JP2021185128A - Soil disease control agent - Google Patents

Abstract

To provide a soil disease control agent and a soil disease control method.SOLUTION: A soil disease control agent contains a compound represented by formula (1) as an active ingredient. (In the formula, X1 to X4 each independently represent H, F, Cl or the like; Xa is a group represented by formula (2), (3), (4), or (5); J represents O or S; Q represents O, S or the like; A represents thiol or the like, Aa represents piperidine-1-yl or the like; Qb represents O, S or the like; Ab represents H, methoxycarbonyl or the like; Z represents H, a halogen atom or the like; m represents an integer of 1-3.)SELECTED DRAWING: None

Description

The present invention relates to a soil disease control agent. More specifically, the present invention relates to a soil disease control agent and a soil disease control method.

Plants have evolved a mechanism of physical and chemical resistance to attack by external pathogens. The physical resistance mechanism is, for example, a coating such as a cuticle layer made of wax or the like, or a cell wall, which serves as a barrier to entry of pathogens. On the other hand, the chemical resistance mechanism is a system that inhibits the growth of pathogens, and examples thereof include resistance factors that are congenitally accumulated in plants and resistance factors that are induced to be biosynthesized and accumulated. Be done.

In recent years, in order to protect plants from disease stress, attempts have been made to improve the resistance of plants by activating the chemical resistance mechanism by administering an external drug. Such agents can be called resistance inducers, and various inducers have been studied so far. For example, it has been clarified that treatment of tobacco with salicylic acid or acetylsalicylic acid induces resistance to tobacco mosaic virus (TMV) (see Non-Patent Document 1).

Inducing plant resistance in this way to protect plants from phytopathogenic or phytopathogenic infections is very useful in growing healthy plants and securing food. However, the resistance of plants to soil diseases such as withering and root rot caused by Fusarium, Pythium and Rhizoctonia inhabiting the soil, and yellowing and wilting of the above-ground parts. There is no known method of controlling the disease by inducing sex.

On the other hand, soil diseases are difficult to control diseases, and control methods by soil disinfection are common. However, these control methods require a great deal of labor and involve dangerous work. Furthermore, the pesticides currently used in soil disinfection have a large environmental load. Therefore, if a control method by spraying treatment or irrigation treatment is put into practical use, it will be highly useful as a simple and safe method.

It is disclosed that the chlorine-substituted isonicotinic acid derivative has a plant disease control effect (Patent Documents 1 to 5). Further, regarding the fluorine-substituted isonicotinic acid derivative, a similar plant disease control agent is disclosed (Patent Documents 6 to 10), but there is no specific description regarding the soil disease control agent of the present invention.

Japanese Unexamined Patent Publication No. 63-93766 Japanese Unexamined Patent Publication No. 1-283270 Japanese Unexamined Patent Publication No. 9-165374 Japanese Unexamined Patent Publication No. 10-95772 International Publication No. 2005-68430 International Publication No. 2008-098928 International Publication No. 96-03047 Japanese Unexamined Patent Publication No. 1-272569 International Publication No. 2009-11305 International Publication No. 2014-124988

R.F.White, Acetylsalicylic acid (aspirin) induces resistance to tobacco mosaic virus in tobacco, Virology, 99, 410 (1979)

An object of the present invention is to provide a soil disease control agent and a soil disease control method.

As a result of detailed examination of the fluorine-substituted pyridine compound, the present inventor has found a compound that exhibits a high control effect on soil diseases by exhibiting resistance-inducing activity without directly exhibiting antibacterial activity against pathogenic bacteria. Completed the invention.

The present invention includes the following aspects.
[1] A soil disease control agent comprising a compound represented by the following formula (1) as an active ingredient.

［式（１）中、Ｘ^１及びＸ^４は同一であっても異なっていてもよく、水素原子、フッ素原子、塩素原子又はトリフルオロメチル基を示すが、Ｘ^１及びＸ^４のいずれか１つはフッ素原子又はトリフルオロメチル基を示し、Ｘ^２及びＸ^３は同一であっても異なっていてもよく、水素原子、フッ素原子、塩素原子又はメチル基であり、但し、Ｘ^１、Ｘ^２及びＸ^４のいずれか１つがフッ素原子を示すとき、他の２つのいずれか１つは水素原子を示さず、
Ｘ^ａは下記式（２）、（３）、（４）又は（５）で示される基であり、

式（２）中、Ｊは酸素原子又は硫黄原子を示し、
Ａは、
下記Ｃ群の基、チオール基、メトキシカルボニル基及びＮ−ｔｅｒｔ−ブトキシカルボニルアミノ基からなる群から選ばれる１〜３個の基で置換されていてもよい炭素数１〜１２のアルキル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数２〜８のアルケニル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数２〜８のアルキニル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜８のアルキルカルボニル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜４のアルキルオキシ基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜８のアルキルスルホニル基、
下記Ｄ群の基、ベンジル基、フェニル基及びフェノキシ基からなる群から選ばれる１〜４個の基で置換されていてもよいフェニルカルボニル基、
下記Ｄ群の基から選ばれる１〜４個の基で置換されていてもよいフェニルスルホニル基、
下記Ｄ群の基、フェノキシ基及びベンジル基からなる群から選ばれる１〜５個の基で置換されていてもよいフェニル基、
５，６，７，８−テトラヒドロナフチル基、
ナフチル基、
下記Ｄ群の基から選ばれる１〜４個の基で置換されていてもよいヘテロ環基（ここで、ヘテロ環基は下記Ｅ群から選ばれる基である。）、又は
下記式（２Ａ）［式（２Ａ）中、Ｘ^１、Ｘ^２、Ｘ^３及びＸ^４は前記式（１）における定義に同じである。］で示される基であり、

Ａが前記式（２Ａ）で示される基である場合、Ｑは、式：−Ｏ−（ＣＨ_２）_ｎ−Ｏ−で示される２価の基、式：−ＮＨ−（ＣＨ_２）_ｎ−Ｏ−で示される２価の基、式：−ＮＨ−（ＣＨ_２）_ｎ−ＮＨ−で示される２価の基、式：−Ｏ−ＣＨ_２−ＣＨ＝ＣＨ−ＣＨ_２−Ｏ−で示される２価の基、式：−ＮＨ−ＣＨ_２−ＣＨ＝ＣＨ−ＣＨ_２−Ｏ−で示される２価の基、式：−ＮＨ−ＣＨ_２−ＣＨ＝ＣＨ−ＣＨ_２−ＮＨ−で示される２価の基、シクロヘキサン−１，４−ジイルジオキシ基、シクロヘキサン−１，４−ジイルジアミノ基、式：−ＮＨ−（シクロヘキサン−１，４−ジイル）−Ｏ−で示される２価の基、１，３−フェニレンジアミノ基、１，４−フェニレンジアミノ基、１，４−フェニレンジオキシ基、式：−ＮＨ−（１，４−フェニレン）−Ｏ−で示される２価の基、又は下記式（２Ｂ）［式（２Ｂ）中、Ｇは、酸素原子、硫黄原子又は式：−ＳＯ_２−で示される２価の基である。］で示される２価の基であり（ここで、ｎは２〜８の整数を示す。）、

Ａが前記式（２Ａ）で示される基でない場合、Ｑは、酸素原子、硫黄原子、式：−ＮＨ−で示される２価の基、又は式：−Ｎ（ＣＨ_３）−で示される２価の基であり、
式（３）中、Ａａは、ピペリジン−１−イル基、１−メチル−１−１Ｈ−ピロール−２−イル基、モルホリン−４−イル基、インドリン−１−イル基、ベンゾイソチアゾール−３（２Ｈ）−オン−１，１−ジオキシド−２−イル基、ピペラジン−１−イル基、アゼチジン−１−イル基、２，５−ジオキソピロリジン−１−イル基、３−オキソイソチアゾール−２（３Ｈ）−イル基、ベンゾ［ｄ］イソチアゾール−２（３Ｈ）−イル基、１，１−ジオキソ−３−オキソベンゾ［ｄ］イソチアゾール−２（３Ｈ）−イル基、５，６−ジヒドロ−４Ｈ−１，３−オキサジン−２−イル基、１Ｈ−ピロール−２−イル基又はイソインドリン−２−イル基を示し、
式（４）中、Ｑｂは、酸素原子、硫黄原子、式：−ＮＨ−で示される２価の基又は式：−Ｎ（ＣＨ_３）−で示される２価の基を示し、
Ａｂは、水素原子、
下記Ｃ群の基、メトキシカルボニル基及びＮ−ｔｅｒｔ−ブトキシカルボニルアミノ基からなる群から選ばれる１〜３個の基で置換されていてもよい炭素数１〜１０のアルキル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数２〜８のアルケニル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数２〜８のアルキニル基、
下記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜８のアルキルカルボニル基、
フェニルカルボニル基、又は
下記Ｄ群の基から選ばれる１〜４個の基で置換されていてもよいヘテロ環基（ここで、ヘテロ環基は下記Ｅ群から選ばれる基である。）を示し、
式（５）中、ｍは１〜３の整数を示し、Ｚは水素原子、ハロゲン原子又はメチル基を示し、
Ｃ群は、ハロゲン原子、水酸基、アミノ基、５−メチル−１，３−ジオキソール−２−オン−４−イル基、フェニルカルボニル基、下記Ｄ群の基から選ばれる１〜３個の基で置換されていてもよいピリジル基、及び下記Ｄ群の基から選ばれる１〜４個の基で置換されていてもよいフェニル基からなる群であり、
Ｄ群は、ハロゲン原子、水酸基、アミノ基、メチルチオ基、１〜３個のハロゲン原子により置換されていてもよい炭素数１〜４のアルキル基、１〜３個のハロゲン原子により置換されていてもよい炭素数１〜４のアルキルオキシ基、炭素数１〜４のアルキルカルボニル基、メトキシカルボニル基、エトキシカルボニル基、ベンジルアミノカルボニル基、アセトキシ基、ニトロ基、及びシアノ基からなる群であり、
Ｅ群は、ピリジル基、チアゾリル基、ピラジニル基、ピリダジニル基、イソチアゾリジル基、イソキサゾリル基、ピリミジニル基、ベンズイミダゾリル基、チエニル基、フラニル基、ベンゾオキサニル基、２，３−ジヒドロベンゾ［ｂ］［１，４］ジオキシン−６−イル基、ジヒドロチアゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基、ベンゾイソチアゾール−３（２Ｈ）−オン−１，１−ジオキジニル基、ジベンゾフラニル基、イソチアゾリル基、及びトリアゾリル基からなる群である。］
［２］前記式（１）中、Ｘ^１、Ｘ^２、Ｘ^３及びＸ^４が水素原子又はフッ素原子であることを特徴とする、［１］に記載の土壌病害防除剤。
［３］前記式（１）中、Ｘ^１及びＸ^４がフッ素原子を示し、Ｘ^２又はＸ^３が水素原子であることを特徴とする、［１］又は［２］に記載の土壌病害防除剤。
［４］前記式（１）中、Ｘ^１及びＸ^４がフッ素原子を示し、Ｘ^２及びＸ^３が水素原子であることを特徴とする、［１］〜［３］のいずれかに記載の土壌病害防除剤。
［５］前記式（２）中、Ｊが酸素原子であることを特徴とする、［１］〜［４］のいずれかに記載の土壌病害防除剤。
［６］前記式（２）中、Ｑが式：−ＮＨ−で示される２価の基であることを特徴とする、［１］〜［５］のいずれかに記載の土壌病害防除剤。
［７］前記式（２）中、Ｑが酸素原子であることを特徴とする、［１］〜［５］のいずれかに記載の土壌病害防除剤。
［８］前記式（２）中、Ａが
前記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜１２のアルキル基、
前記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数２〜８のアルケニル基、
前記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数２〜８のアルキニル基、
前記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜８のアルキルカルボニル基、
前記Ｃ群の基から選ばれる１〜３個の基で置換されていてもよい炭素数１〜４のアルキルオキシ基、
前記Ｄ群の基、ベンジル基、フェニル基及びフェノキシ基からなる群から選ばれる１〜４個の基で置換されていてもよいフェニルカルボニル基、
前記Ｄ群の基から選ばれる１〜４個の基で置換されていてもよいフェニルスルホニル基、
前記Ｄ群の基、フェノキシ基及びベンジル基からなる群から選ばれる１〜５個の基で置換されていてもよいフェニル基、又は
前記Ｄ群の基から選ばれる１〜４個の基で置換されていてもよいヘテロ環基（ここで、ヘテロ環基は前記Ｅ群から選ばれる基である。）であることを特徴とする、［１］〜［７］のいずれか一項に記載の土壌病害防除剤。
［９］［１］〜［８］のいずれかに記載の土壌病害防除剤を、植物体又は種子と接触させるか、あるいは栽培床に含有させることを特徴とする、土壌病害防除方法。

