Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`AMENDMENTS TO THE CLAIMS
`
`This listing of claims will replace all prior versions, and listings, of claims in the
`
`application:
`
`1.
`
`(Original) A compoundof Formula (1)
`
`2
`
`OR
`
`X41
`
`(I)
`
`3
`
`OR
`
`lG
`
`wherein
`
`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;
`
`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;
`
`R‘is selected from the group consisting of C1-Caalkyl, C1-Caalkoxy-, C1-Cshaloalkyl, -
`
`C(O)Ci-Caalkyl, -C(O)C1-Cshaloalkyl, -S(O)nCi-Cealkyl, -S(O)nC1-Cchaloalkyl, -S(O)n-
`(CH2)n-C3-Cecycloalkyl, -S(O)nC(R'RVR, -C(O)H, -C(O)-(CH2)n-C3-Cocycloalkyl,
`-
`C(O)CR'YRPRE, -C(O)C2-Caalkenyl, -C(O)(CR’R!)CN, -C(O)(CR?R™)(CR°R™CN,-
`
`C(O)CH2C(O)-C1-Cealkyl, -C(O)CH2OC(O)-Ci-Cealkyl, -C(O)OC1-Cealkyl, -C(O)OC1-
`
`Cohaloalkyl,
`
`-C(O)(CH2)nS(O)nCi-Cealkyl,
`
`-C(O)Ci-CsalkoxyCi-Cealkyl,
`
`-C(O)C1-
`
`CsalkoxyC2-Cealkenyl,
`
`-C(O)C1-Cs3alkoxyC2-Coalkynyl,
`
`-C(O)C1-CsalkoxyC1-
`
`
`
`Cohaloalkyl, -C(OQ)OCi-C3alkoxyCi-Cealkyl,—--C(O)Ci-CsalkoxyC3-Cocycloalkyl,
`
`
`
`C(O)C1-CsalkoxyCi-CsalkoxyC1-Cealkyl,
`
`-C(O)(CH2)nNR°R®,
`
`-C(O)-(CH2)n-
`
`3
`
`
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`AMENDMENTS TO THE CLAIMS
`
`This listing of claims will replace all prior versions, and listings, of claims in the
`
`application:
`
`1.
`
`(Original) A compoundof Formula (1)
`
`2
`
`OR
`
`X41
`
`(I)
`
`3
`
`OR
`
`lG
`
`wherein
`
`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;
`
`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;
`
`R‘is selected from the group consisting of C1-Caalkyl, C1-Caalkoxy-, C1-Cshaloalkyl, -
`
`C(O)Ci-Caalkyl, -C(O)C1-Cshaloalkyl, -S(O)nCi-Cealkyl, -S(O)nC1-Cchaloalkyl, -S(O)n-
`(CH2)n-C3-Cecycloalkyl, -S(O)nC(R'RVR, -C(O)H, -C(O)-(CH2)n-C3-Cocycloalkyl,
`-
`C(O)CR'YRPRE, -C(O)C2-Caalkenyl, -C(O)(CR’R!)CN, -C(O)(CR?R™)(CR°R™CN,-
`
`C(O)CH2C(O)-C1-Cealkyl, -C(O)CH2OC(O)-Ci-Cealkyl, -C(O)OC1-Cealkyl, -C(O)OC1-
`
`Cohaloalkyl,
`
`-C(O)(CH2)nS(O)nCi-Cealkyl,
`
`-C(O)Ci-CsalkoxyCi-Cealkyl,
`
`-C(O)C1-
`
`CsalkoxyC2-Cealkenyl,
`
`-C(O)C1-Cs3alkoxyC2-Coalkynyl,
`
`-C(O)C1-CsalkoxyC1-
`
`
`
`Cohaloalkyl, -C(OQ)OCi-C3alkoxyCi-Cealkyl,—--C(O)Ci-CsalkoxyC3-Cocycloalkyl,
`
`
`
`C(O)C1-CsalkoxyCi-CsalkoxyC1-Cealkyl,
`
`-C(O)(CH2)nNR°R®,
`
`-C(O)-(CH2)n-
`
`3
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`-S(O)(=NR')R”, —
`-S(O)2NR!°R!’,
`-CN,
`-C(O)-(CH2)n-O-N=CR°R®,
`NR/C(O)R®,
`C(O)C(O)R”", -C(O)C(R*3)=N-O-R”*, —C(O)C(R*)=N-NR*°R”°, -(CH2)n-phenyl, -C(O)-
`
`(CH2)n-phenyl, -S(O)n-(CHz2)n-phenyl, -heterocyclyl, -C(O)-(CH2)n-heterocyclyl, -S(O)n-
`
`(CH2)n-heterocyclyl, wherein each heterocyclyl is a 5- or 6- membered heterocyclyl which
`
`may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms
`
`each independently selected from the group consisting of oxygen, nitrogen and sulphur,
`
`and wherein said heterocyclyl or phenyl groups are optionally substituted by one, two or
`
`three substituents independently selected from the group consisting of Ci-Csalkyl, Ci-
`
`Cshaloalkyl, Ci-Csalkoxy, Co-Csalkenyl, C2-Csalkynyl, halogen, cyano andnitro;
`
`R°is selected from the group consisting of hydrogen and C1-Ce alkyl;
`
`R®°
`
`is selected from the group consisting of hydrogen, Ci-Cealkyl, C2-Cealkenyl, C2-
