Pest control agents

Abstract

A compound represented by formula (1), or an N-oxide or salt of the compound.　In the formula, RC represents a five-membered azole substituent or the like.

Description

[Technical Field]

[0001] The present invention relates to a compound represented by formula (1) or an N-oxide thereof, or a salt thereof, and a pesticide containing the compound as an active ingredient. [Background technology]

[0002] Various compounds have been investigated and put to practical use for the purpose of controlling harmful arthropods. For example, Patent Documents 1, 2, and 3 disclose fused heterocyclic compounds as insecticides. Patent Document 4 discloses certain amide compounds. However, no compounds have been found that have high pest control activity and are highly practical. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2009 / 131237 [Patent Document 2] International Publication No. 2013 / 180194 [Patent Document 3] International Publication No. 2016 / 129684 [Patent Document 4] International Publication No. 2015 / 068719 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide an amidine compound or an N-oxide or a salt thereof that exhibits excellent control activity against various pests, and a pest control agent containing the same as an active ingredient. [Means for solving the problem]

[0005] As a result of extensive research, the present inventors have found that the compound represented by formula (1) has high pesticidal activity, and have thus completed the present invention.

[0006] That is, the present invention relates to, but is not limited to, the following: <Invention 1> A compound represented by formula (1) or an N-oxide thereof, or a salt thereof: [ka] [In formula (1), A represents a structure represented by A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12, or A-13, [ka] R 1 , R 2 , R 3 , R 4 and R 5 are each independently at least one selected from halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, halo(C1-C6)alkylthio, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfonyl, and (C═O)NY 1 Y 2 and other R 1 , R 2 , R 3 , R 4 and R 5 each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C6 alkyl, a C3-C6 cycloalkyl, a halo(C1-C6)alkyl, a C1-C6 alkoxy, a halo(C1-C6)alkoxy, a halo(C1-C6)alkylthio, a halo(C1-C6)alkylsulfinyl, and a halo(C1-C6)alkylsulfonyl; R 6represents a group selected from the group consisting of a hydrogen atom, (C1-C3) alkyl, cyclopropyl, halo(C1-C3) alkyl, (C1-C3) alkoxy, and halo(C1-C3) alkoxy; Y 1 represents halo(C1-C3)alkyl, Y 2 represents a group selected from the group consisting of a hydrogen atom, (C1-C3) alkyl, and halo(C1-C3) alkyl; n represents 0, 1, or 2; R A represents a C1-C3 alkyl group, R B and R D each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, halo(C1-C3)alkyl, cyano, and amino which may be substituted by up to two C1-C3 alkyl groups, R C represents a group selected from the group consisting of phenyl optionally substituted with up to five Z's, pyridinyl optionally substituted with up to four Z's, pyrimidinyl optionally substituted with up to three Z's, pyrazinyl optionally substituted with up to three Z's, pyridazinyl optionally substituted with up to three Z's, and V; V represents a group selected from the group consisting of structures represented by V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8 and V-9; [ka] When there are multiple Z's, each Z's independently represents a hydrogen atom, a halogen atom, C1-C6 alkyl, halo(C1-C6)alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, NY 3 Y 4 , and (C=O)NY 3 Y4 or two Z's and R's to which the Z's are bonded. C A group in which the carbon atoms of the two Z's bonded to each other form a 1,3-dioxole group, and a group in which the carbon atoms of the two Z's bonded to each other form a 1,3-dioxole group. C taken together to form a 1,4-dioxine group, wherein the 1,3-dioxole group and the 1,4-dioxine group are optionally substituted with one or more independent halogen atoms; Q2 represents 0, 1 or 2; Q3 represents 0, 1, 2 or 3; Q4 represents 0, 1, 2, 3 or 4; Y 3 and Y 4 each independently represents a group selected from the group consisting of a hydrogen atom, C1-C3 alkyl, cyclopropyl, and halo(C1-C3)alkyl, D represents a group selected from the group consisting of a hydrogen atom, C1-C6 alkylcarbonyl optionally substituted with T, halo(C1-C6)alkylcarbonyl optionally substituted with T, C3-C6 cycloalkylcarbonyl optionally substituted with T, C2-C6 alkenylcarbonyl optionally substituted with T, halo(C2-C6)alkenylcarbonyl optionally substituted with T, C2-C6 alkynylcarbonyl optionally substituted with T, C1-C6 alkoxycarbonyl optionally substituted with T, halo(C1-C6)alkoxycarbonyl optionally substituted with T, C3-C6 cycloalkylcarbonyl optionally substituted with T, C2-C6 alkenylcarbonyl optionally substituted with T, hydroxy, C1-C6 alkoxy optionally substituted with T, C3-C6 cycloalkoxy optionally substituted with T, and halo(C1-C6)alkoxy optionally substituted with T; E represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl which may be substituted with T, a halo(C1-C6)alkyl which may be substituted with T, a C1-C6 alkylcarbonyl which may be substituted with T, and a halo(C1-C6)alkylcarbonyl which may be substituted with T; The T substitution may be made by multiple T's; When there are two or more T's, each T's independently represents a group selected from the group consisting of C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfinyl, halo(C1-C3)alkylsulfinyl, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, cyano, and a phenyl group optionally substituted with up to five G's; When there are a plurality of Gs, each G independently represents a group selected from the group consisting of a halogen atom, a C1-C3 alkyl, and a halo(C1-C3)alkyl. <Invention 2> A compound represented by formula (1) or an N-oxide thereof, or a salt thereof: [ka] [In formula (1), A represents a structure represented by A-1, A-2, or A-3, [ka] R 1 , R 2 , R 3 , R 4 and R 5 are each independently at least one selected from halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, halo(C1-C6)alkylthio, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfonyl, and (C═O)NY 1 Y 2 and other R 1 , R 2 , R 3 , R 4 and R 5each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C6 alkyl, a C3-C6 cycloalkyl, a halo(C1-C6)alkyl, a C1-C6 alkoxy, a halo(C1-C6)alkoxy, a halo(C1-C6)alkylthio, a halo(C1-C6)alkylsulfinyl, and a halo(C1-C6)alkylsulfonyl; Y 1 represents halo(C1-C3)alkyl, Y 2 represents a group selected from the group consisting of a hydrogen atom, (C1-C3) alkyl, and halo(C1-C3) alkyl; n represents 0, 1, or 2; R A represents a C1-C3 alkyl group, R B and R D each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, and halo(C1-C3)alkyl, R C represents a group selected from the group consisting of phenyl optionally substituted with up to five Z's, pyridinyl optionally substituted with up to four Z's, pyrimidinyl optionally substituted with up to three Z's, pyrazinyl optionally substituted with up to three Z's, pyridazinyl optionally substituted with up to three Z's, and V; V represents a group selected from the group consisting of structures represented by V-1, V-2, V-3, V-4, V-5, V-6, V-7, and V-8; [ka] When there are multiple Z's, each Z's independently represents a hydrogen atom, a halogen atom, C1-C6 alkyl, halo(C1-C6)alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, NY 3 Y4 , and (C=O)NY 3 Y 4 represents a group selected from the group consisting of Q2 represents 0, 1 or 2; Q3 represents 0, 1, 2 or 3; Q4 represents 0, 1, 2, 3 or 4; When Q2, Q3, and Q4 each represent an integer of 2 or more, each Z may be the same as or different from each other; Y 3 and Y 4 each independently represents a group selected from the group consisting of a hydrogen atom, C1-C3 alkyl, cyclopropyl, and halo(C1-C3)alkyl, D represents a group selected from the group consisting of a hydrogen atom, C1-C6 alkylcarbonyl optionally substituted with T, halo(C1-C6)alkylcarbonyl optionally substituted with T, C3-C6 cycloalkylcarbonyl optionally substituted with T, C2-C6 alkenylcarbonyl optionally substituted with T, halo(C2-C6)alkenylcarbonyl optionally substituted with T, C2-C6 alkynylcarbonyl optionally substituted with T, C1-C6 alkoxycarbonyl optionally substituted with T, halo(C1-C6)alkoxycarbonyl optionally substituted with T, C3-C6 cycloalkylcarbonyl optionally substituted with T, C2-C6 alkenylcarbonyl optionally substituted with T, hydroxy, C1-C6 alkoxy optionally substituted with T, C3-C6 cycloalkoxy optionally substituted with T, and halo(C1-C6)alkoxy optionally substituted with T; E represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl which may be substituted with T, a halo(C1-C6)alkyl which may be substituted with T, a C1-C6 alkylcarbonyl which may be substituted with T, and a halo(C1-C6)alkylcarbonyl which may be substituted with T; The T substitution may be made by multiple T's; When there are two or more T's, each T's independently represents a group selected from the group consisting of C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfinyl, halo(C1-C3)alkylsulfinyl, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, cyano, and a phenyl group optionally substituted with up to five G's; When there are a plurality of Gs, each G independently represents a group selected from the group consisting of a halogen atom, a C1-C3 alkyl, and a halo(C1-C3)alkyl. <Invention 3> R 1 , R 2 , R 3 , R 4 and R 5 wherein each independently at least one is halo(C1-C3)alkyl, (C1-C3)alkoxy, halo(C1-C3)alkoxy, halo(C1-C3)alkylthio, halo(C1-C3)alkylsulfinyl, halo(C1-C3)alkylsulfonyl, and (C═O)NY 1 Y 2 and other R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom or a halogen atom, R A is an ethyl group, R B and R D are each independently a hydrogen atom or a halogen atom, R C represents a group selected from the group consisting of a phenyl group optionally substituted with up to five Z's, a pyrimidinyl group optionally substituted with up to three Z's, and V; When there are multiple Z's, each Z's independently represents at least one of a halogen atom, C1-C6 alkyl, halo(C1-C6)alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, NY 3 Y 4 , and (C=O)NY 3 Y 4 and the other Z's are a hydrogen atom, a halogen atom, C1-C6 alkyl, halo(C1-C6)alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, NY 3 Y 4 , and (C=O)NY 3 Y 4 is a group selected from the group consisting of D is a group selected from the group consisting of a hydrogen atom, C1-C6 alkylcarbonyl, halo(C1-C6)alkylcarbonyl, cyclopropylcarbonyl, C1-C6 alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, hydroxy, C1-C6 alkoxy optionally substituted with T, C3-C6 cycloalkoxy optionally substituted with T, and halo(C1-C6)alkoxy optionally substituted with T; E is a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl optionally substituted with T, and a halo(C1-C6)alkyl optionally substituted with T, When there are multiple T's, each T is independently a group selected from the group consisting of C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfinyl, halo(C1-C3)alkylsulfinyl, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, and cyano; 3. The compound according to invention 1 or 2, or an N-oxide thereof, or a salt thereof. <Invention 4> R 1 , R 2 , R 3 , R 4 and R 5 at least one of R is independently a group selected from the group consisting of trifluoromethyl, pentafluoroethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, trifluoromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, and (2,2,2-trifluoroethyl)carbamoyl; 1 , R 2 , R 3 , R 4 and R 5 is a hydrogen atom or a halogen atom, R C is a group selected from the group consisting of structures represented by V-2, V-6, V-7, and V-8, [ka] Z is independently selected from the group consisting of halogen atom, C1-C3 alkyl, halo(C1-C3)alkyl, cyclopropyl, C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfinyl, halo(C1-C3)alkylsulfinyl, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, NY 3 Y 4 , and (C=O)NY 3 Y 4 and the other Z's are a hydrogen atom, a halogen atom, C1-C3 alkyl, halo(C1-C3)alkyl, cyclopropyl, C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfinyl, halo(C1-C3)alkylsulfinyl, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, NY 3 Y 4 , and (C=O)NY 3 Y 4 is a group selected from the group consisting of A compound according to any one of Inventions 1 to 3, or an N-oxide thereof, or a salt thereof. <Invention 5> R 1 , R 2 , R 3 , R 4 and R 5 at least one of R is independently selected from the group consisting of trifluoromethyl, pentafluoroethyl, trifluoromethylthio, trifluoromethylsulfinyl, and trifluoromethylsulfonyl; 1 , R 2 , R 3 , R 4 and R 5 is a hydrogen atom, R B and R D is a hydrogen atom, D is a group selected from the group consisting of a hydrogen atom, C1-C3 alkylcarbonyl, halo(C1-C3)alkylcarbonyl, cyclopropylcarbonyl, C1-C3 alkoxycarbonyl, halo(C1-C3)alkoxycarbonyl, hydroxy, C1-C6 alkoxy optionally substituted with T, C3-C6 cycloalkoxy optionally substituted with T, and halo(C1-C6)alkoxy optionally substituted with T; E is a group selected from the group consisting of a hydrogen atom, a C1-C3 alkyl optionally substituted with T, and a halo(C1-C3)alkyl optionally substituted with T. 5. The compound according to any one of Inventions 1 to 4, or an N-oxide thereof, or a salt thereof. <Invention 6> The compound according to any one of Inventions 1 to 5, or an N-oxide thereof, or a salt thereof, wherein D is a group selected from the group consisting of hydroxy, C1-C6 alkoxy which may be substituted with T, C3-C6 cycloalkoxy which may be substituted with T, and halo(C1-C6)alkoxy which may be substituted with T. <Invention 7> R C is V-7 or V-8, or an N-oxide or a salt thereof according to any one of Inventions 1 to 6. [ka] <Invention 8> 8. The compound or N-oxide thereof, or a salt thereof according to any one of Inventions 1 to 7, wherein A is A-2. [ka] <Invention 9> 8. The compound or N-oxide thereof, or a salt thereof according to any one of Inventions 1 to 7, wherein A is A-3. [ka] <Invention 10> 10. A pest control agent comprising the compound according to any one of Inventions 1 to 9, or an N-oxide thereof, or a salt thereof. [Effects of the Invention]

[0007] The compound of the present invention represented by formula (1) or its N-oxide or salt thereof exhibits an extremely excellent control effect against pests and is useful as a pest control agent. DETAILED DESCRIPTION OF THE INVENTION

[0008] In this specification, the definitions and meanings of the following terms are as follows:

[0009] The compounds encompassed by the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or sulfur atoms or axial asymmetry, and the present invention encompasses all optically active forms or racemic forms.

[0010] Compounds included in the present invention may have tautomers depending on the type of substituent, and the present invention includes all tautomers or mixtures of tautomers containing any ratio.

[0011] The compounds included in the present invention may have geometric isomers due to the imino group, and the present invention includes all geometric isomers or a mixture of geometric isomers containing them in any ratio. [ka] Furthermore, the compounds included in the present invention may have tautomers due to the amidine group as shown in Chemical Formula 4, but the present invention includes all tautomers or mixtures of tautomers containing any ratio. A , R B , R C , R D and D are the same as above, Het is a heterocycle, and n is 0, 1, or 2.

[0012] Among the compounds encompassed by the present invention, those which can be converted into salts by conventional methods include salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; aluminum salts; and quaternary ammonium salts such as tetramethylammonium salt, tetrabutylammonium salt, and benzyltrimethylammonium salt.

[0013] In the compound of the present invention, the N-oxide is a compound in which the nitrogen atom of a tertiary amine or a nitrogen atom constituting a ring on a heterocycle is oxidized. Examples of the heterocycle capable of forming the N-oxide include a pyridine ring and a fused ring containing a pyridine ring.

[0014] Next, specific examples of each substituent shown in the present specification are shown below, where n- means normal, i- means iso, s- means secondary, tert- means tertiary, and c- means cyclo.

[0015] As used herein, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The term "halo" also refers to these halogen atoms.

[0016] In this specification, "C a ~C bThe term "alkyl" represents a linear or branched hydrocarbon group having a to b carbon atoms, and specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a tert-butyl group, an n-pentyl group, a 1,1-dimethylpropyl group, and an n-hexyl group, each of which is selected within the range of the number of carbon atoms specified.

[0017] As used herein, "halo(C a ~C bThe notation "alkyl" refers to a linear or branched hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when substituted with two or more halogen atoms, those halogen atoms may be the same or different. For example, 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 trichloromethyl group, a bromodifluoromethyl group, a 1-fluoroethyl group, a 2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2,2-trichloroethyl group, a 2-bromo-2,2-difluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a 2-chloro-1,1,2-trifluoroethyl group, a 2-chloro-1,1,2,2-tetrafluoroethyl group, a pentafluoroethyl group, a 2,2 Specific examples include a 1,1,2,3,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3-bromo-3,3-difluoropropyl group, a 2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 1,1,2,3,3,3-hexafluoropropyl group, a heptafluoropropyl group, a 2,2,2-trifluoro-1-(methyl)ethyl group, a 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group, a 2,2,3,4,4,4-hexafluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, and a nonafluorobutyl group, and the number of carbon atoms is selected within the range specified for each group.

