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[1,2,4]triazolo[4,3-alpha]pyridine-3(2H)-one derivative, preparation method and applications thereof

A technology of derivatives and pyridine, which is applied in the field of [1,2,4]triazol[4,3-a]pyridin-3-one derivatives and their preparation, achieving simple preparation methods, convenient post-processing, and convenient operation Effect

Inactive Publication Date: 2015-11-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Combining pyridine ring with 1,2,4-triazole ring is considered to be a good way to synthesize new active compounds, but there are no related reports

Method used

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  • [1,2,4]triazolo[4,3-alpha]pyridine-3(2H)-one derivative, preparation method and applications thereof
  • [1,2,4]triazolo[4,3-alpha]pyridine-3(2H)-one derivative, preparation method and applications thereof
  • [1,2,4]triazolo[4,3-alpha]pyridine-3(2H)-one derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 2-benzyl-8-chloro-[1,2,4]triazol[4,3- a ]pyridine-3(2 H )-ketone

[0026] Dicarbonyl imidazole (1.4 mmol), 3-chloro-2-hydrazinopyridine (1 mmol) were added to the reaction flask, the reaction mixture was dissolved in tetrahydrofuran solvent, then reacted at room temperature for 24h, poured into 40ml of water after the reaction A precipitate formed and was filtered, and the crude solid was recrystallized from petroleum ether. Put tetrahydrofuran (3 mL), formula (III) (0.25 g, 1 mmol), benzyl chloride (1.5 mmol) and potassium carbonate (1.5 mmol) into the reaction flask, then react at room temperature for 24 h, pour the crushed Collected by recrystallization on ice. The resulting 2-benzyl-8-chloro-[1,2,4]triazol[4,3- a ]pyridine-3(2 H )-ketone, yield 75%, melting point 109-111℃; 1H NMR (CDCl3, 400 MHz), δ: 5.21 (s, 2H, NCH2), 6.45(t, J =6.8Hz, 1H, Py-H), 7.15(d, J =7.2Hz, 1H, Py-H), 7.31-7.34(m, 3H, Ar-H), 7.43-7.45(m, 2H, Ar-H), 7.75(d, J ...

Embodiment 2

[0028] The synthesis method is the same as that in Example 1, with 1.0 mmol of dicarbonyl imidazole and 1 mmol of 3-chloro-2-hydrazinopyridine, the yield of the target product is 73%, and the melting point is 119-121°C; 1H NMR (CDCl3, 400 MHz), δ: 5.21 (s, 2H, NCH2), 6.45(t, J =6.8Hz, 1H, Py-H), 7.15(d, J =7.2Hz, 1H, Py-H), 7.31-7.34(m, 3H, Ar-H), 7.43-7.45(m, 2H, Ar-H), 7.75(d, J =7.2Hz, 1H, Py-H). Elemental analysis for C13H10ClN3O: found C 59.99, H 3.76, N 16.01; calcd. C, 60.12; H, 3.88; N, 16.18.

Embodiment 3

[0029] Example 3: Synthesis of 2-benzyl-8-chloro-[1,2,4]triazol[4,3,a]pyridin-3(2H)one

[0030]Urea (1 mmol), 3-chloro-2-hydrazinopyridine (143 mg, 1.0 mmol) were added to a CEM specific microwave digestion vessel. Then the microwave-assisted synthesizer worked under the conditions of radiation (150 W, 160 ℃, 200 psi, 5 min). The mixture was cooled to room temperature by compressed air in a microwave chamber for 5 min. Then pour 40ml of water to form a precipitate and filter, and the crude solid is recrystallized with n-hexane. Acetone (4 mL), formula (III) (0.25 g, 1 mmol), benzyl chloride (1.1 mmol) and potassium bicarbonate (1.2 mmol) were added to a CEM 10 ml rated pressure jar. Then under the conditions of (150 w, 90℃, 200 psi, 15 minutes) microwave radiation assisted synthesis. Then cool to below 50 ℃ and pour into crushed ice to recrystallize and collect. The resulting 2-benzyl-8-chloro-[1,2,4]triazol[4,3- a ]pyridine-3(2 H )-ketone, yield 70%, melting point 111-1...

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Abstract

The present invention relates to a [1,2,4]triazolo[4,3-alpha]pyridine-3(2H)-one derivative represented by a formula (I), a preparation method and applications thereof, particularly a preparation method of the compound and applications of the compound in prevention and control of echinochloa crusgalli, setaria viridis (l.) beauv, poa annua, brassica juncea, abutilon theophrasti medicus, amaranthus retroflexus l and chenopodium serotinum l, wherein R in the formula (I) is benzyl, 4-chlorobenzyl, 4-methoxybenzyl, 3-chlorobenzyl, 2-fluorobenzyl, 4-bromobenzyl, 4-(tert-butyl)benzyl, 4-nitrile benzyl, acetonitrile, propyl, undecyl, butyl or allyl. The compound of the present invention is the new compound having weeding activity and provides foundation for research and development of new pesticides.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a [1,2,4]triazole[4,3- a ]pyridine-3(2 H )-ketone derivatives and their preparation methods and applications. Background technique [0002] The application of pesticides is an effective way to increase agricultural output, and herbicides play a very important role in modern agriculture. Today, global herbicide resistance has become a serious problem, and it is urgent to develop novel highly active compounds and new interaction mechanisms to overcome weed resistance. Triazolinone derivatives often show good herbicidal activity, and some of them have been developed into commercial pesticides. For example, mefentrazone, amfentrazone, sulfentrazone, and mefentrazone-ethyl. Similarly, pyridine derivatives also exhibit diverse biological activities. Many commercial herbicides contain pyridine rings, for example, flufenpyrazole, dithiopyr, etc. Fused heterocycles typical...

Claims

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Application Information

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IPC IPC(8): C07D471/04A01P13/00
CPCC07D471/04
Inventor 刘幸海杨明艳赵文翟志文孙召慧翁建全谭成侠
Owner ZHEJIANG UNIV OF TECH
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