WO2022034892A1 - Disease control agent and disease control method for agricultural and horticultural use - Google Patents

Abstract

Provided is a disease control agent for agricultural and horticultural use that exhibits an excellent controlling effect against disease caused by a pathogen with low susceptibility to a sterol biosynthesis inhibitor. This disease control agent for agricultural and horticultural use contains a compound represented by general formula (I) or an N-oxide or pharmaceutically acceptable salt thereof as an active ingredient.

Description

Agricultural and horticultural disease control agents and control methods

The present invention relates to a disease control agent for agriculture and horticulture and a control method.

The sterol biosynthesis inhibitor is a disease control agent having bactericidal activity by inhibiting the biosynthesis of sterols in the cell membrane of pathogenic filamentous fungi, and is an inhibitor of the C14-position demethylase in sterol biosynthesis (hereinafter referred to as "DMI"). Also referred to as "bactericidal agent"). It is known that sterol biosynthesis inhibitors have a high control effect on a wide range of plant diseases, and various compounds such as azole compounds, piperazine compounds, pyridine compounds, and pyrimidine compounds have been developed. It is widely used. However, with the spread of sterol biosynthesis inhibitors, the development of drug-resistant bacteria has become a problem.

For example, Zymoseptoria tritici has many drug-resistant bacteria against ubiquinol oxidase inhibitors or succinate dehydrogenase inhibitors, and the frequency of control using sterol biosynthesis inhibitors has increased. As a result, in recent years, many developments of hyposensitivity to sterol biosynthesis inhibitors have been observed.

To address this problem, Patent Document 1 discloses the use of a known triazole compound in the control of sterol biosynthesis inhibitor-resistant Zymoseptoria trifolium. In Patent Document 1, the existing sterol biosynthesis inhibitor mefentrifluconazole is used against the low-sensitivity wheat leaf blight fungi to the existing sterol biosynthesis inhibitors, epoxyconazole, metconazole, prothioconazole, and tebuconazole. It is described that known sterol biosynthesis inhibitors including the above have exhibited antibacterial activity.

In addition, Non-Patent Document 1 describes the relationship between drug excretion of wheat leaf blight and drug susceptibility. Non-Patent Documents 2 to 5 describe the relationship between amino acid mutations in CYP51 and susceptibility to sterol biosynthesis inhibitors. Non-Patent Document 6 describes that the insertion sequence of a gene encoding a protein (MFS1) involved in a drug efflux pump into the promoter region affects drug susceptibility. Non-Patent Documents 7 to 8 describe that amino acid mutations in CYP51, overexpression of CYP51, development of drug efflux pumps, etc. are involved as causes of resistance of wheat leaf blight fungi to sterol biosynthesis inhibitors. Has been done. Non-Patent Document 9 describes a state of decrease in susceptibility of wheat leaf blight to a sterol biosynthesis inhibitor and a decrease in control effect in a field test. Non-Patent Document 10 describes the relationship between overexpression of CYP51 in a pathogen (Sclerotinia homoeocarpa) that causes Shivadalar spot disease and low sensitivity to sterol biosynthesis inhibitors. Non-Patent Document 11 describes a distribution analysis of CYP51 haplotype of wheat leaf blight fungus in Europe.

On the other hand, Patent Document 2 discloses an azole derivative as a compound showing a high control effect against a wide range of plant diseases.

International Publication No. 2020/078942 Pamphlet International Publication No. 2019/093522 Pamphlet

Zwiers L.H. et al., Antimicrobial Agents and Chemotherapy, Vol.46, No.12, p. 3900-3906, 2002 Cools H.J. et al., Applied and Environmental Microbiology, Vol77, No.11, p.3830-3837, 2011 Mullins J.G.L. et al., PLOS ONE, Vol.6 (6), e20973, 2011 Leroux P. et al., Pest Management Science, Vol.67, p 44-59, 2011 McDonald's M.C. et al., Applied and Environmental Microbiology, Vol.85 (4), e01908-18, 2019 Mae A. et al., Frontiers in Plant Science, Vol.11, Article 385, 2020 Cools H.J. et al., Pest Management Science, Vol.69, p 150-155, 2013 Cools H.J. et al., Pest Management Science, Vol.68, No. 7, p 1034-1040, 2012 Fungicide performance 2019 for wheat, barley and oilseed rape, [online], AHDB, [Search on July 15, 2020], Internet <URL: https://ahdb.org.uk/fungicide-performance> Hulvey J. et al., Applied and Environmental Microbiology, Vol.78, No. 18, p 6674-6682, 2012 Huf A. et al., Plant Pathology, Vol.67, p1706-1712, 2018

In Patent Document 1, mefentrifluconazole, which has been shown to have antibacterial activity against some sterol biosynthesis inhibitor-resistant Zymoseptoria trifolia, was launched in Europe in 2020 and is said to exert the highest effect on wheat leaf blight. It is a sterol biosynthesis inhibitor that has been used. Concentration of use on certain effective drugs, such as mefentrifluconazole, has the problem of increasing the risk of developing resistant strains to that drug. Therefore, there is a need for the development of further agricultural and horticultural disease control agents that show a control effect against diseases caused by pathogens that are less sensitive to sterol biosynthesis inhibitors.

The present invention has been made in view of the above-mentioned demands, and an object thereof is to provide an agricultural and horticultural disease control agent which exhibits an excellent control effect against diseases caused by pathogens having low sensitivity to sterol biosynthesis inhibitors. To provide.

As a result of diligent studies by the present inventors in order to solve the above-mentioned problems, the azole derivative represented by the following general formula (I) is highly resistant to pathogenic bacteria having low sensitivity to sterol biosynthesis inhibitors. It has been found that it exhibits antibacterial properties and exhibits an excellent control effect against diseases caused by the pathogenic bacteria, and has completed the present invention.

　［式（Ｉ）中、
　Ａは、Ｎであり；
　Ｄは、水素であり；
　Ｒ^１は、水素又はＣ_１－Ｃ_６－アルキル基であり；
　Ｒ^２は、－ＯＲ^７であり；
　Ｒ^７は、水素、Ｃ_１－Ｃ_６－アルキル基、又はＣ_３－Ｃ_８－シクロアルキル基であり；
　Ｒ^４は、ハロゲン基、Ｃ_１－Ｃ_４－ハロアルキル基、Ｃ_１－Ｃ_４－アルコキシ基又は－ＳＦ_５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、ハロゲン基、Ｃ_１－Ｃ_４－ハロアルキル基又はＣ_１－Ｃ_４－ハロアルコキシ基であり；
　Ｒ^３は任意の置換位置にｎ個結合しており；
　Ｅがフェニル基である場合、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、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であり；
　Ｚは、フェニル基、ナフチル基、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］。 That is, the agricultural and horticultural disease control agent according to one aspect of the present invention contains the compound represented by the following general formula (I), its N-oxide, or a pesticide-acceptable salt as an active ingredient. It is a horticultural disease control agent, and is a disease control agent caused by pathogenic bacteria that is less sensitive to existing sterol biosynthesis inhibitors than the wild type.

[In formula (I),
A is N;
D is hydrogen;
R ¹ is a hydrogen or C1 _- C6 _- alkyl group;
R ² is -OR ⁷ ;
^R7 is a hydrogen, C1 _- C6 _- alkyl group, or C3 _- C8 _- cycloalkyl group;
^R4 is a halogen group, C1- _{C4 -} haloalkyl group, C1- _{C4 -} alkoxy group or -SF ₅ ;
E is a 6-membered aromatic heterocycle containing 1 or 2 phenyl groups or N atoms.
R3 is a halogen group ^, _a C1- _C4 -haloalkyl group or _a C1- _C4 -haloalkoxy group;
^R3 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;
Y is an oxygen atom that connects to any position in E;
Z is a 5- or 6-membered aromatic heterocycle containing 1 to 4 heteroatoms selected from a phenyl group, a naphthyl group, or O, N, or S.
^R4 is bound to any substitution position by m;
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].

According to one aspect of the present invention, it is possible to provide an agricultural and horticultural disease control agent that exhibits an excellent control effect against diseases caused by pathogens that are less sensitive to sterol biosynthesis inhibitors.

Hereinafter, a suitable mode for carrying out the present invention will be described. It should be noted that the embodiments described below show an example of a typical embodiment of the present invention, and the scope of the present invention is not narrowly interpreted by this.

　一般式（Ｉ）中、Ａは、Ｎ又はＣＨであり、好ましくはＮである。Ｄは、水素、ハロゲン基又はＳＲ^Ｄであり、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る。Ｄは、好ましくは水素である。 [1] Azole derivative The agricultural and horticultural disease control agent according to this embodiment is an azole derivative represented by the following general formula (I) (hereinafter referred to as an azole derivative (I)), or its N-oxide or pesticide. Contains an acceptable salt as an active ingredient.

In the general formula (I), A is N or CH, preferably N. ^D is a hydrogen, halogen group or SRD, and ^RD is a hydrogen, cyano group, C1-C6 _- alkyl group, C1 _- C6 _- haloalkyl group, _{C2 -} C6 _- alkenyl group, C. It is a ₂ -C6 _- haloalkenyl group, a C2 _- C6 _- alkynyl group or a C2 _- C6 _- haloalkynyl group. D is preferably hydrogen.

The C1 _- C6 _- 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, a propyl group, a 1-methylethyl group, 1-. Methylpropyl group, 2-methylpropyl group, 1-ethylpropyl group, butyl group, 2-methylbutyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, pentyl group , 1-Methylpentyl group, 2,2-dimethylpropyl group, and 1,1-dimethylethyl group.

