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Pyrazolopyrimidinone compound and preparation method and application thereof

A technology of pyrazolopyrimidinone and azolopyrimidinone, which is applied in the field of pyrazolopyrimidinone compounds and their preparation, can solve problems such as limitations in the use range, achieve good inhibitory effect, excellent inhibitory activity, and low dosage

Active Publication Date: 2019-07-30
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Patent EP 170191 discloses a N-(7-fluoro-3,4-dihydro-3-oxo-(2-propynyl)-2H-1,4-benzoxazin-6-yl)cyclohexyl -1-ene-1,2-dicarboximide compound (formula C), has good herbicidal activity, is currently the highest-selling PPO herbicide, and has been used as a commercial herbicide so far, but many crops have Sensitive, so its scope of use is limited

Method used

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  • Pyrazolopyrimidinone compound and preparation method and application thereof
  • Pyrazolopyrimidinone compound and preparation method and application thereof
  • Pyrazolopyrimidinone compound and preparation method and application thereof

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preparation example Construction

[0050] The present invention provides a preparation method for the pyrazolopyrimidinone compound described in the above technical scheme, comprising the following steps:

[0051] Will R 1 substituted 5-amino-1H-pyrazole-4-carboxylic acid ethyl ester, tetrahydrofuran, methanol and sodium hydroxide solution are mixed, and hydrolysis is carried out to obtain the first intermediate;

[0052] mixing the first intermediate with thionyl chloride to perform a first substitution reaction to obtain a second intermediate;

[0053] The second intermediate, dichloromethane, pyridine and R 3 , R 4 Substituted 4-propargyl-6-amino-7-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-ones are mixed and subjected to a second substitution reaction to obtain a third intermediate ;

[0054] Mix the third intermediate, triethoxy compound and acetic anhydride for condensation-elimination reaction to obtain pyrazolopyrimidinone compounds; the triethoxy compound is triethyl orthoformate or triethyl orthoacetate ...

Embodiment 1

[0067]Mix 2.01g of 1-methyl-5-amino-1H-pyrazole-4-carboxylic acid ethyl ester, 4mL of tetrahydrofuran, 12mL of anhydrous methanol and 6mL of 3mol / L sodium hydroxide aqueous solution, reflux at 60°C for 4h, and carry out Hydrolysis reaction; after the reaction is completed, the resulting product system is subjected to vacuum distillation to remove most of the solvent, and then the resulting residue is acidified to pH=1 with 6mol / L hydrochloric acid, and a milky white precipitate appears, and the resulting precipitate system is filtered, washed, and Dichloromethane was washed and dried to obtain the first intermediate (1-methyl-5-amino-1H-pyrazole-4-carboxylic acid, 1.59 g), with a yield of 95%;

[0068] Add 0.47g of the first intermediate to the round bottom flask, then cool in an ice bath to control the temperature to 0°C, add 10mL of thionyl chloride dropwise with a dropping funnel to obtain a clear solution, after the dropwise addition, the resulting system is naturally raise...

Embodiment 2

[0073] Mix 2.01g of 1-methyl-5-amino-1H-pyrazole-4-carboxylic acid ethyl ester, 4mL of tetrahydrofuran, 12mL of anhydrous methanol and 6mL of 3mol / L sodium hydroxide aqueous solution, reflux at 60°C for 4h, and carry out Hydrolysis reaction; after the reaction is completed, the resulting product system is subjected to vacuum distillation to remove most of the solvent, and then the resulting residue is acidified to pH=1 with 6mol / L hydrochloric acid, and a milky white precipitate appears, and the resulting precipitate system is filtered, washed, and Dichloromethane was washed and dried to obtain the first intermediate (1-methyl-5-amino-1H-pyrazole-4-carboxylic acid, 1.59 g), with a yield of 95%;

[0074] Add 0.47g of the first intermediate to the round-bottomed flask, then cool in an ice bath to control the temperature to 0°C, add 10mL of thionyl chloride dropwise with a dropping funnel to obtain a clear solution, after the dropwise addition, the resulting system is naturally ra...

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Abstract

The invention belongs to the technical field of herbicides and particularly relates to a pyrazolopyrimidinone compound and a preparation method and application thereof. The provided pyrazolopyrimidinone compound shows good herbicidal activity on four tested plants (rape, amaranth, barnyard grass and crab grass) at the dosage of 1,500 gram / hectare, and a compound 4 and a compound 7 achieve the nearly 100% inhibition rate on the four tested plants (rape, amaranth, barnyard grass and crab grass). At the same time, the dosages of the compounds 4 and 7 are reduced for a herbicidal activity test, and the compound 7 still shows great herbicidal activity at the dosage of 93.75 gram / hectare. The pyrazolopyrimidinone compound has a very great application prospect.

Description

technical field [0001] The invention relates to the technical field of herbicides, in particular to a pyrazolopyrimidinone compound and a preparation method and application thereof. Background technique [0002] Chemically synthesized herbicides play an important role in agricultural production. Many herbicides currently used have disadvantages such as long residual time, large dosage, easy to cause phytotoxicity, and obvious weed resistance. Protoporphyrinogen oxidase (PPO) is an important target enzyme in the development of herbicides in recent years. As a herbicide, its inhibitor has the characteristics of low dosage, quick effect, difficult weed resistance and low toxicity, making this type of herbicide The share of herbicides in the global herbicide market has been increasing year by year, becoming an important class of herbicides. [0003] Patent US20050209251 discloses a pyrazolo[3,4-d]pyrimidin-4(5H)-one compound (Formula A), which has good herbicidal activity and n...

Claims

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Application Information

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IPC IPC(8): C07D487/04A01P13/00
CPCC07D487/04
Inventor 李华斌李露阳古建匡昕怡夏喆张尚中郭丽慧陈芮
Owner NANKAI UNIV
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