Indole heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases

A technology of heterocyclic compounds and compounds, applied in the directions of botanical equipment and methods, applications, plant growth regulators, etc., to achieve 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 heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases
  • Indole heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases
  • Indole heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of indole heterocyclic compound Ia-h

[0047]

[0048] Indole carbonyl acetyl chloride: Weigh 20g of indole (marked as 1) into a 1L four-necked flask, add anhydrous ether (Et 2(0) 350mL, after the solid is completely dissolved, slowly add oxalyl chloride [(COCl) dropwise at 0°C 2 】17.3mL, 30min 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.

[0049] Indolecarbonylacetaldehyde: Add the product 2 prepared above 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 a nitrogen atmosphere at ...

Embodiment 2

[0059] Embodiment 2: the synthesis of indole heterocyclic compound Ii

[0060]

[0061] Take compound Ia (0.4g), add 40mL of tetrahydrofuran, add 60% NaH (0.16g) under mechanical stirring under nitrogen atmosphere at room temperature, react at room temperature for half an hour, then add 0.86g methyl iodide, react at room temperature for 1h, and heat to reflux for 1h. Add 10mL of water and react for 5min. Extraction, drying and finally concentration of the resulting product Ii. Yellow solid, yield 86%, melting point 71-73°C; 1 H NMR (400MHz, DMSO-d 6)δ7.86(d, J=7.8Hz, 1H, Ar-H), 7.73(s, 1H, Ar-H), 7.50(d, J=8.1Hz, 1H, Ar-H), 7.30(s, 1H, Ar-H), 7.27(d, J=7.5Hz, 1H, Ar-H), 7.19(d, J=7.5Hz, 1H, Ar-H), 3.83(s, 3H, N-CH 3 ),2.48(s,3H,Ar-CH 3 ); 13 C NMR (100MHz, DMSO-d 6 )δ158.3, 147.0, 136.8, 126.8, 123.7, 122.1, 120.1, 119.6, 119.2, 110.3, 103.0, 32.6, 13.5; HRMS (ESI) calcd for C 13 h 13 N 2 O(M+H) + 213.1022, found 213.1027.

Embodiment 3

[0062] Embodiment 3: the synthesis of indole heterocyclic compound Ij-n

[0063]

[0064] Indolehydrazone 7a-e:

[0065] Add indole-3-carboxylhydrazide (6mmol), the corresponding aldehyde (6mmol), and absolute ethanol (80mL) to a 100mL round-bottomed flask equipped with a magnetic stirrer, and react the mixture at 80°C for 1 hour, then cool Return to room temperature, use a rotary evaporator to evaporate until 15-20 mL of liquid remains, let it stand, and filter with suction to obtain acylhydrazones 7a-e, which are detected by NMR, and the data are as follows.

[0066] 7a. White solid, melting point 233-234°C, yield 79%; 1 H NMR (400MHz, DMSO-d 6 )δ11.74(s,1H,NH),11.38(s,1H,NH),8.20–8.33(m,3H,Ar-H),7.72(d,J=7.3Hz,2H,Ar-H), 7.47(s,1H,Ar-CH),7.38–7.49(m,3H,Ar-H),7.14–7.22(m,2H,Ar-H); 13 C NMR (100MHz, DMSO-d 6 )δ134.7, 129.5, 128.8, 126.7, 122.2, 120.8, 111.9.

[0067] 7b. White solid, melting point 242-243°C, yield 90%; 1 H NMR (400MHz, DMSO-d 6 )δ11.72(s,1H,NH),11.2...

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Abstract

The invention discloses an indole heterocyclic compound as well as a preparation method and application thereof in prevention and treatment of plant diseases. According to the method, indole is reacted 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 isreacted with a corresponding amino acid under the catalysis of iodine to obtain a compound. The indole heterocyclic compound provided by the invention shows especially excellent plant virus resistingactivity, can well inhibit the tobacco mosaic virus, and also shows broad-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 the preparation of a class of indole heterocyclic compounds and their 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 stud...

Claims

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Application Information

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IPC IPC(8): C07D413/04A01N43/824A01N43/76A01P1/00A01P3/00
CPCC07D413/04A01N43/82A01N43/76
Inventor 王兹稳康锦廖安财张铭君汪清民
Owner TIANJIN NORMAL UNIVERSITY
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