The C2 _- C6 _- alkenyl group is a linear or branched alkenyl group having 2 to 6 carbon atoms, and is, for example, an ethenyl group, a 2-propenyl group, or a 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 thereof include a pentenyl group, a 1-hexenyl group and a 5-hexenyl group.

The C2 _- C6 _- alkynyl group is a linear or branched alkynyl group having 2 to 6 carbon atoms, and is, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, or a 1-butynyl group. Examples include a group, a 2-butynyl group, a 3-butynyl group, a pentynyl group and a 1-hexynyl group.

The C1-C6 _- haloalkyl group, _{C2 -} C6 _- haloalkenyl group, or C2 _- C6 _- haloalkynyl group is the above-mentioned C1-C6 _- alkyl group and _{C2 -} C6 _- alkenyl group, respectively. If one or more halogen atoms are substituted at substitutable positions of the group or C2 _- C6 _- alkynyl group and the number of substituted halogen groups is two or more, the halogen groups may be 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 be. Examples of the C1-C6 _- alkyl group, C2 _- C6 _- alkenyl group, and _{C2 -} C6 _- alkynyl group in ^R1 include the groups listed as examples of the organic group represented by ^RD . 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 . -Alkyl group or COXR ⁵ , most preferably hydrogen or C1 _- C6 _- 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.

In the C ₃ -C ₈ -cycloalkyl-C ₁ -C ₄ -alkyl group, a cyclic cycloalkyl group having 3 to 8 carbon atoms becomes 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 a linear or branched alkyl group having 1 to 4 carbon atoms substituted with a phenyl group, for example, a phenylmethyl group, a 2-phenylethyl group, and 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 phenyl-1-methylethenyl 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 an example of the organic group represented by R ^D and R ¹ . R5 is preferably hydrogen, a C1 ^- C6 _- alkyl group, a _{C2 -} C6 _- alkenyl group or _a C2 _- C6 _- alkynyl group, and more preferably hydrogen or C1- _C6- . 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, phenyl group, phenyl-C ₁ -C ₄ -alkyl group, 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 the organic groups represented by R ^D and R ¹ . R6 is preferably hydrogen, a C1 ^- C6 _- alkyl group, a _{C2 -} C6 _- alkenyl group or a C2 _- C6 _- 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 . ^R7 , R8 and ^R9 are independently hydrogen, C1 ^- C6 _- alkyl group, _{C2 -} C6 _- alkenyl group, C2 _- C6 _- alkynyl group, C3 _- C8 _- 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 -Alkinyl groups, which can be mentioned as an example of the organic groups represented by R ^D and R ¹ . R ⁸ and R ⁹ may form a ring.

^R7 is preferably a C1 _- C6 _- alkyl group.

The aliphatic groups in R ¹ , R ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ may have 1, 2, 3 or the maximum possible number of the same or different groups ^Ra . Often, Ra is selected independently of each other from ^a halogen group, a cyano group, a nitro group, _a C1- _C4 -alkoxy group and _a C1- _C4 -haloalkoxy group. The C1- _{C4 -} 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, a propoxy group, a 1-methylethoxy group, a butoxy group, and the like. Examples thereof include 1-methylpropoxy group and 1,1-dimethylethoxy group.

Further, the C1- _{C4 -} 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. May be.

　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である。ハロゲン基、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、及びＣ_１－Ｃ_４－ハロアルコキシ基は、Ｒ^Ｄ、Ｒ^１又はＲ^ａで表される有機基の例示として挙げた基を挙げることができる。Ｒ^３は、好ましくは、ハロゲン基、シアノ基、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、－ＳＯＲ^１０又は－ＳＦ_５であり、さらに好ましくは、ハロゲン基、シアノ基、Ｃ_１－Ｃ_４－アルキル基、Ｃ_１－Ｃ_４－ハロアルキル基又はＣ_１－Ｃ_４－アルコキシ基である。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る。Ｅがフェニル基の場合、Ｒ^３の置換位置は２位、３位、５位又は６位であり、好ましくは２位である。ｎは、０、１、２又は３であり、好ましくは１である。また、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、Ｒ^３の置換位置は、２位、３位、５位及び６位のうちＮ原子を含まない位置であり、好ましくは２位である。この場合、ｎは、０、１又は２であり、好ましくは１である。 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, C1- _{C4 -} alkyl group, C1- _{C4 -} haloalkyl group, C1- _{C4 -} alkoxy group, and C1- _{C4 -} haloalkoxy group are R ^D , R ¹ or ^Ra . Examples of the organic group represented by the above can be mentioned. R3 is preferably a halogen group ^, a cyano group, a C1- _{C4 -} alkyl group, _a C1- _C4 -haloalkyl group, _a C1- _C4 -alkoxy group, -SOR ¹⁰ or -SF ₅ . More preferably, it is a halogen group, a cyano group, a C1- _{C4 -} alkyl group, _a C1- _C4 -haloalkyl group or _a C1- _C4 -alkoxy group. R ¹⁰ is a C1- _{C4 -} alkyl group or _a C1- _C4 -haloalkyl group. When E is a phenyl group, the substitution position of R ³ is at the 2-position, 3-position, 5-position or 6-position, preferably 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 atom 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.

^R4 is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C1- _{C4 -} alkyl group, _a C1- _C4 -haloalkyl group, and _a C1- _C4 -alkoxy group. Or with C1- _{C4 -} haloalkoxy group, C1- _{C4 -} alkylamino group, C1- _{C4 -} dialkylamino group, C1- _{C4 -} alkylacylamino group, -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 the group mentioned as an example of the organic group represented by ^R3 can be mentioned. ^R4 is preferably a halogen group, a nitro group, an amino group, a C1- _{C4 -} alkyl group, _a C1- _C4 -haloalkyl group, _a C1- _C4 -alkoxy group, and _a C1- _C4 -halo. It is an alkoxy group, _a C1- _C4 -alkylamino group, _a C1- _{C4 -} dialkylamino group, a C1- _C4 -alkylacylamino group, -SOR ¹⁰ or -SF ₅ , and 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 C1- _{C4 -} 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, and is, for example, methylamino. Examples include a group, an ethylamino group, a propylamino group, a 1-methylethylamino group, and a 1,1-dimethylethylamino group.

The C1- _{C4 -} dialkylamino group is an amino group in which both of the hydrogen atoms of the amino group are substituted with a linear or branched alkyl group having 1 to 4 carbon atoms, for example, N. , N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N-di (1-methylethyl) amino group, and N, N-di (1,1-dimethylethyl) ) Amino group is mentioned.

The C1- _{C4 -} alkylacylamino group is an amino group in which one or two of the hydrogen atoms of the amino group are replaced with a linear or branched alkylacyl group having 1 to 4 carbon atoms. For example, methylacylamino group, ethylacylamino group, propylacylamino group, (1-methylethyl) acylamino group, (1,1-dimethylethyl) acylamino group, N, N-dimethylacylamino group, N, N -Diethylacylamino group, N, N-dipropylacylamino group, N, N-di-1-methylethylacylamino group, and N, N-di-1,1-dimethylethylacylamino group can be mentioned.

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 Alternatively, it may have the maximum number of possible identical or different groups R ^b , where R ^b is a halogen group, a cyano group, a nitro group, a C1- _{C4 -} alkyl group, _a C1- _C4 -alkoxy. The groups are independently selected from the C1- _{C4 -} haloalkyl group and the C1- _{C4 -} haloalkoxy group. The halogen group, C1- _{C4 -} alkyl group, C1- _{C4 -} alkoxy group, C1- _{C4 -} haloalkyl group and C1- _{C4 -} haloalkoxy group are R ^D , R ¹ or ^Ra . Examples of the represented organic groups include the groups listed.

Y is an oxygen atom connected to an arbitrary position of the phenyl group to which (R ³ ) _n is bonded, -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 bonded to the ortho-position, meta-position, or para-position of the phenyl group substituted with R3 ^, and is preferably the meta-position 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 composed. 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 pyridazinyl 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 indrill group, an isoindryl group, a benzoimidazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a cinnolyl group, a benzopyranyl group, and a pteridinyl group. Can be mentioned.

R ⁴ is bonded to an arbitrary substitution position by m, 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 one phenyl or benzyl substituent, if desired. Tetrabutylammonium, trimethylbenzylammonium), as well as phosphonium ion, sulfonium ion (preferably tri (C1- _{C4 -} alkyl) sulfonium), and sulfoxonium ion (preferably tri (C1- _{C4 -} alkyl) sulfonium). It is also (xonium). The anions of useful acid addition salts 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, hexafluorosilicate ions, hexafluorophosphate ions, benzoate ions, and C1- _{C4 -} alkanoic acid anions, preferably formate ions, acetate ions, propionate ions and butyrate ions. 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) and its N-oxide form can be produced according to the method described in Patent Document 2.

[3] Application of disease control agent for agriculture and gardening The disease azole derivative (I) has an imidazolyl group or a 1,2,4-triazolyl group, and forms an acid addition salt of an inorganic acid and an organic acid, or a metal complex. .. Then, it acts as a part of an acid addition salt and a metal complex, and exhibits excellent antibacterial activity against pathogens that are less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type. Shows excellent control effect against diseases caused by pathogens.

In the specification of the present application, the "sterol biosynthesis inhibitor" is classified as "sterol biosynthesis (G) of cell membrane" in the action mechanism classification (2021 version) of the fungicide by FRAC (Fungicide Resistance Action Committee). It is a fungicide and means a substance having bactericidal activity by inhibiting the biosynthesis of sterols in the cell membrane of pathogenic filamentous fungi. Further, in the present specification, the “existing sterol biosynthesis inhibitor” means a known sterol biosynthesis inhibitor whose presence of drug-resistant bacteria has been confirmed at the time of filing the application of the present application.

