JP2013216626A - Miticide or insecticide including aryloxyacetamide compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a miticide and/or an insecticide having superior miticidal activity and/or insecticidal activity, being excellently safe, and including industrially advantageously synthesizable compounds as active ingredients.SOLUTION: A miticide or an insecticide includes an aryloxyacetamide compound such as 2-[(3-bromo-6-quinolinyl)oxy]-N-(1,1-dimethyl-2-butyne-1-yl)-2-(methylthio)-acetamide, 2-[(3-bromo-6-quinolinyl)oxy]-N-(1,1-dimethylethyl)-2-(methylthio)-acetamide, 2-[(3,8-dibromo-6-quinolinyl)oxy]-N-(1,1-dimethyl-2-butyne-1-yl)-2-(methylthio)-acetamide, and 2-[(3-bromo-6-quinolinyl)oxy]-N-(1,1-dimethyl-2-butyne-1-yl)-butane amide.

Description

  The present invention relates to an acaricide or insecticide containing an aryloxyacetamide compound. More specifically, the present invention relates to an acaricide and an acaricide containing an aryloxyacetamide compound having an excellent acaricidal activity and / or insecticidal activity, excellent safety and industrially advantageous synthesis as an active ingredient, and / Or pesticides.

  As compounds structurally related to the aryloxyacetic acid amide compound used in the present invention, Patent Documents 1 to 3 disclose compounds represented by Formulas (A) to (C).

Wherein (A), X ₂ represents a hydrogen atom, a halogen atom, etc. C1~8 alkyl group.
Y ₂ represents a hydrogen atom, a halogen atom, a C1-8 alkyl group, or the like.
R ₆ represents a phenyl group, a cyano group, a C1-4 alkyl group, or the like.
R ₇ represents a hydrogen atom, a C1-4 alkyl group, or the like.
R ₈ and R ₉ independently represent a hydrogen atom, a C1-3 alkyl group, or the like.
R ₁₀ represents a halogen atom or a C1-4 alkyl group.

In the formula (B), X ₃ represents a chlorine atom, a bromine atom, or a methyl group.
Y ₃ represents a chlorine atom, a bromine atom, or a methyl group.
R ₁₁ represents an ethyl group or an n-propyl group.
R ₁₂ represents an ethyl group.

In the formula (C), one of X ₄ and Y ₄ represents a nitrogen atom or a nitrogen oxide, and the other represents CR (R represents a hydrogen atom, a halogen atom, etc.), or X ₄ And Y ₄ both represent a nitrogen atom.
Z ₁ represents a hydrogen atom, a halogen atom or the like.
R ₁₃ represents an alkyl group, an alkenyl group, or the like.
R ₁₄ represents a benzyloxymethyl group or the like in which the phenyl ring of the benzyl moiety is optionally substituted with a C1-4 alkoxy group.
R ₁₅ and R ₁₆ are each independently a hydrogen atom, a C1-3 alkyl group, provided that when both are not hydrogen atoms and both are other than hydrogen atoms, the combined carbon atom sum does not exceed 4. Etc.
R ₁₇ represents C1-4 alkyl, C3-6 cycloalkyl and the like.

  Further, Patent Documents 4 to 6 disclose compounds similar to the compound represented by the formula (C).

JP-A-2005-517642 (WO2003 / 048128) JP 2006-507338 A (WO 2004/047537) JP 2006-507339 A (WO 2004/047538) JP 2006-526600 A (WO 2004/108663) JP 2008-521850 A (WO 2006/058699) JP 2008-521851 A (WO 2006/058700)

  The present invention relates to an acaricide and / or insecticide containing an aryloxyacetic acid amide compound or a salt thereof as an active ingredient which is excellent in acaricidal activity and / or insecticidal activity, is excellent in safety, and can be synthesized industrially advantageously. It is an issue to provide.

  As a result of intensive studies to solve the above problems, the present inventor has found that an acaricide and / or insecticide containing an aryloxyacetamide compound having a specific structure or a salt thereof as an active ingredient has excellent acaricidal activity. And / or having insecticidal activity and exhibiting good properties and high safety. The present invention has been completed based on this finding.

That is, the present invention includes the following.
[1] An acaricide or insecticide containing at least one selected from an aryloxyacetamide compound represented by the formula (I) or a salt thereof.

［式（I）中、
Ｃｙは、無置換のもしくは置換基Ｘを有するＣ６〜１０アリール基、または無置換のもしくは置換基Ｘを有するヘテロアリール基を示す。置換基Ｘは、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ３〜８シクロアルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、水酸基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、アミノ基、無置換のもしくは置換基を有するＣ１〜６アルキルアミノ基、無置換のもしくは置換基を有するＣ１〜７アシル基、無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基、無置換のもしくは置換基を有するＣ１〜６アルキルチオ基、無置換のもしくは置換基を有するＣ１〜６アルキルスルホニル基、無置換のもしくは置換基を有するＣ１〜６アルコキシスルホニル基、無置換のもしくは置換基を有するＣ６〜１０アリール基、無置換のもしくは置換基を有するヘテロアリール基、無置換のもしくは置換基を有するヒドロキシイミノＣ１〜６アルキル基、ニトロ基、シアノ基、またはハロゲン原子である。置換基Ｘは２つ以上であってもよく、置換基Ｘを２つ以上有するときＸは互いに同一でも異なっていてもよい。
Ｒ^1aは、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、無置換のもしくは置換基を有するＣ１〜６アルコキシ基、または無置換のもしくは置換基を有するＣ１〜６アルキルチオ基を示す。
Ｒ^1bは、水素原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、または無置換のもしくは置換基を有するＣ２〜６アルキニル基を示す。ここで、Ｒ^1aとＲ^1bは相互に繋がってＲ^1aおよびＲ^1bが結合する炭素原子とともに環を形成してもよい。
Ｚは、酸素原子または硫黄原子を示す。
Ｑは、無置換のもしくは置換基を有する１−ピロリジニル基、無置換のもしくは置換基を有する２，５−ジヒドロ−１Ｈ−ピロール−１−イル基、無置換のもしくは置換基を有する１−ピペリジニル基、無置換のもしくは置換基を有する１−ピペラジニル基、無置換のもしくは置換基を有する４−モルホリニル基、無置換のもしくは置換基を有するオクタヒドロ−２（１Ｈ）−イソキノリニル基、無置換のもしくは置換基を有するＣ６〜１０アリールアミノ基、無置換のもしくは置換基を有するヘテロアリールアミノ基、式（II）で表される基、または式（III）で表される基を示す。

[In the formula (I),
Cy represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted X heteroaryl group. Substituent X is unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or A substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 Alkylsulfonyl group, unsubstituted or substituted C1-6 alkoxysulfonyl group, unsubstituted or substituted C 10 aryl group, an unsubstituted or heteroaryl group having a substituent, hydroxyimino C1~6 alkyl group having unsubstituted or substituted group, a nitro group, a cyano group or a halogen atom. Two or more substituents X may be present, and when two or more substituents X are present, X may be the same or different from each other.
R ^1a is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, an unsubstituted or A C1-6 alkoxy group having a substituent, or an unsubstituted or substituted C1-6 alkylthio group is shown.
R ^1b represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, or an unsubstituted or substituted C2-6 alkynyl group. Show. Here, R ^1a and R ^1b may be connected to each other to form a ring together with the carbon atom to which R ^1a and R ^1b are bonded.
Z represents an oxygen atom or a sulfur atom.
Q represents an unsubstituted or substituted 1-pyrrolidinyl group, an unsubstituted or substituted 2,5-dihydro-1H-pyrrol-1-yl group, an unsubstituted or substituted 1-piperidinyl group Group, unsubstituted or substituted 1-piperazinyl group, unsubstituted or substituted 4-morpholinyl group, unsubstituted or substituted octahydro-2 (1H) -isoquinolinyl group, unsubstituted or A C6-10 arylamino group having a substituent, an unsubstituted or substituted heteroarylamino group, a group represented by formula (II), or a group represented by formula (III) is shown.

