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Pyrazoleoxy acetic acid compounds, preparation method and use

A compound, the technology of oxyacetoxypyrazole, applied in the preparation, the application of fungicides, the field of pyrazoloxyacetic acid compounds, can solve the problems of many times of re-infection, difficult to control plant diseases, epidemic diseases and the like

Inactive Publication Date: 2008-10-15
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the plant diseases caused by oomycetes are difficult to control, especially downy mildew and blight with short incubation periods and many re-infection times, which can develop rapidly within a plant growing season and cause disease epidemics.

Method used

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  • Pyrazoleoxy acetic acid compounds, preparation method and use
  • Pyrazoleoxy acetic acid compounds, preparation method and use
  • Pyrazoleoxy acetic acid compounds, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Under stirring, add 50ml of anhydrous methanol and 0.3g of p-toluenesulfonic acid to 4-methoxycinnamic acid (0.05mol). After reflux reaction for 2h, methanol is distilled off under reduced pressure to obtain methyl 4-methoxycinnamate 8.82g; add methyl 4-methoxycinnamate and 50ml n-butanol to the newly prepared 28% sodium methoxide solution under stirring, react at 100°C for 4h, then add 8ml phenylhydrazine, continue to heat and reflux for 24h Afterwards, cool and filter to obtain 10.11 g of 1-phenyl-5-(4-methoxyphenyl)-3-pyrazolidinone; this compound was dissolved in N,N-dimethylformamide solution, Air was blown in, reacted at 100°C for 1 h, cooled to room temperature, and filtered to obtain 8.92 g of 1-phenyl-5-(4-methoxyphenyl)-3-hydroxypyrazole with a yield of 66.9%; Add 4.42g of hydroxypyrazole to 100ml of water, drop an equivalent amount of ethyl bromoacetate, react at 100°C for 2 hours, extract with ethyl acetate, dry over anhydrous magnesium sulfate, filter, and ...

Embodiment 2

[0023] Under stirring, add 100ml of anhydrous methanol and 0.5g of p-toluenesulfonic acid to 3,4,5-trimethoxycinnamic acid (0.1mol), after reflux for 2h, distill under reduced pressure to obtain 4-methoxycinnamic acid Methyl ester 19.68g; Add methyl 3,4,5-trimethoxycinnamate and 50ml n-butanol to the newly prepared 28% sodium methoxide solution under stirring, react at 100°C for 4h, then add 10ml phenylhydrazine , after continuing to heat and reflux for 24h, cool and filter to obtain 24.96g of 1-phenyl-5-(3,4,5-trimethoxyphenyl)-3-pyrazolidinone; this compound was dissolved in N, In N-dimethylformamide solution, air was blown in, reacted at 100°C for 1h, cooled to room temperature, and filtered to obtain 1-phenyl-5-(3,4,5-trimethoxyphenyl)- 22.61g of 3-hydroxypyrazole, yield 69.3%; take 11.31g of hydroxypyrazole and add it to 100ml of water, add dropwise the same amount of bromoacetic acid, react at 100°C for 2h, extract with ethyl acetate, anhydrous magnesium sulfate After d...

Embodiment 3

[0025] Under stirring, add 20ml of absolute ethanol and 0.3g of p-toluenesulfonic acid to 4-bromocinnamic acid (0.05mol), after reflux reaction for 2h, distill under reduced pressure to obtain 11.29g of ethyl 4-bromocinnamate; under stirring Add ethyl 4-bromocinnamate and 50ml of n-butanol to the newly prepared 28% sodium methoxide solution, react at 100°C for 4 hours, then add 6.55g of p-fluorophenylhydrazine, continue to heat and reflux for 24 hours, cool and filter , to obtain 1-(4-fluorophenyl)-5-(4-bromophenyl)-3-pyrazolidinone 12.1g; this compound was dissolved in N,N-dimethylformamide solution, blown into Air, reacted at 100°C for 1 hour, cooled to room temperature, and filtered to obtain 10.92 g of 1-(4-fluorophenyl)-5-(4-bromophenyl)-3-hydroxypyrazole with a yield of 65.3%; Take 5.32g of hydroxypyrazole and add it to 100ml of water, add an equivalent amount of chloroacetic acid dropwise, react at 100°C for 2 hours, extract with ethyl acetate, dry over anhydrous magnes...

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Abstract

The invention discloses a pyrazolyloxyacetic acid compound, a preparation method and use thereof. In the compound with a structural formula (I), X or Y is respectively hydrogen, C 1-4 alkyl, C 1-4 alkoxyl, substituted or non-substituted phenoxyl, halogen, nitryl or trifluoromethyl; and R is hydrogen or C 1-4 alkyl. The invention also discloses a preparation method for the compound and application thereof in preparing bactericide.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a pyrazole oxyacetic acid compound, a preparation method, and the application of the compound in fungicides. Background technique [0002] Nitrogen-containing heterocycles are a class of compounds with important application value and good biological activity. Many heterocycles have been developed into new medicines and pesticides, which play an important role in human health and agricultural production. At present, many research groups at home and abroad are engaged in research and development in this field. With my country's accession to WTO and implementation of intellectual property protection, there is an urgent need to strengthen research in the field of heterocycles and release new drugs with their own intellectual property rights. At present, the research on new heterocycles is very active. Pyrazole heterocycles have attracted much attention because of their w...

Claims

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Application Information

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IPC IPC(8): C07D231/22A01N43/56A01P3/00
Inventor 朱红军施红贾红圣李玉峰宋广亮刘缓缓孙永丰王锦堂
Owner NANJING UNIV OF TECH
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