JP6413200B2 - Aminopyridine derivatives and agricultural and horticultural fungicides - Google Patents

Description

The present invention relates to an agricultural and horticultural fungicide that can be used safely and safely, and an aminopyridine derivative useful as an active ingredient of the agricultural and horticultural fungicide.
This application claims priority on October 25, 2013 based on Japanese Patent Application No. 2013-222613 for which it applied to Japan, and uses the content here.

  Many control agents are used against diseases of agricultural and horticultural crops. However, many of the conventional control chemicals have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human and livestock fish. And the impact on the environment was not enough. For this reason, there is a strong demand for the appearance of drugs with few such defects.

  In relation to the present invention, Patent Document 1 discloses a compound represented by the formula (I) and the like, and describes that it has an antiallergic action.

  Patent Documents 2 and 3 disclose compounds represented by formula (II) and formula (III), respectively, and both describe that they have a herbicidal effect.

JP 55-22634 A US Patent 4,383,851 JP-A-6-41116

  This invention makes it a subject to provide the aminopyridine derivative useful as an active ingredient of the agricultural and horticultural fungicide which can be used safely and reliably, and the agricultural and horticultural fungicide.

  As a result of intensive studies to solve the above problems, the present inventors have completed the present invention including the following modes.

[1] An aminopyridine compound represented by the formula (1) or a salt thereof.

［式（１）中、
Ｒ¹は、水素原子、ホルミル基、無置換の若しくは置換基を有するＣ１〜８アルキル基、無置換の若しくは置換基を有するＣ１〜８アルコキシ基、無置換の若しくは置換基を有するＣ１〜８アルキルカルボニル基、無置換の若しくは置換基を有するＣ３〜８シクロアルキルカルボニル基、無置換の若しくは置換基を有するＣ６〜１０アリールカルボニル基、無置換の若しくは置換基を有する５〜１０員ヘテロシクリルカルボニル基、無置換の若しくは置換基を有するＣ３〜８シクロアルキルＣ１〜６アルキルカルボニル基、無置換の若しくは置換基を有するＣ６〜１０アリールＣ１〜６アルキルカルボニル基、無置換の若しくは置換基を有する５〜１０員へテロシクリルＣ１〜６アルキルカルボニル基、無置換の若しくは置換基を有するＣ１〜８アルキルオキシカルボニル基、無置換の若しくは置換基を有するＣ２〜８アルケニルオキシカルボニル基、無置換の若しくは置換基を有するＣ２〜８アルキニルオキシカルボニル基、無置換の若しくは置換基を有するＣ３〜８シクロアルキルオキシカルボニル基、無置換の若しくは置換基を有するＣ６〜１０アリールオキシカルボニル基、無置換の若しくは置換基を有する５〜１０員へテロシクリルオキシカルボニル基、無置換の若しくは置換基を有するＣ１〜８アルキルチオカルボニル基、無置換の若しくは置換基を有するジＣ１〜８アルキルスルファモイル基、無置換の若しくは置換基を有するＣ１〜８アルキルスルホニル基、無置換の若しくは置換基を有するＣ３〜８シクロアルキルスルホニル基、無置換の若しくは置換基を有するＣ６〜１０アリールスルホニル基、または無置換の若しくは置換基を有する５〜１０員へテロシクリルスルホニル基を示す。
Ｒ²は、水素原子、無置換の若しくは置換基を有するＣ１〜８アルキル基、無置換の若しくは置換基を有するＣ１〜８アルコキシ基、または無置換の若しくは置換基を有するＣ１〜８アルキルカルボニル基を示す。
Ｒ³¹は、水素原子、ハロゲノ基、シアノ基、無置換の若しくは置換基を有するＣ１〜８アルキル基、無置換の若しくは置換基を有するＣ１〜８アルコキシ基、無置換の若しくは置換基を有するＣ３〜８シクロアルキル基、無置換の若しくは置換基を有するＣ３〜８シクロアルコキシ基、無置換の若しくは置換基を有するＣ６〜１０アリール基、無置換の若しくは置換基を有するＣ６〜１０アリールオキシ基、無置換の若しくは置換基を有する５〜１０員へテロシクリル基、または無置換の若しくは置換基を有する５〜１０員へテロシクリルオキシ基を示す。
Ｒ³²は、ハロゲノ基、シアノ基、無置換の若しくは置換基を有するＣ１〜８アルキル基、無置換の若しくは置換基を有するＣ１〜８アルコキシ基、無置換の若しくは置換基を有するＣ３〜８シクロアルキル基、無置換の若しくは置換基を有するＣ３〜８シクロアルコキシ基、無置換の若しくは置換基を有するＣ６〜１０アリール基、無置換の若しくは置換基を有するＣ６〜１０アリールオキシ基、無置換の若しくは置換基を有する５〜１０員へテロシクリル基、または無置換の若しくは置換基を有する５〜１０員へテロシクリルオキシ基を示す。ｎはＲ³²の個数を示し、０〜２のいずれかの整数である。ｎが２のとき、Ｒ³²は互いに同じでも異なってもよい。
Ｅは、無置換の若しくは置換基を有するベンゼン環からなる２価の基、または無置換の若しくは置換基を有する５〜６員のへテロ環からなる２価の基を示す。
Ｘは、−ＣＨ₂−、−Ｏ−、−Ｓ−、−ＮＨ−、−ＣＨ₂ＣＨ₂−、−ＣＨ₂Ｏ−、−ＯＣＨ₂−、−ＣＨ₂Ｓ−、−ＳＣＨ₂−、−ＣＨ₂ＮＨ−、または−ＮＨＣＨ₂−を示す。
Ａは、無置換の若しくは置換基を有するＣ６〜１０アリール基、または無置換の若しくは置換基を有する５〜１０員へテロシクリル基を示す。］

[In Formula (1),
R ¹ is a hydrogen atom, a formyl group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C1-8 alkoxy group, an unsubstituted or substituted C1-8 alkyl A carbonyl group, an unsubstituted or substituted C3-8 cycloalkylcarbonyl group, an unsubstituted or substituted C6-10 arylcarbonyl group, an unsubstituted or substituted 5-10 membered heterocyclylcarbonyl group, Unsubstituted or substituted C3-8 cycloalkyl C1-6 alkylcarbonyl group, unsubstituted or substituted C6-10 aryl C1-6 alkylcarbonyl group, unsubstituted or substituted 5-10 Membered heterocyclyl C1-6 alkylcarbonyl group, unsubstituted or substituted C1 8 alkyloxycarbonyl group, unsubstituted or substituted C2-8 alkenyloxycarbonyl group, unsubstituted or substituted C2-8 alkynyloxycarbonyl group, unsubstituted or substituted C3-8 cyclo An alkyloxycarbonyl group, an unsubstituted or substituted C6-10 aryloxycarbonyl group, an unsubstituted or substituted 5-10 membered heterocyclyloxycarbonyl group, an unsubstituted or substituted C1 ~ 8 alkylthiocarbonyl group, unsubstituted or substituted diC1-8 alkylsulfamoyl group, unsubstituted or substituted C1-8 alkylsulfonyl group, unsubstituted or substituted C3-8 cyclo Alkylsulfonyl group, unsubstituted or substituted A C6-10 arylsulfonyl group or an unsubstituted or substituted 5-10 membered heterocyclylsulfonyl group is shown.
R ² represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C1-8 alkoxy group, or an unsubstituted or substituted C1-8 alkylcarbonyl group. Indicates.
R ³¹ is a hydrogen atom, a halogeno group, a cyano group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted C 3 -8 cycloalkyl group, unsubstituted or substituted C3-8 cycloalkoxy group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-10 aryloxy group, An unsubstituted or substituted 5- to 10-membered heterocyclyl group, or an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group is shown.
R ³² is a halogeno group, a cyano group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted C 3-8 cyclo group. An alkyl group, an unsubstituted or substituted C3-8 cycloalkoxy group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted Or a 5- to 10-membered heterocyclyl group having a substituent, or an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group. n represents the number of R ³² and is an integer of 0-2. When n is 2, R ³² may be the same as or different from each other.
E represents a divalent group consisting of an unsubstituted or substituted benzene ring or a divalent group consisting of an unsubstituted or substituted 5- to 6-membered hetero ring.
X _{is, -CH 2 -, - O -} , - S -, - NH -, - CH 2 CH 2 -, - CH 2 O -, - OCH 2 -, - CH 2 S -, - SCH 2 -, - CH ₂ NH— or —NHCH ₂ — is shown.
A represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-10 membered heterocyclyl group. ]

[2] R ¹ and R ² are not both hydrogen atoms, or, is not -O- X when R ¹ and R ² are both hydrogen atom, an amino pyridine compound or salt thereof according to claim 1.
[3] The aminopyridine compound or a salt thereof according to claim 1 or 2, represented by any one of the following formulas (1-1) to (1-8).

