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Beta-carbonyl enamine compounds and application for preparing phytopathogen antibacterial agent

A technology for plant pathogenic bacteria and carbonyl enamine, which is applied in the field of preparation of plant pathogenic bacteria antibacterial agents, the field of β-carbonyl enamine compounds, can solve problems such as drug resistance of diseased bacteria, and achieves high efficacy, simple post-processing and synthesis. short step effect

Active Publication Date: 2016-01-06
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional agricultural control—simple methods such as crop rotation have not been well implemented, making these diseases more and more serious. Chemical pesticide control is still the main means of plant disease control at present, but the large-scale and frequent use of chemical antibacterial agents has caused pathogens to affect severe drug resistance

Method used

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  • Beta-carbonyl enamine compounds and application for preparing phytopathogen antibacterial agent
  • Beta-carbonyl enamine compounds and application for preparing phytopathogen antibacterial agent
  • Beta-carbonyl enamine compounds and application for preparing phytopathogen antibacterial agent

Examples

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preparation example Construction

[0043] The synthetic route of the preparation β-carbonyl enamine compound established by the present invention is as follows:

[0044] (1) Synthesis of β-1,3-diketone

[0045] Substituted acetophenone and NaNH 2 Reflux in ethyl acetate for 10-15 hours, that is, substituted acetophenone undergoes Claisen condensation reaction with ethyl acetate under the catalysis of sodium amide, and β-1,3-diketone can be prepared.

[0046]

[0047] (2) Synthesis of β-carbonyl enamine compounds

[0048] β-1,3-diketone and CH 3 COONH 4 Refluxing in methanol solution for 1 to 3 hours, a typical nucleophilic addition reaction unique to ketone compounds that are first added and then eliminated occurs, and the target compound β-carbonyl enamine can be synthesized.

[0049]

[0050] The specific operation steps of synthesizing different types of β-carbonyl enamine compounds are as follows:

[0051] 1. Compound 1 is the synthesis of 4-phenyl-4-oxo-2-butene-2-amine

[0052] (1) Add 6.06g (...

example 1

[0093] In vitro bacteriostatic activity of example 1 compound 8 to rice blast pathogenic fungus

[0094] Accurately weigh 5 mg of compound 8 in a 20 mL vial, inject 0.5 mL of DMSO and 9.5 mL of sterile water into it, and make a 5% DMSO solution of the sample to be tested; Make 100mL culture medium containing the sample to be tested, and pour it into a sterile petri dish to make a flat culture medium with medicine. The same amount of solvent, namely 5% DMSO, was used as a blank control, and the commercially available antibacterial drug kresoxim-methyl was used as a positive control.

[0095] Use a hole puncher with a diameter of 5 mm to take out the rice blast pathogen bacterial cake that grows vigorously on the edge of the colony, transfer it to the above-mentioned flat culture medium with an inoculation needle, and paste it on the culture medium with the mycelium side facing down. Blocks were placed in the center in a triangular shape, covered and placed in a constant temper...

example 2

[0098] In vitro bacteriostatic activity of example 2 compound 14 to watermelon wilt pathogenic fungus

[0099] Accurately weigh 5 mg of compound 14 in a 20 mL vial, inject 0.5 mL of DMSO and 9.5 mL of sterile water into it, and make a 5% DMSO solution of the sample to be tested; Make 100mL culture medium containing the sample to be tested, and pour it into a sterile petri dish to make a flat culture medium with medicine. The same amount of solvent, namely 5% DMSO, was used as a blank control, and the commercially available antibacterial drug kresoxim-methyl was used as a positive control.

[0100] Use a hole puncher with a diameter of 5mm to take out the bacteria cake of watermelon wilt pathogen growing vigorously at the edge of the colony, transfer it to the above-mentioned flat culture medium with an inoculation needle, and paste it on the culture medium with the mycelium side facing down, 3 pieces per dish , placed in the center in a triangular shape, covered and cultured ...

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Abstract

The invention relates to beta-carbonyl enamine compounds and application for preparing a phytopathogen antibacterial agent. With commercially available antibacterial agent kresoxim-methyl as positive control, a hypha linear growth rate method is adopted for measuring inhibitory activity of the 23 target compounds to five kinds of common phytopathogen including apple anthracnose pathogenic bacteria, maize curvularia pathogenic bacteria, rice blast pathogenic bacteria, wheat scab pathogenic bacteria and watermelon wilt pathogenic bacteria, and the result shows that the target compounds have different degrees of inhibiting effects on test bacteria. The activity of the compounds 8, 11, 12, 14 and 16 is good, and EC50 values, namely, half effect concentration of the compounds to multiple kinds of tested pathogenic bacteria are higher than that of the positive control medicine kresoxim-methyl. Particularly, the inhibitory activity (EC50=2.15 microgram / mL) of the compound 8 to the apple anthracnose pathogenic bacteria and the inhibitory activity (EC50=9.14 microgram / mL) of the compound 12 are over eight times higher than the inhibitory activity (EC50=15.45-76.06 microgram / mL) of kresoxim methyl, and the compounds have potential development and application value.

Description

1. Technical field: [0001] The invention relates to a class of compounds with a novel structure that can inhibit the growth of plant pathogenic bacteria, in particular to a β-carbonyl enamine compound and its application as an antibacterial agent for plant pathogenic bacteria. 2. Background technology: [0002] Agriculture is the foundation of our country's national economy. However, plant diseases have brought incalculable losses to agricultural production in our country and the world. Therefore, effective prevention and control of them is one of the fundamental measures to ensure efficient agricultural production and steady development. The current The main means of control is the widespread use of pesticides. Therefore, the research and development of pesticides with my country's independent intellectual property rights has extremely important strategic significance for the development of my country's agriculture and even the national economy. The research and developmen...

Claims

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Application Information

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IPC IPC(8): C07C225/16C07C221/00C07D307/52C07D333/22A01N35/04A01N43/08A01N43/10A01P3/00
Inventor 耿会玲于新池逯嫒琳曹浩强周博航赵忠
Owner NORTHWEST A & F UNIV
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