# US 8,273,764 B2 · Fused heterocyclic compounds and use thereof

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- Number: US 8,273,764 B2
- Document ID: US8273764B2
- Status: Granted
- Kind: B2
- Application number: 13/259,058
- Filed: 2010-04-20
- Published: 2012-01-19
- Granted: 2012-09-25
- Earliest claimed: 2009-04-28
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Masaki Takahashi; Mitsuhiko Iwakoshi; Hiroshi Ikegami
- Web page: https://patentgrep.com/patent/US8273764B2

## CPC

- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A01N 43/52: condensed with carbocyclic rings, e.g. benzimidazoles
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61P 33/14: Ectoparasiticides, e.g. scabicides
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 471/04: Ortho-condensed systems
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- 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
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A fused heterocyclic compound of formula (1): wherein, A1 and A2 represent a nitrogen atom or the like, R1, R2, R3 and R4 represent a halogen atom or the like, R2 and R3 represent a halogen atom or the like, R5 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or the like, R6 and R7 represent a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms, or the like, and n represents 0 or 1, has an excellent noxious arthropod controlling effect.

## Claims

### Claim 1

A fused heterocyclic compound of formula (1):
wherein,
m represents 0, 1 or 2,
R1, R2, R3 and R4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more members selected from the group X, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more members selected from the group X, a phenyl group optionally substituted with one or more members selected from the group Y, a benzyl group optionally substituted with one or more members selected from the group Y, a 5-membered heterocyclic group or 6-membered heterocyclic group optionally substituted with one or more members selected from the group Y, —OR8, —NR8R9, —NR8C(O)R9, —S(O)mR8, —SO2Cl, —SO2NR8R9, —CO2R10, —CONR8R9, —CONR10NR11R12, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 represents a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group optionally substituted with one or more halogen atoms, a cyclopropylmethyl group optionally substituted with one or more halogen atoms, —OR13, —NR13R14 or a cyano group,
R6 and R7 are the same or different and represent a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms, —OR15, —S(O)mR15, a halogen atom or a hydrogen atom (here, either R6 or R7 represents a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms, —OR15, —S(O)mR15), alternatively R6 and R7 may be bonded to form a 5-membered ring or 6-membered ring substituted with one or more halogen atoms together with carbon atoms to which R6 and R7 are connected,
R8 and R9 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more members selected from the group X, a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more members selected from the group X, a phenyl group optionally substituted with one or more members selected from the group Y, a benzyl group optionally substituted with one or more members selected from the group Y, a 5-membered heterocyclic group or 6-membered heterocyclic group optionally substituted with one or more members selected from the group Y, or a hydrogen atom (concerning —S(O)mR8, m represents the same meaning as described above, but when m represents 1 or 2, R8 does not represent a hydrogen atom),
R10 represents a C1-C4 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom,
R11 and R12 are the same or different and represents a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a C2-C5 alkoxycarbonyl group or a hydrogen atom,
R13 and R14 are the same or different and represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group optionally substituted with one or more halogen atoms, or a hydrogen atom,
R15 represents a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms, and
n represents 0 or 1; wherein
group X is selected from the group consisting of a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, —CO2R16 (here, R16 represents a C1-C4 alkyl group optionally substituted by a halogen), a cyano group and a halogen atom; and wherein
group Y is selected from the group consisting of a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, a cyano group, a nitro group and a halogen atom.

### Claim 2 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein
R6 and R7 are the same or different and are a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms, —OR15, —S(O)mR15, a halogen atom or a hydrogen atom (here, either R6 or R7 represents a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms, —OR15, —S(O)mR15).

### Claim 3 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R6 is a C1-C4 chain hydrocarbon group substituted with one or more halogen atoms.

### Claim 4 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R5 is a methyl group, ethyl group, cyclopropyl group or cyclopropylmethyl group.

### Claim 5 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R1 and R4 are hydrogen atoms.

### Claim 6 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R2 is a hydrogen atom or a halogen atom.

### Claim 7 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R3 is a C3-C6 alicyclic hydrocarbon group optionally substituted with one or more members selected from the group X, a phenyl group optionally substituted with one or more members selected from the group Y, a benzyl group optionally substituted with one or more members selected from the group Y, or a 5-membered heterocyclic group or 6-membered heterocyclic group optionally substituted with one or more members selected from the group Y.

### Claim 8 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more members selected from the group X, —OR8, —NR8R9, —NR8C(O)R9, —S(O)mR8, —CO2R10, —CONR8R9, —CONR10NR11R12, a cyano group, a nitro group, a halogen atom or a hydrogen atom, and R8 and R9 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more members selected from the group X, or a hydrogen atom (here, R8 is not a hydrogen atom when m in —S(O)mR8 represents 1 or 2).

### Claim 9 (depends on 1)

The fused heterocyclic compound according to claim 1, wherein R3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more members selected from the group X, —OR8, —NR8R9, —S(O)mR8, a halogen atom or a hydrogen atom, and R8 and R9 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more members selected from the group X, or a hydrogen atom (here, R8 is not a hydrogen atom when m in —S(O)mR8 represents 1 or 2).

### Claim 10 (depends on 1)

A noxious arthropod controlling composition which comprises the fused heterocyclic compound as described in claim 1 and an inert carrier.

### Claim 11 (depends on 1)

A method of controlling a noxious arthropod which comprises applying an effective amount of the fused heterocyclic compound as described in claim 1 to a noxious arthropod or to a habitat of a noxious arthropod.