Metaflumizone synthesis method

A technology of metaflumizone and its synthesis method, which is applied in the field of synthesis of metaflumizone pesticides, can solve the problems of difficult operation and economy, complex post-processing, high cost, etc., and achieve good economy, simple and practical preparation method, and low equipment corrosion small effect

Inactive Publication Date: 2010-07-14
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And the synthetic method of this kind of compound that present document "WO0018714A1, WO03091203A1, EP0462456A1" introduction all has respective characteristics, but for industrialized

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  • Metaflumizone synthesis method

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Embodiment 1

[0020] Embodiment 1: the preparation of compound I

[0021] 1) Synthetic methyl p-trifluoromethoxyphenylcarbamate, synthetic route such as figure 1 .

[0022] In a 500ml three-necked bottle, equipped with a thermometer, a reflux condenser, and a constant pressure dropping funnel, add 26.55g of 4-trifluoromethylaniline, K 2 CO 3 27g and 300ml of dioxane, add 20ml of dioxane and 17.91g of ethyl chloroformate dropwise at room temperature, after the dropwise addition, heat to 50°C and stir for 6h, filter, wash the solid with 50ml of dioxane, The combined filtrates were spin-dried to obtain a white solid. Yield: 85%. The target product was detected by NMR.

[0023] 2) Synthetic p-trifluoromethylanilinohydrazide, the synthetic route is as follows figure 2 .

[0024] In a 500ml two-necked bottle, equipped with a thermometer and a reflux condenser, add 95g of 50% hydrazine hydrate and 35g of methyl p-trifluoromethoxyphenylcarbamate, heat to 90°C, keep warm for 25h, cool down t...

Embodiment 2

[0027] Embodiment 2: the preparation of compound I

[0028] 1) Synthetic methyl p-trifluoromethoxyphenylcarbamate, synthetic route such as figure 1 .

[0029] In a 500ml three-necked bottle, equipped with a thermometer, a reflux condenser, and a constant pressure dropping funnel, add 26.55g of 4-trifluoromethylaniline, K 2 CO 3 27g and 300mlTHF, add 20mlTHF and 17.91g ethyl chloroformate dropwise at room temperature. After the dropwise addition, heat to 50°C and stir for 6h, filter, wash the solid with 50mlTHF, combine the filtrates, and spin dry the liquid to obtain a white solid. Yield: 85%. The target product was detected by NMR.

[0030] 2) Synthetic p-trifluoromethylanilinohydrazide, the synthetic route is as follows figure 2 .

[0031] In a 500ml two-necked bottle, equipped with a thermometer and a reflux condenser, add 95g of 50% hydrazine hydrate and 35g of methyl p-trifluoromethoxyphenylcarbamate, heat to 90°C, keep warm for 25h, cool down to room temperature a...

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Abstract

The invention relates to a metaflumizone synthesis method, in particular to a metaflumizone pesticide synthesis method, belonging to the field of agricultural insecticides. The method is formed by the following steps: synthesis of p-trifluoromethoxybenzene methyl carhamate, synthesis of p-trifluoromethoxybenzene aminooxamide and synthesis of metaflumizone. The invention has the advantages that the preparation method is simple and practical, the efficiency is high and the yield of products at each step is more than 85 percent; the toxicity of the reagent used during the synthesis processes is low, the solvent can be recycled, the side reaction is less, the corrosion to the device is low and the environmental pollution is low; and since the price of the raw materials is cheap, the production cost is reduced, the economy is good and the application prospect is good.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, and in particular relates to a synthesis method of metaflumizone pesticide. Background technique [0002] Because insecticides and fungicides are used for a period of time, pests, germs and other organisms will develop resistance to them. Therefore, it is necessary to continuously invent new compounds with insecticidal and fungicidal activities, and have the possibility of mass production in industry Sexual new varieties, and metaflumizone pesticides meet the above requirements, metaflumizone (metaflumizone) belongs to semicarbazone insecticides. Metaflumizone has a unique mechanism of action, has insecticidal activity itself, does not require biological activation, and has no cross-resistance with existing various insecticides. Metaflumizone can effectively control Lepidoptera pests and some Coleoptera larvae and adults in various places, and can also be used to control ants, termites, ...

Claims

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Application Information

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IPC IPC(8): C07C281/10
Inventor 徐凤波张奉志吴桂平金艳娟孔晓菲
Owner NANKAI UNIV
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