Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2000-05-03
2001-08-21
Stockton, Laura L. (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C548S214000
Reexamination Certificate
active
06277791
ABSTRACT:
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.
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, N-ethyl-3,4-dichloro-isothiazole-5-carboxamide and 3,4,4′-trichloro-isothiazole-5-carboxanilide 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.
This invention, accordingly, provides novel isothiazolecarboxamides of the formula
in which
R represents a radical of the formula
or
in which
R
1
represents cyano, phenyl or cycloalkyl having 3 to 7 carbon atoms, or
R represents a radical of the formula
in which
R
2
represents
cycloalkyl having 3 to 7 carbon atoms or represents —CH
2
—S—R
3
, where
R
3
represents alkyl having 1 to 6 carbon atoms or represents phenyl which is optionally substituted by halogen and/or alkyl having 1 to 6 carbon atoms, or
R represents a radical of the formula
in which
R
4
represents hydrogen or N,N-dialkylaminomethyl having 1 to 4 carbon atoms in each alkyl moiety, or
R represents a radical of the formula
in which
R
5
represents hydrogen or alkoxy having 1 to 4 carbon atoms and
R
6
represents alkoxy having 1 to 4 carbon atoms, alkyl having 1 to 6 carbon atoms, optionally halogen-substituted phenyl or represents optionally halogen-substituted phenoxy, or
R
5
represents optionally halogen-substituted phenoxy and
R
6
represents hydrogen, or
R represents a radical of the formula
—CH
2
—CH
2
—O—R
9
in which
R
7
represents alkyl having 1 to 4 carbon atoms,
R
8
represents alkyl having 1 to 4 carbon atoms, and
R
9
represents hydrogen or a radical of the formula
or
R represents a radical of the formula
in which
R
10
represents halogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms and
n represents integers from 0 to 3.
Furthermore, it has been found that isothiazolecarboxamides of the formula (I) 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—CH
2
—X (V)
in which
X represents a radical of the formula
in which
R
4
, R
5
, R
6
and R
8
are each as defined above,
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 defences of the plants against attack by undesirable microorganisms and as microbicides for the direct control of the microorganisms. Additionally, the compounds according to the invention also exhibit activity against plant-damaging animals.
Surprisingly, the compounds according to the invention have better microbicidal activity than N-ethyl-3,4-dichloro-isothiazole-5-carboxamide and 3,4,4′-trichloro-isothiazole-5-carboxanilide, 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. Preference is given to compounds of the formula (I) in which
R represents a radical of the formula
or
in which
R
1
represents cyano, phenyl, cyclopentyl, cyclohexyl or cycloheptyl, or
R represents a radical of the formula
in which
R
2
represents —C(CH
3
)
3
,
cyclopentyl, cyclohexyl, cycloheptyl or represents —CH
2
—S—R
3
where
R
3
represents alkyl having 1 to 5 carbon atoms or represents phenyl which is optionally mono- to trisubstituted by identical or different constituents selected from the group consisting of fluorine, chlorine, bromine and alkyl having 1 to 4 carbon atoms, or
R represents a radical of the formula
in which
R
4
represents hydrogen or N,N-dialkyl-aminomethyl having 1 or 2 carbon atoms in each alkyl moiety, or
R represents a radical of the formula
in which
R
5
represents hydrogen or alkoxy having 1 or 2 carbon atoms and
R
6
represents alkoxy having 1 or 2 carbon atoms, alkyl having 1 to 4 carbon atoms, phenyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine and bromine or represents phenoxy which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine and bromine, or
R
5
represents phenoxy which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine and bromine and
R
6
represents hydrogen, or
R represents a radical of the formula
or
in which
R
7
represents methyl or ethyl,
R
8
represents methyl or ethyl and
R
9
represents hydrogen or a radical of the formula
or
R represents a radical of the formula
in which
R
10
represents fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy and
n represents integers from 0 to 3, where R
10
represents identical or different radicals if n represents 2 or 3.
The abovementioned substituent definitions can be combined among each other. Additionally, individual definitions may be redundant.
Using 3,4-dichloro-isothiazole-5-carbonyl chloride and 2-cyanoaniline as starting materials, the course of the process (a) according to the invention can be illustrated by the equation below.
Using 3,4-dichloro-isothiazole-5-carboxamide and N-formyl-N-hydroxy-methyl-methylamine as starting materials, the course of the process (b) according to the invention can be illustrated by the equation below.
The 3,4-dichloro-isothiazole-5-carbonyl chloride of the formula (II) required as starting material for carrying out the process (a) according to the invention is known (cf. U.S. Pat. No. 5,240,951).
The formula (III) provides a general definition of the amines furthermore required as reaction components for carrying out the process (a) according to the invention. In this formula, R preferably has those meanings which have already been mentioned in connection with the description of the compounds of the formula (I) according to the invention as being preferred for this radical.
The amines of the formula (III) are known or can be prepared by known methods.
Suitable acid binders for carrying out the process (a) according to the invention are all customary inorganic or organic bases. Preference is given to using alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, furthermore ammonium hydroxide, ammonium acetate or ammonium carbonate, or tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Suitable diluents for carrying out the process (a) according to the invention are all inert organic solvents. Preference is given to using aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as
Assmann Lutz
Dutzmann Stefan
Elbe Hans-Ludwig
Erdelen Christoph
Hanssler Gerd
Bayer Aktiengesellschaft
Gil Joseph C.
Stockton Laura L.
LandOfFree
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