WO2014119494A1

WO2014119494A1 - Pest control composition and method for controlling pest

Info

Publication number: WO2014119494A1
Application number: PCT/JP2014/051599
Authority: WO
Inventors: 央岡本; 吉彦野倉
Original assignee: 住友化学株式会社
Priority date: 2013-01-31
Filing date: 2014-01-21
Publication date: 2014-08-07
Also published as: TW201441212A

Abstract

This pest control composition which contains a compound represented by formula (1) or an N-oxide thereof and one or more compounds selected from the group consisting of pyrethrin, allethrin, prallethrin, imiprothrin, resmethrin, tetramethrin, phenothrin, cyphenothrin, flumethrin, metofluthrin, transfluthrin, profluthrin, dimefluthrin, empenthrin, furamethrin and the like has an excellent controlling effect on pests.

Description

Pest control composition and pest control method

The present invention relates to a pest control composition and a pest control method.

Conventionally, many compounds are known as active ingredients of pest control compositions (see, for example, Non-Patent Document 1).

An object of the present invention is to provide a pest control composition having an excellent control effect against pests.

As a result of studies to find a pest control composition having an excellent control effect against pests, the present inventors have found that the compound represented by the following formula (1) and one or more selected from the following group (A): It has been found that a composition containing a compound has an excellent control effect against pests.

The present invention is as follows.
Item 1.
A compound represented by the following formula (1), or an N-oxide thereof,
A pest control composition containing one or more compounds selected from the following group (A).
Formula (1):

[Where:
A ¹ represents —NR ⁷ —, an oxygen atom or a sulfur atom,
A ² represents a nitrogen atom or = CR ⁸ - represents,
R ¹ represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X;
R ² , R ³ and R ⁴ are the same or different and are a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, —OR ¹⁰ , —S (O) _m R ¹⁰ , —S (O) ₂ NR ¹⁰ R ¹¹ , —NR ¹⁰ R ¹¹ , —NR ¹⁰ CO ₂ R ¹¹ , —NR ¹⁰ C (O) R ¹¹ , —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , -C (O) NR ¹⁰ R ¹¹ , -SF ₅ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ⁵ and R ⁶ are the same or different, and may be a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, —OR ¹⁰ , —S (O) _m R ¹⁰ , — S (O) ₂ NR ¹⁰ R ¹¹ , —NR ¹⁰ R ¹¹ , —NR ¹⁰ CO ₂ R ¹¹ , —NR ¹⁰ C (O) R ¹¹ , —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —C ^{^{(O) NR 10 R 11,}} -OC (O) R 10, -SF 5, a cyano group, a nitro group, a halogen atom or a hydrogen atom (provided that, ^{R 5} and ^{R 6} do not simultaneously represent a hydrogen atom ),
R ⁷ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group W, —CO ₂ R ¹⁰ , —C (O) R ¹⁰ , —CH ₂ CO ₂ R ¹⁰ , Represents a C3-C6 cycloalkyl group or a hydrogen atom,
R ⁸ is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C ( O) represents R ¹⁰ , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R ¹⁰ and R ¹¹ are the same or different and each represents a C1-C6 alkyl group or a hydrogen atom which may have one or more atoms or groups selected from group X (provided that —S (O) _m R ¹⁰ , when m is 1 or 2, R ¹⁰ does not represent a hydrogen atom)
m independently represents 0, 1 or 2, and n represents 0, 1 or 2.
Group X: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl groups A group consisting of a group, a cyano group, a hydroxy group and a halogen atom.
Group W: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, hydroxy group, halogen atom and cyano group A group consisting of ]

Group (A):
The group which consists of following subgroup A-1, A-2, A-3, A-4, A-5, and A-6.
Subgroup A-1:
Pyrethrin (CAS registration number 121-21-1), allethrin (CAS registration number 584-79-2), praretrin (CAS registration number 23031-36-9), imiproton (CAS registration number 72963-72-5), resmethrin ( CAS registration number 10453-86-8), tetramethrin (CAS registration number 7696-12-0), phenothrin (CAS registration number 26002-80-2), cyphenothrin (CAS registration number 39515-40-7), flumethrin (CAS) Registration Number 69770-45-2), Metofluthrin (CAS Registration Number 7696-12-0), Transfluthrin (CAS Registration Number 118712-89-3), Profluthrin (CAS Registration Number 223419-20-3), Dimefluthrin (CAS) Registration number 2712 1-14-6), Empentrin (CAS registration number 54406-48-3), Framethrin (CAS registration number 23031-38-1), Meperfluthrin (CAS registration number 915288-13-0), 2, 3, 5, 6 -Tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxy) Methyl) benzyl = 2,2-dimethyl-3- (3,3,3-trifluoro-1-propenyl) -cyclopropanecarboxylate (generic name: teflumethrin) and 2,3,5,6-tetrafluoro-4 A group of compounds consisting of propargylbenzyl = 2,2,3,3-tetramethylcyclopropanecarboxylate;

Subgroup A-2:
Fenitrothion (CAS registration number 122-14-5), dichlorvos (CAS registration number 62-73-7), propoxur (CAS registration number 114-26-1), bistrifluron (CAS registration number 201593-84-2), Diflubenzuron (CAS registration number 35367-38-5), hexaflumuron (CAS registration number 86479-06-3), amidoflumet (CAS registration number 84466-05-7), chlorfenapyr (CAS registration number 122453-73-0), Cyromazine (CAS registration number 66215-27-8), hydroprene (CAS registration number 41096-46-2), metoprene (CAS registration number 40596-69-8), methoxadiazone (CAS registration number 60589-06-2), etoxazole (CAS registration number 153233-91-1), piperonyl butoxide (CAS registry number 51-03-6) and N- (2-ethylhexyl) -5-norbornene-2,3-dicarboximide (CAS registry number 113-48-4). A group of compounds.

Subgroup A-3:
A group of compounds consisting of a compound represented by the following formula (2).

[Wherein Cy is a phenyl group which may be substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group which may be substituted with a group selected from groups E1 to E2, group E1 Represents a 3- to 7-membered cycloalkyl group optionally substituted with a group selected from ~ E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3, and Q ¹ it is which may be substituted C1 ~ have C4 chain hydrocarbon group with a halogen atom, a halogen atom or a hydrogen atom, Q ² is unsubstituted or may C1 ~ have C4 chain hydrocarbon group with a halogen atom, -C (= G) Q ^{4 represents} a cyano group, a halogen atom or a hydrogen atom, Q ³ represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom, G represents an oxygen atom or a sulfur atom, Q ⁴ is substituted with a halogen atom A C1-C4 alkyl group that may be substituted, a C1-C4 alkoxy group that may be substituted with a halogen atom, a C3-C6 alkenyloxy group that may be substituted with a halogen atom, or a halogen atom. Good C3-C6 alkynyloxy group, C1-C4 alkylamino group optionally substituted with a halogen atom, di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, hydroxyl group, amino group, C2 Represents a C5 cyclic amino group or a hydrogen atom, k represents 0 or 1, h represents 0, 1 or 2, and group E1 is a C1 to C6 chain optionally substituted with a group selected from group L wherein the hydrocarbon group, ~ C3 may be substituted with a halogen atom C6 cycloalkyl ^{^{^{group, -OQ 5, -SQ 5, -S}}} (= O) Q 5, -S (= O) 2 Q 5, -C (= O ) Represents a group of monovalent groups consisting of Q ⁶ , —OC (═O) Q ⁷ , a cyano group, a nitro group, a hydroxyl group and a halogen atom, and Group E2 may be substituted with a group selected from Group L From a good C2-C6 alkanediyl group, a 1,3-butadiene-1,4-diyl group optionally substituted with a group selected from group L, -G-T-G- and -T-G-T- The group E3 represents a group of divalent groups consisting of ═O, ═NO—Q ⁵ , ═C═CH ₂ and ═C (Q ⁸ ) Q ⁹ , and T represents a methylene group Or an ethylene group, and Q ⁵ is a C1-C4 chain hydrocarbon group optionally substituted with a group selected from Group L or a C3-C6 cycloalkyl group optionally substituted with a group selected from Group L the stands, Q ⁶ is substituted C1 may be ~ C4 alkoxy group a halogen atom, c A C3-C6 alkenyloxy group optionally substituted with a hydrogen atom, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, a C1-C4 alkylamino group optionally substituted with a halogen atom, a halogen atom A di (C1-C4 alkyl) amino group optionally substituted with, a C1-C4 alkyl group optionally substituted with a halogen atom, a hydroxyl group, an amino group, a C2-C5 cyclic amino group or a hydrogen atom, Q ⁷ is a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, a C3-C6 alkynyloxy group which may be substituted with a halogen atom, C1-C4 alkylamino group optionally substituted with a halogen atom, di (C1-C4) optionally substituted with a halogen atom Alkyl) amino group, a substituted C1 may be ~ C4 alkyl group with a halogen atom, an amino group, a C2 ~ C5 cyclic amino group or a hydrogen atom, Q ⁸ and Q ⁹ are the same or different, substituted with a halogen atom Represents a C1-C4 alkoxy group which may be substituted, a C1-C4 chain hydrocarbon group which may be substituted with a halogen atom, a halogen atom or a hydrogen atom, and the group L is substituted with a hydroxyl group or a halogen atom C1-C4 alkoxy group which may be substituted, C3-C6 alkenyloxy group which may be substituted by halogen atom, C3-C6 alkynyloxy group which may be substituted by halogen atom, amino group, substituted by halogen atom An optionally substituted C1-C4 alkylamino group, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C2-C5 cyclic group Amino group, —C (═O) Q ⁶ , —OC (═O) Q ⁷
And a group consisting of halogen atoms. ]

Subgroup A-4:
A group of compounds consisting of a compound represented by the following formula (3).

[Wherein, k, h, Q ¹ , Q ² and Q ³ represent the same meaning as described above, and Q ¹¹ may be substituted with a C1-C5 haloalkyl group having at least one fluorine atom or a halogen atom. C3-C5 alkenyl group, C3-C5 alkenyloxy group optionally substituted with a halogen atom, C3-C5 alkynyl group optionally substituted with a halogen atom, or C3-C5 alkynyl optionally substituted with a halogen atom Represents an oxy group, and Q ¹² represents a C1-C4 alkyl group which may be substituted with a halogen atom, a C1-C4 alkoxy group which may be substituted with a halogen atom, or a C1-C4 which may be substituted with a halogen atom. Represents an alkylthio group, a halogen atom or a hydrogen atom (provided that C ¹¹ -C 5 alkenyl optionally substituted with a halogen atom) If a group or an optionally substituted C3-C5 alkynyloxy group with a halogen atom, Q ¹² is a is C1-C4 or may be an alkyl group or a hydrogen atom substituted with a halogen atom.), Q ¹³ is A C1-C4 alkyl group, a halogen atom or a hydrogen atom is represented. ]

Subgroup A-5:
A group of compounds consisting of a compound represented by the following formula (4).

[Wherein L ³ represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group or a hydrogen atom, and L ⁴ represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or C1 represents C1-C6 alkyl group substituted with -C6 alkoxy group, ^{L 5} and ^{L 6} are the same or different, represent a methyl group or a hydrogen atom. ]
Subgroup A-6:
A group of compounds consisting of a compound represented by the following formula (5).

[Wherein, X ¹ represents a 2-methylpropyl group or 2-methyl-1-propenyl group, X ² represents a methyl group, X ³ represents a 2-methyl-1-propenyl group, and X ⁴ represents methyl Represents a group. ]

Item 2.
In the formula (1), the compound represented by the formula (1) or the N-oxide thereof is
R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group Y;
R ² and R ⁴ are hydrogen atoms,
R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom,
R ⁵ is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ , —CO ₂ R ¹⁰ , —SF ₅ or a halogen atom;
R ⁶ is —OR ¹⁰ , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom;
R ⁷ is one or more halogen atoms optionally C1-C6 may be alkyl groups having _{_{^{a, -CH 2 CO 2 R 10,}}} C3-C6 cycloalkyl group or a hydrogen atom,
R ⁸ is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom;
R ¹⁰ and R ¹¹ are the same or different and each is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom (provided that in —S (O) _m R ¹⁰ , m is 1 Or in the case of 2, R ¹⁰ does not represent a hydrogen atom).
Item 2. The pest control composition according to Item 1, wherein the group Y is a compound consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atoms and a halogen atom, or an N-oxide thereof.

Item 3.
In the formula (1), the compound represented by the formula (1) or the N-oxide thereof is
R ¹ is a C1-C3 alkyl group optionally having one or more halogen atoms,
R ² and R ⁴ are hydrogen atoms,
R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom,
R ⁵ is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ or a halogen atom;
R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom,
R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom,
R ¹⁰ and R ¹¹ are the same or different from each other one or more halogen atoms optionally may C1-C3 alkyl group which may have a compound, or a pesticidal composition according to claim 1 which is a N- oxide .

Item 4.
In the formula (1), the compound represented by the formula (1) or the N-oxide thereof is
R ¹ is an ethyl group,
R ² and R ⁴ are hydrogen atoms,
R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom,
R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom;
R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom,
R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms,
R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom,
R ¹⁰ and R ¹¹ are the same or different and each is a C1-C3 alkyl group optionally having one or more halogen atoms,
Compound R ²⁰ is C1-C3 haloalkyl group, or a pesticidal composition according to claim 1 which is a N- oxide.

Item 5.
In the formula (1), the compound represented by the formula (1) or the N-oxide thereof is
Item 5. The pest control composition according to any one of Items 1 to 4, wherein A ¹ is —NR ⁷ — or an N-oxide thereof.
Item 6.
In the formula (1), the compound represented by the formula (1) or the N-oxide thereof is
Item 5. The pest control composition according to any one of Items 1 to 4, wherein A ¹ is a compound having an oxygen atom, or an N-oxide thereof.
Item 7.
In the formula (1), the compound represented by the formula (1) or the N-oxide thereof is
Item 5. The pest control composition according to any one of Items 1 to 4, wherein A ¹ is a sulfur atom compound or an N-oxide thereof.

Item 8.
A compound represented by the following formula (1-2), or an N-oxide thereof,
A pest control composition comprising one or more compounds selected from the group (A) in Item 1.
Formula (1-2):

[Where:
R ^1a represents a C1-C3 alkyl group,
A ^2a represents a nitrogen atom or = CR ^8a- ,
R ^3a represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR ^10a ) ₃ , a halogen atom or a hydrogen atom,
R ^5a represents a C1-C3 haloalkyl group, —OR ^20a , —S (O) _m R ^20a or a halogen atom,
R ^6a represents a cyano group, —NR ^10a R ^11a , a halogen atom or a hydrogen atom,
R ^7a represents a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^8a represents —S (O) _m R ^10a , a cyano group, a halogen atom or a hydrogen atom;
R ^10a and R ^11a are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ^20a represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. ]

Item 9.
A compound represented by the following formula (1-3), or an N-oxide thereof,
A pest control composition comprising one or more compounds selected from the group (A) in Item 1.
Formula (1-3):

[Where:
A ^2b represents a nitrogen atom or = CR ^8b- ,
R ^3b represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR ^10b ) ₃ , a halogen atom or a hydrogen atom,
R ^5b represents a C1-C3 haloalkyl group, —OR ^20b , —S (O) _m R ^20b or a halogen atom,
R ^8b represents —S (O) _m R ^10b , a cyano group, a halogen atom or a hydrogen atom;
R ^10b represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ^20b represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. ]
Item 10.
In the formula (1-3), the compound represented by the formula (1-3) or the N-oxide thereof is
R ^3b is a halogen atom or a hydrogen atom,
R ^5b is a C1-C3 perfluoroalkyl group, —OR ^30b or —S (O) _m R ^30b ,
R ^30b is a C1-C3 perfluoroalkyl group,
Item 10. The pest control composition according to Item 9, wherein R ^8b is a halogen atom or a hydrogen atom, or an N-oxide thereof.

Item 11.
A compound represented by the following formula (1-4), or an N-oxide thereof,
A pest control composition comprising one or more compounds selected from the group (A) in Item 1.
Formula (1-4):

[Where:
A ^2c represents a nitrogen atom or = CR ^8c- ,
R ^3c represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR ^10c ) ₃ , a halogen atom or a hydrogen atom,
R ^5c represents a C1-C3 haloalkyl group, —OR ^20c , —S (O) _m R ^20c or a halogen atom,
R ^8c represents -S (O) _m R ^10c , a cyano group, a halogen atom or a hydrogen atom,
R ^10c represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ^20c represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. ]
Item 12.
In the formula (1-4), the compound represented by the formula (1-4) or the N-oxide thereof is
R ^3c is a halogen atom or a hydrogen atom,
R ^5c is a C1-C3 perfluoroalkyl group, —OR ^30c or —S (O) _m R ^30c ,
R ^30c is a C1-C3 perfluoroalkyl group,
Item 12. The pest control composition according to Item 11, wherein R ^8c is a halogen atom or a hydrogen atom, or an N-oxide thereof.

Item 13.
Any one of Items 1 to 7, wherein the ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight. A pest control composition as described in 1. above.
Item 14.
Any one of Items 1 to 7, wherein the ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight. A pest control composition as described in 1. above.
Item 15.
Item 9. The ratio of the content of the compound represented by the formula (1-2) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight ratio. Pest control composition.
Item 16.
Item 9. The ratio of the content of the compound represented by the formula (1-2) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight ratio. Pest control composition.
Item 17.
Item 9 or 10 wherein the ratio of the content of the compound represented by the formula (1-3) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight. The pest control composition as described.
Item 18.
Item 9 or 10 wherein the ratio of the content of the compound represented by the formula (1-3) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight. The pest control composition as described.
Item 19.
Item 11 or 12 wherein the ratio of the content of the compound represented by the formula (1-4) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight. The pest control composition as described.
Item 20.
Item 11 or 12 wherein the ratio of the content of the compound represented by the formula (1-4) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight. The pest control composition as described.
Item 21.
Item 21. A method for controlling pests comprising a step of applying an effective amount of the pest control composition according to any one of Items 1 to 20 to a pest or a habitat of the pest.
[The invention's effect]

According to the present invention, pests can be controlled.

The pest control composition of the present invention comprises a compound represented by the formula (1) (hereinafter sometimes referred to as the present condensed heterocyclic compound) and one or more compounds selected from the group (A) ( Hereinafter, it may be described as the present insecticidal compound).
In the present condensed heterocyclic compound, N-oxide is a compound in which one or more ring nitrogen atoms of one or more heterocyclic parts are oxidized. Examples of the heterocyclic moiety that can form an N-oxide include a pyridine ring moiety.
For example, the nitrogen atom in the pyridine ring shown in formula (1) can be N → O. For example, in the formula (1), A ² can be N → O.

Examples of groups used in the description of the present specification will be described below.
The notation of the Ca—Cb alkyl group in the present specification represents a linear or branched hydrocarbon group having a carbon number of a to b,
The notation of the Ca—Cb haloalkyl group represents a linear or branched hydrocarbon group having a carbon number of a to b in which one or more hydrogen atoms bonded to a carbon atom are substituted with a halogen atom, At this time, when having two or more halogen atoms, those halogen atoms may be the same or different from each other,
The notation of the Ca—Cb alkoxy group represents a linear or branched alkyl-O— group having a carbon number of a to b,
The notation of Ca—Cb cycloalkyl group represents a cyclic saturated hydrocarbon group having a to b carbon atoms.
In the present specification, the expression “which may have one or more atoms or groups selected from group X” means that when it has two or more atoms or groups selected from group X, those The atoms or groups selected from group X may be the same as or different from each other.
In the present specification, the expression “which may have one or more atoms or groups selected from group W” has two or more atoms or groups selected from group W. The atoms or groups selected from group W may be the same as or different from each other.
In the present specification, the expression “may have one or more halogen atoms” means that when two or more halogen atoms are present, the halogen atoms may be the same as or different from each other. May be.
In the present condensed heterocyclic compound, “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
In the present condensed heterocyclic compound, the notation “C1-C6 alkyl group optionally having one or more atoms or groups selected from group X” is an atom wherein a hydrogen atom bonded to a carbon atom is selected from group X Or a linear or branched saturated hydrocarbon group having 1 to 6 carbon atoms, optionally substituted with a group, wherein two or more atoms or groups selected from group X are substituted If present, the atoms or groups selected from group X may be the same as or different from each other.
Examples of the “C1-C6 alkyl group optionally having one or more atoms or groups selected from group X” include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- Butyl, tert-butyl, pentyl, neopentyl, hexyl, methoxymethyl, ethoxymethyl, propyloxymethyl, isopropyloxymethyl, butyloxymethyl, sec-butyloxymethyl, tert-butyl Oxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, 2-butyloxyethyl group, 2-sec-butyloxyethyl group, 2-tert- Butyloxyethyl group, trifluoromethyl group, trichloromethyl group, 2- Fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, 2-hydroxyethyl group, cyclopropylmethyl group, 1-methylcyclopropylmethyl group, 2,2- C1-C6 alkyl group which may have one or more atoms or groups selected from group X such as difluorocyclopropylmethyl group, trimethoxymethyl group, triethoxymethyl group, etc. It is selected in the range of the number of atoms.
In the present condensed heterocyclic compound, the expression “C1-C6 alkyl group optionally having one or more halogen atoms” is the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a linear or branched hydrocarbon group consisting of 1 to 6, and in this case, when having two or more halogen atoms, these halogen atoms are the same or different from each other It may be.
Examples of the “C1-C6 alkyl group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Group, pentyl group, neopentyl group, hexyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, A C1-C6 alkyl group which may have one or more halogen atoms such as a heptafluoroisopropyl group is exemplified, and each is selected within the range of the designated number of carbon atoms.
In the present condensed heterocyclic compound, examples of the “C1-C6 alkyl group optionally having one or more atoms or groups selected from group W” include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. , Isobutyl group, sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2,2, 2-trifluoroethyl group, pentafluoroethyl group, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyloxymethyl group, butyloxymethyl group, sec-butyloxymethyl group, isobutyloxymethyl group, tert-butyl Oxymethyl group, methoxyethyl group, ethoxyethyl group, propyl Having one or more atoms or groups selected from the group W such as a xylethyl group, an isopropyloxyethyl group, a butyloxyethyl group, a sec-butyloxyethyl group, an isobutyloxyethyl group, a tert-butyloxyethyl group; C2-C6 alkyl group may be mentioned. At this time, when it has two or more atoms or groups selected from the group W, the atoms or groups selected from the group W may be the same as or different from each other.
In the present condensed heterocyclic compound, examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include a methoxy group, a trifluoromethoxy group, an ethoxy group, and 2,2,2-trifluoroethoxy. Group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group and hexyloxy group.
Examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” in the present condensed heterocyclic compound include a cyclopropyl group, a 2,2-difluorocyclopropyl group, and a 2,2-dichlorocyclo group. Examples include propyl group, 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
In the present condensed heterocyclic compound, examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms or one or more C1-C3 alkyl groups” include a cyclopropyl group and 1-methylcyclopropyl. Group, 2-methylcyclopropyl group, 1-fluorocyclopropyl group, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl Groups.
In the present condensed heterocyclic compound, the expression “C1-C3 haloalkyl group” refers to a straight or branched chain having 1 to 3 carbon atoms in which one or more hydrogen atoms bonded to carbon atoms are substituted with halogen atoms. A chain-like hydrocarbon group is represented, and when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
Examples of the “C1-C3 haloalkyl group” include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, and trichloromethyl. Group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group and heptafluoroisopropyl Groups and the like.
In the present condensed heterocyclic compound, examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
Examples of the “C1-C3 perfluoroalkyl group” in the present condensed heterocyclic compound include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.

Examples of the present condensed heterocyclic compound include the following compounds.
In the formula (1), R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group Y, R ² and R ⁴ are hydrogen atoms, and R ³ Is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is having one or more halogen atoms. A C1-C3 alkyl group, —OR ¹⁰ , —S (O) _m R ¹⁰ , —CO ₂ R ¹⁰ , —SF ₅ or a halogen atom, and R ⁶ is —OR ¹⁰ , —NR ¹⁰ R ¹¹ , — CO ₂ R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ⁷ may have one or more halogen atoms. C1-C6 alkyl _group, -CH _² CO ₂ ^{R 10} C3-C6 cycloalkyl group or a hydrogen atom, ^{R 8} is 1 or more halogen atoms include C1-C3 may be an alkyl ^{_{group, -OR 10, -S (O)}} m R 10, a cyano group, A halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are the same or different and each is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom (provided that —S (O) _{In m} R ¹⁰ , when m is 1 or 2, R ¹⁰ does not represent a hydrogen atom.
A compound in which group Y is a group consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atoms and a halogen atom, or an N-oxide thereof.
In the formula (1), R ¹ is a C1-C3 alkyl group which may have one or more halogen atoms, R ² and R ⁴ are hydrogen atoms, and R ³ is one or more halogen atoms. atom optionally may C1-C3 alkyl group which may have, -C ^(oR _{10) 3,} a halogen atom or a hydrogen atom, ^{R 5} is one or more halogen atoms C1-C3 alkyl which may have a A group, —OR ¹⁰ , —S (O) _m R ¹⁰ or a halogen atom, R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, and R ⁷ is one or more halogen atoms. An optionally substituted C1-C6 alkyl group, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are the same or different and are one Even if it has more halogen atoms There is a C1-C3 alkyl group compound, or a N- oxide.
In the formula (1), R ¹ is an ethyl group, R ² and R ⁴ are hydrogen atoms, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom, R ⁶ is a cyano group, —NR ¹⁰ R ^{11 is} a halogen atom or a hydrogen atom, R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, A halogen atom or a hydrogen atom, R ¹⁰ and R ¹¹ are the same or different and may be one or more C1-C3 alkyl groups, and R ²⁰ is a C1-C3 haloalkyl group. Compound or its N -Oxides.
In the formula (1), compounds wherein A ¹ is —NR ⁷ —, or an N-oxide thereof.
In the formula (1), A ¹ is —NR ⁷ —, R ¹ is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group Y, R ² and R ⁴ is a hydrogen atom, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is 1 A C1-C3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , —S (O) _m R ¹⁰ , —CO ₂ R ¹⁰ , —SF ₅ or a halogen atom, and R ⁶ is — OR ¹⁰ , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and one or more R ⁷ C1-C6 alkyl group optionally having a halogen atom _{_{^{-CH 2 CO 2 R 10, C3}}} -C6 cycloalkyl group or a hydrogen atom, ^{R 8} is 1 or more halogen atoms include C1-C3 may be an alkyl ^group, -OR ^10, -S (O ) m _R ^10, a cyano group, a halogen atom or a hydrogen atom, R ¹⁰ and R ¹¹ are the same or different from each other one or more halogen atoms which may have a C1-C3 alkyl group or a hydrogen atom (However, in -S _(O) ^{m R 10,} when m is 1 or ^{2, R 10} can not represent hydrogen atom.),
A compound in which group Y is a group consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atoms and a halogen atom, or an N-oxide thereof.
In the formula (1), A ¹ is —NR ⁷ —, R ¹ is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² and R ⁴ are hydrogen atoms. R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is one or more halogen atoms. A C1-C3 alkyl group which may have, —OR ¹⁰ , —S (O) _m R ¹⁰ or a halogen atom; R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom; R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ is identical or different from each other 1 or more Have androgenic atom also may C1-C3 alkyl group compound, or a N- oxide.
In the formula (1), A ¹ is —NR ⁷ —, R ¹ is an ethyl group, R ² and R ⁴ are hydrogen atoms, and R ³ has one or more halogen atoms. A C1-C3 alkyl group, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom. , R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, and R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are the same or different and are C1-C3 alkyl groups optionally having one or more halogen atoms, R ²⁰ is C1-C3 haloalkyl The compound which is a group, or its N-oxide.
In the above formula (1), a compound wherein A ¹ is an oxygen atom, or an N-oxide thereof.
In the formula (1), A ¹ is an oxygen atom, R ¹ is a C1-C6 alkyl group which may have one or more atoms or groups selected from group Y, and R ² and R ⁴ Is a hydrogen atom, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is one or more A C1-C3 alkyl group optionally having a halogen atom, —OR ¹⁰ , —S (O) _m R ¹⁰ , —CO ₂ R ¹⁰ , —SF ₅ or a halogen atom, and R ⁶ is —OR ^10. , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ⁷ is one or more halogens A C1-C6 alkyl group optionally having an atom,- H is a _{_{^{2 CO 2 R 10, C3-}}} C6 cycloalkyl group or a hydrogen atom, ^{R 8} is one or more halogen atoms optionally C1-C3 may be alkyl groups having ^a, -OR ^10, -S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are the same or different and may be a C1-C3 alkyl group or a hydrogen atom which may have one or more halogen atoms ( However, in -S _(O) ^{m R 10,} when m is 1 or ^{2, R 10} can not represent hydrogen atom.),
A compound in which group Y is a group consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atoms and a halogen atom, or an N-oxide thereof.
In the formula (1), A ¹ is an oxygen atom, R ¹ is a C1-C3 alkyl group optionally having one or more halogen atoms, R ² and R ⁴ are hydrogen atoms, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ has one or more halogen atoms. An optionally substituted C1-C3 alkyl group, —OR ¹⁰ , —S (O) _m R ¹⁰ or a halogen atom, R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, and R ⁷ Is a C1-C6 alkyl group which may have one or more halogen atoms, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ One or more halos that are the same or different The compound which is a C1-C3 alkyl group which may have a gen atom, or its N-oxide.
In the formula (1), A ¹ is a sulfur atom, R ¹ is an ethyl group, R ² and R ⁴ are hydrogen atoms, and R ³ may have one or more halogen atoms. C1-C3 alkyl group, -C ^(oR _{10) 3,} a halogen atom or a hydrogen atom, ^{R 5} is C1-C3 haloalkyl ^group, -OR 20, a -S _(O) ^{m R 20} or halogen atom, R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, and R ⁸ is —S (O ) _m R ^10, a cyano group, a halogen atom or a hydrogen ^atom, an ^{R 10} and ^{R 11} are the same or different from each other one or more halogen atoms optionally C1-C3 may be alkyl groups having ^{a, R 20} Is a C1-C3 haloalkyl group A compound, or a N- oxide.
In the formula (1), A ¹ is a sulfur atom, or an N-oxide thereof.
In the formula (1), A ¹ is a sulfur atom, R ¹ is a C1-C6 alkyl group which may have one or more atoms or groups selected from group Y, and R ² and R ⁴ Is a hydrogen atom, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ is one or more A C1-C3 alkyl group optionally having a halogen atom, —OR ¹⁰ , —S (O) _m R ¹⁰ , —CO ₂ R ¹⁰ , —SF ₅ or a halogen atom, and R ⁶ is —OR ^10. , —NR ¹⁰ R ¹¹ , —CO ₂ R ¹⁰ , —C (O) NR ¹⁰ R ¹¹ , —OC (O) R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ⁷ is one or more halogens A C1-C6 alkyl group optionally having an atom,- H is a _{_{^{2 CO 2 R 10, C3-}}} C6 cycloalkyl group or a hydrogen atom, ^{R 8} is one or more halogen atoms optionally C1-C3 may be alkyl groups having ^a, -OR ^10, -S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ are the same or different and may be a C1-C3 alkyl group or a hydrogen atom which may have one or more halogen atoms ( However, in -S _(O) ^{m R 10,} when m is 1 or ^{2, R 10} can not represent hydrogen atom.),
A compound in which group Y is a group consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atoms and a halogen atom, or an N-oxide thereof.
In the formula (1), A ¹ is a sulfur atom, R ¹ is a C1-C3 alkyl group optionally having one or more halogen atoms, R ² and R ⁴ are hydrogen atoms, R ³ is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, and R ⁵ has one or more halogen atoms. An optionally substituted C1-C3 alkyl group, —OR ¹⁰ , —S (O) _m R ¹⁰ or a halogen atom, R ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, and R ⁷ Is a C1-C6 alkyl group which may have one or more halogen atoms, R ⁸ is —S (O) _m R ¹⁰ , a cyano group, a halogen atom or a hydrogen atom, and R ¹⁰ and R ¹¹ One or more halos that are the same or different The compound which is a C1-C3 alkyl group which may have a gen atom, or its N-oxide.
In the formula (1), A ¹ is a sulfur atom, R ¹ is an ethyl group, R ² and R ⁴ are hydrogen atoms, and R ³ may have one or more halogen atoms. A C1-C3 alkyl group, —C (OR ¹⁰ ) ₃ , a halogen atom or a hydrogen atom, R ⁵ is a C1-C3 haloalkyl group, —OR ²⁰ , —S (O) _m R ²⁰ or a halogen atom; ⁶ is a cyano group, —NR ¹⁰ R ¹¹ , a halogen atom or a hydrogen atom, R ⁷ is a C1-C6 alkyl group optionally having one or more halogen atoms, and R ⁸ is —S (O ) _m R ^10, a cyano group, a halogen atom or a hydrogen ^{atom, R 10} and ^{R 11} are the same or different from each other one or more halogen atoms which may have a C1-C3 alkyl ^{group, R 20} Is a C1-C3 haloalkyl group A compound, or a N- oxide.

