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Pyridinium salt-containing N-(cinnamoyl)-N'-(substituted) propyl hydrazide compound, preparation method and application thereof

A technology of cinnamoyl and propyl hydrazide, which is applied in the field of propyl hydrazide compounds and their preparation, and can solve problems affecting citrus yield and citrus rot

Inactive Publication Date: 2020-07-10
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, Xanthomonas axonopodis pv. Citri causes citrus rot and affects citrus production globally

Method used

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  • Pyridinium salt-containing N-(cinnamoyl)-N'-(substituted) propyl hydrazide compound, preparation method and application thereof
  • Pyridinium salt-containing N-(cinnamoyl)-N'-(substituted) propyl hydrazide compound, preparation method and application thereof
  • Pyridinium salt-containing N-(cinnamoyl)-N'-(substituted) propyl hydrazide compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of 3-(3-pyridine) acrylic acid hydrazide

[0054] Add 3-(3-pyridine)acrylic acid (6.70mmol), EDCI (7.38mmol), HoBt (7.38mmol) into a 500mL round bottom flask, add 5mL of acetonitrile, add about 0.5mL of triethylamine under stirring to dissolve, add 300mL of acetonitrile, then slowly dropwise added 1mL of 60% hydrazine hydrate, and react overnight at room temperature. After the reaction is complete, filter with suction to remove the solids. After the filtrate is decompressed and precipitated, add 5 mL of 10% NaOH aqueous solution and extract with EA to remove unreacted 3-(3-pyridine) acrylic acid. Use anhydrous sodium sulfate for the organic phase After drying, the sample was mixed with silica gel, and the gradient elution of DCM:MeOH=10:1~5:1 was used to purify a yellow solid with a yield of 40%.

[0055] Other hydrazide intermediate compounds are synthesized according to the steps of Example 1 using corresponding raw materials or substituen...

Embodiment 2

[0056] Example 2: Synthesis of (E)-N'-cinnamoyl-3-pyridin-3-yl)acrylhydrazide

[0057] Add cinnamic acid (1.88mmol), EDCI (2.26mmol), HoBt (2.26mmol) into a 25mL round bottom flask, add 15mL of acetonitrile, add about 0.1mL of triethylamine to dissolve it under stirring, then add 3-(3- pyridine) acrylic acid hydrazide (1.88mmol), react at room temperature overnight. After the reaction was completed, it was suction filtered to obtain a solid, which was dispersed by heating with dichloromethane as a solvent. After cooling, it was suction filtered to obtain a yellow solid with a yield of 55%.

[0058] Other (E)-N'-(substituted) cinnamoyl-(3-pyridin-3-yl)propenyl hydrazide intermediate compounds were synthesized by referring to the steps of Example 2 using corresponding raw materials or substituents.

Embodiment 3

[0059] Embodiment 3: Preparation of the pyridinium salt compound of (E) N'-cinnamoyl-3-(pyridin-3-yl)acrylohydrazide structure

[0060] Add (E)-N'-cinnamoyl-(3-pyridin-3-yl)acrylhydrazide (1.02mmol) into a 15mL round-bottomed flask, add 5mL DMF, heat to 100°C to dissolve, and wait to dissolve After adding the corresponding halogenated hydrocarbon (1.23mmol), react at 110-120°C for about 4h. After the reaction is complete, cool to precipitate a solid, add a small amount of ethyl acetate while stirring, then filter with suction, wash the filter cake with ethyl acetate, dry, and recrystallize from methanol to obtain the target product.

[0061] Other target product compounds are synthesized with reference to the steps of Example 3 using corresponding raw materials or substituents.

[0062] The synthetic part of N-(cinnamoyl)-N'-(substituted) propylhydrazide compounds containing pyridinium salts and the H-NMR and C-NMR data are shown in Table 1, and the physicochemical properties...

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Abstract

The invention relates to a pyridinium salt-containing N-(cinnamoyl)-N'-(substituted) propyl hydrazide compound, a preparation method and application thereof. The compound has a structure shown as general formula (I); the compound has a good inhibition effect on pathogenic bacteria and fungi, and has good inhibition effects on Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, cucumber bacterial blight bacteria,konjak bacterial blight bacteria, Xanthomonas axonopodis pv. Citri, botryosphaeria dothidea, Clavibacter michiganensis subsp.michiganensis, pseudomonas syringae pv. actinidiae, applecanker bacteria, cucumber botrytis cinerea, fusarium oxysporum, sclerotinia sclerotiorum, gibberella zeae, phytophthora infestans, P. cinnamomi and the like.

Description

technical field [0001] The application relates to the technical field of medicinal chemistry, in particular to a pyridinium-containing N-(cinnamoyl)-N'-(substituted) propylhydrazide compound and its preparation method and application. Background technique [0002] In recent years, plant bacteria and fungi have seriously affected the yield and quality of crops worldwide, causing huge economic losses to farmers. For example, rice bacterial blight (Xanthomonas oryzaepv.Oryzae) is a rod-shaped Gram-negative bacterium that can cause the leaves of rice to wither and turn white, and it brings at least 10-50% of rice-growing countries every year. Production reduction, serious or even no harvest. Additionally, Xanthomonas axonopodis pv. Citri causes citrus rot, affecting citrus yields globally. In the process of agricultural production, due to the long-term use of traditional medicaments, plant pathogenic bacteria have developed certain resistance to them. Therefore, it is of grea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/56C07D405/12C07D409/12A01N43/40A01P3/00A01P1/00
CPCC07D213/56C07D405/12C07D409/12A01N43/40
Inventor 杨松周翔王培义冯钰梅齐普应邵武斌吴志兵
Owner GUIZHOU UNIV
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