5-Substituent-1,2,4-triazole-thione Schiff base compound and preparation method and application thereof

A technology of substituents and Schiff bases, which is applied in the field of chemical drugs, can solve the problems of drug side effects, increased drug resistance, increased drug toxicity, and high toxicity, and achieve broad-spectrum high-efficiency bactericidal activity, reduced drug concentration, and high toxicity. Effect with few side effects

Active Publication Date: 2022-03-04
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] With the extensive use of 1,2,4-triazole drugs, the toxic side effects and drug resistance of certain crops have increased significantly, so that the bacterial resistance to antibiotics has increased, and the amount of drugs used will continue to increase, which is bound to increase. Lead to increased drug toxicity, more drug residues on crops, great toxicity to the human body and the environment, seriously affecting human health, and causing extreme environmental pollution

Method used

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  • 5-Substituent-1,2,4-triazole-thione Schiff base compound and preparation method and application thereof
  • 5-Substituent-1,2,4-triazole-thione Schiff base compound and preparation method and application thereof
  • 5-Substituent-1,2,4-triazole-thione Schiff base compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0052] Examples 1-3 use intermediate (I) to synthesize 5-substituent-1,2,4-triazole-thione Schiff base compound

Embodiment 1

[0053] Preparation and characterization of embodiment 1 compound TM1

[0054] Synthesis of 4-(3,5-Dimethyl-4-hydroxybenzylideneamino)-5-methyl-2H-1,2,4-triazole-3(4H) by Intermediate (Ⅰ-1) - Thione (Compound TM1). The preparation method comprises the following steps:

[0055] (1) Synthesis of 4-amino-5-methyl-2H-1,2,4-triazole-3(4H)-thione intermediate (I-1)

[0056] Complete through the following synthetic routes, specifically:

[0057]

[0058] (2) Synthesis of 5-methyl-2H-1,2,4-triazole-3(4H)-thione Schiff base compound TM1

[0059] Complete through the following synthetic routes, specifically:

[0060]

[0061] In summary, the specific steps of using intermediate (I-1) to synthesize compound TM1 are as follows:

[0062] Weigh 141 mmol of thiocarbazide, add excess acetic acid to carry out nucleophilic substitution reaction, filter the solution obtained from the reaction, wash, and recrystallize to obtain intermediate (I-1);

[0063] The above-mentioned intermedi...

Embodiment 2

[0068] Preparation and characterization of embodiment 2 compound TM2

[0069] Compound TM2 was synthesized using intermediate (I-2).

[0070] The preparation method of compound TM2 can refer to the preparation method of TM1 in Example 1. But different from Example 1, the fatty acid used is propionic acid, and the yield of compound TM2 is 71.2%.

[0071] Further, the properties of compound TM2 were characterized.

[0072] The melting point of compound TM2 is determined to be 218.1-219.6°C, and it is detected by nuclear magnetic resonance to obtain 1 H NMR spectrum, such as figure 2 shown.

[0073] see figure 2 , 1 H NMR (400MHz, DMSO-d 6 ,ppm)δ13.69(s,1H,NH),9.49(d,J=5.4Hz,1H,OH),9.21(d,J=5.1Hz,1H,CH=N),7.49(d,J= 4.8Hz,2H,benzene),3.39(s,3H,CH 3 ),2.98-2.56(m,2H,CH 2 ), 2.23 (d, J=5.1Hz, 6H, CH 3 );IR(KBr,cm -1 ): ν: 3408(N-H), 3062(OH), 1574(C=N); Anal.Calcd(%) for C 13 h 16 N 4 OS (276.36): C, 56.50; H, 5.84; N, 20.27. Found: C, 56.43; H, 5.45; N, 20.20.

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Abstract

The invention belongs to the technical field of chemical medicines, and relates to a 5-substituent-1,2,4-triazole-thione Schiff base compound and its preparation method and application. Intermediate (I) or intermediate (II) ) respectively reacted with 3,5-dimethyl-4-hydroxybenzaldehyde in glacial acetic acid under reflux, filtered, and dried to obtain 5-substituent-1,2,4-triazole-thione Schiff base compounds. The present invention introduces the active group—imine group into the triazole ring parent body, and prepares and synthesizes a series of triazole Schiff base compounds with multiple active sites, which have good activity, less dosage, less toxic and side effects, and are safe Environmental protection; at the same time, this type of compound can be used as an antifungal drug for crops, which can affect the synthesis of fungal cell walls, thereby inhibiting the growth and proliferation of fungi, and finally play the role of antibacterial or bactericidal.

Description

technical field [0001] The invention belongs to the technical field of chemicals and medicines, and relates to a 5-substituent-1,2,4-triazole-thione Schiff base compound and a preparation method and application thereof. Background technique [0002] Heterocyclic compounds play an important role in the field of pesticides, especially the compounds represented by triazole heterocyclic derivatives have attracted many researchers because of their high efficiency, spectrum and other biological properties, as well as anti-tumor, anti-bacterial, anti-inflammatory and other pharmacological properties. s concern. Schiff bases are a class of compounds containing imine groups, which are widely used in the fields of organic synthesis, catalysis, and biology. The presence of imine groups in their structures makes them have a wide range of biological activities such as antifungal and antibacterial. [0003] With the extensive use of 1,2,4-triazole drugs, the toxic side effects and drug r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12A01N43/653A01P3/00
CPCC07D249/12A01N43/653
Inventor 任莹辉齐乐李谋翠杨斌
Owner NORTHWEST UNIV
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