# US 10,870,638 B2 · Pyridazinone compound or its salt, and herbicide containing it

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- Number: US 10,870,638 B2
- Document ID: US10870638B2
- Status: Granted
- Kind: B2
- Application number: 16/088,722
- Filed: 2017-03-29
- Published: 2020-06-04
- Granted: 2020-12-22
- Earliest claimed: 2016-03-30
- Assignees: Ishihara Sangyo Kaisha, Ltd.
- Applicants: Ishihara Sangyo Kaisha, Ltd.
- Inventors: Toshihiko Ueki; Ryu Yamada; Hisaki Tanaka
- Web page: https://patentgrep.com/patent/US10870638B2

## CPC

- C07D 403/12: linked by a chain containing hetero atoms as chain links
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/06: containing —O—CO—O— groups; Thio analogues thereof
- A01P 13/00: Herbicides; Algicides
- C07D 237/16: Two oxygen atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- 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
- A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS

## Abstract

A novel herbicide having remarkable herbicidal activities against undesired plants is provided. A pyridazinone compound represented by the formula (I) or its salt: wherein X is —O—, —S—, —SO—, —SO2— or —N(Y)—; Q is monocyclic aryl which may be substituted by Z, monocyclic heteroaryl which may be substituted by Z or the like; Y is a hydrogen atom or alkyl; Z is halogen, alkyl or the like; R1 is alkyl, alkenyl or the like; R2 is a hydrogen atom, alkyl or the like; R3 is halogen, hydroxy or the like; R4 is a hydrogen atom, alkyl or the like; and n is an integer of from 0 to 4.

## Claims

### Claim 1

A pyridazinone compound represented by the formula (I) or its salt:
wherein X is —O— and Q is bicyclic heteroaryl which may be substituted by Z; or X is —S—, —SO—, —SO2— or —N(Y)— and Q is monocyclic aryl which may be substituted by Z, monocyclic heteroaryl which may be substituted by Z, bicyclic aryl which may be substituted by Z, or bicyclic heteroaryl which may be substituted by Z
Y is a hydrogen atom or alkyl;
R1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, haloalkyl, monocyclic aryl which may be substituted by Z, monocyclic arylalkyl which may be substituted by Z, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dialkylaminoalkyl, alkoxyalkyl, amino, nitro, alkylcarbonylalkyl, alkoxycarbonylalkyl or hydroxycarbonylalkyl;
R2 is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, halogen, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl or cyano;
R3 is halogen, hydroxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, nitro, amino, alkylcarbonyl or cycloalkyl;
R4 is a hydrogen atom, alkyl, —C(O)R6, —C(S)R6, —SR7, —SOR7, —SO2R7, monocyclic arylalkyl which may be substituted by Z, alkoxyalkyl, —CH(J1)OCOOJ2, alkylcarbonylalkyl, monocyclic aryl which may be substituted by Z, monocyclic arylcarbonylalkyl which may be substituted by Z, alkenyl, alkoxyalkoxyalkyl, alkoxycarbonylalkyl, alkynyl, cyanoalkyl, haloalkoxyalkyl or dialkylaminoalkyl;
R6 is alkyl, alkoxy, morpholino, dialkylamino, (monocyclic aryl which may be substituted by Z)(alkyl)amino, cycloalkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, alkylthio, alkenyl, alkynyl, alkoxycarbonylalkyl, cycloalkylalkyl, cyanoalkyl, alkoxyalkoxyalkyl, monocyclic aryl which may be substituted by Z, monocyclic heteroaryl which may be substituted by Z, monocyclic arylalkyl which may be substituted by Z, monocyclic aryloxy which may be substituted by Z, monocyclic arylthio which may be substituted by Z, monocyclic aryloxyalkyl which may be substituted by Z, monocyclic arylthioalkyl which may be substituted by Z, alkoxycarbonyl, alkoxyalkoxy, haloalkoxy, haloalkoxyalkoxy, alkylthioalkoxy, cycloalkoxyalkoxy, monocyclic arylalkoxy which may be substituted by Z, monocyclic aryloxyalkoxy which may be substituted by Z, monocyclic heteroaryloxyalkoxy which may be substituted by Z, alkenyloxyalkoxy, alkoxyalkoxyalkoxy, alkynyloxy, alkenyloxy, haloalkenyl, dialkylaminoalkyl, alkylthioalkoxyalkoxy, cycloalkylalkoxy, cycloalkylalkoxyalkoxy, monocyclic arylalkoxyalkoxy which may be substituted by Z, monocyclic heteroarylalkoxyalkoxy which may be substituted by Z or cycloalkoxy which may be substituted by Z;
R7 is alkyl, haloalkyl, cycloalkyl or monocyclic aryl which may be substituted by Z;
Z is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, cyano, nitro, —C(O)OR5, formyl, alkylthio, alkylsulfinyl, alkyl sulfonyl, —CH═NOJ3 or dialkylaminocarbonyl;
R5 is a hydrogen atom or alkyl;
J1 is a hydrogen atom or alkyl;
J2 is alkyl or cycloalkyl;
J3 is a hydrogen atom, alkylcarbonyl or alkoxyalkyl; and
n is an integer of from 0 to 4.

### Claim 2 (depends on 1)

The pyridazinone compound or its salt according to claim 1, wherein in the formula (I), X is —O— and Q is bicyclic heteroaryl which may be substituted by Z; or X is —S—, —SO—, —SO2— or —N(Y)— and Q is monocyclic aryl which may be substituted by Z, monocyclic heteroaryl which may be substituted by Z, bicyclic aryl which may be substituted by Z, or bicyclic heteroaryl which may be substituted by Z
Y is a hydrogen atom or alkyl;
Z is halogen, alkyl, haloalkyl, cyano, nitro or —C(O)OR5;
R1 is alkyl, alkenyl, alkynyl or cycloalkyl;
R2 is a hydrogen atom, alkyl, haloalkyl or cycloalkyl;
R3 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy or cycloalkyl;
R4 is a hydrogen atom, alkyl, —C(O)R6 or —SO2R7;
R5 is a hydrogen atom or alkyl;
R6 is alkyl, alkoxy or morpholino;
R7 is alkyl; and
n is an integer of from 1 to 4.

### Claim 3 (depends on 1)

A herbicide containing the pyridazinone compound or its salt as defined in claim 1 as an active ingredient.

### Claim 4 (depends on 1)

A method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the pyridazinone compound or its salt as defined in claim 1 to the undesired plants or to a place where they grow.

### Claim 5 (depends on 4)

The method according to claim 4, wherein the application amount of the pyridazinone compound or its salt is from 0.1 to 5,000 g/ha.