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N-(2-(substituted benzo- thiazole-2- amino formacyl) -phenyl group) - benzamide, as well as preparation method and usages thereof

A carbamoyl, benzothiazole technology, applied in N-(2-(substituted benzothiazole-2-carbamoyl)-phenyl)-benzamide and the fields of preparation and use thereof, can solve the inhibitory activity Weak, unstudied, etc.

Inactive Publication Date: 2012-03-28
贵州阡红农业发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In 2002, El-Gaby et al. (El-Gaby, M.A.; Micky, J.; Tahol, N.Antimicrobial activity of some novel thiourea, hydrazine, fused pyrimidine and 2-(4-substituted)aniline benzoazole derivatives containing sulfonamide moieties[J ].Journal of Chinese Chemical Society, 2002,49,407-414.) synthesized the isothiocyanate containing benzenesulfonamide with 4-aminobenzenesulfonamide and thiophosgene reaction, this isothiocyanate is again Reflux with N,N-dimethylformamide and triethylamine for several hours to synthesize benzobenzothiazole derivatives with fungicidal activity, and use the growth rate method to test the fungicidal activity of this type of compound. The activity test shows that : At the concentration of 1.0mg / ml, this type of compound has higher inhibitory activity to Proteus; wherein one compound has moderate inhibitory activity to Staphylococcus aureus (Staphylococcus aureus) and penicillium (Penicillium); Inhibitory activity of Prodigobacterium and Aspergillus was weak
[0015] It can be seen from the background technology that bisamide compounds such as chlorantraniliprole have good insecticidal activity and are safe to mammals, and benzothiazole compounds such as benthiazil have good antibacterial activity and have excellent effect on rice sheath blight. However, no one has synthesized bisamide compounds containing benzothiazole-containing pyrazole amide, and no one has studied the use of benzothiazole-containing pyrazole amide bisamide compounds in plant viruses

Method used

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  • N-(2-(substituted benzo- thiazole-2- amino formacyl) -phenyl group) - benzamide, as well as preparation method and usages thereof
  • N-(2-(substituted benzo- thiazole-2- amino formacyl) -phenyl group) - benzamide, as well as preparation method and usages thereof
  • N-(2-(substituted benzo- thiazole-2- amino formacyl) -phenyl group) - benzamide, as well as preparation method and usages thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1. Synthesis of compound N-(2-(6-ethoxybenzothiazole-2-carbamoyl)-phenyl)-2,4-dichlorobenzamide (compound number a):

[0036] (1) Synthesis of 2,4-dichlorobenzoyl chloride

[0037] Get 14.32g (0.075mol) of 2,4-dichlorobenzoic acid in a 100ml there-necked flask (with thermometer, drying tube and tail gas absorption device), then add 20ml of thionyl chloride therein, heat and reflux for 10 hours, TLC After tracking, the reaction was complete, and the excess thionyl chloride was distilled off to obtain 10.99 g of liquid;

[0038] (2) Synthesis of 2-(2,4-dichlorobenzamido)benzoic acid

[0039] Get the anthranilic acid of 8.83g (0.064mol) in the there-necked flask of 250ml, then add the dichloromethane of 30ml in the reaction flask, then add 3ml triethylamine solution thereinto, until the solution is brown and clear, then the After the prepared acid chloride was diluted with 30ml of dichloromethane, it was dropped into the reaction solution drop by drop, and stirre...

Embodiment 2

[0044] Embodiment 2, the synthesis of compound N-(2-(6-methylbenzothiazole-2-carbamoyl)-phenyl)-2,4-dichlorobenzamide (compound number is b)

[0045] (1) Synthesis of 2,4-dichlorobenzoyl chloride

[0046] Synthesize as embodiment one (1) condition and method;

[0047] (2) Synthesis of 2-(2,4-dichlorobenzamido)benzoic acid

[0048] Synthesize as embodiment one (2) condition and method;

[0049] (3) Synthesis of 2-(2,4-dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one

[0050] Synthesize as embodiment one (3) condition and method;

[0051] (4) Synthesis of N-(2-(6-methylbenzothiazole-2-carbamoyl)-phenyl)-2,4-dichlorobenzamide

[0052] Synthesized under the same conditions and methods as in Example 1 (4), except that 0.33 g of 2-amino-6-methylbenzothiazole was added, and the reaction time was 6 hours to obtain a light yellow solid. Yield: 40%, mp: 228-229°C.

Embodiment 3

[0053] Example 3, the synthesis of compound N-(2-(6-chlorobenzothiazole-2-carbamoyl)-phenyl)-2,4-dichlorobenzamide (compound number is c)

[0054] (1) Synthesis of 2,4-dichlorobenzoyl chloride

[0055] Synthesize as embodiment one (1) condition and method;

[0056] (2) Synthesis of 2-(2,4-dichlorobenzamido)benzoic acid

[0057] Synthesize as embodiment one (2) condition and method;

[0058] (3) Synthesis of 2-(2,4-dichlorophenyl)-4H-benzo[d][1,3]oxazin-4-one

[0059] Synthesize as embodiment one (3) condition and method;

[0060] (4) Synthesis of N-(2-(6-chlorobenzothiazole-2-carbamoyl)-phenyl)-2,4-dichlorobenzamide

[0061] Synthesized under the same conditions and methods as in Example 1 (4), except that 0.37 g of 2-amino-6-chlorobenzothiazole was added, and the reaction time was 9 hours to obtain a white solid. Yield: 37%, mp: >250°C.

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Abstract

The invention discloses N-(2-(substituted benzo- thiazole -2- amino formacyl) -phenyl group) - benzamide with an effect of plant virus resistance, and a preparation method thereof. The chemical structure is expressed by a general formula (1). The invention introduces a benzothiazole ring benzoyl aminobenzene methanamide compound containing substituted benzoic acid, which adopts raw materials of substituted benzoic acid, substituted anthranllic acid, substituted benzothiazole amine, thionyl chloride and acetic oxide and is synthesized through four steps of chlorination, acidylation, cyclization and ring opening, and the compound has plant virus resisting activity and anticancer activity.

Description

technical field [0001] The invention relates to the synthesis and preparation method of benzothiazole ring-containing o-benzamidobenzamide compounds with anti-plant virus effect. Background technique [0002] The o-benzamidobenzamide compounds are a class of ryanodine receptor analogs with good biological activity, and the structural modification of the ryanodine receptor as the parent has opened up a new field for the creation of new pesticides. At present, several commercialized products have appeared, such as flubendiamide and chlorantraniliprole, two broad-spectrum synthetic insecticides with ryanodine receptor structures discovered by Nippon Pesticides, Bayer and DuPont. The o-benzoylaminobenzamide compound has the same action characteristics as ryanodine, not only has excellent insecticidal activity against pests, but also is safe for mammals. [0003] 2005 Lahm et al (Lahm, G.P.; Selby, T.P.; Freudenberger, J.H.; Stevenson, T.M.; Myers, B.J.; Seburyamo, G.; Smith, B....

Claims

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Application Information

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IPC IPC(8): C07D277/82A01N43/78A01P1/00A61K31/428A61P35/00
Inventor 薛伟何勇陈前进韩菲菲丁晓燕熊壮郑玉国魏学杨松李海畅祁慧雪范会涛
Owner 贵州阡红农业发展有限公司
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