Substituted pyrimidinium compounds for combating animal pests

A substituted pyrimidinium compound of formula (I)

• wherein
• X, Y are each independently O or S;
• Z is a direct bond, O, S(O)m, NRb, C(RaRaa)O, C(═X1), C(═X1)Y1, or Y1C(═X1);
• X1 is O, S, or NRb;
• Y1 is O, S, or NRc;
• A is CH or N and, wherein the nitrogen of the pyrimidinium ring taken together with the contiguous linking carbon atom and A as depicted in formula (I), form a four- to seven-membered ring, wherein each remaining ring member is selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N(Rc)p, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S), and the sulfur atom ring members are independently selected from S(═O)m, wherein each ring may be substituted with up to 3 Ra;
• R3 is C1-C6-alkyl-C(═N(O)pRb)Rbi or C1-C6-alkyl-C(═NNRbRc)Rb1;
• R1 is hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl, C4-C10-cycloalkenyl, C5-C14-cycloalkylcycloalkyl or R1 may form a three- to eleven-membered saturated, or partially unsaturated or aromatic carbo-or heterocyclic ring or ring system, which may contain 1 to 4 heteroatoms selected from N(Rc)p, O, and S, wherein S may be oxidized, and wherein the aforementioned groups and the carbo- or heterocyclic rings system may be unsubstituted, partially or fully substituted with Ra;
• or
• R1 is C(═O)Rb, C(═O)ORe, NRbRc, C(═O)NRbRc, C(═S)NRbRc, SO2NRbRc, OC(═O)Rc, OC(═O)ORe, OC(═O)NRbRe, N(Rc)C(═O)Rc, N(Rc)C(═O)ORe, N(Rc)C(═O)NRbRc, NRcSO2Rb, NRcSO2NRbRc, Si(Rd)3, C(═NRc)Rc, C(═NORc)Rc, C(═NNRbRc)Rc, C(═NN(C(═O)Rb)Rc)Rc, C(═NN(C═O)ORc)(Rc)2, S(═O)o(═NRb)qRc, or N═CRbRc;
• Ra is each independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, CN, ORc, NRbRc, NO2, C(═O)(O)pRc, OC(═O)(O)pRe, C(═O)NRbRc, OC(═O)NRbRe, NRbC(═O)(O)pRe, NRbC(═O)NRbRc, C(═S)NRbRc, S(O)mRb, SO2NRbRc, OSO2Rc, OSO2NRbRc, NRbSO2Rc, NRbSO2NRbRc, N═S(═O)pRcRc, S(═O)o(═NRb)qRc, SF5, OCN, SCN, Si(Rd)3 or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N—(Rc)p, O, and S which may be oxidized, and wherein the aforementioned groups and the carbo- or heterocyclic ring may be partially or fully substituted with Raa, or two geminally bound groups Ra together may form a group selected from ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• Raa is each independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• Rb is each independently hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylcarbonyl, C1-C6-cycloalkylcarbonyl, C1-C6-phenylcarbonyl, or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(Rc)p, O, and S, wherein S may be oxidized, and wherein Rb may be partially or fully substituted with Rab;
• Rab is each independently is each independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, —S—C1-C6-alkyl, phenyl or 5-or 6-aromatic heterocyclic ring;
• wherein Rab may be partially or fully substituted with Raa;
• Rbi is each independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(Rc)p, O, and S, wherein S may be oxidized and which carbo- or heterocyclic ring may be partially or fully substituted with Raa;
• Rc is each independently hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C6 cycloalkyl, or a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(Raa)p, O and S, wherein S may be oxidized and wherein the carbo- or heterocyclic ring may be partially or fully substituted with Raa;
• wherein two geminally bound groups RbRb, RcRb or RcRc together with the atom to which they are bound, may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 2 heteroatoms or heteroatoms groups selected from N, O, S, NO, SO and SO2 and wherein the carbo- or heterocyclic ring may be partially or fully substituted with R4;
