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N-(arylalkyl)aryloxy phenoxy carboxylic acid amide compounds, and preparation method and application thereof

A technology of aryloxyphenoxycarboxylic acid amide and aryl alkyl, which is applied in the field of N-aryloxyphenoxycarboxylic acid amide compounds, and can solve the problems of unsafe rice, low activity, and inability to control weeds in paddy fields, etc.

Active Publication Date: 2015-01-14
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aryloxyphenoxycarboxylic acid herbicides are active against gramineous weeds, and some have very excellent activity. The disadvantage is that most of these herbicides are not safe for gramineous crops (such as wheat, rice, etc.)
Although clodinafop-propargyl shown in (P-1) has high activity on grass weeds, it is only safe to some wheat varieties and is not safe to rice; cyhalofop-methyl shown in formula (P-2) Although fenpyramid shown in formula (P-3) is safe to rice, its activity on grass weeds is far lower than that of clodinafop-propargyl shown in (P-1), and it is also not effective on wheat. Safety
[0004] In order to obtain highly active aryloxyphenoxycarboxylic acid compounds that are safe for grass crops, especially rice and wheat, the inventors introduced O-chain unsaturated hydroxylamine into the structure of aryloxyphenoxycarboxylic acid, designed and synthesized N-unsaturated Saturated chain oxyaryloxyphenoxy carboxylic acid amide compounds (CN201010221128.2), from which it was found that clodinafop-propargyl shown in (P-1) and cyhalofop-methyl shown in (P-2) and (P -3) The fenpyramid shown in -3) has a wider activity spectrum and higher activity compounds such as (P-4), and compared with the clodinafop-propargyl shown in (P-1), our invented (P-4) is safer for wheat, but (P-1) and (P-4) are not safe for rice, so they cannot be used to control weeds in rice fields

Method used

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  • N-(arylalkyl)aryloxy phenoxy carboxylic acid amide compounds, and preparation method and application thereof
  • N-(arylalkyl)aryloxy phenoxy carboxylic acid amide compounds, and preparation method and application thereof
  • N-(arylalkyl)aryloxy phenoxy carboxylic acid amide compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] This example illustrates the preparation of compound 01 in Table 1.

[0109]

[0110] (R)-2-(4-((5-chloro-3-fluoropyridin-2-yl)oxy)phenoxy)propionic acid was added in a 100mL three-necked flask equipped with a magnetic stirrer, thermometer and condenser N,N-Dimethylformamide (DMF) (40mL), (R) 2-(4-hydroxyphenoxy)propionic acid (0.02mol), after stirring and dissolving, add potassium carbonate (0.04mol) in batches, Raise the temperature to 60-80°C and stir for 0.5-1.0 hr. 2,3-Difluoro-5-chloropyridine (0.02 mol) was added dropwise, and the stirring reaction was continued for 6-8 hr. The reactant was cooled to room temperature, poured into ice water (250 mL), and dilute hydrochloric acid was slowly added to the mixture to adjust the pH to 4-5, filtered, washed with water, and dried to obtain 5.92 g of the title compound as a white solid.

[0111] Add N,N-dimethylformamide (40mL), phthalimide (0.05mol) and potassium hydroxide (0.05mol) into a 100mL three-necked flask o...

Embodiment 2

[0114] This example illustrates the preparation of compound 03 in Table 1.

[0115]

[0116] Add 2-chloro-5-chloromethylthiazole (0.05mol), CHCl 3 (50mL), after stirring evenly, add dropwise methylamine aqueous solution (25g, 25-30%) and sodium hydroxide aqueous solution (25ml, 10%), and add a small amount of phase transfer catalyst tetrabutylammonium bromide, and stir at 25-30°C React overnight. Adjust the pH to weakly alkaline with dilute hydrochloric acid, separate the layers, wash the organic phase twice with water, dry over anhydrous sodium sulfate, and extract 6.67 g of the title compound as a pale orange liquid.

[0117] (R)-N-methyl-N-(2-chlorothiazol-5-ylmethyl)-2-(4-((5-chloro-3-fluoropyridin-2-yl)oxy)phenoxy ) Propionamide (compound 03 in Table 1) was added toluene (40mL) in 100mL one-mouth bottle, (R)-2-(4-((3-fluoro-5-chloropyridin-2-yl)oxy)phenoxy ) propionic acid (3.3 mmol) and thionyl chloride (10 mmol). After the reactant was refluxed for 3-5hr, the tol...

Embodiment 3

[0118] Example 3 This example illustrates the preparation of compound 42 in Table 1.

[0119]

[0120] (R)-2-(4-((3-Chloro-5-trifluoromethylpyridin-2-yl)oxy)phenoxy)propionic acid was prepared in a 100mL three-port vessel equipped with a magnetic stirrer, a thermometer and a condenser Add N,N-dimethylformamide (DMF) (40mL), (R)-2-(4-hydroxyphenoxy)propionic acid ([α] 589 20℃ =+59.5° (acetone)) (0.02mol), stir and dissolve, add potassium carbonate (0.04mol) in batches, raise the temperature to 60-80°C and stir for 1.0-1.5hr. 2,3-dichloro-5-trifluoromethylpyridine (0.02 mol) was added dropwise, and the stirring reaction was continued for 8-10 hrs. The reactant was cooled to room temperature, poured into ice water (250 mL), then slowly added dilute hydrochloric acid to the mixture, adjusted to pH=4~5, filtered, washed with water, and dried to obtain 6.56 g of the title compound as a white solid, [α] 589 20℃ =+37.9° (acetone).

[0121] Add N,N-dimethylformamide (DMF) (40mL...

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Abstract

Disclosed are an N-(aryl alkyl) aryloxy phenoxy carboxylic acid amide compound expressed by formula (I) and a preparation method and application thereof. Ar1, Ar2, R1, R2, R3, and n in formula (I) are defined as given in the specification. The compound of formula (I) according to the present invention has weeding and / or sterilizing, insecticidal, and acaricidal bioactivities. Some compounds have a very high herbicidal activity, and desirable effects can be achieved with a dosage of 15 to 75 g effective components per hectare.

Description

technical field [0001] The present invention relates to N-(arylalkyl) aryloxyphenoxy carboxylic acid amide compounds with herbicidal, bactericidal and insecticidal biological activities and their preparation methods, as well as the use of these compounds to control harmful weeds, harmful bacteria and pests with method. Background technique [0002] Aryloxyphenoxycarboxylic acid compounds have the activity of controlling grass weeds, and several active compounds of this type have been successfully developed as herbicides, such as clodinafop-propargyl (clodinafop-propargyl US4505743 ) is an aryloxyphenoxypropionate herbicide developed by Syngenta Crop Protection Co., Ltd., Switzerland, with a dosage of 40-60 grams of active ingredients per hectare, and is used to control vicious grass weeds in certain varieties of wheat fields; and Cyhalofop-butyl EP0302203 represented by formula (P-2) was developed and produced by Dow AgroSciences in 1987. It is a benzene specific for paddy ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D277/32C07D213/643C07D401/12C07D413/12A01N43/78A01N43/40A01N43/60A01N43/76A01P13/00A01P3/00A01P7/04A01P7/02
CPCA01N43/78A01N43/40A01N43/60A01N43/76C07D213/643C07D277/32C07D401/12C07D413/12C07D417/12
Inventor 王晓光柳爱平刘祈星雷满香任叶果欧晓明黄路韩魁元高岗吴曼
Owner HUNAN CHEM RES INST
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