Fungicidal agents containing pyrrolidones as their active...

Details Fungicidal agents containing pyrrolidones as their active... Fungicidal agents containing pyrrolidones as their active...

2002-08-20

2003-07-01

Chang, Ceila (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S546000, C548S235000, C548S247000, C504S225000, C504S248000, C504S270000, C504S271000, C544S141000, C546S208000

Reexamination Certificate

active

06586369

ABSTRACT:

This application is a 371 of PCT/EP01/02059 Feb. 23, 2001.
The present invention relates to novel agrochemical compositions having fungicidal action and 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 halogen, C
1
-C
6
-alkylthio, C
1
-C
6
-alkoxy, C
3
-C
6
-cycloalkyl-C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkoxy, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfinyl, halo-C
1
-C
6
-alkylsulfonyl, cyano or a radical NR
13
R
14
;
R
3
-R
12
are hydrogen, halogen, C
1
-C
8
-cycloalkyl, C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halo-C
1
-C
6
-alkoxy, C
1
-C
6
-alkylsulfonyl, halo-C
1
-C
6
-alkylsulfonyl, formyl, C
1
-C
6
-alkylcarbonyl, cyano, C
1
-C
6
-alkylthio or phenyl, which may be unsubstituted or substituted by halogen, C
1
-C
6
-alkyl or halo-C
1
-C
6
-alkyl,
R
13
is hydrogen, C
1
-C
6
-alkyl,
R
14
is C
1
-C
6
-alkyl, C
1
-C
8
-cycloalkyl or, together with R
13
and the nitrogen atom to which they are attached, a saturated or unsaturated heterocyclic five- or six-membered ring which contains one or two heteroatoms selected from the group consisting of nitrogen and oxygen,
and their agriculturally useful salts.
Some of the compounds of the formula I are known from the literature. Thus, for example, Z. Chem. 13, (1973), 214-216 (M. Augustin and P. Reinemann) describes phenyl substituted pyrrolidones. A fungicidal action of these compounds has hitherto not been described.
Surprisingly, it has been found that compounds of the formula I have a remarkable fungicidal action. They are suitable for controlling harmful fungi in the treatment of plants, and also for the therapeutic treatment of human disorders caused by harmful fungi, and for the veterinary treatment of mammals.
Compounds of the formula I can be prepared similarly to the process described in the literature (Z. Chem. 13, (1973), 214-216). 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. The alkyl radicals mentioned in each case each denote straight-chain or branched alkyl radicals having up to six carbon atoms.
Halogen is in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Examples of Other Meanings are:
C
1
-C
6
-alkyl: a straight-chain or branched alkyl group, such as, for example, 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 which is partially or fully substituted, in particular mono-, di- or trisubstituted, 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: a straight-chain or branched alkoxy radical having up to six carbon atoms, such as, for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, in particular methoxy or ethoxy;
C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl: an alkyl radical as mentioned above which is substituted by C
1
-C
6
-alkoxy, as mentioned above, such as, for example, methoxymethyl, ethoxymethyl, n-propoxymethyl, 1-methylethoxymethyl or n-butoxymethyl;
C
3
-C
8
-cycloalkyl: a saturated cycloalkyl group, such as, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl;
C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkoxy: an alkoxy group as mentioned above which is substituted by C
3
-C
8
-cycloalkyl as mentioned above, such as, for example, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cycloheptylmethoxy, cyclooctylmethoxy, cyclopropylethoxy, cyclobutylethoxy, cyclopentylethoxy, cyclohexylethoxy, cycloheptylethoxy, cyclooctylethoxy;
halo-C
1
-C
6
-alkoxy: a C
1
-C
6
-alkoxy radical as mentioned above which is mono-, di- or trisubstituted by fluorine, chlorine or bromine, such as, for example, chloromethoxy, fluoromethoxy, difluoromethoxy, difluoroethoxy, dichloromethoxy, dichloroethoxy;
C
1
-C
6
-alkyl-carbonyl: a carbonyl group which is substituted by a C
1
-C
6
-alkyl radical as above, such as, for example, acetyl, propionyl, butyryl;
halogen-C
1
-C
6
-alkyl-carbonyl: a C
1
-C
6
-alkyl-carbonyl radical as 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,
C
1
-C
6
-alkylsulfinyl: a sulfinyl 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 unsubstituted or mono- or polysubstituted. Any substituents are possible, for example the following: halogen atoms, C
1
-C
6
-alkyl or halo-C
1
-C
6
-alkyl. The phenyl radical is preferably mono-, di- or trisubstituted.
If R
13
and R
14
together with the nitrogen to which they are attached form a chain of 4-5 carbon atoms, they are saturated or partially unsaturated heterocyclic 5- or 6-membered rings containing one or two heteroatoms (oxygen or nitrogen atoms), such as, for example, pyrrole, oxazole, isoxazole, morpholino or piperidino.
For the purpose of the present invention, preferably with respect to the definitions of substituents mentioned, the following compounds are possible, in each case on their own or in combination with one another:
1. Compounds of the formula I in which R
1
has the following meanings: hydrogen; C
1
-C
3
-alkyl (such as, for example, methyl, ethyl); C
1
-C
3
-alkylcarbonyl (for example acetyl); formyl; in particular hydrogen, formyl, acetyl or methyl.
2. Compounds according to item 1, where R
2
has the following meanings: chlorine, bromine, C
1
-C
3
-alkylthio (for example methylthio); C
1
-C
6
-alkylsulfonyl (for example methylsulfonyl); C
1
-C
6
-alkylsulfinyl (for example methylsulfinyl); C
1
-C
3
-haloalkoxy (for example difluoromethoxy); in particular chlorine and bromine.
3. Compounds according to items 1 or 2, where R
3
-R
12
have the following meanings: hydrogen; fluorine; chlorine; C
1
-C
4
-alkyl (for example methyl, ethyl, propyl, butyl); halo-C
1
-C
3
-alkyl (for example trifluoromethyl, difluoromethyl); halo-C
1
-C
3
-alkoxy (for example trifluoromethoxy, difluoromethoxy); C
1
-C
3
-alkoxy (for example methoxy); C
1
-C
3
-alkylthio (for example methylthio); cyano.
4. Compounds according to items 1 to 3 where at least two of the radicals R
8
-R
12
and furthermore at least two of the radicals R
3
-R
7
are hydrogen and the others are hydrogen, fluorine, chlorine; C
1
-C
4
-alkyl (for example methyl, ethyl, propyl, butyl); halo-C
1
-C
3
-alkyl (for example trifluoromethyl); halo-C
1
-C
3
-alkoxy (for example trifluoromethoxy, difluoromethoxy).
The two phenyl rings are preferably unsubstituted (R
3
-R
12
=H) or preferably mono-, di- or trisubstituted, where preference is given to the following substituents: C
1
-C
6
-alkyl, halogen, halo-C
1
-C
6
-alkyl, halo-C
1
-C
6
-alkoxy. In this context, particular preference is given to the following substituents: methyl, isopropyl, fluorine, chlorine, trifluoromethyl or trifluoromethoxy.
The compounds mentioned above have usually been found to be particularly effective.
For the purpose of the present invention, suitable fungicidally active compounds are, for example, the following compounds

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