Glycosyl isoxazole compounds and their preparation methods and fungicides

A compound, isoxazole technology, applied in the preparation of sugar derivatives, botanical equipment and methods, fungicides, etc., can solve the problems of large agricultural production losses, fungicides resistance, etc., achieve excellent inhibitory activity, obvious mycelium Effect of growth inhibitory effect

Active Publication Date: 2022-05-20
BEIJING UNIV OF AGRI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, plant diseases cause large losses in agricultural production, and the prevention and control of plant diseases is mainly through the use of chemical reagents.
However, under the selection of a single fungicide for a long time, plant pathogenic bacteria have become more and more serious and common in resistance to fungicides.
On the other hand, the residues of fungicides have caused increasingly severe negative impacts on the environment

Method used

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  • Glycosyl isoxazole compounds and their preparation methods and fungicides
  • Glycosyl isoxazole compounds and their preparation methods and fungicides
  • Glycosyl isoxazole compounds and their preparation methods and fungicides

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preparation example Construction

[0074] The present invention also provides a preparation method for glycosylisoxazole compounds, comprising the following steps:

[0075] (a) When R 2 When it is H, compound IV and Under the effect of oxidizing agent and catalyst, react to obtain compound V;

[0076] Wherein, the structural formulas of compound IV and compound V are respectively as follows:

[0077]

[0078] (b) when R 2 When it is an acetyl group, compound V reacts with an acetylating reagent under the action of an organic base to obtain compound VI;

[0079] Wherein, the structural formula of compound VI is as follows:

[0080]

[0081] (c) When R 2 When it is benzyl, compound V reacts with a benzylation reagent under the action of sodium hydride to obtain compound VII;

[0082] Wherein, the structural formula of compound VII is as follows:

[0083]

[0084] (d) when R 2 When it is a propargyl group, compound V reacts with a propargylating reagent under the action of sodium hydride to obtai...

Embodiment 1

[0123] This embodiment provides glycosyl isoxazole compound V 3 And preparation method thereof, synthetic route is as follows:

[0124]

[0125] The specific synthesis steps are as follows:

[0126] Step (i): Weigh 20g of pure diacetone dextrose and pour it into a 1000mL dry round bottom flask, pressurize and pump 400mL of anhydrous pyridine, stir well to dissolve. Slowly add 13.07 mL of acetic anhydride to the reaction system dropwise in an ice-water bath and keep the temperature not exceeding 15°C, remove the ice-water bath, stir at room temperature for 2 hours, and detect by TLC [V (petroleum ether): V (ethyl acetate) = 3: 1] The response is complete. Post-treatment: filter the reacted material with suction and collect the filtrate, concentrate, add dichloromethane to dissolve the concentrated product and extract (3 times, 300 mL each), wash with deionized water (2 times, 150 mL each), and combine the organic phases Then add anhydrous sodium sulfate to dry, filter wit...

Embodiment 2

[0132] This embodiment provides glycosyl isoxazole compound V 1 For its preparation method, refer to the synthetic route of Example 1, the only difference is that the p-chlorophenylacetylene in step (v) is replaced by equimolar phenylacetylene.

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Abstract

The invention relates to the technical field of bactericidal materials, in particular to a glycosyl isoxazole compound, a preparation method and a bactericide. Glycosyl isoxazoles have the following general structural formula: R 1 Any one selected from substituted or unsubstituted aromatic groups, R 2 Any one selected from H, acetyl, benzyl and propargyl. The present invention uses natural sugar compounds as the skeleton, is safe, low in toxicity, high in selectivity, not easy to remain, and has good environmental compatibility, and further introduces an active group isoxazole structure, and the obtained glycosyl isoxazole compounds have It has many advantages such as safety, high efficiency, low toxicity, low residue, broad spectrum, not easy to produce resistance, and has excellent bactericidal activity.

Description

technical field [0001] The invention relates to the technical field of bactericidal materials, in particular to a glycosylisoxazole compound, a preparation method thereof and a bactericide. Background technique [0002] Phytopathogens are closely related to most plant diseases. At present, plant diseases cause large losses in agricultural production, and the prevention and control of plant diseases is mainly through the use of chemical reagents. However, under the long-term selection of a single fungicide, plant pathogenic bacteria have become more and more serious and common in resistance to fungicides. On the other hand, the residues of fungicides have caused increasingly severe negative impacts on the environment. [0003] Therefore, it is of great significance to develop a pesticide lead compound with high efficiency, low toxicity, low residue, not easy to produce resistance and conform to green chemistry. [0004] In view of this, the present invention is proposed. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H9/04C07H1/00A01N43/90A01P3/00
CPCC07H9/04C07H1/00A01N43/90Y02P20/55
Inventor 赵汗青李培霞陈自力
Owner BEIJING UNIV OF AGRI
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