Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-05
2001-02-20
Stockton, Laura E. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S236800, C514S326000, C514S342000, C544S133000, C546S209000, C546S271100, C548S214000
Reexamination Certificate
active
06191155
ABSTRACT:
The present invention relates to novel isothiazolecarboxylic acid derivatives, to a process for their preparation and to their use for protecting plants against attack by undesirable microorganisms and animal pests.
It is already known that numerous isothiazolecarboxylic acid derivatives have fungicidal properties (cf. U.S. Pat. No. 5,240,951 and JP-A 06-009 313). Thus, for example, isopropyl 3,4-dichloro-isothiazol-5-carboxylate can be used for controlling fungi. The activity of this compound is good, but in some cases leaves something to be desired at low application rates.
This invention, accordingly, provides novel isothiazolecarboxylic acid derivatives of the formula
in which
R represents the groups —OR
1
or —SR
2
in which
R
1
represents alkyl having 1 to 12 carbon atoms, where each of these radicals is mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxyl, carboxyl, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbonatoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenylalkoxy having 1 to 4 carbon atoms in the alkoxy moiety and heterocyclylalkoxy having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulphur, in the heterocyclyl moiety and 1 to 4 carbon atoms in the alkoxy moiety, or
R
1
represents aryl having 6 to 10 carbon atoms which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
1
represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the alkyl moiety, where the aryl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
1
represents aroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the oxyalkyl moiety, where the aryl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
1
represents optionally benzo-fused heterocyclylalkyl having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulphur, in the heterocyclyl moiety and 1 to 6 carbon atoms in the alkyl moiety, where the heterocyclyl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy; or
R
1
represents a radical of the formula
in which
m and n independently of one another each represent integers from 1 to 3,
R
3
represents alkyl having 1 to 4 carbon atoms or phenyl and
R
4
represents hydrogen or alkyl having 1 to 4 carbon atoms, and
R
2
represents alkyl having 1 to 12 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenylalkoxy having 1 to 4 carbon atoms in the alkoxy moiety and heterocyclylalkoxy having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulphur, in the heterocyclyl moiety and 1 to 4 carbon atoms in the alkoxy moiety, or
R
2
represents aryl having 6 to 10 carbon atoms which may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
2
represents aralkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the alkyl moiety, where the aryl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
2
represents aroxyalkyl having 6 to 10 carbon atoms in the aryl moiety and 1 to 6 carbon atoms in the oxyalkyl moiety, where the aryl moiety may be mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy moiety, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 6 carbon atoms, dialkylamino having 1 to 6 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
2
represents optionally benzo-fused heterocyclylalkyl having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulphur, in the heterocyclyl moiety and 1 to 6 carbon atoms in the alkyl moiety, where the heterocyclyl moiety may b
Assmann Lutz
Dutzmann Stefan
Elbe Hans-Ludwig
Erdelen Christoph
Hanssler Gerd
Bayer Aktiengesellschaft
Gil Joseph C.
Stockton Laura E.
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