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A kind of n-substituted maleimide compound and its preparation and antibacterial application

A technology of maleimide and compound is applied in the fields of N-substituted maleimide compound and its preparation and antibacterial application, and achieves the effects of simple preparation method and convenient operation

Active Publication Date: 2020-01-14
杭州佳嘉乐生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Domestic control of rice sheath blight mainly uses Jinggangmycin, but long-term single use of the same agent is prone to drug resistance, and Jinggangmycin has already developed resistance in some areas. Invention of safe and efficient new antibacterial agents is imminent

Method used

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  • A kind of n-substituted maleimide compound and its preparation and antibacterial application
  • A kind of n-substituted maleimide compound and its preparation and antibacterial application
  • A kind of n-substituted maleimide compound and its preparation and antibacterial application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: Preparation of N-Jinggangmycin N-substituted maleimide (I-1)

[0033] Weigh 0.176g (1mmol) of Jinggang mycoamine and add it to a round bottom flask, add 10ml of 0.26mol / L methanol solution of sodium methoxide, stir at 30°C for 20min, measure 0.176g (1.8mmol) of maleic anhydride and add it to the round bottom flask In the bottom flask, stir and react at 30°C for 1 hour, then add 235 μL triethylamine, heat the system to 60°C for 2 hours after reaction for 20 minutes, cool to room temperature after the reaction, and distill under reduced pressure to obtain a yellow oily concentrate, which is used for 200 mesh silica gel column separation, the mobile phase is positive V 正丙醇 :V 乙酸 :V 水 =6:1:1, the target solution was collected and concentrated to obtain a light yellow oily product. The obtained product was confirmed to be N-jinggangmycin N-substituted maleimide (I-1) by 1H NMR and MS spectroscopic analysis, and the yield was 91.2% (based on the mass of acid ...

Embodiment 2

[0036] Embodiment 2: the preparation of N-Jinggang mycamine N-substituted maleimide (I-2)

[0037] Weigh 0.175g (1mmol) of Jinggang mycamine enamine into a round bottom flask, add 10ml of 0.26mol / L methanol solution of sodium methoxide, stir at 30°C for 20min, measure 0.175g (1.8mmol) of maleic anhydride and add to In a round-bottomed flask, stir and react at 30°C for 1 hour, then add 235 μL of triethylamine, heat the system to 60°C for 2 hours after reaction for 20 minutes, cool to room temperature after the reaction, and distill under reduced pressure to obtain a yellow oily concentrated solution. Separation on the column with 200 mesh silica gel, the mobile phase is positive V 正丙醇 :V 乙酸 :V 水 =6:1:1, the target solution was collected and concentrated to obtain a light yellow oily product. The resulting product is confirmed to be N-Jinggangmycetamine N-substituted maleimide (I-2) through 1H NMR and MS spectral analysis,

[0038]Yield 35.3% 1 H NMR (500MHz,DMSO)δ6.05(s,1H...

Embodiment 3

[0040] Embodiment 3: the preparation of N-Jinggang mycodolamine N-substituted maleimide (I-3)

[0041] Weigh 0.193g (1mmol) of Jinggang mycophenolamine and add it to a round bottom flask, add 6ml of 0.26mol / L methanol solution of sodium methoxide, stir at 30°C for 20min, measure 0.1176g (1.2mmol) of maleic anhydride and add it to In a round-bottomed flask, stir and react at 30°C for 1 hour, then add 150 μL of triethylamine, heat the system to 60°C for 2 hours after reaction for 20 minutes, cool to room temperature after the reaction, and distill under reduced pressure to obtain a yellow oily concentrated solution. Separation on the column with 200 mesh silica gel, the mobile phase is positive V 正丙醇 :V 乙酸 :V 水 =6:1:1, the target solution was collected and concentrated to obtain a light yellow oily product. The resulting product is confirmed to be N- Jinggang Mycosylamine N-substituted maleimide (I-3) through 1H NMR and MS spectral analysis,

[0042] Yield 70.5% 1 H NMR (50...

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Abstract

The invention discloses an N-substituted cis-butene imidodicarbonic diamide compound as shown in a formula (I), a preparation method of the compound and an application of the compound to inhibition of rice sheath blight fungi or sclerotinia sclerotiorum. The preparation method includes the steps: taking acid anhydride and organic amine as shown in a formula (II) as raw materials; performing amidation and dehydration ring-closure reaction in organic solvents under the action of catalysts and dehydrating agents; separating and purifying reaction liquid to prepare the N-substituted cis-butene imidodicarbonic diamide compound as shown in the formula (I) after reaction. The organic amine is validamine, valienamine, valiolamine or glucosamine hydrochloride, the catalysts are sodium methoxide, and the dehydrating agents are triethylamine. The preparation method is simple and convenient in operation, and a synthetic product has an inhibitory effect on rice sheath blight and sclerotium diseases.

Description

technical field [0001] The present invention relates to the preparation and application of N-substituted maleimide compounds, in particular to the preparation of N-substituted maleimide compounds containing aminocyclopolyols and their use in rice sheath blight-resistant bacteria Applications. Background technique [0002] Rice sheath blight, also known as moire, is an important rice disease caused by Rhizoctonia solani Kühn. It can occur from seedling stage to earing stage, causing rice to fail to ear, and there are more grains in earing, and the thousand-grain weight Rice sheath blight occurs in major rice areas across the country, especially in the Yangtze River Basin and the south. After the disease occurs, crop yields generally decrease by more than 15%. In severe cases, there is no harvest, and it will seriously affect the quality of rice. The disease has been listed in Before rice blast, it ranked first among rice diseases and became a serious obstacle to high and sta...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/452C07H19/044C07D207/456A01N37/32A01N43/16A01P3/00
CPCA01N37/32A01N43/16C07D207/452C07D207/456C07H19/044
Inventor 陈小龙陆跃乐李忠范永仙张丽君李延娟沈寅初
Owner 杭州佳嘉乐生物技术有限公司