JP2008088139A - 3-substituted quinoline compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having high microbicidal activity on various plant pathogenic microbes (especially Pyricularia oryzae), thus useful as an active ingredient for agrochemicals. <P>SOLUTION: An agrochemical is provided, comprising the compound of general formula (I) or a salt thereof as the active ingredient. In general formula (I), A-B moiety is the formula: C=NC(R<SP>1</SP>)(R<SP>2</SP>) group, the formula: NC(O)C(R<SP>1</SP>)(R<SP>2</SP>) group, the formula: C=NC(R<SP>1</SP>)(R<SP>2</SP>)O group or the formula: C=NSO<SB>2</SB>group, wherein R<SP>1</SP>and R<SP>2</SP>are each a halogen atom, (halogen-substituted)alkyl, (halogen-substituted) alkoxy, OH, or joined each other to form =O, =NOH, an alkoxyimino group or alkylene group; X is a halogen atom, (halogen-substituted)alkyl, (halogen-substituted) alkoxy, phenoxy, OH, alkylthio or (alkyl-substituted) amino; n is 0-4; Y is a halogen atom, (halogen-substituted) alkyl, (halogen-substituted) alkoxy, phenyl, phenoxy, (alkyl-substituted) amino, NO<SB>2</SB>, OH or SH; and m is 0-6. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a 3-substituted quinoline compound or a salt thereof, and an agricultural chemical containing it as an active ingredient.

  As for the 3-substituted quinoline compound, its 3-quinolyl-1-cyclohexanecarboxamide derivative is described (Patent Document 1), and 3- (dihydro (tetrahydro) isoquinolin-1-yl) quinoline compound is used for rice blast disease and It is described that it has an effect on cucumber gray mold (Patent Document 2). However, no compound is described in which 3-position is substituted with isoindole, oxindole, 1,3-benzoxazine and benzisothiazole.

Low doses of control against rice blast (Pyricularia oryzae) and tomato, cucumber and green beans (Botrytis cinerea), which often cause severe damage to crops and horticultural crops. The existing agricultural and horticultural fungicides are not satisfactory in terms of their efficacy and residual effect in providing possible compounds, and have properties that do not harm human animals, beneficial insects, the environment, etc. New types of fungicides are desired.
International Publication No. 02/88086 Pamphlet International Publication No. 2005/70917 Pamphlet

  As a result of intensive research on the 3-substituted quinoline compounds, the present inventors have excellent bactericidal activity against various plant diseases and are useful as active ingredients of agricultural chemicals, especially among plant mold diseases. A new low-dose control of rice blast (Pyricularia oryzae), which often causes severe damage to agricultural and horticultural crops, and tomato, cucumber and green beans (Botrytis cinerea) A quinoline compound was found and the present invention was completed.

  The present invention provides a 3-substituted quinoline compound or a salt thereof which has an excellent bactericidal activity against various plant diseases and is useful as an active ingredient of an agricultural chemical, and an agricultural chemical containing it as an active ingredient.

［式中、
Ａ−Ｂ部分は、式 Ｃ＝ＮＣ（Ｒ^１）（Ｒ^２）で表される基、式 ＮＣ（Ｏ）Ｃ（Ｒ^１）（Ｒ^２）で表される基、式 Ｃ＝ＮＣ（Ｒ^１）（Ｒ^２）Ｏで表される基又は式 Ｃ＝ＮＳＯ_２で表される基を示し、
Ｒ^１及びＲ^２は、独立して、ハロゲン原子、置換されていてもよいＣ₁〜Ｃ₆アルキル基（当該置換基は、同一又は異なった１〜３個のハロゲン原子である。）、置換されていてもよいＣ₁〜Ｃ₆アルコキシ基（当該置換基は、同一又は異なった１〜３個のハロゲン原子である。）又は水酸基を表すか、或はそれらが一緒になって、オキソ基、ヒドロキシイミノ基、Ｃ₁〜Ｃ₆アルコキシイミノ基又はＣ_２〜Ｃ_５アルキレン基を形成し、
Ｘは、ハロゲン原子、置換されていてもよいＣ₁〜Ｃ₆アルキル基（当該置換基は、同一又は異なった１〜３個のハロゲン原子である。）、置換されていてもよいＣ₁〜Ｃ₆アルコキシ基（当該置換基は、同一又は異なった１〜３個のハロゲン原子である。）、フェノキシ基、水酸基、Ｃ₁〜Ｃ₆アルキルチオ基又は置換されていてもよいアミノ基（当該置換基は、同一又は異なった１〜２個のＣ₁〜Ｃ₆アルキル基である。）を表し、
ｎは、０〜４の整数を表し、ｎが２以上であるとき、複数のＸは同一であっても異なっていてもよく、
Ｙは、ハロゲン原子、置換されていてもよいＣ₁〜Ｃ₆アルキル基（当該置換基は、同一又は異なった１〜３個のハロゲン原子である。）、置換されていてもよいＣ₁〜Ｃ₆アルコキシ基（当該置換基は、同一又は異なった１〜３個のハロゲン原子である。）、フェニル基、フェノキシ基、置換されていてもよいアミノ基（当該置換基は、同一又は異なった１〜２個のＣ₁〜Ｃ₆アルキル基である。）、ニトロ基、水酸基又はメルカプト基を表し、
ｍは、０〜６の整数を表し、ｍが２以上であるとき、複数のＹは同一であっても異なっていてもよい。］
で表される化合物又はその塩である。 The present invention relates to general formula (I)

[Where:
The A-B moiety is a group represented by the formula C = NC (R ¹ ) (R ² ), a group represented by the formula NC (O) C (R ¹ ) (R ² ), or a formula C = NC (R ¹ ) a group represented by (R ² ) O or a group represented by the formula C═NSO ₂ ;
R ¹ and R ² are each independently a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 halogen atoms), substitution An optionally substituted C ₁ -C ₆ alkoxy group (the substituents are the same or different 1 to 3 halogen atoms) or a hydroxyl group, or they are taken together to form an oxo group , hydroxyimino group, to form a C ₁ -C ₆ alkoxyimino group or _C 2 -C ₅ alkylene group,
X is a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 halogen atoms), and an optionally substituted C _1- C ₆ alkoxy group (said substituents are the same or different 1 to 3 halogen atoms.), a phenoxy group, a hydroxyl group, C ₁ -C ₆ alkylthio group or an optionally substituted amino group (the substituent groups represent the same or different 1-2 C ₁ -C ₆ alkyl group.),
n represents an integer of 0 to 4, and when n is 2 or more, a plurality of Xs may be the same or different,
Y is a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 halogen atoms), and an optionally substituted C _1- C ₆ alkoxy group (the substituent is the same or different 1 to 3 halogen atoms), phenyl group, phenoxy group, optionally substituted amino group (the substituent is the same or different is one to two C ₁ -C ₆ alkyl group.), a nitro group, a hydroxyl group or a mercapto group,
m represents an integer of 0 to 6, and when m is 2 or more, a plurality of Y may be the same or different. ]
Or a salt thereof.

  In the above formula (I), when n is 0, Xn represents a hydrogen atom, and when m is 0, Ym represents a hydrogen atom.

  The compounds of the present invention can be used as agricultural and horticultural fungicides, and without causing damage to the host plant, various phytopathogenic fungi such as rice blast (Pyricularia oryzae) and gray mold of cucumber, tomato and kidney beans. Demonstrate against (Botrytis cinerea).

  In the present invention, the “halogen atom” is a fluorine atom, chlorine atom, bromine atom or iodine atom, preferably a fluorine atom, chlorine atom or bromine atom, more preferably a fluorine atom or chlorine atom. And most preferably a fluorine atom.

In the present invention, “C ₁ -C ₆ alkyl group” means, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, isopentyl group. 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group , 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group A linear or branched alkyl group having 1 to 6 carbon atoms, preferably a linear or branched alkyl group having 1 to 5 carbon atoms (C ₁ -C ₅ alkyl group), and more preferably Is A straight-chain or branched alkyl group having 1 to 4 carbon atoms (C ₁ -C ₄ alkyl group), and even more preferably a straight-chain or branched alkyl group having 1 to 3 carbon atoms (C _{1 to} C ₃ alkyl group), particularly preferably a methyl group, an ethyl group or a propyl group, and most preferably a methyl group or an ethyl group.

In the present invention, “optionally substituted C ₁ -C ₆ alkyl group (the substituents are the same or different 1 to 3 halogen atoms)” means the above “C ₁ -C ₆ alkyl group”. In addition to “group”, for example, trifluoromethyl group, trichloromethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, 2,2,2 -Trichloroethyl group, 2,2,2-trifluoroethyl group, 2-bromoethyl group, 2-chloroethyl group, 2-fluoroethyl group, 3-chloropropyl group, 3,3,3-trifluoropropyl group, 4 -Fluorobutyl group, 3-fluoro-2-methylpropyl group, 3,3,3-trifluoro-2-methylpropyl group, 6,6,6-trichlorohexyl group, etc. The above-mentioned “C ₁ -C ₆ alkyl group” substituted by 1 to 3 “halogen atoms” which are the same or different, and preferably 1 to 3 “halogen atoms” which are the same or different. The “C ₁ -C ₄ alkyl group” which may be substituted, and more preferably, the “C ₁ -C ₄ alkyl group” which may be substituted with ₁ to 3 “fluorine or chlorine atoms” which are the same or different. _{1 to} C ₃ alkyl group ”, more preferably a methyl group, an ethyl group, a propyl group, a chloromethyl group or a trifluoromethyl group, and particularly preferably a methyl group, an ethyl group or a trifluoromethyl group. Group, most preferably a methyl group.

In the present invention, the “C ₁ -C ₆ alkoxy group” means, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, an s-butoxy group, a t-butoxy group, a pentyloxy group, Isopentyloxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropoxy group, hexyloxy group, (4-methylpentyl) oxy group, (3-methylpentyl) oxy group, (2-methylpentyl) Oxy group, (1-methylpentyl) oxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethylbutoxy group A straight or branched alkoxy group having 1 to 6 carbon atoms such as a group, 2,3-dimethylbutoxy group, 2-ethylbutoxy group Ri, preferably a straight or branched alkoxy group having 1 to 4 carbon atoms (C ₁ -C ₄ alkoxy group), more preferably a C ₁ -C ₃ alkoxy group, even more A methoxy group or an ethoxy group is preferable, and a methoxy group is most preferable.

In the present invention, “optionally substituted C ₁ -C ₆ alkoxy group (the substituents are the same or different 1 to 3 halogen atoms)” means the above “C ₁ -C ₆ alkoxy group”. In addition to `` group '', for example, trifluoromethoxy group, trichloromethoxy group, difluoromethoxy group, dichloromethoxy group, dibromomethoxy group, fluoromethoxy group, chloromethoxy group, bromomethoxy group, iodomethoxy group, 2,2, 2-trichloroethoxy group, 2,2,2-trifluoroethoxy group, 2-bromoethoxy group, 2-chloroethoxy group, 2-fluoroethoxy group, 3-chloropropoxy group, 3,3,3-trifluoropropoxy Group, 4-fluorobutoxy group, 3-fluoro-2-methylpropoxy group, 3,3,3-trifluoro-2-methylpropoxy group The “C ₁ -C ₆ alkoxy group” substituted by 1 to 3 “halogen atoms” which are the same or different, such as 6,6,6-trichlorohexyloxy group, Or the above-mentioned “C ₁ -C ₄ alkoxy group” optionally substituted by 1 to 3 different “halogen atoms”, more preferably 1 to 3 “fluorine atoms” which are the same or different. or said optionally substituted by a chlorine atom, "a" C ₁ -C ₃ alkoxy group ", still more preferably, a methoxy group, an ethoxy group, a propoxy group or a trifluoromethoxy group, and most preferably, It is a methoxy group.

