JP5729889B2 - Nitrogen-containing heterocyclic compounds and agricultural and horticultural fungicides - Google Patents

Description

The present invention relates to a nitrogen-containing heterocyclic compound or a salt thereof or an N-oxide compound. More specifically, the present invention relates to an agricultural and horticultural fungicide that can be used safely and safely, and a nitrogen-containing heterocyclic compound or a salt or N-oxide compound useful as an active ingredient of the agricultural and horticultural fungicide.
This application claims priority based on Japanese Patent Application No. 2011-228373 for which it applied to Japan on October 17, 2011, and uses the content here.

  Numerous control agents are known for 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.

  Patent Documents 1 to 3 disclose a quinoline derivative having a chemical structure similar to that of the compound of the present invention and an agricultural and horticultural fungicide containing it as an active ingredient.

WO2005 / 0700917 pamphlet WO2007 / 011022 pamphlet WO2011 / 081174 pamphlet

  An object of the present invention is to provide an agricultural and horticultural fungicide that can be used safely and safely, and a nitrogen-containing heterocyclic compound or a salt or N-oxide compound useful as an active ingredient of the agricultural and horticultural fungicide. To do.

The present invention includes the following aspects.
[1] A nitrogen-containing heterocyclic compound represented by the formula (1), a salt thereof or an N-oxide compound.

In the above formula (1), Cy represents an unsubstituted or substituted 5-membered heteroaryl group, an unsubstituted or substituted 6-membered heteroaryl group, an unsubstituted or substituted partially unsaturated group. A 5-membered heterocyclic group, an unsubstituted or partially unsaturated 6-membered heterocyclic group having a substituent is shown.
B represents a carbon atom.
D represents a benzene ring.
X ¹ is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C3-8 cycloalkyl group, Unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 5-6 membered heterocyclic group, unsubstituted or substituted A C1-8 acyl group having a group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, Unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group, unsubstituted or substituted mercapto group, A sulfonyl group, a halogeno group, a cyano group, or a nitro group having a substituent is shown. m represents the number of X ¹ and is an integer of 0 to 6.
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
X ² is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C3-8 cycloalkyl group, Unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 5-6 membered heterocyclic group, unsubstituted or substituted A C1-8 acyl group having a group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, Unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group, unsubstituted or substituted mercapto group, A sulfonyl group, a halogeno group, a cyano group, or a nitro group having a substituent is shown. n represents the number of ^{X 2,} is any integer of 0 to 4.
X represents an oxygen atom.
[2] The nitrogen-containing heterocyclic compound or the salt or N-oxide compound thereof according to [1], wherein the formula (1) is represented by the formula (2).

In said formula (2), Cy, X < ¹ >, m, X < ² >, n, B, and X show the same meaning as each in said formula (1).
A ¹ , A ² , A ³ , and A ⁴ each independently represent a carbon atom or a nitrogen atom.
[3] The nitrogen-containing heterocyclic compound or a salt or N-oxide compound thereof according to [1], wherein the formula (1) is represented by the formula (3).

In said formula (3), Cy, X < ¹ >, m, X < ² >, B, and X show the same meaning as each in said formula (1). n1 represents the number of X ² and is an integer of 0 to 3.
A ⁵ , A ⁶ , and A ⁷ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
[4] The nitrogen-containing heterocyclic compound according to [1], wherein the formula (1) is represented by the formula (4), or a salt or N-oxide compound thereof.

In the above formula ^{(4), Cy, D,} X 1, m, X 2, and n have the same meanings as each of the above formulas (1).

[5] Agricultural and horticultural sterilization containing, as an active ingredient, at least one selected from the nitrogen-containing heterocyclic compound according to any one of [1] to [4] above, or a salt thereof or an N-oxide compound thereof Agent.

  The nitrogen-containing heterocyclic compound 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 present inventors have found that the nitrogen-containing heterocyclic compounds of the nitrogen-containing heterocyclic compounds represented by the formulas (1) to (4) have a certain effect and can be safely used as active ingredients of agricultural and horticultural fungicides. The present invention has been completed through further studies based on the findings.

  Hereinafter, the present invention will be described in detail by dividing it into 1) nitrogen-containing heterocyclic compounds and 2) agricultural and horticultural fungicides.

1) Nitrogen-containing heterocyclic compound [compound represented by formula (1)]
The nitrogen-containing heterocyclic compound according to the present invention is a compound represented by the formula (1) (hereinafter sometimes referred to as “compound (1)”), a salt thereof, or an N-oxide compound.

  The nitrogen-containing heterocyclic compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the nitrogen-containing heterocyclic compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures 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 (= O); chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group, etc. C1-6 haloalkyl 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 Groups, C2-6 haloalkynyl groups such as 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group A C2-6 haloalkenyloxy group such as 3-bromobutenyloxy group; 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichloro C6-10 haloaryl group such as chlorophenyl 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 group, pyridazinyl group, triazinyl group; saturated heterocyclic groups such as pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethylsilyl group, t-butyl A tri-C1-6 alkylsilyl group such as a dimethylsilyl group; a triphenylsilyl group;

  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.

[Cy]
Cy represents an unsubstituted or substituted oxiranyl group or an unsubstituted or substituted 5- to 6-membered heterocyclic group.
The “5- to 6-membered heterocyclic group” includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring.
Cy includes an unsubstituted or substituted oxiranyl group, an unsubstituted or substituted 5-membered heteroaryl group, an unsubstituted or substituted 6-membered heteroaryl group, an unsubstituted or substituted group. A partially unsaturated 5-membered heterocyclic group, an unsubstituted or substituted partially unsaturated 6-membered heterocycle, an unsubstituted or substituted saturated 5-membered heterocyclic group, or unsubstituted or A saturated 6-membered heterocyclic group having a substituent is preferable.

  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 group; thiazolyl group such as thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group; isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl 1,2,3-triazol-1-yl group, 1,2,3-triazol-4-yl group, 1,2,3-triazol-5-yl group, 1,2,4 -Triazolyl groups such as triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group; 1,2,4-oxadiazole-3- Oxadiazolyl group such as yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazol-2-yl group; 1,2,4-thiadiazol-3-yl group, 1, , 4-thiadiazol-5-yl group, 1,3,4-thiadiazol-2-yl-thiadiazolyl group such as a group; and the like; tetrazol-1-yl group, tetrazolyl group, such as tetrazol-2-yl group.

  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; It is done.

  As partially unsaturated 5-membered heterocyclic group, pyrrolinyl group such as 2-pyrrolin-3-yl group; 2-imidazolin-1-yl group, 2-imidazolin-2-yl group, 2-imidazolin-4-yl Groups, imidazolinyl groups (dihydroimidazolinyl group) such as 2-imidazolin-5-yl group; 3-pyrazolin-1-yl group, 3-pyrazolin-2-yl group, 3-pyrazolin-3-yl group, 3 -Pyrazolinyl groups such as pyrazolin-4-yl group, 3-pyrazolin-5-yl group; oxazolinyl groups such as 2-oxazolin-2-yl group, 2-oxazolin-4-yl, 2-oxazolin-5-yl; Isooxazolin-3-yl group, 2-isoxazolin-4-yl group, 2-isoxazolin-5-yl group, isoxazolin-3-yl group and the like Zoriniru; like; 2-thiazoline-2-yl group, 2-thiazoline-4-yl group, 3-thiazoline-2-yl group thiazolinyl such.

  As the partially unsaturated 6-membered heterocyclic group, pyranyl group such as 2H-pyran-3-yl group; thiopyranyl group such as 2H-thiopyran-3-yl group; 2H-pyridin-1-yl group, 4H-pyridine -1-yl group; and the like.

