JP2021080280A - Agricultural and horticultural disease control agent and plant disease control method - Google Patents

Abstract

To provide a novel disease control agent suitable for specific plants.SOLUTION: An agricultural and horticultural disease control agent contains as an active ingredient a compound represented by the general formula (I) in the figure, or an N-oxide or agrochemically acceptable salt thereof, and is for foliar or non-foliar application.SELECTED DRAWING: None

Description

The present invention relates to an agricultural and horticultural disease control agent and a method for controlling plant diseases.

Conventionally, there has been a demand for agricultural and horticultural chemicals having low toxicity to humans and animals, excellent handling safety, and showing a high control effect against a wide range of plant diseases.

For example, Patent Document 1 discloses an agricultural and horticultural drug containing a novel azole derivative as an active ingredient. Further, Patent Documents 2 and 3 disclose a method for controlling diseases of corn or soybean by a novel triazole compound.

International Publication No. 2019/093522 International Publication No. 2020/20921 International Publication No. 2020/20922

On the other hand, it is not known to control diseases caused by phytopathogens by treating a specific plant such as corn with a novel azole derivative disclosed in Patent Document 1.

One aspect of the present invention is to realize the provision of a novel disease control agent suitable for a specific plant.

［式（Ｉ）中、
Ａは、Ｎ又はＣＨであり；
Ｄは、水素、ハロゲン基又はＳＲ^Ｄであり；
ここで、Ｒ^Ｄは水素、シアノ基、Ｃ_１−Ｃ_６−アルキル基、Ｃ_１−Ｃ_６−ハロアルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−ハロアルケニル基、Ｃ_２−Ｃ_６−アルキニル基又はＣ_２−Ｃ_６−ハロアルキニル基であり；
Ｒ^１は、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基、フェニル−Ｃ_２−Ｃ_４−アルキニル基又はＣＯＸＲ^５であり；
ここで、Ｒ^５は、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基又はフェニル−Ｃ_２−Ｃ_４−アルキニル基であり；
Ｘは、単結合、−Ｏ−又は−ＮＲ^６−であり；
Ｒ^６は、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基又はフェニル−Ｃ_２−Ｃ_４−アルキニル基であり、Ｒ^５とＲ^６とは環を形成していてもよく；
Ｒ^２は、−ＯＲ^７又は−ＮＲ^８Ｒ^９であり；
Ｒ^７、Ｒ^８及びＲ^９は、それぞれ独立に、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基又はフェニル−Ｃ_２−Ｃ_４−アルキニル基であり、Ｒ^８とＲ^９とは環を形成していてもよく；
ここで、Ｒ^１、Ｒ^２、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８及びＲ^９における脂肪族基は、１、２、３若しくは可能な最大数の同一の又は異なる基Ｒ^ａを有していてもよく、Ｒ^ａは、ハロゲン基、シアノ基、ニトロ基、Ｃ_１−Ｃ_４−アルコキシ基及びＣ_１−Ｃ_４−ハロアルコキシ基から互いに独立して選択され；
Ｒ^４は、ハロゲン基、シアノ基、ニトロ基、アミノ基、フェニル基、フェニル−オキシ基、Ｃ_１−Ｃ_４−アルキル基、Ｃ_１−Ｃ_４−ハロアルキル基、Ｃ_１−Ｃ_４−アルコキシ基又はＣ_１−Ｃ_４−ハロアルコキシ基、Ｃ_１−Ｃ_４−アルキルアミノ基、Ｃ_１−Ｃ_４−ジアルキルアミノ基、Ｃ_１−Ｃ_４−アルキルアシルアミノ基、−ＳＯＲ^１０又は−ＳＦ_５であり；
Ｒ^１、Ｒ^２、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８及びＲ^９におけるシクロアルキル基若しくはフェニル基部分又はＲ^４におけるフェニル基部分は、１、２、３、４、５若しくは可能な最大数の同一の又は異なる基Ｒ^ｂを有していてもよく、Ｒ^ｂは、ハロゲン基、シアノ基、ニトロ基、Ｃ_１−Ｃ_４−アルキル基、Ｃ_１−Ｃ_４−アルコキシ基、Ｃ_１−Ｃ_４−ハロアルキル基及びＣ_１−Ｃ_４−ハロアルコキシ基から互いに独立して選択され；
Ｒ^３は、ハロゲン基、シアノ基、ニトロ基、フェニル基、フェニル−オキシ基、Ｃ_１−Ｃ_４−アルキル基、Ｃ_１−Ｃ_４−ハロアルキル基、Ｃ_１−Ｃ_４−アルコキシ基、Ｃ_１−Ｃ_４−ハロアルコキシ基、−ＳＯＲ^１０又は−ＳＦ_５であり；
ここで、Ｒ^１０は、Ｃ_１−Ｃ_４−アルキル基又はＣ_１−Ｃ_４−ハロアルキル基であり；
Ｅは、フェニル基又はＮ原子を１若しくは２つ含む６員の芳香族複素環であり；
Ｒ^３は任意の置換位置にｎ個結合しており；
Ｅがフェニル基の場合、ｎは０、１、２、３又は４であり、ＥがＮ原子を１若しくは２つ含む６員の芳香族複素環である場合は、ｎは０、１又は２であり；
Ｙは、Ｅの任意の位置に接続する酸素原子、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＮＨ−、−Ｎ（−Ｃ_１−Ｃ_４−アルキル）−、−Ｎ（−Ｃ_３−Ｃ_６−シクロアルキル）−又は−Ｓ（Ｏ）_ｐ−であり；
ｐは、０、１又は２であり；
Ｚは、フェニル基若しくはナフチル基である芳香族炭化水素基、又は、Ｏ、Ｎ若しくはＳから選択されるヘテロ原子を１〜４つ含む５員又は６員の芳香族複素環若しくは２環から構成される９員又は１０員の芳香族複素環であり；
Ｒ^４は任意の置換位置にｍ個結合しており；
Ｚがフェニル基である場合、ｍは１、２、３、４又は５であり、Ｚがナフチル基又は芳香族複素環である場合、ｍは０、１、２、３又は４である］ In order to solve the above problems, the agricultural and horticultural disease control agent according to one aspect of the present invention is a compound represented by the following general formula (I), or an N-oxide or a pesticide-acceptable salt thereof. Is a disease control agent for agriculture and horticulture, which contains as an active ingredient and is used for foliage treatment or non-foliage treatment.

[In formula (I),
A is N or CH;
D is hydrogen, halogen or SR ^D;
Here, ^RD is hydrogen, cyano group, C _1- C ₆ -alkyl group, C _1- C ₆ -haloalkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -haloalkenyl group, C ₂ -C ₆ -alkynyl group or C _2- C ₆ -haloalkynyl group;
R ¹ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group, phenyl-C _2- C ₄ -alkynyl group or COXR ⁵ Yes;
Here, R ⁵ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C. ₈ -Cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group Yes;
X is a single bond, -O- or -NR ^6- ;
R ⁶ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group, R ⁵ and R ⁶ may form a ring;
R ² is -OR ⁷ or -NR ⁸ R ⁹ ;
R ⁷ , R ⁸ and R ⁹ are independently hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cyclo. Alkyne group, C _3- C ₈ -cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C ₂ It is a -C ₄ -alkynyl group, and R ⁸ and R ⁹ may form a ring;
^Here, the aliphatic group represented by ^{R 1, R 2, R 5} , R 6, R 7, R 8 and ^{R 9} have the same or different groups ^{R a} 1, 2, 3 or maximum possible number ^Ra may be selected independently of each other from halogen groups, cyano groups, nitro groups, C _1- C ₄ -alkoxy groups and C _1- C _{4-haloalkoxy groups;}
R ⁴ is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, and a C _1- C ₄ -alkoxy group. or _C 1 -C ₄ - haloalkoxy _group, C 1 -C ₄ - alkylamino _group, C 1 -C ₄ - dialkylamino _group, C 1 -C ₄ - alkyl acyl amino group, in -SOR ¹⁰ or -SF ₅ Yes;
The cycloalkyl group or phenyl group moiety in R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ^{9 or the phenyl group moiety in R 4} is 1, 2, 3, 4, 5 or the maximum possible. It may have the same or different number of groups R ^b , where R ^b is a halogen group, a cyano group, a nitro group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -alkoxy group, C ₁ -C ₄ - haloalkyl groups and _C 1 -C ₄ - is selected from haloalkoxy groups independently of each other;
R ³ is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, a C _1- C ₄ -alkoxy group, and a C ₁ -C ₄ -haloalkoxy group, -SOR ¹⁰ or -SF ₅ ;
^{Wherein, R 10} _is, C 1 -C ₄ - alkyl group or a _C 1 -C ₄ - haloalkyl group;
E is a 6-membered aromatic heterocycle containing one or two phenyl groups or N atoms;
R ³ is bound to any substitution position by n;
When E is a phenyl group, n is 0, 1, 2, 3 or 4, and when E is a 6-membered aromatic heterocycle containing 1 or 2 N atoms, n is 0, 1 or 2. Is;
Y is an oxygen atom connected to an arbitrary position of E, -CH ₂ O-, -OCH _2- , -NH-, -N (-C _1- C ₄ -alkyl)-, -N (-C _3-). C ₆ -cycloalkyl)-or -S (O) _p- ;
p is 0, 1 or 2;
Z is composed of an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5- or 6-membered aromatic heterocycle or 2 rings containing 1 to 4 heteroatoms selected from O, N or S. Is a 9- or 10-membered aromatic heterocycle;
R ⁴ is and m pieces bonded to any substitutable position;
If Z is a phenyl group, m is 1, 2, 3, 4 or 5, and if Z is a naphthyl group or an aromatic heterocycle, m is 0, 1, 2, 3 or 4].

According to one aspect of the present invention, it is possible to provide a novel disease control agent suitable for a specific plant.

[Agricultural and horticultural disease control agents]
The agricultural and horticultural disease control agent of the present embodiment is a compound represented by the following general formula (I) (hereinafter, may be referred to as an azole derivative (I)).

In the general formula (I), A is N or CH, preferably N. D is hydrogen, a halogen group or an SR ^{D, R D} is hydrogen, cyano _groups, C 1 -C ₆ - alkyl _groups, C 1 -C ₆ - haloalkyl _groups, C 2 -C ₆ - alkenyl groups, C _{It is a 2-} C ₆ -haloalkenyl group, a C _2- C ₆ -alkynyl group or a C _2- C ₆ -haloalkynyl group. D is preferably hydrogen.

