Substituted pyridazinones as herbicides.

Abstract

To provide: herbicidal substituted phenyl-pyridazine-diones and substituted phenyl-pyridazinone derivatives of formula (I); and processes and intermediates used for the preparation of such derivatives.SOLUTION: The present invention relates to: herbicidal substituted phenyl-pyridazine-diones and substituted phenyl-pyridazinone derivatives of formula (I); and processes and intermediates used for the preparation of such derivatives. The invention further provides: herbicidal compositions comprising such derivatives; and the use of such compounds and compositions in controlling undesirable plant growth, in particular the use in controlling weeds, such as broad-leaved dicotyledonous weeds, in crops of useful plants.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to herbicidal substituted phenyl-pyridazine-dione and substituted phenyl-pyridazinone derivatives of formula (I), as well as processes and intermediates used in the preparation of such derivatives. The invention further extends to herbicidal compositions containing such derivatives, and the use of such compounds and compositions in the control of undesirable plant growth, particularly in the control of weeds, such as broadleaf dicotyledonous weeds, in crops of useful plants. [Background technology]

[0002] Herbicidal pyridazinones are known from WO 2009 / 086041. Furthermore, herbicidal 5 / 6-membered heterocyclyl-substituted pyridazinones are known from WO 2011 / 045271. Meanwhile, WO 2013 / 160126 describes indolyl-pyridazinone derivatives that exhibit herbicidal activity. Summary of the Invention [Means for solving the problem]

[0003] The present invention is based on the discovery of substituted phenyl-pyridazine-dione and substituted phenyl-pyridazinone derivatives of formula (I) which exhibit unexpectedly good herbicidal activity.

[0004] Thus, in a first aspect, a compound of formula (I) [ka] or a salt or N-oxide thereof, wherein: R 1 is selected from the group consisting of C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 alkoxy, C1-C2 alkoxy-C1-C2 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, cyano-C1-C4 alkyl, C2-C4 haloalkenyl, C2-C4 alkynyl, and C2-C4 haloalkynyl; R 2 is hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C6 alkoxy, C1-C3 alkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, -S(O) m selected from the group consisting of C1-C6 alkyl, amino, C1-C6 alkylamino, C1-C6 dialkylamino, -C(C1-C3 alkyl)=NO-C1-C3 alkyl, and C2-C6 haloalkynyl; G is hydrogen or C(O)R 3 and; R 3 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl-S-, C1-C6 alkoxy, -NR 4 R 5 and one or more R 6 phenyl optionally substituted with; Each R 4 and R 5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, and C3-C6 cycloalkyl, or R 4 and R 5 together can form a morpholinyl ring; Each R 4a and R 5a are independently selected from the group consisting of C1-C6 alkoxy and C3-C6 cycloalkyl, or R 4a and R 5a together can form a morpholinyl ring; R 6 is selected from the group consisting of halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy; X and Y are each independently hydrogen, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or halogen; D is R on at least one ring carbon atom 8 and / or substituted on at least one ring nitrogen atom with R 9 a substituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, substituted with At least one R 8 is C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, -NR 4a R 5a , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5, C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1-C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; and ring systems selected from the group consisting of phenyl rings, 5- to 6-membered heteroaryl rings, and 3- to 6-membered heterocyclyl rings, said ring systems being selected from the group consisting of 0-5 R 16 is replaced by; At least one R 9 is C5-C6 alkyl, C5-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C3 alkyl-, C3 alkoxy-C1-C2 alkyl-, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C-C cycloalkyl, cyano-C-C alkyl-, and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 is replaced by; m is an integer of 0, 1, or 2; Each R 16 are independently halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; Or D is at least one R 8 is a phenyl ring substituted with; W is [ka] where: "a" represents the point of attachment to the phenyl-pyridazinedione / phenyl-pyridazinone moiety; "b" represents the attachment point to ring D, R 10 , R 12 , R 14 and R 15 are each independently hydrogen, C1-C3 alkyl, or C1-C3 haloalkyl; Or R 10 and R 12 form, together with the carbon atoms to which they are attached, a C3-C6 carbocyclic ring; R 11 and R 13 are each independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl; However, R 11 or R 13 When one of is halogen, C1-C3 alkyl, or C1-C3 haloalkyl, the other is hydrogen.

[0005] In a second aspect, a compound of formula (I) [ka] or a salt or N-oxide thereof, wherein: R 1 is selected from the group consisting of C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 alkoxy, C1-C2 alkoxy-C1-C2 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, cyano-C1-C4 alkyl, C2-C4 haloalkenyl, C2-C4 alkynyl, and C2-C4 haloalkynyl; R 2is hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C6 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, -S(O) m C1-C6 alkyl, -NR 4 R 5 , —C(C1-C3 alkyl)═NO—C1-C3 alkyl, and C2-C6 haloalkynyl; G is hydrogen or C(O)R 3 and; R 3 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl-S-, C1-C6 alkoxy, -NR 4 R 5 and one or more R 6 phenyl optionally substituted with; Each R 4 and R 5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, and C3-C6 cycloalkyl, or R 4 and R 5 together can form a morpholinyl ring; R 6 is selected from the group consisting of halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy; X is cyclopropyl (preferably X is ortho relative to the pyridazinone / pyridazinedione moiety); Y is hydrogen, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or halogen (Y is ortho (3-position) relative to the -WD moiety); D is a substituted or unsubstituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, and when D is substituted, it is substituted with R on at least one ring carbon atom. 8 and / or substituted on the ring nitrogen atom with R 9 is replaced by; Each R 8 are independently oxygen, hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR 4 R 5 , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5, C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1-C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 is replaced by; m is an integer of 0, 1, or 2 (preferably 0 or 2); Each R 9 are independently C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0 to 5 R 16 is replaced by; Each R 16 are independently halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; Alternatively, D is a substituted or unsubstituted phenyl ring, and when said phenyl ring is substituted, it is selected from 1 to 5 R 8 is replaced by; W is [ka] where: "a" represents the point of attachment to the phenyl-pyridazinedione / phenyl-pyridazinone moiety; "b" represents the attachment point to ring D, R 10 , R 12 , R 14 and R 15 are each independently hydrogen, C1-C3 alkyl, or C1-C3 haloalkyl; Or R 10 and R 12 form, together with the carbon atoms to which they are attached, a C3-C6 carbocyclic ring; R 11 and R 13 are each independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl; However, R 11 or R 13 When one of is halogen, C1-C3 alkyl, or C1-C3 haloalkyl, the other is hydrogen.

[0006] In a third aspect, a compound of formula (I) [ka] or a salt or N-oxide thereof, wherein: R 1 is selected from the group consisting of C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 alkoxy, C1-C2 alkoxy-C1-C2 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, cyano-C1-C4 alkyl, C2-C4 haloalkenyl, C2-C4 alkynyl, and C2-C4 haloalkynyl; R 2is hydrogen, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C6 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, -S(O) m C1-C6 alkyl, -NR 4 R 5 , —C(C1-C3 alkyl)═NO—C1-C3 alkyl, and C2-C6 haloalkynyl; G is hydrogen or C(O)R 3 and; R 3 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl-S-, C1-C6 alkoxy, -NR 4 R 5 and one or more R 6 phenyl optionally substituted with; Each R 4 and R 5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, and C3-C6 cycloalkyl, or R 4 and R 5 together can form a morpholinyl ring; R 6 is selected from the group consisting of halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy; X is hydrogen, C1-C3 alkyl, cyclopropyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or halogen (preferably, X is ortho relative to the pyridazinone / pyridazinedione moiety); Y is cyclopropyl (preferably Y is ortho relative to the -WD moiety); D is a substituted or unsubstituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, and when D is substituted, it is substituted with R on at least one ring carbon atom. 8 and / or substituted on the ring nitrogen atom with R 9 is replaced by; Each R 8 are independently oxygen, hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR 4 R 5 , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5, C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1-C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 is replaced by; m is an integer of 0, 1, or 2; Each R 9 are independently C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0 to 5 R 16 is replaced by; Each R 16 are independently halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; Alternatively, D is a substituted or unsubstituted phenyl ring, and when said phenyl ring is substituted, it is selected from 1 to 5 R 8 is replaced by; W is [ka] where: "a" represents the point of attachment to the phenyl-pyridazinedione / phenyl-pyridazinone moiety; "b" represents the attachment point to ring D, R 10 , R 12 , R 14 and R 15 are each independently hydrogen, C1-C3 alkyl, or C1-C3 haloalkyl; Or R 10 and R 12 form, together with the carbon atoms to which they are attached, a C3-C6 carbocyclic ring; R 11 and R 13 are each independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl; However, R 11 or R 13 When one of is halogen, C1-C3 alkyl, or C1-C3 haloalkyl, the other is hydrogen.

[0007] The compounds of formula (I) may contain asymmetric centers and may exist as single enantiomers, pairs of enantiomers in any ratio, or, if two or more asymmetric centers are present, all possible ratios of diastereoisomers. Typically, one of the enantiomers has improved biological activity compared to the other possible enantiomers.

[0008] Similarly, when disubstituted alkenes are present, they may exist in the E or Z configuration or as a mixture of both in any proportion.

[0009] Furthermore, compounds of formula (I) may be in equilibrium with other tautomers. For example, compounds of formula (Ii), i.e., compounds of formula (I) (wherein R 2 is hydrogen and G is hydrogen) can be depicted as at least three tautomers: [ka]

[0010] It should be understood that all tautomers (single tautomers or mixtures thereof), racemic mixtures and single isomers are included within the scope of the present invention.

[0011] Each alkyl moiety, alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, or dialkylaminocarbonyl), can be straight-chain or branched. Typically, alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, or n-hexyl. Alkyl groups are generally C1-C6 alkyl groups (unless defined more narrowly above), but are preferably C1-C4 alkyl or C1-C3 alkyl groups, and more preferably C1-C2 alkyl groups (such as methyl).

[0012] The alkenyl and alkynyl moieties may be in the form of straight or branched chains, and the alkenyl moieties may be of either the (E)- or (Z)-configuration, as appropriate. The alkenyl or alkynyl moiety is typically a C2-C4 alkenyl or a C2-C4 alkynyl, more particularly vinyl, allyl, ethynyl, propargyl, or prop-1-ynyl. The alkenyl and alkynyl moieties may contain one or more double and / or triple bonds in any combination; preferably, they contain only one double bond (in the case of an alkenyl) or only one triple bond (in the case of an alkynyl).

[0013] Preferably, the term cycloalkyl refers to cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0014] In the present context, the term "aryl" preferably refers to phenyl. The term "heteroaryl," as used herein, refers to an aromatic ring system containing at least one ring heteroatom and consisting of a single ring. Preferably, the single ring contains 1, 2, or 3 ring heteroatoms independently selected from nitrogen, oxygen, and sulfur. Typically, "heteroaryl" is furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, or 1,3,5-triazinyl.

[0015] Heterocyclyl groups and heterocyclic rings (alone or as part of a larger group, e.g., heterocyclyl-alkyl-) are ring systems containing at least one heteroatom and may be monocyclic or bicyclic. Preferably, heterocyclyl groups contain up to two heteroatoms, preferably selected from nitrogen, oxygen, and sulfur. Examples of heterocyclic groups include oxetanyl, thietanyl, azetidinyl, and 7-oxa-bicyclo[2.2.1]hept-2-yl. Heterocyclyl groups containing a single oxygen atom as the heteroatom are most preferred. Heterocyclyl groups are preferably 3- to 8-membered, more preferably 3- to 6-membered, monocyclic rings, which may be fully or partially saturated.

[0016] Halogen (or halo) includes fluorine, chlorine, bromine or iodine. Correspondingly, the same applies to halogen in the context of other definitions such as haloalkyl or halophenyl.

[0017] Haloalkyl groups having a chain length of 1 to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, heptafluoro-n-propyl and perfluoro-n-hexyl.

[0018] The alkoxy group preferably has a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy or pentyloxy or hexyloxy isomers, preferably methoxy and ethoxy. It should also be understood that two alkoxy substituents may be present on the same carbon atom.

[0019] Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy or 2,2,2-trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.

[0020] C1 to C6 alkyl-S-(alkylthio) is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.

[0021] C1-C6 alkyl-S(O)-(alkylsulfinyl) is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

[0022] C1-C6 alkyl-S(O)2-(alkylsulfonyl) is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

[0023] base Q [ka] is referred to herein as a pyridazinedione / pyridazinone moiety, where B indicates the point of attachment to the remainder of the molecule (ie, the optionally substituted phenyl WD moiety).

[0024] The present invention also includes agriculturally acceptable salts that the compounds of formula (I) can form with amines (e.g., ammonia, dimethylamine, and triethylamine), alkali metal and alkaline earth metal bases, or quaternary ammonium bases. Among the hydroxides, oxides, alkoxides, and bicarbonates and carbonates of alkali metals and alkaline earth metals used as salt formers, emphasis is placed on the hydroxides, alkoxides, oxides, and carbonates of lithium, sodium, potassium, magnesium, and calcium, with particular emphasis on the hydroxides, alkoxides, oxides, and carbonates of sodium, magnesium, and calcium. The corresponding trimethylsulfonium salts can also be used. The compounds of formula (I) according to the present invention also include hydrates that can be formed during salt formation. DETAILED DESCRIPTION OF THE INVENTION

[0025] R1 , R 2 , R 3 , R 4 , R 5 , R 4a , R 5a , R 6 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 Preferred values ​​for W, D, Dp, G, X, Y, and m are as described below, and the compounds of formula (I) according to the present invention may include any combination of said values. Those skilled in the art will understand that any given set of values ​​of an embodiment may be combined with any other set of values ​​of an embodiment, provided that the combinations are not mutually exclusive.

[0026] Preferably, R 1 is selected from the group consisting of methyl, ethyl, propyl (especially n- or c-propyl), propargyl or C1 haloalkyl. More preferably, R 1 is methyl, ethyl, cyclopropyl, propargyl or C1 fluoroalkyl. Even more preferably, R 1 is methyl, ethyl, cyclopropyl or propargyl. Most preferably, R 1 is methyl.

[0027] Preferably, R 2 is selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C3 alkoxy-C1-C3 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, and C2-C6 haloalkynyl. More preferably, R 2is selected from the group consisting of chloro, fluoro, methyl, ethyl, cyclopropyl, trifluoromethyl and methoxymethyl, even more preferably chloro, cyclopropyl, trifluoromethyl or methyl, most preferably chloro or methyl. In one set of embodiments of the present invention, R 2 is hydrogen. In a further set of embodiments, R 2 is cyclopropyl, and in a third set of embodiments, R 2 is methyl, and in a fourth set of embodiments, R 2 is trifluoromethyl, and in a fifth set of embodiments, R 2 is chloro.

[0028] As described herein, G is hydrogen or —C(O)—R 3 R 3 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl-S-, C1-C6 alkoxy, -NR 4 R 5 and one or more R 6 phenyl optionally substituted with

[0029] As defined herein, R 4 and R 5 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy-, and C3-C6 cycloalkyl; or they can be taken together to form a morpholinyl ring. The substituents G (and also R 3 ) in the situation, R 4 and R 5 are preferably each independently selected from the group consisting of methyl, ethyl, propyl, methoxy, ethoxy and propoxy, and each R 34 and R 35 Other substituents (e.g., R 2 , R 8 ) in the situation, R 4 and R 5are preferably each independently hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or C3-C6 cycloalkyl, and each R 84 and R 85 It can be called a plurality of R 4 is a larger moiety, e.g., the group -NR 4 C(O)NR 4 R 5 If included in each R 4 are independent, so in such a part, two R 4 One skilled in the art will recognize that the groups can be the same or they can be different from one another.

[0030] R 6 is selected from the group consisting of halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy. 6 is selected from the group consisting of halogen, C1-C3 alkyl, and C1-C3 haloalkyl.

[0031] Preferably, R 3 is C1-C4 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, -C1-C4 alkoxy, -NR 4 R 5 and R 4 and R 5 together form a morpholinyl ring, or phenyl. More preferably, R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy. More preferably, R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, or methoxy.

[0032] In one set of embodiments, G is hydrogen or —C(O)—R 3 where R 3 is C1-C4 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, or -C1-C4 alkoxy. In a further set of embodiments, G is hydrogen or -C(O)-R 3where R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl or methoxy. However, G is hydrogen or -C(O)-R 3 where R 3 However, isopropyl is particularly preferred.

[0033] When Y is cyclopropyl, X is preferably hydrogen, cyclopropyl, halogen, or C1 haloalkyl, more preferably hydrogen, fluoro, chloro, bromo, or C1 fluoroalkyl, more preferably also hydrogen, fluoro, chloro, or trifluoromethyl. Most preferably, when Y is cyclopropyl, X is fluoro. In one set of embodiments, X is preferably ortho (6-position) relative to the pyridazinone / pyridazinedione moiety (group Q). It is particularly preferred that X is fluoro, chloro, or C1-haloalkyl (particularly C1 fluoroalkyl) and ortho (6-position) relative to the pyridazinone / pyridazinedione moiety (group Q). Most preferably, X is fluoro and ortho (6-position) relative to the pyridazinone / pyridazinedione moiety (group Q).

[0034] When X is cyclopropyl, in such embodiments, Y is preferably hydrogen, C1-C3 alkyl, cyclopropyl, C1-C3 haloalkyl, or halogen, more preferably Y is hydrogen, chloro, fluoro, or bromo. Most preferably, when X is cyclopropyl, Y is chloro.

[0035] In one set of embodiments, it is preferred that Y is ortho (position 3) to the WD moiety. In a further set of embodiments, Y is para to the pyridazinone / pyridazine-dione moiety (group Q).

[0036] It is especially preferred that Y is ortho (3-position) to the WD moiety and is halogen, especially chloro or fluoro; more preferably chloro.

[0037] As described herein, D is a substituted or unsubstituted phenyl ring (Dp) or a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, and when D is a substituted heteroaryl ring or a substituted phenyl ring, it is substituted with R on at least one ring carbon atom. 8 and / or, in the case of heteroaryl rings, substituted on the ring nitrogen atom by R 9 When D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring, it is preferably a substituted (as described herein) or unsubstituted furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, or 1,3,5-triazinyl ring.

[0038] In such embodiments, D is preferably a substituted (as described herein) or unsubstituted pyridyl, pyrazolyl, thiazolyl, pyrimidinyl, thienyl, triazolyl, or oxadiazolyl ring, more preferably a pyridyl ring.

[0039] In one set of embodiments, D is a substituted (as described herein) or unsubstituted pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, or pyrazinyl ring.

[0040] In a further set of such embodiments, D is a substituted (as described herein) or unsubstituted oxazolyl, thiazolyl, or pyridyl ring. In certain embodiments, D is a substituted or unsubstituted pyridyl ring, or a substituted or unsubstituted thiazolyl ring.

[0041] R 8 The substitution of D by is determined by the presence or absence of cyclopropyl at positions X and / or Y. However, in general, when D is a substituted 5- or 6-membered heteroaryl ring, it is preferably substituted by one or two R 8 and / or 1 R 9 , more preferably one or two R 8 When D is a 5-membered substituted heteroaryl ring, it is most preferably substituted with one R 8 When D is a substituted phenyl ring, it is preferably substituted with one or two R 8 , more preferably one R 8 is replaced by .