[0018] In this specification, "C a ~C bThe term "alkenyl" refers to a linear or branched unsaturated hydrocarbon group containing a to b carbon atoms and having one or more double bonds in the molecule. Specific examples include vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, and 1,1-dimethyl-2-propenyl groups, and each group is selected within the range of the specified number of carbon atoms.

[0019] As used herein, "halo(C a ~C b The term "alkenyl" refers to a linear or branched unsaturated hydrocarbon group having a to b carbon atoms and one or more double bonds in the molecule, in which hydrogen atoms bonded to carbon atoms are optionally substituted with halogen atoms. In this case, when substituted with two or more halogen atoms, the halogen atoms may be the same or different. Specific examples include a 2,2-dichlorovinyl group, a 2-fluoro-2-propenyl group, a 2-chloro-2-propenyl group, a 2-bromo-2-propenyl group, a 3,3-difluoro-2-propenyl group, a 2,3-dichloro-2-propenyl group, a 3,3-dichloro-2-propenyl group, a 2,3,3-trifluoro-2-propenyl group, a 2,3,3-trichloro-2-propenyl group, a 1-(trifluoromethyl)ethenyl group, a 4,4-difluoro-3-butenyl group, a 3,4,4-trifluoro-3-butenyl group, and a 3-chloro-4,4,4-trifluoro-2-butenyl group, and the like, and each group is selected within the range of the number of carbon atoms specified for each group.

[0020] In this specification, "C a ~C b The term "alkynyl" refers to a linear or branched unsaturated hydrocarbon group containing a to b carbon atoms and having one or more triple bonds in the molecule. Specific examples include an ethynyl group, a propargyl group, a 2-butynyl group, a 1-pentynyl group, a 1-hexynyl group, and a 4,4,4-trifluoro-2-butynyl group, and are selected within the range of the number of carbon atoms specified for each group.

[0021] "C a ~C b The term "cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms, and can form a single ring or multiple ring structures having 3 to 6 members. Each ring may be optionally substituted with an alkyl group within the specified range of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups, each selected within the specified range of carbon atoms.

[0022] "C a ~C b The term "alkoxy" represents an alkyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include a methoxy group, an ethoxy group, an n-propyloxy group, an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and a 2-ethylhexyloxy group, each of which is selected within the range of the number of carbon atoms specified.

[0023] "Haro (C a ~C b The notation of ")alkoxy" represents a haloalkyl-O- group having a to b carbon atoms as defined above, and specific examples thereof include a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a 2-chloro-1,1,2-trifluoroethoxy group, and a 1,1,2,3,3,3-hexafluoropropyloxy group, and the number of carbon atoms is selected within the range specified for each group.

[0024] "C a ~C bThe term "alkylthio" represents an alkyl-S- group having a to b carbon atoms as defined above, and specific examples thereof include a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, and a tert-butylthio group, each of which is selected within the range of the number of carbon atoms specified.

[0025] As used herein, "halo(C a ~C b The notation of "(trifluoromethyl)alkylthio" represents a haloalkyl-S- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a difluoromethylthio group, a trifluoromethylthio group, a chlorodifluoromethylthio group, a bromodifluoromethylthio group, a 2,2,2-trifluoroethylthio group, a 1,1,2,2-tetrafluoroethylthio group, a 2-chloro-1,1,2-trifluoroethylthio group, a pentafluoroethylthio group, a 1,1,2,3,3,3-hexafluoropropylthio group, a heptafluoropropylthio group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylthio group, and a nonafluorobutylthio group, and each group is selected within the range of the specified number of carbon atoms.

[0026] "C a ~C b The term "alkylsulfinyl" represents an alkyl-S(O)- group having a to b carbon atoms as defined above, and specific examples thereof include a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an i-propylsulfinyl group, an n-butylsulfinyl group, an i-butylsulfinyl group, an s-butylsulfinyl group, and a tert-butylsulfinyl group, each selected within the range of the specified number of carbon atoms.

[0027] As used herein, "halo(C a ~C bThe notation of "(1-(trifluoromethyl)ethylsulfinyl)" represents a haloalkyl-S(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a chlorodifluoromethylsulfinyl group, a bromodifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylsulfinyl group, and a nonafluorobutylsulfinyl group, and each group is selected within the specified range of carbon atoms.

[0028] "C a ~C b The term "alkylsulfonyl" represents an alkyl-SO- group having a to b carbon atoms as defined above, and specific examples thereof include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group, an i-butylsulfonyl group, an s-butylsulfonyl group, and a tert-butylsulfonyl group, each of which is selected within the range of the number of carbon atoms specified.

[0029] As used herein, "halo(C b ~C b The notation ")alkylsulfonyl" represents a haloalkyl-SO- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a chlorodifluoromethylsulfonyl group, a bromodifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, a 1,1,2,2-tetrafluoroethylsulfonyl group, and a 2-chloro-1,1,2-trifluoroethylsulfonyl group, and the like, each selected within the range of the specified number of carbon atoms.

[0030] "C a ~C bThe term "alkylcarbonyl" represents an alkyl-C(O)- group having a to b carbon atoms as defined above, and specific examples thereof include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, a hexanoyl group, and a heptanoyl group, each of which is selected within the range of the number of carbon atoms specified.

[0031] "Haro (C a ~C b The notation of ")alkylcarbonyl" represents a haloalkyl-C(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a fluoroacetyl group, a chloroacetyl group, a difluoroacetyl group, a dichloroacetyl group, a trifluoroacetyl group, a chlorodifluoroacetyl group, a bromodifluoroacetyl group, a trichloroacetyl group, a pentafluoropropionyl group, a heptafluorobutanoyl group, and a 3-chloro-2,2-dimethylpropanoyl group, and the like, each selected within the range of the specified number of carbon atoms.

[0032] "C a ~C b The term "alkoxycarbonyl" represents an alkyl-OC(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an i-propyloxycarbonyl group, an n-butoxycarbonyl group, an i-butoxycarbonyl group, an s-butoxycarbonyl group, a tert-butoxycarbonyl group, and a 2-ethylhexyloxycarbonyl group, each selected within the range of the specified number of carbon atoms.

[0033] "Haro (C a ~C bThe notation of ")alkoxycarbonyl" represents a haloalkyl-OC(O)- group having the above-mentioned meaning and containing a to b carbon atoms, and specific examples thereof include a chloromethoxycarbonyl group, a 2-chloroethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, a 2,2,2-trifluoroethoxycarbonyl group, and a 2,2,2-trichloroethoxycarbonyl group, and the like are selected within the range of the number of carbon atoms specified for each group.

[0034] The compound of the present invention is a compound represented by formula (1) or an N-oxide thereof, or a salt thereof, [ka] In formula (1), A represents a structure represented by A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A-12 or A-13, [ka] R 1 , R 2 , R 3 , R 4 and R 5 are each independently at least one selected from halo(C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkoxy, halo(C1-C6)alkylthio, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkylsulfonyl, and (C═O)NY 1 Y 2 and other R 1 , R 2 , R 3 , R 4 and R 5 each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C6 alkyl, a C3-C6 cycloalkyl, a halo(C1-C6)alkyl, a C1-C6 alkoxy, a halo(C1-C6)alkoxy, a halo(C1-C6)alkylthio, a halo(C1-C6)alkylsulfinyl, and a halo(C1-C6)alkylsulfonyl; Y 1 represents halo(C1-C3)alkyl, Y 2 represents a group selected from the group consisting of a hydrogen atom, (C1-C3) alkyl, and halo(C1-C3) alkyl; n represents 0, 1, or 2; R A represents a C1-C3 alkyl group, R B and R D each independently represents a group selected from the group consisting of a hydrogen atom, a halogen atom, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, and halo(C1-C3)alkyl, R C represents a group selected from the group consisting of phenyl optionally substituted with up to five Z's, pyridinyl optionally substituted with up to four Z's, pyrimidinyl optionally substituted with up to three Z's, pyrazinyl optionally substituted with up to three Z's, pyridazinyl optionally substituted with up to three Z's, and V; V represents a group selected from the group consisting of structures represented by V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8 and V-9; [ka] When there are multiple Z's, each Z's independently represents a hydrogen atom, a halogen atom, C1-C6 alkyl, halo(C1-C6)alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, NY 3 Y 4 , and (C=O)NY 3 Y 4 or two Z's and R's to which the Z's are bonded. Ctaken together to form a 1,3-dioxole group, said 1,3-dioxole group being optionally substituted with one or more independent halogen atoms; Q2 represents 0, 1 or 2; Q3 represents 0, 1, 2 or 3; Q4 represents 0, 1, 2, 3 or 4; Y 3 and Y 4 each independently represents a group selected from the group consisting of a hydrogen atom, C1-C3 alkyl, cyclopropyl, and halo(C1-C3)alkyl, D represents a group selected from the group consisting of a hydrogen atom, C1-C6 alkylcarbonyl optionally substituted with T, halo(C1-C6)alkylcarbonyl optionally substituted with T, C3-C6 cycloalkylcarbonyl optionally substituted with T, C2-C6 alkenylcarbonyl optionally substituted with T, halo(C2-C6)alkenylcarbonyl optionally substituted with T, C2-C6 alkynylcarbonyl optionally substituted with T, C1-C6 alkoxycarbonyl optionally substituted with T, halo(C1-C6)alkoxycarbonyl optionally substituted with T, C3-C6 cycloalkylcarbonyl optionally substituted with T, C2-C6 alkenylcarbonyl optionally substituted with T, hydroxy, C1-C6 alkoxy optionally substituted with T, C3-C6 cycloalkoxy optionally substituted with T, and halo(C1-C6)alkoxy optionally substituted with T; E represents a group selected from the group consisting of a hydrogen atom, a C1-C6 alkyl which may be substituted with T, a halo(C1-C6)alkyl which may be substituted with T, a C1-C6 alkylcarbonyl which may be substituted with T, and a halo(C1-C6)alkylcarbonyl which may be substituted with T; The T substitution may be made by multiple T's; When there are two or more T's, each T's independently represents a group selected from the group consisting of C1-C3 alkoxy, halo(C1-C3)alkoxy, C1-C3 alkylthio, halo(C1-C3)alkylthio, C1-C3 alkylsulfinyl, halo(C1-C3)alkylsulfinyl, C1-C3 alkylsulfonyl, halo(C1-C3)alkylsulfonyl, cyano, and a phenyl group optionally substituted with up to five G's; When there are a plurality of Gs, each G independently represents a group selected from the group consisting of a halogen atom, a C1-C3 alkyl, and a halo(C1-C3)alkyl. That is, the compound of the present invention represented by formula (1) is R C is an optionally substituted phenyl group or an optionally substituted nitrogen-containing heterocyclic substituent. The other substituents are as described above.

[0035] Preferably, R 1 , R 2 , R 3 , R 4 and R 5 are each independently at least one selected from halo(C1-C3)alkyl, (C1-C3)alkoxy, halo(C1-C3)alkoxy, halo(C1-C3)alkylthio, halo(C1-C3)alkylsulfinyl, halo(C1-C3)alkylsulfonyl, and (C═O)NY 1 Y 2 and the others are hydrogen atoms or halogen atoms. 1 , R 2 , R 3 , R 4 and R 5 The other group in the formula (I) is more preferably a hydrogen atom. R 1 , R 2 , R 3 , R 4 and R 5More preferred specific examples of the substituent other than a hydrogen atom or a halogen atom in include trifluoromethyl, pentafluoroethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, trifluoromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, and (2,2,2-trifluoroethyl)carbamoyl, and more preferred are trifluoromethyl, pentafluoroethyl, trifluoromethylthio, trifluoromethylsulfinyl, and trifluoromethylsulfonyl.

[0036] R A is a C1 to C3 alkyl, preferably an ethyl group.

[0037] R B and R D each independently represent a group selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C3 alkyl, cyclopropyl, a C1-C3 alkoxy, a halo(C1-C3)alkyl, cyano, and an amino which may be substituted by up to two C1-C3 alkyl groups, preferably each independently represent a hydrogen atom, a methyl group, or a halogen atom, more preferably each independently represent a hydrogen atom or a methyl group.

[0038] R C represents a group selected from the group consisting of phenyl which may be substituted with up to five Z's, pyridinyl which may be substituted with up to four Z's, pyrimidinyl which may be substituted with up to three Z's, pyrazinyl which may be substituted with up to three Z's, pyridazinyl which may be substituted with up to three Z's, and V. V is a nitrogen-containing five-membered ring group (azole) selected from the group consisting of structures represented by V-1, V-2, V-3, V-4, V-5, V-6, V-7, and V-8. R C is two Zs and the R to which the Zs are bonded. CThe carbon atoms of R may be taken together to form a fused ring structure with a 1,3-dioxole group. The 1,3-dioxole group may be substituted with one or more independent halogen atoms. C is preferably a phenyl group which may be substituted with up to five Z's, a pyrimidinyl group which may be substituted with up to three Z's, or a nitrogen-containing five-membered ring group represented by V-1 to V-8, more preferably V-2, V-6, V-7, or V-8 which are nitrogen-containing five-membered ring groups, and even more preferably V-7 or V-8 which are tetrazoles which may have a substituent.

[0039] R C In the phenyl group or nitrogen-containing heterocyclic group, at least one of the substituents Z is preferably a group other than a hydrogen atom, and more preferably a halogen atom, C1-C6 alkyl, halo(C1-C6)alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo(C1-C6)alkoxy, C1-C6 alkylthio, halo(C1-C6)alkylthio, C1-C6 alkylsulfinyl, halo(C1-C6)alkylsulfinyl, C1-C6 alkylsulfonyl, halo(C1-C6)alkylsulfonyl, NY 3 Y 4 , (C=O)NY 3 Y 4 or two Z's and R's to which the Z's are bonded. C A group in which the carbon atoms of the two Z's bonded to each other form a 1,3-dioxole group, and a group in which the carbon atoms of the two Z's bonded to each other form a 1,3-dioxole group. C The carbon atoms of R are taken together to form a 1,4-dioxine group, and the 1,3-dioxole group and the 1,4-dioxine group may be substituted with one or more independent halogen atoms. C is preferably a substituted phenyl group or a substituted nitrogen-containing heterocyclic group.

[0040] D is preferably a hydrogen atom, C1-C6 alkylcarbonyl, halo(C1-C6)alkylcarbonyl, cyclopropylcarbonyl, C1-C6 alkoxycarbonyl, halo(C1-C6)alkoxycarbonyl, hydroxy, C1-C6 alkoxy which may be substituted with T, C3-C6 cycloalkoxy which may be substituted with T, or halo(C1-C6)alkoxy which may be substituted with T. Oxime derivatives or alkyloxime derivatives in which D is hydroxy, C1-C6 alkoxy which may be substituted with T, C3-C6 cycloalkoxy which may be substituted with T, or halo(C1-C6)alkoxy which may be substituted with T can also be mentioned as preferred embodiments of >C=ND.

[0041] A compound of formula (1) in which A is A-2, A-3, A-4, A-5, A-6, A-7, or A-8, or an N-oxide or salt thereof, is also a preferred embodiment. 1 ~R 5 , Y 1 ~Y 4 ,n,R A ~R D , Z, Q2 to Q4, D, E, T, and G have the same meanings as above.

[0042] The compound of the present invention represented by formula (1) or its N-oxide or salt thereof can be produced, for example, by the following production methods, but the present invention is not limited thereto.

[0043] Process a [ka]

[0044] An amidine compound represented by formula (1-1) can be produced by reacting an amine compound represented by formula (2) with a cyano compound represented by formula (3) in the presence of a base and an inert solvent. This reaction can be carried out according to a method described in the literature (e.g., Journal of Organic Chemistry, 2014, 79(10), pp. 4687-4693). In the formula, Het represents the following: [ka] In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R A , R B , R C and R D indicates the same as above.