Among such existing sterol biosynthesis inhibitors, preferably, a DMI bactericide (FRAC code: 3), which is an inhibitor of the C14-position demethylase (CYP51) in sterol biosynthesis, and Δ in sterol biosynthesis. ¹⁴ Reductase and Δ ⁸ → Δ ⁷ -amines that are inhibitors of isomerase (FRAC code: 5), and KRI sterilization that is an inhibitor of 3-keto reductase in C4 position demethylation of sterol biosynthesis system An agent (FRAC code: 17), more preferably a DMI bactericidal agent for which the development of resistant bacteria has been confirmed in a plurality of pathogenic bacteria.

Specific examples of existing sterol biosynthesis inhibitors include the following. Mefentrifluconazole, flukinconazole, metconazole, diphenoconazole, azaconazole, bitertanol, bromconazole, cyproconazole, diniconazole, epoxyconazole, etaconazole, fenbuconazole, flukinconazole, flusilazole, flutriafol, hexaconazole , Imibenconazole, Ipconazole, Microbutanil, Penconazole, Propiconazole, Simeconazole, Prothioconazole, Tebuconazole, Tetraconazole, Triazimephon, Triazimenol, Trithiconazole, Imazalil, Pefrazoate, Prochloraz, Triflumizole, O Kispoconazole, trifolin, pyrifenox, pyrisoxazole, nuarimol, phenalimol.

As used herein, the term "pathogen that is less sensitive to existing sterol biosynthesis inhibitors compared to wild-type" refers to at least one existing sterol biosynthesis inhibitor as compared to wild-type pathogens. It means a pathogen with low susceptibility. Such pathogens are at least selected from the group consisting of mutations in genes encoding target proteins that act as sterol biosynthesis inhibitors, overexpression of the target proteins, and development of drug efflux pumps in the cell membrane. One factor includes pathogens that have acquired low susceptibility to existing sterol biosynthesis inhibitors.

Specific examples of diseases caused by pathogens that are less sensitive to existing sterol biosynthesis inhibitors than wild-type diseases, which are applicable diseases of agricultural and horticultural disease control agents according to this embodiment, are as follows. be able to. The parentheses after each disease indicate the main pathogens that cause the disease. Soybean rust (Phakopsora pachyrhizi, Phakopsora meibomiae), rice fool seedling disease (Fusarium fujikuroi), rice lysoctonia leaf spot disease (Rhizoctonia solani), wheat udonko disease (Erysiphe graminis f. ), Puccinia striiformis, Pyrenophora graminea, Rhynchosporium secalis, Ustilago nuda, Fusarium head blight, Fusarium head blight (Fusarium graminearum, Microdochium nivale), Wheat Udonko disease (Erysiphe graminis f. Sp tritici), Wheat red rust (Puccinia recondita), Wheat yellow rust (Puccinia striiformis), Wheat Fusarium head blight (Pseudocercosporella) Diseases (Fusarium graminearum, Microdochium nivale), Wheat wilt (Phaeosphaeria nodorum), Wheat leaf blight (Zymoseptoria tritici), Wheat Fusarium head blight (Microdochium nivale), Wheat wilt (Gaeumannomyces graminis), Wheat black spots Epicoccum spp), wheat yellow spot disease (Pyrenophora tritici-repentis), wheat small granule nuclear disease (Typhula incarnate, Typhula ishikariensis), wheat spot disease (Ramularia collo-cygni), embaku naked black spike disease (Ustilago avenae) (Sclerotinia homoeocarpa), corn scab (Ustilago maydis), corn charcoal scab (Colletotrichum graminicola), corn brown spot disease (Kabatiella zeae), corn gray spot disease (C) ercospora zeae-maydis), corn panama disease (Setosphaeria turcica), corn northern spot disease (Cochliobolus carbonum), corn spot disease (Physoderma maydis), corn rust (Puccinia spp, Puccinia sorghi), corn sesame leaf blight (Bipolaris) maydis), corn yellow sesame leaf blight (Phyllosticta maydis), corn red mold (Gibberella zeae, Fusarium verticillioides), Uri-type Udonko disease (Sphaerotheca fuliginea), Uri-type charcoal disease (Colletotrichum-lagenarium, Glomerella) Foot rot disease (Fusarium solani), cucumber panama disease (Pseudoperonospora cubeensis), cucumber gray plague (Phytophthora capsici), cucumber vine split disease (Fusarium oxysporum f.sp.cucumerinum), watermelon vine split disease (Fusarium oxyspor) niveum), apple udonko disease (Podosphaera leucotricha), apple scab (Venturia inaequalis), apple morinia disease (Monilinia mali), apple spot foliar disease (Alternaria alternata apple pathotype), apple rot disease (Valsa mali), pear black spot disease (Alternaria alternativea pear pathotype), pear udonko disease (Phyllactinia pyri), pear red spot disease (Gymnosporangium asiaticum), pear scab (Venturia nashicola), strawberry udonko disease (Sphaerotheca humuli), nuclear fruit tree ash star fructicola), nuclear fruit leaf spot disease (Blumeriella jaapii), citrus blue mold (Penicillium italicum), grape udonko disease (Uncinula necator), grape panama disease (Plasmopar) a viticola), Glomerella cingulata, Leaf spots (Phakopsora ampelopsidis), Cercospora beticola, Erysiphe betae, Thanatephorus cucumeris, Tensai Root rot (Thanatephorus cucumeris), Tensai black root disease (Aphanomyces cochlioides), Daikon chlorosis (Fusarium oxysporum f.sp.raphani), Cha charcoal scab (Discula theae-sinensis), Cha moth disease (Exobasidium vexans), Cha brown circle Star disease (Pseudocercospora ocellata, Cercospora chaae), Cha ring spot disease (Pestalotiopsis longiseta, Pestalotiopsis theae), Cha net leaf disease (Exobasidium reticulatum), Wata black spot disease Alternaria leaf spot (Alternaria spp), Wata charcoal , Cotton leaf spot (Ascochyta gossypii), Leaf spot disease (Puccinia spp, Phykopsora spp), Cercospora blight and leaf spot (Cercospora spp), Wata Diplopia bollrot (Diplopia spp), Wata ), Wata's Phomablight (Phomaspp), Wata's Stemphyllium leaf spot (Stemphyllium spp), Banana yellow spot (Mycosphaerella musicoka), Banana black spot (Mycosphaerella fijiensis), Cercospora (Mycovellosiella) Tomato leaf mold (Passalora fulva), citrus green mold (Penicillium digitatum), leaf spots (Sphaerotheca mors-uvae), Pecan scab (Cladosporium cary) igenum), chrysanthemum white rust (Puccinia horiana), powdery mildew (Sphaerotheca pannosa), gray mold (Botrytis cinerea) and sclerotinia sclerotinia (Sclerotinia sclerotirum), etc. Also, Aspergillus, Botryosphaeria, Calonectria, Cochliobolus, Corticium, Diplodia, Penicillium, Fusarium, Gibberella, Mucor, Phoma, Phomopsis, Pyrenophora, Pythium, Rhizoctonia. Diseases of various plants caused by the genera Thielaviopsis, Tilletia, Trichoderma, Ustilago, etc.

The agricultural and horticultural disease control agent according to this embodiment can be used as a fungicide. In addition, the agricultural and horticultural disease control agent according to this embodiment is a wheat leaf blight caused by wheat leaf blight, which is less sensitive to existing sterol biosynthesis inhibitors than the wild type among the above-mentioned diseases. Has an excellent control effect on wheat. Therefore, the agricultural and horticultural disease control agent according to this embodiment is preferably used for controlling wheat, but is not limited thereto.

Zymoseptoria trichophyton, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild-type, is particularly susceptible to mutations in the gene encoding CYP51, which is the site of action of DMI fungicides, overexpression of CYP51, and , Zymoseptoria trichophyton that has acquired low sensitivity to existing sterol biosynthesis inhibitors by at least one factor selected from the group consisting of the development of drug efflux pumps in the cell membrane.

Zymoseptoria trifolium, which has acquired low sensitivity to existing sterol biosynthesis inhibitors, has one or more amino acid mutations in the CYP51 protein, thereby acquiring low sensitivity to existing sterol biosynthesis inhibitors. .. Here, the "amino acid mutation" is intended to replace, delete, or insert an amino acid residue.

Mutations in the gene encoding CYP51 include the 50th, 107th, 134th, 136th, 137th, 145th, 178th, 188th, 208th, 259th, and 284th amino acid sequences of wild-type CYP51. , 303rd, 311th, 312th, 379th, 381st, 410th, 412th, 459th, 460th, 461st, 476th, 490th, 510th, 513th and 524th. Examples include mutations that result in the substitution or deletion of amino acid residues at at least one amino acid position selected.

In a preferred embodiment, the mutation in the gene encoding CYP51 is the amino acid sequence of wild-type CYP51 at positions 50, 107, 134, 136, 188, 379, 381, 459, 460, 461. It may be a mutation that results in the substitution or deletion of an amino acid residue at at least one amino acid position selected from the group consisting of 513th and 524th. In a more preferred embodiment, mutations in the gene encoding CYP51 are in the amino acid sequences of wild-type CYP51 at positions 134, 136, 188, 379, 381, 459, 460, 461, 513 and It may be a mutation that results in the substitution or deletion of an amino acid residue at at least one amino acid position selected from the group consisting of position 524.

