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Coumarin kind compound and its preparation and application

A technology of coumarins and compounds, applied in the fields of fungicides and agricultural insecticides

Inactive Publication Date: 2006-11-29
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the compounds disclosed in the above-mentioned patents do not fall into the scope of the present invention

Method used

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  • Coumarin kind compound and its preparation and application
  • Coumarin kind compound and its preparation and application
  • Coumarin kind compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0070] Example 1 Preparation of Compound 5

[0071]

[0072] At room temperature, 0.2 g of 60% sodium hydride was added to the reaction flask, washed with petroleum ether, 30 ml of dry N,N-dimethylformamide was added to it, stirred for half an hour, and 0.5 g of compound (III -1), continue to stir until no gas is released, add 0.8 g of compound (II-1), and continue to stir for 3 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate 3 times, the extracts were combined, washed 3 times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain 5 g of oily liquid. Column chromatography obtained 0.68 g of the title compound as a pale yellow solid product with a yield of 68%. Melting point: 131-133°C.

[0073] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0074] δppm 2.18 (3H, s), 2.36 (3H, s), 3.77 (3H, s), 3.83 (3H, s), 5.17 (2H, s), 6.84-6.85 (1H, d), 6.89-6.92 (1H) , M), 7.39 (3H, m), 7.4...

example 2

[0075] Example 2 Preparation of compound 49

[0076]

[0077] At room temperature, a mixed solution containing 0.85 g of anhydrous potassium carbonate, 0.6 g of compound (III-2), 0.93 g of compound (II-1) in 20 ml of methyl ethyl ketone was heated under reflux and stirred for reaction for 5 hours, and the reaction mixture was poured into Extract 3 times with ethyl acetate in ice water, combine the extracts, wash 3 times with saturated brine, dry, filter, and concentrate under reduced pressure to obtain a yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:2) was used to obtain 0.89 g of the title compound as a solid, with a yield of 75%. Melting point: 83-85°C.

[0078] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0079] δppm 2.37 (3H, s), 3.77 (3H, s), 3.84 (3H, s), 5.18 (2H, s), 6.88-6.89 (1H, d), 7.39 (1H, m), 7.41 (3H, m ), 7.45 (1H, m), 7.48 (1H, m).

example 3

[0080] Example 3 Preparation of Compound 106

[0081]

[0082] At room temperature, a mixture containing 0.3 g of anhydrous potassium carbonate, 0.22 g of compound (III-3), 0.30 g of compound (II-2) in 10 ml of methyl ethyl ketone was heated under reflux and stirred for reaction for 5 hours, and the reaction mixture was poured into Extract 3 times with ethyl acetate in ice water, combine the extracts, wash 3 times with saturated brine, dry, filter, and concentrate under reduced pressure to obtain a yellow solid as a crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:2) yielded 0.18 g of the title compound as a solid.

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Abstract

A coumarin-type compound with excellent bactericiding activity can be used to prevent and eliminate various diseases and pests of different agricultural crops, such as frosty mildew, rice blast, armyworm, plutella xylostella, etc. Its preparing process is also disclosed.

Description

Technical field [0001] The invention belongs to the field of agricultural insecticides and fungicides. Specifically, it relates to a coumarin compound and its preparation and application. Background technique [0002] The natural product coumarin and methoxy acrylate compounds are both known compounds with biological activity. The document JP04-182461 once disclosed a compound of the following general formula: [0003] [0004] The structural chemistry of compound 51 disclosed in the patent is as follows: [0005] [0006] Before the present invention, the Chinese patent (application number 200310105079.6) we applied for relates to benzopyrone derivatives represented by the following general formula as insecticides and fungicides: [0007] [0008] Where: A is CH or N; B is O, S or NR 9 ; R 8 Is hydrogen or (C 1 -C 12 ) Alkyl; R 1 , R 2 Is hydrogen, C 1 -C 12 Alkyl or halo C 1 -C 12 Alkyl; R 3 Is hydrogen, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl or C 1 -C 12 Alkoxy; R ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/06A01N43/16
Inventor 刘长令李淼关爱莹张弘李志念叶天降
Owner SHENYANG RES INST OF CHEM IND
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