［式（１−１）〜（１−８）中、
Ｒ^１、Ｒ^２、Ｒ^３１、Ｒ^３２、ｎ、Ａは前記同様である。
Ｒ^１２は、無置換の若しくは置換基を有するＣ１〜８アルキル基を示す。
Ｒ^４１〜Ｒ^４８は、それぞれ独立にハロゲノ基を示す。
ｍはＲ^４１〜Ｒ^４８の個数を示し、０〜２のいずれかの整数である。ｍが２のとき、Ｒ^４１〜Ｒ^４８は互いに同じであってもよく異なっていてもよい。
ＱはＣＨ、または窒素原子を示す。］

[In the formulas (1-1) to (1-8),
R ¹ , R ² , R ³¹ , R ³² , n, and A are the same as described above.
R ¹² represents an unsubstituted or substituted C1-8 alkyl group.
R ^{41 to} R ⁴⁸ each independently represent a halogeno group.
m represents the number of ^R 41 ^{to R 48,} which is an integer of 0 to 2. When m is 2, R ^{41 to} R ⁴⁸ may be the same as or different from each other.
Q represents CH or a nitrogen atom. ]

[4] The aminopyridine compound or a salt thereof according to any one of [1] to [3], wherein R ³¹ is an unsubstituted or substituted C1-8 alkyl group.
[5] E is a divalent group consisting of a ring selected from the group consisting of a benzene ring, a pyridine ring, a furan ring, a pyrroline ring, a tetrazoline ring, a thiazoline ring, and a pyrazoline ring, [1] or [2] Or an aminopyridine compound or a salt thereof.
[6] The aminopyridine compound or a salt thereof according to [1] or [2], wherein E is a divalent group consisting of a benzene ring, and X is —O—.
[7] An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the aminopyridine compound according to any one of [1] to [6] or a salt thereof.

The aminopyridine derivative of the present invention is a novel compound useful as an active ingredient of agricultural and horticultural fungicides.
The agricultural and horticultural fungicide of the present invention is a safe drug that has a reliable and excellent control effect, does not cause phytotoxicity on plants, and has little toxicity to human and livestock and environmental impact.

  The aminopyridine derivative according to the present invention is a compound represented by the formula (1) (hereinafter sometimes referred to as “compound (1)”) or a salt thereof.

First, the meanings of “unsubstituted” and “having a substituent” in formula (1) will be described.
The term “unsubstituted” means only the group that is the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure as the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
Terms such as “C1-6” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Examples of groups that can be “substituents” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n-propyl, i-propyl, n-butyl, and s-butyl. A C1-6 alkyl group such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; a C3-6 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group C2-6 alkenyl groups such as nyl group, 3-hexenyl group, 4-hexenyl group and 5-hexenyl group; C3-6 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group and 3-cyclohexenyl group Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl Group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group A C2-6 alkynyl group such as;

  C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy group and butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryl groups such as phenyl group and naphthyl group; phenoxy group and 1-naphthoxy group A C7-10 aralkyl group such as a benzyl group or a phenethyl group; a C7-11 aralkyloxy group such as a benzyloxy group or a phenethyloxy group; a formyl group, an acetyl group, a propionyl group, a benzoyl group, C1- such as a cyclohexylcarbonyl group Acyl group; C1-7 acyloxy group such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group A C1-6 alkoxycarbonyl group such as n-butoxycarbonyl group and t-butoxycarbonyl group; carboxyl group;

  Hydroxyl group; oxo group; C1-6 haloalkyl such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group Group; C2-6 haloalkenyl group such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5- C2-6 haloalkynyl group such as bromo-2-pentynyl group; C1-6 haloalkoxy group such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group, 3-bromo C2-6 haloalkenyloxy groups such as butenyloxy group; 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophen C6-10 haloaryl group such as 4-fluorophenyloxy group, C6-10 haloaryloxy group such as 4-fluorophenyloxy group, 4-chloro-1-naphthoxy group; chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4- A C1-7 haloacyl group such as a chlorobenzoyl group;

  Cyano group; isocyano group; nitro group; isocyanato group; cyanato group; azide group; amino group; C1-6 alkylamino group such as methylamino group, dimethylamino group and diethylamino group; C6 ~ such as anilino group and naphthylamino group 10 arylamino group; C7-11 aralkylamino group such as benzylamino group and phenylethylamino group; formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group, etc. C1-7 acylamino group; C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; carbamoyl group; dimethyl Substituted carbamoyl groups such as rubamoyl group, phenylcarbamoyl group, N-phenyl-N-methylcarbamoyl group; imino C1-6 alkyl such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group Group; hydroxyimino C1-6 alkyl group such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; C1 such as methoxyiminomethyl group and (1-methoxyimino) ethyl group -6 alkoxyimino C1-6 alkyl groups;

  Mercapto group; isothiocyanato group; thiocyanato group; C1-6 alkylthio such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C6-10 arylthio groups such as phenylthio groups and naphthylthio groups; thiazolylthio groups and pyridylthio groups A heteroarylthio group of: C7-11 aralkylthio group such as benzylthio group and phenethylthio group; (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbonyl group, n- butylthio) carbonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) (Cl to 6 alkylthio, such as carbonyl groups) carbonyl group;

  C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group and the like A heteroarylsulfinyl group such as thiazolylsulfinyl group and pyridylsulfinyl group; a C7-11 aralkylsulfinyl group such as benzylsulfinyl group and phenethylsulfinyl group; a methylsulfonyl group, an ethylsulfonyl group, t- C1-6 alkylsulfonyl group such as butylsulfonyl group; C2-6 alkenylsulfonyl group such as allylsulfonyl group; C2 such as propargylsulfonyl group A C6-10 arylsulfonyl group such as a phenylsulfonyl group; a heteroarylsulfonyl group such as a thiazolylsulfonyl group or a pyridylsulfonyl group; a C7-11 aralkylsulfonyl group such as a benzylsulfonyl group or a phenethylsulfonyl group;

  5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Groups, 6-membered heteroaryl groups such as pyrimidinyl groups, pyridinidyl groups, triazinyl groups; saturated heterocyclyl groups such as aziridinyl groups, epoxy groups, pyrrolidinyl groups, tetrahydrofuranyl groups, piperidyl groups, piperazinyl groups, morpholinyl groups; trimethylsilyl groups, triethylsilyl groups A tri-C1-6 alkylsilyl group such as a t-butyldimethylsilyl group; a triphenylsilyl group; and the like.

  These “substituents” may have another “substituent” therein. For example, a butyl group as a substituent and an ethoxy group as another substituent, that is, an ethoxybutyl group may be used.

