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2-pyrimidine oxy-n-aryl 7-nitrile or organic phosphate benzylamine compound, its production and use thereof

A phosphate-based benzylamine and pyrimidinyloxy technology, applied in the field of agrochemical herbicides, can solve the problem of limited new varieties of pesticides

Inactive Publication Date: 2006-03-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the new varieties of pesticides with independent intellectual property rights in our country are still very limited. Therefore, it is still a research topic for people to develop and create new varieties of pesticides and take the road of sustainable development.

Method used

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  • 2-pyrimidine oxy-n-aryl 7-nitrile or organic phosphate benzylamine compound, its production and use thereof
  • 2-pyrimidine oxy-n-aryl 7-nitrile or organic phosphate benzylamine compound, its production and use thereof
  • 2-pyrimidine oxy-n-aryl 7-nitrile or organic phosphate benzylamine compound, its production and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The synthesis of 2-pyrimidinyloxy-N-aryl-7-cyanobenzylamine compound is example with (I-1):

[0057] The first step: 12.2 grams (0.1mol) salicylaldehyde, 21.8 grams (0.1mol) 4,6-dimethoxythiamphenicyl pyrimidine, 27.6 grams (0.2 mol) gram potassium carbonate and 150mL DMF, stirred at room temperature for 72 hours, after the reaction was complete (thin-layer chromatography tracking), the reaction mixture was vigorously stirred and poured into 1000mL ice water, and continued to stir for 3 hours, and a large amount of pyrimidine salicylaldehyde was precipitated. Yield 95%.

[0058] The second step: add 13 grams (50mmol) of pyrimidine salicylaldehyde and 5.2 grams (50mmol) of sodium bisulfite in a 100mL three-necked flask with a thermometer, a reflux condenser, and a magnetic stirrer, and add 50mL of acetic acid / water mixed solution (1:4), heated to 40 degrees Celsius, kept for 0.5 hours, after the pyrimidine salicylaldehyde was completely dissolved, 6.85 grams (50 mmol) o...

Embodiment 2

[0068] Synthesis of I-2:

[0069] The detailed experimental procedure is the same as in Example 1: add 4.06 grams (10 mmol) of 2-(4,6 dimethoxy)-pyrimidinyl oxide in a 100 mL three-necked flask with a thermometer, a reflux condenser, a magnetic stirrer and a dropping funnel Base-N-p-benzoyl-7-cyano-benzylamine, 2.82 grams (30mmol) of phenol, 0.122 grams (1mmol) of DMAP and 60mL of 1,2-dichloroethane, dropped into 10mL at 0 degrees Celsius to dissolve 2.26 grams of (11mmol) 1,2-dichloroethane solution of DCC, added in 30 minutes, raised to room temperature and continued to stir for 24 hours after the addition was completed, the reaction was complete (TLC tracking), filtered, and the filtrate was respectively washed with 1N HCl , saturated sodium bicarbonate, washed with saturated brine, dried over sodium sulfate, spin-dried, and separated by column chromatography to obtain a pure product with a yield of 85%.

[0070] solid

[0071] Melting point.: 127.5±0.5℃

[0072] 1 H NMR ...

Embodiment 3

[0078] Synthesis of I-3:

[0079] Add 4.06 grams (10 mmol) of 2-(4,6 dimethoxy)-pyrimidinyloxy-N-p-benzoic acid to a 100 mL three-necked flask with a thermometer, reflux condenser, magnetic stirrer and dropping funnel -7-cyano-benzylamine, 3.16 grams (30 mmol) of p-cresol, 0.122 grams (1 mmol) of DMAP and 60 mL of dichloromethane, stirred, and 10 mL of dichloromethane dissolved in 2.26 grams (11 mmol) of DCC was added dropwise at 0 degrees Celsius Methane solution was added in 30 minutes. After the addition was completed, it was raised to room temperature and continued to stir for 24 hours. The reaction was complete (TLC tracking), filtered, and the filtrate was washed with 1N HCl, saturated sodium bicarbonate, saturated brine, and sodium sulfate. Dried, spin-dried, and separated by column chromatography to obtain a pure product with a yield of 90%.

[0080] solid

[0081] Melting point: 81±1℃

[0082] 1 H NMR (300MHz, CDCl 3 / TMS): δ2.38(3H, s), 3.78(6H, s), 4.60(1H, d, ...

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Abstract

2-pyrimidine keto-N-aryl-7-hydrazino or phosphate ester benzylamine compound, its production and use are disclosed. Its structural formula is D or E=halogen, C1-C4 alkoxy or C1-C4 halogen alkyl, X=hydrogen, halogen or C1-C4 alkoxy; R1=hydrazine or ester of phosphoric acid C1-C4, R2=hydrogen or alkyl-acyl of C1-C4; X,=hydrogen, C1-C4 alky or halogen atom, R3=hydrogen, uramido, halogen atom, carboxy, alkyl-ester, halogen phenyl-ester, amido, amine-acyl, sulfamide, C1-C4 alkoxy, phenyl or C1-C4 alkyl substituted phenyl.

Description

technical field [0001] The present invention relates to a new class of 2-pyrimidinyloxy-N-aryl-7-nitrile or phosphoryl benzylamine compounds, a preparation method and their use as agrochemical herbicides. Background technique [0002] Pesticides are an indispensable means of production for human beings to obtain food and ensure stable and high yields in agriculture. In the past century, pesticides such as insecticides, fungicides, and herbicides have made great contributions to human beings. In recent years, with the continuous growth of the world population, human beings' demand for food is also increasing, but the growth rate of cultivated land is far behind the speed of population growth. To solve this worldwide problem, we must rely on increasing the food production per unit area. To increase yield and improve crop quality, various means must be adopted, such as breeding, cultivation, fertilization, etc., and the application of pesticides is also one of the indispensable...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34C07F9/09A01N43/54A01N57/16
Inventor 吕龙陈杰王华唐庆红彭伟立董德臻王国超吕强
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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