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US 11,980,188 B2Granted
Spiro cyclohexanedione derivates as herbicides
AssigneeSyngenta Participations AG
InventorsAlan Joseph Hennessy, Elizabeth Pearl Jones, Shuji Hachisu, Nigel James Willetts, Suzanna Dale, Alexander William Gregory, Ian Thomas Tinmouth Houlsby, Yunas Bhonoah, Julia Comas-Barcelo
Life of this patent
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Abstract
The present invention relates to compounds of Formula (I), wherein R1, R2, R3, R4 and G are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds, in particular in crops of useful plants.
Claims15
A compound of Formula (I)
- wherein
- R1 is selected from methyl, 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 or methoxy;
- R3 is methyl or methoxy;
- R4 is selected from the group consisting of C1-C4alkyl, C1-C4alkoxy-, C1-C4haloalkyl, —C(═O)C1-C4alkyl, —C(═O)C1-C4haloalkyl, —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, —(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 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-C6 alkoxy, 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—X—CH2—;
- and
- X is selected from the group consisting of O, S and N—R14;
- 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;
- 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.
31 more elements
A compound selected from:
Dependencies are inferred from the claim text.