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Poly-substituted miazines compound, preparation method and application thereof

A compound and multi-substitution technology, which is applied in the field of multi-substituted pyrimidine compounds and its preparation, can solve the problems of plant virus disease prevention and control, plants without immune metabolism system, etc.

Inactive Publication Date: 2009-11-18
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since viruses are obligately parasitic in plant cells, the substances, energy and places required for their replication are completely dependent on the host, and plants do not have a complete immune and metabolic system, making the prevention and treatment of plant virus diseases particularly difficult

Method used

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  • Poly-substituted miazines compound, preparation method and application thereof
  • Poly-substituted miazines compound, preparation method and application thereof
  • Poly-substituted miazines compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] 1-(2-(Diethylamine)-4-methyl-6-(4-phenoxyphenoxy)-5-pyrimidinyl)-3-(4-methoxyphenyl)thiourea

[0090]

[0091] Its preparation process is as follows:

[0092] Step A: N,N-Diethyl-4-methyl-5-nitro-6-(4-phenoxyphenoxy)pyrimidin-2-amine

[0093] Dissolve 0.4g of 4-chloro-N,N-diethyl-6-methyl-5-nitropyrimidin-2-amine in 20mL of anhydrous benzene, add 0.37g of 4-phenoxyphenol, 0.1g of sodium hydride , stirred at room temperature for 12 hours, evaporated to remove benzene, washed with water and dried to obtain 0.55 g of the expected product with a yield of 85%.

[0094] Step B: N 2 , N 2 -Diethyl-4-methyl-6-(4-phenoxyphenoxy)pyrimidine-2,5-diamine

[0095] Dissolve 2 g of the product obtained in step A in 70 mL of ethanol, and reduce it by hydrogenation at normal temperature and pressure under the catalyst of 0.5 g of Raney Ni. After reacting for 30 hours, the catalyst was filtered off and the solvent was distilled off to obtain 1.85 g of the expected product with a y...

Embodiment 2

[0103] 1-(4-(Diphenyl-4-oxo)-2-(diethylamine)-6-methyl-5-pyrimidinyl)-3-o-tolylthiourea

[0104]

[0105] The preparation steps are basically the same as in Example 1. 4-Phenylphenol was used as a reactant in Step A and 1-isothiocyanato-2-methylbenzene was used as a reactant in Step C.

[0106] The final product is a white solid:

[0107] 1 H NMR (CDCl 3 )(ppm): 7.19~7.61(15H, m), 3.36~3.59(4H, m), 2.38(6H, m), 1.02~1.16(6H, m)

[0108] MS: 498.3 (M-1 + ), 520.3 (M-1+Na + )

[0109] IR: 2960, 1608, 1403, 1210

Embodiment 3

[0111] 1-(4-(Diphenyl-4-oxo-)-2-(diethylamine)-6-methyl-5-pyrimidinyl)-3-(4-methoxyphenyl)thiourea

[0112]

[0113] The preparation steps are basically the same as in Example 2. In Step C 1-isothiocyanato-4-methoxybenzene is used as a reactant.

[0114] The final product is a white solid:

[0115] 1 H NMR (CDCl 3 )(ppm): 6.91~7.61(13H, m), 3.80(3H, s), 3.36~3.58(4H, dm), 2.36(3H, s), 1.01~1.17(6H, m)

[0116] MS: 512.1

[0117] IR: 2960, 1608, 1519, 1249, 842, 759, 693

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Abstract

The invention discloses a poly-substituted miazines compound having anti-plant virus activity, a preparation method and application thereof. The structure of the poly-substituted miazines compound is shown in formula (I). Experiments prove that the poly-substituted miazines compound has remarkable effect of growth inhibition to the tobacco mosaic virus, so that the compound can be made into antiviral agents with different concentrations and types according to the actual production and be applied to agricultural industry.

Description

technical field [0001] The invention relates to a class of compounds and a preparation method, in particular to a class of multi-substituted pyrimidine compounds with anti-plant virus activity and a preparation method. Background technique [0002] Plant virus disease is known as "plant cancer". The proportion of plant diseases is second only to fungal diseases, and it poses a serious threat to agricultural production. It is estimated that the annual loss caused by tobacco mosaic virus (Tobacco mosaic virus, TMV) in the world is more than 100 million US dollars. Since viruses are obligately parasitic in plant cells, the materials, energy and places required for their replication are completely dependent on the host, and plants do not have a complete immune metabolism system, making the prevention and treatment of plant virus diseases particularly difficult. In order to effectively prevent and treat plant virus diseases, many schemes have been put forward to try, such as usi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/48C07D401/12C07D405/12C07D405/14C07D403/12C07D239/50A01N47/36A01N43/54A01P1/00
Inventor 袁德凯徐伟攀王祖元国丹丹敬静王道全杨新玲
Owner CHINA AGRI UNIV
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