n-(Oxoethyl)-2-[4-(pyridin-2-yloxy)phenoxy]amide derivatives

A technology of amide derivatives and oxoethyl groups, which can be applied to biocides, chemicals for biological control, biocides, etc., and can solve the problem that the herbicidal activity of amide derivatives has not been reported.

Inactive Publication Date: 2018-05-08
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The herbicidal activity of N-(oxoethyl)-2-[4-(pyridin-2-yloxy)phenoxy]amide derivatives has not been reported

Method used

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  • n-(Oxoethyl)-2-[4-(pyridin-2-yloxy)phenoxy]amide derivatives
  • n-(Oxoethyl)-2-[4-(pyridin-2-yloxy)phenoxy]amide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of 2-amino-1-(2,2-dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl)ethanone hydrochloride (1a)

[0023]

[0024] 3.50g urotropine, 40mL chloroform, stirred at 45°C, added dropwise 20ml of 6.00g compound 2a chloroform solution, monitored by TLC, the reaction was complete, filtered, and dried to obtain 7.40g white solid; 7.40g white solid, 30mL Ethanol, 20.00g of 36% hydrochloric acid, stirred and refluxed for 4.0h, filtered while hot, cooled the filtrate, precipitated solid, filtered and dried to obtain 3.70g of white solid 2-amino-1-(2,2-dimethyl-7-methoxy -2,3-Dihydrobenzofuran-5-yl)ethanone hydrochloride 1a, yield 58.6%, m.p.157~159℃. 1 H NMR (CDCl 3 , 400MHz) δ: 1.46(s, 6H, 2×CH 3 ), 3.08 (s, 2H, ArCH 2 ), 3.82 (s, 3H, OCH 3 ), 4.51 (d, J=5.2Hz, 2H, COCH 2 ), 7.40 (s, 1H, C 6 h 2 4-H), 7.56(s, 1H, C 6 h 2 6-H), 8.17(s, 2H, NH 2 ).

Embodiment 2

[0026] Preparation of 2-amino-1-(2,2-dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-yl)ethanone hydrochloride (1b)

[0027]

[0028] The operation was the same as in Example 1, and the reaction was carried out for 4.5 hours to obtain 3.00 g of white solid 2-amino-1-(2,2-dimethyl-7-ethoxy-2,3-dihydrobenzofuran-5-yl) Ethanone hydrochloride 1b, yield 47.2%, m.p.220-223°C. 1 H NMR (CDCl 3, 500MHz) δ: 1.34(t, 3H, J=7.0Hz, CH 3 ), 1.46(s, 6H, 2×CH 3 ), 3.08 (s, 2H, ArCH 2 ), 4.12 (q, 2H, J=7.0Hz, OCH 2 ), 4.47 (d, J=4.5Hz, 2H, COCH 2 ), 7.43 (s, 1H, C 6 h 2 4-H), 7.58(s, 1H, C 6 h 2 4-H), 8.51(s, 2H, NH 2 ).

Embodiment 3

[0030] Preparation of 2-amino-1-(2,2-dimethyl-7-propoxy-2,3-dihydrobenzofuran-5-yl)ethanone hydrochloride (1c)

[0031]

[0032] The operation was the same as in Example 1, and the reaction was carried out for 4.5 hours to obtain 3.03 g of white solid 2-amino-1-(2,2-dimethyl-7-propoxy-2,3-dihydrobenzofuran-5-yl) Ethanone hydrochloride 1c, yield 52.9%, m.p.288~292°C. 1 H NMR (CDCl 3 , 500MHz) δ: 0.97(t, 3H, J=7.0Hz, CH 3 ), 1.46(s, 6H, 2×CH 3 ), 1.70~1.77 (m, 2H, CH 2 CH 3 ), 3.08 (s, 2H, ArCH 2 ), 4.02(t, 2H, J=7.0Hz, OCH 2 ), 4.48 (d, J=5.5Hz, 2H, COCH 2 ), 7.42(s, 1H, C 6 h 2 4-H), 7.58(s, 1H, C 6 h 2 6-H), 8.51(s, 2H, NH 2 ).

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Abstract

The invention discloses a N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative of a chemical structure formula I as shown in the specification, in the formula, R and R2 are selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl; R1 and R3 are selected from C1-C2 alkyl, C3-C4linear alkyl or C3-C4 branched alkyl; R1 and R3 are selected from C1-C2 alkyl, C3-C4 linear alkyl or C3-C4 branched alkyl; X1, X2, X4 and X6 are selected from hydrogen and C1-C2 alkyl; X3 is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine or iodine; X5 is selected from hydrogen, C1-C2 alkyl, trifluoromethyl, fluorine, chlorine, bromine or iodine. The N-(oxo-ethyl)-2-[4-(pyridine-2-yl-oxy)phenoxy]amide derivative can be used for preparing herbicides.

Description

technical field [0001] The present invention relates to a class of novel compounds and their preparation methods and applications, specifically N-(oxoethyl)-2-[4-(pyridin-2-yloxy)phenoxy]amide derivatives and their Preparation method and application in preparation of herbicide. Background technique [0002] 4-Aryloxyphenoxyalkanoic acid derivatives have a wide range of biological activities, and aryloxyphenoxypropionic acid derivatives are their typical representatives, and there are more than 20 commercial varieties in agricultural herbicides [DE2640730, DE3004770 , US4713109, EP302203, JP54022371, EP4414, US 20030096706]. The main mode of action of 4-aryloxyphenoxy carboxylic acid derivatives is to inhibit plant acetyl-CoA carboxylase, thereby affecting the synthesis of plant fatty acids and causing plant death to achieve the purpose of weeding. Liu Changling et al. [CN 101747263B, 2012-1-11] prepared compound G, which has good fungicidal activity, and at a concentration...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A01N43/40A01P13/00
CPCA01N43/40C07D405/12
Inventor 胡艾希陈爱羽李贝贝杨子辉李永红
Owner HUNAN UNIV
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