Ferulic acid eugenol and isoeugenol heterozygote and application

A technology of isoeugenol and eugenol, which is applied in the fields of application, chemicals for biological control, biocides, etc., can solve the problem of inactivated virus activity, single structure, and anti-plant virus activity, which only include treatment and protection issues, to achieve the effect of low production cost, simple preparation process and excellent treatment

Active Publication Date: 2021-12-17
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] To sum up, small drug molecules containing ferulic acid structure have good anti-plant virus activity, but the structure of these drug small molecules is relatively simple, and the anti-plant virus activity only includes treatment and protection, and has not performed well. inactivated virus activity

Method used

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  • Ferulic acid eugenol and isoeugenol heterozygote and application
  • Ferulic acid eugenol and isoeugenol heterozygote and application
  • Ferulic acid eugenol and isoeugenol heterozygote and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] The preparation method of ferulic acid eugenol hybrid A1 comprises the steps:

[0117] (1) preparation of methyl ferulate:

[0118] Get ferulic acid (10g, 51.50mmol) in a three-necked flask, add 50mL of methanol, stir for 10 minutes, then add dropwise 98% concentrated sulfuric acid (5.06g, 51.50mmol) and react at a temperature of 80°C for about 8 hours. The solvent was recovered under pressure, 10 mL of water was added to the system, and the pH was adjusted to 8 with saturated sodium bicarbonate solution, and ethyl acetate was added to extract three times (100 mL each time), the extracts were combined, dried over anhydrous sodium sulfate, and the solvent was recovered under reduced pressure to obtain 9.85g of methyl ferulic acid intermediate, yield 91.7%.

[0119] (2) Preparation of bromoethyl ferulic acid methyl ester:

[0120] Take methyl ferulate (5.0g, 24.01mmol) in a three-necked flask, then add 50mL of n-butyl ketone and anhydrous potassium carbonate (3.98g, 28....

Embodiment 2

[0124] The preparation method of ferulic acid isoeugenol hybrid A2 comprises the steps:

[0125] Step (1)~(2) is the same as embodiment 1

[0126] (3) Preparation of target compound A2:

[0127] Take isoeugenol (1.5g, 9.13mmol) in a three-necked flask, then add 20mL of acetonitrile and anhydrous potassium carbonate (1.51g, 10.96mmol), stir at room temperature for 1 hour, then add bromoethyl ferulic acid methyl ester ( 2.88g, 9.13mmol), and reacted at 80°C for about 4 hours, filtered, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethyl acetate to obtain the target compound A2, 2.95g, yield 81.2%.

Embodiment 3

[0129] The preparation method of ferulic acid eugenol hybrid A3 comprises the steps:

[0130] (1) preparation of ethyl ferulate:

[0131] Get ferulic acid (10g, 51.50mmol) in a three-necked flask, add 50mL of ethanol, stir for 10 minutes, then add dropwise 98% concentrated sulfuric acid (5.06g, 51.50mol) and react at a temperature of 80°C for about 8 hours. The solvent was recovered under pressure, water was added to the system, and the pH was adjusted to 8 with saturated sodium bicarbonate solution, then ethyl acetate was added for extraction three times (100 mL each time), the extracts were combined, dried over anhydrous sodium sulfate, and the solvent was recovered under reduced pressure to obtain 10.50 g of ethyl ferulic acid intermediate, yield 91.7%.

[0132] (2) Preparation of bromoethyl ferulic acid ethyl ester:

[0133] Take ethyl ferulate (5.0g, 22.50mmol) in a three-necked flask, then add 50mL of n-butyl ketone and anhydrous potassium carbonate (3.73g, 27.00mmol),...

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Abstract

The invention discloses a ferulic acid eugenol and isoeugenol heterozygote and application. The structural general formula (I) of the ferulic acid eugenol and isoeugenol heterozygote is shown in the description, wherein R1 is hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a benzyl group, a 2-chlorobenzyl group, a 3-methylbenzyl group, a 4-chlorobenzyl group, an eugenol group or an isoeugenol group; R2 is a methyl group, an ethynyl group, a 4-methyl phenyl group, an eugenol group or an isoeugenol group; X is an oxygen atom, an oxyacetyl group, an amine ethylidene group or an ethylidene group; and Y represents a hydrogen atom, a methylene group, an ethylene group or an oxyacetyl group. The ferulic acid eugenol and isoeugenol heterozygote shows excellent treatment, protection and passivation activity on tobacco mosaic virus and cucumber mosaic virus, and is simple in preparation process and low in production cost.

Description

technical field [0001] The invention relates to the fields of chemical engineering and pesticides, in particular to eugenol ferulic acid and isoeugenol hybrids, and at the same time relates to the use of eugenol ferulic acid and isoeugenol hybrids in the preparation and prevention of tobacco mosaic virus disease and cucumber mosaic The application of medicines for plant virus diseases such as virus diseases. Background technique [0002] Plant virus diseases accompany the whole growth cycle of plants and have a huge impact on agricultural production. Due to the absolute parasitic nature of plant viruses, once plants are infected with plant viruses, virus diseases will spread in a large area, and it is difficult to prevent and control. The annual economic loss caused by plant virus diseases is as high as 20 billion US dollars. In recent years, plant virus diseases have shown an outbreak trend, among which the most serious plant viruses are Tobacco mosaic virus (TMV), cucumbe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/734C07C235/34A01N37/38A01P1/00
CPCC07C69/734C07C235/34A01N37/38C07B2200/09Y02P20/55
Inventor 甘秀海刘丹袁婷宋宝安胡德禹
Owner GUIZHOU UNIV
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