JP2014221747A - Nitrogen-containing heterocyclic compound and bactericide for agricultural and horticultural use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a bactericide for agricultural and horticultural use which has reliable effects and can be safely used.SOLUTION: A bactericide for agricultural and horticultural use comprises a nitrogen-containing heterocycle compound represented by formula (I) or salt thereof as an active ingredient.

Description

  The present invention relates to a novel nitrogen-containing heterocyclic compound and an agricultural and horticultural fungicide containing as an active ingredient at least one selected from the nitrogen-containing heterocyclic compounds.

  In the cultivation of agricultural and horticultural crops, many control agents are used against crop diseases. Many of these control agents have insufficient control effects, are restricted in their use due to the emergence of drug-resistant pathogens, cause phytotoxicity and contamination of plants, and are toxic to humans and the environment. It is not fully satisfactory because of the influence of. Therefore, there is a strong demand for the emergence of drugs that can be safely used with few such drawbacks.

  In relation to the present invention, Patent Documents 1 to 3 disclose quinoline derivatives having a chemical structure similar to that of the compound of the present invention, and agricultural and horticultural fungicides containing the same as active ingredients.

WO2005 / 0700917 WO2007 / 011022 WO2011 / 081174

  An object of the present invention is to provide a novel nitrogen-containing heterocyclic compound and a salt thereof, and an agricultural and horticultural use that can be used safely and reliably with an effect of containing at least one selected from the nitrogen-containing heterocyclic compound and a salt thereof as an active ingredient It is to provide a disinfectant.

  As a result of intensive studies to solve the above problems, the present inventors have obtained a novel nitrogen-containing heterocyclic compound and a salt thereof. And it discovered that this nitrogen-containing heterocyclic compound and its salt were useful as an active ingredient of the agricultural and horticultural fungicide which has an effect and can be used safely. The present invention has been further studied and completed based on these findings.

That is, the present invention includes the following aspects.
[1] A nitrogen-containing heterocyclic compound represented by the formula (I) or a salt thereof.

（式（I）中、Ｘ¹は、それぞれ独立して、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Ｃ２〜８アルケニル基、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１〜８アシル基、無置換の若しくは置換基を有する（１−イミノ）Ｃ１〜８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
ｍは、Ｘ¹の個数を示し且つ０〜６のいずれかの整数である。
Ｆは、５〜７員炭化水素環または５〜７員ヘテロ環を示す。
Ｂは、それぞれ独立に、炭素原子または窒素原子を示す。
Ｘ²は、それぞれ独立して、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Ｃ２〜８アルケニル基、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有するＣ１〜８アシル基、無置換の若しくは置換基を有する（１−イミノ）Ｃ１〜８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。
ｎは、Ｘ²の個数を示し且つ０〜４のいずれかの整数である。
Ｅは、５〜７員炭化水素環または５〜７員ヘテロ環を示す。
Ｂ’は、それぞれ独立に、炭素原子または窒素原子を示す。
破線と実線を並べた結合は、単結合または二重結合を示す。
Ａは、多価の有機基を示す。
Ｄは、sp2炭素原子、無置換の若しくは置換基を有するsp3炭素原子、またはsp3窒素原子を示す。）

(In formula (I), each X ¹ is independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group. A C2-8 alkynyl group having an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocyclic group, A substituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted group; Carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group, unsubstituted or substituted mercapto group A sulfonyl group having a substituent group, halogeno group, a cyano group or a nitro group.
m represents the number of X ¹ and is an integer of 0-6.
F represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocycle.
B independently represents a carbon atom or a nitrogen atom.
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 An unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocyclic group, an unsubstituted or substituted group C1-8 acyl group, unsubstituted or substituted (1-imino) C1-8 alkyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, unsubstituted Or a substituted hydroxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted mercapto group, and a substituted group. That a 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.
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
B ′ each independently represents a carbon atom or a nitrogen atom.
A bond in which a broken line and a solid line are arranged indicates a single bond or a double bond.
A represents a polyvalent organic group.
D represents an sp2 carbon atom, an unsubstituted or substituted sp3 carbon atom, or an sp3 nitrogen atom. )

[2] The nitrogen-containing heterocyclic compound or a salt thereof according to [1], wherein the formula (I) is the formula (II).

（式（II）中、Ｘ¹、ｍ、Ｆ、Ｂ、Ｘ²、ｎ、Ａ、およびＤは、式（I）中のそれぞれと同じ意味を示す。
Ｅ¹、Ｅ²、Ｅ³、およびＥ⁴は、それぞれ独立に、炭素原子または窒素原子を示す。ただし、Ｅ¹〜Ｅ⁴は２以上が窒素原子とはならない。）

(In the formula (II), X ¹ , m, F, B, X ² , n, A, and D have the same meaning as in the formula (I).
E ¹ , E ² , E ³ , and E ⁴ each independently represent a carbon atom or a nitrogen atom. However, two or more of E ^{1 to} E ⁴ are not nitrogen atoms. )

[3] The nitrogen-containing heterocyclic compound or a salt thereof according to [2], wherein formula (II) is formula (III).

（式（III）中、Ｘ¹、ｍ、Ｆ、Ｂ、Ｘ²、ｎ、Ｅ¹、Ｅ²、Ｅ³、およびＥ⁴は、式（II）中のそれぞれと同じ意味を示す。
Ｄ¹は、sp2炭素原子（＞Ｃ＝）、無置換の若しくは置換基を有するsp3炭素原子（＞ＣＲ¹−）、またはsp3窒素原子（＞Ｎ−）を示す。
Ａ¹およびＡ²は、それぞれ独立して、無置換の若しくは置換基を有するsp3炭素原子（ＣＲ¹Ｒ²−）、無置換の若しくは置換基を有するsp2炭素原子（−ＣＲ¹＝）、無置換の若しくは置換基を有するsp3窒素原子（−ＮＲ¹−）、sp2窒素原子（−Ｎ＝）、酸素原子（−Ｏ−）、または硫黄原子（−Ｓ−）を示す。
Ｒ¹は、それぞれ独立して、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有する水酸基、ハロゲノ基、またはシアノ基を示す。
Ｒ²は、それぞれ独立して、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有する水酸基、ハロゲノ基、またはシアノ基を示す。Ｒ¹とＲ²は、一緒になってオキソ基を形成してもよい。）

(In the formula (III), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ have the same meanings as in the formula (II).
D ¹ represents an sp2 carbon atom (> C =), an unsubstituted or substituted sp3 carbon atom (> CR ^1- ), or an sp3 nitrogen atom (> N-).
A ¹ and A ² are each independently an unsubstituted or substituted sp3 carbon atom (CR ¹ R ^2- ), an unsubstituted or substituted sp2 carbon atom (-CR ¹ =), A substituted or substituted sp3 nitrogen atom (—NR ¹ —), sp2 nitrogen atom (—N═), oxygen atom (—O—), or sulfur atom (—S—) is shown.
Each R ¹ independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocyclic ring; A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group;
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group. )

[4] The nitrogen-containing heterocyclic compound or a salt thereof according to [3], wherein formula (III) is formula (III-1).

（式（III-1）中、Ｘ¹、ｍ、Ｂ、Ｘ²、ｎ、Ｅ¹、Ｅ²、Ｅ³、Ｅ⁴、Ｄ¹、Ａ¹およびＡ²は、式（III）中のそれぞれと同じ意味を示す。）

(In the formula (III-1), X ¹ , m, B, X ² , n, E ¹ , E ² , E ³ , E ⁴ , D ¹ , A ¹ and A ² are each in the formula (III). Indicates the same meaning.)

が、 >Ｃ＝Ｎ−ＣＲ¹Ｒ²-、 >Ｃ＝Ｎ−Ｏ-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、 >Ｎ−ＣＲ¹＝ＣＲ¹-、 >Ｃ＝ＣＲ¹−Ｓ-、 >Ｃ＝ＣＲ¹−Ｏ-、または >ＣＲ¹−Ｏ−ＣＲ¹Ｒ²-で表わされる基（Ｒ¹およびＲ²は、式（III）中のそれぞれと同じ意味を示す。）である、〔３〕または〔４〕に記載の含窒素ヘテロ環化合物またはその塩。 [5] Consists of D ¹ , A ¹ and A ²

> C = N-CR ¹ R ² -,> C = N-O-,> N-CR ¹ R ² -CR ¹ R ² -,> N-CR ¹ = CR ¹ -,> C = CR ¹ —S—,> C═CR ¹ —O—, or a group represented by> CR ¹ —O—CR ¹ R ² — (R ¹ and R ² have the same meaning as in formula (III). The nitrogen-containing heterocyclic compound or a salt thereof according to [3] or [4].

[6] The nitrogen-containing heterocyclic compound or a salt thereof according to [2], wherein formula (II) is formula (IV).