[R ¹ ]
In formula (1), R ¹ is a hydrogen atom, a formyl group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted group A C1-8 alkylcarbonyl group having an unsubstituted or substituted C3-8 cycloalkylcarbonyl group, an unsubstituted or substituted C6-10 arylcarbonyl group, an unsubstituted or substituted 5-5 10-membered heterocyclylcarbonyl group, unsubstituted or substituted C3-8 cycloalkyl C1-6 alkylcarbonyl group, unsubstituted or substituted C6-10 aryl C1-6 alkylcarbonyl group, unsubstituted or substituted 5- to 10-membered heterocyclyl C1-6 alkylcarbonyl group having a group, unsubstituted or substituted Having C1-8 alkyloxycarbonyl group, unsubstituted or substituted C2-8 alkenyloxycarbonyl group, unsubstituted or substituted C2-8 alkynyloxycarbonyl group, unsubstituted or substituted C3 -8 cycloalkyloxycarbonyl group, unsubstituted or substituted C6-10 aryloxycarbonyl group, unsubstituted or substituted 5- to 10-membered heterocyclyloxycarbonyl group, unsubstituted or substituted Having a C1-8 alkylthiocarbonyl group, unsubstituted or substituted diC1-8 alkylsulfamoyl group, unsubstituted or substituted C1-8 alkylsulfonyl group, unsubstituted or substituted C3 ~ 8 cycloalkylsulfonyl group, unsubstituted or substituted A C6-10 arylsulfonyl group having a substituent or an unsubstituted or substituted 5-10 membered heterocyclylsulfonyl group is shown.

  Examples of the “C1-8 alkyl group” include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group and i-propyl group. I-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like. Of these, C1-6 alkyl groups are preferred.

  Examples of the “substituted C1-8 alkyl group” include cycloalkylalkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, preferably C3-6 cycloalkylC1. -6 alkyl group; cycloalkenyl alkyl group such as cyclopentenylmethyl group, 3-cyclopentenylmethyl group, 3-cyclohexenylmethyl group, 2- (3-cyclohexenyl) ethyl group, preferably C4-6 cycloalkenyl C1 6 alkyl groups;

  Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, 2, 2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl Group, perfluorohexyl group, perchlorohexyl group, perfluorooctyl group, perchlorooctyl group, 2,4,6-trichlorohexyl group, perfluorodecyl group, 2,2,4,4,6,6- A haloalkyl group such as a xachlorooctyl group, preferably a C1-6 haloalkyl group;

  Arylalkyl groups (aralkyl groups) such as benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, preferably C6-10 arylC1-6 alkyl group; 2-pyridylmethyl group 3-pyridylmethyl group, 4-pyridylmethyl group, 2- (2-pyridyl) ethyl group, 2- (3-pyridyl) ethyl group, 2- (4-pyridyl) ethyl group, 3- (2-pyridyl) Propyl group, 3- (3-pyridyl) propyl group, 3- (4-pyridyl) propyl group, 2-pyrazinylmethyl group, 3-pyrazinylmethyl group, 2- (2-pyrazinyl) ethyl group, 2- (3-pyrazinyl) Ethyl group, 3- (2-pyrazinyl) propyl group, 3- (3-pyrazinyl) propyl group, 2-pyrimidylmethyl group, 4-pyrimidylmethyl group, 2 (2-pyrimidyl) ethyl group, 2- (4-pyrimidyl) ethyl group, 3- (2-pyrimidyl) propyl group, 3- (4-pyrimidyl) propyl group, 2-furylmethyl group, 3-furylmethyl group, A heteroarylalkyl group such as 2- (2-furyl) ethyl group, 2- (3-furyl) ethyl group, 3- (2-furyl) propyl group, 3- (3-furyl) propyl group, preferably 5- A 6-membered heteroaryl C1-6 alkyl group;

  Hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1,1-dimethylethyl group, A hydroxyalkyl group such as a 2-hydroxy-1,1-dimethylpropyl group, a 2-hydroxy-2-methylpropyl group, preferably a hydroxy C1-6 alkyl group; a methoxymethyl group, an ethoxymethyl group, a 2-methoxyethyl group, 2-ethoxyethyl group, methoxy n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, 2,2-dimethoxyethyl group, 2,2-dimethoxy- Alkoxyalkyl groups such as 1,1-dimethylethyl group, preferably C1-6 alkyl Carboxymethyl C1~6 alkyl group;

  An acyloxyalkyl group such as formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group, preferably C1-7 acyloxy C1-6 alkyl group; formylmethyl group, 2-formylethyl Group, 3-formylpropyl group, 1-formyl-1-methylethyl group, 2-formyl-1,1-dimethylethyl group, acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl- An acylalkyl group such as a 1-methylethyl group and a 2-acetyl-1,1-dimethylethyl group, preferably a C1-7 acyl C1-6 alkyl group;

  Acylalkyl groups such as acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1-methylethyl group, 2-acetyl-1,1-dimethylethyl group, preferably C1-7 acyl C1 -6 alkyl group; carboxyalkyl group such as carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 1-carboxy-1-methylethyl group, 2-carboxy-1,1-dimethylethyl group, preferably Carboxy C1-6 alkyl group; methoxycarbonylmethyl group, 2-methoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 1-methoxycarbonyl-1-methylethyl group, 2-methoxycarbonyl-1,1-dimethylethyl group, etc. An alkoxycarbonylalkyl group, preferably C1-6 Coxycarbonyl C1-6 alkyl group;

  The “C1-8 alkoxy group” is a group in which the C1-8 alkyl group is bonded to an oxygen atom. Examples of the “C1-8 alkoxy group” include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyl. An oxy group etc. can be mentioned. Examples of the “substituted C1-8 alkoxy group” include a fluoromethoxy group, a chloromethoxy group, a bromomethoxy group, a difluoromethoxy group, a dichloromethoxy group, and a dibromomethoxy group.

  The “C1-8 alkylcarbonyl group” is a group in which the C1-8 alkyl group is bonded to carbonyl. Examples of the “C1-8 alkylcarbonyl group” include acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, t-butylcarbonyl group and the like. Examples of the “substituted C1-8 alkylcarbonyl group” include monofluoroacetyl group, monochloroacetyl group, monobromoacetyl group, difluoroacetyl group, dichloroacetyl group, dibromoacetyl group, trifluoroacetyl group, trichloroacetyl group, C1-8 haloalkylcarbonyl groups such as tribromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3-trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group; methoxy C1-8 alkoxy C1-8 alkylcarbonyl group such as methylcarbonyl group, ethoxymethylcarbonyl group, methoxyethylcarbonyl group, ethoxyethylcarbonyl group; C6-10 aliquot such as phenoxymethylcarbonyl group, 1-naphthoxymethylcarbonyl group Aryloxy such C1~8 alkylcarbonyl group can be exemplified.

  The “C3-8 cycloalkylcarbonyl group” is a group in which a C3-8 cycloalkyl group is bonded to carbonyl. A “C 3-8 cycloalkyl group” bonded to a carbonyl group is an alkyl group composed of 3-8 carbon atoms having a cyclic moiety. Examples of the “C3-8 cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. Of these, C3-6 cycloalkyl groups are preferred. Examples of the “substituted C3-8 cycloalkyl group” bonded to the carbonyl group include 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, and 1,3-dibutylcyclohexyl group. An alkyl-substituted cycloalkyl group such as a group, preferably a C3-6 cycloalkyl group in which 1 to 3 C1-6 alkyl groups are substituted can be exemplified.

  The “C6-10 arylcarbonyl group” is a group in which a C6-10 aryl group is bonded to carbonyl. The “C6-10 aryl group” bonded to the carbonyl group is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms. In the polycyclic aryl group, as long as at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group. Of these, a phenyl group is preferred. Examples of the “substituted C6-10 aryl group” bonded to the carbonyl group include 2-chlorophenyl group, 3,5-dichlorophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, 4-trifluoromethyl. An alkyl-substituted aryl group, a halogeno-substituted aryl group, an alkoxy-substituted aryl group, preferably a C1-6 alkyl-substituted C6-10 aryl group, a halogeno-substituted C6-10 aryl group, such as a phenyl group, a 2-methoxy-1-naphthyl group; A C1-6 alkoxy substituted aryl group can be mentioned.

