throbber
WO 2020/074489
`
`99
`
`PCT/EP2019/077185
`
`A compound of Formula (I)
`
`2
`
`OR
`
`XL)
`
`3
`
`l G
`
`wherein
`
`10
`
`R' is selected from the group consisting of methyl, ethynyl, 1-propynyl, phenyl
`
`and a 5 or 6 membered heteroaryl which comprises one or two nitrogen
`
`heteroatoms, said phenyl and heteroaryl optionally substituted by one or two
`
`R'® substituents;
`
`15
`
`R? is selected from the group consisting of methyl, ethyl, methoxy and chloro;
`
`R? is selected from the group consisting of methyl ethyl, methoxy and chloro;
`
`20
`
`R* is selected from the group consisting of C1-Caalkyl, C1-Csalkoxy-, Cu1-
`
`Cahaloalkyl, -C(OQ)Ci-Caalkyl, -C(O)C1-Cuhaloalkyl, -S(Q)nC1-Cealkyl, -S(O)nCi-
`Cehaloalkyl, -S(O)n-(CH2)n-Cs-Cecycloalkyl, -S(O)nC(R™)R'7R'3, -C(O)H, -C(O)-
`(CH2)n-C3-Cecycloalkyl,
`-C(O)C(R™")RYR,
`-C(O)C2-Caalkenyl,
`-
`C(O)(.CR®ER™)CN,
`-C(O)(CRER)(CRER™)CN,
`-C(O)CH2C(O)-C1-Cealkyl,
` -
`
`C(O)CH20C(O)-Ci-Cealkyl,
`
`-C(O)OC1-Cealkyl,
`
`-C(O)OC1-Cehaloalkyl,
`
`—-
`
`25
`
`C(O)(CH2)nS(O)nC1-Cealkyl, -C(O)C1-CsalkoxyC1-Cealkyl, -C(O)C1-CsalkoxyC2-
`
`Cealkenyl, -C(O)C1-C3alkoxyC2-Cealkynyl, -C(O)C1-CsalkoxyC;-Cehaloalkyl,
`
`-
`
`C(O)C1-CsalkoxyC3-Cecycloalkyl,
`-C(Q)OC1-CaalkoxyCi-Cealkyl,
`-C(O)C1-
`CaalkoxyC.1-CsalkoxyC1-Cealkyl, -C(O)(CH2)nNR®R®, -C(O)-(CH2)n-NR’C(O)RS,
`-C(O)-(CH2)n-O-N=CR®R9,
`-CN,
`-S(O),NR'R™,
`-S(O)=NR)RY,
` —
`C(O)C(O)R”°, —C(O)C(R*?)=N-O-R™, —C(O)C(R*3)=N-NR*°R”S,-(CH2),—phenyl,
`
`-C(O)-(CHa2)n-phenyl,
`
`-S(O)n-(CH2)n-phenyl,
`
`-heterocyclyl,
`
`-C(O)-(CH2)n-
`
`heterocyclyl, -S(O)n-(CHz2),-heterocyclyl, wherein each heterocyclyl is a 5- or 6-
`
`30
`
`

`

`WO 2020/074489
`
`100
`
`PCT/EP2019/077185
`
`membered heterocyclyl which may be aromatic, saturated or partially saturated
`
`and can contain from 1 to 4 heteroatoms each independently selected from the
`
`group consisting of oxygen, nitrogen and sulphur,
`
`and wherein said
`
`heterocyclyl or phenyl groups are optionally substituted by one, two or three
`
`substituents independently selected from the group consisting of C:-Csalkyl,
`
`C.:-Cshaloalkyl, Ci-Csalkoxy, C2-Csalkenyl, C2-Csaalkynyl, halogen, cyano and
`
`nitro;
`
`R°is selected from the group consisting of hydrogen and C:-Cealkyl;
`
`10
`
`R® is selected from the group consisting of hydrogen, C1-Cealkyl, C2-Cealkenyl,
`
`C2-Cealkynyl, Ci-Cehaloalkyl, hydroxyl-, C1-Cealkoxy, C3-Ce cycloalkyl,
`, -C1-
`CaalkoxyC1-Cealkyl,
`-C1-C3alkoxyC1-Cehaloalkyl,
`-(CR°R')C1-Cehaloalkyl,
`-
`(CR°R')C(O)NR®°R®, phenyl,
`-pyridyl, wherein the phenyl and pyridyl are
`
`15
`
`optionally substituted by one, two or three substituents independently selected
`
`from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3
`
`alkenyl, C2-C3 alkynyl, halogen, cyano and nitro; or
`
`R®° and R® together form —CH2zCH2zOCH2CH>2-; and
`
`20
`
`R’is selected from the group consisting of hydrogen and C1-C¢alkyl;
`
`R® is selected from the group consisting of hydrogen, C1-Cé alkyl, C1-Ce alkoxy,
`
`C3-Ce cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally
`
`25
`
`substituted by one, two or three substituents independently selected from the
`
`group consisting of C1-Cz3 alkyl, C1-C3 haloalkyl, Ci1-C3 alkoxy, C2-C3 alkenyl,
`
`C2-C3 alkynyl, halogen, cyano and nitro;
`
`30
`
`R° is hydrogen or methyl;
`
`R'° is hydrogen or methyl; or
`
`R° and R" together form —CH2CH2-; and
`
`35
`
`R"' is hydrogen or methyl;
`
`R'? is selected from the group consisting of hydrogen, C1-Ce alkyl, hydroxyl and
`
`

