# US 8,772,200 B2 · Nitrogen-containing heterocyclic compound and agricultural fungicide

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- Number: US 8,772,200 B2
- Document ID: US8772200B2
- Status: Granted
- Kind: B2
- Application number: 13/519,209
- Filed: 2010-12-28
- Published: 2012-11-15
- Granted: 2014-07-08
- Earliest claimed: 2010-01-04
- Assignees: Nippon Soda Co., Ltd.
- Applicants: Kotaro Shibayama; Jun Inagaki; Yuto Saiki; Akira Mitani; Raito Kuwahara; Motoaki Sato; Satoshi Nishimura; Mami Kuboki
- Inventors: Kotaro Shibayama; Jun Inagaki; Yuto Saiki; Akira Mitani; Raito Kuwahara; Motoaki Sato; Satoshi Nishimura; Mami Kuboki
- Web page: https://patentgrep.com/patent/US8772200B2

## CPC

- A01N 43/42: condensed with carbocyclic rings
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61P 9/06: Antiarrhythmics
- C07D 215/14: Radicals substituted by oxygen atoms
- C07D 215/18: Halogen atoms or nitro radicals
- C07D 215/20: Oxygen atoms
- C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18)
- C07D 221/04: Ortho- or peri-condensed ring systems
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 471/04: Ortho-condensed systems
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 495/04: Ortho-condensed systems
- A01N 43/40: six-membered rings
- C07D 215/60: N-oxides
- 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

Provided is an agricultural fungicide that contains at least one selected from the group consisting of a novel nitrogen-containing heterocyclic compound represented by Formula (I), a salt thereof, or an N-oxide compound thereof. In Formula (I), R represents a group represented by CR1R2R3 or a cyano group. R1 to R3 each independently represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted hydroxyl group, or the like. R4 or R5 represents a halogeno group or the like. Y or Z represents a carbon atom or the like, and A or D represents a benzene ring or the like. X represents an oxygen atom or a nitrogen atom or the like.

## Claims

### Claim 1

A nitrogen-containing heterocyclic compound represented by Formula (II):
or a salt thereof, or an N-oxide compound thereof,
wherein, in Formula (II), R represents a group represented by CR1R2R3;
R1, R2 and R3, each independently represents a hydrogen atom, an unsubstituted or substituted C1-8 alkyl group, an unsubstituted C2-8 alkenyl group, an unsubstituted C2-8 alkynyl group, an unsubstituted C3-8 cycloalkyl group, an unsubstituted C4-8 cycloalkenyl group, an unsubstituted C6-10 aryl group, an unsubstituted heterocyclic group, an unsubstituted C1-8 acyl group, an unsubstituted (1-imino)C1-8 alkyl group, an unsubstituted or substituted carboxyl group, an unsubstituted or substituted carbamoyl group, an unsubstituted or substituted hydroxyl group, an unsubstituted or substituted amino group, a halogeno group, a cyano group, or a nitro group;
excepting in which: R1, R2 and R3 are all hydrogen atoms; R1, R2 and R3 are all unsubstituted C1-8 alkyl groups; any one of R1, R2 and R3 is a hydrogen atom and the remaining two are both unsubstituted C1-8 alkyl groups; and, any one of R1, R2 and R3 is an unsubstituted C1-8 alkyl group and the remaining two are both hydrogen atoms;
R1 and R2 may be joined to form O═;
R4 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted C2-8 alkenyl group, an unsubstituted C2-8 alkynyl group, an unsubstituted C3-8 cycloalkyl group, an substituted or substituted hydroxyl group, a halogeno group, a cyano group, or a nitro group;
m1 represents a number of R4 and is an integer of 0 to 6;
R5 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted C2-8 alkenyl group, an unsubstituted C2-8 alkynyl group, an unsubstituted C3-8 cycloalkyl group, an unsubstituted or substituted hydroxyl group, a halogeno group, a cyano group, or a nitro group;
n represents a number of R5 and is an integer of 0 to 5;
D represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring;
X represents an oxygen atom;
Y represents a carbon atom; and
Z represents a carbon atom; and
wherein the substituted C1-8 alkyl group is a C3-6 cycloalkyl C1-6 alkyl group, a C4-6 cycloalkenyl C1-6 alkyl group, a C1-6 haloalkvl group, a C6-10 aryl C1-6 alkyl group, 5- to 6-membered heteroaryl C1-6 alkyl group, a hydroxyl C1-6 alkyl group, a C1-6 alkoxy C1-6 alkyl group, a C1-7 acyloxy C1-6 alkyl group, a tri C1-6 alkylsilyloxy C1-6 alkyl group, a C1-6 alkyl-substituted C6-10 arylsulfonyloxy C1-6 alkyl group, a cyano C1-6 alkyl group, a C1-6 acyl C1-6 alkyl group, a 2-hydroxyimino C2-6 alkyl group, a formyl C1-6 alkyl group, a carboxy C1-6 alkyl group, a C1-6 alkoxycarbonyl C1-6 alkyl group, or an azido C1-6 alkyl group,
the substituted carboxyl group is a C1-6 alkoxycarbonyl group, a C2-6 alkenyloxycarbonyl group, a C2-6 alkynyloxycarbonyl group, a C6-10 aryloxycarbonyl group, or a C6-10 aryl C1-6 alkoxycarbonyl group,
the substituted carbamoyl group is a mono C1-6 alkylcarbamoyl group, a di C1-6 alkylcarbamoyl group, or a mono C6-10 arylcarbamoyl group,
the substituted hydroxyl group is a C1-6 alkoxy group, a C3-8 cycloalkyl C1-6 alkoxy group, a C6-10 aryl C1-6 alkoxy group, a C1-6 haloalkoxy group, a C2-6 alkenyloxy group, a C2-6 alkynyloxy group, a C3-6 cycloalkyloxy group, a C6-10 aryloxy group, a C6-10 aryl C1-6 alkyloxy group, a C1-7 acyloxy group, a C1-6 alkoxycarbonyl C1-6 alkoxy group, or a tri C1-6 alkylsilyloxy group, and
the substituted amino group is a mono C1-6 alkylamino group, a di C1-6 alkylamino group, a mono C1-6 alkylideneamino group, a mono C6-10 arylamino group, a di C6-10 arylamino group, a C6-10 aryl C1-6 alkylamino group, a C1-6 acylamino group, or a C1-6 alkoxycarbonylamino group.

