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2-[4-(pyridin-2-yloxy)phenoxy]amide derivative and its preparation method and application

A technology of amide derivatives and oxy groups, which is applied in the field of 2-[4-phenoxy]amide derivatives and its application in the preparation of herbicides, and can solve the problem that the herbicidal activity of phenoxy]amide derivatives has not been developed. Reporting and other issues

Active Publication Date: 2019-02-15
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 herbicidal activity of 2-[4-(pyridin-2-yloxy)phenoxy]amide derivatives (I)

Method used

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  • 2-[4-(pyridin-2-yloxy)phenoxy]amide derivative and its preparation method and application
  • 2-[4-(pyridin-2-yloxy)phenoxy]amide derivative and its preparation method and application
  • 2-[4-(pyridin-2-yloxy)phenoxy]amide derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] (R)-N-(2,2-Dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(3-chloro-5-trifluoro Preparation of methylpyridin-2-yloxy)phenoxy]propionamide

[0046]

[0047] 0.25g 2,2-dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-amine, 25mL dichloromethane, 2mL triethylamine, dropwise add (R)- 2-[4-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propionyl chloride in dichloromethane. The reaction was monitored by TLC for 1.5 h, separated by column chromatography to obtain 0.43 g of white solid (R)-N-(2,2-dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl )-2-[4-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propionamide, yield 62.3%, m.p.142~145℃; (c=1, CH 2 Cl 2 ); 1 H NMR (CDCl 3 , 500MHz) δ: 1.50(s, 6H, 2×CH 3 ), 1.67 (d, J=7.0Hz, 3H, CHCH 3 ), 3.01 (s, 2H, CH 2 ), 3.87 (s, 3H, OCH 3 ), 4.75 (q, J=7.0Hz, 1H, CH), 6.94 (d, J=1.5Hz, 1H, C 6 h 2 6-H), 7.02(d, J=1.5Hz, 1H, C 6 h 2 4-H), 7.04(d, J=9.0Hz, 2H, C 6 h 4 2,6-H), 7.14 (d, J=9.0Hz, 2H, C 6 h 4 3,5-H), 7...

Embodiment 2

[0049] (R)-N-(2,2-Dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(3-chloro-5-trifluoro Preparation of methylpyridin-2-yloxy)phenoxy]propionamide

[0050]

[0051] 0.42g 2,2-dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-amine, 25mL dichloromethane, 2mL triethylamine, dropwise add (R)- 2-[4-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propionyl chloride in dichloromethane. The reaction was monitored by TLC for 1.5 h, and separated by column chromatography to obtain 0.64 g of yellow solid (R)-N-(2,2-dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-yl )-2-[4-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propionamide, yield 57.7%, m.p.146~148℃; (c=1, CH 2 Cl 2 ); 1 H NMR (CDCl 3 , 400MHz) δ: 1.42(t, J=6.8Hz, 3H, CH 2 CH 3 ), 1.49(s, 6H, 2×CH 3 ), 1.67 (d, J=6.8Hz, 3H, CHCH 3 ), 2.99 (s, 2H, ArCH 2 ), 4.12 (q, J=6.8Hz, 2H, OCH 2 ), 4.75(q, J=6.8Hz, 1H, CH), 6.94(d, J=1.6Hz, 1H, C 6 h 2 6-H), 6.98(d, J=1.6Hz, 1H, C 6 h 2 4-H), 7.03(d, J=8.8Hz, 2H, C 6 h 4 2,...

Embodiment 3

[0053] (R)-N-(2,2-Dimethyl-7-propoxy-2,3-dihydrobenzofuran-5-yl)-2-[4-(3-chloro-5-trifluoro Preparation of methylpyridin-2-yloxy)phenoxy]propionamide

[0054]

[0055] Add (R)- 2-[4-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propionyl chloride in dichloromethane. The reaction was monitored by TLC for 1.5 h, separated by column chromatography to obtain 0.48 g of white solid (R)-N-(2,2-dimethyl-7-propoxy-2,3-dihydrobenzofuran-5-yl )-2-[4-(3-Chloro-5-trifluoromethylpyridin-2-yloxy)phenoxy]propionamide, yield 52.2%, m.p.151~153℃; (c=1, CH 2 Cl 2 ); 1 H NMR (CDCl 3 , 400MHz) δ: 1.01(t, J=7.2Hz, 3H, CH 2 CH 3 ), 1.49(s, 6H, 2×CH 3 ), 1.67 (d, J=6.8Hz, 3H, CHCH 3 ), 1.79~1.88 (m, 2H, CH 2 ), 2.99 (s, 2H, ArCH 2 ), 4.01(t, J=7.2Hz, 2H, OCH 2 ), 4.75(q, J=6.8Hz, 1H, CH), 6.94(d, J=1.6Hz, 1H, C 6 h 2 6-H), 6.98(d, J=1.6Hz, 1H, C 6 h 24-H), 7.04(d, J=8.8Hz, 2H, C 6 h 4 2, 6-H), 7.14 (d, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.97 (d, J=2.0Hz, 1H, C 5 h 2 N 6-H), ...

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PUM

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Abstract

The invention relates to 2-[4-(pyridyl-2-yl oxyl)phenoxyl]amide derivatives having a chemical structural formula I shown in the description, wherein R and R<1> are selected from C1-C2 alkyl groups, C3-C4 straight chain alkyl groups or C3-C4 branched chain alkyl groups; R<2> is selected from H, C1-C2 alkyl groups, C3-C4 straight chain alkyl groups or C3-C4 branched chain alkyl groups; X<1>, X<2>, X<4>, and X<6> are selected from H and C1-C2 alkyl groups; X<3> is selected from H, C1-C2 alkyl groups, fluorine, chlorine, bromine or iodine; X<5> is selected from H, C1-C2 alkyl groups, trifluoromethyl, fluorine, chlorine, bromine or iodine; n is selected from 0, 1 or 2; and m is selected from 0 or 1. The invention also relates to application of the 2-[4-(pyridyl-2-yl oxyl)phenoxyl]amide derivatives in preparation of herbicides.

Description

technical field [0001] The present invention relates to a class of novel compounds and their uses, specifically 2-[4-(pyridin-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, E...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A01N43/40C07D307/83A01P13/00
CPCA01N43/40C07D307/83C07D405/12
Inventor 胡艾希林定李贝贝叶姣欧晓明
Owner HUNAN UNIV
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