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Diketopiperazine derivatives and their preparation and use

A compound and composition technology, applied in the field of piperazine dione derivatives and their preparation, can solve the problems of rising pest control costs, environmental and ecological damage, and increased pesticide usage.

Active Publication Date: 2017-01-04
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] One is the safety of pesticides. Some traditional pesticides have been eliminated due to their toxicity and impact on the environment and ecology. Phosphorus, omethoate, etc. and highly toxic carbamate insecticides such as aldicarb, carbofuran, methomyl, etc. are increasingly banned. At present, these important insecticide varieties have been banned in the world. disabled or about to be disabled
[0005] The second is the problem of insecticide resistance of pests. Due to the long-term abuse of chemical insecticides, the resistance of pests has increased. On the one hand, the amount of insecticides has continued to increase, forming a vicious circle and causing great damage to the environment and ecology; On the other hand, the cost of pest control continues to rise

Method used

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  • Diketopiperazine derivatives and their preparation and use
  • Diketopiperazine derivatives and their preparation and use
  • Diketopiperazine derivatives and their preparation and use

Examples

Experimental program
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Effect test

preparation example Construction

[0056] A particularly preferred preparation process is as follows:

[0057]

[0058] (5) Dissolve triphosgene (BTC) in an inert solvent (such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, DMF, etc.), and compound 6 and an organic base are dissolved in an inert solvent ( (such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, etc.), add triphosgene in an inert solvent (such as dichloromethane) solution at low temperature to obtain compound 7.

[0059] (6) Drop compound 7 into a solution of compound 5 and an organic base in an inert solvent (such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, DMF, etc.) to obtain compound 10.

[0060] (7) Dissolving compound 6, carbon disulfide, and an organic base into an inert solvent (such as THF, toluene, methylene chloride, 1,2-dichloroethane, chloroform, carbon tetrachloride, etc.) solution to obtain compound 8 , adding triphosgene to give compound 9.

[00...

Embodiment 1

[0096] Embodiment 1: the synthesis of piperazine diketone intermediate 5a

[0097]

[0098] (1) Take ornithine hydrochloride 1a (337mg, 2mmol), di-tert-butyl dicarbonate ((Boc) 2 O) (1310mg, 6mmol), triethylamine (Et 3 N) (404mg, 4mmol) was dissolved in 6ml of acetone and 6ml of water, stirred at room temperature, followed by TCL. After the reaction, the acetone was distilled off under reduced pressure, and extracted three times with dichloromethane. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain the crude product of compound 2a.

[0099] (2) In a 100ml round bottom flask, add the crude product of compound 2a obtained in the first step reaction, tryptophan methyl ester hydrochloride (1019mg, 4mmol), then add triethylamine (6mmol), HOBt (297mg, 2.2mmol), EDCl (460mg, 2.4mmol), add 30ml of dichloromethane, stir in ice bath for 1 hour, and then stir...

Embodiment 2

[0101] Embodiment 2: the synthesis of piperazine diketone urea compound 10a-1

[0102]

[0103] Into a 50ml round bottom flask was added triphosgene (BTC) (223mg, 0.75mmol), dissolved in 5ml of dichloromethane. Then aniline 6a (140mg, 1.5mmol) and triethylamine (152mg, 1.5mmol) were dissolved in 5ml of dichloromethane, added dropwise to the previous flask, stirred in an ice bath, dripped for about half an hour, and stirred at room temperature (TLC tracking reaction) to obtain compound 7a. Take another 50ml round bottom flask, dissolve compound 5a (300mg, 1mmol) in 1ml DMF, add triethylamine (101mg, 1mmol), and stir magnetically. Slowly drop the previous reaction into the flask and react at room temperature. After the dropwise addition, the reaction was complete (TLC followed the reaction). After removing the solvent in the reaction system by distillation under reduced pressure, and washing with water, the obtained crude product was separated and purified by column chroma...

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Abstract

The invention discloses a diketone piperazine derivative and its preparation and application. Specifically, the present invention discloses a compound with the structure shown in formula I or a pharmaceutically acceptable salt or a pesticide acceptable salt thereof. The compound has excellent insecticidal activity and can be used as a human 5-HT2a receptor agonist, and the definition of the compound of the formula I is detailed in the description.

Description

technical field [0001] The invention belongs to the field of pesticides and medicines. Specifically, the present invention relates to a diketone piperazine derivative and its preparation and use. Background technique [0002] Insecticides are the main means of controlling pests and play a very important role in modern agriculture. Most of the currently used insecticides are nerve agents, for example: organophosphorus insecticides and carbamate insecticides mainly inhibit the activity of acetylcholinease in insects, causing insect poisoning and death; Insecticides are nerve agents, and their toxicological mechanism is considered to be directly interacting with the sodium ion channel on the nerve membrane to produce toxic effects; neonicotinoid insecticides are recognized as a kind of acetylcholine receptor poison, which acts on Insecticides of acetylcholine receptors. [0003] However, in the past 20 to 30 years, great changes have taken place in the pesticide market struc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/06C07D241/08C07D401/14C07D417/14C07D409/14C07D405/14A01N47/30A01N47/36A01N43/60A01P7/04A01P5/00
Inventor 宋恭华孙海洋王佳毅黄瑾李晖张小灵
Owner EAST CHINA UNIV OF SCI & TECH
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