Substituted pyridines, processes for their preparation and their use as pesticides and fungicides

A compound of the formula I or an N-oxide or salt thereof ##STR12## in which R.sup.1 is R--O(C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkoxy(C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkoxy-halo(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxyhalo(C.sub.1 -C.sub.4)alkyl, halo(C.sub.2 -C.sub.4)alkenyloxy(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.2 -C.sub.4)alkenylthio(C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkylthio(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkylthio-halo(C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkylthio-halo(C.sub.1 -C.sub.4) or halo(C.sub.2 -C.sub.4)alkenylthio(C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkylsulfinyl, (C.sub.1 -C.sub.4)alkylsulfonyl, fluorine, chlorine, bromine, (C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.4)alkoxy or halo(C.sub.1 -C.sub.4)alkoxy;

• R.sup.2 is (C.sub.2 -C.sub.4)alkenyloxy, (C.sub.2 -C.sub.4)alkynyloxy, (C.sub.3 -C.sub.7)cycloalkenyloxy, halo(C.sub.2 -C.sub.4)alkenyloxy, halo(C.sub.3 -C.sub.7)cycloalkyloxy, R--O--CO--, (C.sub.3 -C.sub.7)cycloalkylthio, halo(C.sub.1 -C.sub.4)alkylthio, (C.sub.3 -C.sub.7)cycloalkylsulfinyl, halo(C.sub.1 -C.sub.4)alkylsulfinyl, (C.sub.3 -C.sub.7)cycloalkylsulfonyl, halogen(C.sub.1 -C.sub.4)alkylsulfonyl, (C.sub.2 -C.sub.4)alkenylthio, (C.sub.3 -C.sub.7)cycloalkenylthio, (C.sub.2 -C.sub.4)alkenylsulfinyl, (C.sub.3 -C.sub.7)cycloalkenylsulfinyl, (C.sub.2 -C.sub.4)alkenylsulfonyl, (C.sub.3 -C.sub.7)cycloalkenylsulfonyl, iodine, cyano, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkylsulfinyl, (C.sub.1 -C.sub.4)alkylsulfonyl, fluorine, chlorine, bromine, (C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.4)alkoxy or halo(C.sub.1 -C.sub.4)alkoxy;
• with the proviso that R.sup.1 and R.sup.2 are not both from the group consisting of (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkylsulfinyl, (C.sub.1 -C.sub.4)alkylsulfonyl, fluorine, chlorine, bromine, (C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.4)alkoxy and halo(C.sub.1 -C.sub.4)alkoxy;
• R.sup.3 and R.sup.4 are identical or different and independently of one another are hydrogen, halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.3 -C.sub.5)cycloalkyl and/or halo(C.sub.3 -C.sub.5)cycloalkyl;
• R is (C.sub.1 -C.sub.10)alkyl, (C.sub.2 -C.sub.10)alkenyl, (C.sub.2 -C.sub.10)alkynyl, (C.sub.3 -C.sub.8)cycloalkyl or aralkyl;
• A is hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)acyl, aryl or aryl(C.sub.1 -C.sub.4)alkyl wherein aryl is a phenyl group which is optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, (C.sub.3 -C.sub.8)cycloalkyl, (C.sub.3 -C.sub.8)cycloalkenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, nitro, --CO--R.sup.8, acetoxy, hydroxyl, cyano, SiR.sup.9 R.sup.10 R.sup.11, O--SiR.sup.9 R.sup.10 R.sup.11, NR.sup.12 R.sup.13, S(O)R.sup.14, SO.sub.2 R.sup.14, optionally substituted (C.sub.1 -C.sub.12)alkyl, optionally substituted (C.sub.2 -C12)alkenyl, optionally substituted (C.sub.2 -C.sub.12)alkoxy, (C.sub.3 -C.sub.7)cycloalkoxy, optionally substituted (C.sub.1 -C.sub.12)alkylthio and (C.sub.3 -C.sub.7)cycloalkylthio, where in the above (C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.12)alkenyl, (C.sub.1 -C.sub.12)alkoxy and (C.sub.1 -C.sub.12)alkylthio radicals one or more CH.sub.2 groups are optionally replaced by CO and/or heteroatoms or heteroatom groups selected from the group consisting of O, S, SO, SO.sub.2, NR.sup.5 or SiR.sup.6 R.sup.7 and where the optional substitutes are one or more identical or different radicals selected from the group consisting of halogen, halo(C.sub.1 -C.sub.4)alkoxy, hydroxyl, (C.sub.3 -C.sub.8)cycloalkyl, (C.sub.3 -C.sub.8)cycloalkenyl, (C.sub.1 -C.sub.4)acyl, phenyl, substituted phenyl, phenoxy, substituted phenoxy, phenylthio and substituted phenylthio;
