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Method for producing harmful-organism control agent, and intermediate thereof

A compound and general formula technology, applied in the preparation of hydrogenated polysulfide/polysulfide, sulfide preparation, organic chemistry, etc., can solve the problem of using a large number of high-valent halogenated alkylating agents

Inactive Publication Date: 2016-09-28
KUMIAI CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the production method, at an early stage in the production route of the pest control agent as the final target compound, since the haloalkylation reaction using the haloalkylation agent is carried out, as a result, there is a need to use a large amount of high-priced The problem with haloalkylating agents

Method used

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  • Method for producing harmful-organism control agent, and intermediate thereof
  • Method for producing harmful-organism control agent, and intermediate thereof
  • Method for producing harmful-organism control agent, and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0598] Production of bis(2,4-dimethyl-5-hydroxyphenyl) disulfide

[0599]

[0600] To the reaction flask were added 44.32 g (28.0 mmol) of 5-mercapto-2,4-dimethylphenol, 42 mg (0.28 mmol) of sodium iodide, and 80 mL of ethyl acetate. While stirring the mixture at room temperature, 1.59 g (14 mmol) of 30% aqueous hydrogen peroxide was slowly added dropwise thereto. The mixture was stirred at room temperature for 1 hour. 5 mL of saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was stirred at room temperature for 10 minutes, then concentrated hydrochloric acid was added thereto to adjust the pH of the aqueous layer to about pH 1-2. The obtained mixture was partitioned into an organic layer and an aqueous layer, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel ...

Embodiment 2

[0604] Production of bis[2,4-dimethyl-5-(6-trifluoromethylthiohexyloxy)phenyl]disulfide

[0605]

[0606] In the reaction flask, add bis(2,4-dimethyl-5-hydroxyphenyl) disulfide 2.60g (8.5mmol), 1-bromo-6-trifluoromethylthiohexane 4.73g (17.9 mmol), potassium carbonate 2.58g (18.7mmol), tetrabutylammonium iodide 0.63g (1.7mmol) and N,N-dimethylformamide 17mL. The mixture was stirred at 80° C. for 20 hours under nitrogen atmosphere. Dilute hydrochloric acid, water and diethyl ether were added to the reaction mixture, the mixture was partitioned into an organic layer and an aqueous layer, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 4.95 g of bis[2,4-dimethyl-5-(6-trifluoromethylthiohexyloxy)phenyl] disulfide, yield 86 %.

[0607] 1 H‐NMR (300MHz, CDCl 3 )δ(ppm): 6.92(s,2H...

Embodiment 3

[0609] Production of 6-trifluoromethylthiohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]ether

[0610]

[0611] Add bis[2,4-dimethyl-5-(6-trifluoromethylthiohexyloxy)phenyl]disulfide 337.4mg (0.50mmol), p-toluenesulfonic acid 2,2, 266.9 mg (1.05 mmol) of 2-trifluoroethyl ester, 152.0 mg (1.10 mmol) of potassium carbonate, 231.2 mg (1.50 mmol) of Rongalite (trade name) (sodium formaldehyde sulfoxylate dihydrate) and N,N-dimethyl 2 mL of methyl formamide. The mixture was stirred at 50 °C under nitrogen atmosphere for 16 hours. Dilute hydrochloric acid, water and diethyl ether were added to the reaction mixture, the mixture was partitioned into an organic layer and an aqueous layer, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 242.0 mg of 6-trifluoromethylthi...

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Abstract

The purpose of the present invention is to provide: a production intermediate suitable for the industrial-scale production of a compound represented by general formula (4) and having a harmful-organism control activity; and a method for producing the same. A compound represented by general formula (4) (In the formula, R1-R4 are as stated below) is produced by causing a reaction between the following, while in the presence of a a compound represented by general formula (b) R4-Y (In the formula, R4 represents a C1-C4 haloalkyl group, and Y is a halogen atom or the like.); and a compound represented by general formula (3) (In the formula, R1 and R2 each independently represent a halogen atom or a C1-C4 alkyl group.), which is obtained by oxidizing a mercaptophenol derivative, and next, while in the presence of a base, causing a reaction with a compound represented by general formula (a) R3-X (In the formula, R3 represents a C1-C4 haloalkyl thio C2-C10 alkyl group, and X is a halogen atom or the like.).

Description

technical field [0001] The present invention relates to the manufacture method of the compound of general formula (4) and intermediate thereof, [0002] [0003] (where, [0004] R 1 and R 2 Each is independently a halogen atom or a C1-C4 alkyl group, [0005] R 3 C1~C4 haloalkylthio C2~C10 alkyl, [0006] R 4 is C1~C4 haloalkyl). [0007] The present invention especially relates to the manufacture intermediate of the compound of above-mentioned general formula (4): [0008] Compounds of general formula (2): [0009] [0010] (where, R 1 and R 2 as defined above); and [0011] Compounds of general formula (3): [0012] [0013] (where R 1 and R 2 and R 3 as defined above); and [0014] Compounds of general formula (5): [0015] [0016] (where, R 1 and R 2 and R 3 as defined above). Background technique [0017] The compound of the above-mentioned general formula (4) is useful as a pest control agent in the form of an agricultural chemical or...

Claims

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Application Information

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IPC IPC(8): C07C323/20C07C319/14C07C319/22C07C319/24
CPCC07C319/14C07C319/22C07C319/24C07C323/20
Inventor 安村信吾
Owner KUMIAI CHEM IND CO LTD
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