In another preferred embodiment, the mutation in the gene encoding CYP51 is a mutation that results in at least one selected from the group consisting of the following amino acid residue substitutions or deletions in the amino acid sequence of wild-type CYP51. It's okay. In addition, Δ means deletion of amino acid residue: L50S, D107V, D134G, V136A / C / G, Y137F, M145L, N178S, S188N, S208T, N284H, H303Y, A311G, G312A, A379G, I381V, A410T, G412A, Y459C / D / N / P / S / Δ, G460D / Δ, Y461D / H / S, V490L, G510C, N513K, S524T.

In another preferred embodiment, the mutation in the gene encoding CYP51 may be a mutation in the amino acid sequence of wild-type CYP51 that results in at least one selected from the group consisting of the mutations listed below: D134G, V136A /. C, S188N, A379G, I381V, Y459S / Δ, G460Δ, Y461H, N513K, S524T.

In another preferred embodiment, mutations in the gene encoding CYP51 may include mutations in the amino acid sequence of wild-type CYP51 that result in a combination of mutations listed below:
I381V + Y461H,
I381V + Y459S,
D134G + V136A + S188N + I381V + Y461H,
V136C + S188N + A379G + I381V + Y459Δ + G460Δ + S524T,
D134G + V136A + S188N + I381V + Y461H + S524T,
V136C + S188N + Y459Δ + G460Δ + N513K,
V136A + Y461H,
S188N + A379G + I381V + Y459Δ + G460Δ + N513K,
D134G + V136A + I381V + Y461H,
S188N + N513K,
S188N + I381V + Y459Δ + G460Δ + N513K.

In the specification of the present application, the notation "+" means "and". For example, "I381V + Y461H" means that the gene encoding CYP51 contains at least a mutation that results in a mutation in the amino acid sequences I381V and Y461H of wild-type CYP51.

Examples of the drug discharge pump that causes low sensitivity to existing sterol biosynthesis inhibitors include membrane transporters that discharge the drug that has flowed into the cell to the outside of the cell, such as an ABC transporter and an MFS transporter. ..

[4] Plants to which agricultural and horticultural disease control agents are applied The agricultural and horticultural disease control agents according to this embodiment are plants that are affected by pathogens that are less sensitive to existing sterol biosynthesis inhibitors, or the plants concerned. It can be used for plants where diseases can occur. Examples of such applicable plants include: Rice, wheat, barley, lime, embaku, triticale, corn, morokoshi (sorghum), sugar cane, shiva, bentgrass, Bermudagrass, fescue and ryegrass and other rice families, soybeans, lacquer tree, green beans, pea, azuki and alfalfa Beans, Hirugao such as sweet potatoes, Tomatoes, peppers, tomatoes, eggplants, potatoes and tobacco, Tade species such as buckwheat, Kiku family such as sunflower, Ukogi family such as butterfly, Abranaceae such as rapeseed, hakusai, cub, cabbage and daikon, Akaza family such as Tensai, Aoi family such as cotton, Akane family such as coffee tree, Aogiri family such as cacao, Tsubaki family such as cha, Uri families such as watermelons, melons, cucumbers and pumpkins, lilies such as onions, onions and garlic, roses such as strawberries, apples, almonds, apricots, sea urchins, peaches, peaches, peaches and pears, carrots, etc. Seri family, 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, Walnut such as Pekan Family, Basho family such as banana, Mokusei family such as olive, Palm family such as Coco palm and Natsume palm, Mikan family such as tangerine, orange, grapefruit and lemon, Grape family such as grape, Flowers and ornamental plants), trees other than fruit trees and other ornamental plants. In addition, wild plants, plant cultivars, plants and plant cultivars obtained by conventional biological breeding such as crossbreeding or progenitor fusion, and genetically modified plant cultivars obtained by genetic engineering and approved in each country can be mentioned. .. Examples of such genetically modified plant cultivars include those accumulated in the database of the International Agribio Corporation (ISAAA). Specifically, Roundup Ready, Liberty Link, IMI, SCS, Clearfield, Enlist, Bt, BXN, Poast Compatible, AgriSure, Genuity, Optimum, Powercore, DroughtGard, YieldGard, Herculex, WideStrike, Twinlink, VipCot, GlyTol, Newleaf, KnockOut, BiteGard, BtXtra, StarLink, Nucotn, NatureGard, Protecta, SmartStax, Power Core, InVigor and Bollgard, Genuity Intacta RR2 Pro, Xtend, Bt Maize, Liberty Link, YieldGard Corn Borner, Roundup Ready, Roundup Ready / YieldGard 2, Herculex 1, YieldGard Rootworm, Herculex RW, AgriSure GT, YieldGard Plus, Herculex XTRA, AgriSure GT / CB / LL, YieldGard VT Triple, AgriSure RW, AgriSure 3000GT, Genuity SmartStax, Genuity VT Double Pro, Genuity VT Triple Pro, Optimum AcreMax I, Optimum AcreMax RW, Optimum Intrasect, AgriSure Viptera 3110, AgriSure Vptera 3111, AgruSure 3122 EZ Refuge, Agrisure 3122 Refuge Renew, AgriSure Viptera 3220 EZ Refuge, AgriSure Viptera 3220 Refuge Renew, Power RIB Complete, Genuity VT Double Pro RIB Complete, Optimum Acre Max, Optimum Intrasect Xtra, Optimum TRIsect, Optimum AcreMax Xtreme, Optimum Intrasect Xtreme, DroughtGard, Genuity VT Triple Pro RIB Complete, Optimum Leptra, AgriSure Artesian 3030A, AgriSure Artesian 3011A, AgriSure Duracade, Advanced Corn , Optimum AcreMax Xtreme-R, Optimum AcreMax RW-R, Optimum AcreMax-R ,, Optimum AcreMax Xtra-R, Bollgard Cotton, BXN Cotton, Sulfonylurea Tolerant Cotton, Bollgard Cotton, Bollgard Cotton, Roundup Ready Cotton, Bollgard / Roundup Ready Cotton , Bt / BXN Cotton, Bollgard II, WideStrike, Bollgard II / Roundup Ready, LibertyLink cotton, RR Flex / Bollgard II, GlyTol Cotton, VipCot Cotton, Twinlink, WideStrike 3, Genuity Bollgard II XtendFlex, Enlist Cotton, Enlist WideStrike 3 Cotton, Examples include those containing registered trademarks such as Bollgard 3 XtendFlex Cotton, IMI Canola, Liberty Link Conola, Roundup Ready Conola and BXN Canola.

[5] Pharmaceuticals The agricultural and horticultural disease control agent according to this embodiment may contain an azole derivative (I) as an active ingredient. The content of the azole derivative (I) in the agricultural and horticultural disease control agent is, for example, 0.1 to 95% by weight, preferably 0.5 to 90% by weight, and preferably 2 to 80% by weight. More preferred. The content of the azole derivative (I) in the spraying liquid at the time of actual spraying is not particularly limited as long as it can exhibit the desired activity.

The azole derivative (I) contained as an active ingredient in the agricultural and horticultural disease control agent may be a single compound or a mixture of two or more kinds of compounds. In addition to the azole derivative (I), agricultural and horticultural disease control may include a solid carrier, a liquid carrier (diluent), a surfactant, a spreading agent, an adjuvant, or other pharmaceutical adjuvants described below.

Further, the agricultural and horticultural disease control agent according to this embodiment is known in addition to the active ingredient for controlling the disease caused by the pathogen, which is less sensitive to the existing sterol biosynthesis inhibitor as compared with the wild type. It can also be used as a mixed agent with enhanced performance as an agricultural and horticultural agent in combination with other active ingredients. Therefore, even if the mixture further contains other known active ingredients, azole is used as an active ingredient for controlling diseases caused by pathogens that are less sensitive to existing sterol biosynthesis inhibitors than the wild type. As long as the derivative (I) is contained, it is included in the scope of the present invention. Other known active ingredients include known active ingredients contained in fungicides, insecticides, acaricides, nematodes, and plant growth regulators.

When the agricultural and horticultural disease control agent according to this embodiment contains two or more kinds of active ingredients, the formulation form is (i) a formulation-embedded type prepared by including the azole derivative (I) and other active ingredients. And, (ii) the first preparation agent containing the azole derivative (I) and the second preparation agent containing another active ingredient independent of this are mixed immediately before use. The tank mix type can be mentioned.

In the agricultural and horticultural disease control agent according to this embodiment, the azole derivative (I) is mixed with a solid carrier or a liquid carrier (diluent), a surfactant, other pharmaceutical adjuncts and the like to treat foliage or non-foliage. It can be formulated and used in various forms such as powders, wettable powders, granules and emulsions. Further, a conventionally known biosurfactant, for example, mannosylargitol lipid, sophorolipid, ramnolipid, trehalose lipid, cellobiose lipid, glucose lipid, oligosaccharide fatty acid ester, surfactin, serauetchin, lykensin, arslofactin and the like is further contained as an adjuvant. You may.

Examples of solid carriers, liquid carriers and surfactants used as formulation aids are as follows. First, solid carriers are used as powder carriers, granular carriers and the like, and clay, talc, diatomaceous earth, zeolite, montmorillonite, bentonite and acidic. Minerals such as white clay, active white clay, attapargite, methodolith, vermiculite, pearlite, pebbles, silica sand; synthetic organic substances such as urea; salts such as calcium carbonate, sodium carbonate, sodium sulfate, limestone, and baking soda; amorphous such as white carbon. Synthetic inorganic substances such as silica and titanium dioxide; plants such as wood flour, corn stalk (cob), walnut shell (hard fruit hull), fruit nucleus, fir, oak, bran, soybean flour, powdered cellulose, starch, dextrin, sugar, etc. Sex carriers; crosslinked lignin, cationic gels, gelatin gelled with heating or polyvalent metal salts, water-soluble polymer gels such as agar, and chlorinated polyethylene, chlorinated polypropylene, polyvinyl acetate, polyvinyl chloride, ethylene-vinyl acetate. Various polymer carriers such as copolymers and urea-aldehyde resins; and the like can be mentioned.

