Cyclic diones as herbicidal compounds

A compound of Formula (I)

• wherein
• R1 is selected from the group consisting of 1-propynyl, phenyl and a 5 or 6 membered heteroaryl which comprises one or two nitrogen heteroatoms, said phenyl and heteroaryl optionally substituted by one or two R15 substituents;
• R2 is methyl, ethyl, methoxy or chloro;
• R3 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
• m is 0 or 1;
• n is 0 or 1;
• R4x is selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxyl, methoxy and halogen;
• R4y is selected from the group consisting of R4a, R4b and R4c:
• R4aa is selected from the group consisting of hydrogen, C1-C6 alkyl and C1-C6alkoxy-;
• R4ab is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, hydroxy-, hydroxyC1-C6alkyl-, C1-C6alkoxy, C3-C6cycloalkyl, —C1-C4alkoxyC1-C6alkyl, —C1-C3alkoxyC1-C6haloalkyl, cyanoC1-C6alkyl-, C(O)R27, S(O)nR27, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• or
• R4aa and R4ab together form —(CH2)q—, —CH2CH2X1CH2CH2— or —C(O)CH2X1CH2CH2— wherein X1 is selected from the group consisting of O, S(O)n and N—R28;
• and
• R4ba is selected from the group consisting of hydrogen, C1-C4 alkyl and C1-C4alkoxy-;
• R4bb is selected from the group consisting of C1-C4alkyl, C1-C4alkoxy-, C1-C4haloalkyl, —C(O)C1-C4alkyl, —C(O)C1-C4haloalkyl, hydroxyC1-C6alkyl-C(O)—, —S(O)nC1-C6alkyl, —S(O)nC1-C6haloalkyl, —S(O)n—(CH2)n—C3-C6cycloalkyl, —S(O)nC(R11)R12R13, —C(O)H, —C(O)—(CH2)n—C3-C6cycloalkyl, —C(O)C(R11)R12R13, —C(O)C2-C4alkenyl, —C(O)(CR9R10)CN, —C(O)(CR9R10)(CR9R10)CN, —C(O)CH2C(O)—C1-C6alkyl, —C(O)CH2OC(O)—C1-C6alkyl, —C(O)OC1-C6alkyl, —C(O)OC1-C6haloalkyl, —C(O)(CH2)nS(O)nC1-C6alkyl, —C(O)C1-C3alkoxyC1-C6alkyl, —C(O)C1-C3alkoxyC2-C6alkenyl, —C(O)C1-C3alkoxyC2-C6alkynyl, —C(O)C1-C3alkoxyC1-C6haloalkyl, —C(O)C1-C3alkoxyC3-C6cycloalkyl, —C(O)OC1-C3alkoxyC1-C6alkyl, —C(O)C1-C3alkoxyC1-C3alkoxyC1-C6alkyl, —C(O)(CH2)nNR5R6, —C(O)—(CH2)n—NR7C(O)R8, —C(O)—(CH2)n—O—N═CR5R5, —CN, —S(O)2NR16R17, —S(O)(═NR18)R19, —C(O)C(O)R20, —C(O)C(R23)═N—O—R24 or —C(O)C(R23)═N—NR25R26, —(CH2)n-phenyl, —C(O)—(CH2)n-phenyl, —S(O)n—(CH2)n—phenyl, -heterocyclyl, —C(O)—(CH2)n-heterocyclyl, —C(O)(CH2)nO—(CH2)n-heterocyclyl, —S(O)n—(CH2)n-heterocyclyl, wherein each heterocyclyl is a 5- or 6-membered heterocyclyl which may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein said heterocyclyl or phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
• R5 is independently selected from the group consisting of hydrogen and C1-C6 alkyl;
• R6 is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, hydroxyl-, C1-C6alkoxy, C3-C6 cycloalkyl, —C1-C4alkoxyC1-C6alkyl, —C1-C3alkoxyC1-C6haloalkyl, —(CR9R10)C1-C6haloalkyl, —(CR9R10)C(O)NR5R5, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• or
• R5 and R6 together form —CH2CH2OCH2CH2—;
• and
• R7 is selected from the group consisting of hydrogen and C1-C6 alkyl;
• R8 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• R9 is hydrogen or methyl;
• R10 is hydrogen or methyl;
• or
• R9 and R10 together form —CH2CH2—;
• and
• R11 is hydrogen or methyl;
• R12 is selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxyl and C1-C6 alkoxy-;
• R13 is selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxyl and C1-C6 alkoxy;
• or
• R12 and R13 together form —CH2—X2—CH2— wherein X2 is selected from the group consisting of O, S and N—R14;
• and
• R14 is selected from the group consisting of hydrogen, C1-C3 alkyl and C1-C3 alkoxy-;
• R15 is independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, cyano and halogen;
• R16 is hydrogen or C1-C6alkyl;
• and
• R17 is selected from the group consisting of hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C1-C6 alkoxy-C1-C3alkyl-, —C(O)C1-C6alkyl, —C(O)OC1-C6alkyl and CH2CN;
• or
• R16 and R17 together form —CH2CH2OCH2CH2—, —CH2CH2S(O)2CH2CH2—;
• and
• R18 is hydrogen or C1-C6alkyl;
• R19 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• R20 is selected from the group consisting of C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy-, C1-C6haloalkoxy, —NR21R22, phenyl and -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• R21 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6alkoxyC1-C3alkyl-, C3-C6 cycloalkyl, C1-C6haloalkyl- and C1-C6haloalkoxy-, —C(O)C1-C6alkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• R22 is hydrogen or C1-C6alkyl;
• or
• R21 and R22 together form —CH2CH2OCH2CH2—;
• and
• R23 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy- and C1-C6haloalkoxy-;
• R24 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C3alkyl-, C3-C6cycloalkyl, —CH2CN, tetrahydropyranyl-, phenyl and -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
• R25 is hydrogen or C1-C6 alkyl;
• R26 is hydrogen or C1-C6 alkyl;
• and
• R4ca is selected from hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, hydroxyl-, C1-C6alkoxy, C3-C6cycloalkyl, —C1-C4alkoxyC1-C6alkyl, —C1-C3alkoxyC1-C6haloalkyl, cyanoC1-C6alkyl-, C(O)R27, S(O)nR27, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• R4cb is selected from the group consisting of hydrogen, C1-C6 alkyl and C1-C6alkoxy-;
• or
• R4ca and R4cb together form —(CH2)q—, —CH2CH2X1CH2CH2— or —C(O)CH2X1CH2CH2— wherein X1 is selected from the group consisting of O, S(O)n and N—R28;
• R27 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6 alkoxy, C3-C6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
• R28 is selected from the group consisting of hydrogen, C1-C3 alkyl, —C(O)C1-C3alkyl and C1-C3 alkoxy-;
• q is 3, 4 or 5;
• and
• G is selected from the group consisting of hydrogen, —(CH2)n—Ra, —C(O)—Ra, —C(O)—(CRcRd)n—O—Rb, —C(O)—(CRcRd)n—S—Rb, —C(O)NRaRa, —S(O)2—Ra and C1-C8alkoxy-C1-C3alkyl-;
• Ra is independently selected from the group consisting of hydrogen, C1-C8alkyl, C1-C3haloalkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
• Rb is selected from the group consisting of C1-C8alkyl, C1-C3haloalkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6 cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
• Rc is hydrogen or C1-C3 alkyl;
• Rd is hydrogen or C1-C3 alkyl;
• and
• n is independently 0, 1 or 2;
• or an agriculturally acceptable salt thereof.