1, 1-dichloropropene ether compound containing n-substituent-3-methylpyrazole oxime unit structure, preparation method and application thereof

A technology of dichloropropene ethers and methylpyrazole oxime, which is applied in the field of pesticides to achieve excellent control effects

Inactive Publication Date: 2015-07-08
NANTONG UNIVERSITY
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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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  • 1, 1-dichloropropene ether compound containing n-substituent-3-methylpyrazole oxime unit structure, preparation method and application thereof
  • 1, 1-dichloropropene ether compound containing n-substituent-3-methylpyrazole oxime unit structure, preparation method and application thereof
  • 1, 1-dichloropropene ether compound containing n-substituent-3-methylpyrazole oxime unit structure, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of compound Ia (n=3 in general formula II, R in III 1 for -CH 3 , R 2 for 4-F)

[0036]

[0037] In a 100 mL flask, 3 mmol of compound III and 20 mL of N,N-dimethylformamide were added, and then 4 mmol of compound II and 9 mmol of potassium carbonate were added thereto. Slowly heated to 80°C for 8 hours. Then the reaction solution was cooled, filtered with suction, and the solid was removed by filtration, the mother liquor was concentrated under reduced pressure, and purified by column chromatography to obtain the target compound Ia as a yellow oil. 1 H NMR (400MHz, CDCl 3 )7.75(s,1H,CH=N),6.98-7.02(m,2H,ArH),6.83-6.88(m,4H,ArH),6.12(t,J=6.0Hz,1H, CH CH 2 ), 4.58 (d, J=6.0Hz, 2H, CHC H 2 O),3.92-4.01(m,4H,CH 2 OAr and C H 2 O-N=CH),3.61(s,3H,N-CH 3 ),2.37(s,3H,CH 3 ),1.80-1.84(m,2H,CH 2 ),1.53-1.67(m,4H,2×CH 2 ).

Embodiment 2

[0039] Synthesis of compound Ib (n=3 in general formula II, R in III 1 for-Ph,R 2 for 4-F)

[0040]In a 100 mL flask, 4 mmol of compound III and 25 mL of butanone were added, and then 4 mmol of compound II and 6 mmol of potassium tert-butoxide were added thereto. Heat to reflux for 11 hours. Then the reaction liquid was cooled, filtered with suction, and the solid was removed by filtration, the mother liquor was concentrated under reduced pressure, and purified by column chromatography to obtain the target compound Ib as a yellow oil. 1 H NMR (400MHz, CDCl 3 )7.82(s, 1H, CH=N), 7.61(d, J=8.0Hz, 2H, ArH), 7.27-7.41(m, 3H, ArH), 6.90-7.00(m, 4H, ArH), 6.86( s,2H,ArH),6.13(t,J=6.4Hz,1H, CH CH 2 ), 4.60 (d, J=6.4Hz, 2H, CHC H 2 O),3.95-4.07(m,4H,CH 2 OAr and C H 2 O-N=CH),2.50(s,3H,CH 3 ),1.84-1.88(m,2H,CH 2 ),1.57-1.72(m,4H,2×CH 2 ).

Embodiment 3

[0042] Synthesis of compound Ic (n=4 in general formula II, R in III 1 for -CH 3 , R 2 for 4-I)

[0043] In a 100mL flask, add 2mmol of compound III and 25mL of THF, then add 4mmol of sodium bicarbonate to it at room temperature, stir for a while, add 2.5mmol of compound II to it, and heat to reflux for 9 hours. Then the reaction solution was cooled, filtered with suction, and the solid was removed by filtration, the mother liquor was concentrated under reduced pressure, and purified by column chromatography to obtain the target compound Ic as a yellow oil. 1 H NMR (400MHz, CDCl 3 )7.77(s,1H,CH=N),7.61(d,J=8.8Hz,2H,ArH),6.85(s,2H,ArH),6.70(d,J=9.2Hz,2H,ArH),6.13 (t,J=6.4Hz,1H, CH CH 2 ), 4.60 (d, J=6.4Hz, 2H, CHC H 2 O),3.94-3.99(m,4H,CH 2 OAr and C H 2 O-N=CH),3.62(s,3H,N-CH 3 ),2.38(s,3H,CH 3 ),1.80-1.87(m,2H,CH 2 ),1.50-1.61(m,4H,2×CH 2 ), 1.38-1.44 (m,2H,CH 2 ).

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Abstract

The invention relates to a 1, 1-dichloropropene ether compound (I) containing N-substituent-3-methylpyrazole oxime unit structure, a preparation method and application thereof. The compound is obtained by reacting N-substituent-3-methylpyrazole oxime (III) with 3-(2, 6-dichloro-4-(3, 3-dichloro-4-(3, 3-dichloro allyloxy)phenoxy)-1-bromoalkane key intermediate (II). The 1, 1-dichloropropene ether compound (I) containing N-substituent-3-methylpyrazole oxime unit structure shows good control effect on harmful insects, and the compound can be used for preparing insecticides of agriculture, gardening and other fields. (general formula I).

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a 1,1-dichloropropene ether compound containing an N-substituent-3-methylpyrazole oxime unit structure 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 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] 1,1-dichloropropene ether insecticides were first proposed by Sumitomo Chemical Company in Japan in 1996. The commercialized species has pyridalyl (S-1812), which is effective against various insecticides on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/20C07D231/22A01N43/56A01P7/04
CPCC07D231/20A01N43/56C07D231/22
Inventor 戴红戴宝江李宏石玉军曹宇锋葛书山朱超方源
Owner NANTONG UNIVERSITY
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