Examples of saturated 5-membered heterocyclic groups include pyrrolidinyl groups such as pyrrolidin-1-yl group, pyrrolidin-2-yl group and pyrrolidin-3-yl group; tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group and the like. A tetrahydrofuranyl group; a dioxolanyl group such as a [1,3] dioxiran-2-yl group; and the like.
Examples of the saturated 6-membered heterocyclic group include piperidin-1-yl group, piperidin-2-yl group, piperidin-3-yl group, piperidin-4-yl group, and the like; piperazin-1-yl group, piperazine Piperazinyl groups such as -2-yl group; morpholinyl groups such as morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group and the like.

  Cy includes pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, oxadiazolyl, pyridyl, isoxazolinyl, pyrrolidinyl, or dioxolanyl. More preferably.

  Examples of the substituent on Cy include the same as those exemplified as the “substituent” above. Preferably, a halogeno group, a C1-6 alkyl group, a C3-6 cycloalkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C6-10 aryl group, a C6-10 aryloxy group, C7-11 aralkyl group, C7-11 aralkyloxy group, C1-7 acyl group, C1-7 acyloxy group, C1-6 alkoxycarbonyl group, carboxyl group, hydroxyl group, oxo group (= O), C1-6 haloalkyl group, C1-6 haloalkoxy group, C1-7 haloacyl group, cyano group, nitro group, amino group, C1-6 alkylamino group, C1-7 acylamino group, C1-6 alkoxycarbonylamino group, carbamoyl group, substituted carbamoyl group, Mercapto group, C1-6 alkylthio group, C1-6 alkylsulfonyl group, C6-10 aryl Sulfonyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, and the like saturated heterocyclic group, and tri C1~6 alkyl silyl group. Among these, a substituent selected from a halogeno group, a C1-6 alkyl group, and a hydroxyl group is preferable.

  Examples of the 5- to 6-membered heterocyclic group having an oxo group (═O) include 2-oxo-pyrrolidin-1-yl, 2-oxo-piperidin-1-yl, 2-oxo-2H-pyridin-1-yl, and the like. Is mentioned. Of these, 2-oxo-pyrrolidin-1-yl is preferred.

When Cy is a 5- to 6-membered heterocyclic group, a substituent on Cy may be present adjacent to each other to form an unsubstituted or substituted 5- to 8-membered ring. Good.
Examples of a 5- to 8-membered ring that can be formed together include an aromatic hydrocarbon ring such as a benzene ring; a C5-8 cycloalkene ring such as a cyclopentene ring, cyclopentadiene ring, cyclohexene ring, cycloheptene ring, and cyclooctene ring; Etc.

[B, D]
B represents a carbon atom or a nitrogen atom. That is, a pyridine ring formed by condensation of “D” or a pyrazine ring formed by condensation of “D” is formed.
D is a part of a ring constituting a pyridine ring or a pyrazine ring, and represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered hetero ring.
Examples of 5- to 7-membered hydrocarbon rings include aromatic hydrocarbon rings such as benzene rings; cycloalkene rings such as cyclopentene rings, cyclohexene rings, and cycloheptene rings; cycloalkane rings such as cyclopentane rings, cyclohexane rings, and cycloheptane rings. Is mentioned.
The 5- to 7-membered heterocycle includes a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring. , Azepine ring, diazepine ring; dihydro-2H-pyran ring, dihydro-2H-thiopyran ring, tetrahydropyridine ring; hexamethyleneimine ring, 2-ketohexamethyleneimine ring, homopiperazine ring and the like.
In Formula (1), as D, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable. Specifically, the compound (1) is preferably a compound having a quinoline ring or a quinoxaline ring.

[X ¹ ]
X ¹ is D and / or a substituent of a pyridine ring or a pyrazine ring, each independently an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 2-8 An alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted Or a substituted C6-10 aryl group, an unsubstituted or substituted 5-6 membered heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted group ( 1-imino) C1-8 alkyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, unsubstituted It represents a substituted or substituted hydroxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group. m represents the number of X ^{1 and} is an integer of 0 to 6 (preferably an integer of 0 to 2).

The “C 1-8 alkyl group” in X ¹ is a saturated hydrocarbon group composed of 1 to 8 carbon atoms. The C1-8 alkyl group may be linear or branched. As C1-8 alkyl group, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, 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 group; 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-trichloro Roethyl 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-hexachlorooctyl group, etc. Haloalkyl groups, preferably C1-6 haloalkyl groups; arylalkyl groups (aralkyl groups) such as benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, preferably C6-10 An aryl C1-6 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, 2- (2-free ) Heteroarylalkyl groups such as ethyl group, 2- (3-furyl) ethyl group, 3- (2-furyl) propyl group, 3- (3-furyl) propyl group, preferably 5-6 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- Hydroxyalkyl groups such as dimethylethyl group, 2-hydroxy-1,1-dimethylpropyl group, 2-hydroxy-2-methylpropyl group, preferably hydroxy C1-6 alkyl group;

  Methoxymethyl group, ethoxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, methoxy n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, Alkoxyalkyl groups such as 2,2-dimethoxyethyl group, 2,2-dimethoxy-1,1-dimethylethyl group, preferably C1-6 alkoxyC1-6 alkyl group; formyloxymethyl group, acetoxymethyl group, 2- Acyloxyalkyl groups such as acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group, preferably C1-7 acyloxy C1-6 alkyl group; trialkylsilyloxy such as trimethylsilyloxymethyl group, t-butyldimethylsilyloxymethyl group Alkyl group, preferred Or tri-C1-6 alkylsilyloxy C1-6 alkyl group; arylsulfonyloxyalkyl groups such as tosyloxymethyl group, 2-tosyloxy-1,1-dimethylethyl group, preferably C1-6 alkyl substituted C6-10 aryl Sulfonyloxy C1-6 alkyl group; cyanoalkyl group such as cyanomethyl group, 2-cyanoethyl group, 1-cyano-1-methylethyl group, preferably cyano 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-1- Acyl alcohol such as methylethyl group and 2-acetyl-1,1-dimethylethyl group Group, preferably C1~6 acyl C1~6 alkyl group;

  2-hydroxyiminoalkyl group such as 2-hydroxyiminoethyl group, 2-hydroxyimino-1-methylethyl group, 2-hydroxy-1,1-dimethylethyl group, 2-hydroxyiminopropyl group, preferably 2-hydroxy An imino C2-6 alkyl group; an acylalkyl group such as an acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1-methylethyl group, 2-acetyl-1,1-dimethylethyl group; Preferably formyl C1-6 alkyl group; carboxyalkyl such as carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 1-carboxy-1-methylethyl group, 2-carboxy-1,1-dimethylethyl group A group, preferably a carboxy C 1-6 alkyl group; Alkoxycarbonylalkyl groups such as til, 2-methoxycarbonylethyl, 3-methoxycarbonylpropyl, 1-methoxycarbonyl-1-methylethyl, 2-methoxycarbonyl-1,1-dimethylethyl, preferably C1 -6 alkoxycarbonyl C1-6 alkyl group; azidoalkyl groups such as azidomethyl group, 2-azidoethyl group, 1-azido-1-methylethyl group, preferably azido C1-6 alkyl group; and the like.

The “C 2-8 alkenyl group” in X ¹ is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon double bond. The C2-8 alkenyl group may be linear or branched. C2-8 alkenyl groups include vinyl, 1-propenyl, isopropenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 6-heptenyl group, 1-octenyl group, 7- Examples include octenyl group, 1-methyl-allyl group, 2-methyl-allyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group and the like. Of these, C2-6 alkenyl groups are preferred.

  Examples of the “substituted C2-8 alkenyl group” include 3-chloro-2-propenyl group, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group, and 4,4-difluoro-3. -Butenyl group, 3,3-dichloro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group, etc. A haloalkenyl group, preferably a C2-6 haloalkenyl group; a hydroxyalkenyl such as a 3-hydroxy-1-propenyl group, a 4-hydroxy-1-butenyl group, a 1-hydroxyallyl group, and a 1-hydroxy-2-methylallyl group Group, preferably a hydroxy C2-6 alkenyl group; and the like.