In the present invention, the “C ₁ -C ₆ alkylthio group” means that, for example, a sulfur atom is bonded to the “C ₁ -C ₆ alkyl group” such as methylthio group, ethylthio group, propylthio group, butylthio group, hexylthio group. Preferably a methylthio group or an ethylthio group.

In the present invention, the “optionally substituted amino group (the substituents are the same or different one or two C ₁ -C ₆ alkyl groups)” is the same as or in addition to the amino group. 1 to 2 different “C _{1 to} C ₆ alkyl groups” are substituted amino groups, and preferably 1 to 2 different “C _{1 to} C ₄ alkyl groups” are substituted An amino group which may be used, more preferably a dimethylamino group or a diethylamino group.

In the present invention, the “C ₂ -C ₆ alkylene group” is, for example, a straight chain or branched chain having 2 to 6 carbon atoms such as ethylene group, tritylene group, tetramethylene group, pentamethylene group, hexamethylene group. An alkylene group, preferably a tetramethylene group or a pentamethylene group.

In the compound (I) of the present invention,
AB section is
(1a) Preferably, a group represented by the formula C = NC (R ¹ ) (R ² ), a group represented by the formula NC (O) C (R ¹ ) (R ² ), or a formula C = NC ( R ¹ ) (R ² ) O is a group represented by
R ¹ and R ² are
(2a) preferably are independently optionally substituted C ₁ -C ₄ alkyl group (the substituent is the same or different one to three fluorine atoms or chlorine atoms.) Is Or they together form a C ₁ -C ₂ alkoxyimino group,
Suitable from (2b), independently, a C ₁ -C ₄ alkyl group,
(2c) Even more preferably, both are methyl groups.

Xn is
(3a) preferably, X is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, optionally substituted C ₁ -C ₄ alkyl group (said substituents may be the same or different 1-3 A fluorine atom or a chlorine atom) or an optionally substituted C ₁ -C ₄ alkoxy group (the substituent is the same or different 1 to 3 fluorine atoms or chlorine atoms), and n is , 0, 1 or 2;
(3b) from suitably, X is a fluorine atom, a chlorine atom, a C ₁ -C ₃ alkyl or C ₁ -C ₃ alkoxy radical, n is 0 or 1,
(3c) Even more preferably, X is a fluorine atom or a methyl group, n is 0 or 1,
Ym is
(4a) preferably, Y is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, optionally substituted C ₁ -C ₄ alkyl group (said substituents may be the same or different 1-3 is a fluorine atom or a chlorine atom.), optionally substituted C ₁ -C ₄ alkoxy group (said substituents are the same or different one to three fluorine atoms or chlorine atoms.), a phenyl group , A phenoxy group, an amino group which may be substituted (the substituent is the same or different C ₁ -C ₄ alkyl group), a nitro group, a hydroxyl group or a mercapto group, and m is 0, 1 or 2;
(4b) than Suitably, Y is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, a C ₁ -C ₃ alkoxy group or a hydroxyl group, m is 0 or 1,
(4c) Even more preferably, Y is a fluorine atom, a chlorine atom, a methyl group, a methoxy group or a hydroxyl group, and m is 0 or 1.

In the compound (I) of the present invention, the AB portion is selected from (1a), R ¹ and R ² are selected from (2a) to (2c), and Xn is selected from (3a) to (3c). A compound obtained by selecting and selecting Y from (4a) to (4c) and combining them is also suitable.

For example,
(A1)
Compounds obtained by combining (1a), (2a), (3a) and (4a),
(A2)
A compound obtained by combining (1a), (2b), (3b) and (4b), or (a3)
It is a compound obtained by combining (1a), (2c), (3c) and (4c).

3- (7-fluoro-1,1-dimethyl-1H-isoindol-3-yl) quinoline,
4-Fluoro-3,3-dimethyl-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one or 8-fluoro-2,2-dimethyl-4-quinolin-3-yl- 2H-1,3-benzoxazine is also preferred.

  The compound (I) of the present invention can be converted to a salt such as sulfate, hydrochloride, nitrate and phosphate. Those salts are included in the present invention as long as they can be used as agricultural and horticultural fungicides.

  Compound (I) and a salt thereof of the present invention can be solvated, and these solvates are also encompassed in the present invention. Such solvates are preferably hydrates.

  Among the compounds (I) of the present invention, there are compounds having an asymmetric carbon, and in this case, the present invention includes a mixture containing one kind of optically active substance and several kinds of optically active substances in an arbitrary ratio. Include.

  Representative compounds of the present invention are exemplified in the following table, but the present invention is not limited to these compounds.

Hereinafter, “Me” represents a methyl group, and “— (CH ₂ ) ₅ —”, “═O”, “═NOH” and “= NOMe” are formed by R ¹ and R ² being joined together. In “Xn” and “Ym”, “H” indicates that n is 0 or m is 0.

Among the above exemplary compounds, suitable compounds are
Compound No. 1-2, Compound No. 1-5, Compound No. 1-37, Compound No. 2-2, Compound No. 2-3, Compound No. 2-4, Compound No. A compound of 2-9, a compound of compound number 3-4, a compound of compound number 3-8, or a compound of compound number 4-1.
Further preferred compounds are the compound No. 1-5, the compound No. 1-37, the compound No. 2-3, the compound No. 2-4, the compound No. 2-9, the compound No. 3- 4 or compound No. 3-8,
Particularly suitable compounds are
Compound No. 1-5: 3- (7-fluoro-1,1-dimethyl-1H-isoindol-3-yl) quinoline,
Compound No. 2-9: 4-fluoro-3,3-dimethyl-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one or compound No. 3-8: 8- Fluoro-2,2-dimethyl-4-quinolin-3-yl-2H-benzoxazine.

上式中、Ｘ、Ｙ、ｍ、ｎ、Ｒ^１及びＲ^２は、前記と同意義を示す。 The 3-substituted quinoline compound of the present invention can be produced by the method described below.
(Method A)

In the above formula, X, Y, m, n, R ¹ and R ² are as defined above.

In the method A, the alcohol compound (II) or the olefin compound (III) is reacted with chloroacetonitrile to obtain a chloroacetamide compound (IV), which is further oxidized at the benzyl position to eliminate the chloroacetyl group and simultaneously close the ring. In the compound (I) of the present invention, the AB portion is represented by the formula C═NC (R ¹ ) (R ² ) (wherein R ¹ and R ² are as defined above). This is a method for producing the compound (Ia) which is a group.

(Step A-1)
Step A-1 is a step for producing chloroacetamide compound (IV) by reacting alcohol compound (II) or olefin compound (III) with chloroacetonitrile in the presence of an acid.

  The amount of chloroacetonitrile used is usually 1 to 60 mol, and preferably 1.1 to 30 mol, per 1 mol of compound (II) or compound (III).

  When a solvent is used in this step, the solvent used is not particularly limited as long as it does not inhibit the reaction. For example, organic acids such as acetic acid and formic acid; hydrocarbons such as hexane, cyclohexane, and octane; benzene, Aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; or ethers such as dioxane, diethyl ether, tetrahydrofuran (THF) and dibutyl ether; Preferred are organic acids, hydrocarbons, aromatic hydrocarbons or halogenated hydrocarbons, and more preferred are organic acids (particularly acetic acid).

  The acid used in this step is not particularly limited as long as it is used as an acid in a normal liter reaction. For example, inorganic acids such as sulfuric acid, formic acid, phosphoric acid, perchloric acid; benzenesulfonic acid, toluene A sulfonic acid such as sulfonic acid or trifluoromethanesulfonic acid; or a Lewis acid such as tin tetrachloride or trifluoroboron, preferably an inorganic acid or sulfonic acid, and more preferably an inorganic acid (particularly , Sulfuric acid).

  The amount of the acid used is usually 1 to 20 mol, preferably 1.1 to 10 mol, per 1 mol of alcohol compound (II) or olefin compound (III).

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 100 ° C., preferably 0 ° C. to 80 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is usually 15 minutes to 120 hours, preferably 30 minutes to 72 hours.

  The alcohol compound (II) which is a starting material of the above-mentioned method A is a method in which a Grignard reagent is reacted with phthalic anhydride or the like {for example, Journal of Organic Chemistry, 27, 76 (1962) Journal of American Chemical Society, 73, 5885 (1951) and Journal of Medicinal Chemistry, 18, 177 1975) and the like, and a method of reacting an organolithium reagent with phthalic anhydride, etc. {eg, Journal of Medicinal Chemistry, 38, 4411 (1995) The carbonyl group of the ketone compound produced according to the method described in {.) Is a known method {for example, lithium aluminum hydride, Reduction with a metal hydride such as aluminum iodide or sodium borohydride, or hydrazone is formed once with hydrazine or arylsulfonyl nidrazine, and then alkali metal alkoxide such as sodium ethoxide or sodium methoxide, potassium hydroxide or tertiary It can be produced by reduction with a so-called Wolf-Kishner reduction in the presence of a base such as butyryloxypotassium.

  The olefin compound (III) used in this step is a known method {for example, Bulletin de la Societe Kimike de France (Bull. Soc. Chim. Fr.), 2, 633 (1935). Dehydration of alcohols with acids as described in Tetrahedron Lett., 35, 4129 (1994) and Journal of Organic Chemistry (J. Org. Chem.) 47, 2928 (1982), a method of dehydrating an alcohol with a leaving group} by dehydrating the alcohol compound (II).

(Step A-2)
Step A-2 is a step for producing the target compound (Ia) by oxidizing the benzyl position of the chloroacetamide compound (IV) to eliminate the chloroacetyl group and simultaneously ring-closing it.

  When a solvent is used in this step, the solvent used is not particularly limited as long as it does not inhibit the reaction. For example, organic acids such as formic acid and acetic acid; hydrocarbons such as hexane, cyclohexane, benzene, toluene, and xylene Halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; or ethers such as dioxane, diethyl ether, tetrahydrofuran (THF) and dibutyl ether, preferably organic acids or hydrocarbons More preferred are organic acids (particularly acetic acid).

  The oxidizing agent used in this step is not particularly limited as long as it is used for oxidizing an active methylene group to a carbonyl group in a normal oxidation reaction. For example, potassium permanganate, barium permanganate, etc. Permanganates; chromic acids such as chromium oxide, dichromate, chromate, chromyl oxide, chromic acid ester; or metal oxides such as ruthenium tetroxide, selenium dioxide, preferably chromic acid Salts, and more preferably chromium oxide.

The amount of the oxidizing agent to be used is usually 1 to 20 mol, preferably 1.1 to 15 mol, per 1 mol of the chloroacetamide compound (IV).
While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally 0 ° C. to 200 ° C., preferably 10 ° C. to 150 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is usually 15 minutes to 120 hours, preferably 30 minutes to 72 hours.

上式中、Ｘ、Ｙ、ｍ、ｎ、Ｒ^１及びＲ^２は、前記と同意義を示す。 (B-1 method)

In the above formula, X, Y, m, n, R ¹ and R ² are as defined above.

