Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides

A process for the preparation of a compound of the formula VI ##STR27## in which R.sup.1 is hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl, or (C.sub.3 -C.sub.5)-cycloalkyl;

• R.sup.2 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.2 -C.sub.4)alkenyl, (C.sub.2 -C.sub.4)-haloalkenyl, (C.sub.2 -C.sub.4)-alkynyl, (C.sub.2 -C.sub.4)-haloalkynyl, (C.sub.1 -C.sub.8)-trialkylsilylalkyryl, phenyl-(C.sub.1 -C.sub.8)-dialkylsilylalkynyl, aryl-(C.sub.1 -C.sub.2)-alkyl-(C.sub.1 -C.sub.8)-dialkyl-silylalkynyl, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.8)-dialkylsilylalkynyl, (1-methylsila-(C.sub.3 -C.sub.8)-cycloalk-1-yl)alkynyl, triphenylsilylalkynyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-haloalkoxy-(C.sub.1 -C.sub.4)-haloalkyl, halogen, hydroxyl, (C.sub.1 -C.sub.4)-hydroxyalkyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 -C.sub.4)-alkanoyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkanoyl, (C.sub.3 -C.sub.5)-cycloalkyl, (C.sub.3 -C.sub.5)-halocycloalkyl, cyano, (C.sub.1 -C.sub.4)-cyanoalkyl, nitro, (C.sub.1 -C.sub.4)-nitroalkyl, thiocyano, (C.sub.1 -C.sub.4)-thiocyanoalkyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkoxycarbonyl, (C.sub.1 -C.sub.4)-alkanoyloxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.1 -C.sub.4)-alkylthio-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkylthio, (C.sub.1 -C.sub.4)-alkylsulfynyl, (C.sub.1 -C.sub.4)-haloalkylsulfynyl, (C.sub.1 -C.sub.4)-alkylsulfonyl or (C.sub.1 -C.sub.4)-haloalkylsulfonyl;
• X is NH, oxygen or S(O).sub.q where q is 0, 1, or 2;
• R.sup.5 is (C.sub.1 -C.sub.4)-perfluoroalkyl, trifluoromethylthio, cyano or (C.sub.1 -C.sub.4)-alkoxy, and when R.sup.9 is (C.sub.1 -C.sub.4)-alkoxy, R.sup.2 is also (C.sub.1 -C.sub.4)-alkyl;
• R.sup.10 is the unit E-Q, wherein
• E is a direct bond or a straight-chain or branched (C.sub.1 -C.sub.4)-alkanediyl group;
• Q is defined for Q.sup.1, and
• Q.sup.1 is a cycloalkyl group of the formula II or II' ##STR28## in which n is an integer from 2 to 7;
• (R.sup.1).sub.p and UR.sup.5 are substituents of the isocyclic ring formed with the participation of (CH.sub.2).sub.n ;
• p is 1 or 2;
• R.sup.4 is hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)alkoxy, or (C.sub.1 -C.sub.4)-alkylthio;
• U is a direct bond, oxygen or a group S(O).sub.m where m=0, 1 or 2;
• R.sup.5 is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, and, if Q.sup.1 is a radical of the formula II and U is a direct bond, R.sup.5 is also hydroxyl, cyano, thiocyano, nitro or halogen, wherein the aryl or heterocyclyl radicals are optionally substituted up to three--and in the case of fluorine up to the maximum number of--by identical or different substitutents and for one or more nonadjacent saturated carbon units in the alkyl, alkenyl or alkynyl radicals mentioned to be replaced by a carbonyl group or by a heteroatom unit selected from the group consisting of oxygen;
• S(O).sub.x where x=0, 1 or 2;
• NR.sup.6 ;
• or SiR.sup.7 R.sup.8, in which R.sup.6 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)alkoxy, or (C.sub.1 -C.sub.4)-alkanoyl and R.sup.7 and R.sup.8 are (C.sub.1 -C.sub.4)-alkyl;
• and in which, furthermore, 3 to 12 atoms of these hydrocarbon radicals, which radicals are modified as above if desired, optionally form a ring and these hydrocarbon radicals, with or without the variations indicated, are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxy-carbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, wherein said cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned are optionally substituted by up to three and in the case of fluorine up to the maximum number of identical or different substituents, or Q is as defined for Q.sup.2 and Q.sup.2 is a radical of the