`

`WO 2020/074489
`
`101
`
`PCT/EP2019/077185
`
`C1-Ce alkoxy-;
`
`R'is selected from the group consisting of hydrogen, C1-Ce alkyl, hydroxyl and
`
`C1-Ce¢ alkoxy; or
`
`R'? and R' together form —CH2-X-CH2-; and
`
`X is selected from the group consisting of O, S and N-R";
`
`10
`
`R'* is selected from the group consisting of hydrogen, C1-C3 alkyl and C1-Cs
`
`alkoxy-;
`
`R'® is independently selected from the group consisting of C1-C4 alkyl, C1-C4
`
`haloalkyl, cyano and halogen;
`
`15
`
`R'® is hydrogen or C1-Cealkyl; and
`
`R'’
`
`is selected from the group consisting of hydrogen, Ci-Cealkyl, C3-
`
`Cecycloalkyl, C1-Ce alkoxy-C1-Caalkyl-,-C(O)C1-Cealkyl, -C(O)OC1-Cealkyl and
`
`20
`
`CH2CN; or
`
`R'® and R'’ together form —CH2CH2z0CH2CH>2-, —CH2zCH28(O)2zCH2CH2-;
`
`R'®is hydrogen or C1-Cealkyl;
`
`25
`
`R'° is selected from the group consisting of hydrogen, C1-Ce alkyl, C1-Ce alkoxy,
`
`C3-Cecycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally
`
`substituted by one, two or three substituents independently selected from the
`
`group consisting of C1-Cz3 alkyl, C1-C3 haloalkyl, Ci1-C3 alkoxy, C2-C3 alkenyl,
`
`30
`
`C2-C3 alkynyl, halogen, cyano and nitro;
`
`R?° is selected from the group consisting of C1-Cealkyl, C1-Cehaloalkyl, C1-
`Cealkoxy-, C1-Cehaloalkoxy, -NR2'R??, phenyl and -pyridyl, wherein the phenyl
`
`and pyridyl are optionally substituted by one,
`
`two or three substituents
`
`35
`
`independently selected from the group consisting of Ci-C3 alkyl, Ci-C3
`
`haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, Co-C3 alkynyl, halogen, cyano and nitro;
`
`

`

`WO 2020/074489
`
`102
`
`PCT/EP2019/077185
`
`R?' is selected from the group consisting of hydrogen, C1-Ce alkyl, C1-Ce alkoxy,
`
`C1-CealkoxyC.1-Caalkyl-, C3-Ce cycloalkyl, C1-Cehaloalkyl- and C1-Cehaloalkoxy-
`
`, -C(O)C1-Cealkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally
`
`substituted by one, two or three substituents independently selected from the
`
`group consisting of C1-C3 alkyl, C1-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl,
`
`C2-C3 alkynyl, halogen, cyano and nitro;
`
`R*2is hydrogen or C1-Cealkyl; or
`
`10
`
`R?' and R22 together form -CH2zCH2zOCH2CH>-;
`
`R?3 is selected from the group consisting of hydrogen, C1-Cealkyl, Cu1-
`
`Cehaloalkyl, C1-Cealkoxy- and C1-Cehaloalkoxy-;
`
`15
`
`R*™ is selected from the group consisting of hydrogen, Ci-Cealkyl, C1-
`
`CealkoxyC.1-Caalkyl-, C3-Cecycloalkyl, -CH2CN, tetrahydropyranyl-, phenyl and
`
`-pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two
`
`or three substituents independently selected from the group consisting of C:-
`
`Caalkyl, C1-Cshaloalkyl, C1-Cgalkoxy, C2-Csaalkenyl, C2-C3alkynyl, halogen,
`
`20
`
`cyano and nitro;
`
`R?° is hydrogen or C1-Ce alkyl;
`
`R26 ig hydrogen or C1-Ce alkyl;
`
`25
`
`G is selected from the group consisting of hydrogen, -(CH2)n-R®, -C(O)-R®, -
`C(O)-(CR°R*)n-O-R®, -C(O)NR?R?, -S(O)2-R* and C1-Cgalkoxy-C1-Caalkyl-;
`
`R* is independently selected from the group consisting of hydrogen, C:-Cegalkyl,
`
`30
`
`C1-Cs3haloalkyl, C2-Cgalkenyl, Co-Cgalkynyl, C3-Cecycloalkyl, heterocyclyl and
`
`phenyl wherein said heterocyclyl and phenyl groups are optionally substituted
`
`by one,
`
`two or three substituents independently selected from the group
`
`consisting of Cui-Caalkyl, Ci-Cshaloalkyl, C1i-Cs3alkoxy, C2-C3alkenyl, C2-
`
`Cszalkynyl, halogen, cyano and nitro;
`
`35
`
`R° is selected from the group consisting of C1-Cgalkyl, C:-Cshaloalkyl, C2-
`
`

