Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Novel spirodiclofen compound and preparation method and application thereof

A technology of ester compounds and compounds, applied in the field of pesticides, can solve the problems of the preparation method of new spirodiclofen compounds and the acaricidal activity that have not been reported.

Active Publication Date: 2012-02-01
HANGZHOU UDRAGON CHEMICAL CO LTD
View PDF2 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the structure, preparation method and acaricidal (mite eggs) activity of the novel spirodiclofen compounds of the present invention have not been reported

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel spirodiclofen compound and preparation method and application thereof
  • Novel spirodiclofen compound and preparation method and application thereof
  • Novel spirodiclofen compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1. A method for synthesizing a novel spirodiclofen compound, the reaction is:

[0026]

[0027] Add 60ml dichloromethane and 6.3g (0.02mol) 3-(2,4-dichlorophenyl)-2-oxygen to a 100ml reaction flask equipped with electromagnetic stirring, condenser, constant pressure dropping funnel and thermometer. Substitute-1-oxaspiro[4,5]-dec-3-en-4-ol and 7.5g (0.075mol) triethylamine, stir to dissolve, add sec-butyl chloroformate 3.3g (0.024 mol), then continue to stir at room temperature, and the thin layer plate controls the reaction time. After the reaction is over, pour the reaction solution into saturated NaHCO 3 Solution (pH about 8), stir for ten minutes, separate, wash the organic layer with 40-60ml of water, and use anhydrous Na for the organic phase 2 SO 4 After drying, the solvent dichloromethane was removed under reduced pressure to obtain a light yellow viscous liquid, which was recrystallized with 50 ml of methanol to obtain 7.08 g of colorless crystals (namely I...

Embodiment 2

[0029] Example 2. A method for synthesizing a new type of spirodiclofen, the reaction is:

[0030]

[0031] Add 60ml 1,2-dichloroethane and 6.3g (0.02mol) 3-(2,4-dichlorophenyl) into a 100ml reaction flask equipped with electromagnetic stirring, condenser, constant pressure dropping funnel and thermometer. )-2-oxo-1-oxaspiro[4,5]-dec-3-en-4-ol and 7.5g (0.075mol) triethylamine, stir to dissolve, add n-butyl chloroformate dropwise under ice water bath Ester 3.3g (0.024mol), then continue to stir at room temperature, and the thin layer plate controls the reaction time. After the reaction is over, pour the reaction solution into saturated NaHCO 3 Solution (pH about 8), stir for ten minutes, separate, wash the organic layer with 40-60ml of water, and use anhydrous Na for the organic phase 2 SO 4 After drying, the solvent 1,2-dichloromethane was removed under reduced pressure to obtain a pale yellow oily liquid, which was recrystallized with 50 ml of methanol to obtain 6.59 g of color...

Embodiment 3

[0033] Example 3. A method for synthesizing a novel spirodiclofen compound, the reaction is:

[0034]

[0035] In a 100ml reaction flask equipped with electromagnetic stirring, condenser, constant pressure dropping funnel and thermometer, 60ml benzene, 6.3g (0.02mol) 3-(2,4-dichlorophenyl)-2-oxo- 1-oxaspiro[4,5]-dec-3-en-4-ol and 5.9g (0.075mol) pyridine, after stirring to dissolve, 3.6g (0.024mol) isoamyl chloroformate was added dropwise under ice water bath, then Continue stirring at room temperature, and the thin layer plate controls the reaction time. After the reaction is over, pour the reaction solution into saturated NaHCO 3 Solution (pH about 8), stir for ten minutes, separate, wash the organic layer with 40-60ml of water, and use anhydrous Na for the organic phase 2 SO 4 After drying, the solvent benzene was removed under reduced pressure to obtain a pale yellow oily liquid, which was recrystallized with 50 ml of methanol to obtain 6.9 g of colorless crystals (namely I c...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a novel spirodiclofen compound and a preparation method and application thereof. The structure of the novel spirodiclofen compound is shown in a general formula I. The synthesis method of the novel spirodiclofen compound comprises the steps of: in the presence of an acid binding agent, in an aprotic solvent, reacting a compound with a structure formula II with chloro-carbonic ester with a structure formula shown in the description at room temperature, and separating and purifying a product to prepare the novel spirodiclofen compound. The novel spirodiclofen compound can be used for killing pests or mites.

Description

Technical field [0001] The invention belongs to the field of pesticides, and relates to a novel spirodiclofen compound and a synthesis method thereof, which are suitable for insecticide and acaricide. Background technique [0002] Spirodicin (structure III) is a highly effective quaternary keto acid acaricide developed by Bayer. It has a different mechanism of action from existing insecticides and acaricides. By inhibiting the synthesis of lipids in the body of harmful mites, it is effective against nymphs. Especially it has an excellent inhibitory effect on mite eggs. [0003] CN101255147A reported the structural formula The compound of chrysanthemum oxychloride was reacted to synthesize a series of spirodiclofen derivatives, and the biological activity of mites and broad bean aphid was tested. [0004] [0005] Due to the large and frequent use of drugs, harmful insects and mites have developed severe resistance to many insecticides and acaricides. The development of insecticide...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94A01N47/06A01P7/04A01P7/02
Inventor 许良忠尹瑞锋冯显国
Owner HANGZHOU UDRAGON CHEMICAL CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com