New haloalkylsulfonanilide derivative, herbicide and use method thereof

A technology of halogenated alkylsulfonanilides and alkylsulfonyl groups, which is applied in the field of novel halogenated alkylsulfonanilide derivatives or their salts, and can solve the problems of unknown preparation methods, physical and chemical properties and herbicidal activity

Inactive Publication Date: 2008-01-23
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, regarding the haloalkylsulfonanilide derivatives of the present invention, their unique preparation methods, physicochemical properties and herbicidal activity have not been known so far

Method used

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  • New haloalkylsulfonanilide derivative, herbicide and use method thereof
  • New haloalkylsulfonanilide derivative, herbicide and use method thereof
  • New haloalkylsulfonanilide derivative, herbicide and use method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0196] Example 1. Preparation of 4-ethyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-2-oxazolidinone (compound number 1-5)

[0197] 1-1) Preparation of 4-ethyl-3-(2-nitrobenzyl)-2-oxazolidinone

[0198] 2-(2-Nitrobenzylamino)-1-butanol (3.2 g, 14 mmol) was dissolved in chloroform (100 ml), and the reaction solution was cooled to 0°C. Next triethylamine (7.1 g, 71 mmol) and triphosgene (2.1 g, 7.1 mmol) were added. The reaction solution was stirred at 0°C for 1.5 hours, added with water and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give 4-ethyl-3-(2-nitrobenzyl)-2-oxazolidinone (2.6 g).

[0199] Yield: 72%

[0200] Nature: n D 1.5514(23℃)

[0201] 1-2) Preparation of 4-ethyl-3-(2-aminobenzyl)-2-oxazolidinone (Compound No. 2-2)

[0202]Dissolv...

Embodiment 2

[0209] Example 2. Preparation of 4-ethyl-3-{2-[N-(isobutoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl}-2-oxazolidinone (Compound No. 1 -6)

[0210] 4-Ethyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-2-oxazolidinone (1.0 g, 2.8 mmol) and sodium bicarbonate (0.48 g, 5.7 mmol) were suspended in acetonitrile (10ml), add isobutyl chloroformate (0.78g, 5.7mmol), and reflux for 2 hours. The reaction solution was cooled to room temperature, and extracted with ethyl acetate after adding water. The ethyl acetate layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to give 4-ethyl-3-{2-[N-(isobutoxycarbonyl)-N-(trifluoromethanesulfonyl) Amino]benzyl}-2-oxazolidinone (1.2 g).

[0211] Yield: 91%

[0212] Properties: Melting point 69.3-71.7℃

Embodiment 3

[0213] Example 3. Preparation of 4,4-dimethyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-2-oxazolidinone (compound number 1-15)

[0214] 3-1) Preparation of 4,4-dimethyl-3-(2-nitrobenzyl)-2-oxazolidinone

[0215] 2-(2-nitrobenzylamino)-2-methyl-1-propanol (2.6g, 12mmol) was dissolved in chloroform (100ml), and the reaction solution was cooled to 0°C, then triethylamine (5.9g , 59mmol) and triphosgene (1.7g, 5.9mmol). The reaction solution was stirred at this temperature for 1.5 hours, and extracted with ethyl acetate after adding water. The ethyl acetate layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:hexane 1:1) to give 4,4-dimethyl-3-(2-nitrobenzyl)-2-oxazolidinone (1.3 g).

[0216] Yield: 43%

[0217] Properties: Melting point 103-106℃

[0218] 3-2) Preparation of 4,4-dimethyl-3-(2-aminobenzyl)-2-oxazolidino...

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Abstract

Halogenated alkylsulfonanilide derivatives shown in formula (I): {wherein R1 represents haloalkyl; R2 represents H, alkylcarbonyl, optionally substituted phenylcarbonyl, alkoxycarbonyl, optionally substituted phenoxycarbonyl, Optionally substituted benzenesulfonyl and the like; R3 and R4 each represent H, alkyl, cycloalkyl, halogen, CN, etc.; R5, R6, R7 and R8 each represent H, halogen, alkyl, cycloalkyl, any Optionally substituted phenyl (C1-6 alkyl), optionally substituted heterocycle, etc.; A and W each represent O or S; and X represents 1-4 each selected from H, halogen, alkyl, alkenyl , optionally substituted phenyl, optionally substituted phenylalkylaminocarbonyl, OH, CN, etc.} and salts thereof; and herbicides containing any one of the aforementioned compounds as an active ingredient. The herbicide has excellent broad applicability, persistence and selectivity to crops, and is effective against various weeds. In particular, it can be excellently used as a herbicide for paddy fields.

Description

technical field [0001] The present invention relates to novel haloalkylsulfonanilide derivatives or salts thereof, herbicides containing the compounds as active ingredients, and methods of using them. Background technique [0002] Compounds in which a haloalkylsulfonanilide and a heterocyclic ring are linked to a nitrogen atom in the heterocyclic ring via a spacer such as an alkylene group are generally known as herbicides (see, for example, JP-A-2004-107322). [0003] However, regarding the haloalkylsulfonanilide derivatives of the present invention, their unique preparation methods, physicochemical properties and herbicidal activities have not been known so far. Contents of the invention [0004] As mentioned above, certain haloalkylsulfonamide derivatives are known to be useful as herbicides. However, its characteristics such as effectiveness, applicability against various weeds including difficult-to-eliminate weeds, residual activity, and selectivity to crops and wee...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/16C07D277/14C07D263/22A01N43/76C07D263/24A01N43/78C07D263/52A01N47/02C07D263/58
CPCC07D263/22A01N47/24A01N47/04C07D277/14C07D263/24C07D263/58C07D263/20
Inventor 日野智和重成俊彦清川贵弘豆塚弘毅山田康子
Owner NIHON NOHYAKU CO LTD
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