In the method B-1, an oxindole compound (V) is reacted with a bromoquinoline compound (VI), and in the compound (I) of the present invention, the AB moiety is of the formula NC (O) C (R ¹ ) (R ² ) (wherein R ¹ and R ² are as defined above), a method for producing compound (Ib), which is a group represented by:

(Process B-1)
Step B-1 is a step for producing the compound (Ib) of the present invention by coupling the oxindole compound (V) with the bromoquinoline compound (VI) in the presence of a catalyst and a base.

  The amount of the brimoquinoline compound (VI) to be used is usually 1 to 5 mol, preferably 1.1 to 3 mol, per 1 mol of the oxindole compound (V).

  The base used in this step is not particularly limited as long as it is used as a base in a normal reaction. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate and potassium bicarbonate Alkali metal bicarbonates; may be alkali metal hydroxides or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, barium hydroxide, preferably alkali metal carbonates, and more preferably Is potassium carbonate.

  The amount of the base to be used is usually 1 to 30 mol, and preferably 1 to 15 mol with respect to 1 mol of the oxindole compound (V).

  The solvent used in this step is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, and toluene; halogenated carbonization such as dichloromethane, dichloroethane, chloroform, and tetrachloroethane. Hydrogens; ethers such as dioxane, diethyl ether, tetrahydrofuran (THF), ethylene glycol dimethyl ether; amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, hexamethylphosphoric triamide (HMPA); acetone, methyl ethyl ketone, methyl Ketones such as isobutyl ketone and cyclohexanone; nitriles such as acetonitrile and isobutyronitrile; or esters such as methyl acetate, ethyl acetate and propyl acetate. An amide, more preferably a N- methylpyrrolidone.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally 0 ° C. to 250 ° C., preferably 20 ° C. to 200 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

  The catalyst that can be used in this step is not particularly limited as long as it can couple an aryl halide and an amide, but is preferably a metal halide such as copper chloride, copper bromide, copper iodide, Preferred is copper bromide or copper iodide.

  In this reaction, the catalyst can be used in an amount of 0.1 equivalent to 1 equivalent or more per 1 equivalent of the oxindole compound (V).

  The oxindole compound (V) which is a starting material of the above-mentioned method B-1 is a known compound or a known method {for example, Journal of American Chemical Society, Vol. 75, 1508 (1953), Chemishe Berichte, 49, 2769 (1916)}.

  The bromoquinoline compound (VI) which is a starting material of the above-mentioned method B-1 is a known compound or is described in a known method {for example, Chemishe Berichte, 19, 2766 (1886). And the method described in Tetrahedron Letters, 38, 4415 (1997)}.

上式中、Ｘ、Ｙ、ｍ、ｎ、Ｒ^１及びＲ^２は、前記と同意義を示す。 (B-2 method)

In the above formula, X, Y, m, n, R ¹ and R ² are as defined above.

In the method B-2, an iodobenzene compound (VII) is reacted with an aminoquinoline compound (VIII) to produce a dimethylamide compound (IX), which is then hydrolyzed and cyclized to give a compound (I ) In which the AB moiety is a group represented by the formula NC (O) C (R ¹ ) (R ² ) (wherein R ¹ and R ² are as defined above) This is a method for separately producing Ib).

(Step B-2)
Step B-2 is a step for producing a dimethylamide compound (IX) by reacting the iodobenzene compound (VII) with an aminoquinoline compound (VIII) in the presence of a catalyst and a base.

  The amount of the aminoquinoline compound (VIII) used is usually 1 to 6 mol, preferably 1 to 3 mol, per 1 mol of the iodobenzene compound (VII).

  The base used in this step is not particularly limited as long as it is used as a base in a normal reaction. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate and potassium bicarbonate Alkali metal hydrogen carbonate; may be an alkali metal hydroxide or alkaline earth metal hydroxide such as sodium hydroxide, potassium hydroxide or barium hydroxide, preferably an alkali metal salt, more preferably , Potassium carbonate.

  The amount of the base used is usually 1 to 30 mol, and preferably 1 to 15 mol per 1 mol of the iodobenzene compound (VII).

  The solvent used in this step is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, and xylene; halogenated carbonization such as dichloromethane, dichloroethane, chloroform, and tetrachloroethane. Hydrogens; ethers such as dioxane, diethyl ether, tetrahydrofuran (THF), ethylene glycol dimethyl ether; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphoric triamide (HMPA); acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. Ketones; nitriles such as acetonitrile and isobutyronitrile; or esters such as methyl acetate, ethyl acetate and propyl acetate, preferably hydrocarbons; To apply, xylene.

  The catalyst that can be used in this step is not particularly limited as long as it can conjugated aryl halide and amine, but is preferably a metal halide such as copper chloride, copper bromide, copper iodide, Preferred is copper bromide or copper iodide.

  In this reaction, the catalyst can be used in an amount of 0.1 to 1 equivalent or more with respect to 1 equivalent of the iodobenzene compound (VII).

  The reaction temperature varies depending on the raw material compound, the reaction reagent, the solvent, and the like, but is usually 20 ° C to 250 ° C, and preferably 20 ° C to 200 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

  The iodobenzene compound (VII) which is a starting material of the above-mentioned method B-2 is a known compound or a known method {for example, Journal of Medicinal Chemistry, Vol. 45, p. 321. (Method described in 2002)}.

  The aminoquinoline compound (VIII), which is the starting material of the above-mentioned method B-2, is a known compound or is a combination of known methods (for example, Journal of Medicinal Chemistry, 39 From 4-hydroxy-3-nitroquinolin-2-one obtained by the method described in Vol. 23, p. 4682 (1996), Journal of Praktical Chemistry, Vol. 336 No. 4, page 311 (1994) to give 2,4-dichloro-3-nitroquinoline, which is described in Chemishe Berichte, Vol. 511, page 1509 (1918). Can be produced by a method for obtaining a target product by a conventional method.

(Step B-3)
Step B-3 is a step of producing the carboxylic acid compound (X) by hydrolyzing the dimethylamide compound (IX) in the presence of a base or an acid.

  When a base is used in this step, the base used is not particularly limited as long as it is used as a base in a normal reaction. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate, Alkali metal hydrogen carbonates such as potassium hydrogen carbonate; alkali metal hydrides such as sodium hydride, lithium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and barium hydroxide or alkaline earth Metal hydroxides; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- (N, N-dimethylamino) Pyridine, N, N-dimethyl Nilin, N, N-diethylaniline, 1,5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [ 5.4.0] -7-undecene (DBU) or other organic bases or organic metals such as butyllithium or lithium diisopropylamide, preferably alkali metal hydroxide or alkaline earth metal hydroxide More preferred are alkali metal hydroxides (particularly sodium hydroxide).

  The amount of the base to be used is usually 1 to 30 mol, preferably 2 to 15 mol, per 1 mol of the dimethylamide compound (IX).

  When an acid is used in this step, the acid used is not particularly limited as long as it is used as an acid in a normal reaction. For example, hydrogen halides such as hydrochloric acid and bromic acid; trifluoroacetic acid and tosylic acid Organic acids such as Lewis acids such as boron trichloride and boron tribromide; or sulfuric acid, preferably a halogen acid, and more preferably hydrochloric acid.

  The amount of the acid used is usually 1 to 30 mol, and preferably 2 to 15 mol, per 1 mol of the dimethylamide compound (IX).

  The solvent used in this step is not particularly limited as long as it does not inhibit the reaction. For example, alcohols such as methanol and ethanol, hydrocarbons such as hexane, cyclohexane, benzene and toluene; dichloromethane, dichloroethane and chloroform Halogenated hydrocarbons such as tetrachloroethane; ethers such as dioxane, diethyl ether, tetrahydrofuran (THF) and ethylene glycol dimethyl ether; amides such as dimethylformamide, dimethylacetamide and hexamethylphosphoric triamide (HMPA); acetone, Ketones such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; nitriles such as acetonitrile and isobutyronitrile; esters such as methyl acetate, ethyl acetate and propyl acetate; vinegar ; Water; a or a mixture thereof, preferably, an alcohol, water or a mixture thereof, more preferably a mixture of ethanol and water.

  When mixing the solvents, the mixing ratio varies depending on the type of the solvent to be combined, but is usually 100: 1 to 1: 100, and preferably 10: 1 to 1:10.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 250 ° C., preferably 0 ° C. to 120 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

(Step B-4)
In the step B-4, the compound (Ib) of the present invention is produced by ring-closing the carboxylic acid compound (X) in the presence or absence of an acid or a base and in the presence or absence of a condensing agent. It is a process to do.

  When an acid is used in this step, the acid used is not particularly limited as long as it is used as an acid in a normal reaction. For example, hydrogen halides such as hydrochloric acid and bromic acid; trifluoroacetic acid and tosylic acid Organic acids such as Lewis acids such as boron trichloride and boron tribromide; or sulfuric acid, preferably a halogen acid, and more preferably hydrochloric acid.

  The amount of the acid used is usually 1 to 30 mol, and preferably 2 to 15 mol, per 1 mol of the carboxylic acid compound (X).

  When a base is used in this step, the base used is not particularly limited as long as it is used as a base in a normal reaction. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate, Alkali metal hydrogen carbonates such as potassium hydrogen carbonate; alkali metal hydrides such as sodium hydride, lithium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and barium hydroxide or alkaline earth Metal hydroxides; alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide; triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- (N, N-dimethylamino) Pyridine, N, N-dimethyl Nilin, N, N-diethylaniline, 1,5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [ 5.4.0] -7-undecene (DBU) and other organic bases; or organometallics such as butyllithium and lithium diisopropylamide, preferably organic bases, more preferably Triethylamine.

  The amount of the base to be used is usually 1 to 30 mol, preferably 1.1 to 15 mol, per 1 mol of the carboxylic acid compound (X).

  When a condensing agent is used in this step, the condensing agent to be used is not particularly limited as long as it is used as a condensing agent in a normal dehydration condensation reaction. For example, dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide (DIPC) Carbodiimides such as N-ethyl-N′-ethyl- (3-dimethylaminopropyl) carbodiimide (EDC); diethyl phosphate cyanide (DEPC), diphenyl phosphate azide (DPPA), benzisoxazol-1-yl- Phosphoric acids such as tris (dimethylamino) phosphonium hexafluorophosphide salt (BOP); pyridinium salts such as 1-methyl-2-chloropyridinium iodide, 1-ethyl-2-fluoropyridinium = tetrafluoroborate; or carbonyl Can be diimidazole (CDI), preferably pyridi A um salts, more preferably a iodide 1-methyl-2-chloro-pyridinium.

  The amount of the condensing agent to be used is usually 1 to 30 mol, preferably 1.1 to 15 mol, per 1 mol of the carboxylic acid compound (X).

  The solvent used in this step is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, and toluene; halogenated carbonization such as dichloromethane, dichloroethane, chloroform, and tetrachloroethane. Hydrogens; ethers such as dioxane, diethyl ether, tetrahydrofuran (THF), ethylene glycol dimethyl ether; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphoric triamide (HMPA); acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. Ketones; nitriles such as acetonitrile and isobutyronitrile; or esters such as methyl acetate, ethyl acetate and propyl acetate, preferably halogenated hydrocarbons It is an ether, more preferably, dichloromethane, dichloroethane, or THF.

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 150 ° C., preferably 0 ° C. to 40 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

上式中、Ｘ、Ｙ、ｍ、ｎ、Ｒ^１及びＲ^２は、前記と同意義を示す。 (Method C)

In the above formula, X, Y, m, n, R ¹ and R ² are as defined above.

