Preparation method of nicotinamide fungicide namely boscalid

A technology of boscalid and nicotinamide, which is applied in the field of preparation of nicotinamide broad-spectrum fungicide boscalid and its intermediates, which can solve the problem of unsatisfactory preparation discovery, high preparation cost, and many side reactions. question

Inactive Publication Date: 2015-04-01
SUZHOU TOKIND CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 1) Through the benzidine intermediate 4-chloro-2'-aminobiphenyl, using o-chloronitrobenzene as a raw material, undergoes a Suziki coupling reaction with p-chlorophenylboronic acid under the catalysis of palladium (II) to obtain the intermediate 4-chloro -2′-Nitrobiphenyl: Adv. Syn. & Cat. 252, 3089-3097, 2010, reported with Pd(PPh 3 ) 4 As a catalyst, n-butanol was used as a solvent, reacted at 160 °C for 15 minutes, and the yield was 91%. WO2006092429 reported using PdCl 2 As a catalyst, triphenylphosphine is used as an auxiliary catalyst, THF is used as a solvent, and the yield is 99% at 66 °C for 18 hours. The amount of catalyst used is very large, making the preparation cost very expensive and not suitable for industrial production.
Tetrahedron, 66, 2301~2305, 2010, reported using PdCl 2 Loaded on 4A molecular sieve as a catalyst, DMF as a solvent, reacted at 120 °C for 18 hours, and the yield was 90%. However, a large number of experiments found that it is difficult to implement the catalyst, and it is not suitable for a little scale-up experiment
[0009] 4-Chloro-2′-nitrobiphenyl and then through iron powder (Adv. Synth. Catal. 2009, 351, 649-655) or SnCl 2 (Chem.Commun. 2007,2926-2928) Reduction to obtain the intermediate 4-chloro-2'-aminobiphenyl, and the

Method used

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  • Preparation method of nicotinamide fungicide namely boscalid
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  • Preparation method of nicotinamide fungicide namely boscalid

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Embodiment 1

[0050] A preparation method of boscalid, a nicotinamide fungicide is provided, comprising the steps of:

[0051] (1) Preparation of p-chlorophenylboronic acid (compound II)

[0052] Under the protection of nitrogen, directly into the 20-liter reaction kettle, add in sequence: 0.55Kg of magnesium chips and 5.0Kg of 2-methyltetrahydrofuran. The temperature was raised to reflux, and 1Kg of 2-methyl THF solution of 3.80Kg of p-chlorobromobenzene was added dropwise. After the dropwise addition, the reflux reaction was maintained for 4-5h. After the reaction was complete, the reaction was stopped and cooled to room temperature. will (i-PrO) 3 B. Add 5.20 Kg of 4.0 Kg 2-methyltetrahydrofuran solution into a 50-liter reaction kettle, and add the above-prepared Grignard reagent dropwise at a temperature not higher than 0°C; Add 16L of 20% HCl, stir for 1h, add 5L of toluene, extract, and filter with suction; continue to stir and filter with 5L of toluene for the solid, combine the l...

Embodiment 2

[0062] A preparation method of boscalid, a nicotinamide fungicide is provided, comprising the steps of:

[0063] (1) Preparation of p-chlorophenylboronic acid (compound II)

[0064] Under the protection of nitrogen, directly into the 20-liter reaction kettle, add in sequence: 0.55Kg of magnesium chips and 5.0Kg of 2-methyltetrahydrofuran. The temperature was raised to reflux, and 1Kg of 2-methyl THF solution of 3.80Kg of p-chlorobromobenzene was added dropwise. After the dropwise addition, the reflux reaction was maintained for 4-5h, the reaction was stopped, and cooled to room temperature. Will (n-BuO) 3 B 6.00 Kg of 4.0 Kg 2-methyltetrahydrofuran solution was added to a 50-liter reaction kettle, and the Grignard reagent prepared above was added dropwise at a temperature not higher than 0°C; after the dropwise addition, stirred for 10 hours; then added 10% H 2 SO 4 16L, stirred for 1h, added 5L toluene, extracted, and suction filtered; the solid was continuously stirred...

Embodiment 3

[0071] A preparation method of boscalid, a nicotinamide fungicide is provided, comprising the steps of:

[0072] (1) Preparation of o-iodonitrobenzene (compound III)

[0073] N 2 Under protection, at room temperature, 1 Kg of o-nitroaniline and 10 L of concentrated hydrochloric acid were added to the above reaction kettle. The above solution was stirred and cooled until the temperature in the bottle reached below 0°C. Dissolve 0.53 Kg of sodium nitrite in 1.2 L of water to form a solution, slowly add it into the reaction kettle, and stir for 1 h. Under the condition of not higher than 0°C, dissolve 1.5 Kg NaI in 1L of water and add it to a new reaction kettle, and stir. The prepared diazonium solution was added dropwise to the above reaction solution, and after the dropwise addition was completed, the reaction was continued for 1 h. After the reaction, it was filtered, dried in the air, recrystallized with ethanol, cooled and precipitated, and filtered to obtain 1.35 Kg of...

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Abstract

The invention discloses a preparation method of a nicotinamide fungicide namely boscalid. The preparation method comprises the following steps: starting from a raw material namely para chlorobromobenzene, performing Grignard reaction, and synthesizing p-chlorobenzeneboronic acid; starting from ortho-nitroaniline, synthesizing o-nitro halogenated benzene, or directly synthesizing o-amino halogenated benzene; and under the action of specific catalysts, enabling p-chlorophenylboronic acid to perform a series of reactions such as coupling, reduction, amidation and the like with o-nitro halogenated benzene or o-amino halogenated benzene to prepare boscalid. The preparation method disclosed by the invention is simple to operate, high in yield, small in pollution, low in cost and high in purity, and is very suitable for industrial production.

Description

technical field [0001] The invention relates to the field of pesticide fungicides, in particular to a preparation method of a nicotinamide broad-spectrum fungicide boscalid and an intermediate thereof. Background technique [0002] Boscalid is a new type of nicotinamide fungicide developed by BASF in Germany. It is mainly used to prevent gray mold, powdery mildew, various rots, brown rots and root rots. Registered in Germany and Switzerland. Boscalid belongs to the succinate coenzyme Q reductase inhibitor in the mitochondrial respiratory chain, which has a strong inhibitory ability to spore germination and has no cross-resistance with other fungicides. Boscalid is a new type of nicotinamide fungicide with a wide bactericidal spectrum and is active against almost all types of fungal diseases. It is very effective in preventing and controlling powdery mildew, gray mold, sclerotinia and various rot diseases, etc. It is also effective for resistant bacteria to other chemicals,...

Claims

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Application Information

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IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 魏开举耿俊俊崔杨
Owner SUZHOU TOKIND CHEM CO LTD
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