（式（II）中、 ＊は結合位置を示す。
Ｒ²は、水素原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、無置換のもしくは置換基を有するＣ１〜７アシル基、または無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基を示す。
Ｒ³およびＲ⁴は、それぞれ独立に、水素原子、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、無置換のもしくは置換基を有するＣ６〜１０アリール基、またはシアノ基を示す。ここで、Ｒ³とＲ⁴は相互に繋がってＲ³およびＲ⁴が結合する炭素原子とともに環を形成してもよい。
Ｒ^5aは、無置換のもしくは置換基を有するＣ１〜６アルキル基、無置換のもしくは置換基を有するＣ３〜８シクロアルキル基、無置換のもしくは置換基を有するＣ２〜６アルケニル基、無置換のもしくは置換基を有するＣ２〜６アルキニル基、無置換のもしくは置換基を有するＣ１〜７アシル基、カルボキシル基、無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基、無置換のもしくは置換基を有するＣ２〜６アルケニルオキシカルボニル基、無置換のもしくは置換基を有するＣ２〜６アルキニルオキシカルボニル基、無置換のもしくは置換基を有するアミノカルボニル基、無置換のもしくは置換基を有するＣ６〜１０アリール基、無置換のもしくは置換基を有するヒドロキシイミノＣ１〜６アルキル基、またはシアノ基を示す。）

(In formula (II), * indicates a bonding position.
R ² represents a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 alkynyl group, A substituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group is shown.
R ³ and R ⁴ each independently have a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted group A C2-6 alkynyl group, an unsubstituted or substituted C6-10 aryl group, or a cyano group is shown. Here, R ³ and R ⁴ may be connected to each other to form a ring together with the carbon atom to which R ³ and R ⁴ are bonded.
R ^5a is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted Or a substituted C2-6 alkynyl group, an unsubstituted or substituted C1-7 acyl group, a carboxyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted group Having a C2-6 alkenyloxycarbonyl group, unsubstituted or substituted C2-6 alkynyloxycarbonyl group, unsubstituted or substituted aminocarbonyl group, unsubstituted or substituted C6-10 aryl group , An unsubstituted or substituted hydroxyimino C1-6 alkyl group, or a cyano group . )

（式（III）中、 ＊は結合位置を示す。
Ｒ²およびＲ³は、前記と同じ意味を示す。
Ｒ^5bは、無置換のもしくは置換基を有するヘテロアリール基を示す。）］

(In formula (III), * indicates a bonding position.
R ² and R ³ have the same meaning as described above.
R ^5b represents an unsubstituted or substituted heteroaryl group. ]]

[2] The killing agent according to [1], wherein Cy is an unsubstituted or substituted quinolyl group, R ^1a is an unsubstituted or substituted C1-6 alkylthio group, and R ^1b is a hydrogen atom. Tick or insecticide.
[3] The acaricide or insecticide according to [1] or [2], wherein Q is a group represented by the formula (II).
[4] R ³ Cl to 6 alkyl groups having an unsubstituted or substituted, having Cl to 6 alkyl group, and R ^5a is an unsubstituted or substituted group having R ⁴ is an unsubstituted or substituted C2 The acaricide or insecticide according to any one of [1] to [3], which is a -6 alkynyl group.

  The acaricide or insecticide according to the present invention can effectively control mites or insects that are problematic in terms of crops and hygiene.

  The acaricide or insecticide according to the present invention contains at least one selected from aryloxyacetamide compounds or salts thereof. The content of the aryloxyacetamide compound or a salt thereof in the acaricide or insecticide according to the present invention is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight. Moreover, the acaricide or insecticide according to the present invention can be used after diluted with water or the like. The content of the aryloxyacetamide compound or a salt thereof in the acaricide or insecticide according to the present invention when diluted is preferably 0.001 to 1% by weight, more preferably 0.01 to 0.1% by weight. %.

  The aryloxyacetic acid amide compound used in the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as compound (I)).

First, in the present invention, 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.
Specific examples of the group that can be a “substituent” include the following groups.
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group An alkyl group;
A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl 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, 3-hexenyl group, 4 -C2-6 alkenyl groups such as a hexenyl group and a 5-hexenyl group;
C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl 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, etc. A C2-6 alkynyl group of

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;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
A C2-6 alkynyloxy group such as an ethynyloxy group or a propargyloxy group;
A C6-10 aryl group such as a phenyl group or a naphthyl group;
C6-10 aryloxy groups such as phenoxy group and 1-naphthoxy group;
A C7-11 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;
C1-7 acyl groups such as formyl group, acetyl group, propionyl group, benzoyl group, cyclohexylcarbonyl group;
C1-7 acyloxy groups such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group;
A C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group;
Carboxyl group;
Hydroxyl group; oxo group;

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

Cyano group; nitro group; amino group;
A C1-6 alkylamino group such as a methylamino group, a dimethylamino group, a diethylamino group;
A C6-10 arylamino group such as an anilino group or a naphthylamino group;
A C7-11 aralkylamino group such as a benzylamino group or a phenylethylamino group;
C1-7 acylamino groups such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group;
A C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group;

An aminocarbonyl group having no substituent or a substituent such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, an N-phenyl-N-methylaminocarbonyl group;
Imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group;
Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; methoxyiminomethyl group, (1-methoxyimino) ethyl group;

A mercapto group;
A C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
A C2-6 alkenylthio group such as a vinylthio group or an allylthio group;
A C2-6 alkynylthio group such as an ethynylthio group or a propargylthio group;
A C6-10 arylthio group such as a phenylthio group or a naphthylthio group;
A heteroarylthio group such as a thiazolylthio group or a pyridylthio group;
A C7-11 aralkylthio group such as a benzylthio group or a 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 A (C1-6 alkylthio) carbonyl group such as a group, (t-butylthio) carbonyl group;

A C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group;
A C2-6 alkenylsulfinyl group such as an allylsulfinyl group;
A C2-6 alkynylsulfinyl group such as a propargylsulfinyl group;
A C6-10 arylsulfinyl group such as a phenylsulfinyl group;
Heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group;
A C7-11 aralkylsulfinyl group such as a benzylsulfinyl group or a phenethylsulfinyl group;
A C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group;
A C2-6 alkenylsulfonyl group such as an allylsulfonyl group;
A C2-6 alkynylsulfonyl group such as a 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;
A 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group;
A heteroaryl group of a condensed ring such as indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group;
Saturated heterocyclic groups such as aziridinyl group, oxiranyl group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group, octahydro-2 (1H) -isoquinolinyl group;
A tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, or a t-butyldimethylsilyl group;
A triphenylsilyl group;
In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure.

[Cy]
In formula (I), Cy represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted heteroaryl group.

The “C6-10 aryl group” may be monocyclic or polycyclic. In the polycyclic aryl group, if 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.

  The “heteroaryl group” is preferably a 5- to 10-membered aryl group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms as atoms constituting the ring. The heteroaryl group may be monocyclic or polycyclic. In the polycyclic heteroaryl group, if at least one ring is heteroaryl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring.

  Examples of the heteroaryl group include the 5-membered heteroaryl group, the 6-membered heteroaryl group and the condensed heteroaryl group exemplified in the above-mentioned “substituent”. Among these, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, indolyl group, benzofuryl group, benzothienyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group It is preferable that it is a quinolyl group.

[Substituent X]
Substituent X is unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or A substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 Alkylsulfonyl group, unsubstituted or substituted C1-6 alkoxysulfonyl group, unsubstituted or substituted C 10 aryl group, an unsubstituted or heteroaryl group having a substituent, hydroxyimino C1~6 alkyl group having unsubstituted or substituted group, a nitro group, a cyano group or a halogen atom. Two or more substituents X may be present. The upper limit of the number of substituents X can be a chemically acceptable number, but is preferably four. When having two or more substituents X, Xs may be the same or different from each other.

  The “C1-6 alkyl group” in X may be a straight chain or a branched chain. As the alkyl group, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl 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.