The C _1- C ₆ -alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms, and is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, or 1-methyl. Propyl group, 2-methylpropyl group, 1-ethylpropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, 2-methylbutyl group, 3,3-dimethylbutyl group, 2,2- Examples thereof include a dimethylbutyl group, a 1,1-dimethylbutyl group, a pentyl group, a 1-methylpentyl group, a neopentyl group, and a 1,1-dimethylethyl group.

C ₂ -C ₆ - alkenyl group, a linear or branched alkenyl group having a carbon atom is 2-6, for example, ethenyl, 2-propenyl group, 1-methyl-2-propenyl group , 2-Methyl-2-propenyl group, 1-butenyl group, 2-butenyl group, 3-methyl-2-butenyl group, 1-methyl-2-butenyl group, 3-butenyl group, 1-pentenyl group, 2- Examples include a pentenyl group, a 1-hexenyl group and a 5-hexenyl group.

C ₂ -C ₆ - alkynyl group, a linear or branched chain alkynyl group having a carbon atom is 2-6, for example, ethynyl group, 1-propynyl, 2-propynyl, 1-butynyl Examples include groups, 2-butynyl groups, 3-butynyl groups, pentynyl groups and 1-hexynyl groups.

The C _1- C ₆ -haloalkyl group, C _2- C ₆ -haloalkenyl group, or C _2- C ₆ -haloalkynyl group is the above-mentioned C _1- C ₆ -alkyl group and C _2- C ₆ -alkenyl group, respectively. group, or a C ₂ -C 6 _- 1 or 2 or more halogen atoms substituted may position is substituted alkynyl group, in the case of the halogen group is 2 or more to be replaced, even if the halogen groups are the same or different good. Examples of the halogen group include a chlorine group, a bromine group, an iodine group and a fluorine group. For example, a chloromethyl group, a 2-chloroethyl group, a 2,3-dichloropropyl group, a bromomethyl group, a chlorodifluoromethyl group, a trifluoromethyl group, and a 3,3,3-trifluoropropyl group can be mentioned.

R ¹ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group, phenyl-C _2- C ₄ -alkynyl group or COXR ⁵ is there. _C 1 -C ₆ in R ¹ - alkyl _group, C 2 -C ₆ - alkenyl, and _C 2 -C ₆ - The alkynyl groups, and the groups mentioned as examples of the organic groups represented by ^{R D} Can be done. R ¹ is preferably hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group or COXR ⁵ , and more preferably hydrogen, C _1- C ₆ - an alkyl group or COXR ^5, and most preferably hydrogen or _C 1 -C ₆ - alkyl group.

The C _3- C ₈ -cycloalkyl group is a cyclic alkyl having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Be done.

The C _3- C ₈ -cycloalkyl-C _1- C ₄ -alkyl group consists of a cyclic cycloalkyl group having 3 to 8 carbon atoms and a linear or branched chain alkyl group having 1 to 4 carbon atoms. Indicates that they are combined. For example, cyclopropylmethyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-cyclopropylethyl group, 1-cyclopropylethyl group, 2-cyclohexylethyl group, 3-cyclopropylpropyl group, 2-cyclo Examples thereof include a propylpropyl group and a 4-cyclopropylbutyl group.

The phenyl-C _1- C ₄ -alkyl group is prepared by substituting a linear or branched alkyl group having 1 to 4 carbon atoms with a phenyl group, for example, a phenylmethyl group, a 2-phenylethyl group, or the like. Examples thereof include 3-phenylpropyl group and 4-phenylbutyl group.

The phenyl-C _2- C ₄ -alkenyl group has a linear or branched alkenyl group having 2 to 4 carbon atoms bonded to the phenyl group, for example, a phenylethenyl group or a phenyl-1-propenyl. Groups include groups, phenylisopropenyl groups, and phenylbutenyl groups.

The phenyl-C _2- C ₄ -alkynyl group has an alkynyl group having 2 to 4 carbon atoms bonded to the phenyl group, and is, for example, a phenylethynyl group, a phenyl-1-propynyl group, or a phenyl-2-propynyl group. , Phenyl-1-butynyl group, phenyl-2-butynyl group, phenyl-3-butynyl group, and phenyl-3-butynyl group.

R ⁵ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group. These can be mentioned as examples of the organic groups represented by ^{R D} and R ^1. R ⁵ is preferably hydrogen, a C _1- C ₆ -alkyl group, a C _2- C ₆ -alkenyl group or a C _2- C ₆ -alkynyl group, and more preferably hydrogen or C _1- C _6-. It is an alkyl group.

X is a single bond, -O- or -NR ^6- , R ⁶ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C ₃ -C ₈ - cycloalkyl _group, C 3 -C ₈ - cycloalkyl _-C 1 -C ₄ - alkyl group, a phenyl group, a phenyl _-C 1 -C ₄ - alkyl group, a phenyl _-C 2 -C ₄ - It is an alkenyl group or a phenyl-C _2- C ₄ -alkynyl group, and these can be mentioned as examples of organic groups represented by ^{R D} and R ^1. R ⁶ is preferably hydrogen, a C _1- C ₆ -alkyl group, a C _2- C ₆ -alkenyl group or a C _2- C ₆ -alkynyl group, and more preferably hydrogen. R ⁵ and R ⁶ may form a ring.

R ² is −OR ⁷ or −NR ⁸ R ⁹ , preferably −OR ⁷ . R ⁷ , R ⁸ and R ⁹ are independently hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cyclo. Alkyl group, C _3- C ₈ -cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C ₂ -C ₄ -alkynyl groups, which can be mentioned as examples of the organic groups represented by ^{R D} and R ^1. R ⁸ and R ⁹ may form a ring.

R ⁷ is _preferably, C 1 -C ₆ - alkyl group.

R ^1, aliphatic group in ^{R 2, R 5, R 6} , R 7, R 8 and ^{R 9} have the same or different groups ^{R a} 1, 2, 3 or maximum possible number well, ^{R a} is halogen, cyano, _nitro, C 1 -C ₄ - alkoxy and _C 1 -C ₄ - haloalkoxy groups independently of each other. The C _1- C ₄ -alkoxy group is a linear or branched alkoxy group having 1 to 4 carbon atoms, and is, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, or an n-butoxy. Groups, sec-butoxy groups, tert-butoxy groups can be mentioned.

Further, the C _1- C ₄ -alkoxy group may be substituted with one or two or more halogen groups at substitutable positions, and when the number of substituted halogen groups is two or more, the halogen groups are the same or different. You may.

E is a 6-membered aromatic heterocycle containing one or two phenyl groups or N atoms. E is preferably a phenyl group. The form in which E is a phenyl group is as shown by the following general formula (I'). Further, the following general formula (I'') is preferable.

R ³ is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, a C _1- C ₄ -alkoxy group, and a C ₁ -C ₄ -haloalkoxy group, -SOR ¹⁰ or -SF ₅ . The halogen group, C _1- C ₄ -alkyl group, C _1- C ₄ -haloalkyl group, C _1- C ₄ -alkoxy group, and C _1- C ₄ -haloalkoxy group are R ^D , R ¹ or ^Ra. Examples of the organic group represented by (1) can be mentioned. R ³ is preferably a halogen group, a cyano group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, a C _1- C ₄ -alkoxy group, -SOR ¹⁰ or -SF ₅ . more preferably, a halogen group, a cyano _group, C 1 -C ₄ - alkoxy group - alkyl _group, C 1 -C ₄ - haloalkyl group or a _C 1 -C _4. R ¹⁰ is a C _1- C ₄ -alkyl group or a C _1- C ₄ -haloalkyl group. When E is a phenyl group, ^{the substitution position of R 3} is the 2-position, 3-position, 5-position or 6-position, preferably the 2-position. n is 0, 1, 2 or 3, preferably 1. When E is a 6-membered aromatic heterocycle containing 1 or 2 N atoms, ^{the substitution position of R 3 is} the position not containing N atoms among the 2-position, 3-position, 5-position and 6-position. Yes, preferably second place. In this case, n is 0, 1 or 2, preferably 1.

R ⁴ is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, and a C _1- C ₄ -alkoxy group. or _C 1 -C ₄ - haloalkoxy _group, C 1 -C ₄ - alkylamino _group, C 1 -C ₄ - dialkylamino _group, C 1 -C ₄ - alkyl acyl amino group, in -SOR ¹⁰ or -SF ₅ Yes, halogen groups, C _1- C ₄ -alkyl C _1- C ₄ -haloalkyl groups, C _1- C ₄ -alkoxy groups or C _1- C ₄ -haloalkoxy groups, and -SOR ¹⁰ are R ^D , R ¹ and it can be a group mentioned as examples of the organic groups represented by R ^3. R ⁴ is preferably a halogen group, a nitro group, an amino group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, a C _1- C ₄ -alkoxy group, and a C _1- C ₄ -halo. alkoxy _groups, C 1 -C ₄ - alkylamino _group, C 1 -C ₄ - dialkylamino _group, C 1 -C ₄ - alkyl acyl amino group, an -SOR ¹⁰ or -SF _5, more preferably a halogen group , C _1- C ₄ -alkyl group, C _1- C ₄ -haloalkyl group, C _1- C ₄ -alkoxy group or C _1- C ₄ -haloalkoxy group.

The C _1- C ₄ -alkylamino group is an amino group in which one of the hydrogen atoms of the amino group is replaced with a linear or branched alkyl group having 1 to 4 carbon atoms, for example, methylamino. Examples include groups, ethylamino groups, n-propylamino groups, isopropylamino groups, and tert-butylamino groups.

C 1 _-C 4 _- dialkylamino group is an amino group in which a hydrogen atom of two co-having amino group substituted by a straight chain or branched chain alkyl group having 1 to 4 carbon atoms, e.g., N , N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group, N, N-diisopropylamino group, and N, N-di-tert-butylamino group.

The C _1- C ₄ -alkyl acyl amino group is an amino group in which one or two of the hydrogen atoms of the amino group are substituted with a linear or branched alkyl acyl group having 1 to 4 carbon atoms. For example, methyl acylamino group, ethyl acylamino group, n-propyl acylamino group, isopropyl acylamino group, tert-butyl acylamino group, N, N-dimethylacylamino group, N, N-diethylacylamino group, Examples thereof include N, N-di-n-propyl acylamino groups, N, N-diisopropyl acylamino groups, and N, N-di-tert-butyl acylamino groups.

The cycloalkyl group or phenyl group moiety in R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ^{9, or the phenyl group moiety in R 3} or R ⁴ is 1, 2, 3, 4, 5 or maximum possible number of may have the same or different groups ^{R b, R b} is halogen, cyano, _nitro, C 1 -C ₄ - alkyl _group, C 1 -C ₄ - alkoxy The groups are independently selected from _{the C 1-} C ₄ -haloalkyl group and the C _1- C _{4-haloalkoxy group.} The halogen group, C _1- C ₄ -alkyl group, C _1- C ₄ -alkoxy group, C _1- C ₄ -haloalkyl group and C _1- C ₄ -haloalkoxy group are R ^D , R ¹ or ^Ra . Examples of the represented organic groups include the groups listed.

