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Substituted benzimidazole, the production thereof and the use thereof as means against parasitic protozoa

A kind of benzimidazole, representative technology, is applied in the field of substituted benzimidazoles

Inactive Publication Date: 2003-12-10
BAYER ANIMAL HEALTH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Serious problems arise even shortly after injection of the reagents due to the development of resistance to the reagents used

Method used

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  • Substituted benzimidazole, the production thereof and the use thereof as means against parasitic protozoa

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] 3.3 g (10 mmol) of 4-bromo-2,6-di-trifluoromethylbenzimidazole was added to 100 ml of dichloromethane, and 1.73 ml (12.5 mmol) of triethylamine was added at 20°C. Then, 10 ml of dichloromethane containing 2.4 g (12.5 mmol) of 4-bromomethyl-5-methyl-1,3-dioxol-2-one was added dropwise at 20°C, and the mixture was refluxed for 24 hours . The dichloromethane solution was washed three times using 30 ml of water each time, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (35-70 μm) using cyclohexane / ethyl acetate (3:1). 1.5 g (34% of the theoretical yield) of the above compound was obtained. Melting point: 141-143°C.

[0168] Implement

Embodiment a

[0170] Add 1400g (6.7mol) of 2,3-tetrafluoro-1,4-benzodioxane and 7g (0.08mol) of FeS (powder), add dropwise at 20-30℃ in the course of about 4 hours 1190 g (7.4 mol) bromine, the mixture was stirred for about 20 hours until the end of gassing. Wash with aqueous sodium sulfite solution and dry over sodium sulfate. The residue is distilled in vacuum.

[0171] Yield: 1540 g (80% of theory), boiling point 10: 70-74°C (GC: 99%).

Embodiment b

[0173] Add 350g (1.2mol) 6-bromo-2,3-tetrafluoro-1,4-benzodioxane dropwise to 273ml (98% concentration) nitric acid and 293ml concentrated sulfuric acid at 20℃ within 75 minutes, the mixture Stir at 20°C for 1 hour and at 40°C for 3 hours. The batch was poured on ice, extracted with dichloromethane, the organic phase was washed with water and aqueous sodium bicarbonate solution and dried over sodium sulfate. The organic phase is evaporated and reacted further as a crude product.

[0174] Yield: 396 g (98% of theory), (crude product, GC: 99.1%), boiling point 16: 121-124°C, nD at 20°C: 1.5065.

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Abstract

The present invention relates to a new substituted benzimidazoles, their preparation and their use as agents against parasitic protazoa.

Description

Technical field [0001] The present invention relates to new substituted benzimidazoles, their preparation and their use as antiparasitic protozoa agents. [0002] The present invention also relates to the use of a mixture of these compounds with polyether antibiotics or synthetic preparations for coccidiosis in the composition for controlling parasitic protozoa, especially coccidia. Background technique [0003] Substituted benzimidazoles and their use as insecticides, fungicides and herbicides have been disclosed (EP-OS 87375, 152360, 181826, 239508, 260744, 266984, US-P 3418318, 3472865, 3576818, 3729994) . [0004] Halogenated benzimidazoles and their effects as helminths, anticoccidials and insecticides have been published (DE-OS 2047369, DE-OS 4237617). A mixture of nitro-substituted benzimidazoles and polyether antibiotics has been disclosed as a coccidiosis agent (US-P 5331003). In all cases, its effect is still unsatisfactory. [0005] Coccidiosis is a disease caused by s...

Claims

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Application Information

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IPC IPC(8): C07D491/048A01N43/28A01N43/52A01N43/90A61K31/4184A61P33/02C07D405/06C07D491/04C07D491/056
CPCC07D491/04C07D405/06A61P33/02C07D491/056
Inventor G·格雷夫A·哈贝尔科恩B·巴尔斯纳F·利布A·马霍尔德J·斯特尔廷
Owner BAYER ANIMAL HEALTH