The “C 2-8 alkynyl group” in X ¹ is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon triple bond. The C2-8 alkynyl group may be linear or branched. Examples of the C2-8 alkynyl group include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4 -Pentynyl group, 1-hexynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1,1-dimethyl -2-butynyl group and the like. Of these, C2-6 alkynyl groups are preferred.

  Examples of the “substituted C2-8 alkynyl group” include a 3-chloro-1-propynyl group, a 3-chloro-1-butynyl group, a 3-bromo-1-butynyl group, a 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3-bromo-1-hexynyl group, 4,4,6,6-tetrafluoro-1-dodecynyl group, 5,5-dichloro-2-methyl-3-pentynyl group, 4 A haloalkynyl group such as a -chloro-1,1-dimethyl-2-butynyl group, preferably a C2-6 haloalkynyl group.

The “C 3-8 cycloalkyl group” in X ¹ is an alkyl group composed of 3 to 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, and a cyclooctyl group. Of these, C3-6 cycloalkyl groups are preferred.

  Examples of the “substituted C3-8 cycloalkyl group” include alkyl substitution such as 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group, etc. Examples thereof include a cycloalkyl group, preferably a C3-6 cycloalkyl group in which 1 to 3 C1-6 alkyl groups are substituted.

The “C4-8 cycloalkenyl group” in X ¹ is an alkenyl group composed of 4-8 carbon atoms having a cyclic moiety. Examples of the C4-8 cycloalkenyl group include 1-cyclobutenyl group, 1-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 3-cyclohexenyl group, 3-cycloheptenyl group, 4-cyclooctenyl group and the like. It is done.

  Examples of the “substituted C4-8 cycloalkenyl group” include alkyl-substituted cycloalkenyl groups such as 2-methyl-3-cyclohexenyl group and 3,4-dimethyl-3-cyclohexenyl group, preferably C1-6 alkyl. And C4-6 cycloalkenyl groups substituted with 1 to 3 groups.

The “C6-10 aryl group” in X ¹ 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” include 2-chlorophenyl group, 3,5-dichlorophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, 4-trifluoromethylphenyl group, 2- Alkyl-substituted aryl group, halogeno-substituted aryl group, alkoxy-substituted aryl group such as methoxy-1-naphthyl group, preferably C1-6 alkyl-substituted C6-10 aryl group, halogeno-substituted C6-10 aryl group, C1-6 alkoxy-substituted An aryl group is mentioned.

Examples of the “5- to 6-membered heterocyclic group” in X ¹ include the same as those exemplified for Cy.

The “C1-8 acyl group” in X ¹ is a carbonyl group, a hydrogen atom, a C1-7 alkyl group, a C2-7 alkenyl group, a C2-7 alkynyl group, a C6-7 aryl group or a 5-7 membered heterocyclic ring. A group to which a group is bonded.
As the C1-8 acyl group, formyl group; acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, pentanoyl group, valeryl group, octanoyl group, i-propylcarbonyl group, i-butylcarbonyl group, An alkylcarbonyl group such as a pivaloyl group and an isovaleryl group, preferably a C1-6 alkylcarbonyl group; an alkenylcarbonyl group such as an acryloyl group and a methacryloyl group, preferably a C2-6 alkenylcarbonyl group; an alkynylcarbonyl group such as a propioroyl group, preferably C2-6 alkynylcarbonyl groups; arylcarbonyl groups such as benzoyl groups; heterocyclic carbonyl groups such as 2-pyridylcarbonyl groups and thienylcarbonyl groups.

  Examples of the “substituted C1-8 acyl group” include a monofluoroacetyl group, a monochloroacetyl group, a monobromoacetyl group, a difluoroacetyl group, a dichloroacetyl group, a dibromoacetyl group, a trifluoroacetyl group, a trichloroacetyl group, a trichloroacetyl group, Haloacyl group such as bromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3-trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, preferably C1-7 haloacyl Group and the like.

The “(1-imino) C1-8 alkyl group” in X ¹ is an iminomethyl group or a group in which a C1-7 alkyl group is bonded to an iminomethyl group. The (1-imino) C1-8 alkyl group includes an iminomethyl group, a (1-imino) ethyl group, a (1-imino) propyl group, a (1-imino) butyl group, a (1-imino) pentyl group, (1 -Imino) hexyl group, (1-imino) heptyl group and the like. Of these, (1-imino) C1-6 alkyl groups are preferred.

  Examples of the “(1-imino) alkyl group having a substituent” include a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, a (1-hydroxyimino) propyl group, and a (1-hydroxyimino) butyl group. 1-hydroxyimino) C1-8 alkyl group; preferably (1-hydroxyimino) C1-6 alkyl group; methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-methoxyimino) ethyl group, (1 (1-t-butoxyimino) ethyl group, (1-ethoxyimino) ethyl group and other (1-alkoxyimino) C1-8 alkyl groups, preferably (1- (C1-6 alkoxy) imino) C1-6 alkyl groups; Etc.

The “carboxyl group having a substituent” in X ¹ is a carbonyl group having a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a C 6-10 aryl C 1-6 alkyl. Or a group to which a 5- or 6-membered heterocyclic group is bonded.
As the “carboxyl group having a substituent”, a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, an i-butoxycarbonyl group, a t-butoxycarbonyl group, n An alkoxycarbonyl group such as a pentyloxycarbonyl group or an n-hexyloxycarbonyl group, preferably a C1-6 alkoxycarbonyl group; an alkenyloxycarbonyl group such as a vinyloxycarbonyl group or an allyloxycarbonyl group, preferably a C2-6 alkenyloxy Carbonyl group; alkynyloxycarbonyl group such as ethynyloxycarbonyl group, propargyloxycarbonyl group, preferably C2-6 alkynyloxycarbonyl group; phenoxycarbonyl group, naphthoxy Aryloxycarbonyl groups such as carbonyl groups, preferably C6~10 aryloxycarbonyl group; aralkyloxycarbonyl groups such as benzyloxycarbonyl group, preferably C6~10 aryl C1~6 alkoxycarbonyl group; and the like.

The “carbamoyl group having a substituent” in X ¹ is a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a C 6-10 aryl C 1-6 alkyl group. Or a group to which a 5- or 6-membered heterocyclic group is bonded. Examples of the “substituted carbamoyl group” include a monoalkylcarbamoyl group or a dialkylcarbamoyl group such as a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group, and a diethylcarbamoyl group, preferably a monoC1-6 alkylcarbamoyl group or a diC1_1 group. 6 alkylcarbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group, preferably monoC6-10 arylcarbamoyl group.

As the “hydroxyl group having a substituent” in X ¹ , a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, a decyloxy group, a dodecyloxy group, lauryl Oxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, 1-ethylpropoxy group, i-hexyloxy group, 4-methylpentoxy group, 3-methylpentoxy group, 2 -Methylpentoxy group, 1-methylpentoxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethyl Alkoxy groups such as butoxy group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group, 2-ethylbutoxy group, preferably C1-6 alkoxy Si group;

  A cycloalkylalkoxy group such as a cyclopropylmethyloxy group and a 2-cyclopentylethyloxy group, preferably a C3-8 cycloalkyl C1-6 alkoxy group; an aralkyloxy group such as a benzyloxy group, preferably a C6-10 aryl C1-6 Alkoxy group; chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc. A haloalkoxy group, preferably a C1-6 haloalkoxy group; vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group Si group, 3-pentenyloxy group, 4-pentenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1-methyl-2 An alkenyloxy group such as a propenyloxy group, 2-methyl-2-propenyloxy group, 1-methyl-2-butenyloxy group, 2-methyl-2-butenyloxy group, preferably a C2-6 alkenyloxy group;

