Preparation method of Boscalid

A technology of boscalid and iodoaniline, applied in the field of fungicide preparation, can solve the problems of low yield, high cost, harsh reaction conditions, etc., and achieve the effect of reducing production cost and increasing yield

Inactive Publication Date: 2013-05-01
LIMIN CHEM CO LTD
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0003] In order to solve the disadvantages of low yield, high cost and harsh reaction conditions in the prior art, the present invention provides a preparation method of boscalid, which reduces the production cost and increases the production cost of the intermediate product 4'-chlorobiphenyl- yield of 2-amines, resulting in an overall yield of over 84%

Method used

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  • Preparation method of Boscalid
  • Preparation method of Boscalid
  • Preparation method of Boscalid

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Experimental program
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Effect test

Embodiment 1

[0017] Embodiment 1: the preparation of 4'-chlorobiphenyl-2-amine

[0018] Add 4-chlorophenylboronic acid (31.3g, 200mmol), o-iodoaniline (39.2g, 180mmol), Pd / C (0.3g, 5%) and toluene (300mL) into a 1L three-necked flask, and stir at room temperature for 15 minutes. Then add Na 2 CO 3 Aqueous solution (300mL, 25%), the mixture was heated and stirred to reflux for 30h, then cooled to room temperature, and the layers were separated. The inorganic layer was extracted twice with toluene (50 mL×2), and the organic layers were combined and washed three times with water (100 mL×3). Anhydrous MgSO for organic phase 4 Dry and recover toluene under reduced pressure. The remaining oil was put into the refrigerator at 0~5°C to freeze to obtain 34.2 g of brown solid, yield: 93.2%. Mp: 39-41°C; (literature value CAS: 1204-44-0, mp: 42-44°C).

[0019] According to the above method, using o-iodoaniline and 4-chlorophenylboronic acid as raw materials, react under different solvents, diff...

Embodiment 2

[0024] Embodiment 2: the preparation of boscalid

[0025] In a dry 250 mL flask add 4'-chlorobiphenyl-2-amine (20.4 g, 100 mmol), dry dichloroethane (150 mL), sodium carbonate (21.2 g, 200 mmol), and a catalytic amount of 1 mL of triethylamine . Then it was cooled to 10°C with ice water, and 2-chloronicotinoyl chloride (19.36 g, 110 mmol) was added in 5 batches (about 4 g per batch), and then the reaction was continued at room temperature for 4 hours. After the reaction, wash with water (30mL), then with hydrochloric acid (20mL, 10%), and finally with water (30mL). Anhydrous MgSO for organic phase 4 After drying, the solvent was recovered by atmospheric distillation, and the remaining solid was recrystallized with a mixed solvent of alcohol and water (volume ratio: 1:1) to obtain 31.2 g of boscalid, with a yield of 91.1%. Mp: 143-144°C; (literature value CAS: 188425-85-6, mp: 142-144°C).

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Abstract

The invention discloses a preparation method of Boscalid, which comprises the following steps that Suzuki coupling reaction occurs between o-iodoaniline and 4-chlorobenzene boronic acid to produce an intermediate product 4'-chlorinated biphenyl-2-amine under the catalytic effect of Pd/C by using methylbenzene and alkaline water as mixed solvent; and condensation reaction occurs between the 4'-chlorinated biphenyl-2-amine and 2-chloronicotinyl chloride to produce the Boscalid. The preparation method of the Boscalid has the advantages that the production cost is reduced, the yield of the intermediate product 4'-chlorinated biphenyl-2-amine is improved, the total yield of the two steps exceeds 84 percent and the industrial production is expected to be realized.

Description

technical field [0001] The invention relates to the field of pesticide preparation, in particular to a method for preparing a fungicide. Background technique [0002] The full name of boscalid is N-(4’-chloro-2-biphenyl)-2-chloro-3-pyridinecarboxamide, which is a highly effective fungicide. The first is a new type of fungicide registered by BASF of Germany and AG of Japan in more than 50 countries including Europe and the United States. It is mainly used to control gray mold and sclerotinia of vegetables and beans. Its mechanism of action is that the medicinal liquid is absorbed by the plant and permeated through the leaves, and then transferred in the plant, which can inhibit the activity of mitochondrial succinate dehydrogenase, thereby hindering the tricarboxylic acid cycle, causing amino acid and sugar deficiency, reducing energy, and interfering with cells. The division and growth have fungicidal activity. The synthesis method of boscalid reported in the literature i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82C07C211/52C07C209/68
Inventor 孙敬权王香善张贤振
Owner LIMIN CHEM CO LTD
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