In the method C, a trifluoromethanesulfonic acid compound (XI) is subjected to a coupling reaction with a boric acid compound (XII), and in the compound (I) of the present invention, the AB portion is represented by the formula C═NC (R ¹ ) (R ² ) A method for producing compound (Ic), which is a group represented by —O (wherein R ¹ and R ² are as defined above).

(Step C-1)
Step C-1 is a step for producing the compound (Ic) of the present invention by coupling the trifluoromethanesulfonic acid compound (XI) with the boric acid compound (XII) in the presence of a catalyst and a base. .

  The amount of the boric acid compound (XII) used is usually 1 to 3 mol, preferably 1 to 1.5 mol, per 1 mol of the trifluoromethanesulfonic acid compound (XI).

  The base used in this step is not particularly limited as long as it is used as a base in a normal reaction. For example, alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate and potassium bicarbonate Alkali metal hydrogen carbonates; alkali metal hydroxides or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide and barium hydroxide; or alkali metals such as sodium methoxide, sodium ethoxide and potassium t-butoxide It can be an alkoxide, preferably an alkali metal carbonate, and more preferably potassium carbonate.

  The amount of the base to be used is usually 1 to 30 mol, preferably 1.1 to 15 mol, per 1 mol of the trifluoromethanesulfonic acid compound (XI).

  The solvent used in this step is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, and toluene; halogenated carbonization such as dichloromethane, dichloroethane, chloroform, and tetrachloroethane. Hydrogens; ethers such as dioxane, diethyl ether, tetrahydrofuran (THF), ethylene glycol dimethyl ether; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphoric triamide (HMPA); acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. Ketones; nitriles such as acetonitrile and isobutyronitrile; or esters such as methyl acetate, ethyl acetate, and propyl acetate, preferably hydrocarbons; Preferably, toluene.

  The catalyst that can be used in this step is not particularly limited as long as it can camp on a trifluoromethanesulfonic acid compound and a boric acid compound, but is preferably palladium carbon, palladium acetate, dichlorobis (triphenylphosphine) palladium, tetrakis. Palladium compounds such as (triphenylphosphine) palladium and tris (dibenzalacetone) palladium, more preferably tetrakis (triphenylphosphine) palladium or tris (dibenzalacetone) palladium, most preferably Is tetrakis (triphenylphosphine) palladium.

  In this reaction, the catalyst can be used in an amount of 0.1 to 1 equivalent or more per 1 equivalent of the trifluoromethanesulfonic acid compound (XI).

  While the reaction temperature varies depending on the raw material compound, reaction reagent, solvent and the like, it is generally −20 ° C. to 250 ° C., preferably 0 ° C. to 140 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is usually 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

  The trifluoromethanesulfonic acid compound (XI) which is a starting material of the above-mentioned method C is a known compound or a known method {for example, Chemical and Pharmaceutical Bulletin, Vol. 44, 734 Page (1996)}.

上式中、Ｘ、Ｙ、ｍ及びｎは、前記と同意義を示す。 (Method D)

In the above formula, X, Y, m and n are as defined above.

In the method D, an alkoxy compound (XIII) is reacted with a bromoquinoline compound (VI), and in the compound (I) of the present invention, the compound (Id) in which the AB portion is a group represented by the formula C═NSO ₂ ).

(Process D-1)
Step D-1 is a step for producing the compound (Id) of the present invention by condensing the alkoxy compound (XIII) with a bromoquinoline compound (VI) in the presence of a base in an inert solvent.

  The amount of the bromoquinoline compound (VI) used is usually 1 to 3 mol, preferably 1.1 to 2 mol, per 1 mol of the alkoxy compound (XIII).

  The base used in this step is not particularly limited as long as it can exchange halogen for lithium, but may be organic metals such as butyl lithium and lithium diisopropylamide, and more preferably butyl lithium. .

  The amount of the base used is usually 1 to 3 mol, preferably 1.1 to 1.5 mol, per 1 mol of the alkoxy compound (XIII).

  The solvent used in this step is not particularly limited as long as it does not inhibit the reaction. For example, hydrocarbons such as hexane, cyclohexane, benzene, and toluene; halogenated carbonization such as dichloromethane, dichloroethane, chloroform, and tetrachloroethane. Hydrogens; ethers such as dioxane, diethyl ether, tetrahydrofuran (THF), ethylene glycol dimethyl ether; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphoric triamide (HMPA); acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc. Ketones; nitriles such as acetonitrile and isobutyronitrile; or esters such as methyl acetate, ethyl acetate and propyl acetate, preferably hydrocarbons or ethers A class, more preferably, hexane, cyclohexane or THF.

  The reaction temperature varies depending on the raw material compound, the reaction reagent, the solvent, and the like, but is usually −120 ° C. to 150 ° C., and preferably −80 ° C. to 40 ° C.

  While the reaction time varies depending on the raw material compound, reaction reagent, solvent, reaction temperature and the like, it is generally 10 minutes to 120 hours, preferably 30 minutes to 72 hours.

  The alkoxy compound (XIII) which is a starting material of the method D is a known compound or a known method {for example, Journal of American Chemical Society, 65, 457 ( 1943)}.

  After completion of each of the above reactions, the target compound of each reaction can be collected from the reaction mixture according to a conventional method. For example, the reaction mixture is appropriately neutralized, and if insoluble matter is present, it is removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, and after washing with water, the organic layer containing the target compound is removed. After separating and drying over anhydrous magnesium sulfate or the like, the solvent is distilled off.

  If necessary, the obtained target compound can be further purified by a conventional method such as recrystallization, reprecipitation or chromatography.

  In the step of producing the salt of the compound (I) of the present invention, an acid is added to an extract concentrate of the reaction mixture containing the compound (I) produced in each step or a solution obtained by dissolving the compound (I) in an appropriate solvent. Is done by.

Examples of the acid used in the reaction include hydrohalic acid such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, inorganic acids such as nitric acid, perchloric acid, sulfuric acid and phosphoric acid; methane Organic acid salts such as C ₁ -C ₆ alkyl sulfonic acids such as sulfonic acid, trifluoromethane sulfonic acid and ethane sulfonic acid, aryl sulfonic acids such as benzene sulfonic acid and p-toluene sulfonic acid, succinic acid and oxalic acid; Alternatively, it may be an organic acid amide compound such as saccharin.

  The acid is generally used in an amount of 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to compound (I).

  The solvent used in the reaction is not particularly limited as long as the reaction is not inhibited, but is preferably an ether such as ether, diisopropyl ether, tetrahydrofuran (THF) or dioxane, or an alcohol such as methanol or ethanol.

The reaction temperature is usually −20 ° C. to 50 ° C., and preferably −10 ° C. to 30 ° C.
The reaction time varies depending on the type and temperature of the solvent used, but is usually 10 minutes to 1 hour.

  The resulting salt is isolated by conventional methods. That is, when it precipitates as a crystal, it is isolated by filtration, and when it is water-soluble, it is isolated as an aqueous solution by separating an organic solvent and water.

  The compounds of the present invention are useful as active ingredients for pest control agents. For example, as an agricultural and horticultural fungicide, it shows an excellent control effect against diseases caused by various plant pathogens. In particular, rice blast, head blight, azuki bean, tomato, cucumber and kidney bean gray mold, mycorrhizal disease, onion white leaf blight, wheat snow rot, powdery mildew, apple moniliosis, spotted leaf disease It exhibits excellent control effects against various diseases such as tea anthracnose, pear scab, black spot, grape black rot, and citrus black spot. Since the compound of the present invention has an excellent therapeutic effect, disease control by treatment after infection is possible.

  When using the compound of the present invention, it can be formulated into various forms such as emulsions, powders, wettable powders, liquids, granules, suspensions, etc. together with adjuvants as in the case of conventional agricultural chemical formulations. . When these preparations are actually used, they can be used as they are or after being diluted to a predetermined concentration with a diluent such as water.

  The auxiliary agent used is a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickening agent, a stabilizer, and the like, and can be appropriately added as necessary.

  Carriers used are divided into solid carriers and liquid carriers, and solid carriers are starch, sugar, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat flour, rice bran powder, wood powder, fish powder, powdered milk and other animal and vegetable powders. Or mineral powder such as talc, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, silica, sulfur powder, etc., and the liquid carrier is Animal and vegetable oils such as soybean oil, nut oil and corn oil; alcohols such as ethyl alcohol and ethylene glycol; ketones such as acetone and methyl ethyl ketone; ethers such as dioxane and tetrahydrofuran; kerosene, kerosene, liquid paraffin, Xylene, trimethylbenzene, tetramethylbenzene Aliphatic / aromatic hydrocarbons such as cyclohexane and solvent naphtha; Halogenated hydrocarbons such as chloroform and chlorobenzene; Acid amides such as dimethylformamide; Esters such as ethyl acetate and glycerol esters of fatty acids; Nitriles; sulfur-containing compounds such as dimethyl sulfoxide; or N-methylpyrrolidone.

  The compounding mass ratio of the compound of the present invention and the adjuvant is usually 0.05: 99.95 to 90:10, and preferably 0.2: 99.8 to 80:20.

  The concentration or amount used of the compound of the present invention varies depending on the target crop, method of use, formulation, application rate, etc., but in the case of foliage treatment, it is usually 0.1 to 10,000 ppm per active ingredient, In the case of soil treatment, it is usually 10 to 100,000 g / ha, and preferably 100 to 10,000 g / ha.

  The compound of the present invention may be used in combination or in combination with other agricultural chemicals such as insecticides, acaricides, attractants, nematicides, fungicides, antiviral agents, herbicides, plant growth regulators, etc., as necessary. Preferably, they are used in combination with or in combination with insecticides, acaricides, nematicides or fungicides.

