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Dibenzocaprolactam pyrazolidine compound, preparation method and application thereof

A technology of pyrazolidine and caprolactam, which is applied in the field of pesticides, can solve the problems that the molting process cannot be carried out completely, kill pests and the like, and achieve the effects of good application prospect, good insecticidal activity and good biological activity.

Inactive Publication Date: 2020-09-22
朱翠萍
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Hydrazide insect growth regulators are a class of highly efficient, selective, and environmentally friendly insect growth regulators developed in recent years. They induce insects to molt in advance, but prevent the molt process from being completed and kill pests.

Method used

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  • Dibenzocaprolactam pyrazolidine compound, preparation method and application thereof
  • Dibenzocaprolactam pyrazolidine compound, preparation method and application thereof
  • Dibenzocaprolactam pyrazolidine compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of compound 3a:

[0035] Weigh 5mmol of 2'-iodo-[1,1'-biphenyl]-2-carbaldehyde into a reaction flask, add 30mL of ethanol, then add 6mmol of benzohydrazide, stir the reaction at 80°C overnight, and detect by TLC The reaction is complete, the reaction is cooled to room temperature, the precipitated solid is filtered, washed with petroleum ether, and the acylhydrazone compound obtained can be directly used in the next step; Add copper fluoromethanesulfonate (1:9) to the reaction flask, add 10 mL of anhydrous toluene, add 2.4 mmol of vinyltributyltin under nitrogen protection, stir and react at room temperature for 1 hour, then raise the temperature to 110°C, and continue to stir and react for 15 hours , TLC detects that the reaction is complete, the obtained reaction mixture is filtered through diatomaceous earth, washed with ethyl acetate, the solvent is concentrated under vacuum and reduced pressure, and the crude product is separated by column chromatograph...

Embodiment 2

[0039] Preparation of compound 3b:

[0040] Weigh 5mmol of 2-(2-iodonaphthalene-1-yl)benzaldehyde in a reaction flask, add 30mL of ethanol, then add 6mmol of benzohydrazide, and stir the reaction at 80°C overnight. TLC detects that the reaction is complete. The reaction was cooled to room temperature, and the precipitated solid was filtered and washed with petroleum ether, and the obtained acylhydrazone compound could be used directly in the next step; Add copper (1:9) to the reaction flask, add 10mL of anhydrous toluene, add 2.4mmol of vinyltributyltin under nitrogen protection, stir and react at room temperature for 1 hour, then raise the temperature to 110°C, continue to stir and react for 15 hours, and detect the reaction by TLC Completely, the obtained reaction mixture is filtered through diatomaceous earth, washed with ethyl acetate, the solvent is concentrated under vacuum and reduced pressure, and the crude product is separated by column chromatography to obtain the pr...

Embodiment 3

[0044] Preparation of compound 3c:

[0045] Weigh 5mmol of 2-(2-iodo-1H-pyrrol-1-yl)benzaldehyde into a reaction flask, add 30mL of ethanol, and then add 6mmol of benzohydrazide, stir the reaction at 80°C overnight, and detect the reaction by TLC Complete, the reaction is cooled to room temperature, the precipitated solid is filtered, washed with petroleum ether, and the acylhydrazone compound obtained can be used directly in the next step; Add copper methanesulfonate (2:8) to the reaction flask, add 10 mL of anhydrous toluene, add 2.6 mmol of vinyltributyltin under nitrogen protection, stir and react at room temperature for 1 hour, then raise the temperature to 110°C, and continue to stir and react for 20 hours. TLC detected that the reaction was complete, and the obtained reaction mixture was filtered through diatomaceous earth, washed with ethyl acetate, the solvent was concentrated under vacuum and reduced pressure, and the crude product was separated by column chromatogra...

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Abstract

The invention provides a dibenzocaprolactam pyrazolidine compound and a preparation method thereof. The preparation method of the compound includes the following steps of: reacting an iodo-biphenyldicarboxaldehyde compound with a hydrazide compound in an alcohol solvent to obtain an acylhydrazone compound, then substituting iodine in the acylhydrazone compound by a double bond, and then carrying out [3+2] cyclization reaction on the double bond and acylhydrazone to obtain the dibenzocaprolactam pyrazolidine compound. The dibenzocaprolactam pyrazolidine compound disclosed by the invention has certain insecticidal activity, particularly has good insecticidal activity on wheat aphids and whiteflies, also has certain insecticidal activity on cotton bollworms and red spiders, and can be appliedto preparation of new pesticides; the dibenzocaprolactam pyrazolidine compound disclosed by the invention has the advantages of good substrate universality and high reaction yield, is low in toxicityto normal cells of a human body, and has good applicability.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a dibenzocaprolactam pyrazolidine compound and a preparation method and application thereof. Background technique [0002] The prothymus of insects can secrete ecdysone, and the molting and metamorphosis characteristics of insects during growth and development are strictly regulated by ecdysone. Ecdysone is an endogenous hormone. When juvenile hormone exists, it mainly plays a role in molting; when juvenile hormone does not exist, ecdysone can also promote the differentiation of internal organs such as larval brain nerves and midgut, and metamorphosis occurs. , Ecdysone can also cause abnormal molting of insects and cause death, which is used to control pests. [0003] Since Nakanishi Koji et al. isolated zinthone, which has insect molting activity, from the leaves of zinnia in 1966, people have isolated more than 100 active substances of plant-derived ecdysone, b...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D487/14A01N59/00A01P7/04A01P7/02
CPCC07D487/04C07D487/14A01N59/00
Inventor 朱翠萍
Owner 朱翠萍
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