[0042] When at least one of X and Y is cyclopropyl and D is substituted, each R 8 is hydrogen, oxygen, hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O)m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR 4 R 5 , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, -NR 4 C(O)NR 4 R 5 , C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1-C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is independently selected from the group consisting of 0 to 5 R 16 is replaced by; m is an integer of 0, 1, or 2 (preferably 0 or 2); 9are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0 to 5 R 16 is replaced by; Each R 16 are independently halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy.

[0043] When both X and Y are other than cyclopropyl and D is a phenyl ring, D is preferably C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, -NR 4a R 5a , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR4 C(O)NR 4 R 5 , C1 ~ C6 alkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylcarbonylamino-, C1 ~ C6 haloalkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 alkylsulfonylamino-, C1 ~ C6 alkylsulfonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylsulfonylamino-, C1 ~ C6 haloalkylsulfonyl(C1 ~ C6 alkyl)amino-, C3 ~ C6 cycloalkylsulfonylamino-, C3 ~ C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; or at least one R selected from the group consisting of a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring 8 and the ring system is substituted with 0 to 5 R 16 and m, R 4 , R 5 and R 16 is as defined herein.

[0044] As defined herein, in the situation where both X and Y are other than cyclopropyl, each R 4a and R 5a are independently selected from the group consisting of C1-C6 alkoxy and C3-C6 cycloalkyl, or R 4 and R 5 together can form a morpholinyl ring.

[0045] Any further R 8Substituents include oxygen, hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR 4 R 5 , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, -NR 4 C(O)NR 4 R 5, C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1-C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0-5 R 16 and m, R 4 , R 5 and R 16 is as defined herein.

[0046] When both X and Y are other than cyclopropyl and D is a monocyclic heteroaryl ring, D may be selected from the group consisting of C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR 4a R 5a , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4C(O)NR 4 R 5 , C1 ~ C6 alkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylcarbonylamino-, C1 ~ C6 haloalkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 alkylsulfonylamino-, C1 ~ C6 alkylsulfonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylsulfonylamino-, C1 ~ C6 haloalkylsulfonyl(C1 ~ C6 alkyl)amino-, C3 ~ C6 cycloalkylsulfonylamino-, C3 ~ at least one R selected from the group consisting of C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring; 8 and the ring system is substituted with 0 to 5 R 16 and / or D is substituted on the ring nitrogen with C5-C6 alkyl, C5-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C3 alkyl-, C3 alkoxy-C1-C2 alkyl-, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m at least one R selected from the group consisting of -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring; 9 and the ring system is substituted with 0 to 5 R 16 and m, R 4 , R 5 , R 4a , R 5aand R 16 is as defined herein.

[0047] In such embodiments, when both X and Y are other than cyclopropyl, any additional ring carbon R 8 Substituents include oxygen, hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 hydroxyalkyl-, C1-C6 alkylcarbonyl-, C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, -NR 4 R 5 , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5, C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1-C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C 6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 and m, R 4 , R 5 and R 16 is as defined herein, and / or any further ring nitrogen R 9 The substituents are C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C-C cycloalkyl, cyano-C-C-alkyl-, and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein said ring system is selected from the group consisting of 0 to 5 R 16 and m, R 4 , R 5 and R 16 is as defined herein.

[0048] In embodiments where at least one of X and Y is cyclopropyl, each R 8 are preferably independently oxo, C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, amino, —NHC(O)CH3, hydroxyl, C1-C4 alkoxy, or C1-C4 alkylthio. More preferably, each R 8 are independently oxo, C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxyl, C1-C4 alkoxy, or C1-C4 alkylthio, and most preferably each R 8 is independently halogen or C1-C4 haloalkyl.

[0049] In embodiments where at least one of X and Y is cyclopropyl, each R 9 is preferably independently C1-C4 alkyl, C1-C4 haloalkyl, hydroxyl, C1-C4 alkoxy, or C1-C4 alkylthio.

[0050] In certain embodiments where at least one of X and Y is cyclopropyl and D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring as defined above, D is selected from the group consisting of 4-chloro-3-pyridyl, 4-trifluoromethylpyridyl, 3-pyridyl, and 2-chloro-thiazo-5-yl, 2-chloro-3-pyridyl, 3-chloro-4-pyridyl, 1-methyl-3-(trifluoromethyl)-pyrazol-4-yl, thiazol-2-yl, thiazol-5-yl, pyrimidin-5-yl, 4-(tert-butoxy)phenyl, 2-chloro-4-pyridyl, 2-methyl-4-pyridyl, 2-trifluoromethyl- and 2-trifluoromethyl-3-pyridyl, 4-pyridyl, 2-amino-4-pyridyl, thiophen-3-yl, 1-methyl-pyrazol-4-yl, 2-methyl-triazol-4-yl, 5-methyl-1,3,4-oxadiazol-2-yl, 5-methyl-3-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 3-methyl-2-pyridyl, 6-chloro-3-pyridyl, 3-trifluoromethyl-3-pyridyl, 4-methyl-2-pyridyl, 2-acetamidothiazol-5-yl, 2-fluoro-4-pyridyl, and 2-trifluoromethyl-3-pyridyl. In a subset of these embodiments, D is selected from the group consisting of 4-chloro-3-pyridyl, 4-trifluoromethylpyridyl, 3-pyridyl, and 2-chloro-thiazo-5-yl, 2-chloro-3-pyridyl, 3-chloro-4-pyridyl, 1-methyl-3-(trifluoromethyl)-pyrazol-4-yl, thiazol-2-yl, thiazol-5-yl, pyrimidin-5-yl, 4-(tert-butoxy)phenyl, 2-chloro-4-pyridyl, 2-methyl-4-pyridyl, 2-trifluoromethyl-4-pyridyl, 4-pyridyl, thiophen-3-yl, 5-methyl-3-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 3-trifluoromethyl-3-pyridyl, 2-fluoro-4-pyridyl, and 2-trifluoromethyl-3-pyridyl.In a further subset of these embodiments, D is selected from the group consisting of 4-chloro-3-pyridyl, 4-trifluoromethylpyridyl, 3-pyridyl, 2-fluoro-4-pyridyl, and 2-chloro-thiazo-5-yl (preferably, 2-fluoro-4-pyridyl).

[0051] When D is a phenyl ring Dp and is substituted, it is 8 and thus may be substituted with the following structure: [ka] wherein at least one R 8p1 , R 8p2 , R 8p3 , R 8p4 and R 8p5 is other than hydrogen. 8p1 , R 8p2 , R 8p3 , R 8p4 and R 8p5 is not hydrogen, any remaining positions on the phenyl ring may be unsubstituted or may alternatively be substituted with additional R 8 Those skilled in the art will recognize that Dp may carry a substituent, the position of which on the phenyl ring is indicated by the number in the superscript p. When Dp is unsubstituted, R 8p1 , R 8p2 , R 8p3 , R 8p4 and R 8p5 does not exist.

[0052] As mentioned above, R 8 The substitution of D by is determined by the presence or absence of cyclopropyl at positions X and / or Y. Thus, in Dp where at least one of X and Y is cyclopropyl, R 8p1 , R 8p2 , R 8p3 , R 8p4 and R 8p5is independently selected from the group consisting of cyano, amino, C1-C3 dialkylamino, hydroxy, C1-C3 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, and halogen, and b is preferably the point of attachment to the remainder of the molecule.

[0053] In one such set of embodiments, R 8p1 , R 8p2 , R 8p3 , R 8p4 and R 8p5 are each independently selected from cyano, C1-C3 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or halogen. 8p1 , R 8p2 , R 8p3 , R 8p4 and R 8p5 is independently selected from cyano, halogen (especially chloro or fluoro), methyl, methoxy, and trifluoromethyl.

[0054] In yet another set of embodiments, R 8p1 , R 8p2 , R 8p4 and R 8p5 Each of the is non-existent and R 8p3 is cyano, C1-C3 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or halogen. Preferably, in this set of embodiments, R 8p3 is halogen, more preferably chloro.

[0055] In a further set of embodiments, R 8p1 , R 8p4 and R 8p5 Each of the is non-existent and R 8p2 and R 8p3 are each independently cyano, C1-C3 alkyl, C1-C4 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, or halogen. 8p2 and R8p3 are each independently particularly preferably halogen, and R 8p2 and R 8p3 More preferably, both are chloro.

[0056] In one particularly preferred set of embodiments in which at least one of X and / or Y is cyclopropyl, D is an unsubstituted phenyl ring.

[0057] In a further embodiment, a particularly preferred set of embodiments in which at least one of X and / or Y is cyclopropyl, D is selected from the group consisting of 4-chloro-phenyl, 4-trifluoromethyl-phenyl, 4-cyanophenyl, 4-fluoro-phenyl, 3,4-di-fluoro-phenyl, 2-trifluoromethyl-phenyl and 4-tolyl.

[0058] W acts as a linker moiety connecting ring D to the rest of the molecule (i.e., to the phenyl-pyridazinone / phenyl-pyridazinedione moiety). Compounds of formula (I) where the linker is W1 are herbicidal, while compounds of formula (I) where the linker is W2 are not only herbicidal but may also be useful intermediates in the production of compounds of formula (I) bearing the W1 linker. Thus, in one set of embodiments, W is W1, while in a second set of embodiments, W is W2. In a third set of embodiments, W is -C≡C-.

[0059] Preferably, R 10 , R 11 , R 12 and R 13 are each independently selected from hydrogen or C1-C3 alkyl. In one set of embodiments, R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0060] Preferably, R 14 and R 15are each independently selected from hydrogen or C1-C3 alkyl. In one set of embodiments, R 14 and R 15 are both hydrogen.

[0061] Specific examples of W include -CH2-CH2-, -CH=CH-, cis [ka] and transformer [ka] and -C≡C-. In a more preferred embodiment, W is -CH2-CH2- or -CH=CH- (especially (E)-CH=CH-), more preferably also -CH2-CH2-.

[0062] In one preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1 is methyl, ethyl, cyclopropyl, propargyl or C1 fluoroalkyl; R 2 is chloro, cyclopropyl, trifluoromethyl or methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro, chloro, or C1-haloalkyl and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is hydrogen, chloro, fluoro, or bromo and is ortho relative to the -WD moiety; D is C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m-C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, -NR 4a R 5a , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C1 ~ C6 alkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylcarbonylamino-, C1 ~ C6 haloalkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 alkylsulfonylamino-, C1 ~ C6 alkylsulfonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylsulfonylamino-, C1 ~ C6 haloalkylsulfonyl(C1 ~ C6 alkyl)amino-, C3 ~ C6 cycloalkylsulfonylamino-, C3 ~ C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, and C1-C6 haloalkoxy(C1-C6 alkyl)amino; or at least one R selected from the group consisting of a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring 8 and the ring system is a phenyl ring substituted with 0 to 5 R 16 is replaced by; Any further R 8 The substituents may be selected from the group consisting of hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C2-C6 alkenyl, and C2-C6 alkynyl; R 4 and R 5 are each independently hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or C3-C6 cycloalkyl; m is an integer of 0, 1, or 2 (preferably 0 or 2); Each R 4a and R 5a are independently selected from the group consisting of C1-C6 alkoxy and C3-C6 cycloalkyl, or R 4a and R 5a together can form a morpholinyl ring; Each R 16 are independently halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0063] In a more preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1 is methyl; R 2 is methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro and ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is one or two R 8 and at least one R 8 is C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m-C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino- and C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 is replaced by; Any further R 8 The substituents may be selected from the group consisting of halogen, C1-C6 alkyl, and C1-C6 haloalkyl; R 4 and R 5 are each independently hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or C3-C6 cycloalkyl; m is 0 or 2 (preferably 0); Each R 16 are independently halogen, cyano, C1-C4 alkyl, C1-C3 haloalkyl, or C1-C4 alkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0064] In an even more preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1 is methyl; R 2 is methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, or methoxy; X is fluoro and ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , —C(O)OH, —C(O)OC1-C6 alkyl and —C(O)NR 4 R 5 or one R selected from the group consisting of a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, or 1,3,5-triazinyl rings; 8 and the ring system is a phenyl ring substituted with 0-2 R 16 is replaced by; R 4 and R 5 are each independently hydrogen or C1-C3 alkyl; m is 0 or 2 (preferably 0); Each R16 are independently halogen or C1-C4 alkyl (preferably methyl); W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen

[0065] Yet in an even more preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1 is methyl; R 2 is methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl; X is fluoro and ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is one R selected from the group consisting of methylsulfanylmethyl, isopropylsulfanylmethyl, sulfamoyl, methylsulfamoyl, and carbamoyl; or a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, 1,2,4-triazolyl, oxazolyl, and thiazolyl rings. 8 and the ring system is a phenyl ring substituted with 0-2 R 16 is replaced by; Each R 16 is methyl; W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0066] In an alternative preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1is methyl, ethyl, cyclopropyl, propargyl or C1 fluoroalkyl; R 2 is chloro, cyclopropyl, trifluoromethyl or methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro, chloro, or C1-haloalkyl and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is hydrogen, chloro, fluoro, or bromo and is ortho relative to the -WD moiety; D is C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR 4a R 5a , -C(S)NR 4 R 5 , -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5, C1 ~ C6 alkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylcarbonylamino-, C1 ~ C6 haloalkylcarbonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 alkylsulfonylamino-, C1 ~ C6 alkylsulfonyl(C1 ~ C6 alkyl)amino-, C1 ~ C6 haloalkylsulfonylamino-, C1 ~ C6 haloalkylsulfonyl(C1 ~ C6 alkyl)amino-, C3 ~ C6 cycloalkylsulfonylamino-, C3 ~ at least one R selected from the group consisting of C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring; 8 and wherein the ring system is a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, substituted with 0 to 5 R 16 is replaced by; Any further R 8 The substituents may be selected from the group consisting of hydroxyl, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C2-C6 alkenyl, and C2-C6 alkynyl; and / or D is selected from the group consisting of C5-C6 alkyl, C5-C6 haloalkyl, C3-C6 cycloalkyl, C1-C3 alkoxy-C3 alkyl-, C3 alkoxy-C1-C2 alkyl-, C1-C3 haloalkoxy-C1-C3 alkyl-, C1-C3 alkoxy-C1-C3 alkoxy-C1-C3 alkyl-, C1-C6 hydroxyalkyl-, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) mat least one R selected from the group consisting of -C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring; 9 and the ring system is substituted with 0 to 5 R 16 is replaced by; R 4 and R 5 are each independently hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or C3-C6 cycloalkyl; m is an integer of 0, 1, or 2 (preferably 0 or 2); Each R 4a and R 5a are independently selected from the group consisting of C1-C6 alkoxy and C3-C6 cycloalkyl, or R 4a and R 5a together can form a morpholinyl ring; Each R 16 are independently halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0067] In an alternative more preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1 is methyl; R 2 is methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro and ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is one or two R on a ring carbon 8 and a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, substituted with at least one R 8 is C1-C6 haloalkylcarbonyl-, C3-C6 cycloalkylcarbonyl-, -S(O) m -C1-C6 haloalkyl, -S(O) m -C3-C6 cycloalkyl, -OS(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m -C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m -C3-C6 cycloalkyl, -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5 , -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino- and C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-; or a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 is replaced by; Any further R 8 The substituents may be selected from the group consisting of halogen, C1-C6 alkyl, and C1-C6 haloalkyl; and / or D may be selected from the group consisting of C5-C6 alkyl, C5-C6 haloalkyl, C3-C6 cycloalkyl, -C1-C3 alkyl-S(O) on the ring nitrogen. m -C1-C6 alkyl, -C1-C3 alkyl-S(O) m-C1-C6 haloalkyl, -C1-C3 alkyl-S(O) m - one R selected from the group consisting of C3-C6 cycloalkyl and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring; 9 and the ring system is substituted with 0 to 5 R 16 is replaced by; R 4 and R 5 are each independently hydrogen, C1-C3 alkyl, C1-C3 alkoxy, or C3-C6 cycloalkyl; m is 0 or 2 (preferably 0); Each R 16 are independently halogen, cyano, C1-C4 alkyl, C1-C3 haloalkyl, or C1-C4 alkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0068] In an alternative even more preferred set of embodiments in compounds of formula (I) where both X and Y are other than cyclopropyl; R 1 is methyl; R 2 is methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, or methoxy; X is fluoro and ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is -C1-C3 alkyl-S(O) on the ring carbon m -C1-C6 alkyl, -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR 4 R 5, —C(O)OH, —C(O)OC1-C6 alkyl and —C(O)NR 4 R 5 or one R selected from the group consisting of a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, or 1,3,5-triazinyl rings; 8 and wherein the ring system is a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 nitrogen atoms substituted with 0-2 R 16 and / or D is substituted on the ring nitrogen with one R selected from the group consisting of C5-C6 alkyl, C3-C6 cycloalkyl, and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring. 9 and the ring system is substituted with 0 to 2 R 16 is replaced by; R 4 and R 5 are each independently hydrogen or C1-C3 alkyl; m is 0 or 2 (preferably 0); Each R 16 are independently halogen or C1-C4 alkyl (preferably methyl); W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0069] Yet another even more preferred set of alternative embodiments in compounds of formula (I) wherein both X and Y are other than cyclopropyl; R 1 is methyl; R 2 is methyl; G is hydrogen or -C(O)-R 3 and R 3 is isopropyl; X is fluoro and ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is one R selected from the group consisting of methylsulfanylmethyl, isopropylsulfanylmethyl, sulfamoyl, methylsulfamoyl, and carbamoyl on a ring carbon; or a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, 1,2,4-triazolyl, oxazolyl, and thiazolyl rings. 8 and the ring system is a pyrazolyl or pyridyl substituted with 0 to 2 R 16 and / or D is substituted on the ring nitrogen with one R selected from cyclopropyl or phenyl 9 is replaced by; Each R 16 is methyl; W is W1; R 10 , R 11 , R 12 , and R 13 are all hydrogen.

[0070] The following Tables A-1, A-2, A-3, A-4, B-1, B-2, B-3, B-4, C-1, C-2, C-3, and C-4 illustrate specific examples of the compounds of formula (I) of the present invention.

[0071] Herbicidal Compounds of the Invention The numbering system used to describe the positions of X and Y in the compounds of formula (I) shown below is presented for clarity purposes only. [ka]

[0072] Table A-1 provides 672 compounds A-1.001 to A-1.672 of formula (I), where G is -H, W is -CH2-CH2-, and R 1 , R 2 , X, Y, and D are as defined for compound numbers 1.001 to 1.672 in Table 1 below.