[In the formula (1), X ¹ and X ⁴ may be the same or different, and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, but any ^one of X ^{1 and X 4 1} One indicates a fluorine atom or a trifluoromethyl group, and X ² and X ³ may be the same or different, and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group, except that X ¹ and X ^2. and when referring to any one of fluorine atom of X ^4, any one other two showed no hydrogen atom,
X ^{a is a group} represented by the following formula (2), (3), (4) or (5).

In formula (2), J represents an oxygen atom or a sulfur atom.
A is
An alkyl group having 1 to 12 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the group C below, a thiol group, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group.
An alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
An alkynyl group having 2 to 8 carbon atoms, which may be substituted with 1 to 3 groups selected from the groups of the C group below.
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the following C group groups.
An alkylsulfonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D below, a benzyl group, a phenyl group and a phenoxy group,
A phenylsulfonyl group which may be substituted with 1 to 4 groups selected from the groups of Group D below,
A phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the group D below, a phenoxy group and a benzyl group,
5,6,7,8-tetrahydronaphthyl group,
Naphthalene group,
A heterocyclic group may be substituted with 1 to 4 groups selected from the groups of the following group D (here, the heterocyclic group is a group selected from the group E below), or the following formula (2A). [In the formula (2A), X ¹ , X ² , X ³ and X ⁴ are the same as the definitions in the formula (1). ] Is the group indicated by

When A is the group represented by the above formula (2A), Q is a _{divalent group represented by the formula: -O- (CH 2} ) _n- O-, and the formula: -NH- (CH ₂ ) _n-. Divalent group represented by O-, formula: -NH- (CH ₂ ) _{divalent group represented by n-} NH-, formula: -O-CH ₂ -CH = CH-CH _2- O- A divalent group represented by the formula: -NH-CH ₂ -CH = CH-CH _2- O-, a divalent group represented by the formula: -NH-CH ₂ -CH = CH-CH _2- NH- Divalent group, cyclohexane-1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, formula: -NH- (cyclohexane-1,4-diyl) -O-, divalent group, 1 , 3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: divalent group represented by -NH- (1,4-phenylene) -O-, or the following formula (2B) [in the formula (2B), G is an oxygen atom, a sulfur atom or the formula: -SO ₂ - is a divalent group represented by. ] Is a divalent group (where n represents an integer of 2 to 8).

If A is not the group represented by the formula (2A), Q is an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH-, or 2 represented by the formula: -N (CH ₃ )-. It is the basis of the price,
In formula (3), Aa is a piperidin-1-yl group, 1-methyl-1-1H-pyrrole-2-yl group, morpholine-4-yl group, indolin-1-yl group, benzoisothiazole-3. (2H) -On-1,1-dioxide-2-yl group, piperazine-1-yl group, azetidine-1-yl group, 2,5-dioxopyrrolidine-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazole-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazole-2 (3H) -yl group, 5,6- Dihydro-4H-1,3-oxadin-2-yl group, 1H-pyrrol-2-yl group or isothiazole-2-yl group,
In formula (4), Qb represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH- or a divalent group represented by the formula: -N (CH ₃ )-.
Ab is a hydrogen atom,
An alkyl group having 1 to 10 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the group C below, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group,
An alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
An alkynyl group having 2 to 8 carbon atoms, which may be substituted with 1 to 3 groups selected from the groups of the C group below.
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
A heterocyclic group which may be substituted with a phenylcarbonyl group or 1 to 4 groups selected from the groups of the following group D (here, the heterocyclic group is a group selected from the group E below) is shown. ,
In formula (5), m represents an integer of 1 to 3 and Z represents a hydrogen atom, a halogen atom or a methyl group.
Group C is a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, and 1 to 3 groups selected from the following groups of the D group. It is a group consisting of a pyridyl group which may be substituted and a phenyl group which may be substituted with 1 to 4 groups selected from the groups of the D group below.
Group D is substituted with a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, and 1 to 3 halogen atoms. It is a group consisting of an alkyloxy group having 1 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, a nitro group, and a cyano group.
Group E includes pyridyl group, thiazolyl group, pyrazinyl group, pyridazinyl group, isothiazolidyl group, isoxazolyl group, pyrimidinyl group, benzimidazolyl group, thienyl group, furanyl group, benzoxanyl group, 2,3-dihydrobenzo [b] [1, 4] Dioxin-6-yl group, dihydrothiazolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoisothiazole-3 (2H) -one-1,1-diokidinyl group, dibenzofuranyl group, isothiazolyl group, And a group consisting of a triazolyl group. ]
[2] The soil disease control agent according to [1], ^{wherein X 1} , X ² , X ³ and X ^{4 in the} above formula (1) are hydrogen atoms or fluorine atoms.
[3] The soil disease control according to [1] or [2], ^{wherein X 1} and X ⁴ represent a fluorine atom and X ² or X ³ is a hydrogen atom in the above formula (1). Agent.
[4] The description according to any one of [1] to [3], ^{wherein X 1} and X ⁴ represent a fluorine atom and X ² and X ³ are hydrogen atoms in the above formula (1). Soil disease control agent.
[5] The soil disease control agent according to any one of [1] to [4], wherein J is an oxygen atom in the above formula (2).
[6] The soil disease control agent according to any one of [1] to [5], wherein Q is a divalent group represented by the formula: -NH- in the above formula (2).
[7] The soil disease control agent according to any one of [1] to [5], wherein Q is an oxygen atom in the above formula (2).
[8] In the formula (2), an alkyl group having 1 to 12 carbon atoms, wherein A may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkynyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D, the benzyl group, the phenyl group and the phenoxy group.
A phenylsulfonyl group which may be substituted with 1 to 4 groups selected from the groups of the D group.
Substituted with 1 to 5 groups selected from the group consisting of the group D, phenoxy group and benzyl group, or 1 to 4 groups selected from the group D. The above-mentioned item 1 in any one of [1] to [7], wherein the heterocyclic group may be a heterocyclic group (here, the heterocyclic group is a group selected from the group E). Soil disease control agent.
[9] A soil disease control method, which comprises contacting the soil disease control agent according to any one of [1] to [8] with a plant or seed, or incorporating the soil disease control agent into a cultivation bed.

According to the present invention, it is possible to provide a soil disease control agent and a soil disease control method. The soil disease control agent of the present invention has excellent resistance-inducing activity and is useful for controlling soil diseases.

式（１）中、Ｘ^１及びＸ^４は同一であっても異なっていてもよく、水素原子、フッ素原子、塩素原子又はトリフルオロメチル基を示すが、Ｘ^１及びＸ^４のいずれか１つはフッ素原子又はトリフルオロメチル基を示す。また、Ｘ^２及びＸ^３は同一であっても異なっていてもよく、水素原子、フッ素原子、塩素原子又はメチル基である。但し、式（１）中、Ｘ^１、Ｘ^２及びＸ^４のいずれか１つがフッ素原子を示すとき、他の２つのいずれか１つは水素原子を示さない。 In one embodiment, the present invention provides a soil disease control agent containing a compound represented by the following formula (1) as an active ingredient. Further, in one embodiment, the present invention provides a compound represented by the following formula (1).

In formula (1), X ¹ and X ⁴ may be the same or different, indicating a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, but any ^one of X ^{1 and X 4.} Indicates a fluorine atom or a trifluoromethyl group. Further, X ² and X ³ may be the same or different, and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group. However, in the formula (1), when ^{any one of X 1} , X ² and X ⁴ shows a fluorine atom, any one of the other two does not show a hydrogen atom.

In the formula (1), X ¹ and X ⁴ are preferably fluorine atoms, and X ² and X ³ are preferably hydrogen atoms or fluorine atoms.

In the formula (1), X ^{a is a group} represented by the following formulas (2), (3), (4) or (5).

