JP2017110003A - Diaryltriazole compound and noxious organism-controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a diaryltriazole compound that is excellent in insecticidal activity and/or acaricidal activity, is excellent in safety, and is industrially advantageously synthesized, and a noxious organism-controlling agent comprising the compound.SOLUTION: There is provided a compound represented by Formula (I) etc. or a salt thereof, wherein Ais C or N; Xis unsubstituted/substituted alkyl group, unsubstituted/substituted alkenyl group, unsubstituted/substituted aryl group, hydroxy group, formyl group, mercapto group etc.; n is an integer of 0-4; Ris halogeno group, unsubstituted/substituted alkylthio group, unsubstituted/substituted C1-6 alkylsulfonyl group etc.; Ris unsubstituted/substituted alkyl group, unsubstituted/substituted alkenyl, hydroxy group etc.; and Ar is unsubstituted/substituted aryl group or unsubstituted/substituted 5-6 membered-ring heteroaryl group.SELECTED DRAWING: None

Description

  The present invention relates to a diaryltriazole compound and a pest control agent. More specifically, the present invention relates to a diaryltriazole compound which has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially, and a pest control agent containing the compound as an active ingredient About.

  Various compounds having insecticidal / miticidal activity have been proposed. In order to put such compounds into practical use as agricultural chemicals, they are not only sufficiently effective but also resistant to drug resistance, do not cause phytotoxicity or soil contamination on plants, and have low toxicity to livestock and fish. Etc. are required.

By the way, Patent Document 1 discloses a compound represented by the formula (A). According to Patent Document 1, this compound is diabetes, hyperglycemia, obesity, insulin resistance, arteriosclerosis. It appears to be useful in the treatment of dyslipidemia, hypertension, and metabolic syndrome.

Patent Document 2 discloses a compound represented by the formula (B).

Special table 2007-530690 gazette WO 2015/144826 A1

  An object of the present invention is to provide a diaryltriazole compound that is excellent in pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously, and effectively It is to provide a pest control agent contained as a component. Furthermore, it is providing the ectoparasite control agent which contains this as an active ingredient.

［式（I）および式（II）中、
Ａ¹は、炭素原子または窒素原子を示す。
Ｘ¹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、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、ホルミル基、無置換のもしくは置換基を有するＣ１〜６アルキルカルボニル基、無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基、メルカプト基、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アルキルスルフィニル基、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Ｃ６〜１０アリール基、無置換のもしくは置換基を有する３〜６員ヘテロシクリル基、無置換のもしくは置換基を有するアミノ基、ハロゲノ基、シアノ基、またはニトロ基を示す。
ｎは化学的に許容されるＸ¹の個数を示しかつ０〜４のいずれかの整数である。ｎが２以上のときＸ¹は互いに同じでも異なってもよい。
Ｒ¹は、ハロゲノ基、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アルキルスルフィニル基、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アルキルスルホニルオキシ基、または−Ｓ（＝Ｏ）（＝Ｎ−Ｒ^a）−Ｒ^bで表される基を示す。ここで、Ｒ^aおよびＲ^bは、それぞれ独立に、無置換のもしくは置換基を有するＣ１〜６アルキル基を示す。
Ｒ²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、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、ホルミル基、無置換のもしくは置換基を有するＣ１〜６アルキルカルボニル基、無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基、または無置換のもしくは置換基を有するＣ１〜６アルキルスルホニル基を示す。
Ａｒは、無置換のもしくは置換基を有するＣ６〜１０アリール基、または無置換のもしくは置換基を有する５〜６員ヘテロアリール基を示す。］ As a result of intensive studies to solve the above problems, the present invention including the following embodiments has been completed.
[1] A compound represented by formula (I) or formula (II) or a salt thereof.

[In Formula (I) and Formula (II),
A ¹ represents a carbon atom or a nitrogen atom.
X ¹ 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, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, mercapto group, unsubstituted Or substituted or unsubstituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted Denotes the 3- to 6-membered heterocyclyl group having a substituent, unsubstituted or amino group having a substituent, halogeno group, cyano group or a nitro group.
n represents the number of chemically acceptable X ¹ and is an integer of 0 to 4. When n is 2 or more, X ¹ may be the same or different.
R ¹ is a halogeno group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group , An unsubstituted or substituted C 1-6 alkylsulfonyloxy group, or a group represented by —S (═O) (═N—R ^a ) —R ^b ; Here, R ^a and R ^b each independently represent an unsubstituted or substituted C 1-6 alkyl group.
R ² 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, a hydroxyl group, an unsubstituted group Or a substituted C1-6 alkoxy group, a formyl group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, or an unsubstituted or The C1-6 alkylsulfonyl group which has a substituent is shown.
Ar represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-6 membered heteroaryl group. ]

［式（III）および式（IV）中、Ａ¹、Ｘ¹、Ｒ¹、およびＲ²は、式（I）および式（II）中のそれらと同じ意味を示す。
Ｘ^1a、Ｘ²およびＸ^2aは、それぞれ独立に、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、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、ホルミル基、無置換のもしくは置換基を有するＣ１〜６アルキルカルボニル基、無置換のもしくは置換基を有するＣ１〜６アルコキシカルボニル基、メルカプト基、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アルキルスルフィニル基、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Ｃ６〜１０アリール基、無置換のもしくは置換基を有する３〜６員ヘテロシクリル基、無置換のもしくは置換基を有するアミノ基、ハロゲノ基、シアノ基、またはニトロ基を示す。
ｋは化学的に許容されるＸ^1aの個数を示しかつ０〜３のいずれかの整数である。ｋが２以上のときＸ^1aは互いに同じでも異なってもよい。
ｈは化学的に許容されるＸ^2aの個数を示しかつ０〜４のいずれかの整数である。ｈが２以上のときＸ^2aは互いに同じでも異なってもよい。］ [2] The compound or a salt thereof according to [1], wherein formula (I) or formula (II) is formula (III) or formula (IV).

[In Formula (III) and Formula (IV), A ¹ , X ¹ , R ¹ , and R ² have the same meanings as those in Formula (I) and Formula (II).
X ^1a , X ² and X ^2a each independently have an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted group C1-6 alkynyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 6 alkoxycarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl Group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C 10 aryl group, an unsubstituted or 3-6 membered heterocyclyl group having a substituent, an amino group having unsubstituted or substituted group, halogeno group, a cyano group or a nitro group.
k represents the number of chemically acceptable X ^1a and is an integer of 0 to 3. When k is 2 or more, X ^1a may be the same as or different from each other.
h represents the number of chemically acceptable X ^2a and is an integer of 0-4. When h is 2 or more, X ^2a may be the same or different. ]

[3] A pest control agent containing at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof as an active ingredient.
[4] An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
[5] An ectoparasite control agent comprising as an active ingredient at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
[6] An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.

  The diaryltriazole compound of the present invention can control pests that are problematic in crops and hygiene. In particular, agricultural pests and mites can be effectively controlled at a lower concentration. Furthermore, ectoparasites that harm human livestock can be effectively controlled.

[Diaryltriazole Compound]
The diaryltriazole compound of the present invention is a compound represented by formula (I) or formula (II) (hereinafter sometimes referred to as compound (I) or compound (II)) or compound (I) or compound (II). Of salt.

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. Examples of groups that can be “substituents” are shown below.
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;
Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc. A C2-6 alkenyl group of
C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;

A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cubanyl group;
A C6-10 aryl group such as a phenyl group or a naphthyl group;
A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
A 3-6 membered heterocyclyl group;
A 3-6 membered heterocyclyl C1-6 alkyl group;

Hydroxyl group;
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;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
A C6-10 aryl C1-6 alkoxy group such as a benzyloxy group or a phenethyloxy group;
5-6 membered heteroaryloxy groups such as thiazolyloxy group, pyridyloxy group;
5-6 membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy group, pyridylmethyloxy group;

Formyl group;
A C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group;
Formyloxy group;
A C1-6 alkylcarbonyloxy group such as an acetyloxy group or a propionyloxy group;
A C6-10 arylcarbonyl group such as a benzoyl 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;
A C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group;
Carboxyl group;

Halogeno groups such as fluoro, chloro, bromo and iodo groups;
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 trifluoromethoxy group, a 2-chloro-n-propoxy group, or a 2,3-dichlorobutoxy group;
A C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;
A C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group;

An amino group;
A C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, or a diethylamino group;
A C6-10 arylamino group such as an anilino group or a naphthylamino group;
A C6-10 aryl C1-6 alkylamino group such as a benzylamino group or a phenethylamino group;
Formylamino group;
A C1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino 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;
N-hydroxy-iminomethyl group, (1- (N-hydroxy) -imino) ethyl group, (1- (N-hydroxy) -imino) propyl group, N-methoxy-iminomethyl group, (1- (N-methoxy) -Imino) N-hydroxyimino C1-6 alkyl group having an unsubstituted or substituted group such as an ethyl group;
An aminocarbonyloxy group;
A C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy 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 C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group;
A C6-10 arylthio group such as a phenylthio group or a naphthylthio group;
A 5- to 6-membered heteroarylthio group such as a thiazolylthio group or a pyridylthio group;
A C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group;
A C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group or a 2,2,2-trifluoroethylsulfinyl group;
A C6-10 arylsulfinyl group such as a phenylsulfinyl group;
5-6 membered heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group;
A C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group;
A C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group;
A C6-10 arylsulfonyl group such as a phenylsulfonyl group;
A 5- to 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group;
A C1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group, or a t-butylsulfonyloxy group;
A C1-6 haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group or a 2,2,2-trifluoroethylsulfonyloxy group;

A tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, or a t-butyldimethylsilyl group;
A tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group;
Cyano group; nitro group;
In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure. In this case, examples of the “substituent” include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

  Moreover, said "3-6 membered heterocyclyl group" contains 1-4 heteroatoms chosen from the group which consists of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring structural atom. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, if at least one ring is a hetero ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3-6 membered heterocyclyl group” include a 3-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

  Examples of the 3-6 membered saturated heterocyclyl group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like.

Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, etc. .
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

In formula (I) and formula (II), A ¹ represents a carbon atom or a nitrogen atom. The carbon atom in A ¹ may have a substituent. When A ¹ is a carbon atom, it means CH or CX ¹ (or CX ^1a ). That is, the compound represented by the formula (I) or the formula (II) is any one of the following formulas (a) to (d).

In Formula (I) and Formula (II), X ¹ represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted group. Having C2-6 alkynyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1 -6 alkoxycarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkyl Sulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10 Aryl group, 3- to 6-membered heterocyclyl group having unsubstituted or substituted group, an amino group having unsubstituted or substituted group, halogeno group, cyano group or a nitro group.

The “C 1-6 alkyl group” in X ¹ may be a straight chain or a branched chain as long as it has 3 or more carbon atoms. 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.

Specific examples of the “C1-6 alkyl group having a substituent” include
Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 -C1-6 haloalkyl group such as trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group;

C1-C1 such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group 6 alkoxy C1-6 alkyl groups;
A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
And C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group, and the like.

As the “C2-6 alkenyl group” for X ¹ , 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.
Specific 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; 2-n-butoxy-vinyl Groups, C1-6 alkoxy C2-6 alkenyl groups such as 1-ethoxy-vinyl group, and the like.

As the “C 2-6 alkynyl group” in X ¹ , an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 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.
Specific examples of the “substituted C2-6 alkynyl group” include C2-6 such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group and the like. And haloalkynyl group.

As the “C1-6 alkoxy group” in X ¹ , a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group , S-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Specific examples of the “C1-6 alkoxy group having a substituent” include a chloromethoxy group, a dichloromethoxy group, a difluoromethoxy group, a trichloromethoxy group, a trifluoromethoxy group, a 1-fluoroethoxy group, and a 1,1-difluoroethoxy group. A C1-6 haloalkoxy group such as a group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, 2,2,3,4,4,4-hexafluoro-butoxy group;
A C1-6 alkoxy C1-6 alkoxy group such as a methoxymethoxy group or a methoxyethoxy group;
A C6-10 aryl C1-6 alkoxy group such as a benzyloxy group or a phenethyloxy group;
A C3-8 cycloalkyl C1-6 alkoxy group such as a cyclopropylmethyloxy group;

Examples of the “C1-6 alkylcarbonyl group” for X ¹ include an acetyl group and a propionyl group.
Specific examples of the “substituted C1-6 alkylcarbonyl group” include C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group, and trichloroacetyl group.

Examples of the “C1-6 alkoxycarbonyl group” for X ¹ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
As a specific example of “C1-6 alkoxycarbonyl group having a substituent”,
Fluoromethoxycarbonyl group, chloromethoxycarbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2 C1-6 haloalkoxycarbonyl group such as 2-propylethoxycarbonyl group; C3 such as cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-cyclopropylethoxycarbonyl group -8 cycloalkyl C1-6 alkoxycarbonyl groups;

Examples of the “C 1-6 alkylthio group” in X ¹ include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, i-butylthio group and the like. It is done.
Specific examples of the “C1-6 alkylthio group having a substituent” include C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.

Examples of the “C1-6 alkylsulfinyl group” for X ¹ include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.
Specific examples of the “substituted C1-6 alkylsulfinyl group” include C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.

Examples of the “C1-6 alkylsulfonyl group” for X ¹ include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
Specific examples of the “substituted C1-6 alkylsulfonyl group” include C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for X ¹ Preferred substituents on the “group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, and “C1-6 alkylsulfonyl group” include C1-6 alkoxy group, halogeno group, cyano group, C3 -8 cycloalkyl group, C6-10 aryl group, 3-6 membered heterocyclyl group, etc. are mentioned.

Examples of the “C 3-8 cycloalkyl group” for X ¹ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.

The “C6-10 aryl group” in X ¹ 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 phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like.

The “3 to 6-membered heterocyclyl group” in X ^{1 includes 1} to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, if at least one ring is a hetero ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3-6 membered heterocyclyl group” include a 3-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

  Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group (specifically, [1,3] dioxolanyl group), Examples include dioxanyl groups (specifically, [1,3] dioxanyl groups or [1,4] dioxanyl groups). Preferably, it is a 5-6 membered saturated heterocyclyl group.

Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl (for details, [1,2,3] triazolyl Or [1,2,4] triazolyl group), oxadiazolyl group (specifically, [1,2,4] oxadiazolyl group or [1,3,4] oxadiazolyl group), thiadiazolyl group, tetrazolyl group and the like. .
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

Examples of the partially unsaturated 5-membered heterocyclyl group include pyrrolinyl group, imidazolinyl group (dihydroimidazolyl group), pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group and the like.
Examples of the partially unsaturated 6-membered heterocyclyl group include a thiopyranyl group, a 2H-pyridin-1-yl group, and a 4H-pyridin-1-yl group.

Examples of the substituent on the “C3-8 cycloalkyl group”, “C6-10 aryl group” and “3-6 membered heterocyclyl group” in X ¹ include a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, C1 -6 alkoxy group, halogeno group, cyano group, nitro group and the like.

Examples of the “amino group having a substituent” in X ¹ include C1-6 alkyl-substituted amino groups such as a methylamino group, an n-butylamino group, a dimethylamino group, and a diethylamino group.

Examples of the “halogeno group” for X ¹ include a fluoro group, a chloro group, a bromo group, and an iodo group.

Of the groups as described above, X ¹ is preferably a C 1-6 haloalkyl group.

In formula (I) and formula (II), n represents the number of chemically acceptable X ¹ and is an integer of 0-4. When n is 2 or more, X ¹ may be the same or different.
If A ¹ is a carbon atom, n represents an integer of 0-4. If A ¹ is a nitrogen atom, n represents an integer of 0 to 3.

In formula (I) and formula (II), R ¹ is a halogeno group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted group Or a substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C1-6 alkylsulfonyloxy group, or a formula: —S (═O) (═N—R ^a ) —R ^b Represents a group.
Here, R ^a and R ^b each independently represent an unsubstituted or substituted C 1-6 alkyl group.

Examples of the “halogeno group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, and “C1-6 alkylsulfonyl group” in R ¹ and the group having a substituent in these groups include the above X ^1. Examples thereof are the same as those exemplified in.

Examples of the “C1-6 alkylsulfonyloxy group” for R ¹ include a methylsulfonyloxy group, an ethylsulfonyloxy group, a t-butylsulfonyloxy group, and the like.
Specific examples of the “substituted C1-6 alkylsulfonyloxy group” include C1-6 haloalkylsulfonyloxy groups such as a trifluoromethylsulfonyloxy group and a 2,2,2-trifluoroethylsulfonyloxy group. .
“C1-6 alkyl group” in R ^a and R ^b in the group represented by the formula: —S (═O) (═N—R ^a ) —R ^b and a group having a substituent in these groups include The same as those exemplified in the above X ¹ can be mentioned.

In formula (I) and formula (II), R ² represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted group. Having C2-6 alkynyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1 -6 alkoxycarbonyl group, or an unsubstituted or substituted C1-6 alkylsulfonyl group.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for R ² Examples of the “group”, “C1-6 alkylsulfonyl group”, and groups having substituents on these groups include the same groups as those exemplified above for X ¹ .

In formula (I) and formula (II), Ar represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-6 membered heteroaryl group.
Examples of the “C6-10 aryl group” and “5-6 membered heteroaryl group” in Ar include the same as those exemplified in the above X ¹ .
The “C6-10 aryl group” in Ar is preferably a phenyl group. The “5- to 6-membered heteroaryl group” in Ar is preferably a thienyl group, pyrazolyl group, thiazolyl group, pyridyl group, pyrimidyl group, or pyridazinyl group.

