Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-05-09
2002-11-05
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S530000
Reexamination Certificate
active
06476061
ABSTRACT:
This application is a 371 of PCT/EP99/08379 Nov. 12, 1999.
The present invention relates to novel agrochemical compositions having fungicidal action comprising pyrrolidones as active compounds, and to their use in the treatment of plants and in agriculture.
The present invention provides compositions comprising as active compounds compounds of the formula I
where:
R
1
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl, formyl or C
1
-C
6
-haloalkylcarbonyl;
R
2
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
3
-R
12
are hydrogen, halogen, C
1
-C
6
-cycloalkyl, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-haloalkylsulfonyl, formyl, C
1
-C
6
-alkylcarbonyl, cyano, C
1
-C
6
-alkylthio or phenyl, which may be unsubstituted or substituted by halogen atoms, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl groups, and their agriculturally useful salts.
Some of the compounds of the formula I are known from the literature (M. Augustin and P. Reinemann, Z. Chem. Volume 13, pp. 214-216 (1973), and/or they are commercially available. These are the following compounds:
1-anilino-3-phenylpyrrole-2,5-dione, 1-anilino-3-p-tolylpyrrole-2,5-dione, 1-(N-methylanilino)-3-p-tolylpyrrole-2,5-dione, 1-anilino-3-(3-chlorophenyl)pyrrole-2,5-dione, 1-anilino-3-(4-chlorophenyl)pyrrole-2,5-dione, 1-anilino-3-(4-bromophenyl)pyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(N-methylanilino)pyrrole-2,5-dione, 1-(4-chloroanilino)-3-p-tolylpyrrole-2,5-dione, 3-(4-bromophenyl)-1-(4-methylanilino)pyrrole-2,5-dione, 1-(4-chloroanilino)-3-(4-chlorophenyl)pyrrole-2,5-dione, 1-anilino-3-(3,4-dichlorophenyl)pyrrole-2,5-dione, 3-(4-bromophenyl)-1-(4-methoxyanilino)pyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(3,4-dichloroanilino)pyrrole-2,5-dione, 3-(4-methoxyphenyl)-1-(N-methylanilino)pyrrole-2,5-dione, 1-anilino-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(4-chloroanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(4-methoxyanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(2-methoxyanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione, 1-(4-fluoroanilino)-3-(4-chlorophenyl)pyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(4-methylanilino)pyrrole-2,5-dione, 1-(4-methylanilino)-3-phenylpyrrole-2,5-dione, 3-(4-chlorophenyl)-1-(2,4-dichloroanilino)pyrrole-2,5-dione, 1-(2,4-dichloroanilino)-3-phenylpyrrole-2,5-dione, 1-(2,4-dichloroanilino)-3-(4-methoxyphenyl)pyrrole-2,5-dione.
A fungicidal activity of these compounds has hitherto not been described.
Surprisingly, it has been found that compounds of the formula I have fungicidal activity. They are suitable for controlling harmful fungi in the treatment of plants, and also for the therapeutic treatment of diseases in humans caused by harmful fungi, and for veterinary treatment in mammals.
Compounds of the formula I can be prepared by the same method as that described in the literature (Z. Chem. Volume 13, pp. 214-216 (1973)). The starting materials are either known from the literature or commercially available.
In the definition of the substituents R
1
to R
12
, the given terms are collective terms for a group of compounds.
In each case, halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Examples of other meanings are:
C
1
-C
6
-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, in particular ethyl;
C
1
-C
6
-haloalkyl: a C
1
-C
6
-alkyl radical as mentioned above such as partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example trichloromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-fluoropropyl, 3-fluoropropyl, 2-chloropropyl or 3-chloropropyl, in particular 2-fluoroethyl or 2-chloroethyl;
C
1
-C
6
-alkoxy: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, in particular methoxy or ethoxy;
C
3
-C
8
-cycloalkyl: for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl;
halo-C
1
-C
6
-alkoxy: a C
1
-C
6
-alkoxy radical as mentioned above which is substituted by fluorine, chlorine or bromine;
C
1
-C
6
-alkylcarbonyl: a carbonyl group which is substituted by a C
1
-C
6
-alkyl radical as mentioned above, such as, for example, acetyl, propionyl, butyryl;
halo-C
1
-C
6
-alkylcarbonyl: a C
1
-C
6
-alkylcarbonyl radical as mentioned above which is substituted by fluorine, chlorine or bromine;
C
1
-C
6
-alkylsulfonyl: a sulfonyl group which is substituted by a C
1
-C
6
-alkyl radical as mentioned above;
halo-C
1
-C
6
-alkylsulfonyl: a C
1
-C
6
-alkylsulfonyl radical as mentioned above which is substituted by fluorine, chlorine or bromine;
C
1
-C
6
-alkylthio: a sulfur atom which is substituted by a C
1
-C
6
-alkyl radical as mentioned above;
an unsubstituted or substituted phenyl radical: a phenyl radical which is mono- or polysubstituted. The substituents can be chosen at will, for example the following: halogen atoms, C
1
-C
6
-alkyl or halo-C
1
-C
6
-alkyl.
