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N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant as well as preparation and application thereof

A technology of pyrimidinyl thiourea and pyridine acyl group, which is applied to N-substituted pyridine acyl-N-substituted pyrimidinyl thiourea derivatives and the fields of preparation and application thereof, and can solve problems such as strong toxicity

Active Publication Date: 2010-10-06
徐州佳兆农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But it was banned for being too toxic

Method used

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  • N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant as well as preparation and application thereof
  • N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant as well as preparation and application thereof
  • N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant as well as preparation and application thereof

Examples

Experimental program
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Effect test

example 1

[0046] Example 1: Preparation of N-pyrimidinyl-N-nicotinoylthiourea

[0047] In a 100mL round bottom flask, add 0.97g (10mmol) of NH in a solution of 10mmol of nicotinoyl chloride dissolved in 20mL of dichloromethane 4 PEG-600 solution of dichloromethane in NCS (10mL, including 9.5mL of dichloromethane and 0.5mL of PEG-6000), stirred and refluxed for 15min, left to cool, and filtered with suction to obtain an orange solution, which was added with 10mmol 2 - A solution of aminopyrimidine dissolved in 5 mL of anhydrous acetonitrile, stirred at room temperature for 10 h, allowed to stand overnight, filtered with suction, and the filter cake was recrystallized with a mixed solvent of DMF and water at a volume ratio of 1:1 to obtain the product.

[0048] Yellow solid, yield 42.3%, melting point 185-186°C; 1 H NMR (DMSO-d 6 )δ: 7.21-9.06 (m, 6H, Py and ph), 12.26 (s, 1H, NH), 13.36 (s, 1H, NH); IR / cm -1 : 3420(N-H), 3167(N-H), 1718(C=O), 1554, 1452(Ar), 1263(C=S); ESI-MS: 258; El...

example 2

[0049] Example 2: Preparation of N-4-methylpyrimidinyl-N-nicotinoylthiourea

[0050] In a 100mL round bottom flask, add 0.97g (10mmol) of NH in a solution of 10mmol of nicotinoyl chloride dissolved in 20mL of dichloromethane 4 NCS dichloromethane PEG-600 solution (10mL, including 9.5mL dichloromethane, PEG-6000.5mL), stirred and refluxed for 15min, left to cool, and suction filtered to obtain an orange solution, which was added with 10mmol of 2-amino - A solution of 4-methylpyrimidine dissolved in 5 mL of anhydrous acetonitrile, stirred at room temperature for 10 h, allowed to stand overnight, filtered with suction, and the filter cake was recrystallized with a mixed solvent of DMF and water at a volume ratio of 1:2 to obtain the product.

[0051] Yellow solid, yield 55.83%, melting point 192-194°C; 1 H NMR (DMSO-d 6 )δ: 2.43(s, 3H, CH 3 ), 7.22-9.15 (m, 6H, Py and ph), 11.88 (s, 1H, NH), 13.98 (s, 1H, NH) IR / cm -1: 3417(N-H), 3125(N-H), 1703(C=O), 1550, 1450(Ar), 1261(C=S...

example 3

[0052] Example 3: Preparation of N-pyrimidinyl-N-2-chloronicotinoylthiourea

[0053] In a 100mL round bottom flask, add 0.97g (10mmol) of NH in a solution of 10mmol of 2-chloronicotinyl chloride dissolved in 20mL of acetonitrile 4 NCS dichloromethane PEG-600 solution (10mL, including 9.5mL dichloromethane, PEG-6000.5mL), stirred and refluxed for 15min, left to cool, and suction filtered to obtain an orange solution, which was added with 10mmol of 2-amino Dissolve pyrimidine in 10 mL of anhydrous acetonitrile, stir at room temperature for 10 h, let stand overnight, filter with suction, take the filter cake and recrystallize with a mixed solvent of DMF and water at a volume ratio of 2:1 to obtain the product.

[0054] Yellow solid, yield 65.87%, melting point 190-191°C; 1 H NMR (DMSO-d 6 )δ: 7.22-8.98 (m, 6H, Py-H and ArH,), 12.34 (s, 1H, NH), 13.21 (s, 1H, NH); IR / cm -1 : 3425(N-H), 3157(N-H), 1720(C=O), 1548, 1450(Ar), 1264(C=S); ESI-MS: 292; Elemental analysis for C 11 h ...

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Abstract

The invention discloses an N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant, a preparation method thereof and application of the N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant as a bactericide. The invention provides a new N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant, as well as the preparation method and the application thereof. The provided N-substituted pyridine acyl-N-substituted pyrimidyl thiourea derivant has excellent bactericidal activity.

Description

(1) Technical field [0001] The invention relates to an N-substituted pyridinoyl-N-substituted pyrimidinylthiourea derivative and its preparation method and application. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. Pyridine and pyrimidine compounds are a category that has developed rapidly in recent years, and many commercial insecticides, fungicides, and herbicides belong to this category. For example, the ultra-high-efficiency herbicide chlorimuron-methyl developed by DuPont is used for weeding in soybean fields and has high killing ability; the pyridine fungicide boscalid developed by BASF is a succinate coenzyme in the mitochondrial respiratory chain. Q reductase inhibitor, has a strong inhibitory ability to spore germination. [0003] Thiourea compounds have various biological activities. Many literatures repo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12A01N47/36A01P3/00
Inventor 刘幸海谭成侠翁建全
Owner 徐州佳兆农业科技有限公司
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