（式（IV）中、Ｘ¹、ｍ、Ｆ、Ｂ、Ｘ²、ｎ、Ｅ¹、Ｅ²、Ｅ³、およびＥ⁴は、式（II）中のそれぞれと同じ意味を示す。
Ｄ¹は、sp2炭素原子（＞Ｃ＝）、無置換の若しくは置換基を有するsp3炭素原子（＞ＣＲ¹−）、またはsp3窒素原子（＞Ｎ−）を示す。
Ａ³、Ａ⁴、およびＡ⁵は、それぞれ独立して、無置換の若しくは置換基を有するsp3炭素原子（−ＣＲ¹Ｒ²−）、無置換の若しくは置換基を有するsp2炭素原子（−ＣＲ¹＝）、無置換の若しくは置換基を有するsp3窒素原子（−ＮＲ¹−）、sp2窒素原子（−Ｎ＝）、酸素原子（−Ｏ−）、または硫黄原子（−Ｓ−）を示す。
Ｒ¹は、それぞれ独立して、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有する水酸基、ハロゲノ基、またはシアノ基を示す。
Ｒ²は、それぞれ独立して、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有する水酸基、ハロゲノ基、またはシアノ基を示す。Ｒ¹とＲ²は、一緒になってオキソ基を形成してもよい。）

(In the formula (IV), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ have the same meanings as in the formula (II).
D ¹ represents an sp2 carbon atom (> C =), an unsubstituted or substituted sp3 carbon atom (> CR ^1- ), or an sp3 nitrogen atom (> N-).
A ³ , A ⁴ , and A ⁵ are each independently an unsubstituted or substituted sp3 carbon atom (—CR ¹ R ² —), an unsubstituted or substituted sp2 carbon atom (—CR ¹ =), an unsubstituted or substituted sp3 nitrogen atom (—NR ¹ —), sp2 nitrogen atom (—N═), oxygen atom (—O—), or sulfur atom (—S—).
Each R ¹ independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocyclic ring; A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group;
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group. )

[7] The nitrogen-containing heterocyclic compound or a salt thereof according to [6], wherein formula (IV) is formula (IV-1).

（式（IV-1）中、Ｘ¹、ｍ、Ｂ、Ｘ²、ｎ、Ｅ¹、Ｅ²、Ｅ³、Ｅ⁴、Ｄ¹、Ａ³、Ａ⁴、およびＡ⁵は、式（IV）中のそれぞれと同じ意味を示す。）

(In the formula (IV-1), X ¹ , m, B, X ² , n, E ¹ , E ² , E ³ , E ⁴ , D ¹ , A ³ , A ⁴ , and A ⁵ are represented by the formula (IV ) Shows the same meaning as each inside.)

が、 >Ｃ＝Ｎ−Ｏ−ＣＲ¹Ｒ²-、 >Ｃ＝Ｎ−Ｎ＝ＣＲ¹-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｓ-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、 >ＣＲ¹−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、 >Ｃ＝ＣＲ¹−ＣＲ¹＝ＣＲ¹-、 >Ｃ＝ＣＲ¹−ＣＲ¹Ｒ²−Ｏ-、または>Ｃ＝ＣＲ¹−ＣＲ¹＝Ｎ-で表わされる基（Ｒ¹およびＲ²は、式（IV）中のそれぞれと同じ意味を示す。）である、〔６〕または〔７〕に記載の含窒素ヘテロ環化合物またはその塩。 [8] Consists of D ¹ , A ³ , A ⁴ , and A ⁵

> C = N-O-CR ¹ R ² -,> C = N-N = CR ¹ -,> N-CR ¹ R ² -CR ¹ R ² -S-,> N-CR ¹ R ^{2- CR 1 R 2 -O-,> N} -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> CR 1 -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> C = ^{CR 1 -CR 1 = CR 1 -} ,> C = CR 1 -CR 1 R 2 -O-, ^{or> C = CR 1 -CR 1 =} N- group represented by (R ¹ and R ² has the formula ( The nitrogen-containing heterocyclic compound or a salt thereof according to [6] or [7], which has the same meaning as in IV).

[9] The nitrogen-containing heterocyclic compound or a salt thereof according to [2], wherein formula (II) is formula (V).

（式（V）中、Ｘ¹、ｍ、Ｆ、Ｂ、Ｘ²、ｎ、Ｅ¹、Ｅ²、Ｅ³、およびＥ⁴は、式（II）中のそれぞれと同じ意味を示す。
Ｄ¹は、sp2炭素原子（＞Ｃ＝）、無置換の若しくは置換基を有するsp3炭素原子（＞ＣＲ¹−）、またはsp3窒素原子（＞Ｎ−）を示す。
Ａ⁶、Ａ⁷、Ａ⁸、およびＡ⁹は、それぞれ独立して、無置換の若しくは置換基を有するsp3炭素原子（−ＣＲ¹Ｒ²−）、無置換の若しくは置換基を有するsp2炭素原子（−ＣＲ¹＝）、無置換の若しくは置換基を有するsp3窒素原子（−ＮＲ¹−）、sp2窒素原子（−Ｎ＝）、酸素原子（−Ｏ−）、または硫黄原子（−Ｓ−）を示す。
Ｒ¹は、それぞれ独立して、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有する水酸基、ハロゲノ基、またはシアノ基を示す。
Ｒ²は、それぞれ独立して、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Ｃ６〜１０アリール基、無置換の若しくは置換基を有するヘテロ環基、無置換の若しくは置換基を有する水酸基、ハロゲノ基、またはシアノ基を示す。Ｒ¹とＲ²は、一緒になってオキソ基を形成してもよい。）

(In the formula (V), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ have the same meanings as in the formula (II).
D ¹ represents an sp2 carbon atom (> C =), an unsubstituted or substituted sp3 carbon atom (> CR ^1- ), or an sp3 nitrogen atom (> N-).
A ⁶ , A ⁷ , A ⁸ , and A ⁹ are each independently an unsubstituted or substituted sp3 carbon atom (—CR ¹ R ² —), an unsubstituted or substituted sp2 carbon atom. (—CR ¹ ═), unsubstituted or substituted sp 3 nitrogen atom (—NR ¹ —), sp 2 nitrogen atom (—N═), oxygen atom (—O—), or sulfur atom (—S—) Indicates.
Each R ¹ independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocyclic ring; A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group;
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group. )

[10] The nitrogen-containing heterocyclic compound or a salt thereof according to [9], wherein formula (V) is formula (V-1).

（式（V-1）中、Ｘ¹、ｍ、Ｂ、Ｘ²、ｎ、Ｅ¹、Ｅ²、Ｅ³、Ｅ⁴、Ｄ¹、Ａ⁶、Ａ⁷、Ａ⁸およびＡ⁹は、式（V）中のそれぞれと同じ意味を示す。）

(In the formula (V-1), X ¹ , m, B, X ² , n, E ¹ , E ² , E ³ , E ⁴ , D ¹ , A ⁶ , A ⁷ , A ⁸ and A ⁹ are (Indicates the same meaning as in (V).)

が、 >Ｃ＝Ｎ−Ｏ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｓ-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ-、 >Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ−ＣＲ¹Ｒ²-、 >ＣＲ¹−Ｏ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、または >ＣＲ¹−Ｏ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ-
で表わされる基（Ｒ¹およびＲ²は、式（V）中のそれぞれと同じ意味を示す。）である、〔９〕または〔１０〕に記載の含窒素ヘテロ環化合物またはその塩。 [11] Consists of D ¹ , A ⁶ , A ⁷ , A ⁸ and A ⁹

But,> C = N-O- CR 1 R 2 -CR 1 R 2 -,> N-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> N-CR 1 R ^{2 -CR 1 R 2 -CR 1 R} 2 -S-,> N-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -O-,> N-CR 1 R 2 -CR 1 R 2 -O ^{-CR 1 R 2 -,> CR} 1 -O-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -, ^{or> CR 1 -O-CR 1 R} 2 -CR 1 R 2 -O-
The nitrogen-containing heterocyclic compound or a salt thereof according to [9] or [10], wherein R ¹ and R ² have the same meanings as in formula (V).

[12] An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the nitrogen-containing heterocyclic compound or a salt thereof according to any one of [1] to [11].

The nitrogen-containing heterocyclic compounds and salts thereof of the present invention are novel compounds useful as active ingredients of agricultural and horticultural fungicides that have reliable effects and can be used safely.
The agricultural and horticultural fungicide of the present invention is an agent that has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human and livestock fish and environmental impact.

[Formula (I)]
The nitrogen-containing heterocyclic compound according to the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as “compound (I)”).

First, the meanings of “unsubstituted” and “having a substituent” in formula (I) and the like will be described. In this specification, the term “unsubstituted” means only a group serving as a 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 from 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 group, pyridinyl group, triazinyl group; saturated heterocyclic groups such as aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethyl Examples thereof include tri-C1-6 alkylsilyl groups such as silyl group and t-butyldimethylsilyl group; triphenylsilyl group.

  Further, these “substituents” may have another “substituent”.