As the “alkyl group having a substituent”,
A C3-8 cycloalkyl C1-6 alkyl group such as a cyclopropylmethyl group, a 2-cyclopropylethyl group, a cyclopentylmethyl group, a 2-cyclohexylethyl group, a 2-cyclooctylethyl 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 A C1-6 haloalkyl group such as a group, a perfluorohexyl group, a perchlorohexyl group, a perfluorooctyl group, a perchlorooctyl group, a 2,4,6-trichlorohexyl group;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 2-hydroxyethyl group;
Methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t A C1-6 alkoxy C1-6 alkyl group such as a butoxyethyl group;
C2-6 alkenyloxy C1-6 alkyl groups such as vinyloxymethyl group, allyloxymethyl group, propenyloxymethyl group, butenyloxymethyl group;
A heteroaryloxy C1-6 alkyl group such as a pyridin-2-yloxymethyl group;
C1-7 acyl group such as formyl group, acetyl group, propionyl group;
C1-7 acyloxy C1-6 alkyl groups such as formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group;
Carboxyl group C1-6 alkyl group such as carboxylmethyl group and carboxylethyl group;
A C1-6 alkoxycarbonyl C1-6 alkyl group such as a methoxycarbonylmethyl group, ethoxycarbonylmethyl group, n-propoxycarbonylmethyl group, i-propoxycarbonylmethyl group;
C1-7 acylamino C1-6 alkyl groups such as formamidomethyl group, acetamidomethyl group, 2-acetamidoethyl group, propionylaminomethyl group, propionylaminoethyl group;
C1-6 alkylamino such as methylaminocarbonylmethyl group, ethylaminocarbonylmethyl group, i-propylaminocarbonylmethyl group, t-butylaminocarbonylmethyl group, s-butylaminocarbonylmethyl group, n-pentylaminocarbonylmethyl group A carbonyl C1-6 alkyl group;
C1-6 such as methoxycarbonylaminomethyl group, ethoxycarbonylaminomethyl group, i-propoxycarbonylaminomethyl group, t-butoxycarbonylaminomethyl group, s-butyloxycarbonylaminomethyl group, n-pentyloxycarbonylaminomethyl group, etc. An alkoxycarbonylamino C1-6 alkyl group;
A C7-11 aralkyl group such as a benzyl group or a phenethyl group;
A C6-10 arylcarbonylamino C1-6 alkyl group such as a benzoylaminomethyl group;
And so on.

  Examples of the “C 3-8 cycloalkyl group” in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.

Examples of the “C2-6 alkenyl group” in X include a 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, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
Examples of the “substituted C2-6 alkenyl group” include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group.

Examples of the “C2-6 alkynyl group” in X include 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 and the like.
“C2-6 alkynyl group having a substituent” is a C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group, etc. And so on.

As the “C 1-6 alkoxy group” in X, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, An s-butoxy group, a t-butoxy group, an i-hexyloxy group, and the like can be given.
Examples of the “substituted C1-6 alkoxy group” include chloromethoxy group, dichloromethoxy group, difluoromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2 , 2,2-trifluoroethoxy group, C1-6 haloalkoxy group such as pentafluoroethoxy group.

  Examples of the “C1-6 alkylamino group” in X include a methylamino group, a dimethylamino group, and a diethylamino group.

Examples of the “C1-7 acyl group” in X include formyl group, acetyl group, propionyl group, benzoyl group and the like.
Examples of the “substituted C1-7 acyl group” include halogen-substituted C1-7 acyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group.

Examples of the “C1-6 alkoxycarbonyl group” in X include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and the like.
As the “C1-6 alkoxycarbonyl group having a substituent”,
Cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-methylcyclopropylmethoxycarbonyl group, 2,3-dimethylcyclopropylmethoxycarbonyl group, 2-chlorocyclopropylmethoxycarbonyl group A C3-8 cycloalkyl C1-6 alkoxycarbonyl group such as 2-cyclopropylethoxycarbonyl group;

Fluoromethoxycarbonyl group, chloromethoxycarbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2 , 2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, pentafluoroethoxycarbonyl group, 4-fluorobutoxycarbonyl group, 3,3,3-trifluoropropoxycarbonyl group, 2,2,2 -C1-6 haloalkoxycarbonyl group such as trifluoro-1-trifluoromethylethoxycarbonyl group, perfluorohexyloxycarbonyl group;
And so on.

  Examples of the “C 1-6 alkylthio group” in X include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group.

  Examples of the “C 1-6 alkylsulfonyl group” in X include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.

  Examples of the “C1-6 alkoxysulfonyl group” in X include a methoxysulfonyl group, an ethoxysulfonyl group, a t-butoxysulfonyl group, and the like.

  Examples of the “C6-10 aryl group” and the “heteroaryl group” in X include the same as those exemplified in the above Cy.

As the substituent on the “C6-10 aryl group” and the “heteroaryl group” in X,
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group An alkyl group;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
A cyano group;
And so on.
Examples of the “heteroaryl group having a substituent” include a 2,5-dimethyl-pyrrol-1-yl group.

Examples of the “hydroxyimino C1-6 alkyl group” in X include a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, and a (1-hydroxyimino) propyl group.
Examples of the “substituted hydroxyimino C1-6 alkyl group” include methoxyiminomethyl group, (1-methoxyimino) ethyl group, (1-methoxyimino) propyl group, ethoxyiminomethyl group, (1-ethoxyimino) C1-6 alkoxyimino C1-6 alkyl group such as ethyl group, (1-ethoxyimino) propyl group; C3-8 cycloalkyl C1-6 alkoxyimino C1-6 alkyl such as (1-cyclopropylmethoxyimino) ethyl group Groups; C7-11 aralkyloxyimino C1-6 alkyl groups such as benzyloxyiminomethyl group and (1-benzyloxyimino) ethyl group;

  Examples of the “halogen atom” in X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  Examples of the ring formed together with atoms on the mother nucleus to which X is connected to each other are a cyclopentene ring, a cyclohexene ring, a 3,4-dihydro-2H-pyran ring, a 3,4-dihydro-2H-thiopyran ring, Examples include 3,4-dihydro-2H-thiopyran 1,1-dioxide ring.

  Of these, Cy is preferably an unsubstituted or quinolyl group having a substituent X.

[R ^1a , R ^1b ]
In the formula (I), R ^1a is an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 alkynyl. Or a C1-6 alkoxy group having an unsubstituted or substituted group, or a C1-6 alkylthio group having an unsubstituted or substituted group.

The “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, and “C1-6 alkylthio group” in R ^1a are exemplified in the above X. The same can be mentioned.
R ^1a is preferably a C 1-6 alkylthio group.

In formula (I), R ^1b has a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, or an unsubstituted or substituted group. C2-6 alkynyl group is shown. Here, R ^1a and R ^1b may be connected to each other to form a ring together with the carbon atom to which they are bonded.

Examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, and “C2-6 alkynyl group” in R ^1b include the same as those exemplified in the above X.
R ^1b is preferably a hydrogen atom.

^{Examples of} the “ring” formed together with the carbon atom to which R ^1a and R ^1b are bonded to each other include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and the like.

[Z]
In formula (I), Z represents an oxygen atom or a sulfur atom. Preferably it is an oxygen atom.

[Q]
In the formula (I), Q is an unsubstituted or substituted 1-pyrrolidinyl group, an unsubstituted or substituted 2,5-dihydro-1H-pyrrol-1-yl group, an unsubstituted or substituted group 1-piperidinyl group having a group, unsubstituted or substituted 1-piperazinyl group, unsubstituted or substituted 4-morpholinyl group, unsubstituted or substituted octahydro-2 (1H) -isoquinolinyl A group, an unsubstituted or substituted C6-10 arylamino group, an unsubstituted or substituted heteroarylamino group, a group represented by formula (II), or a group represented by formula (III) Indicates.

Examples of the “C6-10 arylamino group” in Q include a phenylamino group, a naphthylene-1-ylamino group, and a naphthylene-2-ylamino group.
As the “heteroarylamino group” in Q,
Pyrrolylamino group, furylamino group, thienylamino group, imidazolylamino group, pyrazolylamino group, oxazolylamino group, isoxazolylamino group, thiazolylamino group, isothiazolylamino group, triazolylamino group, oxadiazolyl A 5-membered heteroaryl group such as amino group, thiadiazolylamino group, tetrazolylamino group;
And 6-membered heteroaryl groups such as a pyridylamino group, a pyrazinylamino group, a pyrimidinylamino group, a pyridazinylamino group, and a triazinylamino group.

In Q, “1-pyrrolidinyl group”, “2,5-dihydro-1H-pyrrol-1-yl group”, “1-piperidinyl group”, “1-piperazinyl group”, “4-morpholinyl group”, “octahydro” Examples of the substituent on the “-2 (1H) -isoquinolinyl group”, “C6-10 arylamino group”, and “heteroarylamino group” include the following substituents.
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group An alkyl group;
A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl 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, 3-hexenyl group, 4 -C2-6 alkenyl groups such as a hexenyl group and a 5-hexenyl 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, etc. A C2-6 alkynyl group of

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;
A C6-10 aryl group such as a phenyl group or a naphthyl group;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
Cyano group; nitro group;

式（II）中、 ＊は結合位置を示す。

In formula (II), * indicates a bonding position.

