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Hydrazide-containing quinazolinone derivative, and preparation method and application thereof

A technology of quinazolinone and derivatives, applied in the field of pesticides, can solve problems such as environmental pollution, single plant pathogenic fungus resistance, non-target biological toxicity, etc., and achieve the effect of obvious application value

Active Publication Date: 2020-02-04
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the continuous use of existing agents and the relatively single target of action make the resistance of plant pathogenic fungi gradually appear.
At the same time, the problems of high toxicity to non-target organisms and serious environmental pollution in existing agents have also greatly restricted their production and application.

Method used

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  • Hydrazide-containing quinazolinone derivative, and preparation method and application thereof
  • Hydrazide-containing quinazolinone derivative, and preparation method and application thereof
  • Hydrazide-containing quinazolinone derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis of 2-(4-oxoquinazolin-3(4H)-yl)-N'-(4-fluorophenyl)acethydrazine (I1)

[0040] Combine 2-(4-oxoquinazoline-3(4H)-yl)acetic acid (II-1) (2.50mmol), 4-fluorophenylhydrazine (III-1) (2.50mmol), triethylamine (7.50mmol) mmol), O-benzotriazole-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU) (2.50mmol) and acetonitrile (30mL) were added to a 50mL three-necked flask, After stirring for 4 hours at room temperature, the reaction was stopped. The reaction solution was filtered, the filter cake was washed with ethanol and dichloromethane successively, and dried to obtain the compound 2-(4-oxoquinazolin-3(4H)-yl)-N'-(4-fluorophenyl ) Acetylhydrazine (I1).

[0041]

[0042] Compounds I2-I21 were synthesized sequentially according to the method in Example 1. The structures of the synthesized hydrazide-containing quinazolinone derivatives (I1-I21) all adopted infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR) and high Resolved mass spec...

Embodiment 2

[0065] Example 2: The bactericidal activity of a hydrazide-containing quinazolinone derivative I1-I21 of formula (I) of the present invention

[0066] The mycelial growth rate method was used to determine the inhibitory activity of a quinazolinone derivative I1-I21 containing hydrazide structure against Rhizoctonia solani and Fusarium graminearum. The specific operation Proceed as follows:

[0067] 1. Weigh a certain amount of target compound and dissolve it in a certain volume of dimethyl sulfoxide to obtain a certain mass concentration of mother liquor;

[0068] 2. Measure 100μL of mother liquor and add it to 45mL of autoclaved potato agar medium, shake evenly;

[0069] 3. Pour the above-mentioned medium evenly into 3 petri dishes with a diameter of 9 cm, and after it has solidified, transfer the fungus cake with a diameter of 5 mm to the center of the petri dish;

[0070] 4. After the above-mentioned petri dish is cultured at 25±1°C until the colony is about 7.0 to 7.5 cm directly...

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Abstract

The invention belongs to the field of pesticides, and discloses a hydrazide-containing quinazolinone derivative, and a preparation method and application thereof. The structure of the derivative is shown as a formula (I). The compound is simple in preparation method, has an obvious inhibition effect on rhizoctonia solani and gibberella zeae, and can be applied to preventing and treating plant fungal diseases.

Description

Technical field [0001] The present invention relates to the field of pesticides, in particular to a hydrazide-containing quinazolinone derivative, a preparation method of the derivative, and the application of the derivative in preventing and treating plant fungal diseases. Background technique [0002] Plant pathogenic fungi have the characteristics of wide infestation, rapid onset and difficult control, which have caused huge economic losses to agricultural production. At present, chemical control is still the main method to prevent the epidemic and outbreak of plant pathogenic fungi in agriculture. However, the continuous use of existing drugs and the relatively single target of action have gradually revealed the resistance of plant pathogenic fungi. At the same time, the existing medicaments have large toxicity to non-target organisms and serious environmental pollution, which also greatly restrict their production and application. Therefore, the development of a new type o...

Claims

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Application Information

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IPC IPC(8): C07D239/90A01N43/54A01P3/00
CPCC07D239/90A01N43/54
Inventor 杨春龙王晓斌王濛琪
Owner NANJING AGRICULTURAL UNIVERSITY
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