JP2005089362A - Aryl pyrazoline compound and its application - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having high controlling efficacy against plant disease injuries. <P>SOLUTION: The aryl pyrazoline compound of formula(I) is provided, having high controlling efficacy against plant disease injuries. In formula (I), L<SP>1</SP>is H, a halogen atom, 1-3C alkyl, 1-3C haloalkyl, 1-3C haloalkoxy or cyano; L<SP>2</SP>is H, a halogen atom, 1-3C alkyl or the like; Y is an oxygen atom, sulfur atom or methylene group; X-Y-Z is C(=O)-CH<SB>2</SB>, C(=NOR<SP>2</SP>)-CH<SB>2</SB>-CH<SB>2</SB>, CH<SB>2</SB>-CH<SB>2</SB>-C(=O), CH<SB>2</SB>-CH<SB>2</SB>-C(=NOR<SP>2</SP>), C(=O)-O-CH<SB>2</SB>or the like, wherein R<SP>2</SP>is H or a 1-3C alkyl. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to arylpyrazoline compounds and uses thereof.

  Conventionally, many compounds having a control effect against plant diseases have been developed and put into practical use. Moreover, a certain kind of arylpyrazoline compound is known as a reaction product of nitrile oxide, for example (see Non-Patent Document 1).

Journal of Chemical Research (miniprint), 1981, pp. 137-145 (J. Chem. Res. (M), 1981, p. 137-145).

  An object of the present invention is to provide a compound having an excellent control effect against plant diseases.

〔式中、Ｌ¹は水素原子、ハロゲン原子、Ｃ１−Ｃ３アルキル基、Ｃ１−Ｃ３ハロアルキル基、Ｃ１−Ｃ３ハロアルコキシ基又はシアノ基を表し、Ｌ²は水素原子、ハロゲン原子、Ｃ１−Ｃ３アルキル基、Ｃ１−Ｃ３アルコキシ基、Ｃ１−Ｃ３ハロアルキル基、Ｃ１−Ｃ３ハロアルコキシ基又はシアノ基を表し、Ｒ¹は水素原子又はＣ１−Ｃ５アルキル基を表し、Ｙは酸素原子、硫黄原子又はメチレン基を表し、−Ｘ−Ｙ−Ｚ−は−C(=O)−CH₂−CH₂−基、−C(=NOR²)−CH₂−CH₂−基、−CH₂−CH₂−C(=O)−基、−CH₂−CH₂−C(=NOR²)−基、−C(=O)−O−CH₂−基、−CH₂−O−C(=O)−基、−C(=O)−S−CH₂−基又は−CH₂−S−C(=O)−基を表し、Ｒ²は水素原子又はＣ１−Ｃ３アルキル基を表す。〕で示されるアリールピラゾリン化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有することを特徴とする植物病害防除剤及び本発明化合物の有効量を植物又は植物の生育する土壌に施用することを特徴とする植物病害の防除方法を提供する。 As a result of intensive studies to solve the above problems, the present inventor has found that an arylpyrazoline compound represented by the following formula (I) has an excellent control effect against plant diseases.
That is, the present invention relates to the formula (I)

Wherein, L ¹ is a hydrogen atom, a halogen atom, C1-C3 alkyl group, C1-C3 haloalkyl group, a C1-C3 haloalkoxy group, or a cyano group, L ² is a hydrogen atom, a halogen atom, C1-C3 alkyl Group, a C1-C3 alkoxy group, a C1-C3 haloalkyl group, a C1-C3 haloalkoxy group or a cyano group, R ¹ represents a hydrogen atom or a C1-C5 alkyl group, Y represents an oxygen atom, a sulfur atom or a methylene group. the stands, -X-Y-Z- is _{-C (= O) -CH 2 -CH} 2 - ^{group, -C (= NOR 2) -CH} 2 -CH 2 - group, -CH ₂ -CH ₂ -C (= O) - _{group, -CH 2 -CH 2 -C (=} NOR 2) - group, -C (= O) -O- CH 2 - _{group, -CH 2 -O-C (=} O) - group , -C (= O) -S- CH 2 - group or a _{-CH 2 -S-C (= O} ) - represents a group, R ² represents a hydrogen atom or a C1-C3 alkyl group. ], A plant disease control agent characterized by containing the compound of the present invention as an active ingredient, and an effective amount of the compound of the present invention in the amount of plant or plant growth. The present invention provides a method for controlling plant diseases characterized by being applied to soil.

  Since the plant disease control agent of the present invention has an excellent control effect against plant diseases, the compound of the present invention is useful as an active ingredient of the plant disease control agent.

In the present invention,
Examples of the halogen atom represented by L ¹ and L ² include a chlorine atom, a fluorine atom and a bromine atom,
Examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
Examples of the C1-C3 haloalkyl group include a trifluoromethyl group,
Examples of the C1-C3 haloalkoxy group include a trifluoromethoxy group and a 1,1,2,2-tetrafluoroethoxy group.
Examples of the C1-C3 alkoxy group represented by L ² include a methoxy group, an ethoxy group, a propyl group, and an isopropyl group.

Examples of the C1-C5 alkyl group represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a 1-methylbutyl group. 2-methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group and 1,1-dimethylpropyl group.
Examples of the C1-C3 alkyl group represented by R ² include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following (Production Method 1) to (Production Method 3).

