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N-acyl-1,2-cyclo-nitrogen-p-menthane, as well as preparation method and herbicidal activity application thereof

A technology of ring nitrogen paramentane and acyl group, which is applied in the field of N-acyl-1,2-cyclic nitrogen paramentane and its preparation, can solve the problems of no discovery, inapplicability and the like, and achieves low environmental pollution, low toxicity, Easy to apply effects

Active Publication Date: 2016-09-28
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the products of these synthetic aziridines, the existence of the substance N-acyl-1,2-ringazine p-mentane of the present invention is not found, that is to say, the existing method for synthesizing aziridines is not suitable for the synthesis of this product. Invention substance N-acyl-1,2-cycloaza-p-menthane

Method used

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  • N-acyl-1,2-cyclo-nitrogen-p-menthane, as well as preparation method and herbicidal activity application thereof
  • N-acyl-1,2-cyclo-nitrogen-p-menthane, as well as preparation method and herbicidal activity application thereof
  • N-acyl-1,2-cyclo-nitrogen-p-menthane, as well as preparation method and herbicidal activity application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Add 19.9 mL of 10% HCl aqueous solution, 5.08 g of N,N'-acyl-1,8-p-mentanediamine (such as N, N'-Diacetyl-1,8-p-mentanediamine, N,N'-dibutyryl-1,8-p-mentanediamine, N,N'-dipentanoyl-1,8-p Menthanediamine, N,N'-dicaproyl-1,8-p-mentanediamine, N,N'-dibenzoyl-1,8-p-menthanediamine and N,N'-di Phenylacetyl-1,8-p-menthanediamine, etc.), heated to reflux for 26h. After the reaction was completed, it was left to stand, and the reaction solution was separated into layers. After the pH of the lower layer solution was adjusted to 8-11, the solution was layered, and the upper layer solution was dried and subjected to silica gel column chromatography to obtain the corresponding N-acyl-1,2-cycloaza-p-menthane product.

Embodiment 2

[0048] In the 100mL four-neck flask equipped with a thermometer, a condenser tube and a mechanical stirrer, add 20mL concentration of 10% HCl aqueous solution, 2g N-acyl-3-p-mentene-1-amine (such as N-acetyl-3- p-menten-1-amine, N-butyryl-3-p-menten-1-amine, N-pentanoyl-3-p-menten-1-amine, N-hexanoyl-3-p-menten-1 -amine, N-benzoyl-3-p-menthene-1-amine and N-phenylacetyl-3-p-menthen-1-amine, etc.), heated to reflux for 24h. After the reaction was completed, it was left to stand, and the reaction solution was separated into layers. After the pH of the lower layer solution was adjusted to 8-11, the solution was layered, and the upper layer solution was dried and subjected to silica gel column chromatography to obtain the corresponding N-acyl-1,2-cycloaza-p-menthane product.

Embodiment 3

[0050] Add 198.9mL of 10wt.% HCl aqueous solution and 50.8g of N,N'-diacetyl-1,8-p-mentanediamine to a 500mL four-necked flask equipped with a thermometer, a condenser and a mechanical stirrer, Start stirring, heating to reflux for 30h. After the reaction, it was left standing, and the reaction solution was separated into layers, the upper layer was a yellow liquid, and the lower layer was an aqueous solution. After the pH of the lower layer solution was adjusted to 8-11, the solution was layered, and the upper layer was a yellow transparent liquid. The yellow transparent liquid in the upper layer was vacuum-dried at 70° C. to obtain 11.8 g of the product, with a yield of 30.3%. After silica gel column chromatography, a colorless and transparent liquid product with a purity of 99.85% was obtained, and its main physical parameters and HR-MS, FT-IR, ESI + -MS, 1 H-NMR and 13 C-NMR characterization data are as follows:

[0051] Boiling point B.p.=229.3°C; Refractive index ...

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Abstract

The invention firstly discloses N-acyl-1,2-cyclo-nitrogen-p-menthane, as well as a preparation method and herbicidal activity application thereof. The preparation method comprises the following steps: dissolving N,N'-diacyl-1,8-p-menthane diamine or N-acyl-3-poxlene-1-amine into a strong acid water solution, stirring, and carrying out a reaction under the appropriate temperature condition for 20 h or longer; after the reaction is finished, allowing the reaction liquid to cool and stand still, and stratifying the reaction liquid; adjusting the pH of the lower layer solution to be 8-11 through a sodium hydroxide water solution, and stratifying the solution, wherein the upper layer is yellow transparent liquid; conducting vacuum drying on the upper layer yellow transparent liquid, and purifying through silica gel column chromatography to obtain N-acyl-1,2-cyclo-nitrogen-p-menthane. The product is relatively mild in reaction condition, simple in technology process and easy for raw material preparation, and is very beneficial to development and utilization. The prepared series of N-acyl-1,2-cyclo-nitrogen-p-menthane plays a better growth inhibition effect on annual ryegrass.

Description

technical field [0001] The present invention relates to N-acyl-1,2-cyclonitro-p-menthane and its preparation method, in particular to the use of strong acid to catalyze N,N'-diacyl-1,8-p-mentanediamine to eliminate one molecule of amido A method for ring closing or N-acyl-3-p-menthene-1-amine catalyzed by strong acid to generate N-acyl-1,2-cycloaza-p-menthane. Background technique [0002] A large number of literatures have shown that compounds containing p-mentane skeletons, aziridine compounds and amides have strong biological activities, such as the compound 3,8-p-mentanediol (PMD) containing p-mentane skeletons. And its derivatives have strong repellency to Aedes aegypti (Jeremy Drapeau, Manon Rossano, Didier Touraud, et al., Comptes Rendus Chimie, 2011, 14, 629~635.), aziridine compounds Mitomycin It is a kind of anti-tumor drug used in clinic (Chen X Y, et., Tetrahedron, 2008, 64, 2301-2306.), acyl compound 2-deoxy-2,3-dehydro-N-acetylneuramine Acid has a strong inhi...

Claims

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Application Information

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IPC IPC(8): C07D203/26C07D203/02A01P13/00
CPCC07D203/02C07D203/26
Inventor 赵振东朱守记徐士超陈玉湘李冬梅毕良武王婧古研卢言菊
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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