# US 11,109,593 B2 · Isoxazolin-5-one derivative and herbicide containing same as active ingredient

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- Number: US 11,109,593 B2
- Document ID: US11109593B2
- Status: Granted
- Kind: B2
- Application number: 16/479,099
- Filed: 2018-01-19
- Published: 2020-08-27
- Granted: 2021-09-07
- Earliest claimed: 2017-01-20
- Assignees: Hokko Chemical Industry Co., Ltd.
- Applicants: Hokko Chemical Industry Co., Ltd.
- Inventors: Jun Suzuki; Keiyo Nakai; Kohei Koyama; Yutaro Tanaka; Tsunehiro Kido
- Web page: https://patentgrep.com/patent/US11109593B2

## CPC

- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01P 13/02: selective
- C07D 261/12: Oxygen atoms
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

An isoxazolin-5-one derivative represented by the following (1): wherein R1 represents a C1-C6 haloalkyl group, and R2 to R4 and X each represents a certain substituent or the like; and n represents an integer of 1 to 4, wherein X's may be different from each other when n represents an integer of 2 to 4, and an herbicide containing the isoxazolin-5-one derivative as an active ingredient are provided.

## Claims

### Claim 1

An isoxazolin-5-one derivative of formula (1):
wherein,
R1 is a C1-C6 haloalkyl group;
R2 is a hydrogen atom,
a C1-C6 alkyl group,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group,
a C2-C6 alkynyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 haloalkoxy C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 alkylthio C1-C6 alkyl group,
a C1-C6 alkylcarbonyl C1-C6 alkyl group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a phenoxy C1-C6 alkyl group,
a C7-C11 aralkyloxy C1-C6 alkyl group,
a phenylcarbonyl C1-C6 alkyl group,
a C1-C6 alkylcarbonyl group,
a C1-C6 haloalkylcarbonyl group,
a C2-C6 alkenylcarbonyl group,
a C2-C6 alkynylcarbonyl group,
a C3-C6 cycloalkylcarbonyl group,
a C3-C6 cycloalkyl C1-C6 alkylcarbonyl group,
a C1-C6 alkoxy C1-C6 alkylcarbonyl group,
a C1-C6 haloalkoxy C1-C6 alkylcarbonyl group,
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkylcarbonyl group,
a C1-C6 alkylthio C1-C6 alkylcarbonyl group,
a C1-C6 haloalkylthio C1-C6 alkylcarbonyl group,
a benzoyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic carbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkoxycarbonyl group,
a C1-C6 haloalkoxycarbonyl group,
a C2-C6 alkenyloxycarbonyl group,
a C2-C6 alkynyloxycarbonyl group,
a C3-C6 cycloalkyloxycarbonyl group,
a C3-C6 cycloalkyl C1-C6 alkoxycarbonyl group,
a C1-C6 alkoxy C1-C6 alkoxycarbonyl group,
a C1-C6 haloalkoxy C1-C6 alkoxycarbonyl group,
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkoxycarbonyl group,
a C1-C6 alkylthio C1-C6 alkoxycarbonyl group,
a C1-C6 haloalkylthio C1-C6 alkoxycarbonyl group,
a phenoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkyloxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a phenoxy C1-C6 alkoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic oxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkylthiocarbonyl group,
a C1-C6 haloalkylthiocarbonyl group,
a C1-C6 alkylaminocarbonyl group,
a C1-C6 haloalkylaminocarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
a C1-C6 haloalkylsulfonyl group,
a C2-C6 alkenylsulfonyl group,
a C2-C6 alkynylsulfonyl group,
a C3-C6 cycloalkylsulfonyl group,
a C3-C6 cycloalkyl C1-C6 alkylsulfonyl group,
a C1-C6 alkoxy C1-C6 alkylsulfonyl group,
a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkylaminosulfonyl group,
or a di-C1-C6 alkylaminosulfonyl group wherein the di-C1-C6 alkyl groups may be same or different;
R3 is a hydrogen atom,
a halogen atom,
a C1-C6 alkyl group,
a C1-C6 haloalkyl group,
a C3-C6 cycloalkyl group,
a phenyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
an amino group,
a C1-C6 alkylamino group,
or a di-C1-C6 alkylamino group wherein the di-C1-C6 alkyl groups may be same or different;
R4 is a hydrogen atom,
a C1-C15 alkyl group,
a C1-C15 haloalkyl group,
a C2-C6 alkenyl group,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group,
a C2-C6 haloalkynyl group,
a C3-C6 cycloalkyl group,
a C3-C6 cycloalkyl C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 haloalkoxy C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 alkylthio C1-C6 alkyl group,
a C1-C6 haloalkylthio C1-C6 alkyl group,
a C1-C6 alkylsulfinyl C1-C6 alkyl group,
a C1-C6 alkylsulfonyl C1-C6 alkyl group,
a C1-C6 alkylamino C1-C6 alkyl group,
a di-C1-C6 alkylamino C1-C6 alkyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylcarbonyl C1-C6 alkyl group,
a phenyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group,
an indanyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a tetrahydronaphthyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a heterocyclic C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a phenoxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyloxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a phenylcarbonyl C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group; a benzoyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkoxycarbonyl group,
a C1-C6 alkylaminocarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
a C1-C6 haloalkylsulfonyl group,
a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
or a C7-C11 aralkylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group;
X is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C1-C6 alkoxy group; and
n is an integer of 1 to 4, wherein X's may be different from each other when n represents an integer of 2 to 4.