〔式中、Ｌ¹、Ｌ²及びＲ¹は前記と同じ意味を表し、Ｙ¹はメチレン基を表し、−Ｘ¹−Ｙ¹−Ｚ¹−は−C(=O)−CH₂−CH₂−基又は−CH₂−CH₂−C(=O)−基を表し、−Ｘ²−Ｙ¹−Ｚ²−は−C(=NOH)−CH₂−CH₂−基又は−CH₂−CH₂−C(=NOH)−基を表し、−Ｘ³−Ｙ¹−Ｚ³−は−C(=NOR³)−CH₂−CH₂−基又は−CH₂−CH₂−C(=NOR³)−基を表し、Ｒ³はＣ１−Ｃ３アルキル基を表し、Ｌ³は臭素原子又はヨウ素原子を表す。〕
工程（１−１）
式（３）で示される化合物は、式（２）で示される化合物とヒドロキシルアミン（通常その塩酸塩、硫酸塩等の塩が反応に用いられる。）とを反応させることにより製造することができる。
該反応は通常溶媒の存在下、塩基の存在下又は非存在下で行われる。
反応に用いられる溶媒としては、例えばメタノール、エタノール等のアルコール類、ホルムアミド、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、トルエン、キシレン等の芳香族炭化水素類、クロロホルム、ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、１，４−ジオキサン、テトラヒドロフラン等のエーテル類、ヘキサン、ヘプタン等の脂肪族炭化水素類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えばトリエチルアミン、ピリジン等の有機塩基類、炭酸カリウム、炭酸ナトリウム等の炭酸塩類、水酸化ナトリウム、水酸化カリウム等の水酸化物塩が挙げられる。
反応に用いられる試剤の量は、式（２）で示される化合物１モルに対して、ヒドロキシルアミンが通常１〜３モルの割合、好ましくは１〜１．２モルの割合であり、塩基が通常１〜１０モルの割合であり、好ましくは２〜５モルの割合である。
該反応の反応温度は、通常０〜１００℃の範囲であり、反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、式（３）で示される化合物を単離することができる。単離された式（３）で示される化合物は、有機溶媒による洗浄、再結晶、カラムクロマトグラフィーによりさらに精製することもできる。 (Production method 1)
Among the compounds of the present invention represented by the formula (I), -X-Y- Z- is _{-C (= O) -CH 2 -CH} 2 - ^{group, -C (= NOR 2) -CH} 2 -CH 2 - A compound represented by a group, a —CH ₂ —CH ₂ —C (═O) — group or a —CH ₂ —CH ₂ —C (═NOR ² ) — group can be produced, for example, by the following method.

[Wherein L ¹ , L ² and R ¹ represent the same meaning as described above, Y ¹ represents a methylene group, —X ¹ —Y ¹ —Z ¹ — represents —C (═O) —CH ₂ —CH ₂ -group or -CH ₂ -CH ₂ -C (= O)-group, -X ² -Y ¹ -Z ² -represents -C (= NOH) -CH ₂ -CH ₂ -group or -CH ₂ -X ₂ -C (= NOH)-group, -X ³ -Y ¹ -Z ³ -represents -C (= NOR ³ ) -CH ₂ -CH ₂ -group or -CH ₂ -CH ₂ -C ( = NOR ³ ) — group, R ³ represents a C1-C3 alkyl group, and L ³ represents a bromine atom or an iodine atom. ]
Step (1-1)
The compound represented by the formula (3) can be produced by reacting the compound represented by the formula (2) with hydroxylamine (usually a salt such as hydrochloride or sulfate is used for the reaction). .
The reaction is usually performed in the presence of a solvent, in the presence or absence of a base.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, acid amides such as formamide and N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, aromatic hydrocarbons such as toluene and xylene, chloroform, and the like. , Halogenated hydrocarbons such as dichloroethane and chlorobenzene, ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, 1,4-dioxane and tetrahydrofuran, aliphatic hydrocarbons such as hexane and heptane, and mixtures thereof Is mentioned.
Examples of the base used in the reaction include organic bases such as triethylamine and pyridine, carbonates such as potassium carbonate and sodium carbonate, and hydroxide salts such as sodium hydroxide and potassium hydroxide.
The amount of the reagent used in the reaction is usually 1 to 3 moles, preferably 1 to 1.2 moles of hydroxylamine, and 1 base to 1 mole of the compound represented by the formula (2). The ratio is 1 to 10 moles, preferably 2 to 5 moles.
The reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound represented by the formula (3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound represented by the formula (3) can be further purified by washing with an organic solvent, recrystallization, and column chromatography.

Step (1-2)
The compound represented by the formula (4) can be produced by reacting the compound represented by the formula (3) with the compound represented by the formula (5).
The reaction is usually performed in the presence of a solvent, in the presence or absence of a base.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, acid amides such as formamide and N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, aromatic hydrocarbons such as toluene and xylene, chloroform, and the like. Halogenated hydrocarbons such as dichloroethane and chlorobenzene, ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, 1,4-dioxane and tetrahydrofuran, aliphatic hydrocarbons such as hexane and heptane, pyridine and picoline And nitrogen-containing aromatics and mixtures thereof.
Examples of the base used in the reaction include carbonates such as potassium carbonate and sodium carbonate, and hydroxide salts such as sodium hydroxide and potassium hydroxide.
The amount of the reagent used in the reaction is usually 1 to 3 mol, preferably 1 to 1.2 mol, of the compound represented by the formula (5) with respect to 1 mol of the compound represented by the formula (3). The base is usually in a proportion of 1 to 10 mol, preferably in a proportion of 1 to 5 mol.
The reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound represented by the formula (4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound represented by the formula (4) can be further purified by washing with an organic solvent, recrystallization, and column chromatography.

〔式中、Ｌ¹、Ｌ²、Ｒ¹、Ｒ³及び−Ｘ³−Ｙ¹−Ｚ³−は前記と同じ意味を表す。〕
式（４）で示される化合物は、式（２）で示される化合物と式（６）で示される化合物（通常その塩酸塩、硫酸塩等の塩が反応に用いられる。）とを反応させることにより製造することができる。
該反応は通常溶媒の存在下、塩基の存在下又は非存在下で行われる。
反応に用いられる溶媒としては、例えばメタノール、エタノール等のアルコール類、ホルムアミド、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、トルエン、キシレン等の芳香族炭化水素類、クロロホルム、ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、１，４−ジオキサン、テトラヒドロフラン等のエーテル類、ヘキサン、ヘプタン等の脂肪族炭化水素類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えばトリエチルアミン、ピリジン等の有機塩基類、炭酸カリウム、炭酸ナトリウム等の炭酸塩類、水酸化ナトリウム、水酸化カリウム等の水酸化物塩が挙げられる。
反応に用いられる試剤の量は、式（２）で示される化合物１モルに対して、式（６）で示される化合物が通常１〜３モルの割合、好ましくは１〜１．２モルの割合であり、塩基が通常１〜１０モルの割合であり、好ましくは２〜５モルの割合である。
該反応の反応温度は、通常０〜１００℃の範囲であり、反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、式（４）で示される化合物を単離することができる。単離された式（４）で示される化合物は、有機溶媒による洗浄、再結晶、カラムクロマトグラフィーによりさらに精製することもできる。 (Production method 2)
Among the compounds represented by the formula (I), —X—Y—Z— represents a —C (═NOR ² ) —CH ₂ —CH ₂ — group or a —CH ₂ —CH ₂ —C (= NOR ² ) — group. And a compound in which R ² is a C1-C3 alkyl group can also be produced, for example, by the following method.

