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Synthesis method of olefin-containing difluoro aryloxy ether and application of olefin-containing difluoro aryloxy ether in pesticide

A technology of olefin difluoroaryloxyether and difluoroaryloxyether, which is applied in botanical equipment and methods, formation/introduction of ether group/acetal group/ketal group, application, etc., to achieve good poisoning effect, Novel structure and simple operation effect

Active Publication Date: 2022-06-21
ANHUI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, keeping two C(sp 3 Difluoroalkylaryl etherification of )-F bonds and double bonds is a challenging problem in organic synthesis

Method used

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  • Synthesis method of olefin-containing difluoro aryloxy ether and application of olefin-containing difluoro aryloxy ether in pesticide
  • Synthesis method of olefin-containing difluoro aryloxy ether and application of olefin-containing difluoro aryloxy ether in pesticide
  • Synthesis method of olefin-containing difluoro aryloxy ether and application of olefin-containing difluoro aryloxy ether in pesticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1,3-Dichloro-5-(3,3-difluoro-3-phenoxyprop-1-en-2-yl)benzene

[0041]

[0042] In a 25mL reaction tube, add a magnetic stirrer, 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (48.4mg, 0.2mmol, 1.0eq) , phenol (37.6mg, 0.4mmol, 2.0 equivalents), Cs 2 CO 3 (130.4 mg, 0.4 mmol, 2.0 equiv) and DMF (2.0 mL) were stirred at 30°C for 16 hours. Then the mixture was cooled to room temperature, saturated brine (15 mL) was added, and extracted with EtOAc (15 mL×3). The combined organic phases were washed with anhydrous Na 2 SO 4 It was dried, filtered and concentrated in vacuo. Purification was separated by column chromatography with petroleum ether as the mobile phase, and a colorless oil (47.1 mg, 75%) was isolated.

[0043] Rf=0.7(PE).

[0044] 1 H NMR (600MHz, Chloroform-d) δ7.42(s, 2H), 7.38–7.33(m, 3H), 7.22(t, J=7.4Hz, 1H), 7.18(d, J=7.8Hz, 2H) ,6.07(s,1H),5.74(s,1H).

[0045] 13 C NMR (151MHz, Chloroform-d) δ150.01, 139.74, 138.10, 134.90, 129.39, 128.50,...

Embodiment 2

[0050] 4-((2-(3,5-dichlorophenyl)-1,1-difluoroallyl)oxy)-1,2-dimethylbenzene

[0051]

[0052] Into a 25mL reaction tube, add a magnetic stirrer, 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (48.4mg, 0.2mmol, 1.0 equivalent) , 3,4-dimethylphenol (48.8mg, 0.4mmol, 2.0eq), and DMF (2.0mL) were stirred at 30°C for 16 hours. Then the mixture was cooled to room temperature, saturated brine (15 mL) was added, and extracted with EtOAc (15 mL×3). The combined organic phases were washed with anhydrous Na 2 SO 4 It was dried, filtered and concentrated in vacuo, purified by column chromatography with petroleum ether as the mobile phase, and a colorless oil (54mg, 79%) was isolated.

[0053] Rf=0.7(PE).

[0054] 1 H NMR (600MHz, Chloroform-d) δ7.44(d, J=1.8Hz, 2H), 7.37(d, J=1.8Hz, 1H), 7.09(d, J=8.2Hz, 1H), 6.96(d ,J=2.4Hz,1H),6.93(dd,J=8.3,2.3Hz,1H),6.06(s,1H),5.73(s,1H),2.25(s,3H),2.24(s,3H) .

[0055] 13 C NMR (151MHz, Chloroform-d) δ147.89,139.94(t, 2 J F-C =31...

Embodiment 3

[0060] 1-((2-(3,5-dichlorophenyl)-1,1-difluoroallyl)oxy)-3-ethyl-2-methoxybenzene

[0061]

[0062] Into a 25mL reaction tube, add a magnetic stirrer, 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (48.4mg, 0.2mmol, 1.0 equivalent) , 4-ethyl-2-methoxyphenol (60.8 mg, 0.4 mmol, 2.0 equiv), and DMF (2.0 mL) were stirred at 30° C. for 16 hours. Then the mixture was cooled to room temperature, saturated brine (15 mL) was added, and extracted with EtOAc (15 mL×3). The combined organic phases were washed with anhydrous Na 2 SO 4 It was dried, filtered and concentrated in vacuo, purified by column chromatography with petroleum ether as the mobile phase, and a colorless oil (52 mg, 70%) was isolated.

[0063] Rf=0.7(PE).

[0064] 1 H NMR (600MHz, Chloroform-d) δ7.62(s, 2H), 7.35(s, 1H), 7.17(d, J=8.1Hz, 1H), 6.78(s, 1H), 6.74(d, J= 8.1Hz, 1H), 6.06(s, 1H), 5.78(s, 1H), 3.86(s, 3H), 2.63(q, J=7.4Hz, 2H), 1.24(t, J=7.6Hz, 3H) .

[0065] 13 C NMR (151MHz, Chloroform-d)...

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Abstract

The invention relates to the technical field of pesticides. The structural formula of an olefin difluoro aryloxy ether compound is shown as a formula (I). The invention particularly relates to a synthesis method of olefin-containing difluoro aryloxy ether. The method is mild in reaction condition, high in practicability and wide in substrate application range; meanwhile, metal catalysis is not needed, a high-toxicity reagent does not need to be used, the atom economy is high, the modern green chemistry concept is met, the insecticidal activity on agricultural and forestry pests is good, and the insecticidal activity is not reported in existing known insecticides.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a method for synthesizing an alkene-containing difluoroaryloxyether and its use in insecticidal activity. Background technique [0002] Olefin-containing difluoroaryloxyethers have unique value in agricultural chemistry due to their special structure. For example in anti-virus, insecticide and weed control. At the same time, these compounds usually have the characteristics of high efficiency, low toxicity and easy degradation in the environment. Therefore, in the research and development of pesticides, the compounds containing difluoroaryloxyether of olefins have shown an increasingly important role. [0003] Traditional synthetic method mainly comprises following several: 1) nucleophilic addition (Chambers, R.D. of phenol or alcohol and fluorinated olefin; Mobbs, R.H.Ionic Reactions of Fluoro-olefine in Advances in Fluorine Chemistry, Butterworths, London, 1965,50 -112); 2)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/04C07C41/16C07C43/225C07C319/20C07C323/20A01N31/14A01N31/16A01P7/04
CPCC07B41/04C07C41/16C07C319/20A01N31/14A01N31/16C07C43/225C07C323/20Y02P20/55
Inventor 李亚辉田青强张翅鹰王初夏
Owner ANHUI AGRICULTURAL UNIVERSITY
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