Benzoyl parazole compound as well as synthesis method thereof and application of same as herbicide

A technology for benzoylpyrazoles and benzoylpyrazoles is applied in the field of benzoylpyrazoles and their synthesis, and can solve the problems of low herbicidal activity and the like

Inactive Publication Date: 2013-09-18
HEILONGJIANG SHENGNONG SCI & TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problem that existing benzoylpyrazole compounds have lower herbicidal activity as herbicides, and provide benzoylpyrazole compounds and their synthesis methods and the application of these compounds as herbicides

Method used

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  • Benzoyl parazole compound as well as synthesis method thereof and application of same as herbicide
  • Benzoyl parazole compound as well as synthesis method thereof and application of same as herbicide
  • Benzoyl parazole compound as well as synthesis method thereof and application of same as herbicide

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Experimental program
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specific Embodiment approach 1

[0032] Specific embodiment one: the synthetic method of present embodiment 1,3-dimethyl-5-hydroxyl-4-(2-nitro-4-thiamphenicol) benzoylpyrazole is realized according to the following steps:

[0033] 1. Add 0.1mol of 1,3-dimethyl-5-pyrazolone, 80mL of acetonitrile and 0.125mol of triethylamine into the four-neck flask and stir evenly. Control the reaction temperature in a water bath to 20°C, and then dropwise add 40ml 0.105mol of 2-nitro-4-thiamphenicol benzoyl chloride dissolved in acetonitrile, stirred and reacted at room temperature for 4h, evaporated the solvent under reduced pressure to obtain a solid product, the solid product was dissolved in 50mL of dichloromethane, washed with 100mL of water, separated The solvent was then distilled off under reduced pressure to obtain 2-nitro-4-thiamphenicol-[1,3-dimethyl-pyrazol-5-yl]-ester;

[0034] 2. Add 150mL of acetonitrile and 0.2ml of acetone cyanohydrin with a purity of 98.5% to the reaction vessel, and then add 0.1mol of 2-ni...

specific Embodiment approach 2

[0041] Specific embodiment two: the synthetic method of present embodiment 1-methyl-3-trifluoromethyl-5-hydroxyl-4-(2-nitro-4-thiamphenicol) benzoylpyrazole is realized according to the following steps :

[0042] 1. Add 0.1mol of 1-methyl-3-trifluoromethyl-5-pyrazolone, 80mL of acetonitrile and 0.125mol of triethylamine into the four-necked flask and stir evenly. Control the reaction temperature in a water bath to 20°C, and then Add dropwise 0.105 mol of 2-nitro-4-thiamphenicol benzoyl chloride dissolved in 40 ml of acetonitrile, stir and react at room temperature for 4 h, evaporate the solvent under reduced pressure to obtain a solid product, and dissolve the solid product in 50 mL of dichloromethane, After washing with 100 mL of water and separating the liquid, the solvent was evaporated under reduced pressure to obtain 2-nitro-4-thiamphenicol-[1-methyl-3-trifluoromethyl-pyrazol-5-yl]-ester;

[0043] 2. Add 150mL of acetonitrile and 0.2ml of acetone cyanohydrin with a purit...

specific Embodiment approach 3

[0050] Specific embodiment three: the synthetic method of present embodiment 1-methyl-3-cyclopropyl-5-hydroxyl-4-(2-nitro-4-thiamphenicol) benzoylpyrazole is realized according to the following steps:

[0051] 1. Add 0.1mol of 1-methyl-3-cyclopropyl-5-pyrazolone, 80mL of acetonitrile and 0.125mol of triethylamine into the four-neck flask and stir evenly. Control the reaction temperature in a water bath to 20°C, then drop Add 0.105 mol of 2-nitro-4-thiamphenicol benzoyl chloride dissolved in 40 ml of acetonitrile, stir and react at room temperature for 4 h, evaporate the solvent under reduced pressure to obtain a solid product, dissolve the solid product in 50 mL of dichloromethane, and dissolve the solid product in 100 mL of After washing with water and liquid separation, the solvent was evaporated under reduced pressure to obtain 2-nitro-4-thiamphenicol-[1-methyl-3-cyclopropyl-pyrazol-5-yl]-ester;

[0052] 2. Add 150mL of acetonitrile and 0.2ml of acetone cyanohydrin with a p...

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Abstract

The invention discloses a benzoyl parazole compound as well as a synthesis method of the benzoyl parazole compound and an application of the benzoyl parazole compound as herbicide, relates to the benzoyl parazole compound as the herbicide and a synthesis method of the benzoyl parazole compound, and mainly solves the problem that the conventional benzoyl parazole compound as the herbicide is low in herbicide activity. According to the formula of the benzoyl parazole compound, the synthesis method comprises the following steps of: firstly, mixing a pyrazolone compound, acetonitrile and triethylamine, further dropping an acetonitrile-dissolved benzoyl chloride compound, thus obtaining a benzoyl pyrazol ester compound through reduced pressure distillation; and secondly, mixing the acetonitrile, acetone cyanogens alcohol and the benzoyl pyrazol ester compound, adding triethylamine, raising the reaction temperature, thus obtaining the benzoyl parazole compound through liquid separation and solvent evaporation. The seven benzoyl parazole compounds disclosed by the invention are excellent in herbicide activity and are mainly applied to herbicide as active components.

Description

technical field [0001] The invention relates to a benzoylpyrazole compound which can be used as a herbicide and a synthesis method thereof. Background technique [0002] P-hydroxyphenylpyruvate dioxygenase (HPPD) is a new class of herbicide target enzymes discovered in the 1990s. The HPPD inhibitor targeting this enzyme has the characteristics of high activity, broad herbicidal spectrum, can be used both before and after emergence, low residue, good environmental compatibility, safe use, etc. A hotspot in chemical pesticide research. Benzoylpyrazole compounds are typical representatives of HPPD inhibitors. They have special herbicidal activity. A large number of benzoylpyrazole compounds have been developed, and the commercialized varieties include pyrazolate (Pyrazolate), Benzofenap, Pyazoxyfen, Isoxaflutole, Pyrasulfotole, etc. However, the herbicidal activity against certain types of weeds, such as velvetleaf, retroflexus and other weeds, needs to be further improved. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/20A01P13/00
Inventor 高金胜姚林山刘吉龙左殿发
Owner HEILONGJIANG SHENGNONG SCI & TECH DEV CO LTD
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