Heterocycle-substituted bicyclic azole pesticides

A compound selected from Formula 1, an N-oxide or salt thereof,

• wherein
• A is CH, CF or N;
• X1 is CR1, and X2 is CR2 or N;
• or X1 is CR2 or N, and X2 is CR1;
• X3 is CR2 or N;
• R1 is a 5- to 10-membered aromatic ring or ring system, each ring or ring system containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 3 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, each ring or ring system being substituted with one R3, and optionally further substituted with 1 to 3 Rx;
• or
• R1 is a 3- to 6-membered partially saturated ring, each ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, each ring being substituted with one R3, and optionally further substituted with at least one Rx;
• each R2 is independently H, halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;
• R3 is selected from the group consisting of
• each R4 is independently H or C1-C4 alkyl;
• each R5 is independently H or C1-C4 alkyl;
• or
• R4 and R5 are taken together with the carbon atom to which they are attached to form a 3- to 6-membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being unsubstituted or substituted with up to 4 Rx;
• provided that R4 and R5 are attached to the same carbon atom;
• p is 1, 2, 3 or 4;
• R6 is H, NR13R14, OR15 or C(═NR8)R9;
• or C1-C6 alkyl substituted with at least one Ry;
• or C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, each unsubstituted or substituted with at least one Rx;
• R6a is OC(═NR8)R9, OC(O)R9, NHC(═NR8)R9, NHC(O)R9, SO2NR13R14, SO2OR15, SO2C(═NR8)R9, C(═NR8)NR13R14, C(O)NR13R4, C(═NR8)OR5 or C(O)OR15;
• or
• R6a is YR6b;
• Y is O, S, NH or C(O);
• R6b is C1-C6 alkyl substituted with at least one Ry;
• or C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, each unsubstituted or substituted with at least one Rx;
• R7 is H, C(O)R17 or S(O)nR18;
• or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl or C2-C6 alkynyl, each unsubstituted or substituted with at least one Rx;
• or phenyl or a 5- or 6-membered heterocyclic aromatic ring, or a 5- or 6-membered heterocyclic non-aromatic ring, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C3-C6 cycloalkoxy and C1-C4 haloalkoxy;
• provided that when R3 is R3b, R3d, R3e or R3f, then both R6 and R7 cannot be H;
• each Rx is independently halogen, cyano, nitro, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C(═NR8)R9, C(O)OR16, C(O)NR13R14, OC(O)R17, NR20R21, NR19C(O)R17, C(O)R17, S(O)nR18, Si(R23)3, OSi(R23)3 or Q;
• each Ry is independently cyano, nitro, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C(═NR8)R9, C(O)OR16, C(O)NR13R14, OC(O)R17, NR20R21, NR19C(O)R17, C(O)R17, S(O)nR18, Si(R23)3, OSi(R23)3 or Q;
• each R8 is independently OR10, S(O)nR11 or NHR2;
• each R9 is independently H;
• or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, each unsubstituted or substituted with at least one Rx;
• or C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkoxy, C(O)OR16, C(O)NR13R14, NR20R21, NR19C(O)R17, C(O)R17 or Q;
• each R10 is independently C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C(O)R17, S(O)nR11 or Q;
• each R11 is independently C1-C4 alkyl or C1-C4 haloalkyl;
• R12 is C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C(O)R17 or C(O)OR16;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R13 is independently H, C1-C6 alkyl, C1-C4 haloalkyl, C1-C4 hydroxyalkyl, C(O)R22 or S(O)2R22;
• or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R14 is independently H, C1-C6 alkyl or C1-C4 haloalkyl;
• or
• R13 and R14 are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• R15 is C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkoxy or C1-C4 haloalkyl;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R16 is independently H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R17 is independently C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R18 is independently C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylalkyl or C3-C6 halocycloalkylalkyl;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R19 is independently H or C1-C4 alkyl;
• each R20 is independently H, C1-C4 alkyl or C1-C4 haloalkyl;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R21 is independently H, C1-C4 alkyl or C1-C4 haloalkyl;
• or phenyl, unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• or
• R20 and R21 are independently taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R22 is independently C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or NR24R25;
• or phenyl or a 5- or 6-membered heterocyclic aromatic ring, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R23 is independently C1-C6 alkyl, C3-C6 cycloalkyl or phenyl;
• each R24 is independently H or Q;
• or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each R25 is independently H or Q;
• or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• or
• R24 and R25 are taken together with the nitrogen atom to which they are attached to form a 3- to 10-membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being unsubstituted or substituted with up to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• each Q is independently phenyl, a 5- or 6-membered heterocyclic aromatic ring or a 3- to 6-membered heterocyclic non-aromatic ring, each ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one oxygen atom, one sulfur atom, and up to 2 nitrogen atoms, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O)2, each ring unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy;
• and
• each n is independently 0, 1 or 2.