Heteroaromatic compounds and crop protection agents containing them

A fungicidal composition comprising an inert carrier and a fungicidal amount of a heteroaromatic compound of the formula:

• ##STR236## wherein R.sup.1 and C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylamino or di-C.sub.1 -C.sub.6 -alkylamino;
• R.sup.2 is C.sub.1 -C.sub.6 -alkyl;
• A is a direct bond;
• unsubstituted or substituted alkylene, alkyenylene or alkynylene;
• --(CHR.sup.4).sub.n --O--, --(CHR.sup.4).sub.n --S--, --(CHR.sup.4).sub.n --NH--, --(CHR.sup.4).sub.n --NR.sup.5 --, --(CHR.sup.4).sub.n --S(.dbd.O)--, --(CHR.sup.4).sub.n --S(.dbd.O).sub.2 --, --(CHR.sup.4).sub.n --O--S(.dbd.O)--, --(CHR.sup.4).sub.n --S(.dbd.O)--O--, --(CHR.sup.4).sub.n --O--S(.dbd.O).sub.2 --, --(CHR.sup.4).sub.n --S(.dbd.O).sub.2 --O--, --(CHR.sup.4).sub.n --C(.dbd.O)--, --(CHR.sup.4).sub.n --C(.dbd.O)--, --(CHR.sup.4).sub.n --O--C(.dbd.O)--, --(CHR.sup.4).sub.n --CR.sup.5 .dbd.N--O--, --(CHR.sup.4).sub.n --CR.sup.5 .dbd.N--N.dbd.CR.sup.6 --, --(CR.sup.4).sub.n --O--N.dbd.CR.sup.7 --, n is 0, 1, 2, 3 or 4, and R.sup.4 is the same or different when n is greater than 1;
• R.sup.4, R.sup.5 and R.sup.6 independently of one another are each hydrogen or unsubstituted or substituted C.sub.1 -C.sub.6,-alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6,-alkynyl or aryl;
• R.sup.7 is hydrogen, cyano;
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl, hetaryl;
• unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxyl, cycloalkoxy, cycloalkenyloxy, cycloalkynyloxy, heterocyclyloxy, aryloxy, hetaryloxy;
• or R.sup.7 and B, together with the carbon atom to which they are bonded, form an unsubstituted or substituted, saturated or partially unsaturated alicyclic or heterocyclic ring system;
• B is hydrogen, halogen,
• unsubstituted or substituted alkyl, alkenyl, alkynyl;
• cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl, hetaryl, --(CHR.sup.4).sub.p -cycloalkyl, --(CHR.sup.4).sub.p -cycloalkenyl, --(CHR.sup.4).sub.p -cycloalkynyl, --(CHR.sup.4).sub.p -heterocyclyl, --(CHR.sup.4).sub.p -aryl, --(CHR.sup.4).sub.p -hetaryl, --(CHR.sup.4).sub.p --O-cycloalkyl, --(CHR.sup.4).sub.p --O-cycloalkenyl, --(CHR.sup.4).sub.p --O-cycloalkynyl, --(CHR.sup.4).sub.p --O-heterocyclyl, --(CHR.sup.4).sub.p --O-aryl, --(CHR.sup.4).sub.p --O-hetaryl, --(CHR.sup.4).sub.p --S-cycloalkyl, --(CHR.sup.4).sub.p --S-cycloalkenyl, --(CHR.sup.4).sub.p --S-cycloalkynyl, --(CHR.sup.4 ).sub.p --S-heterocyclyl, --(CHR.sup.4).sub.p --S-aryl, (CHR.sup.4).sub.p --S-hetaryl, --(CHR.sup.4).sub.p --NH-cycloalkyl, --(CHR.sup.4).sub.p --NH-cycloalkenyl, --(CHR.sup.4).sub.p --NH-cycloalkynyl, --(CHR.sup.4).sub.p --NH-heterocyclyl, --(CHR.sup.4).sub.p --NH-aryl, --(CHR.sup.4 .sub.p --NH-hetaryl, --(CHR.sup.4).sub.p --NR.sub.5 -cycloalkyl, --(CHR.sup.4).sub.p --NR.sup.5 -cycloalkenyl, --(CHR.sup.4).sub.p --NR.sup.5 -cycloalkynyl, --(CHR.sup.4).sub.p --NR.sup.5 -heterocyclyl, --(CHR.sup.4).sub.p --NR.sup.5 -aryl, --(CHR.sup.4).sub.p --NR.sup.5 -hetaryl, where the abovementioned cyclic groups may in turn carry substituents;
• p is 1, 2, 3 or 4, and R.sup.4 is the same or different when n is greater than 1;
• X is hydrogen, cyano, nitro, halogen, haloalkyl, haloalkoxy,
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, hetaryl;
• unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, heterocyclyloxy, aryloxy, hetaryloxy;