Y ^{is, (R} _{3) n} is oxygen atom be connected to any position of the phenyl group _{attached, -CH 2 O -, - OCH} 2 -, - NH -, - N (-C 1 -C 4 - Alkyl)-, -N (-C _3- C ₆ -cycloalkyl)-or -S (O) _p- , where p is 0, 1 or 2, preferably an oxygen atom.

Further, Y is ortho position of the phenyl group to which R ³ is substituted, is bonded to meta or para position, preferably meta or para position.

Z is composed of an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5- or 6-membered aromatic heterocyclic group or 2 rings containing 1 to 4 heteroatoms selected from O, N or S. It is a 9- or 10-membered aromatic heterocyclic group. Z is preferably a phenyl group or a 5- or 6-membered aromatic heterocycle containing 1 to 3 heteroatoms selected from N and S, and more preferably a phenyl group.

Examples of the 5- or 6-membered aromatic heterocyclic group include a frill group, a pyrazolyl group, a thienyl group, a pyridyl group, a pyrimidinyl group, a pyridadinyl group, a pyrazinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group and an isothiazolyl group. Examples thereof include a group, an oxazolyl group, an isooxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, or a triazinyl group.

The 9- or 10-membered aromatic heterocyclic group composed of two rings includes an indolyl group, an isoindryl group, a benzoimidazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a synnolyl group, a benzopyranyl group, and a pteridinyl group. Can be mentioned.

R ⁴ is bonded to an arbitrary substitution position in m pieces, and is preferably at the 2-position, 3-position, 4-position, or 5-position. When Z is a phenyl group, m is 1, 2, 3, 4 or 5, and when Z is a naphthyl group or an aromatic heterocycle, m is 0, 1, 2, 3 or 4.

The pesticide-acceptable salts of the azole derivative (I) are, in particular, salts of these cations or acid addition salts of these acids, the cations and anions of which do not adversely affect the action of the azole derivative (I). Including. Suitable cations are particularly ammonium ions of alkali metals (preferably sodium and potassium), alkaline earth metals (preferably calcium, magnesium and barium), transition metals (preferably manganese, copper, zinc and iron) and also. Ammonium ions (preferably diisopropylammonium, tetramethylammonium, which may have _{1 to 4} C1-C4-alkyl substituents and / or 1 phenyl or benzyl substituent, if desired. tetrabutylammonium, trimethylbenzylammonium), furthermore phosphonium ions, sulfonium ions (preferably tri _(C 1 -C ₄ - alkyl) sulfonium), and sulfoxonium ions (preferably tri _(C 1 -C ₄ - alkyl) sulfonium It is also (xonium). Useful acid addition salt anions are mainly chloride ion, bromide ion, fluoride ion, hydrogen sulfate ion, sulfate ion, dihydrogen phosphate ion, hydrogen phosphate ion, phosphate ion, nitrate ion, bicarbonate. ions, carbonate ions, hexafluorosilicic acid ion, hexafluorophosphate ion, benzoate ion, and C ₁ -C 4 _- anions of alkanoic acids, preferably ion formic acid, acetate ion, propionate and butyrate. These can be formed by reacting the azole derivative (I) with the corresponding anionic acid (preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid).

Since the azole derivative (I) has an asymmetric carbon atom, the azole derivative (I) has an enantiomer. The azole derivative (I) contains both such isomers alone and those containing each of these isomers in an arbitrary ratio.

The azole derivative (I) can be produced by a known method. For example, the azole derivative (I) can be produced by referring to the production method described in Patent Document 1.

[Applicable diseases of agricultural and horticultural disease control agents]
The agricultural and horticultural disease control agent in the present embodiment exhibits a control effect on a wide range of plant diseases. Examples of applicable diseases include the following. The parentheses after each disease indicate the main pathogens that cause the disease. Soybean rust (Phakopsora pachyrhizi, Phakopsora meibomiae), soybean brown spot disease (Septoria glycines), soybean purpura (Cercospora kikuchii), soybean brown spot disease (Alternaria spp.), Soybean charcoal disease (Collectotrichum truncatum, Colletotrichum glysines) Frogeye leaf spot (Cercocpora sojina), soybean lysoctonia solani, soybean leaf rot (Rhizoctonia solani), soybean black spot (Diaporthe phaseolorum), soybean stem epidemic (Phytophthora sojae), soybean red mold (Soybean red mold) Fusarium avenaceum, Fusarium oxysporum, soybean wilt (Verticillium dahliae), soybean udon (Erysiphe glycines), soybean brown ring pattern (Corynespora cassiicola), soybean brown spot (Mycosphaerella sojae), soybean black root rot (Calonectria ilici) ), Soybean black root disease (Thielaviopsis spp.), Soybean ring pattern disease (Ascochyta phaseolorum), Soybean black scab (Elsinoe glycines), Soybean acute mortality (Fusariumu genus such as Fusarium virguliforme), Green beans charcoal scab (Colletotrichum lindemuianum), Rapeseed Phoma leaf spot / stem canker (Leptosphaeria maculans, Leptosphaeria biglobosa), Rapeseed Light leaf spot (Pyrenopeziza brassicae), Rapeseed root-knot disease (Plasmodiophora brassicae), Rapeseed verticillium wilt (Verticillium longisporum) Alternaria spp.), Rice blast (Pyricularia oryzae), Rice sesame leaf blight (Cochliobolus miyabeanus) ), Rice white leaf blight (Xanthomonas oryzae), Rice crest blight (Rhizoctonia solani), Wheat small black fungus nucleus disease (Helminthosporium sigmoideun), Rice fool seedling disease (Fusarium fujikuroi), Rice seedling blight (Pythium spp.), Rice blight (Gaeumannomyces graminicola), Wheat Udonko disease (Erysiphe graminis f. Sp hordei), Wheat black rust (Puccinia graminis), Wheat yellow rust (Puccinia striiformis), Wheat small fungus (Puccinia hordei) Pyrenophora graminea, Rhynchosporium secalis, Ustilago nuda, Pyrenophora teres, Fusarium graminearum, Microdochium nivale Diseases (Ramularia collo-cygni), Wheat Udonko disease (Erysiphe graminis f. Sp tritici), Wheat red rust (Puccinia recondita), Wheat yellow rust (Puccinia striiformis), Wheat eye print disease (Pseudocercosporella herpotrichoides), Wheat red mold Diseases (Fusarium graminearum, Microdochium nivale), Wheat wilt (Phaeosphaeria nodorum), Wheat leaf blight (Zymoseptoria tritici), Wheat crimson snow rot (Microdochium nivale), Wheat wilt (Gaeumannomyces graminis), Wheat black spot (Gaeumannomyces graminis) Epicoccum spp.), Wheat yellow spot disease (Pyrenophora tritici-repentis), Wheat snow rot brown small granule nuclei disease (Typhula incarnata), Wheat snow rot black granule nuclei disease (Typhula ishikariensis), Shibadara spot disease (Sclerotinia homoeocarpa), Wheat patch disease (Rhizoctonia) solani), Shiva Brown patch disease (Rhizoctonia solani), Shiva charcoal disease (Colletotrichum graminicola), Shiva's Gray leaf Spot (Pyricularia grisea), Shiba crotic ring spot disease (Ophiosphaerella korrae), Shiva's Red thread (Laetisaria fuciformis), Shiva rust (Puccinia zoysiae), Shiva summer patch disease (Magnaporthe poae), Shiva takeall patch (Gaeumannomyces graminis), Shiva brown ring patch (Waitea circinata), Shiva fairy ring disease (Agaricus, Calvatia cyathiformis, Chlorophyllum molybtes) ., Lepiota spp., Lepista subnuda, Lycoperdon spp., Marasmius oreades, Scleroderma spp., Tricholoma spp. Typhula ishikariensis, Curvularia spp., Binucleate Rhizoctonia, Gaeumannomyces spp., Phialophora spp., Corn black ears Diseases (Ustilago maydis), corn charcoal scab (Colletotrichum graminicola), corn brown spot disease (Kabatiella zeae), corn gray spot disease (Cercospora zeae-maydis), corn soot scab (Exserohilum turcicum), corn northern spot disease (Cochliobolus carbonum) ), Corn spot disease (Physoderma maydis), Corn rust (Puccinia spp.), Corn sesame leaf blight (Cochliobolus heterostrophus), Corn yellow sesame leaf blight (P) hyllosticta maydis), Fusarium red mold (Fusarium asiaticum, Fusarium fujikuroi, Fusarium proliferatum, Fusarium concentricum Fusarium graminearum, Fusarium verticillioides), Phaeosphaeria leal spot (Phaeosphaeria maydis), corn Phaeosphaeria leal spot (Phaeosphaeria maydis), corn Diplo Satoukibi rust (Puccinia spp.), Uri (Podosphaera xanthii), Uri (Colletotrichum orbiculare, Glomerella cingulata), Uri brown spot (Corynespora cassiicola), Uri (Pseudoperonospora) , Cucumber gray plague (Phytophthora capsici), cucumber vine disease (Fusarium oxysporum f.sp.cucumerinum), watermelon vine disease (Fusarium oxysporum f.sp.niveum), apple udonko disease (Podosphaera leucotricha), apple scab (Podosphaera leucotricha) Venturia inaequalis), apple morinia disease (Monilinia mali), apple spot foliar disease (Alternaria alternata apple pathotype), apple rot disease (Valsa ceratosperma), pear black spot disease (Alternaria alternata Japanese pear pathotype), pear udonko disease (Phyllactinia pyri) , Pear red spot disease (Gymnosporangium asiaticum), pear scab (Venturia nashicola), strawberry udonko disease (Podosphaera aphanis), nuclear fruit tree ash (Monilinia fructicola), citrus blue mold (Penicillium italicum), citrus green mold (Penicillium digitatum) , Grape powdery mildew (Uncinula necator), Grape powder (Plasmopara viticola), Grape late rot (Glomerella cingulata, Colletotoricum acutatum), Grape rust (Phakopsora ampelopsidis), Grape black sigato (Elsinoe ampelina), Banana Black sigatoka (Mycosphaerella fijiensis), banana yellow sigatoka (Mycosphaerella musicola), tomato powdery mildew (Erysiphe cichoracearum), tomato ring pattern (Alternaria solani), tomato leaf mold (Passalora fulva), tomato sugatoka (Pseudocercospora) fuligena), tomato brown ring pattern (Corynespora cassiicola), tomato white spot disease (Septoria lycopersici), tomato charcoal disease (Colletotrichum coccodes), eggplant powdery mildew (Erysiphe cichoracearum), potato summer epidemic (Alternaria solani), potato charcoal disease (Colletotrichum coccodes), Jacaimo powdery mildew (Erysiphe cichoracearum, Leveillula taurica), Jacaimo epidemic (Phytophthora infestans), Tobacco powdery mildew (Erysiphe cichoracearum), Tobacco red spot disease (Alternaria longipes), Tensai por Erysiphe betae, Rhizoctonia solani, Thanatephorus cucumeris, Aphanomyces cochlioides, Fusarium oxysporum f.sp.raphani, Cha charcoal Disease (Discula theae-sinensis), Chamochi disease (Exobasidium vexans), Cha brown circle disease (Pseudocercospora ocellata, Cercospora chaae), Cha ring pattern disease (P) estalotiopsis longiseta, Pestalotiopsis theae), Chanet blast (Exobasidium reticulatum), Wata black spot disease (Alternaria spp.), Wata charcoal disease (Glomerella spp.), Wata ring scab (Ascochyta gossypii), Wata rust (Puccinia spp) ., Phykopsora gossypii), Wata's Cercospora blight and leaf spot (Cercospora spp.), Wata's Diplopia boll rot (Diplopia spp.), Wata's Hard lock (Fusarium spp.), Wata's Phoma blight (Phoma spp.), Wata's Stemphyllium leaf spot (Stemphyllium spp.), Lakkasei black astringent disease (Cercosporidium personatum), Lakkasei brown spot disease (Cercospora arachidicola), Lakkasei white silk disease (Sclerotium rolfsii), Lakkasei rust (Puccinia arachidis), various crops Black mold (Botrytis cinerea), diseases of the genus Puccinia (Pythium spp.), Half-body wilt (Verticillium spp.) And cercospora (Sclerotinia sclerotiorum). Also, Aspergillus, Cochliobolus, Corticium, Diplodia, Penicillium, Fusarium, Gibberella, Mucor, Phoma, Phomopsis, Pyrenophora, Pythium, Rhizoctonia, Rhizopus, Thielaviopsis Seed-borne diseases or early-growth diseases of various plants caused by the genus Trichoderma and the genus Ustilago.