  Examples of the substituent on the “C6-10 aryl group” and “5-6 membered heteroaryl group” in Ar include an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2— 6 alkenyl group, unsubstituted or substituted C2-6 alkynyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl Group, unsubstituted or substituted C1-6 alkoxycarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, Substituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C3-8 A chloroalkyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted 3-6 membered heterocyclyl group, an unsubstituted or substituted amino group, a halogeno group, a cyano group, A nitro group etc. are mentioned.

"C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group" in the above-mentioned "substituents on" C6-10 aryl group "and" 5-6 membered heteroaryl group "in Ar" , “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, “C1-6 alkyl” "Sulfonyl group", "C3-8 cycloalkyl group", "C6-10 aryl group", "3-6 membered heterocyclyl group", "amino group", "halogeno group" and groups having substituents on these groups Are the same as those exemplified in X ¹ above.

Examples of the substituent on the “C6-10 aryl group” and “5-10 membered heteroaryl group” in Ar include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, and a C1-6 haloalkoxy group. C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, and halogeno group are preferable.
The number of substituents on the “C6-10 aryl group” and “5-10 membered heteroaryl group” in Ar is preferably 0-3, and more preferably 1 or 2.

式（III）および式（IV）中、Ａ¹、Ｘ¹、Ｒ¹、およびＲ²は、式（I）および式（II）中のそれらと同じ意味を示す。 The diaryltriazole compound of the present invention is preferably a compound represented by formula (III) or formula (IV) (hereinafter sometimes referred to as compound (III) or compound (IV)) or a salt of compound (III) Alternatively, it is a salt of compound (IV).

In formula (III) and formula (IV), A ¹ , X ¹ , R ¹ and R ² have the same meaning as in formula (I) and formula (II).

In formula (III) and formula (IV), X ^1a , X ² and X ^2a are each independently an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6. An alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, a formyl group, an unsubstituted or substituted C1-6 alkylcarbonyl group , Unsubstituted or substituted C1-6 alkoxycarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted Or substituted or unsubstituted C1-6 alkylsulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted Or shown C6~10 aryl group having a substituent, 3- to 6-membered heterocyclyl group having unsubstituted or substituted group, an amino group having unsubstituted or substituted group, a halogeno group, a cyano group or a nitro group.

In the formulas (III) and (IV), k represents the number of chemically acceptable X ^1a and is an integer of 0 to 3. When k is 2 or more, X ^1a may be the same as or different from each other.
In the formulas (III) and (IV), h represents the number of chemically acceptable X ^2a and is an integer of 0-4. When h is 2 or more, X ^2a may be the same or different.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group” in X ^1a , X ² and X ^2a , “C1-6 alkoxycarbonyl group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, “C1-6 alkylsulfonyl group”, “C3-8 cycloalkyl group”, “C6-10 aryl group” ”,“ 3 to 6-membered heterocyclyl group ”,“ amino group ”, and“ halogeno group ”and the group having a substituent in these groups are the same as those exemplified for X ¹ above.
Of these, X ² is preferably a C 1-6 haloalkyl group.

  The salt of compound (I)-(IV) will not be restrict | limited especially if it is an agricultural and horticulturally acceptable salt. Examples of the salts of compounds (I) to (IV) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; calcium and magnesium And salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, and hydrazine.

  The salt of compound (I)-(IV) or compound (I)-(IV) is not specifically limited by the manufacturing method. For example, the compounds (I) to (IV) or the salts of the compounds (I) to (IV) of the present invention can be obtained by known production methods described in Examples and the like. Moreover, the salt of compound (I)-(IV) can be obtained from compound (I)-(IV) by a well-known method.

The diaryltriazole compound of the present invention is excellent in controlling pests such as various agricultural pests and mites that affect the growth of plants.
In addition, the diaryltriazole compound of the present invention is a highly safe compound because it has little phytotoxicity to crops and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or an acaricide.
Furthermore, in recent years, resistance to various existing drugs has been developed in many pests such as moths, leafhoppers, leafhoppers, and aphids, resulting in problems of insufficient efficacy of these drugs. ing. The diaryltriazole compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on pests of various resistant strains and further on mite-resistant strains of mites.

  The diaryltriazole compound of the present invention is excellent in the control effect of ectoparasites and endoparasites harmful to humans and animals. In addition, it is a highly safe compound because of its low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an ectoparasite and endoparasite control agent.

  In addition, the arylimidazole compound of the present invention exhibits efficacy at all stages of development of organisms to be controlled, and has an excellent control effect on, for example, eggs, nymphs, larvae, pupae and adults such as mites and insects. Show.

[Pesticides, insecticides or acaricides]
The pest control agent or insecticide or acaricide of the present invention contains at least one selected from the diaryltriazole compounds of the present invention as an active ingredient. The amount of the arylimidazole compound contained in the pest control agent of the present invention or the insecticide or acaricide is not particularly limited as long as it exhibits a pest control effect.

The pest control agent or insecticide or acaricide of the present invention includes grains, vegetables, root vegetables, potatoes, trees such as fruit trees, tea, coffee, cacao, grasses, turf, cotton, etc. It is preferably used for plants.
In application to plants, the pest control agent or insecticide or acaricide of the present invention may be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used for these parts.
Moreover, the pest control agent or insecticide or acaricide of the present invention is not particularly limited depending on the species of plant to be applied. Examples of plant seeds include original species, varieties, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMO).

  The pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application and the like in order to control various agricultural pests and mites.

  Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.

(1) Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis;
(B) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella;
(C) Carposinidae, for example, Carposina sasakii;
(D) moths of the family Craambidae, for example Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp. , Ostrinia furnacalis, European corn borer (Ostrinia nubilalis), Azuchi no moth (Ostrinia scapulalis); Diatraea grandiosella), Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella;
(E) Gelechiidae moths such as Helcystogramma triannulella, Pectinophora gossypiella, Phthhorimaea operculella, Sitotroga cerealella;
(F) Geometridae moths, for example Ascotis selenaria;
(G) moths of the family Gracillariidae, such as, for example, Caloptilia theivora, citrus leafworm (Phyllocnistis citrella), phleglonorycter ringoniella;
(H) Hesperiidae butterflies such as Parnara guttata;
(I) moths of Lasiocampidae, for example, Malacosoma neustria; (j) moths of Lymantriidae, for example, Lymantria spp., Lymantria dispar, nonnemaimai (Lymantria monacha); Others, Euproctis pseudoconspersa, Orgyia thyellina;

(K) moths of the family Lyonetiidae, for example, Lyonetia clerkella, Lyonetia prunifoliella malinella, from the genus Lyonetia spp .;
(L) Noctuidae moths, for example, Spodoptera spp., Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Spodoptera exigua ), African Spodoptera littoralis, Spodoptera litura; eg, Autographa spp., Autographa gamma, Autographa nigrisigna; eg, Agrotisp. For example, Agrotis ipsilon, Agrotis segetum; for example, Helicoverpa spp., Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea); Of the seed (Heliothis spp.) (Heliothis armigera), fake American tobacco (Heliothis virescens); other, Aedia leucomelas; (Naranga aenescens), Pinola japonica, Peridroma saucia, Soybean looper (Pseudoplusia includens), Trichoplusia ni;
(M) Nolidae moths such as Misaria olinga (Earias insulana);
(N) Pieridae butterflies, for example, Pieris sp., Pieris brassicae, Pieris rapae crucivora;
(O) moths of the family Plutellidae, for example, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella of Acrolepiopsis spp .; Others, Plutella xylostella;
(P) Pyralidae moths, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella;
(Q) Sphingidae moths, for example, Manduca quinquemaculata, Manduca sexta of Manduca spp .;

(R) moths from the family Stahmopodidae, for example, Stahmopoda masinissa;
(S) moths of the family Tineidae, for example, tiger (Tinea translucens);
(T) Tortricidae moths, for example, Adoxophyes honmai, Adoxophyes orana of Adoxophyes spp .; for example, Archips spp. ), Apple chips (Archips breviplicanus), green chips leaf (Archips fuscocupreanus); ), Chamonaki (Homona magnanima), Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Spiananothis pill;
(U) Yponomeutidae moth, for example, Argyresthia conjugella.

(2) Thysanoptera pests (a) from the Phlaeothripidae, for example, Ponticulothrips diospyrosi;
(B) From the Thripidae family, for example, from Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; Thrips palmi, Thrips tabaci; Others, Croton thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.

(3) Hemiptera pests (A) Ceratomas (Archaeorrhyncha)
(A) From the Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, Sogatella furcifera.

(B) Clypeorrhyncha
(A) From the family of Cicadellidae, for example, from the Empoasca spp., The Empoasca fabae, the Empoasca nipponica, the Empoasca onukii, the legume Emporasca sakaii, other, butterfly (Arboridia apicalis), green leafhopper (Balclutha saltuella), leafhopper leafhopper (Epiacanthus stramineus), leafhopper leafhopper (Macrosteles striifrons), nectar hot eps ).