[Wherein, L ¹ , L ² , R ¹ , R ³ and —X ³ —Y ¹ —Z ³ — represent the same meaning as described above. ]
The compound represented by the formula (4) is obtained by reacting the compound represented by the formula (2) with the compound represented by the formula (6) (usually a salt such as its hydrochloride or sulfate is used for the reaction). Can be manufactured.
The reaction is usually performed in the presence of a solvent, in the presence or absence of a base.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, acid amides such as formamide and N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, aromatic hydrocarbons such as toluene and xylene, chloroform, and the like. , Halogenated hydrocarbons such as dichloroethane and chlorobenzene, ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, 1,4-dioxane and tetrahydrofuran, aliphatic hydrocarbons such as hexane and heptane, and mixtures thereof Is mentioned.
Examples of the base used in the reaction include organic bases such as triethylamine and pyridine, carbonates such as potassium carbonate and sodium carbonate, and hydroxide salts such as sodium hydroxide and potassium hydroxide.
The amount of the reagent used in the reaction is usually 1 to 3 mol, preferably 1 to 1.2 mol, of the compound represented by formula (6) with respect to 1 mol of the compound represented by formula (2). The base is usually in a proportion of 1 to 10 mol, preferably in a proportion of 2 to 5 mol.
The reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound represented by the formula (4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound represented by the formula (4) can be further purified by washing with an organic solvent, recrystallization, and column chromatography.

〔式中、Ｌ¹、Ｌ²及びＲ¹は前記と同じ意味を表し、Ｌ⁴は塩素原子又は臭素原子を表し、−Ｘ⁴−Ｙ⁴−Ｚ⁴−は−C(=O)−CH₂−CH₂−基、−CH₂−CH₂−C(=O)−基、−C(=O)−O−CH₂−基、−CH₂−O−C(=O)−基、−C(=O)−S−CH₂−基又は−CH₂−S−C(=O)−基を表す。〕
該反応は通常溶媒の存在下、塩基の存在下で行われる。
反応に用いられる溶媒としては、例えばトルエン、キシレン等の芳香族炭化水素類、クロロホルム、ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、１，４−ジオキサン、テトラヒドロフラン等のエーテル類、ヘキサン、ヘプタン等の脂肪族炭化水素類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えばトリエチルアミン、ピリジン等の有機塩基類、炭酸カリウム、炭酸ナトリウム等の炭酸塩類、水酸化ナトリウム、水酸化カリウム等の水酸化物塩が挙げられる。
反応に用いられる試剤の量は、式（８）で示される化合物１モルに対して、式（７）で示される化合物が通常１〜３モルの割合、好ましくは１〜１．２モルの割合であり、塩基が通常１〜１０モルの割合、好ましく２〜５モルの割合である。
該反応の反応温度は、通常０〜１５０℃の範囲であり、反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、式（９）で示される化合物を単離することができる。単離された式（９）で示される化合物は、有機溶媒による洗浄、再結晶、カラムクロマトグラフィーによりさらに精製することもできる。 (Production method 3)
Among the compounds represented by the formula (I), —X—Y—Z— represents a —C (═O) —CH ₂ —CH ₂ — group, a —CH ₂ —CH ₂ —C (═O) — group, — C (= O) -O-CH 2 - _{group, -CH 2 -O-C (=} O) - group, -C (= O) -S- CH 2 - group or a -CH ₂ -S-C (= The compound represented by the group O)-can be produced, for example, by the following method.

[Wherein L ¹ , L ² and R ¹ represent the same meaning as described above, L ⁴ represents a chlorine atom or a bromine atom, and —X ⁴ —Y ⁴ —Z ⁴ — represents —C (═O) —CH ₂ -CH ₂ - _{group, -CH 2 -CH 2 -C (=} O) - group, -C (= O) -O- CH 2 - _{group, -CH 2 -O-C (=} O) - group, —C (═O) —S—CH ₂ — group or —CH ₂ —S—C (═O) — group is represented. ]
The reaction is usually carried out in the presence of a solvent and in the presence of a base.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform, dichloroethane, and chlorobenzene, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and 1,4-dioxane. , Ethers such as tetrahydrofuran, aliphatic hydrocarbons such as hexane and heptane, and mixtures thereof.
Examples of the base used in the reaction include organic bases such as triethylamine and pyridine, carbonates such as potassium carbonate and sodium carbonate, and hydroxide salts such as sodium hydroxide and potassium hydroxide.
The amount of the reagent used for the reaction is usually 1 to 3 mol, preferably 1 to 1.2 mol, of the compound represented by formula (7) with respect to 1 mol of the compound represented by formula (8). The base is usually in a proportion of 1 to 10 mol, preferably 2 to 5 mol.
The reaction temperature is usually in the range of 0 to 150 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound represented by the formula (9) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound represented by the formula (9) can be further purified by washing with an organic solvent, recrystallization, and column chromatography.

  Examples of the compound represented by the formula (7) include those disclosed in JP-A-62-2286958, J. Pat. Org. Chem. 33, p. 753 (1968), J.A. Org. Chem. USSR, 12, p. 1649-1653 (1976), J. MoI. Heterocyclic Chem. 22, p. It can manufacture according to the method as described in 565-568 (1985).

As an aspect of this invention compound, the following aryl pyrazoline compound is mentioned, for example.
An arylpyrazoline compound represented by the formula (I), wherein L ¹ is a halogen atom;
An arylpyrazoline compound represented by the formula (I), wherein L ¹ is a chlorine atom, a bromine atom or a methyl group;
An arylpyrazoline compound represented by the formula (I), wherein L ¹ is a chlorine atom;
An arylpyrazoline compound represented by the formula (I), wherein L ² represents a hydrogen atom;
An arylpyrazoline compound represented by the formula (I), wherein L ¹ is a halogen atom and L ² is a hydrogen atom;
An arylpyrazoline compound represented by the formula (I), wherein L ¹ is a chlorine atom, a bromine atom or a methyl group, and L ² is a hydrogen atom;
An arylpyrazoline compound represented by the formula (I), wherein L ¹ is a chlorine atom and L ² is a hydrogen atom;

An arylpyrazoline compound represented by formula (I), wherein R ¹ is a C1-C3 alkyl group;
An arylpyrazoline compound represented by formula (I), wherein R ¹ is a methyl group, an ethyl group or an isopropyl group;
An arylpyrazoline compound represented by formula (I), wherein R ¹ represents a methyl group;