`

`WO 2020/074489
`
`103
`
`PCT/EP2019/077185
`
`Cealkenyl, C2-Cgalkynyl, C3-Ce cycloalkyl, heterocyclyl and phenyl wherein said
`
`heterocyclyl and phenyl groups are optionally substituted by one, two or three
`
`substituents independently selected from the group consisting of C1-Casalkyl,
`
`C1-Cshaloalkyl, C;-C3alkoxy, C2-Csalkenyl, C2-Csaalkynyl, halogen, cyano and
`
`nitro;
`
`R° is hydrogen or C1-Cz alkyl;
`
`R* is hydrogen or C1-C3 alkyl; and
`
`10
`
`n is independently 0, 1 or 2;
`
`or an agriculturally acceptable salt thereof.
`
`15
`
`A compound according to claim 1 which is a compound of Formula (la)
`
`OR.
`
`wherein
`
`20
`
`R? is methyl or methoxy;
`
`R? is methyl or methoxy;
`
`25
`
`R* is selected from the group consisting of C1-Caalkyl, C1-Csalkoxy-, C1-
`
`Cahaloalkyl, -C(O)C1-Caalkyl, -C(O)C1-Cahaloalkyl, -S(O)nC1-Cealkyl, -S(O)nC1-
`Cehaloalkyl, -S(O)n-(CH2)n-Ca-Cecycloalkyl, -S(O)nC(R')R'7R'8, -C(O)H, -C(O)-
`(CH2)n-C3-Cecycloalkyl,
`-C(O)C(R")R'R*S,
`-C(O)C2-Caalkenyl,
`-
`C(O)(CRYR")CN,
`-C(O)OC1-Cealkyl,
`-C(O)OC1-Cehaloalkyl,
`-
`C(O)(CH2)nS(O)nC1-Cealkyl, -C(O)C1-C3alkoxyC1-Cealkyl, -C(O)NR®R®, -C(O)-
`(CH2)n-NR’C(O)R®, -CN, -(CH2)n-phenyl, -C(O)-(CH2)n-phenyl, -S(O)n-(CH2)n-
`
`phenyl,
`
`-heterocyclyl,
`
`-C(O)-(CH2),-heterocyclyl,
`
`-S(O)n-(CH2)n-heterocyclyl,
`
`30
`
`

`

`WO 2020/074489
`
`104
`
`PCT/EP2019/077185
`
`wherein each heterocyclyl is a 5- or 6- membered heterocyclyl which may be
`
`aromatic, saturated or partially saturated and can contain from 1
`
`to 4
`
`heteroatoms each independently selected from the group consisting of oxygen,
`
`nitrogen and sulphur, and wherein said heterocyclyl or phenyl groups are
`
`optionally substituted by one, two or three substituents independently selected
`
`from the group consisting of Ci-Csalkyl, Ci-Cshaloalkyl, Ci-Csalkoxy, C2-
`
`Csalkenyl, C2-C3alkynyl, halogen, cyano and nitro;
`
`R°is selected from the group consisting of hydrogen and C:-Ce alkyl;
`
`10
`
`R® is selected from the group consisting of hydrogen, C1-Ce alkyl, C1-Ce alkoxy,
`
`C3-Ce cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally
`
`substituted by one, two or three substituents independently selected from the
`
`group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl,
`
`15
`
`C2-C3 alkynyl, halogen, cyano and nitro; or
`
`R® and R® together form —CH2zCH2zOCH2CH>2-; and
`
`R’is selected from the group consisting of hydrogen and C1-Cgalkyl;
`
`20
`
`R® is selected from the group consisting of hydrogen, C1-Ce alkyl, C1-Ce alkoxy,
`
`C3-Ce cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally
`
`substituted by one, two or three substituents independently selected from the
`
`group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl,
`
`25
`
`C2-C3 alkynyl, halogen, cyano and nitro;
`
`R° is hydrogen or methy];
`
`R'° is hydrogen or methyl; or
`
`30
`
`R®° and R"° together form —CH2CH2-; and
`
`R"1 is hydrogen or methyl;
`
`35
`
`R'? and R‘? together form —CH2-X-CH>-;
`
`X is selected from the group consisting of O, S and N-R"™;
`
`