(C) Stink bug (Heteroptera)
(A) from the family Alydidae, for example, Riptortus clavatus;
(B) From the family Coridae, for example, Cletus punctiger, Leptocorisa chinensis;
(C) From the family of the family Lygaeidae (Lygaeidae), for example
leucopterus), Cavelerius saccharivorus, Togo hemipterus;
(D) From the Miridae family, for example, the black turtle (Halticus insularis), the white turtle (Lygus lineolaris), the cotton-free hopper (Psuedatomoscelis seriatus), the stag beetle (Stenodema sibiricum), the stag moth ru ), Trigonotylus caelestialium;

(E) from the Pentatomidae family, for example, from the Nezara spp., Nezara antennata, Nezara viridula; , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Others, Dolycoris baccarum, Eurydema rugous sword Halyomorpha halys), Piezodorus hybneri, Plautia crossota, Scotinophora lurida;
(F) from the family Pyrrhocoridae, for example, Dysdercus cingulatus;
(G) from the family Rhopalidae, for example, Rhopalus msculatus;
(H) From the family Scutelleridae, for example, Eurygaster
integriceps);
(I) From the Tingidae family, for example, Stephanitis nashi.

(D) Sternorrhyncha
(A) from the family Adelgidae, for example, Adelges laricis;
(B) Aleyrodidae, for example, Bemisia spp., Silver leaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Others, Aleurocanthus spiniferus, citri), Trialeurodes vaporariorum;
(C) Aphididae, for example, from Aphis spp., Aphis craccivora, bean aphid (Aphis fabae), strawberry aphid (Aphis forbesi), cotton aphid (Aphis gossypii) , European apple aphids (Aphis pomi), elder-core aphids (Aphis sambuci), Aphis spiraecola; for example, Rhopalosiphum spp., Corn aphids (Rhopalosiphum maidis), hum For example, Dysaphis plantaginea, Dysaphis radicola of Dysaphis spp .; for example, Macrosiphum avenae, Macrosiphum avenae, Aphid (Macrosiphum euphorbiae); For example, from the genus Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; Other, Acyrthosiphon pisum, potato beetle Aphids (Aulacorthum solani), wheat aphids (Brachycaudus helichrysi), radish aphids (Brevicoryne brassicae), strawberry aphids (Chaetosiphon fragaefolii), peach aphids (Hyalopteruc prae) Lipaphis erysimi, broad bean aphid (Megoura viciae), barley aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hops aphid (Phorodon humuli), barley aphid (Schizaphis graminum), wheat aphid (Sitobion avenae), rice aphid (Toxoptera aurantii);

(D) from the family Coccidae, for example, Ceroplastes ceriferus, Ceroplastes rubens, from the genus Ceroplastes spp .;
(E) Pseudaulacaspis pentagona, Pseudaulacaspis prunicola of Pseudaulacaspis spp. From the family Diaspididae; for example, Unaspisp. , Unaspis euonymi, Unaspis yanonensis; Others, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theoni dia, Poriomae );
(F) from the order of the Margarodidae family, for example, Drosicha corpulenta, Icerya purchasi;
(G) from the family Aphididae (Phylloxeridae), for example, grape aphid (Viteus vitifolii);
(H) From the Pseudococcidae family, for example, from Planococcus spp., Planococcus citri, Planococcus kuraunhiae; other, Phenacoccus sol , Pseudococcus comstocki;
(I) From the Psyllidae family, for example Psylla mali, Psylla malis, Psylla pyrisuga; other, Diaphorina citri.

(4) Polyphaga pests (a) from the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne);
(B) From the Attelabidae family, for example, Byctiscus betulae, Rhynchites heros;
(C) from the family Bostrichidae, for example, Lyctus brunneus;
(D) from the Brentidae family, for example, Cylas formicarius;
(E) from the Buprestidae family, for example, Agrilus sinuatus;
(F) From the Cerambycidae family, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoder;
(G) From the Chrysomelidae family, for example, the Bruchus spp., The pea weevil (Bruchus pisorum), the broad beetle (Bruchus rufimanus); for example, the northern corn of the Diabrotica spp. Rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera); for example, Phyllotreta nemorum, Phyllotreta nemorum, Phyllotreta nemorum ); Others, Aulicophora femoralis, Adzuki beetle (Callosobruchus chinensis), Tortoise beetle (Cassida nebulosa), Tentobi beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), Nekubihoso yzae (Oule) Nagasnetobiham Psylliodes angusticollis;

(H) from the species of the Coccinellidae, for example, Epilachna varivestis, Epilachna vigintioctopunctata, from the genus Epilachna spp .;
(I) from the family Curculionidae, for example, Anthonomus spp., Anthonomus grandis, Anthonomus pomorum; eg, Sitophilus spp. , Granary weevil (Sitophilus granarius), weevil (Sitophilus zeamais); other, weevil (Echinocnemus squameus), weevil (Euscepes postfasciatus), pine weevil (Hylobius abietis), alfalfa weevil (Hylobius abietis) Lissohoptrus oryzophilus, horned weevil (Otiorhynchus sulcatus), red-footed weevil (Sitona lineatus), Sphenophorus venatus;
(J) from the family Elateridae, for example, Melanotus fortnumi, Melanonotus tamsuyensis, from the genus Melanotus spp .;
(K) from the family Nitidulidae, for example, Epuraea domina;
(L) From the family Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; Other, Cetonia aurata, Coretis ), Heptophylla picea, Melonlontha melolontha, Popillia japonica;
(M) from the Scolytidae family, for example, Ips typographus;
(N) from the family Staphylinidae, for example, Paederus fuscipes;
(O) from the family Tenebrionidae, for example, Tenebrio molitor, Tribolium castaneum;
(P) From the family Trogossitidae, for example, Tenebroides mauritanicus.

(5) Flies (Diptera) Pests (A) Brachycera
(A) From the family Agromyzidae, for example, of the genus Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza sativae, Liriomyza sativae, Liriomyza Others, Chromatomyia horticola, Agromyza oryzae;
(B) from the family Anthomyiidae, for example, Delia spp., Delia platura, Cabbage fly (Delia radicum); Other, Pegomya cunicularia;
(C) Drosophila suzukii from the Drosophilidae family, for example, from Drosophila spp., Drosophila melanogaster, Drosophila suzukii;
(D) from the Ephydridae family, for example, Hydrellia griseola;
(E) from the family Psilidae, for example, Psila rosae;
(F) Tephritidae, for example, Bactrocera cucurbitae, Bactrocera dorsalis; for example, Rhagoletis spp. Rhagoletis cerasi), Rhagoletis pomonella; Others, Ceratitis capitata, Olive fruit fly (Dacus oleae).

(B) Nematocera
(A) From the family Cecidomyiidae, for example, the soybean fly (Asphondylia yushimai), the sorghum fly (Contarinia sorghicola), the fly fly (Mayetiola destructor), the squirrel fly fly (Sitodiplosis mosellana).

(6) Orthoptera pests (a) Acrididae, for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; Australian flying grasshopper (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), Tosama locust (Locusta migratoria), Brown locust (Locustana pardalina), Red locust (Nomadacris septemfasciata), Cobaneago (Oxya yezoensis)
(B) From the cricket family (Gryllidae), eg, European cricket (Acheta domestica), Teleogryllus emma;
(C) from the family Gryllotalpidae, for example, Gryllotalpa orientalis;
(D) From the Tettigoniidae family, for example, Tachycines asynamorus.

(7) Tick (Acari)
(A) Astigmata (Acaridida)
(A) Acaridae mites, for example, Rhizoglyphus echinopus, Rhizoglyphus echinipus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acetus tuna (Acarusus phlegm), Acet

(B) Prostigmata mite (Actinedida)
(A) Mites of Tetranychidae, for example, Bryobia spp., Clover spider mite (Bryobia praetiosa), Fowl spider mite (Bryobia rubrioculus); Of the spider mite (Eotetranychus kankitus), tick (Eotetranychus asiaticus), tick (Eotetranychus kantis) (Eotetranychus smithi), Sugimen spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); for example, Oligonis spp. Ma Spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), spider mite (Oligonychus spp. , Citrus spider mite (Panonychus citri), swan spider mite (Panonychus mori), apple spider mite (Panonychus ulmi); , Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis; for example, Aponychus spp. For example, the spider mite (Aponychus firmianae); for example, Sasanychus spp. ), Sponge spider mite (Shizotetranychus longus), Shizotetranychus miscanthi, Shizotetranychus schizopus, Others, Tetella spp sapporensis);

(B) Tenuipalpidae ticks, for example, Brevipalpus spp. From Brevipalpus spi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus), brevipalpus californicus; for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other, pineapple chony tick (Doli)
(C) Mites of the family Eriophyidae, for example, Aceria spos., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Rust mites (Aceria paradianthi), Black mite mites (Aceria tiyingi), Tulip mite (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp. emarginatae); eg, Aculops spp., Aculops lycopersici, Aculops pelekassi; eg, Aculus spp., Aculus fockeui, Aculus fockeui schlechtendali); Others, Acaphyll a theavagrans, Calacarus carinatus, Grape's spider mite (Colomerus vitis), Grape's spider mite (Calepitrimerus vitis), Pterosarid mite (Epitrimerus pyri), Antarctic spider mite (Paraphytoptus kikus), Maxi spider mite (Paracalacarus podocarta) citri);
(D) Tick of the family Miteaceae (Transonemidae), for example, Tarsonemus bilobatus, Tarsonemus waitei of Tarsonemus spp .; );
(E) Penthaleidae ticks, for example, Penthaleus erythrocephalus, Penthaleus major from Penthaleus spp.