[X ¹ ]
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 C2-8 alkynyl group An unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocyclic group, an unsubstituted or substituted group C1-8 acyl group, unsubstituted or substituted (1-imino) C1-8 alkyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, unsubstituted Or a substituted hydroxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted mercapto group, and a substituted group. That a sulfonyl group, a halogeno group, a cyano group or a nitro group.
m represents the number of X ¹ and is an integer of 0-6.

  A “C1-8 alkyl group” 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.

As the “C1-8 alkyl group having a substituent”,
A cycloalkylalkyl group such as a cyclopropylmethyl group, a 2-cyclopropylethyl group, a cyclopentylmethyl group, or a 2-cyclohexylethyl group, preferably a C3-6 cycloalkyl C1-6 alkyl group;
A cycloalkenylalkyl group such as a cyclopentenylmethyl group, a 3-cyclopentenylmethyl group, a 3-cyclohexenylmethyl group, a 2- (3-cyclohexenyl) ethyl group, preferably a C4-6 cycloalkenylC1-6 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-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, 2,2,4,4,6,6-hexachlorooctyl group, etc. A haloalkyl 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, 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 groups;
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 2-hydroxy-1,1-dimethylpropyl group, 2-hydroxy-2-methylpropyl group, preferably a 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 groups;
Acyloxyalkyl groups such as formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group, preferably C1-7 acyloxy C1-6 alkyl group;
A trialkylsilyloxyalkyl group such as a trimethylsilyloxymethyl group or t-butyldimethylsilyloxymethyl group, preferably a triC1-6 alkylsilyloxy C1-6 alkyl group;
Arylsulfonyloxyalkyl groups such as tosyloxymethyl group, 2-tosyloxy-1,1-dimethylethyl group, preferably C1-6 alkyl substituted C6-10 arylsulfonyloxy C1-6 alkyl groups;
A cyanoalkyl group such as a cyanomethyl group, a 2-cyanoethyl group, a 1-cyano-1-methylethyl group, preferably a 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- Acylalkyl groups such as acetylpropyl group, 1-acetyl-1-methylethyl group, 2-acetyl-1,1-dimethylethyl group, preferably C1-6 acylC1-6 alkyl groups;
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;
Acylalkyl groups such as 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 groups 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;
Alkoxycarbonylalkyl groups such as methoxycarbonylmethyl group, 2-methoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 1-methoxycarbonyl-1-methylethyl group, 2-methoxycarbonyl-1,1-dimethylethyl group, preferably Is a C1-6 alkoxycarbonyl C1-6 alkyl group;
An azidoalkyl group such as an azidomethyl group, 2-azidoethyl group, 1-azido-1-methylethyl group, preferably an azido C1-6 alkyl group; and the like.

  A “C 2-8 alkenyl group” 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. Examples of the C2-8 alkenyl group include vinyl group, 1-propenyl group, isopronpenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group and 3-pentenyl group. 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-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 group 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, preferably a hydroxy C2-6 alkenyl group; It is done.

  A “C 2-8 alkynyl group” 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.

  A “C 3-8 cycloalkyl 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, 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 “C6-10 aryl 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” 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.

The “heterocyclic group” includes 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. The heterocyclic group may be monocyclic or polycyclic.
Examples of the heterocyclic group include a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a saturated heterocyclic group, and a partially unsaturated heterocyclic 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 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.

  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; It is done.

  Other heterocyclic groups include 3-membered saturated heterocyclic rings 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 heterocyclic ring 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 6-membered saturated heterocycle such as 1,3-benzodioxol-4-yl group, 1,3-benzodioxol-5-yl group, 1,4-benzodioxan-5-yl 1,4-benzodioxan-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-6-yl group, 3,4-dihydro-2H-1,5-benzodioxe Pin-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 heterocyclic group” include 4-chloro-2-pyridinyl group, 3-chloro-2-pyrazinyl group, 4-methyl-2-pyridinyl group, 5-trifluoromethyl-2-pyrimidinyl group, Examples include 3-methyl-2-quinolyl group.

“C1-8 acyl group” means 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- to 7-membered heterocyclic group bonded to a carbonyl group. It is a group.
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” is an iminomethyl group (HC (═NH) — group) or a group in which an alkyl group (R) of C1-7 is bonded to an iminomethyl group (RC (═NH) — 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 “substituted (1-imino) C1-8 alkyl group” include a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, a (1-hydroxyimino) propyl group, and a (1-hydroxyimino) butyl group. (1-hydroxyimino) alkyl group such as, preferably (1-hydroxyimino) C1-6 alkyl group; methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-methoxyimino) ethyl group, (1 -T-butoxyimino) ethyl group, (1-alkoxyimino) alkyl group such as (1-ethoxyimino) ethyl group, preferably (1- (C1-6 alkoxy) imino) C1-6 alkyl group; It is done.

  The “carboxyl group having a substituent” is a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C6-10 aryl group, a C6-10 aryl C1-6 alkyl group, or a 5-6 membered hetero group. A cyclic group is a group bonded to a carbonyl group.

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 alkenyloxycarbonyl group;
An alkynyloxycarbonyl group such as an ethynyloxycarbonyl group or a propargyloxycarbonyl group, preferably a C2-6 alkynyloxycarbonyl group;
Aryloxycarbonyl groups such as phenoxycarbonyl group and naphthoxycarbonyl group, preferably C6-10 aryloxycarbonyl group;
An aralkyloxycarbonyl group such as a benzyloxycarbonyl group, preferably a C6-10 aryl C1-6 alkoxycarbonyl group;

  “Substituted carbamoyl group” is a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C6-10 aryl group, a C6-10 aryl C1-6 alkyl group, or a 5-6 membered hetero group. A cyclic group is a group bonded to a carbamoyl group.

  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.

  Examples of the “substituted hydroxyl group” include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, decyloxy group, dodecyloxy group, lauryloxy 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-dimethylbutoxy group, 2 , 3-dimethylbutoxy group, 1-ethylbutoxy group, alkoxy group such as 2-ethylbutoxy group, preferably C1-6 alkoxy 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; An aryloxy group such as a tetralinyloxy group, preferably a C6-10 aryloxy group;
Arylalkyloxy groups (aralkyloxy groups) such as benzyloxy group, phenethyloxy group, 2-naphthylmethyloxy group, preferably C6-10 arylC1-6 alkyloxy groups;
Acyloxy groups such as acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, pentanoyloxy group, pivaloyloxy group, preferably A C1-7 acyloxy group;
Alkoxycarbonylalkyloxy groups such as methoxycarbonylmethyloxy group and 1-methoxycarbonyl-1-methylethyloxy group, preferably C1-6 alkoxycarbonyl C1-6 alkoxy groups;
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; .

  The “mercapto group having a substituent” is an alkylthio group such as a methylthio group or an ethylthio group, preferably a C1-6 alkylthio group; an arylthio group such as a phenylthio group or a 4-methylphenylthio group, preferably a C6-10 arylthio group. An acylthio group such as an acetylthio group or a benzoylthio group, preferably a C1-6 acylthio group;

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

  Examples of the “halogeno group” include a fluoro group, a chloro group, a bromo group, and an iodo group.

[F, B]
F represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocycle.
Examples of the 5- to 7-membered hydrocarbon ring in F include aromatic hydrocarbon rings such as a benzene ring; C5-7 cycloalkene rings such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; 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, a pyridazine ring, and an azepine ring. Aromatic 5- to 7-membered heterocycles such as diazepine ring; unsaturated 5- to 7-membered heterocycles such as dihydro-2H-pyran ring, dihydro-2H-thiopyran ring and tetrahydropyridine ring; Of these, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable.

  B independently represents a carbon atom or a nitrogen atom. That is, G in the formula represents a pyridine ring, a pyrazine ring, or a pyridazine ring. Here, the fused heterocycle composed of F and G is preferably a quinoline ring.

[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 An unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocyclic group, an unsubstituted or substituted group C1-8 acyl group, unsubstituted or substituted (1-imino) C1-8 alkyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, unsubstituted Or a substituted hydroxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted mercapto group, and a substituted group. That a 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.
Examples of these groups represented by X ² include the same groups as those exemplified as the group represented by X ¹ .

[E, B ']
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
B ′ each independently represents a carbon atom or a nitrogen atom.
A bond in which a broken line and a solid line are arranged indicates a single bond or a double bond.
Examples of the 5- to 7-membered hydrocarbon ring and the 5- to 7-membered hetero ring include the same as those exemplified for F above. E is preferably a benzene ring.

[A, D]
A represents a polyvalent organic group. Examples of the polyvalent organic group include an unsubstituted or substituted sp3 carbon atom (may be represented by the following formula (-CR ¹ R ^2- )), an unsubstituted or substituted sp2 carbon atom ( It may be represented by the following formula (-CR ¹ =)), an unsubstituted or substituted sp3 nitrogen atom (may be represented by the following formula (-NR ^1- )), sp2 nitrogen atom (following formula (-N =)), an oxygen atom (may be represented by the following formula (-O-)), and a sulfur atom (may be represented by the following formula (-S-)). And those containing 2 to 4 atoms as constituents.
In the above formula, each R ¹ is independently a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C6-10 aryl group, or unsubstituted. Or a substituted heterocyclic group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group.
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group.
Examples of these groups represented by R ¹ and R ² include the same groups as those exemplified as the group represented by X ¹ .

