝修张振国
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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