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

A technology of tetrafluorophenoxynicotine amine and compounds, which is applied in the field of crop bactericidal compounds, can solve problems such as unsatisfactory control effects, and achieve good bactericidal effects, long-lasting effects, and high therapeutic activity

Active Publication Date: 2011-06-08
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, in the prevention and treatment of fungal diseases, metalaxyl, fosfo-alumin

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

Specific embodiment 1:

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

[0017] The structural formula is:

[0018]

[0019] The preparation method is: throw 22.4 g of 2,3,5,6-tetrafluoro-4-methoxybenzoic acid, 200 ml of dichloromethane, 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 out under reduced pressure. During the distillation, the vacuum is controlled at -0.010kpa and the temperature is not more than 100 degrees. After the distillation is completed, the temperature is lowered to room temperature, and 200 ml of dichloromethane is added. Amino-3-chloro-5-trifluoromethylpyridine 21.0g, the temperature is reduced to 0℃, 12.6ml triethylamine is added dropwise at this temperature, the addition is over, keep for 20 hours, add 300ml water to wash away the reaction product Triethylamine hydrochloride, then washed wi...

Example Embodiment

Specific embodiment 2:

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

[0022] The structural formula is:

[0023]

[0024] The preparation method is as follows: throw 23.8 g 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 out under reduced pressure. During the distillation, control the vacuum degree to -0.098kpa, the temperature is not greater than 100 degrees, the distillation is over, and the temperature is lowered to room temperature. Add 200 ml of dichloromethane and add 2-methyl under stirring. Amino-3-chloro-5-trifluoromethylpyridine 21.0g, cool to 5℃, add 63ml triethylamine dropwise at this temperature, after the dropwise addition, keep for 48 hours, add 300ml water to wash away the reaction product Triethylamine hydrochloride, then ...

Example Embodiment

Specific embodiment 3:

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

[0027] The structural formula is:

[0028]

[0029] The preparation method is as follows: 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 out under reduced pressure. During the distillation, the vacuum degree is controlled at -0.050kpa, the temperature is not more than 100 degrees, the distillation is over, the temperature is reduced to room temperature, 200 ml of dichloromethane is added, and 2-methyl is added under stirring 21.0g of amino-3-chloro-5-trifluoromethylpyridine, cool to 4℃, add 38ml of triethylamine dropwise at this temperature, after the dropwise addition, keep for 30 hours, add 300ml of water to wash away the reaction product Triethylamin...

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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 ...

Claims

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Application Information

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IPC IPC(8): C07D213/61A01N43/40A01P3/00
Inventor 唐剑峰王爱玲
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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