Maleimide compound, its preparation and application

A technology of maleimide and dimethyl maleic anhydride is applied to maleimide compounds and their preparation, and the application field in preventing and treating rape sclerotinia, and can solve the problem of affecting enzymes , affecting the growth of bacteria and other problems, to achieve the effect of simple preparation method, convenient operation and improved inhibitory effect

Active Publication Date: 2012-03-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The α and β unsaturated imide ring structures of maleimide compounds can combine with sulfhydryl functional groups, thereby affecting many sulfhydryl-containing enzymes in the body, and then affecting the growth of bacteria

Method used

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  • Maleimide compound, its preparation and application
  • Maleimide compound, its preparation and application
  • Maleimide compound, its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: N-n-butyl-2,3-dimethylmaleimide (I-1)

[0023] Weigh 5.0g (0.04mol) of 2,3-dimethylmaleic anhydride (dimethylmaleic anhydride) into a three-necked flask and dissolve it with 30mL of acetone, measure 3.7mL (0.038mol) of n-butylamine, and use Dilute with 20mL of acetone, then add dropwise into the three-neck flask with a constant pressure dropping funnel, and stir while adding dropwise, for about 8 minutes. The system was heated to 35°C and stirred for 3.0h, cooled to 0°C, and then added 2.28g of sodium acetate in triethylamine (0.1g NaAc and 3.0mL of triethylamine), 0.1g of CuI, and 8.0mL of acetic anhydride, stirred evenly, and heated To 80 ° C, stirring and reflux reaction for 6h. After the reaction, the reaction solution was cooled to room temperature (25° C.), part of the acetone in the reaction solution was evaporated, extracted three times with 50 mL of n-hexane, the organic phases were combined and distilled under reduced pressure to obtain a yellow...

Embodiment 2

[0027] Embodiment 2: N-isobutyl-2,3-dimethylmaleimide (I-2)

[0028]Weigh 5.0g (0.04mol) of dimethyl maleic anhydride and add it to a three-necked flask and dissolve it with 30mL of acetone, measure 3.8mL (0.038mol) of isobutylamine, dilute it with 20mL of acetone, and add it dropwise to In the three-neck flask, stir while adding dropwise for about 10 minutes. The system was heated to 45°C and stirred for 4.0h, cooled to 0°C, and 2.76g of sodium acetate in triethylamine solution (0.15g NaAc and 3.6mL of triethylamine), 0.1g of CuI, and 8.5mL of acetic anhydride were added in sequence, stirred evenly, and heated To 70 ° C, stirred and refluxed for 6.5 hours. After the reaction, the reaction solution was cooled to room temperature, part of the acetone in the reaction solution was evaporated, extracted three times with 50 mL of n-hexane, the organic phases were combined and distilled under reduced pressure to obtain a reddish-brown oily concentrated solution. The concentrated s...

Embodiment 3

[0032] Embodiment 3: N-n-hexyl-2,3-dimethylmaleimide (I-3)

[0033] Weigh 2.5g (0.02mol) of dimethyl maleic anhydride into a three-necked flask and dissolve it with about 20mL of toluene, measure 2.5mL (0.019mol) of n-hexylamine, dilute it with about 10mL of toluene, and add it dropwise to In the three-necked flask, stir while adding dropwise, for about 15 minutes, stir and react at 40° C. for 4.0 hours, and obtain a bright yellow liquid. Add 0.81 g of sodium acetate in triethylamine solution (0.08 g NaAc and 1.0 mL triethylamine), 0.08 g hydroquinone, and 3.0 mL acetic anhydride in sequence, stir evenly, heat to 75° C., and reflux at constant temperature for 8.0 h. After the reaction, the reaction solution was washed with water several times until the water layer was neutral, and the toluene layer was washed with anhydrous Na 2 SO 4 Dry, then use activated carbon and silica gel to absorb and decolorize by heating, filter, and concentrate the filtrate under reduced pressure ...

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Abstract

The invention discloses a maleimide compound as shown in the formula (I). In the formula (I), R is C1-C16 fatty alkyl, phenyl or substituted phenyl, wherein the fatty alkyl is C1-C16 straight-chain alkyl group, C1-C16 branched-chain alkyl group or C1-C16 cycloalkyl; and the substituent of the substituted phenyl is C1-C3 alkyl group, p-chloro group, 3,5-dichloroyl, 2-methyl-3-nitroyl, benzimidazolyl, 3,4,5-trifluoroyl. The preparation method of the maleimide compound is to use 2,3-dimethyl maleic anhydride and organic amine as raw materials to perform amidation reaction and dehydration ring-closing reaction in an organic solvent under the action of a catalyst, a polymerization inhibitor and / or a dehydrant to obtain the maleimide compound as shown in the formula (I). The preparation method of the compound is simple and is convenient to operate; with the adoption of the preparation method, the effect of inhibiting Sclerotinia sclerotiorum is raised and the toxicity is low.

Description

(1) Technical field [0001] The invention relates to the preparation and application of an antibacterial agent, in particular to a maleimide compound, its preparation and its application in preventing and treating rape sclerotinia. (2) Background technology [0002] Sclerotinia sclerotiorum is an important rapeseed disease caused by Sclerotmia sclerotiorum, which can occur in various stages of rapeseed growth, causing seedlings to rot, die or grow poorly. Sclerotinia sclerotiorum is widely distributed in my country, especially in the Yangtze River Basin and the south. The annual occurrence area is more than 5000 mu, accounting for more than 50% of the sown area, which poses a serious threat to the production safety of rapeseed. At present, the medicaments used for the prevention and treatment of rapeseed sclerotinia mainly include sclerotinia, carbendazim and procymidone. However, using the same fungicide for a long time will cause the bacteria to develop corresponding resis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/448C07D207/452C07D403/04A01N43/36A01N43/52A01P3/00
Inventor 陈小龙沈振忠李伟范永仙沈寅初
Owner ZHEJIANG UNIV OF TECH
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