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
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  • 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

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  • 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...

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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

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Application Information

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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
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