### Claim 2 (depends on 1)

The isoxazolin-5-one derivative according to claim 1, wherein R1 is a C1-C6 fluoroalkyl group.

### Claim 3 (depends on 1)

The isoxazolin-5-one derivative according to claim 1, wherein R1 is a trifluoromethyl group.

### Claim 4 (depends on 1)

The isoxazolin-5-one derivative according to claim 1, wherein
R1 is a trifluoromethyl group;
R2 is a hydrogen atom,
a C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group,
a C1-C6 haloalkylcarbonyl group,
a C3-C6 cycloalkylcarbonyl group,
a C1-C6 alkoxy C1-C6 alkylcarbonyl group,
a benzoyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic carbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkoxycarbonyl group,
a C2-C6 alkenyloxycarbonyl group,
a C1-C6 alkoxy C1-C6 alkoxycarbonyl group,
a phenoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkyloxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkylaminocarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
a C1-C6 haloalkylsulfonyl group,
a C3-C6 cycloalkylsulfonyl group,
a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
or a C7-C11 aralkylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group;
R3 is a hydrogen atom,
a C1-C6 alkyl group which may be substituted with a fluorine atom,
or a C3-C6 cycloalkyl group;
R4 is a hydrogen atom,
a C1-C15 alkyl group,
a C1-C15 haloalkyl group,
a C2-C6 alkenyl group,
a C2-C6 alkynyl group,
a C3-C6 cycloalkyl group,
a C3-C6 cycloalkyl C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 alkylthio C1-C6 alkyl group,
a phenyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group,
an indanyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a tetrahydronaphthyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a heterocyclic C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a phenoxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyloxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
or a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group;
X is a hydrogen atom or a halogen atom; and
n is an integer of 1 to 4 wherein X's may be different from each other when n represents an integer of 2 to 4.

### Claim 5 (depends on 1)

A herbicide comprising the isoxazolin-5-one derivative according to claim 1 as an active ingredient.

### Claim 6 (depends on 2)

The isoxazolin-5-one derivative according to claim 2, wherein R1 is a trifluoromethyl group.

