# US 2020/0399278 A1 · Heterocyclic compounds and noxious arthropod control agent containing same

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- Number: US 2020/0399278 A1
- Document ID: US20200399278A1
- Status: Published application
- Kind: A1
- Application number: 16/957,264
- Filed: 2018-12-25
- Published: 2020-12-24
- Earliest claimed: 2017-12-25
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Ayaka TANAKA; Naoya SUGIMOTO; Risa KONO; Yoshihiko NOKURA
- Web page: https://patentgrep.com/patent/US20200399278A1

## CPC

- A01N 25/00: Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- C07D 487/04: Ortho-condensed systems
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a compound having an excellent control effect on a harmful arthropod. A compound represented by formula (I) [wherein Q represents a group represented by Q1 or a group represented b Q2; Z represents an oxygen atom or a sulfur atom; A1 represents a nitrogen atom or the like; A2 represents a CR4a or the like; A3 represents a nitrogen atom, a CR4b, or the like; B1 represents a CR1 or the like; B2 represents a nitrogen atom, a CR6b, or the like; B3 represents a nitrogen atom, a CR6c, or the like; R1 represents a C1-C6 chain hydrocarbon group having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, or the like; R2 represents a C1-C6 chain hydrocarbon group or the like; R3 represents a C1-C6 chain hydrocarbon group or the like; R4a, R4b, R6b, and R6c are identical to or different from each other, and each represent a hydrogen atom or the like; n represents 0, 1, or 2; and q represents 0, 1, 2, or 3] or an N-oxide compound thereof has an excellent control effect on a harmful arthropod.