The “5- to 10-membered heterocyclylcarbonyl group” is a group in which a 5- to 10-membered heterocyclyl group is bonded to carbonyl. The “5- to 10-membered heterocyclyl group” bonded to the carbonyl group is a 5- to 10-membered ring group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. The heterocyclyl group may be monocyclic or polycyclic.
Examples of the heterocyclyl group include a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a saturated heterocyclyl group, and a partially unsaturated heterocyclyl group.

  Examples of the 5-membered heteroaryl group include pyrrolyl groups such as pyrrol-1-yl group, pyrrol-2-yl group and pyrrol-3-yl group; furyl groups such as furan-2-yl group and furan-3-yl group. A thienyl group such as a thiophen-2-yl group and a thiophen-3-yl group; an imidazolyl group such as an imidazol-1-yl group, an imidazol-2-yl group, an imidazol-4-yl group, and an imidazol-5-yl group; A pyrazolyl group such as a pyrazol-1-yl group, a pyrazol-3-yl group, a pyrazol-4-yl group, and a pyrazol-5-yl group; an oxazol-2-yl group, an oxazol-4-yl group, and an oxazole-5 -Oxazolyl groups such as yl groups; isoxazol-3-yl groups, isoxazol-4-yl groups, isoxazol-5-yl groups and the like Isoxazolyl; thiazol-2-yl group, thiazol-4-yl group, a thiazolyl group such as thiazol-5-yl group;

  Isothiazolyl groups such as isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl group; 1,2,3-triazol-1-yl group, 1,2,3-triazole-4 -Yl group, 1,2,3-triazol-5-yl group, 1,2,4-triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazole A triazolyl group such as -5-yl group; 1,2,4-oxadiazol-3-yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazole- Oxadiazolyl groups such as 2-yl group; thiadiazolyl such as 1,2,4-thiadiazol-3-yl group, 1,2,4-thiadiazol-5-yl group, 1,3,4-thiadiazol-2-yl group Group; tetrazole- - yl group, tetrazolyl group, such as tetrazol-2-yl group; and the like.

  Examples of the 6-membered heteroaryl group include pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazinyl groups such as pyrazin-2-yl group and pyrazin-3-yl group A pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; be able to.

  Examples of the condensed heteroaryl group include indol-1-yl group, indol-2-yl group, indol-3-yl group, indol-4-yl group, indol-5-yl group, indol-6-yl group, and indole. Benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group, benzofuran-6-yl group, benzofuran-7-yl group; -2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6-yl group, benzothiophen-7-yl group; -Yl group, benzimidazol-2-yl group, benzimidazol-4-yl group, benzimidazol-5-yl group Benzoxazol-2-yl group, benzoxazol-4-yl group, benzoxazol-5-yl group, benzothiazol-2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group; quinoline- 2-yl group, quinolin-3-yl group, quinolin-4-yl group, quinolin-5-yl group, quinolin-6-yl group, quinolin-7-yl group, quinolin-8-yl group; be able to.

Other saturated heterocyclyl groups include 3-membered saturated heterocyclyl groups such as aziridin-1-yl group, aziridin-2-yl group, and oxiranyl group; pyrrolidin-1-yl group, pyrrolidin-2-yl group, pyrrolidin-3- 5-membered saturated heterocyclyl group such as yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, [1,3] dioxiran-2-yl group; piperidin-1-yl group, piperidin-2-yl group, Piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazin-2-yl group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group, etc. A 6-membered saturated heterocyclyl group; and the like.
Other partially saturated heterocyclyl groups include 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl group, 1,4-benzodioxan-5-yl group, 1 , 4-Benzodioxane-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin- 7-yl group, 2,3-dihydrobenzofuran-4-yl group, 2,3-dihydrobenzofuran-5-yl group, 2,3-dihydrobenzofuran-6-yl group, 2,3-dihydrobenzofuran-7- Yl group; and the like.

  Examples of the “substituted 5- to 10-membered heterocyclyl group having a substituent” bonded to a carbonyl group include a 4-chloro-2-pyridinyl group, a 3-chloro-2-pyrazinyl group, a 4-methyl-2-pyridinyl group, Examples thereof include a fluoromethyl-2-pyrimidinyl group and a 3-methyl-2-quinolyl group.

The “C3-8 cycloalkyl C1-6 alkylcarbonyl group” is a group in which a C3-8 cycloalkyl group is bonded to a C1-6 alkylcarbonyl group.
The “C3-8 cycloalkyl group” and the “C3-8 cycloalkyl group having a substituent” which are bonded to an unsubstituted or substituted C1-6 alkylcarbonyl group are the above-mentioned “C3-8 cycloalkyl”, respectively. The same thing as "C3-8 cycloalkyl group" and "C3-8 cycloalkyl group which has a substituent" mentioned in description of a carbonyl group can be mentioned. In addition, as the “C1-6 alkylcarbonyl group” and the “C1-6 alkylcarbonyl group having a substituent”, C1-6 of those mentioned in the description of the “C1-8 alkylcarbonyl group”, respectively. Examples thereof include the same as “alkylcarbonyl group” and “alkylcarbonyl group having a substituent”.

  The “unsubstituted or substituted C6-10 aryl C1-6 alkylcarbonyl group” is a group in which an unsubstituted or substituted C6-10 aryl group is bonded to a C1-6 alkylcarbonyl group. Examples of the unsubstituted or substituted C6-10 aryl group include the same as those already described.

  "Unsubstituted or substituted 5- to 10-membered heterocyclyl C1-6 alkylcarbonyl group" means that an unsubstituted or substituted 5- to 10-membered heterocyclyl group is bonded to a C1-6 alkylcarbonyl group It is a group. Examples of the unsubstituted or substituted 5- to 10-membered heterocyclyl group include the same as those already described.

  The “unsubstituted or substituted C1-8 alkyloxycarbonyl group” is a group in which an unsubstituted or substituted C1-8 alkyloxycarbonyl group is bonded to a carbonyl group. Examples of the unsubstituted or substituted C1-8 alkyloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group. Can be mentioned.

  The “unsubstituted or substituted C2-8 alkenyloxycarbonyl group” is a group in which an unsubstituted or substituted C2-8 alkenyloxy group is bonded to a carbonyl group. Examples of the unsubstituted or substituted C2-8 alkenyloxy group include vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl 2-propenyloxy group, 2-methyl-2-propenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-methyl-2-butenyloxy group, A 2-methyl-2-butenyloxy group, a 1-hexenyloxy group, a 2-hexenyloxy group, a 3-hexenyloxy group, a 4-hexenyloxy group, a 5-hexenyloxy group, and the like can be given.

  The “unsubstituted or substituted C2-8 alkynyloxycarbonyl group” is a group in which an unsubstituted or substituted C2-8 alkynyloxy group is bonded to a carbonyl group. Examples of the unsubstituted or substituted C2-8 alkynyloxy group include ethynyloxy group, 1-propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1- Methyl-2-propynyloxy group, 2-methyl-3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1-methyl-2 -Butynyloxy group, 2-methyl-3-pentynyloxy group, 1-hexynyloxy group, 1,1-dimethyl-2-butynyloxy group and the like can be mentioned.

  The “unsubstituted or substituted C3-8 cycloalkyloxycarbonyl group” is a group in which an unsubstituted or substituted C3-8 cycloalkyloxy group is bonded to a carbonyl group. Examples of the unsubstituted or substituted C3-8 cycloalkyloxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and a cycloheptyloxy group. Examples of the “substituted C3-8 cycloalkoxy group” include chlorocyclohexyloxy group, bromocyclohexyloxy group, 2-methylcyclopropyloxy group, 2,3-dimethylcyclopropyloxy group, spiro [2.2] penta -1-yloxy group, 1-methyl-spiro [2.2] pent-1-yloxy group, 1-hydroxymethylspiro [2.2] pent-1-yloxy group, 4,4-difluoro-spiro [2. 2] A penta-1-yloxy group, a bicyclopropyl-2-yl group oxy and the like can be mentioned.