[0073] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9] [Table 1-10] [Table 1-11] [Table 1-12] [Table 1-13] [Table 1-14] [Table 1-15] [Table 1-16] [Table 1-17] [Table 1-18] [Table 1-19] [Table 1-20] [Table 1-21] [Table 1-22] [Table 1-23] [Table 1-24] [Table 1-25] [Table 1-26]

[0074] Table A-2 provides 672 compounds A-2.001 to A-2.672 of formula (I), where G is H, W is (E)-CH=CH-, and R 1 , R 2, X, Y, and D are as defined for compound numbers 1.001 to 1.672 in Table 1 above, respectively.

[0075] Table A-3 provides 672 compounds A-3.001 to A-3.672 of formula (I), where G is —(C═O)iPr, W is —CH—CH—, and R 1 , R 2 , X, Y, and D are as defined for compound numbers 1.001 to 1.672 in Table 1 above, respectively.

[0076] Table A-4 provides 672 compounds A-4.001 to A-4.672 of formula (I), where G is —(C═O)iPr, W is (E)—CH═CH—, and R 1 , R 2 , X, Y, and D are as defined for compound numbers 1.001 to 1.672 in Table 1 above, respectively.

[0077] Table B-1 provides 744 compounds B-1.001 to B-1.744 of formula (I), wherein G is -H, W is -CH2-CH2-, X is 6-cyclopropyl, and R 1 , R 2 , Y, and D are as defined for compound numbers 2.001 to 2.744, respectively, in Table 2 below.

[0078] [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] Table 2-6 Table 2-7 Table 2-8 Table 2-9 Table 2-10 Table 2-11 Table 2-12 Table 2-13 Table 2-14 Table 2-15 Table 2-16 Table 2-17 Table 2-18 Table 2-19 Table 2-20 Table 2-21 Table 2-22 [Table 2-23] [Table 2-24] [Table 2-25]

[0079] Table B-2 provides 744 compounds B-2.001 to B-2.744 of formula (I), wherein G is —H, W is (E)—CH═CH—, X is 6-cyclopropyl, and R 1 , R 2 , Y, and D are as defined for compound numbers 2.001 to 2.744, respectively, in Table 2 above.

[0080] Table B-3 provides 744 compounds B-3.001 to B-3.744 of formula (I), wherein G is —(C═O)iPr, W is —CH—CH—, X is 6-cyclopropyl, and R 1 , R 2 , Y, and D are as defined for compound numbers 2.001 to 2.744, respectively, in Table 2 above.

[0081] Table B-4 provides 744 compounds B-4.001 to B-4.744 of formula (I), wherein G is —(C═O)iPr, W is (E)—CH═CH—, X is 6-cyclopropyl, and R 1 , R 2 , Y, and D are as defined for compound numbers 2.001 to 2.744, respectively, in Table 2 above.

[0082] Table C-1 provides 744 compounds C-1.001 to C-1.744 of formula (I), wherein G is -H, W is -CH2-CH2-, Y is 3-cyclopropyl, and R 1 , R 2 , X, and D are as defined for compound numbers 3.001 to 3.744, respectively, in Table 3 below.

[0083] Table 3-1 Table 3-2 Table 3-3 Table 3-4 Table 3-5 Table 3-6 Table 3-7 Table 3-8 Table 3-9 Table 3-10 Table 3-11 Table 3-12 Table 3-13 Table 3-14 Table 3-15 Table 3-16 Table 3-17 [Table 3-18] [Table 3-19] [Table 3-20] [Table 3-21] [Table 3-22] [Table 3-23] [Table 3-24] [Table 3-25]

[0084] Table C-2 provides 744 compounds C-2.001 to C-2.744 of formula (I), wherein G is -H, W is (E)-CH=CH-, Y is 3-cyclopropyl, and R 1 , R 2 , X, Y, and D are as defined for compound numbers 3.001 to 3.744, respectively, in Table 3 above.

[0085] Table C-3 provides 744 compounds C-3.001 to C-3.744 of formula (I), wherein G is —(C═O)iPr, W is —CH—CH—, Y is 3-cyclopropyl, and R 1 , R 2 , X, and D are as defined for compound numbers 3.001 to 3.744, respectively, in Table 3 above.

[0086] Table C-4 provides 744 compounds C-4.001 to C-4.744 of formula (I), wherein G is —(C═O)iPr, W is (E)—CH═CH—, Y is 3-cyclopropyl, and R 1 , R 2 , X, and D are as defined for compound numbers 3.001 to 3.744, respectively, in Table 3 above.

[0087] The compounds of the present invention may be prepared by the following scheme, where the substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , W, D, Dp, G, X, Y, and m have the definitions set forth hereinabove (unless expressly stated otherwise).

[0088] Certain compounds of the present invention (I-ii) can be prepared from compound (2) as shown in Reaction Scheme 1. Compound (I-ii) is a compound of formula (I) where W is -CH-CH-.

[0089] Reaction Scheme 1 [ka] Compound (I-ii) can be prepared by catalytic hydrogenation of compound (2) with hydrogen gas in a suitable solvent (e.g., tetrahydrofuran, methanol, ethanol, acetic acid, or ethyl acetate) in the presence of a suitable catalyst (e.g., Pd / C, Pd / CaCO3, Rh / Al2CO3, or sponge nickel) at a temperature of -10 to 100°C.

[0090] Alternatively, compound (I-ii) can also be prepared by catalytic transfer hydrogenation of compound (2) by treatment with a suitable hydrogen source in a suitable solvent in the presence of a suitable catalyst at temperatures between −10 and 100° C. Examples of suitable systems are tetrahydroxydiboron in dichloromethane / water or dichloromethane / methanol mixtures in the presence of Pd / C, Pd(OAc) or Pd(OH) / C (J. Am. Chem. Soc., 2016, 138, 6107-6110), or diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate in ethanol in the presence of Pd / C (Tetrahedron Letters, 2009, 50, 1026).

[0091] Compound (2) can be prepared from compounds (3) and (4) according to the Suzuki or Heck protocols below, as shown in Reaction Scheme 2. When using the Suzuki protocol, compound (4) is an organoboron compound, such as a boronic acid, a boronic ester, or potassium trifluoroborate. When using the Heck protocol, compound (4) is a styrene.

[0092] Alternatively, compound (I-ii) can also be prepared by reduction with a diimide generated in situ from a suitable precursor in a suitable solvent at a temperature of -10 to 200°C. Examples of suitable reagents for generating the diimide include substituted arylsulfonyl hydrazides, such as 2,4,6-triisopropylbenzenesulfonyl hydrazide, optionally in the presence of a suitable base. Examples of suitable bases include triethylamine, diisopropylethylamine, potassium carbonate, and sodium carbonate. Suitable solvents include tetrahydrofuran, 1,4-dioxane, ethyl acetate, acetonitrile, and dimethylformamide.

[0093] Reaction Scheme 2 [ka] Suzuki Protocol Compound (2) can be prepared by treating compounds (3) and (4) in the presence of a suitable base and a suitable catalyst in a suitable solvent at temperatures between 10 and 150°C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, sodium bicarbonate, and potassium fluoride. Examples of suitable catalysts include 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl2(dppf)·DCM], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], and a catalyst system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine. Examples of suitable solvents include water, 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Many compounds (4) are commercially available (e.g., trans-2-(4-biphenyl)vinylboronic acid) or can be prepared by known methods. An example of compound (3) that has particular utility in the Suzuki protocol is the isobutyryl ester (3-i), where G is isobutyryl.

[0094] Those skilled in the art will recognize that the conditions of the Suzuki Protocol tend to cleave ester groups, and as a result, Reaction Scheme 2 can also describe reactions in which starting material (3) contains an ester moiety [such that G is an acyl group], but product (2) does not contain an ester moiety [such that G is hydrogen].

[0095] Heck Protocol Compound (2) can be prepared by treating compounds (3) and (4) in the presence of a suitable base and a suitable catalyst at a temperature of 10 to 150°C. An additional solvent may optionally be included. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine, and pyridine. Examples of suitable catalysts include tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], a catalyst system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, and a palladacycle precatalyst, such as a catalyst system formed in situ from chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II). Examples of optional additional solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Many compounds 4 are commercially available (e.g., 4-cyanostyrene) or can be made by known methods. An example of a compound 3 that has particular utility in the Heck protocol is the isobutyryl ester 3-i, where G is isobutyryl.

[0096] Compound (3-i) can be prepared from compound (5) as shown in Reaction Scheme 3.

[0097] Reaction Scheme 3 [ka] Compound (3-i) can be prepared by treating compound (5) with isobutyryl chloride in a suitable solvent (e.g., dichloromethane, acetonitrile, or toluene) in the presence of a suitable base (e.g., triethylamine, diisopropylethylamine, or pyridine) at a temperature of −10 to 60° C. A catalyst (e.g., 4-(dimethylamino)pyridine) may optionally be included.

[0098] Compound (5) can be prepared from compound (6) as shown in Reaction Scheme 4 by heating compound (6) with a base (e.g., 1,8-diazabicyclo[5.4.0]undec-7-ene, sodium hexamethyldisilazide, or lithium hexamethyldisilazide) in a solvent (e.g., acetonitrile, N,N-dimethylformamide, or toluene) at a temperature between 50 and 200° C. Conventional or microwave heating can be used.

[0099] Reaction Scheme 4 [ka] Compound (6) can be prepared from phenylacetic acid (7) as shown in Reaction Scheme 5.

[0100] Reaction Scheme 5 [ka] With reference to Reaction Scheme 5, an example of hydrazine 8 is methylhydrazine, and an example of ketoester 10 is ethyl pyruvate. An example of hydrazone 9 is ethyl (2E / Z)-2-(methylhydrazono)propanoate, prepared by the method described in WO 2016 / 008816. An example of phenylacetic acid 7 is (2-bromo-6-fluorophenyl)acetic acid, which can be synthesized according to Reaction Scheme 10. A further example of phenylacetic acid 7 is (2-bromo-3-chloro-6-fluorophenyl)acetic acid, which can be synthesized according to Reaction Scheme 11.

[0101] Certain compounds of the present invention, (I-iii), can be prepared from compound (11), as shown in Reaction Scheme 6, or from compound (I-iv), as shown in Reaction Scheme 12. Compound (I-iii) is a compound of formula (I), where W is —CH—CH— and G is hydrogen.

[0102] Reaction Scheme 6 [ka] Compound (I-iii) can be prepared by heating compound (11) with a base (e.g., 1,8-diazabicyclo[5.4.0]undec-7-ene, sodium hexamethyldisilazide, or lithium hexamethyldisilazide) in a solvent (e.g., acetonitrile, N,N-dimethylformamide, or toluene) at a temperature of 50 to 200° C. Conventional or microwave heating can be used.

[0103] Compound (11) can be prepared from compound (12) as shown in Reaction Scheme 7 below.

[0104] Reaction Scheme 7 [ka] Compound 12 can be prepared from compound 13 as shown in Reaction Scheme 8. Many compounds 13 are commercially available [e.g., methyl 2-phenylacetate and methyl 2-(2-fluorophenyl)acetate].

[0105] Referring to Reaction Scheme 8, phosphorane (15) can be prepared according to Reaction Scheme 9.

[0106] Reaction Scheme 8 [ka] Reaction Scheme 9 [ka] For Reaction Scheme 9, examples of suitable bases are sodium hydride, sodium hexamethyldisilazide, and potassium tert-butoxide. Compound 16 is an electrophile, where LG is a leaving group (e.g., chloride, bromide, iodide, tosylate, or mesylate). Many compounds 16 are commercially available (e.g., 4-chlorobenzyl bromide or 2-chloro-5-chloromethylthiazole).

[0107] Reaction Scheme 10 [ka] With reference to Reaction Scheme 10, (2-bromo-6-fluoro-phenyl)acetic acid ethyl ester can be prepared as described in Lundgren et al. JACS 2016, 138, 13826-13829.

[0108] Reaction Scheme 11 [ka] With reference to Reaction Scheme 11, 2-bromo-1-chloro-4-fluoro-benzene is commercially available.

[0109] Reaction Scheme 12 [ka] Compound (I-iii) can be prepared by treating compound (I-iv) with a metal hydroxide (e.g., sodium hydroxide, lithium hydroxide, or potassium hydroxide) in a mixture of water and a suitable solvent (e.g., methanol, ethanol, or tetrahydrofuran) at a temperature between 0°C and 100°C; or by treating compound (I-iv) with a metal carbonate (e.g., sodium carbonate or potassium carbonate) in an alcohol solvent (e.g., methanol or ethanol). Compound (I-iv) is a compound of formula (I), wherein W is -CH2-CH2- and G is C(O)R 3 is.

[0110] Compound 2 can be prepared from compounds 14 and 15 by the Suzuki Protocol or the Heck Protocol described below, as shown in Reaction Scheme 13. When using the Suzuki Protocol, compound 14 is an organoboron compound, such as a boronic acid, a boronate ester, or potassium trifluoroborate, and compound 15 is a halide or pseudohalide compound, such as a chloride, bromide, iodide, or triflate. When using the Heck Protocol, compound 14 is styrene, and compound 15 is a halide or pseudohalide compound, such as a chloride, bromide, iodide, or triflate.

[0111] Reaction Scheme 13 [ka] Suzuki Protocol Compound (2) can be prepared by treating compounds (14) and (15) in the presence of a suitable base and a suitable catalyst in a suitable solvent at temperatures between 10 and 150 °C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, sodium bicarbonate, and potassium fluoride. Examples of suitable catalysts include 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf)·DCM], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], and a catalyst system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine. Examples of suitable solvents include water, 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Many compounds (15) are commercially available or can be prepared by known methods. An example of compound (14) that has particular utility in the Suzuki protocol is the isobutyryl ester (14-i), where G is isobutyryl.

[0112] Those skilled in the art will recognize that the conditions of the Suzuki Protocol tend to cleave ester groups, and as a result, Reaction Scheme 13 can also describe reactions in which starting material 14 contains an ester moiety [such that G is an acyl group], but product 2 does not contain an ester moiety [such that G is hydrogen].

[0113] Heck Protocol Compound (2) can be prepared by treating compound (14) with compound (15) in the presence of a suitable base and a suitable catalyst at a temperature of 10 to 150°C. An additional solvent may optionally be included. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine, and pyridine. Examples of suitable catalysts include tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], a catalyst system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, and a palladacycle precatalyst, such as a catalyst system formed in situ from chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II). Examples of optional additional solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Many compounds 15 are commercially available or can be made by known methods. An example of a compound 14 that has particular utility in the Heck protocol is the isobutyryl ester 14-i, where G is isobutyryl.

[0114] Compound (14-ii), where J is an organoboron species, such as a boronic ester, can be prepared from compound (3) and compound (16) as shown in Reaction Scheme 14.

[0115] Reaction Scheme 14 [ka] Compound (14-ii) can be prepared by treating compound (3) and compound (16) in the presence of a suitable base and a suitable catalyst at a temperature of 10 to 150°C. An additional solvent may optionally be included. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine, and pyridine. Examples of suitable catalysts include tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], a catalyst system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine, and a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate. Examples of optional additional solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Many compounds (16) are commercially available (e.g., vinylboronic acid MIDA ester or vinylboronic acid pinacol ester) or can be prepared by known methods. An example of a compound (3) that has particular utility in the Heck protocol is the isobutyryl ester (3-i), where G is isobutyryl.

[0116] Compound (14-iii), where J is hydrogen, can be prepared from compound (3) as shown in Reaction Scheme 15.

[0117] Reaction Scheme 15 [ka] Compound (14-iii) can be prepared by treating compound (3) with tributyl(vinyl)stannane in a suitable solvent, optionally in the presence of a suitable base and a suitable catalyst, at a temperature of 10 to 150° C. Examples of the optional base include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine, and pyridine. Examples of suitable catalysts include 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf)·DCM], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], a catalyst system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, and a catalyst system formed in situ from a palladacycle catalyst precursor, such as chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II). Examples of suitable solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. An example of compound (3) with particular utility is the isobutyryl ester (3-i), where G is isobutyryl.

[0118] Compound (18) can be prepared from compound (3) by the Sonogashira reaction as shown in Reaction Scheme 16.

[0119] Reaction Scheme 16 [ka] Compound (18) can be prepared by treating compound (3) and compound (17) in the presence of a suitable base and a suitable catalyst at a temperature of 10 to 150°C. Optionally, an additional solvent may be added. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylamine, diisopropylethylamine, and pyridine. Examples of suitable catalysts include a catalyst system formed in situ from a mixture of bis(triphenylphosphine)palladium(II) dichloride [Pd(PPh3)Cl2], palladium(II) acetate, and triphenylphosphine, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, and a catalyst system formed in situ from a palladacycle catalyst precursor, such as chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II). Optionally, a copper catalyst, such as copper(I) iodide, may also be added. Examples of suitable additional solvents are 1,4-dioxane, tetrahydrofuran, acetonitrile, toluene, and N,N-dimethylformamide. An example of a compound (3) having particular utility is the isobutyryl ester (3-i), where G is isobutyryl.

[0120] Those skilled in the art will recognize that the conditions for the Sonogashira reaction tend to cleave ester groups, and as a result, Reaction Scheme 16 can also describe a reaction in which starting material (3) contains an ester moiety [such that G is an acyl group], but product (18) does not contain an ester moiety [such that G is hydrogen].

[0121] Compound (19) can be prepared via a Suzuki reaction from compound (3) and compound (20), as shown in Reaction Scheme 17, where compound (20) is a suitable organoboron species, such as a boronic acid, a boronic ester, or potassium trifluoroborate.

[0122] Reaction Scheme 17 [ka] Compound (19) can be prepared by treating compound (3) and compound (20) in the presence of a suitable base and a suitable catalyst in a suitable solvent at a temperature of 10 to 150° C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, sodium bicarbonate, and potassium fluoride. Examples of suitable catalysts include 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf)·DCM], a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tricyclohexylphosphine, a catalyst system formed in situ from a palladacycle catalyst precursor, such as chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II), and a catalyst system formed in situ from a palladacycle catalyst precursor, such as chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II). Examples of suitable solvents include water, 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Some compounds 20 are commercially available (e.g., 4,4,5,5-tetramethyl-2-(2-phenyl-cyclopropyl)-[1,3,2]dioxaborolane) or can be made by known methods (see, for example, the methods described in Org. Process Res. Dev. 2012, 16, 87-95). An example of a compound 3 that has particular utility in the Suzuki reaction is the benzyl ether 3-ii, where G is benzyl.

[0123] Reaction Scheme 18 [ka] Compound (I9-ii) can be prepared by catalytic hydrogenation of compound (19-i) with hydrogen gas in a suitable solvent (e.g., tetrahydrofuran, methanol, ethanol, acetic acid, or ethyl acetate) in the presence of a suitable catalyst (e.g., Pd / C, Pd / CaCO, Rh / AlCO, or sponge nickel) at a temperature of −10 to 100° C.

[0124] Certain compounds of the present invention (I-ii) can be prepared from compound (21) as shown in Reaction Scheme 19. Compound (I-ii) is a compound of formula (I) where W is —CH—CH—.

