1,2,4-triazole mannich base derivatives containing substituted piperazidine, and preparation method and application thereof

A derivative, piperazine technology, applied in botany equipment and methods, chemicals for biological control, applications, etc., can solve the problems of preparation of bactericidal and herbicidal activities that have not been disclosed, and achieve good living control effect, high The effect of bactericidal activity and high in vitro inhibitory activity

Inactive Publication Date: 2015-02-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the preparation of some antibacterially active heterocyclic Mannich base compounds has been reported (CN103288816, CN102276555), in the prior art, as shown in the present i

Method used

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  • 1,2,4-triazole mannich base derivatives containing substituted piperazidine, and preparation method and application thereof
  • 1,2,4-triazole mannich base derivatives containing substituted piperazidine, and preparation method and application thereof
  • 1,2,4-triazole mannich base derivatives containing substituted piperazidine, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation method of compound 17.

[0027] Step A: Preparation of (E)-5-methyl-4-((thiophene-2-methylene)amino)-4H-1,2,4-triazole-3-thiol

[0028]

[0029] Add 5.2g (0.04mol) 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol and 5.1g (0.045mol) 2-thiophenecarbaldehyde to a 100mL round bottom flask, add 30mL of Dissolve it in absolute ethanol, then add 7-8 drops (about 0.5 mL) of glacial acetic acid dropwise, and heat to reflux for 5 hours. After cooling to room temperature, crystals were precipitated, filtered with suction, washed with a small amount of ethanol, and dried to obtain 5.46 g of brown crystals, with a yield of 61.2%.

[0030] Step B: Preparation of (E)-5-methyl-2-((4-phenylpiperazin-1-yl)methyl)-4-((thiophene-2-methylene)amino)-2,4 -Dihydro-3H-1,2,4-triazole-3-thione (compound 17)

[0031]

[0032] In a 50 mL round bottom flask, add 0.336 g (1.5 mmol) of (E)-5-methyl-4-((thiophene-2-methylene)amino)-4H-1,2,4-triazole-3 -thiol, 0.243g (1.5mmol) phenylpip...

Embodiment 2

[0034] Preparation method of compound 29.

[0035] Step A: Preparation of (E)-4-(((5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methylene)amino)-5-methyl-4H-1, 2,4-triazole-3-thiol

[0036]

[0037] Add 1.30g (0.01mol) 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol and 1.59g (0.01mol) 5-chloro-1,3- Add 12 mL of glacial acetic acid to dimethyl-1H-pyrazole-4-carbaldehyde, and heat to reflux for 1 hour. Cool to room temperature, filter with suction, wash with a small amount of ethanol, and dry to obtain 2.37 g of white solid, with a yield of 87.6%.

[0038] Step B: Preparation of (E)-2-((4-benzylpiperazin-1-yl)methyl)-4-(((5-chloro-1,3-dimethyl-1H-pyrazole-4 -yl)methylene)amino)-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (compound 29)

[0039]

[0040]In a 50 mL round bottom flask, add 0.27 g (1 mmol) (E)-4-(((5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methylene)amino)- 5-methyl-4H-1,2,4-triazole-3-thiol, 0.176g (1mmol) benzylpiperazine, 20mL N,N-dimethylformamide, and finally 0....

Embodiment 3

[0042] Preparation method of compound 45.

[0043] Step A: Preparation of (E)-4-(((5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)amino)-5-methyl-4H- 1,2,4-triazole-3-thiol

[0044]

[0045] Add 1.30g (0.01mol) 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol and 2.21g (0.01mol) 5-chloro-3-methyl to 100mL round bottom flask -1-Phenyl-1H-pyrazole-4-carbaldehyde, add 20mL of glacial acetic acid, and heat to reflux for 5 hours. Cool to room temperature, filter with suction, wash with a small amount of ethanol, and dry to obtain 3.11 g of white solid with a yield of 93.5%.

[0046] Step B: Preparation of (E)-4-(((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)amino)-5-methyl-2- ((4-(4-methylpyrimidin-2-yl)piperazin-1-yl)methyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (compound 45)

[0047]

[0048] In a 50 mL round bottom flask, add 0.30 g (0.9 mmol) of (E)-4-(((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene) Amino)-5-methyl-4H-1,2,4-triazole-3-thiol, 0.160g...

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Abstract

The invention discloses 1,2,4-triazole Mannich base derivatives containing substituted piperazidine, and a preparation method and application thereof. The structural formulae of the 1,2,4-triazole Mannich base derivatives containing substituted piperazidine are disclosed as general formulae I and II, wherein X, Y and Z are defined as Claim 1. The compounds have high bactericidal activity, have high in-vitro inhibition activity for ring rot of apple, sheath blight of wheat, scab of wheat, early blight of tomato and other plant pathogens, have favorable in-vivo control effects on corynespora leaf spot of cucumber, bacterial spot of cucumber, gummy stem blight of cucumber, downy mildew of cucumber, sclerotinia rot of cucumber and other plant fungi, and especially have special effects for bacterial spot of cucumber and Pseudoperonospora cubensis Rostov. The compounds disclosed as general formula I and general formula II have weeding activity. The 1,2,4-triazole Mannich base derivatives are suitable for integrated control of fungus attack and crop smothering on various crops.

Description

technical field [0001] The invention belongs to the field of agricultural bactericides and herbicides, and relates to the preparation and application of two types of heterocyclic compounds, in particular to the preparation method and application of two types of 1,2,4-triazole Mannich base derivatives containing substituted piperazine. Background technique [0002] The control of plant pathogens and weeds is very important in the realization of various industries such as agriculture, forestry, animal husbandry, sideline, fishery and public health. As people pay more and more attention to environmental issues, scientists need to continue to carry out innovative research, and then develop new pesticide varieties with high efficiency, low toxicity, safety and different modes of action. [0003] Heterocyclic compounds have a very wide range of pharmaceutical and pesticide biological activities and application values. In the field of pesticides, heterocyclic compounds account for...

Claims

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Application Information

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IPC IPC(8): C07D409/12C07D403/12C07D403/14C07D401/14A01N43/653C07D405/12C07D405/14C07D409/14A01P13/00A01P3/00A01P1/00
CPCC07D409/12A01N43/653C07C403/12C07C403/14C07C409/14C07D401/14C07D405/12C07D405/14
Inventor 王宝雷李正名詹益周张丽媛张晓李宝聚石延霞李永红
Owner NANKAI UNIV
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