In formula (2), J represents an oxygen atom or a sulfur atom. Further, in the formula (2), A may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group. A good alkyl group having 1 to 12 carbon atoms; an alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the group C group below; 1 to 1 selected from the groups C group below. Alkinyl group having 2 to 8 carbon atoms which may be substituted with 3 groups; alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group. An alkyloxy group having 1 to 4 carbon atoms may be substituted with 1 to 3 groups selected from the groups of the following C group; and substituted with 1 to 3 groups selected from the groups of the following C group. An alkylsulfonyl group having 1 to 8 carbon atoms may be substituted; a phenylcarbonyl group may be substituted with 1 to 4 groups selected from the group consisting of the group D below, a benzyl group, a phenyl group and a phenoxy group; A phenylsulfonyl group which may be substituted with 1 to 4 groups selected from the group D below; substituted with 1 to 5 groups selected from the group consisting of a group D, a phenoxy group and a benzyl group below. Phyl group which may be; 5,6,7,8-tetrahydronaphthyl group; naphthyl group; a heterocyclic group which may be substituted with 1 to 4 groups selected from the groups of the following D group (here). , a heterocyclic group is a group selected from the following group E);. or in the following formula (2A) [formula ^{(2A), X 1, X} 2, X 3 and ^{X 4} are as defined in the formula (1) It is the same. ] Is the group indicated by.

In formula (2), when A is the group represented by formula (2A), Q is a _{divalent group represented by formula: -O- (CH 2} ) _n- O-, formula: -NH- ( CH ₂ ) _{Divalent group represented by n-} O-, formula: -NH- (CH ₂ ) _{Divalent group represented by n-} NH-, formula: -O-CH ₂ -CH = CH-CH ₂ a divalent group represented by -O-, the _{formula: -NH-CH 2 -CH = CH} -CH 2 -O- divalent group represented the _{formula: -NH-CH 2 -CH = CH} -CH 2 A divalent group represented by -NH-, a cyclohexane-1,4-diyldioxy group, a cyclohexane-1,4-diyldiamino group, and a formula: -NH- (cyclohexane-1,4-diyl) -O-. Group of valence, 1,3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: -NH- (1,4-phenylene) -O- group, or the following formulas (2B) [formula (2B), G is an oxygen atom, a sulfur atom or the formula: -SO ₂ - is a divalent group represented by. ] Is a divalent group (where n represents an integer of 2 to 8).

In formula (2), if A is not the group represented by the formula (2A), Q is an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH-, or the formula: -N (CH _3). )-It is a divalent group indicated by-.

In formula (3), Aa is a piperidin-1-yl group, 1-methyl-1-1H-pyrrole-2-yl group, morpholine-4-yl group, indolin-1-yl group, benzoisothiazole-3. (2H) -On-1,1-dioxide-2-yl group, piperazine-1-yl group, azetidine-1-yl group, 2,5-dioxopyrrolidine-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazole-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazole-2 (3H) -yl group, 5,6- It shows a dihydro-4H-1,3-oxadin-2-yl group, a 1H-pyrrol-2-yl group or an isoindrin-2-yl group.

In formula (4), Qb represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH- or a divalent group represented by the formula: -N (CH ₃ )-. In formula (4), Ab is a hydrogen atom; the group C below,
An alkyl group having 1 to 10 carbon atoms may be substituted with 1 to 3 groups selected from the group consisting of a methoxycarbonyl group and an N-tert-butoxycarbonylamino group; 1 to selected from the following group C group. An alkenyl group having 2 to 8 carbon atoms which may be substituted with 3 groups; an alkynyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group below; An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the group C group below; a phenylcarbonyl group; or 1 to 4 groups selected from the groups D group below. A heterocyclic group which may be substituted with (here, the heterocyclic group is a group selected from the following group E) is shown.

In formula (5), m represents an integer of 1 to 3 and Z represents a hydrogen atom, a halogen atom or a methyl group.

Group C is a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, and 1 to 3 groups selected from the following groups of the D group. It is a group consisting of a pyridyl group which may be substituted and a phenyl group which may be substituted with 1 to 4 groups selected from the groups of the D group below.

Group D is substituted with a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, and 1 to 3 halogen atoms. It is a group consisting of an alkyloxy group having 1 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, a nitro group, and a cyano group.

Group E includes pyridyl group, thiazolyl group, pyrazinyl group, pyridazinyl group, isothiazolidyl group, isoxazolyl group, pyrimidinyl group, benzimidazolyl group, thienyl group, furanyl group, benzoxanyl group, 2,3-dihydrobenzo [b] [1, 4] Dioxin-6-yl group, dihydrothiazolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoisothiazole-3 (2H) -one-1,1-diokidinyl group, dibenzofuranyl group, isothiazolyl group, And a group consisting of a triazolyl group.

In the present embodiment, the alkyl group having 1 to 12 carbon atoms means a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-octyl group and a cyclo. Examples thereof include a propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclohexyl group and an n-. Examples include octyl groups.

The alkenyl group having 2 to 8 carbon atoms means a linear, branched or cyclic alkenyl group having one or more double bonds at any position of the alkyl group having 2 to 8 carbon atoms. Examples of the alkenyl group having 2 to 8 carbon atoms include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, an isopropenyl group, a 3-butenyl group, a 4-pentenyl group and a 5-hexenyl group. Examples thereof include a 1-cyclohexenyl group, and a 2-propenyl group is preferable.

The alkynyl group having 2 to 8 carbon atoms means a linear, branched or cyclic alkynyl group having one or more triple bonds at arbitrary positions of the alkyl group having 2 to 8 carbon atoms. Examples of the alkynyl group having 2 to 8 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 3-butynyl group, a cyclopropylethynyl group and the like, and a 2-propynyl group is preferable.

The alkyloxy group having 1 to 4 carbon atoms means a group consisting of oxygen atoms substituted with linear, branched or cyclic alkyl groups having 1 to 4 carbon atoms. Examples of the alkyloxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropyloxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group and a cyclopropyloxy group. Examples thereof include a group, a cyclobutyloxy group and the like, and a methoxy group is preferable.

The alkylcarbonyl group having 1 to 8 carbon atoms means a carbonyl group substituted with a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. Examples of the alkylcarbonyl group having 1 to 8 carbon atoms include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, an n-butylcarbonyl group, a sec-butylcarbonyl group, an isobutylcarbonyl group, and a tert-. Examples thereof include a butylcarbonyl group, an n-octylcarbonyl group, a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a cyclohexylcarbonyl group and the like.

The alkylsulfonyl group having 1 to 8 carbon atoms means a sulfonyl group substituted with a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. Examples of the alkylsulfonyl group having 1 to 8 carbon atoms include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, an n-butylsulfonyl group, a sec-butylsulfonyl group, an isobutylsulfonyl group, and tert-. Examples thereof include a butylsulfonyl group, an n-octylsulfonyl group, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, and a cyclohexylsulfonyl group.

Examples of the 5,6,7,8-tetrahydronaphthyl group include 5,6,7,8-tetrahydronaphthalene-1-yl group, 5,6,7,8-tetrahydronaphthalene-2-yl group and the like. ..

The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The divalent group represented by the formula: -NH- (cyclohexane-1,4-diyl) -O- includes the group represented by the formula: -NH- and the oxygen atom at the 1st and 4th positions of the cyclohexane ring, respectively. It is a bonded divalent group.

The divalent group represented by the formula: -NH- (1,4-phenylene) -O- is a group represented by the formula: -NH- and an oxygen atom bonded to the 1-position and the 4-position of the benzene ring, respectively. It is a divalent group.

In the present specification, unless otherwise specified, the symbol "-" for bonding an atom and / or a group in the structural formula indicates a single bond, and "=" indicates a double bond. For example, in the equation (1), all the symbols "-" indicate a single bond, and all the symbols "=" indicate a double bond. Further, for example, in the formula (2), Q is _{a divalent group represented by the formula: -O- (CH 2} ) _n- O-, and the divalent group represented by the formula: -NH- (CH ₂ ) _n- O-. Group, formula: -NH- (CH ₂ ) _{divalent group represented by n-} NH-, formula: -O-CH ₂ -CH = CH-CH ₂ -valent group represented by -O-, formula : -NH-CH ₂ -CH = CH-CH ₂ -valent group represented by -O-, formula: -NH-CH ₂ -CH = CH-CH ₂ -valent group represented by -NH-, cyclohexane -1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, formula: -NH- (cyclohexane-1,4-diyl) -O-, divalent group, 1,3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: divalent group represented by -NH- (1,4-phenylene) -O-, or divalent group represented by formula (2B). In the case of groups of, all the symbols "-" in these groups indicate a single bond, and all the symbols "=" indicate a double bond.

In Group D, the alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, sec. -Butyl group, isobutyl group, tert-butyl group, trifluoromethyl group, chloromethyl group, methoxy group, ethoxy group and the like can be mentioned.

In Group D, the alkyloxy groups having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms are, for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group and n-butyloxy. Examples thereof include a group, a sec-butyloxy group, an isobutyloxy group, a tert-butyloxy group, a trifluoromethyloxy group, a chloromethyloxy group and the like.

In formula (2), a more preferred embodiment of A is an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the group C group; 1 selected from the group C group. An alkenyl group having 2-3 carbon atoms which may be substituted with ~ 3 groups; an alkynyl group having 2-3 carbon atoms which may be substituted with 1-3 groups selected from the groups of Group C, Alternatively, it is a phenyl group which may be substituted with 1 to 3 groups selected from the groups of the D group.

In formula (2), a more preferred embodiment of J is an oxygen atom.

In formula (2), a more preferred embodiment of Q is an oxygen atom or a divalent group represented by the formula: -NH-.

The compound represented by the formula (1) may exist as a hydrate or an arbitrary solvate, and these hydrates or solvates are also included in the present embodiment. Further, the compound represented by the formula (1) may have asymmetric carbons, and these asymmetric carbons may have an arbitrary configuration. All of these asymmetric carbon-based pure forms of optical isomers, diastereoisomers and other stereoisomers, mixtures of arbitrary stereoisomers, racemates and the like are included in this embodiment. Further, the compound represented by the formula (1) may have one or more double bonds, and a geometric isomer derived from the double bond or the ring structure may also be present. It goes without saying that any geometric isomer in pure form or a mixture of any geometric isomers is also included in this embodiment.

Next, a method for producing the compound of the present embodiment will be described. The compound of the present embodiment is produced, for example, according to the following methods A to K, but the method for producing the compound of the present embodiment is not limited thereto.