Formula (1-2):

[Where:
R ^1a represents a C1-C3 alkyl group,
A ^2a represents a nitrogen atom or = CR ^8a- ,
R ^3a represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR ^10a ) ₃ , a halogen atom or a hydrogen atom,
R ^5a represents a C1-C3 haloalkyl group, —OR ^20a , —S (O) _m R ^20a or a halogen atom,
R ^6a represents a cyano group, —NR ^10a R ^11a , a halogen atom or a hydrogen atom,
R ^7a represents a C1-C6 alkyl group optionally having one or more halogen atoms,
R ^8a represents —S (O) _m R ^10a , a cyano group, a halogen atom or a hydrogen atom;
R ^10a and R ^11a are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ^20a represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. Or a N-oxide thereof.

Formula (1-3):

[Where:
A ^2b represents a nitrogen atom or = CR ^8b- ,
R ^3b represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR ^10b ) ₃ , a halogen atom or a hydrogen atom,
R ^5b represents a C1-C3 haloalkyl group, —OR ^20b , —S (O) _m R ^20b or a halogen atom,
R ^8b represents —S (O) _m R ^10b , a cyano group, a halogen atom or a hydrogen atom;
R ^10b represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ^20b represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. Or a N-oxide thereof.
In the formula (1-3), R ^3b is a halogen atom or a hydrogen atom, R ^5b is a C1-C3 perfluoroalkyl group, —OR ^30b or —S (O) _m R ^30b , and R ^30b is C1. -C3 perfluoroalkyl group, the compound R ^8b is a halogen atom or a hydrogen atom, or an N- oxide.

Formula (1-4):

[Where:
A ^2c represents a nitrogen atom or = CR ^8c- ,
R ^3c represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR ^10c ) ₃ , a halogen atom or a hydrogen atom,
R ^5c represents a C1-C3 haloalkyl group, —OR ^20c , —S (O) _m R ^20c or a halogen atom,
R ^8c represents -S (O) _m R ^10c , a cyano group, a halogen atom or a hydrogen atom,
R ^10c represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R ^20c represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. Or a N-oxide thereof.
In the formula (1-4), R ^3c is a halogen atom or a hydrogen atom, R ^5c is a C1-C3 perfluoroalkyl group, —OR ^30c or —S (O) _m R ^30c , and R ^30c is C1. The compound which is -C3 perfluoroalkyl group and ^R8c is a halogen atom or a hydrogen atom, or its N-oxide.

Formula (1):

In Formula (1), A ¹ -NR ⁷ -And R ⁷ Is a C1-C6 alkyl group optionally having one or more halogen atoms or a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And R ⁷ Is a methyl group, an ethyl group or a propyl group, or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And R ⁷ Is a methyl group, or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And R ⁷ Wherein N is a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ² Wherein N is a nitrogen atom, or an N-oxide thereof;
In Formula (1), A ² Is a compound (N-oxide) in which = N (→ O)-;
In Formula (1), A ² = CR ⁸ A compound which is-or an N-oxide thereof;
In Formula (1), A ² = CR ⁸ -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfonyl group, a halogen atom or a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ² = CR ⁸ -And R ⁸ Is a C1-C3 alkoxy group, or an N-oxide thereof;
In Formula (1), A ² = CR ⁸ -And R ⁸ Is a C1-C3 alkylsulfonyl group, or an N-oxide thereof;
In Formula (1), A ² = CR ⁸ -And R ⁸ Is a halogen atom, or an N-oxide thereof;
In Formula (1), A ² Wherein ═CH— or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And A ² Wherein N is a nitrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And A ² Is a compound (N-oxide) in which = N (→ O)-;
In Formula (1), A ¹ -NR ⁷ -And A ² = CR ⁸ A compound which is-or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And A ² Wherein ═CH—, or an N-oxide thereof;
In Formula (1), A ¹ Is an oxygen atom and A ² Wherein N is a nitrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ Is an oxygen atom and A ² Is a compound (N-oxide) in which = N (→ O)-;
In Formula (1), A ¹ Is an oxygen atom and A ² = CR ⁸ A compound which is-or an N-oxide thereof;
In Formula (1), A ¹ Is an oxygen atom and A ² Wherein ═CH—, or an N-oxide thereof;
In Formula (1), A ¹ Is a sulfur atom and A ² Wherein N is a nitrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ Is a sulfur atom and A ² Is a compound (N-oxide) in which = N (→ O)-;
In Formula (1), A ¹ Is a sulfur atom and A ² = CR ⁸ A compound which is-or an N-oxide thereof;
In Formula (1), A ¹ Is a sulfur atom and A ² Wherein ═CH—, or an N-oxide thereof;
In formula (1), R ¹ Is a C1-C6 alkyl group optionally having one or more halogen atoms or a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or an N-oxide thereof;
In formula (1), R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, or an N-oxide thereof;
In formula (1), R ¹ Is a methyl group, ethyl group, propyl group, isopropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, cyclopropyl group or cyclopropylmethyl group, or an N-oxide thereof;
In formula (1), R ¹ Is an ethyl group or a cyclopropylmethyl group, or an N-oxide thereof;
In formula (1), R ¹ Is a methyl group, or an N-oxide thereof;
In formula (1), R ¹ Is an ethyl group, or an N-oxide thereof;
In formula (1), R ¹ Is a propyl group, or an N-oxide thereof;
In formula (1), R ¹ Wherein N is an isopropyl group, or an N-oxide thereof;
In formula (1), R ³ Is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, a halogen atom or a hydrogen atom, or an N-oxide thereof;
In formula (1), R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ , A compound which is a halogen atom or a hydrogen atom, or an N-oxide thereof;
In formula (1), R ³ Is a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom, or an N-oxide thereof;
In formula (1), R ³ Is a C1-C3 alkyl group optionally having one or more halogen atoms, or an N-oxide thereof;
In formula (1), R ³ Is -C (OR ¹⁰ ) ₃ Or a N-oxide thereof;
In formula (1), R ³ Is a halogen atom, or an N-oxide thereof;
In formula (1), R ³ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1), R ³ Is a methyl group, trifluoromethyl group, pentafluoroethyl group, hexafluoropropyl group, hexafluoroisopropyl group, trimethoxymethyl group, triethoxymethyl group, fluorine atom, chlorine atom, bromine atom, iodine atom or hydrogen atom A compound, or an N-oxide thereof;
In formula (1), R ³ Wherein R is a trifluoromethyl group, or an N-oxide thereof; in the formula (1), R ³ Is a trimethoxymethyl group, or an N-oxide thereof; in the formula (1), R ² And R ⁴ Or a N-oxide thereof in which both are hydrogen atoms; R in the formula (1) ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ , A compound which is a halogen atom or a hydrogen atom, or an N-oxide thereof;
R in the formula (1) ² And R ⁴ Are both hydrogen atoms and R ³ Wherein N is a hydrogen atom, or an N-oxide thereof;
R in the formula (1) ² And R ⁴ Are both hydrogen atoms and R ³ Is a trifluoromethyl group, or an N-oxide thereof;
R in the formula (1) ² And R ⁴ Are both hydrogen atoms and R ³ Is a trimethoxymethyl group, or an N-oxide thereof;
In formula (1), R ⁵ C 1 -C 3 alkyl group optionally having one or more halogen atoms, —OR ¹⁰ , -S (O) _m R ¹⁰ , -CO ₂ R ¹⁰ , -SF ₅ Or a compound which is a halogen atom, or an N-oxide thereof;
In formula (1), a C1-C3 alkyl group optionally having one or more halogen atoms, -OR ¹⁰ , -S (O) _m R ¹⁰ Or a compound which is a halogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 haloalkyl group, a C1-C3 haloalkoxy group, a C1-C3 haloalkylsulfanyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 haloalkylsulfonyl group or a halogen atom, or an N-oxide thereof; ), R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkyl group, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkoxy group, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group or a C1-C3 perfluoroalkylsulfonyl group, or an N-oxide thereof;
In formula (1), R ⁵ Is a halogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a trifluoromethyl group, -CF ₂ CF ₃ , -CF ₂ CF ₂ CF ₃ , -CF (CF ₃ ) ₂ , -OCF ₃ , -OCF ₂ CF ₃ , -SCF ₃ , -S (O) CF ₃ , -S (O) ₂ CF ₃ , -SCF ₂ CF ₃ , -S (O) CF ₂ CF ₃ , -S (O) ₂ CF ₂ CF ₃ , -SF ₅ , A fluorine atom, a chlorine atom, a bromine atom or an iodine atom, or an N-oxide thereof;
In formula (1), R ⁵ Wherein R is a trifluoromethyl group, or an N-oxide thereof; in the formula (1), R ⁵ -CF ₂ CF ₃ Or a N-oxide thereof;
In formula (1), R ⁵ -SCF ₃ Or a N-oxide thereof;
In formula (1), R ⁵ -S (O) CF ₃ Or a N-oxide thereof;
In formula (1), R ⁵ -S (O) ₂ CF ₃ Or a N-oxide thereof;
In formula (1), R ⁶ Is -OR ¹⁰ , -NR ¹⁰ R ¹¹ , -CO ₂ R ¹⁰ , -C (O) NR ¹⁰ R ¹¹ , A compound which is a cyano group, a halogen atom or a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁶ Is a cyano group, -NR ¹⁰ R ¹¹ , A compound which is a halogen atom or a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 haloalkyl group, a C1-C3 haloalkoxy group, a C1-C3 haloalkylsulfanyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 haloalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkyl group, R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkoxy group and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1), R ⁵ Is a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group or a C1-C3 perfluoroalkylsulfonyl group, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And R ⁷ Is a methyl group and A ² Is a nitrogen atom and R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ A halogen atom or a hydrogen atom, R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ -NR ⁷ -And R ⁷ Is a methyl group and A ² Is = N (→ O)-, and R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ A halogen atom or a hydrogen atom, R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom (N-oxide);
In Formula (1), A ¹ -NR ⁷ -And R ⁷ Is a methyl group and A ² = CR ⁸ -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ A halogen atom or a hydrogen atom, R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ Is an oxygen atom and A ² Is a nitrogen atom and R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ A halogen atom or a hydrogen atom, R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In Formula (1), A ¹ Is an oxygen atom and A ² Is = N (→ O)-, and R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ A halogen atom or a hydrogen atom, R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom (N-oxide);
In Formula (1), A ¹ Is an oxygen atom and A ² = CR ⁸ -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ¹ Is a C1-C3 alkyl group optionally having one or more halogen atoms, and R ² And R ⁴ Are both hydrogen atoms and R ³ C1-C3 alkyl group which may have one or more halogen atoms, -C (OR ¹⁰ ) ₃ A halogen atom or a hydrogen atom, R ⁵ Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ⁶ Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1-2), A ^2a Wherein N is a nitrogen atom, or an N-oxide thereof;
In formula (1-2), A ^2a Is a compound (N-oxide) in which = N (→ O)-;
In formula (1-2), A ^2a = CR ^8a A compound which is-or an N-oxide thereof;
In formula (1-2), A ^2a Wherein ═CH—, or an N-oxide thereof;
In the formula (1-2), R ^1a Is a methyl group, or an N-oxide thereof;
In the formula (1-2), R ^1a Is an ethyl group, or an N-oxide thereof;
In the formula (1-2), R ^1a Is a propyl group, or an N-oxide thereof;
In the formula (1-2), R ^1a Wherein N is an isopropyl group, or an N-oxide thereof; in the formula (1-2), R ^3a Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-2), R ^3a Is a trifluoromethyl group, or an N-oxide thereof;
In the formula (1-2), R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-2), R ^5a Is a trifluoromethyl group and R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-2), R ^5a -CF ₂ CF ₃ And R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-2), R ^5a -SCF ₃ And R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-2), R ^5a -S (O) CF ₃ And R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-2), R ^5a -S (O) ₂ CF ₃ And R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1-2), A ^2a Is a nitrogen atom and R ^1a Is an ethyl group and R ^3a Is a hydrogen atom and R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1-2), A ^2a Is = N (→ O)-, and R ^1a Is an ethyl group and R ^3a Is a hydrogen atom and R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom (N-oxide);
In formula (1-2), A ^2a = CR ^8a -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ^1a Is an ethyl group and R ^3a Is a hydrogen atom and R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1-2), A ^2a Is a nitrogen atom and R ^1a Is an ethyl group and R ^3a Is a trifluoromethyl group and R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1-2), A ^2a Is = N (→ O)-, and R ^1a Is an ethyl group and R ^3a Is a trifluoromethyl group and R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom (N-oxide);
In formula (1-2), A ^2a = CR ^8a -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ^1a Is an ethyl group and R ^3a Is a trifluoromethyl group and R ^5a Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6a Wherein N is a hydrogen atom, or an N-oxide thereof;
In formula (1-3), A ^2b Wherein N is a nitrogen atom, or an N-oxide thereof;
In formula (1-3), A ^2b Is a compound (N-oxide) in which = N (→ O)-;
In formula (1-3), A ^2b = CR ^8b A compound which is-or an N-oxide thereof;
In formula (1-3), A ^2b Wherein ═CH—, or an N-oxide thereof;
In the formula (1-3), R ^3b Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-3), R ^3b Is a trifluoromethyl group, or an N-oxide thereof;
In the formula (1-3), R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In the formula (1-3), R ^5b Is a trifluoromethyl group, or an N-oxide thereof;
In the formula (1-3), R ^5b -CF ₂ CF ₃ Or a N-oxide thereof; in the formula (1-3), R ^5b -SCF ₃ Or a N-oxide thereof;
In the formula (1-3), R ^5b -S (O) CF ₃ Or a N-oxide thereof;
In the formula (1-3), R ^5b -S (O) ₂ CF ₃ Or a N-oxide thereof;
In formula (1-3), A ^2b Is a nitrogen atom and R ^3b Is a hydrogen atom and R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-3), A ^2b Is = N (→ O)-, and R ^3b Is a hydrogen atom and R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom ( N-oxide);
In formula (1-3), A ^2b = CR ^8b -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ^3b Is a hydrogen atom and R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-3), A ^2b Is a nitrogen atom and R ^3b Is a trifluoromethyl group and R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-3), A ^2b Is = N (→ O)-, and R ^3b Is a trifluoromethyl group and R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom ( N-oxide);
In formula (1-3), A ^2b = CR ^8b -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ^3b Is a trifluoromethyl group and R ^5b Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-4), A ^2c Wherein N is a nitrogen atom, or an N-oxide thereof;
In formula (1-4), A ^2c Is a compound (N-oxide) in which = N (→ O)-;
In formula (1-4), A ^2c = CR ^8c A compound which is-or an N-oxide thereof;
In formula (1-4), A ^2c Wherein ═CH—, or an N-oxide thereof;
In the formula (1-4), R ^3c Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-4), R ^3c Is a trifluoromethyl group, or an N-oxide thereof;
In the formula (1-4), R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, and R ^6c Wherein N is a hydrogen atom, or an N-oxide thereof;
In the formula (1-4), R ^5c Is a trifluoromethyl group, or an N-oxide thereof;
In the formula (1-4), R ^5c -CF ₂ CF ₃ Or a N-oxide thereof; in the formula (1-4), R ^5c -SCF ₃ Or a N-oxide thereof;
In the formula (1-4), R ^5c -S (O) CF ₃ Or a N-oxide thereof;
In the formula (1-4), R ^5c -S (O) ₂ CF ₃ Or a N-oxide thereof;
In formula (1-4), A ^2c Is a nitrogen atom and R ^3c Is a hydrogen atom and R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-4), A ^2c Is = N (→ O)-, and R ^3c Is a hydrogen atom and R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom ( N-oxide);
In formula (1-4), A ^2c = CR ^8c -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ^3c Is a hydrogen atom and R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-4), A ^2c Is a nitrogen atom and R ^3c Is a trifluoromethyl group and R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide;
In formula (1-4), A ^2c Is = N (→ O)-, and R ^3c Is a trifluoromethyl group and R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom ( N-oxide);
In formula (1-4), A ^2c = CR ^8c -And R ⁸ Is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom or a hydrogen atom, and R ^3c Is a trifluoromethyl group and R ^5c Is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group or a halogen atom, Or its N-oxide.

Next, the manufacturing method of this condensed heterocyclic compound is demonstrated.
The present condensed heterocyclic compound and intermediate compound can be produced, for example, by the following (Production Method 1) to (Production Method 24).
(Production method 1)
The present condensed heterocyclic compound in which n is 1 or 2 in formula (1) can be produced by oxidizing the present condensed heterocyclic compound in which n is 0.

[Wherein the symbols have the same meaning as in formula (1). ]
The present condensed heterocyclic compound (1-n1) in which n is 1 in the formula (1) is produced by oxidizing the condensed heterocyclic compound (1-n0) in which n is 0 using an oxidizing agent. Can do.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used for the reaction include sodium periodate or m-chloroperbenzoic acid.
In the reaction, the oxidizing agent is usually used at a ratio of 1 to 3 mol with respect to 1 mol of the present condensed heterocyclic compound (1-n0). Preferably, the oxidizing agent is used at a ratio of 1 to 1.2 mol with respect to 1 mol of the present condensed heterocyclic compound (1-n0).
The reaction temperature of the reaction is usually in the range of −20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the present condensed heterocyclic compound (1-n1) can be isolated. The isolated present condensed heterocyclic compound (1-n1) can be further purified by chromatography, recrystallization or the like.
The present condensed heterocyclic compound (1-n2) in which n is 2 in formula (1) is produced by oxidizing the present condensed heterocyclic compound (1-n1) in which n is 1 using an oxidizing agent. Can do.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid and aqueous hydrogen peroxide.
In the reaction, the oxidizing agent is usually used at a ratio of 1 to 4 mol with respect to 1 mol of the present condensed heterocyclic compound (1-n1). Preferably, the oxidizing agent is used in a ratio of 1 to 2 moles with respect to 1 mole of the present condensed heterocyclic compound (1-n1).
The reaction temperature of the reaction is usually in the range of −20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the present condensed heterocyclic compound (1-n2) can be isolated. The condensed heterocyclic compound (1-n2) can be further purified by chromatography, recrystallization, and the like.
In addition, the present condensed heterocyclic compound (1-n2) in which n is 2 in the formula (1) is obtained by oxidizing the present condensed heterocyclic compound (1-n0) in which n is 0 using an oxidizing agent. It can be produced by a step reaction (one pot).
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid and aqueous hydrogen peroxide.
The reaction can be carried out in the presence of a catalyst as necessary.
Examples of the catalyst used in the reaction include sodium tungstate.
In the reaction, with respect to 1 mol of the present condensed heterocyclic compound (1-n0), the oxidizing agent is usually used in a proportion of 2 to 5 mol, and the catalyst is usually used in a proportion of 0.01 to 0.5 mol. Preferably, the oxidizing agent is used in a proportion of 2 to 3 mol and the catalyst is usually used in a proportion of 0.01 to 0.5 mol with respect to 1 mol of the present condensed heterocyclic compound (1-n0).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the present condensed heterocyclic compound (1-n2) can be isolated. The isolated present condensed heterocyclic compound (1-n2) can be further purified by chromatography, recrystallization and the like.

(Production method 2)
This fused heterocyclic compound is produced by reacting the intermediate compound (M1) with the intermediate compound (M2) or the intermediate compound (M18) to produce the intermediate compound (M3), and then obtaining the intermediate compound (M3) It can be produced by condensing M3) within the molecule. Here, the production of the intermediate compound (M3) and the condensation in the molecule occur almost simultaneously, and the production of the intermediate compound (M3) may not be confirmed.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M3) can be produced by reacting intermediate compound (M1) and intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter sometimes referred to as THF), ethers such as tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, Halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, N, N-dimethylformamide (Hereinafter, sometimes referred to as DMF), N-methylpyrrolidone (hereinafter, sometimes referred to as NMP), 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide (hereinafter, sometimes referred to as DMSO). Aprotic polar solvents such as pyridine, quinoline, etc. Containing aromatic compounds and mixtures thereof.
Examples of the condensing agent used in the reaction include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter sometimes referred to as EDCI hydrochloride) and 1,3-dicyclohexylcarbodiimide. Is mentioned.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole (hereinafter sometimes referred to as HOBt).
In the reaction, the intermediate compound (M2) is usually in a proportion of 0.5 to 2 mol, the condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually 0 in 1 mol of the intermediate compound (M1). Used in a ratio of 01 to 1 mol.
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M3) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M3) can be further purified by recrystallization, chromatography or the like.
The intermediate compound (M3) can be produced by reacting the intermediate compound (M1) with the intermediate compound (M18).
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
This reaction can also be performed by adding a base as necessary.
The base used in the reaction includes alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. And the like.
In the reaction, with respect to 1 mol of the intermediate compound (M1), the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M3) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can.
The isolated intermediate compound (M3) can be further purified by chromatography, recrystallization and the like.
This condensed heterocyclic compound (1) can be produced by intramolecular condensation of the intermediate compound (M3).
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, and halogenated carbonization such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrogens, aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2-imidazolidinone, DMSO, etc. Aprotic polar solvents, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
In the reaction, a condensing agent, an acid, a base, or a chlorinating agent can be used as necessary.
Examples of the condensing agent used in the reaction include acetic anhydride, trifluoroacetic anhydride, EDCI hydrochloride, a mixture of triphenylphosphine and base and carbon tetrachloride or carbon tetrabromide, triphenylphosphine and diethyl azodicarboxylate, etc. Examples thereof include a mixture of azo diesters.
Examples of the acid used in the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, polyphosphoric acid, and the like.
Examples of the base used in the reaction include pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU).
), Nitrogen-containing heterocyclic compounds such as 1,5-diazabicyclo [4.3.0] -5-nonene, tertiary amines such as triethylamine and N, N-diisopropylethylamine, tripotassium phosphate, potassium carbonate, An inorganic base such as sodium hydride can be mentioned.
Examples of the chlorinating agent used in the reaction include phosphorus oxychloride.
In the reaction, with respect to 1 mol of the intermediate compound (M3), when a condensing agent is used, the ratio of the condensing agent is usually 1 to 5 mol, and when an acid is used, the acid is usually 0.1 mol to 5 mol. When a base is used, the base is usually used in a proportion of 1 to 5 mol, and when a chlorinating agent is used, the chlorinating agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The condensed heterocyclic compound (1) can be isolated by collecting the obtained solid by filtration.
The isolated present condensed heterocyclic compound (1) can be further purified by recrystallization, chromatography or the like.
The present condensed heterocyclic compound (1) can be produced in a one-step reaction (one pot) by reacting the intermediate compound (M1) and the intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, tert-butyl methyl ether, and halogenations such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. Hydrocarbons, aromatic hydrocarbons such as toluene, benzene, xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl-2-imidazolidinone, DMSO And aprotic polar solvents such as nitrogen, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
Examples of the condensing agent used in the reaction include carbodiimides such as EDCI hydrochloride and 1,3-dicyclohexylcarbodiimide.
This reaction can also be performed by adding a catalyst as needed.
Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole.
In the reaction, with respect to 1 mol of the intermediate compound (M1), the intermediate compound (M2) is usually in a proportion of 0.5 to 2 mol, the condensing agent is usually in a proportion of 1 to 5 mol, and the catalyst is usually in an amount of 0.8. It is used at a ratio of 01 to 1 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time of the reaction is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The condensed heterocyclic compound (1) can be isolated by collecting the obtained solid by filtration.
The isolated present condensed heterocyclic compound (1) can be further purified by recrystallization, chromatography or the like.
In addition, the present condensed heterocyclic compound (1) can be produced in a one-step reaction (one pot) by reacting the intermediate compound (M1) with the intermediate compound (M18).
The reaction is usually performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
This reaction can also be performed by adding a base as necessary.
The base used in the reaction includes alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. And the like.
In the reaction, with respect to 1 mol of the intermediate compound (M1), the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 20 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (1) is isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. be able to. The isolated present condensed heterocyclic compound (1) can be further purified by chromatography, recrystallization and the like.

(Production method 3)
An intermediate compound (M14) is reacted with the intermediate compound (M2) or the intermediate compound (M18) to produce an intermediate compound (M14). Can be reacted to produce the present condensed heterocyclic compound (P20) in which A ¹ is a sulfur atom and A ² is a nitrogen atom in formula (1).