  The “unsubstituted or substituted C6-10 aryloxycarbonyl group” is a group in which an unsubstituted or substituted C6-10 aryloxy group is bonded to a carbonyl group. Examples of the unsubstituted or substituted C6-10 aryloxy group include a phenoxy group and a 1-naphthoxy group.

  The “unsubstituted or substituted 5- to 10-membered heterocyclyloxycarbonyl group” is a group in which an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group is bonded to a carbonyl group. An unsubstituted or substituted 5- to 10-membered heterocyclyloxy group is a group in which an unsubstituted or substituted 5- to 10-membered heterocyclyl group is bonded to an oxy group. Examples of the unsubstituted or substituted 5- to 10-membered heterocyclyl group include the same groups as described above. Examples of the “5- to 10-membered heterocyclyloxy group” include a pyridyloxy group and a pyridazinyloxy group.

  As an unsubstituted or substituted C1-8 alkylthiocarbonyl group, (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbonyl group, (n-butylthio) carbonyl Group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) carbonyl group and the like.

Examples of the unsubstituted or substituted di-C1-8 alkylsulfamoyl group include an N-methylsulfamoyl group and an N-ethylsulfamoyl group.
Examples of the unsubstituted or substituted C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
Examples of the unsubstituted or substituted C3-8 cycloalkylsulfonyl group include a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, and a cyclohexylsulfonyl group.

Examples of the unsubstituted or substituted C6-10 arylsulfonyl group include a phenylsulfonyl group and a naphthylsulfonyl group.
An unsubstituted or substituted 5- to 10-membered heterocyclylsulfonyl group is a group formed by bonding an unsubstituted or substituted 5- to 10-membered heterocyclyl group with a sulfonyl group. Examples of the unsubstituted or substituted 5- to 10-membered heterocyclyl group include the same as those already described.

[R ² ]
R ² represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C1-8 alkoxy group, or an unsubstituted or substituted C1-8 alkylcarbonyl group. Indicates. These can be the same as those already described in the description of R ¹ .

In particular, when R ¹ and R ² are not both hydrogen atoms, or when R ¹ and R ² are both hydrogen atoms, X described later is preferably other than —O—.
That is, when R ² is a hydrogen atom, R ¹ is a formyl group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted group A C1-8 alkylcarbonyl group having an unsubstituted or substituted C3-8 cycloalkylcarbonyl group, an unsubstituted or substituted C6-10 arylcarbonyl group, an unsubstituted or substituted 5-5 10-membered heterocyclylcarbonyl group, unsubstituted or substituted C3-8 cycloalkyl C1-6 alkylcarbonyl group, unsubstituted or substituted C6-10 aryl C1-6 alkylcarbonyl group, unsubstituted or substituted 5- to 10-membered heterocyclyl C1-6 alkylcarbonyl group having a group, unsubstituted or Is a substituted C1-8 alkyloxycarbonyl group, unsubstituted or substituted C2-8 alkenyloxycarbonyl group, unsubstituted or substituted C2-8 alkynyloxycarbonyl group, unsubstituted or substituted C3-8 cycloalkyloxycarbonyl group having a group, unsubstituted or substituted C6-10 aryloxycarbonyl group, unsubstituted or substituted 5-10 membered heterocyclyloxycarbonyl group, unsubstituted Or a substituted C1-8 alkylthiocarbonyl group, an unsubstituted or substituted diC1-8 alkylsulfamoyl group, an unsubstituted or substituted C1-8 alkylsulfonyl group, unsubstituted or substituted C3-8 cycloalkylsulfonyl group having a group, unsubstituted Alternatively, it is preferably a C6-10 arylsulfonyl group having a substituent, or an unsubstituted or substituted 5-10 membered heterocyclylsulfonyl group. When R ¹ and R ² are both hydrogen atoms, X represents —CH ₂ —, —S—, —NH—, —CH ₂ CH ₂ —, —CH ₂ O—, —OCH ₂ —, —CH. _{2 S -, - SCH 2 -} , - CH 2 NH-, or -NHCH ₂ - is preferably.

[R ³¹ ]
R ³¹ is a hydrogen atom, a halogeno group, a cyano group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted C 3 -8 cycloalkyl group, unsubstituted or substituted C3-8 cycloalkoxy group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-10 aryloxy group, An unsubstituted or substituted 5- to 10-membered heterocyclyl group, or an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group is shown.

Among these, R ³¹ is preferably a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, or an unsubstituted or substituted C1-8 alkoxy group; a hydrogen atom, an unsubstituted C1-8 An 8 alkyl group or an unsubstituted C1-8 alkoxy group is more preferred; an unsubstituted C1-8 alkyl group or an unsubstituted C1-8 alkoxy group is more preferred; an unsubstituted C1-8 alkyl group is particularly preferred. The unsubstituted C1-8 alkyl group is preferably a methyl group, and the unsubstituted C1-8 alkoxy group is preferably a methoxy group.

[ ^R32 ]
R ³² is a halogeno group, a cyano group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted C 3-8 cyclo group. An alkyl group, an unsubstituted or substituted C3-8 cycloalkoxy group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted Or a 5- to 10-membered heterocyclyl group having a substituent, or an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group. These can be the same as those already described in the description of R ¹ .

n represents the number of R ³² and is an integer of 0-2. When n is 2, R ³² may be the same as or different from each other.

[E]
E represents a divalent group consisting of an unsubstituted or substituted benzene ring or a divalent group consisting of an unsubstituted or substituted 5- to 6-membered hetero ring. Among these, a divalent group consisting of a ring selected from the group consisting of a benzene ring, a pyridine ring, a furan ring, a pyrroline ring, a tetrazoline ring, a thiazoline ring, and a pyrazoline ring is preferred, and a divalent group consisting of a benzene ring is preferred. More preferred.

[X]
X _{is, -CH 2 -, - O -} , - S -, - NH -, - CH 2 CH 2 -, - CH 2 O -, - OCH 2 -, - CH 2 S -, - SCH 2 -, - CH ₂ NH— or —NHCH ₂ — is shown. Of these, -O- is preferred.

[A]
A represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-10 membered heterocyclyl group. These can be the same as those already described in the description of R ¹ .

  Among these, preferred specific examples of A include phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, pyridin-2-yl group, thiophen-3-yl group and the like. Among these, a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, or pyridin-2-yl group is preferable; phenyl group, 2-fluorophenyl group, or pyridin-2-yl Groups are more preferred.

  Moreover, as an aminopyridine compound which concerns on this invention, the compound represented by following formula (1-1)-(1-8) is also preferable.

［式（１−１）〜（１−８）中、
Ｒ^１、Ｒ^２、Ｒ^３１、Ｒ^３２、ｎ、Ａは前記同様である。
Ｒ^１２は、無置換の若しくは置換基を有するＣ１〜８アルキル基を示す。
Ｒ^４１〜Ｒ^４８は、それぞれ独立にハロゲノ基を示す。
ｍはＲ^４１〜Ｒ^４８の個数を示し、０〜２のいずれかの整数である。ｍが２のとき、Ｒ^４１〜Ｒ^４８は互いに同じであってもよく異なっていてもよい。
ＱはＣＨ、または窒素原子を示す。］

[In the formulas (1-1) to (1-8),
R ¹ , R ² , R ³¹ , R ³² , n, and A are the same as described above.
R ¹² represents an unsubstituted or substituted C1-8 alkyl group.
R ^{41 to} R ⁴⁸ each independently represent a halogeno group.
m represents the number of ^R 41 ^{to R 48,} which is an integer of 0 to 2. When m is 2, R ^{41 to} R ⁴⁸ may be the same as or different from each other.
Q represents CH or a nitrogen atom. ]

  In the above formula, the unsubstituted or substituted C1-8 alkyl group and halogeno group are the same as described above.

