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Indole-based heterocyclic compound as well as preparation method and application thereof in prevention and treatment of plant diseases

A kind of heterocyclic compound and compound technology, which is applied to indole heterocyclic compound and its preparation and application field in preventing and controlling plant diseases, and achieves the effect of good anti-plant virus and pathogenic activity

Active Publication Date: 2020-06-30
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no report about the application of this type of compound in the prevention and treatment of plant diseases so far.

Method used

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  • Indole-based heterocyclic compound as well as preparation method and application thereof in prevention and treatment of plant diseases
  • Indole-based heterocyclic compound as well as preparation method and application thereof in prevention and treatment of plant diseases
  • Indole-based heterocyclic compound as well as preparation method and application thereof in prevention and treatment of plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of indole heterocyclic compound Ia-d

[0050]

[0051] Indole carbonyl acetyl chloride: Weigh 20g of indole and add it to a 1L four-neck flask, add 350mL of anhydrous ether under mechanical stirring, after the solid is completely dissolved, slowly add 17.3mL of oxalyl chloride dropwise at 0°C, and it takes 30 minutes to complete the addition . The reaction solution was reacted at 0° C. for 3 h, then raised to room temperature and then reacted for 1 h. After the reaction was completed, it was filtered with suction and washed three times with anhydrous ether. After drying, 32 g of compound 2 (ie, indolecarbonyl acetyl chloride) was obtained, with a yield of 90%, which could be directly used in the next reaction after being characterized.

[0052] Indolecarbonylacetaldehyde 3: Add the above-prepared product 2 into a 500mL four-necked round-bottomed flask, then add 153mL of ethyl acetate, and add 42.9mL of tri-n-butyltin hydride dropwise in ...

Embodiment 2

[0058] Embodiment 2: the synthesis of indole heterocyclic compound Ie

[0059]

[0060] Indole heterocyclic compound 5: In a 100mL four-neck round bottom flask, add indole carboaldehyde (5.8mmol), alanine amino acid 4e (11.6mmol), 30mL dimethyl sulfoxide solvent, solid iodine (5.8mmol) , the mixture was mechanically stirred and reacted for 30min under a nitrogen atmosphere at 110°C. After the reaction was completed, a saturated sodium thiosulfate solution (20mL) was added to react for 10min, extracted, dried over anhydrous magnesium sulfate, then suction filtered, and the product compound was obtained by column chromatography 5. Brown solid, melting point 202-203°C, yield 66%; 1 HNMR (400MHz, DMSO-d 6 )δ11.54(s,1H,NH),7.84(d,J=7.9Hz,1H,Ar-H),7.74(d,J=2.6Hz,1H,Ar-H),7.47(d,J= 8.0Hz,1H,Ar-H),7.30(s,1H,Ar-H),7.12–7.23(m,2H,Ar-H),2.49(s,3H,CH 3 ); 13 C NMR (100MHz, DMSO-d 6 )δ158.2, 147.3, 136.3, 123.5, 122.8, 122.0, 120.0, 119.4, 119.2, 112.0, 103.9, 13.6; HRMS (ESI) cal...

Embodiment 3

[0062] Embodiment 3: the synthesis of indole heterocyclic compound If-j

[0063]

[0064]Indolehydrazone 8a-e: In a 100mL round bottom flask equipped with a magnetic stirrer, add indole-3-carboxylhydrazide (6mmol), the corresponding aldehyde (6mmol), absolute ethanol (80mL), and the mixture was dissolved at 80 After reacting at ℃ for 1 hour, cool naturally to room temperature, and use a rotary evaporator to evaporate until 15-20 mL of liquid remains, and then stand still and filter with suction to obtain acylhydrazones 8a-e. After nuclear magnetic detection, the data are as follows.

[0065] 8a. White solid, melting point 294-296°C, yield 92%; 1 H NMR (400MHz, DMSO-d 6 )δ11.81(s,1H,NH),11.71(s,1H,NH),8.68(s,1H,Ar-H),8.30(s,1H,Ar-CH),8.23(d,J=7.3 Hz,1H,Ar-H),8.02(dd,J=6.6,1.2Hz,1H,Ar-H),7.70(d,J=8.0Hz,1H,Ar-H),7.46–7.51(m,2H ,Ar-H),7.33–7.37(m,1H,Ar-H),7.16–7.24(m,2H,Ar-H); 13 C NMR (100MHz, DMSO-d 6 )δ136.0, 133.5, 130.1, 131.2, 128.0, 127.0, 123.1, 122.3, 120.9, 112....

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Abstract

The invention discloses an indole-based heterocyclic compound as well as a preparation method and application thereof in prevention and treatment of plant diseases. According to the method, indole isreacted with oxalyl chloride to obtain indole oxalyl chloride, then indole oxalyl chloride is reduced by tributylstannane to obtain indole carbonyl acetaldehyde, and finally indole carbonyl acetaldehyde is reacted with a corresponding amino acid under the catalysis of iodine to obtain a compound; or indole hydrazide is reacted with an aldehyde, and oxidizing with iodobenzene acetate is carried outto obtain the compound. The indole heterocyclic compound provided by the invention shows especially excellent plant virus resisting activity, can well inhibit the tobacco mosaic virus, and also showsbroad-spectrum plant pathogenic bacteria resisting activity.

Description

technical field [0001] The invention belongs to the technical field of agricultural protection, and more specifically relates to a class of indole heterocyclic compounds and their preparation and application in preventing and controlling plant diseases. Background technique [0002] There are many kinds of plant viruses and their distribution is very wide. In agricultural production, virus diseases are the second largest type of plant diseases after fungi. The vast majority of economic crops are affected by plant viruses, which reduce production or quality to varying degrees. Plant viruses are absolutely parasitic in plant cells, and the materials, energy, and places required for their replication are completely provided by host cells. Since plants do not have the same Complete immune system, so the prevention and treatment of plant virus disease is very difficult, known as "plant cancer". Such as tobacco mosaic virus (Tobacco mosaic virus, TMV) is not only a widely studied...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A01P3/00A01P1/00
CPCC07D413/04
Inventor 王兹稳张铭君廖安财康锦汪清民
Owner TIANJIN NORMAL UNIVERSITY
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