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Fused Heterocyclic Compounds and Their Applications

A technology of fused heterocycles and compounds, applied in the field of heterocycles, can solve the problems of high environment, toxicity, and lack of specific selectivity

Active Publication Date: 2019-02-05
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the existing insecticides usually do not have specific selectivity, and have high toxicity to the environment while killing pests. At the same time, the excessive and frequent use of a single pesticide causes serious resistance problems and cross-resistance, which limits the use of pesticides. use, restricting the development of agriculture and forestry

Method used

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  • Fused Heterocyclic Compounds and Their Applications
  • Fused Heterocyclic Compounds and Their Applications
  • Fused Heterocyclic Compounds and Their Applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1: Using method A to synthesize A1~A47 compounds

[0098] Method A

[0099]

[0100] For example, the synthesis of compound A1:

[0101] S1: 5-Amino-1H-pyrazole-3-cyano

[0102] 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.

[0103] S2: 5,5-Dimethyl-4,5-dihydropyrazol[1,5-α]quinazoline-2-cyano

[0104] Under nitrogen protection, 5-amino-1H-pyrazole-3-cyano (1.0mmol), 1-bromo-2-(1-bromo-1-methylethyl)benzene (1.0mmol), cuprous iodide (0.2 mmol) and cesium carbonate (0.5 mmol) in DMF was stirred at 100 °C for 24 hours. C...

Embodiment 2

[0115] Example 2: Using Method B to Synthesize B1~B12 Compounds

[0116] Method B

[0117]

[0118] For example, the synthesis of compound B1:

[0119] S1:2-amino-4-(4-methoxybenzene)-1H-pyrrole-3-cyano

[0120] 2-Bromo-1-(4-methoxyphenyl)-acetyl (1.0mmol) was added in 15 ml of DMF, then sodium azide (10.0mmol) was added to the reaction solution, and the reaction mixture was stirred After 48 hours, the reaction mixture was filtered and the resulting filtrate was extracted several times with diethyl ether. Concentrate in vacuo, the residue is dissolved in methanol, under a hydrogen atmosphere, 10% palladium carbon (0.2 mmol) is added thereto, the reaction mixture is stirred for 24 hours, the mixture is filtered, the obtained filtrate is concentrated in vacuo, the residue is dissolved in tetrahydrofuran, Acetic anhydride (2.0mmol), triethylamine (2.0mmol) were added thereto, and after the reaction mixture was stirred for 5 hours, the mixture was concentrated in vacuo, an...

Embodiment 3

[0130] Example 3: Using method C to synthesize C1~C64 compounds

[0131] Method C

[0132]

[0133] For example, the synthesis of compound C1:

[0134] S1: (2-Amino-3-chloro-5-(trifluoromethyl)phenyl)boronic acid

[0135] Under nitrogen protection, 2-bromo-6-chloro-4-trifluoromethylaniline (1.0 mmol) was dissolved in 20 ml of dry tetrahydrofuran, cooled to 0 degrees Celsius, and n-butyl lithium (2.5 mmol, 1.6M n-hexane solution), stirred for 2 hours, slowly added trimethylchlorosilane (2.5mmol) dropwise to the reaction mixture, the reaction was naturally heated and stirred for 12 hours, concentrated in vacuo to remove the solvent, and obtained the target compound by distillation under reduced pressure (2-Amino-3-chloro-5-(trifluoromethyl)phenyl)boronic acid (yield: 87%).

[0136] S2: 2-chloro-6-(1,2-dichloro-3-buten-2-yl)-4-(trifluoromethyl)aniline

[0137] Under nitrogen protection, 3-bromo-3,4-dichloro-1-butene (1.0mmol), Pd(dppf)Cl 2 (0.15mmol), sodium carbonate (...

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Abstract

The present invention discloses fused heterocyclic compounds as well as optical isomers, cis-trans isomers or agrochemically acceptable salts thereof and an application of a composition. The fused heterocyclic compounds have a structure shown in a formula I in the description. The fused heterocyclic compounds as well as the optical isomers, the cis-trans isomers or the agrochemically acceptable salts thereof provided by the present invention have high killing activity against agricultural and forestry pests, animal parasitic pests, sanitary pests and the like, delayed effects on invasive solenopsis invicta, and lower toxicity to environmental organisms such as apis cerana and bombyx mori.

Description

technical field [0001] The invention belongs to the field of heterocyclic compounds, in particular to condensed heterocyclic compounds and their optical isomers, cis-trans isomers or pesticide acceptable salts and their preparation methods and applications. 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, the existing insecticides usually do not have ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A01N43/90A01N47/22A01N47/38A01P7/04A01P7/02A01P5/00
CPCA01N43/90A01N47/22A01N47/38C07D487/04
Inventor 徐汉虹江薰垣魏孝义张志祥林菲姚光凯邓成菊
Owner SOUTH CHINA AGRI UNIV
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