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Benzopyrone compounds with pest killing and sterilizing activity and preparation and use

A technology of benzopyrone and compounds, applied in the fields of application, organic chemistry, botany equipment and methods, etc., can solve the problem of low activity of compounds

Active Publication Date: 2005-05-18
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through synthesis and bioassay, we found that the compound has low activity

Method used

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  • Benzopyrone compounds with pest killing and sterilizing activity and preparation and use
  • Benzopyrone compounds with pest killing and sterilizing activity and preparation and use
  • Benzopyrone compounds with pest killing and sterilizing activity and preparation and use

Examples

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Effect test

example 1

[0094] Example 1: The preparation method of compound 1

[0095] At room temperature, 0.84 g of 60% sodium hydride was added to the reaction flask, washed with petroleum ether, 30 ml of dry N, N dimethylformamide was added thereto, the reaction was stirred for half an hour, and 1.7 g of 7 -Hydroxycoumarin, continue to stir until no gas is released, add 3 grams of (E)-2-[2-(bromomethyl)phenyl]-3-methoxymethyl acrylate, and continue to stir for 3 hours. The reaction mixture was poured into ice water, extracted three times with ethyl acetate, the combined extracts were washed three times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain 5 g of oily liquid. Column chromatography gave 2.8 g of the title compound as a light reddish-yellow oil with a yield of 76.5%.

example 2

[0096] Example 2: Preparation of compound 2

[0097] At room temperature, 0.45 g of 60% sodium hydride was added to the reaction flask, washed with petroleum ether, 20 ml of dry N,N dimethylformamide was added thereto, the reaction was stirred for half an hour, and 1.0 g of 7 -Hydroxy-4-methylcoumarin, continue to stir until no gas is released, add 1.66 grams of (E)-2-[2-(bromomethyl)phenyl]-3-methoxymethyl acrylate, continue to stir 3 hours. The reaction mixture was poured into ice water, extracted three times with ethyl acetate, the combined extracts were washed three times with saturated brine, dried, filtered, and concentrated 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) gave 1.73 g of the title compound with a melting point of 140-143°C. Yield 80%.

example 3

[0098] Example 3: Preparation of compound 101

[0099] At room temperature, containing 1.2 grams of anhydrous potassium carbonate, 1.0 grams of 7-hydroxy-4-methylcoumarin, 1.70 grams of 2-bromomethyl-α-(methoxyimino) methyl phenylacetate in 20 The mixed solution of butanone in milliliters was heated under reflux and stirred for 5 hours, the reaction mixture was poured into ice water, extracted 3 times with ethyl acetate, the combined extracts were washed 3 times with saturated brine, dried, filtered, and concentrated under reduced pressure to obtain a yellow solid as crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:2) gave 1.77 g of the title compound, melting at 150-152°C. Yield 83%.

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Abstract

The present invention relates to a new kind of benzopyrone derivatives expressed in generatal expression (I), and the benzopyrone derivatives are used as pesticide and bactericide.

Description

technical field [0001] The invention belongs to agricultural insecticide and fungicide. Background technique [0002] The natural products benzopyrone and methoxyacrylate compounds are known biologically active compounds. Document JP04-182461 once disclosed the compound of following general formula: [0003] [0004] The structural chemistry of compound 51 disclosed in this patent is as follows: [0005] [0006] No data on the activity of this compound are disclosed in the literature. Through synthesis and bioassay, we found that the compound has low activity. Contents of the invention [0007] In order to obtain effective compounds that can control various diseases and insect pests at a very small dose, the inventors of the present invention have synthesized a new type of benzopyrone compound, which has broad-spectrum activity-can be used in Control diseases caused by various pathogens such as Oomycetes, Basidiomycetes, Ascomycetes and Deuteromycetes on various...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/16C07D311/16
CPCA01N43/16C07D311/16
Inventor 刘长令关爱莹李志念李林李正名李淼张明星张弘
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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