Ethynyloxy, propynyloxy, propargyloxy, 1-butynyloxy, 2-butynyloxy, 3-butynyloxy, 1-pentynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4- Pentynyloxy group, 1-hexynyloxy group, 1-methyl-2-propynyloxy group, 2-methyl-3-butynyloxy group, 1-methyl-2-butynyloxy group, 2-methyl-3-pentynyloxy group, 1 , 1-dimethyl-2-butynyloxy group and the like, preferably C2-6 alkynyloxy group; cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group Group, 2-methylcyclopropyloxy group, 2 -Ethylcyclopropyloxy group, 2,3,3-trimethylcyclobutyloxy group, 2-methylcyclopentyloxy group, 2-ethylcyclohexyloxy group, 2-ethylcyclooctyloxy group, 4,4,6,6-tetra A cycloalkyloxy group such as a methylcyclohexyloxy group and a 1,3-dibutylcyclohexyloxy group, preferably a C3-6 cycloalkyloxy group; a phenyloxy group, a naphthyloxy group, an azulenyloxy group, an indenyloxy group, an indanyloxy group; Aryloxy groups such as tetralinyloxy group, preferably C6-10 aryloxy groups; arylalkyloxy groups (aralkyloxy groups) such as benzyloxy group, phenethyloxy group, 2-naphthylmethyloxy group, preferably C6 -10 aryl 1-6 alkyloxy groups; acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, pentanoyloxy group, pivaloyloxy group An acyloxy group such as, preferably a C1-7 acyloxy group; an alkoxycarbonylalkyloxy group such as a methoxycarbonylmethyloxy group, 1-methoxycarbonyl-1-methylethyloxy group, preferably a C1-6 alkoxycarbonyl C1-6 alkoxy group A trialkylsilyloxy group such as a trimethylsilyloxy group or t-butyldimethylsilyloxy group, preferably a tri-C1-6 alkylsilyloxy group;
Etc.

  The “amino group having a substituent” is an alkylamino group such as a methylamino group, an ethylamino group, an n-propylamino group, an n-butylamino group, a dimethylamino group or a diethylamino group, preferably a mono-C1-6 alkyl. Amino group or di-C1-6 alkylamino group; mono-C1-6 alkylideneamino group such as methylideneamino group, ethylideneamino group; monoarylamino group such as phenylamino group, 4-methylphenylamino group, preferably monoC6-10 An arylamino group; a diarylamino group such as a di1-naphthylamino group, preferably a diC6-10 arylamino group; an aralkylamino group such as a benzylamino group, preferably a C6-10 arylC1-6 alkylamino group; Group, trifluoroacetylamino Group, acylamino group such as benzoylamino group, preferably C1-6 acylamino group; alkoxycarbonylamino group such as methoxycarbonylamino group, t-butoxycarbonylamino group, preferably C1-6 alkoxycarbonylamino group; .

As the “mercapto group having a substituent” in X ¹ , an alkylthio group such as a methylthio group and an ethylthio group, preferably a C1-6 alkylthio group; an arylthio group such as a phenylthio group and a 4-methylphenylthio group, preferably C6 -10 arylthio group; acylthio groups such as acetylthio group and benzoylthio group, preferably C1-6 acylthio group; and the like.

Examples of the “sulfonyl group having a substituent” in X ¹ include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, and s-butyl. Alkylsulfonyl groups such as sulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, i-pentylsulfonyl group, neopentylsulfonyl group, 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, i-hexylsulfonyl group, Preferably a C1-6 alkylsulfonyl group; a haloalkylsulfonyl group such as a trifluoromethylsulfonyl group, preferably a C1-6 haloalkylsulfonyl group; an arylsulfonyl group such as a phenylsulfonyl group, a 4-methylphenylsulfonyl group, preferably C6-10 arylsulfonyl group; sulfo group; alkoxysulfonyl group such as methoxysulfonyl group and ethoxysulfonyl group, preferably C1-6 alkoxysulfonyl group; sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group A sulfamoyl group such as N, N-dimethylsulfamoyl group, N, N-diethylsulfamoyl group, preferably a mono C1-6 alkylsulfamoyl group or a diC1-6 alkylsulfamoyl group; And a monoarylsulfamoyl group such as a moyl group and 4-methylphenylsulfamoyl group, preferably a mono C6-10 arylsulfamoyl group.

Examples of the “halogeno group” in X ¹ include a fluoro group, a chloro group, a bromo group, and an iodo group.
Among these, X ¹ is preferably a halogeno group or a C1-C8 alkyl group.

[E]
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
As the 5- to 7-membered hydrocarbon ring, an aromatic hydrocarbon ring such as a benzene ring; a C5-7 cycloalkene ring such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; a furan ring, a thiophene ring, a pyrrole ring, and an imidazole ring , Pyrazole ring, thiazole ring, oxazole ring, isoxazole ring, isothiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, azepine ring, diazepine ring and other aromatic 5- to 7-membered heterocycles; .
Of these, an aromatic hydrocarbon ring or an aromatic 5- to 6-membered hetero ring is preferable, a benzene ring or a pyridine ring is more preferable, and a benzene ring is still more preferable.

[X ² ]
X ² is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted A 5- to 6-membered heterocyclic group having, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted group Having a carboxyl group, an unsubstituted or substituted carbamoyl group, an unsubstituted or substituted hydroxyl group, an unsubstituted or substituted group An amino group, an unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group is shown. n represents the number of X ² , and is an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0 or 1.

In X ^2, "C1~8 alkyl group", "C2~8 alkenyl group", "C2~8 alkynyl group", "C3~8 cycloalkyl group", "C4~8 cycloalkenyl group", "C6~10 “Aryl group”, “5- to 6-membered heterocyclic group”, “C1-8 acyl group”, “(1-imino) C1-8 alkyl group”, “carboxyl group having substituent”, “carbamoyl having substituent” “Group”, “hydroxyl group having substituent”, “amino group having substituent”, “mercapto group having substituent”, “sulfonyl group having substituent”, “halogeno group” are those exemplified for X ¹ The same thing is mentioned.
Among these, X ² is preferably a halogeno group or a C1~8 alkyl group.

[X]
X represents an oxygen atom, a sulfur atom, a group represented by a —C (═O) — group, or a group represented by a —CHOH— group. Among these, X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

[Compound represented by Formula (2)]
The compound (1) is preferably a compound represented by the formula (2) (hereinafter sometimes referred to as “compound (2)”).

Here, in the above formula ^{(2), Cy, X 1} , m, X 2, n, B, and X are as defined respectively in the above formula (1).

^{[A 1, A 2, A 3} , A 4 ]
A ¹ , A ² , A ³ , and A ⁴ each independently represent a carbon atom or a nitrogen atom. That is, it forms a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring. As the pyridine ring, a pyridine ring in which A ¹ is a nitrogen atom is preferable. Among these, A ¹ , A ² , A ³ , and A ⁴ preferably constitute a benzene ring or a pyridine ring.

[Compound represented by Formula (3)]
The compound (1) is preferably a compound represented by the formula (3) (hereinafter sometimes referred to as “compound (3)”).

Here, in the formula (3), Cy, X ¹ , m, X ² , B, and X have the same meaning as in the above formula (1). n1 represents the number of X ^{2 and} is an integer of 0 to 3, preferably an integer of 0 to 2.

^{[A 5,} A 6, ^{A 7]}
A ⁵ , A ⁶ , and A ⁷ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
That is, the ring containing A ⁵ , A ⁶ , and A ⁷ constitutes a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, and an isothiazole ring. In this case, the pyrazole ring is preferably a pyrazole ring in which A ⁶ and A ⁷ are nitrogen atoms. As the thiophene ring, a thiophene ring in which A ⁷ is a sulfur atom is preferable.

[Compound represented by Formula (4)]
The compound (1) is preferably a compound represented by the formula (4) (hereinafter sometimes referred to as “compound (4)”).

Here, in the above formula ^{(4), Cy, D,} X 1, m, X 2, and n have the same meanings as each of the above formulas (1).
In formula (4), as D, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable. Specifically, the compound (4) is preferably a compound having a quinoline ring.

  The salt or N-oxide compound of the nitrogen-containing heterocyclic compound according to the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt or N-oxide compound. Examples of the salt include 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; Examples include salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, and hydrazine.