Among the above-mentioned diseases, the agricultural and horticultural disease control agent of the present embodiment exhibits a particularly excellent control effect on the diseases of corn or soybean. Therefore, agricultural and horticultural disease control agents are preferably used for controlling corn or soybeans, but are not limited thereto.

[Plants to which agricultural and horticultural disease control agents are applied]
The agricultural and horticultural disease control agent of the present embodiment can be used for all plants, and examples of applicable plants include the following. Rice, wheat, barley, lime, embaku, rye wheat (tricikeel), corn, morokoshi (sorghum), sugar cane, shiva, bentgrass, Bermudagrass, fescue and ryegrass and other rice families, soybeans, lacquer, green beans, peas, azuki and Mustards such as alfarfa, mustards such as sweet potatoes, mustards such as peppers, peppers, tomatoes, eggplants, potatoes and tobacco, mustards such as buckwheat, kikus such as sunflowers, and sardines such as carrots. Family, rapeseed, hakusai, turnip, cruciferous plants such as cabbage and daikon, cruciferous plants such as tensai, blue-green algae such as cotton, red-green algae such as coffee tree, blue-green algae such as cacao, camellia such as cha Family, Brassicaceae such as watermelon, melon, cucumber and pumpkin, Brassicaceae such as onion, onion and garlic, rose family such as strawberries, apples, almonds, apricots, plums, sweet potatoes, peaches, peaches and pears, Seri family such as carrots, Satoimo family such as Satoimo, Urushi family such as mango, Pineapple family such as pineapple, Papaya family such as papaya, Kakinoki family such as oyster, Tsutsuji family such as blueberry, Pekan Walnut family such as walnut family, basho family such as banana, mokusei family such as olive, palm family such as coco palm and nut palm, orange family such as mandarin orange, orange, grapefruit and lemon, grape family such as grape, flowering plant (Flowers and ornamental plants), non-fruit trees and other ornamental plants. In addition, wild plants, plant cultivars, plants and plant cultivars obtained by conventional biological breeding such as cross-breeding or progenitor fusion, and genetically modified plants and plant cultivars obtained by genetic engineering can be mentioned. Examples of genetically modified plants and plant cultivated varieties include herbicide-resistant crops, pest-resistant crops incorporating an insecticidal protein-producing gene, disease-resistant crops incorporating a disease-resistant inducer-producing gene, taste-enhancing crops, and yield improvement. Examples include crops, crops with improved shelf life, and crops with improved yield. Examples of genetically modified plant cultivars approved in each country include those accumulated in the database of the International Agribio Corporation (ISAAA). Specifically, AgriSure, AgriSure 3000GT, AgriSure 3122 EZ Refuge, AgriSure 3122 Refuge Renew, AgriSure Artesian 3030A, AgriSure Artesian 3011A, AgriSure Duracade, AgriSure Duracade 5222 EZ Refuge, AgriSure GT, AgriSure GT / CB AgriSure Viptera 3110, AgriSure Viptera 3111, AgriSure Viptera 3220 EZ Refuge, AgriSure Viptera 3220 Refuge Renew, BiteGard, Bollgard, Bollgard II, Bollgard II / Roundup Ready, Bollgard 3 XtendFlex Cotton, Bollgard Cotton, Bollgard Cotton / BXN Cotton, Bt Maize, BtXtra, BXN, BXN Canola, BXN Cotton, Clearfield, DroughtGard, Enlist, Enlist Cotton, Enlist WideStrike 3 Cotton, Genuity, Genuity Bollgard II XtendFlex, Genuity Intacta RR2 Pro, Genuity SmartStax, Genuity SmartStax RIB Complete , Genuity VT Double Pro, Genuity VT Double Pro RIB Complete, Genuity VT Triple Pro, Genuity VT Triple Pro RIB Complete, GlyTol, GlyTol Cotton, Herculex, Herculex 1, Herculex RW, Herculex XTRA, IMI, IMI Canola, InVigor, KnockOut, Liberty Link, Liberty Link Conola, Liberty Link cotton, NatureGard, Newleaf, Nucotn, Op timum, Optimum AcreMax, Optimum AcreMax I, Optimum AcreMax-R, Optimum AcreMax RW, Optimum AcreMax RW-R, Optimum AcreMax Xtra-R, Optimum AcreMax Xtreme-R, Optimum AcreMax Xtreme, Optimum Intrasect, Optimum Intrasect , Optimum Leptra, Optimum TRIsect, Poast Compatible, Powercore, Powercore Corn, Powercore Corn Refuge Advanced, Protecta, Roundup Ready, Roundup Ready 2, Roundup Ready Conola, Roundup Ready Cotton, Roundup Ready / YieldGard, RR Flex / Bollgard II, SCS, Examples include those that include registered trademarks such as SmartStax, SmartStax Refuge Advanced, StarLink, Twinlink, VipCot, VipCot Cotton, WideStrike, WideStrike 3, Xtend, YieldGard, YieldGard Corn Borner, YieldGard Rootworm, YieldGard Plus and YieldGard VT Triple.

Corn includes field corn, popcorn, sweet corn, seed corn, dent corn, flint corn, flower corn and waxy corn. Soybeans include finite growth type soybeans and infinite growth type soybeans.

[Preparation]
In the agricultural and horticultural disease control agent of the present embodiment, the azole derivative (I), which is an active ingredient, is mixed with a carrier, a surfactant, other pharmaceutical adjuncts, etc. , Water solvent, emulsion, liquid agent, oil agent, aerosol, microcapsule agent, paste agent, coating agent, fumigant agent, fumigant agent, microspray agent, etc.

These preparations contain the azole derivative (I) as an active ingredient in an amount of 0.1 to 95% by weight, preferably 0.5 to 90% by weight, more preferably 2 to 80% by weight.

Examples of the carrier used as the preparation auxiliary agent include a solid carrier and a liquid carrier. As the solid carrier, it is used as a powder carrier, a granular carrier and the like, and for example, clay, talc, diatomaceous earth, zeolite (boiling stone), montmorillonite, bentonite, kaolinite, kaolin, pyrophyllite, waxy stone, acidic white clay, active white clay, etc. Minerals such as attapargite, attapargas clay, limestone, calcified stone, marble, vermiculite, pearlite, plight stone, silica stone, silica sand, sericite and pottery stone; synthetic organic substances such as urea; calcium carbonate, sodium carbonate, magnesium carbonate , Salts such as sodium sulfate, ammonium sulfate, potassium chloride, limestone and baking soda; Synthetic inorganic substances such as amorphous silica (white carbon, fumed silica, etc.) and titanium dioxide; wood flour, corn stalk (ear shaft), walnut shell ( Vegetable carriers such as (hard fruit hulls), fruit nuclei, fir, coconut husks, sardines, bran, soybean flour, powdered cellulose, starch, dextrin and sugars (lactose, sucrose, etc.); crosslinked lignins, cationic gels, heated or polyvalent metal salts. Various polymers such as gelatin gelled in, water-soluble polymer gel (such as agar), chlorinated polyethylene, chlorinated polypropylene, polyvinyl acetate, polyvinyl chloride, ethylene / vinyl acetate copolymer and urea / amorphous resin. Carrier; etc. can be mentioned.

Examples of the liquid carrier include aliphatic solvents such as paraffins (normal paraffin, isoparaffin, naphthen); aromatic solvents such as xylene, alkylbenzene, alkylnaphthalene and solvent naphtha; mixed solvents such as kerosene (kerosin); purified high boiling point. Machine oils such as aliphatic hydrocarbons; alcohols such as methanol, ethanol, isopropanol, butanol and cyclohexanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, hexylene glycol, polyethylene glycol and polypropylene glycol. Classes: Polyhydric alcohol derivatives such as propylene glycol ethers; Ketones such as acetone, acetophenone, cyclohexanone, methylcyclohexanone and γ-butyrolactone; fatty acid methyl ester (palm oil fatty acid methyl ester), ethylhexyl lactate, propylene carbonate and dibase Esters such as acid methyl esters (dimethyl ester succinate, dimethyl glutamate, dimethyl adipic acid ester); nitrogen-containing solvents such as N-alkylpyrrolidones and acetonitrile; sulfur-containing solvents such as dimethylsulfoxide; palm oil, soybean oil and Oils and fats such as rapeseed oil; dimethylformamide, N, N-dimethyloctaneamide, N, N-dimethyldecaneamide, 5- (dimethylamino) -2-methyl-5-oxo-valeric acid methyl ester and N-acylmorpholin-based An amide-based solvent such as a solvent (CAS No. 887947-29-7, etc.); water and the like can be mentioned.

