Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-11-26
2003-04-22
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S214000
Reexamination Certificate
active
06552056
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel isothiazolecarboxamides, to processes for their preparation and to their use as microbicides.
BACKGROUND OF THE INVENTION
It has been already known that certain isothiazolecarboxamides can be employed for the control of plant pests (see JP-A 119 463/1988, JP-A 121 263/1989, JP-A 199 963/1989, JP-A 149 572/1990, JP-A 59 024/1993 and DE-A 31 33 418). Further, a process for the preparation of certain isothiazolecarboxamides and the use of such compounds as aarochemicals or as intermediates have also been disclosed already (see JP-A 139 672/1985). The fungicidal activity of such known compounds, however, is not always satisfactory.
DETAILED DESCRIPTION
There have now been found novel isothiazolecarboxamides of the formula
wherein
X represents halogen, C
1-4
alkyl or C
1-4
haloalkyl,
Y represents a hydrogen atom, halogen, cyano or C
2-5
alkoxycarbonyl,
R
1
, R
2
and R
4
independently of one another represent a hydrogen atom or C
1-4
alkyl, and
R
3
represents a hydrogen atom, C
1-12
alkyl, C
3-8
cycloalkyl, optionally substituted C
2-6
alkenyl, C
5-8
cycloalkenyl, C
7-8
bicycloalkenyl, C
1-4
haloalkyl, substituted C
1-4
alkyl, optionally substituted phenyl, optionally substituted naphthyl or optionally substituted 5- or 6-membered heterocyclyl having 1 to 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulphur, which heterocyclyl group may also be benzo-condensed, or
R
2
and R
3
, together with the carbon atom to which they are bonded, form an optionally substituted 5- or 6-membered hydrocarbon ring or an optionally substituted 5- or 6-membered heterocyclic ring comprising at least one nitrogen atom, or
R
2
and R
3
, together with the carbon atom to which they are bonded, form a group of the formula C═CH—R
5
, in which
R
5
represents hydrogen or C
1-2
alkyl,
or
R
3
and R
4
, together with the carbon atom and the carboxyl group to which they are bonded, form a 5- or 6-membered heterocyclic ring having at least one ring-constituting oxygen atom and being substituted with at least one oxo group,
with the proviso, however, that
R
3
does not represent isopropyl,
if
X and Y represent chloro,
R
1
and R
2
represent a hydrogen atom and
R
4
represents C
1-4
alkyl
Further, it has been found that the isothiazolecarboxamides of the formula (I) can be prepared by
a) reacting isothiazolecarboxylic acid chlorides of the formula
in which
X and Y have the above-mentioned meanings,
with amines of the formula
in which
R
1
, R
2
, R
3
and R
4
have the above-mentioned meanings,
in the presence of an inert diluent and, if appropriate, in the presence of an acid binding agent and, if appropriate, in the presence of a phase-transfer catalysts,
or
b) reacting isothiazolecarboxylic acid derivatives of the formula
in which
X, Y, R
1
, R
2
and R
3
have the above-mentioned meanings,
with compounds of the formula
HO—R
4
(V)
in which
R
4
has the above-mentioned meanings,
in the presence of an inert diluent and, if appropriate, in the presence of an acid catalyst,
or
c) reacting isothiaz ecarboxamides of the formula
in which
X, Y, R
1
, R
2
and R
3
have the above-mentioned meanings and
M represents C
1-4
alkyl,
with water, if appropriate, in the presence of an inert diluent and, if appropriate, in the presence of an acid binding agent or in the presence of an acid catalyst and, if appropriate, in the presence of a phase-transfer catalyst.
Finally, it has been found that the isothiazolecarboxamides of the formula (I) are outstandingly active as microbicides in agriculture and horticulture, particularly as fungicides for the direct control of plant diseases or for causing resistance in plants against plant pathogens.
Surprisingly, the isothiazolecarboxamides according to the invention have a much better rnicrobicidal activity than the already known compounds, which are structurally most similar and have the same type of action.
In the present context “halogen” represents fluoro, chloro, bromo or iodo.
