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3-coumarin formic acid compound and its application as preparation of plant pathogenic bacteria antibacterial agent

A technology of pathogenic bacteria and coumarin, applied in the directions of plant growth regulators, applications, fungicides, etc., can solve problems such as serious diseases, and achieve the effects of small molecular weight, short steps and convenient operation.

Active Publication Date: 2021-03-23
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional agricultural control—simple methods such as crop rotation have not been well implemented, making these diseases more and more serious; the current main control method is still the use of chemical pesticides, but the long-term and frequent use of chemical antibacterial agents has led to strong drug resistance of the pathogens , therefore, how to adopt efficient, green and environmentally friendly methods to prevent and control pathogenic fungi is the key to increasing farmers' production and income and protecting the ecological environment

Method used

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  • 3-coumarin formic acid compound and its application as preparation of plant pathogenic bacteria antibacterial agent
  • 3-coumarin formic acid compound and its application as preparation of plant pathogenic bacteria antibacterial agent
  • 3-coumarin formic acid compound and its application as preparation of plant pathogenic bacteria antibacterial agent

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Experimental program
Comparison scheme
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preparation example Construction

[0038] The synthetic route of the preparation 3-coumarin formic acid compounds established by the present invention is as follows:

[0039] (1) Synthesis of 3-coumarin ethyl formate compounds

[0040] Using substituted salicylaldehyde as raw material, under the catalysis of piperidine, it was refluxed with diethyl malonate in absolute ethanol for 2 to 5 hours, and the Knoevnagal condensation reaction occurred, and 14 ethyl 3-coumarin formates were prepared. Esters (A1-A14).

[0041]

[0042] (2) Synthesis of 3-coumarin formic acid compounds

[0043] The 3-coumarin formic acid ethyl ester compound was hydrolyzed under alkaline conditions, and then acidified to obtain the corresponding 3-coumarin formic acid compound (B1-B14).

[0044]

[0045] The specific operation steps of synthesizing different types of 3-coumarin formic acid compounds are as follows:

[0046] 1. Synthesis of compound A1——ethyl 3-coumarin formate

[0047] Add salicylaldehyde (4.9g, 4.3mL, 40mmol), ...

example 1

[0079] In vitro bacteriostatic activity of example 1 compound A5 to apple rot pathogenic fungi

[0080] Accurately weigh 5mg of compound A5 with a 20mL vial, inject 0.5mL of DMSO and 9.5mL of sterile water into it, and make the sample to be tested into a 5% DMSO solution; Mix well, 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.

[0081]Use a hole puncher with a diameter of 5mm to take out the cake of apple rot pathogenic bacteria growing vigorously at the edge of the colony, transfer it to the above-mentioned flat medium with an inoculation needle, and stick it on the medium with the mycelium side facing down, 3 pieces per plate , placed in the center in a triangular shape, covered and cultured in a constant tem...

example 2

[0085] The in vitro bacteriostatic activity of example 2 compound B3 to Curvularia maize pathogenic fungus

[0086] Accurately weigh 5 mg of compound B3 in a 20 mL vial, inject 0.5 mL of DMSO and 9.5 mL of sterile water into it, and prepare the sample to be tested into a 5% DMSO solution; Mix well, 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.

[0087] Use a hole puncher with a diameter of 5 mm to take out the vigorously growing Curvularia cornis pathogenic bacteria cake 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. Blocks were placed in the center in a triangular shape, covered...

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Abstract

The invention relates to a compound with simple structure for inhibiting growth activity of phytopathogens, specifically relates to a 3-coumarin formic acid compound and application of the 3-coumarin formic acid compound as an antibacterial agent for preparing the phytopathogens, and discloses application of the 3-coumarin formic acid compound as the antibacterial agent for preparing the phytopathogens. The two 3-coumarin formic acid compounds has the following characteristics of molecular structure: the formulas are as shown in the specification, wherein R is hydrogen, methyl, methoxyl, hydroxyl, halogen and nitryl. The in vitro inhibitory activity of twenty-eight synthetic target compounds on four common plant pathogenic fungi such as apple decay pathogenic bacteria, apple ring spot pathogenic bacteria, maize curvularia pathogenic bacteria and potato dry rot pathogenic bacteria is measured by adopting a hypha linear growth rate method, so that the condition that all compounds have different inhibiting effects on supplied experimental bacteria is found.

Description

[0001] 1. Technical field: [0002] The invention relates to a class of compounds with simple structure and the activity of inhibiting the growth of plant pathogenic bacteria, in particular to 3-coumarin formic acid compounds and their application as preparation of plant pathogenic bacteria antibacterial agents. [0003] 2. Background technology: [0004] my country is a large agricultural and populous country. The steady development of agriculture is conducive to the sustainable development of the national economy. However, plant diseases not only reduce the yield and quality of agricultural products, but also bring huge losses to agricultural production. Therefore, effective prevention Control is one of the fundamental measures to ensure efficient agricultural production and steady development, and the current main means of prevention and control is the widespread use of pesticides. It can be seen that the research and development of new pesticides with my country's independen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/12C07D311/16C07D311/14A01N43/16A01P3/00
CPCA01N43/16C07D311/12C07D311/14C07D311/16
Inventor 耿会玲史晨燕李浩鹏刘睿媛
Owner NORTHWEST A & F UNIV
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