Surfactants used as formulation aids include nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, silicone-based surfactants, fluorine-based surfactants and biosurfactants. And so on. Examples of the nonionic surfactant include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, and polyoxyethylene alkyl. Ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene / polyoxypropylene block polymer, alkylpolyoxyethylene / polyoxypropylene block polymer ether, alkylphenyl Polyoxyethylene / polyoxypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyoxyethylene benzylphenyl (or phenylphenyl) ether, polyoxyethylene styrylphenyl (or) Phenylphenyl) ether, polyoxyethylene glycol oil, polyoxyethylene hydrogenated castor oil, alkylglycoside and the like can be mentioned.

Anionic surfactants include, for example, alkyl sulphates, polyoxyethylene alkyl ether sulphates, polyoxyethylene alkyl phenyl ether sulphates, polyoxyethylene benzyl (or styryl) phenyl (or phenyl phenyl) ether sulphates and polyoxyethylene / poly. Sulfates such as oxypropylene block polymer sulfates; paraffin (alcan) sulfonate, α-olefin sulfonate, dialkyl sulfosuccinate, alkylbenzene sulfonate, mono or dialkylnaphthalene sulfonate, naphthalene sulfonate formalin condensate, alkyldiphenyl ether disulfonate, lignin sulfonate, Sulfonates such as polyoxyethylene alkyl phenyl ether sulfonates and polyoxyethylene alkyl ether sulfosuccinic acid half esters; carboxy such as fatty acids, resin acids, polycarboxylic acids, alkyl ether carboxylates, alkenyl succinic acid, N-acyl amino acids and naphthenic acid. Rats; polyoxyethylene alkyl ether phosphate, polyoxyethylene mono or dialkylphenyl ether phosphate, polyoxyethylene benzyl (or styryl) phenyl (or phenylphenyl) ether phosphate, polyoxyethylene / polyoxypropylene block polymer phosphate and alkyl phosphate. Examples include phosphates.

Cationic surfactants include, for example, salts of amines such as alkylamines and alkylpentamethylpropylene diamines; alkyltrimethylammonium, methylpolyoxyethylene alkylammonium, methylpolyoxyethylene alkylammonium, alkylpyridinium, mono or dialkylmethyl. Examples thereof include salts of ammoniums such as ammonium carbonate, alkyldimethylbenzalkonium and benzethonium (octylphenoxyethoxyethyldimethylbenzylammonium).
Examples of the amphoteric tenside include dialkyldiaminoethyl betaine, alkyldimethylbenzyl betaine and lecithin (phosphatidylcholine, phosphatidylethanolamine, etc.).

Examples of the silicone-based surfactant include trisiloxane ethoxylate and the like.

Examples of the fluorine surfactant include perfluoroalkylcarboxylic acid salt, perfluoroalkyl sulfonate, and perfluoroalkyltrimethylammonium salt.

Biosurfactants include, for example, sophorolipid, ramnolipid, trehalose lipid, mannosylargitol lipid, cellobiose lipid, glucose lipid, oligosaccharide fatty acid ester, spiculsporic acid, corinomicolic acid, agaric acid, surfactin, serauetchin, biscocin, lykensin, Examples thereof include arslovactin, emalzan and alasan.

Other formulation aids include inorganic salts (sodium, potassium, etc.) used as pH adjusters; water-soluble salts such as salt; xatan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxy used as thickeners. Vinyl polymers, acrylic polymers, polyvinyl alcohols, starch derivatives, water-soluble polymers (polysaccharides, etc.), alginic acid and salts thereof; metal stearate used as a disintegrant, sodium tripolyphosphate, sodium hexametaphosphate, etc.; antiseptic As a supplement, benzoic acid and its salt used as an agent, sorbic acid and its salt, propionic acid and its salt, p-hydroxybenzoic acid, methyl p-hydroxybenzoate, 1,2-benzthiazolin-3-one, etc. Sodium polyphosphate, sodium polyacrylate, sodium lignin sulfonate, sodium citrate, sodium gluconic acid / sodium glucoheptate, ethylenediamine tetraacetic acid and its disodium salt or ammonium salt, etc .; pigments and dyes used as colorants. Etc .; Fluorine-based defoaming agents used as defoaming agents, silicone-based defoaming agents, ethylene oxide / propylene oxide copolymers, etc .; Phenolic antioxidants used as antioxidants, amine-based antioxidants, sulfur-based oxidation Inhibitors, phosphoric acid-based antioxidants, etc .; salicylic acid-based UV absorbers used as UV absorbers, benzophenone-based UV absorbers, etc .; freshlime used as desiccants, magnesium oxide, etc.; Examples include agents.

There are two types of pharmaceuticals, one that is used as it is and the other that is diluted to a predetermined concentration with a diluent such as water. The concentration of the azole derivative (I) when diluted and used is preferably in the range of 0.001 to 1.0%.

The amount of the azole derivative (I) used is 20 to 5000 g, more preferably 50 to 2000 g, per 1 ha of agricultural and horticultural fields such as fields, rice fields, orchards and greenhouses. Since the concentration and amount of these substances used vary depending on the dosage form, timing of use, method of use, place of use, target crop, etc., the amount can be increased or decreased without being particular about the above range.

Further, the agricultural and horticultural disease control agent of the present embodiment can be used in combination with other known active ingredients to enhance the performance as an agricultural and horticultural disease control agent. Other known active ingredients include known active ingredients contained in fungicides, insecticides, acaricides, nematodes, and plant growth regulators.

(Active ingredient for fungicides)
Examples of effective components suitable for use as bactericides include sterol biosynthesis inhibitor compounds, benzimidazole compounds, succinate dehydrogenase inhibitor compounds (SDHI compounds), strovirlin compounds, phenylamide compounds, and dicarboxyimide. Examples thereof include system compounds, anilinopyrimidine system compounds, multi-action point compounds, antibiotics, carbamate compounds, quinoline compounds, organic phosphorus compounds and carboxylamide compounds.

Examples of sterol biosynthesis inhibitor compounds include azaconazole, bitertanol, bromconazole, diphenoconazole, cyproconazole, diniconazole, fenbuconazole, fluconazole, flutriazole, hexaconazole, imazalyl, imibenconazole, methylconazole, ipconazole, Microbutanyl, pefrazoate, penconazole, prochloraz, propiconazole, prothioconazole, epoxyconazole, simeconazole, tebuconazole, tetraconazole, triazimefone, triazimenol, triflumizole, triticonazole, fluconazole, oxpoconazole , Mefentrifluconazole, ipfentrifluconazole, 1-((1H-1,2,4-triazole-1-yl) methyl) -5- (4-chlorobenzyl) -2- (chloromethyl) -2- Methylcyclopentan-1-ol, methyl 2-((1H-1,2,4-triazole-1-yl) methyl) -3- (4-chlorobenzyl) -2-hydroxy-1-methylcyclopentane-1 -Carboxylate, phenpropimorph, fenpropidine, spiroxamine, tridemorph, bupilimate, phenalimol, pyriphenox, pyrisoxazole, nuarimol, etaconazole, piperalin, naphthifin, fenpyrazamine, phenhexamide, terbinafine, aldimorph, dodemorph, pyribuchicarb and tripholine, etc. Can be mentioned.

Examples of the benzimidazole compound include carbendazim, benomyl, thiabendazole and fuberidazole.

Examples of succinate dehydrogenase inhibitory compounds (SDHI-based compounds) include bixaphen, benzobindiflupil, boscalide, fluopyram, fenfuram, flutranil, fluxapyroxad, flamethopil, isofetamide, isopyrazam, mepronil, penflufen, penthiopyrado, sedaxane, and tifluzamide. , Fluoripyl, pyraziflumid, pidiflumethophene, benodanyl, carboxin, pyrapropoin, impilfluxam, isoflusiplum, impilfluxam and oxycarboxyne.

Examples of strobilurin compounds include azoxystrobin, dymoxystrobin, enestrovin, phenamistrobin, fluoroxastrobin, cresoximemethyl, metminostrobin, orysustrobin, picoxystrobin, pyracrostrobin, trifloxystrobin, and mann. Examples thereof include destrobin, pyribenecarb, pyraoxystrobin, pyrametostrobi, fluphenoxystrobin, enoxastrobin, spumoxystrobin, triclopyricalve, phenaminestrobin and methyltetraprol.

Examples of the phenylamide compound include benaraxyl, benaraxyl M or kiraluxyl, metalluxyl, metalaxyl M or mephenoxam, flaluxyl, and oxadixyl.

Examples of the dicarboxyimide-based compound include procymidone, iprodion and vinclozoline.

Examples of the anilinopyrimidine-based compound include cyprozinyl, mepanipylim, and pyrimethanyl.

Multi-acting point compounds include mancozeb, manzeb, manneb, methylam, propineb, tiram (thiuram), dineb, dilam, ambam, anilazine, dithianone, fluazinum, thiazole zinc, diclofluanide, trifluanide, dodyne, guazatin, iminoctadine (iminoctadine). Acetate, iminoctadine albesylate), copper, copper compounds (eg, basic copper chloride, cupric hydroxide, basic copper sulfate, copper sulfate, organic copper (oxyn copper), nonylphenol sulfonate copper, DBEDC, etc.) , Hydrogen carbonate (sodium hydrogen carbonate, potassium hydrogen carbonate), silver metal, fentin, sulfur, mineral oil, baking soda, potassium carbonate, ferbum, captan, captahole, fluorimide, quinomethionate, metasulfocarb, dipimethitron, chlorotalonyl (TPN) and Examples include copper.

Antibiotics include kasugamycin, polyoxine, streptomycin, validamycin, oxytetracycline and the like.

Examples of the carbamate compound include bench avaricarb (bench avaricarb isopropyl), dietofencarb, iprovaricarb, propamocarb, iodocarb, prothiocarb and tolprocarb.

Examples of the quinoline compound include oxolinic acid, pyroquilon, quinoxyphen and tebuflokin.

Examples of the organophosphorus compound include dinocup, edifenphos (EDDP), Josetil (Josetyl-aluminum, Josetil potassium, Josetyl sodium), iprobenphos (IBP), pyrazophos, meptirodinocup, and torquelophos methyl.

Examples of the carboxamide compound include carpropamide, etaboxam, phenoxanyl, silthiofam, thiazinyl and isothienyl.