In formula (II), R ² represents a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2 -6 alkynyl group, an unsubstituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group.

As the “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-7 acyl group”, and “C1-6 alkoxycarbonyl group” in R ² , The same thing as those illustrated can be mentioned.

In formula (II), R ³ and R ⁴ are each independently an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, unsubstituted or substituted A C2-6 alkynyl group having a group, an unsubstituted or substituted C6-10 aryl group, or a cyano group is shown. Here, R ³ and R ⁴ may be connected to each other to form a ring together with the carbon atom to which they are bonded.

Examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, and “C2-6 alkynyl group” in R ³ and R ⁴ are the same as those exemplified in X above.
As the “C6-10 aryl group” in R ³ and R ^4, the same groups as those exemplified above for Cy can be mentioned.
R ³ and R ⁴ are preferably unsubstituted or substituted C1-6 alkyl groups, and more preferably C1-6 alkyl groups.

Examples of the “ring” formed together with the carbon atom to which R ³ and R ⁴ are linked to each other include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, and an oxirane ring.

In the formula (II), R ^5a is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C2-6. An alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, an unsubstituted or substituted C1-7 acyl group, a carboxyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, A substituted or substituted C2-6 alkenyloxycarbonyl group, an unsubstituted or substituted C2-6 alkynyloxycarbonyl group, an unsubstituted or substituted aminocarbonyl group, an unsubstituted or substituted group; Having a C6-10 aryl group, an unsubstituted or substituted hydroxyimino C1-6 alkyl group, or It shows the anode group.

In R ^5a , “C1-6 alkyl group”, “C3-8 cycloalkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-7 acyl group”, and “C1-6” Examples of the “alkoxycarbonyl group” include the same groups as those exemplified in the above X.

  Examples of the “C2-6 alkenyloxycarbonyl group” include ethenyloxycarbonyl group, 1-methyl-2-propenyloxycarbonyl group, 2-methyl-1-propenyloxycarbonyl group and the like.

  Examples of the “C 2-6 alkynyloxycarbonyl group” include ethynyloxycarbonyl group, propargyloxycarbonyl group, 1-methylpropargyloxycarbonyl group, 2-butynyloxycarbonyl group and the like.

  Examples of the “substituted aminocarbonyl group” include methylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group, t-butylaminocarbonyl group, s-butylaminocarbonyl group, n-pentylaminocarbonyl group and the like. C1-6 alkylaminocarbonyl group; diC1-6 alkylaminocarbonyl group such as dimethylaminocarbonyl group, diethylaminocarbonyl group; C3-8 cycloalkyl such as cyclopropylaminocarbonyl group, cyclopentylaminocarbonyl group, cyclohexylaminocarbonyl group Aminocarbonyl group; C2-6 alkynylaminocarbonyl group such as 2-propynylaminocarbonyl group; phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group; A C1-6 alkoxy C1-6 alkylaminocarbonyl group such as a ruaminocarbonyl group; a C1-6 haloalkylaminocarbonyl group such as a 2,2,2-trifluoroethylaminocarbonyl group; a C3 such as a cyclopropylmethylaminocarbonyl group; An cycloalkyl C1-6 alkylaminocarbonyl group; a C7-11 aralkylaminocarbonyl group such as a benzylaminocarbonyl group; a 1-position substituted-cyclic aminecarbonyl group such as a piperidin-1-ylcarbonyl group; .

  Examples of the “hydroxyimino C1-6 alkyl group” include a hydroxyiminomethyl group, a (1-hydroxyimino) ethyl group, and a (1-hydroxyimino) propyl group.

  Examples of the “substituted hydroxyimino C1-6 alkyl group” include methoxyiminomethyl group, (1-methoxyimino) ethyl group, (1-methoxyimino) propyl group, ethoxyiminomethyl group, (1-ethoxyimino) C1-6 alkoxyimino C1-6 alkyl group such as ethyl group, (1-ethoxyimino) propyl group; C3-8 cycloalkyl C1-6 alkoxyimino C1-6 alkyl such as (1-cyclopropylmethoxyimino) ethyl group Group; C7-11 aralkyloxyimino C1-6 alkyl group such as benzyloxyiminomethyl group and (1-benzyloxyimino) ethyl group;

式（III）中、 ＊は結合位置を示す。Ｒ²およびＲ³は、前記と同じ意味を示す。

In formula (III), * indicates a bonding position. R ² and R ³ have the same meaning as described above.

In formula (III), R ^5b represents an unsubstituted or substituted heteroaryl group.
^Examples of the “heteroaryl group” in R ^5b include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. A 5-membered heteroaryl group of
A 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group;
A heteroaryl group of a condensed ring such as indolyl group, benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group;
And a partially unsaturated 5-membered heterocycle such as a pyrrolinyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and a thiazolinyl group.

^Examples of the substituent on the “heteroaryl group” in R ^5b include the following substituents.
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group An alkyl group;
A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl 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, 3-hexenyl group, 4 -C2-6 alkenyl groups such as a hexenyl group and a 5-hexenyl 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, etc. A C2-6 alkynyl group of

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;
A C6-10 aryl group such as a phenyl group or a naphthyl group;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
Cyano group; nitro group;
5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl;
A 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group;

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

  The aryloxyacetic acid amide compound or its salt used for this invention can be manufactured by the method as described in patent documents 1-5. Some of the aryloxyacetamide compounds that can be produced by this method are exemplified below.

Butanamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (6-quinolinyloxy)-,
Butanamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (7-isoquinolinyloxy)-,
Butanamide, N- (4-hydroxy-1,1-dimethyl-2-butyn-1-yl) -2- (6-quinolinyloxy)-,
Butanamide, N- (4-methoxy-1,1-dimethyl-2-butyn-1-yl) -2- (6-quinolinyloxy)-,
Propanamide, N- (1,1-dimethyl-2-butyn-1-yl) -3-methoxy-2- (6-quinolinyloxy)-,
Propanamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (7-isoquinolinyloxy) -3-methoxy-,
Butanamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (6-quinazolinyloxy)-,
Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2-ethoxy-2- (6-quinolinyloxy)-,
Butanamide, N- (1,1-dimethyl-2-butyn-1-yl) -2-[(1-oxido-6-quinolinyl) oxy]-,
Butanamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl)-
Butanamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl)-,
Butanamide, 2-[(3-cyano-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl)-,
Propanamide, 3-methoxy-N- (4-methoxy-1,1-dimethyl-2-butyn-1-yl) -2- (6-quinolinyloxy)-,
Butanamide, N- [4-[[(1,1-dimethylethyl) dimethylsilyl] oxy] -1,1-dimethyl-2-butyn-1-yl] -2- (6-quinolinyloxy)-,
Butanamide, N- (6-cyano-1,1-dimethyl-2-hexyn-1-yl) -2-[(3-cyano-6-quinolinyl) oxy]-,
Butanamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl)-,
Butanamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (6-chloro-1,1-dimethyl-2-hexyn-1-yl)-,
Propanamide, 2-[(3-bromo-6-quinolinyl) oxy] -3-methoxy-N- (4-methoxy-1,1-dimethyl-2-butyn-1-yl)-,

Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (6-cyano-1,1-dimethyl-2-hexyn-1-yl) -2- (methylthio)-
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (6-chloro-1,1-dimethyl-2-hexyn-1-yl) -2- (methylthio)-,
Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (6-isoquinolinyloxy) -2- (methylthio)-,
Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (7-isoquinolinyloxy) -2- (methylthio)-,
Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2-[(3-fluoro-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-,
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-,
Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio) -2- (6-quinazolinyloxy)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (4-methoxy-1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-,
Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio) -2- (6-quinolinyloxy)-,

Acetamide, N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio) -2-[(3-phenyl-6-quinolinyl) oxy]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-,
Acetamide, 2-[(7-bromo-2-quinolinyl) oxy] -N- (1-cyano-2-methoxy-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(7-bromo-2-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-fluoro-6-quinolinyl) oxy] -N- [1-cyano-1-methyl-2- (methylthio) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-fluoro-6-quinolinyl) oxy] -N- (1-cyano-2-methoxy-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- (1,1-dimethylpropyl) -2- (methylthio)-,
Acetamide, N- (1-cyano-1,2-dimethylpropyl) -2-[(3,8-dibromo-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, N- (1-cyano-2-methoxy-1-methylethyl) -2-[(3-iodo-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1-cyano-2-methoxy-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1-cyano-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1- (methoxymethyl) cyclopropyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-cyano-1,3-dimethylbutyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1-cyano-3- (4-methoxyphenyl) -1-methylpropyl] -2- (methylthio) -cyano-2- (4- fluorophenyl) -1-methylethyl] -2- (methylthio)-,

