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2-alkyl acrylate compounds and uses thereof

A technology of alkyl acrylates and compounds, which is applied in the field of 2-alkyl acrylate compounds, and can solve the problems that alkacrylate compounds have not been disclosed.

Inactive Publication Date: 2009-04-15
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But as shown in the present invention, the alkyl acrylate compound containing benzoic acid or phenoxy (sulfur) group has not been disclosed

Method used

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  • 2-alkyl acrylate compounds and uses thereof
  • 2-alkyl acrylate compounds and uses thereof
  • 2-alkyl acrylate compounds and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Embodiment 1: the synthesis of compound 1

[0099]

[0100] Add successively 2.2 grams of substituted phenols (6.0 millimoles, made with reference to the operation method provided by EP68822), 10 milliliters of N, N-dimethylformamide and 0.24 grams of sodium hydride (6.0 millimoles) in a 100 milliliter reaction flask, 1.0 g (5.0 mmol) of methyl 2-(bromomethyl)acrylate was stirred at room temperature for 1 hour. The reaction solution was poured into 20 ml of water, extracted with 100 ml of ethyl acetate, the organic layer was washed successively with saturated sodium carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography ( Eluent: ethyl acetate:petroleum ether=1:10), to obtain 0.70 g of white solid compound 1, yield: 36%.

Embodiment 2

[0101] Embodiment 2: the synthesis of compound 12

[0102]

[0103] Add successively 0.62 grams of substituted benzoic acid (2.0 millimoles, prepared with reference to the operation method provided by EP68822), 10 milliliters of dichloromethane and 0.38 grams of oxalyl chloride (3.0 millimoles) and 1 drop of N, N - Dimethylformamide, stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure to obtain 0.67 g of a yellow solid (abbreviated as benzoyl chloride), yield: 99%.

[0104]

[0105] Add 0.36 grams of 2-(1-hydroxyethyl) ethyl acrylate (2.0 mmoles, prepared with reference to the method provided by US3742669), 10 milliliters of dichloromethane and 0.31 grams of triethylamine (3.0 mmol), a solution of 0.67 g (2.0 mmol) of the above benzoyl chloride in dichloromethane (10 ml) was added dropwise, and the mixture was stirred at room temperature for 1 hour after the addition was completed. The reaction solution was poured into ...

Embodiment 3

[0106] Embodiment 3: the synthesis of compound 13

[0107]

[0108] Add 2.40 grams (10.0 mmoles) of 2-chloro-4-fluoro-5-nitrophenol, 20 milliliters of N, N-dimethylformamide, 1.70 grams (12.0 mmoles) of potassium carbonate successively in a 50 ml reaction flask. ) and 2.90 g (10.0 mmol) of ethyl 2-(bromomethyl)acrylate, and stirred at 60° C. for 5 hours. The reaction solution was poured into 20 ml of water, extracted with 100 ml of ethyl acetate, the organic layer was washed successively with saturated sodium carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography ( Eluent: ethyl acetate:petroleum ether=1:12), to obtain 2.37 g of white solid 2-{2-chloro-4-fluoro-5-nitrophenoxymethyl}ethyl acrylate (nitro for short) , Yield: 78%.

[0109]

[0110] 2.37 g (7.0 mmol) of the above-mentioned nitro substance, 20 ml of acetic acid, and 1.6 g (2.89 mmol) o...

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Abstract

The invention discloses a 2-alkyl acrylic ester compound containing benzoic acid or phenoxyl (sulfur) radical with novel structure as is show in general formula I, wherein, Q is chosen from a plurality of nitrogen-containing heterocyclic groups; X is chosen from H or F; P is chosen from a bond or CO; V is chosen from O or S; R1 is chosen from H or C1-C6 alkyl; R2 is chosen from C1-C6 alkyl, C3-C6 alkenyl or C3-C6 alkynyl; and a stereoisomer thereof. The general formula I compound has postemergence herbicide activity and is safe to soy bean and peanut.

Description

technical field [0001] The invention belongs to the field of herbicides, and in particular relates to a 2-alkyl acrylate compound and application thereof. Background technique [0002] Due to the succession and change of weed populations and the emergence and rapid development of resistance to chemical pesticides; the strengthening of people's awareness of ecological environment protection and the awareness of chemical pesticide pollution, the impact of pesticides on non-target organisms, and the fate of pesticides in the ecological environment Pay attention to; the reduction of the world's cultivated land area and the increase in the demand for food due to population growth; the rapid development of agricultural production technology and the continuous improvement of farming systems, etc., need to continuously invent new and improved herbicidal compounds and compositions. [0003] Certain 2-(substituted aryl) alkyl acrylate compounds have been reported as herbicides (JP83-6...

Claims

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Application Information

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IPC IPC(8): C07D209/48C07D471/04C07D487/04A01N43/38A01N43/90A01P13/00
Inventor 李斌于海波崔东亮白丽萍李志念张勇
Owner 中国中化股份有限公司
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