In addition, as compounds for other fungicide applications, thiophanate, thiophanate methyl, pencyclon, amethoctrazine, amysulbrom, siazofamide, siflufenamide, simoxanyl, diclosimet, dichromedin, famoxadon, fenamiden, fenhexamide, fenitropan, fludioxonyl, fluopicolid, flusulfamide, flusulphamide , Harpin, Isoprothiolan, Isonianil, Mandipropamide, Phenamaclyl, Metraphenone, Oxatiapiproline, Fusalide, Proquinazide, Variphenalate, Zoxamide, Diclobenazox, Fempicoxamide, Picalbutrazox, Kinofumerin, Dimethmorph, Fullmorph, Pyrimorph , Felimzone, Acibenzolar (Acibenzolar-S-Methyl), Etridiazol, Himexazole, Provenazole, Tricyclazole, Fenpyrazamine, Tecrophthalam, Hydroxyisoxazole, Fluolimide, Pyriophenone, Diflumethrim, Torfenpyrado, Phenazakin, Kinomethionate, Aminopyridene, Chloroinconadide Dacromethyl, ipfluphenokin, fluoripimamide, florylpicoxamide, fluorapiproline, fenfuran, binapacryl, triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide, offrace, bupyrimate, dimethilimol, etilimol , Octinone, clozoline, dimethacron, phenpicronyl, blastsaidin, triazoxide, dodine, picalbutrazox, quinoprol, biphenyl, chloroneb, dichlorin, quintozen (PCNB), technazen (TCNB), natamicin (pimaricin), laminarin, fluveneteram Acid, phosphate, Shiitake mycelium extract, Gosei Kayupte (tea tree) extract, vegetable oil (eugenol, geraniol, timol), machine oil, organic oil, Oitadori extract, cell wall of Saccharomyces cerevisiae LAS117 strain and biopesticide (Agrobacterium Radiobacter, Pseudomonas Fluorescence, Pseudomonas rodesia, Pseudomonas chlororafis AFS009 strain, Bacillus subtilis, Bacillus symplex, Bacillus amyloliquefaciens, Bacillus mycoides, Nonpathogenic Elvinia carotbola, Lactobacillus Plantalum, Barrioborax paradox, Swingrea glutinosa extract, Trichoderma atroviride I-1237 strain, Trichoderma atroviride LU132 strain, Trichoderma atroviride SC1 strain, Trichoderma asperellam T34 strain, Gliocladium catenuratam J1446 Strain, Chronostakis rosea CR-7 strain, Streptomyces glyceobilides K61 strain, Streptomyces lydicus WYEC108, etc.).

(Active ingredient for pesticide use)
Effective ingredients suitable for pesticide applications include, for example, organic phosphorus compounds, carbamate compounds, pyrethroid compounds, nelystoxin compounds, neonicotinoid compounds, benzoylurea compounds, other insect growth control compounds, and organic chlorine compounds. And compounds derived from natural products.

Organophosphorus compounds include acephate, azamethifos, azinephos-methyl, azinephos-ethyl, cassaphos, chlorethoxyphos, chlorpyrifos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, kumaphos, cyanophos, demethon-S-methyl, diazinon, Dichlorpyrifos (DDVP), dichlorpyrifos, dimethoate, dimethylbinphos, disulfoton, etion, etoplophos, EPN, famfur, phenamiphos, fenitrothion (MEP), fenitrothion (MPP), hostiazeto, heptenophos, imiciaphos, isophenphos, O- (methoxyaminothiohoso) Holyl) salicylate isopropyl, isoxathione, malathion, mecarbam, metamidphos, metidation, mevinphos, chlorpyrifos, naredo, ometoate, oxydemethoate, palatine, palatine-methyl, fenitrothion, holate, hosalon, hosmet, phosphamide, hoxim, Examples thereof include pyrimiphosmethyl, prophenofus, propetanphos, prothiophos, pyracrophos, pyridafenthion, sulfotep, quinalphos, tebupyrimphos, temepos, terbuphos, tetrachlorpyrifos, thiomethon, triazophos, bamidthione and trichlorfon (DEP).

Carbamate compounds include aranicalb, aldicarb, benziocarb, benfuracarb, butocarboxim, butoxycarboxim, carbyl (NAC), carbofuran, carbosulfan, formanate, isoprocarb (MIPC), metolcarb, methomyl, oxamil, pyrimicalve, propoxyl, Examples thereof include thiodicalve, thiofanox, triazamate, trimetacarb, XMC, bendiocarb, ethiophencarb, phenocarb (BPMC), phenothiocarb, fratiocarb, metolcarb and xylylcarb.

Examples of pyrethroid compounds include acrinathrin, allethrin, cypermethrin, bifenthrin, bioallethrin, bioaresrin s-cyclopentyl isomer, bioresmethrin, cycloprothrin, cifluthrin, delmethrin, empentrin, dimefluthrin, esphenvalerate, etofenprox, and fenpropa. Trin, fenvalerate, flubrocitrinate, flucitrinate, flumethrin, fluvalinate, halfenprox, sihalothrin, metoflutrin, monfluorotrin, permethrin, allethrin, pyrethrins or pyrethrum, allethrin, profluthrin, tefluthrin, tetramethrin, tralomethrin, trans Examples include fluthrin, copper bifentrin, imiprothrin, cadesrin, pyrethrin, chloropraletrin, epsilon metoflutrin, chloroallethrin, epsilon monfluorothrin and ciphenotrin.

Examples of the nelystoxin compound include cartap, benzultap, thiocyclam, thiosultap-sodium salt, monosultap and bisultap.

Examples of neonicotinoid compounds include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam and nicotine.

Examples of the benzoylurea compound include bistrifluron, chlorfluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novallon, nobiflumron, teflubenzuron and triflumuron.

Other insect growth control compounds include buprofezin, chromaphenozide, cyromazine, halophenozide, methoxyphenozide, phenoxycarb, tebufenozide and pyriproxyfen.

Examples of the organochlorine compound include chlordane, aldrin, dieldrin, endosulfan, methoxychlor, lindan and DDT.

Naturally-derived compounds include abamectin, Bacillus thuringiensis-derived germs and produced crystalline toxins, and mixtures thereof, Bacillus sphaerix, emamectin benzoate, repimectin, milbemectin, spinetram, spinosad, machine oil, starch, etc. Examples thereof include reduced starch saccharified product, rapeseed oil, sodium oleate, propylene glycol monofatty acid ester, fatty acid glyceride and ferric phosphate.

In addition, as compounds for other pesticide applications, avelmectin, chloranthraniliprol, tetrachlorolantraniliprol, chlorphenapir, cyantranyliprole, diafentiurone, ethiprol, fipronil, flonicamide, flubenzamide, fluenesulfone, etc. Flupyraziflon, indoxacarb, metaflumison, metaaldehyde, pimetrodin, pyridalyl, pyrifluquinazone, silafluofen, spirodion, spirotetramato, sulfoxaflor, tolfenpyrado, afidopyropen, brofuranilide, cyclaniliprol, dichloromesothiaz, fromotkin, fluazind. Lysine, fluhexaphon, fluxametamid, pyriprol, tetraniliprol, triflumesopyrim, hydroprene, quinoprene, metoprene, tyclopyrazoflor, flupyrimin, spiropidione, benzpyrimoxane, sihalodiamide, sulfamide, isocycloceram, DNOC, sulfullamide , Rotenone, Nicofluprol, Jim Propyridaz, Methyl Bromide, Chlorpicrin, Cliolite, Sulfril Fluoride, Boric Acid, Boric Acid, Sodium Heaboate, Sodium Metaborate, Tartrate, Dazomet, Metam, Aluminum Phosphide, Phosphorus Calcium phosphide, phosphine, zinc phosphide, calcium cyanide, potassium cyanide, sodium cyanide, cyprofuranilide, kodringa granulosis virus, kodringa modoki granulosis virus, velvet maikemushi nuclear polyhedron disease virus, barley mosquito nuclear polymorphic disease virus, GS- Omega / Kappa HXTX-Hv1a peptide, azadilactin, dicoform, lime sulfur mixture, manzeb, Burkhorderia spp., Volbakia pipientis (Zap), Aritasou extract, fatty acid monoester with glycerin or propanediol, neem oil, Examples include Beauveria baciana, Metallidium anisoprier, Pekiromyces fumosoroseus and diatomaceous soil.

(Active ingredient for acaricide applications)
Examples of active ingredients (mite-killing active ingredients) suitable for acaricidal use include acequinosyl, amidoflumet, amitraz, azocyclotin, biphenazate, bromopropirate, chlorphenson, quinomethionate, phenisobromolate, benzoximate, and black. Fentezine, Sienopyraphen, Hydramethylnon, Siflumethofen, Sihexatin, Difluorovidadine, Dienochlor, Etoxazole, Phenazakin, Fenbutatin oxide, Fempyroximate, Phenothiocarb, Fluacripirim, Hexithiazox, Propargite (BPPS), Pyphridazox, Propargite (BPPS), Piflubmid, Pyridaben , Tebufenpyrado, Tetradiphon, Asinonapill, Sietopirafen, Flupentiphenox and blended oil.

(Active ingredient for nematode insecticide)
Optimal active ingredients (nematode-killing active ingredients) for nematode-killing agents include, for example, DD (1,3-dichloropropene), DCIP (dichlorodiisopropyl ether), methylisothiocyanate, carbam sodium salt, and kazusaphos. , Hostiazeto, imiciaphos, morantel tartrate, levamisole hydrochloride, nemadetin, cyclobutriflulam and tioxazaphen and the like.

(Active ingredient for plant growth regulators)
Optimal active ingredients for plant growth regulator applications include, for example, aminoethoxyvinylglycine, chlormecoat, chlorprofam, cyclanilide, dikeglac, daminogit, etephone, fluluprimidol, flumethralin, forchlorphenurone, gibberellin, hydrazide maleate. Salt, mepicote chloride, methylcyclopropene, benzylaminopurine, paclobutrazole, prohexadione, tidiazulone, tributylphosphorotrithioate, trinexacacethyl, uniconazole, sodium 1-naphthalene acetate, 1-naphthylacetamide, 1-Methylcyclopropene, 4-CPA (4-chlorophenoxyacetic acid), MCPB (ethyl 2-methyl-4-chlorophenoxybutyrate), isoprothiolane, itaconic acid, indolebutyric acid, ethicrozeto, calcium formate, chlormecoat, choline, cyanamide, Dichlorprop, gibberellin, daminozide, decyl alcohol, sorbitan trioleate, nicosulfone, pyraflufenethyl, butruarin, prohydrojasmon and pendimethalin and the like.

[Method of controlling plant diseases]
The agricultural and horticultural disease control agent of the present embodiment can be used in agricultural or non-agricultural land such as fields, paddy fields, lawns, and orchards. Further, the agricultural and horticultural disease control agent of the present embodiment can be applied not only by foliar treatment such as spraying foliage, but also by non-foliage treatment such as seed treatment including treatment on bulbs and tubers and irrigation treatment. Therefore, the method for controlling plant diseases according to the present embodiment is a method including a procedure for performing foliage treatment or non-foliage treatment using the above-mentioned agricultural and horticultural disease control agent. The non-foliage treatment can reduce the labor as compared with the case of performing the foliage treatment.