  The insecticide, acaricide or nematicide used is, for example, O- (4-bromo-2-chlorophenyl) O-ethyl S-propyl phosphorothioate (generic name: propenophos), O- (2,2-dichloro). Vinyl) O, O-dimethyl phosphate (generic name: dichlorovos), O-ethyl O- {3-methyl-4- (methylthio) phenyl} N-isopropyl phosphoramidate (generic name: phenamiphos), O, O- Dimethyl O- (4-nitro-m-tolyl) phosphorothioate (generic name: fenitrothion), O-ethyl O- (4-nitrophenyl) phenylphosphonothioate (generic name: EPN), O, O-diethyl O- ( 2-Isopropyl-6-methylpyrimidin-4-yl) phosphorothioate (generic name: diazinon), O, O-dimethyl O- (3,5,6-trichloro-2-pyridyl) phosphorothioate (generic name: chlorpyrifosmethyl), O, S-dimethyl N-acetyl phosphoramidothioate (generic name: acephate), O- (2,4 -Dichlorophenyl) Organophosphate compounds such as O-ethyl S-propyl phosphorodithioate (generic name: prothiophos); 1-naphthyl N-methylcarbamate (generic name: carbaryl), 2-isopropoxyphenyl N-methyl Carbamate (generic name: propoxyl), 2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyloxime (generic name: aldicarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methyl Carbamate (generic name: carbofuran), dimethyl N, N '-[Thiobis {(methylimino) carbonyloxy}] bisethaneimidothioate (generic name: thiodicarb), S-methyl N- (methylcarbamoyloxy) thioacetimidate (generic name: mesomil), N, N-dimethyl 2-methylcarbamoyloxyimino-2- (methylthio) acetamide (generic name: oxamyl), 2- (ethylthiomethyl) phenyl N-methylcarbamate (generic name: etiophencarb), 2-dimethylamino-5,6-dimethyl Carbamate compounds such as pyrimidin-4-yl N, N-dimethylcarbamate (generic name: pyrimicarb), 2-sec-butylphenyl N-methylcarbamate (generic name: fenocarb); S, S′-2-dimethylaminotri Methylenebis (thiocarbamate) (generic name : Neratistoxin compounds such as N, N-dimethyl-1,2,3-trithian-5-ylamine (generic name: thiocyclam); 2,2,2-trichloro-1,1-bis (4- Organochlorine compounds such as chlorophenyl) ethanol (generic name: dicophore), 4-chlorophenyl-2,4,5-trichlorophenylsulfone (generic name: tetradiphone); bis {tris (2-methyl-2-phenylpropyl) tin } Organometallic compounds such as oxide (generic name: phenbutadium oxide); (RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate (generic name: Fenvale) Rate), 3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcycl Propanecarboxylate (generic name: permethrin), (RS) -α-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (Generic name: cypermethrin), (S) -α-cyano-3-phenoxybenzyl (1R) -cis-3- (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: Deltamethrin), (RS) -α-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (Generic name: cyhalothrin), 4-methyl-2,3,5,6-tetrafluorobenzyl-3- (2-chloro-3,3) , 3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (generic name: tefluthrin), 2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether (generic name: eth Pyrethroid compounds such as Fenprox; 1- (4-chlorophenyl) -3- (2,6-difluorobenzoyl) urea (generic name: diflubenzuron), 1- [3,5-dichloro-4- (3-chloro) -5-trifluoromethyl-2-pyridyloxy) phenyl] -3- (2,6-difluorobenzoyl) urea (generic name: chlorfluazuron), 1- (3,5-dichloro-2,4-difluoro Phenyl) -3- (2,6-difluorobenzoyl) urea (generic name: teflubenzuron) and other benzoylurea series Compound: Juvenile hormone-like compound such as isopropyl (2E, 4E) -11-methoxy-3,7,11-trimethyl-2,4-dotecadienoate (generic name: metoprene); 2-t-butyl- Pyridazinone compounds such as 5- (4-t-butylbenzylthio) -4-chloro-3 (2H) -pyridazinone (generic name: pyridaben); t-butyl 4-{(1,3-dimethyl-5-phenoxy) Pyrazole compounds such as pyrazol-4-yl) methyleneaminooxymethyl} benzoate (generic name: fenpyroximate); 1- (6-chloro-3-pyridylmethyl) -N-nitro-imidazolidin-2-ylideneamine (generic name) : Nitro compounds such as imidacloprid); dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazides 2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,6-tetrahydro-2H-1,3,5-thiadiazin-4-one (generic name) : Bubrophezine), trans- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxothiazolidinone-3-carboxamide (generic name: hexythiazox), N-methylbis (2,4-xylyliminomethyl) Amine (generic name: amitraz), N ′-(4-chloro-O-tolyl) -N, N-dimethylformamidine (generic name: chlordimeform), (4-ethoxyphenyl)-{3- (4-fluoro- It may be a compound such as 3-phenoxyphenyl) propyl} (dimethyl) silane (generic name: silafluophene). Furthermore, the compound of the present invention can be used in combination or in combination with microbial pesticides such as BT agents and entomopathogenic virus agents, antibiotics such as avermectin and milbemycin.

  Examples of the bactericides used include 2-anilino-4-methyl-6- (1-propynyl) pyrimidine (generic name: mepanipyrim), 4,6-dimethyl-N-phenyl-2-pyrimidinamine (generic name: pyrimethanil). Pyrimidinamine compounds such as 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) butanone (generic name: triazimephone), 1- (biphenyl) -4-yloxy) -3,3-dimethyl-1- (1H, 1,2,4-triazol-1-yl) butan-2-ol (generic name: viteltanol), 1- {N- (4-chloro -2-trifluoromethylphenyl) -2-propoxyacetimidoyl} imidazole (generic name: triflumizole), 1- {2- (2,4-dichlorophenyl)- -Ethyl-1,3-dioxolan-2-ylmethyl} -1H-1,2,4-triazole (generic name: ethaconazole), 1- {2- (2,4-dichlorophenyl) -4-propyl-1,3 -Dioxolan-2-ylmethyl} -1H-1,2,4-triazole (generic name: propiconazole), 1- {2- (2,4-dichlorophenyl) pentyl} -1H-1,2,4-triazole (Generic name: penconazole), bis (4-fluorophenyl) (methyl) (1H-1,2,4-triazol-1-ylmethyl) silane (generic name: flusilazole), 2- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-ylmethyl) hexanenitrile (generic name: microbutanyl), (2RS, 3RS) -2- (4-chlorophenyl) -3-Cyclopropyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol (generic name: cyproconazole), (RS) -1- (4-chlorophenyl) -4 , 4-Dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol (generic name: terbuconazole), (RS) -2- (2,4-dichlorophenyl)- 1- (1H-1,2,4-triazol-1-yl) hexan-2-ol (generic name: hexaconazole), (2RS, 5RS) -5- (2,4-dichlorophenyl) tetrahydro-5 (1H-1,2,4-triazol-1-ylmethyl) -2-furyl 2,2,2-trifluoroethyl ether (generic name: farconazole cis), N-propyl-N- {2- (2 , 4,6-tri Chlorophenoxy) ethyl} imidazole-1-carboxamide (generic name: prochloraz), 2- (4-fluorophenyl) -1- (1H-1,2,4triazol-1-yl) -3-trimethylsilylpropane-2- Azole compounds such as all (generic name: cimeconazole); quinoxaline compounds such as 6-methyl-1,3-dithiolo [4,5-b] quinoxalin-2-one (generic name: quinomethionate); (Dithiocarbamate) polymer (generic name: mannebu), zinc ethylene bis (dithiocarbamate) polymer (generic name: dinecarb), zinc (zinc) and Manganese ethylene bis (dithiocarbamate) (manebu) complex compound (Generic name: manzeb), dizincbis (dimethyldithiocarbamate) ethyl Dithiocarbamate compounds such as bis (dithiocarbamate) (generic name: polycarbamate) and zinc propylene bis (dithiocarbamate) polymer (generic name: provineb); 4,5,6,7-tetrachlorophthalide (general Name: Fusaride), Tetrachloroisophthalonitrile (generic name: chlorothalonil), Organochlorine compounds such as pentachloronitrobenzene (generic name: Kintozen); Methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate (generic name) Benzimidazole compounds such as: benomyl), dimethyl 4,4 ′-(o-phenylene) bis (3-thioallophanate) (generic name: thiophanate methyl), methylbenzimidazol-2-ylcarbamate (generic name: carbendazim); 3-chloro-N- ( -Pyridinamine compounds such as chloro-2,6-dinitro-4-α, α, α-trifluorotolyl) -5-trifluoromethyl-2-pyridinamine (generic name: fluazinam); 1- (2-cyano- Cyanoacetamide compounds such as 2-methoxyiminoacetyl) -3-ethylurea (generic name: simoxanyl); methyl N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate (generic name) : Metalaxyl), 2-methoxy-N- (2-oxo-1,3-oxazolidine-3-yl) aceto-2 ', 6'-xylidide (generic name: oxadixyl), (±) -α-2-chloro -N- (2,6-xylylacetamido) -γ-butyrolactone (generic name: off-race), methyl N-phenylacetyl-N- (2,6-xylyl) -DL- Alaninate (generic name: benalaxyl), methyl N- (2-furoyl) -N- (2,6-xylyl) -DL-alaninate (generic name: furalaxyl), (±) -α- [N- (3-chlorophenyl) ) Cyclopropanecarboxamide] -γ-butyrolactone (generic name: cyprofuran) and other phenylamide compounds; N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfamide (generic name: diclofluuride) Sulfenic acid compounds such as cupric hydroxide (generic name: cupric hydroxide), copper compounds such as copper 8-quinolinolate (generic name: organic copper); 5-methylisoxazol-3-ol Isoxazole compounds such as (generic name: hydroxyisoxazole); aluminum tris (ethylphosphonate) (generic name: fosetyl) Luminium), O-2,6-dichloro-p-tolyl-O, O-dimethyl phosphorothioate (generic name: tolcrophos-methyl), S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphoro Organophosphorous compounds such as dithioate and aluminum ethyl hydrogen phosphonate; N- (trichloromethylthio) cyclohexyl-4-ene-1,2-dicarboximide (generic name: captan), N- (1,1,2,2 N-halogenothioalkyl compounds such as -tetrachloroethylthio) cyclohexyl-4-ene-1,2-dicarboximide (generic name: captaphor), N- (trichloromethylthio) phthalimide (generic name: folpette); N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropyl Pan-1,2-dicarboximide (generic name: procymidone), 3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide (generic name: iprodione), ( RS) -3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione (generic name: vinclozolin) and the like; α, α, benzanilide compounds such as α-trifluoro-3′-isopropoxy-o-toluanilide (generic name: flutolanil), 3′-isopropoxy-o-toluanilide (generic name: mepronil); N, N ′-[piperazine- Piperazine compounds such as 1,4-diylbis {(trichloromethyl) methylene}] diformamide (generic name: triphorin); 2 ′ Pyridine-based compounds such as 4'-dichloro-2- (3-pyridyl) acetophenone O-methyloxime (generic name: pyriphenox); (±) -2,4'-dichloro-α- (pyrimidin-5-yl ) Benzhydryl alcohol (generic name: phenarimol), (±) -2,4′-difluoro-α- (1H-1,2,4-triazol-1-ylmethyl) benzhydryl alcohol (generic name: furtria) Carbinol compounds such as pho); piperidine compounds such as (RS) -1- {3- (4-t-butylphenyl) -2-methylpropyl} piperidine (generic name: phenpropidin); (±) Morpholine compounds such as cis-4- {3- (4-t-butylphenyl) -2-methylpropyl} -2,6-dimethylmorpholine (generic name: phenpropimorph) Organic tin compounds such as triphenyltin hydroxide (generic name: fentin hydroxide) and triphenyltin acetate (generic name: fentin acetate); 1- (4-chlorobenzyl) -1-cyclopentyl-3- Urea compounds such as phenylurea (generic name: pencyclone); (E, Z) 4- {3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl} morpholine (generic name: dimethomorph), etc. Synthetic acid compounds of the above; phenyl carbamate compounds such as isopropyl 3,4-diethoxycarbanilate (generic name: dietophanecarb); 3-cyano-4- (2,2-difluoro-1,3-benzodioxole -4-yl) pyrrole (generic name: fludioxonil), 3- (2 ', 3'-dichloropheny ) -4-cyano - pyrrole (common name: fenpiclonil) may be cyanopyrrole type compounds such as.

  Hereinafter, the compounds of the present invention will be specifically described with reference to Examples, Formulation Examples and Test Examples, but the present invention is not limited thereto.