An arylpyrazoline compound represented by formula (I), wherein Y is an oxygen atom;
An arylpyrazoline compound represented by formula (I), wherein Y is a methylene group;
In the formula (I), -X-Y- Z- is _{-C (= O) -CH 2 -CH} 2 - aryl pyrazoline compound represented by the group;
In the formula (I), -X-Y- Z- is _{-CH 2 -CH 2 -C (= O} ) - aryl pyrazoline compound represented by the group;
In the formula (I), -X-Y- Z- is _{-C (= NOH) -CH 2 -CH} 2 - group or a _{-CH 2 -CH 2 -C (= NOH} ) - aryl pyrazoline compound represented by the group ;
In formula (I), an arylpyramine in which —X—Y—Z— is represented by a —C (═NOCH ₃ ) —CH ₂ —CH ₂ — group or a —CH ₂ —CH ₂ —C (═NOCH ₃ ) — group. Zolin compounds;

Examples of plant diseases to which the compound of the present invention has a controlling effect include the following.
Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), solani);
Wheat powdery mildew (Erysiphe graminis), red mold (Gibberella zeae), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronectriella nivalis), Bare scab (Ustilago tritici, U. nuda), Nagisa scab (Tilletia caries), eye spot disease (Pseudocercosporella herpotrichoides), cloud disease (Rhynchosporium secalis), leaf blight (Septoria tritici), leaf blight (Leptosphaeria nodor citrus) Sunspot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum);
Apple moniliosis (Sclerotinia mali), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), spotted leaf (Alternaria mali), black rot (Venturia inaequalis);
Pear black spot (Venturia nashicola, V. pirina), black spot (Alternaria kikuchiana), red star (Gymnosporangium haraeanum);
Peach ash scab (Sclerotinia cinerea), black scab (Cladosporium carpophilum), Phomopsis sp. (Phomopsis sp.);
Grapes black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola);
Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae);
Colletotrichum lagenarium, powdery mildew (Sphaerothecafuliginea), vine blight (Mycosphaerella melonis), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.) Blight disease (Pythium sp.);
Tomato ring disease (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);
Brassicaceae vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae);
Leek rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), sunspot (Diaporthe phaseolorum var. Sojae);
Kidney anthracnose (Colletotrichum lindemthianum);
Groundnut black rot (Cercospora personata), brown spot (Cercospora arachidicola);
Pea powdery mildew (Erysiphe pisi);
Potato summer plague (Alternaria solani), plague (Phytophthora infestans);
Strawberry powdery mildew (Sphaerotheca humuli);
Tea net blast (Exobasidium reticulatum); white scab (Elsinoe leucospila), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), Plague (Phytophthora nicotianae);
Brown spot of sugar beet (Cercospora beticola);
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum brown spot disease (Septoria chrysanthemi-indici), white rust disease (Puccinia horiana);
Botrytis cinerea and Sclerotinia sclerotiorum in various crops.

The plant disease control agent of the present invention may be the compound of the present invention itself. Usually, the compound of the present invention is mixed with a solid carrier and / or a liquid carrier, and if necessary, a surfactant or other adjuvant for formulation. To form emulsions, wettable powders, granular wettable powders, flowables, powders, granules and the like.
These preparations usually contain 0.1 to 90% by weight of the compound of the present invention.

Examples of solid carriers used in the formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite minerals, corn cob flour, walnut shell powder, etc. Natural organic materials, synthetic organic materials such as urea, salts such as calcium carbonate and ammonium sulfate, fine powders or granular materials made of synthetic inorganic materials such as synthetic silicon hydroxide, etc., and liquid carriers include, for example, xylene, alkylbenzene, methyl Aromatic hydrocarbons such as naphthalene, alcohols such as 2-propanol, ethylene glycol, propylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, and petroleum aliphatic hydrocarbons , Esters, dimethyls Sulfoxide, acetonitrile, and water.
Examples of the surfactant include anions such as alkyl sulfate ester salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates and the like. Nonionic surfactants such as surfactants and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned.
Examples of other adjuvants for preparation include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol Inorganic substances such as preservatives, colorants and stabilizers such as PAP (isopropyl acid phosphate) and BHT.

  The plant disease control agent of the present invention is used to protect the plant from plant diseases, for example, by treating the plant body, and also protects plants growing in the soil from plant diseases by treating the soil. Used for.

When the plant disease control agent of the present invention is used by treating the plant body with foliage treatment or by treating it with soil, the treatment amount depends on the type of crop, the type of disease to be controlled, and the control type. Although it can be changed depending on the degree of occurrence of the target disease, preparation form, treatment time, weather conditions, etc., it is usually 1 to 5000 g, preferably 5 to 1000 g as the compound of the present invention per 10,000 m ² .
Emulsions, wettable powders and flowables are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0001 to 3% by weight, preferably 0.0005 to 1% by weight. Powders, granules, etc. are usually processed without dilution.

  Moreover, the plant disease control agent of this invention can also be used by processing methods, such as seed disinfection. The method includes, for example, a method of immersing seeds in a plant disease control agent of the present invention in which plant seeds are prepared at a concentration of 1 to 1000 ppm of the compound of the present invention. Examples thereof include a method of spraying or smearing the plant disease control agent of the present invention and a method of dressing the plant disease control agent of the present invention on plant seeds.

  The plant disease control method of the present invention is usually carried out by treating an effective amount of the plant disease control agent of the present invention on the plant where the occurrence of the disease is predicted or the soil where the plant grows.

  The plant disease control agent of the present invention is usually used as a plant disease control agent for agricultural and horticultural use, that is, a plant disease control agent for controlling plant diseases such as upland, paddy fields, orchards, tea gardens, pastures, and lawns.

The plant disease control agent of the present invention can be used together with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators and / or fertilizers.
Examples of such fungicides include propiconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, dinicoazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, Azolic fungicidal compounds such as microbutanyl, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, viteltanol, imazalyl and flutriahol, cyclic amine-based fungicidal compounds such as fenpropimorph, tridemorph and fenpropidin Benzimidazole fungicides such as carbendazim, benomyl, thiabendazole, thiophanate methyl, procymidone, cyprodinyl, pyrimethanil, di Tofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpicuronyl, fludioxonil, diclofluanide, folpette, cresoxime methyl, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide, spiroxamine, quinoxyphene, fenhexamide, famoxadone, fenamidone (RP-407213), iprovaricarb, benchavari Examples include carb, cyazofamide, nicobifen, metolaphenone, and cyflufenamide.