Ethanone, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -1- [4- (4-nitrophenyl) -1-piperazinyl]-,
Ethanone, 2-[(3-bromo-6-quinolinyl) oxy] -1- (2,6-dimethyl-4-morpholinyl) -2- (methylthio)-,
Ethanone, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -1- (octahydro-2 (1H) -isoquinolinyl)-,
Ethanone, 2-[(3-bromo-6-quinolinyl) oxy] -1- (2,5-dihydro-2,5-dimethyl-1H-pyrrol-1-yl) -2- (methylthio)-,
Ethanone, 2-[(3-bromo-6-quinolinyl) oxy] -1- (2-ethyl-1-piperidinyl) -2- (methylthio)-
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- [2- (2-pyridinyl) ethyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- [1- (2-naphthalenyl) ethyl]-,
Benzeneacetic acid, a-[[2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) acetyl] amino]-, ethyl ester,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (cyanophenylmethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1- [4- (methylsulfonyl) phenyl] ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- [1- (4-nitrophenyl) ethyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-[(3,4,5-trimethoxyphenyl) methyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-[(2,4,5-trifluorophenyl) methyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2-fluoro-6-methoxyphenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(3,4-dichlorophenyl) methyl] -N- (4-methyl-2-penten-1-yl) -2- (methylthio )-,

Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(4-chloro-2-fluorophenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2,5-difluorophenyl) methyl] -N- (3-methyl-2-buten-1-yl) -2- (methylthio )-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2,6-difluorophenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(4-methoxyphenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(4-chlorophenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(4-fluorophenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(3-methoxyphenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(3-chlorophenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-[[2-[(trifluoromethyl) thio] phenyl] methyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-[[2- (methylthio) phenyl] methyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[[2- (difluoromethoxy) phenyl] methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2-methoxyphenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-[(2-nitrophenyl) methyl]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2-chlorophenyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2-fluorophenyl) methyl] -2- (methylthio)-,

Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-[(2,3-dihydro-5-benzofuranyl) methyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-cyanocyclopropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-methyl-2- (methylthio) -N-2-propyn-1-yl-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- (3-oxo-1-buten-1-yl)-
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N, N-di-2-propen-1-yl-,
Propanamide, 2-[[2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) acetyl] amino] -N, N, 2-trimethyl-
Propanamide, 2-[[2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) acetyl] amino] -N, 2-dimethyl-,
L-Alanine, N-[[((3-bromo-6-quinolinyl) oxy] (methylthio) acetyl]-, methyl ester,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1-cyano-1-methyl-2- (methylthio) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2,2-dimethoxyethyl) -N-methyl-2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N, N-bis (2-ethoxyethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2-methoxy-1- (methoxymethyl) -1-methylethyl] -2- (methylthio)-,

Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2-hydroxy-1- (methoxymethyl) -1-methylethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2-cyanoethyl) -N-methyl-2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -N-methyl-2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N, N-bis (2-methylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-butyl-N-methyl-2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N, N-bis (1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N-methyl-N- (1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N, N-dimethyl-2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2-hydroxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, N- (1,1-dimethylethyl) -2- (methylthio) -2-[(3-phenyl-6-quinolinyl) oxy]-,
Acetamide, N- (1,1-dimethylethyl) -2- (methylthio) -2-[[3- (4-pyridinyl) -6-quinolinyl] oxy]-,
Acetamide, N- (1,1-dimethyl-3-phenyl-2-buten-1-yl) -2- (methylthio) -2-[(3-phenyl-6-quinolinyl) oxy]-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-3-phenyl-2-buten-1-yl) -2- (methylthio)-,
Acetamide, N- (1-cyano-2-methoxy-1-methylethyl) -2-[(3-fluoro-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, N- (1,1-dimethylethyl) -2-[(3-fluoro-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-2-propen-1-yl-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-methyl-1-phenylethyl) -2- (methylthio)-,

Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-2-propyn-1-yl-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-cyano-2-methoxy-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2-furanylmethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-2-thiazolyl-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-cyano-1,2-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- (phenylmethyl)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2- (1-cyclohexen-1-yl) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (4-fluorophenyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-cyano-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- (2-thienylmethyl)-
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N-[(trimethylsilyl) methyl]-,
Alanine, N-[[((3-bromo-6-quinolinyl) oxy] (methylthio) acetyl] -2-methyl-, methyl ester
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N, N-dicyclopropyl-2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- (2,2,2-trifluoro-1,1-dimethylethyl)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N, N-diethyl-2- (methylthio)-,
Pentitol, 1,4-anhydro-3-[[[((3-bromo-6-quinolinyl) oxy] (methylthio) acetyl] amino] -3-C-cyano-2,3,5-trideoxy-,

Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2-[(4-fluorophenyl) methoxy] -1,1-dimethylethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (3-hydroxy-1,1-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (3-ethoxy-1,1-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2-methoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (methylthio) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (3-methoxy-1,1-dimethylpropyl) -2- (methylthio)-,
Ethanone, 2-[(3,8-dibromo-6-quinolinyl) oxy] -2- (methylthio) -1- (4-morpholinyl)-,
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -2- (methylthio) -N- (phenylmethyl)-
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(8-bromo-6-quinolinyl) oxy] -N- (1-cyano-1,2-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -2- (methylthio) -N- (2-thienylmethyl)-

Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -2- (methylthio) -N-2-propyn-1-yl-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -2- (methylthio) -N-[(trimethylsilyl) methyl]-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1-cyano-1,2-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (4-fluorophenyl) -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1-methyl-1-phenylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -2- (methylthio) -N- (2-thienylmethyl)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (2-furanylmethyl) -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -2- (methylthio) -N-2-thiazolyl-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -2- (methylthio) -N-2-propen-1-yl-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -2- (methylthio) -N- (phenylmethyl)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (2-cyanophenyl) -2- (methylthio)-,
Acetamide, 2-[(3-chloro-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2-[[(1,1-dimethylethyl) dimethylsilyl] oxy] -1,1-dimethylethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, N- (1-cyano-2-methoxy-1-methylethyl) -2-[(3-iodo-8-methyl-6-quinolinyl) oxy] -2- (methylthio)-,

Acetamide, N- (1,1-dimethylethyl) -2-[(3-iodo-8-methyl-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (phenylmethoxy) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (2-propen-1-yloxy) ethyl] -2- (methylthio)- ,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- (2-ethoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- (1-cyano-2-methoxy-1-methylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (methylthio) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- (2-methoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- (1,1-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-methyl-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-fluoro-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-iodo-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (phenylmethoxy) ethyl] -2- (methylthio)-

Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (2-propen-1-yloxy) ethyl] -2- (methylthio)- ,
Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- (2-ethoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (methylthio) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-8-chloro-6-quinolinyl) oxy] -N- (2-methoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (phenylmethoxy) ethyl] -2- (methylthio)-
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (2-propen-1-yloxy) ethyl] -2- (methylthio)-
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- (2-ethoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (methylthio) ethyl] -2- (methylthio)-
Acetamide, N- (1-cyano-2-methoxy-1-methylethyl) -2-[(3,8-dibromo-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- (1,1-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(8-bromo-6-quinolinyl) oxy] -N- (1-cyano-2-methoxy-1-methylethyl) -2- (methylthio)-,

Acetamide, 2-[(8-bromo-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, N- (1,1-dimethylethyl) -2-[(3-iodo-6-quinolinyl) oxy] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -2- (methylthio) -N- (2,2,2-trifluoro-1-methylethyl)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2-fluoroethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1-cyclopropylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2- (4-chlorophenyl) -1-cyano-1-methylethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [2- (2-chlorophenyl) -1-cyano-1-methylethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethylpropyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (phenylmethoxy) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- [1,1-dimethyl-2- (2-propen-1-yloxy) ethyl] -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (2-ethoxy-1,1-dimethylethyl) -2- (methylthio)-,
Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-.