[0045] Examples of bases that can be used in this reaction include alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, as well as normal butyllithium, sodium bis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, and lithium diisopropylamide, but the reactants that can be used in this reaction are not limited to these. The amount of base used is usually in the range of about 1 to 3 times the molar amount of the compound represented by formula (2).

[0046] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, etc. These inert solvents can be used alone or in combination of two or more.

[0047] The reaction temperature in this reaction may generally be in the range of from −78° C. to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected in the range of, for example, several minutes to 48 hours. The amino compound represented by formula (2) is usually used in an amount of about 0.3 to 3 times by mole relative to the cyano compound represented by formula (3). This reaction can also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0048] Alternative to step a The amidine compound of formula (1) can be produced by reacting an amine compound of formula (2) with a cyano compound of formula (3) in the presence of a Lewis acid. This reaction can be carried out according to a method described in the literature (e.g., J. Med. Chem. 2002, 45, 21, 4655-4668).

[0049] Examples of Lewis acids that can be used in this reaction include, but are not limited to, trimethylaluminum, aluminum chloride, titanium tetrachloride, etc. The amount of Lewis acid used is usually in the range of about 1 to 5 times the molar amount of the compound represented by formula (2).

[0050] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction. Examples of the inert solvent include aromatic hydrocarbons such as benzene, toluene, and xylene, and halogenated solvents such as dichloromethane and 1,2-dichloroethane. These inert solvents can be used alone or in combination.

[0051] The reaction temperature in this reaction may generally be in the range of from 0° C. to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected in the range of, for example, several minutes to 48 hours. The amino compound represented by formula (2) is usually used in an amount of about 0.3 to 3 times by mole relative to the cyano compound represented by formula (3). This reaction can also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0052] Process b [ka]

[0053] The amidine compound represented by formula (1-2) can be produced by reacting the amidine compound represented by formula (1-1) with a reactant in the presence of an inert solvent and, optionally, a base. A , R B , R C , R D , D and Het are the same as above, except when D is hydrogen.

[0054] Examples of reactants that can be used in the present invention include acid chlorides such as acetyl chloride, trifluoroacetyl chloride, and methyl chlorocarbonate, and acid anhydrides such as acetic anhydride and trifluoroacetic anhydride, but the reactants that can be used in this reaction are not limited to these. The amount of the reactant used can be appropriately selected usually within the range of about 1 to 3 times the molar amount of the compound represented by formula (1-1), and the reaction can be carried out without a solvent by adding an excess amount of a reactant such as acetic anhydride.

[0055] Examples of bases that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, and pyridine, and the amount used can be appropriately selected usually within the range of about 1 to 5 times the molar amount of the compound represented by formula (1-1).

[0056] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated solvents such as dichloromethane, 1,2-dichloroethane, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, etc. These inert solvents can be used alone or in combination of two or more.

[0057] The reaction temperature in this reaction may generally be in the range of about -78°C to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected, for example, in the range of several minutes to 48 hours. This reaction may also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0058] Process c [ka]

[0059] The amidine compound represented by formula (1-3) can be produced by reacting the amidine compound represented by formula (1-2) with a reactant in the presence of a base and an inert solvent. 2 , R 3 , R 4 , R 5 , R A , R B , R C , R D, D, E, and Het are the same as those defined above. However, D may be hydrogen. When the ortho position of "Het" in the 6-membered heterocycle is an N atom, the substituent E may be bonded to the N atom instead of the position described in formula (1-3). For example, an amidine compound represented by formula (1-3-1) and / or formula (1-4) can be produced by reacting an amidine compound represented by formula (1-2-1) with a reactant in the presence of a base and an inert solvent.

[0060] Examples of reactants that can be used in the present invention include alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, dimethyl sulfate, chloromethyl methyl ether, chloromethyl ethyl ether, chloroacetonitrile, bromoacetonitrile, 3-chloroacetonitrile, 3-bromoacetonitrile, and chloromethyl methyl sulfide, but the reactants that can be used in this reaction are not limited to these. The amount of the reactant used can be appropriately selected usually within the range of about 1 to 3 times the molar amount of the compound represented by formula (1-3) or formula (1-4).

[0061] Examples of the base that can be used in the present invention include alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; normal butyllithium; sodium bis(trimethylsilyl)amide; lithium bis(trimethylsilyl)amide; potassium bis(trimethylsilyl)amide; and lithium diisopropylamine. The amount of the base used can be appropriately selected usually within a range of about 1 to 5 times the molar amount of the compound represented by formula (1-2) or formula (1-2-1).

[0062] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, etc. These inert solvents can be used alone or in combination of two or more.

[0063] The reaction temperature in this reaction may generally be in the range of about -78°C to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected, for example, in the range of several minutes to 48 hours. This reaction may also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0064] Process d [ka]

[0065] An amidine compound represented by formula (1-5) or formula (1-6) or an isomer thereof can be produced by reacting an amidine compound represented by formula (1-3) or formula (1-4) or an isomer thereof with a reactant in the presence of an inert solvent. 2 , R 3 , R 4 , R 5 , R A , R B , R C , R D , D, E and Het are the same as above, and n is 1 or 2. However, D may be hydrogen.

[0066] Examples of the reactant that can be used in the present invention include oxidizing agents such as 3-chloroperbenzoic acid and aqueous hydrogen peroxide, but the reactant that can be used in this reaction is not limited thereto. The amount of the reactant used may be appropriately selected usually within the range of about 1 to 10 times the molar amount of the compound represented by formula (1-3) or formula (1-4).

[0067] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated solvents such as dichloromethane, 1,2-dichloroethane, etc.; carboxylic acids such as acetic acid, etc.; and alcohol solvents such as methanol, ethanol, isopropanol, etc. These inert solvents can be used alone or in combination of two or more.

[0068] The reaction temperature in this reaction may generally be in the range of about -78°C to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected, for example, in the range of several minutes to 48 hours. This reaction may also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0069] Process e [ka]

[0070] The amide compound represented by formula (4) can be produced by reacting the compound represented by formula (2) and the compound represented by formula (6) with a reactant in the presence of an inert solvent and, optionally, a base. A , R B , R C , R D and Het are the same as above, and n is 0, 1 or 2.

[0071] Examples of reactants that can be used in the present invention include condensing agents such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, HATU, PyBroP, Mukaiyama reagent, etc., but the reactants that can be used in this reaction are not limited to these. The amount of the reactant used can be appropriately selected usually within the range of about 1 to 3 times the molar amount of the compound represented by formula (2) or formula (6).

[0072] Examples of bases that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, and pyridine, and the amount used can be appropriately selected usually within the range of about 1 to 5 times the molar amount of the compound represented by formula (2) or formula (6).

[0073] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated solvents such as dichloromethane and 1,2-dichloroethane; and polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolinone. These inert solvents can be used alone or in combination.

[0074] The reaction temperature in this reaction may generally be in the range of about -78°C to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected, for example, in the range of several minutes to 48 hours. The amino compound represented by formula (2) is generally used in an amount of about 0.3 to 3 times the molar amount of the compound represented by formula (6). This reaction may also be carried out under an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0075] process f [ka]

[0076] The compound represented by formula (4) can be reacted with a reactant in the presence of an inert solvent to produce the compound represented by formula (5). A , R B , R C , R D , D and Het are the same as above, X is halogen, and n is 0, 1 or 2.

[0077] Examples of reactants that can be used in the present invention include, but are not limited to, phosphorus oxychloride, phosphorus pentachloride, carbon tetrachloride-triphenylphosphine, etc. The amount of the reactant used may be appropriately selected from the range of usually about 1 to 10 times the molar amount of the compound represented by formula (4), and the reaction can be carried out without solvent by adding an excess amount of a reactant such as phosphorus oxychloride.

[0078] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated solvents such as dichloromethane and 1,2-dichloroethane; and polar solvents such as acetonitrile. These inert solvents can be used alone or in combination of two or more.

[0079] The reaction temperature in this reaction may generally be in the range of about -78°C to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected, for example, in the range of several minutes to 48 hours. This reaction may also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0080] Process g [ka]

[0081] The compound represented by formula (1-5) can be produced by reacting the compound represented by formula (5) with a reactant in the presence of an inert solvent and a base. A , R B , R C , R D , D, X and Het are the same as above, and n is 0, 1 or 2. However, D may be hydrogen.

[0082] Examples of reactants that can be used in the present invention include hydroxylamines and their acid addition salts, such as hydroxylamine, O-methylhydroxylamine, and O-ethylhydroxylamine, alkylamines and their acid addition salts, such as methylamine and ethylamine, and ammonium acid addition salts, such as ammonium chloride, but the reactants that can be used in this reaction are not limited to these. The amount of the reactant used may be appropriately selected, usually within the range of about 1 to 5 times the molar amount of the compound represented by formula (5).

[0083] Examples of bases that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, pyridine, sodium carbonate, potassium carbonate, and cesium carbonate. The amount of base used can be appropriately selected usually within the range of about 1 to 10 times the molar amount of the compound represented by formula (5).

[0084] The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, etc.; and halogenated solvents such as dichloromethane, 1,2-dichloroethane, etc. These inert solvents can be used alone or in combination of two or more.

[0085] The reaction temperature in this reaction may generally be in the range of about -78°C to the boiling point of the solvent used. The reaction time may be appropriately selected depending on the reaction scale, reaction temperature, etc., and may be appropriately selected, for example, in the range of several minutes to 48 hours. This reaction may also be carried out in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc. The target product can be produced by the crude product containing the target product, which may be used in the next step without isolation.

[0086] The insect species to be controlled in the present invention (the insect species on which the compound represented by formula (1) exhibits a control effect) are not particularly limited, and the compound can be used to control a wide range of harmful insects in agriculture and horticulture. Preferred examples of the insect species to be controlled include the following:

[0087] Lepidoptera pests {e.g., rice stem borer (Chilo suppressalis), darkheaded stem borer (Chilo polychrysus), white stem borer (Scirpophaga innotata), rice leaf borer (Scirpophaga incertulas), Rupela albina, rice leaf borer (Cnaphalocrocis medinalis), Marasmia patnalis, rice casino borer (Marasmia exigua), cotton borer (Notarcha derogata), European corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), brown spotted borer (Hellula undalis), black rice borer (Herpetogramma luctuosale), grass moth (Pediasia Crambidae, such as the rice sedge moth (Nymphula depunctalis), rice case worm (Nymphula depunctalis), and sugarcane borer (Diatraea saccharalis); Pyralidae, such as the corn moth (Elasmopalpus lignosellus) and the Indian meal moth (Plodia interpunctella);Common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm (Mamestra brassicae), rice armyworm (Sesamia inferens), white armyworm (Spodoptera mauritia), two-banded cutworm (Naranga aenescens), rice armyworm (Spodoptera frugiperda), African armyworm (Spodoptera exempta), cutworm moth (Agrotis ipsilon), rice looper (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean looper (Chrysodeixis includens), Trichoplusia spp., false tobacco budworm (Heliothis Heliothis spp. such as Helicoverpa virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Noctuidae such as Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), and Hop vine borer (Hydraecia immanis); Pieridae such as Pieris rapae;Tortricidae, such as the pear fruit moth (Grapholita molesta), plum fruit moth (Grapholita dimorpha), bean fruit moth (Leguminivora glycinivorella), azuki bean pea moth (Matsumuraeses azukivora), apple tortrix moth (Adoxophyes orana fasciata), tea tortrix moth (Homona magnanima), green tea tortrix moth (Archips fuscocupreanus), codling moth (Cydia pomonella), citrus fruit borer moth (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), and citrus fruit borer (Ecdytolopha aurantiana); theivora and Phyllonorycter ringoniella (Gracillariidae); Carposinidae such as Carposina sasakii (Peach fruit moth); Lyonetiidae such as Leucoptera coffeella (Coffee leaf miner), Lyonetia clerkella (Peach leafminer), and Lyonetia prunifoliella (Lyonetia prunifoliella); Lymantriidae such as Lymantria spp. (Lymantria dispar) and Euproctis spp. (Euproctis pseudoconspersa); Pluteliidae such as Plutella xylostella (Pluteliidae);Gelechiidae (Gelechiidae) such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absoluta; Arctiidae (Arctiidae) such as Hyphantria cunea; Castniidae (Castniidae) such as Telchin licus (Giant Sugarcane Borer); Cossidae (Cossus insularis); Geometridae (Geometridae) such as Ascotis selenaria; Parasa Limacodidae (e.g., Limacodidae), such as Stathmopoda masinissa; Sphingidae (e.g., Acherontia lachesis); Sesiidae (e.g., Nokona feralis); Hesperiidae (e.g., Parnara guttata);

[0088] Hemiptera pests {e.g., the small brown planthopper (Laodelphax striatellus), the brown planthopper (Nilaparvata lugens), the white-backed planthopper (Sogatella furcifera), the corn planthopper (Peregrinus maidis), the yellow leafhopper (Javesella pellucida), the black horned planthopper (Perkinsiella saccharicida), and the Delphacidae family, such as the green rice leafhopper (Nephotettix cincticeps), the Taiwan green rice leafhopper (Nephotettix virescens), the black-striped rice leafhopper (Nephotettix nigropictus), the lightning leafhopper (Recilia dorsalis), and the tea green leafhopper (Empoasca onukii, potato leafhopper (Empoasca fabae), corn leafhopper (Dalbulus maidis), white leafhopper (Cofana spectra), etc.; Cercopidae, such as Mahanarva posticata and Mahanarva fimbriolata;Black bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), willow aphid (Aphis spiraecola), green peach aphid (Myzus persicae), strawberry aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat collar aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari), Japanese black aphid (Tetraneura nigriabdominalis), citrus cotton aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum), and other aphids (Aphididae); grapevine aphid (Daktulosphaira vitifoliae), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera Phylloxeridae, such as Adelges tsugae, Adelges piceae, and Aphrastasia pectinatae; Adelgidae, such as Adelges tsugae, Adelges piceae, and Aphrastasia pectinatae;Black rice bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), green stink bug (Nezara antennata), spiny spotted bug (Eysarcoris aeneus), large spiny spotted bug (Eysarcoris lewisi), white spotted bug (Eysarcoris ventralis), purple spotted bug (Eysarcoris annamita), brown stink bug (Halyomorpha halys), southern green stink bug (Nezara viridula), brown stink bug (Euschistus heros), red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops Pentatomidae (Pentatomidae) such as S. melacanthus; Cydnidae (Cydnidae) such as Scaptocoris castanea (Burrower brown bug); Alydidae (Riptortus pedestris), Leptocorisa chinensis, Leptocorisa acuta, and other Alydidae; Coreidae (Cletus punctiger, Leptoglossus australis, and other Coreidae); Caverelius saccharivorus, Togo hemipterus, and Blissus Lygaeidae, such as Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, and Lygus lineolaris; Miridae, such as Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, and Lygus lineolaris;Whiteflies of the family Aleyrodidae, such as the greenhouse whitefly (Trialeurodes vaporariorum), the tobacco whitefly (Bemisia tabaci), the citrus whitefly (Dialeurodes citri), the citrus spine whitefly (Aleurocanthus spiniferus), the tea spine whitefly (Aleurocanthus camelliae), and the Japanese oak cotton whitefly (Pealius euryae); the palm scale (Abgrallaspis cyanophylli), the red scale (Aonidiella aurantii), the pear scale (Diaspidiotus perniciosus), the white mulberry scale (Pseudaulacaspis pentagona), and the Yanon scale (Unaspis Diaspididae, such as Unaspis citri, false yanonensis; Coccidae, such as Ceroplastes rubens; Margarodidae, such as Icerya purchasi and Icerya seychellarum; Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus sieboldii ... calceolariae), long-legged mealybug (Pseudococcus longispinus), tuttlemea bug (Brevennia rehi), and other mealybugs (Pseudococcidae);Psyllidae, such as the citrus psyllid (Diaphorina citri), the citrus psyllid (Trioza erytreae), the pear psyllid (Cacopsylla pyrisuga), the Chinese pear psyllid (Cacopsylla chinensis), the potato psyllid (Bactericera cockerelli), and the pear psyllid (Cacopsylla pyricola); Tingidae, such as the plane tree earworm (Corythucha ciliata), the goldenrod earworm (Corythucha marmorata), the pear earworm (Stephanitis nashi), and the azalea earworm (Stephanitis pyrioides); Cimicidae, such as the bedbug (Cimex lectularius), and the giant cicada (Quesada Cicada family (Cicadidae) such as (Gigas);