### Claim 7 (depends on 2)

The isoxazolin-5-one derivative according to claim 2, wherein
R1 is a trifluoromethyl group;
R2 is a hydrogen atom,
a C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group,
a C1-C6 haloalkylcarbonyl group,
a C3-C6 cycloalkylcarbonyl group,
a C1-C6 alkoxy C1-C6 alkylcarbonyl group,
a benzoyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic carbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkoxycarbonyl group,
a C2-C6 alkenyloxycarbonyl group,
a C1-C6 alkoxy C1-C6 alkoxycarbonyl group,
a phenoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkyloxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkylaminocarbonyl group; a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
a C1-C6 haloalkylsulfonyl group,
a C3-C6 cycloalkylsulfonyl group,
a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
or a C7-C11 aralkylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
R3 is a hydrogen atom,
a C1-C6 alkyl group which may be substituted with a fluorine atom,
or a C3-C6 cycloalkyl group;
R4 is a hydrogen atom,
a C1-C15 alkyl group,
a C1-C15 haloalkyl group,
a C2-C6 alkenyl group,
a C2-C6 alkynyl group,
a C3-C6 cycloalkyl group,
a C3-C6 cycloalkyl C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 alkylthio C1-C6 alkyl group,
a phenyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group,
an indanyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a tetrahydronaphthyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a heterocyclic C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a phenoxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyloxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
or a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group;
X is a hydrogen atom or a halogen atom; and
n is an integer of 1 to 4 wherein X's may be different from each other when n represents an integer of 2 to 4.

### Claim 8 (depends on 3)

The isoxazolin-5-one derivative according to claim 3, wherein in the formula (1),
R1 is a trifluoromethyl group;
R2 is a hydrogen atom,
a C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group,
a C1-C6 haloalkylcarbonyl group,
a C3-C6 cycloalkylcarbonyl group,
a C1-C6 alkoxy C1-C6 alkylcarbonyl group,
a benzoyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic carbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkylcarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkoxycarbonyl group,
a C2-C6 alkenyloxycarbonyl group,
a C1-C6 alkoxy C1-C6 alkoxycarbonyl group,
a phenoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C7-C11 aralkyloxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a heterocyclic C1-C6 alkoxycarbonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
a C1-C6 alkylaminocarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
a C1-C6 haloalkylsulfonyl group,
a C3-C6 cycloalkylsulfonyl group,
a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group,
or a C7-C11 aralkylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom or a C1-C6 alkyl group;
R3 is a hydrogen atom,
a C1-C6 alkyl group which may be substituted with a fluorine atom,
or a C3-C6 cycloalkyl group;
R4 is a hydrogen atom,
a C1-C15 alkyl group,
a C1-C15 haloalkyl group,
a C2-C6 alkenyl group,
a C2-C6 alkynyl group,
a C3-C6 cycloalkyl group,
a C3-C6 cycloalkyl C1-C6 alkyl group,
a C1-C6 alkoxy C1-C6 alkyl group,
a C1-C6 alkylthio C1-C6 alkyl group,
a phenyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyl group which may be monosubstituted or polysubstituted with a halogen atom, cyano, nitro, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group or a C1-C6 haloalkylthio group,
an indanyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a tetrahydronaphthyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a heterocyclic C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a phenoxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C7-C11 aralkyloxy C1-C6 alkyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,
a C1-C6 alkylcarbonyl group,
a di-C1-C6 alkylaminocarbonyl group wherein the di-C1-C6 alkyl groups may be same or different,
a C1-C6 alkylsulfonyl group,
or a phenylsulfonyl group which may be monosubstituted or polysubstituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group;
X is a hydrogen atom or a halogen atom; and
n is an integer of 1 to 4 wherein X's may be different from each other when n represents an integer of 2 to 4.

### Claim 9 (depends on 2)

A herbicide comprising the isoxazolin-5-one derivative according to claim 2 as an active ingredient.

### Claim 10 (depends on 3)

A herbicide comprising the isoxazolin-5-one derivative according to claim 3 as an active ingredient.

### Claim 11 (depends on 4)

A herbicide comprising the isoxazolin-5-one derivative according to claim 4 as an active ingredient.