The pest control agent of the present invention includes other active ingredients such as fungicides, insecticides / acaricides, nematicides, soil pesticides; plant regulators, synergists, fertilizers, soil improvers, animal use It may be mixed or used together with feed.
A combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect on insecticidal / miticidal activity. The synergistic effect can be confirmed by Colby's formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a standard method.

  Specific examples of insecticides / acaricides, nematicides, soil insecticides, insecticides and the like that can be used in combination or in combination with the pest control agents of the present invention are shown below.

(1) Acetylcholinesterase inhibitor:
(a) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxyl Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;

(b) Organophosphorus: Acephate, azamethiphos, azinephos-ethyl, azinephos-methyl, kazusafos, chlorethoxyphos, chlorfenvinphos, chlormefos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, Dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethione, etoprophos, famfur, phenamiphos, fenitrothion, fenthion, phostiazet, heptenophos, imisiaphos, isofenphos, isocarbophos, isoxathione, malathione, methalmethione, mecarbamethione Monocrotophos, nared, ometoate, oxydimethone-methyl, parathion, parathion-methyl, phentoe Folate, hosalon, phosmet, phosphamidone, phoxime, pyrimiphos-methyl, propenophos, propetamphos, prothiophos, pyracrofos, pyridafenthion, quinalphos, sulfotep, tebupyrine phos, temefos, terbufos, tetrachlorbinphos, thiomethone, triazophos, trichlorfos, bromomidion, bromomidion Ethyl, BRP, carbophenothion, cyanophenphos, CYAP, demeton-S-methylsulfone, diariphos, diclofenthion, dioxabenzophos, etrimphos, phensulfothion, flupyrazophos, phonofos, formomothion, phosmethylan, isazophos, iodofenphos, methacliphos , Pyrimifos-ethyl, phosphocarb, propaphos, protoate, sulfophos.

(2) GABA-agonist chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor, dienochlor.
(3) Sodium channel modulator: Acrinatrin, d-cis-trans allelesine, d-transareleslin, bifenthrin, bioareslin, bioareslin isomers, bioresmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, ciphenothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R) -isomers], esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, tau-fulvalinate, halfenprox, imiprothrin, cade Phosphorus, permethrin, phenothrin [(1R) -trans isomer], praretrin, pyrethram, resmethrin, silafluophene, tefluthrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II , Profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, fulbrocitrinate, flufenprox, methfluthrin, protrifen butto, pyrethmethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine, flupiradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulator: spinetoram, spinosad.
(6) Chloride channel activator: Abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadectin.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen, diophenolan, epofenanane, triprene.
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar.
(9) Homogeneous selective feeding inhibitors: flonicamid, pymetrozine, pyrifluquinazone.

(10) Tick growth inhibitor: clofentezin, difluvidazine, hexythiazox, etoxazole.
(11) Microbial-derived insect midgut lining destroyer: Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutasine oxide, propargite, tetradiphone.
(13) Oxidative phosphorylation uncoupler: chlorfenapyr, sulfuramide, DNOC, binapacryl, dinobutone, dinocup.
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride, nereistoxin, thiosultap monosodium salt, thiocyclam.
(15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron.
(16) Diptera molting agent: cyromazine.
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.
(18) Octopamine receptor agonist: Amitraz, demiditraz, chlordimeform.
(19) Mitochondrial electron transport system complex III inhibitor: acequinosyl, fluacrylpyrim, hydramethylnon.
(20) Mitochondrial electron transport system complex I inhibitor: phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.

(21) Voltage-gated sodium channel blocker: indoxacarb, metaflumizone.
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat.
(23) Mitochondrial electron transport complex IV inhibitor: Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport system complex II inhibitor: Sienopyrafen, cyflumethofene, pivlumide.
(25) Ryanodine receptor modulator: chlorantraniliprole, cyantraniprole, fulvendiamide, cyclaniliprol, tetraniprolol.
(26) Mixed function oxidase inhibitor compound: Piperonyl butoxide.
(27) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (the mechanism of action is unknown): azadirachtin, benzoximate, biphenazate, bromopropyrate, quinomethionate, cryolite, dicofol, pyridalyl, bencrothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, Phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, fluphenazine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, tetrasul, trialacene, aphidopyropene (afidopyropen ), Flometokin, flufiprole, fluenesulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodeca Amide, fluralanel, afoxolanel, floxamethamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2,4 -Triazol-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, and other metadiamides.

(29) Anthelmintic:
(a) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, fulbendazole, fevantel, netobimine, thiophanate, thiabendazole, canbendazole;
(b) Salicylanilide series: closantel, oxyclozanide, rafoxanide, niclosamide;
(c) substituted phenols: nitroxinyl, nitroskanate;
(d) Pyrimidine series: Pirantel, Morantel;
(e) Imidazothiazole series: levamisole, tetramisol;
(f) Tetrahydropyrimidine series: praziquantel, epsiprantel;
(g) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetalamide, melolsamine, arsenamide.

Specific examples of the bactericides that can be used in combination or in combination with the pest control agent of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, cloziracone, off-race;
(b) adenosine deaminase inhibitor: bupilimate, dimethylylmol, ethylimol;
(c) DNA / RNA synthesis inhibitors: Himexazole, octirinone;
(d) DNA topoisomerase II inhibitor: Oxophosphate.

(2) Mitotic fission inhibitor and cell division inhibitor:
(a) β-tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, dietofencarb, zoxamide, ethaboxam;
(b) Cell division inhibitor: Pencyclon;
(c) Delocalization inhibitor of spectrin-like protein: fluopicolide.

(3) Respiratory inhibitor:
(a) Complex I NADH oxidoreductase inhibitor: diflumetrim, tolfenpyrad;
(b) Complex II succinate dehydrogenase inhibitor: benodanyl, flutolanil, mepronil, isophetamide, fluopyram; fenfram, flumeciclox, carboxin, oxycarboxyl, tifluzamide, benzovindiflupyr, bixafen, floxapyroxide , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pyraziflumide;
(c) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin, pyraclostrobin, Pyramethostrobin, triclopyricarb, cresoxime-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, oryastrostrobin, famoxadone, floxastrobin, fenamidone, pyribencarb, mandestrobin;
(d) Complex III ubiquinol reductase Qi inhibitor: cyazofamide, amisulbrom;
(e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocup, dinocup, fluazinam, ferrimzone;
(f) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): Fentine acetate, fentin chloride, fentin hydroxide
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): Amethoctrazine.

(4) Amino acid and protein synthesis inhibitors
(a) Methionine biosynthesis inhibitor: Andoprim, cyprodinil, mepanipyrim, pyrimethanil;
(b) Protein synthesis inhibitor: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

(5) Signaling inhibitor:
(a) Signaling inhibitor: quinoxyphene, proquinazide;
(b) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpicuronyl, fludioxonil, clozolinate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(a) Phospholipid biosynthesis, methyltransferase inhibitor: Edifenphos, iprobenphos, pyrazophos, isoprothiolane;
(b) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl, etridiazole;
(c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb;
(d) Microorganisms that disturb the pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain;
(e) Agent that disturbs the cell membrane: An extract of Goseika Yupte (Tea Tree).

(7) Cell membrane sterol biosynthesis inhibitors:
(a) Demethylation inhibitor at the C14 position in sterol biosynthesis: trifolin, pyrifenox, pyrisoxazole, phenarimol, flurprimidol, nuarimol, imazalyl, imazalyl sulfate, oxpoconazole, pefazoate, prochloraz, triflumizole , Viniconazole, azaconazole, viteltanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole , Fluquinconazole, simeconazole, tebuconazole, tetraconazole triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, main phen triflupromazine Kona tetrazole;
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
(c) 3-keto reductase inhibitors in C4 demethylation of sterol biosynthesis system: phenhexamide, fenpyrazamine;
(d) Sterol biosynthetic squalene epoxidase inhibitors: Pyributibalbu, Naftifine, Terbinafine.

(8) Cell wall synthesis inhibition
(a) trehalase inhibitor: validamycin;
(b) chitin synthase inhibitor: polyoxin, polyoxorim;
(c) Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph, benavalicarb, iprovaricarb, toluprocarb, varifenalate, mandipropamide.

(9) Melanin biosynthesis inhibitor
(a) Reductase inhibitors of melanin biosynthesis: fusaride, pyroxylone, tricyclazole;
(b) Dehydrase inhibitors of melanin biosynthesis: carpropamide, diclosimet, phenoxanyl;
(c) Other: Torprocarb.