• unsubstituted or substituted alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkenylthio, heterocyclylthio, arylthio, hetarylthio;
• amino which may carry one or two of the following groups:
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or hetaryl;
• unsubstituted or substituted alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, cycloalkenylcarbonyl, heterocyclylcarbonyl, arylcarbonyl, hetarylcarbonyl;
• unsubstituted or substituted alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, heterocyclylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy;
• unsubstituted or substituted alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, cycloalkenyloxycarbonyl, heterocyclyloxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl;
• unsubstituted or substituted alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, cycloalkenylcarbonylamino, heterocyclylcarbonylamino, arylcarbonylamino or hetarylcarbonylamino, where these groups may additionally carry one of the following groups on the amino group:
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or hetaryl;
• aminocarbonyl which may carry one or two of the following groups on the amino group:
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or hetaryl;
• unsubstituted or substituted alkyl-S(.dbd.O)--, alkenyl-S(.dbd.O)--, alkynyl-S(.dbd.O)--, cycloalkyl-S(.dbd.O)--, cycloalkenyl-S(.dbd.O)--, heterocyclyl-S(.dbd.O)--, aryl-S(.dbd.O)--, hetaryl-S(.dbd.O)--;
• unsubstituted or substituted alkyl-S(.dbd.O)--O--, alkenyl-S(.dbd.O)--O--, alkynyl-S(.dbd.O)--O--, cycloalkyl-S(.dbd.O)--O--, cycloalkenyl-S(.dbd.O)--O--, heterocyclyl-S(.dbd.O)--O--, aryl-S(.dbd.O)--O--, hetaryl-S(.dbd.O)--O--;
• unsubstituted or substituted alkyl-O--S(.dbd.O)--, alkenyl-O--S(.dbd.O)--, alkynyl-O-S(.dbd.O)--, cycloalkyl-O-S(.dbd.O)--, cycloalkenyl-O--S(.dbd.O)--, heterocyclyl-O-S(.dbd.O)--, aryl-O--S(.dbd.O), hetaryl-O-S(.dbd.O)--;
• unsubstituted or substituted alkyl-S(.dbd.O).sub.2 --, alkenyl-S(.dbd.O).sub.2 --, alkynyl-S(.dbd.O).sub.2, cycloalkyl-S(.dbd.O).sub.2 --, cycloalkenyl-S(.dbd.O).sub.2 --, heterocyclyl-S(.dbd.O).sub.2 --, aryl-S(.dbd.O).sub.2 --, hetaryl-S(.dbd.O).sub.2 --;
• unsubstituted or substituted alkyl-S(.dbd.O).sub.2 --O--, alkenyl-S(.dbd.O).sub.2 --O--, alkynyl-S(.dbd.O).sub.2 --O--, cycloalkyl-S(.dbd.O).sub.2 --O--, cycloalkenyl-S(.dbd.O).sub.2 --O--, heterocyclyl-S(.dbd.O).sub.2 --O--, aryl-S(.dbd.O).sub.2 --O--, hetaryl-S(.dbd.O).sub.2 --O--;
• unsubstituted or substituted alkyl-O--S(.dbd.O).sub.2 --, alkenyl-O--S(.dbd.O).sub.2 --, alkynyl-O--S(.dbd.O).sub.2 --, cycloalkyl-O--S(.dbd.O).sub.2 --, cycloalkenyl-O--S(.dbd.O).sub.2 --, heterocyclyl-O--S(.dbd.O).sub.2 --, aryl-O--S(.dbd.O).sub.2 --, hetaryl-O--S(.dbd.O).sub.2 --;
• unsubstituted or substituted alkyl-ON.dbd.CR.sup.8 --, alkenyl-ON.dbd.CR.sup.8 --, alkynyl-ON.dbd.CR.sup.8 --, cycloalkyl-ON.dbd.CR.sup.8 --, cycloalkenyl-ON.dbd.CR.sup.8 --, heterocyclyl-ON.dbd.CR.sup.8 --, aryl-ON.dbd.CR.sup.8 --, hetaryl-ON.dbd.CR.sup.8 --;
• R.sup.8 is hydrogen, cyano;
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl or hetaryl;
• unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, cycloalkynyloxy, heterocyclyloxy, aryloxy or hetaryloxy;
• Q is oxygen or a substituted nitrogen;
• and its plant-tolerated acid addition products and base addition products.

