Substituted biaryl benzenesulfonamide compound and use

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: 2014-11-19
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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  • Substituted biaryl benzenesulfonamide compound and use
  • Substituted biaryl benzenesulfonamide compound and use
  • Substituted biaryl benzenesulfonamide compound and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0147] Example 1: Ethyl 2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)benzenesulfonamidoformate (Compound 44)

[0148]

[0149] The first step reaction: 3-chloro-2-(4-chlorophenyl)-5-trifluoromethylpyridine

[0150] 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) of potassium carbonate was refluxed in a mixture of 100 ml of toluene and 50 ml of water for 6 hours, monitored by a TLC board, and the reaction of the raw material 4-chlorophenylboronic acid was completed. The reaction mixture was cooled to room temperature, filtered to obtain a filtrate, extracted with (3x80ml) ethyl acetate, combined extracts, washed with (3x60ml) water, washed with 60ml saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a milky white solid 20.4g, yield: 70%, melting point 72-74°C.

[0151] NMR d...

Embodiment 2

[0165] Example 2: Methyl 2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-4-fluorobenzenesulfonyl formate (Compound 22)

[0166]

[0167] The first step reaction: 3-chloro-2-(4-chloro-2-fluorophenyl)-5-trifluoromethylpyridine

[0168] 21.5g (0.10mol) 2,3-dichloro-5-trifluoromethylpyridine, 15.66g (0.09mol) 4-chloro-2-fluorophenylboronic acid, 0.5g (0.44mmol) tetrakistriphenylphosphine palladium And 41.4g (0.30mol) potassium carbonate in the mixture of 100ml toluene and 50ml water reflux reaction for 6 hours, TLC plate monitoring, raw material 4-chloro-2-fluorophenylboronic acid reaction is complete. The reaction mixture was cooled to room temperature, filtered to obtain a filtrate, extracted with (3x80ml) ethyl acetate, combined extracts, washed with (3x60ml) water, washed with 60ml saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to obtain a milky white solid 18.1g, yield: 65%, melting point 34-36°C.

[0169] N...

Embodiment 3

[0183] Example 3: 2-chloro-5-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(cyanomethyl)benzenesulfonamide (Compound 2)

[0184]

[0185] At room temperature, 0.17 g (3 mmol) of 2-aminoacetonitrile was dissolved in 15 ml of tetrahydrofuran, and 0.6 g (1.5 mmol) of 2-chloro-5-(3-chloro-5-( Trifluoromethyl)pyridin-2-yl)benzene-1-sulfonyl chloride, then triethylamine (0.4g, 4mmol) was added to the above mixture to obtain 0.25g of the title compound, yield: 40%.

[0186] NMR data ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0187] δppm 3.87 (2H, d), 5.66 (1H, t), 7.70 (1H, d), 7.95 (1H, d), 8.08 (1H, s), 8.51 (1H, s), 8.86 (1H, s).

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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 relates to a substituted biarylbenzenesulfonamide compound and its application. Background technique [0002] For substituted biarylbenzenesulfonamide compounds, there are many reported patents, such as WO9822443, WO9842700, WO2001070736, WO2001074786, WO2006065646, WO20081224614, WO2009148052, WO2009103440, FR2727413, FR2749584, 5 are mainly used in the research of medicine, etc. 1. [0003] People such as Peter Schafer mentioned that 2-phenylpyridine compounds have certain herbicidal activity in US5783522: [0004] [0005] Where: R 5 is hydrogen, fluorine, chlorine, R 7 for SO 2 NR 9 R 10 , R 9 and R 10 for hydrogen or C 1 -C 8 alkyl. [0006] In practice the herbicidal activity of these known compounds is not always satisfactory. Contents of the invention [0007] The object of the present invention is to provide a novel herbicidal compound, and hope that these compo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/26C07D401/02A01N43/40A01P13/00
CPCA01N47/12C07D213/61A01N41/06C07D213/26A01N47/28A01N47/24A01N47/36C07D401/12A01N47/40A01N43/40
Inventor 刘长令迟会伟王正航张静静马宏娟伍强崔东亮王立增
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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