  The acaricide or insecticide according to the present invention may contain a carrier such as a solid carrier, a liquid carrier and a gaseous carrier in addition to the aryloxyacetamide compound and its salt. Further, the acaricide or insecticide of the present invention may be one obtained by impregnating a substrate such as a porous ceramic plate or a nonwoven fabric with at least one selected from aryloxyacetamide compounds or salts thereof. The acaricide or insecticide according to the present invention may contain a surfactant and other auxiliary agents as necessary.

  The acaricide or insecticide of the present invention is in a form that can be taken by general agricultural chemicals, that is, wettable powder, granule, powder, emulsion, aqueous solvent, suspension, granular wettable powder, flowable, microcapsule, aerosol. In the case of an aerosol, a heat transpiration agent, a smoke agent, and an acaricide, it may be formulated into a form such as a bait agent.

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

  Solvents used in formulating liquid dosage forms include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil , Vegetable oil, water and the like.

  Examples of the gaseous carrier used in formulating a propellant include butane gas, LPG, dimethyl ether, carbon dioxide gas and the like.

  As a base for poison bait, food ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, children such as pepper Pest-attracting fragrances such as anti-fouling agents for pets, cheese fragrances, and onion fragrances can be mentioned.

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

The wettable powder, emulsion, flowable powder, aqueous solvent, and granular wettable powder thus obtained are diluted with water to a predetermined concentration to obtain a solution, suspension or emulsion. Granules can be sprayed on plants or soil as they are.
In addition, when used as an acaricide for prevention of epidemics, preparations supplied in the form of oils, aerosols, fumes, poison baits, mite-proof sheets, etc. can be used as they are.

When the acaricide or insecticide of the present invention is used as an acaricide for controlling mites parasitic on livestock such as cattle and pigs, and pet animals such as dogs and cats, 1 kg of host animals. On the other hand, the aryloxyacetic acid amide compound and its salt can be used in an amount of 0.01 to 1000 mg.
The acaricide for control can be applied by a known veterinary technique. For example, for the purpose of systemic control, the animal is treated by tablets, capsules, immersion liquid, feed mixing, suppositories, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). In the case of non-systemic control, spray or pour-on, drop-on, etc. of oily or aqueous solution And a method in which an acaricide is kneaded into a resin, the kneaded product is formed into an appropriate shape such as a collar and an ear tag, and is attached to an animal.
The acaricide or insecticide according to the present invention is effective for controlling various pests or mites. The aryloxyacetamide compound and salts thereof contained in the acaricide or insecticide of the present invention have actions such as adulticide, nymphicide, larvae, and ovulation.
The acaricide or insecticide of the present invention can be used for controlling ticks attached to agricultural products, for example, controlling ticks attached to fruit trees, flower buds and trees.

Examples of mites (Acari) attached to crops are shown below.
(1) Astigmata (Acaridida):
(a) Acaridae mites, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; Tyrophagus spp., Tyrophagus sp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus similis; Others, Acarus siro, Mysticus (Aleuroglyphus cetus)

(2) Prostigmata mites (Actinedida)
(A) mites of the Tetranychidae family, for example of the genus Bryobia spp., Clover spider mite (Bryobia praetiosa), fake clover spider mite (Bryobia rubrioculus); Aid spider mite (Eotetranychus sidani) (Eotetranychus seidu) (Eotetranychus shii) ), White spider mite (Eotetranychus asiaticus), Eotetranychus kankitus; eg Oligonychus mangiferus, Oligonychus perseae, ulosus Spider mite (Oligonychus karamatus), Sugino spider mite (Oligonychus hondoensis), Crimson spider mite (Oligonychus ununguis), Rice spider mite (Oligonychus shinkajii), sugarcane spider mite (Oligonychus or spp. (Panonychus citri), quail spider mite (Panonychus mori), apple spider mite (Panonychus ulmi); (Tetranychus phaselus), Tetranychus cinnabarinus, Kanzawa spider mite (Tetranychus kanzawai), Nite spider mite (Tetranychus urticae); for example, Aponychus spp. For example, the green spider mite (Sasanychus spp.), The green spider mite (Sasanychus akitanus), the Japanese spider mite (Sasanychus pusillus); ), Spider spider mite (Shizotetranychus longus), Spider spider mite (Shizotetranychus schizopus), Shizotetranychus recki;

(B) Tenuipalpidae ticks, for example, Brevipalpus spp., Brevipalpus lewsulus, Brevipalpus russulus, Brevipalpus obovatus, Penis phoeni ); For example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae from Tenuipalpus spp .; other, Dolichotetranychus floridanus;
(c) Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Carnation mite (Aceria paradianthi), black spider mite (Aceria tiyingi), tulip spider mite (Aceria tulipae), Shibahamaki fushi mite (Aceria zoysiea); for example, Eriophyes spp., Eriophyes chibaensis, For example, Aculops spp., Aculops lycopersici, Aculops pelekassi; eg, Aculus fockeui, Aculus schlechtendali, Aculus schlechtendali; Others, grape ticks (Colomerus vitis), grape rust mites (Cale) pitrimerus vitis), Phyllocotruta citri, Maxillid mite (Paracalacarus podocarpi), White-faced tick (Calacarus carinatus), White-faced tick (Acaphylla theavagrans), Red-footed tick (Paraphytoptus kikus);
(d) Mites of the family Transonemidae (eg, Tarsonemus spp.), Tarsonemus bilobatus, Tarsonemus waitei; ;
(e) Penthaleidae mites, such as Penthaleus erythrocephalus, Penthaleus major of Penthaleus spp.

  The acaricide or insecticide according to the present invention is also excellent in controlling effect against mites parasitizing animals. Mites parasitizing animals that inhabit the back, underarms, lower abdomen, inner thighs, etc. of animals that become hosts (host animals) and obtain nutrients such as blood and dandruff from the animals, and hosts Includes animals that fly to animal backs, buttocks, etc., and obtain nutrients such as blood and dandruff from animals. Target host animals include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; companion birds (eg, pigeons, parrots, nine-birds, wild birds, parakeets, juvenile pine, canary); cattle, horses, Pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); bees (eg, honey bees, Japanese bees);

Examples of mites (Acari) parasitic on animals are shown below.
(1) Mesostigmata mites (mite)
(a) Dermanyssidae mites, such as Dermanyssus gallinae;
(b) Mite of the family Mronidsidae (Macronyssidae), for example, Ornithonyssus spp., Ornithonyssus sylviarum, Ornithonyssus bursa, Ornithonyssus bacoti;
(c) Mites of the family Laelapidae, for example, Laelaps echidninus, Laelaps jettmari; Tropilaelaps clarae
(d) Varroidae ticks, for example, Varroa spp., Varroa destructor, Varroa jacobsoni, Varroa underwoodi;

(2) Metastigmata tick (tick)
(a) mites of the family Argasidae, for example Argas spsi., Argas persicus, Argas reflexus; for example Ornithodoros spp. Ornithodoros moubata;
(b) Ixodidae ticks, for example Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis puncta, Haemaphysalis cinnaina, Haemaphysalis cinnaina Haemaphysalis otophila), Haemaphysalis leachi, Haemaphysalis longicornis, ali flis (Haemaphysalis mageshimaensis), physalis tick (Haemaphysalis yeni), tuna swordfish ), Large tick (Haemaphysalis megaspinosa), tick (Haemaphysalis japonica), Douglas tick (Haemaphysalis douglasi); Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajense Tick species (Ixodes spp.), Tick (Ixodes ricinus), Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes rubicundus, Ixodes rubicundus Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis; Of the subgenus (Boophilus spp.), The tick (Rhipicephalus (Boophilus) microplus), Lipisephalus (Boophilus) decoloratus (Rhipicephalus (Boophilus) decoloratus), Lipisephalas (Boophilus) Annuratus (R.) ) ・ Carceratas (Rhipicephalus (Boophilus) calceratus); for example, Ryuicephalus spp. ), Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus, Rhipicephalus appendiculatus Rhipicephalus turanicus, Rhipicephalus zambeziensis; for example Dermacentor marginatus, Dermacentor marginatus, Dermacentor reticulatica (Dermacentor pictus), Dermacentor albipictus, Dermacentor andersoni, Dermacentor Barrier Squirrel (Dermacentor variabilis);

(3) Astigmata (Acaridida)
(a) Mites of the family Psoroptidae, such as Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi; Psoroptes equi; Chorioptes spp., Chorioptes bovis; Otodectes spp., Otodectes cynotis;
(b) Scaroptidae mites, such as Sarcoptes spabi, Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis), Sarcoptes rupicaprae, Sarcoptes equi, Sarcoptes suis; for example, Notoedres spp., Notoedres cati;
(c) Mites of the family Knemidokoptidae, for example, Knemidokoptes mutans of the genus Knemidokoptes spp .;

(4) Prostigmata mites (Actinedida)
(a) Acaridaceae (Demodixidae) mites, such as Demodex spp., Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex caprae, Democratic mites (Demodex equi), Demodex caballi (Demodex caballi), Scarlet mites (Demodex suis), Caterpillar mites (Demodex cati);
(b) Trombiculidae mites, such as the species of the species of the genus Trombicula spp., Trombicula alfreddugesi, Trombicula akamushi;
(c) Mites from the family Tarsonemidae, for example Acarapis woodi, from the genus Acarapis spp .;

  The acaricide or insecticide according to the present invention can be used to control pests, hygiene pests, storage shell pests, clothing pests, house pests, and the like attached to crops.