  The aminopyridine compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the aminopyridine compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.

  The salt of the aminopyridine compound according to the present invention is a salt of the compound (1). The salt is not particularly limited as long as it is an agro-horticulturally acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron and copper And salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like. The salt of compound (1) can be obtained from compound (1) by a known method.

The aminopyridine derivative according to the present invention is not particularly limited by the production method. The aminopyridine derivative according to the present invention can be produced, for example, by combining known methods described in Patent Document 2 and other known methods. For example, in the above formula (1), R ¹ is an alkylcarbonyl group, R ² , R ³¹ are hydrogen atoms, and n is 0, the aminopyridine derivative according to the present invention is a synthetic method represented by the following formula: Can be manufactured by.

（式中、Ｅ、ＸおよびＡは、それぞれ、前記式（１）に記載されたＥ、ＸおよびＡと同じものを示し、Ｒ’は、無置換の若しくは置換基を有するアルキル基等を示す。）

(In the formula, E, X and A are the same as E, X and A described in the formula (1), respectively, and R ′ represents an unsubstituted or substituted alkyl group or the like. .)

After completion of the synthesis reaction, the target product can be efficiently isolated by subjecting it to conventional post-treatment operations in organic synthetic chemistry and, if necessary, conventionally known separation and purification means.
The structure of the target product can be identified and confirmed by measuring ¹ H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis, etc.

The agricultural and horticultural fungicide according to the present invention contains at least one selected from the group consisting of compound (1) or a salt thereof as an active ingredient.
The amount of the active ingredient contained in the disinfectant of the present invention is preferably 0.01 to 90% by mass, more preferably 0.05 to 85% by mass, and still more preferably 0.05 to About 80% by mass.

  The agricultural and horticultural fungicide can be used in a form that can be used as an agrochemical, for example, a wettable powder, a granule, a powder, an emulsion, an aqueous solvent, a suspension, a granular wettable powder, and the like.

  The agricultural and horticultural fungicide of the present invention includes fertilizers, solid carriers, thickeners, surfactants, spreading agents, additives, solvents and the like as long as they do not affect the effects of the present invention. Also good.

  As fertilizers, compost, oil cake, fish meal, cow dung, chicken dung, etc. or organic materials made by processing these; nitrogen fertilizers such as ammonium sulfate, ammonium nitrate, lime nitrate, urea; lime superphosphate, monoammonium phosphate, molten Phosphoric fertilizers such as phosphorus fertilizers; Potassium fertilizers such as potassium chloride, potassium sulfate, and potassium nitrate; Mashed fertilizers such as limestone lime; Lime fertilizers such as slaked lime; Silicate fertilizers such as potassium silicate; Boron fertilizers such as borate Chemical fertilizers containing various inorganic fertilizers; and the like.

  Examples of the solid carrier include vegetable powders such as soybean grains and wheat flour; mineral fine powders such as silicon dioxide, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, and earth.

  Additives include organic and inorganic compounds such as sodium benzoate, urea, and mirabilite; rapeseed oil, soybean oil, sunflower oil, castor oil, pine oil, cottonseed oil, and derivatives of these oils, An oil concentrate etc. are mentioned.

  Examples of the solvent include kerosene, xylene; petroleum fractions such as solvent naphtha; cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, water, and the like.

  Examples of the surfactant include alkyl phenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, polyoxyethylene Nonionic surfactants such as tristyrylphenyl ether with addition of ethylene, sulfates of alkylphenyl ethers with addition of polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, poly Examples thereof include a carboxylate, a lignin sulfonate, a formaldehyde condensate of an alkyl naphthalene sulfonate, and an isobutylene-maleic anhydride copolymer.

  The thickener is not particularly limited. For example, starch, dextrin, cellulose, methyl cellulose, ethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl starch, pullulan, sodium alginate, ammonium alginate, propylene glycol ester alginate, guar gum, locust bean gum, gum arabic, xanthan gum Gelatin, casein, polyvinyl alcohol, polyethylene oxide, polyethylene glycol, ethylene / propylene block polymer, sodium polyacrylate, polyvinyl pyrrolidone, carrageenan and the like.

  Examples of the spreading agent include sodium alkyl sulfate, sodium alkylbenzene sulfonate, sodium lignin sulfonate, polyoxyethylene glycol alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan fatty acid ester, and the like. .

  A wettable powder, emulsion, flowable powder, aqueous solvent, or granular wettable powder containing at least one selected from the compound represented by the formula (I) and a salt thereof is diluted with water to a predetermined concentration. Then, it can be used by a method of spraying on a plant as a solution, suspension or emulsion. Moreover, a powder agent and a granule can be used by the method of spraying to a plant as it is.

  Examples of useful plants to be treated with the agricultural and horticultural fungicide of the present invention include cereals, vegetables, root vegetables, potatoes, trees, grasses, and turf. Here, each part of these plants can also be processed. Examples of each part of the plant include leaves, stems, patterns, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, and the like. Further, improved varieties and varieties of these plants, cultivated varieties, and mutants, hybrids, and genetically modified organisms (GMO) can also be treated.

Since the compound (1) or a salt thereof has an excellent bactericidal action, the agricultural and horticultural fungicides containing the compound have a wide variety of fungi such as algae (Oomycetes), baby sac (sac) It can be used to control plant diseases derived from fungi belonging to fungi (Ascomycetes), incomplete fungi (Deuteromycetes), and basidiomycetes.
Therefore, the agricultural and horticultural fungicide of the present invention is used for seed treatment, foliage application, soil application, water surface application and the like performed to control various diseases occurring in agricultural and horticultural crops including flower buds, turf, and grass. can do.

Examples of plant diseases to be controlled are shown below.
Sugar beet: brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc. Such

Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea) Anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial disease (Pseudomonas syringae pv. Lecrymans), etc. Mold disease (Botrytis cinerea), leaf mold disease (Cladosporium fulvum), plague (Phytophthora infestans), half body wilt disease (Verticillium albo-atrum), etc. Eggplant: gray mold disease (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew Diseases such as Erysiphe cichoracearum, Mycovellosiella nattrassii, Sclerotinia sclerotiorum Strawberry: Gray mold disease (Botrytis cinerea), powdery mildew Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthora cactorum), etc. Diseases (Peronospora destructor), white plague (Phytophthora porri), etc. Cabbage: root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), black rot disease (Xanthomonas campesrtis pv. Campestris), black spot bacterial disease (Pseudomonas syringae p. maculicala, Pseudomonas syringae pv. alisalensis), downy mildew (Peronospora parasitica), mycorrhizal disease (Sclerotinia sclerotiorum), etc. Kidney: mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea), etc.

Apples: powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), monilinia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star disease (Gymnosporang) yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple coat rot (Helicobasidium mompa), etc. Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), keratofolium (Cercospora kaki), etc. Rot disease (Phomopsis sp.), Perforated bacterial disease (Xanthomonas campestris pv. Pruni), etc. Diseases (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black Rot (Guignardia bidwellii), etc. Pear: Venturia nashicola, Red rot (Gymnosporangium asiaticum), Black spot (Alternaria kikuchiana), Ring rot (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali), Body blight (Phomopsis fukushii), brown spot disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Cha: ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis), etc. Citrus: scab (Elsinoe fawcetti) , Blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), sunspot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri), etc.