[0089] Coleoptera (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica balteata), Cucurbit beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Red-necked leaf beetle (Oulema melanopus), Cucurbit leaf beetle (Aulacophora femoralis), Striped flea beetle (Phyllotreta striolata), Cabbage flea beetle (Phyllotreta cruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea Chrysomelidae, including the beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicaria), sweet potato leaf beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), rice spur beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-legged tortoise beetle (Laccoptera quadrimaculata), and tobacco flea beetle (Epitrix hirtipennis); seedcorn beetle (Stenolophus lecontei), slender seedcorn beetle (Clivina Carabidae, such as impressifrons;Scarabaeidae, such as the Japanese beetle (Anomala cuprea), the Japanese beetle (Anomala rufocuprea), the Japanese beetle (Anomala albopilosa), the Japanese beetle (Popillia japonica), the long-legged beetle (Heptophylla picea), the European chafer (Rhizotrogus majalis), the black beetle (Tomarus gibbosus), the Phyllophaga spp., such as the Holotrichia spp. and the June beetle (Phyllophaga crinita), and the Diloboderus spp., such as Diloboderus abderus;Boll weevil (Araecerus coffeae), sweet potato weevil (Cylas formicarius), potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white earth weevil (Rhabdoscelus lineatocollis), boll weevil (Anthonomus grandis), grass band weevil (Sphenophorus venatus), Southern corn billbug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust gourd weevil (Scepticus griseus), brown gourd weevil (Scepticus uniformis), Brazilian bean weevil (Zabrotes subfasciatus), pine bark beetle (Tomicus piniperda), coffee berry borer (Hypothenemus hampei), Aracanthus spp. such as Aracanthus mourei, cotton root borer (Eutinobothrus brasiliensis), etc. Curculionidae; Tenebrionidae; Tribolium castaneum; Tribolium confusum; Epilachna Coccinellidae (ladybird beetles) such as Lyctus vigintioctopunctata; Bostrychidae (bostrychidae) such as Lyctus brunneus; Ptinidae (leaf beetles);Cerambycidae, such as the Asian longhorn beetle (Anoplophora malasiaca) and Migdolus fryanus; Elateridae, such as the Okinawan wireworm beetle (Melanotus okinawensis), the brown-headed wireworm beetle (Agriotes fuscicollis), the comb beetle (Melanotus legatus), the Anchastus spp., the Conoderus spp., the Ctenicera spp., the Limonius spp., and the Aeolus spp.; Staphylinidae, such as the blue-leaf rove beetle (Paederus fuscipes). ;

[0090] Thysanoptera (Thysanoptera) pests {e.g., Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, and Echinothrips americanus; Phlaeothripidae such as Haplothrips aculeatus}.

[0091] Diptera pests {e.g., Anthomyiidae such as seed fly (Delia platura) and onion fly (Delia antiqua); Ulidiidae such as sugar beetroot maggot (Tetanops myopaeformis); Agromyzidae such as rice leafminer (Agromyza oryzae), tomato leafminer (Liriomyza sativae), bean leafminer (Liriomyza trifolii), and groundminer (Chromatomyia horticola); Chloropidae such as rice stemminer (Chlorops oryzae); melon fly (Bactrocera cucurbitae), oriental fruit fly (Bactrocera dorsalis), and eggplant fly (Bactrocera Tephritidae, such as Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, and Ceratitis capitata; Ephydridae, such as Hydrellia griseola, Hydrellia philippina, and Hydrellia sasakii; Drosophila suzukii, such as Drosophila suzukii; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata; Bradysia spp. Sciaridae (Fungi gnats) such as Sciaridae (Sciaridae), Hessian fly (Mayetiola destructor) and rice gall midge (Orseolia oryzae) and Cecidomyiidae (Cicidomyiidae), such as Diopsis macrophthalma;Tipulidae, including the Japanese cranefly (Tipula aino), the common cranefly (Tipula oleracea), and the European cranefly (Tipula paludosa).

[0092] Hymenoptera pests {for example, Tenthredinidae such as Athalia rosae and Athalia japonica; Formicidae such as Solenopsis spp. and Brown leaf-cutting ant Atta capiguara}.

[0093] Orthoptera pests {e.g., Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red locust (Nomadacris septemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two-striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucida), Desert grasshopper (Schistocerca Acrididae, such as the Japanese grasshopper (Oxya gregaria), the yellow-winged locust (Gastrimargus musicus), the spur-throated locust (Austracris guttulosa), the oriental grasshopper (Oxya yezoensis), the long-winged locust (Oxya japonica), and the Taiwan grasshopper (Patanga succincta); Gryllotalpidae, such as the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and Tettigoniidae, such as the Mormon cricket (Anabrus simplex).

[0094] Blattodea (for example, the family Blattellidae, such as the German cockroach (Blattella germanica)); the family Blattidae, such as the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the brown cockroach (Periplaneta brunnea), the Asian cockroach (Blatta orientalis), the Japanese cockroach (Periplaneta japonica), and the American cockroach (Periplaneta australasiae); the Japanese termite (Reticulitermes speratus), the Formosan termite (Coptotermes formosanus), the American dry-wood termite (Incisitermes minor), the Formosan termite (Cryptotermes domesticus), and the Formosan termite (Odontotermes formosanus, Koshun termite (Neotermes koshunensis), Satsuma termite (Glyptotermes satsumensis), Nakajima termite (Glyptotermes nakajimai), Katan termite (Glyptotermes fuscus), Hodotermopsis sjostedti, Koshu termite (Coptotermes guangzhouensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Formosan termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Snocapritermes (Pericapritermes nitobei), Mushae termite (Sinocapritermes mushae), Cornitermes cumulans, etc. (Termitidae)

[0095] Acari (for example, Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligonychus spp.); Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, and Aculus spp. Eriophyidae, such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae, such as Polyphagotarsonemus latus; Tenuipalpidae, such as Brevipalpus phoenicis; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanensis, Dermacentor variabilis, Ixodes ovatus, Ixodes persulcatus, and Ixodes black-legged ticks. Ixodidae, including Amblyomma scapularis, Amblyomma americanum, Boophilus microplus, and Rhipicephalus sanguineus;Acaridae (Acarid mites) such as Tyrophagus putrescentiae and Tyrophagus similis; Pyroglyphidae (Dermatophagoides farinae and Dermatophagoides pteronyssinus); Cheyletidae (Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei, Cheyletiella yasguri); Sarcoptidae (Sarcoptes scabiei, Otodectes cynotis, Sarcoptes scabiei, Demodex canis); canis, etc.; Listrophoridae; Haplochthoniidae; Macronyssidae, such as Ornithonyssus bacoti and Ornithonyssus sylviarum; Dermanyssidae, such as Dermanyssus gallinae; Trombiculidae, such as Leptotrombidium akamushi;

[0096] Plant-parasitic nematodes {e.g., Aphelenchida nematodes such as the rice root nematode (Aphelenchoides besseyi), the strawberry nematode (Aphelenchoides fragariae), the peel nematode (Aphelenchoides ritzemabosi), and the pine wood nematode (Bursaphelenchus xylophilus), the potato white cyst nematode (Globodera pallida), the potato cyst nematode (Globodera rostochiensis), the wheat cyst nematode (Heterodera avenae), the soybean cyst nematode (Heterodera glycines), the sugar beet cyst nematode (Heterodera schachtii), the clover cyst nematode (Heterodera trifolii), and the root-knot nematode (Meloidogyne nematode)} arenaria), northern root-knot nematode (Meloidogyne hapla), sweet potato root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), apple root-knot nematode (Meloidogyne mali), southern root-leach nematode (Pratylenchus coffeae), sawtooth root-leach nematode (Pratylenchus drenatus), channel root-leach nematode (Pratylenchus loosi), wheat root-leach nematode (Pratylenchus neglectus), northern root-leach nematode (Pratylenchus penetrans), walnut root-leach nematode (Pratylenchus vulnus), citrus root-leach nematode (Radopholus citrophilus), banana root-leach nematode (Radopholus similis, etc.}

[0097] The insect species targeted for control in the present invention (insect species for which the compound represented by formula (1) is effective in controlling) can also be used to control pests such as sanitary pests, shell-storing pests, clothing pests, house pests, and parasitic insects. The control effect is particularly excellent against ectoparasites that harm humans and animals. The ectoparasites targeted for control include those that infest the back, armpits, lower abdomen, inner thighs, etc. of a host animal and live by obtaining nutrients such as blood and dander from animals and birds, and those that fly to the back, buttocks, etc. of a host animal and live by obtaining nutrients such as blood and dander from animals and birds. Examples of ectoparasites include mites, lice, and fleas.

[0098] Host animals on which the control agent of the present invention is effective include dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, and ferrets; pet birds (e.g., pigeons, parrots, mynahs, Java sparrows, parakeets, Bengalese finches, and canaries); cattle, horses, pigs, sheep, and goats; poultry (e.g., ducks, chickens, quails, and geese); and honeybees (e.g., European honeybees and Japanese honeybees).

[0099] That is, the pest control agent of the present invention is effective as an animal ectoparasite control agent for protecting the above animals and birds.

[0100] The target mites (Acari) include the following pests: Mites of the order Mesostigmata (e.g., Dermanyssidae, such as Dermanyssus gallinae); mites of the family Macronyssidae, including Ornithonyssus sylviarum, Ornithonyssus bursa, and Ornithonyssus bacoti; mites of the genus Laelaps, including Laelaps echidninus, Laelaps jettmari, and Tropilaeps clarae; mites of the genus Varroa spp.), mites of the family Varroidae, which includes Varroa destructor, Varroa jacobsoni, and Varroa underwoodi. Ticks of the order Metastigmata (e.g., ticks of the family Argasidae, including Argas spp. such as Argas persicus, Argas reflexus, and Ornithodoros spp. such as Ornithodoros moubata); ticks of the genus Haemaphysalis such as Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, and Haemaphysalis reachii (e.g., ticks of the family Argasidae, including Argas spp. such as Argas persicus, Argas reflexus, and Ornithodoros spp. such as Ornithodoros moubata); ticks of the genus Haemaphysalis such as Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, and Haemaphysalis reachii (e.g., ticks of the family Haemaphysalis leachi, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, Haemaphysalis yeni, Haemaphysalis campanulata, Haemaphysalis pentalagi, Haemaphysalis flava, Haemaphysalis megaspinosa, Haemaphysalis japonica, Haemaphysalis douglasi, Amblyomma spp. including Amblyomma americanum, Amblyomma variegatum, and Amblyomma maculatum. maculatum, Amblyomma hebraeum, Amblyomma cajennense, Amblyomma testudinarium, Ixodes spp.) ticks (Ixodes ricinus), Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus, Ixodes persulcatus, Ixodes nipponensis, Boophilus species Rhipicephalus spp. include the cow tick (Rhipicephalus (Boophilus) microplus), Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, and Rhipicephalus (Boophilus) calceratus, as well as the brown dog tick (Rhipicephalus sanguineus), Rhipicephalus bursa, and Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Dermacentor spp.Mites of the family Ixodidae, including Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, and Dermacentor variabilis. Acaridida mites of the order Astigmata (e.g., Psoroptidae spp., including Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes spp., Chorioptes bovis, Otodectes cynotis); Sarcoptes spp., Sarcoptes scabiei, Sarcoptes spp. ... canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes equi, Sarcoptes suis, Notoedres spp. (Notoedres cati); Knemidokoptidae (Knemidokoptes spp. (Knemidokoptes mutans)). Prostigmata order Actinedida (e.g. Demodex spp. Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Demodex cati; Trombicula spp. Trombiculidae including Trombicula alfreddugesi and Trombicula akamushi).

[0101] The target lice (Phthiraptera) include the following pests: Lice of the suborder Anoplura {e.g., lice of the family Haematopinidae, including the horse louse (Haematopinus asini), the cow louse (Haematopinus eurysternus), and the pig louse (Haematopinus suis) of the genus Haematopinus; lice of the genus Linognathus, including the dog louse (Linognathus setosus), the cow louse (Linognathus vituli), the Linognathus ovillus, the Linognathus oviformis, the Linognathus pedalis, and the goat louse (Linognathus stenopsis, Solenopotes spp., and the hairy cow lice (Solenopotes capillatus) of the Linognathidae family. Biting louse of the suborder Amblycera (e.g., Menacanthus spp., including the chicken louse (Menacanthus stramineus), chicken horn louse (Menacanthus cornutus), and pale chicken louse (Menacanthus pallidulus); biting louse of the family Menoponidae, including Menopon spp., including the chicken louse (Menopon gallinae)). Biting louse of the suborder Ischnocera (e.g., Columbicola spp., pigeon louse (Columbicola columbae), Cuclotogaster spp., leaf louse (Cuclotogaster heterographus), Goniodes spp., chicken louse (Goniodes dissimilis), ground louse (Goniodes gigas), chicken louse (Goniodes gallinae), chicken louse (Lipeurus caponis), and other biting louse of the family Philopteridae; Bovicola spp. Lice of the family Trichodectidae, including the cattle louse (Bovicola bovis), sheep louse (Bovicola ovis), Bovicola limbata, goat louse (Bovicola caprae), horse louse (Bovicola equi), dog louse (Trichodectes canis) of the genus Trichodectes, and cat louse (Felicola subrostrata) of the genus Felicola.

[0102] Targeted fleas (Siphonaptera) include the following pests: fleas of the Tungidae family, including the sand flea (Tunga penetrans) of the genus Tunga; dog fleas (Ctenocephalides canis) and cat fleas (Ctenocephalides felis) of the genus Ctenocephalides; hedgehog fleas (Archaeopsylla erinacei) of the genus Archaeopsylla; Asian mouse fleas (Xenopsylla cheopis) of the genus Xenopsylla; human fleas (Pulex irritans) of the genus Pulex; and chicken lift fleas (Echidnophaga spp.). fleas of the family Pulicidae, including the human flea (Ceratophyllus gallinacea); fleas of the family Ceratophyllidae, including the bird flea (Ceratophyllus gallinae), the Japanese rat flea (Ceratophyllus anisus), and the European mouse flea (Nosopsyllus fasciatus); fleas of the family Leptopsyllidae, including the blind rat flea (Leptopsylla segnis).

[0103] Other target ectoparasites include pests of the order Hemiptera, such as insects of the family Cimicidae, including bedbugs (Cimex lectularius) of the genus Cimex; and insects of the family Reduviidae, including Panstrongylus spp., Rhodnius spp., and Triatoma spp. It is also effective against Diptera pests, which are biting insects (chewing flies, adult blood-sucking flies, migratory dipteran larvae, and parasitic fly maggots). Diptera pests include the following: Nematocera {e.g., (a) Culex spp., Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Armigeres spp., Armigeres subalbatus, Anopheles spp., Anopheles gambiae, Anopheles maculipennis, Anopheles gambiae ... (b) mosquitoes of the Culicidae family, including Aedes spp., Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Aedes togoi, and Aedes vexans nipponii; (c) mosquitoes of the Simulium spp., including Simulium reptans, Simulium ornatum, Simulium venustum, Simulium salopiense, and Prosimulium spp. Black flies of the family Simuliidae, including the yellow-legged black fly (Prosimulium yezoense); Culiodes spp.Ceratopogonidae midges, including the Japanese midge (Culicoides arakawae), the pale-spotted midge (Culicoides pictimargo), the yellow midge (Culicoides kibunensis), the Japanese midge (Culicoides homotomus), the cow midge (Culicoides oxystoma), the Japanese midge (Culicoides nipponensis), the spotted midge (Culicoides punctatus), the mountain midge (Culicoides maculatus), and the Matsuzawa midge (Culicoides matsuzawai). Brachyceratops {e.g., (a) Tabanus spp. such as Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Tabanus trigonus, Tabanus chrysurus, Tabanus trigeminus, Tabanus fulvimedioides, Tabanus iyoensis, and Chrysops spp. such as Chrysops caecutiens, Chrysops relictus, and Chrysops alfonsinosus. Tabanidae horseflies, including Chrysops suavis and Chrysops japonicus; Muscina spp., including Musca domestica, Musca bezzii, Musca hervei, Musca conducens, Musca stabulans, Stomoxys spp., including Stomoxys calcitrans, Haematobia spp., including Haematobia irritans, Haematobia irritans exigua, Haematobia stimulans, and Fannia Flies of the family Muscidae, including the little house fly (Fannia canisularis spp.); flies of the family Glossinidae, including Glossina spp.; flies of the genus Melophagus (Melophagus spp.);Flies of the Hippoboscidae family, including the common pedigree fly (Melophagus ovinus); Calliphora spp., including the blowfly (Calliphora lata); Lucilia spp., including the sheep blowfly (Lucilia (Phaenicia) cuprina), the broad-legged blowfly (Lucilia (Phaenicia) sericata), and the green blowfly (Lucilia illustris); Chrysomyia spp., including the screwworm fly (Chrysomya hominivorax), Chrysomya chloropyga, and Chrysomya veziana Flies of the family Calliphoridae, including Bombyx mori (Burberry Flies); Cuterebrinae, including Cuterebra spp.; Hypodermatinae, including Hypoderma spp., such as Hypoderma bovis and Hypoderma lineatum; Gasterophilinae, including Gasterophilus spp., such as Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, and Gasterophilus nigricornis. nigricornis, Gasterophilus pecorum, and flies of the Oestrinae subfamily, including the sheep fly Oestrus spp., Oestrus ovis.

