Pyridazinone compound and synthesis method thereof

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

Inactive Publication Date: 2012-05-02
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 in agriculture

Method used

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  • Pyridazinone compound and synthesis method thereof
  • Pyridazinone compound and synthesis method thereof
  • Pyridazinone compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A pyridazinone compound, the compound molecular formula is as follows

[0028]

[0029] R 1 is methyl, R 2 for hydrogen, R 3 For morpholine, the synthetic method of this pyridazinone compound comprises the following steps:

[0030] (1) Preparation of 4,5-dichloro-3(2H)pyridazinone

[0031]

[0032] In a 250mL three-necked flask, add 50g of dichlorobutenalic 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%.

[0033] (2) Preparation of 2-bromo-p-methylacetophenone

[0034]

[0035] In a 250mL three-necked flask with a condensation and drying device, add 70mL of toluene, 26.6g of anhydro...

Embodiment 2

[0043] A pyridazinone compound, the compound molecular formula is as follows

[0044]

[0045] R 1 is chlorine, R 2 is ethyl, R 3 Be piperidine, the synthetic method of this pyridazinone compound comprises the following steps:

[0046] (1) Preparation of 2-bromo-1-p-chlorophenyl-1-butanone

[0047]

[0048] In a 250ml three-neck flask equipped with a condensation drying device, add 60ml of chlorobenzene and 26g of anhydrous AlCl3, stir, and slowly add 2-bromobutyryl bromide dropwise under ice-water cooling, and react at low temperature for 2 hours. Then rise to 35oC, heat preservation reaction for 3 hours. The reaction solution was poured into 200ml of ice water and stirred continuously. Separate the organic phase, wash the organic phase with water 6 to 7 times, and dry it with anhydrous MgSO4. Remove chlorobenzene, distill under reduced pressure, collect fractions at 162-164°C, yield 78.2%

[0049] (2) Preparation of 4,5-dichloro-2-[2-(4-chloro-phenyl)-2-oxo-ethy...

Embodiment 3

[0056] A preparation method of pyridazinone compound, comprising the following steps:

[0057] (1) Preparation of 4,5-dichloro-3(2H)pyridazinone

[0058] Mix di-chlorocrotoninic acid and hydrazine sulfate at a molar ratio of 1:1, and under the catalysis of sodium acetate, conduct condensation reaction at 80°C for 1 hour to obtain 4,5-dichloro-3(2H ) pyridazinone, wherein the molar ratio of di-chlorocrotonic acid to sodium acetate is 1:1;

[0059] (2) Preparation of α-halogenated-aromatic aliphatic mixed ketones

[0060] The substituted aromatic hydrocarbon ethylbenzene and α-bromoacetyl bromide are mixed in a molar ratio of 1:1, in AlCl 3 Under the catalysis of α-halogenated-aromatic aliphatic mixed ketones, the AlCl 3 The addition amount is that the molar ratio with ethylbenzene is 1: 1;

[0061] (3) Preparation of 2-substituted-3(2H)-pyridazinone

[0062] The 4,5-dichloro-3 (2H) pyridazinone prepared in step (1) and the α-halogenated-aromatic fatty mixed ketone prepared...

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Abstract

The invention relates to a pyridazinone compound and a synthesis method thereof. The synthesis method comprises the following steps: subjecting a substituted aromatic hydrocarbon and alpha halogen-benzoic acyl halide to Friedel-Crafts acylation to generate alpha halogen aromatic-aliphatic mixed ketone; reacting the alpha halogen aromatic-aliphatic mixed ketone with 4,5-dichloro-3(2H) pyridazinone, and then subjecting the alpha halogen aromatic-aliphatic mixed ketone and cyclamine to substitution reaction in solvent under the catalysis of alkaline reagent to synthesize the pyridazinone compound. Compared with the prior art, the pyridazinone compound is simple in process flow, wide in application range and applicable to the prevention and the treatment of pests such as flies, mosquitoes, fleas and the like and agricultural insects such as rice water weevil, beet armyworm, armyworm and the like, has the performance for inhibiting the growth of insects and particularly larva of the mosquitoes and is an insecticide with a wide application prospect.

Description

technical field [0001] The invention relates to an inhibitor and a synthesis method thereof, in particular to a pyridazinone compound and a synthesis method thereof. Background technique [0002] Pyridazinone compounds are widely used in the control of sanitary pests and crop pests, and many commercial pesticide varieties have been obtained, but the resistance of pests has been continuously enhanced during long-term use. Its application in agriculture is limited. Contents of the invention [0003] The object of the present invention is to provide a kind of pyridazinone compound and its synthesis method with simple technological process and wide application range in order to overcome the above-mentioned defects in the prior art. [0004] The object of the present invention can be achieved through the following technical scheme: a kind of pyridazinone compound, it is characterized in that, this compound molecular formula is as follows: [0005] [0006] Among them, R 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/22A01P7/04
Inventor 李洪森赵琳静陈思浩陆佳妮孙志君高辰杰朱春杰
Owner SHANGHAI UNIV OF ENG SCI
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