Wheat: powdery mildew (Erysiphe graminis f.sp.Tritici), red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eyeprint Disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot microbe nuclei (Typhula incarnata), snow rot large bacilli (Myriosclerotinia borealis), blight (Gaeumanomyces graminis) Barley: Leafy spot disease (Pyrenophora graminea), Reticulum disease (Pyrenophora teres), Cloud shape disease (Rhynchosporium secalis), Bare smut (Ustilago tritici, U.nuda), etc. Rice: Rice blast (Pyricularia oryzae) Disease (Rhizoctonia solani), idiot seedling disease (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum), white leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), Brown streak (Acidovora x avenae), bacterial wilt (Burkholderia glumae), leaf blight (Cercospora oryzae), rice rot (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), belly black rice (Alternaria padwickii), red rice (Epicoccam purpurascenns), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), etc. Tulip: Gray mold (Botrytis cinerea), etc. solani), dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), red blight (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc. Orchardgrass: powdery mildew (Erysiphe graminis), etc. Cercospora kikuchii), downy mildew (Peronospora Manshurica), stem blight (Phytophthora sojae), rust disease (Phakopsora pachyrhizi), mycorrhizal disease ( Sclerotinia sclerotiorum, anthracnose (Colletotrichum truncatum), etc. Potato: Phytophthora infestans, etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola), etc. Decay disease (Phoma lingam), black spot disease (Alternaria brassicae), etc.

  The fungicides of the present invention include other fungicides, insecticides / acaricides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil improvers, animal feeds, other fungicides These may be used together or in combination.

The application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, disease to be controlled, target crop, etc., but usually 1 to 1,000 g as an active ingredient amount per hectare. , Preferably 10 to 100 g.
When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder or the like is diluted with water and applied, the applied concentration is 1 to 1,000 ppm, preferably 10 to 250 ppm.

  The disinfectant of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.

  EXAMPLES Next, although an Example is given and this invention is demonstrated further in detail, this invention is not limited at all by the following example.

Synthesis example 1

  To the flask was added 0.60 g (4.34 mmol) of 2-aminonicotinic acid, and 20 mL of N, N-dimethylformamide was added thereto. To this, 0.94 g (4.34 mmol) of 4-phenoxybenzyl alcohol, 1.32 g (13.02 mmol) of triethylamine and (Benzotriazol-1-yloxy) -tris (benzotriazol-1-yloxy) -tris ( 2.11 g (4.77 mmol) of dimetylamino) phosphonium hexafluorophosphate; abbreviation BOP) was added at room temperature, and the mixture was stirred at room temperature for 24 hours under a nitrogen atmosphere. The obtained liquid was poured into a mixed solution of 100 mL of ethyl acetate and 100 mL of water, and the organic layer was recovered by a liquid separation operation. On the other hand, the aqueous layer was extracted with 100 mL of ethyl acetate, and the organic layer was recovered. The two organic layers were collected together, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated. The resulting residue was purified with a Yamazen column to obtain 1.28 g (yield 92%) of compound (1) as colorless crystals.

Synthesis example 2

  Compound (1) 0.30g (0.94mmol) was put into the flask, and pyridine 10mL was added to this. To this was added 0.15 g (1.40 mmol) of methoxyacetyl chloride at room temperature, and the mixture was stirred at 60 to 70 ° C. for 6 hours under a nitrogen atmosphere. The resulting liquid was cooled to room temperature. Thereafter, the liquid was concentrated. The concentrated solution was poured into a mixed solution of 100 mL of ethyl acetate and 100 mL of water, and the organic layer was recovered by a liquid separation operation. On the other hand, the aqueous layer was extracted with 100 mL of ethyl acetate, and the organic layer was recovered. The two organic layers were collected together, washed with 50 mL brine, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified with a Yamazen column to obtain 0.28 g (yield 77%) of the compound (24) as a colorless oily substance.

Various aminopyridine derivatives were produced in the same manner as in Synthesis Example 1 and Synthesis Example 2. Some of the produced aminopyridine derivatives are shown in Table 1. R ¹ , R ² , R ³¹ , R ³² , E, X, and A in Table 1 represent those in formula (1). In the column E of Table 1, * indicates a bond with X, and + indicates a bond with a carbon atom. In the column A of Table 1, * indicates a bond with X. In Table 1, Ph represents a phenyl group, Py represents a pyridyl group, Me represents a methyl group, and Et represents an ethyl group. In addition, “5-F” in the column of R ³² in Table 1 is

It represents that F is connected to the 5-position of the structure of “5-Cl” is a similar notation.
“−” In the columns of R ³¹ and R ^{32 in} Table 1 indicates that the column has no substituent, and specifically represents a hydrogen atom.
"2-F-Ph" in the column A in Table 1 is

The number represents the position of the substituent, and F represents the type of the substituent of Ph. “3-F-Ph” and “4-F-Ph” and “4-Cl-Ph” are also the same notation.
“2-Py” in the column A of Table 1 is

The number indicates the position of the bond with X. “3-Py” and “4-Py” are similar notations.
“2- (3-F-Py)” in the column A of Table 1 is

The first number indicates the position of the bond with X, the number in parentheses indicates the position of the substituent, and F indicates the type of substituent of Py. “2- (4-F-Py)”, “2- (5-F-Py)” and “2- (6-F-Py)” are also the same notation.

The melting point or refractive index of some of the compounds shown in Table 1 was measured. The results are shown below.
Compound No. 1 Melting point (° C) 130-132
Compound No. 2 Melting point (° C) 124-125
Compound No. 3 Melting point (° C) 124-125
Compound No. 5 Melting point (° C) 155-157
Compound No. 7 Melting point (° C) 119-121
Compound number 24 Refractive index (nD) 1.5920 (20.8 ℃)
Compound number 25 Refractive index (nD) 1.5935 (20.7 ℃)
Compound number 29 Refractive index (nD) 1.5867 (20.7 ℃)
Compound Number 34 Melting Point (° C) 112-113
Compound No. 35 melting point (° C) 116-117
Compound Number 37 Melting Point (° C) 129-130
Compound No. 42 Melting point (° C) 101-103
Compound Number 70 Melting Point (° C) 105-108
Compound No. 75 Melting point (° C) 114-115
Compound No. 76 melting point (° C) 143-144
Compound Number 82 Melting Point (° C) 117-120
Compound Number: 129 Melting Point (° C) 119-120
Compound No. 130 Melting point (° C) 135-137
Compound Number 131 Melting Point (° C) 77-78
Compound Number 132 Melting Point (° C) 112-113
Compound number 133 Refractive index (nD) 1.5822 (21.9 ℃)
Compound number 134 Refractive index (nD) 1.5832 (22.2 ℃)
Compound Number 135 Melting Point (° C) 112-113
Compound number 136 Refractive index (nD) 1.2782 (20.7 ℃)
Compound No. 137 Melting Point (° C) 121-123
Compound number 138 Refractive index (nD) 1.5873 (19.4 ℃)
Compound Number 139 Melting Point (° C) 48-50
Compound number 140 Refractive index (nD) 1.5687 (20.4 ℃)
Compound number 141 Refractive index (nD) 1.5926 (20.0 ℃)
Compound Number 142 Melting Point (° C) 136-138
Compound number 143 Refractive index (nD) 1.5767 (19.2 ℃)
Compound No. 144 Melting point (° C) 99-100
Compound Number 145 Melting Point (° C) 104-105
Compound number 146 Refractive index (nD) 1.5819 (20.7 ℃)
Compound No. 147 melting point (° C) 116-118
Compound Number 148 Melting Point (° C) 155-156
Compound number 149 Melting point (° C) 135-136
Compound Number 152 Melting Point (° C) 141-144

Of the compounds shown in Table 1, the ¹ H-NMR measurement results of Compound Nos. 28, 150 and 151 are shown below.
Compound No. 28: 3.55 (s, 3H), 4.15 (s, 2H), 5.34 (s, 2H), 7.01-7.04 (m, 4H), 7.09 (d, 1H), 7.14 (m, 1H), 7.34- 7.40 (m, 4H), 8.26 (d, 1H), 11.40 (bs, 1H)
Compound No. 150: 2.60 (s, 3H), 3.55 (s, 3H), 4.16 (s, 2H), 5.09 (s, 2H), 5.30 (s, 2H), 6.92 (d, 1H), 6.97-7.00 ( m, 2H), 7.15 (dd, 1H), 7.33-7.38 (m, 4H), 8.19 (d, 1H), 11.36 (bs, 1H)
Compound No. 151: 3.56 (s, 3H), 4.13 (s, 2H), 5.23 (s, 2H), 5.32 (s, 2H), 7.00-7.10 (m, 3H), 7.20-7.30 (m, 1H), 7.38 (d, 2H), 7.52 (d, 1H), 7.70-7.75 (m, 1H), 8.33 (dd, 1H), 8.60-8.67 (m, 2H), 11.6 (br s, 1H)

  Next, formulation examples of the agricultural and horticultural fungicides according to the present invention are shown. However, additives and addition ratios are not limited to these formulation examples, and can be changed in a wide range. . Moreover, the part in a formulation example shows a mass part.

