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Novel bi-halogenated acetylated heterocyclic pyrethroid and preparation and application methods thereof

A technology of bishalogenated acetyl and polycyclanthrin, applied in the field of medicine, can solve the problems of inability to take into account the mosquito killing activity and drug resistance

Inactive Publication Date: 2019-04-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In view of this, the present invention provides a novel bishalogenated acetylated heterocyclethrin and its preparation method and application, which solves the problem that existing pyrethroid insecticides cannot take into account good mosquito killing activity and drug resistance question

Method used

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  • Novel bi-halogenated acetylated heterocyclic pyrethroid and preparation and application methods thereof
  • Novel bi-halogenated acetylated heterocyclic pyrethroid and preparation and application methods thereof
  • Novel bi-halogenated acetylated heterocyclic pyrethroid and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Step 1: methyl m-iodobenzoate (1.0eq.) is put into a 100mL round-bottomed flask, put into a magnetic stirrer, and use N 2 Deaeration, plug the rubber plug, and plug in the N 2 Balloon, use a syringe to add an appropriate amount of dried toluene as a solvent, stir evenly, and then add LiBH with a syringe 4 (in THF) (2.0M, 1.0~2.0eq.), then move the system into an oil bath at 100°C, react for 1h, spot the plate to confirm whether the reaction is complete (TLC method). When the reaction is complete, slowly add an excess of 5% dilute hydrochloric acid as a quenching agent until no bubbles are generated in the reaction system. Then, the reaction system was distilled under reduced pressure with a rotary evaporator to substantially completely dry the solvent, and then extracted three times with ethyl acetate, the organic phase was collected, dried with anhydrous magnesium sulfate, filtered, the filtrate was collected, and the solvent was dried by rotary evaporation under redu...

Embodiment 2

[0033] Weigh a certain amount of C 15 h 15 Br 2 IO 2 (1.0eq.), PdCl 2 (dppf)(0.03~0.05eq.), K 3 PO 4 (3.0~5.0eq.), benzothiophene boronic acid (1.0~3.0eq.) in a 100mL round bottom flask, put a magnetic stirrer, and use N 2 Deaeration, plug the rubber plug, and plug in the N 2 Balloons, add an appropriate amount of dried toluene as a solvent, react in an oil bath at 100°C for 24 hours, and detect the end point of the reaction by TLC. Subsequently, the reaction flask was removed, the magnetic stirring bar was taken out with a magnet, and the stirring bar was washed with dichloromethane several times, and the washing solution was packed in the original reaction flask. Then the reaction system was basically completely spin-dried with a rotary evaporator, and then extracted three times with ethyl acetate. The organic phase was collected and dried with anhydrous magnesium sulfate. The filtrate was evaporated to dryness by rotary evaporation, and then purified by silica gel c...

Embodiment 3

[0035] Weigh a certain amount of C 15 h 15 Br 2 IO 2 (1.0eq.), PdCl 2 (dppf)(0.03~0.05eq.), K 3 PO 4 (3.0~5.0eq.), 5-chlorothiophene-2-boronic acid (1.0~3.0eq.) in a 100mL round bottom flask, put a magnetic stirrer, and use N 2 Deaeration, plug the rubber plug, and plug in the N 2 Balloons were added with an appropriate amount of dried toluene as a solvent, and reacted in an oil bath at 100°C for 24 hours, and the end point of the reaction was detected by TLC. Subsequently, the reaction flask was removed, the magnetic stirring bar was taken out with a magnet, and the stirring bar was repeatedly washed with dichloromethane, and the washing solution was packed in the original reaction flask. Then the reaction system was basically completely spin-dried with a rotary evaporator, and then extracted three times with ethyl acetate. The organic phase was collected and dried with anhydrous magnesium sulfate. The filtrate was evaporated to dryness by rotary evaporation, and then...

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Abstract

The invention relates to the technical field of medicines, particularly to a novel bi-halogenated acetylated heterocyclic pyrethroid and preparation and application methods thereof. The novel bi-halogenated acetylated heterocyclic pyrethroid has a chemical structural formula shown as the formula I. The preparation method of the novel bi-halogenated acetylated heterocyclic pyrethroid comprises thefollowing steps of, firstly, reducing methyl m-iodobenzoate with LiBH4 to obtain m-iodobenzyl alcohol; secondly, mixing dimethylcyclopropane carboxylic acid, oxalyl chloride, N, N-dimethyl formamide and the m-iodobenzyl alcohol for mixed reaction to obtain DCA-O (dimethylcyclopropane carboxylate) compounds; thirdly, through Suzuki coupling, subjecting the DCA-O prepared in the second step, PdCl2(dppf), K3PO4 and boric acid to reaction to obtain the novel bi-halogenated acetylated heterocyclic pyrethroid. The novel bi-halogenated acetylated heterocyclic pyrethroid is applied as a mosquito growth inhibiting pesticide. The novel bi-halogenated acetylated heterocyclic pyrethroid and the preparation and application methods thereof solve the technical problem that pyrethroid pesticides in the prior art cannot integrate mosquito killing activity and pesticide resistance.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to a novel bishalogenated acetylated heterothrin and its preparation method and application. Background technique [0002] The danger of mosquitoes is not only to harass and suck blood, but also to be the vector of many serious diseases. In foreign countries, mosquitoes are the carriers of arboviruses such as encephalitis, dengue, Chikungunya, and Zika; in my country, mosquito coal is one of the four major pests. The vector of malaria, lymphatic filariasis, epidemic hepatitis B encephalitis, etc. Currently, the use of safe and effective insecticides against mosquito-borne populations remains one of the most effective ways to rapidly interrupt the transmission of diseases such as malaria, lymphatic filariasis, dengue, chikungunya, and Zika. [0003] As a first step in understanding the level of Aedes albopictus resistance to insecticides used for control and the mechanisms ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/747C07C67/08C07D333/16C07D333/56C07D333/28C07D333/38C07D213/61C07D213/84C07D213/647C07D213/30C07D215/14A01N53/06A01P7/04
CPCA01N53/00C07C67/08C07C69/747C07D213/30C07D213/61C07D213/647C07D213/84C07D215/14C07D333/16C07D333/28C07D333/38C07D333/56C07C2601/02
Inventor 张焜朱秋雁赵肃清杨洋劳志婷钟颖颖张炳杰洪为歉
Owner GUANGDONG UNIV OF TECH
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