[Wherein the symbols have the same meaning as in formula (1). ]
The intermediate compound (M14) can be produced by reacting the intermediate compound (M9) and the intermediate compound (M2) in the presence of a condensing agent.
The reaction is usually performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, nitrogen-containing compounds such as pyridine and quinoline Aromatic compounds and mixtures thereof are mentioned.
Examples of the condensing agent used in the reaction include EDCI hydrochloride, carbodiimides such as 1,3-dicyclohexylcarbodiimide, and BOP reagent.
In the reaction, the intermediate compound (M2) is usually used in a proportion of 1 to 3 mol and the condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the intermediate compound (M9).
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M14) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (M14) can be further purified by chromatography, recrystallization and the like.
The intermediate compound (M14) can be produced by reacting the intermediate compound (M9) with the intermediate compound (M18).
The reaction is usually performed in the presence or absence of a solvent. A base can be added as necessary.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Aromatic hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, nitrogen-containing compounds such as pyridine and quinoline Aromatic compounds and mixtures thereof are mentioned.
The base used in the reaction includes alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. And the like. In the reaction, with respect to 1 mol of the intermediate compound (M9), the intermediate compound (M18) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M14) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated intermediate compound (M14) can be further purified by chromatography, recrystallization and the like.
This condensed heterocyclic compound (P20) can be produced by reacting the intermediate compound (14) with a sulfurizing agent.
The reaction is performed in the presence or absence of a solvent.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, and diglyme, and halogens such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene. And hydrocarbons, aromatic hydrocarbons such as toluene, benzene and xylene, nitriles such as acetonitrile, nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine and quinoline, and mixtures thereof.
Examples of the sulfurizing agent used in the reaction include niline pentasulfide, Lawesson's reagent (2,4-bis- (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide), and the like. Can be mentioned.
In the reaction, the sulfurizing agent is usually used in a ratio of 1 mol to 3 mol with respect to 1 mol of the intermediate compound (M14).
The reaction temperature of the reaction is usually in the range of 0 ° C. to 200 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The condensed heterocyclic compound (P20) can be isolated by collecting the obtained solid by filtration. The isolated present condensed heterocyclic compound (P20) can be further purified by recrystallization, chromatography or the like.

(Production Method 4)
This condensed heterocyclic compound can be produced by reacting the intermediate compound (M1) and the intermediate compound (M4) in the presence of an oxidizing agent.

[Wherein the symbols have the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether, THF and tert-butyl methyl ether, dichloromethane, chloroform, carbon tetrachloride, 1,2- Halogenated hydrocarbons such as dichloroethane and chlorobenzene, aromatic hydrocarbons such as toluene, benzene and xylene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile, DMF, NMP, 1,3-dimethyl- Examples thereof include aprotic polar solvents such as 2-imidazolidinone and DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof.
The reaction can be carried out by adding an acid as necessary.
Examples of the acid used in the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, polyphosphoric acid, and the like.
The reaction can be carried out by adding sulfite as necessary.
Examples of the sulfite used in the reaction include sulfites such as sodium bisulfite and sodium disulfite.
Examples of the oxidizing agent used in the reaction include oxygen, copper (II) chloride, DDQ and the like.
In the reaction, the intermediate compound (M4) is usually in a proportion of 1 to 2 mol, the acid is usually in a proportion of 0.1 to 2 mol, and the sulfite is usually in a proportion of 1 to 1 mol of the intermediate compound (M1). The proportion of 5 moles and the oxidizing agent are usually used in the proportion of 1 mole to 5 moles.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The condensed heterocyclic compound (1) can be isolated by collecting the obtained solid by filtration.
The isolated present condensed heterocyclic compound (1) can be further purified by recrystallization, chromatography or the like.

(Production method 5)
The present condensed heterocyclic compound (1) in which n is 0 in the formula (1) can be produced by reacting the intermediate compound (M6) and the compound (M7) in the presence of a base.

[Wherein V ² represents a halogen atom, and other symbols have the same meaning as in formula (1). The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
In the reaction, with respect to 1 mol of the intermediate compound (M6), the compound (M7) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (1) in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. it can.
The isolated condensed heterocyclic compound (1) in which n is 0 can be further purified by chromatography, recrystallization or the like.
In the reaction, V ² is preferably a fluorine atom or a chlorine atom.

(Production method 6)
The intermediate compound (M20) is reacted with the intermediate compound (M19) or the intermediate compound (M39) to produce an intermediate compound (M20). The intermediate compound (M6) can be produced by condensation with Here, the production of the intermediate compound (M20) and the condensation in the molecule occur almost simultaneously, and the production of the intermediate compound (M20) may not be confirmed.

[Wherein V ² represents a halogen atom, and other symbols have the same meaning as in formula (1). ]
An intermediate compound (M20) can be produced according to the production method 2 using the intermediate compound (M19) instead of the intermediate compound (M2).
The intermediate compound (M20) can be produced according to the production method 2, using the intermediate compound (M39) instead of the intermediate compound (M18).
The intermediate compound (M6) can be produced according to the production method 2 using the intermediate compound (M20) instead of the intermediate compound (M3).
Further, the intermediate compound (M6) can be produced in a one-step reaction (one pot) according to the production method 2 using the intermediate compound (M19) instead of the intermediate compound (M2).
In addition, the intermediate compound (M6) can be produced in a one-step reaction (one pot) according to the production method 2 using the intermediate compound (M39) instead of the intermediate compound (M2).
In the reaction, V ² is preferably a fluorine atom or a chlorine atom.

(Production method 7)
By reacting the intermediate compound (M20) and the compound (M7), an intermediate compound (M3) in which n is 0 in the formula (M3) can be produced. In addition, the condensed heterocyclic compound (1) in which n is 0 in the formula (1) can be produced by condensing the obtained intermediate compound (M3) in the molecule.

[Wherein V ² represents a halogen atom, and other symbols have the same meaning as in formula (1)]
An intermediate compound (M3) in which n is 0 can be produced according to the production method 5 using the intermediate compound (M20) instead of the intermediate compound (M6).
Using the intermediate compound (M3) in which n is 0 instead of the intermediate compound (M3), the present condensed heterocyclic compound (1) in which n is 0 can be produced according to the production method 2. it can.
Further, the intermediate compound (M20) is used in place of the intermediate compound (M6), and according to the method of production method 5, the present condensed heterocyclic compound (1) in which n is 0 is reacted in one step (one pot). It can also be manufactured.
In the reaction, V ² is preferably a fluorine atom or a chlorine atom.

(Production method 8)
In the present condensed heterocyclic compound (1) in which n is 0 in the formula (1), the intermediate compound (M8) or the intermediate compound (M8 ′) which is a disulfide thereof and the compound (M17) are present in the presence of a base. It can manufacture by making it react below.

[In the formula, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group or a methanesulfonyloxy group, and other symbols have the same meanings as in the formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
When the intermediate compound (M8 ′) that is a disulfide is used, it is usually performed in the presence of a reducing agent.
Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate (trade name Rongalite).
In the reaction, with respect to 1 mol of the intermediate compound (M8), the compound (M17) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol. When an intermediate compound (M8 ′) that is a disulfide is used, the ratio of the compound (M17) is usually 2 to 10 mol and the base is usually 2 to 10 with respect to 1 mol of the intermediate compound (M8 ′). A mole ratio and a reducing agent are usually used in a ratio of 1 to 5 moles.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (1) in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. it can.
The isolated condensed heterocyclic compound (1) in which n is 0 can be further purified by chromatography, recrystallization or the like.

(Production method 9)
The present condensed heterocyclic compound (1) in which n is 0 in the formula (1) is produced by reacting the intermediate compound (M8 ′) with the compound (M17′-1) or the compound (M17′-2). can do.

Wherein, V ³ represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meanings as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
In the reaction, the compound (M17′-1) is usually used at a ratio of 1 to 2 mol with respect to 1 mol of the intermediate compound (M8 ′). When the compound (M17′-2) is used, the compound (M17′-2) is usually used at a ratio of 1 to 2 mol with respect to 1 mol of the intermediate compound (M8 ′).
The reaction temperature of the reaction is usually in the range of -80 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (1) in which n is 0 can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. it can.
The isolated condensed heterocyclic compound (1) in which n is 0 can be further purified by chromatography, recrystallization or the like.

(Production method 10)
The intermediate compound (M8) can be produced by reacting the intermediate compound (M6) with a sulfurizing agent. Moreover, the intermediate compound (M8 ′), which is a disulfide thereof, can be produced by oxidizing the intermediate compound (M8).

[Wherein V ² represents a halogen atom, and other symbols have the same meaning as in formula (1). ]
The intermediate compound (M8) can be produced according to the production method 5 using sodium sulfide, sodium hydrogen sulfide, hydrogen sulfide or the like instead of the compound (M7).
Here, the reaction from the intermediate compound (M8) to the intermediate compound (M8 ′) is likely to occur, and the intermediate compound (M8 ′) may be generated during the synthesis of the intermediate compound (M8). In the reaction, V ² is preferably a fluorine atom or a chlorine atom.
The intermediate compound (M8 ′) can be produced by reacting two molecules of the intermediate compound (M8) in the presence of an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, carboxylic acids such as acetic acid, and mixtures thereof. Examples of the oxidizing agent used in the reaction include oxygen, iodine, aqueous hydrogen peroxide, and potassium ferricyanide.
In the reaction, the oxidizing agent is usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of the intermediate compound (M8).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M8 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M8 ′) can be further purified by chromatography, recrystallization and the like.

(Production method 11)
By reacting the present condensed heterocyclic compound (P2) in which A ¹ is —NH— in the formula (1) and the compound (M10) in the presence of a base, A ¹ in the formula (1) is —NR ^{7. '-} it can be present fused heterocyclic compound (P3) can be produced.

[Wherein R ^{7 ′} represents any one of R ⁷ other than hydrogen atom in formula (1), and L represents a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group, a methanesulfonyloxy group, etc. It represents a leaving group, and other symbols have the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Is mentioned.
In the reaction, the compound (M10) is usually used in a proportion of 1 to 5 mol and the base is usually used in a proportion of 1 to 3 mol with respect to 1 mol of the present condensed heterocyclic compound (P2).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated present condensed heterocyclic compound (P3) can be further purified by chromatography, recrystallization and the like.

(Production method 12)
The intermediate compound (M2) can be produced by hydrolyzing the intermediate compound (M37).

[Wherein the symbols have the same meaning as in formula (1). ]
When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used for the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M2) can be further purified by chromatography, recrystallization and the like.
When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is generally used at a ratio of 1 to 10 mol per 1 mol of the intermediate compound (M37).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate solution (M2) is isolated by acidifying the reaction solution and then performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do. The isolated intermediate compound (M2) can be further purified by chromatography, recrystallization and the like.

(Production method 13)
Intermediate compound (M18) can be produced by reacting intermediate compound (M2) in the presence of a chlorinating agent.

[Wherein the symbols have the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, and aliphatic halogens such as dichloromethane and chloroform. Hydrocarbons and mixtures thereof.
Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl dichloride, phosphorus oxychloride and the like.
In the reaction, the chlorinating agent is usually used at a ratio of 1 to 5 mol with respect to 1 mol of the intermediate compound (M2).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M18) can be isolated by removing the solvent.

(Production method 14)
Intermediate compound (M2), intermediate compound (M4) or intermediate compound (M37) are respectively intermediate compound (M19), intermediate compound (M22) or intermediate compound (M36) and compound (M7). Can be produced by oxidizing the compound obtained as necessary.

[Wherein V ² represents a halogen atom, and other symbols have the same meaning as in formula (1). ]
An intermediate compound (M2) in which n is 0 can be produced according to the production method 5 using the intermediate compound (M19) instead of the intermediate compound (M6).
An intermediate compound (M4) in which n is 0 can be produced according to the production method 5 using the intermediate compound (M22) instead of the intermediate compound (M6).
By using the intermediate compound (M36) instead of the intermediate compound (M6), an intermediate compound (M37) in which n is 0 can be produced according to the method of Production Method 5.
According to the method of production method 1, an intermediate compound (wherein n is 1 or 2) is used in place of the present condensed heterocyclic compound (1) where n is 0, and n is 0. M2) can be manufactured.
In accordance with the method of Production Method 1, an intermediate compound in which n is 1 or 2 is used instead of the present condensed heterocyclic compound (1) in which n is 0, and n is 0. M4) can be manufactured.
According to the method of production method 1, an intermediate compound in which n is 1 or 2 is used instead of the present condensed heterocyclic compound (1) in which n is 0 and n is 0. M37) can be manufactured.
In the reaction, V ² is preferably a fluorine atom or a chlorine atom.

(Production method 15)
An intermediate compound (M30) can be produced by nitration of the intermediate compound (M29) or by reacting the intermediate compound (M33) with the compound (M28). By reducing the intermediate compound (M30) obtained here, an intermediate compound (M1) in which A ¹ is —NR ⁷ — in the formula (M1) can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M30) can be produced by reacting intermediate compound (M33) with compound (M28) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
This reaction can also be performed by adding a base as necessary. Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and N, N-diisopropylethylamine, and pyridine, Examples thereof include nitrogen-containing aromatic compounds such as 4-dimethylaminopyridine.
In the reaction, with respect to 1 mol of the intermediate compound (M33), the compound (M28) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 0 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
Intermediate compound (M30) can be produced by reacting intermediate compound (M29) in the presence of a nitrating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.
Examples of the nitrating agent used in the reaction include concentrated nitric acid.
In the reaction, the nitrating agent is usually used at a ratio of 1 to 3 moles relative to 1 mole of the intermediate compound (M29).
The reaction temperature of the reaction is usually in the range of −10 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extraction with an organic solvent, and drying and concentration of the organic layer. . The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
In addition, when ^{R 7} is a hydrogen atom in the formula (M30), an intermediate compound wherein ^{R 7} is hydrogen atom (M30) used in place of the compound (P2), according to the method of Preparation 11, In the formula (M30), a compound in which R ⁷ is other than a hydrogen atom can also be produced.
The intermediate compound (M1) in which A ¹ is —NR ⁷ — can be produced by reacting the intermediate compound (M30) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in a hydrogen atmosphere at 1 to 100 atm, usually in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water And mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In the reaction, hydrogen is usually used in a proportion of 3 mol and a hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the intermediate compound (M30).
This reaction can also be performed by adding an acid, a base or the like, if necessary.
Examples of the acid used for the reaction include acetic acid and hydrochloric acid, and examples of the base used for the reaction include tertiary amines such as triethylamine, magnesium oxide and the like.
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, an intermediate compound in which A ¹ is —NR ⁷ — is obtained by performing post-treatment operations such as filtration of the reaction mixture, extraction with an organic solvent as necessary, and drying and concentration of the organic layer. (M1) can be isolated. The isolated intermediate compound (M1) in which A ¹ is —NR ⁷ — can be further purified by chromatography, recrystallization, and the like.
The intermediate compound (M30) is prepared by acetylating the intermediate compound (M29) to produce an intermediate compound (M29 ′) as shown below, and then nitration of the obtained intermediate compound (M29 ′). It can also be produced by producing an intermediate compound (M30 ′) and hydrolyzing the obtained intermediate compound (M30 ′).

[Wherein the symbols have the same meaning as in formula (1). ]
The intermediate compound (M29 ′) can be produced by reacting the intermediate compound (M29) in the presence of an acylating agent.
The reaction is usually performed in the presence of a solvent or using an acylating agent as a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, and aromatics such as toluene and xylene. Group hydrocarbons, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP, DMSO and mixtures thereof. Examples of the acylating agent used in the reaction include acetic anhydride and paraacetoxynitrobenzene.
This reaction can also be performed by adding a base as necessary. Examples of the base used in the reaction include tertiary amines such as triethylamine and N, N-diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the acylating agent is usually used in a proportion of 1 mol or more and the base is usually used in a proportion of 0.1 to 10 mol with respect to 1 mol of the intermediate compound (M29).
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (M29 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M29 ′) can be further purified by chromatography, recrystallization and the like.
The intermediate compound (M30 ′) can be produced according to the production method 15, using the intermediate compound (M29 ′) instead of the intermediate compound (M29).
The intermediate compound (M30) can be produced by hydrolyzing the intermediate compound (M30 ′) in the presence of an acid or a base.
When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used in the reaction include mineral acids such as hydrochloric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (M30) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.
When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, hydrazine and the like.
In the reaction, the base is usually used at a ratio of 1 to 10 mol per 1 mol of the intermediate compound (M30 ′).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate solution (M30) is isolated by performing post-treatment operations such as acidification of the reaction solution, extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Can do. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization and the like.

(Production Method 16)
The intermediate compound (M35) is produced by brominating the intermediate compound (M29), and then the obtained intermediate compound (M35) is aminated, whereby A ¹ is —NR ⁷ in the formula (M1). An intermediate compound (M1) that is-can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M35) can be produced by reacting intermediate compound (M29) with a brominating agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, acetic acid, 1,4-dioxane, diethyl ether, THF and other ethers, ethyl acetate, butyl acetate and other esters, dichloromethane, chloroform, carbon tetrachloride, 1,2- Examples thereof include halogenated hydrocarbons such as dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, and mixtures thereof.
Examples of the brominating agent used in the reaction include N-bromosuccinimide and bromine.
The brominating agent is usually used in a proportion of 1 to 3 mol per 1 mol of the intermediate compound (M29).
The reaction temperature of the reaction is usually in the range of −10 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M35) can be isolated by collecting the resulting solid by filtration. The isolated intermediate compound (M35) can be further purified by recrystallization, chromatography or the like.
The intermediate compound (M1) in which A ¹ is —NR ⁷ — can be produced by reacting the intermediate compound (M35) with an aminating agent in the presence of a copper compound.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, ethers such as 1,4-dioxane, diethyl ether and THF, esters such as ethyl acetate and butyl acetate, dichloromethane, chloroform and tetrachloride. Carbon, halogenated hydrocarbons such as 1,2-dichloroethane, nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, nitrogen-containing aromatic compounds such as pyridine and quinoline, and mixtures thereof Can be mentioned.
Examples of the aminating agent used in the reaction include ammonia, aqueous ammonia, and lithium amide.
Examples of the copper compound used in the reaction include copper, copper (I) iodide, copper (I) oxide, copper (II) oxide, acetylacetone copper (II), copper acetate (II), copper sulfate (II) and the like. Can be mentioned.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
This reaction can also be performed by adding a base as necessary.
Examples of the base used in the reaction include pyridine, picoline, 2,6-lutidine, DBU, nitrogen-containing heterocyclic compounds such as 1,5-diazabicyclo [4.3.0] -5-nonene, triethylamine, N, N -Inorganic bases such as tertiary amines such as diisopropylethylamine, tripotassium phosphate, potassium carbonate, cesium carbonate and sodium hydroxide.
The aminating agent is usually used in a proportion of 1 to 5 mol, the copper compound is usually used in a proportion of 0.02 to 0.5 mol, and the ligand is usually used with respect to 1 mol of the intermediate compound (M35). The base is used in a proportion of 0.02 to 2 mol, and the base is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 30 to 200 ° C., and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent and the organic layer is concentrated; the reaction mixture is poured into water and the resulting solid is collected by filtration; or formed in the reaction mixture. The intermediate compound (M1) in which A ¹ is —NR ⁷ — can be isolated by collecting the obtained solid by filtration. The isolated intermediate compound (M1) in which A ¹ is —NR ⁷ — can be further purified by recrystallization, chromatography or the like.

(Production method 17)
After intermediate compound (M32) is prepared by nitration of intermediate compound (M31), the obtained intermediate compound (M32) is reduced, whereby A ¹ is an oxygen atom in formula (M1). Intermediate compound (M1) can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
The intermediate compound (M32) can be produced according to the production method 15 using the intermediate compound (M31) instead of the intermediate compound (M29).
By using the intermediate compound (M32) instead of the intermediate compound (M30), an intermediate compound (M1) in which A ¹ is an oxygen atom can be produced according to the method of Production Method 15.

(Production method 18)
In the formula (M1), an intermediate compound (M34) is produced by reacting the intermediate compound (M33) with a sulfurizing agent, and then the obtained intermediate compound (M34) is reacted with a reducing agent. An intermediate compound (M1) in which A ¹ is a sulfur atom can be produced.

[Wherein the symbols have the same meaning as in formula (1). ]
Intermediate compound (M34) can be produced by reacting intermediate compound (M33) with thiourea in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, with respect to 1 mol of the intermediate compound (M33), thiourea is usually used in a proportion of 0.5 to 3 mol and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, an intermediate compound (M34) can be isolated by performing post-treatment operations such as addition of an acid to the reaction mixture, extraction with an organic solvent, and drying and concentration of the organic layer. .
The isolated intermediate compound (M34) can also be purified by chromatography, recrystallization and the like.
The intermediate compound (M1) in which A ¹ is a sulfur atom can be produced by reacting the intermediate compound (M34) with a reducing agent.
The reduction reaction can be performed, for example, in the presence of metal powder such as iron powder and zinc powder; acid such as hydrochloric acid and acetic acid; and water.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, Examples include aprotic polar solvents such as DMF, NMP, DMSO, and mixtures thereof.
Examples of the reducing agent used in the reaction include metal powders such as iron powder, zinc powder, and tin dichloride.
In the reaction, metal powder is usually used at a ratio of 3 to 10 moles with respect to 1 mole of the intermediate compound (M34).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, an intermediate compound (M1) in which A ¹ is a sulfur atom is obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Can be isolated. The isolated intermediate compound (M1) in which A ¹ is a sulfur atom can also be purified by chromatography, recrystallization, and the like.

(Production Method 19)
The present condensed heterocyclic compound (P7) in which R ⁵ is a C1-C6 perfluoroalkyl group in the formula (1), the present condensed heterocyclic compound (P4) in which R ⁵ is a halogen atom in the formula (1), and a compound (M11) or compound (M11 ′) can be produced by reacting in the presence of a copper compound.

[Wherein, V ¹ represents a halogen atom, Rf represents a C1-C6 perfluoroalkyl group, and other symbols represent the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, aprotic polar solvents such as DMF, NMP, and DMSO, and mixtures thereof. Examples of the copper compound used for the reaction include copper and copper (I) iodide. When the compound (M11) is used in the reaction, the compound (M11) is usually in a proportion of 1 to 10 mol and the copper compound is usually in a proportion of 0.5 to 10 mol with respect to 1 mol of the condensed heterocyclic compound (P4). The reaction temperature of the reaction is usually in the range of 100 to 200 ° C. The reaction time is usually in the range of 0.5 to 48 hours.
When the intermediate compound (M11 ′) is used in the reaction, potassium fluoride may be added. The compound (M11 ′) is usually 1 to 10 mol, the copper compound is usually 0.1 to 10 mol, and the potassium fluoride is usually 0.1 to 1 mol of the fused heterocyclic compound (P4). It is used in a proportion of 5 moles, and the reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 48 hours.
After completion of the reaction, the condensed heterocyclic compound (P7) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated condensed heterocyclic compound (P7) isolated can be further purified by chromatography, recrystallization and the like. In the reaction, V ¹ is preferably a bromine atom or an iodine atom.

(Production method 20)
By reacting the present condensed heterocyclic compound (P4) with a sulfurizing agent, the present condensed heterocyclic compound (P9) in which R ⁵ is —SH in the formula (1) can be produced. Moreover, the intermediate compound (P9 ') which is the disulfide body can be manufactured by oxidizing this condensed heterocyclic compound (P9).

[Wherein V ¹ represents a halogen atom, and other symbols have the same meaning as in formula (1). ]
This condensed heterocyclic compound (P9) can be produced by reacting this condensed heterocyclic compound (P4) in the presence of a thiolating agent and a catalyst.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, aprotic polar solvents such as DMF, NMP, and DMSO, and mixtures thereof.
Examples of the thiolating agent used in the reaction include sodium sulfide, sodium sulfide nonahydrate, and thiourea.
Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
This reaction can also be performed in presence of a base as needed.
Examples of the base used in the reaction include inorganic bases such as potassium carbonate, cesium carbonate, and tripotassium phosphate, and organic bases such as triethylamine.
In the reaction, with respect to 1 mole of the present condensed heterocyclic compound (P4), the ratio of the thiolating agent is usually 1 to 10 moles, the catalyst is usually 0.1 to 5 moles, and the ligand is usually 0.1. The base is used in a proportion of 1 to 5 mol and the base is usually used in a proportion of 1 to 2 mol.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P9) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated present condensed heterocyclic compound (P9) can be further purified by chromatography, recrystallization and the like. In the reaction, V ¹ is preferably a bromine atom or an iodine atom.
Here, the reaction from the condensed heterocyclic compound (P9) to the intermediate compound (P9 ′) is likely to occur, and the intermediate compound (P9 ′) may be generated during the synthesis of the condensed heterocyclic compound (P9). is there.
The intermediate compound (P9 ′) can be produced by reacting the present condensed heterocyclic compound (P9) in the presence of an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, ethers such as 1,4-dioxane, and aromatic hydrocarbons such as toluene and xylene. Nitriles such as acetonitrile, aprotic polar solvents such as DMF, NMP and DMSO, carboxylic acids such as acetic acid, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include oxygen, iodine, hydrogen peroxide solution, potassium ferricyanide, and the like.
In the reaction, the oxidizing agent is usually used at a ratio of 0.5 to 10 mol with respect to 1 mol of the present condensed heterocyclic compound (P9).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the intermediate compound (P9 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (P9 ′) can be further purified by chromatography, recrystallization and the like.
The condensed heterocyclic compound (P9) is produced by thioesterifying the condensed heterocyclic compound (P4) to produce an intermediate compound (P9-1), and then hydrolyzing the obtained intermediate compound (P9-1). Can be manufactured.

[Wherein, R ^{10 ′} represents any one of R ¹⁰ other than a hydrogen atom in Formula (1), and other symbols have the same meaning as in Formula (1). ]
The intermediate compound (P9-1) can be produced by reacting the present condensed heterocyclic compound (P4) in the presence of a thioesterification agent, a base and a catalyst.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, aprotic polar solvents such as DMF, NMP, and DMSO, and mixtures thereof.
Examples of the thioesterifying agent used in the reaction include thiobenzoic acid.
Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
Examples of the base used in the reaction include inorganic bases such as potassium carbonate, cesium carbonate, and tripotassium phosphate, and organic bases such as triethylamine.
In the reaction, with respect to 1 mole of the present condensed heterocyclic compound (P4), the ratio of the thioesterification agent is usually 1 to 10 moles, the catalyst is usually 0.1 to 5 moles, and the ligand is usually 0.1. The base is used in a proportion of 1 to 5 mol and the base is usually used in a proportion of 1 to 2 mol.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (P9-1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (P9-1) can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a bromine atom or an iodine atom.
This condensed heterocyclic compound (P9) can be produced by hydrolyzing the intermediate compound (P9-1).
When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent.
Examples of the acid used for the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P9) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated present condensed heterocyclic compound (P9) can be further purified by chromatography, recrystallization and the like. When hydrolyzing with a base, the reaction is usually carried out in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the intermediate compound (P9-1).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, after acidifying the reaction solution, the condensed heterocyclic compound (P9) is isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. can do. The isolated present condensed heterocyclic compound (P9) can be further purified by chromatography, recrystallization and the like.
Here, the reaction from the condensed heterocyclic compound (P9) to the intermediate compound (P9 ′) is likely to occur, and the intermediate compound (P9 ′) may be generated during the synthesis of the condensed heterocyclic compound (P9). is there.

(Production method 21)
This condensed heterocyclic compound (P9) or an intermediate compound (P9 ′) that is a disulfide thereof is reacted with the compound (M13), R ⁵ is —S (O) mR ^{10 ′} , and m is 0. A certain present condensed heterocyclic compound (P10-m0) can be produced. By oxidizing the condensed heterocyclic compound (P10-m0) in which m is 0, the condensed heterocyclic compound in which R ⁵ is —S (O) mR ^{10 ′} and m is 1 or 2 in the formula (1). A ring compound (P10) can be produced.