Formulation Example 1 (wettable powder)
Compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts The above is uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient.

Formulation Example 2 (Emulsion)
Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts The above components are mixed and dissolved to obtain an emulsion containing 10% active ingredient.

Formulation Example 3 (Dust)
Compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.

Formulation Example 4 (Granule)
Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above components are pulverized and mixed well, mixed well with water, granulated and dried, and 5% active ingredient. Get the granules.

Formulation Example 5 (Suspension)
Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts The above is mixed and wet milled until the particle size is 3 microns or less, A suspension with 10% active ingredient is obtained.

Formulation Example 6 (Granule wettable powder)
Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzene sulfonic acid sodium salt 5 parts Add water and knead to make clay. The clay-like product is granulated and then dried to obtain a granulated wettable powder containing 40% of the active ingredient.

(Biological Test Example 1) Cucumber Gray Mold Control Test The cucumber seedlings (variety “Tokiwa Chiku”, cotyledon stage) cultivated in an unglazed pot were sprayed with the emulsion of the formulation example 2 at a concentration of 125 ppm active ingredient. And allowed to air dry at room temperature. Subsequently, a conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) was inoculated dropwise and kept in a dark room at 20 ° C. and high humidity for 4 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
Numerals 1, 2, 3, 7, 24, 25, 28-29, 34, 35, 37, 42, 75-76, 129-138, 141, 144, 148 and 150 were tested for cucumber gray mold control. went. As a result, all the compounds showed a control value of 75% or more.

(Biological Test Example 2) Wheat powdery mildew control test A wheat seedling (variety “Chihoku”, 1.0-1.2 leaf stage) cultivated in an unglazed pot was mixed with the wettable powder obtained in the formulation of Formulation Example 1. The active ingredient was sprayed at a concentration of 125 ppm and allowed to air dry at room temperature. Thereafter, conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were shaken off and inoculated in a greenhouse at 22 to 25 ° C. for 7 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
No. 1, 2, 3, 7, 24, 25, 28-29, 35, 37, 42, 70, 75-76, 130, 132-138 and 140-145 were subjected to wheat powdery mildew control test. . As a result, all the compounds showed an excellent control value of 75% or more.

Claims (7)

An aminopyridine compound represented by the formula (1) or a salt thereof.

[In Formula (1),
R ¹ is a hydrogen atom, a formyl group, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C1-8 alkoxy group, an unsubstituted or substituted C1-8 alkyl A carbonyl group, an unsubstituted or substituted C3-8 cycloalkylcarbonyl group, an unsubstituted or substituted C6-10 arylcarbonyl group, an unsubstituted or substituted 5-10 membered heterocyclylcarbonyl group, Unsubstituted or substituted C3-8 cycloalkyl C1-6 alkylcarbonyl group, unsubstituted or substituted C6-10 aryl C1-6 alkylcarbonyl group, unsubstituted or substituted 5-10 Membered heterocyclyl C1-6 alkylcarbonyl group, unsubstituted or substituted C1 8 alkyloxycarbonyl group, unsubstituted or substituted C2-8 alkenyloxycarbonyl group, unsubstituted or substituted C2-8 alkynyloxycarbonyl group, unsubstituted or substituted C3-8 cyclo An alkyloxycarbonyl group, an unsubstituted or substituted C6-10 aryloxycarbonyl group, an unsubstituted or substituted 5-10 membered heterocyclyloxycarbonyl group, an unsubstituted or substituted C1 ~ 8 alkylthiocarbonyl group, unsubstituted or substituted diC1-8 alkylsulfamoyl group, unsubstituted or substituted C1-8 alkylsulfonyl group, unsubstituted or substituted C3-8 cyclo Alkylsulfonyl group, unsubstituted or substituted A C6-10 arylsulfonyl group or an unsubstituted or substituted 5-10 membered heterocyclylsulfonyl group is shown.
R ² represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C1-8 alkoxy group, or an unsubstituted or substituted C1-8 alkylcarbonyl group. Indicates.
However, R ¹ and R ² are not both hydrogen atoms.
R ³¹ is a hydrogen atom, a halogeno group, a cyano group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted C 3 -8 cycloalkyl group, unsubstituted or substituted C3-8 cycloalkoxy group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-10 aryloxy group, An unsubstituted or substituted 5- to 10-membered heterocyclyl group, or an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group is shown.
R ³² is a halogeno group, a cyano group, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 1-8 alkoxy group, an unsubstituted or substituted C 3-8 cyclo group. An alkyl group, an unsubstituted or substituted C3-8 cycloalkoxy group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted C6-10 aryloxy group, an unsubstituted Or a 5- to 10-membered heterocyclyl group having a substituent, or an unsubstituted or substituted 5- to 10-membered heterocyclyloxy group. n represents the number of R32 and is an integer of 0-2. When n is 2, R ³² may be the same as or different from each other.
E represents a divalent group consisting of an unsubstituted or substituted benzene ring or a divalent group consisting of an unsubstituted or substituted 5- to 6-membered hetero ring.
X _{is, -CH 2 -, - O -} , - S -, - NH -, - CH 2 CH 2 -, - CH 2 O -, - OCH 2 -, - CH 2 S -, - SCH 2 -, - CH ₂ NH— or —NHCH ₂ — is shown.
A represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-10 membered heterocyclyl group. ] The aminopyridine compound or a salt thereof according to claim 1, which is represented by any one of the following formulas (1-1) to (1-8).

[In the formulas (1-1) to (1-8),
R ¹ , R ² , R ³¹ , R ³² , n, and A are the same as described above.
R ¹² represents an unsubstituted or substituted C1-8 alkyl group.
R ^{41 to} R ⁴⁸ each independently represent a halogeno group.
m represents the number of ^R 41 ^{to R 48,} which is an integer of 0 to 2. When m is 2, R ^{41 to} R ⁴⁸ may be the same as or different from each other.
Q represents CH or a nitrogen atom. ] R ³¹ is a C1~8 alkyl group having unsubstituted or substituted group, an amino pyridine compound or salt thereof according to claim 1 or 2. The aminopyridine compound according to claim 1, wherein E is a divalent group consisting of a ring selected from the group consisting of a benzene ring, a pyridine ring, a furan ring, a pyrroline ring, a tetrazoline ring, a thiazoline ring, and a pyrazoline ring. Its salt. The aminopyridine compound or a salt thereof according to claim 1, wherein E is a divalent group consisting of a benzene ring, and X is -O-. R ¹ Is a hydrogen atom, a formyl group, an unsubstituted or substituted C1-8 alkoxy group, an unsubstituted or substituted C1-8 alkylcarbonyl group, or an unsubstituted or substituted C1-8 Represents an alkyloxycarbonyl group,
  R ² Is an amino group according to any one of claims 1 to 5, which represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, or an unsubstituted or substituted C1-8 alkoxy group. A pyridine compound or a salt thereof.   An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the aminopyridine compound according to any one of claims 1 to 6 or a salt thereof.