Liquid carriers include aliphatic solvents (paraffins), aromatic solvents (xylene, alkylbenzene, alkylnaphthalene, solventnaphtha, etc.), mixed solvents (kerosene), machine oils (refined high boiling weight aliphatic hydrocarbons), alcohols (alcohols). Methanol, ethanol, isopropanol, cyclohexanol, etc.), polyhydric alcohols (ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, etc.), polyhydric alcohol derivatives (propylene-based glycol ether, etc.), ketones Classes (acetone, acetophenone, cyclohexanone, methylcyclohexanone, γ-butyrolactone, etc.), esters (fatty acid methyl ester (palm oil fatty acid methyl ester), ethyl hexyl lactate, propylene carbonate, dibasic acid methyl ester (succinic acid dimethyl ester, glutamate dimethyl ester) Ester, adipic acid dimethyl ester)), nitrogen-containing carriers (N-alkylpyrrolidones), fats and oils (palm oil, soybean oil, rapeseed oil, etc.), amide-based solvents (dimethylformamide, N, N-dimethyloctaneamide, N) , N-dimethyldecaneamide, 5- (dimethylamino) -2-methyl-5-oxo-valeric acid methyl ester, N-acylmorpholin-based solvent (CAS No. 887947-29-7, etc.), dimethyl sulfoxide, acetonitrile , Water, etc.

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, and polyoxyethylene fatty acid diester. , Polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene / polyoxypropylene block polymer, alkylpolyoxyethylene / 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 Examples thereof include ether and ester-type silicon and fluorine-based surfactants, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, and alkyl glycosides. Examples of the anionic surfactant include alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene benzyl (or styryl) phenyl (or phenylphenyl) ether sulfate, polyoxyethylene, and polyoxypropylene. Salts of sulfates such as block polymer sulfate, paraffin (alkane) sulfonate, α-olefin sulfonate, dialkyl sulfosuccinate, alkylbenzene sulfonate, mono or dialkylnaphthalene sulfonate, naphthalene sulfonate formalin condensate, alkyldiphenyl ether disulfonate, lignin sulfonate, Salts of sulfonates such as polyoxyethylene alkylphenyl ether sulfonates, polyoxyethylene alkyl ether sulfosuccinic acid half esters, fatty acids, salts of fatty acids such as N-methyl-fatty acid sarcosinates, resin acids, polyoxyethylene alkyl ether phosphates, Polyoxyethylene mono or dialkylphenyl ether phosphate, polyoxyethylene benzyl (or styryl) phenyl (or phenylphenyl) ether phosphate, polyoxyethylene / polyoxypropylene block polymer, phosphatidylcholine phosphatidylethanolimine (resitin), alkyl phosphate, etc. Kind of salt and the like. Cationic surfactants include ammonium salts such as alkyltrimethylammonium chloride, methylpolyoxyethylene alkylammonium chloride, alkyl N-methylpyridium bromide, mono or dialkylmethylated ammonium chloride, alkylpentamethylpropylenediaminedichloride and alkyldimethyl. Examples thereof include benzalkonium salts such as benzalkonium chloride and benzethonium chloride (octylphenoxyethoxyethyldimethylbenzylammonium chloride).

Other pharmaceutical aids include inorganic salts such as sodium and potassium as pH adjusters, fluorine-based and silicone-based defoaming agents, water-soluble salts such as salt, and xatane gum and guar gum used as thickeners. Water-soluble polymers such as carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, polyvinyl alcohol, starch derivative, polysaccharides, alginic acid and its salts, metal stearate used as a disintegrant dispersant, sodium tripolyphosphate, hexametallin Examples thereof include acid soda, spreading agents, adjuvants, preservatives, coloring agents, antioxidants, ultraviolet absorbers, and chemical damage reducing agents.

The agricultural and horticultural disease control agent for foliage treatment may contain a pharmaceutical adjunct, for example, a spreading agent, an adjuvant, etc., which are usually used for application to foliage treatment such as foliage spraying.

Agricultural and horticultural disease control agents for non-foliage treatment are pharmaceutical adjuvants commonly used for application to non-foliage treatment such as seed treatment including treatment of bulbs and tubers, irrigation treatment, and water surface treatment. , For example, a spreading agent, an adjuvant, etc. may be contained.

[6] Disease control method The disease control method according to the present embodiment uses the above-mentioned agricultural and horticultural disease control agent and is based on a pathogenic bacterium that is less sensitive to existing sterol biosynthesis inhibitors than the wild type. Control the disease.

In the specification of the present application, "controlling" means that when the above-mentioned agricultural and horticultural disease control agent is applied, hyphal elongation of pathogens is compared with the case where the agricultural and horticultural disease control agent is not applied (control). Alternatively, it means that the growth is inhibited or the morbidity of the disease is reduced. The rate of inhibition of hyphal elongation or growth of pathogens (hereinafter also referred to as "hyphal elongation inhibition rate") or reduction rate of disease morbidity (hereinafter also referred to as "control value") with respect to the control shall be at least 40%. Is more preferable, at least 60% is more preferable, at least 70% is further preferable, at least 80% is further preferable, and at least 90% is particularly preferable. The hyphal elongation inhibition rate and the control value can be calculated by, for example, the methods described in Examples described later.

The agricultural and horticultural disease control agent in this embodiment can be used in cultivated or non-agricultural lands such as fields, paddy fields, lawns, and orchards. Further, the agricultural and horticultural disease control agent in the present embodiment is applied not only by foliage treatment such as spraying foliage, but also by non-foliage treatment such as seed treatment including treatment of bulbs and tubers, irrigation treatment, and water surface treatment. can. Therefore, the disease control method in the present embodiment may be one in which foliage treatment or non-foliage treatment is performed using the above-mentioned agricultural and horticultural agents. In addition, when the non-foliage treatment is performed, the labor can be reduced as compared with the case where the foliage treatment is performed.

In the application by seed treatment, the chemicals are attached to the seeds by mixing the wettable powder and powder with the seeds and stirring, or by immersing the seeds in the diluted wettable powder. It also includes a seed coating process. The amount of the azole derivative (I) used in the seed treatment is, for example, 0.01 to 10000 g, preferably 0.1, per 100 kg of seeds in order to achieve the above-mentioned preferable hyphal elongation inhibition rate or control value. It is ~ 1000 g. Seeds treated with agricultural and horticultural disease control agents may be used in the same manner as ordinary seeds.

The application by irrigation treatment is performed by treating the planting hole or its surroundings with granules, etc. at the time of transplanting seedlings, or treating the soil around the seeds or plants with granules, wettable powders, etc. .. The amount of the azole derivative (I) used in the irrigation treatment is, for example, 0.01 to 10000 g per 1 m ² of agricultural and horticultural land, preferably 0.01 to 10000 g, in order to achieve the above-mentioned preferable hyphal elongation inhibition rate or control value. It is 1 to 1000 g.

Application by water surface treatment is performed by treating the surface water of the paddy field with granules or the like. The amount of the azole derivative (I) used in the case of water surface treatment is, for example, 0.1 to 10000 g, preferably 1 to 1000 g per paddy field 10a in order to achieve the above-mentioned preferable hyphal elongation inhibition rate or control value. ..

The amount of the azole derivative (I) used for foliar spraying is, for example, 20 to 20 per ha of agricultural and horticultural fields such as fields, rice fields, orchards and greenhouses in order to achieve the above-mentioned preferable hyphal elongation inhibition rate or control value. It is 5000 g, more preferably 50 to 2000 g.

As described above, the agricultural and horticultural disease control agent according to this embodiment exhibits an excellent bactericidal action against pathogens that are less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type. That is, the agricultural and horticultural disease control agent according to this embodiment has low toxicity to humans and animals, is excellent in handling safety, and is less sensitive to existing sterol biosynthesis inhibitors than the wild type. It can show a high control effect against.

(Additional notes)
The present invention is not limited to the above-described embodiment, and various modifications can be made within the scope of the claims. That is, an embodiment obtained by combining technical means appropriately modified within the scope of the claims is also included in the technical scope of the present invention.

