Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-03-13
2001-10-30
Gerstl, Robert (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S226000, C504S266000, C504S269000, C544S065000, C544S133000, C548S187000, C548S213000
Reexamination Certificate
active
06310005
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel isothiazolecarboxamides, to a plurality of processes for their preparation and to their use for protecting plants against attack by undesirable microorganisms and animal pests.
BACKGROUND OF THE INVENTION
It is already known that numerous isothiazolecarboxylic acid derivatives have fungicidal properties (of U.S. Pat. No. 5,240,951 and JP-A 06-009 313). Thus, for example, N-furfuryl-3,4-dichloro-isothiazole-5-carboxamide and N-morpholinyl-3,4-dichloro-isothiazole-5-carboxamide can be employed for controlling fungi. The activity of these compounds is good, but in some cases leaves something to be desired at low application rates.
SUMMARY OF THE INVENTION
lsothiazolecarboxamides of the formula
may be used for protecting plants against attack by undesirable micoorganisms and animal pests.
DETAILED DESCRIPTION
This invention, accordingly, provides novel isothiazolecarboxamides of the formula
in which
R represents optionally substituted heterocyclyl-alkyl or represents a radical of the formula
in which
R
1
represents hydrogen or alkyl,
R
2
represents alkoxy or represents optionally substituted heterocyclyl and
m represents integers from 1 to 4, or
R represents a radical of the formula
in which
R
3
represents optionally substituted heterocyclyl or represents a radical of the formula
in which
R
4
represents cycloalkyl, and
n represents 1 or 2, or
R represents morpholinyl, piperazinyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl,pyrrolyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, triazinyl, 1,2,3-triazolyl, tetrazolyl, benzotriazolyl, quinolinyl, isoquinolinyl, quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl or benzimidazolyl, where these radicals can be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, carboxyl, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkoxy-carbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, phenyl and phenoxy.
Furthermore, it has been found that isothiazolecarboxamides of the formula (1) are obtained when
a) 3,4-dichloro-isothiazole-5-carbonyl chloride of the formula
is reacted with amines of the formula
H
2
N—R (III)
in which
R is as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or
b) 3,4-dichloro-isothiazole-5-carboxamide of the formula
is reacted with hydroxyl compounds of the formula
HO—A—X (V)
in which
X represents optionally substituted heterocyclyl or a radical of the formula
in which
R
1
and R
2
are each as defined above, and
A represents optionally branched alkylene or (CH
2
)
m
,
in the presence of a diluent and in the presence of a dehydrating agent.
Finally, it has been found that the isothiazolecarboxamides of the formula (I) are highly suitable for protecting plants against attack by undesirable microorganisms. The compounds according to the invention are suitable both for mobilizing defenses of the plants against attack by undesirable microorganisms and as microbicides for the direct control of the microorganisms.
Surprisingly, the compounds according to the invention have better microbicidal activity than N-furfuryl-3,4-dichloro-isothiazole-5-carboxamide and N-morpholinyl-3,4-dichloro-isothiazole-5-carboxamide, which are constitutionally similar prior-art active compounds of the same direction of action.
The formula (I) provides a general definition of the isothiazolecarboxamides according to the invention.
R preferably represents optionally benzo-fused five- or six-membered heterocyclylalkyl having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulfur, in the heterocyclyl moiety and 1 to 4 carbon atoms in the alkyl moiety, where the heterocyclyl moiety may also contain a carbonyl group or a thiocarbonyl group and may furthermore be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, carboxyl, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, phenyl and phenoxy.
R furthermore preferably represents a radical of the formula
in which
R
1
preferably represents hydrogen or alkyl having 1 to 6 carbon atoms,
R
2
preferably represents alkoxy having 1 to 6 carbon atoms, or represents five- or six-membered heterocyclyl having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulfur, where the heterocyclyl moiety may be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, carboxyl, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, phenyl and phenoxy and
m represents the numbers 1, 2 or 3.
R furthermore preferably represents a radical of the formula
in which
R
3
preferably represents five- or six-membered heterocyclyl having 1 to 3 hetero atoms, such as nitrogen, oxygen and/or sulfur, where the heterocyclyl moiety may be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, carboxyl, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, phenyl and phenoxy, or
R
3
represents a radical of the formula
in which
R
4
preferably represents cycloalkyl having 3 to 7 carbon atoms, and
R furthermore preferably represents morpholinyl, piperazinyl, pyrazolyl, imidazolyl, 1,2,4triazolyl, pyrrolyl, thienyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, triazinyl, 1,2,3-triazolyl, benzotriazolyl, quinolinyl, isoquinolinyl, quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl or benzimidazolyl, where these radicals may be mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, carboxyl, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, balogenoalkyl having 1 or 2 carbon atoms and 1 to 3 fluorine, chlorine and/or bromine atoms, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, halogenoal
Assmann Lutz
Elbe Hans-Ludwig
Hanssler Gerd
Kitagawa Yoshinori
Kuck Karl-Heinz
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
Zurcher Jackie Ann
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