[Method for producing nitrogen-containing heterocyclic compound according to the present invention]
The nitrogen-containing heterocyclic compound according to the present invention can be produced, for example, by the synthesis method shown below.

(Synthesis method 1)
The compound represented by formula (A) and the compound represented by formula (B) can be reacted by a known method to produce compound (2).
In the formula, X ¹ , m, X ² , n, A ^{1 to} A ⁴ , B, and X have the same meaning as described above. Q represents a halogeno group.
In the formula, R represents a heterocyclic group listed in the above Cy or a functional group derivable to the heterocyclic group. Examples of functional groups are formyl groups (which can be derived by condensation with isonitriles) in the case of oxazol-2-yl groups; hydroxyimino groups (with olefins) in the case of isoxazolin-3-yl groups. In the case of using Suzuki-Miyaura coupling, a halogen atom or a boron group can be used.
In the present invention, 7,8-difluoro-3-iodo-quinoline is a useful production intermediate.

(Synthesis method 2)
Compound (2) can be produced by reacting the compound represented by formula (C) with the compound represented by formula (D) by a known method.
In the formula, R, X ¹ , m, X ² , n, A ^{1 to} A ⁴ , B, X, and Q have the same meaning as described above.
In the present invention, 8-fluoro-3-hydroxyquinoline, 7,8-difluoro-3-hydroxyquinoline, 8-fluoro-3-hydroxy-2-methylquinoline, or 7,8-difluoro-3-hydroxy-2 -Methylquinoline is a useful production intermediate.

(Synthesis method 3)
Compound (3) can be produced by reacting the compound represented by formula (A) with the compound represented by formula (E) by a known method.
In the formula, R, X ¹ , m, X ² , n, A ^{5 to} A ⁷ , B, X, and Q have the same meaning as described above.

(Synthesis method 4)
Compound (3) can be produced by reacting the compound represented by formula (C) with the compound represented by formula (F) by a known method.
In the formula, R, X ¹ , m, X ² , n, A ^{5 to} A ⁷ , B, X, and Q have the same meaning as described above.

(Synthesis method 5)
Compound (4) can be produced by reacting the compound represented by formula (G) with the compound represented by formula (H) by a known method.

In the formula, X ¹ , X ² , D, m, n, Q, and R represent the same meaning as described above.

(Synthesis method 6)
Compound (4) can be produced by reacting the compound represented by formula (J) with the compound represented by formula (K) by a known method.

In the formula, R, X ¹ , X ² , D, Q, m, and n represent the same meaning as described above.

The salt of the compound according to the present invention can be prepared by bringing an inorganic acid compound, an organic acid compound, an alkali metal compound, an alkaline earth metal compound, a transition metal compound, an ammonium compound or the like into contact with the compound (1).
The N-oxide compound according to the present invention can be prepared by a known oxidation reaction. For example, it can be prepared by bringing compound (1) into contact with a peroxide such as hydrogen peroxide in a solvent or without a solvent.

  In any reaction, after completion of the reaction, the target product can be efficiently isolated by applying a conventional post-treatment operation 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 measurement of ¹ H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis, or the like.

2) Agricultural and horticultural fungicide The agricultural and horticultural fungicide according to the present invention contains at least one selected from the nitrogen-containing heterocyclic compound according to the present invention or a salt thereof or an N-oxide compound as an active ingredient. .

  The agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes Has excellent bactericidal power against bacteria.

  The agricultural and horticultural fungicide of the present invention is used in methods such as seed treatment, foliage application, soil application, and water surface application for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and grass. can do.

For example,
Sugar beet: brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris);
Peanut: brown spot (Mycosphaerella arachidis), black astringency (Mycosphaerella berkeleyi);
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);
Tomato: gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtle mold (Mycovellosiella nattrassii);

Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthora cactorum);
Onion: gray rot (Botrytis allii), gray mold (Botrytis cinerea), white leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor);
Cabbage: root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), downy mildew (Peronospora parasitica);
Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea);
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);
Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), deciduous leaf spot (Cercospora kaki);

Peach: Monilinia fructicola, black scab (Cladosporium carpophilum), homopsis sp. (Phomopsis sp.);
Sweet cherry: Monilinia fructicola;
Grapes: Gray mold (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);
Pear: Black star disease (Venturia nashicola), Red star disease (Gymnosporangium asiaticum), Black spot disease (Alternaria kikuchiana), Ring rot disease (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali);
Cha: Ringa disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis);
Citrus: scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri);
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 microbacilli (Myriosclerotinia borealis), blight (Gaeumanomyces graminis) );

Barley: leafy leaf disease (Pyrenophora graminea), cloud shape disease (Rhynchosporium secalis), naked smut (Ustilago tritici, U.nuda);
Rice: Rice Blast (Pyricularia oryzae), Rhizoctonia solani, Idiot Seedling (Gibberella fujikuroi), Sesame Leaf Blight (Cochliobolus miyabeanus), Seedling Blight (Pythium graminicolum), White Leaf Blight (Xanthomonas oryzae) Bacterial disease (Burkholderia plantarii), Brown disease (Acidovorax avenae), Bacterial disease (Burkholderia glumae);
Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum);
Tulip: Gray mold disease (Botrytis cinerea);
Bentgrass: Sclerotinia borealis, Pythium aphanidermatum;
Orchardgrass: powdery mildew (Erysiphe graminis);
Soybean: Purpura (Cercospora kikuchii), downy mildew (Peronospora Manshurica), stem rot (Phytophthora sojae);
Potato tomato: Phytophthora infestans;
It can be used for controlling such as.

  Moreover, the agricultural and horticultural fungicide of the present invention has an excellent bactericidal effect against resistant bacteria. Resistant fungi include Botrytis cinerea, Cercospora beticola, Venturia inaequalis, and Pear black rot that are resistant to benzimidazole fungicides such as thiophanate methyl, benomyl, and carbendazim. (Venturia nashicola); a gray mold fungus (Botrytis cinerea) resistant to dicarboximide fungicides (for example, vinclozoline, procymidone, iprodione) and the like.

  More preferable diseases to which the agricultural and horticultural fungicide of the present invention is applied include black rot of apple, gray mold of cucumber, powdery mildew of wheat, plague of tomato, red rust of wheat, rice blast of rice, cucumber Examples include vine split disease.

In addition, the agricultural and horticultural fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
The agricultural and horticultural fungicide of the present invention should be used in the form that can be taken as an agrochemical, that is, in the form of an agrochemical formulation such as a wettable powder, a granule, a powder, an emulsion, an aqueous solvent, a suspension, and a granular wettable powder. Can do.

  Additives and carriers used in solid formulations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, sodium benzoate, urea And organic and inorganic compounds such as mirabilite.

  Solvents used in liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. Can be mentioned.

Furthermore, in order to take a uniform and stable form in these preparations, a surfactant can be added as necessary.
The surfactant that can be added is not particularly limited. For example, 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, tristyryl added with polyoxyethylene Nonionic surfactants such as phenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfones Acid salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer.

  The wettable powder, emulsion, flowable powder, aqueous solvent, or granular wettable powder thus obtained is diluted with water to a predetermined concentration and sprayed on plants as a solution, suspension or emulsion. Can be used. In addition, powders and granules can be used by spraying them on plants as they are.

  The amount of the active ingredient in the agricultural and horticultural fungicide of the present invention is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.

  The application amount of the agricultural and horticultural 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 it is usually 1 in terms of the amount of active ingredient compound per hectare. ˜1,000 g, preferably 10 to 100 g.

  When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder, etc. are diluted with water and applied, the applied concentration is 1-1000 ppm, preferably 10-250 ppm.

The agricultural and horticultural fungicide of the present invention can be mixed with other fungicides, insecticides / acaricides, and synergists. Moreover, the agricultural and horticultural fungicide of the present invention and other fungicides, insecticides / acaricides, and synergists can be used simultaneously or in succession.
Representative examples of other fungicides, insecticides, acaricides, and plant growth regulators that can be used in this manner are shown below.