[0125] Reaction Scheme 19 [ka] Compounds (I-ii) can be prepared by treating compound (21) (where [B] can be a trialkylborane, alkylboronic acid, alkylboronic ester, or alkylpotassium trifluoroborate) with compound (15) in the presence of a suitable base and a suitable catalyst in a suitable solvent at temperatures between 10 and 150 °C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, cesium carbonate, sodium bicarbonate, and potassium fluoride. Examples of suitable catalysts include 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf).DCM], [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)dichloropalladium(II) [Pd-PEPPSI™-IPent], and palladacycle precatalysts. In situ formed catalytic systems, such as chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) [RuPhos-Pd-G2], [dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonyl)phosphine, Examples of suitable solvents include [(4-(N,N-dimethylamino)phenyl)di-tert-butylphosphine](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]palladium [XPhos-Pd-G4], and [(4-(N,N-dimethylamino)phenyl)di-tert-butylphosphine](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]palladium [APhos-Pd-G4]. Examples of suitable solvents include water, 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. Many compounds 15 are commercially available or can be made by known methods. An example of compound 21 that has particular utility in the Suzuki protocol is the isobutyryl ester 21-i, where G is isobutyryl.

[0126] Those skilled in the art will recognize that the conditions of the Suzuki Protocol tend to cleave ester groups, and as a result, Reaction Scheme 19 can also describe reactions in which starting material 21 contains an ester moiety [such that G is an acyl group], but product I-ii does not contain an ester moiety [such that G is hydrogen].

[0127] Reaction Scheme 20 [ka] Compound 21 can be prepared by hydroboration of alkene 14-iii using a suitable hydroboration reagent 22 in a suitable solvent, optionally with the addition of a suitable catalyst, at temperatures between 0°C and 100°C. Examples of hydroboration reagents include borane, dichloroborane, dibromoborane, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane [pinacolborane], 1,3,2-benzodioxaborole [catecholborane], or 9-borylbicyclo[3.3.1]nonane [9-BBN]. Examples of suitable solvents include tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, 2-methoxy-2-methylpropane [MTBE], and diethyl ether. An example of a suitable catalyst includes a catalyst system formed in situ from bis(1,5-cyclooctadiene)diiridium(I) dichloride [[Ir(COD)Cl]2] and 4-diphenylphosphanylbutyl(diphenyl)phosphane [DPPB] [J. Am. Chem. Soc., 2004, 126, 9200-9201].

[0128] When [B] is an alkylboronic acid ester, it can be converted to the corresponding boronic acid by treatment with methylboronic acid [MeB(OH)] and trifluoroacetic acid in a suitable solvent, such as dichloromethane [DCM], at a temperature between 0 and 40° C. [Org. Lett., 2019, 21, 3048-3052]. When [B] is an alkylboronic acid or ester, it can be converted to the corresponding alkylpotassium trifluoroborate by treatment with potassium bifluoride in a suitable solvent, such as methanol or acetone, at a temperature between 0 and 40° C.

[0129] Reaction Scheme 21 [ka] Compound (I-iii) (wherein Y is cyclopropyl) can be prepared by treating compound (Iv) with compound (23) (wherein [B] can be trialkylborane, alkylboronic acid, alkylboronic acid ester, or alkylpotassium trifluoroborate) in the presence of a suitable base and a suitable catalyst in a suitable solvent at a temperature of 10 to 150° C. Compound (Iv) is a compound of formula (I) where C is —CH—CH— and G is C(o)R 3and Y is -Cl. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, cesium carbonate, sodium bicarbonate, and potassium fluoride. Examples of suitable catalysts include 1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex [PdCl2(dppf).DCM], [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)dichloropalladium(II) [Pd-PEPPSI™-IPent], palladacycle precatalysts In situ formed catalytic systems, such as chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) [RuPhos-Pd-G2], [dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine](methanesulfonyl)phosphine, Examples of suitable solvents include [(4-(N,N-dimethylamino)phenyl)di-tert-butylphosphine](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]palladium [XPhos-Pd-G4], and [(4-(N,N-dimethylamino)phenyl)di-tert-butylphosphine](methanesulfonato-κO)[2'-(methylamino-κN)[1,1'-biphenyl]-2-yl-κC]palladium [APhos-Pd-G4]. Examples of suitable solvents include water, 1,4-dioxane, tetrahydrofuran, acetonitrile, and toluene. An example of a compound (Iv) having particular utility in the Suzuki protocol is the isobutyryl ester (Iv), where G is isobutyryl.

[0130] Those skilled in the art will recognize that the conditions of the Suzuki Protocol tend to cleave the ester group, and as a result, Reaction Scheme 21 can describe a reaction in which the starting material (Iv) contains an ester moiety [such that G is an acyl group], but the product (I-iii) does not contain an ester moiety [such that G is hydrogen].

[0131] Although the compounds of formula (I) according to the present invention can be used as herbicides themselves, they are generally formulated into herbicidal compositions using formulation adjuvants, such as carriers, solvents and surfactants (SFA).Thus, the present invention further provides a herbicidal composition comprising a herbicidal compound according to any one of the preceding claims and an agriculturally acceptable formulation adjuvant.The composition may be in the form of a concentrate that is diluted before use, but ready-to-use compositions can also be prepared.Final dilution is usually carried out with water, but instead of or in addition to water, it can be carried out with, for example, liquid fertilizer, micronutrients, biological organisms, oil or solvent.

[0132] The herbicidal compositions generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of a compound of formula I and preferably 1 to 99.9% by weight of a formulation adjuvant containing 0 to 25% by weight of a surfactant.

[0133] The compositions can be selected from several formulation types, many of which are known from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999. These include dispersible powders (DP), soluble powders (SP), water-soluble granules (SG), water-dispersible granules (WG), wettable powders (WP), granules (GR) (sustained or rapid release), soluble concentrates (SL), oil-miscible liquids (OL), ultra-low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil-in-water (EW) and water-in-oil (EO)), microemulsions (ME), suspension concentrates (SC), aerosols, capsule suspensions (CS), and seed treatment formulations. The formulation type selected in any case depends on the specific purpose envisaged and the physical, chemical, and biological properties of the compound of formula (I).

[0134] Flourless powders (DP) may be prepared by mixing a compound of formula (I) with one or more solid excipients (e.g., natural clay, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earth, calcium phosphate, calcium and magnesium carbonate, sulfur, lime, wheat flour, talc, and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

[0135] Soluble powders (SP) can be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (e.g., sodium bicarbonate, sodium carbonate, or magnesium sulfate) or one or more water-soluble organic solids (e.g., polysaccharides), and optionally one or more wetting agents, one or more dispersing agents, or a mixture of the above agents to improve water dispersibility / solubility. The mixture is then ground into a fine powder. Similar compositions can also be granulated to form water-soluble granules (SG).

[0136] Wettable powders (WP) can be prepared by mixing a compound of formula (I) with one or more solid excipients or carriers, one or more wetting agents, and preferably one or more dispersing agents, and optionally one or more suspending agents to facilitate dispersion in a liquid. The mixture is then ground to a fine powder. Similar compositions can also be granulated to form water-dispersible granules (WG).

[0137] Granules (GR) can be formed by granulating a mixture of a compound of formula (I) and one or more powdered solid excipients or carriers, or by absorbing a compound of formula (I) (or a solution thereof in a suitable agent) into a porous granular material (e.g., pumice, attapulgite clay, Fuller's earth, porous diatomaceous earth, diatomaceous earth, or ground corn cob) from a preformed blank granule, or by adsorbing a compound of formula (I) (or a solution thereof in a suitable agent) onto a hard core material (e.g., sand, silicate, mineral carbonate, mineral sulfate, or mineral phosphate) and optionally drying. Agents commonly used to aid absorption or adsorption include solvents (e.g., aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones, and esters) and binders (e.g., polyvinyl acetate, polyvinyl alcohol, dextrin, sugar, and vegetable oil). One or more other additives can also be included in the granules (e.g., emulsifiers, wetting agents, or dispersing agents).

[0138] Dispersible concentrates (DC) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol, or glycol ether. These solutions may contain surfactants (e.g., to improve water dilution or prevent crystallization in the spray tank).

[0139] Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents, or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (e.g., alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150, and SOLVESSO 200; SOLVESSO is a registered trademark), ketones (e.g., cyclohexanone or methylcyclohexanone) and alcohols (e.g., benzyl alcohol, furfuryl alcohol, or butanol), N-alkylpyrrolidones (e.g., N-methylpyrrolidone or N-octylpyrrolidone), dimethylamides of fatty acids (e.g., C8-C9 alkyl esters), and the like.10 The EC products emulsify spontaneously upon addition to water, producing emulsions with sufficient stability to allow spray application via suitable equipment.

[0140] Preparation of an EW involves obtaining a compound of formula (I) as a liquid (if it is not liquid at room temperature, it may melt at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in a suitable solvent), and then emulsifying the resulting liquid or solution into water containing one or more SFAs under high shear to produce an emulsion. Suitable solvents for use in an EW include vegetable oils, chlorinated hydrocarbons (e.g., chlorobenzene), aromatic solvents (e.g., alkylbenzenes or alkylnaphthalenes), and other suitable organic solvents that have poor solubility in water.

[0141] Microemulsions (MEs) can be prepared by mixing water with a blend of one or more solvents with one or more SFAs, resulting in the spontaneous formation of a thermodynamically stable, isotropic liquid formulation. The compound of formula (I) is initially present in the water or solvent / SFA blend. Suitable solvents for use in MEs include those described above for use in ECs or EWs. MEs can be oil-in-water or water-in-oil systems (which system is present can be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. MEs either remain as microemulsions or form conventional oil-in-water emulsions, suitable for dilution into water.

[0142] Suspension concentrates (SCs) may comprise aqueous or non-aqueous suspensions of finely divided, insoluble solid particles of a compound of formula (I). SCs may be prepared by ball milling or bead milling a solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition, and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula (I) may be dry-milled and added to water containing the above-mentioned agents to produce the desired final product.

[0143] Aerosol formulations include a compound of formula (I) and a suitable propellant (e.g., n-butane). The compound of formula (I) may also be dissolved or dispersed in a suitable vehicle (e.g., water or a water-miscible liquid, such as n-propanol) to provide a composition for use in a non-pressurized, manually operated spray pump.

[0144] Capsule suspensions (CS) can be prepared in a similar manner to the preparation of EW formulations, but with an additional polymerization step to obtain an aqueous dispersion of oil droplets, where each oil droplet is encapsulated by a polymer shell and contains the compound of formula (I), and therefore optionally a carrier or excipient. The polymer shell can be produced by an interfacial polycondensation reaction or a coacervation procedure. The composition can achieve controlled release of the compound of formula (I), which can be used for seed treatment. The compound of formula (I) can also be formulated in a biodegradable polymer matrix to achieve controlled sustained release of the compound.

[0145] The composition may contain one or more additives that improve the biological performance of the composition, for example, by improving wetting, retention, or distribution on a surface; resistance to rain on the treated surface; or uptake or mobility of the compound of formula (I). Such additives include surfactants (SFAs), oil-based spray additives, such as certain mineral oils or natural vegetable oils (e.g., soybean oil and rapeseed oil), and blends thereof with other bioavailability-enhancing adjuvants (components that can assist or modify the action of the compound of formula (I)).

[0146] Wetting agents, dispersing agents and emulsifying agents may be SFAs of the cationic, anionic, amphoteric or non-ionic type.

[0147] Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethylammonium bromide), imidazolines and amine salts.

[0148] Suitable anionic SFAs include alkali metal salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (e.g., sodium lauryl sulfate), salts of sulfonated aromatic compounds (e.g., sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalenesulfonate, and mixtures of sodium diisopropylnaphthalenesulfonate and sodium triisopropylnaphthalenesulfonate), ether sulfates, alcohol ether sulfates (e.g., sodium laureth-3-sulfate), ether carboxylates (e.g., sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (mainly monoesters) or phosphorus pentoxide (mainly diesters), for example, between lauryl alcohol and tetraphosphoric acid; further, these products may be ethoxylated), sulfosuccinamates, paraffins or sulfonated olefins, taurates, and lignosulfonates.

[0149] Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

[0150] Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (e.g., oleyl alcohol or cetyl alcohol) or alkylphenols (e.g., octylphenol, nonylphenol or octylcresol); partial esters derived from long-chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (containing ethylene oxide and propylene oxide); alkanolamides; simple esters (e.g., fatty acid polyethylene glycol esters); amine oxides (e.g., lauryl dimethylamine oxide); and lecithin.

[0151] Suitable suspending agents include hydrocolloids (eg, polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (eg, bentonite or attapulgite).

[0152] The compositions of the present invention may further comprise at least one additional pesticide. For example, the compounds according to the present invention can also be used in combination with other herbicides or plant growth regulators. In a preferred embodiment, the additional pesticide is a herbicide and / or a safener for a herbicide. Specific examples of such mixtures include (where "I" represents a compound of formula (I)): I + acetochlor; I + acifluorfen (including acifluorfen-sodium); I + aclonifen; I + ametryn; I + amicarbazone; I + aminopyralid; I + aminotriazole; I + atrazine; I + beflubutamid-M; I + benquitrione; I + bensulfuron (including bensulfuron-methyl); I + bentazon; I + bicyclopyrone; I + vilanaphos ... Spirivac-sodium; I + bixlozone; I + bromacil; I + bromoxynil; I + butachlor; I + butafenacil; I + carfentrazone (including carfentrazone-ethyl); I + cloransulam (including cloransulam-methyl); I + chlorimuron (including chlorimuron-ethyl); I + chlorotoluron; I + chlorsulfuron; I + cinmethylin; I + clasifos; I + clethodim; I + clodinafop (including clodinafop-propargyl) including); I + Clomazone; I + Clopyralid; I + Cyclopyranil; I + Cyclopirimorate; I + Cyclosulfamuron; I + Cyhalofop (including cyhalofop butyl); I + 2,4-D (including its choline salt and 2-ethylhexyl ester); I + 2,4-DB; I + Desmedipham; I + Dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloropropion, diglycolamine, dimethylamine, dimethylammonium) I + diclosulam; I + diflufenican; I + diflufenzopyr; I + dimethachlor; I + dimethenamid-P; I + diquat dibromide; I + diuron; I + epirifenacil; I + ethalfluralin; I + ethofumesate; I + fenoxaprop (including fenoxaprop-P-ethyl); I + fenoxasulfone; I + fenquinotrione; I + fentrazamide; I + flazasulfuron; I + florasulam;I + Florpyrauxifen (including Florpyrauxifen-benzyl); I + Fluazifop (including Fluazifop-p-butyl); I + Flucarbazone (including Flucarbazone-sodium); I + Flufenacet; I + Flumetsulam; I + Flumioxazin; I + Fluometuron; I + Flupyrsulfuron (including Flupyrsulfuron-methyl-sodium); I + Fluroxypyr (including Fluroxypyr-meptyl); I + Fomesafen; I + Foramsulfuron; I + Glufosinate (including its ammonium salt); I + Glyphosate (including its diammonium, isopropylammonium, and potassium salts); I + Halauxifen (including haloxyfop-methyl); I + Haloxyfop (including haloxyfop-methyl); I + Hexazinone; I + Hydantocidin; I + Imazamox; I + Imazapic; I + Imazapyr; I + Imazethapyr; I + Indaziflam; I + Iodosulfuron (including iodosulfuron-methyl-sodium); I + Iofensulfuron (including iofensulfuron-sodium); I + Ioxynil; I + Isoproturon; Isooxaflutole; Ilancotrione; IMCPA; IMCPB; Imecoprop-P; Imesosulfuron (including mesosulfuron-methyl); Imesotrione; Imetamitron; Imetazachlor; Imethiozolin; Imetolachlor; Imetosulam; Imetribuzin; Imetsulfuron; Inapropamide; Inicosulfuron; Inorflurazon; Ioxadiazon; Ioxasulfuron; Ioxyfluorfen; Iparaquat dichloride; Ipendimethalin; I Penoxulam; I + Phenmedipham; I + Picloram; I + Pinoxaden; I + Pretilachlor; I + Primisulfuron-methyl; I + Prometryn; I + Propanil; I + Propaquizafop; I + Propyrisulfuron; I + Propyzamide; I + Prosulfocarb; I + Prosulfuron; I + Pyraclonil; I + Pyraflufen (including Pyraflufen-ethyl); I + Pyrasulfotole; I + Pyridate; I + Pyriftalid; I + Pyrimisulfan; I + Pyroxasulfone; I + Pyroxulam; I + Quinclorac; I + Quinmelac;I + Quizalofop (including Quizalofop-P-ethyl and Quizalofop-P-tefuryl); I + Rimsulfuron; I + Saflufenacil; I + Sethoxydim; I + Simazine; I + S-Metallochlor; I + Sulfentrazone; I + Sulfosulfuron; I + Tebuthiuron; I + Tefuryltrione; I + Tembotrione; I + Terbuthylazine; I + Terbutryn; I + Tetflupyrrolimet; I + Thiencarbazone; I + Thifensulfuron; I + Thiafenacil; I + Tolpyralate; I + Topramezone; I + Tralkoxydim; I + Triafamone; I + To Triallate;I + Triasulfuron;I + Tribenuron (including tribenuron-methyl);I + Triclopyr;I + Trifloxysulfuron (including trifloxysulfuron-sodium);I + Trifludimoxadine;I + Trifluralin;I + Triflusulfuron;I + 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester;I + 4-hydroxy -1-Methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I + 4-Hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I + 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I + 4-Hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one;I + 4-Hydroxy-1,5-dimethyl-3-[1-methyl-5 -(Trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one;I+(4R)1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one;I+3-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione;I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione;I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione;I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione;I+6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione;I+2-[2-(3, 4-Dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-ethyl-cyclohexane-1,3-dione;I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-4,4,6,6-tetramethyl-cyclohexane-1,3-dione;I+2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione;I+3-[6-Cyclopropyl- 2-(3,4-Dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione;I+2-[6-Cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione;I+6-[6-Cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione;I+2-[ 6-Cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione;I + 4-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione;I + 4-[6-Cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione;I+4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (its agrochemically acceptable esters, e.g., methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, prop-2-ynyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, -carboxylate and cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate; I + 3-ethylsulfanyl-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide; I + 3-(isopropylsulfanylmethyl)-N-(5-methyl-1, 3,4-Oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide;I+3-(Isopropylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide;I+3-(Ethylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide (xadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide;I + ethyl 2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy]acetate;I + 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one;I+1-[2-chloro-6-(5-chloropyrimidin-2-yl)oxy-phenyl]-4,4,4-trifluoro-butan-1-one and I+5-[2-chloro-6-(5-chloropyrimidin-2-yl)oxy-phenyl]-3-(difluoromethyl)isoxazole. The mixing partners of the compounds of formula (I) may also be in the form of esters or salts, as for example mentioned in The Pesticide Manual, Fourteenth Edition, British Crop Protection Council, 2006.

[0153] The compounds of formula (I) may also be used in mixtures with other pesticides such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual.

[0154] The mixing ratio of the compound of formula (I) to the mixing partner is preferably 1:100 to 1000:1.

[0155] Mixtures may be advantageously used in the above mentioned formulations (in which case "active ingredient" relates to the respective mixture of the compound of formula (I) with the mixing partner).

