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Aryloxyphenoxies propionate compound and its preparation method and application

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

Inactive Publication Date: 2017-09-19
赣州市正畅塑胶有限公司
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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][1,3]dioxa-5-methyl-2-(4-(6-chloroquinoxalin-2-yloxy)phenoxy)propionate has no herbicidal activity R & D report

Method used

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  • Aryloxyphenoxies propionate compound and its preparation method and application
  • Aryloxyphenoxies propionate compound and its preparation method and application
  • Aryloxyphenoxies propionate compound and its preparation method and application

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 10mL dichloromethane solution containing 1.2mmol 2-(4-(6-chloroquinoxalin-2-yloxy)phenoxy)propionyl chloride under the conditions, and drop it in about 25min. After 3.0h, 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%, (c=1, CH 2 C...

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]diox-5-methyl-2-(4-((6-chloropyridin-2-yl) Oxygen) phenoxy) propionate, yield 75.1%. (c=1, CH 2 Cl 2 ); 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 ,...

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Abstract

The invention discloses a piperonyl-containing aryloxyphenoxies propionate compound, which has the following structure: the formula is shown in the specification. The specific preparation method includes steps of taking catechol as raw material, and compounding heliotropin through two-step reaction; performing reduction reaction with NaBH4 to prepare 3, 4- methylenedioxy phemethylol; reacting 2-(4-aryloxyphenoxies) propionyl chloride with prepare 3, 4- methylenedioxy phemethylol to prepare two piperonyl-containing aryloxyphenoxies propionate compounds. The compound has good weeding activity; especially, the weeding activity of monocotyledon weed is better than that of dicotyledonous weed; the preparation method is simple to operate, and the yield is high.

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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A01P13/00
CPCC07D405/12
Inventor 杨子辉田昊张莉王晓凤程学军何曼王佳琦魏坤
Owner 赣州市正畅塑胶有限公司
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