Compound of N-(substituted pyridyl)amide, preparation and application thereof

A kind of amide compound and compound technology, which is applied in the field of N-amide compound and its preparation and application, and can solve the problem of no biological activity report and the like

Active Publication Date: 2007-03-14
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Patent US6316632B1 reports the preparation process of the compound of the following general formula, but there is no biological activity report

Method used

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  • Compound of N-(substituted pyridyl)amide, preparation and application thereof
  • Compound of N-(substituted pyridyl)amide, preparation and application thereof
  • Compound of N-(substituted pyridyl)amide, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0056] Example 1: Preparation of Compound 1

[0057]

[0058] At room temperature, 1.1 g of (III-1) was added dropwise to a solution of 0.6 g of triethylamine and 0.64 g of (II-1) in 20 ml of dichloromethane, and the reaction was stirred for 5 hours. Concentrate the reaction mixture under reduced pressure, add saturated aqueous sodium bicarbonate solution to the residue, extract 3 times with ethyl acetate, combine the extracts, wash 3 times with saturated brine, dry, filter, and concentrate under reduced pressure to obtain a light yellow solid as crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:4) gave 0.98 g of the title compound with a melting point of 82-84°C. Yield 70.5%.

[0059] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 ) as follows: δppm 7.22 (1H, m), 7.40 (2H, d), 7.45 (3H, m), 7.55 (4H, m), 7.86 (1H, d), 8.02 (1H, d), 8.83 (1H, d).

example 2

[0060] Example 2: Preparation of compound 32

[0061]

[0062]At room temperature, 1.1 g of (III-1) was added dropwise to a solution of 0.6 g of triethylamine and 0.96 g of (II-32) in 20 ml of dichloromethane, and the reaction was stirred for 6 hours. Concentrate the reaction mixture under reduced pressure, add saturated aqueous sodium bicarbonate solution to the residue, extract 3 times with ethyl acetate, combine the extracts, wash 3 times with saturated brine, dry, filter, and concentrate under reduced pressure to obtain a light yellow solid as crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:4) gave 1.28 g of the title compound, melting at 69-71°C. Yield 68.5%.

[0063] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 ) as follows: δppm 4.61 (2H, m), 6.96 (1H, m), 7.36 (2H, t), 7.42 (3H, m), 7.56 (4H, m), 7.76 (1H, dd), 7.83 (1H, dd), 8.75 (1H,d).

example 3

[0064] Example 3: Preparation of Compound 96

[0065]

[0066] At room temperature, 0.9 g of (III-96) was added dropwise to a solution of 0.6 g of triethylamine and 1.11 g of (II-96) in 20 ml of dichloromethane, and the reaction was stirred for 8 hours. Concentrate the reaction mixture under reduced pressure, add saturated aqueous sodium bicarbonate solution to the residue, extract 3 times with ethyl acetate, combine the extracts, wash 3 times with saturated brine, dry, filter, and concentrate under reduced pressure to obtain a light yellow solid as crude product. Column chromatography with a mixture of ethyl acetate and petroleum ether (1:3) gave 1.19 g of the title compound, melting at 112-114°C. Yield 66.2%.

[0067] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 ) as follows: δppm 7.12 (1H, dd), 7.18 (2H, d), 7.21 (2H, m), 7.44 (2H, d), 7.58 (1H, m), 7.90 (1H, dd), 8.80 (1H, dd).

[0068] Other compounds were synthesized according to the above me...

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Abstract

The present invention belongs to the field of farm germicide, and is especially one kind of N-(substitutional pyridyl) amide compounds with general expression as shown and its preparation and application. The compounds have broad spectrum germicidal activity of preventing rice blast, wheat powdery mildew, cucumber powdery mildew, cucumber gray mold, etc, especially on powdery mildew.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, and in particular relates to an N-(substituted pyridine) amide compound and its preparation and application. Background technique [0002] Pyridine is a very important heterocycle in the development of pesticides. Because the pyridine ring has good properties such as systemic, hydrophobic, and selectivity, its introduction can change the performance of the compound. Although there are many commercial species containing pyridine groups (see Clive Tomlin, The Pesticide Manual, 13th ed. 2003), there is still a need for compounds with novel structures. [0003] Patent US6316632B1 reports the preparation process of the compound of the following general formula, but there is no biological activity report. [0004] [0005] Patents WO9845268A1, WO0023420A1, EP527016A1, etc. have also reported related pyridine amine derivatives, but they are obviously different from the present invention and do...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/40A01N43/40
Inventor 刘长令迟会伟李志念欧阳津罗艳梅
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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