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N-2-pyrimidinyl oxy-benzyl substituted cyclic amine compound, its preparation process and uses

A technology of pyrimidinyloxybenzyl, compounds, applied in the field of agrochemical herbicides

Active Publication Date: 2009-06-24
ZHEJIANG RES INST OF CHEM IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although pyrimidine salicylates have high herbicidal activity, they are currently only suitable for weed control in cotton fields and rice fields

Method used

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  • N-2-pyrimidinyl oxy-benzyl substituted cyclic amine compound, its preparation process and uses
  • N-2-pyrimidinyl oxy-benzyl substituted cyclic amine compound, its preparation process and uses
  • N-2-pyrimidinyl oxy-benzyl substituted cyclic amine compound, its preparation process and uses

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0050] Synthesis of intermediate 2-methyl-3-chlorophenol (III-1):

[0051] Add 80ml of concentrated sulfuric acid and 400ml of water to the flask, and add 64.5 grams (0.4mol) of 2-methyl-3-chloroaniline under mechanical stirring in an ice bath for about half an hour, then stir for another half an hour, and add 34 grams (0.4 mol) of sodium nitrite and 70ml of water takes about half an hour, and stir at 0°C for 1 hour to obtain a diazonium salt solution. Add 150g of sodium sulfate, 200ml of sulfuric acid and 200ml of water into a 1000ml flask, stir and heat to Reflux (the temperature in the bottle is 130-135°C), keep the temperature, drop the above diazonium salt solution for about 2 hours, and distill out about the same amount of water at the same time, add 500ml of water after the addition, and distill out the same amount of water , cooled, the distillation fraction was extracted with chloroform (100ml*3), the chloroform layer was dried over sodium sulfate and then precipitate...

example 2

[0054] Preparation of intermediate 2-(4,6-dimethoxy-2-pyrimidinyloxy)-6-chlorotoluene (VI-1):

[0055] In a 250mL flask, add 0.1mol of 2-methyl-3-chlorophenol (III-1), 15.0 grams of anhydrous potassium carbonate, 0.1mol4,6-dimethoxy 2-methylsulfonylpyrimidine and 200ml tetrahydrofuran, and reflux for 4 hour, cooling, suction filtration, steaming off tetrahydrofuran, adding 50ml of methanol, stirring to precipitate a white solid, filtering, and drying to obtain intermediate 2-(4,6-dimethoxy-2-pyrimidinyloxy)-6 chlorotoluene ( IV-1), the yield is 86%.

[0056] Using the same method, using different raw materials - 4-D-6-E-2-methylsulfonylpyrimidine can synthesize intermediate 2-(4-D-6-E-2-pyrimidinyloxy)-6-chloro Toluene (IV), (D, E represent other substituents in the structural formula (I)).

example 3

[0058] Preparation of intermediate 2-(4,6-dimethoxy-2-pyrimidinyloxy)-6-chlorobenzyl bromide (V-1):

[0059] In a 150mL flask, add 20mmol 2-(4,6-dimethoxy-2-pyrimidinyloxy)-6 chlorotoluene (IV-1), 20mmol N-bromosuccinimide, 0.3 g of azobis Isobutyronitrile, dry CCl 4 100ml, connect the reflux condenser and drying tube, heat and reflux for 4 hours, cool, filter, desolvate under reduced pressure, add 15ml methanol and stir at room temperature, a white solid precipitates, filter, and dry to obtain the intermediate 2-(4,6-dimethoxy yl-2-pyrimidinyloxy)-6-chlorobenzyl bromide (V-1), the yield was 80.7%.

[0060] In the same way, using a different starting material - 2-(4-D-6-E-2-pyrimidinyloxy)-6-R 1 -Toluene (IV) can synthesize intermediate 2-(4-D-6-E-2-pyrimidinyloxy)-6-R 1 -Benzyl bromide (V), (D, E, R 1 represent other substituents in formula (I)).

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Abstract

The invention relates to an N-2-pyrimidinyloxybenzyl-substituted cyclic amine compound, a preparation method and its use as an agricultural chemical herbicide. Its structural formula is as follows: where: D and E = halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or C1-C4 haloalkoxy; R1 = hydrogen, halogen, nitro, C1-C4 Alkyl, hydroxyl, tolyloxy or C1-C4 alkoxy, R1 can be located at any position 3, 4, 5 or 6 of the benzene ring; R2, R3, R4 = hydrogen, halogen, nitro, nitrile group , hydroxyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, formic acid and its alkali metal salts, formic acid C1~6 ester group, formamide or N-C1~4 alkyl or phenyl substitution Formamide.

Description

field of invention [0001] The present invention relates to a new class of N-2-pyrimidinyloxybenzyl substituted cyclic amine compounds, a preparation method and its use as an agricultural chemical herbicide. Background of the invention [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 esse...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/34C07D403/12C07D413/12A01N43/54A01N43/84A01P13/00
Inventor 彭伟立唐庆红徐小燕陈杰王国超台文俊刘燕君吕龙
Owner ZHEJIANG RES INST OF CHEM IND CO LTD