Substituted spiroalkylamino and alkoxy heterocycles, processes for their preparation, and their use as pesticides and fungicides

A compound of the formula I ##STR31## in which R.sup.1 is hydrogen, halogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.3 -C.sub.5)-cycloalkyl or (C.sub.3 -C.sub.5)-halocycloalkyl;

• R.sup.2 and R.sup.3 are identical or different and are in each case 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, tri(C.sub.1 -C.sub.4)-alkylsilyl-(C.sub.2 -C.sub.4)-alkynyl, (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)-alkoxycarbonyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkoxycarbonyl, (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)-alkylsulfinyl, (C.sub.1 -C.sub.4)-haloalkylsulfinyl, (C.sub.1 -C.sub.4)-alkylsulfonyl or (C.sub.1 -C.sub.4)-haloalkylsulfonyl;
• or
• R.sup.2 and R.sup.3 together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered carbocyclic ring which, if it is a 5-membered ring, optionally contains an oxygen or sulfur atom in place of CH.sub.2 or which, if it is a 6-membered ring, optionally contains one or two nitrogen atoms in place of one or two CH units, and which is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, halogen, (C.sub.1 -C.sub.4)-alkoxy or (C.sub.1 -C.sub.4)-haloalkoxy, or
• R.sup.2 and R.sup.3 together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7-membered carbocyclic ring which contains oxygen and/or sulfur in place of one or two CH.sub.2 groups and which is optionally substituted by 1, 2 or 3 (C.sub.1 -C.sub.4)-alkyl groups;
• X is NH, oxygen or S(O).sub.q where q is 0, 1 or 2;
• E is a direct bond or a straight-chain or branched (C.sub.1 -C.sub.4)alkanediyl group;
• Y and Z are identical or different and independently of one another are in each case CH.sub.2, oxygen or a group S(O).sub.x where x is 0, 1 or 2;
• W is a group (CH.sub.2).sub.n where n is an integer from 1 to 4, or
• W, in the event that Y and/or Z are CH.sub.2, is optionally a direct bond between Y and Z;
• one or more hydrogen atoms in the group --Y--W--Z-- are optionally replaced by .dbd.U.dbd.V.dbd.R.sup.6 and, optionally, by R.sup.5, as shown in formula I and described hereinbelow;
• a and b are identical or different and independently of one another are the numbers 0, 1, 2 or 3, a and b not simultaneously being 0;
• R.sup.4 and R.sup.5 are identical or different and independently of one another are in each case halogen, (C.sub.2 -C.sub.20)-alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;
• r and s are identical or different and independently of one another are 0, 1 or 2;
• U is a single bond, oxygen, a group S(O).sub.y where y is 0, 1 or 2 or a croup NR.sup.7 where R.sup.7 is hydrogen, (C.sub.1 -C.sub.4)-alkyl or (C.sub.1 -C.sub.4)-alkoxy;
• V is a single bond, carbonyl or a group of the formula ##STR32## or ##STR33## where Q is oxygen, sulfur or (C.sub.1 -C.sub.4)-alkylimino, T is oxygen, sulfur or a group NR.sup.7', and T' is (C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.4)-alkylthio or NR.sup.7' R.sup.7", and where R.sup.7' and R.sup.7" are identical or different and are as defined above for R.sup.7 ;
• or
• U and V together are a double bond;
• and
• a) R.sup.6 is (C.sub.2 -C.sub.20)-alkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted heterocyclyl or cyano, or, in the event that U and V together are a direct single bond,
• b) R.sup.6 is as defined above or is halogen, hydroxyl, carboxyl, nitro or a group SiR.sup.8 R.sup.9 R.sup.10 where R.sup.8 and R.sup.9 are (C.sub.1 -C.sub.4)-alkyl and R.sup.10 is alkyl or optionally substituted aryl, or, in the event that U and V together are a double bond,
• c) R.sup.6 is alkylidene or alkyloximino;
• and the alkyl, alkenyl, alkynyl, alkylidene or alkyloximino radicals mentioned under a), b) or c) for R.sup.6, R.sup.8, R.sup.9 and R.sup.10 have at least one of the following characteristics:
• i. one or more non-adjacent CH.sub.2 groups are replaced by CO and/or heteroatom units selected from the group consisting of 0, S(0).sub.x, NR.sup.11, and SiR.sup.12 R.sup.13 wherein x is 0, 1, or 2, R.sup.11 is H, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, or (C.sub.1 -C.sub.4)alkanoyl;
• R.sup.12 and R.sup.13 are (C.sub.1 -C.sub.4)alkyl;
• ii. 3 to 8 atoms of these radicals form an up to 8-membered ring;
• iii. the hydrocarbon radicals, with or without the abovementioned variations, 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, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, wherein said cycloaliphatic, aromatic or heterocyclic ring systems in the substituents which have just been mentioned are unsubstituted or substituted with up to three, in the case of halogen, also up to the maximum number of, identical or different substituents;
• and furthermore, in the event that R.sup.5 and R.sup.6 are alkyl radicals, these variables are optionally linked cyclically or spirocyclically;
• with the exception of those compounds of formula I, wherein R.sup.1 is hydrogen;
• R.sup.3 is CH.sub.2 OCH.sub.3 ;
• R.sup.3 is OCH.sub.3 ;
• X is NH;
• E is a direct bond;
• and Q is ##STR34## wherein heterocycle, if not further specified, means a heteroaromatic system selected from the group consisting of thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo›b!thiophene, benzo›b!furan, indole, benzo›c!thiophene, benzo›c!furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinolizine or a (C.sub.3 -C.sub.8)-cycloalkyl radical in which at least one carbon unit is replaced by O, S or a group NR.sup.14 and R.sup.14 is hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or aryl;
• and
• wherein substituted, if not further specified is selected from the group consisting of halogen, nitro, cyano, di- (C.sub.1 -C.sub.4)-alkylamino, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl, (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 O!.sub.1,2 -ethoxy, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.1 -C.sub.4)-alkylsulfinyl, (C.sub.1 -C.sub.4)-alkyl-sulfonyl, thiocyano, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-haloalkylthio, (C.sub.2 -C.sub.4)-haloalkylsulfinyl, (C.sub.1 -C.sub.4)-haloalkylsulfonyl, (C.sub.2 -C.sub.4)-alkenyl, (C.sub.2 -C.sub.4 )-haloalkenyl, trimethylsilylethynyl, (C.sub.1 -C.sub.4)-alkanoyl, (C.sub.1 -C.sub.4)-alkoxycarbonyl, 4-acetylpiperanzin-1-yl, phenyl, benzyl, phenoxy, halophenoxy, (C.sub.1 -C.sub.4)-alkylphenoxy, (C.sub.1 -C.sub.4)-alkoxyphenoxy, phenylthio, heterocyclyl, heterocyclylthio or heterocyclyloxy, it being possible for one or more hydrogen atoms, in the case of fluorine also up to the maximum number of hydrogen atoms, in the alkyl radicals and the radicals derived therefrom to be replaced by halogen or a salt thereof.