[0104] When the compound represented by formula (1) is used as an agricultural or horticultural insecticide, the compound represented by formula (1) may be used as is, or may be mixed with a suitable solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, other formulation adjuvant, etc. to prepare an agrochemical formulation. Examples of the agrochemical formulation include emulsifiable concentrates, EW formulations, liquid formulations, suspensions, wettable powders, water dispersible granules, dusts, DL dusts, powder granules, granules, tablets, oils, aerosols, flowable formulations, dry flowable formulations, and microcapsules. These agrochemical formulations can be used in any dosage form. The term "carrier" used in the present invention refers to a solid carrier, liquid carrier, gaseous carrier, etc.

[0105] Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, silica sand, silica stone, zeolite, perlite, attapulgite, pumice, ammonium sulfate, sodium sulfate, and urea. Examples of the liquid carrier include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol, and propylene glycol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; aliphatic hydrocarbons such as n-hexane, kerosene, and heating oil; aromatic hydrocarbons such as toluene, xylene, and methylnaphthalene; ethers such as diethyl ether, dioxane, and tetrahydrofuran; esters such as ethyl acetate; nitriles such as acetonitrile and isobutyronitrile; acid amides such as dimethylformamide and dimethylacetamide; vegetable oils such as soybean oil and cottonseed oil; dimethyl sulfoxide; and water. Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide, and dimethyl ether. Examples of the surfactant and dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, alkyl sulfosuccinates, formalin condensates of alkyl naphthalene sulfonates, polycarboxylates, POE polystyrylphenyl ether sulfates and phosphates, and POE-POP block polymers. Furthermore, examples of the formulation adjuvants include carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, polyethylene glycol, liquid paraffin, calcium stearate, antifoaming agents, preservatives, etc. The above-mentioned various carriers, surfactants, dispersants, and formulation adjuvants can be used either alone or in combination, as required.

[0106] The content of the compound represented by formula (1), which is the active ingredient in the pesticide formulation, is not particularly limited, but is preferably 1 to 75% by weight for emulsifiable concentrates, 0.3 to 25% by weight for dusts, 1 to 90% by weight for wettable powders, and 0.1 to 10% by weight for granules.

[0107] When the compound represented by formula (1) is used as an acaricide for controlling mites that parasitize livestock such as cattle and pigs, and pets such as dogs and cats, the active ingredient can be used in an amount of 0.01 to 1000 mg per kg of the host animal. Acaricides for control can be applied by known veterinary methods. For example, when the purpose is systemic control, they can be administered to animals by tablets, capsules, immersion liquids, inclusion in feed, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc., and when the purpose is non-systemic control, they can be administered by spraying, pouring, spot-on, etc. of oily or aqueous liquids, or by kneading the acaricide into resin, molding the kneaded product into a suitable shape such as a collar or ear tag, and attaching it to the animal.

[0108] The pesticide according to the present invention can be used as it is or after dilution. The pesticide according to the present invention can be mixed or used in combination with other insecticides, nematicides, fungicides, miticides, herbicides, plant growth regulators, fertilizers, etc. Examples of pesticides that can be mixed or used in combination include those listed in the Pesticide Manual (18th edition, published by The British Crop Protection Council), Shibuya Index (SHIBUYA INDEX 17th edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP), Mode of Action Classification Scheme Version 9.3, published by IRAC, and FRAC Code List (C) 2020: Fungicides sorted by mode of action, 2020 edition, published by FRAC) and those whose structures can be identified on the Internet (http: / / www.alanwood.net / pesticides / sitemap.html).

[0109] More specifically, the insecticides, nematicides and acaricides include the following compounds: Alanycarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathioca carbamate compounds such as rb), isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, metolcarb, fenothiocarb, and fenoxycarb; Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyfos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, etoprophos, famphur, fenamifos, fenitrothion, fenthion, fosthiazate, heptenophos, and imicyafos , isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton ethyl, parathion, parathion-methyl, PAP, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos organophosphate ester compounds such as terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazophos, phenthoate, fonofos, and tribufos; Organochlorine compounds such as endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, and methoxychlor; phenylpyrazole compounds such as acetoprole, fipronil, ethiprole, pyrafluprole, pyriprole, and flufiprole; metadiamide compounds such as broflanilide; isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, fluxametamide, lotilaner, and isocycloseram; Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esphethrin esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin,pyrethroid compounds such as tetramethrin, tralomethrin, transfluthrin, metoxadiazone, metofluthrin, profluthrin, pyrethrum, terallethrin, momfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, and protrifenbut; Neonicotinoid compounds such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam; sulfoxamine compounds such as sulfoxaflor, butenolide compounds such as flupyradifurone, Mesoionic compounds such as triflumezopyrim and dichloromezotiaz; 2-aminopyridine compounds such as flupyrimin, spinosyn compounds such as spinosad and spinetoram; Macrolide compounds such as abamectin, ivermectin, emamectin benzoate, milbemectin, and lepimectin; Juvenile hormone-like compounds such as hydroprene, quinoprene, diofenolan, and methoprene; 4-phenoxyphenoxy compounds such as pyriproxyfene, pyridine azomethine compounds such as pymetrozine, pyridinecarboxamide compounds such as flonicamid; oxazole compounds such as ethoxazole; Bacillus thuringiensis and Bacillus sphaericus agents such as Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, and Bt subsp. tenebrionis, and the insecticidal proteins they produce; insecticidal proteins produced by the Bt crops corresponding to the above; thiourea compounds such as diafenthiuron; organometallic compounds such as azocyclotin, cyhexatin, and fenbutatin oxide; Sulfite ester and diphenyl ether compounds such as propargite, Diphenyl sulfone compounds such as tetradifon, Pyrrole compounds such as chlorfenapyr and tralopyril, Dinitro compounds such as DNOC, Nereistoxin analogues such as bensultap, cartap, thiocyclam, thiosultap, and thiosultap sodium; benzoyl urea compounds such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and bistrifluron; thiadiazine compounds such as buprofezin, triazole compounds such as cyromazine, diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide; Amidine compounds such as amitraz amidinohydrazone compounds such as hydramethylnon, naphthoquinone compounds such as acequinocyl; Strobilurin compounds such as fluacrypyrim, pyriminostrobin, and flufenoxystrobin; quinazoline compounds such as fenazaquin, phenoxypyrazole compounds such as fenpyroximate; phenoxyethylamine compounds such as pyrimidifen, pyridazinone compounds such as pyridaben, pyrazole-4-carboxamide compounds such as tebufenpyrad, tolfenpyrad, pyflubumide, dimpropyridaz; hydrazinecarboxamide compounds such as metaflumizone, Tetronic acid and tetramic acid compounds such as spirodiclofen, spirotetramat, spiromesifen, and spiropidion; beta-ketonitrile compounds such as cyflumetofen, cyenopyrafen, and cyetpyrafen; phthalic acid amide compounds such as flubendiamide, anthranilic acid amide compounds such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, and tetrachlorantraniliprole; quinoxaline compounds such as quinomethionate, thiazolidinone compounds such as hexythiazox, hydrazine compounds such as bifenazate, pyridinamine compounds such as flufenerim, Aminoquinazoline compounds such as pyrifluquinazon, 6-phenoxyquinoline compounds such as flometoquin, pyridinylethylbenzamide compounds such as fluopyram; pyridinylcyclobutynylamide compounds such as cyclobutrifluram; sulfonamide compounds such as fluazaindolizine and amidoflumet; pyridylpyrazole compounds such as tyclopyrazoflor, oxadiazole compounds such as tioxazafen; Benzoxazole compounds such as oxazosulfyl. Other insecticides, nematicides, and miticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, indoxacarb, and piperonyl butoxide. butoxide, chlordimeform, pyridalyl, azadirachtin, benzoxymate, afidopyropen, fluhexafon, fluensulfone, benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate Examples of suitable pesticides include entomopathogenic bacteria, insect pathogenic viruses, insect pathogenic fungi, and other microbial pesticides.

[0110] Examples of disinfectants that can be used include: Phenylamido compounds such as metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, chiralaxyl, ofurase, furalaxyl, and cyprofuram; Hydroxypyrimidine compounds such as bupyrimate, dimethilimol, and ethilimol; isoxazole compounds such as hymexazole and hydroxyisoxazole; piperidinylthiazole isoxazoline compounds such as oxathiapiprolin and fluoxapiprolin; isothiazolone compounds such as octhilinone, Carboxylic acid compounds such as oxolinic acid, benomyl, thiophanate-methyl, carbendazole, fuberidazole, thiabendazole, debacarb, and other benzimidazole-thiophanate compounds; N-phenylcarbamate compounds such as diethofencarb, toluamide compounds such as zoxamide, Ethylaminothiazolecarboxamide compounds such as ethaboxam, phenylurea compounds such as pencycuron, pyridinylmethylbenzamide compounds such as fluopicolide and fluopimomide; pyrimidineamine compounds such as diflumetorim and bupirimate; benzanilide compounds such as benodanil, flutolanil, and mepronil; phenyloxoethylthiopheneamide compounds such as isofetamide; pyridinylethylbenzamide compounds such as fluopyram; furancarboxamide compounds such as fenfuram; Oxathiincarboxamide compounds such as oxycarboxin and carboxin; thiazolecarboxamide compounds such as thifluzamide, pyrazole-4-carboxamide compounds such as fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, inpyrfluxam, fluindapyr, isoflucypram, pyrapropoyne, and flubeneteram; pyridinecarboxamide compounds such as boscalid, Strobilurin compounds such as azoxystrobin, coumetoxystrobin, kresoxim-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, metominostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, flufenoxystrobin, phenaminestrobin, enoxastrobin, coumoxystrobin, mandestrobin, and triclopyricarb; oxazolidinedione compounds such as famoxadone, Imidazolinone compounds such as fenamidone, benzyl carbamate compounds such as triclopyricarab and pyribencarb; cyanoimidazole compounds such as cyazofamid, sulfamoyltriazole compounds such as amisulbrom; Dinitrophenylcroton compounds such as binapacryl, meptyldinocap, and dinocap; 2,6-dinitroaniline compounds such as fluazinam, pyrimidinone hydrazone compounds such as ferimzone, Organic and inorganic metal compounds such as fentin acetate, fentin chloride, fentin hydroxide, triphenyltin hydroxide, fenthin acetate, and oxine copper; thiophenecarboxamide compounds such as silthiofam; triazolopyrimidine amine compounds such as ametoctradin; anilinopyrimidine compounds such as mepanipyrim, nitrapyrin, pyrimethanil, and cyprodinil; enopyranuronic acid antibiotics such as blasticidin-S, hexopyranosyl antibiotics such as kasugamycin and kasugamycin hydrochloride hydrate; glucopyranosyl antibiotics such as streptomycin, tetracycline antibiotics, such as oxytetracycline; Allyloxyquinoline compounds such as quinoxyfen, quinazoline compounds such as proquinazid, cyanopyrrole compounds such as fludioxonil and fenpiclonil, dicarboximide compounds such as fluoroimide, procymidone, iprodione, and vinclozolin; phosphorothiolate compounds such as edifenphos, iprobenfos, and pyrazophos; Dithiolane compounds such as isoprothiolane, Propylcarbamate compounds such as propamocarb and propamocarb hydrochloride; Bacillus species, such as Bacillus subtilis (strains QST713, FZB24, MBI600, D747) and the bactericidal proteins produced therefrom, and bactericidal proteins produced by said Bt crops; Terpene hydrocarbons and terpene alcohols such as extracts of Gosei-kajuput, piperazine compounds such as triforine, pyridine compounds such as pyrifenox and pyrisoxazole, pyrimidine compounds such as fenarimol and nuarimol; Azaconazole, bromuconazole, diniconazole, diniconazole-M, epoxyconazole, fluquinconazole, oxpoconazole, pefurazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole azole compounds such as iconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriafol, myclobutanil, paclobutrazol, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, and ipfentrifluconazole; Aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, Morpholine compounds such as flumorph and pyrimorph; Piperidine compounds such as piperalin and fenpropidin; Spiroketalamine compounds such as spiroxamine, hydroxyanilide compounds such as fenhexamid, aminopyrazolinone compounds such as fenpyrazamine, Thiocarbamate and dithiocarbamate compounds such as ferbam, metam, metasulphocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate, propineb, thiuram, and pyributicarb; glucopyranosyl antibiotics such as validamycin, Nucleoside antibiotics such as mildiomycin and polyoxin, Valinamide carbamate compounds such as benthiavalicarb, benthiavalicarb-isopropyl, valifenalate, and iprovalicarb; mandelic acid amide compounds such as mandipropamid; Picolinamide compounds such as fenpicoxamid and florylpicoxamid; isobenzofuranone compounds such as fthalide, Pyrroloquinolinone compounds such as pyroquilone, triazolobenzothiazole compounds such as tricyclazole; cyclopropanecarboxamide compounds such as carpropamid; Carboxamide compounds such as diclocymet, propionamide compounds such as fenoxanil, benzothiadiazole compounds such as acibenzolar-S-methyl, Benzisothiazole compounds such as probenazole and dichlobentiazox, thiadiazolecarboxamide compounds such as tiadinil, isothiazolecarboxamide compounds such as isotianil, cyanoacetamide oxime compounds such as cymoxanil, ethylphosphonate compounds such as fosetyl, phthalamic acid compounds such as techlophthalam, benzotriazine compounds such as triazoxide, benzenesulfonic acid compounds such as flusulfamide, pyridazinone compounds such as diclomezine, phenylacetamide compounds such as cyflufenamide, benzophenone compounds such as metrafenone, benzoylpyridine compounds such as pyriophenone, cyanomethylene thiazolidine compounds such as flutianil; 4-quinolylacetic acid compounds such as tebufloquin, 3-phenoxyquinoline compounds such as ipflufenoquin, Organophosphate compounds such as fosetylaluminium and tolclofos-methyl, 1,2,4-thiadiazole compounds such as echlomezole, trifluoroethylcarbamate compounds such as tolprocarb, Copper compounds such as Bordeaux mixture, copper acetate, basic copper sulfate, copper oxychloride, copper hydroxide, and oxine-copper; Inorganic compounds such as copper and sulfur, N-halogenothioalkyl compounds such as captan, captafol, and folpet; Organochlorine compounds such as anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, and quintozene; Guanidine compounds such as iminoctadine acetate salt, iminoctadine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate salt, and albesilate; anthraquinone compounds such as dithianon; quinoxaline compounds such as quinomethionate, maleimide compounds such as fluoroimide; sulfenic acid compounds such as tolylfluanid and dichlofluanid; dinitrophenolic compounds such as dinobuton, cyclic dithiocarbamate compounds such as dazomet; anilide compounds such as pyraziflumid, nicotinic acid ester compounds such as aminopyrifen, tetrazolinone compounds such as methyltetraprole; Pyridazine compounds such as pyridaclomethyl.

[0111] Other fungicides include dipymetitrone, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium, bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodocarb, and prothiocarb.