• Rd is each independently hydrogen, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3—C-cycloalkyl, or C1-C6-alkoxyalkyl, wherein the above mentioned groups may be substituted with one or more halogen;
• Re is each independently, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C6 cycloalkyl, or a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N(Raa)p, O and S, wherein S may be oxidized and wherein the carbo- or heterocyclic ring may be partially or fully substituted with Raa;
• n is 0, 1 or 2;
• m is 0, 1, or 2;
• p is 0 or 1;
• R2 is H, halogen, CN, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C10 cycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C6-C14 cycloalkylcycloalkyl, C5-C10 alkylcycloalkylalkyl, or C3-C6 cycloalkenyl, wherein the aforementioned groups may be unsubstituted, partially, or fully substituted with R2a, or R2 may form a carbo-or heterocyclic three- to ten-membered ring or a seven- to eleven-membered rings system, which ring or ring system may be saturated, partially unsaturated, or aromatic, and which ring or ring system may contain 1 to 4 heteroatoms selected from N(Rc)p, O, and S, wherein S may be oxidized, and wherein the carbo- or heterocyclic ring or rings system may be unsubstituted, partially, or fully substituted with R2a;
• R2a is each independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, CN, ORc, NRbRc, NO2, C(═O)(O)pRc, OC(═O)(O)pRe, C(═O)NRbRc, OC(═O)NRbRe, NRbC(═O)(O)pRe, NRbC(═O)NRbRc, C(═S)NRbRc, S(O)mRb, SO2NRbRc, OSO2Rc, OSO2NRbRc, NRbSO2Rc, NRbSO2NRbRc, SF5, OCN, SCN, Si(Rd)3, C(═N(O)pRb) Rb, C(═NNRbRc)Rb, C(═NN(C(═O)OpRc)Rc)Rb, ON═CRbRc, ONRbRc, S(═O)o(═NRb)qRc, SO2NRb(═O)NRbRc, P(═X2)RbRc, OP(═X2)(OpRc)Rb, OP(═X2)(ORc)2, N═CRbRc, NRbN═CRbRc, NRbNRbRc, NRbC(═S)NRbRc, NRbC(═NRb)NRbRc, NRbNRbC(═X2)NRbRc, NRbNRbSO2NRbRc, N═S(═O)pRcRc, or a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from N—(Rc)p, O, and S, wherein S may be oxidized, and wherein the aforementioned groups and the carbo- or heterocyclic ring may be partially or fully substituted with R2aa;
• or
• two geminally bound groups R2a together may form a group selected from ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• R2aa is each independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, CN, ORc, NRbRc, NO2, C(═O)(O)pRc, OC(═O)(O)pRe, C(═O)NRbRc, OC(═O)NRbRe, NRbC(═O)(O)pRe, NRbC(═O)NRbRc, C(═S)NRbRc, S(O)mRb, SO2NRbRc, OSO2Rc, OSO2NRbRc, NRbSO2Rc, NRbSO2NRbRc, SF5, OCN, SCN, Si(Rd)3, C(═N(O)pRb)Rb, C(═NNRbRc)Rb, C(═NN(C(═O)OpRc)Rb)Rb, ON═CRbRc, ONRbRc, S(═O)o(═NRb)qRc, SO2NRb(═O)NRbRc, P(═X2)RbRc, OP(═X2)(OpRc)Rb, OP(═X2)(ORc)2, N═CRbRc, NRbN═CRbRc, NRbNRbRc, NRbC(═S)NRbRc, NRbC(═NRb)NRbRc, NRbNRbC(═X2)NRbRc, NRbNRbSO2NRbRc, or N═S(═O)pRcRc, or
• two geminally bound groups R2aa together may form a group selected from ═O, ═S,═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• X2 is independently O or S;
• R4 is each independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, CN, ORc, NRbRc, NO2, C(═O)(O)pRc, OC(═O)(O)pRe, C(═O)NRbRc, OC(═O)NRbRe, NRbC(═O)(O)pRe, NRbC(═O)NRbRc, C(═S)NRbRc, S(O)mRb, SO2NRbRc, OSO2Rc, OSO2NRbRc, NRbSO2Rc, NRbSO2NRbRc, SF5, OCN, SCN, Si(Rd)3, C(═N(O)pRb)Rb, C(═NNRbRc)Rb, C(═NN(C(═O)OpRc)Rb)Rb, ON═CRbRc, ONRbRc, S(═O)o(═NRb)qRc, SO2NRb(═O)NRbRc, P(═X2)RbRc, OP(═X2)(OpRc)Rb, OP(═X2)(ORc)2, N═CRbRc, NRbN═CRbRc, NRbNRbRc, NRbC(═S)NRbRc, NRbC(═NRb)NRbRc, NRbNRbC(═X2)NRbRc, NRbNRbSO2NRbRc, or N═S(═O)pRcRc, or
• two geminally bound groups R4 together may form a group selected from ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• or a stereoisomer, tautomer, salt, or N-oxide thereof.