[A method]

Among the compounds represented by the formula (1), the compound represented by the formula (2') is a compound of the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1). ) And the compound of formula (52) (in formula (52), A is the same as the definition in formula (2), Q'is oxygen atom, sulfur atom, formula: -NH. Manufactured by reacting a divalent group represented by − or a divalent group represented by the formula: −N (CH ₃ ) − in the presence or absence of a base or in the presence of a condensing agent. Will be done.

As the compound represented by the formula (51) as a starting material, a commercially available reagent may be used, or a synthesized compound may be used. The compound represented by the formula (51) is, for example, JP-A-63-93766, JP-A-1-283270, RE Banks, et al., Heterocyclic polyfluoro-compounds. Part XII. Synthesis and some reactions of 2. , 3,5,6-tetrafluoro-4-iodopyridine, J. Chem. Soc. (C), 2091-2095 (1967) and the like.

Examples of the solvent used in the reaction include dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and the like.

Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.

Examples of the base used in the reaction include 4-dimethylaminopyridine. The amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).

The amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51). The amount of the compound of the formula (52) used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).

The reaction temperature is selected, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. The reaction time is, for example, in the range of 10 minutes to 24 hours, preferably in the range of 30 minutes to 4 hours.

[B method]

Among the compounds represented by the formula (1), the compound represented by the formula (2') is a compound of the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1). ) is the same as defined in.) from the compound of formula (53) (in the formula ^(53), X ^1, X 2, ^{X 3} and ^{X 4} via the same as defined in the formula (1).) It can also be manufactured by the following method.

First, in the first step, the compound of the formula (53) is produced by chlorinating the compound of the formula (51).

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, dichloromethane, chloroform, acetonitrile and the like, but it can also be carried out without a solvent.

Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl chloride and the like. The amount of the chlorinating agent used is in the range of 1 to 5 equivalents based on the compound of the formula (51). The reaction temperature is, for example, in the range of -20 to 100 ° C, preferably in the range of 10 ° C to 80 ° C. The reaction time is in the range of 10 minutes to 6 hours, preferably 30 minutes to 2 hours.

Next, in the second step, the compound represented by the formula (2') can be produced by reacting the compound of the formula (53) with the compound of the formula (52) in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and mixed solvents thereof.

Examples of the base used in the reaction include triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base used is in the range of 1 to 10 equivalents based on the carboxyl chloride (53).

The amount of the compound represented by the formula (52) to be used is in the range of 1 to 2 equivalents based on the carboxyl chloride product (53). The reaction temperature is, for example, in the range of -20 to 100 ° C, preferably in the range of 10 ° C to 50 ° C. The reaction time is in the range of 10 minutes to 6 hours, preferably 30 minutes to 3 hours.

Further, the compound represented by the formula (2') is prepared by adding a solvent, a chlorinating agent and a formula (52) to the compound represented by the formula (51) in the same container without isolating the compound represented by the formula (53). It can also be produced by adding the compound represented by (1) and a base and reacting.

[C method]

Compounds represented by among formulas of the compounds represented by formula (1) (55) is a compound of Formula (51) (in the formula ^(51), X ^1, X 2, ^{X 3} and ^{X 4,} the formula (1) the same as defined as in.) (compound 54) (formula (54) wherein, a is the same as defined in the formula (2), X ⁵ represents a halogen atom.) with the presence of a base It can be produced by reacting.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and the like.

Examples of the base used in the reaction include sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like. The amount of the base used is in the range of 1.0 to 1.5 equivalents based on the carboxylic acid (51).

The amount of the compound represented by the formula (54) to be used is in the range of 1 to 2 equivalents based on the carboxylic acid (51). The reaction temperature is, for example, in the range of -20 to 120 ° C, preferably in the range of 10 to 80 ° C. The reaction time is in the range of 10 minutes to 8 hours, preferably 30 minutes to 6 hours.

[D method]

Compounds represented by among formulas of the compounds represented by formula (1) (55), in the compound represented by the formula (51) (Formula ^(51), X ^1, X 2, ^{X 3} and ^{X 4,} the formula ( By reacting the compound represented by the formula (56) with the compound represented by the formula (56) (where A is the same as the definition in the formula (2)) in the presence of an acid. Can also be manufactured.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and the like, but the reaction can also be carried out without a solvent. ..

The amount of the compound represented by the formula (56) to be used is in the range of 1 to 10 equivalents based on the carboxylic acid (51). Examples of the acid used in the reaction include sulfuric acid and hydrogen chloride, and the amount of the acid used is in the range of 0.01 to 3 equivalents based on the carboxylic acid (51). The reaction temperature is, for example, in the range of -20 to 120 ° C, preferably in the range of 10 to 90 ° C. The reaction time is in the range of 10 minutes to 8 hours, preferably 30 minutes to 6 hours.

[E method]

Compounds represented by among formulas of the compounds represented by formula (1) (71), in the compound represented by the formula (51) (Formula ^(51), X ^1, X 2, ^{X 3} and ^{X 4,} the formula ( The same as the definition in 1)) and the compound represented by the formula (57) (in the formula (57), Q'is an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH-, or a compound. Formula: A _{divalent group represented by −N (CH 3} ) −, where E is a divalent group represented by the formula: _{− (CH 2} ) _n − (where n is an integer of 2-4. Shown.), Formula: A _{divalent group represented by −CH 2} −CH = CH −CH ₂ −, a cyclohexane-1,4-diyl group, a 1,4-phenylene group, or a formula (2B ′) below. divalent (in the formula (2B '), G is an oxygen atom, a sulfur atom or the formula. where: -SO 2 _- represents a divalent group represented by) group) the presence of a base or absence, condensation It can be produced by reacting in the presence of an agent.

Examples of the solvent used in the reaction include dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and the like.

Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.

Examples of the base used in the reaction include 4-dimethylaminopyridine. The amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).

The amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51). The amount of the compound represented by the formula (57) to be used is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid (51). The reaction temperature is, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. The reaction time is in the range of 10 minutes to 24 hours, preferably in the range of 30 minutes to 18 hours.

[F method]

Compounds represented by among formulas of the compounds represented by formula (1) (71), in the compound represented by the formula (53) (Formula ^(53), X ^1, X 2, ^{X 3} and ^{X 4,} the formula ( Reaction in the presence of a base of the compound represented by the formula (57) and the compound represented by the formula (57) (where Q'and E are the same as the definition of the formula (57) in the method E). It can also be manufactured by making it.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and mixtures thereof.

Examples of the base used in the reaction include triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base used is in the range of 1 to 10 equivalents based on the carboxyl chloride (53).

The amount used represented by the formula (57) is in the range of 0.5 to 0.6 equivalent based on the carboxyl chloride product (53). The reaction temperature is, for example, in the range of -20 to 100 ° C, preferably in the range of 10 to 50 ° C. The reaction time is in the range of 10 minutes to 6 hours, preferably 30 minutes to 4 hours.

[G method]

Compounds represented by among formulas of the compounds represented by formula (1) (59), in the compound represented by the formula (51) (Formula ^(51), X ^1, X 2, ^{X 3} and ^{X 4,} the formula ( as defined in 1) is the same.) with a compound represented by the formula (58) (in the formula (58), ^{X 5} represents a halogen atom, E is the same as defined in the formula (57) in the method E There is.) Can be produced by reacting in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and the like.

Examples of the base used in the reaction include sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like. The amount of the base used is in the range of 1.0 to 1.1 equivalents based on the carboxylic acid (51).

The amount of the compound represented by the formula (58) to be used is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid (51). The reaction temperature is -20 to 120 ° C, preferably in the range of 10 to 80 ° C. The reaction time is in the range of 10 minutes to 8 hours, preferably 30 minutes to 6 hours.

[H method]

Among the compounds represented by the formula (1), the compound represented by the formula (3') is the compound represented by the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are the formulas. (Same as the definition in (1)) and the compound represented by the formula (60) (in the formula (60), Aa is the same as the definition in the formula (3)) in the presence or absence of the base. Below, it can be produced by reacting in the presence of a condensing agent.

Examples of the solvent used in the reaction include dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and the like.

Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.

Examples of the base used in the reaction include 4-dimethylaminopyridine. The amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).

The amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51). The amount of the compound represented by the formula (60) used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51). The reaction temperature is in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. The reaction time is in the range of 10 minutes to 6 hours, preferably 30 minutes to 3 hours.

[I method]

Among the compounds represented by the formula (1), the compound represented by the formula (3') is the compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are the formulas. By reacting the compound represented by the formula (60) with the compound represented by the formula (60) (Aa is the same as the definition in the formula (3)) in the presence of a base. Can also be manufactured.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and mixed solvents thereof.

Examples of the base used in the reaction include triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base used is in the range of 1 to 10 equivalents based on the carboxyl chloride (53).

The amount of the compound represented by the formula (60) to be used is in the range of 1 to 2 equivalents based on the carboxyl chloride product (53). The reaction temperature is in the range of -20 to 100 ° C, preferably in the range of 10 to 50 ° C. The reaction time is in the range of 10 minutes to 6 hours, preferably 30 minutes to 4 hours.

[J method]

Among the compounds represented by the formula (1), the compound represented by the formula (4') is the compound represented by the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are the formulas. The compounds represented by the formula (61) from (the same as the definition in (1)) (X ¹ , X ² , X ³ and X ⁴ in the formula (61) are the same as the definition in the formula (1). It can be manufactured by the following method via.).

First, in the first step, the compound represented by the formula (61) can be produced by reducing the compound represented by the formula (51).

Examples of the solvent used in the reaction include tetrahydrofuran, dimethoxyethane, 1,4-dioxane, dichloromethane, chloroform, toluene and the like.

Examples of the reducing agent used in the reaction include borane-tetrahydrofuran complex and borane-dimethyl sulfide complex. The amount of the reducing agent used is in the range of 3 to 6 equivalents based on the compound represented by the formula (51).

The reaction temperature is in the range of -20 to 80 ° C, preferably in the range of 0 to 40 ° C. The reaction time is in the range of 10 minutes to 8 hours, preferably 30 minutes to 6 hours.

Then, in a second step, in the compound represented by the formula (61) compound represented by the formula (54) (Formula (54), Ab is the same as defined in the formula (4), ^{X 5} is a halogen The compound represented by the formula (4') can be produced by reacting (indicating an atom) in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and mixtures thereof.

Examples of the base used in the reaction include triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base used is in the range of 1 to 10 equivalents based on the compound represented by the formula (61).

