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Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative

A technology of dichloropropene and pyrazole oxime is applied in the field of pesticides to achieve excellent control effects

Active Publication Date: 2014-12-10
上海湘申诚瑞新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative
  • Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative
  • Pyrazole oxime derivative containing dichloropropene as well as preparation method and application method of derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of Compound Ia (n=1, R=3-F)

[0034]

[0035] 5 mmol of compound II was dissolved in an appropriate amount of N,N-dimethylacetamide, and 6 mmol of compound III and 10 mmol of cesium carbonate were added thereto. Heat to reflux for 18h, and TLC detects that the reaction is complete. After filtration, the filtrate was concentrated under reduced pressure. The crude product was dissolved in dichloromethane, washed with water, dried, concentrated, and separated by column chromatography to obtain the target product Ia as a light yellow oil. 1 H NMR (400MHz, CDCl 3 )7.78(s,1H,CH=N),7.23-7.29(m,1H,ArH),6.78-6.82(m,3H,ArH),6.63-6.69(m,2H,ArH),6.11(t,J =6.4Hz,1H, CH CH 2 ), 4.57 (d, J=6.4Hz, 2H, CHC H 2 O), 4.22(t, J=6.4Hz, 2H, CH 2 OAr), 3.99(t, J=6.4Hz, 2H, C H 2 O-N=CH),3.62(s,3H,N-CH 3 ),2.38(s,3H,CH 3 ),2.04-2.11(m,2H,CH 2 C H 2 CH 2 ).

Embodiment 2

[0037] Synthesis of compound Ib (n=1, R=4-F)

[0038]

[0039] Dissolve 5mmol of compound II in an appropriate amount of acetonitrile, add 6.5mmol of compound III and 15mmol of K 2 CO 3 . Heat to reflux for 15h, and TLC detects that the reaction is complete. After filtration, the filtrate was concentrated under reduced pressure. The crude product was dissolved in dichloromethane, washed with water, dried, concentrated, and separated by column chromatography to obtain the target product Ib as a light yellow oil. 1 H NMR (400MHz, CDCl 3 )7.78(s,1H,CH=N),6.86-7.04(m,4H,ArH),6.84(s,2H,Ar-H),6.13(t,J=6.0Hz,1H,C H CH 2 ), 4.60 (d, J=4.0Hz, 2H, CHC H 2 O), 4.24(t, J=6.0Hz, 2H, C H 2 OAr), 4.01(t, J=6.0Hz, 2H, C H 2 O-N=CH),3.63(s,3H,N-CH 3 ),2.39(s,3H,CH 3 ),2.06-2.13(m,2H,CH 2 C H 2 CH 2 ).

Embodiment 3

[0041] Synthesis of compound Ic (n=1, R=4-OCF 3 )

[0042]

[0043] 5 mmol of compound II was dissolved in an appropriate amount of N,N-dimethylformamide, and 7 mmol of compound III and 14 mmol of 4-N,N-lutidine were added thereto. Heat to reflux for 20h, and TLC detects that the reaction is complete. After filtration, the filtrate was concentrated under reduced pressure. The crude product was dissolved in dichloromethane, washed with water, dried, concentrated, and separated by column chromatography to obtain the target product Ic as a light yellow oil. 1 H NMR (400MHz, CDCl 3)7.70(s,1H,CH=N),7.09(d,J=8.8Hz,2H,ArH),6.84(J=9.2Hz,2H,ArH),6.75(s,2H,Ar-H),6.03 (t,J=8.0Hz,1H,C H CH 2 ), 4.50 (d, J=6.4Hz, 2H, CHC H 2 O), 4.12(t, J=6.4Hz, 2H, C H 2 OAr), 3.91(t, J=6.4Hz, 2H, C H 2 O-N=CH),3.55(s,3H,N-CH 3 ),2.30(s,3H,CH 3 ),1.95-2.00(m,2H,CH 2 C H 2 CH 2 ).

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Abstract

The invention relates to a preparation method and an application method of a pyrazole oxime derivative (I) containing dichloropropene. The pyrazole oxime derivative is obtained by condensing pyrazole hydroxyl oxime (II) and a terminated bromo compound (III) containing dichloropropene. The pyrazole oxime derivative containing dichloropropene has an effective effect of preventing and controlling harmful insects, and the pyrazole oxime derivative can be used for preparing insecticides in such fields as agriculture and horticulture (As shown in Specification).

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a dichloropropene-containing pyrazole oxime derivative, a preparation method and application thereof. 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] Dichloropropene is the active fragment of a variety of insecticides, such as pyridalyl developed by Sumitomo Chemical: [0004] [0005] Pyrazole oxime ether structure is another common insecticide active fragment, which represents compounds such as pyrac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/20A01N43/56A01P7/04
CPCA01N43/56C07D231/20
Inventor 戴红戴宝江石玉军王森林何海兵李刚李阳方源
Owner 上海湘申诚瑞新材料有限公司
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