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Substituted thiophenecarboxamides and analogues as antibacterials agents

A compound, methylpropyl technology, applied in the direction of compounds, biocides, disinfectants, etc.

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

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

[0270] Preparation Example 1 : Preparation of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine methyl ester (compound II.01)

[0271] To a solution of 250 mg (1.08 mmol) of 3,4,5-trichlorothiophene-2-carboxylic acid and 210 mg (1.67 mmol) of ethyl glycine hydrochloride (1:1) dissolved in 4.2 mL of tetrahydrofuran was added 0.23 mL (1.62 mmol) of triethylamine followed by the addition of 1.0 mL (1.68 mmol) of a 50% (w / w) solution of propanephosphonic anhydride in ethyl acetate. The reaction mixture was stirred at room temperature for 20 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 / ethyl acetate) to afford 178 mg (93% purity, 51% yield) of N-[(3,4,5-trichloro-2 -thienyl)carbonyl]glycine methyl ester. LogP = 2.8. (M+H)=302.

preparation Embodiment 2

[0272] Preparation Example 2 : Preparation of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine (compound II.05)

[0273] To a solution of 178 mg (0.59 mmol) of N-[(3,4,5-trichloro-2-thienyl)carbonyl]glycine methyl ester dissolved in 3 mL of tetrahydrofuran, 1.3 mL of 1 M aqueous lithium hydroxide was added dropwise (1.3 mmol). The reaction was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, water and saturated aqueous sodium bicarbonate solution. 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 afford 159 mg (98% purity, 92% yield) of N-[(3,4,5-trichloro-2- Thienyl)carbonyl]glycine. LogP = 2.14. (M-H)=286.

preparation Embodiment 3

[0274] Preparation Example 3 : Preparation of ethyl 1-{[(3,4,5-trichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound II.02)

[0275] step 1 : Preparation of ethyl 1-{[(3-amino-4,5-dichloro-2-thienyl)carbonyl]amino}cyclopropanecarboxylate (compound XVIIc.01)

[0276] To 150mg (0.60mmol) of 3-amino-4,5-dichlorothiophene-2-formic acid hydrochloride (1:1) (compound XIXc.01) and 255mg (1.50mmol) of 1-aminocyclopropane formic 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 reduced pressure. The resi...

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Abstract

The present disclosure relates to substituted thiophene carboxamides and analogues thereof of formula (II) 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/38A01N43/10A01N43/28A01P1/00
CPCC07D333/38A01N43/10A01N43/28C07D413/04A01P1/00A01N55/00C07D409/12C07F7/0812C07F7/083A61P33/00A61P31/04A01P13/00A01N43/76
Inventor D·伯尼尔S·布鲁奈特P-Y·科奎罗恩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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