The amount of the compound represented by the formula (54) to be used is in the range of 1 to 2 equivalents based on the compound represented by the formula (61). The reaction temperature is in the range of -20 to 100 ° C, preferably in the range of 10 to 60 ° C. The reaction time is in the range of 10 minutes to 6 hours, preferably 30 minutes to 3 hours.

[K method]

Among the compounds represented by the formula (1), the compound represented by the formula (5') is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are the formulas. (1) the same as defined in the.) (compound represented by 62) (formula (62) wherein, ^{X 5} represents a halogen atom, L is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms (Shown) can be produced by reacting in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and mixed solvents thereof.

Examples of the base used in the reaction include triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base used is in the range of 1 to 10 equivalents based on the carboxyl chloride (53).

The amount used in the formula (62) is in the range of 1 to 2 equivalents based on the carboxyl chloride product (53). The reaction temperature is in the range of -20 to 100 ° C, preferably in the range of 10 to 90 ° C. The reaction time is in the range of 10 minutes to 10 hours, preferably 30 minutes to 8 hours.

[L method]

Among the compounds represented by the formula (1), the compound represented by the formula (3') is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are The compound represented by the formula (1) and the compound represented by the formula (60) (in the formula (60), Aa is the same as the definition in the formula (3)) in the presence or absence of an acid. It can also be produced by reacting in the presence.

Examples of the solvent used in the reaction include toluene, dichloromethane, chloroform, dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, nitromethane, nitrobenzene and a mixed solvent thereof, but the solvent can also be used without a solvent. can.

Examples of the acid used in the reaction include aluminum trichloride, aluminum tribromide, lanthanoid triflate, zeolite, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, hydrochloric acid, paratoluenesulfonic acid, iron trichloride, zinc dichloride, and polyphosphorus. Examples thereof include acid, titanium tetrachloride, titanium tetrabromide, tin chloride, zinc trifluoromethanesulfonate and the like. The amount of acid used is in the range of 0.01 to 10 equivalents based on the carboxyl chloride (53).

The amount of the compound represented by the formula (60) to be used is in the range of 0.5 to 2 equivalents based on the carboxyl chloride product (53). The reaction temperature is in the range of -20 to 250 ° C, preferably in the range of 10 to 100 ° C. The reaction time is in the range of 10 minutes to 48 hours, preferably in the range of 30 minutes to 16 hours.
[Specific compound represented by the formula (2'')]
Among the compounds represented by the formula (1), specific embodiments of the compound represented by the formula (2 ″) are shown in Tables 1 to 8 below.

As specific compounds represented by the formula (2 ″), X ¹ , X ² , X ³ and X ⁴ are combinations of substituents shown in Table 1 below, and Q and A are Tables 2 to 8. Examples thereof include compounds which are a combination of substituents indicated by. Further, J represents an oxygen atom or a sulfur atom.

Hereinafter, the following abbreviations may be used in the present specification.

n: normal sec: secondary tert: tertiary

Among the compounds represented by the formula (2 ″), as the compound in which A is the group represented by the formula (2A), X ¹ , X ² , X ³ and X ⁴ are the substituents shown in Table 9 below. It is a combination, and Q is a _{divalent group represented by the formula: -O- (CH 2} ) _n- O-, a divalent group represented by the formula: -NH- (CH ₂ ) _n- O-, a formula. : -NH- (CH ₂ ) _{divalent group represented by n-} NH-, formula: -O-CH ₂ -CH = CH-CH ₂ -valent group represented by -O-, formula: -NH- CH ₂ -CH = CH-CH ₂ -valent group represented by -O-, formula: -NH-CH ₂ -CH = CH-CH ₂ -valent group represented by -NH-, cyclohexane-1,4 -Diyldioxy group, cyclohexane-1,4-diyldiamino group, formula: -NH- (cyclohexane-1,4-diyl) -divalent group represented by -O-, 1,3-phenylenediamino group, 1,4- A phenylenediamino group, a 1,4-phenylenedioxy group, a divalent group represented by the formula -NH- (1,4-phenylene) -O-, or a divalent group represented by the formula (2B). Examples include compounds.

[Specific compound represented by the formula (3')]
Among the compounds represented by the formula (1), specific embodiments of the compound represented by the formula (3') are shown in Table 10 below.

As specific compounds represented by the formula (3'), X ¹ , X ² , X ³ and X ⁴ are combinations of substituents shown in Table 10 below, and Aa is a piperidine-1-yl group. 1-Methyl-1-1H-pyrrole-2-yl group, morpholine-4-yl group, indolin-1-yl, benzoisothiazole-3 (2H) -one-1,1-dioxide-2-yl, piperazine -1-yl group, azetidine-1-yl group, 2,5-dioxopyrrolidine-1-yl group, 3-oxoisothiazole-2 (3H) -yl group, benzo [d] isothiazole-2 (3H) ) -Il group, 1,1-dioxo-3-oxobenzo [d] isothiazole-2 (3H) -yl group, 5,6-dihydro-4H-1,3-oxadin-2-yl group, 1H-pyrrole Examples include compounds that are a -2-yl group or an isoindolin-2-yl group.

[Specific compound represented by the formula (5')]
Specific embodiments of the compound represented by the formula (5') among the compounds represented by the formula (1) are shown in Tables 11 and 12 below.

As specific compounds represented by the formula (5'), X ¹ , X ² , X ³ and X ⁴ are combinations of substituents shown in Table 11 below, the substituents of Z and their substitution positions, and the substitution positions thereof. Examples thereof include compounds in which m is a combination shown in Table 12 below.

[Plant pathogen]
The plant pathogen to be controlled by the soil disease control agent of the present embodiment is not particularly limited, and examples thereof include fungi, bacteria, actinomycetes, and viruses.

Examples of phytopathogenic fungi include vegetable seedling blight fungus (Pythium ultimum), vegetable blight fungus (Rhizoctonia solani), sclerotium sclerotium (Fusarium oxysporum), and vegetable wilt fungus (Fusarium oxysporum). Homopsis sclerotioides, Plasmodiophora brassicae, Spongospora subterranea, fruit tree Sclerotium sclerotium , Soybean white silk disease (Sclerotium rolfsii), tomato brown root rot (Pyrenochateta lycoperici), wheat streak disease (Cefalosporium gramineum), soybean foliage disease (Phialophora green rot), soybean black root rot Sclerotium incarnata, black rot sclerotium sclerotium (Typula ishikariensis), Aphanomyces cochlioides, tobacco black root disease (Thielaviopsis basicola) Disease fungus (Alternaria alternata), pear black spot fungus (Alternaria kikutiana), gray mold fungus (Botrytis cinerea), rice sesame leaf blight fungus (Cochliobolus miyaberia), potato charcoal fungus (Jagaimo charcoal) Fusarium oxysporum f. Sp. Lycoperisi, Gibberella fujikuroi, Glomerella sclerota, Sclerotium sclerotium, Sclerotium sclerotium, Sclerotium sclerotium Half-body wilt fungus (Verticilli) um albumo-atrum, wheat red rust fungus (Puccinia recondita), powdery mildew fungus (Erysipe gramines), potato epidemic fungus (Phytophthora infestans), cucumber powdery mildew (Pseudo) Alternaria solani, vegetable powdery mildew (Sclerotinia sclerotiorum), apple scab (Venturia inaequualis), peach powdery mildew (Moniliina fructiciori) spiori spores ), Cercospora beticola, Leptosphaeria nodolum, Blumeria powdery mildew,
And so on. Particularly preferable examples of the phytopathogenic fungi include vegetable seedling blight fungus (Pythium ultimum), vegetable blight fungus (Rhizoctonia solani), sclerotium sclerotium (Fusarium oxysporum), and vegetable wilt fungus (Fusarium spurium). , Sclerotium root rot fungus (Phomopsis sclerotioides), Abranaceae vegetable root rot fungus (Plasmodiophora brassicae), potato powdery scab fungus (Spongospora subterranea), fruit tree crest Rosellinia necatrix, soybean white silk disease (Sclerotium rolfsii), tomato brown root rot (Pyrenochateta lycoperici), wheat streak disease (Cefalosporium gramineum), soybean foliage disease (Phiradio) Cyphula incarnata, Snow rot black sclerotium (Typula ishikariensis), Tensai seedling blight (Aphanomyces cochlioides), Tobacco black root disease (Thielaviopsis basis) Can be mentioned.

Examples of phytopathogenic bacteria include Pseudomonas, Erwinia, Pectobacterium, Xanthomonas, Burkholderia, Streptomyces, Ralstonia, Clavibacter, Rhizomania, Rhizomonas, and Rhizomonas. , The genus Acidovorax, the genus Artrobacter, the genus Rhodococcus and the like. Preferred examples of the phytopathogenic bacterium include Pseudomonas, Agrobacterium, Ralstonia, and Erwinia.

Examples of plant pathogenic actinomycetes include the genus Streptomyces.

Further, as phytopathogenic viruses, wheat wilt virus (Soil-born female virus), soybean mosaic virus (Soybean mosaic virus), alfalfa mosaic virus (Alfalfa mosaic virus), potato leaf curl virus (Pota) and potato virus (Pota). Examples thereof include a virus (Cucuber mosaic virus) and a tobacco mosaic virus (Tobacco mosaic virus).

The soil disease control agent of the present embodiment contains the compound represented by the formula (1) as an active ingredient. In the present specification, "containing the compound represented by the formula (1) as an active ingredient" means that the compound represented by the formula (1) is contained in an amount sufficient to obtain a soil disease control effect. , The content of the compound represented by the formula (1) is not particularly limited as long as it is contained as an active ingredient in the form of a free form, a hydrate, an arbitrary solvate, a salt or the like.

When the soil disease control agent of the present embodiment is used as an active ingredient of the disease control agent for agriculture and horizons, the above-mentioned compound may be used as it is, or the above-mentioned compound may be used as it is, or according to the conventional method of the disease control agent for agriculture and horizons, agriculture and horizons. Allowable carriers for use, such as solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants, emulsions, liquids, suspensions, wettable powders, powders, granules, tablets, oils. , Aerosol, flowable agent and the like may be used in the form of a composition (formulation) for controlling soil diseases of any dosage form. The composition for controlling soil diseases may further contain other pharmaceutical aids.

