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Diamide compound as well as preparation method and application thereof

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

Active Publication Date: 2012-08-08
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 synthesis of 2-(2-(3,4-disubstituted phenyl)(en)propionylamino)-3-methyl-N-(4-substituted phenyl)butyramide derivatives Literature reports on the study of its biological activity

Method used

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  • Diamide compound as well as preparation method and application thereof
  • Diamide compound as well as preparation method and application thereof
  • Diamide compound as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0027] Taking the preparation of IIa as an example, oxalyl chloride (2.86 g, 22.5 mmol) was added to a 50 ml single-necked bottle, and 3,4-dimethoxyphenylacetic acid IVa (2.94 g, 15 mmol) was dissolved in an ice-water bath. in 20ml of dichloromethane) was added dropwise to the reaction system, and the dripping was completed in 30 min, and reacted at room temperature for 24 h, then the solvent and excess oxalyl chloride in the reaction liquid were rotated out, and the remaining liquid was set aside, and the valine (2.11 g, 18mmol) was dissolved in 36 ml of sodium hydroxide (1.44g, 36mmol) solution, and then slowly added dropwise the remaining acid chloride solution prepared above, after 4 hours, the reaction was carried out at room temperature for 10 hours, and the pH of the reaction solution was adjusted to be about 1 , a solid was precipitated, suction filtered, and the filter cake was dried to obtain 2.98 g of white powder. IIb preparation method is similar, just R in the fo...

Embodiment 1

[0033] Example 1: 2-(3-(3,4-dimethoxyphenyl)propionylamino)-3-methyl-N-(1-phenylethyl)butyramide: (I-1) Synthesis

[0034] Add 2-(3-(3,4-dimethoxyphenyl)propionylamino)-3-methylbutanoic acid (IIa, 2.5 mmol) into 10 ml of dried dichloromethane in ice-salt Stir evenly under bath conditions, control the temperature at -15~-10°C, add triethylamine (2.75 mmol), then dropwise add isobutyl chloroformate (2.5 mmol), stir for 1 h under ice-water bath, still under the conditions , dropwise added 1-phenylethylamine (2.75 mmol dissolved in 10ml of dichloromethane), 15min to complete the drop, 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 white solid , the yield is 64%, 1 H NMR (400MHz, CDCl 3 ): δ7.33-7.30(m, 5H, Ar-H), 6.80-6.72(m, 3H, Ar-H), 6.66(s, 1H, NH), 6.39(s, 1H, NH), 5.08( s, 1H, NH CH CH 3 ), 4.26(s, 1H, (CH 3 ) 2 CH CH ), 3.86(s, 6H, OMe), ...

Embodiment 2

[0035] Embodiment 2: 2-(3-(3-methoxy-4-propynyloxyphenyl) propionylamino)-3-methyl-N-(1-phenylethyl) butyramide: ( I-2) Synthesis

[0036] 2-(3-(3-methoxy-4-propargyloxyphenyl)propionylamino)-3-methylbutanoic acid (IIb, 2.5mmol) was added to 10 ml of dried dichloromethane, Stir well under the condition of ice-salt bath, control the temperature at -15~-10°C, add triethylamine (2.75 mmol), then dropwise add isobutyl chloroformate (2.5 mmol), stir for 1 h under ice-water bath, still Under this condition, 1-phenylethylamine (2.75mmol dissolved in 10ml of dichloromethane) was added dropwise, and after 15min, the reaction was completed at room temperature for 1h, washed with 10wt% dilute hydrochloric acid, spin-dried, the crude product was recrystallized with ethanol, and suction filtered A yellow solid was obtained with a yield of 51%, 1 HNMR (400 MHz, CDCl 3 ): δ7.34-7.29(m, 5H, Ar-H), 6.99-6.72(m, 3H, Ar-H), 6.52(s, 1H, NH), 5.01(s, 1H, NH), 4.75( s, 2H, O CH 2 C≡CH), 4.29-...

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Abstract

The invention discloses a diamide compound as shown in a formula (I) and a preparation method thereof. The diamide compound can be applied as an insecticide and a bactericide and has a remarkable effect.

Description

(1) Technical field [0001] The invention relates to a preparation method of bisamide compounds, namely 2-(2-(3,4-disubstituted phenyl)propionylamino)-3-methyl-N-(4-substituted phenyl)butyl Preparation method and application of amido derivatives. (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: cinna...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/20C07C231/02A01N37/20A01P3/00A01P7/04
Inventor 刘幸海赵卫光翁建全
Owner JASAN BIO MEDICINE JIAXING CO LTD
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