# US 5,705,453 A · Indazole compounds and the use thereof

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- Number: US 5,705,453 A
- Document ID: US5705453A
- Status: Granted
- Kind: A
- Application number: 08/599,340
- Filed: 1996-02-08
- Granted: 1998-01-06
- Earliest claimed: 1995-02-09
- Assignees: Mitsubishi Chemical Corporation
- Inventors: Nobuo Kyomura; Shuko Okui; Yoshiya Ikeda; Shigeru Suzuki; Hirohumi Tomita; Yoshiaki Higashino
- Web page: https://patentgrep.com/patent/US5705453A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: 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

## Abstract

A indazole compound useful as an agricultural and horticultural insecticide, miticide, and/or fungicide which is represented by the formula set out below, wherein R.sup.1 represents hydrogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, or a halogen; R.sup.2 and R.sup.3 are preferably hydrogen atoms; and R.sup.4 represents, for example, hydrogen, a C.sub.1 -C.sub.8 alkyl, a C.sub.1 -C.sub.8 alkoxy, a halogen, a C.sub.1 -C.sub.4 haloalkoxy, a 5- to 7-membered cycloalkoxy, a C.sub.1 -C.sub.4 alkylthio, a phenylamino, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino, pyrrole-yl, imidazole-yl, pyrrolidino, piperidino, or phenoxy. ##STR1##

## Claims

### Claim 1

An indazole compound represented by the following formula: ##STR13## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -c.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, or a halogen atom; R.sup.2 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.5 alkanoyl group, methoxymethyl group, or 2-methoxy ethyl group, a C.sub.2 -C.sub.5 alkanoyl group, methoxymethyl group, or 2-methoxy ethyl group; R.sup.3 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group; R.sup.4 represents a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.8 alkoxy group, a halogen atom, a C.sub.1 -C.sub.4 haloalkoxy group, a 5-membered to 7-membered cycloalkoxy group which may be substituted, a C.sub.1 -C.sub.4 alkylthio group, a phenylamino group which may be substituted, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino group, pyrrolyl group, imidazolyl group, pyrrolidino group, a piperidino group which may be substituted, or a phenoxy group which may be substituted, and where a functional group selected from the group consisting of said cycloalkoxy, phenylamino, piperidino, and phenoxy groups has two or more substituents on its nucleus, any two adjacent substituents among said substituents may form a ring structure together with two atoms on the nucleus to which the adjacent substituents bind, and said ring structure may further has one more substitutents on the ring.

### Claim 2 (depends on 1)

The indazole compounds according to claim 1, wherein R.sup.4 is a hydrogen atom, a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.8 alkoxy group, a halogen atom, a C.sub.1 -C.sub.4 haloalkoxy group, a 5- to 7-membered cycloalkoxy group which may optionally have one or more C.sub.1 -C.sub.4 alkyl groups or a condensed benzene ring, a phenylamino group which may optionally have one or more halogen atoms or one or more C.sub.1 -C.sub.4 haloalkyl group, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino group, pyrrolyl group, imidazolyl group, pyrrolidino group, a piperidino group which may optionally have a condensed benzene ring, or a phenoxy group which may optionally have one to three substituents selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.8 alkoxy group, a halogen atom, nitro group, cyano group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, phenyl group, phenoxy group, a C.sub.2 -C.sub.5 alkanoyl group whose oxo group may be protected with a ketal group, benzoyl group, a C.sub.1 -C.sub.4 alkoxycarbonyl group, a C.sub.1 -C.sub.4 alkylthio group, trifluoromethylthio group, and methylenedioxy group and where said phenoxy group has two or three substituents, the substituents may be the same or different, and the benzene ring of said phenoxy group may have a condensed benzene ring which ring may further be substituted with one or more halogen atoms or one or more C.sub.1 -C.sub.4 alkoxy groups or a condensed saturated furan ring which ring may further be substituted with one or more C.sub.1 -C.sub.4 alkyl groups.

### Claim 3 (depends on 1)

The indazole compound according to claim 1, wherein R.sup.4 is a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a halogen atom, a C.sub.1 -C.sub.4 haloalkoxy group, a 5- to 7-membered cycloalkoxy group which may optionally have one or more C.sub.1 -C.sub.4 alkyl groups or one condensed benzene ring, a phenylamino group which may optionally have one or more halogen atoms or one or more C.sub.1 -C.sub.4 haloalkyl groups, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino group, pyrrolyl group, imidazolyl group, pyrrolidino group, a piperidino group which may optionally have one condensed benzene ring, or a phenoxy group which may optionally have one to three substituents selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.8 alkoxy group, a halogen atom, nitro group, cyano group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, phenyl group, phenoxy group, a C.sub.2 -C.sub.5 alkanoyl group whose oxo group may be protected with a ketal group, a C.sub.1 -C.sub.4 alkoxycarbonyl group, a C.sub.1 -C.sub.4 alkylthio group, and methylenedioxy group (where said phenoxy group has two or three substituents, the substituents may be the same or different), and the benzene ring of said phenoxy group may have one condensed benzene ring the benzene ring of the phenoxy group may have one condensed benzene ring which ring may further be substituted with one or more halogen atoms or one condensed saturated furan ring which ring may further be substituted with one or more C.sub.1 -C.sub.4 alkyl groups.