[0156] The compounds of formula (I) of the present invention may also be combined with herbicide safeners. Preferred combinations (where "I" represents the compound of formula (I)) include: I + benoxacor, I + cloquintocet (including cloquintocet-mexyl); I + cyprosulfamide; I + dichlormid; I + fenchlorazole (including fenchlorazole-ethyl); I + fenclorim; I + fluxofenim; I + furilazole I + isoxadifen (including isoxadifen-ethyl); I + mefenpyr (including mefenpyr-diethyl); I + metcamifen and I + oxabetrinil.

[0157] Particularly preferred are mixtures of compounds of formula (I) with cyprosulfamide, isoxadifen (including isoxadifen-ethyl), cloquintocet (including cloquintocet-mexyl) and / or N-(2-methoxybenzoyl)-4-[(methyl-aminocarbonyl)amino]benzenesulfonamide.

[0158] The safeners of the compounds of formula (I) can also be used as pesticides, for example as described in The Pesticide Manual, 14 th Edition (BCPC), 2006. A reference to cloquintocet-mexyl also applies to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, a reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.

[0159] Preferably, the mixing ratio of the compound of formula (I) to the safener is from 100:1 to 1:10, in particular from 20:1 to 1:1.

[0160] The compounds of formula (I) can also be used in mixtures with other agricultural chemicals, such as fungicides, nematicides or insecticides, examples of which are given in the Pesticide Manual.

[0161] The mixing ratio of the compound of formula (I) to the mixing partner is preferably 1:100 to 1000:1.

[0162] The mixtures can be used advantageously in the abovementioned formulations (in this case "active ingredient" relates to the respective mixture of compound of formula I with mixing partner).

[0163] The present invention still further provides a method for selectively controlling weeds in a habitat containing crops and weeds, the method comprising applying a weed-controlling amount of a composition according to the present invention to the habitat. "Controlling" means killing, reducing or delaying growth, or preventing or reducing germination. Generally, the plants to be controlled are unwanted plants (weeds). "Habitat" means the area in which plants are growing or will grow.

[0164] The application rates of the compounds of formula (I) may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application in the seed furrow; no tillage application, etc.), the crop, the weeds to be controlled, the prevailing climatic conditions, and other factors influenced by the method of application, the time of application, and the target crop. The compounds of formula I according to the invention are generally applied at a rate of 10 to 2000 g / ha, in particular 50 to 1000 g / ha.

[0165] Application is generally by spraying the composition, typically with a tractor-mounted sprayer for broad areas, although other methods such as dusting (for dusts), drip or drench can also be used.

[0166] Useful plants on which the compositions of the present invention can be used include crops such as cereals, e.g., barley and wheat, cotton, oilseed rape, sunflower, corn, rice, soybeans, sugar beets, sugarcane and turf.

[0167] Crops may also include trees such as fruit trees, palm trees, coconut trees or other nuts, as well as vines such as grapes, fruit bushes, fruit plants and vegetables.

[0168] It should be understood that crops also include those that have been made tolerant to herbicides or types of herbicides (e.g., ALS-, GS-, EPSPS-, PPO-, ACCase-, and HPPD inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been made tolerant to imidazolinones, such as imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made tolerant to herbicides by genetic engineering methods include, for example, glyphosate-resistant and glufosinate-resistant corn varieties commercially available under the trade names RoundupReady® and LibertyLink®. In a particularly preferred embodiment, the crop is engineered to overexpress homogentisate solanesyltransferase, as taught, for example, in WO 2010 / 029311.

[0169] Crops should also be understood to be crops that have been made resistant to pests by genetic engineering methods, such as Bt corn (resistant to the European corn borer), Bt cotton (resistant to the Mexican boll weevil), and even Bt potato (resistant to the Colorado potato beetle). An example of Bt corn is the Bt 176 corn hybrid from NK® (Syngenta Seeds). Bt toxins are proteins naturally formed by the soil bacterium Bacillus thuringiensis. Examples of toxins, or transgenic plants capable of synthesizing such toxins, are described in EP-A-451878, EP-A-374753, WO-A-93 / 07278, WO-A-95 / 34656, WO-A-03 / 052073, and EP-A-427529. Examples of transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard®, and Protexcta®. Either the plant crop or its seed material can be tolerant to herbicides and at the same time resistant to insect feeding ("stacked transgenic events"). For example, seeds can have the ability to express the insecticidal Cry3 protein and at the same time be tolerant to glyphosate.

[0170] Crops should also be understood to include crops obtained by traditional breeding methods or by genetic modification and containing so-called output traits (e.g., improved storage stability, higher nutritional value and improved flavor).

[0171] Other useful plants include turfgrass, for example in golf courses, lawns, parks and roadsides, or commercially grown for lawns, and ornamental plants such as flowers or shrubs.

[0172] The compositions can be used to control unwanted plants (collectively, "weeds"), including monocotyledonous species such as Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitalia, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum. This includes both Sorghum and dicotyledonous species such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium. Weeds may also be considered crops, but may include plants that grow outside of the crop area ("escapes") or that grow from seeds left over from a different crop that was previously planted ("volunteers"). Such volunteers or escapes may be resistant to certain other herbicides.

[0173] Various aspects and embodiments of the invention will now be illustrated in more detail by way of example, it being understood that modifications of detail can be made without departing from the scope of the invention. Another aspect of the present invention may be as follows. [1] Compound of formula (I) [ka] or its salt or N-oxide [In the formula, R 1 is C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Alkoxy, C 1 ~C 2 Alkoxy-C 1 ~C 2 Alkyl, C 2 ~C 4 Alkenyl, C 1 ~C 4 Haloalkyl, Cyano-C 1 ~C 4 Alkyl, C 2 ~C 4 Haloalkenyl, C 2 ~C 4 Alkynyl and C 2 ~C 4 haloalkynyl; R 2 is hydrogen, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 3 Haloalkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 6 Alkoxy, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 3 ~C 6 Cycloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 1 ~C 6 Hydroxyalkyl-, C 1 ~C 6 Alkylcarbonyl-, -S(O) m C 1 ~C 6 Alkyl, Amino, C 1 ~C 6 Alkylamino, C 1 ~C 6 Dialkylamino, -C(C 1 ~C 3 alkyl)=NOC 1 ~C 3 Alkyl and C 2 ~C 6 haloalkynyl; G is hydrogen or C(O)R 3 and; R 3 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 1 ~C 6 Alkyl-S-, C 1 ~C 6 Alkoxy, -NR 4 R 5 and one or more R 6 phenyl optionally substituted with; Each R 4 and R 5 is hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, and C 3 ~C 6 cycloalkyl; or R 4 and R 5 together can form a morpholinyl ring; Each R 4a and R 5a is C 1 ~C 6 Alkoxy, and C 3 ~C 6 cycloalkyl; or R 4a and R 5a together can form a morpholinyl ring; R 6 is halogen, cyano, nitro, C 1 ~C 3 Alkyl, C 1 ~C 3 Haloalkyl, C 1 ~C 3 Alkoxy and C 1 ~C 3 haloalkoxy; X and Y are each independently hydrogen, C 1 ~C 3 Alkyl, cyclopropyl, C 1 ~C 3 Alkoxy, C 1 ~C 3 Haloalkyl, C 1 ~C 3 haloalkoxy, or halogen; D is R on at least one ring carbon atom 8 and / or substituted on at least one ring nitrogen atom with R 9 a substituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, substituted with At least one R 8 is C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, -S(O) m -C 3 ~C 6 Cycloalkyl, -OS(O) 2 C 1 ~C 3 Alkyl, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, -C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -Alkyl-, -NR 4a R 5a , -C(S)NR4 R 5 , -S(O) 2 NHC(O)C 1 ~C 3 Alkyl, -S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, -C(O)NHS-(O) 2 C 1 ~C 6 Alkyl, -C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 、C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 Alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 Alkyl)amino-, C 1 ~C 6 Alkylsulfonylamino-, C 1 ~C 6 Alkyl sulfonyl (C 1 ~C 6 Alkyl)amino-, C 1 ~C 6 Haloalkylsulfonylamino-, C 1 ~C 6 Haloalkylsulfonyl (C 1 ~C 6 Alkyl)amino-, C 3 ~C 6 Cycloalkylsulfonylamino-, C 3 ~C 6 Cycloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, hydroxyamino-, hydroxy(C 1 ~C 6 Alkyl)amino, C 1 ~C 6 Alkoxyamino, C 1 ~C 6 Alkoxy (C 1 ~C 6 Alkyl)amino, C 1 ~C 6 Haloalkoxyamino, C 1 ~C 6 Haloalkoxy(C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, wherein the ring system is selected from the group consisting of 0 to 5 R 16 is replaced by; At least one R9 is C 5 ~C 6 Alkyl, C 5 ~C 6 Haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 3 Alkoxy-C 3 Alkyl-, C 3 Alkoxy-C 1 ~C 2 Alkyl-, C 1 ~C 3 Haloalkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 6 Hydroxyalkyl-, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, -C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -alkyl- and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0 to 5 R 16 is replaced by; m is an integer of 0, 1, or 2; Each R 16 are independently halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy or C 1 ~C 6 Is it haloalkoxy; Or D is at least one R 8 is a phenyl ring substituted with; W is

change

change

change

change

change

[10] above, selected from the group consisting of haloalkynyl.

[12] The compound according to any one of the above [1] to

[11] , wherein D is a substituted or unsubstituted monocyclic heteroaryl ring.

[13] The compound according to any one of the above [1] to

[11] , wherein D is a substituted or unsubstituted phenyl ring.

[14] W is W1 and R 10 、R 11 、R 12 , and R 13 The compound according to any one of the above [1] to

[13] , wherein each of

[15] W is W2 and R 14 and R 15 The compound according to any one of the above [1] to

[13] , wherein each of

[16] The compound according to any one of the above [1] to

[13] , wherein W is W3.

[17] A herbicidal composition comprising the herbicidal compound according to any one of the above [1] to

[16] and an agriculturally acceptable formulation aid.

[18] The herbicidal composition according to

[17] , further comprising at least one additional pest control agent.

[19] The herbicidal composition according to

[18] , wherein the additional pest control agent is a herbicide or a herbicide safener.

[20] A method for controlling undesirable plant growth, comprising the step of applying the compound of formula (I) described in any one of [1] to

[16] above or the herbicidal composition described in any one of

[17] to

[19] above to the undesirable plants or a location thereof.

[21] Use of the compound of formula (I) described in any one of the above [1] to

[16] as a herbicide.

[0174] Typical abbreviations used herein include the following: br = widened t Bu = tert-butyl d=double line dba = dibenzylideneacetone DCM = dichloromethane DMSO = dimethyl sulfoxide DPPA = diphenylphosphoryl azide Et2O = diethyl ether EtOAc = ethyl acetate h=time m=multiplet Me = methyl MeOH = methanol Ph = phenyl i Pr = isopropyl rt=room temperature s=single line t=triple line THF = tetrahydrofuran [Example]

[0175] Example 1 Preparation of 4-[3-chloro-6-fluoro-2-[2-(4-phenylphenyl)ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.027) [ka] 1.1 3-Allyl-2-bromo-1-chloro-4-fluoro-benzene A solution of lithium diisopropylamide (2 M in tetrahydrofuran, 3.6 ml, 7.2 mmol) was cooled to −78° C. under nitrogen. A solution of 2-bromo-1-chloro-4-fluoro-benzene (1.0 g, 4.8 mmol) in tetrahydrofuran was added dropwise at −78° C. The mixture was stirred at the same temperature for 45 minutes and then treated with allyl bromide (0.3 ml, 5.7 mmol). The reaction was continued at −78° C. for 2 hours and then warmed to room temperature. The reaction was quenched with saturated NH4Cl (aq.) and extracted with ethyl acetate. The organics were separated, retained, and then washed with brine. The organics were dried over sodium sulfate and concentrated under reduced pressure to give 3-allyl-2-bromo-1-chloro-4-fluoro-benzene (1.2 g, 100%) as an oil. [ka] 1 H NMR (400 MHz, CDCl3) δ H :7.34-7.30(m,1H),7.01-6.96(m,1H),5.94-5.83(m,1H),5.10-5.00(m,2H),3.64-3.58(m,2H).

[0176] 1.2 2-(2-Bromo-3-chloro-6-fluoro-phenyl)acetic acid A solution of 3-allyl-2-bromo-1-chloro-4-fluoro-benzene (15.0 g, 60.1 mmol) in dichloromethane (200 mL) in a two-neck flask was cooled to -78 °C. One side tube was connected to a trap containing an aqueous solution of KI. Ozone was bubbled through the solution until the starting material was completely consumed (5 h). Air was bubbled through the solution for 10 min to remove excess ozone. Dimethyl sulfide (44 ml, 601 mmol) was added, and the mixture was allowed to warm to room temperature. The reaction was continued at room temperature for 16 h.

[0177] The mixture was washed with brine (2 x 100 mL) and the organic layer was retained. The organics were dried over NaSO, filtered, and concentrated under reduced pressure to give crude 2-(2-bromo-3-chloro-6-fluoro-phenyl)acetaldehyde (15.3 g), which was used for the next step without further purification.

[0178] Crude 2-(2-bromo-3-chloro-6-fluoro-phenyl)acetaldehyde (15.3 g, 60.8 mmol) was dissolved in a mixture of tert-butanol (92 mL) and water (46 mL) and then cooled to 0 °C. 2-Methylbut-2-ene (64.5 mL, 608 mmol), sodium dihydrogen phosphate (34.6 g, 243 mmol), and sodium chlorite (16.5 g, 163 mmol) were added. The mixture was stirred for 2 hours and then diluted with brine (150 mL) and 2 M hydrochloric acid (150 mL). The mixture was extracted with ethyl acetate (3 × 100 mL). The combined organic extracts were washed with a saturated aqueous solution of sodium metabisulfite (100 mL), then dried over Na SO , filtered, and concentrated under reduced pressure to give a pale yellow solid. The crude solid was dissolved in a mixture of water (100 mL) and 2.0 M NaOH (30 mL). The aqueous solution was washed with ethyl acetate (100 mL) and the organics were discarded. The aqueous layer was acidified by adding concentrated hydrochloric acid (20 mL), resulting in the formation of a white suspension. The mixture was extracted with ethyl acetate (3 x 200 mL). The combined organics were washed with brine, dried over Na2SO4, filtered, and evaporated to give 2-(2-bromo-3-chloro-6-fluoro-phenyl)acetic acid (8.0 g, 49%) as a white solid. [ka] 1 H NMR (400 MHz, DMSO-d6) δ H :12.79(br.s,1H),7.67-7.59(m,1H),7.39-7.31(m,1H),3.82(s,2H).

[0179] 1.3 2-(2-Bromo-3-chloro-6-fluoro-phenyl)-N-methyl-acetohydrazide To a stirred solution of 2-(2-bromo-3-chloro-6-fluorophenyl)acetic acid (2.0 g, 7.5 mmol) in dichloromethane (20 mL) at 0 °C was added N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride [EDC·HCl] (1.4 g, 9.0 mmol), followed by the dropwise addition of methylhydrazine (0.4 mL, 7.5 mmol). The temperature of the reaction mixture was maintained at 0 °C for 3 h. The reaction was then quenched with water and extracted into dichloromethane. The organics were separated, washed with brine, and dried over Na SO . Concentration under reduced pressure gave crude 2-(2-bromo-3-chloro-6-fluorophenyl)-N-methyl-acetohydrazide (1.8 g, 81%), which was used in the next step without further purification. [ka] 1 H NMR (400 MHz, DMSO-d6) δ H :7.59(dd,J=8.9 and 5.4,1H),7.30(t,J=8.9,1H),4.91(s,2H),4.10(br.s,2H),3.02(s,3H).

[0180] 1.4 2-{[2-(2-Bromo-3-chloro-6-fluoro-phenyl)-acetyl]-methyl-hydrazono}-propionic acid ethyl ester To a stirred solution of 2-(2-bromo-3-chloro-6-fluoro-phenyl)-N-methyl-acetohydrazide (1.8 g, 6.09 mmol) in ethanol (5 ml) was added dropwise ethyl pyruvate (0.7 ml, 6.7 mmol). The reaction was heated at 80° C. for 4 hours. The reaction mixture was then cooled to room temperature and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give the desired compound 2-{[2-(2-bromo-3-chloro-6-fluoro-phenyl)-acetyl]-methyl-hydrazono}-propionic acid ethyl ester (1.8 g, 75%) as an off-white solid. [ka] 1 H NMR (400 MHz, CDCl3) δ H :7.40-7.35(m,1H),7.04-6.98(m,1H),4.32(q,J=7.1,2H),4.24(s,2H),3.41(s,3H),2.32(s,3H),1.36(t,J=7.1,3H).

[0181] 1.5 4-(2-Bromo-3-chloro-6-fluoro-phenyl)-5-hydroxy-2,6-dimethyl-pyridazin-3-one 2-{[2-(2-Bromo-3-chloro-6-fluoro-phenyl)-acetyl]-methyl-hydrazono}-propionic acid ethyl ester (500 mg, 1.27 mmol) was dissolved in acetonitrile (2.5 ml) and treated with 1,8-diazabicyclo[5.4.0]undec-7-ene [DBU] (0.47 ml, 3.2 mmol). The mixture was heated to 125 °C using microwave irradiation for 1 hour. The reaction mixture was then evaporated under reduced pressure. The residue was dissolved in water and acidified to pH 1 with 2 N hydrochloric acid. The mixture was extracted with DCM, and the organics were separated and washed with brine solution. The organic solution was dried over Na2SO4 and concentrated under reduced pressure to give the crude product. The crude material was purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give 4-(2-bromo-3-chloro-6-fluoro-phenyl)-5-hydroxy-2,6-dimethyl-pyridazin-3-one (340 mg, 77.1%) as an off-white solid. [ka] 1 H NMR (400 MHz, DMSO-d6) δ H :11.01(s,1H),7.77-7.73(m,1H),7.39(t,J=8.7,1H),3.58(s,3H),2.24(s,3H).

[0182] 1.6 [5-(2-bromo-3-chloro-6-fluoro-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate To a stirred solution of 4-(2-bromo-3-chloro-6-fluoro-phenyl)-5-hydroxy-2,6-dimethyl-pyridazin-3-one (1.4 g, 4.02 mmol) in dichloromethane (32 ml) was added triethylamine (1.1 ml, 8.06 mmol), 4-(dimethylamino)pyridine [DMAP] (49 mg, 0.40 mmol) and isobutyryl chloride (0.6 ml, 4.83 mmol) at room temperature.

[0183] Upon determination of completion, the reaction was diluted with dichloromethane and water. The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure to give the crude product. The crude material was purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give [5-(2-bromo-3-chloro-6-fluoro-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate (1.47 g, 87%). [ka] 1 H NMR (400 MHz, CDCl3) δ H :7.51-7.47(m,1H),7.10-7.05(m,1H),3.82(s,3H),2.60-2.55(m,1H),2.25(s,3H),1.02-0.98(m,6H).

