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3-Arylacrylic acid and its derivatives anti-plant virus agent

An anti-plant virus agent, anti-plant virus technology, applied in the field of anti-plant virus agent, plant virus disease prevention and control, the field of new anti-plant virus agent, can solve the problems of poor control effect, environmental risk, difficult quality control and the like, Achieve the effect of extremely low toxicity, good environmental compatibility and simple chemical structure

Active Publication Date: 2016-05-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many practical varieties of these existing anti-plant virus agents, and the control effect is poor, generally lower than 60%. Quality control is relatively difficult, and there is a certain environmental risk in long-term use.

Method used

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  • 3-Arylacrylic acid and its derivatives anti-plant virus agent
  • 3-Arylacrylic acid and its derivatives anti-plant virus agent
  • 3-Arylacrylic acid and its derivatives anti-plant virus agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of 3-Aryl Acrylic Acids 14-22 and 24-29:

[0023]

[0024] A mixture of aromatic aldehyde (2.16mmol), malonic acid (0.45g, 4.32mmol), piperidine (2.0mL) and pyridine (20mL) was heated under reflux for 3-40h. Cool to room temperature, add 25% K to the reaction solution 2 CO 3 solution, heating with stirring, liquid separation, acidification of the aqueous phase with dilute hydrochloric acid, filtration, and drying to obtain the crude product, and recrystallization or column chromatography to obtain the pure product.

[0025] (E)-3-(2-furyl)acrylic acid (14)

[0026] Purified by column chromatography (petroleum ether: ethyl acetate = 2:1) to obtain a yellow solid with a yield of 66%. Melting point 143-144°C;1 HNMR (400MHz, CDCl 3 ): δ7.53(d, 3 J HH =15.6Hz, 1H), 7.52(d, J=1.6Hz, 1H), 6.68(d, J=3.6Hz, 1H), 6.50(dd, J=3.6Hz, 1.6Hz, 1H), 6.32(d, J=15.6Hz, 1H).

[0027] (E)-3-(2-thienyl)acrylic acid (15)

[0028] Purified by column chromatogra...

Embodiment 2

[0056] Embodiment 2: Synthesis of (E)-3-(2-hydroxyl-1-naphthyl)acrylic acid (23)

[0057]

[0058] Formethoxymethyl triphenylphosphine bromide (3.73 g, 8.72 mmol) and 2-hydroxy-1-naphthaldehyde (1.50 g, 8.72 mmol) in methanol (20 mL) were slowly added potassium carbonate (2 g) in methanol (20 mL) solution, the reaction was stirred at room temperature for 6 h, then concentrated. Dichloromethane (50 mL) and water (50 mL) were added, the layers were separated, the aqueous phase was extracted with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was added into 2mol / L potassium hydroxide (30mL) and stirred for 2h. Dichloromethane (50 mL) was added, the layers were separated, the aqueous phase was acidified with 2 mol / L dilute hydrochloric acid, filtered, washed with water, and dried to obtain a white solid 24 (1.34 g), yield 72%. Melting point 179-180°C; 1 HNMR (400M...

Embodiment 3

[0059] Example 3: (E)-methyl 3-(7-benzo[1,2,3]thiadiazolyl)acrylate (30) and (E)-3-(2-hydroxy-1-naphthyl) Synthesis of Methyl Acrylate (31)

[0060]

[0061] Dissolve (E)-3-arylacrylic acid 22 or 23 (2mmol) in methanol (25mL), add concentrated sulfuric acid (0.72g) at room temperature, and heat to reflux for 8h. Cool to room temperature, add dichloromethane (50mL) and water (50mL), separate the layers, extract the aqueous phase with dichloromethane, combine the organic phases, wash the organic phase with sodium bicarbonate, dry over anhydrous sodium sulfate, filter, and concentrate to obtain product.

[0062] (E)-methyl 3-(7-benzo[1,2,3]thiadiazolyl)acrylate (30)

[0063] White solid, yield 94%. The melting point is 118-120°C. 1 HNMR (400MHz, CDCl 3 ): δ8.70(d, J=8.4Hz, 1H), 7.95(d, J=16.0Hz, 1H), 7.84(d, J=7.2Hz, 1H), 7.73(t, J=8.0Hz, 1H ), 6.46(d, J=16.0Hz, 1H), 3.88(s, 3H). 13 CNMR (100MHz, CDCl 3 ): δ166.7, 159.6, 142.3, 138.8, 131.5, 127.8, 125.9, 122.0, 77.5, ...

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Abstract

The invention relates to an application of 3-aryl acrylic acid represented by a general formula (I) and a derivative thereof in pesticides, wherein the 3-aryl acrylic acid and the derivative thereof can be adopted as novel anti-plant virus agents, can be provided for well inhibiting tobacco mosaic virus, pepper virus, tomato virus, sweet potato virus, potato virus, melon virus, maize dwarf mosaic virus and the like, and can be provided for effectively preventing and controlling virus diseases of a plurality of crops such as tobacco, pepper, tomato, melon vegetables, grains, vegetables, beans and the like, especially tobacco mosaic diseases. (Wherein Ar and R are defined in an instruction).

Description

technical field [0001] The present invention relates to a new type of anti-plant virus agent and its application, in particular to 3-aryl acrylic acid and its derivatives as anti-plant virus agents, and the interaction between 3-aryl acrylic acid and its derivatives and anti-plant virus active ingredients Compositions as anti-plant virus agents and their application in preventing and treating plant virus diseases belong to the technical field of pesticides. Background technique [0002] 3-Arylacrylic acid is an important intermediate in organic synthesis, widely used in spices, medicines, pesticides, sweeteners, plastics and photosensitive resins. It is an indispensable growth regulator in some plant life activities and plays an important role in plant cell growth and division, and its derivatives are widely found in natural medicines. According to literature reports, 3-phenylacrylic acid derivatives have multiple biological and pharmacological activities, such as anti-infl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/64C07C59/52C07C57/44C07D317/60C07D319/18C07D307/54C07D333/24C07D213/55C07D277/30C07D261/08C07D231/16C07D285/14C07C69/734A01N37/38A01N37/10A01N43/30A01N43/32A01N43/08A01N43/10A01N43/40A01N43/78A01N43/80A01N43/56A01N43/828A01P1/00
CPCA01N37/10A01N37/38A01N43/08A01N43/10A01N43/30A01N43/32A01N43/40A01N43/56A01N43/78A01N43/80A01N43/82C07C57/44C07C59/52C07C59/64C07C69/734C07D213/55C07D231/16C07D261/08C07D277/30C07D285/14C07D307/54C07D317/60C07D319/18C07D333/24
Inventor 汪清民吴萌王兹稳孟垂松王开亮呼艳娜王力钟
Owner NANKAI UNIV
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