D is an sp2 carbon atom (may be represented by the following formula (> C =)), an unsubstituted or substituted sp3 carbon atom (may be represented by the following formula (> CR ^1- )), Or an sp3 nitrogen atom (may be represented by the following formula (> N-)).
Examples of these groups represented by R ¹ include the same groups as those exemplified above for the polyvalent organic group “A”.

[Formula (II)]
The nitrogen-containing heterocyclic compound according to the present invention is preferably a compound represented by the formula (II) (hereinafter sometimes referred to as “compound (II)”).
In formula (II), X ¹ , m, F, B, X ² , n, A, and D have the same meaning as in formula (I).
^{[E 1, E 2, E 3} , E 4 ]
E ¹ , E ² , E ³ , and E ⁴ each independently represent a carbon atom or a nitrogen atom. However, two or more of E ^{1 to} E ⁴ are not nitrogen atoms. That is, E ′ in the formula represents a benzene ring or a pyridine ring, and preferably a benzene ring.

[Formula (III)]
The nitrogen-containing heterocyclic compound according to the present invention is preferably a compound represented by the formula (III) (hereinafter sometimes referred to as “compound (III)”), more preferably the formula (III-1). ) (Hereinafter sometimes referred to as “compound (III-1)”).
It is.
In formula (III) or formula (III-1), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ are each in the above formula (II). Indicates the same meaning.

[D ^1, A ^1, A ^2]
In formula (III) or formula (III-1), D ¹ is an sp2 carbon atom (may be represented by the following formula (> C =)), an unsubstituted or substituted sp3 carbon atom (following formula (> CR ^1- )), or an sp3 nitrogen atom (may be represented by the following formula (> N-)).
In Formula (III) or Formula (III-1), A ¹ and A ² are each independently an unsubstituted or substituted sp3 carbon atom (may be represented by the following formula: (—CR ¹ R) ^2- )), an unsubstituted or substituted sp2 carbon atom (may be represented by the following formula (-CR ¹ =)), an unsubstituted or substituted sp3 nitrogen atom (expressed by the following formula ^{is. (- NR 1 -))} , sp2 nitrogen atom (which may be represented by the following formula (-. N =)), (may be represented by the following formula (. - O-) oxygen atoms), or sulfur An atom (may be represented by the following formula (-S-)) is shown.

は、>Ｃ＝Ｎ−ＣＲ¹Ｒ²-、>Ｃ＝Ｎ−Ｏ-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、>Ｎ−ＣＲ¹＝ＣＲ¹-、>Ｃ＝ＣＲ¹−Ｓ-、>Ｃ＝ＣＲ¹−Ｏ-、または>ＣＲ¹−Ｏ−ＣＲ¹Ｒ²-で表わされる基であることが好ましい。
Ｒ¹およびＲ²が示すこれらの基としては、上記の多価の有機基「Ａ」において例示したものと同じものが挙げられる。 Consists of D ¹ , A ¹ and A ²

> C = N-CR ¹ R ² -,> C = N-O-,> N-CR ¹ R ² -CR ¹ R ² -,> N-CR ¹ = CR ¹ -,> C = CR ¹ A group represented by —S—,> C═CR ¹ —O—, or> CR ¹ —O—CR ¹ R ² — is preferable.
Examples of these groups represented by R ¹ and R ² include the same groups as those exemplified above for the polyvalent organic group “A”.

[Formula (IV)]
The nitrogen-containing heterocyclic compound according to the present invention is preferably a compound represented by formula (IV) (hereinafter sometimes referred to as “compound (IV)”), more preferably formula (IV-1). ) (Hereinafter sometimes referred to as “compound (IV-1)”).
In formula (IV) or formula (IV-1), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ are each in the above formula (II). Indicates the same meaning.

^{[D 1, A 3, A 4} , A 5 ]
In formula (IV) or formula (IV-1), D ¹ is an sp2 carbon atom (may be represented by the following formula (> C =)), an unsubstituted or substituted sp3 carbon atom (following formula (> CR ^1- )), or an sp3 nitrogen atom (may be represented by the following formula (> N-)).
In formula (IV) or formula (IV-1), A ³ , A ⁴ , and A ⁵ are each independently an unsubstituted or substituted sp3 carbon atom (may be represented by the following formula: -CR ¹ R ^2- )), an unsubstituted or substituted sp2 carbon atom (may be represented by the following formula (-CR ¹ =)), an unsubstituted or substituted sp3 nitrogen atom (following (-NR ^1- )), sp2 nitrogen atom (may be represented by the following formula (-N =)), oxygen atom (may be represented by the following formula (-O-)). ) Or a sulfur atom (may be represented by the following formula (-S-)).
Examples of these groups represented by R ¹ and R ² include the same groups as those exemplified above for the polyvalent organic group “A”.

は、>Ｃ＝Ｎ−Ｏ−ＣＲ¹Ｒ²-、>Ｃ＝Ｎ−Ｎ＝ＣＲ¹-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｓ-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、>ＣＲ¹−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、>Ｃ＝ＣＲ¹−ＣＲ¹＝ＣＲ¹-、>Ｃ＝ＣＲ¹−ＣＲ¹Ｒ²−Ｏ-、または>Ｃ＝ＣＲ¹−ＣＲ¹＝Ｎ-で表わされる基であることが好ましい。
Ｒ¹およびＲ²が示すこれらの基としては、上記の多価の有機基「Ａ」において例示したものと同じものが挙げられる。 Consists of D ¹ , A ³ , A ⁴ , and A ⁵

> C = N-O-CR ¹ R ² -,> C = N-N = CR ¹ -,> N-CR ¹ R ² -CR ¹ R ² -S-,> N-CR ¹ R ^{2- CR 1 R 2 -O -,>} N-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> CR 1 -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> C = ^{CR 1 -CR 1 = CR 1 -} , is preferably ^{a> C = CR 1 -CR 1 R} 2 -O-, or> C = CR ¹ -CR ¹ = group represented by N-.
Examples of these groups represented by R ¹ and R ² include the same groups as those exemplified above for the polyvalent organic group “A”.

[Formula (V)]
The nitrogen-containing heterocyclic compound according to the present invention is preferably a compound represented by formula (V) (hereinafter sometimes referred to as “compound (V)”), more preferably formula (V-1). ) (Hereinafter sometimes referred to as “compound (V-1)”).
In the formula (V) or the formula (V-1), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ are each in the above formula (II). Indicates the same meaning.

^{[D 1, A 6, A 7} , A 8, A 9 ]
In Formula (V) or Formula (V-1), D ¹ is an sp2 carbon atom (may be represented by the following formula (> C =)), an unsubstituted or substituted sp3 carbon atom (the following formula (> CR ^1- )), or an sp3 nitrogen atom (may be represented by the following formula (> N-)).
In the formula (V) or the formula (V-1), A ⁶ , A ⁷ , A ⁸ , and A ⁹ are each independently an unsubstituted or substituted sp3 carbon atom (which may be represented by the following formula: (—CR ¹ R ² —)), unsubstituted or substituted sp2 carbon atom (may be represented by the following formula (—CR ¹ =)), unsubstituted or substituted sp3 nitrogen Atom (may be represented by the following formula (-NR ^1- )), sp2 nitrogen atom (may be represented by the following formula (-N =)), oxygen atom (may be represented by the following formula (-). O-)) or a sulfur atom (may be represented by the following formula (-S-)).

は、>Ｃ＝Ｎ−Ｏ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｓ-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ-、>Ｎ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ−ＣＲ¹Ｒ²-、>ＣＲ¹−Ｏ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²-、または>ＣＲ¹−Ｏ−ＣＲ¹Ｒ²−ＣＲ¹Ｒ²−Ｏ-で表わされる基であることが好ましい。
Ｒ¹およびＲ²が示すこれらの基としては、上記の多価の有機基「Ａ」において例示したものと同じものが挙げられる。 ^{D 1, A 6, A 7} , A 8, and composed of A ⁹

Is,> C = N-O- CR 1 R 2 -CR 1 R 2 -,> N-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> N-CR 1 R ² —CR ¹ R ² —CR ¹ R ² —S—,> N—CR ¹ R ² —CR ¹ R ² —CR ¹ R ² —O—,> N—CR ¹ R ² —CR ¹ R ² —O ^{-CR 1 R 2 -,> CR} 1 -O-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -, ^{or> CR 1 -O-CR 1 R} 2 -CR 1 R 2 -O- in formula It is preferable that it is a group.
Examples of these groups represented by R ¹ and R ² include the same groups as those exemplified above for the polyvalent organic group “A”.