Examples of pests to be controlled are shown below.
(1) Lepidoptera pests such as Spodoptera litura, Mamestra brassicae, Agrotis ypsilon, Autographa nigrisigna, Plutella xylostella, Adeno hon, mai, hon Homona magnanima), peach sigai (Carposina sasakii), pear tiger squirrel (Grapholitha molesta), mandarin moth (Phyllocnistis citrella), chanohosoga (Caloptilia theivora), kinmonhosoga (Phyllonorycter ringoniella), maiparigai (Lymanttis quaga) suppressalis, Cnaphalocrocis medinalis, European corn borer (Ostrinia nubilalis), Hyphantria cunea, Cadra cautella, Heliothis spp., Heliobelpa (. Agrotis spp) (Helioverpa), Agurotisu species, clothes moth (Tinea translucens), codling moth (Cydia pomonella), etc. pink bollworm (Pectinophora gossypiella);
(2) Hemiptera pests, for example, Myzus persicae, Aphis gossypii, Lipaphis erysimi, Rhopalosiphum padi, Riptortus clavatus, Riptortus clavatus Acrosternum hilare, Unaspis yanonensis, Pseudococcus comstocki, Trialeurodes vaporariorum, Bemisia tabaci, Silver leaf white genta Stephanitis nashi, Japanese green planthopper (Nilaparvata lugens), Japanese green planthopper (Laodelphax stratella), Japanese white planthopper (Sogatella furcifera), Nephotettix cincticeps, etc .;
(3) Coleoptera pests, for example, Phyllotreta striolata, Aulacophora indica, Colorado potato beetle (Leptinotarsa decemlineata), rice weevil (Lissorhoptrus oryzophilus), Pond weevil (Sitophilus orbru japonica), Anomala rufocuprea, Diabrotica spp., Tobacco beetle (Lasioderma serricorne), Lyctus brunneus, Monochamus alternatus, Malocasi pl Agriotes spp.), Epilachna vigintioctomaculata, Tenebroides mauritanicus, cotton weevil (Anthonomus grandis), etc .;
(4) Diptera pests, for example, Bactrocera cucurbitae, Bactrocera dorsalis, Delia platura, Hydrellia griseola, Drosophila melanogaster, etc .;
(5) Thripidae pests, for example, Thrips palmi, Scirtothrips dorsalis, etc .;
(6) Hymenoptera, for example, Monomorium pharaonis, Vespa simillima, Athalia rosae, etc .;
(7) Diptera pests, such as Locusta migratoria;
(8) Cockroach (Blattodea) pests such as German cockroach (Blattella germanica), Black cockroach (Periplaneta fuligginosa), Japanese cockroach (Periplaneta japonica), American cockroach (Periplaneta americana), Black cockroach (Periplaneta australasiae);
(9) Termite pests such as termites (Coptotermes formosanus), termites (Reticulitermes speratus),
(10) Plant parasitic nematodes such as, for example, Meloidogyne incognita, Negusale nematodes, soybean cyst nematodes (Heterodera glycines), rice nesting nematodes (Aphelenchoides besseyi), pine wood nematodes (Bursaphelenchus xylophil;

The acaricide or insecticide of the present invention is a fungicide, other insecticide / acaricide, nematicide, soil insecticide, plant regulator, synergist, fertilizer, soil improver, animal feed, etc. May be used together or in combination.
Typical examples of fungicides, other insecticides / acaricides, nematicides and soil insecticides that can be used in combination with or together with the acaricide or insecticide of the present invention are shown below.

Insecticides, acaricides, nematicides, soil insecticides:
(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, fenamifos, 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, pyridafenthion, furiothiocarb, XMC, aldoxicarb, arixicarb, aminocarb, bendiocarb, bufencarb, butacarb, butcarboxyme, butoxycarboxyme, cloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metolcarb, promecarb Fanox, 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, nobarulone, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiazox, etoxazole, clofente Gin, fluazuron, penfluron;
(b) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, chromafenozide, azadirachtin;
(c) juvenile hormone-like substances: pyriproxyfen, metoprene, geophenolan, epofenanane, hydroprene, quinoprene, triprene;
(d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat, flonicamid;

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

(11) Oxidative phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin;
(12) molting disruptor: cyromazine;
(13) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(14) Sodium channel blocker compounds: indoxacarb, metaflumizone;
(15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp. Lilium species;
(16) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
(17) Octopaminergic agent: Amitraz;
(18) Ryanodine derivative agonist: fulvendiamide, chlorantraniliprole, cyantraliniprol (19) Inhibitor of magnesium-stimulated ATPase: thiocyclam, thiosultap, nereistoxin;
(20) Antifeedant: Pymetrozine;
(21) Tick growth inhibitor: clofentezin, etoxazole;
(22) Others: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzomate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzo Ximate, bromopropyrate, quinomethionate, chlorbenzilate, chloropicrin, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, flufenzine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, sulfluramide, tetrasul, trialacene;

Fungicide:
(1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl, etc .;
(2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin and the like;
(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 etc .;

(4) Phenylamide: Benalaxyl, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, ophthalse and the like;
(5) Amine type: aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine and the like;
(6) phosphorothiolate type: EDDP, iprobenphos, pyrazophos, etc .;
(7) Dithiolane type: isoprothiolane and the like;
(8) Carboxamide: benodanyl, boscalid, carboxin, fenfuran, flutolanyl, furamethopyl, mepronil, oxycarboxin, pentiopyrad, tifluzamide and the like;
(9) Hydroxy- (2-amino) pyrimidine series: bupyrimeto, dimethylolymol, ethylimole, etc .;

(10) AP fungicide (anilinopyrimidine) type: cyprodinil, mepanipyrim, pyrimethanil, etc .;
(11) N-phenyl carbamate type: dietofencarb, etc.
(12) QoI-bactericidal (Qo inhibitor) system: azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, Famoxadone, floxastrobin, phenamidon, metminophen, etc .;
(13) PP fungicide (phenylpyrrole): Fenpiconyl, fludioxonil, etc .;
(14) Quinoline series: quinoxyphene, etc .;

(15) AH fungicide (aromatic hydrocarbon) series: biphenyl, chloronebu, dichlorane, kintozen, technazen, tortofos-methyl, etc .;
(16) MBI-R series: fusaride, pyrokilone, tricyclazole, etc .;
(17) MBI-D system: carpropamide, diclocimet, phenoxanyl, etc .;
(18) SBI agents: fenhexamide, pyributicarb, terbinafine, etc .;
(19) Phenylurea: Pencyclon, etc .;
(20) QiI-bactericides (Qi inhibitors): cyazofamide, etc .;
(21) Benzamide series: Zoxamide and the like;
(22) Enopyranuron series: blastcidin, mildiomycin, etc .;
(23) Hexopyranosyl: Kasugamycin, etc.
(24) Glucopyranosyl: streptomycin, validamycin, etc .;
(25) Cyanoacetamide series: Simoxanyl and the like;
(26) Carbamate series: iodocarb, propamocarb, prothiocarb, polycarbamate, etc .;
(27) Uncouplers: Vinapacryl, Zinocup, Ferimzone, Fluazinam, etc .;
(28) Organotin compounds: triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide, etc .;

