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Ferulic acid phenethyl alcohol amine derivative and application thereof

A technology of phenylethanolamine and derivatives, applied in the field of pesticides, can solve the problems of crop yield reduction, damage to plant nutrient conduction, deformity, etc.

Inactive Publication Date: 2013-10-16
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After infecting the host, the virus not only competes with the host for the nutrients necessary for plant growth, but also destroys the nutrient conduction of the plant, changes some metabolic balance of the host plant and the activity of some enzymes, resulting in difficulty in plant growth, deformity, yellowing, etc. Symptoms, severe ones also cause the death of the host plant, resulting in reduced crop yield and quality

Method used

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  • Ferulic acid phenethyl alcohol amine derivative and application thereof
  • Ferulic acid phenethyl alcohol amine derivative and application thereof
  • Ferulic acid phenethyl alcohol amine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of ferulic acid phenylethanolamine derivative

[0034] 1) Preparation of acetyl ferulic acid 2

[0035] Dissolve 0.52 mol (20.8 g) of sodium hydroxide in 200 mL of water, add 0.20 mol (38.8 g) of ferulic acid, stir until completely dissolved, and lower the temperature of the reaction system below 10°C in an ice-water bath. Another 0.25mol (25.4g) of acetic anhydride was slowly added dropwise to the cold reaction solution, stirred for 1h after the dropwise addition, then raised to room temperature and continued to stir for 2h. Use concentrated hydrochloric acid to adjust the pH of the reaction solution to 4-5, a large amount of white solids precipitate out, filter with suction, and recrystallize with ethanol to obtain the solid that is the product. Acetyl ferulic acid is a white solid with a melting point of 200-202°C. 1 HNMR (DMSO) δ (ppm) 400MHz: 2.24 (s, 3H, COCH 3 ), 3.80 (s, 3H, OCH 3 ), 6.57 (d, 1H, J=16.0Hz, COCH), 7.08-7.53 (m, 3...

Embodiment 2

[0063] Embodiment 2: Preparation of hydrogenated ferulic acid phenylethanolamine derivatives

[0064] 1) Preparation of ethyl 3-methoxy-4-hydroxyphenylpropionate 8

[0065] Dissolve 0.1 mol (20 g) of 1 in a mixed solution of 170 mL of absolute ethanol and 60 mL of tetrahydrofuran, add 10 mL of concentrated hydrochloric acid at room temperature, and stir. Nitrogen gas was introduced under standard atmospheric pressure to remove the air in the reaction system, and then 1 g of 10% palladium carbon was added. Keep the reaction temperature at 40°C in the hot water bath, replace nitrogen with hydrogen and continue to feed in, monitor the gas feed with a bubbler and isolate it from the outside air once; after about 20 hours, the reaction is complete, and the palladium carbon is separated by suction filtration, and the organic solvent is removed under reduced pressure , washed the remaining mixed solution with saturated brine, extracted three times with 100 mL ethyl acetate, combined...

Embodiment 3

[0091] Embodiment 3: Determination of biological activity of aphids

[0092] Cut the faba bean plants (leaves of bean seedlings unfolded, plant height about 12 cm) with about 60 bean aphid nymphs that have grown to adults in the same order two days ago from potted plants, and put them in a certain concentration of medicinal solution that has been cultivated in advance. Soak in the medium for 3 seconds, take out and shake off the remaining liquid, insert it on a 12-hole foam plastic plate to moisturize (the foam plastic plate is 3.5cm thick, put it in a 35×45cm porcelain plate, and soak it with water), and wait for the liquid medicine to dry. Cover it with a glass cover (the upper opening is sealed with gauze and a rubber band). After processing, place it under standard constant temperature and humidity conditions. After 96 hours, the death of the test insects was investigated by pulling the needle and lightly touching the insect body, and those who did not move were considere...

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PUM

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Abstract

A ferulic acid phenethyl alcohol amine derivative is a compound having the general formula (I) in the original text, wherein R and R1 refer to 1-12 carbon alkyl, carbon alkenyl, carbon alkynyl or substituted benzyl; and R2 refers to 1-6 carbon alkyl, carbon alkoxy, carbon alkane amide, carbon alkyl sulphanyl, substituted benzyloxy group, halogen, hydroxyl, cyan, nitryl or carboxyl. When X-X is a carbon-to-carbon double bond, the configuration of the double bond is of a trans-form, a cis-form or a cis-trans mixed form; and when X-X is a carbon-to-carbon single bond, the compound is the ferulic acid phenethyl alcohol amine derivative. The ferulic acid phenethyl alcohol amine derivative has the advantages that the compound plays a fine inhibitory role in plant viruses and insects for transmitting the viruses, serves as insecticide to be capable of preventing and treating injurious insects such as homoptera, acarina and the like, serves as anti-plant viral agent to be capable of effectively inhibiting tobacco mosaic viruses, pepper viruses, tomato viruses, sweet potato viruses and the like, and is capable of effectively preventing and treating viral diseases of various crops such as tobacco, grains, vegetables, beans and the like.

Description

【Technical field】 [0001] The invention belongs to the technical field of pesticides, in particular to a derivative of phenylethanolamine ferulic acid and its application. 【Background technique】 [0002] There are 716 kinds of known plant viruses (Zhang Chengliang et al., Taxonomy of Plant Viruses, China Agricultural Press, 1996, 283), and some literatures believe that there are more than 1000 kinds of plant viruses. [0003] Plant viruses harm a variety of plants and microorganisms such as monocots and dicotyledons, and their distribution is very common. Every crop in common cultivated plants has one or more viruses. The damage is second only to fungal diseases. After infecting the host, the virus not only competes with the host for the nutrients necessary for plant growth, but also destroys the nutrient conduction of the plant, changes some metabolic balance of the host plant and the activity of some enzymes, resulting in difficulty in plant growth, deformity, yellowing, et...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/34C07C231/12A01P7/04A01P7/02A01P1/00
Inventor 赵卫光崔灿黄广英王立钟李永强李正名
Owner NANKAI UNIV
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