[Salt of the compound of the present invention]
The salt of the compound of the present invention is not particularly limited as long as it is an agricultural and horticulturally acceptable salt. 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.

[Fungicide for agriculture and horticulture]
The agricultural and horticultural fungicide according to the present invention has the formula (I), formula (II), formula (III), formula (III-1), formula (IV), formula (IV-1), formula (V) or formula It contains at least one selected from the nitrogen-containing heterocyclic compound represented by (V-1) and a salt thereof as an active ingredient.
The nitrogen-containing heterocyclic compound and the salt thereof according to the present invention include hydrates, various solvates and crystal polymorphs. Furthermore, the nitrogen-containing heterocyclic compounds and salts thereof according to the present invention include stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.

  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.

The agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae fungi (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes. Has excellent bactericidal power against bacteria. 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);
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 disease (Botrytis cinerea), leaf mold disease (Cladosporium fulvum), plague (Phytophthora infestans), half body wilt disease (Verticillium albo-atrum);
Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtle mold (Mycovellosiella nattrassii), mycosis (Sclerotinia sclerotiorum);
Strawberries: 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), white plague (Phytophthora porri);
Cabbage: root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. Campestris), black spot bacterial disease (Pseudomonas syringae pv. Maculicala, Pseudomonas syringae pv. Alisalensis), downy mildew Peronospora parasitica), Sclerotinia sclerotiorum;
Kidney bean: 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), purple coat rot (Helicobasidium mompa);
Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), deciduous leaf spot (Cercospora kaki);
Peach: Monilinia fructicola, Cladosporium carpophilum, Homopsis sp. (Phomopsis sp.), Perforated bacterial disease (Xanthomonas campestris pv. Pruni);
Sugar beet: Monilinia fructicola, anthracnose (Colletotrichum acutatum);
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), Body blight (Phomopsis fukushii), Brown spot Disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata);
Tea: Ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis);
Citrus: common scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), sunspot (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 large bacilli (Myriosclerotinia borealis), blight (Gaeumanomyces graminis) );
Barley: leafy leaf disease (Pyrenophora graminea), net leaf disease (Pyrenophora teres), 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) , Seedling Bacterial Diseases (Burkholderia plantarii), Brown Stripe Diseases (Acidovorax avenae), Blastknot Bacterial Diseases (Burkholderia glumae), Stem Leaf Blight (Cercospora oryzae), Rice Blight (Ustilaginoidea virens), Brown Rice (Alternaria alternata) , Curvularia intermedia), black rice (Alternaria padwickii), red rice (Epicoccam purpurascenns);
Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum);
Tulip: Gray mold disease (Botrytis cinerea);
Bentgrass: Sclerotinia borealis, large patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), Red fire (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola) ;
Orchardgrass: powdery mildew (Erysiphe graminis);
Soybean: Purpura (Cercospora kikuchii), downy mildew (Peronospora Manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), mycorrhizal disease (Sclerotinia sclerotiorum), anthracnose (Colletotrichum truncatum);
Potato: Phytophthora infestans;
Bananas: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola);
Rapeseed: Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae);

  The agricultural and horticultural fungicides of the present invention include other fungicides, insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil improvers, animal feeds, etc. It may be used in combination with or in combination with other fungicides. Specific examples of those that can be mixed or used together 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, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromuconazole, 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; Diclobutrazole, Diniconazole 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: buprimate, dimethylolmol, ethylimolmol;
(10) AP fungicide (anilinopyrimidine) type: cyprodinil, mepanipyrim, pyrimethanil, and prim;
(11) N-phenyl carbamate series: 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) type: fenpiconyl, fludioxonil;
(14) Quinoline series: quinoxyphene;
(15) AH fungicide (aromatic hydrocarbon) series: biphenyl, chloronebu, dichlorane, kintozen, technazen;
(16) MBI-R system: fusaride, pyroxylone, tricyclazole;
(17) MBI-D system: carpropamide, diclocimet, phenoxanyl;
(18) SBI agent: fenhexamide, piributicalbu, turbinafine;
(19) Phenylurea: Pencyclone;
(20) QiI-bactericides (Qi inhibitors): cyazofamide, amisulbrom, flumeciclos;
(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) type: dimethomorph, fulmorph, benava varicarb-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, Caputahol , Folpet, chlorothalonil, diclofluuranide, tolylfluanid, dodine, guazatine, iminoctadine, iminoctadine acetate, iminoctadine dodecylbenzenesulfonate, anila , Dithianone, chloropicrin, dazomet, quinomethionate, ciprofram, agrobacterium, fluorimide; isophetamide, toluprocarb, fenpyrazamine, pliophenone, tebufloquine, fluopyram, zaliramide; fluorophorpet, propamidine, edifenphos; bench azole, betoxazine, capsaicin, capsaicin, capsaicin, capsaicin Cufraneb, mancozeb, cyprosulfamide, devacarb, dichlorophen, diphenzoquat, diphenzoquat methylsulfonate, diphenylamine, flumethoverl, fluoroimide, flutianil, fosetyl aluminum, fosetyl calcium, fosetyl sodium, ilumamycin , Methyl isothiocyanate (MITC), mildeomycin, natamycin, ni B tar isopropyl, Okisamokarubu, oxyphencyclimine Ji in, propamocarb-fosetylate, Puropamoshin sodium, Pirimorufu, Pyrrolnitrin, Torunifanido, trichlamide;

Insecticides, acaricides, nematicides, soil insecticides, anthelmintics:
(1) Organic (thio) phosphates: acephate, azamethiphos, azinephos methyl, azinephos ethyl, bromophos ethyl, bromfenbinphos, BRP, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos ethyl, chlorfenvinphos, kazusafos, Carbophenothione, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimeton-S-methylsulfone, diariphos, diazinon , Diclofenthion, dioxabenzophos, disulfoton, ethion, etoprophos, etrimphos, EPN, phenamiphos, fenitrothion, fenthion, phensulfothio , Flupyrazophos, phonophos, formothione, phosmethylan, heptenophos, isazophos, iodofenphos, isofenphos, isoxathione, iprobenphos, malathion, mevinphos, methamidophos, methidathion, monocrotophos, mecarbam, methalyphos, nared, ometoate, oxydimethone parathione , Parathion methyl, phentoate, hosalon, phosmet, phosphamidone, folate, phoxime, pyrimifos methyl, pyrimifos ethyl, propenophos, prothiophos, phosthiazate, phosphocarb, propaphos, propetamphos, protoate, pyridafenthion, pyracrophos, quinalphos, sulthiote, sulfophos , Tetrachlorbinphos, ter Host, triazophos, trichlorfon, tebupirimfos, temephos, thiometon, vamidothion;
(2) Carbamate series: alanic carb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, phenothiocarb, methiocarb, mesomil, oxamyl, pirimicurve, propoxyl, thiodicarb, triazamate, etiofencarb, MPPC, MPC , MTMC, furthiocarb, XMC, aldoxicarb, alixicarb, aminocarb, butencarb, 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, cyclomethrin, promethrin , Halfenprox, flucitrinate, bioareslin, bioethanomethrin, bio Rumetorin, 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, novallon, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiaxox, 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 agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents; Bacillus spp., White scabs, black scabs, Pekir Myces 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, Sienopyrafen, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Axipodene (Afidopyropen), piflumbide (pyflubumide), flometokin, flufiprol (flufipr) ole), fluenesulfone, meperfluthrin, tetramethylfluthrin, sulfoxafurol, imiciaphos, tralopyril, difluvidazine, dimefluthrin, methylneodecanamide;
(23) Anthelmintic
(a) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole;
(b) Salicylanilide series: closantel, oxyclozanide;
(c) substituted phenol type: nitroxinyl;
(d) pyrimidine series: pyrantel;
(e) imidazothiazole series: levamisole;
(f) tetrahydropyrimidine: praziquantel;
(g) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole, demiditraz;

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 example.