Example 1
3- (1,1-Dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-4, Method A)
(1) 2-Chloro-N- {1-methyl-1- [2- (quinolin-3-ylmethyl) phenyl] ethyl} acetamide To a mixed solution of acetic acid (0.25 mL) and sulfuric acid (21.3 μL, 0.39 mmol), A solution of 3- (2-isopropylbenzyl) quinoline (0.05 g, 0.19 mmol) in chloroacetonitrile (0.12 mL, 1.9 mmol) was added at room temperature. Then, it stirred at room temperature for 25 hours, water and saturated sodium carbonate aqueous solution were added, and ethyl acetate extracted. The organic phase was dried over magnesium sulfate, filtered, concentrated under reduced pressure, and purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane / ethyl acetate = 1/1) to obtain the desired product (21.1 mg). Yield 31%.
Melting point: 165-166 ° C.
¹ H-NMR vector (500 MHz, CDCl ₃ ) δppm: 1.86 (6H, s), 3.42 (2H, s), 4.46 (2H, s), 6.75 (1H, br s), 7.09 (1H, dd, J = 1.6, 7.7Hz), 7.25-7.28 (1H, m), 7.33 (1H, ddd, J = 1.6, 7.7, 8.8Hz), 7.49 (1H, ddd, J = 1.1, 7.1, 8.2Hz), 7.55 ( 1H, d, J = 2.2Hz), 7.58 (1H, dd, J = 1.1, 8.2Hz), 7.65-7.68 (2H, m), 8.08 (1H, d, J = 8.8Hz), 8.80 (1H, d , J = 2.2Hz).
Mass spectrum (M / Z): 352 (M ⁺ ), 259, 244, 230.

(2) 3- (1,1-Dimethyl-1H-isoindol-3-yl) quinoline The compound (12.3 mg, 0.035 mmol) of (1) above was dissolved in acetic acid (0.12 mL), and chromic acid (7.0 mg , 0.07 mmol) and refluxed for 1 hour. Then, it cooled to room temperature, sodium sulfite aqueous solution and saturated sodium carbonate aqueous solution were added, and ethyl acetate extracted. The organic phase was dried over magnesium sulfate, filtered, concentrated under reduced pressure, purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane / ethyl acetate = 1/1), and the desired product (4.3 mg). Yield 45%.
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.62 (6H, s), 7.42-7.48 (2H, m), 7.56 (1H, d, J = 7.1Hz), 7.60 (1H, t, J = 7.4 Hz), 7.79-7.82 (2H, m), 7.96 (1H, d, J = 7.7Hz), 8.21 (1H, d, J = 8.2Hz), 8.74 (1H, d, J = 2.2Hz), 9.49 ( 1H, d, J = 2.2Hz).
Mass spectrum (M / Z): 272 (M ⁺ ), 257, 242, 231, 216, 128.
The following compounds of Examples 2 to 11 were obtained in the same manner as in Example 1.

Example 2
3′-Quinolin-3-ylspiro [cyclohexane-1,1′-isoindole] (Compound No. 1-2)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.59-1.61 (3H, m), 1.86-1.95 (5H, m), 2.12-2.14 (2H, m), 7.26-7.61 (2H, m), 7.62 (2H, t, J = 7.4Hz), 7.79 (2H, t, J = 7.4Hz), 7.96 (1H, d, J = 8.2Hz), 8.21 (1H, d, J = 8.8Hz), 8.71 (1H , d, J = 1.6 Hz), 9.48 (1H, d, J = 1.6 Hz).
Mass spectrum (M / Z): 312 (M ⁺ ), 283, 271, 257, 128.

Example 3
3- (7-Fluoro-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-5)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.72 (6H, s), 7.12 (1H, t, J = 8.6 Hz), 7.40-7.44 (1H, m), 7.58-7.62 (2H, m), 7.77-7.81 (1H, m), 7.94 (1H, d, J = 8.0Hz), 8.20 (1H, d, J = 8.6Hz), 8.71 (1H, d, J = 1.7Hz), 9.47 (1H, d , J = 1.7Hz).
Mass spectrum (M / Z): 290 (M ⁺ ), 275, 260, 249, 234, 131.

Example 4
3- (6-Fluoro-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-6)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.59 (6H, s), 7.25 (1H, t, J = 8.5 Hz), 7.23 (1H, dd, J = 2.2, 7.7 Hz), 7.60 (1H, t, J = 7.5Hz), 7.71-7.79 (2H, m), 7.93 (1H, d, J = 7.7Hz), 8.18 (1H, d, J = 8.8Hz), 8.69 (1H, d, J = 1.7 Hz), 9.43 (1H, d, J = 1.7 Hz).
Mass spectrum (M / Z): 290 (M ⁺ ), 275, 260, 249, 234, 145.

Example 5
3- (5-Fluoro-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-7)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δ ppm: 1.61 (6H, s), 7.18 (1H, dt, J = 1.6, 8.2 Hz), 7.45-7.50 (2H, m), 7.62 (1H, t, J = 7.4Hz), 7.79 (1H, t, J = 7.4Hz), 7.95 (1H, d, J = 8.2Hz), 8.21 (1H, d, J = 8.2Hz), 8.69 (1H, d, J = 1.6 Hz), 9.46 (1H, d, J = 1.6 Hz).
Mass spectrum (M / Z): 290 (M ⁺ ), 275, 260, 249, 234, 137.

Example 6
3- (6-Chloro-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-10)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.61 (6H, s), 7.41 (1H, d, J = 8.2 Hz), 7.54 (1H, s), 7.61 (1H, t, J = 7.4 Hz) 7.71 (1H, d, J = 8.2Hz), 7.79 (1H, t, J = 7.7Hz), 7.94 (1H, d, J = 8.2Hz), 8.19 (1H, d, J = 8.8Hz), 8.70 ( 1H, d, J = 1.6Hz), 9.46 (1H, d, J = 1.6Hz).
Mass spectrum (M / Z): 308 (M ⁺ +2), 306 (M ⁺ ), 293, 291, 271, 255.

Example 7
3- (5-Chloro-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-11)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.60 (6H, s), 7.41 (1H, dd, J = 1.6, 8.2 Hz), 7.46 (1H, d, J = 8.2 Hz), 7.61 (1H, t, J = 7.4Hz) 7.75-7.79 (2H, m), 7.94 (1H, d, J = 8.2Hz), 8.19 (1H, d, J = 8.2Hz), 8.68 (1H, d, J = 2.2Hz ), 9.46 (1H, d, J = 2.2 Hz).
Mass spectrum (M / Z): 308 (M ⁺ +2), 306 (M ⁺ ), 293, 291, 271, 256.

Example 8
3- (6-Methyl-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-14)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.60 (6H, s), 2.49 (3H, s), 7.24 (1H, d, J = 7.7 Hz), 7.37 (1H, s), 7.60 (1H, t, J = 7.7Hz), 7.67 (1H, d, J = 7.7Hz), 7.78 (1H, t, J = 7.4Hz), 7.94 (1H, d, J = 8.2Hz), 8.19 (1H, d, J = 8.2Hz), 8.72 (1H, d, J = 1.6Hz), 9.48 (1H, d, J = 1.6Hz).
Mass spectrum (M / Z): 286 (M ⁺ ), 271, 256, 245, 230, 149, 128.

Example 9
3- (5-Methyl-1,1-dimethyl-1H-isoindol-3-yl) quinoline (Compound No. 1-15)
Physical properties: Oil.
¹ H-NMR spectrum (270 MHz, CDCl ₃ ) δppm: 1.60 (6H, s), 2.46 (3H, s), 7.29 (1H, d, J = 7.7Hz), 7.44 (1H, d, J = 7.7Hz) , 7.59-7.64 (2H, m), 7.79 (1H, t, J = 7.7Hz), 7.96 (1H, d, J = 8.2Hz), 8.20 (1H, d, J = 8.5Hz), 8.72 (1H, s), 9.48 (1H, s).
Mass spectrum (M / Z): 286 (M ⁺ ), 271, 255, 245, 230, 128.

Example 10
3- (7-Fluoro-1,1-dimethyl-1H-isoindol-3-yl) -4-methylquinoline (Compound No. 1-33)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.75 (6H, s), 2.75 (3H, s), 7.09-7.12 (2H, m), 7.34-7.37 (1H, m), 7.66 (1H, t , J = 7.7Hz), 7.80 (1H, t, J = 7.4Hz), 8.14 (1H, d, J = 8.2Hz), 8.18 (1H, d, J = 8.2Hz), 8.94 (1H, s).
Mass spectrum (M / Z): 304 (M ⁺ ), 303, 287, 273, 248.

Example 11
3- (7-Fluoro-1,1-dimethyl-1H-isoindol-3-yl) -8-methoxyquinoline (Compound No. 1-37)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.71 (6H, s), 4.14 (3H, s), 7.11-7.16 (2H, m), 7.43-7.44 (1H, m), 7.51-7.56 (3H m), 8.69 (1H, d, J = 1.6 Hz), 9.43 (1H, d, J = 1.6 Hz).
Mass spectrum (M / Z): 320 (M ⁺ ), 304, 291, 276, 260.

Example 12
3,3-Dimethyl-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one (Compound No. 2-8, method B-1)
3,3-dimethyl-1,3-dihydro-2H-indol-2-one (117 mg, 0.72 mmol), 3-bromoquinoline (300 mg, 1.44 mmol), copper (I) iodide (27.6 mg, 0.14) mmol) and potassium carbonate (100 mg, 0.72 mmol) were suspended in N-methylpyrrolidone (210 mg, 2.16 mmol) and stirred at 180 ° C. for 3 hours. Thereafter, the mixture was cooled to room temperature, followed by addition of water and extraction with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, concentrated under reduced pressure, and the resulting residue is purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane / ethyl acetate = 5/2). , The desired product (131.3 mg) was obtained. Yield 63%.
Melting point: 115 ° C.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.55 (6H, s), 6.92 (1H, d, J = 7.6 Hz), 7.16 (1H, d, J = 7.6 Hz), 7.23 (1H, d, J = 7.6Hz), 7.33 (1H, d J = 7.6Hz), 7.62 (1H, t, J = 7.6Hz), 7.79 (1H, t, J = 7.6Hz), 7.88 (1H, d, J = 8.2 Hz), 8.19 (1H, d, J = 8.2 Hz), 8.29 (1H, d, J = 2.7 Hz), 9.01 (1H, d, J = 2.7 Hz).
Mass spectrum (M / Z): 288 (M ⁺ ), 273, 245.

Example 13
1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one (Compound No. 2-1, Method B-2)
(1) N, N-dimethyl-2- {2- (quinolin-3-ylamino) phenyl} acetamide 2- (2-iodophenyl) -N, N-dimethylacetamide (0.95 g, 3.29 mmol), 3-amino Quinoline (0.95 g, 6.58 mmol), copper (0.10 g, 1.65 mmol), copper (I) iodide (0.31 g, 1.65 mmol) and potassium carbonate (0.45 g, 3.29 mmol) suspended in xylene (6.6 mL) The mixture was heated to reflux for 4.5 hours and then cooled to 40 ° C. Subsequently, after filtration through celite, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate) to obtain the desired product (0.66 g). Yield 66%.
Melting point: 158-159 ° C.
Mass spectrum (M / Z): 305 (M ⁺ ), 260, 232.

(2) {2- (Quinolin-3-ylamino) phenyl} acetic acid Compound (0.12 g, 0.39 mmol) of (1) above was dissolved in ethanol (7.8 mL) and sodium hydroxide dissolved in water (1.3 mL) (0.16 g, 3.9 mmol) was added, and the mixture was heated to reflux for 1 hour. After cooling to room temperature, the mixture was concentrated under reduced pressure, water and diethyl ether were added to the resulting residue, washed and separated, and the aqueous phase was acidified with 1N hydrochloric acid. Next, ethyl acetate was added and extracted. The organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to obtain the desired product (90.9 mg). Yield 84%.
Melting point: 173-178 ° C.
Mass spectrum (M / Z): 278 (M ⁺ ), 260, 231.

