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Bisamide compound and synthesizing method and application thereof

A synthesis method and compound technology, applied in the field of synthesis of bisamide compounds, can solve the problem of low activity of homopteran pests, achieve excellent insecticidal activity, simple preparation method, and low price

Active Publication Date: 2018-05-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, its activity against homopteran pests is relatively low. In practical application, it often needs to be used in combination with thiamethoxam, such as Fugo developed by Syngenta. At the same time, because chlorantraniliprole is widely used , field populations of diamondback moth in some areas have developed severe resistance to chlorantraniliprole

Method used

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  • Bisamide compound and synthesizing method and application thereof
  • Bisamide compound and synthesizing method and application thereof
  • Bisamide compound and synthesizing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Step A: Add 20mL of 50% hydrazine hydrate to an ethanol solution containing 20mL of 2,3-dichloropyridine (7.35g, 0.05mol) at room temperature, heat to reflux for 5h, cool to room temperature, and collect the white needle-like solid by filtration Product 3-chloro-2-hydrazinopyridine 6.75g, yield 94.4%;

[0025] Step B: Add 50mL ethanol in the 100mL reaction flask equipped with mechanical stirring, slowly add 1.2g metal sodium, reflux reaction makes sodium ethylate solution, add 3-chloro-2-hydrazinopyridine ( 6.75 g, 0.05mol), diethyl maleate (9m L, 0.055mol), continue to reflux for 30min, then cool down, filter to obtain a light yellow solid 3-hydroxyl-1-(3-chloropyridin-2-yl)- 1H-pyrazole-5-carboxylic acid ethyl ester (6.48g, 0.024mol), yield 52%;

[0026] Step C: 0.5g sodium hydroxide and 10mL methanol were added to 3-hydroxy-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid ethyl ester (2.7g, 0.01mol ) in a 100mL reaction flask, stirred at room temperature for ...

Embodiment 2-4

[0030] 6-Chloro-2-(3-hydroxy-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-8-methyl-4H-3,1-benzoxazine-4 -Reaction of ketones with different amines, the specific steps are the same as in Example 1, and the new compounds obtained by the reaction are shown in Table 1, and their characterization data are shown in Table 2.

Embodiment 5

[0032] Step A: Add 20mL of 50% hydrazine hydrate to an ethanol solution containing 20mL of 2,3-dichloropyridine (7.35g, 0.05mol) at room temperature, heat to reflux for 5 hours, cool to room temperature, and collect white needles by filtration Solid product 3-chloro-2-hydrazinopyridine 6.75g, yield 94.4%;

[0033] Step B: add 50mL ethanol in the 100mL reaction bottle that mechanical stirring is housed, slowly add 1.2g metallic sodium, reflux reaction makes sodium ethylate solution, add 3-chloro-2-hydrazinopyridine ( 6.75g, 0.05mol), diethyl maleate (9m L, 0.055mol), continue to reflux for 30min, then cool down, filter to obtain light yellow solid 3-hydroxyl-1-(3-chloropyridin-2-yl)- 1H-pyrazole-5-carboxylic acid ethyl ester (6.48g, 0.024 mol), yield 52%;

[0034] Step C: 0.5g sodium hydroxide and 10mL methanol were added to 3-hydroxy-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid ethyl ester (2.7g, 0.01mol ) in a 100mL reaction flask, stirred at room temperature for ...

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Abstract

The invention discloses a bisamide compound and a synthesizing method and application thereof. The synthesizing method includes: allowing 2,3-dichloropyridine to have reaction with hydrazine hydrate to obtain 3-hydrazino-2-chloropyridine; subjecting the 3-hydrazino-2-chloropyridine and diethyl maleate to cyclization and hydrolysis to obtain 3-hydroxy-1-(3-chloropyridine-2-yl)-1H-pyrazol-5-formic acid; subjecting the 3-hydroxy-1-(3-chloropyridine-2-yl)-1H-pyrazol-5-formic acid and substituted o-amino-benzoic acid to cyclization to obtain 2-(-1-(3-chloropyridine-2-yl)-1-H-pyrazol-5-yl)-8-methyl-4H-3,1- benzoxazine-4-ketone; subjecting the 2-(-1-(3-chloropyridine-2-yl)-1-H-pyrazol-5-yl)-8-methyl-4H-3,1- benzoxazine-4-ketone and 40% ammonia water solution to aminolysis to obtain the bisamide compound. The compound containing the bisamide group is simple to prepare, excellent in insecticidal activity and capable of being used as an insecticide.

Description

technical field [0001] The invention relates to a synthesis method and application of a bisamide compound, belonging to the field of agricultural pesticides. Background technique [0002] Chlorantraniliprole (chlorantraniliprole) is an o-formamidobenzamide compound developed by DuPont, which belongs to the ryanodine receptor inhibitor class of insecticides, and still has quite good insecticidal activity at very low concentrations, such as The LC50 value of Plutella xylostella is 0.01mg / L, and it has broad spectrum, long residual period, low toxicity and environmental friendliness. It is an effective insecticide for controlling Lepidoptera pests. [0003] However, its activity against homopteran pests is relatively low. In practical application, it often needs to be used in combination with thiamethoxam, such as Fugo developed by Syngenta. At the same time, because chlorantraniliprole is widely used , field populations of diamondback moth in some areas have developed severe ...

Claims

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Application Information

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IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCA01N43/56C07D401/04
Inventor 谭成侠张冬林杨忍
Owner ZHEJIANG UNIV OF TECH
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