For the purpose of the present invention, the compounds listed under items 1-4 below are preferred with a view to the definitions of substituents mentioned, in each case on their own or in combination with one another:
1. Compounds of the formula 1, where R
1
is as defined below: hydrogen, methyl, ethyl or formyl, in particular hydrogen or methyl.
2. Compounds according to 1, where R
2
is as defined below: hydrogen, methyl, ethyl, trifluoromethyl, in particular hydrogen.
3. Compounds according to 1 or 2, where R
3
-R
12
are as defined below: hydrogen, fluorine, chlorine, methyl, ethyl, propyl, butyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methoxy, methylthio, cyano.
4. Compounds according to 1 to 3, where at least two of the radicals R
8
-R
12
and in addition at least two of the radicals R
3
-R
7
are hydrogen and the others are hydrogen, fluorine, chlorine, methyl, ethyl, propyl, butyl, trifluoromethyl, trifluoromethoxy or difluoromethoxy.
The two phenyl rings are preferably unsubstituted (R
3
—R
12
=H) or preferably mono-, di- or trisubstituted, suitable substituents being mainly the following: C
1
-C
6
-alkyl, halogen, halo-C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkoxy, in particular methyl, isopropyl, fluorine, chlorine, trifluoromethyl or trifluoromethoxy.
In general, the abovementioned compounds have been found to be particularly effective.
For the purpose of the present invention, for example the following compounds in Table 1 are suitable fungicidally active compounds:
TABLE 1
Phys.
No.
R
1
R
2
R
3
R
4
Data
1)
H
H
phenyl
phenyl
2)
H
H
phenyl
4-methylphenyl
3)
H
H
phenyl
2,4-dichloro-
phenyl
4)
H
H
4-methylphenyl
phenyl
5)
H
H
4-methylphenyl
4-chlorophenyl
6)
H
H
4-methoxy-
phenyl
phenyl
7)
H
H
4-methoxy-
4-methoxyphenyl
phenyl
8)
H
H
4-methoxy-
2-methoxyphenyl
phenyl
9)
H
H
4-methoxy-
4-chlorophenyl
phenyl
10)
H
H
4-methoxy-
2,4-dichloro-
phenyl
phenyl
11)
H
H
3-chlorophenyl
phenyl
12)
H
H
3,4-dichloro-
phenyl
m.p.
phenyl
208-
210° C.
13)
H
H
4-chlorophenyl
phenyl
14)
H
H
4-chlorophenyl
4-chlorophenyl
m.p.
192-
193° C.
15)
H
H
4-Chlorophenyl
3,4-dichloro-
phenyl
16)
H
H
4-chlorophenyl
2,4-dichloro-
phenyl
17)
H
H
4-chlorophenyl
4-fluorophenyl
18)
H
H
4-chlorophenyl
4-methylphenyl
19)
H
H
4-bromophenyl
4-methoxyphenyl
20)
H
H
4-bromophenyl
4-methylphenyl
21)
Methyl
H
4-methylphenyl
phenyl
22)
Methyl
H
4-methoxy-
phenyl
phenyl
23)
Methyl
H
4-chlorophenyl
phenyl
m.p.
149-
150° C.
24)
Acetyl
H
phenyl
phenyl
25)
Tri-
H
phenyl
phenyl
fluoro-
acetyl
26)
H
H
phenyl
4-isopropyl-
1H-NMR
phenyl
(DMSO-
d
6
): &dgr; =
1.15 (d);
2.78 (m);
6.65 (d);
7.05 (d);
7.40 (s);
7.57 (m);
8.05 (m);
8.30 (s).
27)
H
H
phenyl
4-fluorophenyl
28)
H
H
phenyl
3-fluorophenyl
29)
H
H
phenyl
2-fluorophenyl
30)
H
H
phenyl
2,3,5,6-tetra-
m.p.
fluorophenyl
123-
125° C.
31)
H
H
phenyl
4-trifluoro-
m.p.
methylphenyl
211-
214° C.
32)
H
H
phenyl
3-trifluoro-
methylphenyl
33)
H
H
phenyl
4-methyl-
m.p.
sulphonylphenyl
168-
170° C.
34)
H
H
phenyl
4-chlorophenyl
m.p.
175-
177° C.
35)
H
H
Ammermann Eberhard
Eicken Karl
Grote Thomas
Hamprecht Gerhard
Lorenz Gisela
BASF - Aktiengesellschaft
Keil & Weinkauf
McKane Joseph K.
Small Andrea D.
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