[Wherein, R ^{10 ′} represents any one of R ¹⁰ other than R ¹⁰ in Formula (1), and L represents a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group, a methanesulfonyloxy group, or the like. It represents a leaving group, and other symbols have the same meaning as in formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
When an intermediate compound (P9 ′) that is a disulfide is used, it is usually carried out in the presence of a reducing agent.
Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate (trade name Rongalite).
In the reaction, with respect to 1 mole of the present condensed heterocyclic compound (P9), the compound (M13) is usually used at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 1 to 10 moles.
When the intermediate compound (P9 ′) that is a disulfide is used, the compound (M13) is usually 2 to 10 moles and the base is usually 2 to 10 moles with respect to 1 mole of the intermediate compound (P9 ′). A mole ratio and a reducing agent are used in a ratio of 1 to 5 moles.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P10-m0) in which m is 0 is isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. be able to. The isolated condensed heterocyclic compound (P10-m0) in which m is 0 can also be further purified by chromatography, recrystallization, and the like.
Further, among the present condensed heterocyclic compounds (P10-m0) in which m is 0, compounds in which R ^{10 ′} is C1-C6 perfluoroalkyl are intermediate compounds (P9 ′), perfluoroalkyl iodide, and reduction. It can manufacture by making an agent react. The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
Examples of the reducing agent used in the reaction include tetrakis (dimethylamino) ethylene.
Examples of perfluoroalkyl iodide include trifluoromethane iodide, pentafluoroethane iodide, heptafluoro-2-iodopropane, and the like.
In the reaction, perfluoroalkyl iodide is usually used in a proportion of 2 to 10 mol and a reducing agent in a proportion of 1 to 5 mol per 1 mol of the intermediate compound (P9 ′).
The reaction temperature of the reaction is usually in the range of −80 to 50 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P10-m0) in which m is 0 is isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. be able to. The isolated condensed heterocyclic compound (P10-m0) in which m is 0 can also be further purified by chromatography, recrystallization, and the like.
In this condensed heterocyclic compound (P10), this condensed heterocyclic compound in which m is 1 or 2 is reacted with this condensed heterocyclic compound (P10-m0) in which m is 0 in the presence of an oxidizing agent. Can be manufactured.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, alcohols such as methanol and ethanol, acetic acid, water, and mixtures thereof.
Examples of the oxidizing agent used in the reaction include m-chloroperbenzoic acid or hydrogen peroxide water.
The reaction can be carried out in the presence of a catalyst as necessary.
Examples of the catalyst used in the reaction include sodium tungstate.
In this reaction, the amount of the oxidizing agent is usually 1 to 5 mol and the catalyst is usually 0.01 to 0.5 mol with respect to the present condensed heterocyclic compound (P10-m0) in which 1 mol of m is 0. Used in proportions.
In the case of producing a compound in which m is 1, the ratio of the oxidizing agent is usually 0.8 to 1.2 moles relative to the present condensed heterocyclic compound (P10-m0) in which 1 mole of m is 0. Is usually used in a proportion of 0.05 to 0.2 mol, and in the case of producing a compound in which m is 2, with respect to the present condensed heterocyclic compound (P10-m0) in which 1 mol of m is 0, The oxidizing agent is usually used in a proportion of 1.8 to 5 mol, and the catalyst is usually used in a proportion of 0.05 to 0.2 mol.
The reaction temperature of the reaction is usually in the range of −20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary, dried, By performing post-treatment operations such as concentration, the present condensed heterocyclic compound (P10) in which m is 1 or 2 can be isolated. The isolated fused heterocyclic compound (P10) in which isolated m is 1 or 2 can be further purified by chromatography, recrystallization or the like.

(Production method 22)
The present condensed heterocyclic compound (P11) in which R ⁵ is —OH in the formula (1) can be produced from the present condensed heterocyclic compound (P4) through an intermediate compound (P11 ′).

[Wherein V ¹ represents a halogen atom, and other symbols have the same meaning as in formula (1). The intermediate compound (P11 ′) can be produced by reacting the present condensed heterocyclic compound (P4) with benzyl alcohol in the presence of a base.
The reaction is usually performed in the presence of a solvent or benzyl alcohol as a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, aprotic polar solvents such as DMF, NMP, and DMSO, and mixtures thereof. This reaction can also be performed by adding a catalyst as needed. Examples of the catalyst used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
This reaction can also be performed by adding a ligand as necessary.
Examples of the ligand used in the reaction include acetylacetone, salen, phenanthroline, and the like.
The reaction is usually performed in the presence of a base.
Examples of the base used in the reaction include inorganic bases such as potassium carbonate, cesium carbonate, and tripotassium phosphate.
In this reaction, benzyl alcohol is usually in a proportion of 1 to 10 mol, catalyst is usually in a proportion of 0.1 to 5 mol, and ligand is usually in a proportion of 0.1 mol per mol of the condensed heterocyclic compound (P4). The base is used in a proportion of ˜5 mol, and the base is usually used in a proportion of 1 mol to 2 mol.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (P11 ′) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated intermediate compound (P11 ′) can be further purified by chromatography, recrystallization and the like.
In the reaction, V ¹ is preferably a bromine atom or an iodine atom.
This condensed heterocyclic compound (P11) can be produced by reacting the intermediate compound (P11 ′) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is usually performed in a hydrogen atmosphere at 1 to 100 atm, usually in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, water And mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
In the reaction, hydrogen is usually used in a proportion of 3 mol and a hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the intermediate compound (P11 ′).
This reaction can also be performed by adding an acid, a base or the like, if necessary.
Examples of the acid used for the reaction include acetic acid and hydrochloric acid, and examples of the base used for the reaction include tertiary amines such as triethylamine, magnesium oxide and the like.
The reaction temperature of the reaction is usually in the range of −20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P11) is isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction with an organic solvent as necessary, and drying and concentration of the organic layer. be able to. The isolated present condensed heterocyclic compound (P11) can be further purified by chromatography, recrystallization or the like.

(Production Method 23)
The condensed heterocyclic compound (P12) in which R ⁵ is —OR ^{10 ′} in the formula (1) can be produced by reacting the condensed heterocyclic compound (P11) and the compound (M13).

[Wherein, R ^{10 ′} represents any one of R ¹⁰ other than a hydrogen atom in Formula (1), and other symbols have the same meaning as in Formula (1). ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, DMF, Examples include aprotic polar solvents such as NMP and DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, inorganic bases such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine. Can be mentioned.
In the reaction, with respect to 1 mol of the present condensed heterocyclic compound (P11), the compound (M13) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P12) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated present condensed heterocyclic compound (P12) can be further purified by chromatography, recrystallization or the like.
Moreover, this condensed heterocyclic compound (P12) whose R < ^{10 '} > is a trifluoromethyl group among this condensed heterocyclic compounds (P12) can be manufactured with the following manufacturing methods.

[Wherein the symbols have the same meaning as in formula (1). ]
The intermediate compound (P11 ″) can be produced by reacting the present condensed heterocyclic compound (P11) with a base, carbon disulfide and a methylating agent.
The reaction is performed in the presence of a solvent.
Examples of the solvent used in the reaction include aprotic polar solvents such as DMF, NMP, and DMSO.
Examples of the base used for the reaction include alkali metal hydrides such as sodium hydride.
As a methylating agent used for reaction, methyl iodide is mentioned, for example.
In the reaction, with respect to 1 mol of the present condensed heterocyclic compound (P11), the base is usually in a proportion of 1 to 2 mol, the carbon disulfide is usually in a proportion of 1 to 10 mol, and the methylating agent is usually in a proportion of 1 to 10 mol. It is used in the ratio.
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the intermediate compound (P11 ″) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The intermediate compound (P11 ″) can be further purified by chromatography, recrystallization and the like.
Among the condensed heterocyclic compounds (P12), the condensed heterocyclic compound (P12) in which R ^{10 ′} is a trifluoromethyl group reacts the intermediate compound (P11 ″) with a fluorinating agent in the presence of a base. Can be manufactured.
The reaction is performed in the presence of a solvent.
Examples of the solvent used in the reaction include halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane.
The reaction is carried out in the presence of a base and a fluorinating agent.
Examples of the base used in the reaction include 1,3-dibromo-5,5-dimethylhydantoin.
Examples of the fluorinating agent used in the reaction include tetra-n-butylammonium fluoride and a hydrogen fluoride pyridine complex.
In the reaction, with respect to 1 mol of the intermediate compound (P11 ″), the base is usually used in a proportion of 1 to 10 mol, and the fluorinating agent is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of −80 to 50 ° C. The reaction time of the reaction is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the condensed heterocyclic compound (P12) in which R ^{10 ′} is a trifluoromethyl group is obtained by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying of the organic layer, and concentration. It can be isolated. The isolated condensed heterocyclic compound (P12) in which the isolated R ^{10 ′} is a trifluoromethyl group can be further purified by chromatography, recrystallization, and the like.

(Production method 24)
Of the condensed heterocyclic compound and the intermediate compound described above, by reacting a compound having a nitrogen-containing heterocyclic moiety having a lone pair on the nitrogen atom with an oxidizing agent, the nitrogen atom may be oxidized in some cases. N-oxide can be produced.
Examples of the nitrogen-containing heterocyclic moiety include a pyridine ring.
The reaction can be carried out by a known method, for example, in a solvent such as halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene, alcohols such as methanol and ethanol, acetic acid, water and a mixture thereof. It is carried out using an oxidizing agent such as chloroperbenzoic acid or hydrogen peroxide.

Pyrethrin, allethrin, praretrin, imiprothrin, resmethrin, tetramethrin, phenothrin, ciphenothrin, flumethrin, metofluthrin, transfluthrin, profluthrin, dimethylfluthrin, empentrin, flamethrin, meperfluthrin, fechlorthion, dichlorvos Diflubenzuron, hexaflumuron, amidoflumet, chlorfenapyr, cyromazine, hydroprene, metoprene, methoxadiazone, etoxazole, piperonyl butoxide and N- (2-ethylhexyl) -5-norbornene-2,3-dicarboximide are known compounds, for example "THE PESTICIDE MANUAL-15th EDITION (B It is described in the PC published) ISBN 978-1-901396-18-8 ". These compounds can be obtained from commercially available preparations or produced by known methods.
Among the insecticidal compounds, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate is It is a compound described in Japanese Unexamined Patent Publication No. 2004-2363, and can be produced by the method described in the publication. 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2-dimethyl-3- (3,3,3-trifluoro-1-propenyl) -cyclopropanecarboxylate is a Chinese patent It is a compound described in Japanese Patent Publication No. 10137722, and can be produced by the method described in the publication. 2,3,5,6-tetrafluoro-4-propargylbenzyl = 2,2,3,3-tetramethylcyclopropanecarboxylate is a compound described in JP 2001-302591 A, and It can be produced by the method described in 1.
Among the insecticidal compounds, the compound represented by the formula (2) is a compound described in JP 2010-150157 A, and can be produced by the method described in the publication. The compound represented by the formula (3) is a compound described in JP 2010-116346 A, and can be produced by the method described in the publication. The compound represented by the formula (4) is a compound described in JP 2012-36098 A, and can be produced by the method described in the publication. The compound represented by the formula (5) is a compound described in an international publication number WO2012 / 066660 publication pamphlet, and can be produced by a method described in the pamphlet.

The pest control composition of the present invention may be a mixture of the condensed heterocyclic compound and the insecticidal compound, but usually the mixed heterocyclic compound, the insecticidal compound and an inert carrier are mixed, Add surfactants and other formulation adjuvants as needed, oil, emulsion, flowable, wettable powder, wettable powder, powder, granule, microcapsule, aerosol, smoke , Poisonous baits, resin preparations, shampoos, paste preparations, foams, carbon dioxide preparations, tablets and the like are used.
These preparations may be used after being processed into mosquito coils, electric mosquito mats, liquid mosquito traps, fumigants, fumigants, sheet preparations, spot-on agents, or oral treatments.
The pest control composition of the present invention usually contains 0.01 to 95% by weight of the present condensed heterocyclic compound.
Further, the formulated pest control composition can be used as a pest control agent as it is or by adding other inactive components.
The total amount of the present condensed heterocyclic compound and the present insecticidal compound in the pest control composition of the present invention is usually 0.1% to 100% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80%. Within the weight percent range.

Examples of the inert carrier used for formulation include a solid carrier, a liquid carrier, and a gaseous carrier. Examples of the solid support include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate). , Hydrated silica, etc.), fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.) Polyester resin, nylon resin such as nylon-6, nylon-11, nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer).
Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyro Tolyl), ethers (diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc. ), Acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oil (Soybean oil, cottonseed oil, etc.).
Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
Examples of other formulation adjuvants include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
Examples of the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid. Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.

Although the content ratio of the present condensed heterocyclic compound and the present insecticidal compound in the pest control composition of the present invention is not particularly limited, The amount is usually 10 to 100,000 parts by weight, preferably 100 to 10,000 parts by weight. That is, the ratio of the content of the present condensed heterocyclic compound and the present insecticidal compound is usually 100: 1 to 1: 100 by weight, and particularly 10: 1 to 1:10.

In the pest control method of the present invention, an effective amount of the pest control composition is applied directly to pest arthropods and / or to pest arthropod habitats (plants, soil, households, animal bodies, etc.). Is done. In the pest control method of the present invention, the pest control composition of the present invention is usually used in the form of a pest control agent.
Moreover, pests can be controlled by applying an effective amount of the pest control composition of the present invention to the plant or the soil where the plant is cultivated. Furthermore, pests can be controlled by applying to plant seeds and bulbs in advance.
In the present invention, when the pest control composition of the present invention is applied to a plant, it is carried out by applying an effective amount of the pest control composition of the present invention to the plant and / or its cultivation place, plant seed, bulb. .
Specific examples of the method for applying the pest control composition of the present invention include application to foliage, flower vases or ears of plants such as foliage spraying, application to seedlings in nursery boxes, etc., or before planting plants. Application to cultivated land and soil after soaking, seed disinfection, seed soaking and application to seeds such as seed coat, application to seedlings, application to bulbs such as seed pods and the like.
In the present invention, the plant seed means the seed of the plant in a state before being sown in the soil or the culture medium, and the bulb is a bulb, a bulb of the plant in a state before being planted in the soil or the culture medium. It means tubers, rhizomes and tuberous roots.

Examples of pests for which the composition of the present invention is effective include harmful insects and harmful mites. Specific examples of such pests include the following.
Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetle aphids iphum euphorbiae), potato beetle aphid (Aulacorthum solani), wheat pea aphid (Rhopalosiphum padi), citrus aphid (Tomoptera citricidus), peach beetle (Homoptera) Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorina chinensis), bark beetles (Eysarcoris parvus), winged bugs (Halyomorpha mista) m), whitefly (Bemisia tabaci), whitefly (Dialeurodes citri), whitefly (Aleurocanthus spiniferus) and other whitefly, Aonidiella aspora ), Ruby Beetle (Ceroplastes rubens), Icerya purchasi, Fujino scale, Planococcus kraunhiae, Pseudococcus longispiris, Pseudococcus longispiris daulacaspis pentagona) scale insects such as, tingidae such, bedbug (Cimex lectularius), bed bugs such as network Thailand bed bugs (Cimex hemipterus), and psyllid class.
Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Common moths such as Shibatatsuga (Pediasateterrellus), Spodoptera (Spodopteraritura), Spodoptera exigua, Pseudoteria sepata, Matoga assicae), agrotis ipsilon, tamanaginawaba (plusia nigrisigna), trichopulsia, heliotis, helicoberpa, etc., moth, ), Azuki beetle (Matsumuraeses azukivivora), Apple wolfberry (Adoxophyes orana fasciata), Chinese wolfberry (Adoxophyshonamii.), Chamonamaki (Homomonaki). ps fuscopupleunus, Cydia pomonella, and the like, genus genus, genus cyno Species of the genus Curtis, Suga such as Plutella xylostella, Pterophora gossypiella potato moth, such as Phthorimaea operculella, Hyphatria (Hypha) ea translucens), Hirozukoga such as webbing clothes moth (Tineola bisselliella).
Thrips pests: Frankliniella occidentalis, Thrips parmi, Scitotrips dorsalis, and Thrips thrips
Diptera: Culex (Culex pipiens pallens), Culex (Culex tritaeniorhynchus), Culex such as Culex quinquefasciatus (Culex quinquefasciatus), Aedes aegypti (Aedes aegypti), Aedes albopictus (Aedes albopictus) Aedes genus such as Anopheles sinensis (Anopheles sinensis), etc. Genus Anopheles, chironomid, housefly (Musca domestica), housefly (Muscina stabulans), etc. (A romyza oryzae), rice Hime leafminer (Hydrellia griseola), tomato leafminer, (Liriomyza sativae), legume leafminer (Liriomyza trifolii), leafminer such as the pea (Chromatomyia horticola), chloropidae such as Inekimoguribae (Chlorops oryzae), melon fly (Dacus cucurbitae), fruit flies such as Ceratitis capitata, fruit flies such as Drosophila, flea flies such as Megaselia spiracularis, Clogmia alboba, etc. Blackfly acids, Abu acids, keds acids and stable flies such as gadfly (Tabanus trigonus).
Coleoptera pests: Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoprus oryzophilus), Azuki beetle (Callosobrchuchus chiensis), Echonocnemus quail (Echinocnemus squatium) weevil such as Onomus grandis and Sphenophorus venatus Potato beetles such as Phyllotreta sriolata, Colorado potato beetle (Leptinotarsa decemlineata), Anthrenus verbasci, larvae moth beetle (Dermestes calcifers L, etc.) Iderma serricorne, etc., Epilacunas such as Epilachna vigintioctopuntata, Lyctus brunneus, pine beetle longhorn beetles such as malasica), click beetles (Agriotes spp.), and Paederus fuscipes.
Diptera: Locusta migratoria, Kelly (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, and crickets.
Lepidoptera: Cat fleas (Ctenocephalides felis), Dog fleas (Ctenocephalides canis), Human fleas (Pulex irritans), Xenopsilla cheopes, etc.
Anoplura: body louse (Pediculus humanus corporis), head lice (Pediculus humanus humanus), crab louse (Phthirus pubis), Ushijirami (Haematopinus eurysternus), Hitsujijirami (Dalmalinia ovis), Butajirami (Haematopinus suis), Inujirami (Linognathus setosus) and the like.
Mallophaga pests: sheep body louse (Dalmalinia ovis), Ushihajirami (Dalmalinia bovis), chicken body louse (Menopongallinae), Inuhajirami (Trichodectes canis), Nekohajirami (Felicola subrostrata) etc. Hymenoptera: Iehimeari (Monomorium pharaosis), Formica japonica (Formica fusca japonica, Ruriari (Ochetellus glaber), Psylmyrme pungens, Psidole noda, Achillyrmex spp., Fire Ant (Solenopsis spp.) ants such as Pithema humile), wasps such as hornets, scallops, and wasps such as Athala rosae and Athalia japonica.
Cockroach insects: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta furiginosa), American cockroaches (Periplaneta americana), Japanese cockroaches (Periplaneta brunet)
Termite insect pests: Reticulites speratus, Cypterterms worm, Incitermes munus, Cyptotermes domesticus Glypoptermes satsumensis), Glypoptermes nakajimai, Caterpillars (Glyptotermes fuscus), Gyptotermes kodamai (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R. flavipes (Reticulitermes flaviceps amamianus), Kang Mont termites (Reticulitermes sp.), Takasago termite (Nasutitermes takasagoensis), Nitrobe termites (Pericapritermes nitobei), Musya termites (Sinocapriters mushae) and the like.
Mite order pests: Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor tivalica, Dermacentor varix, Dermacentor varix Tick such as (Ixodes scapularis), Amaryloma americanum, Bophilus microplus, Rhipicephalus sanguineus, hagus putrescentiae), grain mites such as Tyrophagus (Tyrophagus similis), farinae (Dermatophagoides farinae), D. pteronyssinus (Dermatophagoides ptrenyssnus) house dust mite such as, Hosotsumedani (Cheyletus eruditus), Stag Tsumedani (Cheyletus malaccensis), Minami Tsumedani (Cheyletus moorei) Claw mites (Cheeletiella yasguri), mites, mites, mites, mites, mites, mites, mites (Decrode) Acne mites such as x canis, tsutsu mite, sardine mites, house dust mites (Ornithonysus sylvairum), ummo moths such as ummo mites, ummo moths such as ummo mites, ummo moths such as umm Spiders such as Chiracanthium japonicum and Latrodictus hasseltii.
Lip and limb class: Geeu (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes) and the like.
Double leg class: Oxidus gracilis, Nedyopus tambanus, etc.
Isopods: Armadillium vulgare, etc.

When the pest control composition of the present invention is used for pest control in the agricultural field, the application amount is usually 1 to 10,000 g in terms of the amount of the present condensed heterocyclic compound per 10,000 m ² . When the pest control composition of the present invention is formulated into an emulsion, a wettable powder, a flowable, etc., it is usually diluted with water so that the active ingredient concentration is 0.01 to 10,000 ppm, Granules, powders, etc. are usually applied as they are.
These preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit cultivated soil. You may process to soil.
When the pest control composition of the present invention is used for controlling pests living in a house, the amount applied is the amount of the present condensed heterocyclic compound per 1 m ² treated area when treated on the surface. In the case of treatment in a space, the amount of the present condensed heterocyclic compound per 1 m ³ of treatment space is usually 0.01 to 500 mg. When the pest control composition of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm. , Aerosols, fumigants, poison baits, resin formulations, shampoos, pastes, foams, carbon dioxide formulations, tablets, mosquito coils, electric mosquito traps, liquid mosquito traps, smoke, fumigants, sheet formulations, Spot-on agents, oral treatment agents, etc. are applied as they are.
When the pest control composition of the present invention is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, it is well known in veterinary medicine. Can be used on animals in any way. As a specific method of use, for the purpose of systemic suppression, for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression. In this case, for example, an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag. The amount of the present condensed heterocyclic compound when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.

The pest control composition of the present invention can be used in farmland where the following “crop” is cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
Fruit trees: berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricot, prunes, etc.) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, black beetle, Japanese cypress, Japanese cypress, pine, spruce, yew, elm, cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi.
Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, cymbidium, begonia, etc.), foliage plants, etc.
“Crop” also includes genetically modified crops.

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples.
First, a manufacture example is shown about manufacture of this condensed heterocyclic compound.

Production Example 1 (1)
A mixture of 0.76 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.50 g of 3-fluoropyridine-2-carbaldehyde, 0.50 g of sodium hydrogen sulfite and 3 ml of DMF was stirred at 120 ° C. for 8 hours. did. Saturated aqueous sodium hydrogen carbonate solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2- (3-fluoropyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter, intermediate compound) (It may be described as (M6-2).) 0.43 g was obtained.
Intermediate compound (M6-2)

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, d), 8.66-8.63 (1H, m), 8.40 (1H, d), 7.73-7.67 (1H , M), 7.56-7.51 (1H, m), 4.16 (3H, s).

Production Example 1 (2)
To a mixture of 1.23 g of the intermediate compound (M6-2) and 3.5 ml of DMF, 0.48 g of sodium ethanethiolate was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine”). May be referred to as the present condensed heterocyclic compound 1.) 1.39 g was obtained.
This condensed heterocyclic compound 1

¹ H-NMR (CDCl ₃ ) δ: 8.73 (1H, d), 8.53 (1H, dd), 8.39 (1H, d), 7.80 (1H, dd), 7.40 ( 1H, dd), 4.04 (3H, s), 2.97 (2H, q), 1.35 (3H, t).

Production Examples 2 and 3
2- (3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 1) 0.62 g and chloroform 10 ml To the mixture, 0.79 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfinylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as “(2) , And may be referred to as the present condensed heterocyclic compound 2.) 87 mg, and 2- (3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b ] 0.49 g of pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 3) was obtained.
This condensed heterocyclic compound 2

¹ H-NMR (CDCl ₃ ) δ: 8.85 (1H, dd), 8.77 (1H, s), 8.67 (1H, dd), 8.34 (1H, s), 7.69 ( 1H, dd), 4.36 (3H, s), 3.72-3.62 (1H, m), 3.14-3.04 (1H, m), 1.47 (3H, t).
This condensed heterocyclic compound 3

¹ H-NMR (CDCl ₃ ) δ: 9.01 (1H, dd), 8.76 (1H, s), 8.55 (1H, dd), 8.31 (1H, s), 7.74 ( 1H, dd), 3.88 (3H, s), 3.83 (2H, q), 1.37 (3H, t).

Production Example 4 (1)
N2-methyl-5-trifluoromethylpyridine-2,3-diamine 0.70 g, 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid 0.53 g, EDCI hydrochloride 0.82 g, HOBt 42 mg and pyridine 4 0.5 ml of the mixture was stirred at 60 ° C. for 4 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain an intermediate compound (M20-3).
Intermediate compound (M20-3)

A mixture of the total amount of the obtained intermediate compound (M20-3), 1.04 g of p-toluenesulfonic acid monohydrate and 4 mL of N-methylpyrrolidinone was heated and stirred at 150 ° C. for 2.5 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-chloro-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5- b] 0.71 g of pyridine (hereinafter sometimes referred to as intermediate compound (M6-3)) was obtained.
Intermediate compound (M6-3)

¹ H-NMR (CDCl ₃ ) δ: 8.96 (1H, d), 8.79 (1H, d), 8.42 (1H, d), 8.22 (1H, d), 4.02 ( 3H, s).

Production Example 4 (2)
2- (3-Chloro-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (intermediate compound (M6-3)) To a mixture of 0.71 g and 4 ml of DMF, 0.24 g of sodium ethanethiolate was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate.
The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H. -0.76 g of imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 4) was obtained.
This condensed heterocyclic compound 4

¹ H-NMR (CDCl ₃ ) δ: 8.77 (1H, d), 8.75 (1H, d), 8.43
(1H, d), 7.93 (1H, d), 4.11 (3H, s), 3.02 (2H, q), 1.40 (3H, t).

Production Example 5
2- (3-Ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (present condensed heterocyclic compound 4) 0 0.66 g of m-chloroperbenzoic acid (purity 65% or more) was added to a mixture of .61 g and 10 ml of chloroform under ice cooling, followed by stirring at room temperature for 10 hours. A 10% aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl- 0.62 g of 3H-imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 5) was obtained.
This condensed heterocyclic compound 5

¹ H-NMR (CDCl ₃ ) δ: 9.25 (1H, d), 8.80 (1H, d), 8.79 (1H, d), 8.34 (1H, d), 3.96 ( 2H, q), 3.94 (3H, s), 1.42 (3H, t).

Production Example 6
1. 835 mg of 2- (3-ethylsulfanyl-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine, 2.0 g of sodium pentafluoropropionate, copper iodide A mixture of 0 g, NMP 10 mL, and xylene 50 mL was heated and stirred at 150 ° C. for 8 hours. After cooling to room temperature, a 40% aqueous ammonia solution and a saturated aqueous sodium hydrogen carbonate solution were added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present). (It may be referred to as condensed heterocyclic compound 6.) 303 mg was obtained.
This condensed heterocyclic compound 6

¹ H-NMR (CDCl ₃ ) δ: 8.69 (1H, d), 8.52 (1H, dd), 8.40 (1H, d), 7.80 (1H, dd), 7.39 ( 1H, dd), 4.06 (3H, s), 2.97 (2H, q), 1.34 (3H, t).

Production Examples 7 and 8
To a mixture of 254 mg of 2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine and 10 mL of chloroform was added m-chloro under ice cooling. 266 mg of perbenzoic acid (purity 65% or more) was added. The mixture was warmed to room temperature and stirred for 0.5 hour, and then a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethanesulfinyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present). May be referred to as fused heterocyclic compound 7.) 8 mg and 2- (3-ethanesulfonyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (Hereafter, it may be described as the present condensed heterocyclic compound 8) 235 mg was obtained.
This condensed heterocyclic compound 7

¹ H-NMR (CDCl ₃ ) δ: 8.85 (1H, dd), 8.72 (1H, d), 8.68 (1H, dd), 8.31 (1H, d), 7.69 ( 1H, dd), 4.36 (3H, s), 3.72-3.61 (1H, m), 3.17-3.06 (1H, m), 1.47 (3H, t).
This condensed heterocyclic compound 8

¹ H-NMR (CDCl ₃ ) δ: 9.00 (1H, dd), 8.72 (1H, d), 8.55 (1H, dd), 8.30 (1H, d), 7.73 ( 1H, dd), 3.89 (3H, s), 3.84 (2H, q), 1.37 (3H, t).

Production Example 9 (1)
To a mixture of 1.9 g 5-iodo-N2-methyl-pyridine-2,3-diamine and 6 mL pyridine, add 1.28 g EDCI hydrochloride, 86 mg HOBt and 1.3 g 3-chloro-pyridine-2-carboxylic acid, Stir at room temperature for 9 hours. Water was poured into this reaction mixture, and the precipitated powder was collected by filtration and washed with chloroform to give 3-chloro-pyridin-2-carboxylic acid (5-iodo-2-methylamino-pyridin-3-yl). ) -Amide (hereinafter sometimes referred to as intermediate compound (M20-7)) 3.6 g was obtained.
Intermediate compound (M20-7)

¹ H-NMR (DMSO-D ₆ ) δ: 9.95 (1H, s), 8.65 (1H, d), 8.15-8.10 (2H, m), 8.00 (1H, d ), 7.65 (1H, dd), 6.30 (1H, d), 2.81 (3H, d).

Production Example 9 (2)
A mixture of intermediate compound (M20-7) 3.4 g, p-toluenesulfonic acid monohydrate 5.8 g, DMF 30 mL, toluene 120 mL was heated and stirred at 130 ° C. for 12 hours. After allowing to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-chloro-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as intermediate compound ( M6-7))) 2.0 g was obtained.
Intermediate compound (M6-7)

¹ H-NMR (CDCl ₃ ) δ: 8.70 (1H, d), 8.66-8.63 (1H, m), 8.47-8.44 (1H, m), 7.95 (1H , D), 7.45 (1H, dd), 3.90 (3H, s).

Production Example 9 (3)
A mixture of 2.0 g of the intermediate compound (M6-7), 888 mg of sodium ethanethiolate and 45 mL of DMF was heated and stirred at 50 ° C. for 12 hours. After allowing to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2- (3-ethylsulfanyl-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as this condensed complex). (It may be referred to as ring compound 9.) 1.0 g was obtained.
This condensed heterocyclic compound 9

¹ H-NMR (CDCl ₃ ) δ: 8.61 (1H, d), 8.51 (1H, dd), 8.45 (1H, d), 7.76 (1H, dd), 7.37 ( 1H, dd), 3.96 (3H, s), 2.94 (2H, q), 1.33 (3H, t).

