Tetrafluorophenoxy nicotinamide compound as well as preparation method and application thereof for sterilizing

Abstract

The invention discloses a tetrafluorophenoxy nicotinamide compound as well as a preparation method and application thereof for sterilizing and relates to the field of agricultural pesticide compounds and in particular to a crop bactericidal compound as well as a preparation method and application thereof. The tetrafluorophenoxy nicotinamide compound has the general formula (I) shown in the specification, in the formula, R is the groups of -CH3, -CH2CH3, -CH2CH2CH3, -CH(CH3)2, -CH2CH2CH2CH3, -C(CH3)3, -CH2CH(CH3)2, -CH2CF3 or -CH2CHF2. The compound can be used for controlling eumycetes diseases, such as epidemic diseases and downy mildews, and has bactericidal activity on drug-resistant mildews and drug-sensitive mildews.

Description

technical field

[0001] The invention relates to the field of pesticide compounds, in particular to a crop bactericidal compound, its preparation method and its use. Background technique

[0002] At present, in the prevention and treatment of fungal diseases, metalaxyl, fosfo-aluminum, chlorothalonil, etc. are commonly used, but the control effect is not ideal. "Research Progress on Phytophthora capsici Resistant to Fungicides" ("Pesticides", Vol. 49, No. 2, February 2010) mentioned that Phytophthora capsici is prone to resistance to metalaxyl. It is mentioned in the article: Tonghua area Phytophthora capsici has 78.48% of strains resistant to metalaxyl, and only 21.52% of metalaxyl-sensitive strains, and its resistance multiple is 200-500 times, indicating that the resistance to mold to metalaxyl is ubiquitous and The level of resistance is high. Contents of the invention

[0003] Purpose of the invention: In view of the deficiencies in the prior art, the purpose of the ...

Examples

specific Embodiment 1

[0016] Compound 1: N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl)-2,3,5,6-tetrafluoro-4-methoxybenzoic acid carboxamide

[0017] The structural formula is:

[0018]

[0019] The preparation method is: put 22.4 grams of 2,3,5,6-tetrafluoro-4-methoxybenzoic acid, 200 ml of dichloromethane, and 15 ml of thionyl chloride into a three-necked flask, and stir at 0°C for 10 hours , the solvent and residual thionyl chloride are distilled off under reduced pressure. During distillation, the vacuum degree is controlled at -0.010kpa, and the temperature is not more than 100 degrees. Amino-3-chloro-5-trifluoromethylpyridine 21.0 g, cool down to 0 °C, add 12.6 ml of triethylamine dropwise at this temperature, after the addition is complete, keep it warm for 20 hours, add 300 ml of water to wash away the reaction formed Triethylamine hydrochloride was washed with 300 ml of water, dried, and the solvent was removed to obtain 38 to 39 grams of off-white solid N-(3-chloro-5-trifluoromet...

specific Embodiment 2

[0021] Compound 2: N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl)-2,3,5,6-tetrafluoro-4-ethoxybenzoic acid carboxamide

[0022] The structural formula is:

[0023]

[0024] The preparation method is: put 23.8 grams of 2,3,5,6-tetrafluoro-4-ethoxybenzoic acid, 200 ml of dichloromethane, and 25 ml of thionyl chloride into a three-necked flask, and stir at 20°C for 24 hours , the solvent and residual thionyl chloride are distilled off under reduced pressure. During distillation, the vacuum degree is controlled at -0.098kpa, and the temperature is not more than 100 degrees. Amino-3-chloro-5-trifluoromethylpyridine 21.0 g, cooled to 5 ° C, at this temperature, 63 ml of triethylamine was added dropwise, after the addition was completed, it was kept for 48 hours, and 300 ml of water was added to wash away the reaction formed Triethylamine hydrochloride, washed with 300 ml of water, dried, and stripped of the solvent gave 40-42 g of N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)m...

specific Embodiment 3

[0026] Compound 3: N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl)-2,3,5,6-tetrafluoro-4-propoxybenzoic acid carboxamide

[0027] The structural formula is:

[0028]

[0029] The preparation method is: put 25.2 grams of 2,3,5,6-tetrafluoro-4-propoxybenzoic acid, 200 ml of dichloromethane, and 20 ml of thionyl chloride into a three-necked flask, and stir at 10°C for 17 hours , the solvent and residual thionyl chloride are distilled off under reduced pressure. During distillation, the vacuum degree is controlled at -0.050kpa, and the temperature is not more than 100 degrees. Amino-3-chloro-5-trifluoromethylpyridine 21.0 g, cool down to 4 °C, add 38 ml of triethylamine dropwise at this temperature, after the addition is complete, keep it warm for 30 hours, add 300 ml of water to wash away the reaction formed Triethylamine hydrochloride, washed with 300 ml of water, dried, and stripped of the solvent gave 42-44 g of N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl )-2,3,5...