  Next, although the specific example of this invention compound is shown, this invention is not limited to these compounds.

An arylpyrazoline compound represented by formula (i);

An arylpyrazoline compound represented by formula (ii);

An arylpyrazoline compound represented by formula (iii);

An arylpyrazoline compound represented by formula (iv);

An arylpyrazoline compound represented by the formula (v);

An arylpyrazoline compound represented by formula (vi);

An arylpyrazoline compound represented by formula (vii);

An arylpyrazoline compound represented by the formula (viii);

An arylpyrazoline compound represented by the formula (ix);

式（i）〜（x）において、Ｒ¹、Ｌ¹及びＬ²で示される各置換基は下記の（表１）、（表２）及び（表３）に示される基との組み合わせのいずれかを表す。なお、本発明化合物の化合物番号は前記式（i）〜（x）と下記の（表１）、（表２）及び（表３）に記載の番号との組み合わせで示され、例えば本発明化合物（i−21）とは、化合物

を表す。 An arylpyrazoline compound represented by the formula (x);

In the formulas (i) to (x), each of the substituents represented by R ¹ , L ¹ and L ² is any combination of the groups shown in the following (Table 1), (Table 2) and (Table 3). Represents In addition, the compound number of this invention compound is shown by the combination of the said Formula (i)-(x) and the number as described in following (Table 1), (Table 2), and (Table 3), for example, this invention compound (I-21) is a compound

Represents.

  Next, the present invention will be described with reference to production examples, formulation examples, test examples, and the like.

油状物質
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．０８（３Ｈ，ｓ）、２．２−２．４（４Ｈ，ｍ）、３．７３（１Ｈ，ｄ，Ｊ＝１０．４Ｈｚ）、４．８−４．９（１Ｈ，ｍ）、６．９４（２Ｈ，ｄ、Ｊ＝８．６Ｈｚ）、７．２２（２Ｈ，ｄ、Ｊ＝８．６Ｈｚ）
本発明化合物（ii-21）

融点 １１４．０℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．１０（３Ｈ，ｓ）、２．１−２．７（４Ｈ，ｍ）、３．８−３．９（１Ｈ，ｍ）、４．２２（１Ｈ，ｄ，Ｊ＝１０．８Ｈｚ）、７．２０（４Ｈ，ｓ） First, the manufacture example of this invention compound is shown below.
Production Example 1
In 15 ml of chloroform, 0.5 g of N- (p-chlorophenyl) acetohydrazonoyl chloride and 0.2 g of 2-cyclopenten-1-one were dissolved, and 0.5 g of triethylamine was added dropwise at room temperature, and 1.5 g at room temperature. Stir for hours. Chloroform was added to the reaction mixture, washed successively with 5% hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and 1- (4-chlorophenyl) -3-methyl-1,3a, 4,5,6,6a-hexahydrocyclopenta [c] pyrazol-4-one (the following physical properties were measured). Compound shown below, hereinafter referred to as the present compound (i-21).) 0.12 g and 1- (4-chlorophenyl) -3-methyl-1,3a, 4,5,6,6a-hexahydrocyclopenta [ c] 0.1 g of pyrazol-6-one (a compound having the following physical properties, hereinafter referred to as the present compound (ii-21)) was obtained.
Compound (i-21) of the present invention

Oily substance
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.08 (3H, s), 2.2-2.4 (4H, m), 3.73 (1H, d, J = 10. 4 Hz), 4.8-4.9 (1 H, m), 6.94 (2 H, d, J = 8.6 Hz), 7.22 (2 H, d, J = 8.6 Hz)
Compound (ii-21) of the present invention

Melting point 114.0 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.10 (3H, s), 2.1-2.7 (4H, m), 3.8-3.9 (1H, m) 4.22 (1H, d, J = 10.8 Hz), 7.20 (4H, s)

融点１６０．７℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．０６（３Ｈ，ｓ）、２．０６−２．１９（３Ｈ，ｍ）、２．９６−３．０２（１Ｈ，ｍ）、３．６８−３．７４（１Ｈ，ｍ）、４．７９（１Ｈ，ｄ，Ｊ＝１０．２Ｈｚ）、７．１６（２Ｈ、ｄ，Ｊ＝９．２Ｈｚ）、７．２１（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ）、７．４１（１Ｈ、ｓ） Production Example 2
This compound (ii-21) 0.19g was melt | dissolved in 5 ml of pyridines, 0.06g of hydroxylamine hydrochloride was added here, and it stirred at room temperature for 4 hours. The reaction mixture was acidified with 5% hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude crystals were washed with a mixed solvent of hexane / ethyl acetate, and 1- (4-chlorophenyl) -3-methyl-6-hydroxyimino-1,3a, 4,5,6,6a-hexahydrocyclopenta [ c] 0.09 g of pyrazole (a compound having the following physical properties, hereinafter referred to as the present compound (viii-21)) was obtained.
The compound of the present invention (viii-21)

Melting point 160.7 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.06 (3H, s), 2.06-2.19 (3H, m), 2.96-3.02 (1H, m) 3.68-3.74 (1H, m), 4.79 (1H, d, J = 10.2 Hz), 7.16 (2H, d, J = 9.2 Hz), 7.21 (2H, d, J = 9.2 Hz), 7.41 (1H, s)

融点 １４２．１℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．２３（３Ｈ，ｓ）、４．１３（１Ｈ，ｄ，Ｊ＝１０．８Ｈｚ）、４．４−４．５（１Ｈ，ｍ）、４．７−４．８（１Ｈ，ｍ）、４．９−５．０（１Ｈ，ｍ）、６．８５（２Ｈ，ｄ，Ｊ＝８．８Ｈｚ）、７．２４（２Ｈ，ｄ，Ｊ＝８．８Ｈｚ） Production Example 3
In 15 ml of chloroform, 0.7 g of N- (p-chlorophenyl) acetohydrazonoyl chloride and 0.29 g of 2 (5H) furanone were dissolved, 0.7 g of triethylamine was added dropwise at room temperature, and the mixture was stirred at room temperature for 1.5 hours. did. The reaction mixture was washed successively with 5% hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 1- (4-chlorophenyl) -3-methyl-3a, 4,6,6a-tetrahydro-1H-furo [3,4-c] pyrazol-4-one (the following physical properties) (Hereinafter referred to as the present compound (iii-21).) 0.21 g was obtained.
Compound (iii-21) of the present invention