(3) 1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one The compound (0.41 g, 1.47 mmol) of the above (2) was dissolved in ethanol (3.7 mL), and 10% hydrochloric acid was dissolved. An ethanol solution (3.7 mL) was added, and the mixture was heated to reflux for 1 hour. After cooling to room temperature, the mixture was concentrated under reduced pressure, water was added to the resulting residue, and the mixture was extracted with diethyl ether. Next, an aqueous sodium carbonate solution was added to the aqueous phase to neutralize it, followed by extraction with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude crystals were crystallized from acetone and diethyl ether to obtain the desired product (0.15 g). Yield 39%.
Melting point: 181-183 ° C.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 3.81 (2H, s), 6.87 (1H, d, J = 7.6 Hz), 7.14 (1H, t, J = 7.6 Hz), 7.24-7.26 (1H, m), 7.37 (1H, d J = 7.6Hz), 7.63 (1H, t, J = 7.6Hz), 7.78-7.81 (1H, m), 7.89 (1H, d, J = 8.2Hz), 8.19 (1H , d, J = 8.2 Hz), 8.27 (1H, d, J = 2.1 Hz), 9.00 (1H, d, J = 2.1 Hz).
Mass spectrum (M / Z): 260 (M ⁺ ), 231.
The following compounds of Examples 14 to 21 were obtained in the same manner as in Example 12 (Method B-1) or Example 13 (Method B-2).

Example 14
1-quinolin-3-yl-1H-indole-2,3-dione (Compound No. 2-2, Method B-2)
Melting point: 227-228 ° C.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 6.96 (1H, d, J = 7.9 Hz), 7.23-7.26 (1H, m), 7.58-7.62 (1H, m), 7.67 (1H, t J = 7.3Hz), 7.77 (1H, d, J = 7.3Hz), 7.82-7.85 (1H, m), 7.92 (1H, d, J = 7.9Hz), 8.21 (1H, d, J = 8.6Hz), 8.29 (1H, d, J = 1.8Hz), 9.00 (1H, d, J = 1.8Hz).
Mass spectrum (M / Z): 274 (M ⁺ ), 246, 218, 128.

Example 15
1-quinolin-3-yl-1H-indole-2,3-dione 3-oxime (compound number 2-3, method B-2)
Melting point:> 250 ° C.
¹ H-NMR spectrum (500MHz, DMSO-d6) δppm: 6.97 (1H, d, J = 7.9Hz), 7.21 (1H, t, J = 7.3Hz), 7.41-7.44 (1H, m), 7.72 (1H , t, J = 7.3Hz), 7.88 (1H, ddd, J = 1.2, 6.7, 7.9Hz), 8.10-8.16 (3H, m), 8.61 (1H, d, J = 2.4Hz), 9.02 (1H, d, J = 2.4Hz), 13.70 (1H, br s).
Mass spectrum (M / Z): 289 (M ⁺ ), 273, 245.

Example 16
1-quinolin-3-yl-1H-indole-2,3-dione 3- (O-methyloxime) (Compound No. 2-4, method B-2)
Physical properties: amorphous.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 4.38 (3H, s), 6.89 (1H, d, J = 7.9 Hz), 7.17 (1H, t, J = 7.9 Hz), 7.36-7.39 (1H, m), 7.65 (1H, t, J = 7.9Hz), 7.79-7.82 (1H, m), 7.90 (1H, d J = 8.6Hz), 8.10 (1H, d, J = 7.9Hz), 8.19 (1H , d, J = 8.6 Hz), 8.28 (1H, d, J = 2.4 Hz), 8.99 (1H, d, J = 2.4 Hz).
Mass spectrum (M / Z): 303 (M ⁺ ), 272, 244, 128.

Example 17
3,3-Dichloro-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one (Compound No. 2-5, method B-2)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 6.89 (1H, d, J = 7.6 Hz), 7.29 (1H, d, J = 7.6 Hz), 7.37-7.40 (1H, m), 7.67 (1H, t J = 7.6Hz), 7.77 (1H, d, J = 7.6Hz), 7.82-7.86 (1H, m), 7.91 (1H, d, J = 8.2Hz), 8.21 (1H, d, J = 8.2Hz ), 8.34 (1H, d, J = 2.1Hz), 9.00 (1H, d, J = 2.1Hz).
Mass spectrum (M / Z): 328 (M ⁺ ), 293, 365.

Example 18
3,3-Difluoro-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one (Compound No. 2-6, method B-2)
Melting point: 109 ° C.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 6.94 (1H, d, J = 7.9 Hz), 7.29 (1H, t, J = 7.9 Hz), 7.49 (1H, t, J = 7.9 Hz), 7.67 (1H, t J = 7.9Hz), 7.70 (1H, d, J = 7.9Hz), 7.84 (1H, d, J = 7.9Hz), 7.91 (1H, d, J = 7.9Hz), 8.21 (1H, d, J = 8.6Hz), 8.30 (1H, d, J = 2.4Hz), 8.99 (1H, d, J = 2.4Hz).
Mass spectrum (M / Z): 296 (M ⁺ ), 267, 248, 218.

Example 19
3-Methyl-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one (Compound No. 2-7, method B-2)
Melting point: 246-247 ° C.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δ ppm: 1.97 (3H, s), 6.60 (1H, d, J = 7.6 Hz), 6.99-7.02 (1H, m), 7.11-7.14 (1H, m), 7.27 (1H, d J = 7.6Hz), 7.66 (1H, t, J = 7.6Hz), 7.81-7.84 (1H, m), 7.90 (1H, d, J = 8.2Hz), 8.18 (1H, d, J = 2.7Hz), 8.21 (1H, d, J = 8.2Hz), 8.74 (1H, d, J = 2.7Hz).
Mass spectrum (M / Z): 274 (M ⁺ ), 273, 245, 128.

Example 20
4-Fluoro-3,3-dimethyl-1-quinolin-3-yl-1,3-dihydro-2H-indol-2-one (Compound No. 2-9, method B-1)
Melting point: 129-130 ° C.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.65 (6H, s), 6.70 (1H, d, J = 8.2 Hz), 6.83 (1H, t, J = 8.2 Hz), 7.18-7.22 (1H, m), 7.63 (1H, t J = 7.6Hz), 7.80 (1H, t, J = 7.6Hz), 7.89 (1H, d, J = 8.2Hz), 8.19 (1H, d, J = 8.2Hz), 8.27 (1H, d, J = 2.1Hz), 8.97 (1H, d, J = 2.1Hz).
Mass spectrum (M / Z): 306 (M ⁺ ), 291, 263.

Example 21
4′-Fluoro-1′-quinolin-3-ylspiro [cyclohexane-1,3′-indole] -1′H-2′-one (Compound No. 2-29, method B-1)
Physical properties: amorphous.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.48-1.52 (1H, m), 1.70-1.77 (2H, m), 1.84-1.86 (1H, m), 1.96-1.99 (2H, m), 2.12 -2.21 (4H, m), 6.65 (1H, d, J = 7.6Hz), 6.81 (1H, t, J = 8.9Hz), 7.17 (1H, td., J = 5.5, 8.2Hz), 7.62 (1H , t J = 7.6Hz), 7.87-7.89 (1H, m), 7.88 (1H, d, J = 8.2Hz), 8.18 (1H, d, J = 8.2Hz), 8.25 (1H, d, J = 2.7 Hz), 8.95 (1H, d, J = 2.7 Hz).
Mass spectrum (M / Z): 346 (M ⁺ ), 317, 291.

Example 22
2,2-Dimethyl-4-quinolin-3-yl-2H-benzoxazine (Compound No. 3-4)
To a toluene solution (1 mL) of 2,2-dimethyl-4-trifluoromethanesulfonyloxy-2H-benzoxazine (211.2 mg, 0.68 mmol), quinolin-3-ylboric acid (118.1 mg, 0.68 mmol), tetrakistriphenylphosphine Palladium (39.5 mg, 0.034 mmol) and potassium carbonate (207.7 mg, 1.5 mmol) were added and refluxed for 4 hours. Water was added to the reaction solution, extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane / ethyl acetate = 4/1) to obtain the desired product (31.9 mg). Got. Yield 20%.
Physical properties: Oil.
¹ H-NMR spectrum (270 MHz, CDCl ₃ ) δ ppm: 1.71 (6H, s), 6.90-6.98 (2H, m), 7.20 (1H, d, J = 7.7 Hz), 7.41 (1H, t, J = 7.8 Hz), 7.60 (1H, t, J = 7.5Hz), 7.78 (1H, t, J = 7.5Hz), 7.89 (1H, d, J = 7.9Hz), 8.17 (1H, d, J = 8.5Hz) , 8.37 (1H, d, J = 1.9Hz), 9.11 (1H, d, J = 1.9Hz).
Mass spectrum (M / Z): 288 (M ⁺ ), 273, 246, 232, 204, 176.
The following compounds of Examples 23 and 24 were obtained in the same manner as in Example 22.

Example 23
8-Fluoro-2,2-dimethyl-4-quinolin-3-yl-2H-benzoxazine (Compound No. 3-8)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.76 (6H, s), 6.89-6.90 (1H, m), 7.00 (1H, d, J = 7.6 Hz), 7.23 (1H, t, J = 5.8 Hz), 7.61 (1H, t, J = 7.6Hz), 7.80 (1H, t, J = 7.6Hz), 7.89 (1H, d, J = 8.2Hz), 8.18 (1H, d, J = 8.2Hz) 8.37 (1H, d, J = 2.1 Hz), 9.11 (1H, d, J = 2.1 Hz).
Mass spectrum (M / Z): 306 (M ⁺ ), 291, 264, 250, 221, 153, 128, 101.

Example 24
8-chloro-2,2-dimethyl-4-quinolin-3-yl-2H-benzoxazine (Compound No. 3-12)
Physical properties: Oil.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 1.76 (6H, s), 6.88 (1H, t, J = 7.6 Hz), 7.11 (1H, dd, J = 1.5, 7.6 Hz), 7.47 (1H, dd, J = 1.5, 7.6Hz), 7.61 (1H, t, J = 7.6Hz), 7.79 (1H, t, J = 7.6Hz), 7.89 (1H, d, J = 8.6Hz), 8.17 (1H, d, J = 8.6Hz), 8.36 (1H, d, J = 2.4Hz), 9.09 (1H, d, J = 2.4Hz).
Mass spectrum (M / Z): 322 (M ⁺ ), 307, 287, 266, 203.

Example 25
3- (1,1-Dioxo-1,2-benzisothiazol-3-yl) quinoline (Compound No. 4-1)
N-Butyllithium (1.6M hexane solution, 1.2 mL, 1.92 mmol) was added to a THF solution (10 mL) of 3-bromoquinoline (0.2 mL, 1.47 mmol) at −78 ° C., and the mixture was stirred at the same temperature for 2 hours. . To the reaction solution was added a THF solution (10 mL) of 3-ethoxy-1,1-dioxo-1,2-benzisothiazole (211 mg, 1.0 mmol), and the mixture was stirred at −78 ° C. for 2 hours. After returning to room temperature, an aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane / ethyl acetate = 1/1) to obtain the desired product (100 mg). Got. Yield 34%.
Physical properties: amorphous.
¹ H-NMR spectrum (500 MHz, CDCl ₃ ) δppm: 7.72 (1H, t, J = 7.9 Hz), 7.81-7.87 (2H, m), 7.92 (1H, t, J = 7.9 Hz), 7.98 (1H, d, J = 6.7Hz), 8.02 (1H, d, J = 7.3Hz), 8.07 (1H, d, J = 6.7Hz), 8.23 (1H, d, J = 8.6Hz), 8.84 (1H, d, J = 1.8Hz), 9.44 (1H, d, J = 1.8Hz).
Mass spectrum (M / Z): 294 (M ⁺ ), 230, 203, 154, 127, 101, 76.

