(1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof

A technology of ethyl benzoate and carboxamide group, which is applied to (1H-pyrazole-4-carboxamido) ethyl benzoate compounds and the fields of preparation and application thereof, can solve problems such as difficulty in controlling diseases and insect pests, and achieves the preparation of Simple method, convenient operation effect

Active Publication Date: 2019-12-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of pesticides has also brought many disadvantages. The excessive and improper use of pesticides has also made many germs resistant to existing pesticides, making it more and more difficult to control pests and diseases. At the same time, some highly toxic pesticides also bring environmental pollution had a certain impact

Method used

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  • (1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof
  • (1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof
  • (1H-pyrazole-4-carboxamido) ethyl benzoate compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of ethyl 2-(3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamido)-2-methylbenzoate

[0032] (1) Synthesis of ethyl 4,4-difluoro-2-(methoxymethylene)-3-oxobutanoate (Ⅱ-1):

[0033] Add acetic anhydride (150.0mmol), ethyl difluoroacetoacetate (50.0mmol) and triethyl orthoformate (60.0mmol) into a 100mL reaction flask, heat up to reflux for 8 hours, stop heating, and wait for the reaction solution to cool to After room temperature, it was concentrated under reduced pressure to remove the acetic anhydride solvent, and ethyl 4,4-difluoro-2-(methoxymethylene)-3-oxobutanoate represented by formula (II-1) was obtained.

[0034] (2) Synthesis of ethyl 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate formula (Ⅲ-1):

[0035] Stir and mix ethyl 4,4-difluoro-2-(methoxymethylene)-3-oxobutanoate (48mmol) represented by formula (II-1) with 10mL ethanol, and then Add dropwise to the mixed solution of 8.3g of 40% methylhydrazine aqueous solution and 15mL ethan...

Embodiment 2

[0045] Example 2 Preparation of ethyl 2-(3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamido)-2,6-difluorobenzoate

[0046] The 2-methylbenzoyl chloride in the step (5) of Example 1 was replaced by 2,6-difluorobenzoyl chloride in an equivalent molar amount, and other operations were the same as in Example 1 to obtain (A2).

[0047] Ethyl 2-(3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamido)-2,6-difluorobenzoate: white solid, yield: 51.6%, mp : 102-104°C; 1 H NMR (CDCl 3 ,500MHz), δ:7.91(s,1H,py),7.49-7.44(m,1H,ph),7.36-7.41(m,2H,ph),6.81(d,J=54.5Hz,1H),6.68 (s,1H,NH),4.56-4.52(m,2H,CH 2 ),3.94(s,3H,CH 3 ), 3.81 (q, J=5.5Hz, 2H, CH 2 ); HRMS(ESI) for C 15 h 13 f 4 N 3 o 3 m / z: Calculated, 360.0966, Found, 360.0968 [M+H] + .

Embodiment 3

[0048] Example 3 Preparation of ethyl 2-(3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamido)-2,6-dichlorobenzoate

[0049] The 2-methylbenzoyl chloride in the step (5) of Example 1 was replaced by 2,6-dichlorobenzoyl chloride in an equivalent molar amount, and other operations were the same as in Example 1 to obtain (A3).

[0050] Ethyl 2-(3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamido)-2,6-dichlorobenzoate: white solid, yield: 47.3%, mp : 92-94°C; 1 H NMR (CDCl 3 ,500MHz), δ:7.84(s,1H,py),7.24(d,J=4.0Hz,2H,ph),7.19-7.16(m,1H,ph),7.04-6.81(m,2H,CHF 2 ,NH),4.46(t,J=5.5Hz,2H,CH 2 ),3.81(s,3H,CH 3 ), 3.67 (q, J=5.5Hz, 2H, CH 2 ); HRMS(ESI) for C 15 h 13 Cl 2 f 2 N 3 o 3 m / z: Calculated, 392.0375, Found, 392.0380 [M+H] + .

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Abstract

The invention discloses an ethyl (1H-pyrazole-4-carboxamido) benzoate compound as well as a preparation method and application thereof. The structural formula of the (1H-pyrazole-4-carboxamido) ethylbenzoate compound is as shown in the formula (I), wherein the substituent groups R1 are phenyl or substituted phenyl, the number of substituent groups on a benzene ring of the substituted phenyl is one or more, and each substituent group is independently selected from H, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C3 halogenated alkyl or nitro; and the substituent R2 is methyl, monofluoromethyl, difluoromethyl or trifluoromethyl. The invention discloses a novel compound with bactericidal activity, which is simple in preparation method and convenient to operate, and the obtained compound has betterinhibitory activity on pathogenic bacteria such as cucumber botrytis cinerea, fusarium oxysporum, cucumber corynespora leaf spot and the like under the concentration of 50 mg / mL.

Description

technical field [0001] The invention relates to a (1H-pyrazole-4-carboxamido) ethyl benzoate compound and a preparation method and application thereof. Background technique [0002] Now the world's total population has reached 7.5 billion, and with the population growth, the demand for food has also increased. Therefore, in today's world, food production is undoubtedly very important, and pesticides have been an important factor to ensure high food production since they came out. means. However, the use of pesticides has also brought many disadvantages. The excessive and improper use of pesticides has also made many germs resistant to existing pesticides, making it more and more difficult to control pests and diseases. At the same time, some highly toxic pesticides also bring environmental pollution had a certain impact. As the requirements for the quality of the living environment continue to increase, people's requirements for pesticides are becoming more and more string...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/14A01P3/00
CPCC07D231/14
Inventor 刘幸海郭长飞金涛谭成侠翁建全武宏科
Owner ZHEJIANG UNIV OF TECH
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