[0184] 1.7 4-[3-chloro-6-fluoro-2-[(E)-2-(4-phenylphenyl)vinyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-2.027) [5-(2-Bromo-3-chloro-6-fluoro-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (0.54 g, 1.3 mmol), KCO (0.55 g, 3.9 mmol), trans-2-(4-phenylphenyl)vinylboronic acid (0.44 g, 2.00 mmol), PdCl(dppf).DCM (53 mg, 0.065 mmol), 1,4-dioxane (13 ml) and HO (3.3 mL) were combined in a 20 mL microwave vial and then heated at 140 °C under microwave irradiation for 30 minutes.

[0185] The reaction mixture was concentrated in vacuo to remove 1,4-dioxane and then partitioned between 2N HCl (aq) and DCM. The organic layer was separated and the aqueous layer was extracted with two additional portions of DCM. The combined organics were concentrated in vacuo to give a crude residue that was purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give 4-[3-chloro-6-fluoro-2-[(E)-2-(4-phenylphenyl)vinyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (343 mg, 53%, A-2.027)) as a yellow foam. [ka] 1 H NMR (400 MHz, chloroform) δ = 7.59-7.33 (m, 10H), 7.07 (t, J = 8.6 Hz, 1H), 7.01 (d, J = 16.4 Hz, 1H), 6.70 (d, J = 16.5 Hz, 1H), 5.63 (s, 1H), 3.73 (s, 3H), 2.28 (s, 3H)

[0186] 1.8 4-(3-chloro-6-fluoro-2-phenethyl-phenyl)-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.027) To a 10 mL round-bottom flask was added 5% Pd / C (73 mg, 0.034 mmol), followed by a 10:1 (v / v) DCM / MeOH (4 mL) solution of 4-[3-chloro-6-fluoro-2-[(E)-2-(4-phenylphenyl)vinyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (308 mg, 0.69 mmol). B2(OH)4 (325 mg, 3.45 mmol) was then added, and the reaction mixture was stirred at room temperature overnight.

[0187] The reaction mixture was then filtered through Celite® eluting with 10:1 (v / v) DCM / MeOH. The filtrate was dry-loaded onto silica gel and purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give 4-[3-chloro-6-fluoro-2-[2-(4-phenylphenyl)ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (299 mg, 97% yield, A-1.027) as a yellow oil that solidified upon standing. [ka] 1 H NMR (400 MHz, chloroform) δ = 7.57-7.52 (m, 2H), 7.50-7.40 (m, 5H), 7.37-7.30 (m, 1H), 7.07 (d, J = 8.2 Hz, 2H), 7.02 (t, J = 8.6 Hz, 1H), 5.47 (s, 1H), 3.75 (s, 3H), 2.88-2.80 (m, 3H), 2.27 (s, 3H).

[0188] Example 2 Preparation of 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]benzonitrile (A-1.036) [ka] 2.1 [5-[3-chloro-2-[(E)-2-(4-cyanophenyl)vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (4.036) [5-(2-Bromo-3-chloro-6-fluoro-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate (1.10 g, 2.63 mmol) [prepared as described in Example 1] and chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II) (68 mg, 0.13 mmol) were combined in degassed toluene (12 mL). 4-Vinylbenzonitrile (408 mg, 3.16 mmol) and Hunig's base (0.92 mL, 5.27 mmol) were then added, and the reaction mixture was heated to 95° C. for 2.5 hours.

[0189] The reaction mixture was cooled to room temperature, then diluted with dichloromethane, filtered through Celite, and washed with additional dichloromethane. The filtrate was concentrated in vacuo and then purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give [5-[3-chloro-2-[(E)-2-(4-cyanophenyl)vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate (781 mg, 64% yield, A-4.036) as a white solid. [ka] 1 H NMR (400MHz, chloroform) δ=7.62-7.55(m,2H),7.45(dd,J=5.0,8.5Hz,1H),7.45-7.40(m,1H),7.13(d,J=16.5Hz,1H),7.05(t,J=8.5 Hz,1H),6.68(d,J=16.5Hz,1H),3.69(s,3H),2.65(spt,J=7.0Hz,1H),2.23(s,3H),1.11(d,J=7.0Hz,3H),1.07(d,J=7.0Hz,3H).

[0190] 2.2 [5-[3-chloro-2-[2-(4-cyanophenyl)ethyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (A-3.036) [5-[3-chloro-2-[(E)-2-(4-cyanophenyl)vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (900 mg, 1.93 mmol) was subjected to catalytic hydrogenation in EtOAc (20 mL) over 5% Pd / C (50% wet) catalyst (0.82 g) at 4 bar H.

[0191] After 1.5 hours, LC / MS indicated complete reaction. The reaction mixture was filtered through a pad of Celite® and washed with ethyl acetate. The filtrate was concentrated in vacuo to give a crude residue.

[0192] The residue was adsorbed onto silica and purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to afford [5-[3-chloro-2-[2-(4-cyanophenyl)ethyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (800 mg, 81% yield, A-3.036) as a white solid. [ka] 1 H NMR (400MHz, chloroform) δ=7.56-7.51(m,2H),7.42(dd,J=5.2,8.9Hz,1H),7.26-7.21(m,2H),7.00(t,J=8.9Hz,1H),3.84(s,3H),3.02-2 .92(m,1H),2.91-2.80(m,2H),2.75-2.65(m,1H),2.54(spt,J=7.0Hz,1H),2.25(s,3H),0.98(d,J=7.0Hz,3H),0.95(d,J=7.0Hz,3H).

[0193] 2.3 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]benzonitrile (A-1.036) [[5-[3-chloro-2-[2-(4-cyanophenyl)ethyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate (400 mg, 0.855 mmol) was dissolved in ethanol (6 mL). The mixture was treated with a solution of lithium hydroxide (108 mg, 2.56 mmol) in water (2 mL). The reaction was stirred at room temperature for 2 hours.

[0194] The reaction mixture was concentrated in vacuo to remove ethanol. The remaining aqueous solution was diluted with water (15 mL) and then acidified with 2 M HCl to approximately pH 3 and extracted with DCM (3 x 10 mL). The combined organics were dried over MgSO, filtered, and concentrated in vacuo to give the crude product.

[0195] The crude product was purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]benzonitrile (83 mg, 91% yield, A-1.036)) as a white solid. [ka] 1 H NMR(400MHz,CDCl3)δ ppm 7.46-7.51(m,2H)7.26-7.31(m,1H)7.08(d,J=8.19Hz,2H)6.86(t,J=8.50Hz,1H)3.63(s,3H)2.61-2.77(m,4H)2.24(s,3H).

[0196] Example 4 Preparation of 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]-N-ethyl-2-fluoro-N-methyl-benzamide (A-1.028) [ka] 4.1 [5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate [5-(2-Bromo-3-chloro-6-fluoro-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (5.00 g, 11.97 mmol, 1.0 equiv.), 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (2.63 g, 14.36 mmol, 1.2 equiv.), and chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II) (307 mg, 0.60 mmol, 0.05 equiv.) were charged into a 250 ml round-bottom flask equipped with a condenser, stir bar, and nitrogen bubbler. Under a stream of nitrogen, THF (100 mL) was added followed by N,N-diisopropylethylamine (4.2 mL, 23.94 mmol, 2.0 equiv) and the mixture was heated to reflux for 3 h.

[0197] The reaction mixture was cooled to room temperature, then diluted in DCM and filtered through Celite®, washing with a further portion of DCM, and the eluent was then concentrated to dryness.

[0198] The crude product was purified by flash column chromatography to give [5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (5.91 g, 11.4 mmol, 95% yield) as an off-white solid. [ka] 1 H NMR(400MHz,DMSO-d6)δ=7.63(dd,J=5.1,8.9Hz,1H),7.31(t,J=8.9Hz,1H),6.65(d,J=18.3Hz,1H),5.68(d,J=18.3Hz,1H),4.24(dd,J =11.9,17.2Hz,2H),3.95-3.83(m,2H),3.70(s,3H),2.66(spt,J=7.0Hz,1H),2.16(s,3H),0.90(d,J=7.0Hz,3H),0.89(d,J=7.0Hz,3H)

[0199] 4.2 [5-[3-chloro-2-[2-[4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl]ethyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (A-3.028) [5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (500 mg, 0.96 mmol), KPO (886 mg, 3.85 mmol), and 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf).DCM] (39 mg, 0.05 mmol) were added to a 20 mL microwave vial. THF (10 mL), 4-bromo-N-ethyl-2-fluoro-N-methyl-benzamide (500 mg, 1.92 mmol) and water (0.35 mL) were added and the reaction mixture was then heated to 100° C. under microwave irradiation for 2 h.

[0200] The reaction mixture was concentrated in vacuo to remove THF and then diluted with water (20 mL) and DCM (20 mL). The organic layer was separated and the aqueous layer was extracted with DCM (3 × 5 mL). The combined organics were dried and concentrated in vacuo to give a crude residue which was purified by column chromatography on silica gel eluting with a gradient of cyclohexane / ethyl acetate to give [5-[3-chloro-2-[(E)-2-[4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl]vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (397 mg, 76% yield, A-4.028) as an off-white solid.

[0201] [5-[3-chloro-2-[(E)-2-[4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl]vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (300 mg, 0.55 mmol) was subjected to catalytic hydrogenation in EtOAc (6 mL) over 5% Pd / C (50% wet) catalyst (0.12 g) at 3 bar H.

[0202] After 5.5 hours, LC / MS indicated complete reaction. The reaction mixture was filtered through a pad of Celite® and washed with ethyl acetate / methanol. The filtrate was concentrated in vacuo to give a crude residue.

[0203] The residue was adsorbed onto silica and purified by column chromatography on silica gel (eluent, ethyl acetate / hexane gradient) to give [5-[3-chloro-2-[2-[4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl]ethyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (285 mg, 95% yield, A-3.028) as a colorless gum. [ka] [NMR of a mixture of rotamers] 1H NMR (400MHz, chloroform) δ=7.42(dd,J=5.1,8.9Hz,1H),[7.25(t,J=7.2Hz,0.5H),7.21(t,J=7.5Hz,0.5H)],6.99(t,J=8.9Hz,1H),6.96(dd,J=1.2,7.5Hz ,1H),[6.89(dd,J=1.2,6.9Hz,1H),6.86(dd,J=1.2,6.9Hz,1H)],3.85(s,3 H),[3.59(q,J=7.4Hz,1H),3.24(q,J=7.4Hz,1H)],[3.08(s,1.5H),2.90(br s,1.5H)],2.88-2.78(m,3H),2.75-2.64(m,1H),2.55(spt,J=7.0Hz,1H),2.26(s,3H),[1.2 3(t,J=7.2Hz,1.5H),1.10(t,J=7.2Hz,1.5H)],0.98(d,J=7.0Hz,3H),0.96(d,J=7.1Hz,3H)

[0204] 4.3 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]-N-ethyl-2-fluoro-N-methyl-benzamide (A-1.028) [5-[3-chloro-2-[2-[4-[ethyl(methyl)carbamoyl]-3-fluoro-phenyl]ethyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate (300 mg, 0.55 mmol) was dissolved in ethanol (3 mL). The mixture was treated with a solution of lithium hydroxide (69 mg, 1.65 mmol) in water (3 mL). The reaction was stirred at room temperature for 2 hours.

[0205] The reaction mixture was concentrated in vacuo to remove ethanol. The remaining aqueous solution was diluted with water (15 mL) and then acidified with 2 M HCl to approximately pH 3 and extracted with DCM (3 x 10 mL). The combined organics were dried and concentrated in vacuo to give the crude product.

[0206] The crude product was purified by column chromatography on silica gel (eluent, DCM / methanol gradient) to give 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]-N-ethyl-2-fluoro-N-methyl-benzamide (224 mg, 86% yield, A-1.028) as a white solid. [ka] [NMR of a mixture of rotamers] 1 H NMR(400MHz,DMSO-d6)δ=10.86(br s,1H),7.55-7.49(m,1H),7.25-7.19(m,2H),6.95-6.89(m,2H),3.61(s,3H),3.46(q,J=7.1Hz,1H),3.12(q,J=7.1Hz, 1H),2.95(s,1.5H),2.78(s,1.5H),2.78-2.63(m,4H),2.26(s,3H),1.11(t,J=7.1Hz,1.5H),1.00(t,J=7.1Hz,1.5H).

[0207] Example 5 Preparation of [5-[3-chloro-2-[(E)-2-(4-cyclopropylphenyl)vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (A-4.038) [ka] 5.1 [5-(3-chloro-6-fluoro-2-vinyl-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate [5-(2-Bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate (4.177 g, 10.00 mmol, 1.0 equiv.) and tributyl(vinyl)stannane (4.384 mL, 15.00 mmol, 1.50 equiv.) were dissolved in toluene (60.00 mL), and then 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf).DCM] (408 mg, 0.50 mmol, 0.05 equiv.) was added. The reaction mixture was heated to reflux overnight.

[0208] The reaction mixture was cooled to room temperature and then concentrated in vacuo. The crude product was then purified by flash column chromatography to give [5-(3-chloro-6-fluoro-2-vinyl-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]-2-methylpropanoate as an off-white solid (3.02 g, 83% yield). [ka] 1 H NMR(400MHz,CDCl3)δ=7.40(dd,J=5.1,8.7Hz,1H),6.99(t,J=8.7Hz,1H),6.65(dd,J=11.6,17.6Hz,1H),5.37 -5.30(m,2H),3.79(s,3H),2.59(spt,J=7.0Hz,1H),2.23(s,3H),1.04(d,J=7.0Hz,4H),1.03(d,J=7.0Hz,1H)

[0209] 5.2 [5-[3-chloro-2-[(E)-2-(4-cyclopropylphenyl)vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (A-4.038) A stirred mixture of [5-(3-chloro-6-fluoro-2-vinyl-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (300 mg, 1.0 equiv.), chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II) (21 mg, 0.05 equiv.), 1-bromo-4-cyclopropylbenzene (243 mg, 1.5 equiv.) and N,N-diisopropylethylamine (0.29 mL, 2.0 equiv.) in toluene (5 mL) was heated to reflux under nitrogen for 3 hours.

[0210] The reaction mixture was cooled to room temperature, then diluted with DCM and filtered through a pad of Celite eluting with a further portion of DCM. The filtrate was concentrated in vacuo to give the crude product.

[0211] The crude product was purified by flash column chromatography to give [5-[3-chloro-2-[(E)-2-(4-cyclopropylphenyl)vinyl]-6-fluoro-phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (285 mg, 72% yield) as a pale yellow gum. [ka] 1 H NMR(400MHz,CDCl3)δ=7.41(dd,J=5.1,8.9Hz,1H),7.26-7.22(m,2H),7.02-6.98(m ,2H),6.99(t,J=8.9Hz,1H),6.93(d,J=16.5Hz,1H),6.59(d,J=16.5Hz,1H),3.71(s, 3H),2.62(spt,J=7.0Hz,1H),2.19(s,3H),1.87(tt,J=5.0,8.4Hz,1H),1.07(d,J=7. 0Hz,3H),1.06(d,J=7.0Hz,1H),0.99-0.93(m,J=2.0,8.4Hz,2H),0.73-0.64(m,2H).

[0212] Example 6 Preparation of 4-[3-chloro-6-fluoro-2-[2-(4-methylsulfanylphenyl)ethyl]-phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.039) [ka] 6.1 [5-[3-chloro-6-fluoro-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate An oven-dried round-bottom flask was then charged with Ir(COD)Cl (299 mg, 0.45 mmol) and 4-diphenylphosphanylbutyl(diphenyl)phosphane (0.380 mg, 0.89 mmol). The flask was evacuated and backfilled with nitrogen (×3), then THF (75 mL) was added, and the reaction was stirred at room temperature for 30 minutes. A THF solution of [5-(3-chloro-6-fluoro-2-vinyl-phenyl)-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate [prepared as described in Example 4] (6.7 g, 17.8 mmol) was added dropwise, and the mixture was stirred for 10 minutes, followed by the dropwise addition of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.02 mL, 20.8 mmol). The reaction was stirred at 60 °C overnight.

[0213] After 24 hours, the reaction was cooled to room temperature and then concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with a gradient of cyclohexane / ethyl acetate to give [5-[3-chloro-6-fluoro-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (4.50 g, 51% yield) as a yellow solid. [ka] 1H NMR (500MHz, chloroform) δ=7.35(dd,J=5.2,8.9Hz,1H),6.90(t,J=8.6Hz,1H),3.81(s,3H),2.59(t,J=8.5Hz,2H),2.53( spt,J=7.0Hz,1H),2.24(s,3H),1.32-1.16(m,12H),1.08-1.00(m,2H),0.98(d,J=7.0Hz,3H),0.94(d,J=7.0Hz,3H).

[0214] 6.2 4-[3-chloro-6-fluoro-2-[2-(4-methylsulfanylphenyl)ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.039) [5-[3-chloro-6-fluoro-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (100 mg, 0.20 mmol), 1-bromo-4-methylsulfanyl-benzene (62 mg, 0.30 mmol), chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (24 mg, 0.03 mmol), KCO (84 mg, 0.61 mmol), 1,4-dioxane (2 mL), and water (0.2 mL) were combined in a 5 mL microwave vial. The reaction mixture was then heated under microwave irradiation at 140° C. for 90 minutes.

[0215] The reaction mixture was cooled to room temperature, then diluted with water (10 mL), acidified with 2 M HCl to approximately pH 3, and extracted with DCM (4×). The combined organics were concentrated in vacuo, and the crude product was purified by mass-directed reverse-phase HPLC to give 4-[3-chloro-6-fluoro-2-[2-(4-methylsulfanylphenyl)ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one as a white solid (22 mg, 22% yield, A-1.039). [ka] 1 H NMR (400 MHz, chloroform) δ = 7.46-7.39 (m, 3H), 7.12 (d, J = 8.0 Hz, 2H), 6.98 (t, J = 8.6 Hz, 1H), 6.90 (d, J = 8.0 Hz, 2H), 3.73 (s, 3H), 2.84-2.64 (m, 4H), 2.45 (s, 3H), 2.29 (s, 3H).

[0216] Example 7 Preparation of 4-[3-chloro-6-fluoro-2-[2-[4-(methylsulfanylmethyl)phenyl]ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.388) [ka] 7.1 4-[3-chloro-6-fluoro-2-[(E)-2-[4-(methylsulfanylmethyl)phenyl]vinyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one [5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (500 mg, 0.96 mmol), 1-bromo-4-(methylsulfanylmethyl)benzene (324 mg, 1.44 mmol), 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf).DCM] (41 mg, 0.05 mmol), and potassium carbonate (417 mg, 2.89 mmol) were added to a 10-20 mL microwave vial under a nitrogen atmosphere. Degassed acetonitrile (11.5 mL) and water (2.9 mL) were added and the mixture was heated to 150° C. under microwave irradiation for 20 minutes.