Production Example 10 (1)
3-amino-5-trifluoromethylpyridine-2-thiol 0.45 g, 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid 0.55 g, EDCI hydrochloride 0.67 g, HOBt 31 mg and pyridine 4.5 ml Was stirred at 60 ° C. for 4 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain an intermediate compound (M20-9). Intermediate compound (M20-9)

A mixture of the total amount of the obtained intermediate compound (M20-9), 1.04 g of p-toluenesulfonic acid monohydrate and 3.5 mL of N-methylpyrrolidinone was heated and stirred at 150 ° C. for 2 hours.
Saturated aqueous sodium hydrogen carbonate solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate.
The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2- (3-chloro-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter referred to as “(3-chloro-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine”) And may be referred to as an intermediate compound (M6-9).) 0.29 g was obtained.
Intermediate compound (M6-9)

¹ H-NMR (CDCl ₃ ) δ: 8.94 (1H, d), 8.90 (1H, d), 8.69 (1H, d), 8.19 (1H, d).

Production Example 10 (2)
2- (3-Chloro-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (intermediate compound (M6-3)) The intermediate compound (M6-9) was used instead of 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -6- () according to the method described in Production Example 4 (2). Trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 10) was obtained.
The present condensed heterocyclic compound 10

¹ H-NMR (CDCl ₃ ) δ: 8.91 (1H, d), 8.70-8.67 (2H, m), 7.91 (1H, s), 3.09 (2H, q), 1.51 (3H, t).

Production Example 11
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine was used according to the method described in Preparation Example 5. 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 11). There is.)
This condensed heterocyclic compound 11

¹ H-NMR (CDCl ₃ ) δ: 9.19 (1H, d), 8.98 (1H, d), 8.89 (1H, d), 8.61 (1H, d), 4.17 ( 2H, q), 1.49 (3H, t).

Production Example 12 (1)
A mixture of 0.45 g 3-amino-5-trifluoromethylpyridine-2-thiol, 0.39 g 3-chloropyridine-2-carboxylic acid, 0.67 g EDCI hydrochloride, 31 mg HOBt and 4 ml pyridine was stirred for 12 hours at room temperature. Stir. Water was poured into the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was washed with water and n-hexane and then dried to give 3-chloropyridin-2-carboxylic acid (2-mercapto-5-trifluoromethylpyridin-3-yl) -amide (hereinafter, intermediate compound) (It may be described as (M20-11).) 0.45 g was obtained.
Intermediate compound (M20-11)

Production Example 12 (2)
A mixture of 0.45 g of the intermediate compound (M20-11), 0.70 g of p-toluenesulfonic acid monohydrate and 4 mL of NMP was stirred at 150 ° C. for 2 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 2- (3-chloropyridin-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine (hereinafter referred to as intermediate compound (M6)). -11))) 0.47 g was obtained.
Intermediate compound (M6-11)

Production Example 12 (3)
Intermediate compound instead of 2- (3-fluoropyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (intermediate compound (M6-2)) (M6-11) and 2- (3-ethylsulfanyl-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine according to the method described in Production Example 1 (2) (Hereinafter may be referred to as the present condensed heterocyclic compound 41).
The present condensed heterocyclic compound 41

¹ H-NMR (CDCl ₃ ) δ: 8.87 (1H, d), 8.64 (1 H, d), 8.48 (1 H, dd), 7.76 (1 H, dd), 7.37 ( 1H, dd), 3.06 (2H, q), 1.49 (3H, t).

Production Example 12 (4)
To a mixture of 2- (3-ethylsulfanyl-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine 0.35 g and chloroform 5 ml, m-chloroperbenzoic acid (purity 65% or more ) 0.56 g was added and stirred at room temperature for 12 hours. A 10% aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 2- (3-ethylsulfonyl-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine ( Hereinafter, this may be referred to as the present condensed heterocyclic compound 12.) 0.27 g and 2- (3-ethylsulfonyl-2-yl) -6- (trifluoromethyl) thiazolo [5,4-b] pyridine 4 91 mg of oxide (hereinafter sometimes referred to as the present condensed heterocyclic compound 22) was obtained.
This condensed heterocyclic compound 12

¹ H-NMR (CDCl ₃ ) δ: 8.98-8.93 (2H, m), 8.66 (1H, dd), 8.57 (1H, d), 7.69 (1H, dd), 4.13 (2H, q), 1.45 (3H, t).
The present condensed heterocyclic compound 22

¹ H-NMR (CDCl ₃ ) δ: 8.96 (1H, dd), 8.68 (1H, dd), 8.62 (1H, s), 8.20 (1H, s), 7.74 ( 1H, dd), 4.06 (2H, q), 1.44 (3H, t).

Production Example 13 (1)
2- (3-Ethylsulfanyl-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine 1.1 g, copper iodide 160 mg, sodium sulfide nonahydrate 2 A mixture of 0.7 g and 10 mL of DMF was stirred at 110 ° C. for 5 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography.

710 mg (hereinafter sometimes referred to as intermediate compound (P9′-1)) was obtained.
Intermediate compound (P9′-1)
¹ H-NMR (DMSO-D ₆ ) δ: 8.56-8.55 (2H, m), 8.53-8.50 (2H, m), 8.38-8.36 (2H, m) , 8.04 (2H, d), 7.61-7.56 (2H, m), 3.87 (6H, brs), 3.00 (4H, q), 1.23-1.16 (6H) , M).

Production Example 13 (2)
A mixture of 710 mg of the intermediate compound (P9′-1) and 12 mL of DMF was cooled to −60 ° C., and 10 g of trifluoroiodomethane was added. To this mixture, 1.2 mL of tetrakis (dimethylamino) ethylene was added dropwise at -40 ° C. It heated up to -10 degreeC and stirred at -10 degreeC for 5 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter, This may be referred to as the present condensed heterocyclic compound 13.) 530 mg was obtained.
This condensed heterocyclic compound 13

¹ H-NMR (CDCl ₃ ) δ: 8.67 (1H, d), 8.52 (1H, dd), 8.46 (1H, d), 7.79 (1H, dd), 7.39 ( 1H, dd), 4.03 (3H, s), 2.97 (2H, q), 1.36 (3H, t).

Production Examples 14 and 15
2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (present condensed heterocyclic compound 13) 200 mg, m-chloro A mixture of perbenzoic acid (purity 65% or more) 230 mg and chloroform 10 mL was stirred for 5 hours under ice cooling. Saturated aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfinyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter, It may be described as the present condensed heterocyclic compound 14.
) 89 mg and 2- (3-ethylsulfonyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as the present condensed heterocyclic compound 15) In some cases, 130 mg was obtained.
The present condensed heterocyclic compound 14

¹ H-NMR (CDCl ₃ ) δ: 8.87-8.83 (1H, m), 8.73-8.64 (2H, m), 8.41 (1H, d), 7.72-7 .66 (1H, m), 4.34 (3H, s), 3.72-3.62 (1H, m), 3.17-3.05 (1H, m), 1.47 (3H, t ).
This condensed heterocyclic compound 15

¹ H-NMR (CDCl ₃ ) δ: 9.01-8.98 (1H, m), 8.71 (1H, d), 8.55-8.52 (1H, m), 8.39 (1H , D), 7.72 (1H, dd), 3.90-3.81 (5H, m), 1.36 (3H, t).

Production Example 16
270 mg of 2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (present condensed heterocyclic compound 13), sodium tungstate To a mixture of 110 mg of dihydrate and 5 mL of acetonitrile, 2 mL of 30% aqueous hydrogen peroxide was added at 40 ° C. The temperature was raised to 80 ° C. and stirred for 24 hours. A saturated aqueous sodium thiosulfate solution was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfonyl-3H-imidazo [4,5-b] pyridine (hereinafter, This may be referred to as the present condensed heterocyclic compound 16.) 280 mg was obtained.
The present condensed heterocyclic compound 16

¹ H-NMR (CDCl ₃ ) δ: 9.08 (1H, d), 9.04 (1H, dd), 8.71 (1H, d), 8.57 (1H, dd), 7.79 ( 1H, dd), 3.93 (3H, s), 3.82 (2H, q), 1.38 (3H, t).

Production Example 17 (1)
A mixture of 590 mg N2-methyl-5-pentafluoroethyl-pyridine-2,3-diamine, 560 mg 3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid, 520 mg EDCI hydrochloride, 35 mg HOBt, 5 mL pyridine, Stir at room temperature for 5 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain an intermediate compound (M20-17).
Intermediate compound (M20-17)

The obtained intermediate compound (M20-17) was dissolved in a mixed solvent of 7.5 mL of DMF and 30 mL of toluene, 1.5 g of p-toluenesulfonic acid monohydrate was added, and the mixture was stirred at 160 ° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with t-butyl methyl ether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b]. It may be described as pyridine (hereinafter referred to as intermediate compound (M6-17)).
) 540 mg was obtained.
Intermediate compound (M6-17)

¹ H-NMR (CDCl ₃ ) δ: 8.96 (1H, d), 8.74 (1H, d), 8.40
(1H, d), 8.23 (1H, d), 4.03 (3H, s).

Production Example 17 (2)
Instead of 2- (3-fluoropyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (intermediate compound (M6-2)), an intermediate Using compound (M6-17), 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-penta according to the method described in Production Example 1 (2) Fluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 17) was obtained.
The present condensed heterocyclic compound 17

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, d), 8.71 (1H, d), 8.42 (1H, d), 7.93 (1H, d), 4.12 ( 3H, s), 3.03 (2H, q), 1.41 (3H, t).

Production Examples 18 and 19
Instead of 2- (3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 1), 2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine, the method according to Preparation Examples 2 and 3 2- (3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as this) And may be referred to as fused heterocyclic compound 18.) and 2- (3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H Imidazo [4,5-b] pyridine (hereinafter, may be referred to as present condensed heterocyclic compound 19.) Was obtained.
The present condensed heterocyclic compound 18

¹ H-NMR (CDCl ₃ ) δ: 9.10 (1H, d), 8.94 (1H, d), 8.76 (1H, d), 8.36 (1H, d), 4.41 ( 3H, s), 3.76-3.66 (1H, m), 3.18-3.07 (1H, m), 1.49 (3H, t).
The present condensed heterocyclic compound 19

¹ H-NMR (CDCl ₃ ) δ: 9.27 (1H, d), 8.80 (1H, d), 8.76 (1H, s), 8.34 (1H, s), 4.01- 3.94 (5H, m), 1.41 (3H, t).

Production Example 20
To a mixture of 2- (3-ethylsulfonyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (500 mg) and chloroform (10 mL) was added m- 429 mg of chloroperbenzoic acid (purity 65% or more) was added, and the mixture was stirred at room temperature for 1 hour and at 50 ° C. for 2 hours. A sodium thiosulfate aqueous solution and a sodium hydrogen carbonate aqueous solution were poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfinyl-3H-imidazo [4,5-b] pyridine (hereinafter, This may be referred to as the present condensed heterocyclic compound 20.) 353 mg was obtained.
The present condensed heterocyclic compound 20

¹ H-NMR (CDCl ₃ ) δ: 9.02 (1H, dd), 8.77 (1H, d), 8.60-8.52 (2H, m), 7.75 (1H, dd), 3.91 (3H, s), 3.83 (2H, q), 1.38 (3H, t).

Production Example 21 (1)
To a mixture of 2.0 g of 4-iodo-2-nitro-phenylamine, 330 mg of 60% sodium hydride (oil) and 20 mL of DMF, 470 μL of iodomethane was added dropwise under ice cooling. The reaction mixture was warmed to room temperature and stirred for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.0 g of (4-iodo-2-nitro-phenyl) -methyl-amine.

Production Example 21 (2)
A mixture of 1.7 g of iron powder, 2.2 mL of acetic acid, 80 mL of ethanol, and 25 mL of water was stirred at 70 ° C. A mixture of (4-iodo-2-nitro-phenyl) -methyl-amine (2.0 g) and ethanol (20 mL) was added dropwise to the reaction mixture. After dropping, the mixture was stirred at 70 ° C. for 6 hours.
The reaction mixture was filtered and washed with THF. The obtained filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was poured into the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.6 g of 4-iodo-N1-methyl-benzene-1,2-diamine.

Production Example 21 (3)
A mixture of 4-iodo-N1-methyl-benzene-1,2-diamine 850 mg, 3-chloro-pyridine-2-carboxylic acid 590 mg, EDCI hydrochloride 790 mg, HOBt 46 mg, and pyridine 10 mL was stirred at 100 ° C. for 12 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. When the residue is subjected to silica gel column chromatography and described as 2- (3-chloro-pyridin-2-yl) -5-iodo-1-methyl-1H-benzimidazole (hereinafter referred to as intermediate compound (M6-21)) 930 mg was obtained.
Intermediate compound (M6-21)

Production Example 21 (4)
Instead of 2- (3-fluoropyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (intermediate compound (M6-2)), an intermediate Using compound (M6-21), 2- (3-ethylsulfanyl-pyridin-2-yl) -5-iodo-1-methyl-1H-benzimidazole (in accordance with the method described in Production Example 1 (2)) Hereinafter, this may be referred to as the present condensed heterocyclic compound 21).
This condensed heterocyclic compound 21

¹ H-NMR (CDCl ₃ ) δ: 8.49 (1H, dd), 8.22 (1H, d), 7.75 (1H, d), 7.62 (1H, dd), 7.35 ( 1H, dd), 7.21 (1H, d), 3.87 (3H, s), 2.92 (2H, q), 1.32 (3H, t).

Production Example 22 (1)
A mixture of 5.2 g of 4-aminophenylsulfur pentafluoride, 2.7 mL of acetic anhydride, 6.6 mL of triethylamine and 20 mL of chloroform was stirred at room temperature for 3 hours.
Water was poured into the reaction mixture, and the mixture was extracted with chloroform. The obtained residue was recrystallized using hexane and ethyl acetate to obtain 5.4 g of 4-acetamidophenylsulfur pentafluoride.

Production Example 22 (2)
To a mixture of 5.4 g of 4-acetamidophenylsulfur pentafluoride and 15 mL of sulfuric acid, 905 mL of fuming nitric acid was added dropwise under ice cooling. After dropping, the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice, and the precipitated crystals were collected by filtration. The crystals were washed with water and dried to obtain 5.2 g of 4-amino-3-nitrophenylsulfur pentafluoride.

Production Example 22 (3)
To a mixture of 2.0 g of 4-amino-3-nitrophenylsulfur pentafluoride, 310 mg of 60% sodium hydride (oil) and 15 mL of DMF, 447 μL of iodomethane was added dropwise under ice cooling. After dropping, the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and the precipitated solid was collected by filtration. The solid was washed with water and dried to obtain 2.0 g of methyl- (2-nitro-4-pentafluorosulfanyl-phenyl) -amine.

¹ H-NMR (CDCl ₃ ) δ: 8.60 (1H, d), 8.28 (1H, brs), 7.78 (1H, dd), 6.89 (1H, d), 3.10 ( 3H, d).

Production Example 22 (4)
Instead of (4-iodo-2-nitro-phenyl) -methyl-amine, methyl- (2-nitro-4-pentafluorosulfanyl-phenyl) -amine was used, and the method described in Production Example 21 (2) was used. Accordingly, N1-methyl-4-pentafluorosulfanyl-benzene-1,2-diamine was obtained.

Production Example 22 (5)
Instead of 5-iodo-N2-methyl-pyridine-2,3-diamine, N1-methyl-4-pentafluorosulfanyl-benzene-1,2-diamine was used and the method described in Production Example 9 (1) was used. Accordingly, 3-chloro-pyridine-2-carboxylic acid (2-methylamino-5-pentafluorosulfanyl-phenyl) -amide (hereinafter sometimes referred to as intermediate compound (M20-23)) was obtained. .
Intermediate compound (M20-23)

¹ H-NMR (CDCl ₃ ) δ: 9.57 (1H, s), 8.55 (1H, dd), 7.91 (1H, dd), 7.81 (1H, d), 7.59 ( 1H, dd), 7.50-7.45 (1H, m), 6.71 (1H, d), 4.52 (1H, d), 2.93 (3H, d).

Production Example 22 (6)
To a mixture of 405 mg of the intermediate compound (M20-23) and 10 ml of DMF, 193 mg of sodium ethanethiolate was added under ice cooling, and the mixture was stirred at room temperature for 8 hours and at 60 ° C. for 2 hours.
Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -1-methyl-5-pentafluorosulfanyl-1H-benzimidazole (hereinafter referred to as “(2-ethyl-3-sulfanyl-5-trifluoromethyl-pyridin-2-yl) -1”). , Sometimes referred to as the present condensed heterocyclic compound 23.) 411 mg was obtained.
The present condensed heterocyclic compound 23

¹ H-NMR (CDCl ₃ ) δ: 8.50 (1H, dd), 8.33 (1H, d), 7.79-7.74 (2H, m), 7.46-7.43 (1H M), 7.37 (1H, dd), 3.92 (3H, s), 2.94 (2H, q), 1.33 (3H, t).

Production Example 23
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanyl-pyridin-2-yl) -1-methyl-5-pentafluorosulfanyl-1H-benzimidazole was used according to the method described in Production Example 11 and 2- (3 -Ethylsulfonyl-pyridin-2-yl) -1-methyl-5-pentafluorosulfanyl-1H-benzimidazole (hereinafter may be referred to as the present condensed heterocyclic compound 24) was obtained.
The present condensed heterocyclic compound 24

¹ H-NMR (CDCl ₃ ) δ: 8.96 (1H, dd), 8.50 (1H, dd), 8.24 (1H, d), 7.79 (1H, dd), 7.68 ( 1H, dd), 7.48 (1H, d), 3.82 (2H, q), 3.75 (3H, s), 1.34 (3H, t).

Production Example 24 (1)
In place of 3-chloro-pyridine-2-carboxylic acid, 3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid was used, and 3-chloro- 5-trifluoromethyl-pyridine-2-carboxylic acid (5-iodo-2-methylamino-pyridin-3-yl) -amide (hereinafter sometimes referred to as intermediate compound (M20-35)) is obtained. It was.
Intermediate compound (M20-35)

¹ H-NMR (CDCl ₃ ) δ: 9.33 (1H, s), 8.80 (1H, d), 8.28 (1H, d), 8.17 (1H, d), 8.00 ( 1H, d), 4.60 (1H, s),
3.01 (3H, d).

Production Example 24 (2)
Instead of 3-chloro-pyridine-2-carboxylic acid (5-iodo-2-methylamino-pyridin-3-yl) -amide (intermediate compound (M20-7)), intermediate compound (M20-35) In accordance with the method described in Production Example 9 (2), 2- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4 5-b] pyridine (hereinafter, intermediate compound (M6-35) was obtained.
Intermediate compound (M6-35)

¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, s), 8.68 (1H, s), 8.49 (1H, s), 8.20 (1H, s), 3.95 ( 3H, s).

Production Example 24 (3)
Instead of 2- (3-fluoropyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (intermediate compound (M6-2)), an intermediate Using compound (M6-35), 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -6-iodo-3-methyl according to the method described in Production Example 1 (2) -3H-imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 42) was obtained.
The present condensed heterocyclic compound 42

¹ H-NMR (CDCl ₃ ) δ: 8.73 (1H, s), 8.65 (1H, d), 8.49 (1H, d), 7.91 (1H, s), 4.04 ( 3H, s), 3.01 (2H, q),
1.39 (3H, t).

Production Example 24 (4)
2- (3-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -6-iodo-3-methyl-3H-imidazo [4,5-b] pyridine 900 mg, thiobenzoic acid 320 μL, copper iodide A mixture of 45 mg, 1,10-phenanthroline 85 mg, diisopropylethylamine 940 μL, and toluene 25 mL was stirred at 110 ° C. for 8 hours.
Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and thiobenzoic acid S- [2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-3H-imidazo [4,5-b 990 mg of pyridine] ester were obtained.

¹ H-NMR (CDCl ₃ ) δ: 8.74 (1H, s), 8.54 (1H, d), 8.33 (1H, d), 8.07 (2H, dd), 7.92 ( 1H, s), 7.63 (1H, t), 7.51 (2H, t), 4.10 (3H, s), 3.01 (2H, q), 1.39 (3H, t).

Production Example 24 (5)
1.8 g of thiobenzoic acid S- [2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-3H-imidazo [4,5-b] pyridine] ester, potassium carbonate A mixture of 1.1 g and 20 mL of methanol was stirred at room temperature for 4.5 hours.
Saturated aqueous ammonium chloride solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, and concentrated under reduced pressure to give 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl- 1.2 g of 3H-imidazo [4,5-b] pyridine-6-thiol (hereinafter sometimes referred to as the present condensed heterocyclic compound 43) was obtained.
The present condensed heterocyclic compound 43

¹ H-NMR (CDCl ₃ ) δ: 8.73 (1H, s), 8.46 (1H, d), 8.19 (1H, d), 7.90 (1H, s), 4.04 ( 3H, s), 3.01 (2H, q), 1.39 (3H, t).

Production Example 24 (6)
2- (3-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-3H-imidazo [4,5-b] pyridine-6-thiol 1.2 g, iodine 20 mg, DMF 30 mL mixture Was stirred in an air atmosphere at room temperature for 12 hours. The reaction mixture is concentrated, and the residue is subjected to silica gel column chromatography.

800 mg (hereinafter sometimes referred to as intermediate compound (P9′-4)) was obtained.
Intermediate compound (P9'-4)
¹ H-NMR (CDCl ₃ ) δ: 8.73 (2H, s), 8.52 (2H, d), 8.35 (2H, d), 7.91 (2H, d), 4.06 ( 6H, s), 3.04-2.98 (4H, m), 1.39 (6H, t).

Production Example 24 (7)
Instead of the intermediate compound (P9′-1), the intermediate compound (P9′-4) was used and 2- (3-ethylsulfanyl-5-trifluoro) was prepared according to the method described in Preparation Example 13 (2). Methyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 28) was obtained. .
The present condensed heterocyclic compound 28

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, d), 8.71 (1H, d), 8.50 (1H, d), 7.93 (1H, d), 4.10 ( 3H, s), 3.03 (2H, q), 1.41 (3H, t).

Production Example 24 (8)
To a mixture of 299 mg 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine and 30 mL chloroform Then, 0.34 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, and the mixture was stirred for 5 hours under ice cooling. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with chloroform.
The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4 , 5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 44) 0.24 g was obtained.
The present condensed heterocyclic compound 44

¹ H-NMR (CDCl ₃ ) δ: 9.24 (1H, d), 8.79 (1H, d), 8.74 (1H, d), 8.40 (1H, d), 3.97 ( 2H, q), 3.93 (3H, s), 1.42 (3H, t).
Production Example 24 (9)
Instead of 2- (3-ethylsulfanyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine (present condensed heterocyclic compound 13), 2 Using-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine, According to the method, 2- (3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-trifluoromethylsulfonyl-3H-imidazo [4,5-b] pyridine (hereinafter May be referred to as the present condensed heterocyclic compound 25).
This condensed heterocyclic compound 25

¹ H-NMR (CDCl ₃ ) δ: 9.28 (1H, d), 9.10 (1H, d), 8.80 (1H, d), 8.72 (1H, d), 3.98 ( 3H, s), 3.93 (2H, q), 1.43 (3H, t).

Production Example 25
A mixture of 340 mg 2- (3-ethylsulfanyl-pyridin-2-yl) -5-iodo-1-methyl-1H-benzimidazole, 410 mg copper iodide, 800 mg sodium pentafluoropropionate, 5 mL NMP, 5 mL xylene, Stir at 5 ° C. for 5 hours. The reaction mixture was allowed to cool to room temperature, saturated aqueous sodium hydrogen carbonate solution and 28% ammonia solution were added, and the mixture was extracted with t-butyl methyl ether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-pyridin-2-yl) -1-methyl-5-pentafluoroethyl-1H-benzimidazole (hereinafter referred to as the present condensed heterocyclic compound 26). In some cases) 240 mg was obtained.
The present condensed heterocyclic compound 26

¹ H-NMR (CDCl ₃ ) δ: 8.50 (1H, dd), 8.16 (1H, s), 7.77 (1H, dd), 7.57 (1H, d), 7.53 ( 1H, d), 7.36 (1H, dd), 3.93 (3H, s), 2.94 (2H, q), 1.33 (3H, t).

Production Example 26
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanyl-pyridin-2-yl) -1-methyl-5-pentafluoroethyl-1H-benzimidazole was used according to the method described in Production Example 5, and 2- (3 -Ethylsulfonyl-pyridin-2-yl) -1-methyl-5-pentafluoroethyl-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 27) was obtained.
This condensed heterocyclic compound 27

¹ H-NMR (CDCl ₃ ) δ: 8.98 (1H, dd), 8.53 (1H, dd), 8.06 (1H, s), 7.70 (1H, dd), 7.60 ( 1H, d), 7.56 (1H, d), 3.86-3.78 (5H, m), 1.34 (3H, t).

Production Example 27
Mixture of 0.18 g 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4,5-b] pyridine and 4 ml chloroform To the solution, 0.21 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, and the mixture was stirred for 5 minutes under ice cooling. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo [4 0.16 g of 5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 29) was obtained.
This condensed heterocyclic compound 29

¹ H-NMR (CDCl ₃ ) δ: 9.10-9.07 (1H, m), 8.94-8.91 (1H, m), 8.77-8.74 (1H, m), 8 .46-8.44 (1H, m), 4.38 (3H, s), 3.76-3.65 (1H, m), 3.16-3.05 (1H, m), 1.49 (3H, t).

Production Example 28 (1)
Instead of 5-iodo-N2-methyl-pyridine-2,3-diamine, N1-methyl-4-trifluoromethyl-benzene-1,2-diamine was used, and the method described in Production Example 9 (1) was used. Accordingly, 3-chloro-pyridine-2-carboxylic acid (2-methylamino-5-trifluoromethyl-phenyl) -amide (hereinafter sometimes referred to as intermediate compound (M20-29)) was obtained. .
Intermediate compound (M20-29)

¹ H-NMR (CDCl ₃ ) δ: 9.56 (1H, s), 8.55-8.54 (1H, m), 7.91 (1H, dd), 7.70 (1H, d), 7.49-7.43 (3H, m), 6.79 (1H, d), 2.93 (3H, d).

Production Example 28 (2)
A mixture of 800 mg of the intermediate compound (M20-29), 350 mg of sodium ethanethiolate and 10 mL of DMF was stirred at 100 ° C. for 5 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-pyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as the present condensed heterocyclic compound 30). 410 mg was obtained.
This condensed heterocyclic compound 30

¹ H-NMR (CDCl ₃ ) δ: 8.51 (1H, dd), 8.17 (1H, d), 7.78 (1H, dd), 7.61 (1H, dd), 7.52 ( 1H, d), 7.38 (1H, dd), 3.93 (3H, s), 2.94 (2H, q), 1.33 (3H, t).

Production Examples 29 and 30
Instead of 2- (3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (3-ethylsulfanyl-pyridine-2 2- (3-Ethylsulfinyl-pyridin-2-yl) -1 using -yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole according to the methods described in Preparation Examples 2 and 3 -Methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 31) and 2- (3-ethylsulfonyl-pyridine-2-)
Yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter may be referred to as the present condensed heterocyclic compound 32).
This condensed heterocyclic compound 31

¹ H-NMR (CDCl ₃ ) δ: 8.77 (1H, d), 8.61 (1H, d), 8.05 (1H, s), 7.61 (1H, dd), 7.55 ( 1H, d), 7.48 (1H, d), 4.20 (3H, s), 3.73-3.61 (1H, m), 3.11-3.00 (1H, m), 1 .47 (3H, t).
The present condensed heterocyclic compound 32

¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, dd), 8.50 (1H, dd), 8.09 (1H, d), 7.66 (1H, dd), 7.61 ( 1H, d), 7.53 (1H, d), 3.83 (2H, q), 3.75 (3H, s), 1.33 (3H, t).

Production Example 31 (1)
Instead of 5-iodo-N2-methyl-pyridine-2,3-diamine, N1-methyl-4-trifluoromethyl-benzene-1,2-diamine was used to give 3-chloro-pyridine-2-carboxylic acid. Instead, 3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid was used according to the method described in Production Example 9 (1) using 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid. An acid (2-methylamino-5-trifluoromethyl-phenyl) -amide (hereinafter sometimes referred to as intermediate compound (M20-31)) was obtained.
Intermediate compound (M20-31)

¹ H-NMR (CDCl ₃ ) δ: 9.42 (1H, s), 8.80 (1H, d), 8.16 (1H, d), 7.71 (1H, s), 7.47 ( 1H, d), 6.81 (1H, d), 4.32 (1H, s), 2.93 (3H, d).