A method for controlling fungi, wherein the fungi or the materials, plants or seed threatened by fungal attack or the soil is or are treated by fungal attack or the soil is or are treated wtih a fungicidal amount of a heteroaromatic compound of the formula:

• ##STR237## wherein R.sup.1 is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylamino or di-C.sub.1 -C.sub.6 -alkylamino;
• R.sup.2 is C.sub.1 -C.sub.6 -alkyl;
• A is a direct bond;
• unsubstituted or substituted alkylene, alkenylene or alkynylene;
• --(CHR.sup.4).sub.n --O--, (CHR.sup.4).sub.n --S--, --(CHR.sup.4).sub.n --NH--, --(CHR.sup.4).sub.n --NR.sup.5 --, --(CHR.sup.4).sub.n --S(.dbd.O)--, --(CHR.sup.4).sub.n --S(.dbd.O).sub.2 --, --(CHR.sup.4).sub.n --O--S(.dbd.O)--, --(CHR.sup.4).sub.n --S(.dbd.O)--O--, --(CHR.sup.4).sub.n --O--S(.dbd.O).sub.2 --, --(CHR.sup.4).sub.n --S(.dbd.O).sub.2 --O--, --(CHR.sup.4).sub.n --C(.dbd.O)--, --(CHR.sup.4).sub.n --C(.dbd.O)O--, --(CHR.sup.4).sub.n --O--, C(.dbd.O)--, (CHR.sup.4).sub.n --CR.sup.5 .dbd.N--O--, --(CHR.sup.4).sub.n--CR--.sup.5 .dbd.N--N.dbd.CR.sup.6 --, --(CHR.sup.4).sub.n --O--N.dbd.CR.sup.7 --, n is 0, 1, 2, 3 or 4, and the radicals R.sup.4 may be different when n is greater than 1;
• R.sup.4, R.sup.5 and R.sup.6 independently of one another are each hydrogen or unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl or aryl;
• R.sup.7 is hydrogen, cyano;
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl, hetaryl;
• unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxyl cycloalkoxy, cycloalkenyloxy, cycloalkynyloxy, heterocyclyloxy, aryloxy, hetaryloxy;
• or R.sup.7 and B, together with the carbon atom to which they are bonded, form an unsubstituted or substituted, saturated or partially unsaturated alicyclic or heterocyclic ring system;
• B is hydrogen, halogen,
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl, hetaryl, --(CHR.sup.4).sub.p -cycloalkyl, --(CHR.sup.4).sub.p -cycloalkenyl, --(CHR.sup.4).sub.p -cycloalkynyl, --(CHR.sup.4).sub.p -heterocyclyl, --(CHR.sup.4).sub.p -aryl, --(CHR.sup.4).sub.p -hetaryl, --(CHR.sup.4).sub.p --O-cycloalkyl, --(CHR.sup.4).sub.p --O-cycloalkenyl, --(CHR.sup.4).sub.p --O-cycloalkynyl, --(CHR.sup.4).sub.p --O-heterocyclyl, --(CHR.sup.4).sub.p O-aryl, --(CHR.sup.4).sub.p --O-hetaryl, --(CHR.sup.4).sub.p --S-cycloalkyl, --(CHR.sup.4).sub.p --S-cycloalkenyl, --(CHR.sup.4).sub.p --S-cycloalkynyl, --(CHR.sup.4).sub.p --S-heterocyclyl, --(CHR.sup.4).sub.p 13 S-aryl, --(CHR.sup.4).sub.p --S-hetaryl, --(CHR.sup.4).sub.p --NH-cycloalkyl, --(CHR.sup.4).sub.p --NH-cycloalkenyl, (CHR.sup.4).sub.p --NH-cycloalkynyl, --(CHR.sup.4).sub.p --NH-heterocyclyl, --(CHR.sup.4)--NH-aryl, --(CHR.sup.4).sub.p --NH-hetaryl, --(CHR.sup.4).sub.p --NR.sup.5 -cycloakyl, --(CHR.sup.4).sub.p --NR.sup.5 --cycloalkenyl, --(CHR.sup.4).sub.p --NR.sup.5 -cycloalkynyl, --(CHR.sup.4).sub.p --NR.sup.5 -heterocyclyl, --(CHR.sup.4).sub.p --NR.sup.5 -aryl, --(CHR.sup.4).sub.p --NR.sup.5 -hetaryl, where the abovementioned cyclic groups may in turn carry substituents;
• p is 1, 2, 3 or 4, and R.sup.4 is the same or different when n is greater than 1;
• X is hydrogen, cyano, nitro, halogen, haloalkyl, haloalkoxy,
• unsubsituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, hetaryl;
• unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, heterocyclyloxy, aryloxy, hetaryloxy;
