# US 11,078,181 B2 · Diaryl pyrazole compound and formulation for controlling harmful organisms

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- Number: US 11,078,181 B2
- Document ID: US11078181B2
- Status: Granted
- Kind: B2
- Application number: 16/469,937
- Filed: 2017-12-14
- Published: 2019-11-28
- Granted: 2021-08-03
- Earliest claimed: 2016-12-19
- Assignees: Nippon Soda Co., Ltd.
- Applicants: Nippon Soda Co., Ltd.
- Inventors: Keita Sakanishi; Takao Iwasa; Norifumi Sakiyama; Hikaru Aoyama; Tomomi Kobayashi
- Web page: https://patentgrep.com/patent/US11078181B2

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 47/02: the carbon atom having no bond to a nitrogen atom
- A01N 47/18: containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/53: having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine (melarsoprol A61K31/555 {; with four nitrogen atoms A61K31/495})
- 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)

## Abstract

A compound represented by the following Formula (I) or a salt thereof, as well as a formulation for controlling harmful organisms, and in particular, an insecticidal formulation, a miticidal formulation, a formulation for controlling ectoparasites or a formulation for controlling or killing endoparasites, which contains at least one compound selected from the compounds of Formula (I) and salts thereof as an active ingredient wherein, each of R1 and R2 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or the like, with the proviso that when R2 represents a hydrogen atom, R1 represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 3- to 6-membered heterocyclyl group; R3 represents a C1-6 alkylthio group or the like; each of R4 and R5 independently represents a hydrogen atom, a halogeno group or the like; and Ar represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

## Claims

### Claim 1

A compound represented by Formula (I) or a salt thereof
wherein
each of R1 and R2 independently represents a hydrogen atom, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyl group, with the proviso that in the case of R2 being a hydrogen atom, R1 is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyl group, and in the case of R1 being a hydrogen atom, R2 is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyl group,
wherein the substituted group on the “C6-10 aryl group” or “3- to 6-membered heterocyclyl group” of R1 and R2 is a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, an amino group, a mono C1-6 alkoxy carbonyl amino group, a cyano group, or an oxo group,
R3 represents a C1-6 alkylsulfonyl group,
R4 represents C1-6 alkyl group, or a substituted or unsubstituted amino group,
wherein the substituted amino group of R4 is a C1-6 alkyl amino group, a C3-8 cycloalkyl amino group, a C1-6 alkyl carbonylamino group, a mono(C1-6 alkoxy carbonyl) amino group, or a di(C1-6 alkoxy carbonyl) amino group,
R5 represents a hydrogen atom, and
Ar represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted, 5- to 6-membered heteroaryl group,
wherein the substituted group of “C6-10 aryl group” and “5- to 6-membered heteroaryl group” of Ar is a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C1-6 haloalkylthio group, or a C1-6 haloalkylsulfonyl group.

### Claim 2 (depends on 1)

A formulation for controlling harmful organisms, containing at least one compound selected from the group consisting of the compounds as recited in claim 1, and salts thereof, as an active ingredient.

### Claim 3 (depends on 1)

An insecticidal formulation or an acaricidal formulation, containing at least one compound selected from the group consisting of the compounds as recited in claim 1, and salts thereof, as an active ingredient.

### Claim 4 (depends on 1)

A formulation for controlling ectoparasites, containing at least one compound selected from the group consisting of the compounds as recited in claim 1, and salts thereof, as an active ingredient.

### Claim 5 (depends on 1)

A formulation for controlling endoparasites or for expelling endoparasites, containing at least one compound selected from the group consisting of the compounds as recited in claim 1, and salts thereof, as an active ingredient.