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Substitutional biaryl base benzene sulfonamide compound and application

A kind of benzene sulfonamide and compound technology, applied in the field of substituted biaryl benzene sulfonamide compounds, can solve the problem that the herbicidal activity is not always satisfactory and the like

Active Publication Date: 2014-01-01
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In practice the herbicidal activity of these known compounds is not always satisfactory

Method used

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  • Substitutional biaryl base benzene sulfonamide compound and application
  • Substitutional biaryl base benzene sulfonamide compound and application
  • Substitutional biaryl base benzene sulfonamide compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0150] Example 1: Preparation of ethyl 2-(2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)benzenesulfonamide) acetate (compound 1)

[0151]

[0152] 1) Preparation of 3-chloro-2-(4-chlorophenyl)-5-trifluoromethylpyridine

[0153] 21.5g (0.10mol) 2,3-dichloro-5-trifluoromethylpyridine, 14.04g (0.09mol) 4-chlorophenylboronic acid, 0.5g (0.44mmol) tetrakistriphenylphosphine palladium and 41.4g ( (0.30 mol) potassium carbonate was refluxed in a mixture of 100 ml toluene and 50 ml water for 6 hours, monitored by a TLC panel, and the reaction of the raw material 4-chlorophenylboronic acid was completed. The reaction mixture was cooled to room temperature, filtered, the filtrate was extracted with (3×80ml) ethyl acetate, the extracts were combined, washed with (3×60ml) water, 60ml saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain Milky white solid 20.4g, yield: 70%, melting point 72-74°C.

[0154] NMR data ( 1 HNMR, 3...

Embodiment 2

[0161] Example 2: Ethyl 2-(2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-methylbenzenesulfonamide) acetate (Compound 20) Preparation

[0162]

[0163] At room temperature, 0.28 g (2.4 mmol) of ethyl 2-(methylamino) acetate was dissolved in 15 ml of tetrahydrofuran, and 2-chloro-5-(3-chloride was added dropwise to the above solution at 0-5°C. -5-(trifluoromethyl)pyridin-2-yl)benzene-1-sulfonyl chloride (0.8g, 2mmol), then triethylamine (0.4g, 4mmol) was added to the above mixture, and the mixture was stirred at room temperature for reaction After 4 hours, monitored by a TLC panel, the reaction of the starting material 2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)benzene-1-sulfonyl chloride was completed. The solvent tetrahydrofuran was removed under reduced pressure to obtain a crude product. Column chromatography (eluent: a mixture of ethyl acetate and petroleum ether (1:4)) gave 0.47 g of the title compound, yield 50%, melting point 76-78°C.

[0164] NMR data (...

Embodiment 3

[0165] Example 3: Preparation of 2-(2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-methylbenzenesulfonamide)acetic acid (compound 18)

[0166]

[0167] At room temperature, ethyl 2-(2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-methylbenzenesulfonamide) acetate 4.7g ( 10mmol) was dissolved in 30ml of tetrahydrofuran, a saturated aqueous solution containing 0.8g (20mmol) of sodium hydroxide was added dropwise to the above solution at room temperature, the mixture was stirred at room temperature for 6 hours, monitored by TLC panel, the raw material ethyl 2-(2- The reaction of chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-methylbenzenesulfonamide) acetate is complete. The solvent tetrahydrofuran was removed under reduced pressure, the residue was dissolved in 15 ml of water, extracted with ethyl acetate (2×15 ml), the aqueous layer was adjusted to pH2 with concentrated hydrochloric acid, and filtered to obtain 2.66 g of the crude product, yield 60%, meltin...

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Abstract

Disclosed is a substituted biaryl benzenesulfonamide compound or a salt thereof, which has a structure as shown in formula(I): each of the substituents being defined as in the description. The compound of the formula(I)or its salt has a wide spectrum of herbicidal activity, and can be used for preventing and controlling many kinds of broadleaf weeds (such as Chinese jute, Zinnia elegans, etc.), gramineae weeds (such as Echinochloa crusgalli, Setaria viridis, etc.), and also used as a sterilizing herbicide, and as a herbicide for transgenic crop fields, while being relatively safe for use on rice, etc.

Description

Technical field [0001] The invention belongs to the field of agricultural herbicides, and specifically relates to a substituted biarylbenzenesulfonamide compound and its use. Background technique [0002] For substituted biarylbenzenesulfonamide compounds, many patents have been reported, such as WO9822443(A1), WO9842700(A1), WO2001070736(A1), WO2001074786(A1), WO2006065646(A1), WO2009148052(A1), WO2009103440( A1), FR2727413(A1), FR2749584(A1), JP61050975(A), etc., mainly used in medical research. [0003] Peter Schafer et al. mentioned in US5783522(A) that 2-phenylpyridine compounds have certain herbicidal activity: [0004] [0005] Where: R 5 Is hydrogen, fluorine, chlorine, R 7 For SO 2 NR 9 R 10 , R 9 And R 10 Is hydrogen or C 1 -C 8 alkyl. [0006] In fact, the herbicidal activity of these known compounds is not always satisfactory. Summary of the invention [0007] The purpose of the present invention is to provide a biarylbenzenesulfonamide herbicidal compound with novel stru...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D417/12C07D409/12C07D213/61C07D213/75A01P13/00C07D213/34C07D401/12
CPCA01N41/06C07D401/12C07D213/26A01N47/24A01N47/36A01N47/28A01N47/40A01N43/40C07D213/61A01N47/12
Inventor 刘长令迟会伟王正航张静静马宏娟王立增
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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