A compound containing hexafluorosulfonamide structure with herbicidal properties and its synthesis method

A synthesis method and compound technology, which are applied in the fields of sulfonic acid amide preparation, botanical equipment and methods, organic chemistry, etc., can solve the problem of no obvious herbicidal effect of Fructus chinensis, and achieve good herbicidal effect, small dosage and wide herbicidal spectrum. Effect

Active Publication Date: 2022-04-08
JIANGSU FUDING CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, penoxsulam has no obvious herbicidal effect on D. chinensis, so it is necessary to develop new herbicides to make up for the shortcomings of penoxsulam

Method used

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  • A compound containing hexafluorosulfonamide structure with herbicidal properties and its synthesis method
  • A compound containing hexafluorosulfonamide structure with herbicidal properties and its synthesis method
  • A compound containing hexafluorosulfonamide structure with herbicidal properties and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 460g of toluene and 162.3g of compound I into a 1000ml three-necked flask, and stir for 30min at a temperature of 60-65°C to dissolve compound I in toluene.

[0034] Add 62.5g of compound II, 160.7g of 3,5-lutidine, and 2.5g of DMSO into a 2000ml three-necked flask, stir, raise the temperature to 65°C, and add the toluene solution of compound I dropwise to the mixture containing compound II within about 2 hours. solution, keep warm for 2h after the dropwise addition. Reaction finishes, and reaction solution is cooled to 10 ℃, and hydrochloric acid (concentration is 10%) is added dropwise to adjust pH value to 2, layering, organic phase rotary steaming, adds 500g concentrated hydrochloric acid (concentration is 30%), 0~10 ℃ of crystallization, Filter, wash with water until the pH value reaches 7, filter, and dry to obtain 195 g of the finished product (Compound III, white solid), with a content of 98.3% and a yield of 94.36%.

[0035] 1 H NMR (DMSO-d 6 ,300MHz) δ:...

Embodiment 2

[0037] Add 500g of toluene and 162.3g of compound I into a 1000ml three-neck flask, keep the temperature at 60-65°C and stir for 30min to dissolve compound I in toluene.

[0038] Add 62.5g of compound II, 160.7g of 3,5-lutidine, and 2.5g of DMSO into a 2000ml three-necked flask, stir, raise the temperature to 65°C, and add the toluene solution of compound I dropwise to the mixture containing compound II within about 2 hours. solution, keep warm for 2h after the dropwise addition. Reaction finishes, and reaction solution is cooled to 10 ℃, and hydrochloric acid (concentration is 10%) is added dropwise to adjust pH value to 2, layering, organic phase rotary steaming, adds 500g concentrated hydrochloric acid (concentration is 30%), 0~10 ℃ of crystallization, Filter, wash with water until the pH value reaches 7, filter, and dry to obtain 194 g of the finished product, with a content of 98.2% and a yield of 93.87%.

Embodiment 3

[0040] Add 460g of toluene and 162.3g of compound I into a 1000ml three-neck flask, keep the temperature at 60-65°C and stir for 30min to dissolve compound I in toluene.

[0041]Add 62.5g of compound II, 107g of 3,5-lutidine, and 2.5g of DMSO into a 2000ml three-necked flask, stir, raise the temperature to 65°C, and add the toluene solution of compound I to the mixture containing compound II dropwise within about 2 hours After the dropwise addition, keep warm for 2h. Reaction finishes, and reaction solution is cooled to 10 ℃, and hydrochloric acid (concentration is 10%) is added dropwise to adjust pH value to 2, layering, organic phase rotary steaming, adds 500g concentrated hydrochloric acid (concentration is 30%), 0~10 ℃ of crystallization, Filter, wash with water until the pH value reaches 7, filter, and dry to obtain 163 g of the finished product, with a content of 96.5% and a yield of 78.89%.

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Abstract

The invention discloses a compound containing a hexafluorosulfonamide structure with herbicidal properties, and the compound structure is shown in formula (III). The invention also discloses a synthesis method of the compound, using 2-(2,2-difluoroethoxy)-6-trifluoromethylbenzenesulfonyl chloride and 2-fluoro-N-methylaniline as raw materials, Under the catalysis of organic base and catalyst, the target product is obtained by reaction. The present invention has a wide weeding spectrum, and has good control effect on grass weeds such as barnyard grass and daughter chinensis, annual sedge family weeds such as sedge, and broad-leaved weeds such as auricularia amaranthus in rice fields. There is no adverse effect on the normal growth of similar crops, no safener is needed, and the dosage is small, which is more conducive to the use in agricultural production.

Description

technical field [0001] The invention belongs to the field of organic molecule synthesis, and relates to a compound containing a hexafluorosulfonamide structure with herbicidal properties and a synthesis method thereof, in particular to a 2-(2,2-difluoroethoxy)- N-(2-fluorophenyl)-N-methyl-6-(trifluoromethyl)benzenesulfonamide and its synthesis method. Background technique [0002] Penoxsulam is a post-emergence herbicide developed by Dow AgroSciences in the United States. It is a triazolopyrimidine sulfonamide herbicide, which acts by inhibiting acetolactate synthase (ALS). effect. [0003] It was officially registered with the US EPA on September 24, 2004. It was promoted and applied in the southern rice fields of the United States in 2005, and it was registered in China in 2008. Penoxsulam has attracted people's attention due to its low toxicity, high efficiency and safety. It will be further developed in the application of rice and become one of the important products. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/29C07C303/38A01N41/06A01P13/00A01G13/00
CPCC07C311/29C07C303/38A01N41/06A01G13/00
Inventor 刘东卫张彦飞
Owner JIANGSU FUDING CHEM
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