[0217] The reaction mixture was concentrated to dryness. The residue was treated with water (20 ml) and the aqueous phase was acidified to pH 3 by the addition of 2 M HCl, resulting in the formation of a precipitate. DCM (20 ml) was added to dissolve the precipitate. Brine (20 ml) was added and the phases were separated. The aqueous phase was extracted with two further portions of DCM, and the combined organic extracts were then dried and concentrated directly onto silica. The crude material was purified by automated flash chromatography on silica gel eluting with a gradient of cyclohexane / ethyl acetate to give 4-[3-chloro-6-fluoro-2-[(E)-2-[4-(methylsulfanylmethyl)phenyl]vinyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (341 mg, 82% yield) as an off-white solid. [ka] 1 H NMR(500MHz,DMSO-d6)δ=10.78(br s,1H),7.60(dd,J=5.2,8.7Hz,1H),7.30-7.24(m,5H),6.93(d,J=16.5Hz,1H ),6.56(d,J=16.5Hz,1H),3.67(s,2H),3.54(s,3H),2.19(s,3H),1.94(s,3H)

[0218] 7.2 4-[3-chloro-6-fluoro-2-[2-[4-(methylsulfanylmethyl)phenyl]ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.388) To a solution of 4-[3-chloro-6-fluoro-2-[(E)-2-[4-(methylsulfanylmethyl)phenyl]vinyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (335 mg, 0.78 mmol) in tetrahydrofuran (12 mL) was added N,N-diisopropylethylamine (1.08 mL, 6.20 mmol) under a nitrogen atmosphere. The stirred reaction mixture was heated to 70 °C, and 2,4,6-triisopropylbenzenesulfonylhydrazide (2.06 g, 6.21 mmol) was added portionwise over 6 hours. The mixture was then heated to reflux for 16 hours. Additional N,N-diisopropylethylamine (0.68 mL, 3.89 mmol) was added to the reaction mixture, followed by 2,4,6-triisopropylbenzenesulfonylhydrazide (1.29 g, 3.89 mmol), and the mixture was heated to reflux for an additional 6 hours.

[0219] The reaction mixture was cooled to room temperature and then concentrated directly onto silica gel. The crude material was partially purified by automated flash chromatography on silica gel eluting with a gradient of cyclohexane / ethyl acetate. The resulting material was further purified by mass-directed reverse-phase HPLC to give 4-[3-chloro-6-fluoro-2-[2-[4-(methylsulfanylmethyl)phenyl]ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one as a white solid (208 mg, 62% yield, A-1.388). [ka] 1 H NMR(400MHz,d6-DMSO),δ=10.83(s,1H),7.56-7.53(m,1H),7.23-7.16(m,3H),6.96 -6.94(d,2H),3.62(s,2H),3.60(s,3H),2.68-2.54(m,4H),2.26(s,3H),1.92(s,3H)

[0220] Example 8 4-[3-chloro-6-fluoro-2-[2-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.385) [ka] 8.1 [4-(1,2,4-triazol-1-yl)phenyl]trifluoromethanesulfonate 4-(1,2,4-Triazol-1-yl)phenol (1.22 g, 7.57 mmol) was dissolved in dichloromethane (10 mL) under nitrogen and cooled to approximately 0° C. A solution of pyridine (1.22 mL, 15.1 mmol) in dichloromethane (5 mL) was added dropwise over approximately 2 minutes. The mixture was stirred for 5 minutes, and then a solution of trifluoromethanesulfonic anhydride (1.53 mL, 9.08 mmol) in dichloromethane (5 mL) was added dropwise over approximately 2 minutes. The cooling was removed, and the reaction mixture was allowed to warm to room temperature and then stirred at room temperature for 16 hours.

[0221] The reaction was quenched by the addition of 2 M aqueous HCl (20 ml), and the organic phase was then separated. The aqueous phase was further extracted with dichloromethane (2 × 20 ml). The combined organics were washed with water (20 ml), dried, and then concentrated under reduced pressure to give a cream-colored solid. The crude material was purified by automated flash chromatography on silica eluting with a gradient of cyclohexane / ethyl acetate to give [4-(1,2,4-triazol-1-yl)phenyl]trifluoromethanesulfonate as a white solid (2.02 g, 91% yield). [ka] 1 H NMR (400 MHz, chloroform) δ = 8.59 (s, 1H), 8.14 (s, 1H), 7.86-7.78 (m, 2H), 7.50-7.41 (m, 2H).

[0222] 8.2 [5-[3-chloro-6-fluoro-2-[(E)-2-[4-(1,2,4-triazol-1-yl)phenyl]vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate [5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (500 mg, 0.96 mmol), 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl(dppf).DCM] (39 mg, 0.048 mmol), [4-(1,2,4-triazol-1-yl)phenyl]trifluoromethanesulfonate (367 mg, 1.25 mmol), and potassium phosphate (834 mg, 3.85 mmol) were added to a 10-20 mL microwave vial.

[0223] Tetrahydrofuran (10 ml) and water (0.5 ml) were added and the reaction mixture was then degassed by stirring under vacuum and then backfilled with nitrogen (x3). The reaction mixture was heated under microwave irradiation in a microwave at 120°C for 60 minutes.

[0224] The reaction mixture was filtered through a plug of Celite® and washed with EtOAc and EtOH. The filtrate was concentrated under reduced pressure to give a brown gum (840 mg). The crude material was purified by automated flash chromatography on silica gel eluting with a gradient of cyclohexane / ethyl acetate to give a pale yellow gum (389 mg). The purified material was dissolved in acetonitrile (10 ml) and treated with SiliCycle SiliaMetS® thiol (SH) metal scavenger resin (365 mg) at room temperature. The suspension was stirred at room temperature for 3 hours, then filtered to remove the resin and washed with additional acetonitrile. The filtrate was concentrated in vacuo to give [5-[3-chloro-6-fluoro-2-[(E)-2-[4-(1,2,4-triazol-1-yl)phenyl]vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate as a colorless gum (361 mg, 73% yield). [ka] 1 H NMR (400 MHz, chloroform) δ ppm 8.55 (s, 1H), 8.11 (s, 1H), 7.60-7.66 (m, 2H), 7.42-7.53 (m, 3H), 7.01-7.10 (m, 2H), 6.69 (d, J = 16.5 Hz, 1H), 3.70 (s, 3H), 2.66 (spt, J = 7.0 Hz, 1H), 2.23 (s, 3H), 1.11 (d, J = 7.0 Hz, 1H), 1.08 (d, J = 7.1 Hz, 1H)

[0225] 8.3 [5-[3-chloro-6-fluoro-2-[2-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (A-3.385) [5-[3-Chloro-6-fluoro-2-[(E)-2-[4-(1,2,4-triazol-1-yl)phenyl]vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (365 mg, 0.72 mmol) was subjected to catalytic hydrogenation in EtOAc (10 mL) over 5% Pd / C (50% wet) catalyst (0.15 g) at 3 bar H for 24 h.

[0226] The reaction mixture was filtered through a pad of Celite® and washed with ethyl acetate. The filtrate was concentrated in vacuo to give a crude residue (350 mg), which was adsorbed onto silica gel and purified by automated flash chromatography on silica gel eluting with a gradient of cyclohexane / ethyl acetate. [5-[3-chloro-6-fluoro-2-[2-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (A-3.385) was obtained as a colorless gum (321 mg, 88% yield). [ka] 1 H NMR (400MHz, chloroform) δ=8.51(s,1H),8.09(s,1H),7.55(d,J=8.2Hz,2H),7.43(dd,J=5.2,8.7Hz,1H),7.27(d,J=8.2Hz,2H),7.00(t,J=8.7H) z,1H),3.84(s,3H),2.97-2.80(m,3H),2.79-2.67(m,1H),2.55(spt,J=7.0Hz,1H),2.25(s,3H),0.98(d,J=7.0Hz,3H),0.96(d,J=7.0Hz,1H)

[0227] 8.4 4-[3-chloro-6-fluoro-2-[2-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.385) [5-[3-chloro-6-fluoro-2-[2-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl]2-methylpropanoate (320 mg, 0.63 mmol) was stirred in ethanol (5 ml) at room temperature.

[0228] A solution of lithium hydroxide monohydrate (81 mg, 1.88 mmol) in water (2 ml) was added dropwise and the reaction stirred at room temperature for 1 hour.

[0229] The ethanol solvent was removed under reduced pressure, and the residue was diluted with water (20 ml). The aqueous phase was acidified to approximately pH 3-4 by adding 2 M HCl (aq) and then extracted with EtOAc (3 x 10 ml). The combined organic extracts were concentrated under reduced pressure to give a white solid (292 mg). The crude residue was purified by automated flash chromatography on silica eluting with a gradient of cyclohexane / ethyl acetate and ethyl acetate / ethanol to give 4-[3-chloro-6-fluoro-2-[2-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (A-1.365) as a white solid (260 mg, 94% yield). [ka] 1 H NMR (400MHz, methanol), δ ppm 9.03(s,1H),8.14(s,1H),7.65-7.70(m,2H),7.51(dd,J=5.2,8.7Hz,1H),7. 20(m,2H),7.11(t,J=8.7Hz,1H),3.72(s,3H),2.72-2.89(m,4H),2.32(s,3H)

[0230] Example 9 4-[3-cyclopropyl-6-fluoro-2-[2-(2-fluoro-4-pyridyl)ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (C-1.013) [5-[3-chloro-6-fluoro-2-[2-(2-fluoro-4-pyridyl)ethyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (250 mg, 0.54 mmol), potassium phosphate trihydrate (374 mg, 1.62 mmol), and RuPhos Pd G2 (42 mg, 0.05 mmol) were charged into a 2-5 mL microwave vial equipped with a stir bar. The reaction vessel was evacuated and backfilled with nitrogen (×3). 1,4-Dioxane (4 mL) was added, followed by cyclopropylboronic acid (139 mg, 1.62 mmol) and water (1 mL) (both solvents were degassed). The mixture was then heated to 120 °C under microwave irradiation for 1 h.

[0231] The reaction was cooled to room temperature, after which additional cyclopropylboronic acid (139 mg, 1.62 mmol) and RuPhos Pd G2 (42 mg, 0.05 mmol) were added and the reaction was heated to 120° C. for an additional 2.5 hours: The reaction mixture was concentrated in vacuo to remove dioxane. The residue was diluted with water (20 ml) and DCM (20 mL) and the layers were separated. The aqueous phase was extracted with a further portion of DCM (3 x 5 ml), and the combined organic extracts were then dried and concentrated to give a dark solid (331 mg).

[0232] The crude residue was purified by mass-directed reverse phase HPLC to give 4-[3-cyclopropyl-6-fluoro-2-[2-(2-fluoro-4-pyridyl)ethyl]phenyl]-5-hydroxy-2,6-dimethyl-pyridazin-3-one (C-1.013) as a white solid [ka] 1H NMR (400MHz, methanol) δ=8.01(d,J=5.1Hz,1H),7.13(dd,J=5.6,8.3Hz,1H),7.02-6.93(m,2H),6.72(br s,1H),3.72(s,3H),3.02-2.75(m,4H),2.32(s,3H),1.97-1.87(m,1H),1.02-0.89(m,2H),0.74-0.61(m,2H)

[0233] Compounds A-1.023, A-1.024, A-1.025, A-1.026, A-1.027, A-1.028, A-1.029, A-1.030, A-1.031, A-1.032, A-1.033, A-1.034, A-1.035, A-1.03 6, A-1.037, A-1.038, A-1.039, A-1.040, A-1.041, A-1.042, A-1.043, A-1.044, A-2.027, A-2.030, A-2.037, A-3.028, A-3.029, A-3.030 , A-3.035, A-3.036, A-3.038, A-4.029, A-4.030, A-4.035, A-4.036, A-1.373, A-1.374, A-1.375, A-1.376, A-1.377, A-1.378, A-1.379, A-1.380, A-1.381, A-1.382, A-1.383, A-1.384, A-1.386, A-1.387, A-1.389, A-1.390, A-1.391 and A-1.392 were prepared using the general method described above. Table 4 below shows the structures and NMR characterization data of these compounds.

[0234] [Table 4-1] [Table 4-2] [Table 4-3] [Table 4-4] [Table 4-5] [Table 4-6] [Table 4-7] [Table 4-8] [Table 4-9] [Table 4-10] [Table 4-11] [Table 4-12] [Table 4-13] [Table 4-14] [Table 4-15] [Table 4-16] [Table 4-17]

[0235] B1 Post-emergence efficacy - Test 1 Seeds of the various test species are sown in standard soil in pots: nightshade (Solanum nigrum) (SOLNI), redroot pigweed (Amaranthus retoflexus) (AMARE), foxtail (Setaria faberi) (SETFA), barnyardgrass (Echinochloa crus-galli) (ECHCG), morning glory (Ipomoea hederacea) (IPOHE), ryegrass (Lolium perenne) (LOLPE). After 8 days (after emergence) of cultivation in a greenhouse under controlled conditions (24 / 16 ℃, day / night; 14 hours of light; 65% humidity), spray the plants with an aqueous spray solution derived from a formulation of technical active ingredient in acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5).Apply the compound at 1000g / ha.Then, grow the test plants in a greenhouse under controlled conditions (24 / 16 ℃, day / night; 14 hours of light; 65% humidity) and water them twice a day.After 13 days, evaluate the test for the percentage of damage caused to the plants. Bioactivity is assessed on a 5-point scale (5 = 80-100%; 4 = 60-79%; 3 = 40-59%; 2 = 20-39%; 1 = 0-19%). Blank values ​​in the tables indicate that the compound was not tested on that species.

[0236] [Table 5]

[0237] B2 Post-emergence efficacy - Study 2 Seeds of various test species are sown in standard soil in pots: nightshade (Solanum nigrum) (SOLNI), redroot pigweed (Amaranthus retoflexus) (AMARE), foxtail (Setaria faberi) (SETFA), barnyardgrass (Echinochloa crus-galli) (ECHCG), morning glory (Ipomoea hederacea) (IPOHE), and ryegrass (Lolium perenne) (LOLPE). After 8 days of cultivation (post-emergence) in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from a technical active ingredient blend in acetone / water (50:50) containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN9005-64-5). The compounds are applied at 250 g / ha. The test plants are then grown in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days, the test is evaluated for the percentage of damage caused to the plants. Biological activity is assessed on a 5-point scale (5 = 80-100%; 4 = 60-79%; 3 = 40-59%; 2 = 20-39%; 1 = 0-19%). Blank values ​​in the tables indicate that the compound was not tested on the corresponding species.

[0238] [Table 6]

[0239] B3 Post-emergence efficacy - Study 3 Seeds of various test species are sown in standard soil in pots: Amaranthus retoflexus (AMARE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE), Zea mays (ZEAMX), and Abutilon theophrasti (ABUTH). After 8 days of cultivation (post-emergence) in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from a technical active ingredient blend in acetone / water (50:50) containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN9005-64-5). The compounds are applied at 250 g / ha. The test plants are then grown in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days, the test is evaluated for the percentage of damage caused to the plants. Bioactivity is assessed on a 5-point scale (5 = 80-100%; 4 = 60-79%; 3 = 40-59%; 2 = 20-39%; 1 = 0-19%). Blank values ​​in the tables indicate that no compounds were tested on that species.

[0240] [Table 7]

[0241] B4 Pre-emergence efficacy - Study 1 Seeds of various test species were sown in standard soil in pots: nightshade (Solanum nigrum) (SOLNI), redroot pigweed (Amaranthus retoflexus) (AMARE), foxtail (Setaria faberi) (SETFA), barnyardgrass (Echinochloa crus-galli) (ECHCG), morning glory (Ipomoea hederacea) (IPOHE), and ryegrass (Lolium perenne) (LOLPE). After one day of cultivation (before emergence) in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from a technical active ingredient blend in acetone / water (50:50) containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN9005-64-5). The compounds are applied at 1000 g / ha. The test plants are then grown under controlled conditions in a greenhouse (24 / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days, the test is evaluated for the percentage of damage caused to the plants. Bioactivity is assessed on a 5-point scale (5 = 80-100%; 4 = 60-79%; 3 = 40-59%; 2 = 20-39%; 1 = 0-19%). Blank values ​​in the tables indicate that no compounds were tested on that species.

[0242] [Table 8]

[0243] B5 Pre-emergence efficacy - Study 2 Seeds of various test species were sown in standard soil in pots: nightshade (Solanum nigrum) (SOLNI), redroot pigweed (Amaranthus retoflexus) (AMARE), foxtail (Setaria faberi) (SETFA), barnyardgrass (Echinochloa crus-galli) (ECHCG), morning glory (Ipomoea hederacea) (IPOHE), and ryegrass (Lolium perenne) (LOLPE). After one day of cultivation (before emergence) in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from a technical active ingredient blend in acetone / water (50:50) containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN9005-64-5). The compounds are applied at 250 g / ha. The test plants are then grown under controlled conditions in a greenhouse (24 / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days, the test is evaluated for the percentage of damage caused to the plants. Bioactivity is assessed on a 5-point scale (5 = 80-100%; 4 = 60-79%; 3 = 40-59%; 2 = 20-39%; 1 = 0-19%). Blank values ​​in the tables indicate that no compounds were tested on that species.

[0244] [Table 9]

[0245] B6 Pre-emergence efficacy - Study 3 Seeds of various test species were sown in standard soil in pots: Amaranthus retoflexus (AMARE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE), Zea mays (ZEAMX), and Abutilon theophrasti (ABUTH). After one day of cultivation (before emergence) in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from a technical active ingredient blend in a 50:50 acetone / water solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN9005-64-5). The compounds are applied at 250 g / ha. The test plants are then grown under controlled conditions in a greenhouse (24 / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days, the test is evaluated for the percentage of damage caused to the plants. Bioactivity is assessed on a 5-point scale (5 = 80-100%; 4 = 60-79%; 3 = 40-59%; 2 = 20-39%; 1 = 0-19%). Blank values ​​in the tables indicate that no compounds were tested on that species.

