Diheterocyclic compound as well as synthesis method and application thereof

A synthesis method and compound technology, applied in the fields of botanical equipment and methods, application, organic chemistry, etc., can solve the problem of less research

Inactive Publication Date: 2014-02-05
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, from a structural point of view, there are relatively few studies on nitrogen-containing compounds with a biheterocyclic structure. Compounds become a new direction of research

Method used

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  • Diheterocyclic compound as well as synthesis method and application thereof
  • Diheterocyclic compound as well as synthesis method and application thereof
  • Diheterocyclic compound as well as synthesis method and application thereof

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specific Embodiment approach 1

[0019] Specific embodiment 1: The general structural formula (I) of the biheterocyclic compound in this embodiment is:

[0020]

[0021] where R 1 is methyl or trifluoromethyl; R 2 is methyl or phenyl; R 3 It is a phenoxy group, a para-substituted phenoxy group or a chlorine atom, and the para-substituent in the para-substituted phenoxy group is a halogen, an alkyl group with 1 to 3 carbon atoms, an alkoxy group or a tert-butyl group .

[0022] The following table is an example, listing 10 biheterocyclic compound compounds with the general formula (I), but the present invention is not limited to the compounds in the following table.

[0023]

specific Embodiment approach 2

[0024] Specific embodiment two: The biheterocyclic compound in this embodiment is 4-(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carbonitrile, 4-(5 -(4-fluorophenoxy)-1,3-dimethyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carbonitrile, 4-(4-(tert-butyl)phenoxy) -1,3-Dimethyl-1H-pyrazol-4-yl)-1H-pyrrole-3-carbonitrile, 4-(5-(4-methylphenoxy)-1-methyl-3-( Trifluoromethyl)-1H-pyrazol-4-yl)-1H-pyrrole-3-carbonitrile or 4-(5-(4-fluorophenoxy)-1-methyl-3-(trifluoromethyl )-1H-pyrazol-4-yl)-1H-pyrrole-3-carbonitrile.

specific Embodiment approach 3

[0025] Specific embodiment three: the synthetic method of the biheterocyclic compound of the present embodiment is implemented according to the following steps:

[0026] 1. According to the molar ratio of acyl ethyl ester compound and hydrazine compound as 1: (1~1.1), add hydrazine compound dropwise into the reaction bottle containing acyl ethyl ester compound, and control the temperature at 15~20°C through a cold water bath. React under the condition of ℃ for 1-2 hours, then use vacuum distillation for 2.5-3.5 hours, then add toluene to the reaction system to reflux and divide the water, after removing water, cool down to precipitate the solid phase, and the solid phase is filtered and dried After obtaining the 5-pyrazolone compound;

[0027] 2. Add the 5-pyrazolone compound obtained in step 1 into the DMF (N,N-dimethylformamide) solution, add phosphorus oxychloride dropwise at a temperature of 10-20°C, and then raise the temperature to 110- 115°C, react for 5-10 hours, pour...

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Abstract

The invention relates to a diheterocyclic compound as well as a synthesis method, which belongs to the organic synthesis field, and particularly relates to a pyrazol-pyrrole heterocyclic compound as well as a synthesis method, and aims at further improving the sterilizing activity of a nitrogen-containing heterocyclic sterilizing agent. The structural formula of the diheterocyclic compound is shown in the specification. The preparation method comprises the following steps of synthesizing an acyl-ethyl-ester compound and a hydrazine compound into a 5-pyrazolone compound, synthesizing by utilizing DMP (dimethyl formamide) and phosphorus oxychloride to obtain 5-chloride-4-formylpyrazole, adding potassium hydroxide and phenol compound to prepare five-replaced formylpyrazole, then carrying out the condensation reaction to form the acrylamide compound, and finally facilitating the ring-closing reaction of the formylpyrazole and p-toluenesulfonyl methylisocyanide to obtain the diheterocyclic compound. When used as a sterilizing agent, the diheterocyclic compound has the bacteriostatic activity for the rice sheath blight disease, cucumber gray mold and cucumber downy mildew.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to pyrazolidine-pyrrole heterocyclic compounds and their synthesis method and application. Background technique [0002] Due to the unique biological activity of nitrogen-containing heterocyclic compounds, the research and development of such pesticides has become the top priority of people's research. Among them, the most representative nitrogen-containing heterocyclic compounds - pyrazole compounds, because of their own Multiple substitution sites endow this type of compound with better biological activity, and now it has also been involved in many fields such as sterilization, insecticide, and herbicide; another representative nitrogen-containing heterocyclic compound-pyrrole compound, In recent years, some new pesticide varieties with broad market prospects have appeared one after another. [0003] Among them, fluroxynil is a new type of non-systemic phenylpyrrole b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04A01N43/56A01P3/00
CPCA01N43/56C07D403/04
Inventor 王子时高金胜张爽宫艳波胡毓婕
Owner HEILONGJIANG UNIV
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