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A kind of glucosamide compound and its preparation and application

A kind of technology of glucoamide and compound, applied in the field of glucoamide compound

Active Publication Date: 2019-06-14
BEIJING BOQUANJIAN PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there is no information about the synthesis of 6-(acetoxymethyl)-3-(substituted benzamide)tetrahydro-2H-pyran-2,4,5-triyltriacetate derivatives and their biological Bibliographic reports on activity studies

Method used

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  • A kind of glucosamide compound and its preparation and application
  • A kind of glucosamide compound and its preparation and application
  • A kind of glucosamide compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (2S, 3R, 4R, 5S, 6R)-6-(acetoxymethyl)-3-((4-(tert-butyl)benzamido)tetrahydro-2H-pyran-2,4, 5-Triyltriacetate (N1): white needle-like crystals, yield 47.5%, melting point 171-172°C; 1 H NMR (500MHz, CDCl 3 )δ: 1.32(s, 9H, -CH 3 ), 2.00 (s, 3H, -CH 3 ), 2.02(s, 3H, -CH 3 ), 2.05(s, 3H, -CH 3), 2.08(s, 3H, -CH 3 ), 3.81-3.87 (m, 1H, -CH), 4.14-4.18 (m, 1H, -CH 2 -), 4.28-4.31 (m, 1H, -CH 2 -), 4.49-4.54 (m, 1H, -CH), 5.20-5.25 (m, 2H, -CH), 5.79-5.82 (d, J=8.0Hz, 1H, -CH), 6.22-6.23 (d, J=4.5Hz, 1H, -NH), 7.41-7.42(d, J=8.4Hz, 2H, Ph-H), 7.47-7.49(d, J=8.4Hz, 2H, Ph-H).

Embodiment 2

[0040] (2S, 3R, 4R, 5S, 6R)-6-(Acetoxymethyl)-3-benzamidotetrahydro-2H-pyran-2,4,5-triyltriacetate (N2 ): white needle-like crystals, yield 48.0%, melting point 233-234°C; 1 H NMR (500MHz, CDCl 3 )δ: 2.02(s, 3H, -CH 3 ), 2.09 (s, 3H, -CH 3 ), 2.10 (s, 3H, -CH 3 ), 2.14(s, 3H, -CH 3 ), 3.86-3.90 (m, 1H, -CH), 4.17-4.20 (m, 1H, -CH 2 -), 4.31-4.35 (m, 1H, -CH 2 -), 4.51-4.66 (m, 1H, -CH), 5.23-5.30 (m, 2H, -CH), 5.82-5.84 (d, J=8.0Hz, 1H, -CH), 6.24-6.25 (d, J=2.6Hz, 1H, -NH), 7.43-7.47(t, J=7.2Hz, 2H, Ph-H), 7.53-7.56(m, 1H, Ph-H), 7.69-7.71(d, J= 7.1Hz, 2H, Ph-H).

Embodiment 3

[0042] (2S, 3R, 4R, 5S, 6R)-6-(Acetoxymethyl)-3-(3-nitrobenzamido)tetrahydro-2H-pyran-2,4,5-triyl Triacetate (N3): white needle-like crystals, yield 53.1%, melting point 196-197°C; 1 H NMR (500MHz, CDCl 3 )δ: 2.07(s, 3H, -CH 3 ), 2.10 (s, 3H, -CH 3 ), 2.12(s, 3H, -CH 3 ), 2.13 (s, 3H, -CH 3 ), 3.96-4.00 (m, 1H, -CH), 4.19-4.23 (m, 1H, -CH 2 -), 4.32-4.36 (m, 1H, -CH 2 -), 4.62-4.70 (m, 1H, -CH), 5.25-5.30 (m, 1H, -CH), 5.43-5.49 (m, 1H, -CH), 5.85-5.87 (d, J=8.8Hz, 1H, -CH), 6.97-7.03 (m, 1H, -NH), 7.62-7.67 (t, J = 8.2Hz, 1H, Ph-H), 8.17-8.19 (d, J = 7.7Hz, 1H, - CH), 8.31-8.33(d, J=8.2Hz, 1H, Ph-H), 8.52(s, 1H, Ph-H).

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Abstract

The invention relates to a glucosamide compound and a preparation method thereof. The glucosamide compound has a structure as shown in the formula (I). In the formula (I), R is methoxy group, nitro group, amino-group, hydroxyl group, C1-4 alkyl group or halogen, n is the number of substituent groups, and n is 1 or 2. The glucosamide compound is simple to prepare, has excellent plant induced resistance activity, and can be used as a plant induced resistance agent for controlling cucumber bacterial angular leaf spot, cucumber target leaf spot and tomato late blight. The invention also relates to a plant induced resistant agent containing the compound.

Description

(1) Technical field [0001] The invention relates to a glucose amide compound, namely 3-amino-6-(hydroxymethyl)tetrahydro-2H-glucopyranose compound and its preparation and application. (2) Background technology [0002] Glucose compounds have good development prospects in the development of new pesticides in the future, and among the glucose compounds, glucosamine compounds are the main ones. 3-Amino-6-(hydroxymethyl)tetrahydro-2H-glucopyranose compounds also have very important biological activities, which can induce active immunity in plants, and are effective against tobacco mosaic virus, rice blast fungus, black shank, nuclear Pan mold, anthracnose, etc. have broad-spectrum resistance. The application of pesticides has become one of the more and more popular research fields in recent years. Therefore, exploring the synthesis of 3-amino-6-(hydroxymethyl)tetrahydro-2H-glucopyranose compounds has important theoretical and practical value. [0003] However, there is no inf...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/08C07H5/06C07H1/00A01N43/16A01P1/00A01P3/00
CPCA01N43/16C07H1/00C07H5/06C07H13/08
Inventor 刘幸海沈钟华杨明艳余玉叶孙召慧翁建全谭成侠
Owner BEIJING BOQUANJIAN PHARMA TECH CO LTD