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Preparation method and application of 6-chloropyrazine-2-amide compounds containing diphenyl ether groups

A technology of amide compounds and chloropyrazine, which is applied in the field of preparation and application of 6-chloropyrazine-2-amide compounds containing diphenyl ether groups, and can solve the problems of no research report on herbicidal activity and the like

Inactive Publication Date: 2018-12-14
陈磊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Regarding the herbicidal activity of 6-chloro-N-(2-phenoxyphenyl)pyrazine-2-carboxamide and 6-chloro-N-(4-phenoxyphenyl)pyrazine-2-carboxamide No research report

Method used

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  • Preparation method and application of 6-chloropyrazine-2-amide compounds containing diphenyl ether groups
  • Preparation method and application of 6-chloropyrazine-2-amide compounds containing diphenyl ether groups
  • Preparation method and application of 6-chloropyrazine-2-amide compounds containing diphenyl ether groups

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 6-chloro-N-(2-phenoxyphenyl)pyrazine-2-carboxamide:

[0027] Add 2-phenoxyaniline (0.185g, 1.0mmol), 6-chloropyrazine-2-carboxylic acid (0.158g, 1.0mmol) and 30mL dichloromethane in the reaction flask, add Et 3 N (0.202g, 2.0mmol), then added EDCI (0.287mg, 1.5mmol), HOBt (0.20g, 1.5mmol), reacted at 25°C for 2.5 hours, TLC detected that the reaction was complete, the reaction was complete, and the reaction solution was washed twice with water , washed once with saturated brine, dried the organic phase with anhydrous sodium sulfate, precipitated to obtain a crude product, recrystallized from ethanol to obtain a brick red solid, m.p.138-140°C, yield 79.0%, 1 H-NMR (400MHz, CDCl 3 )δ: 9.62(s,1H,NH), 9.58(s,1H,pyrazine), 8.83(s,1H,pyrazine), 8.54(s,1H,C 6 h 4 ), 7.82 (d, J=8.4Hz, 2H, C 6 h 4 ), 7.33–7.42 (m,2H,C 6 h 4 ), 7.00–7.15 (m,4H,C 6 h 5 ).HRMS(EI)(calcd.m / z): 325.0612(325.0618,M + ).

Embodiment 2

[0029] Preparation of 6-chloro-N-(4-phenoxyphenyl)pyrazine-2-carboxamide:

[0030] Add 4-phenoxyaniline (0.185g, 1.0mmol), 6-chloropyrazine-2-carboxylic acid (0.158g, 1.0mmol) and 30mL dichloromethane in the reaction flask, add Et 3 N (0.202g, 2.0mmol), then added EDCI (0.287mg, 1.5mmol), HOBt (0.20g, 1.5mmol), reacted at 25°C for 2.0 hours, TLC detected that the reaction was complete, and the reaction was completed, and the reaction solution was washed twice with water , washed once with saturated brine, dried the organic phase with anhydrous sodium sulfate, and desolvated to obtain a crude product, which was recrystallized from ethanol to obtain a white solid, m.p.160-162°C, yield 83.0%, 1 H-NMR (400MHz, CDCl 3 )δ: 9.66(s,1H,NH), 9.53(s,1H,pyrazine), 8.82(s,1H,pyrazine), 8.61(s,1H,C 6 h 4 ), 7.74 (d, J=8.4Hz, 2H, C 6 h 4 ), 7.31–7.39 (m,2H,C 6 h 4 ), 6.95–7.13 (m, 4H, C 6 h 5 ).HRMS(EI)(calcd.m / z): 325.0610(325.0618,M + ).

Embodiment 3

[0032] Determination of Herbicidal Activity of 6-Chloropyrazine-2-amide Compounds Containing Diphenyl Ether Group

[0033] Test design

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Abstract

The invention discloses 6-chloropyrazine-2-amide compounds containing diphenyl ether groups, and the compounds have the following general formulas. The preparation method comprises the following specific steps: taking 2-phenoxyaniline and 4-phenoxylaniline as raw materials, and respectively carrying out one-step reactions with 6-chloropyrazine-2-carboxylic acid under a condition of an alkali, a condensing agent and an organic solvent to synthesize a target compound (I) and a target compound (II). The compounds disclosed by the invention have relatively good herbicidal activity, particularly have certain prevention effects on dicotyledonous weeds under a usage amount of 2000 g / hm<2>, and can be used for preparing herbicides.

Description

technical field [0001] The present invention relates to a class of novel compounds and their uses, in particular to the preparation method of 6-chloropyrazine-2-amide compounds containing diphenyl ether groups and their application in the preparation of herbicides. Background technique [0002] Pyrazinamide compounds have a wide range of pharmaceutical and pesticide activities. In the field of pesticides, Nippon Nosho Co., Ltd. launched Pyraziflumid in 2014 with the development code NNF-0721. Mainly used for rice, fruit trees, vegetables and lawns, etc., to prevent and control powdery mildew, scab, gray mold, sclerotinia, ring spot, fruit spot and dollar spot, etc. The dosage of active ingredients is 100-375g / hm 2 , is a fungicide variety with market potential. [0003] [0004] In recent years, existing literature has reported that pyrazinamide compounds have potential herbicidal activity, and in 2005 Tumova et al. -5 There is better herbicidal activity under mol / L c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/24A01N43/60A01P13/00
CPCA01N43/60C07D241/24
Inventor 陈磊
Owner 陈磊
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