# US 12,180,178 B2 · Heteroaryl azole compound and pest control agent

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- Number: US 12,180,178 B2
- Document ID: US12180178B2
- Status: Granted
- Kind: B2
- Application number: 17/271,531
- Filed: 2019-09-02
- Published: 2021-09-02
- Granted: 2024-12-31
- Earliest claimed: 2018-09-03
- Assignees: Nippon Soda Co., Ltd.
- Applicants: Nippon Soda Co., Ltd.
- Inventors: Keita Sakanishi; Hikaru Aoyama; Daisuke Ushijima; Takao Iwasa; Norifumi Sakiyama; Maki Matsui
- Web page: https://patentgrep.com/patent/US12180178B2

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/50: 1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61P 33/00: Antiparasitic agents
- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C07D 401/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A heteroaryl azole compound of the following formula (II): an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds. In the formula (II), R1 represents a substituted or unsubstituted C1-6 alkylthio group or the like; B1 represents a nitrogen atom or CR2; R2 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or the like; R3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or the like; R represents a substituted or unsubstituted C1-6 alkyl group or the like; A represents a carbon atom or a nitrogen atom; X represents a substituted or unsubstituted C1-6 alkyl group or the like; n represents a number of chemically acceptable X, and is an integer of 0 to 2; and X is the same or different when n is 2.

## Claims

### Claim 1

A compound of formula (II), an N-oxide compound, stereoisomer, tautomer or hydrate thereof, or a salt of any of these compounds:
wherein
R1 represents a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group or a substituted or unsubstituted C1-6 alkylsulfonyl group;
B1 represents a nitrogen atom or CR2;
R2 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted amino group, a cyano group or a halogeno group;
R3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group;
R represents a C1-6 haloalkyl group, a C1-6 haloalkoxy C1-6 haloalkyl group, a C2-6 haloalkenyl group, or a C1-6 haloalkoxy C2-6 haloalkenyl group;
A represents a carbon atom or a nitrogen atom;
X represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxy group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group;
n represents a number of chemically acceptable X, and is an integer of 0 to 2; and
X is the same or different when n is 2.

### Claim 2 (depends on 1)

A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

### Claim 3 (depends on 1)

An insecticide or acaricide comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

### Claim 4 (depends on 1)

An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.

### Claim 5 (depends on 1)

An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to claim 1, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds.