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Pyrazole oxime derivatives containing dichloropropene and methods for their preparation and application

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

Active Publication Date: 2017-08-29
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 derivatives containing dichloropropene and methods for their preparation and application
  • Pyrazole oxime derivatives containing dichloropropene and methods for their preparation and application
  • Pyrazole oxime derivatives containing dichloropropene and methods for their preparation and application

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. After heating under reflux for 18h, the reaction was detected by TLC. 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, a pale 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 5 mmol of compound II in an appropriate amount of acetonitrile, add 6.5 mmol of compound III and 15 mmol of K to it 2 CO 3 . After heating under reflux for 15h, the reaction was detected by TLC. 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, a pale 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. After heating under reflux for 20h, the reaction was detected by TLC. 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, a pale 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 and 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 pesticides has enabled most pests to be effectively controlled. However, with the continuous expansion of the application scale of pesticides, the problem of drug resistance of traditional pesticide varieties has become increasingly prominent, and the continuous emergence of new pests and diseases has made the continued research and development of new pesticides an inevitable choice. [0003] Dichloropropene is the active fragment of various insecticides, such as acetamiprid developed by Japan's Sumitomo Chemical: [0004] [0005] Pyrazole oxime ether structures are another common insecticide active fragment, which represents compounds...

Claims

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Application Information

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Patent Type & Authority Patents(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