　［式（Ｉ）中、
　Ａは、Ｎであり；
　Ｄは、水素であり；
　Ｒ^１は、水素又はＣ_１－Ｃ_６－アルキル基であり；
　Ｒ^２は、－ＯＲ^７であり；
　Ｒ^７は、水素、Ｃ_１－Ｃ_６－アルキル基又はＣ_３－Ｃ_８－シクロアルキル基であり；
　Ｒ^４は、ハロゲン基、Ｃ_１－Ｃ_４－ハロアルキル基、Ｃ_１－Ｃ_４－アルコキシ基又は－ＳＦ_５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、ハロゲン基、Ｃ_１－Ｃ_４－ハロアルキル基又はＣ_１－Ｃ_４－ハロアルコキシ基であり；
　Ｒ^３は任意の置換位置にｎ個結合しており；
　Ｅがフェニル基である場合、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、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であり；
　Ｚは、フェニル基、ナフチル基、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］。
〔２〕茎葉処理用または非茎葉処理用であることを特徴とする、上記〔１〕に記載の農園芸用病害防除剤。
〔３〕上記病害が、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるコムギ葉枯病菌によるコムギ葉枯病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるオオムギ網班病菌によるオオムギ網班病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性である菌核病菌による菌核病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるイネばか苗病菌によるイネばか苗病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるうどんこ病菌によるうどんこ病（オオムギうどんこ病、コムギうどんこ病、ウリ類うどんこ病、リンゴうどんこ病、ナシうどんこ病、イチゴうどんこ病、ブドウうどんこ病、及びテンサイうどんこ病）、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるRamularia collo-cygni菌によるムギ斑点病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるオオムギ雲形病菌によるオオムギ雲形病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるさび病菌によるさび病（ダイズさび病、オオムギ黒さび病、オオムギ黄さび病、コムギ赤さび病、コムギ黄さび病、トウモロコシさび病、ブドウのさび病、及びワタさび病）、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるテンサイ褐斑病菌によるテンサイ褐斑病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるSetosphaeria turcica菌によるトウモロコシすす紋病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるBipolaris maydis菌によるトウモロコシごま葉枯病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるリンゴ黒星病菌によるリンゴ黒星病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるAlternaria菌によるAlternaria病（リンゴ斑点落葉病、ナシ黒斑病、及びワタ黒斑病Alternaria leaf spot）、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるsclerotinia菌によるシバダラースポット病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるバナナシガトカ病菌によるバナナシガトカ病（バナナイエローシガトカ病、及びバナナブラックシガトカ病）、野生型と比較して既存のステロール生合成阻害剤に対して低感受性である灰色かび病菌による灰色かび病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるナシ赤星病菌によるナシ赤星病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるナスすすかび病菌によるナスすすかび病、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるトマト葉かび病菌によるトマト葉かび病、及び、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるカンキツ緑かび病菌によるカンキツ緑かび病からなる群より選択される、上記〔１〕または〔２〕に記載の農園芸用病害防除剤。
〔４〕上記病害が、野生型と比較して既存のステロール生合成阻害剤に対して低感受性であるコムギ葉枯病菌によるコムギ葉枯病であることを特徴とする、上記〔１〕～〔３〕のいずれかに記載の農園芸用病害防除剤。
〔５〕上記コムギ葉枯病菌の上記既存のステロール生合成阻害剤に対する低感受性が、ステロール脱メチル化酵素であるＣＹＰ５１をコードする遺伝子の変異、ＣＹＰ５１の過剰発現、及び、細胞膜における薬剤排出ポンプの発達、からなる群より選択される少なくとも１つに起因することを特徴とする、上記〔４〕に記載の農園芸用病害防除剤。
〔６〕上記ＣＹＰ５１をコードする遺伝子の変異が、野生型ＣＹＰ５１のアミノ酸配列の、５０番目、１０７番目、１３４番目、１３６番目、１３７番目、１４５番目、１７８番目、１８８番目、２０８番目、２５９番目、２８４番目、３０３番目、３１１番目、３１２番目、３７９番目、３８１番目、４１０番目、４１２番目、４５９番目、４６０番目、４６１番目、４７６番目、４９０番目、５１０番目、５１３番目及び５２４番目、からなる群より選択される少なくとも一つのアミノ酸位置におけるアミノ酸残基の置換または欠失をもたらす変異である、上記〔５〕に記載の農園芸用病害防除剤。
〔７〕上記〔１〕～〔６〕のいずれかに記載の農園芸用病害防除剤を使用する、野生型と比較して既存のステロール生合成阻害剤に対して低感受性である病原菌による病害の防除方法。
〔８〕茎葉処理または非茎葉処理を行う、上記〔７〕に記載の防除方法。
〔９〕前記コムギ葉枯病菌が、ＣＹＰ５１をコードする遺伝子の変異が要因の一つとなり、ＤＭＩ殺菌剤に対して低感受性であることを特徴とする、上記〔５〕に記載の農園芸用病害防除剤。 〔summary〕
[1] A farming and horticultural disease control agent containing a compound represented by the following general formula (I), or an N-oxide thereof or a pesticide-acceptable salt as an active ingredient, wherein the disease is wild. An agricultural and horticultural disease control agent that is a disease caused by pathogens that are less sensitive to existing sterol biosynthesis inhibitors than the type.

[In formula (I),
A is N;
D is hydrogen;
R ¹ is a hydrogen or C1 _- C6 _- alkyl group;
R ² is -OR ⁷ ;
^R7 is a hydrogen, C1 _- C6 _- alkyl group or C3 _- C8 _- cycloalkyl group;
^R4 is a halogen group, C1- _{C4 -} haloalkyl group, C1- _{C4 -} alkoxy group or -SF ₅ ;
E is a 6-membered aromatic heterocycle containing 1 or 2 phenyl groups or N atoms.
R3 is a halogen group ^, _a C1- _C4 -haloalkyl group or _a C1- _C4 -haloalkoxy group;
^R3 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;
Y is an oxygen atom that connects to any position in E;
Z is a 5- or 6-membered aromatic heterocycle containing 1 to 4 heteroatoms selected from a phenyl group, a naphthyl group, or O, N, or S.
^R4 is bound to any substitution position by m;
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].
[2] The agricultural and horticultural disease control agent according to the above [1], which is for foliage treatment or non-foliage treatment.
[3] Wheat leaf blight caused by wheat leaf blight, which is less sensitive to the existing sterol biosynthesis inhibitor than the wild type, and the existing sterol biosynthesis inhibitor compared to the wild type. Compared to wild-type, mycorrhizal disease caused by mycorrhizal fungus, which is less sensitive to existing sterol biosynthesis inhibitors, compared to wild-type. Rice fool seedling disease caused by rice fool seedling disease bacteria that are less sensitive to existing sterol biosynthesis inhibitors, and udon caused by udonko disease bacteria that are less sensitive to existing sterol biosynthesis inhibitors compared to wild type Compared to wild type Due to wheat spot disease caused by Ramularia collo-cygni, which is less sensitive to existing sterol biosynthesis inhibitors, and barley cloud disease, which is less sensitive to existing sterol biosynthesis inhibitors than wild-type. Omugi cloud disease, rust caused by rust fungi that are less sensitive to existing sterol biosynthesis inhibitors than wild type (soybean rust, Omugi black rust, Omugi yellow rust, wheat red rust, wheat yellow Rust, corn rust, grape rust, and cotton rust), Tensai brown spot caused by Tensai brown spot, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type, wild type Setosphaeria turcica, which is less sensitive to existing sterol biosynthesis inhibitors, is less sensitive to corn soot, and Bipolaris maydis, which is less sensitive to existing sterol biosynthesis inhibitors than wild-type. Corn sesame leaf blight caused by apple scab, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type, apple scab caused by apple scab, against existing sterol biosynthesis inhibitors compared to wild type Alternaria disease (Apple spot foliar disease, pear black spot, and cotton black spot Alternaria leaf spot) due to Alternaria, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type Shivadara spot disease caused by a certain sclerotinia bacterium, banana sigatoka disease caused by banana stag beetle, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type Nanashigatoka disease (banana yellow shigatoka disease and banana black shigatoka disease), gray mold caused by gray mold fungus, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type, compared to wild type Pear scab caused by pear scab, which is less sensitive to existing sterol biosynthesis inhibitors, and sardine succulent caused by nasal scab, which is less sensitive to existing sterol biosynthesis inhibitors than the wild type. For tomato leaf mold caused by tomato leaf mold, which is less sensitive to mold and existing sterol biosynthesis inhibitors compared to the wild type, and to existing sterol biosynthesis inhibitors compared to the wild type. The agricultural and horticultural disease control agent according to the above [1] or [2], which is selected from the group consisting of citrus green mold caused by citrus green mold that is less sensitive.
[4] The above-mentioned disease is characterized by wheat leaf blight caused by wheat leaf blight fungus, which is less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type. 3] The agricultural and horticultural disease control agent according to any one of.
[5] The low sensitivity of the wheat leaf blight fungus to the existing sterol biosynthesis inhibitor is a mutation in the gene encoding the sterol demethylase CYP51, overexpression of CYP51, and a drug excretion pump in the cell membrane. The agricultural and horticultural disease control agent according to the above [4], which is caused by at least one selected from the group consisting of development.
[6] The mutation in the gene encoding CYP51 is the 50th, 107th, 134th, 136th, 137th, 145th, 178th, 188th, 208th, 208th, 259th amino acid sequence of the wild-type CYP51. From the 284th, 303rd, 311th, 312th, 379th, 381st, 410th, 412th, 459th, 460th, 461st, 476th, 490th, 510th, 513th and 524th. The agricultural and horticultural disease control agent according to the above [5], which is a mutation resulting in substitution or deletion of an amino acid residue at at least one amino acid position selected from the group.
[7] Diseases caused by pathogens that use the agricultural and horticultural disease control agent according to any one of the above [1] to [6] and are less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type. Control method.
[8] The control method according to the above [7], which comprises foliage treatment or non-foliage treatment.
[9] The agricultural and horticultural use according to the above [5], wherein the wheat leaf blight is characterized by a mutation in a gene encoding CYP51 and low sensitivity to a DMI fungicide. Disease control agent.

Hereinafter, the present invention will be specifically described with reference to test examples. The present invention is not limited to the following test examples as long as the gist of the present invention is not exceeded.