Formulation Example 1
Powder: Compound of Example 1 (1.0 part by mass), Doreless A (alkyl ether phosphate ester, Nippon Kayaku Co., Ltd., 0.4 part by mass), Carplex # 80-D (white carbon, Shionogi Pharmaceutical) Co., Ltd., 1.5 parts by mass), calcium carbonate (manufactured by Adachi Lime Co., Ltd., 0.5 parts by mass) and Keiwa clay-style HI (Keiwa Furnace Co., Ltd., 32.1 parts by mass) After that, it was pulverized with Ek sample KII-1 type (hammer mill, manufactured by Fuji Paudal Co., Ltd.), and 1.5 times the amount of DL clay Keiwa (Keiwa furnace material) with respect to the mass of the obtained pulverized product Co., Ltd.) was added and mixed to obtain a powder DL.

Formulation Example 2
Emulsion The compound of Example 2 (10 parts by mass) was dissolved in a mixed solution of xylene (40 parts by mass manufactured by Wako Pure Chemical Industries, Ltd.) and dimethyl sulfoxide (DMSO: 35 parts by mass manufactured by Wako Pure Chemical Industries, Ltd.) Parakol KPS (a mixture of an anionic surfactant and a nonionic surfactant, Nippon Emulsifier Co., Ltd., 25 parts by mass) was added to and mixed with the solution to obtain an emulsion.

Formulation Example 3
Wettable Compound of Example 3 (1 part by mass), Carplex # 80-D (10 parts by mass), Gohsenol GL05 (polyvinyl alcohol, manufactured by Nippon Synthetic Chemical Co., Ltd., 2 parts by mass), New Coal 291PG (Dioctylsulfosucci) Sodium salt, Nippon Emulsifier Co., Ltd., 0.5 parts by mass), Neogen powder (linear alkylbenzene sulfonate sodium salt, Daiichi Kogyo Seiyaku Co., Ltd., 5 parts by mass), Radiolite # 200 (calcined diatomaceous earth, Showa Kagaku Kogyo Co., Ltd., 10 parts by mass) and H fine powder (Kaolinite clay, Keiwa Furnace Co., Ltd., 71.5 parts by mass) are thoroughly mixed and pulverized with an EX sample KII-1 type pulverizer. To obtain a wettable powder.

Formulation Example 4
Granule The compound of Example 4 (2 parts by mass), sodium tripolyphosphate (manufactured by Mitsui Chemicals, 2 parts by mass), Amicolic NO. 1 (dextrin, manufactured by Nippon Starch Chemical Co., Ltd., 1.5 parts by mass), bentonite (produced by Toyshun Mining Co., Ltd., 25 parts by mass) and Calhin 600 (calcium carbonate, manufactured by Adachi Lime Co., Ltd., 69.5 parts by mass) Were mixed and extruded and granulated using Dome Gran (Fuji Paudal Co., Ltd., screen 0.9 mmφ). The obtained granulated material was dried with a shelf dryer (manufactured by Tabai Co., Ltd., PERFECT OVEN PS-222 type, 60 ° C.) and then sieved to 600 to 1180 μm to obtain granules.

Test example 1
Rice blast control trial (therapeutic effect)
The plant cultivation test plant (rice: Kofu) at the 3rd to 4th leaf stage was spray-inoculated with the pathogen spore suspension, and the pot was placed in an inoculation room having a room temperature of 20 to 23 ° C. to promote disease. The compound of the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solution (volume ratio: 7/3) to prepare a spray solution containing 300 ppm of the compound of the present invention and sprayed uniformly in the pot. The severity of the disease 7 days after the inoculation was investigated. The test was performed in duplicate.
In addition, the disease severity was determined by the following criteria by visually observing the disease severity of the test plant, and expressed in 4 stages of 0 to 3.
Disease severity: 0 (no disease at all)
1 (onset of disease is less than 40% of untreated area)
2 (onset of disease is 40% or more and less than 80%)
3 (onset of disease is 80% or more)
As a result of this test, the compound of Example 3 (Compound No. 1-5), the compound of Example 14 (Compound No. 2-2), the compound of Example 15 (Compound No. 2-3), and Example 16 (Compound No.) 2-4), Example 20 (Compound No. 2-9), Example 22 (Compound No. 3-4), Example 23 (Compound No. 3-8) and Example 25 (Compound No. 3-8) The compound No. 4-1) had a disease severity of 0.

Test example 2
Tomato gray mold control test (preventive effect)
A compound of the present invention is dissolved in dimethyl sulfoxide and methanol (volume ratio 7: 3) in a pot cultivation test plant (tomato: large-scale longevity) in the second to third leaf stages, and contains 300 ppm of the compound of the present invention. A spray solution was prepared and sprayed uniformly. After cultivating for one day, the pot was spray-inoculated with the pathogen spore suspension, and the pot was placed in an inoculation room having a room temperature of 20 to 23 ° C. to promote disease. The degree of disease onset 2 days after the inoculation was investigated. The test was performed in duplicate.
In addition, the disease severity was determined by the following criteria by visually observing the disease severity of the test plant, and expressed in 4 stages of 0 to 3.
Disease severity: 0 (no disease at all)
1 (onset of disease is less than 40% of untreated area)
2 (onset of disease is 40% or more and less than 80%)
3 (onset of disease is 80% or more)
As a result of this test, the compound of Example 2 (Compound No. 1-2), the compound of Example 3 (Compound No. 1-5), the compound of Example 11 (Compound No. 1-37), Example 20 (Compound No.) The compound of 2-9), the compound of Example 22 (Compound No. 3-4) and the compound of Example 23 (Compound No. 3-8) had a disease severity of 0.

The compound of the present invention can be used as an agricultural and horticultural fungicide and exhibits excellent effects on various phytopathogenic fungi, particularly rice blast, without causing damage to the host plant. As an excellent one.
The plant diseases in which the compound of the present invention exhibits excellent efficacy are, for example, rice blast (Pyricularia oryzae) and cucumber, tomato and kidney bean (Botrytis cinerea). However, it is not limited to these.

Claims (13)

Formula (I)

[Where:
The A-B moiety is a group represented by the formula C = NC (R ¹ ) (R ² ), a group represented by the formula NC (O) C (R ¹ ) (R ² ), or a formula C = NC (R ¹ ) represents a group represented by (R ² ) O or a group represented by the formula C═NSO ₂ ,
R ¹ and R ² are each independently a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 halogen atoms), substitution An optionally substituted C ₁ -C ₆ alkoxy group (the substituents are the same or different 1 to 3 halogen atoms) or a hydroxyl group, or they are taken together to form an oxo group , hydroxyimino group, to form a C ₁ -C ₆ alkoxyimino group or _C 2 -C ₆ alkylene group,
X is a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 halogen atoms), and an optionally substituted C _1- C ₆ alkoxy group (said substituents are the same or different 1 to 3 halogen atoms.), a phenoxy group, a hydroxyl group, C ₁ -C ₆ alkylthio group or an optionally substituted amino group (the substituent groups represent the same or different 1-2 C ₁ -C ₆ alkyl group.),
n represents an integer of 0 to 4, and when n is 2 or more, a plurality of Xs may be the same or different,
Y is a halogen atom, an optionally substituted C ₁ -C ₆ alkyl group (the substituent is the same or different 1 to 3 halogen atoms), and an optionally substituted C _1- C ₆ alkoxy group (the substituent is the same or different 1 to 3 halogen atoms), phenyl group, phenoxy group, optionally substituted amino group (the substituent is the same or different is one to two C ₁ -C ₆ alkyl group.), a nitro group, a hydroxyl group or a mercapto group,
m represents an integer of 0 to 6, and when m is 2 or more, a plurality of Y may be the same or different. ]
Or a salt thereof. The A-B moiety is a group represented by the formula C = NC (R ¹ ) (R ² ), a group represented by the formula NC (O) C (R ¹ ) (R ² ), or a formula C = NC (R ¹⁾ (R 2) is a group represented by ^O, a compound or a salt thereof according to claim 1. R ¹ and R ² are each independently an optionally substituted C ₁ -C ₄ alkyl group (the substituents are the same or different 1 to 3 fluorine atoms or chlorine atoms). or, or they together form a C ₁ -C ₂ alkoxyimino group, the compound or a salt thereof according to claim 1 or 2. R ¹ and ^{R 2} is independently C ₁ -C ₄ alkyl group, compound or salt thereof according to claim 1 or 2. The compound or a salt thereof according to claim 1 or 2, wherein R ¹ and R ² are both methyl groups. X is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an optionally substituted C ₁ -C ₄ alkyl group (the substituent is the same or different 1 to 3 fluorine atoms or chlorine atoms) Or an optionally substituted C ₁ -C ₄ alkoxy group (the substituent is the same or different 1 to 3 fluorine atoms or chlorine atoms), and n is 0, 1 or 6. The compound according to any one of claims 1 to 5, or a salt thereof, which is 2. X is a fluorine atom, a chlorine atom, a C ₁ -C ₃ alkyl or C ₁ -C ₃ alkoxy radical, n is 0 or 1 A compound according to any one of claims 1 to 5, Or a salt thereof.   The compound or salt thereof according to any one of claims 1 to 5, wherein X is a fluorine atom or a methyl group, and n is 0 or 1. Y is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an optionally substituted C ₁ -C ₄ alkyl group (the substituent is the same or different 1 to 3 fluorine atoms or chlorine atoms) ), An optionally substituted C ₁ -C ₄ alkoxy group (the substituent is the same or different 1 to 3 fluorine atoms or chlorine atoms), a phenyl group, a phenoxy group, and a substituted group. An amino group (the substituent is the same or different 1 to 2 C ₁ -C ₄ alkyl groups), a nitro group, a hydroxyl group or a mercapto group, and m is 0, 1 or 2 The compound according to any one of claims 1 to 8, or a salt thereof. Y is a fluorine atom, a chlorine atom, a bromine atom, C ₁ -C ₃ alkyl group, a C ₁ -C ₃ alkoxy group or a hydroxyl group, m is 0, 1 or 2, any of Claim 1-8 2. The compound or salt thereof according to claim 1.   The compound or a salt thereof according to any one of claims 1 to 8, wherein Y is a fluorine atom, a chlorine atom, a methyl group, a methoxy group, or a hydroxyl group, and m is 0 or 1.   The compound represented by the general formula (I) is 3- (7-fluoro-1,1-dimethyl-1H-isoindol-3-yl) quinoline, 4-fluoro-3,3-dimethyl-1-quinoline- 2. 3-yl-1,3-dihydro-2H-indol-2-one or 8-fluoro-2,2-dimethyl-4-quinolin-3-yl-2H-1,3-benzoxazine. Or a salt thereof.   An agrochemical containing the compound according to any one of claims 1 to 12 or a salt thereof as an active ingredient.