Examples of the carrier that can be used include a liquid carrier, a solid carrier, a gaseous carrier, a surfactant, a dispersant and the like. In addition, examples of the auxiliary agent for the pharmaceutical product include those usually used in a composition for controlling soil diseases.

Examples of the solid carrier include clays (carion clay, diatomaceous earth, bentonite, acidic white clay, etc.), synthetic silicon hydroxide-containing silicon, talc, ceramics, and other inorganic minerals (serinite, quartz, sulfur, activated charcoal, calcium carbonate, silica hydrate, etc.). ) And other fine powders and granules, starch, lactose, vinyl chloride-based polymers, and synthetic polymers such as polyurethane.

Examples of the liquid carrier include alcohols (methanol, ethanol, isopropanol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, glycerin, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzyl). Alcohol, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (paraffin, n-hexane, cyclohexane, kerosine, kerosene, etc.), ethers (diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diisopropyl ether, etc.) Diethyl ether, dioxane, tetrahydrofuran, etc.), esters (propylene carbonate, ethyl acetate, butyl acetate, benzyl benzoate, isopropyl mythylate, fatty acid esters of propylene glycol, etc.), nitriles (acetohydrate, isobutyronitrile, etc.), amides Classes (dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), animal and vegetable oils such as soybean oil, cottonseed oil, dimethylsulfoxide, silicone oil, higher fatty acids, etc. Examples include glycerol formal, water and the like.

Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

Surfactants for emulsification, dispersion, spreading, etc., examples of the dispersant include alkyl sulfate esters, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, and lignin. A sulfonate or the like is used. Further, as an auxiliary agent for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like are used.

The above carriers, surfactants, dispersants, and auxiliaries can be used alone or in combination, if necessary.

The content of the soil disease control agent (compound represented by the formula (1)) in the composition for controlling soil disease is not particularly limited, and for example, the emulsion is usually 1 to 50% by mass, and the wettable powder is usually 1 to 1 to 50% by mass. 50% by mass, usually 0.1 to 30% by mass for powders, usually 0.1 to 15% by mass for granules, usually 0.1 to 10% by mass for oils, usually 0.1 to 10% by mass for aerosols. ..

The soil disease control agent or the soil disease control composition of the present embodiment may be used as it is, or may be diluted and used as necessary.

The soil disease control agent or the soil disease control composition can be used in combination with other pest control agents, for example, a resistance inducer and another pest control agent may be mixed and sprayed separately. May be sprayed at different times or at the same time.

Examples of other pest control agents include insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers and the like, and specifically, for example, The Pesticide Manual, No. 1. 17th edition The British Crop Protection Council published) and Shibuya Index (SHIBUYA INDEX 17th edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP).

Examples of the insecticide include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiophos, prophophos, prophophos, profophos, and profenphos. methyl, chlorfenvinphos, demethon, ethion, malathion, comaphos, isoxathion, fenthion, diazion, diazinon. , Aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, ethiofencarb, phenothiocarb, phenothicarb carbosulfan, furathiocarb, hyquincarb, alanycarb, mesomyll, benmuracarb, benfuracarb, cartap, thiocyclam tetradifon, acrinathrin, bifenthrin, cycloprothrin, cyfluthrin, dimefluthrin, empentrin, empentrin, empentrin (Imiprothrin), metoflutrin, permethrin, phenothrin, resmethrin, tef luthrin, tetramethrin, tralomethrin, transfluthrin, cypermethrin, deltamethrin, deltamethrin, cihalothrin, cyhalothrin, cypermethrin, cihalothrin Prox (ethofenprox), flufenprox, halfenprox, silafluofen, cyromazine, diflubenzuron, diflubenzuron, teflubenzuron, teflubenzuron (Flufenoxuron), hexaflumuron, lufenuron, novaluron, penfluron, triflumuron, chlorfluazuron (chlorfluazuron), difluthrin, difluthrin, difluthrin. ), fenoxycarb (fenoxycarb), pyriproxyfen (pyriproxyfen), halofenozide (halofenozide), tebufenozide (tebufenozide), methoxyfenozide (methoxyfenozide), chromafenozide (chromafenozide), dicyclanil (dicyclanil), buprofezin (buprofezin), hexythiazox (hexythiazox), amitraz (amitraz), chlordimeform (chlordimeform), pyridaben (pyridaben), fenpyroximate (fenpyroxymate), flufenerim (flufenerim), pyrimidifen (pyrimidifen), tebufenpyrad (tebufenpyrad), tolfenpyrad (tolfenpyrad), fluacrypyrim (fluacrypyrim), acequinocyl (acequinocyl), Cyflumethofen, flubenzia Midi (flubendiamide), ethiproll, fipronil, etoxazole, imidacloprid, nitipacloprid, nitenpyram, thiamethoxam, c1othian Thiamethoxam, pymetrozine, biphenazate, spinosadylofen, spiromethifen, firomesisifen, flonicamide, fronicamid, chlorphenipyl, chlorphenapyl indoxacarb), pyridalyl, spinosad, avermictin, milbemicin, azadiractin, nicotine, nicotine, nicotine, scented agent, rotenone, rotenon (Emectinbenzoate), spinetram, pyrifluquinazon, chlorantraniliprole, thiamethoxam (cyantraniliprole), sienopyraphen (cyenopyraten) metaflumizone, pyrafluple, pyriple, dimefluthrin, fenazaflor, hydramethylnon, thiramethoxam, triazamate, etc. ..

Examples of the bactericidal agent include azoxystrobin, cresoxym-methyl, trifluorostrobin, orysastrobin, picoxystrobin, and floxastrobin. ) And the like; anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil; triadimephon, bitertanol, triflumizol, triflumizol, triflumizol , Compoundonazole, penconazole, flusilazole, microbutanil, cyproconazol, cyproconazol, tebuconazol, tebuconazol, tebuconazol, tebuconazol, tebuconazol, tebuconazol ) And the like; quinoxalin compounds such as quinomethionate; manneb, zineb, mancozeb, polycarbamate, propineb and dicarbeb. Phenylcarbamate compounds such as (diethofencarb); organic chlorine compounds such as chlorothalonil and quintozene; venomyl, thiophanate-methyl, carbendazyl (carbendazyl) and carbendazole compounds. Phenylamide compounds such as (metalaxyl), oxadixyl, offurase, benaluxyl, furalaxyl, cyprofuram; diclofluanide (dichlofluan), etc. Ethic acid-based compounds; Copper-based compounds such as cupper hydroxide and oxyquine-copper; Isoxazole-based compounds such as hydroxyisoxazole; Josetyl-alluminium. , Organic phosphorus compounds such as torquelophos-methyl; N-halogenothioalkyl compounds such as captan, captafol, folpet; procymidone, iprodion. , Dicarboxyimide compounds such as vinchlosolin; benzanilide compounds such as flutranil and mepronil; morpholine compounds such as fenpropimorph and dimethomorph; Organic tin-based compounds such as tin (fenthin hydroxide) and triphenyltin acetate (fenthin acetate); cyanopyrrole-based compounds such as fludioxonil and fenpiclonil; S-methyl (acibenzalar-S-methyl), thiazinil (tiadinil), isothianil (isotianil), carpropamide (carpropamide), diclocymet (diclocymet), phenoxanil (fenoxanil), tricyclazole (tricylon) Fluazinam, cymoxanil, trifoliane, pylifenox, fenarimol, fenpropidin, fenpropidin, pencyclonyl, pencyclonyl, cyazophenac (Boscalid), penthiopyrad, compound (p) roquinazid, quinoxyphen, famoxadone, fenamidone, iprovalicarb, benchavalicalbu isopropyl (benthiavalicarb-isopropanol) (Isopyrazam), fenpicoxamid, kasugamycin, validamycin and the like can be mentioned.

Examples of the acaricide include bromopropylate, tetradiphon, propargite, amitraz, phenothiocarb, hexithiozine, hexithiazine, and hexithiazox. Dienochlor, fenpyroximate, tebufenpyrad, pyridaben, pyrimidifen, clofentezine, clofentezine, exofenhexine, exomilbemectin (Acequinocyl), bifenazate, fluacrypyrim, spirodichlofen, spiromesifen, clofentezine, chlorphenapyl, avermectin, etc. Will be.

Examples of the herbicide include phenoxy acid-based compounds such as bialaphos butyl (cyhalophos-butyl) and 2,4-D; carbamate-based compounds such as esprocarb and desmedipham; alachlor ( Acid amide compounds such as alachlor and metolachlor; urea compounds such as diuron and tebutiuron; sulfonylurea compounds such as halosulfuron and frazasulfuron; Pyrimidyloxybenzoic acid compounds such as pyriminobac-methyl; amino acid compounds such as glyphosate, bialaphos, glufosinate-ammonium and the like can be mentioned.

Examples of the plant growth regulator include ethylene agents such as ethephon; auxin agents such as indolebutyric acid and ethichlocate; cytokinin agents; gibberellin agents; auxin antagonists; dwarfing agents; evaporation. Examples include inhibitors.

Examples of the fertilizer include nitrogenous fertilizers such as urea, ammonium nitrate, ammonium nitrate and ammonium chloride; and phosphoric acid fertilizers such as lime perphosphate, ammonium phosphate, perphosphoric acid, and phosphoric acid. Potassium fertilizers such as potassium chloride, potassium bicarbonate, potassium nitrate, potassium nitrate, potassium potassium nitrate, etc .; manganese fertilizers such as manganese sulfate, manganese nitrate; boron fertilizers such as boric acid and borate. Be done.

In one embodiment, the present invention provides a soil disease control method in which the above-mentioned soil disease control agent or the above-mentioned compound is brought into contact with a plant or seed or contained in a cultivation bed. The soil disease control agent may be used in the form of the above-mentioned soil disease control composition.

When the above-mentioned soil disease control agent is brought into contact with a plant, it may be brought into contact with the foliage, roots, rhizomes, tubers, bulbs, germinated buds and the like of the plant. In addition, the above-mentioned soil disease control agent may be brought into contact with the seeds of the plant. Examples of the cultivation floor include soil, rice field water for growing rice, carriers for growing plants, and hydroponic water. Hydroponically grown water may contain nutrients.

In the method of the present embodiment, the method of bringing the above-mentioned soil disease control agent into contact with a plant or seed, or the method of incorporating the above-mentioned soil disease control agent into a cultivation bed is particularly limited as long as it is an application method generally applied in agriculture and horticulture. However, for example, foliage spraying, water surface application, soil treatment, nursery box application, seed treatment, soaking treatment, fertilizer mixing, irrigation water mixing and the like can be mentioned.