technical field

[0001] The invention relates to the field of pesticide compounds, in particular to a crop bactericidal compound, its preparation method and its use. Background technique

[0002] At present, in the prevention and treatment of fungal diseases, metalaxyl, fosfo-aluminum, chlorothalonil, etc. are commonly used, but the control effect is not ideal. "Research Progress on Phytophthora capsici Resistant to Fungicides" ("Pesticides", Vol. 49, No. 2, February 2010) mentioned that Phytophthora capsici is prone to resistance to metalaxyl. It is mentioned in the article: Tonghua area Phytophthora capsici has 78.48% of strains resistant to metalaxyl, and only 21.52% of metalaxyl-sensitive strains, and its resistance multiple is 200-500 times, indicating that the resistance to mold to metalaxyl is ubiquitous and The level of resistance is high. Contents of the invention

[0003] Purpose of the invention: In view of the deficiencies in the prior art, the purpose of the ...

Examples

specific Embodiment 1

[0016] Compound 1: N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl)-2,3,5,6-tetrafluoro-4-methoxybenzoic acid carboxamide

[0017] The structural formula is:

[0018]

[0019] The preparation method is: put 22.4 grams of 2,3,5,6-tetrafluoro-4-methoxybenzoic acid, 200 ml of dichloromethane, and 15 ml of thionyl chloride into a three-necked flask, and stir at 0°C for 10 hours , the solvent and residual thionyl chloride are distilled off under reduced pressure. During distillation, the vacuum degree is controlled at -0.010kpa, and the temperature is not more than 100 degrees. Amino-3-chloro-5-trifluoromethylpyridine 21.0 g, cool down to 0 °C, add 12.6 ml of triethylamine dropwise at this temperature, after the addition is complete, keep it warm for 20 hours, add 300 ml of water to wash away the reaction formed Triethylamine hydrochloride was washed with 300 ml of water, dried, and the solvent was removed to obtain 38 to 39 grams of off-white solid N-(3-chloro-5-trifluoromet...

specific Embodiment 2

[0021] Compound 2: N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl)-2,3,5,6-tetrafluoro-4-ethoxybenzoic acid carboxamide

[0022] The structural formula is:

[0023]

[0024] The preparation method is: put 23.8 grams of 2,3,5,6-tetrafluoro-4-ethoxybenzoic acid, 200 ml of dichloromethane, and 25 ml of thionyl chloride into a three-necked flask, and stir at 20°C for 24 hours , the solvent and residual thionyl chloride are distilled off under reduced pressure. During distillation, the vacuum degree is controlled at -0.098kpa, and the temperature is not more than 100 degrees. Amino-3-chloro-5-trifluoromethylpyridine 21.0 g, cooled to 5 ° C, at this temperature, 63 ml of triethylamine was added dropwise, after the addition was completed, it was kept for 48 hours, and 300 ml of water was added to wash away the reaction formed Triethylamine hydrochloride, washed with 300 ml of water, dried, and stripped of the solvent gave 40-42 g of N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)m...

specific Embodiment 3

[0026] Compound 3: N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl)-2,3,5,6-tetrafluoro-4-propoxybenzoic acid carboxamide

[0027] The structural formula is:

[0028]

[0029] The preparation method is: put 25.2 grams of 2,3,5,6-tetrafluoro-4-propoxybenzoic acid, 200 ml of dichloromethane, and 20 ml of thionyl chloride into a three-necked flask, and stir at 10°C for 17 hours , the solvent and residual thionyl chloride are distilled off under reduced pressure. During distillation, the vacuum degree is controlled at -0.050kpa, and the temperature is not more than 100 degrees. Amino-3-chloro-5-trifluoromethylpyridine 21.0 g, cool down to 4 °C, add 38 ml of triethylamine dropwise at this temperature, after the addition is complete, keep it warm for 30 hours, add 300 ml of water to wash away the reaction formed Triethylamine hydrochloride, washed with 300 ml of water, dried, and stripped of the solvent gave 42-44 g of N-(3-chloro-5-trifluoromethyl)pyridin-2-yl)methyl )-2,3,5...

Images