Production Example 31 (2)
Instead of 3-chloro-pyridine-2-carboxylic acid (2-methylamino-5-trifluoromethyl-phenyl) -amide (intermediate compound (M20-29)), intermediate compound (M20-31) was used. According to the method described in Production Example 28 (2), 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole ( Hereinafter, this may be referred to as the present condensed heterocyclic compound 33.) and 3-ethylsulfanyl-5-trifluoromethyl-pyridine-2-carboxylic acid (2-methylamino-5-trifluoromethyl-phenyl) -amide ( Hereinafter, it may be referred to as an intermediate compound (M3-32)).
This condensed heterocyclic compound 33

¹ H-NMR (CDCl ₃ ) δ: 8.72 (1H, d), 8.21 (1H, d), 7.91 (1H, d), 7.63 (1H, d), 7.54 ( 1H, d), 4.00 (3H, s), 3.00 (2H, q), 1.38 (3H, t).
Intermediate compound (M3-32)

¹ H-NMR (CDCl ₃ ) δ: 9.64 (1H, s), 8.53 (1H, d), 7.86 (1H, s), 7.76 (1H, d), 7.41 ( 1H, dd), 6.76 (1H, d), 4.35 (1H, d), 2.96 (2H, q), 2.90 (3H, d), 1.44 (3H, t).

Production Examples 32 and 33
Instead of 2- (3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 1), 2- ( 3-Ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole and 2- ( 3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 34) and 2 -(3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, present May be referred to as case heterocyclic compound 35.) Was obtained.
The present condensed heterocyclic compound 34

¹ H-NMR (CDCl ₃ ) δ: 9.05 (1H, d), 8.91 (1H, d), 8.12 (1H, d), 7.67 (1H, dd), 7.60 ( 1H, d), 4.32 (3H, s), 3.80-3.70 (1H, m), 3.15-3.05 (1H, m), 1.51 (3H, t).
This condensed heterocyclic compound 35

¹ H-NMR (CDCl ₃ ) δ: 9.22 (1H, d), 8.77 (1H, d), 8.10 (1H, d), 7.66 (1H, dd), 7.57 ( 1H, d), 3.98 (2H, q), 3.84 (3H, s), 1.40 (3H, t).

Production Examples 34 and 35
To a mixture of 550 mg of 2- (3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine and 15 ml of chloroform was added m-chloroperbenzoic acid (purity). 750 mg (65% or more) was added, and the mixture was heated to reflux for 20 hours. A 10% aqueous sodium thiosulfate solution was poured into the reaction mixture, and the mixture was extracted with chloroform.
The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-1-oxypyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b. 168 mg of pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 36), and 2- (3-ethylsulfonylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4 , 5-b] pyridine 4-oxide (hereinafter sometimes referred to as the present condensed heterocyclic compound 37) (73 mg) was obtained.
The present condensed heterocyclic compound 36

¹ H-NMR (CDCl ₃ ) δ: 8.79 (1H, d), 8.54 (1H, dd), 8.33 (1H, d), 7.99 (1H, dd), 7.69 ( 1H, dd), 3.85-3.74 (4H, m), 3.52-3.42 (1H, m), 1.34 (3H, t).
The present condensed heterocyclic compound 37

¹ H-NMR (CDCl ₃ ) δ: 9.03 (1H, dd), 8.53 (1H, dd), 8.47 (1H, d), 7.92 (1H, d), 7.77 ( 1H, dd), 4.29 (3H, s), 3.69 (2H, q), 1.36 (3H, t).

Production Example 36 (1)
Instead of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 4-iodo-N1-methyl-benzene-1,2-diamine was used according to the method described in Production Example 4 (1). 2- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -5-iodo-1-methyl-1H-benzimidazole (hereinafter referred to as intermediate compound (M6-41)). )
Intermediate compound (M6-41)

¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, d), 8.23 (1H, d), 8.17 (1H, d), 7.66 (1H, dd), 7.23 ( 1H, d), 3.85 (3H, s).

Production Example 36 (2)
Prepared by using intermediate compound (M6-41) instead of 2- (3-fluoropyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine. In accordance with the method described in Example 1 (2), 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -5-iodo-1-methyl-1H-benzimidazole (hereinafter referred to as the present) May be referred to as a condensed heterocyclic compound 45).
This condensed heterocyclic compound 45

Production Example 36 (3)
Instead of 2- (3-ethylsulfanyl-pyridin-2-yl) -5-iodo-1-methyl-1H-benzimidazole, 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -5-Iodo-1-methyl-1H-benzimidazole and according to the method described in Preparation Example 25, 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl) -1- Methyl-5-pentafluoroethyl-1H-benzimidazole (hereinafter may be referred to as the present condensed heterocyclic compound 38) was obtained.
The present condensed heterocyclic compound 38

¹ H-NMR (CDCl ₃ ) δ: 8.72 (1H, d), 8.20 (1H, s), 7.91 (1H, d), 7.60 (1H, d), 7.55 ( 1H, d), 4.00 (3H, s), 3.01 (2H, q), 1.39 (3H, t).

Production Examples 37 and 38
Instead of 2- (3-ethylsulfanylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine, 2- (3-ethylsulfanyl-5-tri According to the method described in Preparation Examples 2 and 3, 2- (3-ethylsulfinyl-5-trimethyl) was used using fluoromethyl-pyridin-2-yl) -1-methyl-5-pentafluoroethyl-1H-benzimidazole. Fluoromethyl-pyridin-2-yl) -1-methyl-5-pentafluoroethyl-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 39) and 2- (3-ethylsulfonyl-5) -Trifluoromethyl-pyridin-2-yl) -1-methyl-5-pentafluoroethyl-1H-benzimidazole (hereinafter, this condensed heterocyclic compound 4) May be referred to as.) Was obtained.
The present condensed heterocyclic compound 39
¹ H-NMR (CDCl ₃ ) δ: 9.05 (1H, d), 8.91 (1H, d), 8.10 (1H, s), 7.66-7.60 (2H, m), 4.33 (3H, s), 3.80-3.69 (1H, m), 3.17-3.07 (1H, m), 1.50 (3H, t).
The present condensed heterocyclic compound 40

¹ H-NMR (CDCl ₃ ) δ: 9.22 (1H, d), 8.77 (1H, d), 8.08 (1H, s), 7.63 (1H, d), 7.58 ( 1H, d), 3.99 (2H, q), 3.84 (3H, s), 1.40 (3H, t).

Production Example 39 (1)
15 g of N-bromosuccinimide was added to a mixture of 16 g of methyl- (2-nitro-4-trifluoromethyl-phenyl) -amine and 200 mL of acetonitrile under ice cooling. The reaction mixture was stirred at room temperature for 5 hours. Saturated aqueous sodium hydrogen carbonate solution was poured into the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 15 g of (2-bromo-6-nitro-4-trifluoromethyl-phenyl) -methyl-amine.
(2-Bromo-6-nitro-4-trifluoromethyl-phenyl) -methyl-amine

¹ H-NMR (CDCl ₃ ) δ: 8.12 (1H, s), 7.86 (1H, s), 6.48 (1H, brs), 3.07 (3H, d).

Production Example 39 (2)
To a mixture of 11 g of iron powder, 12 mL of acetic acid, 40 mL of THF, and 10 mL of water, a mixture of 10 g of 2-bromo-6-nitro-4-trifluoromethyl-phenyl) -methyl-amine and 50 mL of THF was added dropwise at 70 ° C. with stirring. . After dropping, the mixture was heated and stirred at 70 ° C. for 3 hours. The resulting reaction mixture was filtered through Celite (registered trademark) and washed with THF. The obtained filtrate was concentrated under reduced pressure. A 10% aqueous sodium hydroxide solution was poured into the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 11 g of 3-bromo-N2-methyl-5-trifluoromethyl-benzene-1,2-diamine.
3-Bromo-N2-methyl-5-trifluoromethyl-benzene-1,2-diamine

Production Example 39 (3)
Instead of 5-iodo-N2-methyl-pyridine-2,3-diamine, 3-bromo-N2-methyl-5-trifluoromethyl-benzene-1,2-diamine was used, and Production Example 9 (1) was used. According to the method described, 3-chloro-pyridine-2-carboxylic acid (3-bromo-2-methylamino-5-trifluoromethyl-phenyl) -amide (hereinafter referred to as intermediate compound (M20-43)) There is a case.)
Intermediate compound (M20-43)

¹ H-NMR (CDCl ₃ ) δ: 10.63 (1H, s), 8.77 (1H, d), 8.58 (1H, dd), 7.91 (1H, dd), 7.56 ( 1H, d), 7.47 (1H, dd), 3.75-3.68 (1H, m), 2.83 (3H, d).

Production Example 39 (4)
In place of the intermediate compound (M20-29), the intermediate compound (M20-43) was used and 2- (3-ethylsulfanyl-pyridin-2-yl) was prepared according to the method described in Production Example 28 (2). -7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 75), 3-ethylsulfanyl-pyridine-2-carboxylic acid (3- Bromo-2-methylamino-5-trifluoromethyl-phenyl) -amide (hereinafter sometimes referred to as intermediate compound (M3-42)) and 2- (3-chloro-pyridin-2-yl)- 7-Bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter sometimes referred to as intermediate compound (M6-43)) was obtained.
This condensed heterocyclic compound 75

¹ H-NMR (CDCl ₃ ) δ: 8.54 (1H, dd), 8.08 (1H, d), 7.79 (1H, dd), 7.72 (1H, d), 7.40 ( 1H, dd), 4.13 (3H, s), 2.94 (2H, q), 1.32 (3H, t).
Intermediate compound (M3-42)

¹ H-NMR (CDCl ₃ ) δ: 10.80 (1H, s), 8.82 (1H, s), 8.38 (1H, dd), 7.74 (1H, d), 7.54 ( 1H, s), 7.42 (1H, dd), 3.75-3.65 (1H, brm), 2.97 (2H, q), 2.82 (3H, d), 1.45 (3H , T).
Intermediate compound (M6-43)

¹ H-NMR (CDCl ₃ ) δ: 8.71 (1H, dd), 8.08 (1H, d), 7.95 (1H, dd), 7.74 (1H, d), 7.47 ( 1H, dd), 4.09 (3H, s).

Production Example 40
2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanyl-pyridin-2-yl) -7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole was used according to the method described in Preparation Example 2, and 2- (3-Ethylsulfonyl-pyridin-2-yl) -7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter may be referred to as the present condensed heterocyclic compound 46) was obtained. .
The present condensed heterocyclic compound 46

¹ H-NMR (CDCl ₃ ) δ: 8.99 (1H, dd), 8.51 (1H, dd), 8.00 (1H, d), 7.75 (1H, d), 7.72 ( 1H, dd), 4.03 (3H, s), 3.73 (2H, q), 1.33 (3H, t).

Production Examples 41 and 42
2- (3-Ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (present condensed heterocyclic compound 4) 1 A mixture of 0.0 g, 2.72 g of m-chloroperbenzoic acid (purity 65% or more) and 5 ml of chloroform was refluxed for 8 hours, and 2.0 g of m-chloroperbenzoic acid (purity 65% or more) was added. Refluxed for 5 hours. A 10% aqueous sodium thiosulfate solution was poured into the cooled reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6- 362 mg of trifluoromethyl-3H-imidazo [4,5-b] pyridine 4-oxide (hereinafter sometimes referred to as the present condensed heterocyclic compound 48), and 2- (3-ethylsulfonyl-1-oxy-5) -Trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 51) 45 mg Obtained.
The present condensed heterocyclic compound 48

¹ H-NMR (CDCl ₃ ) δ: 9.27 (1H, d), 8.76 (1H, d), 8.49 (1H, d), 7.94 (1H, d), 4.33 ( 3H, s), 3.80 (2H, q), 1.40 (3H, t).
This condensed heterocyclic compound 51

¹ H-NMR (CDCl ₃ ) δ: 8.75 (1H, s), 8.50 (1H, s), 8.12 (1H, s), 7.94 (1H, s), 4.28 ( 3H, s), 3.75-3.65 (1H, m), 3.55-3.44 (1H, m), 1.38 (3H, t).

Production Example 43 (1)
2.60 g of 2-chloro-3-nitro-5-trifluoromethylpyridine, 0.79 g of 2,2,2-trifluoroethylamine, 1.04 g of N, N-diisopropylethylamine and 5 ml of N-methyl-2-pyrrolidone The mixture was stirred at room temperature for 10 hours. A 10% aqueous citric acid solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain 1.83 g of (3-nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl) amine. Got.
(3-Nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl) amine

¹ H-NMR (CDCl ₃ ) δ: 8.72 (1H, d), 8.68 (1H, d), 8.59 (1H, brs), 4.54-4.41 (2H, m).

Production Example 43 (2)
To a mixture of iron powder 2.12 g, ethanol 6 ml, water 4 ml and acetic acid 0.1 ml, (3-nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl) amine 1 A mixture of .83 g and 10 ml of ethanol was added dropwise at 70 ° C., followed by stirring at 70 ° C. for 1 hour. The reaction mixture allowed to cool was filtered, and the filtrate was extracted with ethyl acetate and water. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain 1.59 g of N2- (2,2,2-trifluoroethyl) -5-trifluoromethylpyridine-2,3-diamine. .
N2- (2,2,2-trifluoroethyl) -5-trifluoromethylpyridine-2,3-diamine

¹ H-NMR (CDCl ₃ ) δ: 8.04-8.02 (1H, m), 7.10-7.07 (1H, m), 4.81 (1H, brs), 4.31-4 .20 (2H, m), 3.34 (2H, brs).

Production Example 43 (3)
N2- (2,2,2-trifluoroethyl) -5-trifluoromethylpyridine-2,3-diamine 0.52 g, 3-ethylsulfanylpyridine-2-carboxylic acid 0.37 g, EDCI hydrochloride 0.46 g , HOBt 27 mg and pyridine 2 ml were stirred at room temperature for 3 hours. A 10% aqueous citric acid solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, concentrated under reduced pressure, and 3-ethylsulfanylpyridine-2-carboxylic acid [2- (2,2,2-trifluoroethyl) amino-5-trifluoromethylpyridine. 0.75 g of -3-yl] amide (hereinafter sometimes referred to as intermediate compound (M3-43)) was obtained.
Intermediate compound (M3-43)

Production Example 43 (4)
A mixture of 0.75 g of the intermediate compound (M3-43) and 5 ml of acetic acid was stirred for 2 days with heating under reflux. After cooling to room temperature, the mixture was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfanylpyridin-2-yl) -3- (2,2,2-trifluoroethyl) -6-trifluoromethyl-3H-imidazo [ 4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 65) 0.53 g was obtained.
This condensed heterocyclic compound 65

¹ H-NMR (CDCl ₃ ) δ: 8.77-8.74 (1H, m), 8.48 (1H, dd), 8.45-8.42 (1H, m), 7.82 (1H , Dd), 7.40 (1H, dd), 5.64 (2H, q), 2.99 (2H, q), 1.35 (3H, t).

Production Example 44 (1)
N2- (2,2,2-trifluoroethyl) -5-trifluoromethylpyridine-2,3-diamine 0.52 g, 3-ethylsulfanyl-5-trifluoromethylpyridine-2-carboxylic acid 0.50 g, A mixture of 0.46 g EDCI hydrochloride, 27 mg HOBt and 2 ml pyridine was stirred at room temperature for 3 hours. A 10% aqueous citric acid solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, concentrated under reduced pressure, and 3-ethylsulfanyl-5-trifluoromethylpyridine-2-carboxylic acid [2- (2,2,2-trifluoroethyl) amino- 0.89 g of 5-trifluoromethylpyridin-3-yl] amide (hereinafter sometimes referred to as intermediate compound (M3-44)) was obtained.
Intermediate compound (M3-44)

Production Example 44 (2)
A mixture of 0.89 g of the intermediate compound (M3-44), 1.14 g of p-toluenesulfonic acid monohydrate, 10 ml of N-methyl-2-pyrrolidone and 10 ml of xylene was dehydrated using a Dean-Stark apparatus. The mixture was heated to reflux for 8 hours. The reaction mixture was allowed to cool, water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3- (2,2,2-trifluoroethyl) -6-trifluoro. 0.76 g of methyl-3H-imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 66) was obtained.
The present condensed heterocyclic compound 66

¹ H-NMR (CDCl ₃ ) δ: 8.80 (1H, d), 8.70 (1H, d), 8.48 (1H, d), 7.96 (1H, d), 5.67 ( 2H, q), 3.04 (2H, q),
1.40 (3H, t).

Production Example 45
To a mixture of 0.32 g of this condensed heterocyclic compound 65 and 2 ml of chloroform, 0.36 g of m-chloroperbenzoic acid (purity 65% or more) is added under ice cooling, and then the temperature is raised to room temperature and stirred for 1 hour. did. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfonylpyridin-2-yl) -3- (2,2,2-trifluoroethyl) -6-trifluoromethyl-3H-imidazo [ There was obtained 0.32 g of 4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 67).
The present condensed heterocyclic compound 67

¹ H-NMR (CDCl ₃ ) δ: 8.98 (1H, dd), 8.80 (1H, d), 8.59 (1H, dd), 8.37 (1H, d), 7.75 ( 1H, dd), 5.31 (2H, q), 3.95 (2H, q), 1.40 (3H, t).

Production Example 46
To a mixture of 0.32 g of this condensed heterocyclic compound 66 and 2 ml of chloroform, 0.31 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, and then the mixture was warmed to room temperature and stirred for 1 hour. did. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crude product was washed with hexane to give 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -3- (2,2,2-trifluoroethyl) -6-trifluoro. 0.28 g of methyl-3H-imidazo [4,5-b] pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 68) was obtained.
The present condensed heterocyclic compound 68

¹ H-NMR (CDCl ₃ ) δ: 9.22 (1H, d), 8.83-8.83 (2H, m), 8.40 (1H, d), 5.36 (2H, q), 4.05 (2H, q), 1.45 (3H, t).

Production Example 47 (1)
A mixture of 20.0 g of 2-chloro-5-iodopyridine, 77.8 g of sodium pentafluoropropionate, 31.8 g of copper (I) iodide, 84 ml of xylene and 84 ml of N-methylpyrrolidone was heated to 160 ° C. and heated. The mixture was stirred for 6 hours under reflux. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain 2-chloro-5-pentafluoroethylpyridine.
2-chloro-5-pentafluoroethylpyridine

¹ H-NMR (CDCl ₃ ) δ: 8.65-8.62 (1H, m), 7.85-7.81 (1H, m), 7.48-7.44 (1H, m)

Production Example 47 (2)
Half amount of 2-chloro-5-pentafluoroethylpyridine obtained in Production Example 47 (1), 14.4 g of zinc (II) cyanide, 2.42 g of tetrakistriphenylphosphine palladium and 84 ml of N-methylpyrrolidone The mixture was heated to 80 ° C. and stirred with heating for 2.5 hours. After the reaction mixture was cooled to room temperature, water and methyl-tert-butyl ether were added, the precipitate was filtered through Celite (registered trademark), and the residue was washed with methyl-tert-butyl ether. The filtrate was extracted with methyl-tert-butyl ether, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to obtain 4.19 g of 2-cyano-5-pentafluoroethylpyridine.
2-Cyano-5-pentafluoroethylpyridine

¹ H-NMR (CDCl ₃ ) δ: 8.97-8.96 (1H, m), 8.12-8.09 (1H, m), 7.90-7.87 (1H, m)

Production Example 47 (3)
A mixture of 17 ml of water and 17 ml of concentrated sulfuric acid was heated to 100 ° C., and 3.81 g of 2-cyano-5-pentafluoroethylpyridine was added dropwise with heating, followed by stirring at 100 ° C. for 2.5 hours. After cooling to room temperature, the reaction mixture was poured into ice water. The precipitated solid was filtered and washed with water. The obtained solid was dried under reduced pressure to obtain 3.52 g of 5-pentafluoropyridine-2-carboxylic acid.
5-pentafluoropyridine-2-carboxylic acid

¹ H-NMR (CDCl ₃ ) δ: 8.92-8.88 (1H, m), 8.44-8.39 (1H, m), 8.25-8.20 (1H, m)

Production Example 47 (4)
A mixture of 5.5 ml of tetramethylpiperidine and 58 ml of THF was cooled to −78 ° C., 1.6 M n-butyllithium hexane solution was added dropwise, and the mixture was warmed to room temperature and stirred for 10 minutes. The mixture was cooled again to −78 ° C., a THF solution of 3.52 g of 5-pentafluoropyridine-2-carboxylic acid was added dropwise, and the mixture was stirred at −78 ° C. for 1 hour. After dropwise addition of 4.0 ml of diethyl disulfide at −78 ° C., the mixture was warmed to room temperature and stirred for 1 hour. After adding 1N hydrochloric acid to the reaction mixture, 5N aqueous sodium hydroxide solution was added, and the aqueous layer was washed with methyl-tert-butyl ether. 12N hydrochloric acid was poured into the aqueous layer, and the precipitated solid was filtered and then dissolved in methyl-tert-butyl ether. After drying with sodium sulfate, the mixture was concentrated under reduced pressure, and 1.99 g of 3-ethylsulfanyl-5-pentafluoroethylpyridine-2-carboxylic acid (hereinafter sometimes referred to as intermediate compound (M2-7)). Got.
Intermediate compound (M2-7)

¹ H-NMR (CDCl ₃ ) δ: 8.51-8.50 (1H, m), 7.89-7.87 (1H, m), 3.01 (2H, q), 1.46 (3H , T)

Production Example 47 (5)
A mixture of 0.50 g N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.79 g intermediate compound (M2-7), 0.37 g EDCI hydrochloride, 35 mg HOBt and 5 ml pyridine at room temperature Stir for hours. Water was poured into the reaction mixture, and the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 3-ethylsulfanyl-5-pentafluoroethylpyridine-2-carboxylic acid (2-methylamino-5-trifluoromethylpyridin-3-yl) amide. (Hereinafter, it may be referred to as intermediate compound (M3-45)).
Intermediate compound (M3-45)

¹ H-NMR (CDCl ₃ ) δ: 9.57 (1H, brs), 8.54-8.52 (1H, m), 8.37-8.35 (1H, m), 7.94-7 .92 (1H, m), 7.89-7.87 (1H, m), 4.97 (1H, brs), 3.08 (3H, d), 2.99 (2H, q), 1. 45 (3H, t)
A mixture of the total amount of the obtained intermediate compound (M3-45) and 5 ml of acetic acid was heated to 120 ° C. and stirred for 3 hours while heating under reflux. After cooling to room temperature, the mixture was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-pentafluoroethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5- b] 0.77 g of pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 71) was obtained.
The present condensed heterocyclic compound 71

¹ H-NMR (CDCl ₃ ) δ: 8.78-8.76 (1H, m), 8.71-8.69 (1H, m), 8.44-8.42 (1H, m), 7 .91-7.89 (1H, m), 4.13 (3H, s), 3.02 (2H, q), 1.39 (3H, t)

Production Example 48
To a mixture of 0.47 g of this condensed heterocyclic compound 71 and 10 ml of chloroform, 0.57 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, and then the mixture was warmed to room temperature and stirred for 1 hour. . Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure.
The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-pentafluoroethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5- b] 0.39 g of pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 72) was obtained.
The present condensed heterocyclic compound 72

¹ H-NMR (CDCl ₃ ) δ: 9.21-9.19 (1H, m), 8.81-8.79 (1H, m), 8.76-8.75 (1H, m), 8 .35-8.33 (1H, m), 3.99-3.93 (5H, m), 1.41 (3H, t)

Production Example 49
A mixture of N2-methyl-5-pentafluoroethylpyridine-2,3-diamine 0.50 g, intermediate compound (M2-7) 0.62 g, EDCI hydrochloride 0.29 g, HOBt 28 mg and pyridine 4 ml Stir for hours. Water was poured into the reaction mixture, and the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 3-ethylsulfanyl-5-pentafluoroethylpyridine-2-carboxylic acid (2-methylamino-5-pentafluoroethylpyridin-3-yl) amide. (Hereinafter, it may be referred to as an intermediate compound (M3-46)).
Intermediate compound (M3-46)

¹ H-NMR (CDCl ₃ ) δ: 9.59 (1H, brs), 8.54-8.52 (1H, m), 8.32-8.30 (1H, m), 7.89-7 .87 (1H, m), 7.85-7.83 (1H, m), 5.04 (1H, brs), 3.09 (3H, d), 2.99 (2H, q), 1. 45 (3H, t)
A mixture of the total amount of the obtained intermediate compound (M3-46) and 4 ml of acetic acid was heated to 120 ° C. and stirred for 3 hours while heating under reflux. After cooling to room temperature, the mixture was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-pentafluoroethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5- b] 0.84 g of pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 73) was obtained.
This condensed heterocyclic compound 73

¹ H-NMR (CDCl ₃ ) δ: 8.72-8.69 (2H, m), 8.42-8.41 (1H, m), 7.90-7.89 (1H, m), 4 .15-4.12 (3H, m), 3.02 (2H, q), 1.40 (3H, t)

Production Example 50
To a mixture of 0.54 g of this condensed heterocyclic compound 73 and 11 ml of chloroform, 0.59 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, and then the mixture was warmed to room temperature and stirred for 1 hour. . Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and concentrated under reduced pressure.
The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-pentafluoroethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5- b] 0.34 g of pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 74) was obtained.
The present condensed heterocyclic compound 74

¹ H-NMR (CDCl ₃ ) δ: 9.21-9.20 (1H, m), 8.77-8.74 (2H, m), 8.32-8.31 (1H, m), 4 .00-3.94 (5H, m), 1.41 (3H, t)

Production Example 51
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanylpyridin-2-yl) -1-methyl-5-trifluoromethoxy-1H-benzimidazole was used and 2- (3-ethylsulfonyl) was prepared according to the method described in Preparation Example 5. Pyridin-2-yl) -1-methyl-5-trifluoromethoxy-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 50) was obtained.
This condensed heterocyclic compound 50

¹ H-NMR (CDCl ₃ ) δ: 8.93 (1H, dd), 8.49 (1H, dd), 7.68-7.62 (2H, m), 7.43 (1H, d), 7.25 (1H, d), 3.84 (2H, q), 3.73 (3H, s), 1.31 (3H, q).

Production Example 52
2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanylpyridin-2-yl) -5-trifluoromethyl-benzthiazole was used and 2- (3-ethylsulfonylpyridin-2-yl) was prepared according to the method described in Production Example 5. -5-trifluoromethyl-benzthiazole (hereinafter may be referred to as the present condensed heterocyclic compound 53) was obtained.
This condensed heterocyclic compound 53

¹ H-NMR (CDCl ₃ ) δ: 8.92 (1H, dd), 8.65 (1H, dd), 8.37 (1H, s), 8.11 (1H, d), 7.72 ( 1H, dd), 7.66 (1H, dd), 4.19 (2H, q), 1.45 (3H, t).

Production Example 53
2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanylpyridin-2-yl) -6-trifluoromethyl-oxazolo [5,4-b] pyridine was used and 2- (3-ethyl) was prepared according to the method described in Preparation Example 5. Sulfonylpyridin-2-yl) -6-trifluoromethyl-oxazolo [5,4-b] pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 81) was obtained.
This condensed heterocyclic compound 81

¹ H-NMR (CDCl ₃ ) δ: 9.06 (1H, dd), 8.79 (1H, d), 8.58 (1H, dd), 8.43 (1H, d), 7.78 ( 1H, dd), 3.88 (2H, q), 1.44 (3H, t).

Production Example 54
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanylpyridin-2-yl) -5-trifluoromethyl-benzoxazole was used and 2- (3-ethylsulfonylpyridin-2-yl) was prepared according to the method described in Production Example 5. -5-trifluoromethyl-benzoxazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 85) was obtained.
The present condensed heterocyclic compound 85

¹ H-NMR (CDCl ₃ ) δ: 9.03 (1H, dd), 8.60 (1H, dd), 8.16-8.13 (1H, m), 7.82-7.71 (3H M), 4.01 (2H, q), 1.43 (3H, t).

Production Example 55
Under ice-cooling, this condensed heterocyclic compound 48 (0.20 g) was added to 2.04 g of phosphorus oxychloride, and the mixture was stirred at 110 ° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, poured into a saturated aqueous sodium hydrogencarbonate solution under ice cooling, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 5-chloro-2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo. 0.21 g of [4,5-b] pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 89) was obtained.
This condensed heterocyclic compound 89

¹ H-NMR (CDCl ₃ ) δ: 9.25 (1H, d), 8.78 (1H, d), 8.43 (1H, s), 3.97-3.87 (5H, m), 1.41 (3H, t).

Production Example 56
0.3 ml of dimethylamine (methanol solution, 2.0 mol / L) was added to a mixture of this condensed heterocyclic compound 89 (0.20 g) and 0.5 ml of NMP, and the mixture was stirred at room temperature for 1 hour and at 50 ° C. for 3 hours. To the reaction mixture allowed to cool to room temperature, 0.3 ml of dimethylamine (methanol solution, 2.0 mol / L) was added and stirred at 50 ° C. for 3 hours. Water was poured into the reaction mixture allowed to cool to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 5-dimethylamino-2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H- 0.03 g of imidazo [4,5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 99) was obtained.
This condensed heterocyclic compound 99

¹ H-NMR (CDCl ₃ ) δ: 9.20 (1H, d), 8.76 (1H, d), 8.26 (1H, s), 4.02 (2H, q), 3.84 ( 3H, s), 3.04 (6H, s), 1.41 (3H, t).