Melting point 142.1 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.23 (3H, s), 4.13 (1H, d, J = 10.8 Hz), 4.4-4.5 (1H, m), 4.7-4.8 (1H, m), 4.9-5.0 (1H, m), 6.85 (2H, d, J = 8.8 Hz), 7.24 (2H, d, J = 8.8 Hz)

融点 １８７．２℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．１５（３Ｈ，s）、３．４−３．５（１Ｈ，ｍ）、３．８−３．９（１Ｈ，ｍ）、４．１１（１Ｈ，ｄ，Ｊ＝１０．０Ｈｚ）、５．０−５．１（１Ｈ，ｍ）、６．９９（２Ｈ，Ｊ＝９．２Ｈｚ）、７，２６（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ）
本発明化合物（vi-21）

油状物質
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．１１（３Ｈ，s）、３．４−３．５（１Ｈ，ｍ）、３．８−３．９（１Ｈ，ｍ）、４．０−４．１（１Ｈ，ｍ）、４．７７（１Ｈ，ｄ，Ｊ＝１０．０Ｈｚ）、７．２０（４Ｈ，s） Production Example 4
In 30 ml of chloroform, 1.0 g of N- (p-chlorophenyl) acetohydrazonoyl chloride and 0.49 g of 2 (5H) thiophenone were dissolved, and 1.0 g of triethylamine was added dropwise thereto at room temperature, followed by stirring at room temperature for 1.5 hours. did. The reaction mixture was washed successively with 5% hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 1- (4-chlorophenyl) -3-methyl-3a, 4,6,6a-tetrahydro-1H-thieno [3,4, c] pyrazol-4-one (the following physical properties) (Hereinafter referred to as the present compound (v-21).) 0.1 g and 1- (4-chlorophenyl) -3-methyl-3-3a, 4,6,6a-tetrahydro-1H-thieno [ 3,4-c] pyrazol-6-one (a compound having the following physical properties, hereinafter referred to as the present compound (vi-21)) was obtained in an amount of 0.1 g.
The present compound (v-21)

Melting point 187.2 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.15 (3H, s), 3.4-3.5 (1H, m), 3.8-3.9 (1H, m) 4.11 (1H, d, J = 10.0 Hz), 5.0-5.1 (1 H, m), 6.99 (2H, J = 9.2 Hz), 7, 26 (2H, d, J = 9.2Hz)
Compound (vi-21) of the present invention

Oily substance
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.11 (3H, s), 3.4-3.5 (1H, m), 3.8-3.9 (1H, m) 4.0-4.1 (1H, m), 4.77 (1H, d, J = 10.0 Hz), 7.20 (4H, s)

融点 ９０．６℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１．２７（３Ｈ，ｄ，Ｊ＝６．８Ｈｚ）、１．３１（３Ｈ，ｄ，Ｊ＝６．８Ｈｚ）、２．９４（１Ｈ，ｓｅｐ，Ｊ＝６．８Ｈｚ）、４．２７（１Ｈ，ｄ，Ｊ＝１０．８Ｈｚ）、４．４０（１Ｈ，ｄ、Ｊ＝１０．０Ｈｚ）、４．７−４．８（１Ｈ，ｍ）、４．９−５．０（１Ｈ，ｍ）、６．８６（２Ｈ，ｄ，Ｊ＝９．０Ｈｚ）、７．２３（２Ｈ，ｄ，Ｊ＝９．０Ｈｚ）
本発明化合物（iv-57）

融点 ９２．５℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１．２１（３Ｈ，ｄ，Ｊ＝７．２Ｈｚ）、１．２８（３Ｈ，ｄ，Ｊ＝７．２Ｈｚ）、２．７０（１Ｈ，ｓｅｐ，Ｊ＝７．２Ｈｚ）、４．２−４．４（２Ｈ，ｍ）、４．６−４．７（２Ｈ，ｍ）、７．２４（２Ｈ，ｄ、Ｊ＝９．４Ｈｚ）、９．３５（２Ｈ，ｄ，Ｊ＝９．４Ｈｚ） Production Example 5
In 20 ml of chloroform, 1.0 g of N- (p-chlorophenyl) -2-methylpropionohydrazonoyl chloride and 0.36 g of 2 (5H) furanone were dissolved, and 0.9 g of triethylamine was added dropwise at room temperature. Stir for 1.5 hours. The reaction mixture was washed with 5% hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 1- (4-chlorophenyl) -3-isopropyl-3a, 4,6,6a-tetrahydro-1H-furo [3,4-c] pyrazol-4-one (the following physical properties) (Hereinafter referred to as the present compound (iii-57).) 0.1 g and 1- (4-chlorophenyl) -3-isopropyl-3a, 4,5,5a-tetrahydro-1H-furo [3, 4-c] pyrazol-6-one (compound exhibiting the following physical properties. Hereinafter, referred to as the present compound (iv-57))
The compound of the present invention (iii-57)

Melting point 90.6 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 1.27 (3H, d, J = 6.8 Hz), 1.31 (3H, d, J = 6.8 Hz), 2.94 ( 1H, sep, J = 6.8 Hz), 4.27 (1H, d, J = 10.8 Hz), 4.40 (1H, d, J = 10.0 Hz), 4.7-4.8 (1H) , M), 4.9-5.0 (1H, m), 6.86 (2H, d, J = 9.0 Hz), 7.23 (2H, d, J = 9.0 Hz)
The compound of the present invention (iv-57)

Melting point 92.5 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 1.21 (3H, d, J = 7.2 Hz), 1.28 (3H, d, J = 7.2 Hz), 2.70 ( 1H, sep, J = 7.2 Hz), 4.2-4.4 (2H, m), 4.6-4.7 (2H, m), 7.24 (2H, d, J = 9.4 Hz) ), 9.35 (2H, d, J = 9.4 Hz)

  Next, this invention compound manufactured by the method according to the said manufacture example and its physical-property value are shown.