<Azole derivative (I)>
The following azole derivative (I) was synthesized according to the method described in Patent Document 2.
Azole Derivative I-1: Methyl 2-hydroxy-2- (2-chloro-4- (4-chlorophenoxy) phenyl) -3- (1H-1,2,4-triazol-1-yl) propanoate Azole derivative I -2: Methyl 2- (4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole-1-yl) propanoate azole derivative I-3: Methyl 2- (2-bromo-4- (4-chlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-4 : Ethyl 2- (2-chloro-4- (4-chlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-5: Methyl 2 -(2-Chloro-4- (4-chlorophenoxy) phenyl) -2-methoxy-3- (1H-1,2,4-triazol-1-yl) propionate azole derivative I-6: methyl 2- (4) -(4-Chlorophenoxy) -2-fluorophenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-7: Methyl-2- (2-chloro -4- (2,4-dichlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-8: methyl 2- (2-chloro- 4- (2-Chlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-9: Methyl 2- (2-chloro-4-( 3-Chlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-10: Methyl 2- (2-chloro-4- (4- (4- (4) Trifluoromethoxy) phenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole-1-yl) propanoate azole derivative I-11: methyl 2- (2-chloro-4- (4-) Bromophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazol-1-yl) propanoate azole derivative I-12: methyl 2- (2-chloro-4- (4-fluorophenoxy) Phenyl) -2-hydroxy-3- (1H-1,2,4 -Triazole-1-yl) propanoate azole derivative I-13: 1,1-dimethylethyl 2- (4- (4-bromophenoxy) -2-chlorophenyl) -2-hydroxy-3- (1H-1,2, 4-Triazole-1-yl) propanoate azole derivative I-14: isopropyl2- (2-chloro-4- (4-chlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole) -1-yl) propanoate azole derivative I-15: 2- (2-chloro-4- (4- (pentafluoro-λ ⁶ -sulfanyl) phenoxy) phenyl) -2-hydroxy-3- (1H-1,2) , 4-Triazole-1-yl) Methylazole derivative of propionate I-16: Cyclopropylmethyl 2- (2-chloro-4- (4-chlorophenoxy) phenyl) -2-hydroxy-3- (1H-1, 2,4-Triazole-1-yl) propanoate Azole derivative I-17: Methyl 2- (2-chloro-4- (3,4-dichlorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2) , 4-Triazole-1-yl) propanoate Azole derivative I-18: Methyl 2- (4- (4-chlorophenoxy) -2- (trifluoromethoxy) phenyl) -2-hydroxy-3- (1H-1, 2,4-Triazole-1-yl) propanoate azole derivative I-19: Methyl 2- (2-chloro-4- (3,4-difluorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2) , 4-Triazole-1-yl) propanoate azole derivative I-20: Methyl 2- (2-chloro-4- (naphthalen-2-yloxy) phenyl) -2-hydroxy-3- (1H-1,2,4) -Triazole-1-yl) propanoate azole derivative I-21: Methyl 2- (2-chloro-4- (4-chloro-3-fluorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2, 4-Triazol-1-yl) propanoate azole derivative I-22: 2- (2-chloro-4- (2,4-difluorophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4- Triazole-1-yl) Methylazole Propionate Derivative I-23: 2- (2-bromo-4- (bromophenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole-1-) Il) Propio Methylazole derivative I-24: 2- (4- (4-bromophenoxy) -2- (trifluoromethyl) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole-1-) Il) Methylazole derivative of propionate I-25: Methyl 2- (2-bromo-4- (4- (trifluoromethyl) phenoxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole) -1-yl) Propanoate Azole Derivative I-26: 2- (2-Chloro-4- (quinolin-6-yloxy) phenyl) -2-hydroxy-3- (1H-1,2,4-triazole-1-) Il) Methyl propionate <Control compound>
The following compounds were prepared as control compounds.

　テブコナゾール：(RS)-1-p-クロロフェニル-4,4-ジメチル-3-(1H-1,2,4-トリアゾール-1-イルメチル)ペンタン-3-オール
　プロピコナゾール：1-[[2-(2,4-ジクロロフェニル)-4-プロピル-1,3-ジオキソラン-2-イル]メチル]-1,2,4-トリアゾール Mefentrifluconazole (compound described in Patent Document 1): 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1,2,4-triazole-1-) Il) Propan-2-olflukinconazole: 3- (2,4-dichlorophenyl) -6-fluoro-2- (1H-1,2,4-triazole-1-yl) quinazoline-4 (3H) -one Metconazole: (1RS, 5RS; 1RS, 5SR) -5- (4-chlorobenzyl) -2,2-dimethyl-1- (1H-1,2,4-triazole-1-ylmethyl) cyclopentanol Diphenoconazole: 1 -({2- [2-Chloro-4- (4-chlorophenoxy) phenyl] -4-methyl-1,3-dioxolan-2-yl} methyl) -1H-1,2,4-triazole Chemical formula A below Control compound A (compound described in Patent Document 1): 2- (6- (4-chlorophenoxy) -2- (trifluoromethyl) pyridine-3-yl) -1- (1H-1) , 2,4-Triazole-1-yl) Propan-2-ol

Tebuconazole: (RS) -1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazole-1-ylmethyl) pentane-3-olpropiconazole: 1-[[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-yl] methyl] -1,2,4-triazole

<Wheat leaf blight, which is less sensitive to existing sterol biosynthesis inhibitors than the wild type>
As pathogens, strains A to K of wheat leaf blight were prepared. These strains are less sensitive to existing sterol biosynthesis inhibitors compared to wild-type by having mutations in specific amino acid positions in the wild-type CYP51 protein. The positions and types of mutations in each strain are shown in Table 9 below. In the table, "Del" means a missing mutation. In addition, the amino acid sequence of the wild-type CYP51 protein can be easily obtained from public databases such as M. graminicola genome sequencing project (https://mycocosm.jgi.doe.gov/Mycgr1/Mycgr1.home.html) and GenBank. It can be, for example, disclosed in "https://mycocosm.jgi.doe.gov/cgi-bin/getDbSeq?db=Mycgr1&searchTabList=protein,proteinHitDesc&hitSeqList=97669".

<Test Example 1: Antibacterial activity test against strains A to I using azole derivative I-1>
The antibacterial property of the azole derivative I-1 against the strains A to I was tested by the Petri dish test. Mefentrifluconazole and fluconazole were used as control compounds.

After autoclave sterilization, 1% (V / V) of a dimethyl sulfoxide solution in which a predetermined concentration of the test compound was dissolved was added to a PDA medium (potato-dextrose-agar medium) cooled to around 60 ° C. The test compound was mixed well so that the concentration of the test compound in the PDA medium was uniform, and the medium was poured into a petri dish to prepare a plate medium containing the test compound.

On the other hand, the flora of each strain previously cultured on the PDA medium was punched out with a cork borer having a diameter of 4 mm and inoculated into a plate medium containing the above-mentioned test compound.

After culturing at 25 ° C. for 14 days, the bacterial flora diameter on the plate medium was measured. The hyphal elongation inhibition rate (%) was calculated by the following formula in comparison with the diameter of the flora on the untreated flat plate containing no test compound.

R = 100 (dc-dt) / dc
(In the formula, R = hyphal elongation inhibition rate (%), dc = flora diameter on untreated plate, dt = flora diameter on drug-treated plate.)
The greater the rate of hyphal elongation inhibition, the better the antibacterial property. The results are shown in Tables 10-15.

As shown in Tables 2-4, the azole derivative I-1 is a control compound (mefentrifluconazole and mefentrifluconazole and) at all concentrations of the compound concentration 0.16 to 40 mg / L in the medium with respect to the strains A to I. It showed a higher hyphal elongation inhibition rate than any of fluconazole) and was excellent in antibacterial activity.

<Test Examples 2 to 20: Azole derivatives I-4, I-6, I-7, I-8, I-9, I-11, I-12, I-14, I-15, I-16, I Antibacterial activity test against strains A to K using -17, I-18, I-19, I-20, I-21, I-22, I-23, I-24, and I-26>
In this test example, the azole derivatives I-4 (Test Example 2), I-6 (Test Example 3), I-7 (Test Example 4), I-8 (Test Example 5), I-9 (Test Example 6) ), I-11 (Test Example 7), I-12 (Test Example 8), I-14 (Test Example 9), I-15 (Test Example 10), I-16 (Test Example 11), I-17 (Test Example 12), I-18 (Test Example 13), I-19 (Test Example 14), I-20 (Test Example 15), I-21 (Test Example 16), I-22 (Test Example 17) , I-23 (Test Example 18), I-24 (Test Example 19), and I-26 (Test Example 20) were tested for antibacterial properties against strains A to K. Mefentrifluconazole was used as a control compound. The test method, evaluation method, etc. are the same as those in Test Example 1 above. The results are shown in Tables 5-23.

As shown in Tables 5-23, azole derivatives I-4, I-6, I-7, I-8, I-9, I-11, I-12, I-14, I-15, I-16. , I-17, I-18, I-19, I-20, I-21, I-22, I-23, I-24, and I-26 are in the medium against the strains A to K. At various compound concentrations, it showed a higher inhibition rate of mycelial elongation than the control compound (mefentrifluconazole) and was excellent in antibacterial activity.

<Test Examples 21 to 22: Antibacterial activity test against strains A to G, J and K using azole derivatives I-2 and I-3>
In this test example, the antibacterial properties of the azole derivatives I-2 (Test Example 21) and I-3 (Test Example 22) against the strains A to G, J and K were tested. Mefentrifluconazole and metconazole were used as control compounds. The test method, evaluation method, etc. are the same as those in Test Example 1 above. The results are shown in Tables 24-29.

As shown in Tables 24-29, the azole derivatives I-2 and I-3 are control compounds (mefentrifluconazole and methconazole) at various compound concentrations in the medium relative to the strains A-G, J and K. ), It showed a higher hyphal elongation inhibition rate and was excellent in antibacterial activity.

<Test Example 23: Control effect test against wheat leaf blight by strain G using azole derivative I-1>
Using the azole derivative I-1, the control effect of the strain G on wheat leaf blight was tested. As control compounds, mefentrifluconazole, metconazole, diphenoconazole, and control compound A were used.