Fungicide:
(1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl, chlorphenazole;
(2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin;
(3) DMI-bactericidal system: imazalyl, oxpoconazole, pefrazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, Epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafor, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, prothioconazole, cimeconazole, tebuconazole, tetraconazole, triazimephone, Triadimenol, Triticonazole, Etaconazole, Farconazole cis; Diclobutrazol, Diniconazo Le -M, dodemorph acetate, fluconazole, imazalil-sulphate, Nafuchifen, uniconazole P, Binikonazoru, voriconazole;

(4) Phenylamide: Benalaxyl, Benalaxyl-M, Cloziracone, Furaraxyl, Metalaxyl, Metalaxyl-M, Oxadixyl, Offrase;
(5) Amine-based: aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
(6) phosphorothiolate type: EDDP, iprobenphos, pyrazophos;
(7) Dithiolane type: isopropylthiolane;
(8) Carboxamides: benodanyl, boscalid, carboxin, fenfuran, flutolanil, furamethpyr, mepronil, oxycarboxin, pentiopyrad, tifluzamide, bixaphene, isopyrazam, penflufen, floxapyroxad, sedaxane;
(9) Hydroxy- (2-amino) pyrimidine series: bupilimate, dimethylolmol, ethylmol;

(10) AP fungicide (anilinopyrimidine) type: cyprodinil, mepanipyrim, pyrimethanyl, and prim;
(11) N-phenylcarbamate system: Dietophenecarb;
(12) QoI-bactericidal (Qo inhibitor) system: azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, Famoxadone, fluoxastrobin, fenamidone, metminophen; amethoctrazine, pyramethostrobin, pyroxystrobin, pyribencarb; cumethoxystrobin, cumoxystrobin, enestrobrin, phenoxystrobin, triclopyricarb;
(13) PP fungicide (phenylpyrrole) system: fenpiconyl, fludioxonil;
(14) Quinoline series: quinoxyphene;

(15) AH fungicide (aromatic hydrocarbon) type: biphenyl, chloronebu, dichlorane, kintozen, technazen, tortofos-methyl;
(16) MBI-R system: fusaride, pyroxylone, tricyclazole;
(17) MBI-D system: carpropamide, diclocimet, phenoxanyl;
(18) SBI agent: fenhexamide, pyributicalbu, turbinafine;
(19) Phenylurea: Pencyclone;
(20) QiI-fungicide (Qi inhibitor): cyazofamid, amisulbrom, flumeciclox;
(21) Benzamide series: Zoxamide;
(22) Enopyranuron series: blastcidin, mildiomycin;
(23) Hexopyranosyl system: Kasugamycin, Kasugamycin hydrochloride;
(24) Glucopyranosyl system: streptomycin, validamycin, validamycin A;
(25) Cyanoacetamide series: Simoxanyl;
(26) Carbamate series: iodocarb, propamocarb, prothiocarb, polycarbamate;
(27) Uncoupler: Vinapacryl, dinocup, ferrimzone, fluazinam, meptyldinocup;
(28) Organotin compounds: triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide;

(29) Phosphate ester: phosphorous acid, torquelophosmethyl, fosetyl, torquetophosmethyl;
(30) Phthalamic acid type: Teclophthalam;
(31) Benzotriazine type: triazoxide;
(32) benzenesulfonamide series: fursulfamide;
(33) Pyridazinone: Dichromedin;
(34) CAA fungicide (carboxylic amide) system: dimethomorph, fulmorph, benavalicarb-isopropyl, iprovaricarb, mandipropamide, varifenalate;
(35) Tetracycline: oxytetracycline;
(36) Thiocarbamate system: metasulfocarb;
(37) Resistance inducer: acibenzoral S methyl, probenazole, thiazinyl, isothianyl;
(38) Other compounds: etridiazole, polyoxin, polyoxorim, oxolinic acid, hydroxyisoxazole, octirinone, silthiofam, diflumetrim, ethaboxam, cyflufenamide, proquinazide, metolaphenone, fluopicolide, Bordeaux solution, copper naphthalate, copper oxide, copper oxychloride, sulfuric acid Copper, Mancopper, Bis (8-quinolinolato) copper (II), Cupric hydroxide, Organic copper, Sulfur, Calcium polysulfide, Farbum, Manzeb, Mannebu, Methylam, Propineb, Thiuram, Ginebu, Zillam, Captan, Captohol , Folpet, chlorothalonil, dichlorfluanide, tolylfluanid, dodine, guazatine, iminoctadine, iminoctadine acetate, iminoctadine dodecylbenzenesulfonate Anilazine, dithianone, chloropicrin, dazomet, quinomethionate, ciprofuram, Agrobacterium, fluorimide; isophetamide, tolprocarb, fenpyrazamine, piophenone, tebufloquine, fluopyram, zaliramide; fluorophorpet, propamidine, edifenphos; Cufraneb, mancozeb, cyprosulfamide, devacarb, dichlorophen, diphenzoquat, diphenzoquat methylsulfonate, diphenylamine, flumethoverl, fluoroimide, flutianil, fosetyl aluminum, fosetyl calcium, fosetyl sodium, ilumamycin , Methyl isothiocyanate (MITC), mildeomycin, na Mycin, nitro tar isopropyl, Okisamokarubu, oxyphencyclimine Ji in, propamocarb-fosetylate, Puropamoshin sodium, Pirimorufu, Pyrrolnitrin, Torunifanido, trichlamide;

Insecticides, acaricides, nematicides, soil insecticides, anthelmintics:
(1) Organic (thio) phosphate system: acephate, azamethiphos, azinephos methyl, azinephos ethyl, bromophos ethyl, bromofenvinphos, BRP, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos ethyl, chlorfenvinphos, kazusafos, Carbophenothione, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimethone-S-methylsulfone, diariphos, diazinon , Diclofenthion, dioxabenzophos, disulfoton, ethione, etoprophos, etrimfos, EPN, phenamifos, fenitrothion, fenthion, fu Sulfothione, flupyrazophos, phonophos, formothione, phosmethylan, heptenophos, isazophos, iodofenphos, isofenphos, isoxathion, iprobenphos, malathion, mevinphos, methamidophos, methidathion, monocrotophos, mecarbam, methalyphos, nared, ometoate, paramethicone, oxydimethone methyl Parathion, parathion methyl, phentoate, hosalon, phosmet, phosphamidone, folate, phoxime, pyrimifos methyl, pyrimifos ethyl, propenofos, prothiophos, hosthiazate, phosphocarb, propaphos, propetamphos, protoate, pyridafenthione, pyraclophos, quinalphos, phosphatione, sulthione Sulfotep, Tetrachlorbi Nphos, terbufos, triazophos, trichlorfone, tebupyrimfos, temefos, thiometone, bamidithione;

(2) Carbamate series: alanic carb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, phenothiocarb, methiocarb, mesomil, oxamyl, pirimicurve, propoxyl, thiodicarb, triazamate, etiofencarb, MPC, MC , MTMC, furthiocarb, XMC, aldoxicarb, alixicarb, aminocarb, bufencarb, butacarb, butcarboxyme, butoxycarboxyme, cloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metocarb, promecarb, thiophanox, trimetacarb, xylylcarb ;

(3) Pyrethroids: alletrin, bifenthrin, cyfluthrin, beta cyfluthrin, cyhalothrin, lambda cyhalothrin, ciphenothrin, cypermethrin, alpha cypermethrin, beta cypermethrin, zeta cypermethrin, deltamethrin, esfenvalerate, eth Fenprox, fenpropatoline, fenvalerate, imiprothrin, permethrin, praretrin, pyrethrin, pyrethrin I, pyrethrin II, resmethrin, silafluophene, fulvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, promethrin , Halfenprox, flucitrinate, bioareslin, bioethanomethrin, Oh permethrin, bioresmethrin, trans permethrin, empenthrin, fenfluthrin Trinh, Fen pyridinium Trinh, full Bro shea tri sulphonate, full Fen flufenprox, flumethrin, metofluthrin, phenothrin, protrifenbute, pyresmethrin, terallethrin;