油状物質
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１． ２２（３Ｈ，ｔ，Ｊ＝７．４Ｈｚ）、２．２−２．４（５Ｈ，ｍ）、２．５−２．６（１Ｈ，ｍ）、３．７９（１Ｈ，ｄ，Ｊ＝１０．８Ｈｚ）、４．７−４．８（１Ｈ，ｍ）、６．９９（２Ｈ，ｄ，Ｊ＝８．８Ｈｚ）、７．２４（２Ｈ，ｄ，Ｊ＝８．８Ｈｚ） Compound (i-39) of the present invention

Oily substance
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 22 (3H, t, J = 7.4 Hz), 2.2-2.4 (5H, m), 2.5-2.6 (1H, m), 3.79 (1H, d, J = 10) .8 Hz), 4.7-4.8 (1 H, m), 6.99 (2 H, d, J = 8.8 Hz), 7.24 (2 H, d, J = 8.8 Hz)

油状物質
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１．２１（３Ｈ，ｄ，Ｊ＝６．４Ｈｚ）、１．２５（３Ｈ，ｄ，Ｊ＝６．４Ｈｚ）、２．３−２．４（４Ｈ，ｍ）、２．７２ (１Ｈ，ｓｅｐ，Ｊ＝６．４Ｈｚ)、３．８９（１Ｈ，ｄ，Ｊ＝１０．４Ｈｚ）、４．７−４．８（１Ｈ，ｍ）、７．００（２Ｈ，ｄ，Ｊ＝８．６Ｈｚ）７．２２（２Ｈ，ｄ，Ｊ＝８．６Ｈｚ） Compound (i-57) of the present invention

Oily substance
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 1.21 (3H, d, J = 6.4 Hz), 1.25 (3H, d, J = 6.4 Hz), 2.3 2.4 (4H, m), 2.72 (1H, sep, J = 6.4 Hz), 3.89 (1H, d, J = 10.4 Hz), 4.7-4.8 (1H, m ), 7.00 (2H, d, J = 8.6 Hz) 7.22 (2H, d, J = 8.6 Hz)

油状物質
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１．２５（３Ｈ，ｔ，Ｊ＝７．５Ｈｚ）、２．１−２．６（６Ｈ，ｍ）、３，９−４．０（１Ｈ，ｍ）、４．２０（１Ｈ，ｄ、Ｊ＝１０．７Ｈｚ）、７．１−７．２（４Ｈ，ｍ） The compound of the present invention (ii-39)

Oily substance
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 1.25 (3H, t, J = 7.5 Hz), 2.1-2.6 (6H, m), 3, 9-4. 0 (1H, m), 4.20 (1H, d, J = 10.7 Hz), 7.1-7.2 (4H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１．２２（３Ｈ，ｄ，Ｊ＝７．２Ｈｚ）、１．３１（３Ｈ，ｄ，Ｊ＝７．２Ｈｚ）、２．１１−２．４（４Ｈ，ｍ）、２．７４（１Ｈ，ｓｅｐ）、３．９−４．０（１Ｈ，ｍ）、４．１９（１Ｈ，ｄ，Ｊ＝１０．４Ｈｚ）、７．１９（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ）、７．２５（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ） The compound of the present invention (ii-57)

¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 1.22 (3H, d, J = 7.2 Hz), 1.31 (3H, d, J = 7.2 Hz), 2.11 2.4 (4H, m), 2.74 (1 H, sep), 3.9-4.0 (1 H, m), 4.19 (1 H, d, J = 10.4 Hz), 7.19 ( 2H, d, J = 9.2 Hz), 7.25 (2H, d, J = 9.2 Hz)

融点 １３８．３℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：１．２８（３Ｈ，ｔ，Ｊ＝７．５Ｈｚ）、２．５−２．６（１Ｈ，ｍ）、２．７−２．８（１Ｈ，ｍ）、４．１９（１Ｈ，ｄ，Ｊ＝１１．０Ｈｚ）、４．４−４．５（１Ｈ，ｍ）、４．７−４．８（１Ｈ，ｍ）、４．９−５．０（１Ｈ，ｍ）、６．８６（２Ｈ，ｄ，Ｊ＝８．９Ｈｚ）、７．２３（２Ｈ，ｄ，Ｊ＝８．９Ｈｚ） Compound (iii-39) of the present invention

Melting point 138.3 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 1.28 (3H, t, J = 7.5 Hz), 2.5-2.6 (1H, m), 2.7-2. 8 (1H, m), 4.19 (1H, d, J = 11.0 Hz), 4.4-4.5 (1H, m), 4.7-4.8 (1H, m), 4. 9-5.0 (1H, m), 6.86 (2H, d, J = 8.9 Hz), 7.23 (2H, d, J = 8.9 Hz)

融点 １７３．４℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．０９（１．８Ｈ，ｓ）、２．１２（１．２Ｈ，ｓ）、２．０−２．５（３．４Ｈ，ｍ）、２．８−２．９（０．６Ｈ，ｍ）、４．０５（０．６Ｈ，ｄ，Ｊ＝９．８Ｈｚ）、４．６−４．７（１．４Ｈ，ｍ）、６．９６（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ）、７．２０（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ）、７．５７（０．４Ｈ，ｓ）、７．６２（０．６Ｈ，ｓ） Compound of the present invention (vii-21)

Melting point 173.4 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.09 (1.8 H, s), 2.12 (1.2 H, s), 2.0-2.5 (3.4 H, m), 2.8-2.9 (0.6 H, m), 4.05 (0.6 H, d, J = 9.8 Hz), 4.6-4.7 (1.4 H, m), 6.96 (2H, d, J = 9.2 Hz), 7.20 (2H, d, J = 9.2 Hz), 7.57 (0.4 H, s), 7.62 (0.6 H, s) )

融点 １１７．０℃
¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）、δ（ｐｐｍ）：２．０６（２．１Ｈ，ｓ）、２．１０（０．９Ｈ，ｓ）、２．０−２．５（３．７Ｈ，ｍ）、２．７−２．８（０．３Ｈ，ｍ）、３．９０（３Ｈ，ｓ）、４．０３（０．３Ｈ，ｄ，Ｊ＝９．８Ｈｚ）、４．５−４．６（１．７Ｈ，ｍ）、６．９４（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ）、７．２０（２Ｈ，ｄ，Ｊ＝９．２Ｈｚ） Compound of the present invention (ix-21)

Melting point 117.0 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 2.06 (2.1 H, s), 2.10 (0.9 H, s), 2.0-2.5 (3.7 H, m), 2.7-2.8 (0.3H, m), 3.90 (3H, s), 4.03 (0.3H, d, J = 9.8 Hz), 4.5-4. 6 (1.7 H, m), 6.94 (2 H, d, J = 9.2 Hz), 7.20 (2 H, d, J = 9.2 Hz)

Next, formulation examples are shown. In addition, a part represents a weight part.
Formulation Example 1
Compounds of the present invention (i-1) to (i-72), (ii-1) to (ii-72), (iii-1) to (iii-72), (iv-1) to (iv-72) , (V-1) to (v-72), (vi-1) to (vi-72), (vii-1) to (vii-72), (viii-1) to (viii-72), ( 50 parts of each of ix-1) to (ix-72) and (x-1) to (x-72), 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed. Thus, each wettable powder is obtained.

