Thiazole amide compound and application thereof

Abstract

Belonging to the field of bactericides, the invention in particular relates to a thiazole amide compound and application thereof. The thiazole amide compound is shown as general formula I in the specification, wherein all the substituent groups are defined in the specification. The general formula I compound has excellent antibacterial activity, and can be used for controlling plant fungal diseases.

Description

technical field

[0001] The invention belongs to the field of fungicides, in particular to a thiazole amide compound and its application. Background technique

[0002] Since diseases develop resistance to fungicides after a period of use, there is a constant need to invent new and improved compounds and compositions with fungicidal activity.

[0003] The bactericidal activity of thiazole amide compounds has been reported, such as JPS5657776 discloses the bactericidal activity of compound KC (compound 1 in the patent).

[0004]

[0005] In the prior art, no thiazole amide compound having a structure as shown in the general formula I of the present invention has been reported. Contents of the invention

[0006] The object of the present invention is to provide a kind of thiazole amide compound and application thereof.

[0007] To achieve the above object, the technical scheme of the present invention is as follows:

[0008] A thiazole amide compound, as shown in general...

Examples

Embodiment 1

[0075] The synthesis of embodiment 1 compound 13

[0076]

[0077] Add 2-chloro-5-isopropoxyaniline (210 mg, 1.131 mmol), triethylamine (137 mg, 1.357 mmol) and 10 ml of dichloromethane into the reaction flask, add 2 dropwise under stirring at room temperature, 10 mL of dichloromethane solution of 4-bistrifluoromethylthiazole-5-carbonyl chloride (321 mg, 1.131 mmol). After dropping, react at room temperature for 1.5 hours, pour the reaction solution into 30 ml of water, take the organic layer, wash the organic layer with saturated aqueous sodium bicarbonate solution and saturated brine, dry over anhydrous magnesium sulfate, and evaporate the solvent under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=20:1, 10:1) to obtain 210 mg of compound 13, a yellow solid, melting point 89-90°C.

Embodiment 2

[0078] The synthesis of embodiment 2 compound 41

[0079]

[0080] Add 2-chloro-5-isopropoxyaniline (220 mg, 1.185 mmol), triethylamine (144 mg, 1.422 mmol) and 10 ml of dichloromethane into the reaction flask, and add 4- Ethyl-2-methylthiazole-5-carbonyl chloride (225 mg, 1.185 mmol) in dichloromethane 10 mL. After dropping, the reaction was completed after 1.5h. The reaction solution was poured into 30 ml of water, and the organic layer was taken. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether = 10:1) to obtain 150 mg of compound 41 as a brown oil.

Embodiment 3

[0081] The synthesis of embodiment 3 compound 44

[0082]

[0083]Add 2-fluoro-5-isopropoxyaniline (200 mg, 1.182 mmol), triethylamine (144 mg, 1.418 mmol) and 10 ml of dichloromethane into the reaction flask, and add 2- A solution of trifluoromethyl-4-ethylthiazole-5-carbonyl chloride (288 mg, 1.182 mmol) in dichloromethane (10 mL). After dropping, the reaction was completed after 1.5 hours. The reaction solution was poured into 30 ml of water, and the organic layer was taken. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=20:1) to obtain 110 mg of compound 44 as a yellow solid with a melting point of 87-88°C.

[0084] Other compounds of general formula I of the present invention can be synthesized with reference to the above-mentioned m...

technical field

[0001] The invention belongs to the field of fungicides, in particular to a thiazole amide compound and its application. Background technique

[0002] Since diseases develop resistance to fungicides after a period of use, there is a constant need to invent new and improved compounds and compositions with fungicidal activity.

[0003] The bactericidal activity of thiazole amide compounds has been reported, such as JPS5657776 discloses the bactericidal activity of compound KC (compound 1 in the patent).

[0004]

[0005] In the prior art, no thiazole amide compound having a structure as shown in the general formula I of the present invention has been reported. Contents of the invention

[0006] The object of the present invention is to provide a kind of thiazole amide compound and application thereof.

[0007] To achieve the above object, the technical scheme of the present invention is as follows:

[0008] A thiazole amide compound, as shown in general...

Examples

Embodiment 1

[0075] The synthesis of embodiment 1 compound 13

[0076]

[0077] Add 2-chloro-5-isopropoxyaniline (210 mg, 1.131 mmol), triethylamine (137 mg, 1.357 mmol) and 10 ml of dichloromethane into the reaction flask, add 2 dropwise under stirring at room temperature, 10 mL of dichloromethane solution of 4-bistrifluoromethylthiazole-5-carbonyl chloride (321 mg, 1.131 mmol). After dropping, react at room temperature for 1.5 hours, pour the reaction solution into 30 ml of water, take the organic layer, wash the organic layer with saturated aqueous sodium bicarbonate solution and saturated brine, dry over anhydrous magnesium sulfate, and evaporate the solvent under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=20:1, 10:1) to obtain 210 mg of compound 13, a yellow solid, melting point 89-90°C.

Embodiment 2

[0078] The synthesis of embodiment 2 compound 41

[0079]

[0080] Add 2-chloro-5-isopropoxyaniline (220 mg, 1.185 mmol), triethylamine (144 mg, 1.422 mmol) and 10 ml of dichloromethane into the reaction flask, and add 4- Ethyl-2-methylthiazole-5-carbonyl chloride (225 mg, 1.185 mmol) in dichloromethane 10 mL. After dropping, the reaction was completed after 1.5h. The reaction solution was poured into 30 ml of water, and the organic layer was taken. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether = 10:1) to obtain 150 mg of compound 41 as a brown oil.

Embodiment 3

[0081] The synthesis of embodiment 3 compound 44

[0082]

[0083]Add 2-fluoro-5-isopropoxyaniline (200 mg, 1.182 mmol), triethylamine (144 mg, 1.418 mmol) and 10 ml of dichloromethane into the reaction flask, and add 2- A solution of trifluoromethyl-4-ethylthiazole-5-carbonyl chloride (288 mg, 1.182 mmol) in dichloromethane (10 mL). After dropping, the reaction was completed after 1.5 hours. The reaction solution was poured into 30 ml of water, and the organic layer was taken. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluent: ethyl acetate:petroleum ether=20:1) to obtain 110 mg of compound 44 as a yellow solid with a melting point of 87-88°C.

[0084] Other compounds of general formula I of the present invention can be synthesized with reference to the above-mentioned m...

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