Method for controlling harmful arthropods using heterocyclic compounds

Abstract

To provide a method for controlling harmful arthropods.SOLUTION: A compound represented by the formula (I) in the figure or an N-oxide thereof can be used for controlling harmful arthropods, where the symbols in the formula have the meanings described in the specification.SELECTED DRAWING: None

Claims

1. Formula (I) [wherein Q represented by the following formula represents a group represented by formula Q1, a group represented by formula Q2, a group represented by formula Q3, a group represented by formula Q4, a group represented by formula Q5, a group represented by formula Q6, or a group represented by formula Q7 (# represents a bonding site to a sulfur atom, and ● represents a bonding site to Het), A 1 is a nitrogen atom or CR 1 represents R 1 represents a halogen atom or a hydrogen atom, G 1 is a nitrogen atom or CR 10a represents G 2 is a nitrogen atom or CR 10b represents G 3 is a nitrogen atom or CR 10c represents G 4 is a nitrogen atom or CR 10d represents G 5 is a nitrogen atom or CR 10e represents G 6 is a nitrogen atom or CR 10f represents G 7 is a nitrogen atom or CR 10g represents n represents 0, 1 or 2; R 2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropyl group, a cyclopropylmethyl group, or NR 5 R 6 represents R 5 and R 6 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, or R 5 and R 6 may be taken together with the nitrogen atom to which they are attached to form an aziridinyl, azetidinyl, pyrrolidinyl, or piperidyl group; Y 1 is NR 7 , an oxygen atom, or a sulfur atom; R 7 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from Group H}, R 3a , R 3b , R 3d , R 10a , R 10b , R 10c , R 10d , R 10e , R 10f and R 10g are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, OR 12 , N.R. 11 R 12 , N.R. 18 R 19 , N.R. 24 NR 11 R 12 , N.R. 24 OR 11 , N.R. 11 C(O)R 13 , N.R. 24 NR 11 C(O)R 13 , N.R. 11 C(O)OR 14 , N.R. 24 NR 11 C(O)OR 14 , N.R. 11 C(O)NR 31 R 32 , N.R. 24 NR 11 C(O)NR 31 R 32 , N=CHNR 31 R 32 , N=S(O) p R 15 R 16 , C(O)R 13 , C(O)OR 17 , C(O)NR 31 R 32 , C(O)NR 11 S (O) 2 R 23 , C.R. 30 = NOR 17 , N.R. 11 CR 24 = NOR 17 , S(O) q R 23 , a cyano group, a nitro group, a hydrogen atom, or a halogen atom; R 3a , R 3b , and R 3d two adjacent substituents among the above may be taken together with the two carbon atoms to which they are bonded to form a benzene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring or a pyrazine ring {the benzene ring, the pyrrole ring, the furan ring, the thiophene ring, the pyrazole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the isothiazole ring, the pyridine ring, the pyridazine ring, the pyrimidine ring and the pyrazine ring are optionally substituted with one or more substituents selected from Group H} or a triazole ring optionally substituted with one or more substituents selected from Group I, p represents 0 or 1; q represents 0, 1 or 2; R 11 , R 24 , R 36 , and R 37 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group J, a phenyl group optionally substituted with one or more substituents selected from Group D, a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, a hydrogen atom, or S(O) 2 R 23 represents R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, or a hydrogen atom; R 14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group (the phenyl moiety in the phenyl C1-C3 alkyl group optionally substituted with one or more substituents selected from Group D), R 15 and R 16 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, R 17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group D, or a hydrogen atom; R 18 and R 19 represent, together with the nitrogen atom to which they are bonded, a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E; R 23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from Group D, R 30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 35 , N.R. 36 R 37 or a hydrogen atom, R 31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, S(O) 2 R 23 or a hydrogen atom, R 32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group J, or a hydrogen atom; R 35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, Het is a group represented by the formula Het1, a group represented by the formula Het2, or a group represented by the formula Het3 (# 1 represents the binding site to Q), B 1 is NR 51a , or CR 61a R 61b represents B 2 is NR 51b , C.R. 61c R 61d , C.R. 61e R 61f -CR 61g R 61h -*, NR 51c -CR 61i R 61j - *, CR 61k R 61m -CR 61n R 61p -CR 61q R 61r -* or NR 51d -CR 61s R 61t -CR 61u R 61v - represents *, * is B 1 represents the bonding position with W 1 represents an oxygen atom or a sulfur atom, R 51a , R 51b , R 51c , and R 51d are the same or different, and the group K 2 a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group optionally substituted by one or more halogen atoms, or a hydrogen atom; R 61a , R 61b , R 61c , R 61d , R 61e , R 61f , R 61g , R 61h , R 61i , R 61j , R 61k , R 61 , R 61m , R 61n , R 61p , R 61q , R 61r , R 61s , R 61t , R 61u , and R 61v are the same or different and are each a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a nitro group, OR 63 , N.R. 63 R 64 , a cyano group, a halogen atom, or a hydrogen atom; R 61a and R 61b , R 61c and R 61d , R 61e and R 61f , R 61g and R 61h , R 61i and R 61j , R 61k and R 61m , R 61n and R 61p , R 61q and R 61r , R 61s and R 61t , and R 61u and R 61v may each be taken together with the carbon atom to which they are attached to form a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom; R 63 is the group T 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group J 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of , R 64 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; X 1 is CR 62a or a nitrogen atom, X 2 is CR 62b or a nitrogen atom, X 3 is CR 62c or a nitrogen atom, Z 1 is NR 52a , an oxygen atom, or a sulfur atom; Z 2 is NR 52b , an oxygen atom, or a sulfur atom; Z 3 is NR 52c , an oxygen atom, or a sulfur atom; R 52a , R 52b , and R 52c are the same or different, and the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 73 , C(O)OR 74 , C(O)NR 91 R 92 , C(O)NR 71 S (O) 2 R 83 , C.R. 90 = NOR 77 , S(O) v R 83 or a hydrogen atom, R 62a , R 62b , and R 62c are the same or different, and the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 72 , N.R. 71 R 72 , N.R. 76a R 76b , N.R. 84 NR 71 R 