Example 1
Production of 3- (4,4,5,5-tetramethyl-1,3-dihydro-2-benzoxepin-1-yl) quinoline (3-23) n-BuLi solution (solvent: n-hexane) in 4 mL of dehydrated tetrahydrofuran ; Concentration 2.6M) 1.05 mL was added and cooled to -10 ° C. To this, 1.5 mL of n-BuMgCl solution (solvent: tetrahydrofuran; concentration 0.91M) was added. To this solution, 0.85 g of 3-bromoquinoline was added and stirred at −10 ° C. for 20 minutes. Thereafter, 1.13 g of 2- [3- [tert-butyl (dimethyl) silyl] oxy-1,1,2,2-tetramethyl-propyl] -3-fluoro-benzaldehyde was added and stirred for 1 hour. The reaction solution was poured into ice water and neutralized with 1M HCl aqueous solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.98 g of [2- [3- [tert-butyl (dimethyl) silyl] oxy-1,1,2,2-tetramethyl-propyl] -phenyl] -(3-quinolyl) methanol was obtained.
[2- [3- [tert-butyl (dimethyl) silyl] oxy-1,1,2,2-tetramethyl-propyl] -phenyl]-(3-quinolyl) methanol (0.32 g) was dissolved in tetrahydrofuran (1.5 mL). 1 mL of (n-Bu) ₄ NF solution (tetrahydrofuran solvent; concentration 1.0 M) was added to the solution, and the mixture was stirred at room temperature.
On the way, 1 mL of (n-Bu) ₄ NF solution (tetrahydrofuran solvent; concentration 1.0 M) was added, and the mixture was stirred at room temperature for a total of 7.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.13 g of 3- [2- [hydroxy (3-quinolyl) methyl] phenyl] -2,2,3-trimethyl-butan-1 -ol got.
3- [2- [hydroxy (3-quinolyl) methyl] phenyl] -2,2,3-trimethyl-butan-1-ol 0.13g was dissolved in 1.5mL of N, N-dimethylformamide, and p- Toluenesulfonic acid pyridine salt (19 mg) was added, and the mixture was stirred in a microwave reactor at 150 ° C. for 60 minutes. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the desired 3- (4,4,5,5-tetramethyl-1,3-dihydro-2-benzoxepin-1-yl) quinoline 0.12 g was obtained.

(Example 2)
Production of 2,2-dimethyl-4- (3-quinolyl) -1,4-benzothiazin-3-one (2-5)
To 5 mL of N-methylpyrrolidone were added 6.24 g of 3-bromoquinoline, 3.3 g of 4H-1,4-benzothiazin-3-one, 0.76 g of copper iodide, and 3.45 g of potassium carbonate, and the mixture was stirred at 200 ° C. for 1 hour. The reaction was cooled and poured into water. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 3.6 g of 4- (3-quinolyl) -1,4-benzothiazin-3-one.
Diisopropylamine (0.79 g) was added to 10 mL of dehydrated and dried tetrahydrofuran, and the mixture was cooled to 0 ° C. To this, 3 mL of n-BuLi solution (solvent: n-hexane; concentration 2.6 M) was added at 0 ° C., and the mixture was stirred for 10 minutes. To this, 1.0 g of 4- (3-quinolyl) -1,4-benzothiazin-3-one was added, cooled to −78 ° C., and stirred for 1 hour. At −78 ° C., 1.1 g of methyl iodide was added to the reaction solution. The mixture was warmed to room temperature and stirred at room temperature for 2 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.33 g of the desired product, 2,2-dimethyl-4- (3-quinolyl) -1,4-benzothiazin-3-one.

Example 3
Production of 8-fluoro-3- (2-methoxy-3,3-dimethyl-indolin-1-yl) quinoline (1-6)
1.10 g of 1- (8-fluoro-3-quinolyl) -3,3-dimethyl-indolin-2-one was dissolved in 20 mL of tetrahydrofuran. To this, 0.204 g of LiAlH ₄ was added and stirred at room temperature for 3 days. To the reaction solution, 0.8 g of water and 0.2 g of a 1M NaOH solution were added at 0 ° C. and stirred for 1 hour. Insolubles were removed by Celite filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.3 g of 1- (8-fluoro-3-quinolyl) -3,3-dimethyl-indolin-2-ol (1-4).
1- (8-fluoro-3-quinolyl) -3,3-dimethyl-indolin-2-ol 0.15g was dissolved in 5mL of tetrahydrofuran, and this was mixed with sodium hydride (60% oil dispersion) 29.16mg, methyl iodide 0.103 g were sequentially added and stirred at room temperature for 1 day. Thereafter, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.1 g of the desired product 8-fluoro-3- (2-methoxy-3,3-dimethyl-indolin-1-yl) quinoline.

Example 4
Production of 5,5-dimethyl-1- (3-quinolyl) -4,1-benzoxazepin-2-one (3-16) To 15 mL of diglyme, 0.65 g of 3-bromoquinoline, 60 mg of copper iodide, N, N ' -Dimethylethane-1,2-diamine 55 mg, potassium carbonate 0.87 g, and 5,5-dimethyl-1H-4,1-benzoxazepin-2-one 0.6 g were sequentially added. Stir the day. The reaction solution was cooled to room temperature, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. By purifying the obtained residue by column chromatography using silica gel and amino silica gel, 0.11 g of 5,5-dimethyl-1- (3-quinolyl) -4,1-benzoxazepin-2-one was obtained. Obtained.

(Example 5)
Preparation of 4,4-dimethyl-1- (3-quinolyl) -5H-3,2-benzoxazepine (3-2) ) 0.4 g of metanone oxime was dissolved, 4 mL of trifluoroacetic acid was added thereto, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.23 g of 4,4-dimethyl-1- (3-quinolyl) -5H-3,2-benzoxazepine.

(Example 6)
Manufacture of 1,1-dimethyl-4- (3-quinolyl) -2,3-benzoxazine (2-2) 0.5 g of (2-isopropenylphenyl)-(3-quinolyl) methanone oxime was dissolved in 4 mL of tetrahydrofuran. 5 mL of trifluoroacetic acid was added and stirred at room temperature for 13 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.09 g of 1,1-dimethyl-4- (3-quinolyl) -2,3-benzoxazine.

(Example 7)
Production of 3,3,4,4-tetramethyl-1- (3-quinolyl) -2H-quinoline (2-13) 3,3,4,4-tetramethyl-1- (3-quinolyl) quinolin- in 5 mL of tetrahydrofuran dissolved 2-one 0.15 g, which in the LiAlH ₄ 49 mg, followed by heating to reflux for 6 hours. Next, 49 mg of LiAlH ₄ was added to the reaction solution, and the mixture was heated to reflux for 8 hours. To the obtained liquid, 49 mg of LiAlH ₄ was added and heated under reflux for 8 hours. Thereafter, the reaction solution was cooled to 0 ° C. To this, 0.6 g of water and 0.15 g of 15% NaOH solution were added and stirred at room temperature for 30 minutes. Next, the mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.03 g of 3,3,4,4-tetramethyl-1- (3-quinolyl) -2H-quinoline.

(Example 8)
Production of 3- (2,2-dimethylchromen-4-yl) quinoline (2-19) 1.77 g of 3-Bromoquinoline was added to 30 mL of dehydrated and dried diethyl ether and cooled to -78 ° C. To this, 5.26 mL of 1.7 M t-BuLi solution was added dropwise. After the completion, the mixture was stirred at -78 ° C for 1 hour. Dissolved in 5 mL of dehydrated and dried diethyl ether, added 1.5 g of 2,2-dimethylchroman-4-one, stirred at -78 ° C for 1 hour, and then stirred at 0 ° C for 1 hour. To the reaction solution was added 100 mL of saturated ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.58 g of 2,2-dimethyl-4- (3-quinolyl) chroman-4-ol (2-16).
0.22-g of 2,2-dimethyl-4- (3-quinolyl) chroman-4-ol was dissolved in 10 mL of benzene. To this, 13.7 mg of p-toluenesulfonic acid monohydrate was added, and the mixture was refluxed for 19 hours while dehydrating with a Dean-Stark apparatus. The reaction was cooled to room temperature. It was poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.18 g of 3- (2,2-dimethylchromen-4-yl) quinoline.

  The compounds of the present invention obtained in the above Examples and the compounds of the present invention synthesized by the same method as in any of the above Examples are shown in Tables 1 to 4. Table 1 shows substituents in the compound represented by formula (III-2), Table 2 shows substituents in the compound represented by formula (IV-2), and Table 3 shows formula (V-2). The substituent in the represented compound is shown. Further, the melting point [° C.] or the refractive index is also shown in the physical property column.

The compounds referred to as Amorphous physical properties ^{column, 1 H-NMR (300MHz,} CDCl 3) were measured [delta]. The measurement results are shown below.

1-1: δ 1.71 (s, 6H), 7.39-7.49 (m, 3H), 7.62 (m, 1H), 7.73-7.84 (m, 2H), 7.96 (m, 1H), 8.17 (d, J = 8.7Hz, 1H), 9.22 (d, J = 1.8 Hz, 1H), 9.53 (d, J = 2.1Hz, 1H).
1-5: δ 1.29 (s, 3H), 1.48 (s, 3H), 3.32 (s, 3H), 3.83 (s, 2H), 4.90 (s, 1H), 6.92 (m, 1H), 7.09-7.19 (m, 3H), 7.49-7.63 (m, 2H), 7.74 (m, 1H), 8.05-8.08 (m, 2H), 9.11 (d, 1H).
1-6: δ 1.26 (s, 3H), 1.49 (s, 3H), 3.33 (s, 3H), 4.92 (s, 1H), 6.95 (m, 1H), 7.14-7.30 (m, 4H), 7.41 -7.53 (m, 2H), 8.05 (m, 1H), 9.16 (d, 1H).
1-7: δ 3.83 (s, 2H), 6.89 (m, 1H), 7.12-7.19 (m, 2H), 7.26 (m, 1H), 7.46-7.57 (m, 2H), 7.69-7.72 (m, 2H), 8.03 (d, 1H), 9.06 (d, 1H).
1-9: δ 3.22 (t, 2H), 4.09 (t, 2H), 6.84 (t, 1H), 7.1-7.3 (m, 3H), 7.4-7.8 (m, 4H), 8.03 (dd, 1H) , 9.06 (d, 1H).

