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Silicon acyl acetonitrile compounds and preparation method and application thereof

A technology of silicyl acetonitrile and compound, which is applied in the field of insecticides and/or acaricides, and silicyl acetonitrile-containing compounds, and can solve the problems that the research of new acaricides cannot meet the needs and other problems.

Active Publication Date: 2019-12-10
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing acaricides have problems such as mite resistance, and the research on new acaricides cannot meet the needs

Method used

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  • Silicon acyl acetonitrile compounds and preparation method and application thereof
  • Silicon acyl acetonitrile compounds and preparation method and application thereof
  • Silicon acyl acetonitrile compounds and preparation method and application thereof

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preparation example Construction

[0149] The preparation method of the compound of the present invention

[0150] The preparation method of the compound of formula I of the present invention is described in more detail below, but these specific methods do not constitute any limitation to the present invention. The compounds of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art, and such combinations can be easily performed by those skilled in the art to which the present invention belongs.

[0151] The present invention also provides a general method for preparing the compound described in the first aspect, namely the compound of formula I.

[0152] In a specific embodiment, the compound of formula I is prepared by the following reaction:

[0153] Reaction 1:

[0154]

[0155] Reaction 2:

[0156]

[0157] Reaction 3:

[0158]

[0159] Reaction 4:

[0160]

[0161] Reaction 5:

[0162] ...

Embodiment 1

[0192] The preparation of embodiment 1 compound 4

[0193] (1). Preparation of p-trimethylsilylbromobenzene:

[0194]

[0195]Weigh 2.9g of p-dibromobenzene into the Schlenk reaction flask, add 100ml of anhydrous THF to dissolve, stir at -78°C, slowly add 5ml of n-BuLi (2.5M) dropwise, and continue at -78°C Stirring was followed by the dropwise addition of 1.8 ml trimethylchlorosilane. Gradually warm to room temperature, add saturated NH 4 Cl solution, extracted with ethyl acetate (30 mL×3), combined organic phases, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and purified by column chromatography to obtain the target compound as a colorless oil with a yield of 74.7%. 1 H NMR (400MHz, Chloroform-d) δ 7.48 (d, J = 8.2Hz, 2H), 7.37 (d, J = 8.3Hz, 2H), 0.25 (s, 9H) ppm.

[0196] (2). Preparation of p-trimethylsilylphenylacetonitrile:

[0197]

[0198] Weigh 37 mg of allylpalladiu...

Embodiment 2

[0208] The preparation of embodiment 2 compound 6

[0209] (1). Preparation of 2-(4-trimethylsilylbenzene)-2-methoxyisobutyl cyanoacetate:

[0210]

[0211] Weigh 600mg of ethyl 2-(4-trimethylsilylphenyl)-cyanoacetate and dissolve it in 15ml of isobutanol, add two drops of concentrated sulfuric acid as a catalyst dropwise, and react at 100°C for 12 hours. The reaction solution was poured into 30ml of water, extracted with ethyl acetate (20mL×3), the combined organic phases were washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and purified by column chromatography to obtain the target compound as a light yellow oil with a yield of 82.2%; 1 H NMR (400MHz, Chloroform-d) δ7.44 (d, J = 8.1Hz, 2H), 7.31 (d, J = 8.0Hz, 2H), 4.02 (ddd, J = 29.5, 10.5, 6.5Hz, 2H) , 2.09–1.94 (m, 1H), 0.95 (d, J=6.7Hz, 6H), 0.30 (s, 9H) ppm.

[0212] (2).(RS)-2-(4-trimethylsilylphenyl)2-cyano-3-oxo-3-(α,α,α,-tri...

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Abstract

The invention discloses silicon acyl acetonitrile compounds, or geometric isomers, or stereoisomers, or salts thereof. In particular, the invention relates to compounds represented by the formula I and a composition containing the compounds represented by the formula I, and a use thereof. The compounds have excellent acaricidal activity.

Description

technical field [0001] The invention belongs to the field of insecticides and acaricides, and in particular relates to a silyl acetonitrile compound with insecticide / acaricide activity, a preparation method of the compound and its use and method as an insecticide and / or acaricide. Background technique [0002] Insects and harmful mites often cause heavy losses to economic crops such as fruits, cotton, vegetables, and ornamental plants. The use of chemical insecticides and acaricides to control them is very important to ensure the safety of economic crops and improve people's living standards. Acaricides can also bring considerable socio-economic benefits. The resistance of insects and harmful mites to existing insecticides and acaricides, as well as the ecological environment safety problems of existing insecticides and acaricides also promote the innovative research of new insecticides and acaricides. However, the existing acaricides have problems such as mite resistance, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07F7/10A01N55/10A01P7/02A01P7/04A01P3/00
CPCA01N55/00C07F7/081C07F7/0812C07F7/0814C07F7/0825
Inventor 程家高彼得·迈恩菲什周聪李忠邵旭升徐晓勇钱旭红
Owner EAST CHINA UNIV OF SCI & TECH
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