[0246] [Table 10]

Claims

1. Formula (I) 【Chemistry 1】 Compounds of [In the formula, R 1 is C 1 ~C 4 Alkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Alkoxy, C 1 ~C 2 Alkoxy-C 1 ~C 2 Alkyl, C 2 ~C 4 Alkenyl, C 1 ~C 4 Haloalkyl, cyano-C 1 ~C 4 Alkyl, C 2 ~C 4 Haloalkenyl, C 2 ~C 4 Alkynyl and C 2 ~C 4 haloalkynyl; R 2 is hydrogen, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 3 Haloalkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 6 Alkoxy, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 3 ~C 6 Cycloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 1 ~C 6 Hydroxyalkyl-, C 1 ~C 6 Alkylcarbonyl-, -S(O) m C 1 ~C 6 Alkyl, amino, C 1 ~C 6 Alkylamino, C 1 ~C 6 Dialkylamino, -C(C 1 ~C 3 alkyl)=N—O—C 1 ~C 3 Alkyl and C 2 ~C 6 haloalkynyl; G is hydrogen or C(O)R 3 and R 3 is C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 1 ~C 6 Alkyl-S-, C 1 ~C 6 Alkoxy, —NR 4 R 5 and one or more R 6 phenyl optionally substituted with; Each R 4 and R 5 is hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, and C 3 ~C 6 cycloalkyl; or R 4 and R 5 can together form a morpholinyl ring; Each R 4a and R 5a is C 1 ~C 6 Alkoxy, and C 3 ~C 6 cycloalkyl; or R 4a and R 5a can together form a morpholinyl ring; R 6 is halogen, cyano, nitro, C 1 ~C 3 Alkyl, C 1 ~C 3 Haloalkyl, C 1 ~C 3 Alkoxy and C 1 ~C 3 haloalkoxy; X and Y are each independently hydrogen, C 1 ~C 3 Alkyl, cyclopropyl, C 1 ~C 3 Alkoxy, C 1 ~C 3 Haloalkyl, C 1 ~C 3 haloalkoxy, or halogen; (i) D has R on at least two ring carbon atoms. 8 or substituted on at least two ring carbon atoms with R 8 and on at least one ring nitrogen atom with R 9 a substituted monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, substituted with At least one R 8 is C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, —S(O) m -C 3 ~C 6 cycloalkyl, —O—S(O) 2 C 1 ~C 3 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -Alkyl-, -NR 4a R 5a , -C(S)NR 4 R 5 , -S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NHS—(O) 2 C 1 ~C 6 Alkyl, —C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Alkylsulfonylamino-, C 1 ~C 6 Alkyl sulfonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylsulfonylamino-, C 1 ~C 6 Haloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, C 3 ~C 6 Cycloalkylsulfonylamino-, C 3 ~C 6 Cycloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, hydroxyamino-, hydroxy(C 1 ~C 6 alkyl)amino, C 1 ~C 6 Alkoxyamino, C 1 ~C 6 Alkoxy (C 1 ~C 6 alkyl)amino, C 1 ~C 6 Haloalkoxyamino, C 1 ~C 6 Haloalkoxy (C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-5 R 16 is substituted with; At least one R 9 is C 5 ~C 6 Alkyl, C 5 ~C 6 Haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 3 Alkoxy-C 3 Alkyl-, C 3 Alkoxy-C 1 ~C 2 Alkyl-, C 1 ~C 3 Haloalkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 6 Hydroxyalkyl-, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -alkyl- and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0 to 5 R 16 is substituted with; at least one further R 8 The substituents are hydroxyl, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl, C 1 ~C 3 Haloalkoxy-C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 1 ~C 6 Hydroxyalkyl-, C 1 ~C 6 Alkylcarbonyl-, C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, —S(O) m -C 3 ~C 6 cycloalkyl, —O—S(O) 2 C 1 ~C 3 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -Alkyl-, NR 4 R 5 , -C(S)NR 4 R 5 , -S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NHS—(O) 2 C 1 ~C 6 Alkyl, —C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Alkylsulfonylamino-, C 1 ~C 6 Alkyl sulfonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylsulfonylamino-, C 1 ~C 6 Haloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, C 3 ~C 6 Cycloalkylsulfonylamino-, C 3 ~C 6 Cycloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, hydroxyamino-, hydroxy(C 1 ~C 6 alkyl)amino, C 1 ~C 6 Alkoxyamino, C 1 ~C 6 Alkoxy (C 1 ~C 6 alkyl)amino, C 1 ~C 6 Haloalkoxyamino, C 1 ~C 6 Haloalkoxy (C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-5 R 16 is substituted with; m is an integer of 0, 1, or 2; Each R 16 are independently halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy or C 1 ~C 6 haloalkoxy; or (ii) D is a group having at least two R 8 is a phenyl ring substituted with; At least one R 8 is C 1 -C 6 haloalkylcarbonyl-, C 3 -C 6 cycloalkylcarbonyl-, —S(O) m —C 1 -C 6 haloalkyl, —S(O) m —C 3 -C 6 cycloalkyl, —O—S(O) 2 C 1 -C 3 alkyl, —C 1 -C 3 alkyl-S(O) m —C 1 -C 6 alkyl, —C 1 -C 3 alkyl-S(O) m —C 1 -C 6 haloalkyl, —C 1 -C 3 alkyl-S(O) m —C 3 -C 6 cycloalkyl, cyano-C 1 -C 6 -alkyl-, —NR 4a R 5a , —C(S)NR 4 R 5 , —S(O) 2 NHC(O)C 1 -C 3 alkyl, -S(O)2NR4R5, -C(O)OH, -C(O)OC1-C6 alkyl, -C(O)NHS-(O)2C1-C6 alkyl, -C(O)NR4R5, -NR4C(O)NR4R5, C1-C6 alkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylcarbonylamino-, C1-C6 haloalkylcarbonyl(C1-C6 alkyl)amino-, C1-C6 alkylsulfonylamino-, C1-C6 alkylsulfonyl(C1-C6 alkyl)amino-, C1-C6 haloalkylsulfonylamino-, C1-C6 haloalkylsulfonyl(C1 -C6 alkyl)amino-, C3-C6 cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; and ring systems selected from the group consisting of phenyl rings, 5-6 membered heteroaryl rings and 3-6 membered heterocyclyl rings, said ring systems being substituted with 0-5 R16; At least one further R 8 substituent is selected from the group consisting of hydroxyl, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 1 -C 3 haloalkoxy-C 1 -C 3 alkyl, C 1 -C 3 alkoxy-C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 hydroxyalkyl-, C 1 -C 6 alkylcarbonyl-, C 1 -C 6 haloalkylcarbonyl-, C 3 -C 6 Cycloalkylcarbonyl-, -S(O)m-C1-C6 haloalkyl, -S(O)m-C3-C6 cycloalkyl, -O-S(O)2C1-C3 alkyl, -C1-C3 alkyl-S(O)m-C1-C6 alkyl, -C1-C3 alkyl-S(O)m-C1-C6 haloalkyl, -C1-C3 alkyl-S(O)m-C3-C6 cycloalkyl, cyano-C1-C6-alkyl-, NR4R5, -C(S)NR4R5, -S(O)2NHC(O)C1-C3 alkyl, -S(O)2NR4R5 , —C(O)OH, —C(O)OC 1 -C 6 alkyl, —C(O)NHS—(O) 2 C 1 -C 6 alkyl, —C(O)NR 4 R 5 , —NR 4 C(O)NR 4 R 5 , C 1 -C 6 alkylcarbonyl(C 1 -C 6 alkyl)amino-, C 1 -C 6 haloalkylcarbonylamino-, C 1 -C 6 haloalkylcarbonyl(C 1 -C 6 alkyl)amino-, C 1 -C 6 alkylsulfonylamino-, C 1 -C 6 alkylsulfonyl(C 1 -C 6 alkyl)amino-, C 1 -C 6 haloalkylsulfonylamino-, C 1 -C 6 haloalkylsulfonyl(C 1 -C 6 alkyl)amino-, C 3 -C 6 Cycloalkylsulfonylamino-, C3-C6 cycloalkylsulfonyl(C1-C6 alkyl)amino-, hydroxyamino-, hydroxy(C1-C6 alkyl)amino, C1-C6 alkoxyamino, C1-C6 alkoxy(C1-C6 alkyl)amino, C1-C6 haloalkoxyamino, C1-C6 haloalkoxy(C1-C6 alkyl)amino; and ring systems selected from the group consisting of phenyl rings, 5-6 membered heteroaryl rings, and 3-6 membered heterocyclyl rings, said ring systems being substituted with 0-5 R16; m is an integer of 0, 1, or 2; each R 16 is independently halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, or C 1 -C 6 haloalkoxy; W is the base of the following formula 【Chemistry 2】 wherein: "a" represents the point of attachment to the phenyl-pyridazinedione / phenyl-pyridazinone moiety; "b" represents the point of attachment to ring D; R 10 , R 12 , R 14 and R 15 are each independently hydrogen, C 1 ~C 3 Alkyl, or C 1 ~C 3 haloalkyl; Or R 10 and R 12 together with the carbon atoms to which they are attached, C 3 ~C 6 forming a carbocyclic ring; R 11 and R 13 are each independently hydrogen, halogen, or C 1 ~C 3 Alkyl, or C 1 ~C 3 haloalkyl; However, R 11 or R 13 One of them is halogen, C 1 ~C 3 Alkyl or C 1 ~C 3 when one is haloalkyl, the other is hydrogen.

2. R 1 is methyl, ethyl, cyclopropyl, propargyl or C 1 is fluoroalkyl; R 2 is chloro, cyclopropyl, trifluoromethyl or methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro, chloro or C 1 -haloalkyl and ortho relative to the pyridazinone / pyridazinedione moiety; Y is hydrogen, chloro, fluoro, or bromo and is ortho relative to the -WD moiety; D is a phenyl ring substituted with at least two R 8 ; At least one R 8 is C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, —S(O) m -C 3 ~C 6 cycloalkyl, —O—S(O) 2 C 1 ~C 3 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -Alkyl-, -NR 4a R 5a , -C(S)NR 4 R 5 , -S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NHS—(O) 2 C 1 ~C 6 Alkyl, —C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Alkylsulfonylamino-, C 1 ~C 6 Alkyl sulfonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylsulfonylamino-, C 1 ~C 6 Haloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, C 3 ~C 6 Cycloalkylsulfonylamino-, C 3 ~C 6 Cycloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, hydroxyamino-, hydroxy(C 1 ~C 6 alkyl)amino, C 1 ~C 6 Alkoxyamino, C 1 ~C 6 Alkoxy (C 1 ~C 6 alkyl)amino, C 1 ~C 6 Haloalkoxyamino, C 1 ~C 6 Haloalkoxy (C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-5 R 16 is substituted with; at least one further R 8 The substituents are hydroxyl, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 Alkoxy, C 2 ~C 6 Alkenyl, and C 2 ~C 6 alkynyl; R 4 and R 5 are each independently hydrogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, or C 3 ~C 6 is cycloalkyl; m is an integer of 0, 1, or 2; Each R 4a and R 5a is C 1 ~C 6 Alkoxy, and C 3 ~C 6 cycloalkyl; or R 4a and R 5a can together form a morpholinyl ring; Each R 16 are independently halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy or C 1 ~C 6 haloalkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

3. R 1 is methyl; R 2 is methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is two R 8 and a phenyl ring substituted with at least one R 8 is C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, —S(O) m -C 3 ~C 6 cycloalkyl, —O—S(O) 2 C 1 ~C 3 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, —S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NHS—(O) 2 C 1 ~C 6 Alkyl, —C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-5 R 16 is substituted with; at least one further R 8 The substituents are halogen, C 1 ~C 6 Alkyl and C 1 ~C 6 haloalkyl; R 4 and R 5 are each independently hydrogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, or C 3 ~C 6 is cycloalkyl; m is 0 or 2; Each R 16 are independently halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 3 Haloalkyl or C 1 ~C 4 is alkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

4. R 1 is methyl; R 2 is methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, or methoxy; X is fluoro and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is a phenyl ring substituted with at least two R 8 ; At least one R 8 is —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NR 4 R 5 and ring systems selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, and 1,3,5-triazinyl rings, said ring systems being selected from the group consisting of 0-2 R 16 is substituted with; R 4 and R 5 are each independently hydrogen or C 1 ~C 3 is alkyl; m is 0 or 2; Each R 16 are independently halogen or C 1 ~C 4 is alkyl; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

5. R 1 is methyl; R 2 is methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl; X is fluoro and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is a phenyl ring substituted with two R 8 ; At least one R 8 is selected from the group consisting of methylsulfanylmethyl, isopropylsulfanylmethyl, sulfamoyl, methylsulfamoyl, carbamoyl; and a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, 1,2,4-triazolyl, oxazolyl, and thiazolyl rings, said ring system containing zero to two R 16 is substituted with; Each R 16 is methyl; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

6. R 1 is methyl, ethyl, cyclopropyl, propargyl or C 1 is fluoroalkyl; R 2 is chloro, cyclopropyl, trifluoromethyl or methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro, chloro or C 1 -haloalkyl and ortho relative to the pyridazinone / pyridazinedione moiety; Y is hydrogen, chloro, fluoro, or bromo and is ortho relative to the -WD moiety; D is a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, substituted on at least two ring carbon atoms with at least two R8, or substituted on at least two ring carbon atoms with at least two R8 and substituted on at least one ring nitrogen atom with R9; At least one R 8 is C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, —S(O) m -C 3 ~C 6 cycloalkyl, —O—S(O) 2 C 1 ~C 3 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -Alkyl-, NR 4a R 5a , -C(S)NR 4 R 5 , -S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NHS—(O) 2 C 1 ~C 6 Alkyl, —C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Alkylsulfonylamino-, C 1 ~C 6 Alkyl sulfonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylsulfonylamino-, C 1 ~C 6 Haloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, C 3 ~C 6 Cycloalkylsulfonylamino-, C 3 ~C 6 Cycloalkylsulfonyl (C 1 ~C 6 alkyl)amino-, hydroxyamino-, hydroxy(C 1 ~C 6 alkyl)amino, C 1 ~C 6 Alkoxyamino, C 1 ~C 6 Alkoxy (C 1 ~C 6 alkyl)amino, C 1 ~C 6 Haloalkoxyamino, C 1 ~C 6 Haloalkoxy (C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-5 R 16 is substituted with; at least one further R 8 The substituents are hydroxyl, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 Alkoxy, C 2 ~C 6 Alkenyl, and C 2 ~C 6 alkynyl; At least one R 9 is C 5 ~C 6 Alkyl, C 5 ~C 6 Haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 3 Alkoxy-C 3 Alkyl-, C 3 Alkoxy-C 1 ~C 2 Alkyl-, C 1 ~C 3 Haloalkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl-, C 1 ~C 6 Hydroxyalkyl-, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, cyano-C 1 ~C 6 -alkyl- and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0 to 5 R 16 is substituted with; R 4 and R 5 are each independently hydrogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, or C 3 ~C 6 is cycloalkyl; m is an integer of 0, 1, or 2; Each R 4a and R 5a is C 1 ~C 6 Alkoxy, and C 3 ~C 6 cycloalkyl; or R 4a and R 5a can together form a morpholinyl ring; Each R 16 are independently halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy or C 1 ~C 6 haloalkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

7. R 1 is methyl; R 2 is methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy, or tert-butoxy; X is fluoro and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is a group consisting of two R 8 or is substituted on at least two ring carbon atoms with two R8 and on one ring nitrogen atom with R9; At least one R 8 is C 1 ~C 6 Haloalkylcarbonyl-, C 3 ~C 6 Cycloalkylcarbonyl-, -S(O) m -C 1 ~C 6 Haloalkyl, —S(O) m -C 3 ~C 6 cycloalkyl, —O—S(O) 2 C 1 ~C 3 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 Cycloalkyl, —S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NHS—(O) 2 C 1 ~C 6 Alkyl, —C(O)NR 4 R 5 , -NR 4 C(O)NR 4 R 5 , C 1 ~C 6 Alkylcarbonyl (C 1 ~C 6 alkyl)amino-, C 1 ~C 6 Haloalkylcarbonylamino-, C 1 ~C 6 Haloalkylcarbonyl (C 1 ~C 6 and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-5 R 16 is substituted with; at least one further R 8 The substituents are halogen, C 1 ~C 6 Alkyl and C 1 ~C 6 haloalkyl; One R 9 is C 5 ~C 6 Alkyl, C 5 ~C 6 Haloalkyl, C 3 ~C 6 -cycloalkyl, -C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Haloalkyl, —C 1 ~C 3 Alkyl-S(O) m -C 3 ~C 6 cycloalkyl, and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring, and a 3- to 6-membered heterocyclyl ring, said ring system having 0 to 5 R 16 is substituted with; R 4 and R 5 are each independently hydrogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxy, or C 3 ~C 6 is cycloalkyl; m is 0 or 2; Each R 16 are independently halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 3 Haloalkyl or C 1 ~C 4 is alkoxy; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

8. R 1 is methyl; R 2 is methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl, t-butyl, methyl, ethyl, propargyl, or methoxy; X is fluoro and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is a 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 nitrogen atoms, substituted on at least two ring carbon atoms with R 8 or substituted on at least two ring carbon atoms with R 8 and on at least one ring nitrogen atom with R 9 ; At least one R 8 is —C 1 ~C 3 Alkyl-S(O) m -C 1 ~C 6 Alkyl, —S(O) 2 NHC(O)C 1 ~C 3 Alkyl, —S(O) 2 NR 4 R 5 , -C(O)OH, -C(O)OC 1 ~C 6 Alkyl, —C(O)NR 4 R 5 and a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, or 1,3,5-triazinyl ring, wherein said ring system is selected from the group consisting of 0 to 2 R 16 is replaced by; One R 9 is C 5 ~C 6 Alkyl, C 3 ~C 6 -cycloalkyl and a ring system selected from the group consisting of a phenyl ring, a 5- to 6-membered heteroaryl ring and a 3- to 6-membered heterocyclyl ring, said ring system being selected from the group consisting of 0-2 R 16 is substituted with; R 4 and R 5 are each independently hydrogen or C 1 ~C 3 is alkyl; m is 0 or 2; Each R 16 are independently halogen or C 1 ~C 4 is alkyl; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

9. R 1 is methyl; R 2 is methyl; G is hydrogen or —C(O)—R 3 and R 3 is isopropyl; X is fluoro and is ortho relative to the pyridazinone / pyridazinedione moiety; Y is chloro and is ortho relative to the -WD moiety; D is pyrazolyl or pyridyl substituted on at least two ring carbon atoms with R 8 or substituted on at least two ring carbon atoms with R 8 and on at least one ring nitrogen atom with R 9 ; At least one R 8 is selected from the group consisting of methylsulfanylmethyl, isopropylsulfanylmethyl, sulfamoyl, methylsulfamoyl, carbamoyl; and a ring system selected from the group consisting of phenyl, morpholinyl, tetrahydrofuranyl, furyl, thienyl, pyrrolyl, pyrazolyl, 1,2,4-triazolyl, oxazolyl, and thiazolyl rings, said ring system containing zero to two R 16 is replaced by; one R 9 is selected from cyclopropyl or phenyl; Each R 16 is methyl; W is W1; R 10 , R 11 , R 12 , and R 13 The compound of formula (I) according to claim 1, wherein are all hydrogen.

10. The compound of formula (I) according to claim 1, which is 4-[2-[6-chloro-3-fluoro-2-(5-hydroxy-2,6-dimethyl-3-oxo-pyridazin-4-yl)phenyl]ethyl]-N-ethyl-2-fluoro-N-methyl-benzamide (A-1.028).

11. 10. A herbicidal composition comprising a compound of formula (I) according to claim 1 and an agriculturally acceptable formulation adjuvant.

12. 12. The herbicidal composition of claim 11, further comprising at least one additional pesticide.

13. 13. The herbicidal composition of claim 12, wherein the additional pest control agent is a herbicide or a herbicide safener.

14. 14. A method for controlling undesired plant growth, comprising the step of applying a compound of formula (I) as defined in claim 1 or a herbicidal composition as defined in any one of claims 11 to 13 to the undesired plants or their locus.

15. 10. Use of a compound of formula (I) according to claim 1 as a herbicide.

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