1-12: δ 2.40 (s, 3H), 7.13-7.21 (m, 3H), 7.59-7.68 (m, 2H), 7.80-7.92 (m, 2H), 8.23 (m, 2H), 8.95 (d, 1H).
1-13: δ 7.17 (m, 1H), 7.23-7.32 (m, 2H), 7.65-7.71 (m, 2H), 7.83-7.94 (m, 2H), 8.24 (m, 2H), 8.96 (d, 1H).
1-18: δ 6.31 (s, 1H (a)), 6.54 (s, 1H (b)), 6.70 (s, 1H (a)), 6.81 (s, 1H (b)), 7.09 (m, 1H ), 7.32-7.50 (m, 2H), 7.52-7.58 (m, 2H), 7.67-7.81 (m, 2H), 8.08-8.18 (m, 2H), 8.76 (d, 1H (a)), 8.94 ( d, 1H (b)).
1-19: δ 6.34 (s, 1H (a)), 6.60 (s, 1H (b)), 6.82-7.08 (m, 3H), 7.29-7.62 (m, 4H), 8.12 (s, 1H (a )), 8.27 (s, 1H (b)), 8.86 (d, 1H (a)), 9.10 (d, 1H (b)).

2-1: δ 5.12 (s, 2H), 7.25-7.44 (m, 3H), 7.56-7.66 (m, 2H), 7.78-7.92 (m, 2H), 8.19 (d, 1H), 8.47 (d, 1H), 9.21 (d, 1H).
2-3: δ 2.47 (s, 3H), 5.43 (m, 1H), 5.81 (m, 1H), 7.6-8.45 (m, 8H), 8.63 (d, 1H), 9.35 (d, 1H).
2-5: δ 1.59 (s, 6H), 6.4-6.5 (m, 1H), 7.0-7.1 (m, 2H), 7.4-7.45 (m, 1H), 7.5-7.65 (m, 1H), 7.7- 7.85 (m, 2H), 8.07 (d, 1H), 8.18 (d, 1H), 8.70 (d, 1H).
2-6: δ 1.61 (s, 6H), 6.24 (d, 1H), 6.86 (dt, 1H), 6.95-7.05 (m, 1H), 7.55-7.65 (m, 1H), 7.75-7.85 (m, 2H), 8.06 (d, 1H), 8.18 (d, 1H), 8.68 (d, 1H).
2-7: δ 1.62 (s, 6H), 6.36 (dd, 1H), 6.96 (t, 1H), 7.15 (dd, 1H), 7.55-7.65 (m, 1H), 7.75-7.85 (m, 2H) , 8.05 (d, 1H), 8.18 (d, 1H), 8.66 (d, 1H).
2-8: δ 1.58 (s, 6H), 2.43 (s, 3H), 6.25-6.35 (m, 1H), 6.85-7.00 (m, 2H) 7.55-7.65 (m, 1H), 7.70-7.85 (m , 2H), 8.06 (d, 1H), 8.15-8.20 (m, 1H), 8.68 (d, 1H).

2-12: δ 1.02 (s, 6H), 1.42 (s, 6H), 3.47 (s, 2H), 6.52 (m, 1H), 6.60 (m, 1H), 6.88 (m, 1H), 7.52 (m , 1H), 7.62 (m, 1H), 7.71 (m, 1H), 7.83 (d, 1H), 8.06 (d, 1H), 8.89 (d, 1H).
2-13: δ 1.00 (s, 6H), 1.31 (s, 6H), 3.51 (s, 2H), 6.82-6.87 (m, 2H), 6.97 (m, 1H), 7.35 (m, 1H), 7.50 (m, 1H), 7.59 (m, 1H), 7.70 (m, 1H), 7.82 (d, 1H), 8.04 (d, 1H), 8.92 (d, 1H).
2-14: δ 2.10 (m, 2H), 2.89 (t, 2H), 3.75 (t, 2H), 6.75-7.80 (m, 8H), 8.03 (d, 1H), 8.92 (d, 1H).
2-17: δ 2.6-3.1 (m, 4H), 7.2-7.85 (m, 8H), 7.82 (dd, 1H), 8.08 (dd, 1H).
2-18: δ 7.3-8.0 (m, 9H), 8.21 (d, 1H), 8.28 (d, 1H), 9.08 (d, 1H).
2-19: δ 1.55 (s, 6H), 5.76 (s, 1H), 6.84 (m, 1H), 6.92-6.99 (m, 2H), 7.20 (m, 1H), 7.58 (m, 1H), 7.74 (m, 1H), 7.83 (m, 1H), 8.13-8.16 (m, 2H), 8.90 (d, 1H).

3-6: δ 1.16 (s, 6H), 2.26 (s, 2H), 6.86 (m, 1H), 7.16-7.31 (m, 3H), 7.53 (m, 1H), 7.66-7.76 (m, 2H) , 8.00 (m, 1H), 8.09 (d, 1H), 8.73 (d, 1H).
3-7: δ 1.15 (s, 6H), 2.73 (bs, 2H), 6.85 (d, 1H), 7.1-7.6 (m, 6H), 8.04 (d, 1H), 8.78 (d, 1H).
3-9: δ 1.18 (s, 6H), 2.82 (bs, 2H), 6.65 (d, 1H), 6.9-7.6 (m, 5H), 8.03 (d, 1H), 8.75 (d, 1H).
3-10: δ 1.51 (s, 6H), 2.15 (t, 2H), 2.50 (t, 2H), 6.82 (dd, 1H), 7.1-7.3 (m, 2H), 7.4-7.8 (m, 4H) , 7.9-8.1 (m, 2H), 8.73 (d, 1H).

3-11: δ 1.53 (s, 6H), 2.15 (t, 2H), 2.53 (t, 2H), 6.85 (dd, 1H), 7.1-7.6 (m, 6H), 8.10 (d, 1H), 8.76 (d, 1H).
3-12: δ 1.18 (d, 3H), 1.51 (s, 6H), 1.92 (m, 1H), 2.08 (m, 1H), 2.71 (m, 1H), 6.85 (m, 1H), 7.14-7.30 (m, 2H), 7.50-7.54 (m, 2H), 7.65-7.74 (m, 2H), 8.03-8.08 (m, 2H), 8.72 (d, 1H).
3-19: δ 1.99 (s, 6H), 4.34 (s, 2H), 6.73 (m, 1H), 6.99 (m, 1H), 7.29 (m, 1H), 7.39 (m, 1H), 7.51 (m , 1H), 7.62 (m, 1H), 8.39 (m, 1H), 8.65 (d, 1H).

3-22: δ 1.53 (s, 3H), 1.69 (s, 3H), 3.30 (m, 1H), 4.04 (m, 1H), 5.48 (m, 1H), 7.06 (m, 1H), 7.15-7.32 (m, 3H), 7.36-7.48 (m, 3H), 7.78 (m, 1H), 8.55 (d, 1H).
3-23: δ 0.84 (s, 3H), 0.95 (s, 3H), 1.40 (s, 3H), 1.52 (s, 3H), 3.6-3.8 (m, 1H), 3.94 (bs, 1H), 6.31 (s, 1H), 6.70 (bs, 1H), 7.0-7.8 (m, 6H), 8.03 (bs, 1H), 8.13 (d, 1H), 8.92 (s, 1H).
3-24: δ 1.23 (s, 3H), 1.38 (s, 3H), 3.85 (q, 1H), 6.02 (s, 1H), 6.60 (d, 3H), 6.92 (t, 1H), 7.06 (d , 1H), 7.2-7.3 (m, 1H), 7.5-7.9 (m, 3H), 8.1-8.2 (m, 2H), 8.95 (d, 1H)
3-25: δ 1.14 (s, 3H), 1.71 (s, 3H), 3.34 (s, 3H), 3.61 (d, 1H), 3.96 (d, 1H), 6.84 (m, 1H), 7.10-7.21 (m, 2H), 7.51 (m, 1H), 7.66 (m, 1H), 7.76 (m, 1H), 7.83 (m, 1H), 8.04 (d, 1H), 8.45 (d, 1H), 9.18 ( d, 1H).

  Next, formulation examples of the agricultural and horticultural fungicide according to the present invention will be shown. However, additives and addition ratios should not be 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 wettable powder Compound of the present invention 40 parts Clay 48 parts Dioctylsulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts Get.

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.

  Next, the usefulness of the compounds of the present invention for agricultural and horticultural fungicides will be explained by biological test examples.