Formulation Example 2
Compounds of the present invention (i-1) to (i-72), (ii-1) to (ii-72), (iii-1) to (iii-72), (iv-1) to (iv-72) , (V-1) to (v-72), (vi-1) to (vi-72), (vii-1) to (vii-72), (viii-1) to (viii-72), ( An aqueous solution containing 20 parts of each of ix-1) to (ix-72) and (x-1) to (x-72) and 1.5 parts of sorbitan trioleate and 2 parts of polyvinyl alcohol 28. After mixing with 5 parts and finely pulverizing by a wet pulverization method, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate was added thereto, and 10 parts of propylene glycol was further added. And stirring to mix to obtain each flowable preparation.

Formulation Example 3
Compounds of the present invention (i-1) to (i-72), (ii-1) to (ii-72), (iii-1) to (iii-72), (iv-1) to (iv-72) , (V-1) to (v-72), (vi-1) to (vi-72), (vii-1) to (vii-72), (viii-1) to (viii-72), ( Each part of ix-1) to (ix-72) and (x-1) to (x-72), 88 parts of kaolin clay and 10 parts of talc are pulverized and mixed well to obtain each powder.

Formulation Example 4
Compounds of the present invention (i-1) to (i-72), (ii-1) to (ii-72), (iii-1) to (iii-72), (iv-1) to (iv-72) , (V-1) to (v-72), (vi-1) to (vi-72), (vii-1) to (vii-72), (viii-1) to (viii-72), ( ix-1) to (ix-72) and (x-1) to (x-72), 5 parts each, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene. Each emulsion is obtained by mixing well.

Formulation Example 5
Compounds of the present invention (i-1) to (i-72), (ii-1) to (ii-72), (iii-1) to (iii-72), (iv-1) to (iv-72) , (V-1) to (v-72), (vi-1) to (vi-72), (vii-1) to (vii-72), (viii-1) to (viii-72), ( ix-1) to (ix-72) and 2 parts each of (x-1) to (x-72), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay After thoroughly pulverizing and mixing, each granule is obtained by adding water and kneading and granulating and drying.

Formulation Example 6
Compounds of the present invention (i-1) to (i-72), (ii-1) to (ii-72), (iii-1) to (iii-72), (iv-1) to (iv-72) , (V-1) to (v-72), (vi-1) to (vi-72), (vii-1) to (vii-72), (viii-1) to (viii-72), ( ix-1) to (ix-72) and 10 parts each of (x-1) to (x-72), 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water are mixed. Each formulation is obtained by finely pulverizing by a wet pulverization method.

（以下、比較物（Ａ）と記す。）を供試した。 Next, Test Examples show that the compounds of the present invention are effective for controlling plant diseases. The control effect was evaluated by observing the area of the lesion on the test plant with the naked eye and comparing the area of the lesion in the untreated area with the area of the lesion in the drug-treated area.
In order to show the effect of the present invention more clearly, as a comparative control, J.M. Chem. Research (M), 1981, pp. The following products (11) and (12) described in 135-158,

(Hereinafter referred to as a comparative product (A)) was used.

A plastic pot was filled with sandy loam, cucumber (Sagamihanjiro) was sown and grown in a greenhouse for 10 days. The compound of the present invention (i-21), (i-39), (i-57), (ii-21), (ii-39), (ii-57), (iii) obtained according to Formulation Example 6 -21), (iii-39), (iii-557), (iv-57), (v-21), (vi-21), (vii-21), (viii-21) and (ix-21) Each of the test chemical solutions obtained by diluting the formulation of (1) with water to 500 ppm was sprayed on the foliage so that it sufficiently adhered to the cucumber cotyledon surface. After the chemical solution was air-dried, a PDA medium containing spores of gray mold was placed on the cotyledon surface of cucumber. The cucumber was allowed to stand at 12 ° C. and high humidity for 5 days, and then the control effect was investigated. As a result, the lesion area on the plant on which the compound of the present invention was tested was 10% or less of the lesion area in the untreated section. On the other hand, the lesion area of the treatment group of the test chemical solution prepared in the same manner as described above using the comparative product (A) was similar to that of the non-treatment group.

Claims (7)

Formula (I)

[Where,
L ¹ represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 haloalkoxy group or a cyano group,
L ² represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkyl group, a C1-C3 haloalkoxy group or a cyano group,
R ¹ represents a hydrogen atom or a C1-C5 alkyl group,
Y represents an oxygen atom, a sulfur atom or a methylene group,
-X-Y-Z- is _{-C (= O) -CH 2 -CH} 2 - ^{group, -C (= NOR 2) -CH} 2 -CH 2 - _{group, -CH 2 -CH 2 -C (=} O ) - _{group, -CH 2 -CH 2 -C (=} NOR 2) - group, -C (= O) -O- CH 2 - _{group, -CH 2 -O-C (=} O) - group, -C _{(= O) -S-CH 2} - group or a _{-CH 2 -S-C (= O} ) - group, wherein
R ² represents a hydrogen atom or a C1-C3 alkyl group. ]
An arylpyrazoline compound represented by: The arylpyrazoline compound according to claim 1, wherein L ² is a hydrogen atom. The arylpyrazoline compound according to claim 1 or 2, wherein L ¹ is a chlorine atom, a bromine atom or a methyl group. The arylpyrazoline compound according to any one of claims 1 to 3, wherein R ¹ is a hydrogen atom, a methyl group, an ethyl group or an isopropyl group. The arylpyrazoline compound according to claim 1, wherein —X—Y—Z— represents a —C (═NOR ² ) —CH ₂ —CH ₂ — group, and R ² is a hydrogen atom.   A plant disease control agent comprising the arylpyrazoline compound according to any one of claims 1 to 5 as an active ingredient. A method for controlling plant diseases, which comprises applying an effective amount of the arylpyrazoline compound according to any one of claims 1 to 5 to a plant or soil in which the plant grows.