[0112] The compound of the present invention represented by formula (1) or its N-oxide or a salt thereof (all of these are also referred to as "the compound of the present invention") can be used to control target pests by applying an effective amount to plants, soil, or animals. That is, a method for controlling pests in these fields is provided. Here, the control method according to the present invention also includes a method in which the compound of the present invention is applied by fumigation in an enclosed space. Agriculturally and horticulturally acceptable salts and veterinary acceptable salts can be selected as the "salt." The compounds of the present invention also enhance the vigor of crops by treating or contacting the crops, the seeds from which the crops grow, or the placenta of the crops in a biologically effective amount. When the target of treatment or contact is a seed, the amount of the compound of the present invention is not limited, but it is preferable that the compound of the present invention is contained in an amount of about 0.0001 to about 1% by mass of the whole seed after treatment. The present invention further provides the use of a compound of the present invention as an active ingredient in a composition for protecting animals and birds from parasitic invertebrate pests. The composition contains a compound of the present invention in an amount that is parasiticidally effective but not harmful to the target animal or bird. In this use, the compound of the present invention is contacted with the invertebrate pests or their habitat in a biologically effective amount to control the invertebrate pests.

[0113] Next, specific examples of the compound of the present invention are shown below.

[0114] A in formula (1) is A-1, R A In formula (1-7) where R is ethyl, 2 , R 3 , R 4 , and R 5 is a substituent described in Table 1-1, Table 1-2, Table 1-3, Table 1-4, Table 1-5 and Table 1-6, D is a substituent described in Table 2, E is a substituent described in Table 3, R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 2] [Table 3] [Table 4] [Table 5-1] [Table 5-2] [Table 6]

[0115] A in formula (1) is A-2, R A In formula (1-8) where R is ethyl, 1 , R 3 , R 4 , and R5 is a substituent listed in Table 7-1, Table 7-2, Table 7-3, Table 7-4, Table 7-5 and Table 7-6, D is a substituent listed in Table 2, E is a substituent listed in Table 3, R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 7-1] [Table 7-2] [Table 7-3] [Table 7-4] [Table 7-5] [Table 7-6]

[0116] A in formula (1) is A-4, R A In formula (1-9) where R is ethyl, 1 , R 2 , R 4 , and R 5 is a substituent listed in Table 8-1, Table 8-2, Table 8-3, Table 8-4, Table 8-5 and Table 8-6, D is a substituent listed in Table 2, E is a substituent listed in Table 3, R B and R D is a substituent listed in Table 4, and R Cis a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 8-1] [Table 8-2] [Table 8-3] [Table 8-4] [Table 8-5] [Table 8-6]

[0117] A in formula (1) is A-5, R A In formula (1-10) where R is ethyl, 3 , R 4 , and R 5 is a substituent listed in Table 9-1, Table 9-2, and Table 9-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 9-1] [Table 9-2] [Table 9-3]

[0118] A in formula (1) is A-6, R A In formula (1-11) where R is ethyl, 2 , R 4 , and R 5 is a substituent listed in Table 10-1, Table 10-2, and Table 10-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 10-1] [Table 10-2] [Table 10-3]

[0119] A in formula (1) is A-7, R A In formula (1-12) where R is ethyl, 2 , R 3 , and R 4 is a substituent listed in Table 11-1, Table 11-2, and Table 11-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 11-1] [Table 11-2] [Table 11-3]

[0120] A in formula (1) is A-8, R A In formula (1-13) where R is ethyl, 2 , R 3 , and R 5 is a substituent listed in Table 12-1, Table 12-2, and Table 12-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Table 12-1] [Table 12-2] [Table 12-3]

[0121] A in formula (1) is A-9, R A In formula (1-14) where R is ethyl, 3 , R 4 and R 5is a substituent listed in Table 9-1, Table 9-2, and Table 9-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group described in Tables 5-1 and 5-2, n is an integer described in Table 6, and R 6 is a substituent group described in Table 13. [ka] [Table 13]

[0122] A in formula (1) is A-3, R A In formula (1-15), where R 2 , R 3 , R 4 , and R 5 is a substituent described in Table 1-1, Table 1-2, Table 1-3, Table 1-4, Table 1-5 and Table 1-6, D is a substituent described in Table 2, E is a substituent described in Table 3, R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka]

[0123] A in formula (1) is A-10, R A In formula (1-16) where R is ethyl, 3 , R 4 , and R 5 is a substituent listed in Table 9-1, Table 9-2, and Table 9-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R Cis a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka]

[0124] A in formula (1) is A-11, R A In formula (1-17) where R is ethyl, 2 , R 4 , and R 5 is a substituent listed in Table 10-1, Table 10-2, and Table 10-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka]

[0125] A in formula (1) is A-12, R A In formula (1-18) where R is ethyl, 2 , R 3 , and R 4 is a substituent listed in Table 11-1, Table 11-2, and Table 11-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka]

[0126] A in formula (1) is A-13, R A In formula (1-19) where R is ethyl, 2 , R 3 , and R 5is a substituent listed in Table 12-1, Table 12-2, and Table 12-3, D is a substituent listed in Table 2, E is a substituent listed in Table 3, and R B and R D is a substituent listed in Table 4, and R C is a substituent group shown in Tables 5-1 and 5-2, and n is an integer shown in Table 6. [ka] [Example]

[0127] <Synthesis Example> The present invention will be described in detail below with reference to examples, but is not limited to these examples. In the NMR data, "s" indicates singlet, "d" indicates doublet, "t" indicates triplet, "q" indicates quartet, "m" indicates multiplet, and "broad" indicates a broad line, and J indicates a coupling constant.

[0128] Synthesis Example 1-1: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)picolinonitrile [ka] 5-Bromo-3-(ethylthio)picolinonitrile (0.48 g, 1.97 mmol) prepared by the method described in WO2017 / 016922A1, p. 57, was dissolved in 1,4-dioxane (25 mL). The system was degassed using a pump and then purged with nitrogen. Dichlorobis(triphenylphosphine)palladium(II) (0.14 g, 0.20 mmol) was added and the mixture was heated and stirred at 60°C for 10 minutes under a nitrogen atmosphere. (4-(trifluoromethyl)phenyl)boronic acid (0.45 g, 2.37 mmol) and 2M aqueous sodium carbonate (5 mL) were then added. The mixture was degassed again, purged with nitrogen, and stirred under reflux for 2 hours. After cooling to room temperature, ethyl acetate and water were added, and the mixture was filtered through a filter aid to remove insoluble material. Water was added to the filtrate, which was then extracted twice with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target product (0.60 g, 98.6%). 1 H NMR(CDCl3) δ 8.69(1H, d, J=1.8Hz), 7.87(1H, d, J=2.1Hz), 7.80(2H, d, J=8.4Hz), 7.70(2H, d, J=8.4Hz), 3.13(2H, q, J=7.5Hz), 1.43(3H, t, J=7.5Hz)

[0129] Synthesis Example 1-2: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 39) [ka] 5-(Trifluoromethyl)pyridin-2-amine (106 mg, 0.65 mmol) was dissolved in N,N-dimethylformamide (4 mL), and sodium hydride (55% content, 31 mg, 0.71 mmol) was added, followed by stirring at room temperature for 15 minutes. The product of Synthesis Example 1-1 (200 mg, 6.49 mol) was added thereto, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was extracted twice with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography, then suspended in a mixture of ethyl acetate and hexane, and the solid was collected by filtration and dried to obtain the target product. 1 H NMR(CDCl3) δ 10.07(1H, broad), 8.65(1H, s), 8.55(1H, d, J=1.8Hz), 7.86(1H, dd, J=8.4Hz, 2.4Hz), 7.84(1H, d, J=2.1Hz), 7.78(2H, d, J=8.1Hz), 7.72(2H, d, J=8.1Hz), 7.46(1H, d, J=8.4Hz), 2.97(2H, q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)

[0130] Synthesis Example 1-3: Preparation of 3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 40) [ka] The product of Synthesis Example 1-2 (0.27 g, 0.57 mmol) was dissolved in dichloromethane (5.5 mL), 3-chloroperbenzoic acid (65%, 0.31 g, 1.15 mmol) was added, and the mixture was stirred at room temperature for 18 hours. Aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target product (0.26 g, 91.5%). 1H NMR(CDCl3) δ 10.17(1H, broad), 9.05(1H, d, J=2.1Hz), 8.71(1H, d, J=1.5Hz), 8.69(1H, s), 7.95-7.75(6H, m), 7.20(1H, d, J=2.4Hz), 4.05(2H, q, J=7.5Hz), 1.42(3H, t, J=7.5Hz)

[0131] Synthesis Example 1-4: Preparation of N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 41) [ka] The product of Synthesis Example 1-3 (0.20 g, 0.40 mmol) was dissolved in dichloromethane (4 mL), and acetic anhydride (0.11 mL, 1.2 mmol), triethylamine (0.33 mL, 2.4 mmol), and N,N-dimethylaminopyridine (catalytic amount) were added and stirred at room temperature for 24 hours. The reaction solution was concentrated under reduced pressure, and the resulting crude product was purified by silica gel chromatography to obtain the target product (0.16 g, 72.0%). 1 H NMR(CDCl3) δ 13.41(1H, s), 9.04(1H, d, J=2.1Hz), 8.81(1H, s), 8.51(1H, d, J=2.1Hz), 8.01(1H, dd, J=8.7Hz, 2.4Hz), 7.85-7.75(4H, m), 7.38(1H, d, J=8.7Hz), 3.49(2H, q, J=7.5Hz), 2.23(3H, s), 1.35(3H, t, J=7.5Hz)

[0132] Synthesis Example 1-5: N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 42) and Preparation of N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)((1-methyl-5-(trifluoromethyl)pyridin-2(1H)-ylidene)amino)methylene)acetamide (Compound No. 85) [ka] [ka] The product of Synthesis Example 1-4 (0.10 g, 0.18 mmol) was dissolved in N,N-dimethylformamide (2 mL). Sodium hydride (55% content, 10 mg, 0.23 mmol) was added under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. Iodomethane (28 mg, 0.20 mmol) was added, and the mixture was returned to room temperature and stirred at the same temperature for 2 hours. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target compounds, Compound 42 (44 mg, 42.9%) and Compound 85 (22 mg, 21.4%). compound 42 1 H NMR(CDCl3) δ 8.81(1H, s), 8.29(1H, s), 8.20(1H, s), 7.90-7.60(5H, m), 7.15(1H, d, J=8.4Hz), 3.80-3.20(5H, m), 2.32(3H, s), 1.35(3H, t, J=7.5Hz) compound 85 1H NMR(CDCl3) δ 9.05(1H, d, J=.21Hz), 8.30(1H, d,J=2.1Hz), 8.26(1H, s), 7.90-7.70(5H, m), 8.70(1H, d, J=8.7Hz), 3.56(3H, s), 3.51(2H, q, J=7.5Hz), 2.23(s, 3H), 1.34(3H, t, J=7.5Hz)

[0133] Synthesis Example 2-1: Preparation of 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)picolinonitrile [ka] 5-Bromo-3-(ethylthio)picolinonitrile (1.00 g, 4.11 mmol) prepared by the method described in WO2017 / 016922A1, p. 57 was dissolved in N,N-dimethylformamide (10 mL). 1H-1,2,3-triazole (0.31 g, 4.49 mmol) and potassium carbonate (0.85 g, 6.15 mmol) were added and stirred at 80 °C for 5 hours. After cooling to room temperature, water was added, and the mixture was extracted twice with ethyl acetate and washed with saturated brine. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target product (0.49 g, 51.5%). 1 H NMR(CDCl3) δ 9.21(1H, d, J=2.4Hz), 8.36(1H, d, J=2.1Hz), 7.93(2H, s), 3.17(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)

[0134] Synthesis Example 2-2: Preparation of 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 17) [ka] 5-(Trifluoromethyl)pyridin-2-amine (130 mg, 0.80 mmol) was dissolved in N,N-dimethylformamide (4 mL), and sodium hydride (55% content, 35 mg, 0.89 mmol) was added, followed by stirring at room temperature for 15 minutes. The product of Synthesis Example 2-1 (186 mg, 0.80 mol) was added thereto, followed by stirring at room temperature for 4 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate and washed with saturated brine. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography, then suspended in a mixture of ethyl acetate and hexane, and the solid was filtered and dried to obtain the target product (92 mg, 29.1%). 1 H NMR(CDCl3) δ 10.06(1H, broad), 9.08(1H, d, J=2.1Hz), 8.65(1H, s), 8.40(1H, d, J=2.1Hz), 7.90(2H, s), 7.86(1H, dd, J=8.7, 2.7Hz), 7.45(1H, d, J=8.4Hz), 3.02(2H, q, J=7.5Hz), 1.48(3H, t, J=7.5Hz)

[0135] Synthesis Example 2-3: Preparation of 3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 18) [ka] The product of Synthesis Example 2-2 (62 mg, 0.16 mmol) was dissolved in dichloromethane (2.5 mL), 3-chloroperbenzoic acid (65%, 86 g, 0.32 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target product (45 mg, 67.1%). 1H NMR(CDCl3) δ 9.55(1H, d, J=2.4Hz), 9.18(1H, d, J=1.8Hz), 8.68(1H, s), 8.05-7.92(3H, m), 7.88(1H, dd, J=8.7Hz, 2.1Hz), 7.20(1H, d, J=8.7Hz), 4.07(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)

[0136] Synthesis Example 3-1: Preparation of 3-(ethylthio)-5-(4-iodo-2H-1,2,3-trizol-2-yl)picolinonitrile [ka] 4-Iodo-2H-1,2,3-triazole (1.42 g, 7.28 mmol) prepared by the method described in Tetrahedron Letters (2017), 58(32), 3188-3190 was dissolved in N,N-dimethylformamide (10 mL). 5-Bromo-3-(ethylthio)picolinonitrile (1.77 g, 7.28 mmol) prepared by the method described in WO2017 / 016922A1, p. 57 and potassium carbonate (1.21 g, 8.74 mmol) were added and stirred at 110 °C for 2 h. After cooling to room temperature, water was added and the mixture was extracted four times with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the desired product (1.55 g, 59.6%). 1 H NMR(CDCl3) δ 9.16(1H, d, J=2.1Hz), 8.30(1H, d, J=2.4Hz), 7.95(1H, s), 3.17(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)

[0137] Synthesis Example 3-2: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)-2H-1,2,3-triazol-2-yl)picolinonitrile [ka] Dimethyl sulfoxide (20 mL) was added to the product of Synthesis Example 3-1 (1.50 g, 4.20 mmol), copper(I) iodide (0.240 g, 1.01 mmol), and 1,10-phenanthroline (0.228 g, 1.01 mmol). Under stirring, potassium fluoride (1.22 g, 16.80 mmol) was added, the reactor was degassed, and the atmosphere inside was replaced with nitrogen gas. Trimethyl borate (2.34 mL, 16.80 mmol) and trifluoromethyltrimethylsilane (3.08 mL, 16.80 mmol) were added, and the mixture was stirred at 80°C for 4 hours. Water was added to the reaction mixture, diluted with ethyl acetate, and filtered using a filter aid. The filtrate was separated with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target product (318 mg, 25.2%). 1 H NMR(CDCl3) δ 9.21(1H, d, J=2.1Hz), 8.37(1H, d, J=2.1Hz), 8.15(1H, s), 3.19(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)

[0138] Synthesis Example 3-3: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)-2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide [ka] The product of Synthesis Example 3-2 (0.58 mg, 1.94 mmol) was dissolved in toluene (30 mL), and the reactor was degassed and purged with nitrogen. 1.8 M trimethylaluminum (2.15 mL, 3.88 mmol) was added and stirred at room temperature for 1 hour. 5-(trifluoromethyl)pyridin-2-amine (0.16 g, 0.96 mmol) was then added and stirred at 80 °C for 10 hours. Water was added to the reaction mixture, and the mixture was filtered using a filter aid. The filtrate was extracted twice with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to yield a mixture of the target product and by-products (50 mg, 6% assuming all of it was the target product). 1 H NMR(CDCl3) δ 10.15(1H, broad), 9.09(1H, d, J=2.1Hz), 8.66(1H, s), 8.40(1H, d, J=2.1Hz), 8.12(1H, s), 7.88(1H, dd, J=8.4Hz, 2.1Hz), 7.60-7.43(1H, broad), 3.03(2H, q, J=7.2Hz), 1.49(3H, t, J=7.2Hz)