## Claims

### Claim 1

A compound represented by formula (I)
[wherein:
Q represents a group represented b Q1 or a group represented by Q2;
Z represents an oxygen atom or a sulfur atom;
A1 represents a nitrogen atom or a CR5;
R5 represents a halogen atom or a hydrogen atom;
A2 and A3 represents a combination, which is
a combination wherein A2 represents a CR4a and A3 represents a nitrogen atom or a CR4b; or
a combination wherein A2 represents a nitrogen atom and A3 represents a CR4b;
B1, B2, and B3 represents a combination, which is a combination wherein B1 represents a CR1, B2 represents a nitrogen atom or a CR6b, and B3 represents a nitrogen atom or a CR6;
a combination wherein B1 represents a nitrogen atom or a CR6, B2 represents a CR1, and B3 represents a nitrogen atom or a CR6a; or
a combination wherein B1 represents a nitrogen atom or a CR6, B2 represents a nitrogen atom or a CR6, and B3 represents a CR1;
R1 represents a C1-C6 chain hydrocarbon group having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group optionally having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, a —SR8, a —S(O)R8, a —S(O)2R8, a —OR8, or a —OS(O)2RS;
R8 represents a C1-C6 chain hydrocarbon group having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, or a C3-C4 cycloalkyl group optionally having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom;
R4, R4, R6, R6, and R6 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C3-C7 cycloalkyl group optionally having one or more halogen atom(s), a C1-C6 alkoxy group optionally having one or more halogen atom(s), a —NR9R10, a —C(O)R7, a —C(O)OR7, a —C(O)NR19R20, a-NR9C(O)R18, a-NR9C(O)OR18, a-NR9C(O)NR19R20, a cyano group, a halogen atom, or a hydrogen atom;
R9 and R19 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), or a hydrogen atom;
R10 represents a C1-C6 chain hydrocarbon group optionally having one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally having one or more substituent(s) selected from Group J, a phenyl group optionally having one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group D, a hydrogen atom, or a —S(O)2R21;
R21 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C3-C7 cycloalkyl group optionally having one or more halogen atom(s), or a phenyl group optionally having one or more substituent(s) selected from Group D;
R7, R18, and R20 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally having one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituent(s) selected from Group J, or a hydrogen atom;
R2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a cyclopropylmethyl group;
n represents 0, 1, or 2;
R3 represents a C1-C6 chain hydrocarbon group optionally having one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituent(s) selected from Group E, a C3-C7 cycloalkenyl group optionally having one or more substituent(s) selected from Group J, a phenyl group optionally having one or more substituent(s) selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group H, a —OR12, a —NR11R12, a —NR11aR12a, a —NR24NR11R12, a —NR24OR11, a —NR11C(O)R13, a —NR24NR11C(O)R13, a —NR11C(O)OR14, a —NR24NR11C(O)OR14, a —NR11C(O)NR15aR16, a —NR24NR11C(O)NR15aR16, a-N═CR24NR15aR16a, a-N═S(O)xR15R16, a-C(O)R13, a-C(O)OR17, a-C(O)NR15aR16a, a-C(O)NR11S(O)2R23, a —CR24═NOR17, a —NR11CR24═NOR17, a cyano group, a nitro group, or a halogen atom;
q represents 0, 1, 2, or 3, wherein when q represents 2 or 3, two or three R3 may be identical to or different from each other;
When two R3 are adjacent with each other, the two R3 may be combined with the two carbon atoms to which they are attached to form a benzene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, a triazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring (wherein said benzene ring, said pyrrole ring, said furan ring, said thiophene ring, said pyrazole ring, said imidazole ring, said triazole ring, said oxazole ring, said isoxazole ring, said thiazole ring, said pyridine ring, said pyridazine ring, said pyrimidine ring, and said pyrazine ring may optionally have one or more substituent(s) selected from Group H);
R17 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a phenyl group optionally having one or more substituent(s) selected from Group D, or a hydrogen atom;
R11, R15a, and R24 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), or a hydrogen atom;
R12 represents a C1-C6 chain hydrocarbon group optionally having one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally having one or more substituent(s) selected from Group J, a phenyl group optionally having one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group D, a hydrogen atom, or a —S(O)2R23;
R23 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C3-C7 cycloalkyl group optionally having one or more halogen atom(s), or a phenyl group optionally having one or more substituent(s) selected from Group D;
R11a and R12a may be combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituent(s) selected from Group E;
R13 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C3-C7 cycloalkyl group optionally having one or more halogen atom(s), a (C3-C6 cycloalkyl)C1-C3 an alkyl group optionally having one or more halogen atom(s), a phenyl group optionally having one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group D, or a hydrogen atom;
R14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C3-C7 cycloalkyl group optionally having one or more halogen atom(s), a (C3-C6 cycloalkyl)C1-C3 an alkyl group optionally having one or more halogen atom(s), or a (phenyl optionally having one or more substituent(s) selected from Group D)C1-C3 an alkyl group;
R15 and R16 are identical to or different from each other, and each represent a C1-C6 an alkyl group optionally having one or more halogen atom(s);
R16a represents a C1-C6 chain hydrocarbon group optionally having one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituent(s) selected from Group J, or a hydrogen atom; and
x represents 0 or 1;
Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atom(s), a C3-C6 alkenyloxy group optionally having one or more halogen atom(s), a C3-C6 alkynyloxy group optionally having one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally having one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally having one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally having one or more halogen atom(s), a C3-C6 cycloalkyl group optionally having one or more halogen atom(s), a (C1-C6 alkyl optionally having one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally having one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionally having one or more halogen atom(s))aminocarbonyl group, a (di(C1-C4 alkyl)amino optionally having one or more halogen atom(s))carbonyl group, a (C2-C6 alkoxycarbonyl optionally having one or more halogen atom(s))amino group, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl)amino group optionally having one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom;
Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C1-C6 alkoxy group optionally having one or more halogen atom(s), a C3-C6 alkenyloxy group optionally having one or more halogen atom(s), a C3-C6 alkynyloxy group optionally having one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally having one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally having one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally having one or more halogen atom(s), a C3-C6 cycloalkyl group optionally having one or more halogen atom(s), a (C1-C6 alkyl optionally having one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally having one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionally having one or more halogen atom(s))aminocarbonyl group, a (di(C1-C4 alkyl)amino optionally having one or more halogen atom(s))carbonyl group, a (C2-C6 alkoxycarbonyl optionally having one or more halogen atom(s))amino group, a (C2-C6 alkoxycarbonyl)C1-C6 alkyl)amino group optionally having one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom;
Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C1-C6 alkoxy group optionally having one or more halogen atom(s), a C3-C6 alkenyloxy group optionally having one or more halogen atom(s), a C3-C6 alkynyloxy group optionally having one or more halogen atom(s), a (C1-C6 alkyl optionally having one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally having one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionally having one or more halogen atom(s))aminocarbonyl group, a (di(C1-C4 alkyl)amino optionally having one or more halogen atom(s))carbonyl group, a (C2-C6 alkoxycarbonyl optionally having one or more halogen atom(s))amino group, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl)amino group optionally having one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, an oxo group, and a halogen atom;
Group F: a group consisting of a C3-C6 cycloalkyl group optionally having one or more halogen atom(s), a phenyl group optionally having one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group D, a C1-C6 alkoxy group optionally having one or more halogen atom(s), a (C1-C6 alkyl optionally having one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally having one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom;
Group H: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atom(s), a C3-C6 cycloalkyl group optionally having one or more halogen atom(s), a phenyl group optionally having one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group D, a C1-C6 alkoxy group optionally having one or more halogen atom(s), a (C1-C6 alkyl optionally having one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally having one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionally having one or more halogen atom(s))aminocarbonyl group, a (di(C1-C4 alkyl)amino optionally having one or more halogen atom(s))carbonyl group, a (C2-C6 alkoxycarbonyl optionally having one or more halogen atom(s))amino group, a (C2-C6 alkoxycarbonyl)C1-C6 alkyl)amino group optionally having one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom;
Group J: a group consisting of a C1-C6 an alkyl group optionally having one or more halogen atom(s), a C1-C6 alkoxy group optionally having one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally having one or more halogen atom(s), an amino group, a cyano group, and a halogen atom]
or an N-oxide compound thereof.