In the application by seed treatment, the chemicals are attached to the seeds by mixing a wettable powder, a powder or the like with the seeds and stirring, or by immersing the seeds in a diluted wettable powder or the like. It also includes a seed coating process. The amount of the active ingredient used in the seed treatment is, for example, 0.01 to 10000 g, preferably 0.1 to 1000 g per 100 kg of seeds. Seeds treated with agricultural and horticultural disease control agents may be used in the same manner as ordinary seeds.

Application by irrigation treatment is performed by treating the planting hole or its surroundings with granules, etc. at the time of transplanting seedlings, or by treating the soil around the seeds or plants with granules, wettable powders, etc. .. The amount of the active ingredient used in the irrigation treatment is, for example, 0.01 to 10000 g, preferably 0.1 to 1000 g per ^{1 m 2 of agricultural and horticultural land.}

The amount of the active ingredient used for foliar spraying is, for example, 20 to 5000 g, more preferably 50 to 2000 g, per 1 ha of agricultural and horticultural fields such as fields, rice fields, orchards and greenhouses.

Since the concentration and amount used vary depending on the dosage form, timing of use, method of use, place of use, target crop, etc., the amount can be increased or decreased without being particular about the above range.

As described above, the azole derivative (I) exhibits an excellent bactericidal action against many bacteria that cause plant diseases. That is, the agricultural and horticultural disease control agent containing the azole derivative (I) as an active ingredient has low toxicity to humans and animals, is excellent in handling safety, and can exhibit a high control effect on a wide range of plant diseases.

［式（Ｉ）中、
Ａは、Ｎ又はＣＨであり；
Ｄは、水素、ハロゲン基又はＳＲ^Ｄであり；
ここで、Ｒ^Ｄは水素、シアノ基、Ｃ_１−Ｃ_６−アルキル基、Ｃ_１−Ｃ_６−ハロアルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−ハロアルケニル基、Ｃ_２−Ｃ_６−アルキニル基又はＣ_２−Ｃ_６−ハロアルキニル基であり；
Ｒ^１は、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基、フェニル−Ｃ_２−Ｃ_４−アルキニル基又はＣＯＸＲ^５であり；
ここで、Ｒ^５は、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基又はフェニル−Ｃ_２−Ｃ_４−アルキニル基であり；
Ｘは、単結合、−Ｏ−又は−ＮＲ^６−であり；
Ｒ^６は、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基又はフェニル−Ｃ_２−Ｃ_４−アルキニル基であり、Ｒ^５とＲ^６とは環を形成していてもよく；
Ｒ^２は、−ＯＲ^７又は−ＮＲ^８Ｒ^９であり；
Ｒ^７、Ｒ^８及びＲ^９は、それぞれ独立に、水素、Ｃ_１−Ｃ_６−アルキル基、Ｃ_２−Ｃ_６−アルケニル基、Ｃ_２−Ｃ_６−アルキニル基、Ｃ_３−Ｃ_８−シクロアルキル基、Ｃ_３−Ｃ_８−シクロアルキル−Ｃ_１−Ｃ_４−アルキル基、フェニル基、フェニル−Ｃ_１−Ｃ_４−アルキル基、フェニル−Ｃ_２−Ｃ_４−アルケニル基又はフェニル−Ｃ_２−Ｃ_４−アルキニル基であり、Ｒ^８とＲ^９とは環を形成していてもよく；
ここで、Ｒ^１、Ｒ^２、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８及びＲ^９における脂肪族基は、１、２、３若しくは可能な最大数の同一の又は異なる基Ｒ^ａを有していてもよく、Ｒ^ａは、ハロゲン基、シアノ基、ニトロ基、Ｃ_１−Ｃ_４−アルコキシ基及びＣ_１−Ｃ_４−ハロアルコキシ基から互いに独立して選択され；
Ｒ^４は、ハロゲン基、シアノ基、ニトロ基、アミノ基、フェニル基、フェニル−オキシ基、Ｃ_１−Ｃ_４−アルキル基、Ｃ_１−Ｃ_４−ハロアルキル基、Ｃ_１−Ｃ_４−アルコキシ基又はＣ_１−Ｃ_４−ハロアルコキシ基、Ｃ_１−Ｃ_４−アルキルアミノ基、Ｃ_１−Ｃ_４−ジアルキルアミノ基、Ｃ_１−Ｃ_４−アルキルアシルアミノ基、−ＳＯＲ^１０又は−ＳＦ_５であり；
Ｒ^１、Ｒ^２、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８及びＲ^９におけるシクロアルキル基若しくはフェニル基部分又はＲ^４におけるフェニル基部分は、１、２、３、４、５若しくは可能な最大数の同一の又は異なる基Ｒ^ｂを有していてもよく、Ｒ^ｂは、ハロゲン基、シアノ基、ニトロ基、Ｃ_１−Ｃ_４−アルキル基、Ｃ_１−Ｃ_４−アルコキシ基、Ｃ_１−Ｃ_４−ハロアルキル基及びＣ_１−Ｃ_４−ハロアルコキシ基から互いに独立して選択され；
Ｒ^３は、ハロゲン基、シアノ基、ニトロ基、フェニル基、フェニル−オキシ基、Ｃ_１−Ｃ_４−アルキル基、Ｃ_１−Ｃ_４−ハロアルキル基、Ｃ_１−Ｃ_４−アルコキシ基、Ｃ_１−Ｃ_４−ハロアルコキシ基、−ＳＯＲ^１０又は−ＳＦ_５であり；
ここで、Ｒ^１０は、Ｃ_１−Ｃ_４−アルキル基又はＣ_１−Ｃ_４−ハロアルキル基であり；
Ｅは、フェニル基又はＮ原子を１若しくは２つ含む６員の芳香族複素環であり；
Ｒ^３は任意の置換位置にｎ個結合しており；
Ｅがフェニル基の場合、ｎは０、１、２、３又は４であり、ＥがＮ原子を１若しくは２つ含む６員の芳香族複素環である場合は、ｎは０、１又は２であり；
Ｙは、Ｅの任意の位置に接続する酸素原子、−ＣＨ_２Ｏ−、−ＯＣＨ_２−、−ＮＨ−、−Ｎ（−Ｃ_１−Ｃ_４−アルキル）−、−Ｎ（−Ｃ_３−Ｃ_６−シクロアルキル）−又は−Ｓ（Ｏ）_ｐ−であり；
ｐは、０、１又は２であり；
Ｚは、フェニル基若しくはナフチル基である芳香族炭化水素基、又は、Ｏ、Ｎ若しくはＳから選択されるヘテロ原子を１〜４つ含む５員又は６員の芳香族複素環若しくは２環から構成される９員又は１０員の芳香族複素環であり；
Ｒ^４は任意の置換位置にｍ個結合しており；
Ｚがフェニル基である場合、ｍは１、２、３、４又は５であり、Ｚがナフチル基又は芳香族複素環である場合、ｍは０、１、２、３又は４である］ [Summary]
The agricultural and horticultural disease control agent of the present embodiment contains a compound represented by the following general formula (I), or an N-oxide thereof or a pesticide-acceptable salt as an active ingredient, and is used for foliar treatment or non-foliage treatment. For foliage treatment.

[In formula (I),
A is N or CH;
D is hydrogen, halogen or SR ^D;
Here, ^RD is hydrogen, cyano group, C _1- C ₆ -alkyl group, C _1- C ₆ -haloalkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -haloalkenyl group, C ₂ -C ₆ -alkynyl group or C _2- C ₆ -haloalkynyl group;
R ¹ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group, phenyl-C _2- C ₄ -alkynyl group or COXR ⁵ Yes;
Here, R ⁵ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C. ₈ -Cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group Yes;
X is a single bond, -O- or -NR ^6- ;
R ⁶ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group, R ⁵ and R ⁶ may form a ring;
R ² is -OR ⁷ or -NR ⁸ R ⁹ ;
R ⁷ , R ⁸ and R ⁹ are independently hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cyclo. Alkyne group, C _3- C ₈ -cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C ₂ It is a -C ₄ -alkynyl group, and R ⁸ and R ⁹ may form a ring;
^Here, the aliphatic group represented by ^{R 1, R 2, R 5} , R 6, R 7, R 8 and ^{R 9} have the same or different groups ^{R a} 1, 2, 3 or maximum possible number ^Ra may be selected independently of each other from halogen groups, cyano groups, nitro groups, C _1- C ₄ -alkoxy groups and C _1- C _{4-haloalkoxy groups;}
R ⁴ is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, and a C _1- C ₄ -alkoxy group. or _C 1 -C ₄ - haloalkoxy _group, C 1 -C ₄ - alkylamino _group, C 1 -C ₄ - dialkylamino _group, C 1 -C ₄ - alkyl acyl amino group, in -SOR ¹⁰ or -SF ₅ Yes;
The cycloalkyl group or phenyl group moiety in R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ^{9 or the phenyl group moiety in R 4} is 1, 2, 3, 4, 5 or the maximum possible. It may have the same or different number of groups R ^b , where R ^b is a halogen group, a cyano group, a nitro group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -alkoxy group, C ₁ -C ₄ - haloalkyl groups and _C 1 -C ₄ - is selected from haloalkoxy groups independently of each other;
R ³ is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, a C _1- C ₄ -alkoxy group, and a C ₁ -C ₄ -haloalkoxy group, -SOR ¹⁰ or -SF ₅ ;
^{Wherein, R 10} _is, C 1 -C ₄ - alkyl group or a _C 1 -C ₄ - haloalkyl group;
E is a 6-membered aromatic heterocycle containing one or two phenyl groups or N atoms;
R ³ is bound to any substitution position by n;
When E is a phenyl group, n is 0, 1, 2, 3 or 4, and when E is a 6-membered aromatic heterocycle containing 1 or 2 N atoms, n is 0, 1 or 2. Is;
Y is an oxygen atom connected to an arbitrary position of E, -CH ₂ O-, -OCH _2- , -NH-, -N (-C _1- C ₄ -alkyl)-, -N (-C _3-). C ₆ -cycloalkyl)-or -S (O) _p- ;
p is 0, 1 or 2;
Z is composed of an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5- or 6-membered aromatic heterocycle or 2 rings containing 1 to 4 heteroatoms selected from O, N or S. Is a 9- or 10-membered aromatic heterocycle;
R ⁴ is and m pieces bonded to any substitutable position;
If Z is a phenyl group, m is 1, 2, 3, 4 or 5, and if Z is a naphthyl group or an aromatic heterocycle, m is 0, 1, 2, 3 or 4].

