Aryloxy-phenoxy propionate compounds and preparation method and application thereof

A technology of aryloxyphenoxypropionate and aryloxyphenyl, which is applied to aryloxyphenoxypropionate compounds and the fields of their preparation and application, and can solve problems such as no research and development reports on herbicidal activity.

Inactive Publication Date: 2017-07-25
杨子辉
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] (R)-Benzo[d][1,3]dioxa-5-methyl-2-(4-((6-chloropyridin-2-yl)oxy)phenoxy)propionate and ( R)-Benzo[d][1

Method used

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  • Aryloxy-phenoxy propionate compounds and preparation method and application thereof
  • Aryloxy-phenoxy propionate compounds and preparation method and application thereof
  • Aryloxy-phenoxy propionate compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of pepper rings

[0036] Under the catalysis of tetrabutylammonium bromide (TBAB), dimethyl sulfoxide is used as a solvent, mixed with dichloromethane evenly, and the reaction is heated to 110 ° C, and dimethyl sulfoxide containing catechol is added dropwise to it at the same time. The sulfone solution and 50% inorganic alkali solution continue to react for about 3 hours, then stop the reaction, add water, continue heating and distilling, and collect fractions at 99-104°C. The distillate was treated to obtain pepper rings with a yield of 85.6%.

[0037] Preparation of piperonal:

[0038] Synthesis of N-methylbenzamide from N-methylaniline: Put 5.0g N-methylaniline, 5.0g 85% formic acid and 20ml toluene into a 100ml three-necked flask, and slowly raise the temperature to reflux under stirring. After about 5 minutes of reflux, the reflux liquid is continuously separated from the water through the water separator, and the toluene is returned to the reaction b...

Embodiment 2

[0043] Preparation of (R)-benzo[d][1,3]dioxa-5-methyl-2-(4-(6-chloroquinoxalin-2-yloxy)phenoxy)propionate

[0044]

[0045]0.152g (1.0mmol) of 3,4-methylenedioxybenzyl alcohol was dissolved in 30mL of dichloromethane, after stirring for 5min, 1.0mmol of triethylamine was added, and a catalytic amount of 4-dimethylaminopyridine (DMAP) was added in an ice bath Add dropwise a 10mL dichloromethane solution containing 1.2mmol 2-(4-(6-chloroquinoxalin-2-yloxy)phenoxy)propionyl chloride under conditions, and drop it in about 25 minutes. After 3.0 hours, the reaction is complete. , the organic layer was washed once with dilute hydrochloric acid, washed three times with saturated brine, and the organic layer was washed with Na 2 SO 4 dry. Desolvation, the crude product was subjected to column chromatography [V 石油醚 :V 乙酸乙酯 =7:1~5:1] to obtain white solid (R)-benzo[d][1,3]diox-5-methyl-2-(4-(6-chloroquinoxalin-2-yloxy Base) phenoxy) propionate, m.p.111~113°C, yield 79.3%, 1 ...

Embodiment 3

[0047] Preparation of (R)-benzo[d][1,3]dioxa-5-methyl-2-(4-((6-chloropyridin-2-yl)oxy)phenoxy)propionate

[0048]

[0049] The preparation method is the same as in Example 2, 0.152g (1.0mmol) 3,4-methylenedioxybenzyl alcohol, 1.0mmol triethylamine, catalytic amount of 4-dimethylaminopyridine (DMAP), 20mL dichloromethane, Add 1.2mmol (R)-2-(4-((6-chloropyridin-2-yl)oxy)phenoxy)propionyl chloride solution in dichloromethane dropwise under ice-bath condition, drop it in about 15 minutes, and Reaction 1.0h. After completion of the reaction, the organic layer was washed with dilute hydrochloric acid, washed with saturated brine, dried, and precipitated, and the crude product was subjected to column chromatography [V 石油醚 :V 乙酸乙酯 =7:1~5:1] to obtain oily liquid (R)-benzo[d][1,3]dioxa-5-methyl-2-(4-((6-chloropyridin-2-yl) Oxygen) phenoxy) propionate, yield 75.1%. 1 H NMR (400MHz, CDCl 3 )δ: 7.59 (d, J=2.2Hz, 1H, pyridine-H),) 6.97-7.08 (m, 3H, C 6 h 4, pyridine-H), 6.86 (d...

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Abstract

The invention discloses aryloxy-phenoxy propionate compounds containing piperonyl. The compounds have a following structure. The preparation method specifically includes following preparation steps: using catechol as a raw material; synthesizing heliotropin through two-step reaction; enabling heliotropin to be in reductive reaction with NaBH4 to prepare 3, 4-methylene dioxybenzyl alcohol; enabling 2-(4-aromatic oxygen phenyl) propionyl chloride to react with 3, 4-methylene dioxybenzyl alcohol to prepare two aryloxy-phenoxy propionate compounds containing piperonyl. The compounds have higher weeding activity, especially for monocotyledon weed than dicotyledon weed. The preparation method is simple to operate and high in yield.

Description

technical field [0001] The present invention relates to a class of novel compounds and their uses, in particular to piperonyl-containing aryloxyphenoxy propionate derivatives and their use in the preparation of herbicides. 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[Sic sin Chin,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 The characteristics of water and oil solubility. Such as compound A1 at 24g / hm 2 Under the application concentration, the inhibitory rate to crabgrass and...

Claims

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Application Information

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IPC IPC(8): C07D405/12A01N43/60A01N43/40A01P13/00
CPCC07D405/12A01N43/40A01N43/60
Inventor 杨子辉田昊张莉王晓凤程学军何曼王佳琦魏坤
Owner 杨子辉
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