Production Example 57
2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead of 7-cyano-2- (3-ethylsulfanylpyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole, 7-cyano was prepared according to the method described in Preparation Example 5. 2- (3-Ethylsulfonylpyridin-2-yl) -1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 130) was obtained.
The present condensed heterocyclic compound 130

¹ H-NMR (CDCl ₃ ) δ: 9.02 (1H, dd), 8.54 (1H, dd), 8.28 (1H, s), 7.95 (1H, s), 7.77 ( 1H, dd), 4.06 (3H, s), 3.74 (2H, q), 1.35 (3H, t).

Production Example 58
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead of 2- (5-chloro-3-ethylsulfanylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine, the method according to Preparation Example 5 2- (5-chloro-3-ethylsulfonylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter referred to as this condensed heterocyclic ring) Compound 312 may be indicated.).
This condensed heterocyclic compound 312

¹ H-NMR (CDCl ₃ ) δ: 8.95 (1H, d), 8.72-8.71 (1H, m), 8.53 (1H, d), 8.30-8.28 (1H , M), 3.94-3.87 (5H, m), 1.40 (3H, t)

To a mixture of this condensed heterocyclic compound 48 (0.30 g), 0.14 ml of triethylamine and 1 ml of acetonitrile, 0.35 ml of trimethylsilylcyanide was added and stirred at 110 ° C. for 3 hours. Water was poured into the reaction mixture allowed to cool to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 5-cyano-2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo. 0.23 g of [4,5-b] pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 399) was obtained.
This condensed heterocyclic compound 399

¹ H-NMR (CDCl ₃ ) δ: 9.28 (1H, d), 8.79 (1H, d), 8.48 (1H, s), 3.96 (3H, s), 3.89 ( 2H, q), 1.42 (3H, t).

Production Example 60
To a mixture of 2- (3-ethylsulfanylpyridin-2-yl) -1-methyl-7-methylsulfanyl-5-trifluoromethyl-1H-benzimidazole and 5 ml of chloroform was added m-chloro under ice cooling. After adding 0.32 g of perbenzoic acid (purity 65% or more), the mixture was stirred at room temperature for 5 hours. The reaction mixture was ice-cooled, 0.32 g of m-chloroperbenzoic acid (purity 65% or more) was added, and the mixture was stirred at room temperature for 3 hours. A 10% aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture, and the mixture was extracted with chloroform.
The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 2- (3-ethylsulfonylpyridin-2-yl) -1-methyl-7-methylsulfonyl-5-trifluoromethyl-1H. -0.62 g of benzimidazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 404) was obtained.
This condensed heterocyclic compound 404

¹ H-NMR (CDCl ₃ ) δ: 9.08-8.97 (1H, m), 8.58-8.46 (1H, m), 8.41-8.26 (2H, m), 7 84-7.70 (1H, m), 4.12 (3H, s), 3.72-3.59 (2H, m), 3.33 (3H, s), 1.39-1.22 (3H, m).

Production Example 61
To a mixture of the present condensed heterocyclic compound 19 (2.0 g) and chloroform (20 ml), m-chloroperbenzoic acid (purity 65% or more) (3.03 g) was added under ice-cooling, and the mixture was stirred with heating under reflux for 3 hours. The reaction mixture was ice-cooled, m-chloroperbenzoic acid (purity 65% or more) (3.03 g) was added, and the mixture was stirred for 3 hours with heating under reflux. The reaction mixture was ice-cooled, m-chloroperbenzoic acid (purity 65% or more) (3.03 g) was added, and the mixture was stirred for 3 hours with heating under reflux. A 10% aqueous sodium thiosulfate solution and a saturated aqueous sodium hydrogen carbonate solution were added to the reaction mixture regulated to room temperature, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2- (3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl. 1.10 g of -3H-imidazo [4,5-b] pyridine 4-oxide (hereinafter sometimes referred to as the present condensed heterocyclic compound 409) was obtained.
This condensed heterocyclic compound 409

¹ H-NMR (CDCl ₃ ) δ: 9.27 (1H, d), 8.77 (1H, d), 8.45 (1H, s), 7.92 (1H, s), 4.34 ( 3H, s), 3.81 (2H, q), 1.40 (3H, t).

Production Example 62
To a mixture of this condensed heterocyclic compound 19 (0.65 g), 6 ml of methanol, 6 ml of THF and 2 ml of water, 0.54 g of sodium hydroxide was added, and the mixture was stirred for 1 day with heating under reflux. Water was poured into the reaction mixture allowed to cool to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-trimethoxymethyl-pyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4 0.25 g of 5-b] pyridine (hereinafter sometimes referred to as the present condensed heterocyclic compound 414) was obtained.
This condensed heterocyclic compound 414

¹ H-NMR (CDCl ₃ ) δ: 9.16 (1H, d), 8.74 (1H, d), 8.70 (1H, d), 8.31 (1H, d), 3.93 ( 3H, s), 3.88 (2H, q), 3.28 (9H, s), 1.38 (3H, t).

Production Example 63
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead of 2- (3-methylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine, described in Production Example 5 In accordance with the method of 2- (3-methylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter, This may be referred to as this condensed heterocyclic compound 419).
The present condensed heterocyclic compound 419

¹ H-NMR (CDCl ₃ ) δ: 9.25 (1H, s), 8.85 (1H, s), 8.75 (1H, s), 8.32 (1H, s), 3.96 ( 3H, s), 3.73 (3H, s)

Production Example 64
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead of 2- (3-propylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine, described in Production Example 5 According to the method of 2- (3-propylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter, This may be referred to as this condensed heterocyclic compound 421).
The present condensed heterocyclic compound 421

¹ H-NMR (CDCl ₃ ) δ: 9.24 (1H, s), 8.79 (1H, s), 8.74 (1H, s), 8.31 (1H, s), 3.95- 3.88 (5H, m), 1.92-1.81 (2H, m), 1.13 (3H, t)

Production Example 65
2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead of 2- (3-isopropylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine, described in Production Example 5 According to the method of 2- (3-isopropylsulfonyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-pentafluoroethyl-3H-imidazo [4,5-b] pyridine (hereinafter, This may be referred to as the present condensed heterocyclic compound 423).
This condensed heterocyclic compound 423

¹ H-NMR (CDCl ₃ ) δ: 9.24 (1H, s), 8.75 (2H, d), 8.31 (1H, s), 4.71-4.60 (1H, m), 3.93 (3H, s), 1.39 (6H, d)

Production Example 66
2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanylpyridin-2-yl) -6-pentafluoroethyl-oxazolo [5,4-b] pyridine was used and 2- (3-ethyl) was prepared according to the method described in Preparation Example 5. Sulfonylpyridin-2-yl) -6-pentafluoroethyl-oxazolo [5,4-b] pyridine (hereinafter may be referred to as the present condensed heterocyclic compound 464) was obtained.
This condensed heterocyclic compound 464

¹ H-NMR (CDCl ₃ ) δ: 9.07 (1H, dd), 8.74 (1H, d), 8.59 (1H, dd), 8.41 (1H, d), 7.80 ( 1H, dd), 3.91 (2H, q), 1.45 (3H, t).

Production Example 67
To 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -3-methyl-6-trifluoromethyl-3H-imidazo [4,5-b] pyridine (this condensed heterocyclic compound 4) Instead, 2- (3-ethylsulfanylpyridin-2-yl) -5-pentafluoroethyl-benzoxazole was used and 2- (3-ethylsulfonylpyridin-2-yl) was prepared according to the method described in Production Example 5. -5-pentafluoroethyl-benzoxazole (hereinafter sometimes referred to as the present condensed heterocyclic compound 467) was obtained.
This condensed heterocyclic compound 467

¹ H-NMR (CDCl ₃ ) δ: 9.04 (1H, dd), 8.61 (1H, dd), 8.12 (1H, d), 7.82 (1H, d), 7.75 ( 1H, dd), 7.72 (1H, dd), 4.04 (2H, q), 1.44 (3H, t).

Production Example 68 (1)
A mixture of 1.0 g 2-amino-4- (trifluoromethylsulfanyl) phenol, 0.87 g 3-ethylsulfanylpicolinic acid, 1.10 g EDCI hydrochloride and 10 ml chloroform was stirred at room temperature for 30 minutes. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.32 g of 3-ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide.
3-ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide

¹ H-NMR (CDCl ₃ ) δ: 10.40 (1H, brs), 9.63 (1H, s), 8.36 (1H, dd), 7.75 (1H, dd), 7.53 ( 1H, d), 7.45 (1H, dd), 7.41 (1H, dd), 7.08 (1H, d), 2.97 (2H, q), 1.44 (3H, t).

Production Example 68 (2)
3-ethylsulfanyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide 1.23 g, di-2-methoxyethyl azodicarboxylate (hereinafter referred to as DMEAD) 1.28 g, tri A mixture of 1.39 g of phenylphosphine and 30 ml of THF was stirred at room temperature for 1 hour and at 50 ° C. for 1 hour. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography, and may be referred to as 2- (3-ethylsulfanylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic compound 441). There was 1.21 g.
This condensed heterocyclic compound 441

¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, dd), 8.27 (1H, s), 7.78 (1H, dd), 7.75-7.69 (2H, m), 7.42 (1H, dd), 3.07 (2H, q), 1.47 (3H, t).

Production Example 69
To a mixture of this condensed heterocyclic compound 441 (1.06 g) and 30 ml of chloroform, 1.47 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice-cooling, followed by stirring at room temperature for 6 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform.
The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography, and may be referred to as 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic compound 443). 0.87 g and 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfinyl) benzoxazole (hereinafter may be referred to as the present condensed heterocyclic compound 444) 0.17 g. It was.
This condensed heterocyclic compound 443

¹ H-NMR (CDCl ₃ ) δ: 9.03 (1H, dd), 8.60 (1H, dd), 8.19 (1H, d), 7.80-7.71 (3H, m), 4.02 (2H, q), 1.43 (3H, t).
This condensed heterocyclic compound 444

¹ H-NMR (CDCl ₃ ) δ: 9.04 (1H, dd), 8.61 (1H, dd), 8.35 (1H, d), 7.96-7.86 (2H, m), 7.77 (1H, dd), 4.01 (2H, q), 1.44 (3H, t).

Production Example 70
To a mixture of this condensed heterocyclic compound 443 (0.35 g) and chloroform 8 ml, 0.43 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, followed by stirring at 40 ° C. for 6 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture allowed to cool to room temperature, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue were added 4 ml of acetonitrile, 30 mg of sodium tungstate dihydrate and 4 ml of aqueous hydrogen peroxide (30%), and the mixture was stirred at 80 ° C. for 6 hours. Water was added to the reaction mixture allowed to cool to room temperature, the precipitated solid was collected by filtration, 10% aqueous sodium sulfite solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography, and may be referred to as 2- (3-ethylsulfonylpyridin-2-yl) -5- (trifluoromethylsulfonyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic compound 445). There was 0.35 g.
The present condensed heterocyclic compound 445

¹ H-NMR (CDCl ₃ ) δ: 9.05 (1H, dd), 8.61 (1H, dd), 8.59 (1H, d), 8.17 (1H, dd), 7.96 ( 1H, d), 7.80 (1H, dd), 3.98 (2H, q), 1.45 (3H, t).

Production Example 71 (1)
A mixture of 1.0 g of 2-amino-4- (trifluoromethylsulfanyl) phenol, 1.08 g of 3-chloro-5-trifluoromethylpicolinic acid, 1.10 g of EDCI hydrochloride and 10 ml of chloroform was stirred at room temperature for 1 hour. did. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 3-chloro-5-trifluoromethyl-N- [2-hydroxy- 1.94 g of 5- (trifluoromethylsulfanyl) phenyl] picolinamide was obtained.
3-Chloro-5-trifluoromethyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide

¹ H-NMR (CDCl ₃ ) δ: 8.78 (1H, d), 8.15 (1H, d), 8.09 (1H, d), 7.37 (1H, dd), 7.04 ( 1H, d).

Production Example 71 (2)
To a mixture of 1.93 g of 3-chloro-5-trifluoromethyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide, 6 ml of DMF, 1 ml of THF and 0.38 ml of ethyl mercaptan, 0.62 g of potassium tert-butoxide was added, and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.45 g of 3-ethylsulfanyl-5-trifluoromethyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide.
3-Ethylsulfanyl-5-trifluoromethyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide

¹ H-NMR (CDCl ₃ ) δ: 10.31 (1H, s), 8.96 (1H, brs), 8.58 (1H, d), 7.91 (1H, d), 7.70 ( 1H, d), 7.43 (1H, dd), 7.07 (1H, d), 3.00 (2H, q), 1.47 (3H, t).

Production Example 71 (3)
A mixture of 1.45 g of 3-ethylsulfanyl-5-trifluoromethyl-N- [2-hydroxy-5- (trifluoromethylsulfanyl) phenyl] picolinamide, 1.19 g of DMEAD, 1.29 g of triphenylphosphine and 30 ml of THF, The mixture was stirred at room temperature for 1 hour and at 50 ° C. for 1 hour. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic ring). 1.31 g) was obtained.
The present condensed heterocyclic compound 451

¹ H-NMR (CDCl ₃ ) δ: 8.78 (1H, d), 8.30 (1H, s), 7.94 (1H, d), 7.77-7.75 (2H, m), 3.11 (2H, q), 1.51 (3H, t).

Production Example 72
To a mixture of this condensed heterocyclic compound 451 (1.13 g) and chloroform 25 ml, 0.56 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, followed by stirring at 0 ° C. for 40 minutes. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform.
The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfinyl-5-trifluoromethylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic ring). 1.01 g was obtained.
This condensed heterocyclic compound 452

¹ H-NMR (CDCl ₃ ) δ: 9.13 (1H, d), 8.91 (1H, d), 8.25 (1H, s), 7.85-7.79 (2H, m), 3.60-3.49 (1H, m), 3.13-3.02 (1H, m), 1.44 (3H, t).

Production Example 73
To a mixture of this condensed heterocyclic compound 452 (1.01 g) and 20 ml of chloroform, 0.56 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, followed by stirring at room temperature for 6 hours. Further, 0.20 g of m-chloroperbenzoic acid (purity 65% or more) was added to the reaction mixture, and the mixture was stirred at room temperature for 3 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -5- (trifluoromethylsulfanyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic ring). 0.53 g) (sometimes referred to as compound 453) and 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -5- (trifluoromethylsulfinyl) benzoxazole (hereinafter referred to as the present condensed heterocyclic compound) 0.48 g was obtained.
This condensed heterocyclic compound 453

¹ H-NMR (CDCl ₃ ) δ: 9.25 (1H, d), 8.84 (1 H, d), 8.22 (1 H, d), 7.82 (1 H, dd), 7.77 ( 1H, d), 4.11 (2H, q), 1.47 (3H, t).
The present condensed heterocyclic compound 454

¹ H-NMR (CDCl ₃ ) δ: 9.27 (1H, d), 8.85 (1H, d), 8.39 (1H, s), 7.96 (1H, d), 7.92 ( 1H, d), 4.09 (2H, q), 1.48 (3H, t).

Production Example 74
This condensed heterocyclic compound 454 (0.26 g), 4 ml of acetonitrile, 18 mg of sodium tungstate dihydrate and 3.5 ml of hydrogen peroxide (30%) were added and stirred at 85 ° C. for 5 hours. To the reaction mixture allowed to cool to room temperature, 0.5 ml of hydrogen peroxide (30%) was added and stirred at 85 ° C. for 3 hours. Water was added to the reaction mixture allowed to cool to room temperature, the precipitated solid was collected by filtration, 10% aqueous sodium sulfite solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -5- (trifluoromethylsulfonyl) benzoxazole (hereinafter, this condensed heterocycle). 0.24 g was obtained (may be referred to as Compound 455).
This condensed heterocyclic compound 455

¹ H-NMR (CDCl ₃ ) δ: 9.28 (1H, d), 8.84 (1H, d), 8.62 (1H, d), 8.21 (1H, dd), 8.00 ( 1H, d), 4.05 (2H, q), 1.49 (3H, t).

Production Example 75 (1)
A mixture of 27 ml of tert-butanol and 3.15 g of potassium hydroxide was stirred with heating under reflux for 1 hour, 6.0 g of 2-chloro-5-trifluoromethylsulfanylpyridine and 3 mL of tert-butanol were added with a dropping funnel, and the mixture was heated under reflux. Stir for 5 hours. The reaction mixture was allowed to cool to room temperature, concentrated hydrochloric acid was added, the solid was filtered and washed with ethanol. The obtained filtrate was concentrated under reduced pressure, 1N hydrochloric acid was added, the precipitated solid was collected by filtration, washed with water, washed with hexane, and dried to give 2-hydroxy-5-trifluoromethylsulfanylpyridine. 42 g were obtained.
2-hydroxy-5-trifluoromethylsulfanylpyridine

¹ H-NMR (CDCl ₃ ) δ: 7.73 (1H, d), 7.62 (1H, dd), 6.61 (1H, d).

Production Example 75 (2)
To a mixture of 2 g of 2-hydroxy-5-trifluoromethylsulfanylpyridine and 10 mL of concentrated sulfuric acid, 0.74 mL of fuming nitric acid was added under ice cooling, and the mixture was stirred at 60 ° C. for 2 hours. The reaction mixture was allowed to cool to room temperature, poured into 50 mL of ice water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained solid was washed with tert-butyl methyl ether to obtain 2.13 g of 2-hydroxy-3-nitro-5-trifluoromethylsulfinylpyridine.
2-hydroxy-3-nitro-5-trifluoromethylsulfinylpyridine

¹ H-NMR (DMSO-D ₆ ) δ: 8.67 (1H, brs), 8.59 (1H, brs).

Production Example 75 (3)
A mixture of 4.6 g of iron powder, 0.5 mL of acetic acid, 20 mL of ethanol and 15 mL of water was stirred at 70 ° C., and 2 g of 2-hydroxy-3-nitro-5-trifluoromethylsulfinylpyridine was added thereto. Stir for hours. The reaction mixture was allowed to cool to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained solid was washed with tert-butyl methyl ether to obtain 1.45 g of 3-amino-2-hydroxy-5-trifluoromethylsulfinylpyridine.
3-Amino-2-hydroxy-5-trifluoromethylsulfinylpyridine

¹ H-NMR (DMSO-D ₆ ) δ: 12.23 (1H, brs), 7.49 (1H, s), 6.68 (1H, s), 5.72 (2H, brs).

Production Example 75 (4)
A mixture of 0.63 g of 3-amino-2-hydroxy-5-trifluoromethylsulfinylpyridine, 0.55 g of 3-ethylsulfanylpicolinic acid, 0.68 g of EDCI hydrochloride and 20 ml of pyridine was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration and dried under reduced pressure to obtain 0.73 g of 3-ethylsulfanyl-N- [2-hydroxy-5-trifluoromethylsulfinylpyridin-3-yl] picolinamide.
3-Ethylsulfanyl-N- [2-hydroxy-5-trifluoromethylsulfinylpyridin-3-yl] picolinamide
¹ H-NMR (DMSO-D ₆ ) δ: 10.83 (1H, s), 8.71 (1H, s), 8.48 (1H, dd), 8.09 (1H, d), 7. 98 (1H, d), 7.65 (1 H, dd), 2.99 (2H, q), 1.31 (3H, t).

Production Example 75 (5)
A mixture of 0.67 g of 3-ethylsulfanyl-N- [2-hydroxy-5-trifluoromethylsulfinylpyridin-3-yl] picolinamide, 0.64 g of DMEAD, 0.68 g of triphenylphosphine and 40 ml of THF was added at 50 ° C. Stir for hours. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanylpyridin-2-yl) -6- (trifluoromethylsulfinyl) oxazolo [5,4-b] pyridine (hereinafter referred to as the present condensed complex). 0.59 g was obtained.
This condensed heterocyclic compound 474

¹ H-NMR (CDCl ₃ ) δ: 8.76 (1H, d), 8.70 (1H, d), 8.64 (1H, dd), 7.82 (1H, dd), 7.47 ( 1H, dd), 3.09 (2H, q), 1.47 (3H, t).

Production Example 76
To a mixture of the present condensed heterocyclic compound 474 (0.43 g) and chloroform 30 ml, 0.53 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, followed by stirring at room temperature for 5 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonylpyridin-2-yl) -6- (trifluoromethylsulfinyl) oxazolo [5,4-b] pyridine (hereinafter referred to as this condensed complex). 0.34 g was obtained (may be referred to as ring compound 439).
This condensed heterocyclic compound 439

¹ H-NMR (CDCl ₃ ) δ: 9.08 (1H, dd), 8.80 (1H, d), 8.69 (1H, d), 8.60 (1H, dd), 7.81 ( 1H, dd), 3.91 (2H, q), 1.45 (3H, t).

Production Example 77
The condensed heterocyclic compound 439 (0.17 g), 4 ml of acetonitrile, 14 mg of sodium tungstate dihydrate and 4 ml of hydrogen peroxide (30%) were added, and the mixture was stirred at 80 ° C. for 4 hours. Water was added to the reaction mixture allowed to cool to room temperature, the precipitated solid was collected by filtration, this solid and a 10% aqueous sodium sulfite solution were mixed, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonylpyridin-2-yl) -6- (trifluoromethylsulfonyl) oxazolo [5,4-b] pyridine (hereinafter referred to as this condensed complex). 0.09 g was obtained (may be referred to as ring compound 440).
The present condensed heterocyclic compound 440

¹ H-NMR (CDCl ₃ ) δ: 9.13 (1H, d), 9.09 (1H, dd), 8.79 (1H, d), 8.60 (1H, dd), 7.83 ( 1H, dd), 3.88 (2H, q), 1.46 (3H, t).

Production Example 78 (1)
A mixture of 0.67 g 3-amino-2-hydroxy-5-trifluoromethylsulfinylpyridine, 0.75 g 3-ethylsulfanyl-5-trifluoromethylpicolinic acid, 0.68 g EDCI hydrochloride and 20 ml pyridine is stirred at room temperature. Stir for 1.5 hours. Water was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration and dried under reduced pressure to give 1.28 g of 3-ethylsulfanyl-5-trifluoromethyl-N- [2-hydroxy-5-trifluoromethylsulfinylpyridin-3-yl] picolinamide. Got.
3-Ethylsulfanyl-5-trifluoromethyl-N- [2-hydroxy-5-trifluoromethylsulfinylpyridin-3-yl] picolinamide

¹ H-NMR (CDCl ₃ ) δ: 10.99 (1H, s), 8.90 (1H, s), 8.68 (1H, s), 7.91 (1H, s), 7.81 ( 1H, s), 3.02 (2H, q), 1.48 (3H, t).

Production Example 78 (2)
Mixture of 1.24 g of 3-ethylsulfanyl-5-trifluoromethyl-N- [2-hydroxy-5-trifluoromethylsulfinylpyridin-3-yl] picolinamide, 1.01 g of DMEAD, 1.06 g of triphenylphosphine and 40 ml of THF Was stirred at 50 ° C. for 3 hours. The reaction mixture allowed to cool to room temperature was concentrated under reduced pressure, water was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethylsulfinyl) oxazolo [5,4-b] pyridine. 0.94 g was obtained (hereinafter may be referred to as the present condensed heterocyclic compound 478).
The present condensed heterocyclic compound 478

¹ H-NMR (CDCl ₃ ) δ: 8.83 (1H, d), 8.81 (1H, d), 8.75 (1H, d), 7.97 (1H, d), 3.13 ( 2H, q), 1.51 (3H, t).

Production Example 79
To a mixture of this condensed heterocyclic compound 478 (0.74 g) and 30 ml of chloroform, 0.77 g of m-chloroperbenzoic acid (purity 65% or more) was added under ice cooling, followed by stirring at room temperature for 4 hours. A 10% aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethylsulfinyl) oxazolo [5,4-b] pyridine. 0.75 g was obtained (hereinafter may be referred to as the present condensed heterocyclic compound 449).
This condensed heterocyclic compound 449

¹ H-NMR (CDCl ₃ ) δ: 9.31 (1H, d), 8.84-8.81 (2H, m), 8.73 (1H, d), 3.98 (2H, q), 1.49 (3H, t).

Production Example 80
The condensed heterocyclic compound 449 (0.14 g), 4 ml of acetonitrile, 27 mg of sodium tungstate dihydrate and 4 ml of hydrogen peroxide (30%) were added, and the mixture was stirred at 80 ° C. for 4.5 hours. Water was added to the reaction mixture allowed to cool to room temperature, the precipitated solid was collected by filtration, this solid and a 10% aqueous sodium sulfite solution were mixed, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl) -6- (trifluoromethylsulfonyl) oxazolo [5,4-b] pyridine. 0.21 g was obtained (hereinafter may be referred to as the present condensed heterocyclic compound 450).
The present condensed heterocyclic compound 450

¹ H-NMR (CDCl ₃ ) δ: 9.32 (1H, d), 9.17 (1H, d), 8.85-8.82 (2H, m), 3.95 (2H, q), 1.50 (3H, t).

Production Example 81
After adding 5 mmol of m-chloroperbenzoic acid (purity 65% or more) to a mixture of this condensed heterocyclic compound 440 (1 mmol) and chloroform 10 ml under ice-cooling, the mixture was stirred for 6 hours with heating under reflux, and the reaction mixture was stirred at room temperature. Then, 5 mmol of m-chloroperbenzoic acid (purity 65% or more) is added, and the mixture is stirred for 6 hours with heating under reflux. A 10% aqueous sodium sulfite solution is added to the reaction mixture which is allowed to cool to room temperature, and the mixture is extracted with chloroform. The organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (3-ethylsulfonylpyridin-2-yl) -6- (trifluoromethylsulfonyl) oxazolo [5,4-b] pyridine 4-oxide (hereinafter referred to as “the following”). The condensed heterocyclic compound 456) and 2- (3-ethylsulfonyl-1-oxy-pyridin-2-yl) -6- (trifluoromethylsulfonyl) oxazolo [5,4-b] pyridine ( Hereinafter, this condensed heterocyclic compound 458 may be referred to).
The present condensed heterocyclic compound 456

The present condensed heterocyclic compound 458

The compounds described in the above production examples and the compounds produced by the production methods according to the methods described in the above production examples are shown in the following table.
The compound represented by Formula (1).

In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , A ¹ , A ² , and n represent the combinations described in the following [Table 1] to [Table 20].

Here, the description of “*” in the condensed heterocyclic compounds of the above Tables [Table 1] to [Table 20] means N-oxide. Specifically, it is the following compound.

The present condensed heterocyclic compound 22

The present condensed heterocyclic compound 36

The present condensed heterocyclic compound 37

The present condensed heterocyclic compound 47

The present condensed heterocyclic compound 48

This condensed heterocyclic compound 51

The present condensed heterocyclic compound 70

The present condensed heterocyclic compound 400

The present condensed heterocyclic compound 401

This condensed heterocyclic compound 409

The present condensed heterocyclic compound 410

The present condensed heterocyclic compound 456

This condensed heterocyclic compound 457

The present condensed heterocyclic compound 458

This condensed heterocyclic compound 459

The present condensed heterocyclic compound 460

The present condensed heterocyclic compound 461

(In the above [Table 1] to [Table 20], Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, and tBu represents a tertiary butyl group. IPr represents an isopropyl group, and CycPr represents a cyclopropyl group.)

Hereinafter, formulation examples of the pest control composition of the present invention will be shown. In the following formulation examples, the present insecticidal compounds 1-118 mean the following compounds.

In the above structural formula, Me means a methyl group, and Et means an ethyl group.

Next, formulation examples are shown.
Formulation Example 1
5 parts of any one of the present condensed heterocyclic compounds 1 to 481 and 5 parts of the present insecticidal compound 1 are dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and polyoxyethylene styryl phenyl ether 14 And 6 parts of calcium dodecylbenzenesulfonate are added and mixed to obtain each emulsion.
Formulation Example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 10 parts of any one of the condensed heterocyclic compounds 1 to 481 and the insecticidal compound 2 are mixed. Add 10 parts and mix to obtain each wettable powder.
Formulation Example 3
1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 1 part of the present insecticidal compound 3 are added 1 part of synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay. Mix. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
Formulation Example 4
1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 1 part of the present insecticidal compound 4 are dissolved in an appropriate amount of acetone, to which 5 parts of a synthetic silicon hydroxide-containing fine powder, 0.3 part of PAP, and Fubasami clay 92. Add 7 parts, mix well with stirring, and evaporate and remove acetone to obtain each powder.
Formulation Example 5
35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 5 parts of any one of the present condensed heterocyclic compounds 1-481, 5 parts of the present insecticidal compound 5 and water Each flowable agent is obtained by mixing 55 parts and finely pulverizing with a wet pulverization method.