formula III ##STR29## in which R.sup.11 is aryl or heteroaromatic ring system and the aryl or heteroaromatic ring system are optionally substituted by up to three--and in the case of fluorine up to the maximum number of--identical or different substituents, or a salt thereof, wherein the substituents for the aromatic and heterocyclic ring systems are halogen, nitro, cyano, di-(C.sub.1 -C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-trialkylsilyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.2)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.2)-alkoxy-(CH.sub.2 CH.sub.2).sub.1,2 -ethoxy, (C.sub.1 -C.sub.4)-alkylthio (C.sub.1 -C.sub.4)-alkylsulfinyl, (C.sub.1 -C.sub.4)-alkylsulfonyl, phenyl, benzyl, phenoxy, halophenoxy, (C.sub.1 -C.sub.4)-alkylphenoxy, (C.sub.1 -C.sub.4)-alkylthiophenoxy, phenylthio, heterocyclyl, heterocyclythio, heterocyclyloxy, haloheterocyclyloxy, alkylheterocyclyloxy or alkoxyheterocyclyloxy, wherein said alkyl radicals and the radicals derived therefrom are optimally substituted one or more times--and in the case of fluorine up to the maximum number of--by halogen;
• R.sup.10 is a (C.sub.1 -C.sub.20)-alkyl radical in which one or more, nonadjacent saturated carbon units are optionally replaced by heteroatom units selected from the group consisting of oxygen;
• S(O).sub.x where x=0, 1 or 2;
• NR.sup.6' or SiR.sup.7' R.sup.8', where R.sup.6' is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkanoyl or (C.sub.1 -C.sub.4)-alkoxy, and where R.sup.7' and R.sup.8' are (C.sub.1 -C.sub.4)-alkyl, and in which furthermore these alkyl radicals, with or without the variations indicated, are optionally substituted by one or more times--and in the case of halogen up to the maximum number of--identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, whercin the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned to be unsubstituted or substituted by up to three--and in the case of fluorine up to the maximum number of--identical or different substituents, wherein the substituent for the aliphatic, aromatic or heterocyclic ring systems are halogen, nitro, cyano, di-(C.sub.1 -C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-trialkylsilyl, (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.2)-alkoxy-›CH.sub.2 CH.sub.2 !.sub.1,2 -ethoxy, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.1 -C.sub.4)-alkylsulfinyl, (C.sub.1 -C.sub.4)-alkylsulfonyl, phenyl, benzyl, phenoxy, phenylthio, halophenoxy, (C.sub.1 -C.sub.4)-alkylphenoxy, (C.sub.1 -C.sub.4)-alkoxyphenoxy, (C.sub.1 -C.sub.4)-alkylthiophenoxy, heterocyclyl, heterocyclylthio, heterocyclyloxy, haloheterocyclyloxy, alkylheterocyclyloxy or alkoxyheterocyclyloxy, where in the alkyl radicals and the radicals derived therefrom one or more--and in the case of fluorine up to the maximum number of--hydrogen atoms can be replaced by halogen;
• and
• wherein heterocyclyl means a heteroaromatic or heteroaliphatic ring system, where a heteroaromatic ring system is a (C.sub.6 -C.sub.14 ) aryl group in which at least one CH group is replaced by N and/or at least two adjacent CH groups are replaced by S, NH or O and heteroaliphatic ring system is a (C.sub.3 -C.sub.8)-cycloalkyl radical in which at least one carbon unit has been replaced by O, S or a group N.sup.12, and R.sup.12 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or aryl
• which comprises reacting a compound of the formula VII ##STR30## for which R.sup.1, R.sup.2, A, X and R.sup.10 are as defined for formula VI and, if R.sup.9 is (C.sub.1 -C.sub.4)-alkoxy, R.sup.2 is also (C.sub.1 -C.sub.4)-alkyl, and L is a leaving group selected from the group consisting of halogen, alkylthio, alkanesulfonyloxy, arylsulfonyloxy, alkylsulfonyl or arylsulfonyl
• with a compound MR.sup.9, where M is an alkali metal or alkaline earth metal.