The application rate of the soil disease control agent of the present embodiment is determined according to the type and degree of onset of the target disease, the type of the target crop, and the target site in consideration of the application mode such as aviation spraying and ultra-trace spraying in addition to the application method. , Can be decided.

For example, when the soil disease control agent is sprayed on the foliage of a plant, an emulsion, a wettable powder or a flowable agent obtained by diluting 1 to 1000 g of the pharmaceutical product with 50 to 1000 L of water per 10 ares is used. In the form of a powder, about 1 to 10 kg of the pharmaceutical product can be used per 10 ares.

When the soil disease control agent is applied to soil, for example, in the form of granules, about 1 to 10 kg per 10 ares can be used.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited to these Examples.

Hereinafter, the following abbreviations may be used in the examples.
ESI: Electrospray ionization method MS: Mass spectrum IR: Infrared absorption spectrum n: Normal tert: Tershary

[Example 1]
2,3,6-trifluoroisonicotinic acid (1.76 g) is dissolved in N, N-dimethylformamide (10 mL), and bromoethane (1.08 g) and potassium carbonate (1.38 g) are added to the solution. In addition, the mixture was stirred at 80 ° C. for 2 hours. Then, the reaction mixture was returned to room temperature, ethyl acetate was added, and the mixture was extracted with water, and then the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain the compound of Example 1-117 (yield 1.44 g).

[Example 2]
2,3,6-trifluoroisonicotinic acid (5.28 g) was dissolved in thionyl chloride (30 mL), and the mixture was heated under reflux for 1 hour. After the reaction was concentrated, it was dissolved in acetonitrile (30 mL), 3-chloro-4-methylaniline (5.64 g) and pyridine (3.20 g) were added, and the mixture was heated under reflux for 1 hour. Then, the reaction mixture was returned to room temperature, ethyl acetate was added, and the mixture was washed successively with 1N hydrochloric acid and 1N sodium hydroxide, and then the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain the compound of Example 1-30 (yield 7.70 g).

[Example 3]
Dissolve 2,3,6-trifluoro-4-pyridinemethanol (106 mg) in dichloromethane (8 mL), add acetyl chloride (65 mg) to the solution, cool to 0 ° C., and cool to N, N-diisopropyl. Ethylamine (130 mg) was added and stirred overnight at room temperature. Then, after distilling off the solvent, it was dissolved in diethyl ether, washed successively with saturated sodium carbonate, 2% hydrochloric acid and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent with an evaporator, the residue was purified by silica gel chromatography to obtain the compound of Example 3-1 (yield 63.2 mg).

[Example 4]
2,6-Difluoroisonicotinic acid (50 mg) is dissolved in chloroform (3.1 mL), and aniline (29 μL) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (65 mg) are added to the solution. ), 4-Dimethylaminopyridine (catalytic amount) was added, and the mixture was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and then washed successively with saturated ammonium chloride and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 1-143 (yield 66.3 mg).

[Example 5]
2,3,6-trifluoroisonicotinic acid (30 mg) is dissolved in chloroform (3.1 mL), and ethylenediamine (6.0 μL), 1-ethyl-3- (3-dimethylaminopropyl) is added to the solution. Carbodiimide hydrochloride (38 mg), 1-hydroxybenzotriazole (27 mg) and triethylamine (30 μL) were added and stirred overnight at room temperature. Again, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (38 mg) and 1-hydroxybenzotriazole (27 mg) were added, and the mixture was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and then washed successively with saturated ammonium chloride and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 1-150 (yield 20.1 mg).

[Example 6]
2,3,6-trifluoroisonicotinic acid (100 mg) was dissolved in N, N-dimethylformamide (5.6 mL), 2-chloroethylamine hydrochloride (79 mg), 1-ethyl-3- (3-dimethyl). Aminopropyl) carbodiimide hydrochloride (128 mg), 1-hydroxybenzotriazole (92 mg) and triethylamine (101 μL) were added, and the mixture was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and then washed successively with saturated ammonium chloride and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography to obtain N- (2-chloroethyl) -2,3,6-trifluoroisonicotinamide (yield). 100 mg).

The N- (2-chloroethyl) -2,3,6-trifluoroisonicotinamide (20 mg) obtained above was dissolved in tetrahydrofuran (8.4 mL), and 55% sodium hydride (3. 8 mg) was added, and the mixture was stirred for 3 hours. Then, water was added to the reaction mixture and the mixture was extracted with ethyl acetate, and then the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain the compound of Example 4-2 (yield 16 mg).

[Example 7]
2,6-Difluoroisonicotinic acid (80 mg) is dissolved in acetonitrile (1 mL), and cyclohexyl alcohol (50 mg) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (96 mg) are added to the solution. , 4-Dimethylaminopyridine (61 mg) was added, and the mixture was stirred at room temperature for 24 hours. Then, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and then washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by Preparative TLC to give the compound of Example 1-205 (yield 42 mg).

[Example 8]
2,3,6-trifluoroisonicotinic acid (177 mg, 1.0 mmol) was dissolved in dichloroethane, thionyl chloride (1 mL) was added to the solution, and the mixture was heated under reflux and stirred for 2 hours. After distilling off the solvent of the reaction product with an evaporator, nitromethane (3 mL), 1-methylpyrrole (54 mg, 0.67 mmol) and zinc trifluoromethanesulfonate (II) (24 mg, 0.066 mmol) were added at room temperature. Stirred overnight. After adding sodium hydrogen carbonate to the reaction mixture, water was added and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off with an evaporator, the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 1/1 (volume ratio)), and then washed with hexane. Compound 2-2 was obtained (yield 44 mg, 0.18 mmol, yield 27%).

The compounds of Examples 1-1 to Example 1-218 represented by the formula (2 ″) shown in Tables 13 to 34 below were produced according to the methods of Examples 1 to 8. In addition, the compounds of Examples 2-1 to 2-5 represented by the formula (3') shown in Table 35 below were produced. In addition, the compounds of Example 3-1 and Example 3-2 represented by the formula (4') shown in Table 36 below were produced. In addition, the compounds of Examples 4-1 to 4-4 represented by the formula (5') shown in Table 37 below were produced.

^{The MS, IR, and 1} H-NMR data of each compound represented by the formulas (2 ″), (3 ′), (4 ′) and (5 ′) are collected together with the compounds obtained in Examples 1 to 8. It is shown in Tables 13-37. As a ¹ H-NMR (400 MHz, 500 MHz or 600 MHz) measurement solvent, the compounds of Examples 1-8, 1-69, 1-175, 1-176 and 4-2 are heavy. Deuterated chloroform: deuterated methanol = 1: 1 was used for acetone and the compound of Example 1-93, and deuterated chloroform was used for the other compounds of Example. MS was measured by the ESI-MS method. IR was measured by the KBr method.

The compounds of Examples 1-1 to 1-218 represented by the formula (2 ″) are shown in Tables 13 to 34.

The compounds of Examples 2-1 to 2-5 represented by the formula (3') are shown in Table 35.

The compounds of Examples 3-1 and 3-2 represented by the formula (4') are shown in Table 36.

The compounds of Examples 4-1 to 4-4 represented by the formula (5') are shown in Table 37.

[Example 9]
<Activity against Oriental melon Panama disease>
An acetone solution of the Example compound prepared to 0.5 mg / mL was diluted 10-fold with water and subjected to the test. 3 mL per pot was soil-irrigated to the root of the cotyledonous oriental melon (variety: golden melon) cultivated in the pot. The day after the treatment, a yeast-like cell suspension of Fusarium oxysporum f. Sp melonis adjusted to ^{5 × 10 7 cells / mL was inoculated by irrigation.} Then, it was cultivated in a greenhouse, and 28 days after inoculation, it was investigated according to the following index. The degree of disease of each true leaf and stem was calculated based on this index, and the control value was calculated from the obtained degree of disease by the following formula.
Index (0-2)
0: No lesions, 1: Yellowing of true leaves or stems, 2: Bacterial control value = ((Disease rate of untreated plot-Sickness of treated plot) / Disease degree of untreated plot) x 100

The following compounds showed a control value of 60 or more, and the control effect on the Oriental melon Panama disease was confirmed.
1-30, 1-41, 1-98, 1-126, 1-134, 1-135, 1-139, 1-143, 1-218, 3-1, 3-2, 4-2, 4- 4

An acetone solution of the Example compound prepared to be 0.25 mg / mL was diluted 10-fold with water and subjected to the test. 3 mL per pot was soil-irrigated to the root of the one-leaf stage oriental melon (variety: golden melon) cultivated in the pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a Fusarium oxysporum f.sp melanis culture and a culture soil. Then, it was cultivated in a greenhouse, and 28 days after planting, it was investigated according to the following index. The degree of disease of each true leaf and stem was calculated based on this index, and the control value was calculated from the obtained degree of disease by the following formula.
Index (0-2)
0: No lesions, 1: Yellowing of true leaves or stems, 2: Bacterial control value = ((Disease rate of untreated plot-Sickness of treated plot) / Disease degree of untreated plot) x 100

The following compounds showed a control value of 60 or more, and the control effect on the Oriental melon Panama disease was confirmed.
1-131, 1-134, 1-135, 1-136, 1-137, 1-138, 1-143, 1-144, 1-154, 1-161, 1-162, 1-163, 1- 168, 1-170, 1-173, 1-174, 1-175, 1-176, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-191, 1-198, 1-199, 1-200, 1-201, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1- 209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-216, 1-218

An acetone solution of the Example compound prepared to be 0.15 mg / mL was diluted 10-fold with water and used for the test. 0.5 mL was sprayed on the first true leaf of the one-leaf stage oriental melon (variety: golden makuwauri) cultivated in a pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a Fusarium oxysporum f.sp melanis culture and a culture soil. Then, it was cultivated in a greenhouse, and 28 days after planting, it was investigated according to the following index. The degree of disease of each true leaf and stem was calculated based on this index, and the control value was calculated from the obtained degree of disease by the following formula.
Index (0-2)
0: No lesions, 1: Yellowing of true leaves or stems, 2: Bacterial control value = ((Disease rate of untreated plot-Sickness of treated plot) / Disease degree of untreated plot) x 100

The following compounds showed a control value of 60 or more, and the control effect on the Oriental melon Panama disease was confirmed.
1-134, 1-218, 4-2