72 , N.R. 84 OR 71 , N.R. 71 C(O)R 73 , N.R. 84 NR 71 C(O)R 73 , N.R. 71 C(O)OR 74 , N.R. 84 NR 71 C(O)OR 74 , N.R. 71 C(O)NR 91 R 92 , N.R. 84 NR 71 C(O)NR 91 R 92 , N=CHNR 91 R 92 , N=S(O) r R 75 R 76 , C(O)R 73 , C(O)OR 77 , C(O)NR 91 R 92 , C(O)NR 71 S (O) 2 R 83 , C.R. 90 = NOR 77 , N.R. 71 CR 84 = NOR 77 , S(O) t R 83 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; r represents 0 or 1; t represents 0, 1 or 2; v represents 0, 1 or 2; R 71 , R 84 , R 96 and R 97 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 72 is the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of S(O) 2 R 83 or a hydrogen atom, R 73 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of: R 74 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group V 2 represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of: R 75 and R 76 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, R 76a and R 76b together with the nitrogen atom to which they are attached, form the group P 2 and forming a 3- to 7-membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from the group consisting of R 77 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group V 2 represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of: R 83 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group V 2 represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of R 90 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 95 , N.R. 96 R 97 or a hydrogen atom, R 91 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 92 is the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O) 2 R 83 , or a hydrogen atom. R 95 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. Group D: a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, NR 101 R 102 , C(O)R 101 , O.C.(O.)R 101 , C(O)OR 101 The group consisting of , a cyano group, a nitro group, and a halogen atom. R 101 and R 102 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. Group E: a group consisting of C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxy groups, cyano groups, and nitro groups. Group F: C1-C6 alkoxy group optionally substituted with one or more halogen atoms, Group D 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of: a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 3 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of NR 101 R 102 , a halogen atom, and a cyano group. Group H: C1-C6 alkyl groups optionally substituted with one or more halogen atoms, Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 104 , N.R. 103 R 104 , C(O)R 104 , C(O)NR 103 R 104 , O.C.(O.)R 103 , OC(O)OR 103 , N.R. 104 C(O)R 103 , N.R. 104 C(O)OR 103 , C(O)OR 104 The group consisting of halogen atoms, nitro groups, cyano groups, and amino groups. R 103 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 104 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. Group I: C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms, Group D 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 103 , C(O)OR 103 , and C(O)NR 103 R 104 A group consisting of: Group J: A group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group. Group L: a group consisting of C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms, cyano groups, hydroxy groups, and halogen atoms. Group J 2 The group consisting of C1-C6 alkyl groups optionally substituted with one or more halogen atoms, halogen atoms, and cyano groups. Group K 2 Group D: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms; 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms, and a group M 3 The group consisting of 3- to 7-membered non-aromatic heterocyclic groups optionally substituted with one or more substituents selected from the following: Group M 2 The group consisting of C1-C6 alkyl groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms, and halogen atoms. Group T 2 Group D: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms; 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of: a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 3 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of an amino group, NHR 101 , N.R. 101 R 102 , a halogen atom, and a cyano group. Group P 2 : Group U 3 the group consisting of a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the above, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, a phenyl group, and a halogen atom. Group U 3 : A group consisting of C1-C3 alkyl groups and halogen atoms. Group V 2 The group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl)amino group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. Group D 3 : a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, an amino group, NHR 101 , N.R. 101 R 102 , C(O)R 101 , O.C.(O.)R 101 , C(O)OR 101 The group consisting of , a cyano group, a nitro group, and a halogen atom. Group M 3 The group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C2 alkynyloxy group optionally substituted with one or more halogen atoms, and a halogen atom. or an N-oxide thereof, or a salt thereof to arthropod pests, habitats of arthropod pests, plants, or cultivation carriers of plants.

2. 2. The method for controlling arthropod pests according to claim 1, wherein the support for growing plants is soil.

3. A composition comprising the compound represented by formula (I) according to claim 1 or an N-oxide thereof, and one or more components selected from the group consisting of group (a), group (b), group (c), group (d), group (e), group (f), group (g), group (h), group (i), and group (j): Group (a): a group consisting of arthropodicidal active ingredients and nematicidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): phytotoxicity safeners; Group (e): synergists; Group (f): repellent components; Group (g): molluscicidal ingredients; Group (h): insect pheromones; Group (i): herbicidal active ingredients; Group (j): biological control materials.

4. A method for controlling arthropod pests, which comprises applying an effective amount of the composition according to claim 3 to arthropod pests, their habitats, plants, or plant cultivation carriers.

5. 5. The method for controlling arthropod pests according to claim 4, wherein the support for cultivating plants is soil.

6. A seed or vegetative reproductive organ carrying an effective amount of the compound of formula (I) or its N-oxide as defined in claim 1, or the composition as defined in claim 3.

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