2-pyrimidine oxy-benzoic acid [2-(pyrimidine amino methyl)]benester compound, its preparation and use thereof

A technology of pyrimidineoxybenzoic acid and pyrimidine aminomethyl is applied in the field of agrochemical herbicides to achieve the effects of good post-emergence herbicidal effect, high-efficiency herbicidal activity, and good pre-emergence herbicidal effect

Inactive Publication Date: 2008-04-30
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

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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  • 2-pyrimidine oxy-benzoic acid [2-(pyrimidine amino methyl)]benester compound, its preparation and use thereof
  • 2-pyrimidine oxy-benzoic acid [2-(pyrimidine amino methyl)]benester compound, its preparation and use thereof
  • 2-pyrimidine oxy-benzoic acid [2-(pyrimidine amino methyl)]benester compound, its preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0045] Intermediate (IV-1) synthesis

[0046] D. 2 =OMe,E 2 =OMe

[0047] 415g (3.398mol) of salicylaldehyde, 740g (3.398mol) of 4,6-dimethoxy-2-thiamphenicol pyrimidine, and 938g (6.796mol) of potassium carbonate were placed in 3500mlDMF and stirred at room temperature for 2 days, followed by TLC. Completely, then the reaction product was slowly poured into 15L of water under mechanical stirring, stirred for 2 hours, a large amount of solids precipitated, stood for 1 hour, filtered, air-dried, and weighed to obtain 800g of IV-1.

example 2

[0049] Intermediate (IV-1) synthesis

[0050] D. 2 =OMe,E 2 =OMe

[0051] With 13.4g (0.11mol) salicylaldehyde and 21.8g (0.1mol) 4,6-dimethoxy-2-thiamphenicol pyrimidine, 20.7g (0.15mol) potassium carbonate in 1,4-dioxane Medium reflux for 4.5 hours, after cooling, filter with suction, rinse the filter cake with 1,4-dioxane, evaporate the solvent under reduced pressure to obtain a yellow solid, recrystallize from ethyl acetate:petroleum ether=1:10 to obtain pyrimidine salicylaldehyde white crystals of IV-1, 18.4 g.

example 3

[0053] Intermediate (IV-11) synthesis

[0054] D. 2 =OMe,E 2 =OMe

[0055] 17.1g (0.11mol) of 6-chloro salicylaldehyde and 21.8g (0.1mol) of 4,6-dimethoxy-2-thiamphenicol pyrimidine, 20.7g (0.15mol) of potassium carbonate in 1,4-bis Reflux in oxane for 14 hours, suction filter after cooling, rinse the filter cake with 1,4-dioxane, evaporate the solvent under reduced pressure to obtain a yellow solid, recrystallize from ethyl acetate:petroleum ether=1:10 to obtain pyrimidine Salicylaldehyde as white crystals IV-11, 15.8 g.

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Abstract

A 2-pyrimidine oxo-benzene carboxylic acid (2-pyrimidine amino-methyl) benzene ester compound, its production and use are disclosed. In its structural formual, D1, D2, E1 and E2=halogen, C1-C4 alkyl, C1-C4 alkoxy, X=hydrogen, halogen, nitryl, nitrile, C1-C4 alkyl, C1-C4 alkoxy, Y=hydrogen, halogen, C1-C8 alkyl and A=O or S. It can be used for agricultural chemical herbicide.

Description

technical field [0001] The invention relates to a new class of 2-pyrimidinyloxybenzoic acid [2-(pyrimidinylaminomethyl)]phenyl ester compounds, a preparation method and an application as an agricultural chemical herbicide. Background technique [0002] The invention relates to a new class of 2-pyrimidinyloxybenzoic acid [2-(pyrimidinylaminomethyl)]phenyl ester compounds, a preparation method and an application as an agricultural chemical herbicide. [0003] 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 t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12A01N43/54A01P13/00
Inventor 吕龙陈杰唐庆红王华付群梅吕强王学跃彭伟立
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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