Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-06-06
2004-07-13
Balasubramanian, Venkataraman (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S336000, C514S344000, C514S345000, C514S256000, C514S269000, C548S263200, C546S272400, C544S310000, C544S315000, C544S319000
Reexamination Certificate
active
06762197
ABSTRACT:
TECHNICAL FIELD
The present invention relates to triazolone compounds, use thereof and production intermediates thereof.
BACKGROUND ART
WO99/07687 describes that a certain kind of triazolone compounds has a fungicidal activity.
DISCLOSURE OF THE INVENTION
The present invention provides compounds having a fungicidal activity, particularly an excellent fungicidal activity on fungi causing plant diseases and useful for controlling plant diseases.
Namely, the present invention provides a triazolone compound of the formula [I] (hereinafter, referred to as the compound of the invention):
wherein,
R
1
represents a A
1
-L
1
-, A
1
-ON═CA
2
—, A
1
-ON═C(Me)CH
2
ON═CA
2
—, A
1
-C(A
2
)═N—OCH
2
—, A
1
S—C(A
2
)═N—, A
1
-C(═S)NH—, A
1
S—C(═S)NH—, A
1
S—C(SA
2
)═N—, A
1
-ON═C(CN)—, A
1
-ON═C(Me)CH
2
ON═C(CN)—, A
1
-C(CN)═N—OCH
2
—, halogen atom, nitro or cyano;
wherein, L
1
represents single bond, oxygen atom, sulfur atom, carbonyl, —OCH
2
—, —SCH
2
—, —C(═O)O—, —OC(═O)—, —C(═O)OCH
2
—, —NH— or C
1
-C
6
alkylimino;
A
1
and A
2
, which are the same or different, represent hydrogen atom, C
1
-C
10
alkyl, C
2
-C
10
alkenyl, C
2
-C
10
alkynyl, C
3
-C
10
cycloalkyl, (C
3
-C
10
cycloalkyl) C
1
-C
10
alkyl, C
5
-C
10
cycloalkenyl, (C
5
-C
10
cycloalkenyl) C
1
-C
10
alkyl, phenyl, naphthyl, phenyl C
1
-C
10
alkyl, naphtyl C
1
-C
10
alkyl, 5- or 6-membered heterocyclic group optionally condensed with a benzene ring, or methyl substituted by 5- or 6-membered heterocyclic group optionally condensed with a benzene ring;
the alkyl, the alkenyl, the alkynyl, the cycloalkyl, the cycloalkylalkyl, the cycloalkenyl and the cycloalkenylalkyl, represented by A
1
and A
2
, may optionally be each substituted by one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C
1
-C
10
alkoxy, C
1
-C
10
haloalkoxy, C
1
-C
10
alkylthio, C
1
-C
10
haloalkylthio, (C
1
-C
9
alkyl)carbonyl, (C
1
-C
9
alkoxy)carbonyl, (C
1
-C
9
alkyl)carbonylamino, phenyl, phenoxy, benzyloxy and tri(C
1
-C
10
alkyl)silyl;
the phenyl, the naphthyl, the benzene ring in the phenylalkyl, the naphthalene ring in the phenylnaphthyl, the heterocyclic group, and the heterocyclic ring in the methyl substituted by heterocylic group, represented by A
1
and A
2
, may optionally be each substituted by one or more substituents selected from the group consisting of halogen atom(s), cyano, nitro, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
10
cycloalkyl, C
1
-C
10
alkoxy, C
1
-C
10
haloalkoxy, C
1
-C
10
alkylthio, C
1
-C
10
haloalkylthio, (C
1
-C
9
alkyl)carbonyl, (C
1
-C
9
alkoxy)carbonyl, (C
1
-C
9
alkyl)carbonylamino, phenyl, phenoxy, benzyloxy, tri(C
1
-C
10
alkyl)silyl, methylenedioxy and difluoromethylenedioxy;
with the proviso, when L
1
is single bond, A
1
is not a hydrogen atom;
T represents optionally substituted m-phenylene, optionally substituted m-azaphenylene (m-pyridinediyl) or optionally substituted m-diazaphenylene (m-diazinediyl, namely, m-pyridazinediyl, m-pyrimidinediyl or m-pyrazinediyl) bonded to R
1
and to CH
2
each via a carbon atom;
wherein the substituents are one or more substituents selected from the group consisting of halogen atoms, cyano, nitro, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio, C
1
-C
6
haloalkylthio and (C
1
-C
5
alkoxy)carbonyl;
and a fungicidal composition containing this compound as an active ingredient.
The present invention provides also 5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula [L]:
a difluoroacetyl semicarbazide compound of the formula [XXVI]:
wherein R
1
and T have the same meanings as described above; a semicarbazide compound of the formula [VII]:
wherein R
1
and T have the same meanings as described above; 2-methyl-5-phenylbenzylamine of the formula [XVI-1]:
inorganic acid salt (for example, hydrochloric acid addition salt, hydrobromic acid addition salt, sulfuric acid addition salt) and sulfonic acid salt (for example, methanesulfonic acid addition salt) of 2-methyl-5-phenylbenzylamine; 2-methyl-5-phenylbenzyl chloride of the formula [XIII-1]:
a sulfonate compounds of the formula [XIII-2]:
wherein R
9
represents a methyl or p-tolyl; N,N-dimethyl-(2-methyl-5-phenylbenzyl)amine of the formula [LI]:
inorganic acid salt (for example, hydrochloric acid addition salt, hydrobromic acid addition salt, sulfuric acid addition salt) and sulfonic acid salt (for example, methanesulfonic acid addition salt) of N,N-dimethyl-(2-methyl-5-phenylbenzyl)-amine, useful as a production intermediate for a compound of the invention.
In the present invention; as the C
1
-C
10
alkyl represented by A
1
and A
2
, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, hexyl, 1-methylpentyl, 1-ethylpentyl, 3,3-dimethylbutyl, heptyl, 3,7-dimethyloctyl and the like are listed; as the C
2
-C
10
alkenyl represented by A
1
and A
2
, for example, vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 2-pentenyl, 3-methyl-2-butenyl and the like are listed; as the C
2
-C
10
alkynyl represented by A
1
and A
2
, for example, ethynyl, proparqyl, 1-methyl-2-propynyl, 2-butynyl and the like are listed; as the C
3
-C
10
cycloalkyl represented by A
1
and A
2
, for example, cyclopropyl, cyclopentyl, cyclohexyl and the like are listed; as the (C
3
-C
10
cycloalkyl)alkyl represented by A
1
and A
2
, for example, cyclopropylmethyl, cyclopentylmethyl, 2-cyclopentylethyl, cyclohexylmethyl and the like are listed; as the C
5
-C
10
cycloalkenyl represented by A
1
and A
2
, for example, cyclopentenyl, cyclohexenyl and the like are listed; as the (C
5
-C
10
cycloalkenyl)alkyl represented by A
1
and A
2
, for example, cyclopenten-1-ylmethyl, cyclohexen-1-ylmethyl and the like are listed; as the phenyl C
1
-C
10
alkyl represented by A
1
and A
2
, for example, phenylmethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl and the like are listed; as the naphthyl C
1
-C
10
alkyl represented by A
1
and A
2
, for example, &agr;-naphthylmethyl, &bgr;-naphthylmethyl and the like are listed; as the 5- or 6-membered heterocyclic group optionally condensed with a benzene ring represented by A
1
and A
2
, for example, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isooxazolyl, 4-isooxazolyl, 5-isooxazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1-(1,2,4-triazolyl), 3-(1,2,4-triazolyl), 4-(1,2,4-triazolyl), 2-benzothienyl, 3-benzothienyl, benzothiazol-2-yl, 2-quinolyl and the like are listed; and as the methyl substituted by a 5- or 6-membered heterocyclic group optionally condensed with a benzene ring represented by A
1
and A
2
, for example, 2-eyridylmethyl, 4-pyridylmethyl, 2-pyrimidinylmethyl, 4-pyrimidinylmethyl, 3-pyrazolylmethyl, 2-thiazolylmethyl, 2-imidazolylmethyl, 3-(1,2,4-triazolyl)methyl, 2-quinolylmethyl and the like are listed.
Here, the alkyl, the alkenyl, the alkynyl, the cycloalkyl, the cycloalkylalkyl, the cycloalkenyl and the cycloalkenylalkyl represented by A
1
and A
2
may optionally be each substituted by one or more substituents selected from the group consisting of halogen atom(s) (fluorine atom, chlorine atom, bromine atom, iodine atom), cyano, nitro, C
1
-C
10
alkoxy, C
1
-C
10
haloalkoxy, C
1
-C
10
alkylthio, C
1
-C
10
haloalkylthio, (C
1
-C
9
alkyl)carbonyl, (C
1
-C
9
alkoxy)carbonyl, (C
1
-C
9
alkyl)carbonylamino, phenyl, phenoxy, benzyloxy and tri(C
1
-C
10
alkyl)silyl; and as the alkoxy, for example
Araki Tomohiro
Kinoshita Yoshiharu
Manabe Akio
Sakaguchi Hiroshi
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