“Alkyl” represents straight-chain or branched groups, such as methyl, ethyl, n- or iso-propyl, n-, iso, sec- or tert-butyl, n-pentyl, iso-pentyl, tert-amyl, pentan-3-yl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl.
“Alkoxy” represents straight-chain or branched groups, such as methoxy, ethoxy, n-or iso-propoxy, n-, iso-, sec- or tert-butoxy etc.
“Alkylthio” represents straight-chain or branched groups, such as methylthio, ethylthio, n- or iso-propylthio, n-, iso-, sec- or tert-butylthio etc.
“Alkylsulfinyl” represents straight chain or branched groups, such as methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl etc.
“Alkylsulfonyl” represents straight-chain or branched groups, such as methyl-sulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert- butylsulfonyl etc.
“Alkoxycarbonyl” represents straight-chain or branched groups, such as methoxy-carbonyl, ethoxycarbonyl, n- or iso-propoxycarbonyl, n-butoxycarbonyl etc.
“Alkylenedioxy” represents groups, in which the alkylene part is straight-chain or branched, and includes methylenedioxy, ethylenedioxy, methylmethylenedioxy, dimethylmethylenedioxy, propylenedioxy, tetramethylethylenedioxy etc.
“Alkenylidene” represents a bivalent group, in which the carbon atom in position 1 is double bonded with the carbon atom in position 2. As examples there may be mentioned vinylidene, 1-propenylidene, 1-butenylidene etc.
“Cycloalkyl” represents a cyclic alkyl group and includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl etc.
“Alkenyl” represents straight-chain or branched groups and includes, for example, vinyl, allyl, 1-propenyl, 1-methylvinyl, 2-methyl-1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl etc.
“Cycloalkenyl” represents a cyclic alkenyl group and includes, for example, cyclo-butenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl etc.
“Bicycloalkenyl” represents a bicyclic alkenyl group and includes, for example, bicyclo[2.2.1]-2-heptenyl, bicyclo[2.2.1]hepta-2,5-dienyl, bicyclo[2.2.2]octadienyl etc.
“Haloalkyl” represents straight-chain or branched alkyl groups, which are substituted with one or more halogen atoms, preferably fluoro, chloro andlor bromo. As examples there may be mentioned trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 3-chloropropyl, 3-bromopropyl, 1-chloropropan-2-yl, 1-bromopropan-2-yl, 1,3-difluoropropan-2-yl, 2,3-dibromopropyl, 2,2-dichloro-3,3,3-trifluoropropyl etc.
As substituents of “alkyl” and “allenyl” there may be mentioned hydroxy; alkoxy such as methoxy, ethoxy, n- or iso-propoxy, n-butoxy etc.; mercapto; alkylthio such as methylthio, ethylthio, n- or iso-propylthio, n-butylthio etc.; alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-butylsulfinyl etc.; alkyl-sulfonyl such as methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-butylsulfonyl etc.; phenyl; a 5-membered heterocyclic group which has 1-3 nitrogen atoms and may be benzo-condensed such as a univalent group derived from pyrrolidine, imidazolidine, pyrrole, imidazole, pyrazole, indole, benzimidazole etc.
“Phenyl” and “naphthyl” may be substituted with one or more substituents and if substituted with a plurality of substituents, these substituents may be identical or different. As examples of the substituents there may be mentioned halogen such as fluoro, chloro, bromo and iodo; alkyl such as methyl, ethyl, n- or iso-propyl, n-, tert-, sec-, or iso-butyl etc.; alkoxy such as methoxy, ethoxy, n- or iso-propoxy, n-, tert-, sec- or iso-butoxy etc.; alkylthio such as methylthio, ethylthio, n- or iso-propylthio, n-, tert-, sec- or iso-butylthio etc.; alkylenedioxy such as methylenedioxy, ethylene-dioxy, methylmethylenedioxy, dimethylmethylenedioxy, propylenedioxy, tetra-methylethylenedioxy etc.; di-C
1-4
alkylamino such as dimethylamino, N-methy
Araki Yasuo
Assmann Lutz
Imanishi Kinya
Ishikawa Koichi
Kinbara Taro
Gerstl Robert
Harmuth Raymond J.
Henderson Richard E. L.
Nihon Bayer Agrochem K.K.
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