Substituted Pyrimidinium Compounds and Derivatives for Combating Animal Pests

A compound of formula (I)

• wherein
• X, Y are each independently O or S;
• Z is selected from the group consisting of a direct bond, O, S(O)m, NRb, C(RaRaa)O, C(═X1), C(═X1)Y1, and Y1C(═X1);
• X1 is selected from the group consisting of O, S, and NRb;
• Y1 is selected from the group consisting of O, S, and NRc;
• A is CH, 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 a carbon atom, wherein each ring member may be substituted with up to 3 Ra;
• Het is selected from any one of the following ring systems D-1 to D-56:
• where # denotes the bond to A in formula (I);
• R1 is selected from the group consisting of hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl, C4-C10-cycloalkenyl, and 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 the group consisting of 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 by Ra;
• or
• R1 is selected from the group consisting of C(═O)Rb, C(═O)ORe, NRbRc, (═O)NRbRc, C(═S)NRbRc, SO2NRbRc, OC(═O)Rc, OC(═O)ORe, OC(═O)NRbRc, 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 and N═CRbRc;
• Ra is each independently selected from the group consisting of 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, NRb SO2NRbRc, N═S(═O)pRcRc, S(═O)o(═NRb)qRc, SF5, OCN, SCN, Si(Rd)3 and a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from the group consisting of 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 by Raa, or
• two geminally bound groups Ra together may form a group selected from the group consisting of ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• Raa is each independently selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
• Rb is each independently selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy and a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from the group consisting of N(Rc)p, O, and S, wherein S may be oxidized and which carbo- or heterocyclic ring may be partially or fully substituted by Raa;
• Rc is each independently selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C6 cycloalkyl, and a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from the group consisting of N(Raa)p, O and S, wherein S may be oxidized and wherein the carbo- or heterocyclic ring may be partially or fully substituted by 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 the group consisting of N, O, S, NO, SO and SO2 and wherein the carbo- or heterocyclic ring may be partially or fully substituted by R3;
• Rd is each independently selected from the group consisting of hydrogen, phenyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, and C1-C6-alkoxyalkyl, wherein the above mentioned groups may be substituted by one or more halogen;
• Re is each independently selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C6 cycloalkyl, and a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from the group consisting of N(Raa)p, O and S, wherein S may be oxidized and wherein the carbo- or heterocyclic ring may be partially or fully substituted by Raa;
• n is 0, 1 or 2;
• m is 0, 1, or 2;
• p is 0 or 1;
• R2 is selected from the group consisting of 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, and 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 the group consisting of 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 by R2a;
• with the proviso that if R2 is halogen or CN, then Z is a direct bond;
• R2a is each independently selected from the group consisting of 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)pRc, C(═O)NRbRc, OC(═O)NRbRe, NRbC(═O)(O)pRe, NRbRc (═O)NRbRc, C(═S)NRbRc, S(O)mRb, SO2NRbRc, OSO2Rc, OSO2NRbRc, NRb SO2Rc, NRb SO2NRbRc, 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, NRbNRbRcNRbC(═S)NRbRc, NRbC(═NR)NRbRc, NRbNRbC(═X2)NRbRc, NRbNRbSO2NRbRc, N═S(═O)pRcRc, and a three- to six-membered saturated, or partially unsaturated or aromatic carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms selected from the group consisting of 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 by R2aa or
• two geminally bound groups R2a together may form a group selected from the group consisting of ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• R2aa is each independently selected from the group consisting of 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)pRc, C(═O)NRbRc, OC(═O)NRbRe, NRbC(═O)(O)pRc, 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, and N═S(═O)pRcRc or
• two geminally bound groups R2aa together may form a group selected from the group consisting of ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• X2 is independently O or S;
• R3 is each independently selected from the group consisting of 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)pRc, 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, and N═S(═O)pRcRc or
• two geminally bound groups R3 together may form a group selected from the group consisting of ═O, ═S, ═CRbRc, ═NRc, ═NORc, and ═NNRcRc;
• and/or stereoisomers or agriculturally or veterinary acceptable salts or tautomers or N-oxides thereof.