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: 2011-05-18
HANGZHOU UDRAGON CHEMICAL CO LTD
View PDF2 Cites 127 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] Embodiment 1, a kind of synthetic method of novel spirodiclofen compound, its reaction is:

[0026]

[0027] Add 60ml of methylene chloride, 6.3g (0.02mol) of 3-(2,4-dichlorophenyl)-2-oxo Generation-1-oxaspiro[4,5]-dec-3-en-4-alcohol and 7.5g (0.075mol) triethylamine, after stirring and dissolving, add dropwise 3.3g (0.024mol) of sec-butyl chloroformate under ice-water bath mol), then continue to stir at room temperature, and the thin-layer plate controls the reaction time. After the reaction, the reaction solution was poured into saturated NaHCO 3 solution (about pH 8), stirred for ten minutes, separated, washed the organic layer with 40-60ml of water, and used anhydrous Na 2 SO 4 Dry, and remove the solvent methylene chloride under reduced pressure to obtain a light yellow viscous liquid, which is recrystallized with 50 ml of methanol to obtain 7.08 g of colorless crystals (namely I a in Table 1), yield: 86%. Melting point: 100~102℃.

[0028] 1 H NMR (500Hz, ...

Embodiment 2

[0029] Embodiment 2, a kind of synthetic method of novel spirodiclofen compound, its reaction is:

[0030]

[0031] Add 60ml 1,2-dichloroethane, 6.3g (0.02mol) 3-(2,4-dichlorophenyl )-2-oxo-1-oxaspiro[4,5]-dec-3-en-4-alcohol and 7.5g (0.075mol) triethylamine, after stirring and dissolving, add n-butyl chloroformate dropwise under ice-water bath 3.3 g (0.024 mol) of ester, and then continue stirring at room temperature, and the reaction time is controlled by a thin-layer plate. After the reaction, the reaction solution was poured into saturated NaHCO 3 solution (about pH 8), stirred for ten minutes, separated, washed the organic layer with 40-60ml of water, and used anhydrous Na 2 SO 4 Drying, removing the solvent 1,2-dichloromethane under reduced pressure to obtain a light yellow oily liquid, which was recrystallized with 50ml of methanol to obtain 6.59g of colorless crystals (i.e. Ib in Table 1), yield: 80%. Melting point: 92-93°C.

[0032] 1 H NMR (500Hz, CDCl 3 , ...

Embodiment 3

[0033] Embodiment 3, a kind of synthetic method of novel spirodiclofen compound, its reaction is:

[0034]

[0035] Add 60ml of benzene, 6.3g (0.02mol) 3-(2,4-dichlorophenyl)-2-oxo- 1-oxaspiro[4,5]-dec-3-en-4-alcohol and 5.9g (0.075mol) pyridine, after stirring and dissolving, 3.6g (0.024mol) of isoamyl chloroformate was added dropwise under ice-water bath, and then Stirring was continued at room temperature, and the reaction time was controlled by a TLC plate. After the reaction, the reaction solution was poured into saturated NaHCO 3 solution (about pH 8), stirred for ten minutes, separated, washed the organic layer with 40-60ml of water, and used anhydrous Na 2 SO 4 After drying, the solvent benzene was removed under reduced pressure to obtain a light yellow oily liquid, which was recrystallized with 50 ml of methanol to obtain 6.9 g of colorless crystals (ie Ic in Table 1), yield: 82%. Melting point: 95~96℃.

[0036] 1 H NMR (500Hz, CDCl 3 , δppm): 7.41~7.21 (3H,...

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, relates to a novel spirodiclofen compound and a synthesis method thereof, and is suitable for use as an insecticide and acaricide. Background technique [0002] Spirodiclofen (structural formula is III) is a tetronic acid high-efficiency acaricide developed by Bayer. It has a different mechanism of action from the existing insecticides and acaricides. In particular, it has an excellent inhibitory effect on mite eggs. [0003] CN101255147A has reported the use of structural formula A series of spirodiclofen derivatives were synthesized by reacting the compound with chrysanthemum acid chloride, and the biological activity test was done on mites and broad bean aphid. [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 insecticides and acaricides with new structures and mechani...

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 Applications(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 Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap