Herbicidal compounds

A compound of Formula (I) or an agronomically acceptable salt or zwitterionic species thereof:

• wherein
• R1 is selected from the group consisting of hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6haloalkyl, —OR7, —OR15a, —N(R6)S(O)2R15, —N(R6)C(O)R15, —N(R6)C(O)OR15, —N(R6)C(O)NR16R17, —N(R6)CHO, —N(R7a)2 and —S(O)rR15;
• R2 is selected from the group consisting of hydrogen, halogen, C1-C6alkyl and C1-C6haloalkyl;
• and wherein when R1 is selected from the group consisting of —OR7, —OR15a, —N(R6)S(O)2R15, —N(R6)C(O)R15, —N(R6)C(O)OR15, —N(R6)C(O)NR16R17, —N(R6)CHO, —N(R7a)2 and —S(O)rR15, R2 is selected from the group consisting of hydrogen and C1-C6alkyl;
• or
• R1 and R2 together with the carbon atom to which they are attached form a C3-C6cycloalkyl ring or a 3- to 6-membered heterocyclyl, which comprises 1 or 2 heteroatoms individually selected from N and O;
• Q is (CR1aR2b)m,
• m is 0, 1, 2 or 3;
• each R1a and R2b are independently selected from the group consisting of hydrogen, halogen, C1-C6alkyl, C1-C6haloalkyl, —OH, —OR7, —OR15a, —NH2, —NHR7, —NHR15a, —N(R6)CHO, —NR7bR7c and —S(O)rR15;
• or
• each R1a and R2b together with the carbon atom to which they are attached form a C3-C6cycloalkyl ring or a 3- to 6-membered heterocyclyl, which comprises 1 or 2 heteroatoms individually selected from N and O;
• and
• R3, R4 and R5 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, —S(O)rR15, C1-C6alkyl, C1-C6fluoroalkyl, C1-C6fluoroalkoxy, C1-C6alkoxy, C3-C6cycloalkyl and —N(R6)2;
• each R6 is independently selected from hydrogen and C1-C6alkyl;
• each R7 is independently selected from the group consisting of C1-C6alkyl, —S(O)2R15, —C(O)R15, —C(O)OR15 and —C(O)NR16R17;
• each R7a is independently selected from the group consisting of —S(O)2R15, —C(O)R15, —C(O)OR15—C(O)NR16R17 and —C(O)NR6R15a;
• R7b and R7c are independently selected from the group consisting of C1-C6alkyl, —S(O)2R15, —C(O)R15, —C(O)OR15, —C(O)NR16R17 and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• or
• R7b and R7c together with the nitrogen atom to which they are attached form a 4- to 6-membered heterocyclyl ring which optionally comprises one additional heteroatom individually selected from N, O and S;
• and
• A is a 6-membered heteroaryl, which comprises 1, 2, 3 or 4 nitrogen atoms and wherein the heteroaryl may be optionally substituted by 1, 2, 3 or 4 R8 substituents, which may be the same or different,
• and wherein when A is substituted by 1 or 2 substituents, each R8 is independently selected from the group consisting of halogen, nitro, cyano, —NH2, —NHR7, —N(R7)2, —OH, —OR7, —S(O)rR15, —NR6S(O)2R15, —C(O)OR10, —C(O)R15, —C(O)NR16R17, —S(O)2NR16R17, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6cycloalkoxy, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C1-C3alkoxyC1-C3alkyl-, hydroxyC1-C6alkyl-, C1-C3alkoxyC1-C3alkoxy-, C1-C6haloalkoxy, C1-C3haloalkoxyC1-C3alkyl-, C3-C6alkenyloxy, C3-C6alkynyloxy, N—C3-C6cycloalkylamino, —C(R6)═NOR6, phenyl, a 3- to 6-membered heterocyclyl, which comprises 1 or 2 heteroatoms individually selected from N and O, and a 5- or 6-membered heteroaryl, which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein said phenyl, heterocyclyl or heteroaryl are optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• and wherein when A is substituted by 3 or 4 substituents, each R8 is independently selected from the group consisting of halogen, —NH2, —NHR7, —N(R7)2, —OH, —OR7, —C(O)NR16R17, —S(O)2NR16R17, C1-C6alkyl and C1-C6haloalkyl;
• and
• each R9 is independently selected from the group consisting of halogen, cyano, —OH, —N(R6)2, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl and C1-C4haloalkoxy;
• X is selected from the group consisting of C3-C6cycloalkyl, phenyl, a 5- or 6-membered heteroaryl, which comprises 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and a 4- to 6-membered heterocyclyl, which comprises 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein said cycloalkyl, phenyl, heteroaryl or heterocyclyl moieties are optionally substituted by 1 or 2 R9 substituents, and wherein the aforementioned CR1R2, Q and Z moieties may be attached at any position of said cycloalkyl, phenyl, heteroaryl or heterocyclyl moieties;
• n is 0 or 1;
• Z is selected from the group consisting of —C(O)OR10, —CH2OH, —CHO, —C(O)NHOR11, —C(O)NHCN, —OC(O)NHOR11, —OC(O)NHCN, —NR6C(O)NHOR11, —NR6C(O)NHCN, —C(O)NHS(O)2R12, —OC(O)NHS(O)2R12, —NR6C(O)NHS(O)2R12, —S(O)2OR10, —OS(O)2OR10, —NR6S(O)2OR10, —NR6S(O)OR10, —NHS(O)2R14, —S(O)OR10, —OS(O)OR10, —S(O)2NHCN, —S(O)2NHC(O)R18, —S(O)2NHS(O)2R12, —OS(O)2NHCN, —OS(O)2NHS(O)2R12, —OS(O)2NHC(O)R18, —NR6S(O)2NHCN, —NR6S(O)2NHC(O)R18, —N(OH)C(O)R15, —ONHC(O)R15, —NR6S(O)2NHS(O)2R12, —P(O)(R13)(OR10), —P(O)H(OR10), —OP(O)(R13)(OR10), —NR6P(O)(R13)(OR10) and tetrazole;
• R10 is selected from the group consisting of hydrogen, C1-C6alkyl, phenyl and benzyl, and wherein said phenyl or benzyl are optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• R11 is selected from the group consisting of hydrogen, C1-C6alkyl and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• R12 is selected from the group consisting of C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, —OH, —N(R6)2 and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• R13 is selected from the group consisting of —OH, C1-C6alkyl, C1-C6alkoxy and phenyl;
• R14 is C1-C6haloalkyl;
• R15 is selected from the group consisting of C1-C6alkyl and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• R15a is phenyl, wherein said phenyl is optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• R16 and R17 are independently selected from the group consisting of hydrogen and C1-C6alkyl;
• or
• R16 and R17 together with the nitrogen atom to which they are attached form a 4- to 6-membered heterocyclyl ring which optionally comprises one additional heteroatom individually selected from N, O and S;
• and
• R18 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, —N(R6)2 and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R9 substituents, which may be the same or different;
• and
• r is 0, 1 or 2.