2-butenolide acetamide compound, and preparation method and application thereof

A technology of ester acetamide and butenoic acid, applied in the field of pesticide chemistry, can solve the problems of inapplicability in the field and poor stability, and achieve the effect of promoting germination and high stability

Active Publication Date: 2020-01-31
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to overcome the poor stability of compounds with root parasitic weed seed germination promoting activity in the prior art and cannot be applied to the field, and to provide a

Method used

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  • 2-butenolide acetamide compound, and preparation method and application thereof
  • 2-butenolide acetamide compound, and preparation method and application thereof
  • 2-butenolide acetamide compound, and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example 1

[0093] Synthesis of compound 1

[0094] Potassium carbonate (1.9 g), 5-hydroxy-3-methylfuran-2(5H)-one (0.64 g) were added into the reaction flask, and acetone (50 mL) was added under stirring. After reacting at room temperature for 15 minutes, 2-bromo-N-phenylacetamide (1.2 g) was added, and the stirring reaction was continued for 10 hours. After the reaction was completed. Diatomaceous earth assisted suction filtration to remove insoluble matter, and the acetone in the solution was removed under reduced pressure, and the obtained residue was subjected to column chromatography to obtain 0.95 g of colorless oily compound 1, and its yield (calculated by weight, the same below) was 68% , the NMR data are 1 H NMR (400MHz, CDCl 3 )δ8.07(s,1H),7.54(d,J=7.6Hz,2H),7.34(t,J=8.0Hz,3H),7.15(t,J=7.6Hz,1H),6.95–6.90( m, 1H), 5.94 (s, 1H), 4.34 (dd, J=35.6, 14.8Hz, 2H), 2.17 (s, 3H).

preparation example 2

[0096] Synthesis of compound 1

[0097] Cesium carbonate (4.6g) and 2-hydroxy-N-phenylacetamide (0.8g) were added to the reaction flask, and N,N-dimethylformamide (50mL) was added under stirring. After reacting at room temperature for 15 minutes, 1.03 g of 5-bromo-3-methylfuran-2(5H)-one was added, and the stirring reaction was continued for 10 hours. After the reaction was completed. Add 100 mL of ice water and 100 mL of ethyl acetate to the system, and stir vigorously for 10 min. The organic layer was separated, and the aqueous layer was extracted once with 50 mL of ethyl acetate, and the organic layers were combined. The organic layer was extracted once with 50 mL of water and 50 mL of saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was subjected to column chromatography to obtain 0.46 g of a colorless oily compound 1 with a yield of 46 %, NMR data is 1 H NMR (400MHz, CDCl 3 )δ8.07(s,1H),7.5...

preparation example 3

[0099] Synthesis of compound 1

[0100] Potassium carbonate (1.2g), N,N-diisopropylethylamine (1.1g), 5-hydroxy-3-methylfuran-2(5H)-one (0.64g) were added to the reaction flask, stirred Acetonitrile (50 mL) was added at the same time. After reacting at room temperature for 15 minutes, 2-bromo-N-phenylacetamide (1.2 g) was added, and the stirring reaction was continued for 10 hours. After the reaction was completed. Diatomaceous earth assisted suction filtration to remove insoluble matter, and the acetonitrile in the solution was removed under reduced pressure, and the resulting residue was subjected to column chromatography to obtain 1.1 g of colorless oily compound 1, and the yield was 78%, and the NMR data was 1 H NMR (400MHz, CDCl 3 )δ8.07(s,1H),7.54(d,J=7.6Hz,2H),7.34(t,J=8.0Hz,3H),7.15(t,J=7.6Hz,1H),6.95–6.90( m, 1H), 5.94 (s, 1H), 4.34 (dd, J=35.6, 14.8Hz, 2H), 2.17 (s, 3H).

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Abstract

The invention relates to the field of pesticide chemistry, and discloses a 2-butenolide acetamide compound, and a preparation method and an application thereof. The compound has a structure represented by a formula (1). A synthesis method of a compound represented by the formula (2) comprises the steps: carrying out a first reaction on a compound represented by a formula (3) and a compound represented by a formula (4) in the presence of a first alkaline substance and a first solvent. The synthesis method of the compound represented by the formula (1) comprises the steps: carrying out a secondreaction on the compound represented by the formula (2) and a compound represented by a formula (5) in the presence of a second alkaline substance and a second solvent. The 2-butenolide acetamide compound disclosed by the invention can promote germination of root parasitic weed seeds, has relatively high stability, and can be well applied to prevention and treatment of root parasitic weeds in fields.

Description

technical field [0001] The invention relates to the field of pesticide chemistry, in particular to a 2-butenolactone acetamide compound and a preparation method and application thereof. Background technique [0002] Striga and letang are root parasitic weeds, which parasitize the roots of crops, such as corn, sorghum, sunflower, melons, tomatoes and cereals, absorb water and nutrients from the host roots, causing severe crop yield reduction, or even failure . Striga and Liedang are distributed all over the world, among which Striga is mainly distributed in subtropical and tropical regions, and Liedang is mainly distributed in subpolar and temperate regions. At present, there is no effective herbicide for controlling root parasitic weeds, and the annual economic loss caused by root parasitic weeds is as high as 10 billion US dollars. [0003] Strigolactones and their derivatives are a class of natural products with a tetracyclic structure isolated from plants, which can sti...

Claims

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Application Information

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IPC IPC(8): C07D307/60C07D405/12C07D307/79A01N43/08A01N43/30A01N43/12A01N43/38A01P13/00
CPCC07D307/60C07D405/12C07D307/79A01N43/08A01N43/30A01N43/12A01N43/38
Inventor 席真王大伟庞智黎
Owner NANKAI UNIV
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