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Iminopyridazine derivative as well as preparation method, application and insecticide thereof

A technology of imino and derivatives is applied in the field of pesticide chemistry to achieve obvious inhibitory effect and good control effect.

Active Publication Date: 2021-04-13
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the long-term use of certain insecticides, pests have developed resistance to them, and most insecticides will have a negative impact on the environment, so the development of new high-efficiency green insecticides is an urgent task

Method used

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  • Iminopyridazine derivative as well as preparation method, application and insecticide thereof
  • Iminopyridazine derivative as well as preparation method, application and insecticide thereof
  • Iminopyridazine derivative as well as preparation method, application and insecticide thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Synthesis of Target Compound 3-(6-imino-3-arylpyridazin-1-yl)propionic acid (2a-k)

[0073]

[0074] In a 50 mL one-necked flask, add intermediate 1a-k (1.0 mmol), ethyl 3-bromopropionate (0.27 g, 1.5 mmol), DMF (0.5 mL), and heat and stir at 80° C. for 8 h. Then sodium hydroxide (0.16 g, 4.0 mmol) and water (10 mL) were added to the reaction solution, and heating and stirring at 80° C. was continued for 12 h. After cooling, 20 ml of ethyl acetate was added, followed by extraction with water (20 ml×3). Add 4mol / L hydrochloric acid to the aqueous phase, stir, and adjust the pH to 1-2. Stirring was then continued for 30 min under an ice bath, and a solid precipitated out. The solid was recrystallized to give 3-(6-imino-3-arylpyridazin-1-yl)propanoic acids (2a-k).

[0075] 3-(6-imino-3-phenylpyridazin-1-yl)propanoic acid (2a):

[0076] White solid, yield 34.6%. 1 H NMR (400MHz, DMSO-d 6 )δ12.39(s,1H,COOH),8.05(d,J=9.6Hz,1H,ArH),7.90(d,J=7.3Hz,2H,ArH),7.54-7.42(m,3...

Embodiment 2

[0098] Synthesis of Target Compound 3-(6-imino-3,5-diarylpyridazin-1-yl)propionic acid (4a-c)

[0099]

[0100] In a 50mL single-necked bottle, add 3-amino-4,6-diarylpyridazine (3a-c) (1.0mmol), ethyl 3-bromopropionate (0.27g, 1.5mmol), DMF (0.5mL ), heated and stirred at 80°C for 8h. Then sodium hydroxide (0.16 g, 4.0 mmol) and water (10 mL) were added to the reaction solution, and heating and stirring at 80° C. was continued for 12 h. After cooling, 20 mL of ethyl acetate was added, followed by extraction with water (20 mL×3). Add 4mol / L hydrochloric acid to the aqueous phase, stir, and adjust the pH to 1-2. Stirring was then continued for 30 min under an ice bath, and a solid precipitated out. The solid was recrystallized to give 3-(6-iminopyridazin-1-yl)propanoic acid (4a-c).

[0101] 3-(6-imino-3,5-diphenylpyridazin-1-yl)propanoic acid (4a):

[0102] White solid, 19.2% yield. 1 H NMR (400MHz, DMSO-d 6 )δ12.35(s,1H,COOH),8.14(s,1H,ArH),8.04-7.92(m,4H,ArH),7.54-7....

Embodiment 3

[0108] Synthesis of intermediate 3-amino-4,6-diarylpyridazine (6a-b)

[0109]

[0110] In a 50mL two-necked flask, add 3-amino-4-bromo-6-chloropyridazine (5) (0.63g, 3.0mmol), arylboronic acid (6.0mmol), potassium carbonate (0.83g, 6.0mmol), Tetrakis(triphenylphosphine)palladium (0.21g), 1,4-dioxane (20mL) and water (5mL) were stirred evenly under the protection of argon, heated to 100°C and stirred under reflux for 8h. After the reaction was monitored by TLC, the system was cooled to room temperature, 20 mL of water was added, and then extracted with ethyl acetate (50 mL×3). The organic phase was washed with saturated brine (50mL×2), dried over a small amount of anhydrous sodium sulfate, and then rotary evaporated under reduced pressure. The crude product was separated and purified by silica gel column chromatography [V (ethyl acetate): V (petroleum ether) = 1: 2] Intermediates 6a and 6b are obtained.

[0111] 3-Amino-4,6-diphenylpyridazine (6a):

[0112] Reddish-brown ...

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Abstract

The invention belongs to the technical field of pesticide chemistry, and particularly relates to an iminopyridazine derivative, a preparation method and application thereof and an insecticide. On the basis of an iminopyridazine structure, propionic acid or butyric acid side chains are introduced to the first position of the iminopyridazine structure, aryl is introduced to the third position and the fifth position of the iminopyridazine structure respectively or simultaneously, and the polysubstituted iminopyridazine derivative is synthesized and has an obvious inhibiting effect on GABA receptors of public health pests such as houseflies and agricultural pests such as prodenia litura. Meanwhile, the derivative also has good insecticidal activity on prodenia litura, and has an application prospect of preparing or developing insecticides.

Description

technical field [0001] The invention belongs to the technical field of pesticide chemistry, and in particular relates to iminopyridazine derivatives, their preparation method, application and insecticide. Background technique [0002] In the process of agricultural production, the use of pesticides is an essential link. Due to the long-term use of certain insecticides, pests have developed resistance to them, and most insecticides will have negative impacts on the environment. Therefore, it is an urgent task to develop new high-efficiency green insecticides. [0003] Some iminopyridazine derivatives show certain antagonism on insect GABA receptors, and can be used as insect GABA receptor antagonists to prepare novel insecticides. Contents of the invention [0004] In order to solve the deficiencies of the prior art, the invention provides that the invention belongs to the technical field of pesticide chemistry, and specifically relates to iminopyridazine derivatives and t...

Claims

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Application Information

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IPC IPC(8): C07D237/20C07D405/04C07D409/04A01N43/58A01P7/04
CPCC07D237/20C07D405/04C07D409/04A01N43/58
Inventor 刘根炎周聪伟张志松陈达黄成吴风收罗晓刚巨修练
Owner WUHAN INSTITUTE OF TECHNOLOGY
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