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Fused heterocycle compounds containing pyrazolone rings and applications thereof

A technology of fused heterocyclic compounds, applied in the field of fused heterocyclic compounds, can solve the problems of restricting the development of agriculture and forestry, reducing the efficacy of pesticides, and restricting the application of pesticides, etc.

Active Publication Date: 2018-06-08
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, due to the excessive and frequent use of a single pesticide, coupled with the fact that the existing pesticides have high toxicity to the environment while killing pests, serious problems of resistance and cross-resistance have been caused, resulting in a decrease in the efficacy of pesticides. The application of pesticides has been greatly restricted, thereby restricting the development of agriculture and forestry

Method used

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  • Fused heterocycle compounds containing pyrazolone rings and applications thereof
  • Fused heterocycle compounds containing pyrazolone rings and applications thereof
  • Fused heterocycle compounds containing pyrazolone rings and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Embodiment 1 uses method A to synthesize a-1~a-138 compounds

[0091] Method A:

[0092]

[0093] Taking compound a-44 as an example, its specific preparation process is as follows:

[0094] S1: 5-Amino-1H-pyrazole-3-cyano

[0095] Add ethyl 2,3-dicyanopropionate (1.0 mmol) to 20.0 mL of ethanol, stir vigorously, add hydrazine hydrate (2.0 mmol) to the reaction solution, heat to reflux, stop heating after 3 hours, and cool to room temperature. The mixture was concentrated in vacuo, the mixture was extracted with ethyl acetate and water, and the extracted ethyl acetate was concentrated in vacuo to give 5-amino-1H-pyrazole-3-cyano as a white solid, which was used without further purification in in the next step.

[0096] S2: 5,5-dichloro-7-trifluoromethyl-4,5-dihydropyrazol[1,5-α]quinazoline[3,2-e]pyridine-2-cyano

[0097]Under the protection of nitrogen, 5-amino-1H-pyrazole-3-cyano (1.0mmol), 2-bromo-3-(trichloromethyl)-5-trifluoromethylpyridine (1.0mmol), iodide ...

Embodiment 2

[0105] Embodiment 2 uses method B to synthesize b-1~b-138 compound

[0106] Method B:

[0107]

[0108] Taking compound b-87 as an example, its specific synthesis process is as follows:

[0109] S1: 5-amino-1H-pyrazole-3-trifluoromethyl (reference Journal of medicinal chemistry (2017) 60:5099)

[0110] Under nitrogen protection, sodium hydride (2.5 mmol) was added to 20 ml of anhydrous tetrahydrofuran at 0°C, followed by anhydrous acetonitrile (2.0 mmol) and ethyl trifluoroacetate (1.0 mmol) were added to the reaction solution, heated to reflux, 20 After 2 hours, the heating was stopped, cooled to room temperature, and the mixture was concentrated in vacuo. The mixture was extracted with ether and water, the pH was adjusted to 2 by adding dilute hydrochloric acid, extracted with ether, and concentrated in vacuo to give 4,4,4-trifluoro-3-carbonylbutyronitrile as a brown oil, the intermediate was not further purified, used directly in the next step.

[0111] Add methanesu...

Embodiment 3

[0122] Example 3 Using method C to synthesize c-1~c-349 compounds

[0123] Method C:

[0124]

[0125] Taking compound c-27 as an example, its specific synthesis process is as follows:

[0126] S1: 6-Chloro-2-cyano-5-(2'2-diethoxy)-8-trifluoromethyl-4,5-dihydropyrazol[1,5-α]quinazoline- 5-ethyl carboxylate

[0127] Under nitrogen protection, 5-amino-1H-pyrazole-3-cyano (1.0mmol), 2-bromo-2-(2-bromo-6-chloro-4-trifluoromethylphenyl) malic acid diethyl A DMF mixture of ester (1.0 mmol), cuprous iodide (0.2 mmol) and cesium carbonate (0.5 mmol) was stirred at 100 °C for 24 hours. Cooled to room temperature, the mixture was filtered, concentrated in vacuo, and the residue was purified by column chromatography to obtain the target compound 6-chloro-2-cyano-5-(2'2-diethoxy)-8-trifluoromethyl-4, Ethyl 5-dihydropyrazolo[1,5-α]quinazoline-5-carboxylate (yield: 30%).

[0128] S2: 6-chloro-2-cyano-5-(2'2-diethoxy)-8-trifluoromethyl-3-trifluoromethylsulfinyl-4,5-dihydropyrazole[ ...

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Abstract

The invention provides a type of fused heterocycle compounds containing pyrazolone rings, optical isomers, cis-trans-isomers or pharmaceutically acceptable salts of fused heterocycle compounds and applications of the fused heterocycle compounds, and the optical isomers, cis-trans-isomers or pharmaceutically acceptable salts of the fused heterocycle compounds. The fused heterocycle compounds have astructure represented by a formula (I) (shown in the description). The fused heterocycle compounds containing the pyrazolone rings, and the optical isomers, the cis-trans-isomers or the pharmaceutically acceptable salts of the fused heterocycle compounds have high killing activity to agriculture and forestry pests, health pests and the like, furthermore, and the compounds have a delayed action effect to pests such as red imported fire ants, so the pests can carry the drug to a nest, and the whole nest and an queen ant can be well killed; and the compounds have very good application prospects.

Description

technical field [0001] The invention belongs to the field of heterocyclic compounds, and in particular relates to a class of condensed heterocyclic compounds containing pyrazole rings, optical isomers, cis-trans isomers or pesticide acceptable salts, preparation methods and applications thereof. Background technique [0002] Heterocyclic new pesticides represented by nitrogen-containing heterocyclic rings have high insecticidal activity, broad insecticidal spectrum, low toxicity to mammals, and appropriate field stability. Heterocyclic compounds have become an important hot spot for new pesticide creation . In recent years, among the newly developed pesticides, Flupyrimin, Flupyrfurone, Cyclofenpyr, Sulfoxaflor, Fluonicamid, Spirotetramat, Cyflumetate, Nipyridofen, Cyanotranil 酰胺等无一不属于含氮杂环化合物(参见专利US2013150414、CN103960242、CN103254125、CN102892290、DE102006015467、WO2010069266、WO2007095229、EP 580374、WO 9805638、WO 2002014263、JP 2003201280、WO 2004067528)。 [0003] However, due to ...

Claims

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Application Information

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IPC IPC(8): C07D471/14C07D487/04A01N43/90A01P7/04A01P7/02
CPCA01N43/90C07D471/14C07D487/04
Inventor 徐汉虹江薰垣魏孝义张志祥林菲邓成菊赵晨杨帅赵伟靖
Owner SOUTH CHINA AGRI UNIV
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