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N-pyridine aryloxyphenoxy carboxylic acid derivatives, preparation method and applications thereof

A technology of pyridine aryloxyphenoxycarboxylic acid and derivatives, which can be used in the fields of herbicide, insecticide/acaricide, and sterilization, and can solve the problems of unsatisfactory rice safety and inability to control weeds and the like

Active Publication Date: 2016-02-10
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Similarly, 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 chain oxyaryloxyphenoxy carboxylic acid amide compounds (P-7CN201010221128.2), from which it was found that clodinafop-propargyl shown in (P-1) and cyhalofop shown in (P-2) Ester and the oxafenamide shown in (P-3) have a wider activity spectrum and higher active compounds such as (P-8), etc., compared with the clodinafop-propargyl shown in (P-1), The (P-8) we invented is safer for wheat, but (P-1) and (P-8) are not ideal for rice safety, so they cannot be used to control weeds in rice fields

Method used

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  • N-pyridine aryloxyphenoxy carboxylic acid derivatives, preparation method and applications thereof
  • N-pyridine aryloxyphenoxy carboxylic acid derivatives, preparation method and applications thereof
  • N-pyridine aryloxyphenoxy carboxylic acid derivatives, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0188] Example 1 This example illustrates the preparation of compound 01(R / S) in Table 1.

[0189]

[0190] (R / S)-2-(4-Hydroxyphenoxy)propionic acid Add 2-bromopropionic acid to 50% NaOH (0.1mol) solution at 15-25°C, stir to dissolve and add 30mL of water , continue to stir for 5-10 minutes, set aside. Under the condition of 15-25°C, add hydroquinone (0.4mol) and 50mL of water into the reaction bottle, add 50% NaOH (0.8mol) under stirring, then add the NaOH solution of the above-mentioned 2-bromopropionic acid, 50-60 React at ℃ for 4-6 hours, cool, adjust the pH to 4.0-4.5 with dilute hydrochloric acid, extract with ethyl acetate, adjust the pH to 1.0-1.5 with dilute hydrochloric acid, extract with isopropyl acetate, add water to the organic phase to azeotropically remove isopropyl acetate, Adjust the pH of the aqueous solution to 2.0-2.5 with 50% NaOH solution, cool, extract with ethyl acetate, dry over anhydrous sodium sulfate, and remove the solvent to obtain (R / S)-2-(4...

Embodiment 2

[0195] Example 2 This example illustrates the preparation of compound 02(R) in Table 1.

[0196]

[0197] (R)-2-(4-((5-Chloro-3-fluoropyridin-2-yl)oxy)phenoxy)propanoic acid was replaced by (R)2-(4-hydroxyphenoxy)propanoic acid (R / S) 2-(4-hydroxyphenoxy)propionic acid, synthesize (R)-2-(4-((5-chloro-3-fluoropyridin-2-yl) oxygen with reference to the method of Example 1 base) phenoxy) propionic acid.

[0198] (R)-N-(3-nitropyridin-2-yl)-2-(4-((3-fluoro-5-chloropyridin-2-yl)oxy)phenoxy)propionamide (R) -2-[4-(3-fluoro-5-chloropyridin-2-yl)oxy)phenoxy]propanoic acid (1.04g, 3.3mmol), dichloromethane (40mL), 2-amino-3- Nitropyridine (3.3mmol), add triethylamine (10mmol) and methanesulfonyl chloride (3.3mmol) dropwise under ice cooling condition, react overnight at room temperature, pour into 100-200mL ice water, extract with dichloromethane, anhydrous sulfuric acid Dry over sodium, remove the solvent, and purify by column chromatography to give 0.30 g of the light yellow tit...

Embodiment 3

[0199] Example 3 This example illustrates the preparation of compound 03(R / S) in Table 1.

[0200]

[0201] 3-nitropyridine-2-methylamine 2-chloro-3-nitropyridine (0.02mol), 25~30% methylamine solution (0.2mol,), potassium carbonate (0.04mol), catalytic amount of potassium iodide, DMF ( 50 mL), react at room temperature for 10-12 h, pour the reaction solution into 200 mL of water, filter, wash with water, and dry to obtain 2.93 g of the title compound as a yellow solid, with a yield of 95.8%.

[0202] (R / S)N-Methyl-N-(3-nitropyridin-2-yl)-2-(4-((3-fluoro-5-chloropyridin-2-yl)oxy)phenoxy ) Propionamide reaction flask was added (R / S)-2-(4-(3-fluoro-5-chloropyridin-2-yloxy)phenoxy)propionyl chloride (3.3mmol), dichloromethane (40mL ), 3-nitropyridine-2-methylamine (3.3mmol) and catalytic amount of 4-dimethylaminopyridine (DMAP), stirred at room temperature for 10min, after dripping triethylamine (10mmol), the temperature was raised to reflux reaction 3 ~5hr, pour into 100~20...

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Abstract

The invention discloses N-pyridine aryloxyphenoxy carboxylic acid derivatives represented by the formula (I), a preparation method and applications thereof. In the formula (I), the definitions of Ar1, Ar2, R, R', R1, R2, R3, R4, m, n, p, q, and X are represented in the description. The compounds (I) has activities on killing weeds, bacteria, and insects, and has extremely high activity on killing monocotyledon weeds such as Chinese sprangletop.

Description

technical field [0001] The invention belongs to the fields of herbicide, bactericide, and insecticide / mite agent, and specifically relates to N-pyridine aryloxyphenoxycarboxylic acid derivatives with herbicide, bactericide, and insecticide biological activities, a preparation method thereof, and a herbicide and bactericide containing the compound. , insecticide composition, and use and method of controlling harmful weeds, harmful bacteria, and pests with these compounds. Background technique [0002] Aryloxyphenoxycarboxylic acid compounds have the activity of controlling grass weeds, and a plurality of active compounds of this type have been successfully developed as herbicides, such as clodinafop-propargyl (clodinafop-propargyl) shown in formula (P-1) It is an aryloxyphenoxypropionate herbicide developed by Syngenta Crop Protection Co., Ltd. in Switzerland with a dose of 40-60 grams of active ingredients / ha for the control and elimination of vicious grass weeds in certain ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75C07D213/77C07D213/84C07D413/12C07D401/12A01N43/40A01N43/76A01N43/60A01P13/00A01P7/02A01P7/04A01P3/00
Inventor 柳爱平任叶果雷满香庞怀林刘祈星黄路何莲韩魁元高岗何丽英
Owner HUNAN CHEM RES INST
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