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Compound containing indole ring structure, preparation method and application of compound, and bactericide

A compound, the technology of indole ring, applied in the field of pesticides, can solve problems such as irrational use, prolonged use time, pathogenic bacteria resistance, etc.

Inactive Publication Date: 2021-07-30
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the prolonged use of these fungicides and long-term unreasonable use, many pathogenic bacteria have developed serious drug resistance.

Method used

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  • Compound containing indole ring structure, preparation method and application of compound, and bactericide
  • Compound containing indole ring structure, preparation method and application of compound, and bactericide
  • Compound containing indole ring structure, preparation method and application of compound, and bactericide

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0069] The preparation method of the compound represented by the formula (2-6) will be described.

[0070]

[0071] Step a: At 25°C, take the compound (790.12mmol) represented by formula (2-1) and place it in a 1L two-necked flask, add 400mL of 2M diethyl ether hydrochloride solution, and slowly add tert-butyl nitrite dropwise into the reaction flask (534.62mmol, 1eq.), reacted for 3 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure into a semi-solid, washed with 1-chlorobutane, and filtered with suction to obtain a white crystalline solid, the filtrate was concentrated, and the above process was repeated twice, and the filtered solids were combined to obtain a total of 81.10 g, to obtain the formula The compound represented by (2-2). used directly in the next reaction.

[0072] Step b: In a 500mL eggplant-shaped bottle, add magnets, the compound shown in formula (2-2) (193.48mmol, 1eq.), 250mL acetonitrile, sodium bicar...

preparation example 2

[0077] The production method of the compound represented by formula (I) will be described.

[0078]

[0079] In a 50mL eggplant-shaped bottle, add magneton and the compound (0.80mmol) represented by formula (2-7), dissolve it in 20mL ultra-dry tetrahydrofuran, cool to -5°C, add sodium hydride (1.40mmol), and react for 30 minutes, then add the compound (0.70mmol, 1eq.) shown in formula (2-6) to the system, about 1 hour, TLC monitors that the reaction of raw materials is complete, add 1.5mL water to quench, silica gel column chromatography (eluent extremely Sex is V 石油醚 :V 乙酸乙酯 =2:1~1:3) to obtain the compound shown in formula (I).

preparation example 3

[0081] The production method of some compounds represented by the formula (2-7) will be described.

[0082] The synthetic method of compound shown in intermediate formula (2-7-1):

[0083]

[0084]1-Chloromethyl-4-fluoro-1,4-diazidebicyclo[2.2.2]octanebis(tetrafluoroborate) salt (16.00mmol), lithium carbonate (32.00mmol), dichloromethane ( 26mL), water (13mL) were successively added to a round-bottom flask equipped with a stirring magnet, and indole-3-carboxylic acid (8.00mmol, 1eq.) was added, and the mixed system was stirred under ice bath for 4 hours. The completion of the reaction was monitored by TLC, moved to room temperature, diluted with water, extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and the crude product was purified by silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =20:1). The compound represented by the formula (2-7-1) was obtained as a purple-black flaky solid with a yield (based on i...

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Abstract

The invention belongs to the field of pesticides and discloses a compound containing an indole ring structure, a preparation method and application of the compound and a bactericide. The compound has the structure shown in the formula (I), and the compound has an excellent prevention and treatment effect on cucumber downy mildew, is equivalent to the current commercial oomycete disease prevention and treatment agent oxathiapiprolin, and has a good market development prospect.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a compound containing an indole ring structure, a preparation method and application thereof, and a fungicide. Background technique [0002] Oomycete is one of the important pathogenic bacteria that cause plant diseases. It has the characteristics of wide parasitic range, strong destructiveness, great harm and rapid development. [0003] Downy mildew is one of the most representative oomycetes. It has a short incubation period and can infect multiple times. It can cause a pandemic in a very short period of time. All cucumbers will die. [0004] Generally, plant diseases caused by downy mildew can be divided into the following three categories: 1) leaf disease, mainly downy mildew; 2) root and crown diseases of annual and perennial crops, such as wet soil, seedling withering, root, neck and stem rot 3) systemic disease, refers to the disease caused by the root infection of soil or seed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14A01N43/80A01P3/00
CPCC07D417/14A01N43/80
Inventor 杨光富周立明成传祥
Owner HUAZHONG NORMAL UNIV
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