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Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent

A technology of azole derivatives and production method, applied in the field of azole derivatives, can solve problems such as no specific disclosed compounds, and achieve the effect of excellent bactericidal effect

Inactive Publication Date: 2014-02-05
KUREHA KAGAKU KOGYO KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, in Patent Document 3, there is no description about agricultural and horticultural chemicals and industrial material protection agents, and there is no specific disclosure of the compounds included in the present invention.

Method used

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  • Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent
  • Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent
  • Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent

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preparation example Construction

[0284] Metal alkoxides can be prepared by making alcohols (R 3 OH) is obtained by reacting with alkyllithium, metal sodium, metal lithium or sodium hydride in solvents such as THF and diethyl ether. Among them, a method of reacting with metal lithium is preferably used, and a method of reacting with alkyllithium is more preferably used.

[0285] The amount of the metal alkoxide is usually 0.5-fold mol to 20-fold mol, preferably 0.8-fold mol to 10-fold mol, based on the lactone compound (X).

[0286] As a solvent, THF, diethyl ether, dioxane or the like can be used, and it is preferable to use the same solvent as that used for the preparation of the metal alkoxide.

[0287] The reaction temperature and reaction time are appropriately set and used according to the reagents used. The reaction temperature is preferably -100°C to 200°C, more preferably -80°C to 150°C. In addition, the reaction time is preferably 0.1 hour to several days, more preferably 0.5 hour to 2 days.

[0...

manufacture example 1

[0448] (1SR,2SR,3RS)-3-(4-chlorobenzyl)-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1- Cyclopentane carboxylic acid (compound (I-1): R 1 =CH 3 , R 2 =COOH, A=N, Ym=4-Cl, stereo configuration CC) synthesis

[0449] 6.03 g of chromic acid was dissolved in 11.3 ml of water, and 5.2 ml of concentrated sulfuric acid was slowly added dropwise. 1.8 ml of water was added to the salt generated here to dissolve it, and Jones reagent was prepared. (1RS, 2SR, 3RS)-3-(4-chlorobenzyl)-2-hydroxy-1-methyl-2-(1H- 1,2,4-triazol-1-ylmethyl)-1-cyclopentanemethanol (compound (III-1):R 1 =CH 3 , A=N, Ym=4-Cl, stereo configuration CC) 1.44 g was dissolved in 45 ml of acetone, 3.3 ml of the previously prepared Jones reagent was added thereto, and stirred at room temperature for 1.5 hours.

[0450] After the reaction was completed, isopropanol was added, the green insoluble matter was filtered off, and then washed with acetone, the filtrate and the washing liquid were combined, the combi...

manufacture example 2

[0453] (1RS,2SR,3RS)-3-(4-chlorobenzyl)-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1- Cyclopentane carboxylic acid (compound (I-131): R 1 =CH 3 , R 2 =COOH, A=N, Ym=4-Cl, stereo configuration TC)

[0454] Instead of using (1SR,2SR,3RS)-3-(4-chlorobenzyl)-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)- 1-cyclopentanemethanol (compound number (III-2): R 1 =CH 3 , A=N, Ym=4-Cl, stereo configuration TC) to replace (1RS, 2SR, 3RS)-3-(4-chlorobenzyl)-2-hydroxyl-1-methyl-2-(1H- 1,2,4-Triazol-1-ylmethyl)-1-cyclopentanemethanol (compound number (III-1)) was used as a raw material, by the same method as the method for obtaining the above-mentioned compound (I-1) to obtain the target compound.

[0455]

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Abstract

Provided is an azole derivative which can be contained as an active ingredient in an agricultural or horticultural chemical agent having an excellent disease control effect. This azole derivative is represented by general formula (I). (In formula (I), R1 represents a C1-C6 alkyl group which may be substituted; R2 represents a functional group containing a carbonyl group, wherein a carbon atom in the carbonyl group is bonded to both a carbon atom substituted by R1 in the cyclopentane ring and any one selected from a hydrogen atom, a hydroxyl group, R3, OR3 and NR3R4; R3 and R4 independently represent a C1-C6 alkyl group, a C2-C6 alkenyl group or a C2-C6 alkynyl group; Y represents a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a phenyl group, a cyano group or a nitro group; m represents 0-5; and A represents a nitrogen atom or a methine group.).

Description

technical field [0001] The present invention relates to a novel azole derivative. It also relates to an agricultural and horticultural agent and an industrial material protection agent containing the derivative as an active ingredient, and a method for producing the derivative. Furthermore, intermediate compounds thereof are also involved. Background technique [0002] Certain 2-substituted-5-benzyl-1-azolylmethylcyclopentanol derivatives are known to exhibit fungicidal activity (see, for example, Patent Documents 1 to 2). [0003] In addition, it has been reported that some compounds included in 2-(halogenated hydrocarbon substituted)-5-benzyl-1-azolylmethylcyclopentanol derivatives exhibit anticonvulsant or anxiolytic activity (refer to patent Document 3). In addition, Patent Document 3 is silent on agricultural and horticultural chemicals and industrial material protection agents, and does not specifically disclose the compounds included in the present invention. [0...

Claims

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Application Information

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IPC IPC(8): C07D233/60A01N43/653A01P3/00C07D249/08C07D405/06
CPCC07D405/06C07D249/08A01N43/50A01N43/653C07D233/60A01N43/80C07D233/56C07D249/12C07D405/04A01N25/04A01N25/28
Inventor 荒木信行三宅泰司今井央由小畑惠美子
Owner KUREHA KAGAKU KOGYO KK
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