• and
• R.sup.8 is (C.sub.1 -C.sub.7)alkyl, halo(C.sub.1 -C.sub.7)alkyl, (C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, (C.sub.1 -C.sub.7)alkoxy, (C.sub.1 -C.sub.7)alkylthio, phenyl or substituted phenyl;
• R.sup.9, R.sup.10 and R.sup.11 are identical or different and independently of one another are (C.sub.1 -C.sub.4)alkyl, phenyl and/or substituted phenyl;
• R.sup.12 and R.sup.13 are identical or different and independently of one another are hydrogen, (C.sub.1 -C.sub.4)alkyl and/or (C.sub.1 -C.sub.4)acyl;
• R.sup.14 is (C.sub.1 -C.sub.10)alkyl, phenyl or substituted phenyl;
• R.sup.5 is hydrogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)acyl;
• R.sup.6 and R.sup.7 identical or different, each independently are (C.sub.1 -C.sub.4)alkyl, phenyl and/or substituted phenyl;
• Y-Z together is an optionally substituted (C.sub.1 C.sub.15)-hydrocarbon radical which is unbranched or branched and in which one or more CH.sub.2 groups are optionally replaced by a heteroatom group, selected from the group consisting of O, NR.sup.5, S, SO, SO.sub.2 or Si.sup.6 R.sup.7 wherein said radical is optionally substituted by one or more identical or different substituents and the substituents are selected from the group consisting of (C.sub.1 -C.sub.7)alkyl, (C.sub.2 -C.sub.4)alkenyl, (C.sub.2 -C.sub.4)alkynyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkenyl, halogen, halo(C.sub.1 -C.sub.4)alkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.1 -C.sub.4)alkoxy, halo(C.sub.3 -C.sub.7)cycloalkoxy, hydroxyl, cyano and (C.sub.1 -C.sub.4)acyl;
• or, if not embraced by the above definitions,
• Y is a bond or a bivalent hydrocarbon radical having 1 to 6 carbon atoms which is optionally substituted by one or more identical or different radicals selected from the group consisting of (C.sub.1 -C.sub.7)alkyl, (C.sub.2 -C.sub.4)alkenyl, (C.sub.3 -C.sub.7)alkynyl, (C.sub.3 -C.sub.7)cycloalkyl, (C.sub.3 -C.sub.7)cycloalkenyl, halogen, halo(C.sub.1 -C.sub.4)alkyl, halo(C.sub.3 -C.sub.7)cycloalkyl, halo(C.sub.1 -C.sub.4)alkoxy, halo(C.sub.3 -C.sub.7)cycloalkoxy, hydroxyl, cyano and (C.sub.1 -C.sub.4)acyl;
• and
• Z is aryl as defined above;
• or O-aryl if Y is not a direct bond;
• or (C.sub.3 -C.sub.7)cycloalkyl or (C.sub.5 -C.sub.8)cycloalkenyl wherein one CH.sub.2 group of the carbocycle is optionally replaced by NR.sup.15 wherein R.sup.15 is phenyl or substituted phenyl;
• and the above-mentioned (C.sub.3 -C.sub.8)cycloalkyl or C.sub.5 -C.sub.8)cycloalkenyl is optionally substituted by one or more identical or different radicals selected from the group consisting of (C.sub.1 -C.sub.15)alkyl, (C.sub.1 -C.sub.16)alkenyl, (C.sub.2 -C.sub.18)alkynyl, (C.sub.1 -C.sub.12)alkoxy, (C.sub.1 -C.sub.12)alkanoyloxy, (C.sub.2 -C.sub.12)acyl, (C.sub.1 -C.sub.12)alkyloxycarbonyl, (C.sub.1 -C.sub.18)alkanediyl, (C.sub.1 -C.sub.18)alkylidene, SiR.sup.9 R.sup.10 R.sup.11, NR.sup.16 R.sup.17, hydroxyl, oxo, halogen or aryl and wherein one or more