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Diacylhydrazine derivatives as well as preparation method and application thereof

A derivative, bishydrazide technology, applied in the field of synthesis of agricultural chemical insecticides, to achieve the effect of improving fat solubility and high insecticidal activity

Inactive Publication Date: 2018-07-20
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to unscientific and large-scale overuse in recent years, there are more and more reports of resistance to these two types of insecticides

Method used

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  • Diacylhydrazine derivatives as well as preparation method and application thereof
  • Diacylhydrazine derivatives as well as preparation method and application thereof
  • Diacylhydrazine derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 3-Bromo-N-(2-(1-tert-butyl-2-(2-chlorobenzoyl)-1-formylhydrazino)-4-chloro-6-methylphenyl)-1-( Synthesis of 3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (derivative 01):

[0059] Step A: Preparation of N'-tert-butyl-2-chlorobenzohydrazide

[0060] At 0°C, add tert-butylhydrazine hydrochloride (20mmol) and sodium hydroxide to a 100mL round-bottomed flask, then add a mixed solvent of tetrahydrofuran / water, and slowly drop into a dichloromethane solution of 2-chlorobenzoyl chloride After completion of the dropwise reaction at room temperature, ethyl acetate was added after the reaction, and the organic layer was separated. After precipitation of the organic layer, the title compound was obtained, 4.2g of white powder, m.p.113-114°C.

[0061] Step B: Preparation of 2-amino-N-tert-butyl-5-chloro-N'-(2-chlorobenzoyl)-3-methylbenzohydrazide

[0062] In a 100 mL round bottom flask was added 2-amino-5-chloro-3-methylbenzoic acid (5 mmol), SOCl 2 , reflux, decompression to re...

Embodiment 2

[0066] 3-Bromo-N-(2-(1-tert-butyl-2-(3,5-dimethylbenzoyl)-1-carbohydrazino)-4-chloro-6-methylphenyl) - Synthesis of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (derivative 23):

[0067] Step A: Preparation of N'-tert-butyl-3,5-dimethylbenzohydrazide

[0068] At 0°C, add tert-butylhydrazine hydrochloride (20mmol) and sodium hydroxide to a 100mL round-bottomed flask, then add a mixed solvent of tetrahydrofuran / water, and slowly drop in 3,5-dimethylbenzoyl chloride Dichloromethane solution, dropwise, react at room temperature, add ethyl acetate after the reaction, separate the organic layer, and precipitate the organic layer to obtain the title compound, 4.1g white powder, m.p.117-118°C.

[0069] Step B: Preparation of 2-amino-N-tert-butyl-5-chloro-N'-(3,5-dimethylbenzoyl)-3-methylbenzohydrazide

[0070] In a 100 mL round bottom flask was added 2-amino-5-chloro-3-methylbenzoic acid (5 mmol), SOCl 2 , reflux, decompression to remove excess SOCl 2 , to obtain the crude aci...

Embodiment 3

[0074] 3-Bromo-N-(2-(2-tert-butyl-2-(3,5-dimethylbenzoyl)-1-carbohydrazino)-4-chloro-6-methylphenyl) - Synthesis of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (derivative 34):

[0075] Step A: Preparation of 3-bromo-N-(2-(2-tert-butyl-1-carbohydrazino)-4-chloro-6-methylphenyl)-1-(3-chloro-2-pyridine base)-1H-pyrazole-5-carboxamide

[0076] Compound 6-chloro-2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-8-methyl-4H-3,1-benzox Dissolve oxazin-4-one (5mmol) and tert-butylhydrazine hydrochloride (10mmol) in dimethyl sulfoxide, slowly drop into 1,8-diaza-bicyclo(5,4,0)undeca- 7-ene, dropwise, reacted at room temperature, added ethyl acetate after the reaction, separated the organic layer, and precipitated the organic layer to obtain the title compound, 1.6g white powder, m.p.211-212°C.

[0077] Step B: Preparation of 3-bromo-N-(2-(2-tert-butyl-2-(3,5-dimethylbenzoyl)-1-carbohydrazino)-4-chloro-6-methanol phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (der...

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Abstract

The invention belongs to the field of agricultural insecticides and particularly provides a preparation method and an application of diacylhydrazine insecticides. The compounds improve lipid solubility of original compounds and further have excellent insecticidal activity; after the insecticides are applied, injurious insects stop eating and muscles lose control, people can observe that insect bodies obviously shrink and paralyze, precocious molt of the insects can be caused, and finally, the injurious insects are dead. The compounds are quite effective for lepidoptera pests such as oriental armyworms, plutella xylostella and the like and are insecticides with broad application prospect.

Description

technical field [0001] The invention belongs to the synthesis technology of agricultural chemical insecticides, and in particular relates to an anthranilamide derivative of a bishydrazide group and a preparation method and application thereof. Background technique [0002] The ryanodine receptor insecticide is a novel pesticide with a unique mechanism of action (Bioorg.Med.Chem.Lett., 2007, 17, 6274-6279; Bioorg.Med.Chem., 2009, 17 , 4127-4133). This kind of insecticide has the characteristics of broad spectrum, high efficiency, safety to non-target organisms, and no cross-resistance with traditional pesticides, and has attracted great attention from scientific researchers. Representatives of this class of insecticides are highly active insecticides developed by Nippon Agricultural Chemicals and DuPont: phthalamides and o-formamidobenzamides. Currently commercialized such insecticides are flubendiamide, chlorantraniliprole and cyantraniliprole. These two types of insectic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCA01N43/56C07D401/04
Inventor 周蕴赟朱亮亮
Owner FUDAN UNIV
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