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Phenylsulphonyl ureas, processes for their preparation and their use as herbicides and plant-growth regulators

An alkyl and group technology, which is applied in the field of phenylsulfonylurea herbicides and plant growth regulators, can solve problems such as insufficient selectivity and high persistence

Inactive Publication Date: 2004-03-03
HOECHST SCHERING AGREVO GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds have some drawbacks in their use, such as high persistence or insufficient selectivity in important crops

Method used

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  • Phenylsulphonyl ureas, processes for their preparation and their use as herbicides and plant-growth regulators
  • Phenylsulphonyl ureas, processes for their preparation and their use as herbicides and plant-growth regulators
  • Phenylsulphonyl ureas, processes for their preparation and their use as herbicides and plant-growth regulators

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A12

[0078] Embodiment A12-(tert-butylaminosulfonyl)-4-cyanomethylbenzoic acid methyl ester

[0079] 100 grams of 61.5% 2-(tert-butylaminosulfonyl)-4-bromomethylbenzoic acid methyl ester (61.5 grams = 0.169 moles), 12.09 grams (0.186 moles) of potassium cyanide and 10.89 grams (33.8 mg mol) of tetrabutylammonium bromide in 750 ml of dichloromethane and 150 ml of water was stirred at room temperature for 6 hours.

[0080] The mixture was diluted with water, the phases were separated and the aqueous phase was extracted twice with dichloromethane for further processing. The combined organic extracts were dried over sodium sulfate. The crude product obtained by concentration is chromatographed on silica gel with an ethyl acetate / petroleum ether mixture (1:2, v / v) as eluent. Concentration of the fractions with RF=0.18 afforded 48.1 g (91.8%) of methyl 2-(tert-butylaminosulfonyl)-4-cyanomethylbenzoate, melting point 86-88°C. Embodiment A24-(2-aminoethyl)-2-tert-butylaminosulfonylbenzo...

Embodiment A2

[0080] The mixture was diluted with water, the phases were separated and the aqueous phase was extracted twice with dichloromethane for further processing. The combined organic extracts were dried over sodium sulfate. The crude product obtained by concentration is chromatographed on silica gel with an ethyl acetate / petroleum ether mixture (1:2, v / v) as eluent. Concentration of the fractions with RF=0.18 afforded 48.1 g (91.8%) of methyl 2-(tert-butylaminosulfonyl)-4-cyanomethylbenzoate, melting point 86-88°C. Embodiment A24-(2-aminoethyl)-2-tert-butylaminosulfonylbenzoic acid methyl ester

[0081] A solution of 2.5 g (8.05 mmol) of methyl 2-(tert-butylaminosulfonyl)-4-cyanomethylbenzoate in 200 ml of methanol and 4 ml of concentrated hydrochloric acid was added to the Hydrogenation was carried out at room temperature under 20 bar hydrogen pressure for 10 hours. The catalyst was filtered off and the filtrate was concentrated. After taking up the residue in ethyl acetate, th...

Embodiment A5

[0092] A solution of 1.4 g (3.8 mmol) of methyl 2-tert-butylaminosulfonyl-4-[2-(methoxycarbonylamino)ethyl]benzoate in 20 ml of trifluoroacetic acid was stirred at room temperature for 8 Hour. The mixture was concentrated well, reevaporated with toluene and the residue was crystallized from ethyl acetate / diisopropyl ether. 0.54 g (45%) of methyl 2-aminosulfonyl-4-[2-(methoxycarbonylamino)ethyl]benzoate of melting point: 146 to 149° C. are obtained. Example A5 2-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonylaminosulfonyl]-4-[2-(methoxycarbonylamino)ethyl]benzoic acid methyl ester

[0093] In 0.54 g (1.7 mmol) of 2-aminosulfonyl-4-[2-(methoxycarbonylamino) ethyl]benzoic acid methyl ester and 0.47 g (1.7 mmol) of N-(4,6-dimethyl To a suspension of oxypyrimidin-2-yl)phenylcarbamate in 15 ml acetonitrile was added dropwise 0.26 ml (1.7 mmol) DBU. after 2 hours. Dilute with water and diethyl ether, acidify to pH 1 to 2 with hydrochloric acid, filter the precipitated product, wash w...

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Abstract

The present invention relates to compounds of the formula(I)and salts thereof in which R1-R9, W and A are as defined in claim 1 are suitable as herbicides and plant growth regulators. They can be prepared by processes according to claim 5 via intermediates according to claim 9, some of which are novel.

Description

Technical field [0001] The present invention relates to phenylsulfonylurea herbicides and plant growth regulators and their preparation methods. Background technique [0002] Some phenylsulfonylureas are known to have herbicidal and plant growth regulating properties, see for example US-A-4,786,314, US-A-4,927,453, WO89 / 10921 and WO95 / 10507 (=ZA94 / 8063). However, these compounds suffer from some drawbacks in their use, such as high persistence or insufficient selectivity in important crops. Contents of the invention [0003] A new phenylsulfonylurea with specific groups on the benzene ring has now been discovered, which can be advantageously used as a herbicide and plant growth regulator. [0004] The present invention relates to a compound represented by formula (I) or a salt thereof where R 1 Is the formula S(O) n -R 10 or CO-Q-R 11 acyl group, R 2 ,R 3 ,R 4 ,R 5 Is the same or different, selected from the following groups: H, (1-6) alkyl, (1-4) alkoxy, (1-4) ...

Claims

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Application Information

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IPC IPC(8): C07D251/46A01N47/36A01P13/00A01P21/00C07C309/88C07C309/89C07C311/39C07C311/41C07C311/47C07C311/58C07C311/65C07D213/85C07D239/42C07D239/47C07D239/48C07D239/52C07D239/54C07D249/12C07D251/42C07D251/52C07D401/12C07D405/12C07D417/12C07D491/048C07D521/00
CPCC07C311/47C07D521/00A01N47/36C07C311/65C07C311/39C07C309/89
Inventor K·洛伦茨L·威廉斯K·鲍尔H·比林格C·罗辛格
Owner HOECHST SCHERING AGREVO GMBH
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