### Claim 2 (depends on 1)

The compound represented by formula (I) according to claim 1.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein A1 represents a CH.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein A1 represents a nitrogen atom.

### Claim 5 (depends on 1)

The compound according to any claim 1, wherein Q represents the group represented by Q1.

### Claim 6 (depends on 1)

The compound according claim 1, wherein Q represents the group represented by Q2.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R1 represents a C1-C6 an alkyl group having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, a cyclopropyl group optionally having one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, or a —OS(O)2R8.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R3 represents a C1-C6 an alkyl group optionally having one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituent(s) selected from Group E, a phenyl group optionally having one or more substituent(s) selected from Group J, a 5 membered aromatic heterocyclic group comprising 1 to 4 nitrogen atom(s) optionally having one or more substituent(s) selected from Group J, a 6 membered aromatic heterocyclic group optionally having one or more substituent(s) selected from Group J, a —OR12, a —NR11R12, a —NR11C(O)OR14, or a halogen atom.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R2 represents an ethyl group.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein Z represents an oxygen atom.

### Claim 11 (depends on 1)

A composition for controlling a harmful arthropod comprising the compound according to claim 1 and an inert carrier.

### Claim 12 (depends on 1)

A method for controlling a harmful arthropod which comprises applying an effective amount of the compound according to claim 1 to a harmful arthropod or a habitat where a harmful arthropod lives.

### Claim 13 (depends on 1)

A composition comprising one or more ingredient(s) selected from the group consisting of Group (a) and Group (b), and the compound according to claim 1:
Group (a): a group consisting of insecticidal active ingredients, miticidal active ingredients, and nematicidal active ingredients;
Group (b): fungicidal active ingredients.

### Claim 14 (depends on 13)

A method for controlling a harmful arthropod which comprises applying an effective amount of the composition according to claim 13 to a harmful arthropod or a habitat where a harmful arthropod lives.

### Claim 15 (depends on 1)

A seed or a vegetative reproduction organ holding an effective amount of the compound according to claim 1.

### Claim 16 (depends on 13)

A seed or a vegetative reproduction organ holding an effective amount of the composition according to claim 13.