### Claim 4 (depends on 1)

The indazole compound according to claim 1, wherein R.sup.4 is a C.sub.1 -C.sub.8, alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a halogen atom, a C.sub.1 -C.sub.4 haloalkoxy group, a 5- to 7-membered cycloalkoxy group which may optionally have one C.sub.1 -C.sub.4 alkyl group or one condensed benzene ring, a phenylamino group which may optionally have one halogen atom or one C.sub.1 -C.sub.4 haloalkyl group, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino group, pyrrolyl group, imidazolyl group, pyrrolidino group, a piperidino group which may optionally have one condensed benzene ring, or a phenoxy group which may optionally have one or two substituents selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.8 alkoxy group, a halogen atom, nitro group, Cyano group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, phenyl group, phenoxy group, a C.sub.2 -C.sub.5 alkanoyl group whose oxo group may be protected with a ketal group, a C.sub.1 -C.sub.4 alkoxycarbonyl group, a C.sub.1 -C.sub.4 alkylthio group, and a methylenedioxy group and where said phenoxy group has two substituents, the substituents may be the same or different, and the benzene ring of said phenoxy group may have one condensed benzene ring which ring may further be substituted with one halogen atom or one condensed saturated furan ring which ring may further be substituted with one C.sub.1 -C.sub.4 alkyl group.

### Claim 5 (depends on 1)

The indazole compound according to claim 1, wherein R.sup.2 and R.sup.3 are hydrogen atoms. compounds represented by general formula (II) and general formula (III) can be prepared by methods which are known to those skilled in the art.

### Claim 6

An agricultural and horticultural pesticide which comprises an effective amount of an indazole compound represented by the formula ##STR14## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, or a halogen atom; R.sup.2 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.5 alkanoyl group, methoxymethyl group, or 2-methoxy ethyl group; R.sup.3 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group; R.sub.4 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a halogen atom, a C.sub.1 -C.sub.4 haloalkoxy group, a 5-membered to 7-membered cycloalkoxy group which may be substituted, a C.sub.1 -C.sub.4 alkylthio group, a phenylamino group which may be substituted, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino group, pyrrolyl group, imidazolyl group, pyrrolidino group, a piperidino group which may be substituted, or a phenoxy group which may be substituted, and where a functional group selected from the group consisting of said cycloalkoxy, phenylamino, piperidino, and phenoxy groups has two or more substituents on its nucleus, any two adjacent substituents among said substituents may form a ring structure together with two atoms on the nucleus to which the adjacent substituents bind, and said ring structure may further has one or more substitutents on the ring, and an agrochemical adjuvant therefor.

### Claim 7 (depends on 6)

An agricultural and horticultural pesticide according to claim 6 wherein R.sup.4 is a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a halogen atom, a C.sub.1 -C.sub.4 haloalkoxy group, a 5- to 7-membered cycoalkoxy group which may optionally have one or more C.sub.1 -C.sub.4 alkyl groups or one condensed benzene ring, a phenylamino group which may optionally have one or more halogen atoms or one or more C.sub.1 -C.sub.4 haloalkyl groups, an N-(C.sub.1 -C.sub.4 alkyl)-phenylamino group, pyrrolyl group, imidazolyl group, pyrrolidino group, a piperidino group which may optionally have one condensed benzene ring, or a phenoxy group which may optionally have one to three substituents selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a halogen atom, nitro group, cyano group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.4 haloalkoxy group, phenyl group, phenoxy group, a C.sub.2 -C.sub.5 alkanoyl group whose oxo group may be protected with a ketal group, a C.sub.1 -C.sub.4 alkoxycarbonyl group, a C.sub.1 -C.sub.4 alkylthio group, and methylenedioxy group and where said phenoxy group has two or three substituents, the substituents may be the same or different, and the benzene ring of said phenoxy group may have one condensed benzene ring which ring may further be substituted with one or more halogen atoms or one condensed saturated furan ring which ring may further be substituted with one or more C.sub.1 -C.sub.4 alkyl groups.