Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-04-06
2001-04-24
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S065000
Reexamination Certificate
active
06221862
ABSTRACT:
It has already been disclosed that certain compounds which are structurally similar to those described below have fungicidal properties (compare, for example, WO 95-04728). However, the fungicidal action of these compounds leaves something to be desired, especially when low amounts are applied.
The new thioimides of the general formula (I),
in which
Q represents a single bond, oxygen or sulphur,
R represents alkyl or optionally substituted cycloalkyl having 3 to 5 carbon atoms,
Z represents in each case optionally substituted cycloalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another in each case represent hydrogen, halogen, cyano, nitro or in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl have now been found.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, also when linked with heteroatoms, such as in alkoxy or alkylthio, are in each case straight-chain or branched.
Halogen in general represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Heterocyclyl represents saturated or unsaturated and aromatic, cyclic compounds, in which at least one ring member is a heteroatom, that is to say an atom other than carbon. If the ring contains several heteroatoms, these can be identical or different. Heteroatoms are preferably oxygen, nitrogen or sulphur. If the ring contains several oxygen atoms, these are not adjacent. If appropriate, the cyclic compounds form a polycyclic ring system together with other carbocyclic or heterocyclic, fused-on or bridged rings. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic, aromatic ring systems.
It has furthermore been found that the new thioimides of the general formula (I) are obtained by a process in which thioamides of the general formula (II)
in which
Q, R and Z have the abovementioned meanings,
are reacted with a halogenomethyl compound of the general formula (III)
in which
L
1
, L
2
, L
3
and L
4
have the abovementioned meanings and
Y represents halogen,
optionally in the presence of a diluent and optionally in the presence of an acid acceptor.
Finally, it has been found that the new thioimides of the general formula (I) show a very potent fungicidal action.
Where appropriate, the compounds according to the invention can be in the form of mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z isomers, or optical isomers. Both the E and the Z isomers, the individual enantiomers, the racemates and also any desired mixtures of these isomers are claimed.
Preferred thioimides of the formula (I) are those in which
Q represents a single bond, oxygen or sulphur,
R represents alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms which is optionally monosubstituted to tetrasubstituted by halogen or alkyl,
Z represents cycloalkyl or cycloalkylalkyl which has in each case 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the alkyl part and is in each case optionally monosubstituted to tetrasubstituted by halogen or alkyl;
or represents heterocyclyl or heterocyclylalkyl which has in each case 3 to 7 ring members and 1 to 4 carbon atoms in the alkyl part and is optionally substituted by halogen or alkyl having 1 to 4 carbon atoms;
or represents aryl or arylalkyl which has in each case 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part and is in each case optionally monosubstituted to tetrasubstituted in an identical or different manner in the aryl part, the possible substituents preferably being chosen from the following list:
halogen, cyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyl-oxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino or dialkylamino;
alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaniinocarbonyl, arylalkylaminocarbonyl, alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in the particular hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;
in each case divalent alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, in each case optionally monosubstituted to tetrasubstituted in an identical or different manner by fluorine, chlorine, oxo, methyl, trifluoromethyl or ethyl;
or a grouping
wherein
A
1
represents hydrogen or alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, methyl, phenyl, benzyl, alkoxy, alkylamino or dialkylamino having 1 to 4 carbon atoms in the particular alkyl chains and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another in each case represent hydrogen, halogen, cyano, nitro or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl which has in each case 1 to 6 carbon atoms and is in each case optionally substituted by 1 to 5 halogen atoms, preferably hydrogen or methyl, and in particular hydrogen.
Particularly preferred thioimides of the formula (I) are those in which
Q represents a single bond, oxygen or sulphur and
R represents methyl, ethyl, n- or i-propyl or, in particular, cyclopentyl, cyclobutyl or, in particular, cyclopropyl, in each case optionally monosubstituted to tetrasubstituted by fluorine, chlorine, methyl and/or ethyl.
Thioimides of the formula (I) which are also particularly preferred are those in which
Z represents cyclopentyl or cyclohexyl, in each case optionally monosubstituted to tetrasubstituted by fluorine, chlorine, methyl or ethyl;
or represents thienyl, pyridyl, furyl, thienylmethyl, pyridylmethyl or furylmethyl, optionally substituted by methoxy, methyl, ethyl, fluorine, chlorine or bromine;
or represents benzyl, 1-phenylethyl or 2-phenylethyl, in each case optionally monosubstituted to tetrasubstituted in an identical or different manner, and in particular represents optionally substituted phenyl, the possible substituents preferably being chosen from the following list:
fluorine, chlorine, bromo, cyano, nitro, amino, formyl, carbamoyl, thiocarbamoyl,
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxymethyl,
methoxy, ethoxy, n- or i-propoxy,
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,
methylaminomethyl, dimethylaminomethyl,
vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;
trifluoromethyl, trifluoroethyl,
difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, pentafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl,
methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino,
acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acryloyl, propioloyl,
cyclopentyl, cyclohexyl,
in each case divalent propanediyl
Dutzmann Stefan
Hanssler Gerd
Kruger Bernd-Wieland
Mauler-Machnik Astrid
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Shah Mukund J.
Truong Tamthom N.
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