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Thioether compounds containing pyrimidine, thiadiazole ring and amide structures and application thereof

A technology of thiadiazole rings and compounds, which is applied in the field of thioether compounds, can solve the problems of structure and biological activity that have not been reported in literature, and achieve the effect of simple preparation and good antibacterial activity

Inactive Publication Date: 2016-08-17
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The thioether compound containing pyrimidine, thiadiazole ring and amide structure designed and synthesized by the present invention has no literature report on its structure and biological activity research

Method used

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  • Thioether compounds containing pyrimidine, thiadiazole ring and amide structures and application thereof
  • Thioether compounds containing pyrimidine, thiadiazole ring and amide structures and application thereof
  • Thioether compounds containing pyrimidine, thiadiazole ring and amide structures and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthesis of embodiment 1 derivative Ia (Rn=o-chloro)

[0031] Synthesis of 5-((4,6-dimethylpyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol: In a 250 mL one-necked flask, weigh 2.60 g KOH (0.045 mol) was slowly added into 100 mL of absolute ethanol with stirring until dissolved, and 0.03 mol of 2-((4,6-dimethylpyrimidin-2-yl)thio)acetylhydrazide was weighed added to the solution. Under the condition of ice bath, slowly add 0.5 mL CS2 (0.045 mol) dropwise, after the dropwise addition, continue to stir at room temperature for 5 h, then filter with suction, wash with ether, and dry to obtain the intermediate. Under ice-bath conditions, in a 50 mL single-necked flask, add 20 mL of concentrated sulfuric acid, slowly add 0.014mol 2-((4,6-dimethylpyrimidin-2-yl)thio)acetylhydrazinodithio Potassium formate, after all the solids are dissolved, stir at room temperature for 2 h, slowly pour the mixture into ice water and stir, a large amount of white solids will appear ...

Embodiment 2

[0036] Example 2 Synthesis of Derivatives Ib (Rn=m-chloro)

[0037] Dissolve 5 mmol of 5-((4,6-dimethylpyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol in NaOH aqueous solution, then add dissolved 5.5 mmol of N-substituted m-chlorophenyl-2-chloroacetamide in 5 mL of absolute ethanol reacted in an alkaline aqueous solution to precipitate a solid product, and finally obtained a white powder after suction filtration, washing, drying, and ethanol recrystallization Like solid, that is, the product. The melting point is 128°C, and the yield is 83.4%.

[0038] of the compound 1 H NMR and IR spectroscopic data are described below,

[0039] 1 H NMR (CDCl 3 ) δ: 9.83 (s, 1H, -NH), 7.71 (s, 1H, Ar-H), 7.39 (s, 1H, Ar-H), 7.25 – 7.18 (m, 1H, Ar-H), 7.07 ( d, J = 7.4 Hz, 1H, Ar-H), 6.86 (s, 1H, CH), 4.76 (s, 2H, CH 2 ), 4.05 (s, 2H,CH 2 ), 2.52 (s, 6H, (CH 3 ) 2 ) ; IR (KBr)ν:3210, 3063, 2917, 1681, 1626, 1596, 1482, 1272, 1071 cm -1 .

Embodiment 3

[0040] Example 3 Synthesis of Derivatives Ic (Rn=Pair Chlorine)

[0041] Dissolve 5 mmol of 5-((4,6-dimethylpyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol in NaOH aqueous solution, then add dissolved 5.5 mmol of N-substituted p-chlorophenyl-2-chloroacetamide in 5 mL of absolute ethanol reacted in an alkaline aqueous solution to precipitate a solid product, and finally obtained a white powder after suction filtration, washing, drying, and ethanol recrystallization Like solid, that is, the product. The melting point is 135-137°C, and the yield is 91.3%.

[0042] of the compound 1 H NMR and IR spectroscopic data are described below,

[0043] 1 H NMR (CDCl 3 ) δ: 9.82 (s, 1H, -NH), 7.50 (d, J = 8.8 Hz, 2H, Ar-H), 7.25(d, J = 8.8 Hz, 2H, Ar-H), 6.80 (s, 1H , CH), 4.71 (s, 2H,CH 2 ), 4.02 (s, 2H,CH 2 ), 2.45 (s, 6H, (CH 3 ) 2 ) ; IR (KBr)ν: 3201, 3045, 2914, 1692, 1584, 1488, 1269, 1066 cm -1 .

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Abstract

The invention relates to thioether compounds containing pyrimidine, thiadiazole ring and amide structures and an application thereof; the bactericidal activity of the compounds on colletotrichum orbiculare, botrytis cinerea and rhizoctonia solani are measured, and the general screening concentration is 50 mg / L; measurement results indicate that the compounds (I) having nonsubstituted H in a benzene ring show a certain inhibitory activity on all the tested strains; the compounds Ia (Rn=p-chloro), Id (Rn=o-methyl), Ie (Rn=m-methyl) and If (Rn=p-methyl) have all the inhibition rates on colletrichum orbiculare of more than or equal to 50%, wherein the inhibition rate of the Ie is 77.31%; the compounds Id (Rn=o-methyl), Ie (Rn=m-methyl) and If (Rn=p-methyl) have all the inhibition rates on botrytis cinerea of more than or equal to 50%, wherein the inhibition rate of the Ie is more than 60%; the compounds Id (Rn=o-methyl) and Ie (Rn=m-methyl) have the inhibition rates on rhizoctonia solani of more than or equal to 40%.

Description

technical field [0001] The invention relates to thioether compounds containing pyrimidine, thiadiazole ring and amide structure and application thereof. Background technique [0002] Compounds containing a pyrimidine ring have a wide range of biological activities, such as insecticidal (Chem. Res. Chin. Univ., 2002, 18(4): 481), herbicidal (Pestic. Biochem. Physiol., 2001, 70(2): 86), bactericidal (Tetrahedron, 2000, 56(27): 4739) and other activities play an important role in the creation of new pesticides. Thioether structure compounds are also widely used in the field of pesticides and medicines, such as insecticide (US 4206235, 1980-06-03), anti-tumor (Chin. J. Struct. Chem., 2003, 22: 411), anti- Virus (Eur. J. Med. Chem., 2003, 38:811) and other activities. In addition, amide compounds also have a wide range of biological activities, such as herbicide (Organic Chemistry, 2011, 3(31): 317~323), bactericide (JP 7285942, 1995-10-31), acaricide (JP, 2005060255, 2005 -03...

Claims

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Application Information

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IPC IPC(8): C07D403/12A01N43/824A01P3/00
CPCA01N43/82C07D403/12
Inventor 翁建全朱亚波阮铃莉许萌沈振陆
Owner ZHEJIANG UNIV OF TECH
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