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Bisamide type compound and application thereof

A compound and amide technology, applied in the field of preparation of bisamide compounds

Active Publication Date: 2012-08-01
JASAN BIO MEDICINE JIAXING CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there is no literature report on the synthesis and biological activity of 3-methyl-N-(1-phenylethyl)-2-(2-(4-substituted phenyl) acetamido) butyramide derivatives

Method used

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  • Bisamide type compound and application thereof
  • Bisamide type compound and application thereof
  • Bisamide type compound and application thereof

Examples

Experimental program
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preparation example Construction

[0027] Taking the preparation of IIa as an example, oxalyl chloride (2.86g, 22.5mmol) was added to a 50ml single-necked bottle, and phenylacetic acid IVa (2.04g, 15mmol dissolved in 20ml of dichloromethane) was added dropwise in an ice-water bath. Into the reaction system, after 30 minutes of dripping, react at room temperature for 24 hours, then spin out the solvent and excess oxalyl chloride in the reaction solution, and the remaining liquid is for subsequent use. Dissolve valine (2.11g, 18mmol) in 36ml of sodium hydroxide (1.44 g, 36mmol) solution, then slowly drop in the above-mentioned prepared acid chloride residual liquid, drop it in 4h, react at room temperature for 10h, adjust the pH of the reaction solution to be about 1, solids are precipitated, suction filtered, and the filter cake is dried to obtain White powder 2.9g g. The preparation methods of IIb and IIc are similar, except that R in the formula IV 1 Respectively for the corresponding substituent groups, that...

Embodiment 1

[0034] Embodiment 1: 3-Methyl-N-(1-phenylethyl)-2-(2-(4-propargyloxyphenyl) acetamido) butyramide: Synthesis of (I-1)

[0035] 2-(2-(4-propargyloxyphenyl)acetamido)-3-methylbutanoic acid (2.5mmol) was added to 10ml of dried dichloromethane, stirred evenly under ice-salt bath conditions, Control the temperature at -15~-10°C, add triethylamine (2.75mmol), then dropwise add isobutyl chloroformate (2.5mmol), stir in an ice-water bath for 1h, and still under this condition, add dropwise 1-benzene Ethylamine (2.75mmol dissolved in 10ml of dichloromethane), dripped for 15min, reacted at room temperature for 1h, washed with 10wt% dilute hydrochloric acid, spin-dried, the crude product was recrystallized with ethanol, and suction filtered to obtain a khaki solid with a yield of 67 %, 1 H NMR (400MHz, CDCl 3 ): δ7.36-7.25 (m, 5H, Ar-H), 7.20 (d, J=8.0Hz, 2H, Ar-H), 6.95 (d, J=8.4Hz, 2H, Ar-H), 6.64 (s, 1H, NH), 6.32 (s, 1H, NH), 5.07-5.04 (m, 1H, NH CH CH 3 ), 4.69 (s, 2H, O CH 2...

Embodiment 2

[0036] Example 2: 3-methyl-2-(2-(4-propargyloxyphenyl) acetamido)-N-(1-(p-tolyl) ethyl) butyramide: (I-2) Synthesis

[0037] 2-(2-(4-propargyloxyphenyl)acetamido)-3-methylbutanoic acid (2.5mmol) was added to 10ml of dried dichloromethane, stirred evenly under ice-salt bath conditions, Control the temperature at -15~-10°C, add triethylamine (2.75mmol), then dropwise add isobutyl chloroformate (2.5mmol), stir in an ice-water bath for 1h, still under this condition, add dropwise 1-( 4-Methylphenyl)ethylamine (2.75mmol dissolved in 10ml of dichloromethane), after 15 minutes of dripping, reacted at room temperature for 1h, washed with 10wt% dilute hydrochloric acid, spin-dried, the crude product was recrystallized with ethanol, and filtered to obtain soil Yellow solid, 50% yield, 1 H NMR (400MHz, CDCl 3 ): δ7.22-7.15 (m, 6H, Ar-H), 6.96 (t, J=8.4Hz, 2H, Ar-H), 6.24 (dd, J 1 =8.4Hz,J 2 = 17.2Hz, 1H, NH), 6.07(dd, J 1 =8.0Hz,J 2 =20.8Hz, 1H, NH), 5.06-4.99 (m, 1H, NH CH CH 3...

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Abstract

The invention discloses a bisamide type compound which is shown as a formula (I) and discloses a preparation method thereof. The bisamide type compound provided by the invention can be applied as an insecticide and has an obvious effect.

Description

(1) Technical field [0001] The present invention relates to a kind of preparation method of bisamide compound namely 3-methyl-N-(1-phenethyl)-2-(2-(4-substituted phenyl) acetamido) butyramide derivative Preparation method and application. (2) Background technology [0002] Pesticides play an important role in human life, food production, and environmental protection. In order to improve human life, increase the yield per unit area of ​​crops, and prevent environmental degradation, it is necessary to develop and create newer, more efficient, and safer agrochemicals. Taste. At the same time, as people use pesticides for a long time, the problem of resistance is becoming more and more serious, and the seriousness of pesticides to soil pollution is also increasing, so there is an urgent need to continuously research and develop new pesticides. [0003] Carboxylic acid amide fungicides are new fungicides developed in recent years. It contains three types of amides: cinnamic ami...

Claims

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Application Information

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IPC IPC(8): C07C237/22C07C231/02A01N37/18A01P7/04
Inventor 刘幸海赵卫光翁建全
Owner JASAN BIO MEDICINE JIAXING CO LTD
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