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Pyridyloxy phenoxy propionamide compound with herbicidal activity and synthesis method and application thereof

A synthesis method and compound technology, applied in herbicides and algicides, botanical equipment and methods, organic chemistry, etc., can solve problems such as production and storage restrictions, and achieve good control performance and the effect of small dosage

Inactive Publication Date: 2020-10-09
JIANGSU FUDING CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, clodinafop-propargyl is easily hydrolyzed under alkaline conditions, which limits its production and preservation.

Method used

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  • Pyridyloxy phenoxy propionamide compound with herbicidal activity and synthesis method and application thereof
  • Pyridyloxy phenoxy propionamide compound with herbicidal activity and synthesis method and application thereof
  • Pyridyloxy phenoxy propionamide compound with herbicidal activity and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Add 322g of toluene and 115.8g of compound IV into a 1000ml three-necked flask, stir at a temperature of 60-65°C for 30min, add 119g of thionyl chloride dropwise within about 1 hour, and after the addition is complete, raise the temperature to 80°C and keep it for 2h to obtain The reaction solution of compound I.

[0045]Add 62.5g of compound II, 230g of toluene, and 120g of sodium hydroxide into a 2000ml three-neck flask, stir; keep the temperature at 20-25°C, and add the reaction solution containing compound I dropwise to the mixed solution containing compound II within about 1.5 hours After the dropwise addition, keep warm at 20-25°C for 2h. After the reaction is over, filter to remove the inorganic salts and excessive inorganic bases generated by the reaction, add 10% hydrochloric acid dropwise to the filtrate to adjust the pH value to 2, separate layers, rotate the organic phase, add 300g of 90% ethanol, crystallize at 0-5 ° C, filter, After drying, 196 g of compo...

Embodiment 2

[0049] Add 322g of toluene and 115.8g of compound Ⅳ into a 1000ml three-neck flask, stir at a temperature of 60-65°C for 30min, add 89.2g of thionyl chloride dropwise within about 1 hour, after the addition is complete, raise the temperature to 80°C and keep it for 2h, and set aside .

[0050] Add 62.5g of compound II, 230g of toluene, and 120g of sodium hydroxide into a 2000ml three-neck flask, stir, keep the temperature at 20-25°C, and add the reaction solution containing compound I dropwise to the mixed solution containing compound II within about 1.5 hours After the dropwise addition, keep warm for 2h. After the reaction is completed, filter, add 10% hydrochloric acid dropwise to the filtrate to adjust the pH value to 2, separate layers, rotate the organic phase, add 300g 90% ethanol, crystallize at 0-5°C, filter, and dry to obtain 202g of finished product with a content of 98.2%. The rate is 96.46%.

Embodiment 3

[0052] Add 322g of toluene and 115.8g of compound Ⅳ into a 1000ml three-neck flask, stir at a temperature of 60-65°C for 30min, add 89.2g of thionyl chloride dropwise within about 1 hour, after the addition is complete, raise the temperature to 80°C and keep it for 2h, and set aside .

[0053] Add 62.5g of compound II, 230g of toluene, and 168g of potassium hydroxide into a 2000ml three-necked flask, stir, keep the temperature at 20-25°C, and add the reaction solution containing compound I dropwise to the mixed solution containing compound II within about 1.5 hours After the dropwise addition, keep warm for 2h. After the reaction is completed, filter, add 10% hydrochloric acid dropwise to the filtrate to adjust the pH value to 2, separate layers, rotate the organic phase, add 300 g of 90% ethanol, crystallize at 0-5 ° C, filter, and dry to obtain 194 g of finished product with a content of 97.4%. The rate is 92.64%.

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Abstract

The invention discloses a pyridyloxy phenoxy propionamide compound with herbicidal activity. The pyridyloxy phenoxy propionamide compound is shown as a structural formula (III). The invention also discloses application of the compound in crop weeding, preferably application in prevention and removal of gramineous weeds and broadleaf weeds, and more preferably application in prevention and removalof gramineous weeds such as barnyard grass, moleplant seeds, crab grass and the like and broadleaf weeds in rice and wheat fields. The compound is stable under acid and alkali conditions, has good prevention and treatment performance on gramineous weeds such as barnyard grass, moleplant seeds and digitaria sanguinalis, is small in use dosage, has no adverse effect on normal growth of rice and wheat crops, does not need to be added with a safener, and is particularly safe to the wheat crops at low temperature.

Description

technical field [0001] The invention belongs to the field of organic molecule synthesis, and relates to a pyridyloxyphenoxypropionamide compound with herbicidal activity and its synthesis method and application, in particular to a new compound (R)-2-(4-((5- Chloro-3-fluoropyridin-2-yl)oxy)phenoxy)-N-(2-fluorophenyl)-N-methylpropionamide and its synthesis method and use. Background technique [0002] Clodinafop-propargyl (Clodinafop-propargyl), chemical name: (R)-2-[4-(5-chloro-3-fluoro-2-pyridyloxy)phenoxy]propargyl propionate, belongs to aryloxybenzene Oxypropionic acid herbicide can effectively inhibit the biosynthesis of esters, is an acetyl cosensitizing A hydroxylase inhibitor, and is a selective systemic conduction post-emergence stem and leaf treatment agent. The medicament is absorbed by the plant leaves and sheaths and then transmitted to the meristem, inhibiting acetyl-CoA carboxylase, thereby inhibiting the biosynthesis of fatty acids, and eventually leading to t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/643A01N43/40A01P13/00
CPCA01N43/40C07D213/643
Inventor 刘东卫张彦飞
Owner JIANGSU FUDING CHEM
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