(10) Host plant resistance inducer:
(a) Agents acting on the salicylic acid synthesis pathway: Acibenzoral-S-methyl;
(b) Others: Probenazole, thiazinyl, isothianyl, laminarin, giant redbird extract.

(11) Agents whose activity is unknown: Simoxanyl, fosetyl aluminum, phosphoric acid (phosphate), teclophthalam, triazoxide, fursulfamide, dichromedin, metasulfocarb, cyflufenamide, metolaphenone, pyriophenone, dodine, dodine free base, fluthianyl.

(12) Agents with multiple action points: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, farbum, mancozeb, maneb, Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram, captan, captahol, phorpet, chlorothalonil, dichlorfluanid, tolylfluanid, guazatine, iminoctadine acetate (iminoctadine albecate (iminoctadine) trialbesilate), anilazine, dithianone, quinomethionate, fluorimide.

(13) Other agents: DBEDC, fluorophorpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methyl isothiocyanate (MITC ), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat methylsulfonate, Flumetober, Focetyl calcium, Focetyl sodium, Irumamycin, Natamycin, Nitrotal isopropyl , Oxamocarb, pyrrolnitrin, tebufloquine, torniphanide, zaliramide, Algophase, amicaliazole (Amicarthiazol), oxathiapiproline, methylam zinc, Thiazole, trichlamide, uniconazole, mill Deo mycin, oxyphencyclimine Ji-in (Oxyfenthiin), Pical -but Ratho box (picarbutrazox), phen Pico alkylcarboxamide (Fenpicoxamid), dichloride bench azo box (dichlobentiazox), Kinofumerin (Quinofumelin)

Specific examples of plant regulators that can be used in combination or in combination with the pest control agent of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenothiol, 1 -Naphtylacetamide, Ethiclozate, Cloxiphonac, Maleic acid hydrazide, 2,3,5-Triiodobenzoic acid, Salicylic acid, Methyl salicylate, (-)-Jasmonic acid, Methyl jasmonate, (+)-Strigol, (+) -Deo Cysts Rigoru, (+) - Orobankoru, (+) - Sorugorakuton, 4-oxo-4- (2-phenylethyl) amino acid; ethephon, chlormequat, mepiquat chloride, benzyl adenine, 5-aminolevulinic acid.

[External parasite control agent]
The ectoparasite control agent of the present invention contains at least one selected from the diaryltriazole compounds of the present invention as an active ingredient. The diaryltriazole compound of the present invention is excellent in the control effect of ectoparasites harmful to humans and animals.

Examples of ectoparasites include ticks, lice, fleas, mosquitoes, flies, and flyflies.
Examples of host animals to be treated with the ectoparasite control agent of the present invention include pets such as dogs and cats; pets; domestic animals such as cattle, horses, pigs, and sheep; It is done. Other examples include bees, stag beetles, and beetles.
Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, it infests the back, underarms, lower abdomen, and inner crotch of the host animal and obtains nutrients such as blood and dandruff from the animal.

  The ectoparasite control agent of the present invention can be applied by a known veterinary technique (topical, oral, parenteral or subcutaneous administration). As the method, it is administered orally to animals by tablet, capsule, feed mixing, etc .; it is administered to animals by immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc .; kneading an ectoparasite-controlling agent into a resin, shaping the kneaded product into an appropriate shape such as a collar or ear tag, and applying it to an animal A method of wearing and administering locally;

  Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Tick (Acari)
Dermanyssidae ticks, Macronyssidae ticks, Laelapidae ticks, Varroidae ticks, Argasidae ticks, Ixodidae ticks, cucumber genus mite Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodixidae mites, Trombiculidae mites, stag beetles and other parasitic insect mites .
(2) Phythiraptera
Haematopinidae lice, Linognathidae lice, Mennoponidae lice, Philopteridae lice, Trichodectidae lice
(3) Flea eyes (Siphonaptera)
Pulicidae fleas, for example, Ctenocephalides canis, Ctenocephalides felis of Ctenocephalides spp .;
Fleas from the family Tungidae, fleas from the Ceratophyllidae family, and fleas from the Leptopsyllidae family.
(4) Hemiptera.
(5) Diptera mosquitoes of Culicidae, Simuliidae mosquitoes, Ceratopogonidae mosquitoes, Tabanidae abu, Muscidae flies, Glossinidae shave flies, moss flies, hippoboscidae flies, Calliphoridae flies, Oestridae flies.

[Internal parasite control or control agent]
The endoparasite control or control agent of the present invention contains at least one selected from the diaryltriazole compounds of the present invention as an active ingredient.

  Parasites that are targets of the endoparasite control or pesticide of the present invention parasitize in host animals, particularly warm-blooded animals and fish (endoparasites). Examples of host animals in which the endoparasite control or control agent of the present invention is effective include humans, livestock mammals (eg, cows, horses, pigs, sheep, goats, etc.), laboratory animals (eg, mice, rats, gerbils, etc.). , Pets (eg, hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalos, etc.), poultry (turkeys, ducks, chickens, quails) , Geese, etc.), warm-blooded animals such as pets (parves, parrots, sovereign birds, wild birds, parakeets, juvenile pine, canaries, etc.); or fishes such as salmon, trout, swordfish. By controlling and controlling the parasite, it is possible to prevent or treat a parasitic disease mediated by the parasite.

Examples of parasites to be controlled or controlled include the following.
(1) nematodes of the order of Dioctophymatida (a) nematodes of the family Dioctophymatidae, for example, Dioctophyma renale of Dioctophyma spp .;
(B) Nematodes of the Soboliphymatidae family, for example, Soboliphyme abei, Soboliphyme baturini from the species of the genus Soboliphyme spp.

(2) Trichocephalida nematodes (a) Trichinellidae trichinella, for example, Trichinella spp. Trichinella spiralis;
(B) Trichuridae trichinella, for example Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic trichomes (Capillaria spp.) Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris vulpis, Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.

(3) Rhabditida nematodes: Strongyloides spp., For example, Strongyloides papillosus, cat feces from Strongyloides spp. Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .

(4) Strongylida nematodes: Ancylostomatidae worms, for example, Ancylostoma braziliense, Ancylostoma caninum, Zubini worms of the genus Ancylostoma spp. (Ancylostoma duodenale), cat helminth (Ancylostoma tubaeforme); Uncinaria stenocephala; Uncinaria stenocephala; Bunostomum spp. Bunostomum trigonocephalum).

(5) Strongylida nematodes (a) Nematodes of the Angiostrongylidae family, for example, Aelurostrongylus abstrusus, of the genus Aelurostrongylus spp. From the genus Angiostrongylus spp., Angiostrongylus vasorum, Angiostrongylus cantonesis;
(B) Crenosomatidae nematodes, for example, Crenosoma aerophila, Crenosoma vulpis of Crenosoma spp .;
(C) Nematodes of the family Filaroididae, for example, Filaroides hirthi, Filaroides osthori (Filaroides spp.)
osleri);
(D) Pneumonia from the family Phyllidae (Metastrongylidae), for example, Metastrongylus aprius, Metastrongylus asymmetricus, Metastrongylus asymmetricus, Metastrongylus asymmetricus (Metastrongylus spp.) Metastrongylus pudendotectus), Metastrongylus salmi;
(E) Kaigamiworms of the Syngamidae family, for example, Cyathostoma bronchialis of the genus Cyathostoma spp .; Syngamus skrjabinomorpha), chicken worm (Syngamus trachea).

(6) Nematodes of Strongylida (a) Nematodes of the family Molineidae, for example, Nematodirus filicollis, Nematodirus filicollis of Nematodirus spp. Tigger (Nematodirus spathiger);
(B) Nematodes of the Dictyocaulidae family, for example, Dictyocaulus spp., Dictyocaulus filaria, Bovine pneumoniae (Dictyocaulus viviparus);
(C) Haemonchidae nematodes, for example, Haemonchus contortus from Haemonchus spp .; Cattle tortoises from Mecistocirrus spp. (Mecistocirrus digitatus);
(D) Haemonchidae nematodes, for example, Ostertagia ostertagi from the genus Ostertagia spp .;
(E) Nematodes of the family Heligmonellidae, for example Nippostrongylus braziliensis, of the genus Nippostrongylus spp .;
(F) Trichostrongylidae nematodes, for example, Trichostrongylus axei, Trichostrongylus colubriformis of the genus Trichostrongylus spp. ), Trichostrongylus tenuis; Hyostrongylus spp., Hyostrongylus rubidus; Obeliscoides spp., Obeliscoides cuniculi ).

(7) Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, Shabertia spp., Chabertia ovina; Intestinal nodules From the genus Oesophagostomum spp., Oesophagostomum brevicaudatum, Oesophagostomum dentatum, Oesophagostomum dentatum, Oesophagostomum dentatum, Oesophagostomum spp. Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophanastomum (Oeswat)
(B) Nematodes of Stephanuridae, for example, Stephanurus dentatus of Stephanurus spp .;
(C) C. elegans (Strongylidae), for example, the species of the genus C. elegans (Strongylus spp.), D. e. , Common roundworm (Strongylus vulgaris).