(4) Growth regulator:
(A) Chitin synthesis inhibitor: chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, nobarulone, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiazox, etoxazole, clofente Gin, fluazuron, penfluron;
(B) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, chromafenozide, azadirachtin;
(C) juvenile hormone-like substances: pyriproxyfen, metoprene, geophenolan, epofenanane, hydroprene, quinoprene, triprene;
(D) Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat, flonicamid;

(5) Nicotine receptor agonist / antagonist compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap, flupiradiflon;
(6) GABA antagonist compound:
(A) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole;
(B) Organochlorine type: camfechlor, chlordane, endosulfan, HCH, γ-HCH, heptachlor, methoxychlor;
(7) Macrocyclic lactone insecticides: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin, milbemycin, milbemycin oxime;
(8) METI I compounds: phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, hydramethylnon, fenpyroximate, pyrimidifen, dicophor;
(9) METI II and III compounds: acequinosyl, fluacrylpyrim, rotenone;
(10) Uncoupler compounds: chlorfenapyr, binapacryl, dinobutone, dinocup, DNOC;

(11) Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin;
(12) molting disrupting compound: cyromazine;
(13) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(14) Sodium channel blocker compounds: indoxacarb, metaflumizone;
(15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp., White scab fungus, black scab fungus, Pekirmyces spp., Thuringiensins, Vertici Lilium species;
(16) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
(17) Octopaminergic agent: Amitraz;
(18) Ryanodine derivative agonist: fulbenzamide, chlorantraniliprole, cyantraliniprol;
(19) Inhibitors of magnesium-stimulated ATPase: thiocyclam, thiosultap, nereistoxin;
(20) antifeedant: pymetrozine;
(21) Tick growth inhibitor: clofentezin, etoxazole;
(22) Other compounds: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Axipodene (Afidopyropen), piflubumide, furometokin, fulphip Le (flufiprole), full-ene sulfone, Meperufurusurin, tetramethyl full Surin, sulfo hexa Flore, Imishiahosu, Toraropiriru, Jifurobidajin, Jimefurusurin, methyl neo decanoic amide;
(23) Anthelmintic:
(A) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole;
(B) Salicylanilide series: closantel, oxyclozanide;
(C) substituted phenolic: nitroxinyl;
(D) pyrimidine series: pyrantel;
(E) imidazothiazole series: levamisole;
(F) tetrahydropyrimidine: praziquantel;
(G) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole;

Plant growth regulator:
Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium maleate hydrazide, 1-naphthyl Acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride;

  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 examples.

Example 1
Process for producing 8-fluoro-3- (3-fluoro-2-isoxazol-3-ylphenoxy) -quinoline [Step 1]

0.42 g of 2-fluoro-6- (8-fluoroquinolin-3-yloxy) benzaldehyde oxime was dissolved in 4 mL of N, N-dimethylformamide. The solution was heated to 50 ° C., 0.19 g of N-chlorosuccinimide was added thereto, and the mixture was reacted for 2.5 hours. Next, 0.18 g of ethynyltrimethylsilane was added to the reaction solution and cooled to 0 ° C. Next, a solution prepared by dissolving 0.18 g of triethylamine in 1.4 mL of N, N-dimethylformamide was added dropwise to the reaction solution. After completion of the addition, the solution was returned to room temperature and allowed to react for 5 hours. Thereafter, the reaction solution was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the residue was purified by silica gel column chromatography to obtain 0.47 g of 8-fluoro-3- [3-fluoro-2- (5-trimethylsilylisoxazol-3-yl) phenoxy] -quinoline.
[Step 2]

  0.30 g of 8-fluoro-3- [3-fluoro-2- (5-trimethylsilylisoxazol-3-yl) phenoxy] -quinoline was dissolved in a mixed solvent of 4.5 mL of acetonitrile and 1.5 mL of ethanol. Cesium fluoride 0.16g was added to this solution, and it stirred at room temperature for 1 hour. Then, saturated ammonium chloride aqueous solution was added to the reaction solution, and reaction was stopped. This solution was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Then, it refine | purified with silica gel column chromatography, and obtained 0.12 g of 8-fluoro-3- (3-fluoro-2-isoxazol-3-ylphenoxy) -quinoline.

Example 2
Process for producing 8-fluoro-3- (3-fluoro-2-oxazol-5-ylphenoxy) -2-methylquinoline

  2-Fluoro-6- (8-fluoro-2-methylquinolin-3-yloxy) benzaldehyde (0.32 g) and p-toluenesulfonylmethyl isocyanide (0.21 g) were dissolved in 3.2 mL of methanol. To this solution, 0.15 g of potassium carbonate was added at room temperature, and then heated to reflux with stirring for 4.5 hours. Then, the reaction solution was returned to room temperature and the solvent was distilled off. The obtained residue was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the residue was purified by silica gel column chromatography to obtain 0.27 g of 8-fluoro-3- (3-fluoro-2-oxazol-5-ylphenoxy) -2-methylquinoline.

Example 3
Process for producing 8-fluoro-3- (3-fluoro-2-furan-3-ylphenoxy) -quinoline

  8-fluoro-3- (3-fluoro-2-iodophenoxy) -quinoline 0.50 g, furan-3-boronic acid pinacol ester 0.25 g, [1,1′-bis (diphenylphosphino) ferrocene] palladium ( II) 0.11 g of dichloride and 0.55 g of potassium phosphate were dissolved in a mixed solvent of 10 mL of 1,4-dioxane and 2 mL of water. The solution was heated to reflux with stirring for 5 hours. Thereafter, the reaction solution was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the residue was purified by silica gel column chromatography to obtain 0.27 g of 8-fluoro-3- (3-fluoro-2-furan-3-ylphenoxy) -quinoline.

  Tables 1 to 4 show the nitrogen-containing heterocyclic compounds obtained in the above Examples and the nitrogen-containing heterocyclic compounds that can be synthesized by the same method as in any of the above Examples. The symbol in a table | surface is a substituent of the compound represented by Formula (5)-Formula (8). Py means pyridine. In the column of physical properties, melting point (° C.), refractive index (nD), and properties (Amr. Means amorphous and Oil means oil at normal temperature) are shown.