[0139] Synthesis Example 3-4: Preparation of 3-(ethylsulfonyl)-5-(4-(trifluoromethyl)-2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 82) [ka] The mixture obtained in Synthesis Example 3-3 (46 mg, 0.100 mmol assuming all of it was the target product) was dissolved in dichloromethane (10 mL), 3-chloroperbenzoic acid (65%, 58 mg, 0.219 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by silica gel chromatography to obtain the target product. 1H NMR(CDCl3) δ 9.65(1H, d, J=2.7Hz), 9.20(1H, s), 8.69(1H, s), 8.18(1H, s), 7.89(1H, dd, J=2.1Hz, 8.4Hz), 7.23(1H, broad), 4.07(2H, q, J=7.2Hz), 1.45(3H, t, J=7.5Hz)

[0140] Synthesis Example 4-1: Preparation of 3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidoyl chloride [ka] 3-(Ethylthio)-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinamide was prepared from 5-(trifluoromethyl)pyridin-2-amine, prepared by a method similar to that described in WO2014 / 021468A1, p. 156, and 3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)picolinic acid. Next, the amide (600 mg, 1.23 mmol) was dissolved in acetonitrile (40 mL), and carbon tetrachloride (0.5 mL, 2.06 mmol) and triphenylphosphine (1.98 g, 7.55 mmol) were added, followed by stirring under reflux for 2 hours. Approximately 80% of the acetonitrile in the reaction mixture was distilled off, and the mixture was purified by silica gel chromatography to obtain the target product (172 mg, 27.6%). 1 H NMR(CDCl3) δ 8.86(1H, s), 8.71(1H, d, J=1.5Hz), 8.03(1H, dd, J=8.1, 2.1Hz), 7.85(1H, s), 7.66(2H, d, J=8.7Hz), 7.39(2H, d, J=8.4Hz), 7.16(1H, d, J=8.4Hz), 3.05(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)

[0141] Synthesis Example 4-2: Preparation of 3-(ethylthio)-N'-methoxy-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 83) [ka] The following was carried out according to the method described in JP2004-210764A, p. 19. The product of Synthesis Example 4-1 (170 mg, 0.34 mmol) was dissolved in pyridine (5 mL), O-methylhydroxylamine hydrochloride (200 mg, 2.39 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. The pyridine in the reaction mixture was removed using an evaporator, water was added, and the pH of the reaction mixture was adjusted to 1 with dilute hydrochloric acid, followed by extraction twice with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography to obtain the target product (98 mg, 52.9%). 1 H NMR(CDCl3) δ 8.57(1H, d, J=2.1Hz), 8.26(1H, s), 8.11(1H, broad), 7.79(1H, d, J=2.1Hz), 7.68-7.54(3H, m), 7.36(2H, d, J=8.1Hz), 6.39(1H, d, J=8.7Hz), 4.05(3H, s), 2.98(q, 2H, J=7.5Hz), 1.31(3H, t, J=7.5Hz)

[0142] Synthesis Example 4-3: Preparation of 3-(ethylsulfonyl)-N'-methoxy-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 84) [ka] The product of Synthesis Example 4-2 (95 mg, 0.18 mmol) was dissolved in dichloromethane (10 mL), 3-chloroperbenzoic acid (65%, 50 mg, 0.19 mmol) was added, and the mixture was stirred at room temperature for 5 minutes. After confirming conversion to the sulfoxide by TLC, 3-chloroperbenzoic acid (65%, 50 mg, 0.19 mmol) was added, and the mixture was stirred at room temperature overnight. Most of the dichloromethane was removed using an evaporator. The resulting crude product was purified by silica gel chromatography to obtain the target product (83 mg, 82.2%). 1 H NMR(CDCl3) δ 8.97(1H, d, J=2.4Hz), 8.55(1H, d, J=2.4Hz), 8.18(1H, s), 8.12(1H, s), 7.72(2H, d, J=8.7Hz), 7.61(1H, dd, J=8.7, 2.1Hz), 7.40(2H, d, J=8.1Hz), 6.56(1H, d, J=8.7Hz), 4.01(3H, s), 3.64(2H, q, J=7.5Hz), 1.38(3H, t, J=7.5Hz)

[0143] Synthesis Example 5-1: Preparation of 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinamide [ka] 3-(Ethylthio)-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinamide (1.45 g, 1.23 mmol), prepared as an intermediate in Synthesis Example 4-1, was dissolved in dichloromethane (30 mL), and 3-chloroperbenzoic acid (65%, 1.58 g, 5.95 mmol) was added and stirred at room temperature for 2 hours. After most of the dichloromethane was distilled off using an evaporator, the precipitated solid was suspended in a mixed solvent of 75% ethyl acetate and 25% normal hexane, and the solid was collected by filtration and dried to obtain the target product (1.35 g, 87.1%). 1H NMR(CDCl3) δ 10.35(1H, s), 9.04(1H, d, J=2.1Hz), 8.82(1H, d, J=2.1Hz), 8.65(1H, s), 8.56(1H, d, J=8.7Hz), 8.01(1H, dd, J=9.0, 2.4Hz), 7.80-7.70(2H, m), 7.43(2H, d, J=8.1Hz), 4.00(2H, q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)

[0144] Synthesis Example 5-2: Preparation of 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline imidamide (Compound No. 93) [ka] The product of Synthesis Example 5-1 (218 mg, 0.42 mmol) was dissolved in acetonitrile (7 mL), and carbon tetrachloride (122 μL, 1.25 mmol) and triphenylphosphine (0.66 g, 2.52 mmol) were added, followed by stirring under reflux for 1 hour. After cooling to room temperature, 50% aqueous hydroxylamine solution (1 mL) was added dropwise, and the mixture was stirred overnight at room temperature. Most of the acetonitrile in the reaction mixture was distilled off, and the mixture was purified by silica gel chromatography to obtain the target product. 1 H NMR(CDCl3) δ 8.97(11H, d, J=2.4Hz), 8.70-8.30(1H, broad), 8.57(1H, d, J=2.1Hz), 8.14(1H, s), 7.76-7.69(2H, m), 7.65(1H, dd, J=8.7, 2.4Hz), 7.40(2H, d, J=8.1Hz), 6.63(1H, d, J=8.7Hz), 3.60(2H, q, J=7.5Hz), 1.36(3H, t, J=7.5Hz)

[0145] Synthesis Example 6: Preparation of 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(6-(trifluoromethyl)pyridin-3-yl)picoline imidamide (Compound No. 130) [ka] In the method described in Synthesis Example 5-2, the target product was obtained by carrying out the three steps in the same manner except that 6-(trifluoromethyl)pyridin-3-amine was used instead of 5-(trifluoromethyl)pyridin-2-amine used in the previous step (Synthesis Example 5-1) (intermediate step in Synthesis Example 4-1). 1 H NMR(CDCl3) δ 8.92(1H, d, J=2.1Hz), 8.56(1H, d, J=2.1Hz), 8.31(1H, s), 7.80-7.60(3H, m), 7.44-7.33(3H, m), 7.21(1H, dd, J=8.4, 2.4Hz), 3.71(2H, q, J=7.5Hz), 1.39(3H, t, J=7,5Hz)

[0146] Synthesis Example 7: Preparation of 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(2-(trifluoromethyl)pyridin-4-yl)picoline imidamide (Compound No. 135) [ka] In the method described in Synthesis Example 5-2, the target product was obtained by carrying out the three steps in the same manner except that 2-(trifluoromethyl)pyridin-4-amine was used instead of 5-(trifluoromethyl)pyridin-2-amine used in the previous step (Synthesis Example 5-1) (intermediate step in Synthesis Example 4-1). 1H NMR (heavy DMSO) δ 11.48(1H, s), 9.80(1H, s), 9.20(1H, d, J=2.1Hz), 8.64(1H, d, J=2.1Hz), 8.25(1H, d, J=5.7Hz), 8.06-7.98(2H, m), 7.56(2H, d, J=8.1Hz), 7.17(1H, d, J=2.1Hz), 6.75(1H, dd, J=5.7, 2,1Hz), 3.82(2H, q. J=7.5Hz), 1.29(3H, t, J=7.5Hz)

[0147] Synthesis Example 8: Preparation of 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyrazin-2-yl)picoline imidamide (Compound No. 133) [ka] In the method described in Synthesis Example 5-2, the target product was obtained by carrying out the three steps in the same manner as above, except that 2-(trifluoromethyl)pyrazine-5-amine was used instead of 5-(trifluoromethyl)pyridin-2-amine used in the previous step (Synthesis Example 5-1) (intermediate step in Synthesis Example 4-1). 1 H NMR(CDCl3) δ 8.98(1H, d, J=2.1Hz), 8.56(1H, d, J=2.1Hz), 8.38(1H, broad), 8.13(1H, s), 8.08(1H, s), 7.78-7.68(2H, m), 7.41(2H, d, J=8.1Hz), 3.56(2H, q, J=7.5Hz), 1.36(3H, t, J=7.5Hz)

[0148] The structures and NMR data of the compounds of the present invention are shown below, but the present invention is not limited to these compounds.

[0149] [ka]

Table 14-1

Table 14-2

Table 14-3

Table 14-4

Table 14-5

Table 14-6

Table 14-7

Table 14-8

Table 14-9

[0150]

change

Table 15

[0151]

change

Table 16-1

Table 16-2

[0152]

Table 17

[0153]

Table 18-1

Table 18-2

Table 18-3

Table 18-4

Table 18-5

Table 18-6

Table 18-7

Table 18-8

Table 18-9

Table 18-10

Table 18-11

Table 18-12

[0154] <Formulation example> Examples of pesticide formulations containing the compound represented by formula (1) according to the present invention as an active ingredient are given below.

[0155] Formulation Example 1 [Wettable powder] The following ingredients were mixed uniformly and pulverized to obtain wettable powders. Compound of the present invention 30% by weight Clay 30% by weight Diatomaceous earth 35% by weight Sanex P252 4% by weight (Calcium lignosulfonate: Trade name of Nippon Paper Industries Co., Ltd.) Sorpol 8070 1% by weight (Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.)

[0156] Formulation Example 2 [Powder] The following ingredients were mixed uniformly to obtain a powder. Compound of the present invention 2% by weight Clay 90% by weight Talc 7% by weight Calcium stearate 1% by weight

[0157] Formulation Example 3 [Emulsion] The above ingredients were mixed uniformly and dissolved to obtain an emulsion. Compound of the present invention 20% by weight N,N-dimethylformamide 20% by weight T-SOL 150 50% by weight (Aromatic solvents: product name of JXTG Nippon Oil & Energy Corporation) New Calgen CL-H 10% by weight (POE alkyl phenyl ether: product name of Takemoto Oil Co., Ltd.)

[0158] Formulation Example 4 [Emulsion 2] The following ingredients were mixed uniformly and dissolved to obtain an emulsion. Compound of the present invention 5% by weight Xylene 42.5% by weight DMSO 42.5% by weight New Calgen 2003 10% by weight (Mixture of POE allyl phenyl ether formaldehyde condensate and metal alkylbenzene sulfonate: product name of Takemoto Oil & Fat Co., Ltd.)

[0159] Formulation Example 5 [Granules] The above ingredients were uniformly pulverized and mixed, water was added, the mixture was thoroughly kneaded, and then the mixture was granulated and dried to obtain granules. Compound of the present invention 5% by weight Bentonite 40% by weight Talc 10% by weight Clay 43% by weight Sanex P252 2% by weight (Calcium lignosulfonate: Trade name of Nippon Paper Industries Co., Ltd.)

[0160] Formulation Example 6 (Flowable formulation) The entire amount of the above formulation, excluding the 1% aqueous solution of xanthan gum and an appropriate amount of water, was premixed and then pulverized in a wet pulverizer. The 1% aqueous solution of xanthan gum and the remaining water were then added to the pulverized mixture to obtain a 100% by weight flowable formulation. Compound of the present invention 25% by weight Sorpol 7556 5% by weight (POE styryl phenyl ether sulfate: product name of Toho Chemical Industry Co., Ltd.) Propylene glycol 6% by weight Bentonite 1% by weight Xanthan gum 1% aqueous solution 3% by weight Water 60% by weight

[0161] Formulation Example 7 [Granules] The above ingredients were uniformly pulverized and mixed, water was added, the mixture was thoroughly kneaded, and then the mixture was granulated and dried to obtain granules. Compound of the present invention 5% by weight Bentonite 40% by weight Talc 10% by weight Clay 43% by weight Sanex P252 2% by weight (Calcium lignosulfonate: Trade name of Nippon Paper Industries Co., Ltd.)

[0162] <Biological test example> The following tests demonstrate the control effect of the compounds of the present invention against specific pests. "Control effect" means inhibition of the development of harmful invertebrates (mortality rate (including a significant reduction in feeding)) or prevention of damage from harmful invertebrates (feeding prevention effect). However, the pests controlled by the compounds of the present invention are not limited to these species. Compound numbers refer to the compounds in Tables 14-1 to 16-2.

[0163] The insect mortality rate and the feeding damage prevention effect shown in the biological test examples were calculated based on the following formulas. Mortality rate (%) = (total number of abnormal insects and dead insects) / (total number of insects) x 100 Damage prevention effect (%) = (total leaf area - leaf area damaged by target pests) / (total leaf area) x 100 Here, the term "abnormal insect count" means the number of insects whose feeding has been significantly reduced by the compound of the present invention.

[0164] Biological test example 1: Cotton aphid (Aphis gossypii) control test (leaf spray treatment) Cucumber leaves were cut into pieces 3.5 cm in diameter and placed on absorbent cotton soaked in water. Two adult cotton aphids were released onto the cut pieces and allowed to lay offspring for 24 hours, after which the adults were removed. 2 mL of a diluted solution of the test compound diluted to 200 ppm was sprayed onto the cucumber leaves using a spray tower. After air drying, the cucumber leaves and the parasitic larvae were placed in a plastic cup with the absorbent cotton and placed in a lid in a constant temperature room at 25°C. Five days after treatment, the number of live or dead aphids was observed and the mortality rate was calculated. As a result, compounds 3, 4, 5, 6, 7, 13, 14, 16, 18, 21, 24, 28, 36, 44, 93, 94, 96, 101, 107, 108, 109, 112, 113, 114, 116, 117, 118, 119, 122, 124, 125, 126, 128, 129, and 133 of the present invention showed insect mortality rates of 80% or more.

[0165] Biological test example 2: Cotton aphid (Aphis gossypii) control test (root dipping treatment) A single cucumber seedling (cotyledon stage) was fixed with urethane so that the roots were submerged in a vial (inner diameter 2.7 cm x 6 cm) containing 10 mL of a 3.1 ppm diluted solution. One day after immersion, five first-instar cotton aphid larvae were released into the vial and reared in a constant temperature room at 25°C. Five to seven days after release, the insects were examined for mortality and abnormalities. As a result, the compounds 3, 4, 5, 14, 18, 20, 21 and 89 of the present invention showed a mortality rate of 80% or more.

[0166] Biological test example 3: Tobacco whitefly (Bemisia tabaci) control test (foliage spray treatment) Cucumber leaves were cut into pieces 6.0 cm in diameter and placed on absorbent cotton soaked in water. 2 mL of a 200 ppm diluted solution of the test compound was sprayed onto the cucumber leaves using a spray tower. After air drying, the cucumber leaves were placed in plastic cups, and 20 adult female Bemisia tabaci were released into the cups. The cups were then covered and reared in a constant temperature room at 25°C. Five days after treatment, the number of live or dead insects was observed, and the mortality rate was calculated. As a result, compounds 18, 20, 21, 24, 29, 42, 59, 60, 62, 68, 82, 85 and 88 of the present invention showed a mortality rate of 50% or more.