(8) Oxyurida nematodes Oxyuridae nematodes, for example, Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris of Enterobius spp. spp.), Oxyuris equi; Passalurus spp., Passalurus ambiguus.

(9) Ascaridida nematodes (a) Nematodes of Ascaridiidae, for example, Ascaridia galli from Ascaridia spp .;
(B) Heterakidae nematodes, such as Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum of the genus Heterakis spp. , Heterakis pusilla, Heterakis putaustralis;
(C) Anisakidae nematodes, for example, Anisakis simplex from the genus Anisakis spp .;
(D) Ascarididae nematodes, eg, Ascaris spp., Ascaris lumbricoides, Ascaris suum; Parascaris spp., Ascaris (Parascaris equorum);
(E) Toxocaridae nematodes, for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasum, Toxocara vitulorum ), Toxocara cati.

(10) Spirurida nematodes (a) Onchocercidae nematodes, for example, Brugia spp., Brugia malayi, Brugia pahangi (Brugia pahangi), Brugia patei; Dipetalonema reconditum of Dipetalonema spp .; Dirofilaria spp., Dirofilaria spp. immitis); Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca cervicalis, Gibson filamentous (Onchocerca gibsoni), Pharyngeal Insect (Onchocerca gutturosa);
(B) Cetaceae (Setariidae) nematodes, for example, Setaria spp., Setaria digitata, Horseworm (Setaria equina), Lipid papillary (Setaria labiatopapillosa) , Setaria marshalli; from Wuchereria spp., Wuchereria bancrofti;
(C) Nematodes of Filariidae, for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria spum. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.

(11) Nematodes of Spirurida (a) Nematodes of Gnathostomatidae, for example, Gnathostoma doloresi of Gnathostoma spp. , Gnathostoma spinigerum;
(B) Nematodes of the family Habronematidae (Habronema spp.), For example, Habronema majus, Habronema microstoma, Habronema muscae; Draschia megastoma of the genus species (Draschia spp.);
(C) Nematodes of the family Physalopteridae, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaoptera pseudopraerutialis rara), Physaloptera sibirica, Physaloptera vulpineus;
(D) Nematodes of the Gongylonematidae family, for example, Gongylonema pulchrum of the genus Gongylonema spp .;
(E) Spirocercidae nematodes, for example, Ascarops strongylina from Ascarops spp .;
(F) Nematodes of Thelaziidae, for example, Thelazia spip., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eyes Insects (Thelazia rhodesi), Scriabin eyeworms (Thelazia skrjabini).

[Control agents for other pests]
In addition, pests that have poisonous needles and venom and cause damage to humans, pests that carry various pathogens and pathogens, and pests that cause discomfort to humans (toxic pests, sanitary pests, and unpleasant pests) Is excellent.
The specific example is shown below.
(1) Hymenoptera pest bee of Argidae, bee of Cynipidae, bee of Diprionidae, bee of Formicidae, bee of Mutillidae, A wasp of the vespidae family (Vespidae).

(2) Other pest cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes (crustacea), paddybirds (Cimex lectularius).

[Prescription formulation]
The formulation of the pest control agent, insecticide or acaricide of the present invention, ectoparasite control agent, or endoparasite control or control agent is shown in a few, but the additives and addition ratios are limited to these examples It is not something that can be changed and can be varied over a wide range. The parts in the formulation of the preparation indicate parts by weight.

  The formulation for agricultural and horticultural and paddy rice is shown below.

(Formulation 1: wettable powder)
40 parts of diaryltriazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate ester and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient. .

(Formulation 2: Emulsion)
30 parts of the diaryltriazole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkylallyl ether are mixed and dissolved to obtain an emulsion of 30% active ingredient.

(Formulation 3: Granules)
5 parts of the diaryltriazole compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated to a diameter of 0.5 to 1.0 mm. Granulate to obtain granules with 5% active ingredient.

(Formulation 4: Granules)
After 5 parts of the diaryltriazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate are thoroughly pulverized and mixed, water is added and kneaded well, and then granulated. Dry to obtain granules with 5% active ingredient.

(Formulation 5: Suspension)
10 parts of diaryltriazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water are mixed, and the particle size is 3 microns. Wet mill until the following content is obtained to obtain a 10% active ingredient suspension.

  The formulation of ectoparasite control agent or endoparasite control or control agent is shown below.

(Formulation 6: Granule)
5 parts of the diaryltriazole compound of the invention are dissolved in an organic solvent to obtain a solution, which is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.

(Formulation 7: Injection)
0.1 to 1 part of the diaryltriazole compound of the present invention and 99 to 99.9 parts of peanut oil are mixed uniformly, and then sterilized by filtration through a sterilizing filter.

(Formulation 8: Pour-on agent)
A pour-on agent is obtained by uniformly mixing 5 parts of the diaryltriazole compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.

(Formulation 9: Spot-on agent)
The spot-on agent is obtained by uniformly mixing 10 to 15 parts of the diaryltriazole compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.

(Formulation 10: Spray)
A spray is obtained by uniformly mixing 1 part of a diaryltriazole compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol.

  Next, compound examples will be shown to explain the present invention more specifically. However, this invention is not restrict | limited at all by the following compound examples.

[Example 1]
Synthesis of 5- (2- (Ethylsulfonyl) -4- (trifluoromethyl) phenyl) -1-methyl-3- (4- (trifluoromethyl) phenyl) -1H-1,2,4-triazole (Compound No. 1-6)

ＷＯ２０１１／００６９０３Ａ１に記載の方法に従って合成した３,５−ジブロモ−１−メチル−１Ｈ−１，２，４−トリアゾール（０．５ｇ）をジオキサン（２０ｍｌ）に溶解させて、室温で撹拌した。これに水（３ｍｌ）、２−フルオロ−４−（トリフルオロメチル）フェニルボロン酸（０．４３ｇ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（０．１２ｇ）、炭酸セシウム（１．０ｇ）を加え、反応容器内を窒素で置換し、加熱還流下で一晩撹拌した。該反応溶液を水へ注加し、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．３１ｇ（収率４６％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 7.79（t, 1H）, 7.60（d, 1H）, 7.54（d, 1H）, 3.87（d, 3H）. (Process 1)
Synthesis of 3-Bromo-5- (2-fluoro-4- (trifluoromethyl) phenyl) -1-methyl-1H-1,2,4-triazole

3,5-Dibromo-1-methyl-1H-1,2,4-triazole (0.5 g) synthesized according to the method described in WO2011 / 006903A1 was dissolved in dioxane (20 ml) and stirred at room temperature. Water (3 ml), 2-fluoro-4- (trifluoromethyl) phenylboronic acid (0.43 g), tetrakis (triphenylphosphine) palladium (0) (0.12 g), cesium carbonate (1.0 g) Was added, the inside of the reaction vessel was replaced with nitrogen, and the mixture was stirred overnight with heating under reflux. The reaction solution was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.31 g of the desired product (yield 46%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 7.79 (t, 1H), 7.60 (d, 1H), 7.54 (d, 1H), 3.87 (d, 3H).

3-Bromo-5-（2-fluoro-4-（trifluoromethyl）phenyl）-1-methyl-1H-1,2,4-triazole（０．３１ｇ）をジオキサン（１０ｍｌ）に溶解させて、室温で撹拌した。これに水（１．５ｍｌ）、４−（トリフルオロメチル）フェニルボロン酸（０．２７ｇ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（０．０５５ｇ）、炭酸セシウム（０．４７ｇ）を加え、反応容器内を窒素で置換し、１００℃で一晩撹拌した。該反応溶液を水へ注加し、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．２７ｇ（収率７２％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.25（d, 2H）, 7.86（t, 1H）, 7.71（d, 2H）, 7.63（d, 1H）, 7.55（d, 1H）, 3.94（d, 3H）. (Process 2)
Synthesis of 5- (2-Fluoro-4- (trifluoromethyl) phenyl) -1-methyl-3- (4- (trifluoromethyl) phenyl) -1H-1,2,4-triazole

3-Bromo-5- (2-fluoro-4- (trifluoromethyl) phenyl) -1-methyl-1H-1,2,4-triazole (0.31 g) was dissolved in dioxane (10 ml) and stirred at room temperature. did. To this was added water (1.5 ml), 4- (trifluoromethyl) phenylboronic acid (0.27 g), tetrakis (triphenylphosphine) palladium (0) (0.055 g), cesium carbonate (0.47 g). The inside of the reaction vessel was replaced with nitrogen, and the mixture was stirred at 100 ° C. overnight. The reaction solution was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.27 g (yield 72%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.25 (d, 2H), 7.86 (t, 1H), 7.71 (d, 2H), 7.63 (d, 1H), 7.55 (d, 1H), 3.94 ( d, 3H).