In the agricultural and horticultural disease control agent of the present embodiment, the disease may be a disease of corn or soybean.

The method for controlling plant diseases of the present embodiment includes a step of using the above-mentioned agricultural and horticultural disease control agent.

In the agricultural and horticultural disease control agent of the present embodiment, the step may be a foliage treatment step or a non-foliage treatment step using the agricultural and horticultural disease control agent.

Examples are shown below, and embodiments of the present invention will be described in more detail. Of course, the present invention is not limited to the following examples, and it goes without saying that various aspects are possible for details. Furthermore, the present invention is not limited to the above-described embodiment, and various modifications can be made within the scope of the claims, and the present invention also relates to an embodiment obtained by appropriately combining the disclosed technical means. It is included in the technical scope of the invention. In addition, all the documents described in the present specification are incorporated by reference.

[Synthesis Example] Synthesis of Azole Derivative (I) Compound I-1 which is the following azole derivative (I) was synthesized according to the method described in Patent Document 1.
Compound I-1: Methyl 2-hydroxy-2- (2-chloro-4- (4-chlorophenoxy) phenyl) -3- (1H-1,2,4-triazole-1-yl) propanoate

[Preparation Example 1] Preparation of wettable powder A wettable powder was prepared as follows using the compound I-1 obtained in the above synthetic example.
Compound I-1 20.0 parts Sodium lauryl sulfate 2.0 parts Alkylnaphthalene sulfonic acid Formarin condensate sodium salt 5.0 parts Zinc stearate 0.2 parts White carbon 3.0 parts Clay 69.8 parts mixed. It was pulverized to obtain a wettable powder.

[Formation Example 2] Preparation of flowable agent A flowable agent was prepared as follows using the compound I-1 obtained in the above synthetic example.
Compound I-1 20.0 parts Alkylbenzene sulfonic acid metal salt 1.2 parts Silicon emulsion (Pronal EX-300 manufactured by Toho Kagaku Kogyo) 0.5 parts Acrylic copolymer (ATLOX4913 manufactured by Crowder) 5.0 parts Xanthan gum 0.2 parts 1 , 2-Benzothiazolin-3-one (Proxel GXL manufactured by Ronza) 0.2 part propylene glycol 8.0 part sardine glass 0.8 part water 64.1 parts were mixed and pulverized to prepare a flowable agent.

[Pharmaceutical Example 3] Preparation of Emulsion An emulsion was prepared as follows using the compound I-1 obtained in the above synthetic example.
Compound I-1 5.0 parts Polyoxyalkylene alkyl ether / alkylbenzene sulfonic acid metal salt / alkylbenzene mixture 15.0 parts 5- (dimethylamino) -2-methyl-5-oxopentanoate methyl 12.0 parts N, N 44.0 parts of a mixture of -dimethyloctaneamide / N and N-dimethyldecaneamide 24.0 parts of solvent naphtha were uniformly mixed and dissolved to prepare an emulsion.

[Test Example 1] Field test of field corn Using the emulsion obtained in Formulation Example 3, a control effect test against corn gray spot disease was conducted in a test field. Field corn (variety: Golden Harvest G11U58-3122) was used as corn. The spray solution prepared so that the dosage contained in the emulsion was 90 g / ha was sprayed once 63 days after sowing (140 L / ha). 41 days after spraying, the diseased area rate of gray spot disease and the area rate of green leaves were visually evaluated, and corn was harvested 93 days after spraying. The test results are shown in Table 1. In Table 1, "no treatment" is the result at the same time when the foliage spraying treatment with the emulsion containing the compound I-1 was not performed.

As shown in Table 1, by spraying compound I-1 on field corn that had been damaged by corn gray spot disease, the diseased area rate of corn gray spot disease was higher than that in the case of no treatment. Decreased. In addition, the foliage spraying treatment of Compound I-1 improved the green leaf area ratio and the yield of field maize as compared with the case of no treatment.

[Test Example 2] Field test of sweet corn Using the emulsion obtained in Formulation Example 3, a control effect test against corn rust, corn soot and corn gray spot disease was carried out in a test field. Sweet corn (variety: Remedy) was used as corn. The spray solution prepared so that the dosage contained in the emulsion was 90 g / ha was sprayed once 76 days after seeding (280 L / ha). The onset area rate and green leaf area rate of rust, soot spot disease and gray spot disease were visually evaluated 35 days after spraying, and corn was harvested 21 days after spraying. The test results are shown in Table 2. In Table 2, "no treatment" is the result at the same time when the foliage spraying treatment with the emulsion containing the compound I-1 was not performed.

As shown in Table 2, by spraying compound I-1 on sweet corn damaged by corn rust, corn soot stain, or corn gray spot disease, the diseased area rate of each disease is increased. Diminished. In addition, the foliage spraying treatment of Compound I-1 improved the green leaf area ratio and yield of sweet corn.

[Test Example 3] Greenhouse test of soybean A control effect test against soybean rust was conducted in a greenhouse using the compound I-1 obtained in the synthetic example. A finite growth type variety (Enrei) was used as soybean. A spray solution prepared so that the dosage of the compound was 100 g / ha (acetone was added to 5% and Gramin S was added to 60 ppm, respectively) was sprayed once 26 days after sowing (1000 L / ha). The day after spraying, spores of soybean rust ( ^{prepared to 1 × 10 6} cells / mL and added with grammine to 60 ppm) were spray-inoculated and kept under high humidity conditions for 24 hours. After that, it was managed in the greenhouse. Eighteen days after inoculation, the diseased area rate of rust was visually evaluated, and the weight of the above-ground part of soybean was measured. The test results are shown in Table 3. In Table 3, "no treatment" is the result at the same time when the foliage spraying treatment with the compound I-1 was not performed.

As shown in Table 3, when the diseased area rate of soybean rust is untreated by spraying compound I-1 on the finite growth type soybean that has been damaged by soybean rust. It decreased in comparison. In addition, the above-ground weight of soybean was improved by the foliar spraying treatment of Compound I-1 as compared with the case of no treatment.

The present invention has a disease control action suitable for a specific plant, and can be used in fields such as agriculture and horticulture.

Claims (4)

The compound represented by the following general formula (I), or its N-oxide or pesticide-acceptable salt is contained as an active ingredient.
Agricultural and horticultural disease control agents for foliage treatment or non-foliage treatment.

[In formula (I),
A is N or CH;
D is hydrogen, halogen or SR ^D;
Here, ^RD is hydrogen, cyano group, C _1- C ₆ -alkyl group, C _1- C ₆ -haloalkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -haloalkenyl group, C ₂ -C ₆ -alkynyl group or C _2- C ₆ -haloalkynyl group;
R ¹ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group, phenyl-C _2- C ₄ -alkynyl group or COXR ⁵ Yes;
Here, R ⁵ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C. ₈ -Cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group Yes;
X is a single bond, -O- or -NR ^6- ;
R ⁶ is hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cycloalkyl group, C _3- C ₈ -cyclo. Alkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C _2- C ₄ -alkynyl group, R ⁵ and R ⁶ may form a ring;
R ² is -OR ⁷ or -NR ⁸ R ⁹ ;
R ⁷ , R ⁸ and R ⁹ are independently hydrogen, C _1- C ₆ -alkyl group, C _2- C ₆ -alkenyl group, C _2- C ₆ -alkynyl group, C _3- C ₈ -cyclo. Alkyne group, C _3- C ₈ -cycloalkyl-C _1- C ₄ -alkyl group, phenyl group, phenyl-C _1- C ₄ -alkyl group, phenyl-C _2- C ₄ -alkenyl group or phenyl-C ₂ It is a -C ₄ -alkynyl group, and R ⁸ and R ⁹ may form a ring;
^Here, the aliphatic group represented by ^{R 1, R 2, R 5} , R 6, R 7, R 8 and ^{R 9} have the same or different groups ^{R a} 1, 2, 3 or maximum possible number ^Ra may be selected independently of each other from halogen groups, cyano groups, nitro groups, C _1- C ₄ -alkoxy groups and C _1- C _{4-haloalkoxy groups;}
R ⁴ is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, and a C _1- C ₄ -alkoxy group. or _C 1 -C ₄ - haloalkoxy _group, C 1 -C ₄ - alkylamino _group, C 1 -C ₄ - dialkylamino _group, C 1 -C ₄ - alkyl acyl amino group, in -SOR ¹⁰ or -SF ₅ Yes;
The cycloalkyl group or phenyl group moiety in R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ^{9 or the phenyl group moiety in R 4} is 1, 2, 3, 4, 5 or the maximum possible. It may have the same or different number of groups R ^b , where R ^b is a halogen group, a cyano group, a nitro group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -alkoxy group, C ₁ -C ₄ - haloalkyl groups and _C 1 -C ₄ - is selected from haloalkoxy groups independently of each other;
R ³ is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C _1- C ₄ -alkyl group, a C _1- C ₄ -haloalkyl group, a C _1- C ₄ -alkoxy group, and a C ₁ -C ₄ -haloalkoxy group, -SOR ¹⁰ or -SF ₅ ;
^{Wherein, R 10} _is, C 1 -C ₄ - alkyl group or a _C 1 -C ₄ - haloalkyl group;
E is a 6-membered aromatic heterocycle containing one or two phenyl groups or N atoms;
R ³ is bound to any substitution position by n;
When E is a phenyl group, n is 0, 1, 2, 3 or 4, and when E is a 6-membered aromatic heterocycle containing 1 or 2 N atoms, n is 0, 1 or 2. Is;
Y is an oxygen atom connected to an arbitrary position of E, -CH ₂ O-, -OCH _2- , -NH-, -N (-C _1- C ₄ -alkyl)-, -N (-C _3-). C ₆ -cycloalkyl)-or -S (O) _p- ;
p is 0, 1 or 2;
Z is composed of an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5- or 6-membered aromatic heterocycle or 2 rings containing 1 to 4 heteroatoms selected from O, N or S. Is a 9- or 10-membered aromatic heterocycle;
R ⁴ is and m pieces bonded to any substitutable position;
If Z is a phenyl group, m is 1, 2, 3, 4 or 5, and if Z is a naphthyl group or an aromatic heterocycle, m is 0, 1, 2, 3 or 4]. The agricultural and horticultural disease control agent according to claim 1, wherein the disease is a disease of corn or soybean. A method for controlling plant diseases, which comprises the step of using the agricultural and horticultural disease control agent according to claim 1 or 2. The control method according to claim 3, wherein the step is a foliage treatment step or a non-foliage treatment step using a disease control agent for agriculture and horticulture.