[0167] Biological test example 4: Diamondback moth (Plutella xylostella) control test (leaf immersion treatment) Cabbage leaves were cut into pieces 5.0 cm in diameter, immersed in 20 mL of a 200 ppm diluted solution of the test compound, and air-dried. After air-drying, the cabbage leaves were placed in plastic cups, and 10 third-instar diamondback moth larvae were released into them. The cups were then covered and reared in a constant temperature room at 25°C. Five days after treatment, the number of larvae alive or dead was observed, and the mortality rate was calculated. As a result, the compounds of the present invention 3, 4, 5, 6, 7, 8, 10, 11, 12, 13, 14, 16, 18, 20, 21, 24, 28, 29, 30, 32, 38, 40, 41, 42, 44, 46, 48, 49, 54, 56, 59, 60, 62, 64, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 85, 86, 88, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155 2, 93, 94, 95, 96, 98, 99, 100, 101, 102, 103, 104, 106, 107, 108, 109, 110, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 129, 133, 134, and 136 showed mortality rates of over 80%.

[0168] Biological test example 5: Control test of brown planthopper (Nilaparvata lugens) (stem and leaf dipping treatment) Ten rice seedlings were immersed in 20 mL of a solution of the test compound diluted to 200 ppm and air-dried. After air-drying, they were held in place in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane and placed in a plastic cup containing 40 mL of water. Third-instar brown planthopper larvae were released into the cylinder, which was then covered with a medical paper and reared in a constant temperature room at 25°C. Five days after treatment, the number of surviving larvae was observed, and the mortality rate was calculated. As a result, compounds 2, 3, 18, 21, 64, 82, 93, 101, 109, 114, 116, 117, 120, 124, 125, 129, and 133 of the present invention showed a mortality rate of 80% or more.

[0169] Biological Test Example 6: Control test of common cutworm (Spodoptera litura) (stem and leaf dipping treatment) Cabbage leaves were cut into pieces 5.0 cm in diameter, immersed in 20 mL of a 200 ppm diluted solution of the test compound, and air-dried. After air-drying, the cabbage leaves were placed in plastic cups, and five second-instar larvae of the common cutworm (Spodoptera litura) were released into them. The cups were then covered and reared in a constant temperature room at 25°C. Five days after treatment, the number of larvae alive or dead was observed, and the mortality rate was calculated. As a result, the compounds of the present invention 3, 4, 10, 16, 18, 21, 24, 28, 32, 38, 40, 41, 42, 44, 46, 48, 49, 54, 56, 59, 60, 62, 71, 74, 75, 76, 77, 78, 79, 80, 81, 82, 85, 86, 88, 90, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 8, 99, 100, 101, 102, 103, 104, 106, 107, 108, 109, 110, 112, 113, 114, 115, 116, 117, 118, 120, 121, 122, 123, 124, 125, 126, 127, 133, 134, and 136 showed mortality rates of over 80%.

[0170] Biological test example 7: Control test of palm thrips (Thrips palmi) (leaf spray treatment) Cucumber leaves were cut into pieces 1.5 cm in diameter and placed on absorbent cotton soaked in water. 2 mL of a 200 ppm diluted solution of the test compound was sprayed onto the cucumber leaves using a spray tower. After air drying, the leaves were placed in a plastic cup together with the absorbent cotton. Five first-instar larvae of the southern melon thrips were released into the cup, which was then covered and reared in a constant temperature room at 25°C. Two days after treatment, the number of dead or alive insects was observed, and the mortality rate and the effectiveness of the treatment to prevent feeding damage were calculated. As a result, compounds 24, 59, 68, 74, 82, 98, 107, 109, 113, 114, 115, 116, 117, 123, 124 and 125 of the present invention showed an insect mortality rate or feeding damage prevention effect of 50% or more.

Claims

1. A compound represented by formula (1) or an N-oxide thereof, or a salt thereof: 【Chemistry 1】 [In formula (1), A represents a structure represented by A-1, A-2, A-3, A-4, A-5, A-6, A-8, or A-9; 【Chemistry 2】 R １ , R ２ , R ３ , R ４ and R ５ Each independently represents at least one halo(C １ ~C ６ ) alkyl, (C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, and (C═O)NY １ Y ２ represents a group selected from the group consisting of Other R １ , R ２ , R ３ , R ４ and R ５ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, and halo(C １ ~C ６ ) alkylsulfonyl; R ６ is a hydrogen atom, (C １ ~C ３ ) alkyl, cyclopropyl, halo(C １ ~C ３ ) alkyl, (C １ ~C ３ ) alkoxy, and halo (C １ ~C ３ ) alkoxy; Y １ is Haro (C １ ~C ３ ) alkyl; Y ２ is a hydrogen atom, (C １ ~C ３ ) alkyl, and halo(C １ ~C ３ ) alkyl, n represents 0, 1, or 2; R Ａ is C １ ~C ３ represents an alkyl group, R Ｂ and R Ｄ are each independently a hydrogen atom, a halogen atom, or C １ ~C ３ Alkyl, cyclopropyl, C １ ~C ３ Alkoxy, halo(C １ ~C ３ ) alkyl, cyano, and up to two C １ ~C ３ represents a group selected from the group consisting of amino optionally substituted with alkyl, R Ｃ represents a group selected from the group consisting of phenyl which may be substituted with up to five Z's, pyridinyl which may be substituted with up to four Z's, pyrimidinyl which may be substituted with up to three Z's, pyrazinyl which may be substituted with up to three Z's, pyridazinyl which may be substituted with up to three Z's, and V; V represents a group selected from the group consisting of structures represented by V-1, V-2, V-3, V-4, V-5, V-6, V-7, V-8 and V-9; 【Chemistry 3】 When there are multiple Z's, each Z is independently a hydrogen atom, a halogen atom, or C. １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) Alkylsulfonyl, NY ３ Y ４ and (C=O)NY ３ Y ４ or two Z's and R's to which the Z's are bonded Ｃ A group in which the carbon atoms of the two groups are joined together to form a 1,3-dioxole group, and two Z's and R's to which the Z's are bonded Ｃ the carbon atoms of which together form a 1,4-dioxine group, said 1,3-dioxole group and said 1,4-dioxine group being optionally substituted by one or more independent halogen atoms; Q2 represents 0, 1 or 2; Q3 represents 0, 1, 2 or 3; Q4 represents 0, 1, 2, 3 or 4; Y ３ and Y ４ Each independently represents a hydrogen atom, C １ ~C ３ Alkyl, cyclopropyl, and halo(C １ ~C ３ ) alkyl, D represents a group selected from the group consisting of hydroxy, C 1 -C 6 alkoxy optionally substituted with T, C 3 -C 6 cycloalkoxy optionally substituted with T, and halo(C 1 -C 6 )alkoxy optionally substituted with T; E is a hydrogen atom, C which may be substituted with T １ ~C ６ Alkyl, halo optionally substituted with T (C １ ~C ６ ) alkyl, C optionally substituted with T １ ~C ６ Alkylcarbonyl and halo (C １ ~C ６ ) alkylcarbonyl; The T replacement may be made by multiple T's, When there are multiple T's, each T is independently C １ ~C ３ Alkoxy, halo(C １ ~C ３ ) Alkoxy, C １ ~C ３ Alkylthio, halo(C １ ~C ３ ) alkylthio, C １ ~C ３ Alkyl sulfinyl, halo(C １ ~C ３ ) alkylsulfinyl, C １ ~C ３ Alkyl sulfonyl, halo(C １ ~C ３ ) a group selected from the group consisting of alkylsulfonyl, cyano, and a phenyl group optionally substituted with up to five Gs; When there are two or more G's, each independently represents a halogen atom, C １ ~C ３ Alkyl and halo (C １ ~C ３ ) alkyl.

2. A compound represented by formula (1) or an N-oxide thereof, or a salt thereof: 【Chemistry 4】 [In formula (1), A represents a structure represented by A-1, A-2 or A-3; 【Chemistry 5】 R １ , R ２ , R ３ , R ４ and R ５ Each independently represents at least one halo(C １ ~C ６ ) alkyl, (C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, halo(C １ ~C ６ ) alkylsulfonyl, and (C═O)NY １ Y ２ represents a group selected from the group consisting of Other R １ , R ２ , R ３ , R ４ and R ５ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C ３ ~C ６ Cycloalkyl, halo(C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) alkoxy, halo (C １ ~C ６ ) alkylthio, halo(C １ ~C ６ ) alkylsulfinyl, and halo(C １ ~C ６ ) alkylsulfonyl; Y １ is Haro (C １ ~C ３ ) alkyl; Y ２ is a hydrogen atom, (C １ ~C ３ ) alkyl, and halo(C １ ~C ３ ) alkyl, n represents 0, 1, or 2; R Ａ is C １ ~C ３ represents an alkyl group, R Ｂ and R Ｄ are each independently a hydrogen atom, a halogen atom, or C １ ~C ３ Alkyl, cyclopropyl, C １ ~C ３ Alkoxy and halo (C １ ~C ３ ) alkyl, R Ｃ represents a group selected from the group consisting of phenyl which may be substituted with up to five Z's, pyridinyl which may be substituted with up to four Z's, pyrimidinyl which may be substituted with up to three Z's, pyrazinyl which may be substituted with up to three Z's, pyridazinyl which may be substituted with up to three Z's, and V; V represents a group selected from the group consisting of structures represented by V-1, V-2, V-3, V-4, V-5, V-6, V-7, and V-8; 【Chemistry 6】 When there are multiple Z's, each Z is independently a hydrogen atom, a halogen atom, or C. １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) Alkylsulfonyl, NY ３ Y ４ and (C=O)NY ３ Y ４ represents a group selected from the group consisting of Q2 represents 0, 1 or 2; Q3 represents 0, 1, 2 or 3; Q4 represents 0, 1, 2, 3 or 4; When Q2, Q3, and Q4 each represent an integer of 2 or more, each Z may be the same as or different from each other; Y ３ and Y ４ Each independently represents a hydrogen atom, C １ ~C ３ Alkyl, cyclopropyl, and halo(C １ ~C ３ ) alkyl, D represents a group selected from the group consisting of hydroxy, C 1 -C 6 alkoxy optionally substituted with T, C 3 -C 6 cycloalkoxy optionally substituted with T, and halo(C 1 -C 6 )alkoxy optionally substituted with T; E is a hydrogen atom, C which may be substituted with T １ ~C ６ Alkyl, halo optionally substituted with T (C １ ~C ６ ) alkyl, C optionally substituted with T １ ~C ６ Alkylcarbonyl and halo (C １ ~C ６ ) alkylcarbonyl; The T replacement may be made by multiple T's, When there are multiple T's, each T is independently C １ ~C ３ Alkoxy, halo(C １ ~C ３ ) Alkoxy, C １ ~C ３ Alkylthio, halo(C １ ~C ３ ) alkylthio, C １ ~C ３ Alkyl sulfinyl, halo(C １ ~C ３ ) alkylsulfinyl, C １ ~C ３ Alkyl sulfonyl, halo(C １ ~C ３ ) a group selected from the group consisting of alkylsulfonyl, cyano, and a phenyl group optionally substituted with up to five Gs; When there are two or more G's, each independently represents a halogen atom, C １ ~C ３ Alkyl and halo (C １ ~C ３ ) alkyl.

3. R １ , R ２ , R ３ , R ４ and R ５ At least one of each independently is halo(C １ ~C ３ ) alkyl, (C １ ~C ３ ) alkoxy, halo (C １ ~C ３ ) alkoxy, halo (C １ ~C ３ ) alkylthio, halo(C １ ~C ３ ) alkylsulfinyl, halo(C １ ~C ３ ) alkylsulfonyl, and (C═O)NY １ Y ２ is a group selected from the group consisting of Other R １ , R ２ , R ３ , R ４ and R ５ are each independently a hydrogen atom or a halogen atom, R Ａ is an ethyl group, R Ｂ and R Ｄ are each independently a hydrogen atom or a halogen atom, R Ｃ represents a group selected from the group consisting of a phenyl group which may be substituted with up to five Z's, a pyrimidinyl group which may be substituted with up to three Z's, and V; When Z is a plurality of Z, each Z is independently at least one halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) Alkylsulfonyl, NY ３ Y ４ and (C=O)NY ３ Y ４ is a group selected from the group consisting of Other Z's are hydrogen atoms, halogen atoms, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo(C １ ~C ６ ) Alkoxy, C １ ~C ６ Alkylthio, halo(C １ ~C ６ ) alkylthio, C １ ~C ６ Alkyl sulfinyl, halo(C １ ~C ６ ) alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, halo(C １ ~C ６ ) Alkylsulfonyl, NY ３ Y ４ and (C=O)NY ３ Y ４ is a group selected from the group consisting of D is a group selected from the group consisting of hydroxy, C 1 -C 6 alkoxy optionally substituted with T, C 3 -C 6 cycloalkoxy optionally substituted with T, and halo(C 1 -C 6 )alkoxy optionally substituted with T; E is a hydrogen atom, or C optionally substituted with T １ ~C ６ Alkyl and halo (C １ ~C ６ ) alkyl, T, when there are multiple T, each independently represents C １ ~C ３ Alkoxy, halo(C １ ~C ３ ) Alkoxy, C １ ~C ３ Alkylthio, halo(C １ ~C ３ ) alkylthio, C １ ~C ３ Alkyl sulfinyl, halo(C １ ~C ３ ) alkylsulfinyl, C １ ~C ３ Alkyl sulfonyl, halo(C １ ~C ３ ) a group selected from the group consisting of alkylsulfonyl and cyano; The compound according to claim 1 or 2, or an N-oxide or a salt thereof.

4. R １ , R ２ , R ３ , R ４ and R ５ at least one of these independently represents a group selected from the group consisting of trifluoromethyl, pentafluoroethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, trifluoromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, and (2,2,2-trifluoroethyl)carbamoyl; Other R １ , R ２ , R ３ , R ４ and R ５ is a hydrogen atom or a halogen atom, R Ｃ is a group selected from the group consisting of structures represented by V-2, V-6, V-7, and V-8, 【Chemistry 7】 Z is independently at least one halogen atom, C １ ~C ３ Alkyl, halo (C １ ~C ３ ) alkyl, cyclopropyl, C １ ~C ３ Alkoxy, halo(C １ ~C ３ ) Alkoxy, C １ ~C ３ Alkylthio, halo(C １ ~C ３ ) alkylthio, C １ ~C ３ Alkyl sulfinyl, halo(C １ ~C ３ ) alkylsulfinyl, C １ ~C ３ Alkyl sulfonyl, halo(C １ ~C ３ ) Alkylsulfonyl, NY ３ Y ４ and (C=O)NY ３ Y ４ is a group selected from the group consisting of Other Z's are hydrogen atoms, halogen atoms, C １ ~C ３ Alkyl, halo (C １ ~C ３ ) alkyl, cyclopropyl, C １ ~C ３ Alkoxy, halo(C １ ~C ３ ) Alkoxy, C １ ~C ３ Alkylthio, halo(C １ ~C ３ ) alkylthio, C １ ~C ３ Alkyl sulfinyl, halo(C １ ~C ３ ) alkylsulfinyl, C １ ~C ３ Alkyl sulfonyl, halo(C １ ~C ３ ) Alkylsulfonyl, NY ３ Y ４ and (C=O)NY ３ Y ４ is a group selected from the group consisting of The compound according to any one of claims 1 to 3, or an N-oxide or a salt thereof.

5. R １ , R ２ , R ３ , R ４ and R ５ at least one of these independently represents a group selected from the group consisting of trifluoromethyl, pentafluoroethyl, trifluoromethylthio, trifluoromethylsulfinyl, and trifluoromethylsulfonyl; Other R １ , R ２ , R ３ , R ４ and R ５ is a hydrogen atom, R Ｂ and R Ｄ is a hydrogen atom, D is a group selected from the group consisting of hydroxy, C 1 -C 6 alkoxy optionally substituted with T, C 3 -C 6 cycloalkoxy optionally substituted with T, and halo(C 1 -C 6 )alkoxy optionally substituted with T; E is a hydrogen atom, or C optionally substituted with T １ ~C ３ Alkyl and halo (C １ ~C ３ ) alkyl, The compound according to any one of claims 1 to 4, or an N-oxide or a salt thereof.

6. R Ｃ The compound according to any one of claims 1 to 5, or an N-oxide or a salt thereof, wherein is V-7 or V-8. 【Chemistry 8】

7. The compound or its N-oxide or salt according to any one of claims 1 to 6, wherein A is A-2. 【Chemistry 9】

8. The compound or its N-oxide or salt according to any one of claims 1 to 6, wherein A is A-3. 【Chemistry 10】

9. A pest control agent comprising the compound according to any one of claims 1 to 8, or an N-oxide thereof, or a salt thereof.

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