(29) Phosphate ester: phosphorous acid, tolcrofosmethyl, fosetyl and the like;
(30) Phthalamic acid type: Teclophthalam, etc .;
(31) Benzotriazine series: triazoxide and the like;
(32) Benzenesulfonamide series: fullsulfamide and the like;
(33) Pyridazinone: Dichromedin and the like;
(34) CAA disinfectant (carboxylic amide) type: dimethomorph, fullmorph, benchavaricarb, iprovaricarb, mandipropamide, etc .;
(35) Tetracycline: oxytetracycline, etc .;
(36) Thiocarbamate type: metasulfocarb, etc.
(37) Other compounds: etridiazole, polyoxin, oxolinic acid, hydroxyisoxazole, octinoline, silthiofam, diflumetrim, acibenzoral S methyl, probenazole, thiazinyl, ethaboxam, cyflufenamide, proquinazide, metolaphenone, fluopicolide, cupric hydroxide, organic Copper, sulfur, farbum, manzeb, mannebu, manebu, methylam, propineb, thiuram, dineb, diram, captan, captahol, phorpet, chlorothalonil, diclofluuride, tolylfluanid, dodine, guazatine, iminocazine acetate, iminoctadine dodecylbenzenesulfonic acid Salt, anilazine, dithianone, chloropicrin, dazomet, quinomethionate, ciprofuram, silthiofam, agro Kuteriumu, Furuoruimido) and the like;

  Next, an Example is shown and this invention is demonstrated more concretely. However, the present invention is not limited by the following examples.

Although some formulation examples of the acaricide or insecticide of the present invention are shown, the additives and addition ratios should not be limited to these examples, and can be varied in a wide range. The part in a formulation example shows a weight part. The aryloxyacetamide compound or a salt thereof is simply referred to as “the compound of the present invention”.
Examples of formulations for agricultural and horticultural use are shown below.

Formulation Example 1 (wettable powder)
Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above was uniformly mixed and finely pulverized to obtain a wettable powder with 40% active ingredient.

Formulation Example 2 (Emulsion)
Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts The above components were mixed and dissolved to obtain an emulsion containing 30% active ingredient.

  Examples of formulation for prevention of disease and animals are shown below.

Formulation Example 3 (Granule)
Compound of the present invention 5 parts Kaolin 94 parts White carbon 1 part The compound of the present invention is dissolved in an organic solvent, sprayed onto a carrier, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.

Formulation Example 4 (Injection)
Compound of the present invention 0.1-1 part Peanut oil Balance After preparation, filter sterilize with a sterilization filter.

Formulation Example 5 (Pour-on agent)
Compound of the present invention 5 parts Myristic acid ester 10 parts Isopropanol Balance

Formulation Example 6 (Spot-on agent)
Compound of the present invention 10-15 parts Palmitic acid ester 10 parts Isopropanol Balance

Formulation Example 7 (Spray-on agent)
Compound of the present invention 1 part Propylene glycol 10 parts Isopropanol Balance

[Biological test]
The following test examples show that the acaricide or insecticide of the present invention is useful.
The following compounds were used for the test.
Compound 1: Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-
Compound 2: Acetamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethylethyl) -2- (methylthio)-
Compound 3: Acetamide, 2-[(3,8-dibromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl) -2- (methylthio)-
Compound 4: Butanamide, 2-[(3-bromo-6-quinolinyl) oxy] -N- (1,1-dimethyl-2-butyn-1-yl)-

Test Example 1 Efficacy test against nymph spider mite (Tetranychus urticae) Ten adult male nymph mite resistant to organophosphates were inoculated on the primary leaves 7 to 10 days after germination of green beans seeded in 3-inch pots. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated after 3 days from the spraying. Furthermore, it was investigated whether the eggs laid after 14 days from spraying could develop to adults.
The above tests were carried out on emulsions containing compounds 1, 2, 3 and 4, respectively. All compounds had an insecticidal rate after 3 days or an insecticidal rate after 10 days of 90% or more.

Test Example 2 Efficacy test against citrus spider mite (Panonychus citri) On a mandarin leaf placed in a petri dish, 8 adult females of acaricide resistant citrus spider mite from Wakayama Prefecture were inoculated. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the mandarin orange using a rotary spray tower. The mandarin orange was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated after 3 days from the spraying. Furthermore, it was investigated whether the eggs laid after 10 days from spraying could develop to adults.
The above tests were conducted on emulsions containing compounds 2 and 4, respectively. All compounds had an insecticidal rate after 3 days or an insecticidal rate after 10 days of 90% or more.

Test Example 3 Efficacy test against citrus mite (Aculops pelekassi) 20 miticide-resistant citrus mite insects were inoculated on citrus leaves placed in a petri dish. Next, an emulsion having the formulation shown in Formulation Example 2 was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the mandarin orange using a rotary spray tower. The mandarin orange was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated after 3 days from the spraying. Furthermore, it was investigated whether the eggs laid after 10 days from spraying could develop to adults.
The above tests were carried out on emulsions containing compounds 1, 2, 3 and 4, respectively. All compounds had an insecticidal rate after 3 days or an insecticidal rate after 10 days of 90% or more.

Claims (4)

An acaricide or insecticide containing at least one selected from aryloxyacetamide compounds represented by the formula (I) or salts thereof.

[In the formula (I),
Cy represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted X heteroaryl group. Substituent X is unsubstituted or substituted C1-6 alkyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C2-6 alkenyl group, unsubstituted Or a substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an unsubstituted or A substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 Alkylsulfonyl group, unsubstituted or substituted C1-6 alkoxysulfonyl group, unsubstituted or substituted C 10 aryl group, an unsubstituted or heteroaryl group having a substituent, hydroxyimino C1~6 alkyl group having unsubstituted or substituted group, a nitro group, a cyano group or a halogen atom. Two or more substituents X may be present, and when two or more substituents X are present, X may be the same or different from each other.
R ^1a is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, an unsubstituted or A C1-6 alkoxy group having a substituent, or an unsubstituted or substituted C1-6 alkylthio group is shown.
R ^1b represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, or an unsubstituted or substituted C2-6 alkynyl group. Show. Here, R ^1a and R ^1b may be connected to each other to form a ring together with the carbon atom to which R ^1a and R ^1b are bonded.
Z represents an oxygen atom or a sulfur atom.
Q represents an unsubstituted or substituted 1-pyrrolidinyl group, an unsubstituted or substituted 2,5-dihydro-1H-pyrrol-1-yl group, an unsubstituted or substituted 1-piperidinyl group Group, unsubstituted or substituted 1-piperazinyl group, unsubstituted or substituted 4-morpholinyl group, unsubstituted or substituted octahydro-2 (1H) -isoquinolinyl group, unsubstituted or A C6-10 arylamino group having a substituent, an unsubstituted or substituted heteroarylamino group, a group represented by formula (II), or a group represented by formula (III) is shown.

(In formula (II), * indicates a bonding position.
R ² represents a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 alkynyl group, A substituted or substituted C1-7 acyl group, or an unsubstituted or substituted C1-6 alkoxycarbonyl group is shown.
R ³ and R ⁴ each independently have a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted group A C2-6 alkynyl group, an unsubstituted or substituted C6-10 aryl group, or a cyano group is shown. Here, R ³ and R ⁴ may be connected to each other to form a ring together with the carbon atom to which R ³ and R ⁴ are bonded.
R ^5a is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted Or a substituted C2-6 alkynyl group, an unsubstituted or substituted C1-7 acyl group, a carboxyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted group Having a C2-6 alkenyloxycarbonyl group, unsubstituted or substituted C2-6 alkynyloxycarbonyl group, unsubstituted or substituted aminocarbonyl group, unsubstituted or substituted C6-10 aryl group , An unsubstituted or substituted hydroxyimino C1-6 alkyl group, or a cyano group . )

(In formula (III), * indicates a bonding position.
R ² and R ³ have the same meaning as described above.
R ^5b represents an unsubstituted or substituted heteroaryl group. ]] The acaricide according to claim 1, wherein Cy is an unsubstituted or substituted quinolyl group, R ^1a is an unsubstituted or substituted C 1-6 alkylthio group, and R ^1b is a hydrogen atom. Insecticide.   The acaricide or insecticide according to claim 1 or 2, wherein Q is a group represented by the formula (II). R ³ is unsubstituted or substituted C 1-6 alkyl group, R ⁴ is unsubstituted or substituted C 1-6 alkyl group, and R ^5a is unsubstituted or substituted C 2-6 alkynyl. The acaricide or insecticide according to any one of claims 1 to 3, which is a group.