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Preparation method and applications of 3-(benzotriazolmethoxyl)pyrazole derivatives containing aryl isoxazole

A technology of benzotriazole and benzyloxy is applied in the field of preparation of 3-pyrazole derivatives to achieve excellent control effects

Active Publication Date: 2020-02-28
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice

Method used

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  • Preparation method and applications of 3-(benzotriazolmethoxyl)pyrazole derivatives containing aryl isoxazole
  • Preparation method and applications of 3-(benzotriazolmethoxyl)pyrazole derivatives containing aryl isoxazole
  • Preparation method and applications of 3-(benzotriazolmethoxyl)pyrazole derivatives containing aryl isoxazole

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Experimental program
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Effect test

Embodiment 1

[0030]

[0031] 6 mmol of compound IIa was dissolved in 30 mL of 1,4-dioxane, then 30 mmol of pyridine was added, and then 8 mmol of intermediate III was added thereto under ice-cooling conditions. After the addition was complete, the reaction was continued at room temperature for 13 hours. The reaction was stopped, and the reaction solution was rotary evaporated to dryness under reduced pressure, and the obtained crude product was separated by column chromatography to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 ): δ8.49(d, J=4.0Hz, 1H, Py-H), 8.15(d, J=8.4Hz, 1H, Ar-H), 7.90(d, J=7.6Hz, 1H, Py-H ),7.80(d,J=8.4Hz,2H,Ar-H),7.68~7.76(m,5H,Ar-H),7.54~7.58(m,1H,Ar-H),7.43~7.46(m, 4H,Ar-H),7.38~7.41(m,1H,Py-H),7.08(s,1H,NH),6.49(s,1H,Isoxazole-H),6.36(s,1H,Pyrazole-H) ,5.42(s,2H,CH 2 ), 4.62 (d, J=5.6Hz, 2H, CH 2 ).

Embodiment 2

[0033]

[0034] 8 mmol of compound IIb was dissolved in 25 mL of dichloromethane, then 30 mmol of triethylamine was added, and then 9 mmol of intermediate III was added thereto under ice-cooling conditions. After the addition was complete, stirring was continued at room temperature for 12 hours. The reaction was stopped, and the reaction solution was rotary evaporated to dryness under reduced pressure, and the obtained crude product was separated by column chromatography to obtain the target object Ib; 1 H NMR (400MHz, CDCl 3 ):δ8.46~8.48(m,1H,Py-H),8.34(d,J=8.8Hz,2H,Ar-H),7.88~7.93(m,3H,Py-H and Ar-H), 7.68~7.71(m,2H,Ar-H),7.61(d,J=8.4Hz,2H,Ar-H),7.40~7.43(m,2H,Ar-H),7.38~7.40(m,1H, Py-H),7.10~7.14(m,2H,Ar-H),6.42(s,1H,Isoxazole-H),6.34(s,1H,Pyrazole-H),5.37(s,2H,CH 2 ), 4.57 (d, J=6.0Hz, 2H, CH 2 ).

Embodiment 3

[0036]

[0037] 5 mmol of compound IIc was dissolved in 20 mL of acetone, then 20 mmol of 4-dimethylaminopyridine (DMAP) was added, and then 6 mmol of intermediate III was added thereto under ice-cooling conditions. After the addition, the reaction was heated to reflux for 20 hours. The reaction was stopped, and the reaction liquid was rotary evaporated to dryness under reduced pressure, and the obtained crude product was separated by column chromatography to obtain the target compound Ic. 1 H NMR (400MHz, CDCl 3 ): δ8.48(d, J=4.0Hz, 1H, Py-H), 8.35(d, J=8.4Hz, 2H, Ar-H), 7.91~7.94(m, 2H, Ar-H), 7.89 (d, J=8.0Hz, 1H, Py-H), 7.61~7.66(m, 4H, Ar-H), 7.41~7.43(m, 2H, Ar-H), 7.36~7.40(m, 1H, Py -H), 7.15(s,1H,NH),6.94(d,J=8.4Hz,2H,Ar-H),6.35(s,1H,Isoxazole-H),6.34(s,1H,Pyrazole-H) ,5.38(s,2H,CH 2 ), 4.58 (d, J=4.8Hz, 2H, CH 2 ),3.83(s,3H,OCH 3 ).

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Abstract

The invention relates to a preparation method and applications of 3-(benzotriazolmethoxyl)pyrazole derivatives (I) containing aryl isoxazole. The derivatives are prepared through reactions between isoxazole methyl amine (II) and chloro-pyridine bipyrazole acyl chloride (III). The 3-(benzotriazolmethoxyl)pyrazole derivatives containing aryl isoxazole can effectively control harmful pests and can beused to prepare pesticides for agriculture and gardening.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to a preparation method and application of arylisoxazole-containing 3-(benzotriazole benzyloxy)pyrazole derivatives. Background technique [0002] Pest control has always been the core field of pesticide scientific research, and the widespread use of insecticides has enabled most pests to be effectively controlled. However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice. [0003] Pyrazole derivatives are an important class of nitrogen-containing heterocyclic compounds, which are widely used in agricultural production, such as pyrazole insecticides tonpyradram and tebufenpyrad. [0004] Isoxazole compounds are also important ...

Claims

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Application Information

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IPC IPC(8): C07D413/14A01N43/80A01P7/04
CPCC07D413/14A01N43/80
Inventor 戴红张敏李金峰王杨张燕张海军施磊李建华高磊郑丹丹
Owner NANTONG UNIVERSITY
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