2-pyrimidinyloxy benzoic acid derivative and preparation method thereof, and herbicide for water weed

A technology of pyrimidinyloxybenzoic acid and derivatives, applied in the field of pesticides, can solve the problems of time-consuming and laborious, easy precipitation, poor water solubility, etc., and achieve high-efficiency herbicidal effect and good water-solubility effect.

Active Publication Date: 2017-07-14
GANNAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such compounds that have been reported so far, such as bispyribac, have poor water solubility and are easily precipitated after entering water. Before use, a large amount of surface active substances need to be added, otherwise the efficacy will be affected; and when applied, the method of spraying is generally adopted. , is time-consuming and labor-intensive, and does not meet the current research goals of labor-saving pesticides

Method used

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  • 2-pyrimidinyloxy benzoic acid derivative and preparation method thereof, and herbicide for water weed
  • 2-pyrimidinyloxy benzoic acid derivative and preparation method thereof, and herbicide for water weed
  • 2-pyrimidinyloxy benzoic acid derivative and preparation method thereof, and herbicide for water weed

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preparation example Construction

[0055] The present invention provides the preparation method of 2-pyrimidinyloxybenzoic acid derivative described in above-mentioned technical scheme, comprises the following steps:

[0056] Mix 2-pyrimidinyloxybenzoic acid compounds, aprotic solvents and organic salts, and carry out a substitution reaction at -10 to 150°C for 0.5 to 48 hours under the action of a catalyst to obtain 2-pyrimidinyloxybenzoic acid derivatives;

[0057] The organic salt is quaternary ammonium salt, sulfonate or organic sulfate.

[0058] In the present invention, the molar ratio of the 2-pyrimidinyloxybenzoic acid compound, aprotic solvent, catalyst and organic salt is preferably 1: (100-1000): (0.001-2): (1-10), More preferably 1:(200-800):(0.05-1.5):(2-8), most preferably 1:(400-600):(0.5-1):(3-6).

[0059] In the present invention, the selection of the 2-pyrimidinyloxybenzoic acid compound corresponds to the 2-pyrimidinyloxybenzoic acid derivative having the structure shown in formula I, formul...

Embodiment 1

[0084] Mix 2-pyrimidinyloxybenzoic acid (1 mmol), 1-bromo-N,N,N trimethyldodecylammonium bromide (5 mmol), sodium hydroxide (2 mmol) and dimethyl sulfoxide (800 mmol) , at a stirring rate of 500rpm, the substitution reaction was carried out at 120°C for 24h;

[0085] Filter the obtained material, remove the solvent in the obtained filtrate by distillation under reduced pressure, wash with saturated aqueous sodium hydroxide solution, extract with dichloromethane (3×20 mL), wash with water, and dry with anhydrous sodium sulfate to obtain a dry material;

[0086] The solvent in the obtained dry material was distilled off under reduced pressure, and a mixed solvent of ethyl acetate and petroleum ether was used as an eluent (the volume ratio of ethyl acetate and petroleum ether was 1:1), and separated by column chromatography to obtain a light yellow liquid , which is N,N,N-trimethyl-12-((2-(pyrimidine-2-oxy)benzaldehyde)oxy)dodecyl-1-ammonium bromide, the structure is as follows: ...

Embodiment 2

[0092] (4-methoxy)-2-pyrimidinyloxy-5-chlorobenzoic acid (1mmol), 1-bromo-N,N,Ntrimethyldodecylammonium bromide (5mmol), potassium hydroxide ( 2mmol) and dimethyl sulfoxide (800mmol) were mixed, and at a stirring rate of 400rpm, a substitution reaction was carried out at 120°C for 24h;

[0093] Filter the obtained material, remove the solvent in the obtained filtrate by distillation under reduced pressure, wash with saturated aqueous sodium hydroxide solution, extract with dichloromethane (3×20 mL), wash with water, and dry with anhydrous sodium sulfate to obtain a dry material;

[0094] The solvent in the obtained dried material was distilled off under reduced pressure, and a mixed solvent of ethyl acetate and petroleum ether was used as an eluent (the volume ratio of ethyl acetate and petroleum ether was 1:1.2), and separated by column chromatography to obtain a light yellow liquid , which is 12-((5-chloro-2-((4-methoxypyrimidin-2-yl)oxy)benzoyl)oxy)-N,N,N-trimethyldodecyl ...

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Abstract

The invention provides a 2-pyrimidinyloxy benzoic acid derivative with a structure shown as in a formula I, II or III. The 2-pyrimidinyloxy benzoic acid derivative has high herbicidal activity. A herbicide for water weed with the 2-pyrimidinyloxy benzoic acid derivative as an active ingredient is effort-saving and time-saving when being applied. Experimental results in the embodiment show that the herbicide for water weed with the 2-pyrimidinyloxy benzoic acid derivative as the active ingredient can kill 78% of barnyard grass and 57% of ammannia arenaria in paddy in 72 hours if the concentration of the 2-pyrimidinyloxy benzoic acid derivative is 0.5g / m<2> on the water surface.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a 2-pyrimidinyloxybenzoic acid derivative, a preparation method thereof and a water surface weed herbicide. Background technique [0002] my country has a long history of planting rice and has a vast territory. It is one of the main rice producing countries in the world. Regardless of planting area or output, rice ranks first among food crops in my country. There have always been a large number of weeds in the paddy fields of all rice-growing areas in my country. Weeds compete with rice for glory, fertilizer and water, seriously affecting the growth of rice, reducing the yield and quality of rice, and even causing failure. [0003] 2-pyrimidinyloxybenzoic acid compounds have excellent herbicidal effect. However, such compounds that have been reported so far, such as bispyribac, have poor water solubility and are easily precipitated after entering water. Before use, a large ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/34C07D239/52A01N43/54A01P13/00
CPCA01N43/54C07D239/34C07D239/52
Inventor 郭维郑绿茵吴勇权李勋范小林
Owner GANNAN NORMAL UNIV
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