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Herbicide and production method for intermediate thereof

A manufacturing method and a halogenating agent technology, applied in the field of sulfone derivatives, can solve problems such as chemical damage to crops, separation difficulties, and quality decline

Pending Publication Date: 2021-06-15
KUMIAI CHEM IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compounds of formula (6) mixed into products such as herbicides may cause quality degradation and chemical damage to crops
However, since the physical and chemical properties of the compound of formula (6) are very similar to those of the compound of formula (5), it is difficult to separate the compound of formula (6) to purify the compound of formula (5)

Method used

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  • Herbicide and production method for intermediate thereof
  • Herbicide and production method for intermediate thereof
  • Herbicide and production method for intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0890]

[0891] [Chemical 44]

[0892] WO2004 / 013106A1, Example 14

[0893]

[0894] However, the compound of formula (2) is preferably produced by the method of the present invention. That is, when X in formula (2) 1 In the case of a halogen atom, the compound of the formula (2) is preferably produced by a method including the step i described in this specification.

[0895] In formula (2), R 1 , R 2 and R 3 as defined above. In formula (2), R 1 , R 2 and R 3 Examples, preferred examples, more preferred examples and particularly preferred examples are as described above.

[0896] X in formula (2) 1 for the leaving group. As long as it functions as a leaving group in the reaction of step ii, X in formula (2) 1 Can be any atom or group of atoms.

[0897] From the viewpoints of productivity, availability, price, etc., X in formula (2) 1 Preferred examples include halogen atoms, (C1-C4) alkylsulfonyloxy, (C1-C4) haloalkylsulfonyloxy, benzenesulfonyloxy optiona...

Embodiment 1

[1321] 3-[(5-Difluoromethoxy-1-methyl-3-trifluoromethylpyrazol-4-yl)methylthio]-4,5-dihydro-5,5-dimethyliso Production of oxazole (compound 4-a)

Embodiment 1-1

[1323] (Process i)

[1324] Production of 4-chloromethyl-5-difluoromethoxy-1-methyl-3-trifluoromethylpyrazole (compound 2-a)

[1325] [Chemical 53]

[1326]

[1327] To 5-difluoromethoxy-4-hydroxymethyl-1-methyl-3-trifluoromethylpyrazole (1-a) (46.7 g, purity: 68.6%, containing acetonitrile, 0.13 mol, 100 mol %), thionyl chloride (17.0 g, 0.14 mol, 110 mol %) was added dropwise over 1 hour at an internal temperature of 20°C to 30°C. After the dropwise addition, the mixture was aged at an internal temperature of 20°C to 30°C for 1 hour. After the reaction was completed, nitrogen was purged into the reaction mixture for 30 minutes to remove excess thionyl chloride, and ethyl acetate (78 mL, 0.6 L / mol) was added. The ethyl acetate solution of the obtained title compound (2-a) was 134 g.

[1328] (Process ii)

[1329] 3-[(5-Difluoromethoxy-1-methyl-3-trifluoromethylpyrazol-4-yl)methylthio]-4,5-dihydro-5,5-dimethyliso Production of oxazole (compound 4-a)

[1330] [Chemica...

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Abstract

The present invention provides a sulfone derivative that is useful as a herbicide, and an industrially preferable production method for an intermediate of said derivative. Provided is a production method for a compound of formula (4), the method including step ii, wherein step ii is a step for producing a compound of formula (4) by reacting a compound of formula (2) with a compound of formula (3) in the presence of a base. Also provided is a production method for a compound of formula (5), the method including step iii, wherein step iii is a step for producing a compound of formula (5) by reacting a compound of formula (4) with hydrogen peroxide in the presence of a metal catalyst.

Description

Technical field [0001] The present invention relates to a method for producing a sulfone derivative useful as a herbicide, that is, a compound of the following formula (5). [0002] [Chemical 1] [0003] [0004] In the formula, R 1 ,R 2 ,R 3 ,R 4 and R 5 As described in this manual. Background technique [0005] As disclosed in WO2002 / 062770A1 (Patent Document 1), the sulfone derivative of the above formula (5) is known to have herbicidal activity. Among them, Pyroxasulfone is known to be an excellent herbicide. [0006] As a method for producing the compound of formula (5), a method of oxidizing a sulfide derivative, that is, a compound of formula (4) is known, which is shown below. [0007] [Chemicalization 2] [0008] [0009] As shown in the figure below, Reference Example 3 of WO2004 / 013106A1 (Patent Document 2) describes the use of m-chloroperoxybenzoic acid (mCPBA) to convert 3-(5-difluoromethoxy-1-methyl-3-trifluoro Methyl-1H-pyrazol-4-ylmethylthio)-...

Claims

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Application Information

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IPC IPC(8): C07D413/12A01N43/80A01P13/00
CPCC07D413/12A01N43/80C07B2200/13A01P13/00A01N25/12A01N25/04C07B61/00
Inventor 内田幸生渥美真也谷真树冈田弘二村井勇太阿鲁诺特·克伊宾
Owner KUMIAI CHEM IND CO LTD
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