Substituted pyridines/pyrimidines, their preparation, and their use as pesticides

A compound of the formula I

• in which
• R1 is hydrogen, fluorine or chlorine
• R2 and R3 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, tri-(C1-C4)-alkylsilyl-(C2-C4)-alkynyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C4)-haloalkoxy-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-haloalkyl, (C1-C4)-haloalkoxy-(C1-C4)-haloalkyl, halogen, hydroxyl, (C1-C4)-hydroxyalkyl, (C1-C4)-alkanoyl, (C1-C4)-alkanoyl-(C1-C4)-alkyl, (C2-C4)-haloalkanoyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, (C4-C5)-cycloalkenyl, (C4-C5)-halocycloalkenyl, (C3-C5)-cycloalkoxy, cyano, cyan-(C1-C4)-alkyl, nitro, nitro-(C1-C4)-alkyl, thiocyano, thiocyano-(C1-C4)-alkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkoxycarbonyl-(C1-C4)-alkyl, (C1-C4)-haloalkoxycarbonyl, (C1-C4)-alkylthio, (C1-C4)-haloalkylthio, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C1-C4)-haloalkylthio-(C1-C4)-alkyl, (C1-C4)alkylthio-(C1-C4)-haloalkyl, (C1-C4)-alkylsulfmyl, (C1-C4)-haloalkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-haloalkylsulfonyl;
• or
• R2 and R3 together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-member carbocyclic ring which, it is a 5-membered ring, a CH2 is optionally replaced by an oxygen or sulfur atom or which, if it is a 6-membered ring, one or two CH units is optionally replaced by a nitrogen atom, and which is optionally substituted by 1, 2 or 3 identical or different radicals and these radicals are (C1-C4)-alkyl, (C1-C4)-haloalkyl, halogen, (C1-C4)-alkoxy or (C1-C4)-haloalkoxy;
• or
• R2 and R3 together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7- membered carbocyclic ring in which on CH2-group is optionally replaced by oxygen or sulfur and which is optionally substituted by 1, 2 or 3 (C1-C4)-alkyl groups;
• A is N;
• X is NH, oxygen or S(O)q where q=0, 1 or 2;
• Y is a direct bond or CH2;
• Z is oxygen or sulfur;
• R4, R5 and W-R6 are substituents of the heteroaliphatic ring system, where
• R4 and R5 independently of one another are hydrogen, halogen, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (C3-C6)-cycloalkyl, (C4-C6)-Cycloalkenyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkanoyloxy, (C1-C4)-haloalkanoyloxy, (C1-C4)-alkylthio or (C1-C4)-haloalkylthio;
• W is a direct bond, oxygen, —NR12, —CO—, —COO—, CONR12—, sulfur, —C═N—, —C═N—O— or —NR12O—;
• R6 is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl wherein the last-mentioned 5 radicals are optionally substituted by one or more, in the case of fluorine up to the maximum number of, identical or different radicals D1R16, or
• R6 is aryl which is unsubstituted or substituted by up to three, in the case of fluorine also up to the maximum number of, identical or different radicals D2R17, or
• R4 and R6 together form a three- to eight-membered ring system which is linked spirocyclically to the ring system containing Y and Z and in which one CH2 group in the ring formed by R4 and R6 is optionally replaced by hetero atom units selected from the group consisting of oxygen, S(O)n where n=0, 1 or 2, or NR18
• where
• R12 is hydrogen, (C1-C4)-alkyl, (C1-C4)-alkanoyl or (C3-C5)-cycloalkyl;
• R18 is hydrogen, alkyl, alkanoyl, alkoxy, benzyl, or aryl, wherein the last-mentioned 2 radicals are unsubstituted substituted with up to three, in the case of fluorine also up to the maximum number of, identical or different substituents R19;
• R19 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, cyano, nitro or halogen,
• and the ring system formed by R4 and R6 is unsubstituted or substituted with up to three substituents D3R20, or
• the ring system formed by R4 and R6 together with a fither benzene ring or cyclohexane ring forms a fused ring system and the benzene ring in these fused systems are unsubstituted or substituted with up to three, in the case of fluorine also up to the maximum number of, identical or different substituents D4R21, where
• D1, D2, D3 and D4 are in each case independent of one another and are a direct bond, oxygen, S(O)k, SO2O, OSO2, CO, OCO, COO, SO2NR22, NR22SO2, NR22O, ONR22, NR22, NR22CO, CONR22 or SiR23R24, where k is 0, 1 or 2;
• and
• R16, R17, R20 and R21 in each case independently of one another are hydrogen, cyano, nitro, halogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)alkynyl, (C2-C8)-haloalkynyl, (C1-C8)-alkoxy(C1-C4)-alkyl, (C1-C8)-haloalkoxy(C1-C4)-alkyl, (C1-C8)-alkylthio(C1-C4)-alkyl, (C1-C8)-haloalkylthio (C1-C4)-alkyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C1-C4)-alkyl, (C4-C8)-cycloalkenyl-(C1-C4)-alkyl, aryl or aryl-(C1-C4)-alkyl wherein the cycloaliphatic or aromatic ring systems in the last-mentioned 6 radicals are unsubstituted or substituted with up to three, in the case of fluorine also up to the maximum number of, identical or different substituents R25, where
• R22 radicals independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkanoyl or (C3-C5)-cycloalkyl and
• R23 and R24 independently of one another are (C1-C4)-alkyl and
• R25 radicals independently of one another are (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, cyano, nitro, halogen, (C1-C4)-alkanoyl or (C2-C4)-haloalkanoyl, or two of the radicals R16, R17, R20, R21, R25 on the same carbon atom together and in each case independently of one another are an oxo group;
• or a salt thereof.