5-（2-Fluoro-4-（trifluoromethyl）phenyl）-1-methyl-3-（4-（trifluoromethyl）phenyl）-1H-1,2,4-triazole（０．２２ｇ）をＮ，Ｎ−ジメチルホルムアミド（６ｍｌ）へ溶解させて、室温で攪拌した。これにエチルメルカプタンナトリウム（８０%，０．０８９ｇ）を加え６０℃で２時間攪拌した。該反応溶液を室温まで冷却した後に、水に注ぎ、次いで酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．２１ｇ（収率８５％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.27（d, 2H）, 7.70（d, 2H）, 7.66（s, 1H）, 7.56（s, 2H）, 3.83（s, 3H）, 2.96（q, 2H）, 1.31（t, 3H）. (Process 3)
Synthesis of 5- (2- (Ethylthio) -4- (trifluoromethyl) phenyl) -1-methyl-3- (4- (trifluoromethyl) phenyl) -1H-1,2,4-triazole

5- (2-Fluoro-4- (trifluoromethyl) phenyl) -1-methyl-3- (4- (trifluoromethyl) phenyl) -1H-1,2,4-triazole (0.22 g) was converted to N, N-dimethyl. Dissolved in formamide (6 ml) and stirred at room temperature. Ethyl mercaptan sodium (80%, 0.089 g) was added thereto, and the mixture was stirred at 60 ° C. for 2 hours. The reaction solution was cooled to room temperature, poured into water and then extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.21 g of the desired product (yield 85%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.27 (d, 2H), 7.70 (d, 2H), 7.66 (s, 1H), 7.56 (s, 2H), 3.83 (s, 3H), 2.96 ( q, 2H), 1.31 (t, 3H).

5-（2-（Ethylthio）-4-（trifluoromethyl）phenyl）-1-methyl-3-（4-（trifluoromethyl）phenyl）-1H-1,2,4-triazole（０．１６ｇ）をジクロロメタン（５ｍｌ）へ溶解させて、０℃で攪拌した。これにメタクロロ過安息香酸（７０％，０．２０ｇ）を加え室温で一晩攪拌した。該反応溶液を飽和炭酸水素ナトリウム水溶液と飽和チオ硫酸ナトリウム水溶液の混合溶液へ注加し、ジクロロメタンで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．１７ｇ（収率９７％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR（400 MHz, CDCl₃）: δ 8.49（d, 1H）, 8.22-8.20（m, 2H）, 8.08（dd, 1H）, 7.73-7.70（m, 3H）, 3.79（s, 3H）, 3.44（q, 2H）, 1.28（t, 3H）. (Process 4)
Synthesis of 5- (2- (Ethylsulfonyl) -4- (trifluoromethyl) phenyl) -1-methyl-3- (4- (trifluoromethyl) phenyl) -1H-1,2,4-triazole

5- (2- (Ethylthio) -4- (trifluoromethyl) phenyl) -1-methyl-3- (4- (trifluoromethyl) phenyl) -1H-1,2,4-triazole (0.16 g) in dichloromethane (5 ml) ) And stirred at 0 ° C. To this was added metachloroperbenzoic acid (70%, 0.20 g) and stirred at room temperature overnight. The reaction solution was poured into a mixed solution of a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.17 g of the desired product (yield 97%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 8.49 (d, 1H), 8.22-8.20 (m, 2H), 8.08 (dd, 1H), 7.73-7.70 (m, 3H), 3.79 (s, 3H ), 3.44 (q, 2H), 1.28 (t, 3H).

The compounds of the present invention produced by the same method as in the above Examples are shown in Tables 1 and 2. Table 1 shows the substituents of the compound represented by the formula (a). Table 2 shows the substituents of the compound represented by the formula (b). The physical property data of the compound was entered in the “Physical property” column. As physical property data, properties, melting point (mp), or refractive index (n _D ) was described. Abbreviations in the table, Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group.
It should be noted that other compounds not specifically shown in the present specification, that is, those substituted with various groups that do not depart from the spirit and scope of the present invention can be produced and used by the above-described method and the like. Those skilled in the art can easily understand the description.

[Biological test]
The following test examples show that the diaryltriazole compound of the present invention (hereinafter referred to as the present compound) is useful as an active ingredient of a pest control agent, particularly an insecticide. “Parts” are based on weight.

(Preparation of test emulsion)
5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion (I) containing 5% active ingredient.

(Test Example 1) Efficacy test against scallops Artificial feed (Insector LFS, Nippon Agricultural Industry Co., Ltd.) 0.8 g and Emulsion (I) 1 μl are mixed well, and each treatment is performed in a plastic test container (1.4 ml volume). 0.2 g per ward was packed into a test feed.
Two instar larvae were inoculated per treatment group and sealed with a plastic lid. It was placed in a constant temperature room at 25 ° C., and the insecticidal rate and food intake were examined on the fifth day. The test was performed in duplicate.

  About compound No. 2-4 and 2-5, the efficacy test with respect to Ayatoru was carried out. All of the compounds were effective against the pearl millet, with an insecticidal rate of 100% or a food intake of 10% or less compared to the solvent control group.

(Test Example 2) Efficacy test against Spodoptera litura Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 31 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were placed in a petri dish and 5 second instar larvae were released. The petri dish was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release, life / death determination was performed and the insecticidal rate was calculated. The test was performed in duplicate.

  The compound Nos. 1-6 and 2-5 were tested for efficacy against Spodoptera litura. All the compounds showed 100% insecticidal rate against Spodoptera litura.

Test Example 3 Efficacy Test against Cotton Aphid Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cucumbers were raised in 3-inch pots, and cotton aphid nymphs were inoculated on the first true leaves. The diluted solution was sprayed on cucumber seedlings. The cucumber was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 4 days have passed since spraying, cotton aphids were evaluated for life and death, and the insecticidal rate was calculated. The test was performed in duplicate.

  Compound Nos. 1-1, 1-2 and 1-3 were tested for efficacy against cotton aphids. All compounds had an insecticidal rate of 80% or more.

(Test Example 4) Efficacy test against bean aphids Cowpeas were raised in 3-inch pots, and bean aphid nymphs were inoculated on primary leaves. Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm, and the diluted solution was sprayed on the cowpea infested with aphid larvae. The cowpea was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 4 days have passed since spraying, the aphid of the bean aphid was determined and the insecticidal rate was calculated. The test was performed in duplicate.

  About the compound numbers 1-1 and 1-2, the efficacy test with respect to a bean aphid was conducted. All the compounds showed an insecticidal rate of 80% or more against bean aphids.

  Since the compounds selected at random from the compounds of the present invention have the effects as described above, the compounds of the present invention include pest control, particularly insecticides, acaricides, and ectoparasites. It can be understood that it is a compound that has effects such as insect control, does not cause phytotoxicity to plants, and has little toxicity to human fish and environmental impact.

Claims (6)

A compound represented by formula (I) or formula (II) or a salt thereof.

[In Formula (I) and Formula (II),
A ¹ represents a carbon atom or a nitrogen atom.
X ¹ 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, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, mercapto group, unsubstituted Or substituted or unsubstituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted Denotes the 3- to 6-membered heterocyclyl group having a substituent, unsubstituted or amino group having a substituent, halogeno group, cyano group or a nitro group.
n represents the number of chemically acceptable X ¹ and is an integer of 0 to 4. When n is 2 or more, X ¹ may be the same or different.
R ¹ is a halogeno group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group , An unsubstituted or substituted C 1-6 alkylsulfonyloxy group, or a group represented by —S (═O) (═N—R ^a ) —R ^b ; Here, R ^a and R ^b each independently represent an unsubstituted or substituted C 1-6 alkyl group.
R ² 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, a hydroxyl group, an unsubstituted group Or a substituted C1-6 alkoxy group, a formyl group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, or an unsubstituted or The C1-6 alkylsulfonyl group which has a substituent is shown.
Ar represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-6 membered heteroaryl group. ] The compound or a salt thereof according to [1], wherein formula (I) or formula (II) is formula (III) or formula (IV).

[In Formula (III) and Formula (IV), A ¹ , X ¹ , R ¹ , and R ² have the same meanings as those in Formula (I) and Formula (II).
X ^1a , X ² and X ^2a each independently have an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted group C1-6 alkynyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 6 alkoxycarbonyl group, mercapto group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl Group, unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C 10 aryl group, an unsubstituted or 3-6 membered heterocyclyl group having a substituent, an amino group having unsubstituted or substituted group, halogeno group, a cyano group or a nitro group.
k represents the number of chemically acceptable X ^1a and is an integer of 0 to 3. When k is 2 or more, X ^1a may be the same as or different from each other.
h represents the number of chemically acceptable X ^2a and is an integer of 0-4. When h is 2 or more, X ^2a may be the same or different. ]   A pest control agent comprising at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof as an active ingredient.   An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof.   An ectoparasite control agent comprising at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof as an active ingredient.   An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof.