Cinnolinium compounds for use in a method of controlling unwanted plant growth

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 is selected from the group consisting of hydrogen, halogen, cyano, nitro, —S(O)rR15, C1-C6alkyl, C1-C6halooalkyl, C1-C6haloalkoxy, C1-C6alkoxy, C3-C6cycloalkyl, —N(R6)2, phenyl, a 5- or 6-membered heteroaryl comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and a 4- to 6-membered heterocyclyl comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein said phenyl, heteroaryl or heterocyclyl moieties are optionally substituted by 1 or 2 R9 substituents;
• A is selected from the group consisting of:
• —C(O)OR410, —CHO, —C(O)R424, —C(O)NHOR411, —C(O)NHCN, —C(O)NHR425, —S(O)2NHR425, —C(O)NHS(O)2R414, —C(O)NR46(CR462)q—C(O)OR410, —C(O)NR46(CR462)qS(O)2OR410, —C(O)NR46(CR462)qP(O)(R413)OR410, —C(O)NR46S(O)2(CR462)qC(O)OR410—(CR462)qC(O)OR410, —(CR462)qS(O)2OR410, —(CR462)qP(O)(R413)(OR410), —OC(O)NHOR411—O(CR462)qC(O)OR410, —OC(O)NHCN, —O(CR462)qS(O)2OR410—O(CR462)qP(O)(R413)(OR410), —NR46C(O)NHOR411, —NR46C(O)NHCN, —C(O)NHS(O)2R412, —OC(O)NHS(O)2R412, —NR46C(O)NHS(O)2R412, —S(O)2OR410, —OS(O)2OR410, —NR46S(O)2OR410, —NR46S(O)OR410, —NHS(O)2R414, —S(O)OR410, —S(CR462)qC(O)OR410, —S(CR462)qS(O)2OR410, —S(CR462)qP(O)(R413)(OR410), —OS(O)2OR410—S(O)2NHCN, —S(O)2NHC(O)R418, —S(O)2NHS(O)2R412, —OS(O)2NHCN, —OS(O)2NHS(O)2R412, —OS(O)2NHC(O)R418, —NR46S(O)2NHCN, —NR46S(O)2NHC(O)R418, —N(OH)C(O)R415—ONHC(O)R415—NR46S(O)2NHS(O)2R412, —P(O)(R413)(OR410), —P(O)H(OR410), —OP(O)(R413)(OR410), —NR46P(O)(R413)(OR410) and tetrazole;
• each R46 is independently selected from hydrogen and C1-C6alkyl;
• each R49 is independently selected from the group consisting of halogen, cyano, —OH, —N(R46)2, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl and C1-C4haloalkoxy;
• R410 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 R49 substituents, which may be the same or different;
• R411 is selected from the group consisting of hydrogen, C1-C6alkyl, —C(O)OR410, and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R49 substituents, which may be the same or different;
• R412 is selected from the group consisting of C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, C1-C6alkoxy, —OH, —N(R46)2, phenyl, a 5- or 6-membered heteroaryl comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and a 4- to 6-membered heterocyclyl comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein said phenyl, heteroaryl or heterocyclyl moieties are optionally substituted by 1 or 2 R420 substituents;
• R413 is selected from the group consisting of —OH, C1-C6alkyl, C1-C6alkoxy and phenyl;
• R414 is selected from the group consisting of C1-C6alkyl, C1-C6haloalkyl, and N(R46)2;
• R415 is selected from the group consisting of C1-C6alkyl and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R49 substituents, which may be the same or different;
• R418 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, —N(R46)2 and phenyl, and wherein said phenyl is optionally substituted by 1, 2 or 3 R49 substituents, which may be the same or different;
• each R420 is independently C1-C6 alkyl, C1-C6alkoxy, halogen, C1-C6haloalkyl, C1-C6haloalkoxy, or C1-C3alkoxyC1-C3alkyl;
• R424 is a peptide moiety comprising 1, 2, or 3 amino acid moieties, each amino acid moiety independently selected from the group consisting of Ala, Cys, Asp, Glu, Phe, Gly, His, Ile, Lys, Leu, Met, Asn, Pro, Gln, Arg, Ser, Thr, Val, Trp and Tyr, wherein said peptide moiety is bonded to the rest of the molecule via a nitrogen atom in the amino acid moiety;
• R425 is phenyl optionally substituted by 1 or 2 R49 substituents, or a 5- or 6-membered heteroaryl comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S and optionally substituted by 1 or 2 R49 substituents;
• q is an integer of 1, 2, or 3;
• each R5 is 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;
• k is an integer of 0, 1, 2, 3, or 4;
• 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;
• 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;
• 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;
• Z is selected from the group consisting of hydrogen, methoxy, —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, —NRS(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)(OR1), —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,
• with the proviso that:
• (i) when A is —P(O)(OH)(OR410) and R410 is C1-C6alkyl, and R1 and R2 are both hydrogen, m is 0, and n is 0, then Z is not hydrogen, and
• (ii) the compound of formula (I) is not methyl 2,3-dimethylcinnolin-2-ium-4-carboxylate.