`

`WO 2020/074489
`
`105
`
`PCT/EP2019/077185
`
`R™ is selected from the group consisting of hydrogen, C:-Csalkyl and C1-Cs
`
`alkoxy-;
`
`G is selected from the group consisting of hydrogen, -(CHz2)n-R?, -C(O)-R?, -
`C(O)-(CR°R®)n-O-R®, -C(O)NR'R4, -S(O)2-R? and C1-Csalkoxy-C1-Csalkyl-;
`
`R* is independently selected from the group consisting of hydrogen, C1-Cealkyl,
`
`C.:-Cshaloalkyl, C2-Csalkenyl, C2-Csalkynyl, C3-Cecycloalkyl, heterocyclyl and
`
`10
`
`phenyl wherein said heterocyclyl and phenyl groups are optionally substituted
`
`by one,
`
`two or three substituents independently selected from the group
`
`consisting of Cu.i-Caalkyl, C:-Cshaloalkyl, C.i-Csalkoxy, Cz2-C3alkenyl, C2-
`
`Csalkynyl, halogen, cyano and nitro;
`
`15
`
`R®°
`
`is selected from the group consisting of Ci-Cgalkyl, Ci-Cshaloalkyl, C2-
`
`Cealkenyl, C2-Csalkynyl, C3-Ce cycloalkyl, heterocyclyl and phenyl wherein said
`
`heterocyclyl and phenyl groups are optionally substituted by one, two or three
`
`substituents independently selected from the group consisting of C1-Csalkyl,
`
`C.1-Cs3haloalkyl, C1-C3alkoxy, C2-Caalkenyl, Co-Cs3alkynyl, halogen, cyano and
`
`20
`
`nitro;
`
`R° is hydrogen or C1-C3 alkyl;
`
`R* is hydrogen or C1-Cs alkyl; and
`
`25
`
`n is independently O, 1 or 2;
`
`or an agriculturally acceptable salt thereof.
`
`30
`
`A compound according to claim 1 or claim 2, wherein R? is methyl.
`
`A compound according to any one of the previous claims, wherein R° is methyl.
`
`A compound according to any one of the previous claims 1, 2 or 3, wherein R®?
`
`35
`
`is methoxy.
`
`A compound according to any one of the previous claims, wherein R* is -
`
`

`

`WO 2020/074489
`
`106
`
`PCT/EP2019/077185
`
`C(O)OC1-Cealkyl.
`
`A compound according to any one of the claims 1
`C(O)NR®R®.
`
`to 5, wherein R?*
`
`is -
`
`A compound according to any one of the previous claims, wherein G is
`
`hydrogen.
`
`A compound according to any one of claims 1
`
`to 7, wherein G is -C(O)C:-
`
`10
`
`Cealkyl.
`
`10.
`
`A compound according to any one of claims 1 to 7, wherein G is -C(OQ)-O-Ci-
`
`Cealkyl.
`
`15
`
`11.
`
`A herbicidal composition comprising a compound of Formula (I) or Formula (la)
`
`according to any one of the previous claims and an agriculturally acceptable
`
`formulation adjuvant.
`
`12.
`
`A herbicidal composition according to claim 11, further comprising at least one
`
`20
`
`additional pesticide.
`
`13.
`
`A herbicidal composition according to claim 12, wherein the additional pesticide
`
`is a herbicide or herbicide safener.
`
`25
`
`14.
`
`A methodof controlling weeds at a locus comprising application to the locus of
`
`a weedcontrolling amount of a composition according to any one of claims 11
`
`to 13.
`
`15.
`
`Use of a compound of Formula (I) as defined in claim 1 as a herbicide.
`
`

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