The test compound was dissolved in acetone so as to have a predetermined drug concentration, and 5% (V / V) was added to ion-exchanged water containing Gramin S (final concentration of Gramin S 60 ppm). The prepared chemical solution was sprayed on wheat (variety: Norin 61) in the second leaf stage cultivated in a square plastic pot (6 cm × 6 cm) at a ratio of 1000 L / ha (chemical treatment plot). The untreated plot was obtained by spraying wheat with ion-exchanged water containing 5% acetone (final concentration of Gramin S 60 ppm) containing no test compound. After spraying, the spray solution on the wheat leaves was air-dried, and the spore solution of wheat leaf blight (200 spores / adjusted to the field of view, 60 ppm Gramin S) was spray-inoculated and kept at 23 ° C. and high humidity conditions for 48 hours. After that, it was managed in the artificial meteorological machine. On the 28th day after inoculation, the prevalence of wheat leaf blight was investigated, and the control value was calculated by the following formula.
Control value (%) = (1-Average morbidity in drug-treated plots / Average morbidity in untreated plots) x 100
The degree of illness was determined based on Table 30 below. The results are shown in Tables 31-34.

As shown in Tables 31 to 34, the azole derivative I-1 showed a control value of 75% or more against wheat leaf blight caused by the strain G at a concentration of only 12.5 g / ha. In addition, it showed a higher control value than any of the control compounds (mefentrifluconazole, metconazole, and diphenoconazole) at all concentrations of 12.5 to 200 g / ha, and was higher than control compound A at a concentration of 200 g / ha. It showed a high control value.

<Test Examples 24-36: Azole derivatives I-3, I-5, I-7, I-8, I-9, I-10, I-11, I-13, I-17, I-19, I -21, I-23, and I-25 control effect test against wheat leaf blight by strain G>

Azol Derivatives I-3 (Test Example 24), I-5 (Test Example 25), I-7 (Test Example 26), I-8 (Test Example 27), I-9 (Test Example 28), I-10 (Test Example 29), I-11 (Test Example 30), I-13 (Test Example 31), I-17 (Test Example 32), I-19 (Test Example 33), I-21 (Test Example 34) , I-23 (Test Example 35), and I-25 (Test Example 36) were used to test the control effect of strain G on wheat leaf blight. Mefentrifluconazole and metconazole were used as control compounds. The test method, evaluation method, and the like are the same as those in Test Example 23 above. The results are shown in Tables 35-43.

As shown in Tables 35-39, the azole derivatives I-3, I-5, I-7, I-8, and I-9 are only 25-100 g / ha against wheat leaf blight caused by the strain G. In terms of concentration, it showed a control value of 99% or more. In addition, at all concentrations of 3.125 to 100 g / ha, the control value was higher than that when the control compound (methconazole) was used. In addition, as shown in Tables 40 to 43, I-10, I-11, I-13, I-17, I-19, I-21, I-23, and I-25 are referred to as mefentrifluconazole. It showed the same control value.

<Apple scab, which is less sensitive to existing sterol biosynthesis inhibitors than wild-type>
Strains b and d of apple scab were prepared as pathogens. These strains are less sensitive to existing sterol biosynthesis inhibitors compared to wild type.

<Test Examples 37 to 39: Antibacterial activity test against strains b and d using azole derivative I-1>
In this test example, the antibacterial property of the azole derivative I-1 against the strains b and d was tested. As control compounds, diphenoconazole (Test Example 37), tebuconazole (Test Example 38), and metconazole (Test Example 39) were used. The test method, evaluation method, etc. are the same as those in Test Example 1 above. The results are shown in Tables 44-46.

As shown in Tables 44-46, the azole derivative I-1 has a higher hyphal elongation inhibition rate for strains b and d than the control compounds (diphenoconazole, tebuconazole and metconazole) at various compound concentrations in the medium. It showed excellent antibacterial activity.

<Sclerotinia bacteria that are less sensitive to existing sterol biosynthesis inhibitors than wild type>
As a pathogen, a strain g of Sclerotinia that causes Shivadara spot disease was prepared. This strain is less sensitive to existing sterol biosynthesis inhibitors compared to wild type.

<Test Examples 40 to 44: Antibacterial activity test against strain g using azole derivative I-1>
In this test example, the antibacterial property of the azole derivative I-1 against the strain g was tested. As control compounds, mefentrifluconazole (Test Example 40), diphenoconazole (Test Example 41), tebuconazole (Test Example 42), metconazole (Test Example 43), and propiconazole (Test Example 44) were used. The test method, evaluation method, etc. are the same as those in Test Example 1 above. The results are shown in Tables 47-51.

As shown in Tables 47-51, the azole derivative I-1 is a control compound (mefentrifluconazole, diphenoconazole, tebuconazole, metconazole, and propiconazole) at various compound concentrations in the medium with respect to the strain g. It showed a higher hyphal elongation inhibition rate and was excellent in antibacterial activity.

The agricultural and horticultural disease control agent according to the present invention can be suitably used as a control agent for controlling diseases caused by pathogenic bacteria that are less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type.

Claims (9)

An agricultural and horticultural disease control agent containing the compound represented by the following general formula (I) or its N-oxide or a pesticide-acceptable salt as an active ingredient.
An agricultural and horticultural disease control agent, wherein the disease is a disease caused by a pathogen that is less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type.

[In formula (I),
A is N;
D is hydrogen;
R ¹ is a hydrogen or C1 _- C6 _- alkyl group;
R ² is -OR ⁷ ;
^R7 is a hydrogen, C1 _- C6 _- alkyl group or C3 _- C8 _- cycloalkyl group;
^R4 is a halogen group, C1- _{C4 -} haloalkyl group, C1- _{C4 -} alkoxy group or -SF ₅ ;
E is a 6-membered aromatic heterocycle containing 1 or 2 phenyl groups or N atoms.
R3 is a halogen group ^, _a C1- _C4 -haloalkyl group or _a C1- _C4 -haloalkoxy group;
^R3 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;
Y is an oxygen atom that connects to any position in E;
Z is a 5- or 6-membered aromatic heterocycle containing 1 to 4 heteroatoms selected from a phenyl group, a naphthyl group, or O, N, or S.
^R4 is bound to any substitution position by m;
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 disease control agent for agriculture and horticulture according to claim 1, which is for foliage treatment or non-foliage treatment. The disease is less sensitive to existing sterol biosynthesis inhibitors than wild-type wheat leaf blight, and to existing sterol biosynthesis inhibitors compared to wild-type. Low-sensitivity worm-spot disease, spore-causing disease caused by spore-forming fungus, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild-type spores. Rice scabs caused by rice scabs that are less sensitive to sterol biosynthesis inhibitors, Udonko disease caused by scabs that are less sensitive to existing sterol biosynthesis inhibitors compared to wild type, Low sensitivity to existing sterol biosynthesis inhibitors compared to wild type Wheat spot disease caused by Ramularia collo-cygni, low sensitivity to existing sterol biosynthesis inhibitors compared to wild type Omugi cloud disease caused by Omugi cloud disease, rust caused by rust fungus, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type, and existing sterol biosynthesis inhibitor compared to wild type Tensai brown spot disease caused by the less sensitive Tensai brown spot disease, corn soot scab caused by Setosphaeria turcica, which is less sensitive to existing sterol biosynthesis inhibitors compared to the wild type, existing compared to the wild type Corn sesame leaf blight caused by Bipolaris maydis, which is less sensitive to sterol biosynthesis inhibitors, and apple scab caused by apple scab, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type. , Alternaria disease caused by Alternaria, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type, and sclerotinia, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type Shivadaler spot disease, less sensitive to existing sterol biosynthesis inhibitors compared to wild type Banana Shigatoka disease due to banana shigatoka disease, less sensitive to existing sterol biosynthesis inhibitors compared to wild type Gray mold caused by a certain gray mold, pear erythema caused by pear erythema, which is less sensitive to existing sterol biosynthesis inhibitors compared to wild type, existing sterol biosynthesis inhibitor compared to wild type Less sensitive to eggplant scab, which is less sensitive to existing sterol biosynthesis inhibitors than wild type. Selected from the group consisting of tomato leaf mold caused by Mato leaf mold and Botrytis cinerea caused by Botrytis cinerea, which is less sensitive to existing sterol biosynthesis inhibitors than the wild type. The agricultural and horticultural disease control agent according to Item 1 or 2. One of claims 1 to 3, wherein the disease is wheat leaf blight caused by wheat leaf blight, which is less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type. Agricultural and horticultural disease control agents described in the section. The low sensitivity of the Zymoseptoria trifolium to the existing sterol biosynthesis inhibitor is due to mutations in the gene encoding the sterol demethylase CYP51, overexpression of CYP51, and the development of drug efflux pumps in the cell membrane. The agricultural and horticultural disease control agent according to claim 4, wherein the agent is caused by at least one selected from the group. The mutation in the gene encoding CYP51 is the 50th, 107th, 134th, 136th, 137th, 145th, 178th, 188th, 208th, 259th, 284th amino acid sequence of the wild-type CYP51. , 303rd, 311th, 312th, 379th, 381st, 410th, 412th, 459th, 460th, 461st, 476th, 490th, 510th, 513th and 524th. The agricultural and horticultural disease control agent according to claim 5, which is a mutation resulting in substitution or deletion of an amino acid residue at at least one amino acid position selected. A method for controlling diseases caused by pathogens, which uses the agricultural and horticultural disease control agent according to any one of claims 1 to 6, and is less sensitive to existing sterol biosynthesis inhibitors as compared with the wild type. The control method according to claim 7, wherein the foliage treatment or the non-foliage treatment is performed. The agricultural and horticultural disease control agent according to claim 5, wherein the wheat leaf blight fungus is characterized by a mutation in a gene encoding CYP51 and low sensitivity to a DMI fungicide.