(Biological test example 1) Apple scab control test The emulsion of the compound of the present invention was diluted with water. The diluted solution was sprayed on apple seedlings (variety “Kunimitsu”, 3-4 leaf stage) cultivated in an unglazed pot. Air dried at room temperature. After that, conidia spores of Venturia inaequalis were inoculated. 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 No. 1-1, 1-4, 1-6, 1-8, 1-19, 2-2, 2-5, 2-6, 2-7, 2-8, 2-12, 2-13, 2-14, 2-19, 3-1, 3-2, 3-3, 3-4, 3-5, 3-7, 3-9, 3-10, 3-11, 3-12, 3- About the compounds of 16, 3-18, 3-20, 3-21, 3-22, and 3-23, the apple scab control test was done with the dilution liquid of an active ingredient density | concentration of 100 ppm, respectively. 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 of the compound of the present invention was diluted with water. The diluted solution was sprayed on cucumber seedlings (variety “Sagamihanjiro”, cotyledon stage) grown in an unglazed pot. Air dried at room temperature. Thereafter, a conidial spore suspension of Botrytis cinerea was inoculated dropwise. It was kept for 4 days in a dark place at 20 ° C and in a high humidity room. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound Nos. 1-4, 1-6, 1-8, 2-2, 2-5, 2-6, 2-12, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-11, 3-12, 3-14, 3-15, 3-16, 3-17, 3-20, 3-21, 3-22, 3- About the compound of 23 and 3-24, the cucumber gray mold control test was done with the dilution liquid of an active ingredient density | concentration of 100 ppm, respectively. As a result, all the compounds showed a control value of 75% or more.

Claims (12)

A nitrogen-containing heterocyclic compound represented by the formula (I) or a salt thereof.

(In formula (I), each X ¹ is independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted group. A C2-8 alkynyl group having an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocyclic group, A substituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted group; Carbamoyl group, unsubstituted or substituted hydroxyl group, unsubstituted or substituted amino group, unsubstituted or substituted mercapto group A sulfonyl group having a substituent group, halogeno group, a cyano group or a nitro group.
m represents the number of X ¹ and is an integer of 0-6.
F represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocycle.
B independently represents a carbon atom or a nitrogen atom.
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 An unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted heterocyclic group, an unsubstituted or substituted group C1-8 acyl group, unsubstituted or substituted (1-imino) C1-8 alkyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, unsubstituted Or a substituted hydroxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted mercapto group, and a substituted group. That a 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.
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
B ′ each independently represents a carbon atom or a nitrogen atom.
A bond in which a broken line and a solid line are arranged indicates a single bond or a double bond.
A represents a polyvalent organic group.
D represents an sp2 carbon atom, an unsubstituted or substituted sp3 carbon atom, or an sp3 nitrogen atom. ) The nitrogen-containing heterocyclic compound or a salt thereof according to claim 1, wherein the formula (I) is the formula (II).

(In the formula (II), X ¹ , m, F, B, X ² , n, A, and D have the same meaning as in the formula (I).
E ¹ , E ² , E ³ , and E ⁴ each independently represent a carbon atom or a nitrogen atom. However, two or more of E ^{1 to} E ⁴ are not nitrogen atoms. ) The nitrogen-containing heterocyclic compound or a salt thereof according to claim 2, wherein the formula (II) is the formula (III).

(In the formula (III), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ have the same meanings as in the formula (II).
D ¹ represents an sp2 carbon atom (> C =), an unsubstituted or substituted sp3 carbon atom (> CR ^1- ), or an sp3 nitrogen atom (> N-).
A ¹ and A ² are each independently an unsubstituted or substituted sp3 carbon atom (CR ¹ R ^2- ), an unsubstituted or substituted sp2 carbon atom (-CR ¹ =), A substituted or substituted sp3 nitrogen atom (—NR ¹ —), sp2 nitrogen atom (—N═), oxygen atom (—O—), or sulfur atom (—S—) is shown.
Each R ¹ independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocyclic ring; A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group;
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group. ) The nitrogen-containing heterocyclic compound or a salt thereof according to claim 3, wherein the formula (III) is the formula (III-1).

(In the formula (III-1), X ¹ , m, B, X ² , n, E ¹ , E ² , E ³ , E ⁴ , D ¹ , A ¹ and A ² are each in the formula (III). Indicates the same meaning.) Consists of D ¹ , A ¹ and A ²

> C = N-CR ¹ R ² -,> C = N-O-,> N-CR ¹ R ² -CR ¹ R ² -,> N-CR ¹ = CR ¹ -,> C = CR ¹ —S—,> C═CR ¹ —O—, or a group represented by> CR ¹ —O—CR ¹ R ² — (R ¹ and R ² have the same meaning as in formula (III). The nitrogen-containing heterocyclic compound or a salt thereof according to claim 3 or 4, wherein The nitrogen-containing heterocyclic compound or a salt thereof according to claim 2, wherein the formula (II) is the formula (IV).

(In the formula (IV), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ have the same meanings as in the formula (II).
D ¹ represents an sp2 carbon atom (> C =), an unsubstituted or substituted sp3 carbon atom (> CR ^1- ), or an sp3 nitrogen atom (> N-).
A ³ , A ⁴ , and A ⁵ are each independently an unsubstituted or substituted sp3 carbon atom (—CR ¹ R ² —), an unsubstituted or substituted sp2 carbon atom (—CR ¹ =), an unsubstituted or substituted sp3 nitrogen atom (—NR ¹ —), sp2 nitrogen atom (—N═), oxygen atom (—O—), or sulfur atom (—S—).
Each R ¹ independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocyclic ring; A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group;
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group. The nitrogen-containing heterocyclic compound or a salt thereof according to claim 6, wherein the formula (IV) is the formula (IV-1).

(In the formula (IV-1), X ¹ , m, B, X ² , n, E ¹ , E ² , E ³ , E ⁴ , D ¹ , A ³ , A ⁴ , and A ⁵ are represented by the formula (IV ) Shows the same meaning as each inside.) Consists of D ¹ , A ³ , A ⁴ , and A ⁵

> C = N-O-CR ¹ R ² -,> C = N-N = CR ¹ -,> N-CR ¹ R ² -CR ¹ R ² -S-,> N-CR ¹ R ^{2- CR 1 R 2 -O-,> N} -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> CR 1 -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> C = ^{CR 1 -CR 1 = CR 1 -} ,> C = CR 1 -CR 1 R 2 -O-, ^{or> C = CR 1 -CR 1 =} N- group represented by (R ¹ and R ² has the formula ( The nitrogen-containing heterocyclic compound or a salt thereof according to claim 6 or 7, which has the same meaning as in IV). The nitrogen-containing heterocyclic compound or a salt thereof according to claim 2, wherein the formula (II) is the formula (V).

(In the formula (V), X ¹ , m, F, B, X ² , n, E ¹ , E ² , E ³ , and E ⁴ have the same meanings as in the formula (II).
D ¹ represents an sp2 carbon atom (> C =), an unsubstituted or substituted sp3 carbon atom (> CR ^1- ), or an sp3 nitrogen atom (> N-).
A ⁶ , A ⁷ , A ⁸ , and A ⁹ are each independently an unsubstituted or substituted sp3 carbon atom (—CR ¹ R ² —), an unsubstituted or substituted sp2 carbon atom. (—CR ¹ ═), unsubstituted or substituted sp 3 nitrogen atom (—NR ¹ —), sp 2 nitrogen atom (—N═), oxygen atom (—O—), or sulfur atom (—S—) Indicates.
Each R ¹ independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocyclic ring; A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group;
R ² each independently represents a hydrogen atom, an unsubstituted or substituted C 1-8 alkyl group, an unsubstituted or substituted C 6-10 aryl group, an unsubstituted or substituted heterocycle A group, an unsubstituted or substituted hydroxyl group, a halogeno group, or a cyano group; R ¹ and R ² may together form an oxo group. ) The nitrogen-containing heterocyclic compound or a salt thereof according to claim 9, wherein the formula (V) is the formula (V-1).

(In the formula (V-1), X ¹ , m, B, X ² , n, E ¹ , E ² , E ³ , E ⁴ , D ¹ , A ⁶ , A ⁷ , A ⁸ and A ⁹ are (Indicates the same meaning as in (V).) Consists of D ¹ , A ⁶ , A ⁷ , A ⁸ and A ⁹

But,> C = N-O- CR 1 R 2 -CR 1 R 2 -,> N-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -,> N-CR 1 R ^{2 -CR 1 R 2 -CR 1 R} 2 -S-,> N-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -O-,> N-CR 1 R 2 -CR 1 R 2 -O ^{-CR 1 R 2 -,> CR} 1 -O-CR 1 R 2 -CR 1 R 2 -CR 1 R 2 -, ^{or> CR 1 -O-CR 1 R} 2 -CR 1 R 2 -O-
The nitrogen-containing heterocyclic compound or a salt thereof according to claim 9 or 10, wherein R ¹ and R ² have the same meanings as those in formula (V).   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 11 or a salt thereof.