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Acyl benzylamine compound and use thereof

A technology of acylbenzylamines and compounds, applied in the preparation and application of organic compounds, preparation of carboxylic acid amides, etc.

Active Publication Date: 2012-05-23
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Acylbenzylamine compounds such as tolfenpyrad (tolfenpyrad) [US 5039693], tebufenpyrad (tebufenpyrad) [US 4950668], CN1927860, etc. are mostly used as insecticides and acaricides, and CN1919838 and WO2002083647 report that the compounds have insecticidal and bactericidal activities. But use as bactericide as the acylbenzylamine compound of general structural formula of the present invention has no bibliographical information

Method used

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  • Acyl benzylamine compound and use thereof
  • Acyl benzylamine compound and use thereof
  • Acyl benzylamine compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0185] Embodiment 1: the preparation of intermediate II-1

[0186] 1).

[0187]

[0188] Add 19.80 g (0.067 mol) of solid phosgene in small portions to a solution containing 13.70 g (0.1 mol) of anthranilic acid in 150 ml of tetrahydrofuran under stirring at room temperature, and complete the addition in about 1.5 hours. Continue stirring at room temperature for 2-3 hours, TLC After monitoring the reaction, the solvent was evaporated under reduced pressure, the residue was added to 80ml of water, stirred until the excess phosgene was completely decomposed, filtered and washed with 50ml of water and petroleum ether in turn to obtain 14.00g of white solid, yield 86.0%, melting point 239- 240°C.

[0189] 2).

[0190]

[0191] Slowly add 40% methylamine aqueous solution dropwise to 100ml acetonitrile solution containing 16.30g (0.1mol) benzoxazinone under stirring at room temperature, until the solution becomes clear, add about 80ml methylamine aqueous solution dropwise, d...

Embodiment 2

[0201] Embodiment 2: the preparation of compound 23

[0202]

[0203] Add 0.313g (0.001mol) of benzylamine (II-1) and 0.12g (0.0012mol) of triethylamine into 20ml of dichloromethane, and add dropwise 0.17g (0.0011mol) of (III-1) in 10ml of dichloromethane under stirring at room temperature. Chloromethane solution, after dropping, continue stirring at room temperature for 1 hour, TLC monitors the reaction to the end point, pours the reaction mixture into 30ml of water, shakes and separates the organic layer, and the organic phase is sequentially washed with 10% dilute hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated salt After washing with 20ml of water, the product was dried and precipitated to obtain the product, which was washed with ethyl acetate to obtain a white solid, and 0.38g of pure product was obtained by column chromatography, with a yield of 87.5% and a melting point of 168-169°C.

Embodiment 3

[0204] Embodiment 3: the preparation of compound 62

[0205]

[0206] Add 0.313g (0.001mol) of benzylamine (II-1) and 0.12g (0.0012mol) of triethylamine into 20ml of dichloromethane, and add dropwise 0.22g (0.0011mol) of (III-2) in 10ml of dichloromethane while stirring at room temperature. Chloromethane solution, after dropping, continue stirring at room temperature for 1 hour, TLC monitors the reaction to the end point, pours the reaction mixture into 30ml of water, shakes and separates the organic layer, and the organic phase is sequentially washed with 10% dilute hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated salt The product was washed with 20 ml of water, dried and precipitated to obtain the product, washed with ethyl acetate to obtain a white solid, and 0.39 g of pure product was obtained by column chromatography, with a yield of 82.0% and a melting point of 154-156°C.

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Abstract

The invention discloses an acyl benzylamine compound and a use thereof. The acyl benzylamine compound has wide-spectrum bactericidal activity and has a general structural formula shown in the formula I, wherein definitions of all substituent groups in the formula I are shown in the patent specification. The acyl benzylamine compound has wide-spectrum bactericidal activity, has effects of treating symptoms caused by cucumber downy mildew, corn rust and wheat powdery mildew, and especially, has excellent effects of preventing cucumber downy mildew and corn rust. The acyl benzylamine compound also has good effects of preventing and treating wheat powdery mildew. The acyl benzylamine compound has the advantages of high activity, low use amount and good safety.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, and in particular relates to an acylbenzylamine compound and an application thereof. Background technique [0002] Germs cause great damage to crops, especially agricultural products such as grain and fiber that can meet the basic needs of human beings, such as cotton, rice, corn, wheat, soybeans, etc. Avoiding or reducing damage to crops while killing or inhibiting the growth of pathogens is an effective way to improve agricultural production. Therefore, it is necessary to continuously develop new and more effective fungicides. Acyl benzylamine compounds such as tolfenpyrad (tolfenpyrad) [US 5039693], tebufenpyrad (tebufenpyrad) [US 4950668], CN1927860, etc. are mostly used as insecticides and acaricides. CN1919838 and WO2002083647 report that the compounds have insecticidal and bactericidal activities. However, the use of the acylbenzylamine compound of the general structural formula of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/30C07C231/14C07C255/57C07C253/30C07C239/20C07C235/24C07C255/63C07C237/40C07C317/44C07C243/38C07C241/04C07C291/02C07D213/82C07D239/30C07D239/28C07D307/68C07D277/56C07D417/04C07D231/16C07D231/14C07D401/04C07D295/192C07D265/30C07C235/16C07C231/12A01N53/12A01N39/04A01N39/02A01N41/10A01N43/40A01N43/54A01N43/08A01N43/78A01N43/836A01N43/56A01P3/00
Inventor 刘长令王立增兰杰张茜李志念迟会伟
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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