Oxadiazole compound and preparation method thereof

A technology for oxadiazole compounds, which is applied in the field of oxadiazole compounds and their preparation, can solve problems such as application limitations, and achieve the effects of wide application range and simple process flow

Inactive Publication Date: 2014-06-18
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

limit its use

Method used

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  • Oxadiazole compound and preparation method thereof
  • Oxadiazole compound and preparation method thereof
  • Oxadiazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] An oxadiazole compound, the compound molecular formula is as follows

[0036]

[0037] Among them, R 1 for hydrogen, R 2 is chlorine, R 3 For n-propylamine, the preparation method of this oxadiazole compound comprises the following steps:

[0038] (1) Preparation of 4,5-dichloro-3(2H)pyridazinone

[0039]

[0040] In a 250mL three-necked flask, add 50g of di-chlorobutenalonic acid and a small amount of water, stir to make an aqueous solution, then add 39g of hydrazine sulfate and 38.2g of sodium acetate, heat to 80-100°C, and react for 2 hours. After complete reaction, cool down, pour the reaction solution into cold water, a large amount of light yellow precipitate appears, filter it with suction, and dry it. The obtained product was recrystallized with absolute ethanol, and the yield was 89.5%.

[0041] (2) Synthesis of Benzohydrazide

[0042]

[0043] In a 250ml three-necked flask, add 70ml (0.485mol) of ethyl benzoate and 51.5ml (0.485mol) of hydrazine...

Embodiment 2

[0057] An oxadiazole compound, the compound molecular formula is as follows

[0058]

[0059] R 1 for hydrogen, R 2 is chlorine, R 3 Isopropylamine, the preparation method of this oxadiazole compound comprises the following steps:

[0060] (1) Preparation of 2-(substituted) aryl-5-chloromethyl-1,3,4-oxadiazole

[0061]

[0062] In a 250ml single-necked bottle equipped with a drying device, add 5g (0.024mol) of bishydrazide (N-p-methylbenzoyl-N'-chloroacetyl), 2.684ml (0.0288mol) of phosphorus oxychloride, Stir the reaction at 130° C. in an oil bath, and keep the temperature for 8 hours. After completion, the reaction solution was poured into 150ml of ice water, stirred and left for a period of time, a large amount of precipitation would occur, filtered to obtain a gray solid product, and the yield was 85.32%.

[0063] (2) Synthesis of 4,5-dichloro-2-(2-phenyl-5-methyl-1,3,4-oxadiazole)-3(2H)pyridazinone

[0064]

[0065] In a 250ml single-necked bottle, add 2-ph...

Embodiment 3

[0070] An oxadiazole compound, the compound molecular formula is as follows

[0071]

[0072] R 1 for hydrogen, R 2 is chlorine, R 3 For morpholine, the preparation method of this oxadiazole compound comprises the following steps:

[0073] (1) Preparation of 4,5-dichloro-3(2H)pyridazinone

[0074] Condensation of di-chlorocrotonic acid and hydrazine sulfate into 4,5-dichloro-3(2H)pyridazinone under the catalysis of sodium acetate;

[0075] (2) Preparation of Benzohydrazide

[0076] Ethyl benzoate and hydrazine hydrate were heated to reflux in ethanol solution and reacted for 8 hours to produce benzohydrazide, wherein the molar ratio of ethyl benzoate and hydrazine hydrate reaction was 1:2

[0077] (3) Preparation of bishydrazide

[0078] Mix the benzoyl hydrazide and α-haloacetyl halide prepared in step (2) with a molar ratio of 1:1 in THF, and react at 50°C for 5 hours under the catalysis of alkaline reagent potassium carbonate to synthesize bis hydrazide. The mola...

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Abstract

The present invention relates to an oxadiazole compound and a preparation method thereof, wherein the molecular formula of the compound is as the follow, R1 is halogen, hydrogen, C1-C4 alkyl or alkoxy, R2 is halogen, hydrogen or alkyl, and R3 is methylamine, dimethylamine, isopropylamine, propylamine, butylamine, morpholine, piperidine or imidazole. Compared with the oxadiazole compound and the preparation method in the prior art, the oxadiazole compound and the preparation method of the present invention have the following characteristics that: the process is simple, the application range is wide, and the oxadiazole compound is suitable for prevention and control of health pests such as flies, mosquitoes, fleas and the like and agricultural pests such as lissorhoptrus oryzophilus, spodoptera exigua hiibner, mythimna separata (walker) and the like, can be provided for inhibiting growth of insects, especially mosquito larvae, and is an insecticide with an application prospect.

Description

technical field [0001] The invention relates to an inhibitor and a preparation method thereof, in particular to an oxadiazole compound and a preparation method thereof. Background technique [0002] Azole-containing heterocyclic compounds have a wide range of biological activities and play an important role in the development of pesticides. 1,3,4-oxadiazole is an important class of five-membered heterocyclic compounds, and many 1,3,4-oxadiazole derivatives have been successfully used in medicine, pesticides and other fields. [0003] Oxadiazole compounds are widely used in the control of sanitary pests and crop pests, and many commercial pesticide varieties have been obtained, but in the process of long-term use, the resistance of pests continues to increase. Its application in agriculture is limited. It is necessary to develop an oxadiazole compound that can inhibit the growth of insects, especially mosquito larvae. Contents of the invention [0004] The object of the ...

Claims

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Application Information

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IPC IPC(8): C07D413/06C07D413/14A01P7/04
CPCC07D413/06C07D413/14
Inventor 李洪森汤佳蓉成嫕喆郑志怡陈婕孙海琳牛慧芳陈晶懿周向明沈菲杨通
Owner SHANGHAI UNIV OF ENG SCI
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