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1,2,4-triazolethione derivative containing (hetero)aryl group and piperazine, preparation method and application

A technology of triazolethione and its derivatives, which is applied in 1 field, and can solve the problems that the inhibitory activity of bactericidal ARI enzyme has not been disclosed, etc.

Active Publication Date: 2018-05-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, the preparation of 1,2,4-triazolethione derivatives containing (hetero)aryl and piperazine as shown in the present invention and their bactericidal and ARI enzyme inhibitory activities have not been disclosed

Method used

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  • 1,2,4-triazolethione derivative containing (hetero)aryl group and piperazine, preparation method and application
  • 1,2,4-triazolethione derivative containing (hetero)aryl group and piperazine, preparation method and application
  • 1,2,4-triazolethione derivative containing (hetero)aryl group and piperazine, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of compound 15

[0031] Step A: Preparation of 5-(furan-2-yl)-1,3,4-oxadiazole-2-thiol

[0032]

[0033] Add 9.00g (71.4mmol) of 2-furyl hydrazide and 300mL of absolute ethanol to a 500mL round bottom flask, and add 21.66g (285.5mmol) of CS 2 And 4.00g (71.4mmol) KOH, remove the ice bath after the addition is complete, and heat to reflux for 7h. Cool to room temperature and spin off the solvent, add an appropriate amount of water to dissolve the residue, adjust the pH to 2-3 with hydrochloric acid, stir for 2 hours, filter with suction, recrystallize with ethanol, and dry to obtain 9.36 g of white solid with a yield of 78%.

[0034] Step B: Preparation of 4-amino-5-(furan-2-yl)-4H-1,2,4-triazole-3-thiol

[0035]

[0036]In the 100mL round bottom flask, add 8.90g (52.9mmol) 5-(furan-2-yl)-1,3,4-oxadiazole-2-thiol, 17.00g (264.6mmol) hydrazine hydrate (80%) and 30mL of absolute ethanol, stirred and heated to reflux for 7h. Cool to room tem...

Embodiment 2

[0044] The preparation method of compound 23

[0045] Step A: Preparation of 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-thiol

[0046]

[0047] Add 17.00g (123.9mmol) 3-pyridinecarbohydrazide and 100mL absolute ethanol to a 250mL round bottom flask, and add 37.83g (324.3mmol) CS 2 And 6.93g (123.9mmol) KOH, remove the ice bath after the addition is complete, and heat to reflux for 10h. Cool to room temperature and spin off the solvent, dissolve the residue in water and adjust the pH to 2-3 with hydrochloric acid, stir for 2 h, filter with suction, recrystallize with ethanol, and dry to obtain 9.10 g of white solid, yield 41%.

[0048] Step B: Preparation of 4-amino-5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiol

[0049]

[0050] Add 8.75g (55.8mmol) 5-(pyridin-3-yl)-1,3,4-oxadiazole-2-thiol in 250mL round bottom flask, 20.95g (334.8mmol) hydrazine hydrate (80%) and 100mL absolute ethanol, heated to reflux for 12h. Cool to room temperature and spin off the solvent, dissolve the ...

Embodiment 3

[0058] Preparation method of compound 34.

[0059] Step A: Preparation of 5-phenyl-1,3,4-oxadiazole-2-thiol

[0060]

[0061] Add 19.00g (139.6mmol) of benzohydrazide and 100mL of absolute ethanol to a 250mL round bottom flask, and add 42.43g (558.2mmol) of CS 2 And 7.81g (139.6mmol) KOH, remove the ice bath after the addition is complete, and heat to reflux for 7h. Cool to room temperature and spin off the solvent, add an appropriate amount of water to dissolve the residue, adjust the pH to 2-3 with hydrochloric acid, stir for 2 hours, filter with suction, and recrystallize from ethanol to obtain 18.16 g of white solid with a yield of 73%.

[0062] Step B: Preparation of 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol

[0063]

[0064] Add 30.00g (168.3mmol) 5-phenyl-1,3,4-oxadiazole-2-thiol, 80.00g (1.3mol) hydrazine hydrate (80%) and 100mL absolute ethanol to a 250mL round bottom flask, Stirring and heating at reflux for 6h. Cool to room temperature and spin off the so...

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Abstract

The invention discloses a 1,2,4-triazolethione derivative containing a (hetero)aryl group and piperazine, and a preparation method and an application thereof. The synthesis method has the advantages of few reaction steps, simple and mild conditions, simple operation and high yield. The derivative has a structural formula represented by general formula I and general formula II, and R<1>, R<2> and R<3> in the general formula I and the general formula II are as defined in claim 1. The above compounds have certain in vitro inhibition activity to cucumber fusarium wilt, Cercospora arachidicola Hori, Macrophoma kawatsukai, Altemaria solani, Fusarium graminearum, Rhizoctonia cerealis and other plant pathogens, and especially have high in vitro inhibition activity on the cucumber fusarium wilt, Cercospora arachidicola Hori, Macrophoma kawatsukai and Rhizoctonia cerealis. The compounds of the general formula I and general formula II simultaneously have rice KARI enzyme in vitro inhibition activity. The derivative is suitable for comprehensive control of fungus damages on various crops.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, and relates to a preparation method and application of 1,2,4-triazolethione derivatives containing (hetero)aryl and piperazine. Background technique [0002] The prevention and control of plant pathogens is one of the important topics in the realization of various industries such as agriculture, forestry, animal husbandry, sideline, fishery and public health. With the deepening of people's awareness of environmental protection, some old pesticides that pollute the environment, kill beneficial organisms, produce drug resistance, and are difficult to degrade are gradually being eliminated. The direction of new pesticide creation in the future will be to develop low-toxic and efficient green pesticides and environmentally friendly type pesticides. Among them, heterocyclic compounds have become the focus of current pesticide development due to their good efficacy, low dosage, easy degradation,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D401/14C07D403/12C07D405/14A01N43/653A01P3/00
CPCA01N43/653C07D401/14C07D403/12C07D405/04C07D405/14
Inventor 王宝雷李正名张丽媛张燕张晓
Owner NANKAI UNIV