2-[4-(quinoxaline-2-yloxy)phenoxy]amide derivatives and preparation method and application thereof

A technology of amide derivatives and base oxy groups, applied in the field of 2-[4-phenoxy]amide derivatives and its application in the preparation of herbicides, can solve the problem of 2-[4-(quinoxaline-2 -yloxy)phenoxy]amide derivatives herbicidal activity has no research and development reports and other issues

Active Publication Date: 2017-03-08
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] There is no research and development report on the herbici

Method used

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  • 2-[4-(quinoxaline-2-yloxy)phenoxy]amide derivatives and preparation method and application thereof
  • 2-[4-(quinoxaline-2-yloxy)phenoxy]amide derivatives and preparation method and application thereof
  • 2-[4-(quinoxaline-2-yloxy)phenoxy]amide derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (R)-N-(2,2-Dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(6-chloroquinoxaline-2- Preparation of oxy)phenoxy]propionamide

[0045]

[0046] Add (R)- 2-[4-(6-Chloroquinoxalin-2-yloxy)phenoxy]propionyl chloride in dichloromethane. The reaction was monitored by TLC for 1.5 h, and separated by column chromatography to obtain 0.28 g of gray solid (R)-N-(2,2-dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl )-2-[4-(6-Chloroquinoxalin-2-yloxy)phenoxy]propionamide, yield 45.2%, m.p.161~164℃; (c=1, CH 2 Cl 2 ); 1 H NMR (CDCl 3 , 400MHz) δ: 1.50(s, 6H, 2×CH 3 ), 1.69 (d, J=6.8Hz, 3H, CHCH 3 ), 3.02(s, 2H, CH 2 ), 3.87 (s, 3H, OCH 3 ), 4.78(q, J=6.8Hz, 1H, CH), 6.96(s, 1H, C 6 h 2 6-H), 7.04(s, 1H, C 6 h 2 4-H), 7.07(d, J=8.8Hz, 2H, C 6 h 4 2,6-H), 7.25 (d, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.60 (dd, J 1 =8.8Hz,J 2 =2.0Hz, 1H, quinoxaline 7-H), 7.68(d, J=8.8Hz, 1H, quinoxaline 8-H), 8.05(d, J=2.0Hz, 1H, quinoxaline 5-H ), 8.11 (s, 1H, NH), 8.69 (s, 1H, quinoxa...

Embodiment 2

[0048] (R)-N-(2,2-Dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(6-chloroquinoxaline-2- Preparation of oxy)phenoxy]propionamide

[0049]

[0050] Add (R)- 2-[4-(6-Chloroquinoxalin-2-yloxy)phenoxy]propionyl chloride in dichloromethane. The reaction was monitored by TLC for 1.5 h, separated by column chromatography to obtain 0.35 g of gray solid (R)-N-(2,2-dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-yl )-2-[4-(6-Chloroquinoxalin-2-yloxy)phenoxy]propionamide, yield 48.6%, m.p.176~178°C; (c=1, CH 2 Cl 2 ); 1 H NMR (CDCl 3 , 400MHz) δ: 1.43(t, J=6.8Hz, 3H, CH 2 CH 3 ), 1.50(s, 6H, 2×CH 3 ), 1.69 (d, J=6.8Hz, 3H, CHCH 3 ), 3.00 (s, 2H, ArCH 2 ), 4.13 (q, J=6.8Hz, 2H, OCH 2 ), 4.78(q, J=6.8Hz, 1H, CH), 6.97(s, 1H, C 6 h 2 6-H), 7.01(s, 1H, C 6 h 2 4-H), 7.06(d, J=8.8Hz, 2H, C 6 h 4 2,6-H), 7.24(d, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.60 (dd, J 1 =8.8Hz,J 2 =2.4Hz, 1H, quinoxaline 7-H), 7.68(d, J=8.8Hz, 1H, quinoxaline 8-H), 8.05(d, J=2.4Hz, 1H, quinoxaline 5-H ...

Embodiment 3

[0052] (R)-N-(2,2-Dimethyl-7-propoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(6-chloroquinoxaline-2- Preparation of oxy)phenoxy]propionamide

[0053]

[0054] Add (R)- 2-[4-(6-Chloroquinoxalin-2-yloxy)phenoxy]propionyl chloride in dichloromethane. The reaction was monitored by TLC for 1.5 h, separated by column chromatography to obtain 0.61 g of yellow solid (R)-N-(2,2-dimethyl-7-propoxy-2,3-dihydrobenzofuran-5-yl )-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide, yield 58.7%, m.p.166~169℃; (c=1, CH 2 Cl 2 ); 1 H NMR (CDCl 3 , 400MHz) δ: 1.01(t, J=7.2Hz, 3H, CH 2 CH 3 ), 1.50(s, 6H, 2×CH 3 ), 1.69 (d, J=6.8Hz, 3H, CHCH 3 ), 1.79~1.88 (m, 2H, CH 2 ), 3.00 (s, 2H, ArCH 2 ), 4.01(t, J=6.8Hz, 2H, OCH 2 ), 4.77(q, J=6.8Hz, 1H, CH), 6.97(s, 1H, C 6 h 2 6-H), 7.01(s, 1H, C 6 h 2 4-H), 7.06(d, J=8.8Hz, 2H, C 6 h 4 2,6-H), 7.24(d, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.60 (dd, J 1 =8.8Hz,J 2 =2.0Hz, 1H, quinoxaline 7-H), 7.68(d, J=8.8Hz, 1H, quinoxaline 8-H), 8.05(d, ...

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Abstract

The invention relates to 2-[4-(quinoxaline-2-yloxy)phenoxy]amide derivatives shown in chemical structural formula I shown in the specification, wherein R and R1 are selected from C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl, R2 is selected from H, C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl, X1-X3 and X5-X6 are selected from hydrogen and C1-C2 alkyl, X4 is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, and bromine, n is selected from 0, 1 or 2, and m is selected from 0 or 1. Application of 2-[4-(quinoxaline-2-yloxy)phenoxy]amide derivatives in the preparation of herbicides is also disclosed.

Description

technical field [0001] The present invention relates to a class of novel compounds and their uses, specifically 2-[4-(quinoxalin-2-yloxy)phenoxy]amide derivatives and their use in the preparation of herbicides. Background technique [0002] 4-Aryloxyphenoxycarboxylic acid derivatives have good biological activity [2-(4-aryloxyphenoxy)alkanamide and its application, Chinese invention patent, ZL201310041239.9, authorized on May 14, 2014; 2 -[4-(Benzoxazol-2-yloxy)phenoxy]alkanamide and its application, Chinese invention patent, ZL201310040974.8, authorized on 20148.13; N-picolyl / methoxy-2-benzene Medical use of oxyamide, Chinese invention patent, ZL201310437071.3, authorized on October 22, 2014; medical use of N-thiazolemethyl / methoxy-2-phenoxyamide, ZL201310437111.4, authorized on May 13, 2015]; Among them, there are more than 20 commercial varieties of aryloxyphenoxypropionic acid derivatives in agricultural herbicides [DE2640730, DE3004770, US4713109, EP0302203, JP54022371...

Claims

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Application Information

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IPC IPC(8): C07D405/12A01P13/00C07D307/86
CPCC07D307/86C07D405/12
Inventor 胡艾希陈爱羽李贝贝叶姣欧晓明
Owner HUNAN UNIV
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