Preparation method and application of aryloxyphenoxypropionamide compound

A technology of aryloxyphenoxypropionamide and aryloxyphenoxy, which is applied in the field of preparation of aryloxyphenoxypropionamide compounds, can solve problems such as differences in crop varieties, and achieve the effect of strong removal effect

Inactive Publication Date: 2018-10-23
ANHUI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0021] Although there are many reports about the herbicidal activity of aryloxyphenoxypropionamide compounds and the herbicide products developed on this basis, the herbicidal activity of different kinds of aryloxyphenoxypropionamide derivatives is relatively large. Therefore, it is necessary to continuously develop new herbicide varieties to meet the needs of different types of crops.

Method used

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  • Preparation method and application of aryloxyphenoxypropionamide compound
  • Preparation method and application of aryloxyphenoxypropionamide compound
  • Preparation method and application of aryloxyphenoxypropionamide compound

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preparation example Construction

[0044] The present invention also provides a preparation method for the above-mentioned aryloxyphenoxypropionamide compounds, the steps comprising: using 2-(4-aryloxyphenyl)propionyl chloride as raw material, and 2-phenoxyethylamine, in alkali, The reaction is obtained under the conditions of acylation catalyst and reaction solvent, wherein, 2-(4-aryloxyphenyl) propionyl chloride is (R)-2-[4-(3-chloro-5-trifluoromethylpyridine-2- Oxyphenoxy]propionyl chloride is used to synthesize compound I, 2-(4-aryloxyphenyl)propionyl chloride is (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy Synthetic compound II when propionyl chloride.The reaction solvent is one or more mixtures in dichloromethane, tetrahydrofuran, chloroform, and the acylation catalyst is 4-dimethylaminopyridine (DMAP). The base is triethylamine (Et 3 N).

[0045] The general reaction formula is as follows:

[0046]

[0047] The feed ratio of 2-(4-aryloxyphenyl)propionyl chloride to 2-phenoxyethylamine is 1.2:1.

Embodiment 1

[0048]Embodiment 1: (R)-2-N-(2-phenoxyethyl)-2-[4-(3-chloro-5-trifluoromethylpyridine-2-oxyphenoxy] propionamide ( Compound I) Preparation

[0049] 0.137g (1mmol) phenoxyethylamine, 1.0mmol triethylamine, catalytic amount of 4-dimethylaminopyridine (DMAP), 20mL dichloromethane, drop 1.2mmol (R)-2-[ 4-(3-Chloro-5-trifluoromethylpyridine-2-oxyphenoxy]propionyl chloride in dichloromethane solution, dripped in about 15 minutes, and reacted at room temperature for 1 hour. After the reaction was completed, the organic layer was washed with water and saturated with salt Washing with water, drying, precipitation, the crude product was subjected to column chromatography [V petroleum ether: V ethyl acetate = 7:1 ~ 5:1] to obtain a white solid (R)-N-(4-tert-butylthiazol-2-yl )-2-[4-(3-Chloro-5-trifluoromethylpyridine-2-oxyphenoxy]propionamide, m.p.138~140°C, yield 80.1%.

[0050] 1H NMR (400MHz, CDCl 3 )δ: 7.85(d, J=2.2Hz, 1H), 7.50(dd, J=9.1, 2.2Hz, 1H), 7.29(s, 1H), 7.25(s, 1H), 7...

Embodiment 2

[0051] Example 2: (R)-2-N-(2-phenoxyethyl)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide (compound Ⅱ) preparation

[0052] 0.137g (1mmol) phenoxyethylamine, 1.0mmol triethylamine, catalytic amount of 4-dimethylaminopyridine (DMAP), 20mL dichloromethane, drop 1.2mmol (R)-2-[ 4-(6-Chloroquinoxalin-2-yloxy)phenoxy]propionyl chloride in dichloromethane solution, dripped in about 15 minutes, and reacted at room temperature for 1 hour. After the reaction was completed, the organic layer was washed with water, washed with saturated brine, dried, and precipitated. The crude product was subjected to column chromatography [V petroleum ether: V ethyl acetate = 7:1 ~ 5:1] to obtain a white solid (R)-2-N- (2-phenoxyethyl)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionamide, m.p.150~153℃, yield 78.3%, 1 HNMR (400MHz, CDCl 3 )δ: 8.65 (s, 1H, quinoxaline 3-H)), 8.03 (d, J = 2.2Hz, 1H, quinoxaline 5-H), 7.64 (d, J = 8.9Hz, 1H quinoxaline 8-H), 7.57(dd, J=8.9, 2.3Hz, 1H, quinoxa...

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Abstract

The invention discloses an aryloxyphenoxypropionamide compound and a preparation method and application thereof. The compound is (R)-2-N-(2-phenoxyethyl)-2-[4-(3-cholo-5-trifluoromethylpyridine-2-oxyphenoxy]propanamide or (R)-2-N-(2-phenoxyethyl)-2-[4-(6-chloroquinoxaline-2-yl-oxo)phenoxy]propanamide. The compound has herbicidal activity and can be used as an active ingredient of herbicide to develop a new herbicide product. Compared with the existing herbicide, the aryloxyphenoxypropionamide compound has strong removal effects on monocotyledonous weeds and can remove weeds around dicotyledonous crops without damaging the dicotyledonous crops.

Description

technical field [0001] The present invention relates to a new compound, in particular to a preparation method and application of an aryloxyphenoxypropionamide compound. Background technique [0002] There are more than 20 commercial varieties of aryloxyphenoxypropionic acid derivatives in agricultural herbicides, such as fluazifop-p-p, fenhalofop, quizalofop and clodinafop-propargyl [DE2640730, DE3004770, US4713109, EP0302203, JP54022371, EP0004414, US20030096706], but at present only cyhalofop-methyl and fenpyramid are used in wheat and rice fields. [0003] Zou Xiaomao et al [SicsinChin, 2016, 46:1226-1234] introduced morpholine, piperidine and tetrahydropyrrole rings into the structure of 2-(4-aryloxyphenoxy)propionic acid, and synthesized a class of compounds with water-oil Compatibility characteristics. Such as compound A1 at 24g / hm 2 Under the application concentration, the inhibitory rate to crabgrass and barnyardgrass can reach 100%, and can control the growth of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/643C07D241/44A01N43/40A01N43/60A01P13/00
CPCA01N43/40A01N43/60C07D213/643C07D241/44
Inventor 田胜尼杨子辉叶爱华黄世霞李军红田琪
Owner ANHUI AGRICULTURAL UNIVERSITY
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