# US 10,945,434 B2 · Azole derivative, intermediate compound, method for producing azole derivative, agricultural or horticultural chemical agent, and protective agent for industrial material

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- Number: US 10,945,434 B2
- Document ID: US10945434B2
- Status: Granted
- Kind: B2
- Application number: 16/636,502
- Filed: 2018-11-13
- Published: 2020-09-17
- Granted: 2021-03-16
- Earliest claimed: 2017-11-13
- Assignees: Kureha Corporation
- Applicants: Kureha Corporation
- Inventors: Ryo Harigae; Atsushi Ito; Taiji Miyake; Toru Yamazaki
- Web page: https://patentgrep.com/patent/US10945434B2

## CPC

- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01P 3/00: Fungicides
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 401/12: 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

It is provided a plant disease controlling agent having low toxicity to human and animals and excellent handling safety, and showing excellent controlling effects on various plant diseases and high antibiotic action to plant disease germs. A compound represented by the following the general formula (I), or an N-oxide or agrochemically acceptable salt thereof.

## Claims

### Claim 1

A compound represented by Formula (I),
or an N-oxide or agrochemically acceptable salt thereof, wherein:
A is N;
D is a hydrogen, a halogen group, or SRD;
where RD is a hydrogen, a cyano group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C2-C6-alkenyl group, a C2-C6-haloalkenyl group, a C2-C6-alkynyl group or a C2-C6-haloalkynyl group;
R1 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, a phenyl-C2-C4-alkynyl group, or COXR5;
where R5 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group;
X is a single bond, —O—, or —NR6—;
R6 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group; and R5 and R6 may form a ring;
R2 is —OR7 or —NR8R9;
R7, R8 and R9 are each independently a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group, and R8 and R9 may form a ring,
where aliphatic groups in R1, R2, R5, R6, R7, R8, and R9 may have 1, 2, 3 or the possible maximum number of the same or different groups Ra, and Ra is independently selected from a halogen group, a cyano group, a nitro group, a C1-C4-alkoxy group, and a C1-C4-haloalkoxy group;
R4 is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, a C1-C4-alkylamino group, a C1-C4-dialkylamino group, a C1-C4-alkylacylamino group, —SOR10, or —SF5;
the cycloalkyl group or phenyl group parts in R1, R2, R5, R6, R7, R8, and R9, or the phenyl group part in R4 may have 1, 2, 3, 4, 5, or the possible maximum number of the same or different groups Rb, and Rb is independently selected from a halogen group, a cyano group, a nitro group, a C1-C4-alkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkyl group, and a C1-C4-haloalkoxy group;
R3 is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, —SOR10, or —SF5;
where R10 is a C1-C4-alkyl group or a C1-C4-haloalkyl group;
E is a phenyl group or a 6-membered heteroaromatic ring containing 1 or 2 N atoms;
n R3 are bonded to any substitution sites;
when E is a phenyl group, then n is 0, 1, 2, 3, or 4, and when E is a 6-membered heteroaromatic ring containing 1 or 2 N atoms, then n is 0, 1, or 2;
Y is an oxygen atom, —CH2O—, —OCH2—, —NH—, —N(—C1-C4-alkyl)-, —N(—C3-C6-cycloalkyl)-, or —S(O)p—, which bonds to any sites of E;
where p is 0, 1, or 2;
Z is an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5-membered or 6-membered heteroaromatic ring or 9-membered or 10-membered heteroaromatic ring formed of 2 rings, containing 1 to 4 heteroatoms selected from O, N, and S; and
m R4 are bonded to any substitution sites;
when Z is a phenyl group, then m is 1, 2, 3, 4, or 5 and when Z is a naphthyl group or a heteroaromatic ring, then m is 0, 1, 2, 3, or 4.

### Claim 2 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I),
R1 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, or COXR5;
R2 is —OR7;
R5 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, or a C2-C6-alkynyl group;
R6 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, or a C2-C6-alkynyl group;
R3 is a halogen group, a cyano group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, —SOR10, or —SF5; and
R4 is a halogen group, a nitro group, a cyano group, an amino group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, a C1-C4-alkylamino group, a C1-C4-dialkylamino group, a C1-C4-alkylacylamino group, —SOR10, or —SF5.

### Claim 3 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I),
R1 is a hydrogen, a C1-C6-alkyl group, or COXR5;
R5 is a hydrogen, or C1-C6-alkyl group;
R6 is a hydrogen;
R3 is a halogen group, a cyano group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, —SOR10, or —SF5; and
R4 is a halogen group, a nitro group, a cyano group, an amino group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, a C1-C4-alkylamino group, a C1-C4-dialkylamino group, a C1-C4-alkylacylamino group, —SOR10, or —SF5.