• unsubstituted or substituted alkylthio, alkenylthio, alkynylthio, cycloalkylthio, cycloalkenylthio, heterocyclylthio, arylthio, hetarylthio;
• amino which may carry one or two of the following groups;
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or hetaryl;
• unsubstituted or substituted alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, cycloalkenylcarbonyl, heterocyclylcarbonyl, arylcarbonyl, hetarylcarbonyl;
• unsubstituted or substituted alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkenylcarbonyloxy, heterocyclylcarbonyloxy, arylcarbonyloxy, hetarylcarbonyloxy;
• unsubstituted or substituted alkoxycarbonyl, alkenyloxyarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, cycloalkenyloxycarbonyl, heterocyclyloxycarbonyl, aryloxycarbonyl, hetaryloxycarbonyl;
• unsubstituted or substituted alkylcarbonylamino, alkenylcarbonylamino, alkynylcarbonylamino, cycloalkylcarbonylamino, cycloalkenylcarbonylamino, heterocyclylcarbonylamino, arylcarbonylamino or hetarylcarbonylamino, where these groups may additionally carry one of the following groups on the amino group:
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or hetaryl;
• aminocarbonyl which may carry one or two of the following groups on the amino group:
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or hetaryl;
• unsubstituted or substituted alkyl-S(.dbd.O)--, alkenyl-S(.dbd.O)alkynyl-S(.dbd.O)--, cycloalkyl-S(.dbd.O)--, cycloalkenyl-S(.dbd.O)--, heterocyclyl-S(.dbd.O), aryl-S(.dbd.O)--, hetaryl-S(.dbd.O)--;
• unsubstituted or substituted alkyl-S(.dbd.O)--O--, alkenyl-S(.dbd.O)--O--, alkynyl-S(.dbd.O)--O--, cycloalkyl-S(.dbd.O)--O--, cycloalkenyl-S(.dbd.O)--O--, heterocyclyl-S(.dbd.O)--O--, aryl-S(.dbd.O)O--, hetaryl-S(.dbd.O)O--;
• unsubstituted or substituted alkyl-O--S(.dbd.O)--, alkenyl-O--S(.dbd.O)--, alkynyl-O--S(.dbd.O)--, cycloalkyl-O--S(.dbd.O)--, cycloalkenyl-O--S(.dbd.O)--, heterocyclyl-O--S(.dbd.O)--, aryl-O--S(.dbd.O)--, hetaryl-O--S(.dbd.O)--;
• unsubstituted or substituted alkyl-S(.dbd.O).sub.2 --, alkenyl-S(.dbd.O).sub.2 --, alkynyl-S(.dbd.O).sub.2 --, cycloalkyl-S(.dbd.O).sub.2 --, cycloalkenyl-S(.dbd.O).sub.2 --, heterocyclyl-S(.dbd.O).sub.2 --, aryl-S(.dbd.O).sub.2 --, hetaryl-S(.dbd.O).sub.2 --;
• unsubstituted or substituted alkyl-S(.dbd.O).sub.2 --O--, alkenyl-S(.dbd.O).sub.2 --O, alkynyl-S(.dbd.O).sub.2 --O--, cycloalkyl-S(.dbd.O).sub.2 --O--, cycloalkenyl-S(.dbd.O).sub.2 -O--, heterocyclyl-S(.dbd.O).sub.2 --O--, aryl-S(.dbd.O.sub.2 --O--, hetaryl-S(.dbd.O).sub.2 --O--;
• unsubstituted or substituted alkyl-O--S(.dbd.O).sub.2 --, alkenyl-O--S(.dbd.O).sub.2 --, alkynyl-O--S(.dbd.O).sub.2 --, cycloalkyl-O--S(.dbd.O).sub.2 --, cycloalkenyl-O--S(.dbd.O).sub.2 --, heterocyclyl-O--S(.dbd.O).sub.2 --, aryl-O--S(.dbd.O).sub.2, hetaryl-O--S(.dbd.O).sub.2 ;
• unsubstituted or substituted alkyl-ON.dbd.CR.sup.8 --, alkenyl-ON.dbd.CR.sup.8 --, alkynyl-ON.dbd.CR.sup.8 --, Cycloalkyl-ON.dbd.CR.sup.8 --, cycloalkenyl-ON.dbd.CR.sup.8 --, heterocyclyl-ON.dbd.CR.sup.8 --, aryl-ON.dbd.CR.sup.8 --, hetaryl-ON.dbd.CR.sup.8 --;
• R.sup.8 is hydrogen, cyano;
• unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, heterocyclyl, aryl or hetaryl;
• unsubstituted or substituted alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, cycloalkynyloxy, heterocyclyloxy, aryloxy or hetaryloxy;
• Q is oxygen or unsubstitutea nitrogen;
• and its plant-tolerated acid addition products and base addition products.