CH.sub.2 groups in the first 11 hydrocarbon radicals mentioned above are optionally replaced by a group selected from the group consisting of O, S, SO, SO.sub.2, NR.sup.5 or SiR.sup.6 R.sup.7, where R.sup.5, R.sup.6 and R.sup.7 are as defined above and where additionally three to six carbon atoms of these hydrocarbon radicals optionally form an optionally substituted cycle ring these hydrocarbon radicals, containing one or more identical or different substituents selected from the group consisting of halogen, haloalkyl, cycloalkyl, acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio;
• R.sup.9, R.sup.10, R.sup.11 and aryl are as defined above and R.sup.16 and R.sup.17 are identical or different and independently of one another are (C.sub.1 -C.sub.4)acyl, (C.sub.3 -C.sub.6)cycloalkyl, phenyl and/or substituted phenyl;
• or
• Z is a furyl radical of the formula II ##STR13## in which R.sup.18 is hydrogen, halogen, halo(C.sub.1 -C.sub.4)alkyl, cyano, nitro, (C.sub.1 -C.sub.4)alkyl, phenyl, (C.sub.1 -C.sub.4)alkoxy or halo(C.sub.1 -C.sub.4)alkoxy;
• or
• Z is a thienyl radical of the formula III ##STR14## in which R.sup.19 is hydrogen, halogen, halo(C.sub.1 -C.sub.4)alkyl, cyano, nitro, (C.sub.1 -C.sub.4)alkyl, phenyl, (C.sub.1 -C.sub.4)alkoxy, halo(C.sub.1 -C.sub.4)alkoxy or thienyl;
• or
• if not embraced by the above definitions, is a radical of the formula IV or V ##STR15## in which R.sup.19 is as defined above, J is N or CH and G is O, NR.sup.20 or S, with the proviso that, if J.noteq.N, then G is NR.sup.20, where R.sup.20 is hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)acyl, phenylsulfonyl or substituted phenylsulfonyl;
• or
• Z is a radical selected from the group consisting of optionally substituted naphthyl, dihydronaphthyl, tetrahydronaphthyl and decahydronaphthyl;
• or
• optionally substituted indolyl;
• or
• 1. 3-benzodioxolyl, 2,6-dimethyl-4-morpholinyl and 1-adamantyl;
• or
• Z is a radical of the formula VI ##STR16## in which R.sup.21 radicals are identical or different and independently of one another are hydrogen, halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, halo(C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkoxy, NO.sub.2, CN, (C.sub.1 -C.sub.4)alkylcarbonyl, formyl, phenoxy and/or substituted phenoxy, with the proviso that at least two of the radicals R.sup.21 are selected from the group consisting of hydrogen and fluorine,
• and Y.sup.2 is pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, benzoxazolyl or benzothiazolyl, which are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, halo(C.sub.1 -C.sub.4)alkyl, halo(C.sub.1 -C.sub.4)alkoxy, nitro, cyano and (C.sub.1 -C.sub.4)alkanoyl;
• or
• Z is a radical of the formula VII ##STR17## in which one of the groups X.sup.2 or X.sup.3 is N, and the other group is CH;
• R.sup.22 is --W--R.sup.23, phenyl or substituted phenyl;
• W is O or S;
• and
• R.sup.23 is (C.sub.1 -C.sub.7)alkyl, halo(C.sub.1 -C.sub.7)alkyl, (C.sub.1 -C.sub.7)alkoxy, halo(C.sub.1 -C.sub.7)alkoxy, naphthyl or phenyl, where, if not embraced by the above definitions, each of the abovementioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, (C.sub.1 -C.sub.10)alkyl, halo(C.sub.1 -C.sub.7)alkyl, hydroxy(C.sub.1 -C.sub.7)alkyl, (C.sub.1 -C.sub.4)alkoxymethyl, (C.sub.1 -C.sub.4)alkoxy, halo(C.sub.1 -C.sub.4)alkoxy, phenoxy, substituted phenoxy, phenyl, substituted phenyl, cyano, nitro, hydroxyl, (C.sub.1 -C.sub.4)alkanoyloxy or benzyloxy.