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Substituted thiophenecarboxamides and analogues as antibacterials agents

A compound, the technology of haloalkyl, applied in the field of substituted thiophene carboxamide and its analogues, can solve the problem of not providing etc.

Pending Publication Date: 2021-04-02
BAYER AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

WO2004 / 024692 also indicates that these compounds are useful in controlling bacterial diseases, but does not provide any evidence of such activity

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

[0352] Preparation Example 1 : Preparation of N-[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]glycine ethyl ester (Compound I.03)

[0353] step 1 : Preparation of methyl 3-amino-4,5-dichlorothiophene-2-carboxylate

[0354] 1.35 g (5.04 mmol) of methyl 3-acetamido-4,5-dichlorothiophene-2-carboxylate was dissolved in a mixture of 2.1 mL (25.18 mmol) of 37% (w / w) aqueous hydrochloric acid and 8.2 mL of methanol middle. The mixture was heated at 75°C for 3 hours. The cooled reaction mixture was treated with 30% (w / w) sodium hydroxide solution at 0°C. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 812 mg (98% purity, 70% yield) of 3-amino-4,5-dichlorothiophene-2-carboxylic acid as a brown solid methyl ester, which was used as such in the next step. LogP=3.11. (M+H)=226.

[0355] Step 2 : Preparation of methyl 3-bromo-4,5-dichlorothiophene-2-car...

preparation Embodiment 2

[0363] Preparation Example 2 : Preparation of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]-valine ethyl ester (Compound I.04)

[0364] To a solution of 154 mg (0.50 mmol) of 4,5-dibromo-3-methylthiophene-2-carboxylic acid and 183 mg (1.00 mmol) of DL-valine ethyl ester hydrochloride dissolved in 3 mL of tetrahydrofuran was added 0.21 mL (1.51 mmol) of triethylamine followed by the addition of 0.45 mL (0.75 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 saturated aqueous sodium bicarbonate solution 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 / ethyl acetate) to give 103 mg (95% purity, 45% yield) of N-[(4,5-dibromo-3-methyl) as a white solid -2-Thienyl)carbony...

preparation Embodiment 3

[0365] Preparation Example 3 : Preparation of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]-valine (Compound I.07)

[0366] To a solution of 164 mg (0.38 mmol) of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]-valine ethyl ester in 3 mL of tetrahydrofuran was added dropwise 0.81 mL of 1 M hydrogen Lithium oxide solution (0.81 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed twice with saturated aqueous sodium bicarbonate solution. The combined aqueous layers were carefully acidified with 37% (w / w) aqueous hydrochloric acid at 0°C and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 151 mg (98% purity, 96% yield) of N-[(4,5-dibromo-3-methyl) as a white solid -2-Thienyl)carbonyl]-valine. LogP=2.92. (M+H)=398.

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Abstract

The present disclosure relates to substituted thiophene carboxamides and analogues thereof of formula (I) 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 substituted thiophene carboxamides and their analogues, which are useful for protecting plants against bacterial diseases, in particular caused by bacteria belonging to the genus Xanthomonas. Background technique [0002] Phytopathogenic bacteria cause serious and economically damaging diseases worldwide. Among plant pathogenic bacteria, those belonging to the genus Xanthomonas are considered the most destructive. They are the cause of various diseases on different host plants of agronomic importance. Examples of such diseases include bacterial spot affecting peppers and tomatoes (caused by Xanthomonas campestris pv. vesicatoria); affecting all cultivated Brassica species (e.g. Black rot (caused by Xanthomonas campestrispv.campestris) of cruciferous plants (Brussels sprouts, cabbage, cauliflower and broccoli); affects citrus Citrus canker (caused by Xanthomonas axonopodis pv. citri) of the genus (lime, tangerine, gra...

Claims

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Application Information

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IPC IPC(8): C07D333/38A01N43/10A01N43/28C07D413/04A01P1/00C07D333/40
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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