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Substituted thiophenecarboxamides and analogues as antibacterials agents

A methyl and plant-based technology, which is applied to compounds, biocides, and disinfectants of elements of group 4/14 of the periodic table, and can solve problems such as poor effects

Pending Publication Date: 2021-04-09
BAYER AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventors of the present invention have found that these compounds have poor efficacy against Xanthomonas campestris pv. campestris at low doses

Method used

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  • Substituted thiophenecarboxamides and analogues as antibacterials agents
  • Substituted thiophenecarboxamides and analogues as antibacterials agents
  • Substituted thiophenecarboxamides and analogues as antibacterials agents

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0333] Preparation Example 1 : Preparation of 5-(4,5-dibromo-3-fluoro-2-thienyl)-6-oxa-4-azaspiro[2.4]hept-4-en-7-one (Compound III.01)

[0334] step 1 : Preparation of ethyl 1-{[(4,5-dibromo-3-fluoro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (Compound XXI.01)

[0335] To 200 mg (0.66 mmol) of 4,5-dibromo-3-fluorothiophene-2-carboxylic acid and 170 mg (1.32 mmol) of ethyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) were dissolved in 3 mL of tetrahydrofuran To the solution was added 0.14 mL (1.00 mmol) of triethylamine followed by 0.59 mL (1.00 mmol) of a 50% (w / w) solution of propanephosphonic anhydride in ethyl acetate. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / et...

preparation Embodiment 2

[0340] Preparation Example 2 : Preparation of intermediate ethyl 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (Compound XXI.11)

[0341] Under an inert atmosphere, 100 mg (0.23 mmol) of ethyl 1-{[(4,5-dichloro-3-iodo-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound XXI.08), 21 mg (0.34 mmol) of methylboronic acid, 2.6 mg (0.01 mmol) of palladium(II) acetate, 6.5 mg (0.02 mmol) of tricyclohexylphosphine and 172 mg (0.80 mmol) of tripotassium phosphate, Degassed toluene (1.25 mL) and water (0.13 mL) were then added. The vial was sealed and the reaction mixture was stirred at 100°C for 18 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were passed through Chem Elut TM The cartridge was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient n-heptane / ethyl acetate) to give 29 mg (purity 100%, yield 39%) ...

preparation Embodiment 3

[0342] Preparation Example 3 : Preparation of intermediate ethyl 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (Compound XXI.05)

[0343] step 1 : Preparation of ethyl 1-{[(3-amino-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (Compound XXVIII.01)

[0344] To 150 mg (0.60 mmol) of 3-amino-4,5-dichlorothiophene-2-carboxylate hydrochloride (1:1) (compound XXXa.02) and 255 mg (1.50 mmol) of 1-aminocyclopropanecarboxylic acid To a solution of ethyl ester hydrochloride (1:1) dissolved in 4.0 mL of dichloromethane was added 0.45 mL (2.59 mmol) of N,N-diisopropylethylamine, followed by 255 mg (1.50 mmol) of 2- A solution of chloro-1,3-dimethylimidazolium chloride in 2.0 mL of dichloromethane. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduce...

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Abstract

The present disclosure relates to thienyloxazolones and analogues thereof of formula (III) that may be used for protecting plants from bacterial diseases, in particular from bacterial diseases caused by bacteria belonging to the genus Xanthomonas.

Description

technical field [0001] The present invention relates to thienyloxazolones and analogs thereof, which can be used to protect plants from bacterial diseases, especially those caused by bacteria belonging to the genus Xanthomonas. Background technique [0002] Phytopathogenic bacteria can cause serious and economically devastating diseases worldwide. Among phytopathogenic bacteria, bacteria belonging to the genus Xanthomonas are considered to be the most destructive. They are the causative agent of various diseases on different host plants of agronomic interest. Examples of such diseases include: bacterial spot (caused by Xanthomonas campestris pv. vesicatoria) affecting peppers and tomatoes; affecting all cultivated Brassica species (e.g. , black rot (caused by Xanthomonas campestrispv. campestris) of cruciferous plants of Brussels sprout, cabbage, cauliflower and broccoli; affects citrus Citrus canker (caused by Xanthomonas axonopodis pv. citri) of genus species (lime, cit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/38A01N43/10A01N43/28C07D413/04A01P1/00
CPCC07D333/38A01N43/10A01N43/28C07D413/04A01P1/00A01N55/00C07D409/12C07F7/0812C07F7/083A61P33/00A61P31/04A01P13/00A01N43/76
Inventor D·伯尼尔S·布鲁奈特J·杜弗尔T·克诺博罗齐L·尼古拉斯土屋知己
Owner BAYER AG
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