Formulation Example 6
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 1 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 7
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 2 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 8
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 3 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 9
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 4 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 10
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 5 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 11
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 6 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 12
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 7 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 13
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 8 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 14
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 9 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 15
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 10 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 16
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 11 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 17
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 12 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 18
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 13 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 19
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 14 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 20
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 15 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 21
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 16 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 22
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 17 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 23
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 18 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 24
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 19 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 25
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 20 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 26
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 21 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 27
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 22 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 28
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 23 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 29
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 24 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 30
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 25 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 31
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 26 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 32
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 27 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 33
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 28 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 34
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 29 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 35
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 30 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 36
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 31 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 37
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 32 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 38
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 33 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 39
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 34 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 40
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 35 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 41
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 36 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 42
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 37 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 43
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 38 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 44
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 39 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 45
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 40 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 46
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 41 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 47
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 42 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 48
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 43 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 49
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 44 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 50
0.1 part of any one of the present condensed heterocyclic compounds 1-481 and 0.1 part of the present insecticidal compound 45 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 51
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 46 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 52
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 47 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 53
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 48 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 54
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 49 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 55
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 50 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 56
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 51 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 57
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 52 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 58
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 53 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 59
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 54 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 60
0.1 part of any one of the present condensed heterocyclic compounds 1-481 and 0.1 part of the present insecticidal compound 55 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 61
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 56 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 62
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 57 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 63
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 58 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 64
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 59 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 65
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 60 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 66
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 61 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 67
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 62 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 68
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 63 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 69
0.1 part of any one of the present condensed heterocyclic compounds 1-481 and 0.1 part of the present insecticidal compound 64 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 70
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 65 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 71
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 66 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 72
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 67 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 73
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 68 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 74
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 69 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 75
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 70 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 76
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 71 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 77
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 72 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 78
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 73 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 79
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 74 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 80
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 75 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 81
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 76 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 82
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 77 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 83
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 78 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 84
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 79 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 85
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 80 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 86
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 81 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 87
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 82 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 88
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 83 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 89
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 84 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 90
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 85 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 91
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 86 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 92
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 87 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 93
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 88 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 94
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 89 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 95
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 90 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 96
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 91 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 97
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 92 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 98
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 93 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 99
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 94 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 100
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 95 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 101
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 96 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 102
0.1 part of any one of the present condensed heterocyclic compounds 1-481 and 0.1 part of the present insecticidal compound 97 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 103
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 98 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 104
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 99 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 105
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 100 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 106
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 101 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 107
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 102 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 108
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 103 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 109
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 104 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 110
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 105 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 111
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 106 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 112
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 107 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 113
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 108 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 114
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 109 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 115
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 110 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 116
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 111 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 117
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 112 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 118
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 113 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 119
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 114 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 120
0.1 part of any one of the condensed heterocyclic compounds 1 to 481 and 0.1 part of the insecticidal compound 115 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 121
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 116 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 122
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 117 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.
Formulation Example 123
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 part of the present insecticidal compound 118 are dissolved in a mixed solvent of 5 parts of xylene and 5 parts of trichloroethane, and this is dissolved in 89.8 parts of deodorized kerosene. To obtain each oil.

Formulation Example 124
10 mg of any one of the present condensed heterocyclic compounds 1 to 481 and 10 mg of the present insecticidal compound 36 are dissolved in 0.5 ml of acetone, and this solution is mixed with animal solid feed powder (solid feed powder CE-2 for breeding, Japan Treat to 5g, and mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.
Formulation Example 125
0.1 part of any one of the present condensed heterocyclic compounds 1 to 481, 0.1 part of the present insecticidal compound 11 and 49.8 parts of neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can and equipped with an aerosol valve. Thereafter, 25 parts of dimethyl ether and 25 parts of LPG are filled, shaken, and an oil aerosol is obtained by mounting the actuator.
Formulation Example 126
0.6 part of any one of the present condensed heterocyclic compounds 1 to 481, 0.6 part of the present insecticidal compound 12, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), xylene 5 parts, 3.33 parts of deodorized kerosene and 1 part of an emulsifier {Atmos 300 (registered trademark name of Atmos Chemical)} and 50 parts of distilled water are filled in an aerosol container, and a valve is attached. Then, 40 parts of propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.
Formulation Example 127
A porous ceramic plate having 4.0 × 4.0 cm and a thickness of 1.2 cm obtained by dissolving 0.1 g of any one of the present condensed heterocyclic compounds 1 to 481 and 0.1 g of the present insecticidal compound 13 in 2 ml of propylene glycol. So as to obtain a heating smoke.
Formulation Example 128
Any one of the present condensed heterocyclic compounds 1-481, 3 parts of the present insecticidal compound 14 and ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT WD301, 95 parts by Sumitomo Chemical Co., Ltd. were melt-kneaded with a closed pressure kneader (Moriyama Seisakusho), and the resulting kneaded product was extruded from an extrusion molding machine through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm. obtain.
Formulation Example 129
Any one of the condensed heterocyclic compounds 1 to 481, 2 parts, 3 parts of the insecticidal compound 15 and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product Is extruded through a molding die from an extrusion molding machine to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
Formulation Example 130
Any one of the present condensed heterocyclic compounds 1 to 481 100 mg, the present insecticidal compound 16 100 mg, lactose 68.75 mg, corn starch 237.5 mg, microcrystalline cellulose 43.75 mg, polyvinylpyrrolidone 18.75 mg, sodium carboxymethyl starch 28.75 mg and 2.5 mg of magnesium stearate are mixed and the resulting mixture is compressed to an appropriate size to obtain a tablet.
Formulation Example 131
25 mg of any one of the present condensed heterocyclic compounds 1 to 481, 50 mg of the present insecticidal compound 17, 60 mg of lactose, 25 mg of corn starch, 6 mg of carmellose calcium, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is hardened Capsules are obtained by filling shell gelatin capsules or hydroxypropyl methylcellulose capsules.
Formulation Example 132
Any one of the present condensed heterocyclic compounds 1 to 481 1000 mg, the present insecticidal compound 18 1000 mg, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, VeegumK ( Vanderbilt Co.) 100 mg, fragrance 35 mg, and colorant 500 mg are added with distilled water to a final volume of 100 ml and mixed to obtain a suspension for oral administration.
Formulation Example 133
2% by weight of any one of the condensed heterocyclic compounds 1 to 481 and 3% by weight of the insecticidal compound 52 are dissolved in 5% by weight of polysorbate 85, 3% by weight of benzyl alcohol, and 30% by weight of propylene glycol. A phosphate buffer solution is added so that the pH of the solution becomes 6.0 to 6.5, and then water is added until the final volume is reached to obtain a solution for oral administration.
Formulation Example 134
5% by weight of aluminum distearate is dispersed by heating in 57% by weight of fractionated coconut oil and 3% by weight of polysorbate 85. This is cooled to room temperature and 25% by weight of saccharin in the oil vehicle is dispersed. To this, 5% by weight of any one of the present condensed heterocyclic compounds 1 to 481 and 5% by weight of the present insecticidal compound 56 are distributed to obtain a paste preparation for oral administration.
Formulation Example 135
5% by weight of any one of the present condensed heterocyclic compounds 1 to 481 and 5% by weight of the present insecticidal compound 58 are mixed with 90% by weight of limestone powder to obtain granules for oral administration using a wet granule formation method.
Formulation Example 136
5 parts of any one of the present condensed heterocyclic compounds 1 to 481 and 5 parts of the present insecticidal compound 61 are dissolved in 75 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate are mixed therewith to obtain a spot-on solution. .
Formulation Example 137
10 parts of any one of the present condensed heterocyclic compounds 1 to 481 and 10 parts of the present insecticidal compound 67 are dissolved in 60 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed therewith to prepare a pour-on solution. Get.
Formulation Example 138
0.5 part of any one of the present condensed heterocyclic compounds 1 to 481 and 0.5 part of the present insecticidal compound 68, 60 parts of Nikkor TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine), propylene After adding 20 parts of glycol and sufficiently stirring and mixing until a uniform solution is obtained, 19.0 parts of water is added and further sufficiently stirring and mixing to obtain a shampoo agent of a uniform solution.
Formulation Example 139
Any one of the present condensed heterocyclic compounds 1-481, 0.15% by weight, 0.15% by weight of the present insecticidal compound 69, 95% by weight of animal feed, and dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) And 4.85% by weight of the mixture consisting of) is sufficiently stirred and mixed to obtain an animal feed premix.
Formulation Example 140
3.6 g of any one of the present condensed heterocyclic compounds 1 to 481, 3.6 g of the present insecticidal compound 70, and 92.8 g of Phosco S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C., and suppository. Pour into shape and cool and solidify to obtain a suppository.

Next, the pest control efficacy of the pest control composition of the present invention can be confirmed, for example, by the following test method.

Test example 1
An acetone solution having a predetermined concentration (% w / v) of the present condensed heterocyclic compound and the present insecticidal compound was prepared. After 1 μl of the acetone solution was dropped on the chest abdominal side of adult female German cockroaches (Blatella germanica), the test insects were transferred to a plastic cup having a diameter of about 9 cm and a height of about 4.5 cm and left at 25 ° C. with food and water. did. Seven days later, the life and death of the test insects were observed to determine the death rate. The number of German cockroaches tested was 10 for one test.
The test results are described by listing the combinations of the present condensed heterocyclic compound and the insecticidal compound, the concentration of each compound in the acetone solution, and the death rate of the test insects as follows.

Composition: [Test concentration of each compound (%), mortality (%)], [Test concentration (%) of each compound, mortality (%)].
The present condensed heterocyclic compound 3 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 3 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 4 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 4 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 5 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 5 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 9 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 9 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 15 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 25: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 26: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 27: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 28: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 29: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 30: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 31: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 32: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 33: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 34: [5 + 0.5, 100], [5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 15 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 16 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 16 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 17 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 17 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 18 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 18 + this insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 18 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 19 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 19 + this insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 19 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 25 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 25 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 27 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 25: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 26: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 27: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 28: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 29: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 30: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 31: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 32: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 33: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 34: [5 + 0.5, 100], [2 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 27 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 28 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 28 + this insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 28 + this insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 28 + this insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 28 + this insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 28 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 29 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 29 + this insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 29 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 48 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 25: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 26: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 27: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 28: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 29: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 30: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 31: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 32: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 33: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 34: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 48 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 50 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 50 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 53 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 53 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 71 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 71 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 72 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 72 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 74 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 74 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 81 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 81 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 85 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 85 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 89 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 89 + this insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 89 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 130 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 130 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 399 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The condensed heterocyclic compound 399 + the insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
This condensed heterocyclic compound 399 + this insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 399 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 409 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 409 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 414 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 414 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 419 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 25: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 26: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 27: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 28: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 29: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 30: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 31: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 32: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 33: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 34: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 419 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 421 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 6: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 12: [5 + 1, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 14: [5 + 2, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 15: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 16: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 17: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 18: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 19: [5 + 4, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 421 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 423 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 25: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 26: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 27: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 28: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 29: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 30: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 31: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 32: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 33: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 34: [5 + 0.5, 100], [1 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 423 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 443 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 25: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 26: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 27: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 28: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 29: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 30: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 31: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 32: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 33: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 34: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 443 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 444 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 25: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 26: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 27: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 28: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 29: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 30: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 31: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 32: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 33: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 34: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 444 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 445 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 25: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 26: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 27: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 28: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 29: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 30: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 31: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 32: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 33: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 34: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 445 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The present condensed heterocyclic compound 467 + the present insecticidal compound 1: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 2: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 3: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 4: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 5: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 6: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 7: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 8: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 9: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 10: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 11: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 12: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 13: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 14: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 15: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 16: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 17: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 18: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 19: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 20: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 21: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 22: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 23: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 24: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 25: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 26: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 27: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 28: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 29: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 30: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 31: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 32: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 33: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 34: [5 + 0.5, 100], [4 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 61: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 62: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 63: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 64: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 65: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 66: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 67: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 92: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 104: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 107: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 113: [5 + 0.5, 100], [0.5 + 5, 100].
The present condensed heterocyclic compound 467 + the present insecticidal compound 115: [5 + 0.5, 100], [0.5 + 5, 100].

The pest control composition of the present invention showed a high control effect.

The pest control composition of the present invention can be used to control pests.

Claims

A compound represented by the following formula (1), or an N-oxide thereof,
A pest control composition containing one or more compounds selected from the following group (A).
Formula (1):

[Where:
A 1 represents —NR 7 —, an oxygen atom or a sulfur atom,
A 2 represents a nitrogen atom or = CR 8 - represents,
R 1 represents a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X;
R 2 , R 3 and R 4 are the same or different and are a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, —OR 10 , —S (O) m R 10 , —S (O) 2 NR 10 R 11 , —NR 10 R 11 , —NR 10 CO 2 R 11 , —NR 10 C (O) R 11 , —CO 2 R 10 , —C (O) R 10 , -C (O) NR 10 R 11 , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R 5 and R 6 are the same or different, and may be a C1-C6 alkyl group optionally having one or more atoms or groups selected from group X, —OR 10 , —S (O) m R 10 , — S (O) 2 NR 10 R 11 , —NR 10 R 11 , —NR 10 CO 2 R 11 , —NR 10 C (O) R 11 , —CO 2 R 10 , —C (O) R 10 , —C (O) NR 10 R 11, -OC (O) R 10, -SF 5, a cyano group, a nitro group, a halogen atom or a hydrogen atom (provided that, R 5 and R 6 do not simultaneously represent a hydrogen atom ),
R 7 is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group W, —CO 2 R 10 , —C (O) R 10 , —CH 2 CO 2 R 10 , Represents a C3-C6 cycloalkyl group or a hydrogen atom,
R 8 is a C1-C6 alkyl group optionally having one or more halogen atoms, —OR 10 , —S (O) m R 10 , —NR 10 R 11 , —CO 2 R 10 , —C ( O) represents R 10 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R 10 and R 11 are the same or different and each represents a C1-C6 alkyl group or a hydrogen atom which may have one or more atoms or groups selected from group X (provided that —S (O) m R 10 , when m is 1 or 2, R 10 does not represent a hydrogen atom)
m independently represents 0, 1 or 2, and n represents 0, 1 or 2.
Group X: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl optionally having one or more halogen atoms or one or more C1-C3 alkyl groups A group consisting of a group, a cyano group, a hydroxy group and a halogen atom.
Group W: C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 cycloalkyl group optionally having one or more halogen atoms, hydroxy group, halogen atom and cyano group A group consisting of ]
Group (A):
The group which consists of following subgroup A-1, A-2, A-3, A-4, A-5, and A-6.
Subgroup A-1:
Pyrethrin, allethrin, praretrin, imiprothrin, resmethrin, tetramethrin, phenothrin, ciphenothrin, flumethrin, methfluthrin, transfluthrin, profluthrin, dimefluthrin, empentrin, framethrin, meperfluthrin, 2,3,5,6-tetrafluoro-4- (methoxy Methyl) benzyl = 2,2-dimethyl-3- (2-cyano-1-propenyl) -cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl = 2,2- Dimethyl-3- (3,3,3-trifluoro-1-propenyl) -cyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4-propargylbenzyl = 2,2,3,3-tetramethyl Cyclopropanecarbo Consisting Shireto, the group of compounds.
Subgroup A-2:
Fenitrothion, Dichlorvos, Propoxur, Bistrifluron, Diflubenzuron, Hexaflumuron, Amidoflumet, Chlorfenapyr, Cyromazine, Hydroprene, Metoprene, Metoxiazone, Etoxazole, Piperonyl butoxide and N- (2-Ethylhexyl) -5-norbornene-2,3-di A group of compounds consisting of carboximide.
Subgroup A-3:
A group of compounds consisting of a compound represented by the following formula (2).

[Wherein Cy is a phenyl group which may be substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group which may be substituted with a group selected from groups E1 to E2, group E1 Represents a 3- to 7-membered cycloalkyl group optionally substituted with a group selected from ~ E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3, and Q 1 it is which may be substituted C1 ~ have C4 chain hydrocarbon group with a halogen atom, a halogen atom or a hydrogen atom, Q 2 is unsubstituted or may C1 ~ have C4 chain hydrocarbon group with a halogen atom, -C (= G) Q 4 represents a cyano group, a halogen atom or a hydrogen atom, Q 3 represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom, G represents an oxygen atom or a sulfur atom, Q 4 is substituted with a halogen atom A C1-C4 alkyl group that may be substituted, a C1-C4 alkoxy group that may be substituted with a halogen atom, a C3-C6 alkenyloxy group that may be substituted with a halogen atom, or a halogen atom. Good C3-C6 alkynyloxy group, C1-C4 alkylamino group optionally substituted with a halogen atom, di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, hydroxyl group, amino group, C2 Represents a C5 cyclic amino group or a hydrogen atom, k represents 0 or 1, h represents 0, 1 or 2, and group E1 is a C1 to C6 chain optionally substituted with a group selected from group L wherein the hydrocarbon group, ~ C3 may be substituted with a halogen atom C6 cycloalkyl group, -OQ 5, -SQ 5, -S (= O) Q 5, -S (= O) 2 Q 5, -C (= O ) Represents a group of monovalent groups consisting of Q 6 , —OC (═O) Q 7 , a cyano group, a nitro group, a hydroxyl group and a halogen atom, and Group E2 may be substituted with a group selected from Group L From a good C2-C6 alkanediyl group, a 1,3-butadiene-1,4-diyl group optionally substituted with a group selected from group L, -G-T-G- and -T-G-T- The group E3 represents a group of divalent groups consisting of ═O, ═NO—Q 5 , ═C═CH 2 and ═C (Q 8 ) Q 9 , and T represents a methylene group Or an ethylene group, and Q 5 is a C1-C4 chain hydrocarbon group optionally substituted with a group selected from Group L or a C3-C6 cycloalkyl group optionally substituted with a group selected from Group L the stands, Q 6 is substituted C1 may be ~ C4 alkoxy group a halogen atom, c A C3-C6 alkenyloxy group optionally substituted with a hydrogen atom, a C3-C6 alkynyloxy group optionally substituted with a halogen atom, a C1-C4 alkylamino group optionally substituted with a halogen atom, a halogen atom A di (C1-C4 alkyl) amino group optionally substituted with, a C1-C4 alkyl group optionally substituted with a halogen atom, a hydroxyl group, an amino group, a C2-C5 cyclic amino group or a hydrogen atom, Q 7 is a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, a C3-C6 alkynyloxy group which may be substituted with a halogen atom, C1-C4 alkylamino group optionally substituted with a halogen atom, di (C1-C4) optionally substituted with a halogen atom Alkyl) amino group, a substituted C1 may be ~ C4 alkyl group with a halogen atom, an amino group, a C2 ~ C5 cyclic amino group or a hydrogen atom, Q 8 and Q 9 are the same or different, substituted with a halogen atom Represents a C1-C4 alkoxy group which may be substituted, a C1-C4 chain hydrocarbon group which may be substituted with a halogen atom, a halogen atom or a hydrogen atom, and the group L is substituted with a hydroxyl group or a halogen atom C1-C4 alkoxy group which may be substituted, C3-C6 alkenyloxy group which may be substituted by halogen atom, C3-C6 alkynyloxy group which may be substituted by halogen atom, amino group, substituted by halogen atom An optionally substituted C1-C4 alkylamino group, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C2-C5 cyclic group Amino group, —C (═O) Q 6 , —OC (═O) Q 7
And a group consisting of halogen atoms. ]
Subgroup A-4:
A group of compounds consisting of a compound represented by the following formula (3).

[Wherein, k, h, Q 1 , Q 2 and Q 3 represent the same meaning as described above, and Q 11 may be substituted with a C1-C5 haloalkyl group having at least one fluorine atom or a halogen atom. C3-C5 alkenyl group, C3-C5 alkenyloxy group optionally substituted with a halogen atom, C3-C5 alkynyl group optionally substituted with a halogen atom, or C3-C5 alkynyl optionally substituted with a halogen atom Represents an oxy group, and Q 12 represents a C1-C4 alkyl group which may be substituted with a halogen atom, a C1-C4 alkoxy group which may be substituted with a halogen atom, or a C1-C4 which may be substituted with a halogen atom. Represents an alkylthio group, a halogen atom or a hydrogen atom (provided that C 11 -C 5 alkenyl optionally substituted with a halogen atom) If a group or an optionally substituted C3-C5 alkynyloxy group with a halogen atom, Q 12 is a is C1-C4 or may be an alkyl group or a hydrogen atom substituted with a halogen atom.), Q 13 is A C1-C4 alkyl group, a halogen atom or a hydrogen atom is represented. ]
Subgroup A-5:
A group of compounds consisting of a compound represented by the following formula (4).

[Wherein L 3 represents a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group or a hydrogen atom, and L 4 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group or C1 represents C1-C6 alkyl group substituted with -C6 alkoxy group, L 5 and L 6 are the same or different, represent a methyl group or a hydrogen atom. ]
Subgroup A-6:
A group of compounds consisting of a compound represented by the following formula (5).

[Wherein, X 1 represents a 2-methylpropyl group or 2-methyl-1-propenyl group, X 2 represents a methyl group, X 3 represents a 2-methyl-1-propenyl group, and X 4 represents methyl Represents a group. ]
The compound represented by the formula (1), or an N-oxide thereof,
In the formula (1),
R 1 is a C1-C6 alkyl group optionally having one or more atoms or groups selected from group Y;
R 2 and R 4 are hydrogen atoms,
R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR 10 ) 3 , a halogen atom or a hydrogen atom,
R 5 is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR 10 , —S (O) m R 10 , —CO 2 R 10 , —SF 5 or a halogen atom;
R 6 is —OR 10 , —NR 10 R 11 , —CO 2 R 10 , —C (O) NR 10 R 11 , —OC (O) R 10 , a cyano group, a halogen atom or a hydrogen atom;
R 7 is one or more halogen atoms optionally C1-C6 may be alkyl groups having a, -CH 2 CO 2 R 10, C3-C6 cycloalkyl group or a hydrogen atom,
R 8 is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR 10 , —S (O) m R 10 , a cyano group, a halogen atom or a hydrogen atom;
R 10 and R 11 are the same or different and each is a C1-C3 alkyl group which may have one or more halogen atoms or a hydrogen atom (provided that in —S (O) m R 10 , m is 1 Or in the case of 2, R 10 does not represent a hydrogen atom).
The pest control composition according to claim 1, wherein the group Y is a compound which is a group consisting of a C3-C6 cycloalkyl group which may have one or more halogen atoms and a halogen atom, or an N-oxide thereof. .
The compound represented by the formula (1), or an N-oxide thereof,
In the formula (1),
R 1 is a C1-C3 alkyl group optionally having one or more halogen atoms,
R 2 and R 4 are hydrogen atoms,
R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR 10 ) 3 , a halogen atom or a hydrogen atom,
R 5 is a C1-C3 alkyl group optionally having one or more halogen atoms, —OR 10 , —S (O) m R 10 or a halogen atom;
R 6 is a cyano group, —NR 10 R 11 , a halogen atom or a hydrogen atom,
R 7 is a C1-C6 alkyl group optionally having one or more halogen atoms,
R 8 is —S (O) m R 10 , a cyano group, a halogen atom or a hydrogen atom,
The pest control composition according to claim 1, wherein R 10 and R 11 are the same or different and are a C1-C3 alkyl group optionally having one or more halogen atoms, or an N-oxide thereof. object.
The compound represented by the formula (1), or an N-oxide thereof,
In the formula (1),
R 1 is an ethyl group,
R 2 and R 4 are hydrogen atoms,
R 3 is a C1-C3 alkyl group optionally having one or more halogen atoms, —C (OR 10 ) 3 , a halogen atom or a hydrogen atom,
R 5 is a C1-C3 haloalkyl group, —OR 20 , —S (O) m R 20 or a halogen atom;
R 6 is a cyano group, —NR 10 R 11 , a halogen atom or a hydrogen atom,
R 7 is a C1-C6 alkyl group optionally having one or more halogen atoms,
R 8 is —S (O) m R 10 , a cyano group, a halogen atom or a hydrogen atom,
R 10 and R 11 are the same or different and each is a C1-C3 alkyl group optionally having one or more halogen atoms,
The pest control composition according to claim 1, wherein R 20 is a compound having a C1-C3 haloalkyl group, or an N-oxide thereof.
The compound represented by the formula (1), or an N-oxide thereof,
In the formula (1),
The pest control composition according to any one of claims 1 to 4, which is a compound in which A 1 is -NR 7- or an N-oxide thereof.
The compound represented by the formula (1), or an N-oxide thereof,
In the formula (1),
The pest control composition according to any one of claims 1 to 4, which is a compound wherein A 1 is an oxygen atom, or an N-oxide thereof.
The compound represented by the formula (1), or an N-oxide thereof,
In the formula (1),
The pest control composition according to any one of claims 1 to 4, which is a compound in which A 1 is a sulfur atom, or an N-oxide thereof.
A compound represented by the following formula (1-2), or an N-oxide thereof,
A pest control composition comprising one or more compounds selected from the group (A) in claim 1.
Formula (1-2):

[Where:
R 1a represents a C1-C3 alkyl group,
A 2a represents a nitrogen atom or = CR 8a- ,
R 3a represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR 10a ) 3 , a halogen atom or a hydrogen atom,
R 5a represents a C1-C3 haloalkyl group, —OR 20a , —S (O) m R 20a or a halogen atom,
R 6a represents a cyano group, —NR 10a R 11a , a halogen atom or a hydrogen atom,
R 7a represents a C1-C6 alkyl group optionally having one or more halogen atoms,
R 8a represents —S (O) m R 10a , a cyano group, a halogen atom or a hydrogen atom;
R 10a and R 11a are the same or different and each represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R 20a represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. ]
A compound represented by the following formula (1-3), or an N-oxide thereof,
A pest control composition comprising one or more compounds selected from the group (A) in claim 1.
Formula (1-3):

[Where:
A 2b represents a nitrogen atom or = CR 8b- ,
R 3b represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR 10b ) 3 , a halogen atom or a hydrogen atom,
R 5b represents a C1-C3 haloalkyl group, —OR 20b , —S (O) m R 20b or a halogen atom,
R 8b represents —S (O) m R 10b , a cyano group, a halogen atom or a hydrogen atom;
R 10b represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R 20b represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. ]
The compound represented by the formula (1-3), or an N-oxide thereof,
In the formula (1-3),
R 3b is a halogen atom or a hydrogen atom,
R 5b is a C1-C3 perfluoroalkyl group, —OR 30b or —S (O) m R 30b ,
R 30b is a C1-C3 perfluoroalkyl group,
The pest control composition according to claim 9, which is a compound in which R 8b is a halogen atom or a hydrogen atom, or an N-oxide thereof.
A compound represented by the following formula (1-4), or an N-oxide thereof,
A pest control composition comprising one or more compounds selected from the group (A) in claim 1.
Formula (1-4):

[Where:
A 2c represents a nitrogen atom or = CR 8c- ,
R 3c represents a C1-C3 alkyl group which may have one or more halogen atoms, —C (OR 10c ) 3 , a halogen atom or a hydrogen atom,
R 5c represents a C1-C3 haloalkyl group, —OR 20c , —S (O) m R 20c or a halogen atom,
R 8c represents -S (O) m R 10c , a cyano group, a halogen atom or a hydrogen atom,
R 10c represents a C1-C3 alkyl group optionally having one or more halogen atoms,
R 20c represents a C1-C3 haloalkyl group,
m independently represents 0, 1 or 2, and n represents 0, 1 or 2. ]
The compound represented by the formula (1-4), or an N-oxide thereof,
In the formula (1-4),
R 3c is a halogen atom or a hydrogen atom,
R 5c is a C1-C3 perfluoroalkyl group, —OR 30c or —S (O) m R 30c ,
R 30c is a C1-C3 perfluoroalkyl group,
The pest control composition according to claim 11, which is a compound wherein R 8c is a halogen atom or a hydrogen atom, or an N-oxide thereof.
The ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight ratio. A pest control composition according to claim 1.
The ratio of the content of the compound represented by the formula (1) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight ratio. A pest control composition according to claim 1.
The ratio of the content of the compound represented by the formula (1-2) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight. Pest control composition.
The ratio of the content of the compound represented by the formula (1-2) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight. Pest control composition.
The ratio of the content of the compound represented by the formula (1-3) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight ratio. A pest control composition as described in 1. above.
The ratio of the content of the compound represented by the formula (1-3) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight. A pest control composition as described in 1. above.
The ratio of the content of the compound represented by the formula (1-4) and one or more compounds selected from the group (A) is 100: 1 to 1: 100 by weight. A pest control composition as described in 1. above.
The ratio of the content of the compound represented by the formula (1-4) and one or more compounds selected from the group (A) is 10: 1 to 1:10 by weight. A pest control composition as described in 1. above.
A pest control method comprising a step of applying an effective amount of the pest control composition according to any one of claims 1 to 20 to a pest or a habitat of the pest.