Pyrilamine compounds with herbicidal activity and application thereof

A technology of pyrimidine amines and compounds, which is applied in the field of pyrimidine amines and can solve problems such as herbicides having no research effect

Inactive Publication Date: 2014-11-12
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Patents WO2011 / 121418A9, JP2008534472, CA2551944, and US2008 / 0275064A1 disclose the application of pyrimidine amine derivatives as adenosine A2a receptor antagonists in medicine, but their effects have not been studied in terms of herbicides

Method used

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  • Pyrilamine compounds with herbicidal activity and application thereof
  • Pyrilamine compounds with herbicidal activity and application thereof
  • Pyrilamine compounds with herbicidal activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the preparation of intermediate 3-trifluoromethyl-5 methylpyrazole

[0022]

[0023] Add 1.57g (10mmol, 98%) of 1,1,1-trifluoro-2,4-pentanedione and 0.42g (10.5mmol, 80%) of hydrazine hydrate into 60mL of ethanol, reflux for 6h, and stop the reaction , concentrated under reduced pressure to leave about 10mL of solvent, left to stand, crystallized, and the solid was recrystallized with 95% ethanol to obtain the target compound. Dry to obtain 1.20 g of white solid, yield 80%, melting point 88-90 ° C, IR (KBr, cm -1 )ν: 3256(NH), 2943(CH 3 ), 1594 and 1485 (pyrazolyl); 1 H NMR (CDCl 3 ,300MHz):2.35(s,3H,CH 3 ), 6.30 (s, 1H, pyrazole-4H).

Embodiment 2

[0025] Intermediate 4-amino-6-chloropyrimidine preparation of

[0026] Add 2.98g (20mmol) of 4,6-dichloropyrimidine and 10mL DMF to a 100mL two-necked bottle, stir to dissolve, then add 40mL concentrated ammonia water to react at 30°C, follow the reaction process by TLC, and stop the reaction when no more products are formed. Then add 40mL of ice water, let it stand still, a large amount of crystals are precipitated, filter, wash with water, and dry to obtain 2.04g of milky white solid product 4-amino-6-chloropyrimidine, melting point 208-210°C, yield 78.8%, IR (KBr tablet, cm -1 ): 3313 (NH 2 ), 3134 (NH 2 ), 1665, 1583, 1528, 1410, 1347, 1259, 1086, 989, 923, 752. Infrared data indicated that the amino group was attached.

Embodiment 3

[0027] Embodiment 3: Intermediate 6-chloro-4-methylaminopyrimidine preparation of

[0028] Add 2.98g (20mmol) of 4,6-dichloropyrimidine and 40mL of ethanol to a 100mL two-necked bottle with a reflux condenser and a tail gas absorption device, stir to dissolve, then add 1.62g (24mmol) of methylamine hydrochloride and 3.35 mL (24mmol) triethylamine, heated to reflux, when TLC monitors that no more products are produced, stop the reaction, cool, pour the reaction solution into a 100mL round bottom flask, desolvate under reduced pressure, a large amount of white solid appears, add a small amount of water, Filtered, washed 3 times with a small amount of water, suction filtered, and dried to obtain 2.13 g of white solid product 6-chloro-4-methylaminopyrimidine, melting point: 136-138 ° C, yield 74.2%, IR (KBr tablet, cm -1 ): 3264 (b, NH), 2930, 1601, 1130, 972, 848.

[0029]

[0030] Intermediates 6-chloro-4-N, N-dimethyl-pyrimidinyl-4-amine, 6-chloro-N-ethyl-pyrimidinyl-4-am...

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Abstract

The invention relates to the technical field of herbicides and in particular discloses pyrilamine compounds with herbicidal activity and application thereof. The pyrilamine compounds with the herbicidal activity are the compounds represented by a general formula. In the specification, six compounds are particularly disclosed. The test result shows that the compounds represented by the general formula have good herbicidal activity, especially for gramineous weeds; and through using the compounds, crab grass, barnyard grass, Chinese pennisetum and the like suffer from albefaction so that the roots can not normally grow to be died. Thus, the compounds represented by the general formula are expected to serve as the herbicides in the fields of agriculture and others.

Description

technical field [0001] The invention relates to the technical field of herbicides, in particular to a pyrimidine amine compound with herbicide activity and an application thereof. Background technique [0002] Patents WO2011 / 121418A9, JP2008534472, CA2551944, and US2008 / 0275064A1 disclosed the medical application of pyrimidine amine derivatives as adenosine A2a receptor antagonists, but did not study their effects on herbicides. There are still structural differences between the compounds disclosed in the above patents and the compounds of the general formula with herbicidal activity proposed by the present invention. Contents of the invention [0003] In order to meet the requirements of agricultural development and address the deficiencies in the prior art, the object of the present invention is to provide a new pyrimidine amine derivative and its application in agriculture to prevent and control weeds and the composition of these compounds. Instructions. The pyrimidin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04A01N43/54A01P13/00
Inventor 马洪菊张建华李建洪陈长水夏向东许孟涵
Owner HUAZHONG AGRI UNIV
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