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Benzylamine compound, and its preparing method and use

A kind of technology of benzylamines and derivatives, applied in the field of new benzylamine derivatives

Active Publication Date: 2006-03-08
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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  • Benzylamine compound, and its preparing method and use
  • Benzylamine compound, and its preparing method and use
  • Benzylamine compound, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of intermediate 2-methyl-3-chlorothiophenol (V):

[0048] Add 80ml concentrated hydrochloric acid to the flask, ice bath, add 64.5g (0.4mol) 2-methyl-3-chloroaniline under mechanical stirring, it takes about half an hour, then stir for half an hour, keep 0℃ and add 34g (0.4mol) dropwise The solution of sodium nitrite and 68ml water takes about half an hour. Stir at 0℃ for 1 hour to obtain the diazonium salt solution. Add 64g (0.4mol) potassium ethanoate and 100ml water in a 1000ml flask, stir and heat to 40 -45℃, keep the temperature, drop in the above diazonium salt solution for about 2 hours, stir for 1 hour after the addition, cool, separate the lower oily substance, extract the water layer with ether, evaporate the ether, add 200mL anhydrous Ethanol, add 90 grams (1.6 mol) of potassium hydroxide in batches. The addition speed is appropriate to maintain a slight boiling. After the addition, heat to reflux for 6 hours, cool and reduce the pressure to evaporate t...

Embodiment 2

[0050] Preparation of intermediate 2-(4.6-dimethoxy-2-pyrimidinyl mercapto)-6 chlorotoluene (VI-1):

[0051] Add 15.8 grams of 2-methyl-3-chlorothiophenol (0.1 mol), 13.8 grams of anhydrous potassium carbonate (0.1 mol), 21.8 grams (0.1 mol) of 4.6-dimethoxy-2-methane sulfonate into a 250 mL flask Acylpyrimidine and 200mL tetrahydrofuran, reflux for 4 hours, cool, filter with suction, wash a small amount of tetrahydrofuran, evaporate the tetrahydrofuran, add 100mL methanol, stir to precipitate a white solid, filter and dry, get 18.9 g, then concentrate and cool to crystallize to get 3.6 g, yield 76%.

Embodiment 3

[0053] Preparation of intermediate 2-(4.6-dimethoxy-2-pyrimidinyl mercapto)-6-chlorobenzyl bromide (VII-1):

[0054] Add 5.93 grams (20m mol) of 2-(3,5-dimethoxypyrimidinylmercapto)-6-chlorotoluene, 3.63 grams (20m mol) of N-bromosuccinimide, 0.3g Nitrogen diisobutyronitrile, dry CCl 4 100mL, connected to reflux condenser and drying tube, heated and refluxed for 4 hours, cooled, filtered, and dissolved under reduced pressure. 15mL of methanol was added and stirred at room temperature. A white solid was precipitated, filtered and dried to obtain 5.9 g. The yield was 78.7%.

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Abstract

This invention relates to a group of benzyl amine derivatives and their preparation method, as well as their application as chemical herbicide in agriculture. In their general structural formula at right, D or E = H, halogens, C1~C4 alkyl, C1~C4 alkoxy, C1~C4 halogenated alkyl and C1~C4 halogenated alkyloxyl; R1, which can be placed on either of positions on benzene ring from 3 to 6, is = H, halogens, nitro, C1~C4 alkyl, C1~C4 alkyloxyl; R2 and R3=C1~C4 alkyl, C1~C4 halogenoalkyl, -CH2COOCH3, aryl-substituted C1~C4 alkyl, phenyl, R5-(or R6)-substituted phenyl or naphthyl and heterocyclic radical ( including pyridyl, thienyl, thiazyl and pyrimidinyl); or R2 , R3 and N combine to form circular amidogen, n= 0-2; R5 (or R6) is among H, halogens, nitro, hydroxyl, methyl, ethyl, teriarybutyl, chloromethyl, methoxyl, trifluoromethyl, trifluromethoxyl, ethoxyl, cyano and phenoxyl.

Description

Invention field [0001] The invention relates to a new type of benzylamine derivatives, specifically 2-pyrimidine sulfoxide or sulfoxide group, sulfonyl benzylamine compounds, a preparation method and its use as agrochemical herbicides. Background technique [0002] Pesticides are an indispensable means of production for humans to obtain food and ensure stable and high yields in agriculture. In the past century, pesticides such as pesticides, fungicides, and herbicides have made great contributions to mankind. In recent years, with the continuous growth of the world’s population, human needs for food are also increasing, but the growth rate of arable land is far behind the rate of population growth. To solve this worldwide problem, we must rely on increasing the amount of food per unit area. Yield and improvement of crop quality require various methods, such as breeding, cultivation, fertilization, etc., and the application of pesticides is also one of the indispensable methods. H...

Claims

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Application Information

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IPC IPC(8): C07D239/38A01N43/54
Inventor 王国超唐庆红付群梅傅荣幸董德臻彭伟立陈杰吕龙
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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