3,4-dihalogenoisothiazole derivative and agent for controlling agricultural or horticultural plant disease

一种异噻唑、衍生物的技术，应用在杀生物剂、植物生长调节剂、杀生剂等方向，能够解决没有公开等问题，达到高防除效果的效果

Active Publication Date: 2009-07-15
KUMIAI CHEM IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compound described in this document is a compound in which a methyl group is bonded to the 3-position of the isothiazole ring, and the 3,4-dihaloisothiazole derivative represented by the general formula [I] of the present application is not disclosed.

Method used

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  • 3,4-dihalogenoisothiazole derivative and agent for controlling agricultural or horticultural plant disease
  • 3,4-dihalogenoisothiazole derivative and agent for controlling agricultural or horticultural plant disease
  • 3,4-dihalogenoisothiazole derivative and agent for controlling agricultural or horticultural plant disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0159] Production of (3,4-dichloroisothiazol-5-yl)methylbenzoate (Compound No. II-1 of the present invention)

[0160] Add 8 ml of oxalyl chloride and a catalytic amount of N,N-dimethylformamide (DMF) to 4.0 g (20.3 mmol) of 3,4-dichloroisothiazole-5-carboxylic acid, and stir at 50° C. for 30 minutes. The reaction mixture was concentrated under reduced pressure to obtain 3,4-dichloroisothiazole-5-carbonyl chloride.

[0161] Suspend 1.9g (50.5mmol) of sodium borohydride in 40ml of water, and drop THF (4ml ) solution. Stir at 15°C for 30 minutes, then add aqueous citric acid to make the solution weakly acidic, and extract with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The obtained crystals were washed with hexane to obtain 3.0 g (yield 81%) of colorless crystals of (3,4-dichloroisothiazol-5-yl)methanol (melting point 94-95°C).

[0162] 1 H-NMR data (CDCl 3 / TMSδ (ppm)): 2.28 (1H, bs), 4.96 (2H, s) ppm

...

Embodiment 2

[0166] Production of (3,4-dichloroisothiazol-5-yl)methylthioacetate (Compound No. I-28 of the present invention)

[0167] To a solution of 2.85 g (10.9 mmol) of triphenylphosphine in THF 50 ml, 2.2 g (10.9 mmol) of diisopropyl azodicarboxylate was added under ice-cooling, followed by stirring for 30 minutes. A THF 5 ml solution of 1.0 g (5.43 mmol) of (3,4-dichloroisothiazol-5-yl)methanol and 0.83 g (10.9 mmol) of thioacetic acid was added to this solution, and stirred at room temperature for 5 hours. After completion of the reaction, ethyl acetate was added to the reaction mixture to wash with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to obtain 0.42 g (yield 32%) of (3,4-dichloroisothiazol-5-yl) methylthioacetate as a light red oily substance (refractive index 1.5855).

[0168] 1 H-NMR data (CDCl 3 / TMS δ (ppm)): 2.41 (3H, s), 4.24 (2H, s)

[0169] The physical property values ​​of the co...

Embodiment 3

[0176] [embodiment 3] powder

[0177] 2 parts of the compound of compound number I-1

[0178] Diatomaceous earth 5 parts

[0179] Clay 93 parts

[0180] The above ingredients are uniformly mixed and pulverized to make a powder. In addition, powders can be obtained in the same manner by using the compounds described in Tables 1 to 10 instead of Compound No. I-1.

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Abstract

To provide a 3,4-dihalogenoisothiazole derivative or a salt thereof which is not harmful to a crop and has a high controlling effect on an agricultural or horticultural plant disease such as rice blast disease, cucumber anthracnose, wheat powdery mildew and wheat glume blotch, and to provide an agent for controlling an agricultural or horticultural plant disease comprising the derivative or the salt thereof as an active ingredient. A 3,4-dihalogenoisothiazole derivative represented by the general formula [I] or a salt thereof. [I] wherein X and X independently represent a halogen atom; A represents an oxygen atom or a sulfur atom; and R represents a C1-C6 alkyl group, a C2-C5 alkenyl group, a C2-C5 alkynyl group, a C3-C6 cycloalkyl group, a phenyl group, or a 5- to 10-membered heterocyclic group containing at least one member selected from an oxygen atom, a sulfur atom and a nitrogen atom.

Description

technical field [0001] The present invention relates to a 3,4-dihalogenated isothiazole derivative or its salt, and an agricultural or horticultural plant disease control agent containing the derivative or its salt as an active ingredient. Background technique [0002] Conventionally, certain isothiazole derivatives are known to have plant disease controlling activity (see Patent Document 1). However, the compound described in this document is a compound in which a methyl group is bonded to the 3-position of the isothiazole ring, and the 3,4-dihalogenated isothiazole derivative represented by the general formula [I] of the present application is not disclosed. [0003] Patent Document 1: JP-A-2005-82486 Contents of the invention [0004] The problem to be solved by the invention [0005] In the cultivation of agricultural or horticultural crops, a variety of control agents are being used for crop diseases. Their control effects are insufficient, their use is limited due ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/02A01N43/80A01N43/828A01P3/00C07D417/12
CPCA01N43/82C07D417/12C07D275/02A01N43/80
Inventor 永田俊浩小暮笃史金子功米仓范久花井凉
Owner KUMIAI CHEM IND CO LTD
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