### Claim 2 (depends on 1)

A nitrogen-containing heterocyclic compound, a salt thereof, or an N-oxide compound, according to claim 1, wherein the nitrogen-containing heterocyclic compound is represented by Formula (III):
wherein each of R, R4, R5, m1 and X represents the same meaning as those in Formula (II); and
n1 represents a number of R5 and is an integer of 0 to 4.

### Claim 3 (depends on 1)

An agricultural fungicide comprising, as an active ingredient, at least one selected from the group consisting of the nitrogen-containing heterocyclic compound, the salt thereof, and the N-oxide compound thereof, of claim 1.

### Claim 4 (depends on 1)

A nitrogen-containing heterocyclic compound, a salt thereof, or an N-oxide compound, according to claim 1, wherein R1 represents the unsubstituted or substituted hydroxyl group, R2 represents the hydrogen atom or the unsubstituted or substituted C1-8 alkyl group, and R3 represents the hydrogen atom, the unsubstituted or substituted C1-8 alkyl group, the unsubstituted C2-8 alkenyl group, the unsubstituted C2-8 alkynyl group, the unsubstituted C3-8 cycloalkyl group, the unsubstituted C6-10 aryl group, the unsubstituted hererocyclic group, the unsubstituted C1-8 acyl group, the unsubstituted (1-imino)C1-8 alkyl group, the C1-6 alkoxycarbonyl group, the unsubstituted or substituted hydroxyl group, or, the cyano group.

### Claim 5 (depends on 1)

A nitrogen-containing heterocyclic compound, a salt thereof, or an N-oxide compound, according to claim 1, wherein R4 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group, a C3-8 cycloalkyl group, a hydroxyl group, a C1-6 alkoxy group, or a halogeno group.

### Claim 6 (depends on 1)

A nitrogen-containing heterocyclic compound, a salt thereof, or an N-oxide compound according to claim 1, wherein R5 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C6-10 aryl C1-6 alkyl group, a C3-8 cycloalkyl group, a C1-6 alkoxy group, a halogeno group, a cyano group or a nitro group.

### Claim 7 (depends on 6)

A nitrogen-containing heterocyclic compound, a salt thereof, or an N-oxide compound, according to claim 6, wherein the nitrogen-containing heterocyclic compound is 2-[2-fluoro-6-(8-fluoroquinolin-3-yloxy)-phenyl]-3,3-dimethyl-butan-2-ol, 2-[2-fluoro-6-(8-fluoroquinolin-3-yloxy)-phenyl]-propan-2-ol, 2-[2-fluoro-6-(8-fluoro-2-methylquinolin-3-yloxy)-phenyl]-propan-2-ol, or 2-[2-fluoro-6-(7,8-difluoro-2-methylquinolin-3-yloxy)-phenyl]-propan-2-ol.

### Claim 8 (depends on 1)

An agricultural fungicide for seed treatment comprising, as an active ingredient, at least one selected from the group consisting of the nitrogen-containing heterocyclic compound, the salt thereof, and the N-oxide compound thereof, of claim 1.

### Claim 9 (depends on 1)

A method for treating a seed using an agricultural fungicide comprising, as an active ingredient, at least one selected from the group consisting of the nitrogen-containing heterocyclic compound, the salt thereof, and the N-oxide compound thereof, of claim 1.