[Example 10]
<Activity against cucumber seedling blight>
An acetone solution of the Example compound prepared to 0.5 mg / mL was diluted 10-fold with water and subjected to the test. The roots of cotyledonous cucumbers (variety: four-leaf clover) cultivated in pots were soil-irrigated with 3 mL per pot. One day after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a cucumber seedling blight fungus (Pythium ultimum var. Ultimum) culture and culture soil. Then, it was cultivated in a greenhouse, and 15 days after planting, it was investigated according to the following index. The degree of morbidity was calculated based on this index, and the control value was calculated from the obtained degree of morbidity by the following formula.
Index (0-6)
0: No disease, 1: Root pot formation 80% or more, 2: Root pot formation less than 80% -50%, 3: Root pot formation less than 50% -25%, 4: Root pot formation less than 25%, 5: Root No pot formation, 6: Bacterial control value = ((onset degree of untreated plot-onset degree of treated plot) / onset degree of untreated plot) × 100

The following compounds showed a control value of 50 or more, and the control effect on cucumber seedling blight was confirmed.
1-189, 1-209

[Example 11]
<Activity against Chinese cabbage buttock rot>
An acetone solution of the Example compound prepared to 0.5 mg / mL was diluted 10-fold with water and subjected to the test. The roots of Chinese cabbage (variety: Musou) in the three-leaf stage of the true leaves cultivated in pots were soil-irrigated with 3 mL per pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a Rhizoctonia solani culture and a culture soil. Then, it was cultivated in a greenhouse, and 15 days after planting, it was investigated according to the following index. The degree of morbidity was calculated based on this index, and the control value was calculated from the obtained degree of morbidity by the following formula.
Index (0-6)
0: No disease, 1: Root pot formation 80% or more, 2: Root pot formation less than 80% -50%, 3: Root pot formation less than 50% -25%, 4: Root pot formation less than 25%, 5: Root No pot formation, 6: Bacterial control value = ((onset degree of untreated plot-onset degree of treated plot) / onset degree of untreated plot) × 100

The following compounds showed a control value of 50 or more, and the control effect on Chinese cabbage ass rot was confirmed.
1-30, 1-41, 1-117, 1-189, 1-193, 1-197

[Example 12]
<Activity against lettuce root rot>
A wettable powder was prepared according to Formulation Example 1. It was diluted 5000 times with water, irrigated with 2 L of lettuce (variety: Raptor) 20 days after sowing cultivated in a 220-well paper pot, and planted the next day. 44 days after planting, the number of strains by disease index in the underground was investigated according to the following index, and the degree of disease was calculated. From the obtained degree of morbidity, the control value was calculated by the following formula.
Index (0-3)
Index 0: No browning, Index 1: Part of the vascular bundle is browned, Index 2: Browning extends around the crown, Index 3: Browning of the crown is severe or hollowed out, or withered (due to the death of the entire strain) ).
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The control effect of the following compounds on lettuce root rot was confirmed.
1-199

[Example 13]
<Growth inhibitory activity against pathogenic fungi of soil diseases>
The Example compound was dissolved in DMSO to 12.8 mg / mL. Cucumber seedlings cultivated in a potato sucrose liquid medium (Pythium ultimum), Rhizoctonia solani, Fusarium oxysporum, and Homopsis rhizoctonia bacillus (Phomoss It was ground in an instrument factory) and appropriately diluted with a potato sucrose medium to prepare a bacterial solution. 200 μL of the bacterial solution was added to 1 μL of the DMSO solution of the example compound, and the cells were cultured at 25 ° C. for 3 days, and then the presence or absence of inhibition of hyphal elongation was visually determined.

The following compounds did not show inhibition of hyphal elongation.
1-198, 1-199

[Pharmaceutical example 1]
Example Compound 10 parts by mass, lauryl sulfate 2 parts by mass, polyoxyethylene alkyl ether 2 parts by mass, lignin sulfonate 3 parts by mass, white carbon 4 parts by mass, and clay 79 parts by mass are mixed and pulverized to prepare a wettable powder. Got

According to the present invention, it is possible to provide a method for controlling soil diseases. The soil disease control agent of the present invention has excellent resistance-inducing activity and is useful for controlling soil diseases.

Claims (9)

A soil disease control agent comprising a compound represented by the following formula (1) as an active ingredient.

[In the formula (1), X ¹ and X ⁴ may be the same or different, and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, but any ^one of X ^{1 and X 4 1} One indicates a fluorine atom or a trifluoromethyl group, and X ² and X ³ may be the same or different, and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group, except that X ¹ and X ^2. and when referring to any one of fluorine atom of X ^4, any one other two showed no hydrogen atom,
X ^{a is a group} represented by the following formula (2), (3), (4) or (5).

In formula (2), J represents an oxygen atom or a sulfur atom.
A is
An alkyl group having 1 to 12 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the group C below, a thiol group, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group.
An alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
An alkynyl group having 2 to 8 carbon atoms, which may be substituted with 1 to 3 groups selected from the groups of the C group below.
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the following C group groups.
An alkylsulfonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D below, a benzyl group, a phenyl group and a phenoxy group,
A phenylsulfonyl group which may be substituted with 1 to 4 groups selected from the groups of Group D below,
A phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the group D below, a phenoxy group and a benzyl group,
5,6,7,8-tetrahydronaphthyl group,
Naphthalene group,
A heterocyclic group may be substituted with 1 to 4 groups selected from the groups of the following group D (here, the heterocyclic group is a group selected from the group E below), or the following formula (2A). [In the formula (2A), X ¹ , X ² , X ³ and X ⁴ are the same as the definitions in the formula (1). ] Is the group indicated by

When A is a group represented by the above formula (2A), Q is a _{divalent group represented by the formula: -O- (CH 2} ) _n- O-, and the formula: -NH- (CH ₂ ) _n-. Divalent group represented by O-, formula: -NH- (CH ₂ ) _{divalent group represented by n-} NH-, formula: -O-CH ₂ -CH = CH-CH _2- O- A divalent group represented by the formula: -NH-CH ₂ -CH = CH-CH _2- O-, a divalent group represented by the formula: -NH-CH ₂ -CH = CH-CH _2- NH- Divalent group, cyclohexane-1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, formula: -NH- (cyclohexane-1,4-diyl) -O-, divalent group, 1 , 3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: divalent group represented by -NH- (1,4-phenylene) -O-, or the following formula (2B) [in the formula (2B), G is an oxygen atom, a sulfur atom or the formula: -SO ₂ - is a divalent group represented by. ] Is a divalent group (where n represents an integer of 2 to 8).

If A is not the group represented by the formula (2A), Q is an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH-, or 2 represented by the formula: -N (CH ₃ )-. It is the basis of the price,
In formula (3), Aa is a piperidin-1-yl group, 1-methyl-1-1H-pyrrole-2-yl group, morpholine-4-yl group, indolin-1-yl group, benzoisothiazole-3. (2H) -On-1,1-dioxide-2-yl group, piperazine-1-yl group, azetidine-1-yl group, 2,5-dioxopyrrolidine-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazole-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazole-2 (3H) -yl group, 5,6- Dihydro-4H-1,3-oxadin-2-yl group, 1H-pyrrol-2-yl group or isothiazole-2-yl group,
In formula (4), Qb represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: -NH- or a divalent group represented by the formula: -N (CH ₃ )-.
Ab is
Hydrogen atom,
An alkyl group having 1 to 10 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the group C below, a hydrogen atom, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group.
An alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
An alkynyl group having 2 to 8 carbon atoms, which may be substituted with 1 to 3 groups selected from the groups of the C group below.
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of C group.
A heterocyclic group which may be substituted with a phenylcarbonyl group or 1 to 4 groups selected from the groups of the following group D (here, the heterocyclic group is a group selected from the group E below) is shown. ,
In formula (5), m represents an integer of 1 to 3 and Z represents a hydrogen atom, a halogen atom or a methyl group.
Group C is a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, and 1 to 3 groups selected from the following groups of the D group. It is a group consisting of a pyridyl group which may be substituted and a phenyl group which may be substituted with 1 to 4 groups selected from the groups of the D group below.
Group D is substituted with a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, and 1 to 3 halogen atoms. It is a group consisting of an alkyloxy group having 1 to 4 carbon atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, a nitro group, and a cyano group.
Group E includes pyridyl group, thiazolyl group, pyrazinyl group, pyridazinyl group, isothiazolidyl group, isoxazolyl group, pyrimidinyl group, benzimidazolyl group, thienyl group, furanyl group, benzoxanyl group, 2,3-dihydrobenzo [b] [1, 4] Dioxin-6-yl group, dihydrothiazolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoisothiazole-3 (2H) -one-1,1-diokidinyl group, dibenzofuranyl group, isothiazolyl group, And a group consisting of a triazolyl group. ] The soil disease control agent according to claim 1, wherein in the formula (1), X ¹ , X ² , X ³ and X ^{4 are hydrogen atoms or fluorine atoms.} The soil disease control agent according to claim 1 or 2, wherein in the formula (1), X ¹ and X ⁴ represent a fluorine atom, and X ² or X ^{3 is a hydrogen atom.} The soil disease control according to any one of claims 1 to 3, wherein in the formula (1), X ¹ and X ⁴ represent a fluorine atom, and X ² and X ^{3 are hydrogen atoms.} Agent. The soil disease control agent according to any one of claims 1 to 4, wherein J is an oxygen atom in the formula (2). The soil disease control agent according to any one of claims 1 to 5, wherein Q is a divalent group represented by the formula: -NH- in the formula (2). The soil disease control agent according to any one of claims 1 to 5, wherein Q is an oxygen atom in the formula (2). In the formula (2), an alkyl group having 1 to 12 carbon atoms, wherein A may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkynyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the C group.
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D, the benzyl group, the phenyl group and the phenoxy group.
A phenylsulfonyl group which may be substituted with 1 to 4 groups selected from the groups of the D group.
Substituted with 1 to 5 groups selected from the group consisting of the group D, phenoxy group and benzyl group, or 1 to 4 groups selected from the group D. The soil disease according to any one of claims 1 to 7, wherein the heterocyclic group may be a heterocyclic group (here, the heterocyclic group is a group selected from the group E). Control agent. A method for controlling soil diseases, which comprises contacting the soil disease control agent according to any one of claims 1 to 8 with a plant or seed, or incorporating the soil disease control agent into a cultivation bed.