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Cyanoacrylate compound containing pyrazole structure and its preparation method and use

A technology of cyanoacrylate and compound is applied in the field of cyanoacrylate compound and its preparation, and achieves the effect of excellent control effect

Active Publication Date: 2019-11-05
上海易恩化学技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in recent years, with the enhancement of people's awareness of food safety and environmental protection, the status of traditional herbicides has been increasingly challenged.

Method used

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  • Cyanoacrylate compound containing pyrazole structure and its preparation method and use
  • Cyanoacrylate compound containing pyrazole structure and its preparation method and use
  • Cyanoacrylate compound containing pyrazole structure and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Add 4mmol of compound IIIa and 2mmol of intermediate II into a reaction flask, and add an appropriate amount of carbon tetrachloride, heat to reflux, react for 12 hours, evaporate the solvent under reduced pressure, and the residue is subjected to column chromatography [V (petroleum ether): V (ethyl acetate)=4:1] separation to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 ): δ10.37(s,1H,NH),7.93(d,J=2.4Hz,1H,Pyrazole-H),7.74(d,J=1.2Hz,1H,Pyrazole-H),7.71(d,J =8.4Hz, 2H, Ar-H), 7.34(d, J=8.4Hz, 2H, Ar-H), 6.49(t, J=2.0Hz, 1H, Pyrazole-H), 4.81(d, J=6.0 Hz, 2H, CH 2 ), 4.31(t, J=4.8Hz, 2H, CH 2 ), 3.66(t, J=4.8Hz, 2H, CH 2 ),3.41(s,3H,OCH 3 ),2.68(s,3H,SCH 3 ).

Embodiment 2

[0033]

[0034] Add 4mmol of compound IIIb and 5mmol of intermediate II into a reaction flask, and add an appropriate amount of DMA, heat to 80°C, react for 16 hours, evaporate the solvent under reduced pressure, and the residue is subjected to column chromatography [V (petroleum ether): V (Ethyl acetate)=4:1] separation to obtain the target compound Ib; 1 H NMR (400MHz, CDCl 3 ):δ10.34(s,1H,NH),7.93(d,J=2.4Hz,1H,Pyrazole-H),7.71-7.74(m,3H,Pyrazole-H and Ar-H),7.34(d, J=8.8Hz, 2H, Ar-H), 7.00-7.06(m, 1H, Ar-H), 6.76-6.87(m, 2H, Ar-H), 6.49(t, J=2.0Hz, 1H, Pyrazole -H),4.81(d,J=6.0Hz,2H,CH 2 ),4.50(t,J=4.8Hz,2H,CH 2 ), 4.28(t, J=4.8Hz, 2H, CH 2 ),2.69(s,3H,SCH 3 ).

Embodiment 3

[0036]

[0037] Add 11mmol of compound IIIc and 9mmol of intermediate II into a reaction flask, add an appropriate amount of n-butanol, heat to 50°C, and react for 7 hours. The solvent was evaporated under reduced pressure, and the residue was separated by column chromatography [V (petroleum ether): V (ethyl acetate) = 4: 1] to obtain the target compound Ic; 1 H NMR (400MHz, CDCl 3): δ10.36(s,1H,NH),7.92(d,J=2.4Hz,1H,Pyrazole-H),7.73(d,J=1.6Hz,1H,Pyrazole-H),7.71(d,J =8.4Hz, 2H, Ar-H), 7.33(d, J=8.8Hz, 2H, Ar-H), 6.48(t, J=2.0Hz, 1H, Pyrazole-H), 4.80(d, J=6.0 Hz,2H,CH2),4.15-4.21(m,3H,CH 2 and CH),3.75~3.95(m,2H,CH 2 ),2.67(s,3H,SCH 3 ),1.75~2.04(m,4H,2×CH 2 ).

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Abstract

The invention relates to a cyanoacrylate compound (I) containing a pyrazol structure as well as a preparation method and application of the cyanoacrylate compound. The cyanoacrylate compound is obtained by taking a pyrazol biphenyl methylamine compound and 2-cyano-3,3-substituted dimethylthioacrylate to react. The cyanoacrylate compound containing the pyrazol structure, provided by the invention, has a relatively good prevention and control effect on broadleaf weeds and grassy weeds; the compound can be used for preparing herbicides used in the fields including agriculture, gardening and the like.

Description

technical field [0001] The invention relates to the field of chemical pesticides, in particular to a cyanoacrylate compound containing a pyrazole structure and a preparation method and application thereof. Background technique [0002] Herbicides are one of the most widely used pesticides. In the global herbicide market, traditional herbicides still occupy a dominant position and have made great contributions to social development. However, in recent years, with the enhancement of people's awareness of food safety and environmental protection, the status of traditional herbicides has been increasingly challenged. In view of its various drawbacks, it is imperative to find new herbicides. However, the increasingly higher herbicide standards require not only that these new herbicides can kill weeds efficiently, but also require them to be low-toxic, green and safe. [0003] Cyanoacrylate compounds are photosystem II (PS II) electron transfer inhibitors, which can interfere w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/12C07D405/12A01P13/00
CPCC07D231/12C07D405/12
Inventor 戴红石玉军杜显超姚勇姚炜陈佳王祥龙冯浩樊丽余陈庆文
Owner 上海易恩化学技术有限公司