### Claim 4 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I),
R1 is a hydrogen, or a C1-C6-alkyl group;
R7 is a C1-C6-alkyl group;
R3 is a halogen group, a cyano group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, or a C1-C4-alkoxy group; and
R4 is a halogen group, a cyano group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, or a C1-C4-haloalkoxy group.

### Claim 5 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I), E is a phenyl group.

### Claim 6 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I), Z is a phenyl group, a naphthyl group, or a 5-membered or 6-membered heteroaromatic ring containing 1 to 3 heteroatoms selected from N and S.

### Claim 7 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I), Z is a phenyl group.

### Claim 8 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I), Y is an oxygen atom.

### Claim 9 (depends on 1)

The compound or the salt thereof according to claim 1, wherein in the general formula (I), A is N, and D is a hydrogen.

### Claim 10 (depends on 1)

The compound or the salt thereof according to claim 1, wherein the compound is represented by Formula (II),

### Claim 11 (depends on 1)

A method for producing a compound represented by Formula (I) according to claim 1,
the method comprising a step of converting a compound represented by Formula (V),
into a compound represented by Formula (VI),
by using a dialkyl sulfate represented by Formula (VII),
or R7-LG, with LG being a nucleophilically substitutable leaving group, and iodine and a carbonate in dimethyl sulfoxide.

### Claim 12 (depends on 11)

The production method according to claim 11, wherein LG in R7-LG is a halogen group.

### Claim 13 (depends on 11)

The production method for producing the compound represented by the general formula (VI) described above according to claim 11,
the method comprising a step of converting the compound represented by the general formula (V) into the compound represented by the general formula (VI) by using R7-LG, with LG being a nucleophilically substitutable leaving group, and iodine and a carbonate in dimethyl sulfoxide.

### Claim 14 (depends on 1)

An agricultural or horticultural chemical agent, or a protective agent for industrial material comprising a compound represented by Formula (I) according to claim 1 as an active ingredient.

### Claim 15

A compound represented by Formula (I),
or agrochemically acceptable salt thereof, wherein:
A is N;
D is a hydrogen;
R1 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, a phenyl-C2-C4-alkynyl group, or COXR5;
where R5 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group;
X is a single bond, —O—, or —NR6—;
R6 is a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group; and R5 and R6 may form a ring;
R2 is —OR7 or —NR8R9;
R7, R8 and R9 are each independently a hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyl-C1-C4-alkyl group, a phenyl group, a phenyl-C1-C4-alkyl group, a phenyl-C2-C4-alkenyl group, or a phenyl-C2-C4-alkynyl group, and R8 and R9 may form a ring,
where aliphatic groups in R1, R2, R5, R6, R7, R8, and R9 may have 1, 2, 3 or the possible maximum number of the same or different groups Ra, and Ra is independently selected from a halogen group, a cyano group, a nitro group, a C1-C4-alkoxy group, and a C1-C4-haloalkoxy group;
R4 is a halogen group, a cyano group, a nitro group, an amino group, a phenyl group, a phenyl-oxy group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, a C1-C4-alkylamino group, a C1-C4-dialkylamino group, a C1-C4-alkylacylamino group, —SOR10, or —SF5;
the cycloalkyl group or phenyl group parts in R1, R2, R5, R6, R7, R8, and R9, or the phenyl group part in R4 may have 1, 2, 3, 4, 5, or the possible maximum number of the same or different groups Rb, and Rb is independently selected from a halogen group, a cyano group, a nitro group, a C1-C4-alkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkyl group, and a C1-C4-haloalkoxy group;
R3 is a halogen group, a cyano group, a nitro group, a phenyl group, a phenyl-oxy group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, —SOR10, or —SF5;
where Rm is a C1-C4-alkyl group or a C1-C4-haloalkyl group;
E is a phenyl group or a 6-membered heteroaromatic ring containing 1 or 2 N atoms;
n R3 are bonded to any substitution sites;
when E is a phenyl group, then n is 0, 1, 2, 3, or 4, and when E is a 6-membered heteroaromatic ring containing 1 or 2 N atoms, then n is 0, 1, or 2;
Y is an oxygen atom;
Z is an aromatic hydrocarbon group which is a phenyl group or a naphthyl group, or a 5-membered or 6-membered heteroaromatic ring or 9-membered or 10-membered heteroaromatic ring formed of 2 rings, containing 1 to 4 heteroatoms selected from O, N, and S; and
m R4 are bonded to any substitution sites;
when Z is a phenyl group, then m is 1, 2, 3, 4, or 5 and when Z is a naphthyl group or a heteroaromatic ring, then m is 0, 1, 2, 3, or 4.