¹ H-NMR (CDCl ₃ , δ ppm) of the compounds shown in the above table was measured. Some of the measurement results are shown below.
Compound 1-1: 6.94 (d, 1H, J = 8.4 Hz), 7.12 (m, 1H), 7.28-7.32 (m, 2H), 7.38-7.46 (m, 4H), 7.79 (m, 1H), 8.54 (m, 1H), 8.69 (d, 1H, J = 2.8 Hz), 8.72 (s, 1H).
Compound 1-5: 6.89 (d, 1H, J = 8.4 Hz), 7.11 (m, 1H), 7.32-7.53 (m, 7H), 8.41 (d, 1H, 5.2 Hz), 8.72 (d, 1H, J = 2.8 Hz).
Compound 1-11: 1.37 (s, 6H), 3.07 (s, 2H), 6.87 (d, 1H), 7.06 (t, 1H), 7.27-7.51 (m, 5H), 8.83 (d, 1H)
Compound 1-13: 0.31 (s, 9H), 2.69 (s, 3H), 6.64 (s, 1H), 6.88 (d, 1H), 7.11 (t, 1H), 7.25-7.46 (m, 5H)
Compound 1-15: 3.95 (t, 2H), 4.28 (t, 2H), 6.88 (d, 1H), 7.05 (t, 1H), 7.29-7.53 (m, 5H), 8.87 (d, 1H).
Compound 1-17: 4.65 (dd, 1H), 4.83 (dd, 1H), 6.21 (t, 1H), 6.74 (d, 1H), 6.99 (t, 1H), 7.37-7.53 (m, 4H), 7.69 (d, 1H), 8.83 (d, 1H).
Compound 1-20: 2.73 (s, 3H), 6.61 (t, 1H), 6.86 (d, 1H), 7.12 (t, 1H), 7.25-7.49 (m, 5H), 8.45 d, 1H).
Compound 1-21: 2.38 (s, 3H), 2.70 (s, 3H), 6.18 (s, 1H), 6.82 (d, 1H), 7.07 (t, 1H), 7.22-7.44 (m, 5H)
Compound 2-1: 4.09-4.15 (m, 1H), 4.34 (t, 1H), 5.70 (t, 1H), 6.69 (d, 1H), 6.94 (t, 1H), 7.24-7.36 (m, 2H) , 7.48-7.50 (m, 2H), 7.64 (s, 1H), 8.84 (d, 1H)
Compound 2-8: 6.48 (d, 1H), 6.99-7.03 (m, 1H), 7.26-7.34 (m, 1H), 7.37-7.44 (m, 5H), 8.44 (d, 1H), 8.71 (d, 1H)
Compound 2-9: 0.28 (s, 9H), 6.49 (s, 1H), 7.04 (t, 1H), 7.26-7.28 (m, 1H), 7.39-7.47 (m, 5H), 8.69 (d, 1H)
Compound 2-11: 7.03 (d, 1H), 7.29-7.48 (m, 7H), 7.91 (s, 1H), 8.76 (d, 1H)
Compound 2-12: 6.96 (d, 1H), 7.14 (dd, 1H), 7.25-7.46 (m, 5H), 8.09 (d, 1H), 8.85 (d, 1H)
Compound 2-13: 4.02 (s, 3H), 6.89 (d, 1H), 7.10 (t, 1H), 7.32-7.38 (m, 1H), 7.47-7.54 (m, 4H), 7.74 (s, 1H) , 8.67 (d, 1H)
Compound 2-24: 2.62 (s, 3H), 6.86 (dd, 1H), 7.25-7.35 (m, 5H), 7.57-7.61 (m, 2H), 7.92 (s, 1H)
Compound 2-26: 2.01 (s, 3H), 6.93 (d, 1H), 7.12 (t, 1H), 7.28-7.33 (m, 1H), 7.45-7.52 (m, 4H), 8.24 (d, 1H) , 8.74 (d, 1H)
Compound 2-45: 2.00 (m, 1H), 2.14-2.30 (m, 2H), 2.46 (m, 1H), 3.70-3.75 (m, 2H), 6.89 (d, J = 8.4 Hz, 1H), 7.07 (m, 1H), 7.30-7.36 (m, 2H), 7.43-7.50 (m, 2H), 7.61 (m, 1H), 8.87 (d, J = 2.8 Hz, 1H)

(Formulation)
Next, some examples of the agricultural and horticultural fungicide according to the present invention are shown. However, the additive and the addition ratio are not limited to these examples, and can be changed in a wide range. Moreover, the part in a formulation Example shows a weight part.

Formulation Example 1 Wetting agent Nitrogen-containing heterocyclic 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 ingredients are uniformly mixed and finely pulverized, and the active ingredient 40 % Wettable powder is obtained.

Formulation Example 2 Emulsion Nitrogen-containing heterocyclic compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts An emulsion containing 10% active ingredient by mixing and dissolving the above. Get.

Formulation Example 3 Dust The nitrogen-containing heterocyclic 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 Granules Nitrogen-containing heterocyclic 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 was pulverized and mixed well, and water was added and kneaded well. Thereafter, granulation and drying are performed to obtain a granule containing 5% of the active ingredient.

Formulation Example 5 Suspending agent Nitrogen-containing heterocyclic 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 Wet mill until the particle size is 3 microns or less to obtain a 10% active ingredient suspension.

Formulation Example 6 Granule wettable powder Nitrogen-containing heterocyclic compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt
After mixing 5 parts or more uniformly and finely pulverizing, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.

(Biological Test Example 1) Apple scab control test The emulsion obtained in Formulation Example 2 was diluted to a concentration of 100 ppm active ingredient. The diluted solution was sprayed on apple seedlings (variety “Kunimitsu”, 3-4 leaf stage) cultivated in an unglazed pot and allowed to air dry at room temperature. Then, conidia of apple scab (Venturia inaequalis) were inoculated, and the light and darkness was repeated every 12 hours and kept in a room at 20 ° C. and high humidity for 2 weeks. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound Nos. 1-1, 1-4, 1-5, 1-6, 1-7, 1-9, 1-11, 1-12, 1-16, 1-18, 1-19, 2-1, 2-2, 2-7, 2-8, 2-10, 2-11, 2-16, 2-17, 2-20, 2-21, 2-22, 2-23, 2-24, 2- 26, 2-30, 2-35, 2-37, 2-38, 2-39, 2-41, 2-42, 2-44, 2-45, and 3-1, the apple scab control test As a result, all the compounds showed a control value of 75% or more.

(Biological Test Example 2) Cucumber Gray Mold Control Test The emulsion obtained in Formulation Example 2 was diluted to a concentration of 100 ppm active ingredient. The diluted solution was sprayed on cucumber seedlings grown in an unglazed pot (variety “Sagamihanjiro”, cotyledon stage) and air-dried at room temperature. Thereafter, a conidial spore suspension of 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 obtained.
Compound Nos. 1-9, 1-10, 1-14, 1-20, 1-22, 1-22, 2-2, 2-8, 2-10, 2-11, 2-21, 2-22, 2-23, 2-24, 2-26, 2-29, 2-30, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-41, 2- As a result of conducting a cucumber gray mold control test on the compounds 42, 2-44, and 3-1, all compounds showed a control value of 75% or more.

  From these results, it can be seen that the nitrogen-containing heterocyclic compound of the present invention exhibits bactericidal performance and is useful as an active ingredient of agricultural and horticultural fungicides.

Claims (5)

Formula (1):

In formula (1),
Cy is an unsubstituted or substituted 5-membered heteroaryl group, an unsubstituted or substituted 6-membered heteroaryl group, an unsubstituted or substituted partially unsaturated 5-membered heterocyclic group, Represents a substituted or substituted partially unsaturated 6-membered heterocyclic group;
B represents a carbon atom;
D represents a benzene ring;
X ¹ is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C3-8 cycloalkyl group, Unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 5-6 membered heterocyclic group, unsubstituted or substituted A C1-8 acyl group having a group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, Unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group, unsubstituted or substituted mercapto group, A substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group;
m represents the number of X ¹ and is an integer of 0 to 6;
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring;
X ² is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C3-8 cycloalkyl group, Unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 5-6 membered heterocyclic group, unsubstituted or substituted A C1-8 acyl group having a group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, Unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group, unsubstituted or substituted mercapto group, A substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group;
n represents the number of X ² and is an integer of 0 to 4;
X represents an oxygen atom,
Or a salt or N-oxide compound thereof. Formula (1) is converted to Formula (2):

In formula (2),
Cy, X ¹ , m, X ² , n, B, and X have the same meaning as in formula (1);
A ¹ , A ² , A ³ , and A ⁴ each independently represent a carbon atom or a nitrogen atom,
The nitrogen-containing heterocyclic compound according to claim 1, or a salt thereof, or an N-oxide compound. Formula (1) is converted to Formula (3):

In formula (3),
Cy, X ¹ , m, X ² , B and X have the same meaning as in formula (1);
n1 represents the number of X ² and is an integer of 0 to 3;
A ⁵ , A ⁶ , and A ⁷ each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom; however, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are adjacent to each other. Never
The nitrogen-containing heterocyclic compound according to claim 1, or a salt thereof, or an N-oxide compound. Formula (1) is converted to Formula (4):

In formula (4), Cy, X ¹ , m, X ² , n and D have the same meaning as in formula (1),
The nitrogen-containing heterocyclic compound of Claim 1 represented by these, its salt, or N-oxide compound.   An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the nitrogen-containing heterocyclic compound according to any one of claims 1 to 4, a salt thereof, or an N-oxide compound.