`
`Cealkynyl, Ci-Cohaloalkyl, hydroxyl-, Ci-Cealkoxy, C3-Ce cycloalkyl, , -Ci-CsalkoxyC1-
`Cealkyl,
`-Ci-CsalkoxyCi-Cehaloalkyl,
`-(CR°R!°)C1-Cchaloalkyl,
`-(CR’R'!°)C(O)NR°R?,
`
`phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or
`
`three substituents independently selected from the group consisting of Ci-C3 alkyl, Ci-C3
`
`haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano andnitro; or
`
`R° and R° together form —CH2CH2OCH2CH-; and
`
`R/is selected from the group consisting of hydrogen and C1-Ce alkyl;
`
`R®is selected from the group consisting of hydrogen, C1-Co alkyl, Ci-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 Ci-C3
`
`alkyl, Ci-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and
`
`nitro;
`
`R?is hydrogen or methyl,
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`R!° is hydrogen or methyl; or
`
`R’ and R™®together form —CH2CH?-; and
`
`R" is hydrogen or methyl,
`
`R”is selected from the group consisting of hydrogen, Ci-Ce alkyl, hydroxyl and Ci-Ce
`
`alkoxy-;
`
`R}is selected from the group consisting of hydrogen, Ci-Ce alkyl, hydroxyl and Ci-Ce
`
`alkoxy; or
`
`Rand R'? together form —CH2-X-CH-; and
`
`X is selected from the group consisting of O, S and N-R";
`
`R"is selected from the group consisting of hydrogen, Ci-C3 alkyl and C1-C3 alkoxy-;
`
`R}is independently selected from the group consisting of C1-C4 alkyl, Ci-C4 haloalkyl,
`
`cyano and halogen;
`
`R'° is hydrogen or Ci-Cealkyl; and
`
`R!’ is selected from the group consisting of hydrogen, C1-Cealkyl, C3-Cecycloalkyl, Ci-Ce
`
`alkoxy-C1-Csalkyl-,-C(O)Ci-Cealkyl, -C(O)OCi-Cealkyl and CH2CN;or
`
`R'° and R"’ together form —CH2CH2O0CH2CH2-, -CH2CH2S(O)2CH2CH2-;
`
`Ris hydrogen or Ci-Cealkyl;
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`R”is selected from the group consisting of hydrogen, C1-Ce alkyl, Ci-Co alkoxy, C3-
`
`Cocycloalkyl, 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, Ci-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and
`
`nitro;
`
`R”’is selected from the group consisting of C1-Cealkyl, Ci-Cehaloalkyl, Ci-Cealkoxy-, C1-
`Cchaloalkoxy,
`-NR?'R”, phenyl and -pyridyl, wherein the phenyl and pyridyl are
`
`optionally substituted by one, two or three substituents independently selected from the
`
`group consisting of Ci-C3 alkyl, Ci-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3
`
`alkynyl, halogen, cyano andnitro;
`
`R*! is selected from the group consisting of hydrogen, C1-Ce alkyl, Ci-Ce alkoxy, Ci-
`
`CoalkoxyC1-Caalkyl-, C3-Ce cycloalkyl, Ci-Cehaloalkyl- and Ci-Cehaloalkoxy-, -C(O)C1-
`
`Cealkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one,
`
`twoor three substituents independently selected from the group consisting of C1-C3 alkyl,
`
`Ci-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano andnitro;
`
`R”is hydrogen or C1-Cealkyl; or
`
`R*! and R”together form -CH2CH20CH2CH>-;
`
`R®is selected from the group consisting of hydrogen, Ci-Cealkyl, Ci-Cehaloalkyl, C1-
`
`Cealkoxy- and Ci-Cehaloalkoxy-;
`
`R**is selected from the group consisting of hydrogen, C1-Cealkyl, C1-CealkoxyC1-C3alkyl-
`
`, C3-Cocycloalkyl, -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 Ci-Csalkyl, Ci-Cshaloalkyl, Ci-Csalkoxy, C2-
`
`Csalkenyl, C2-C3alkynyl, halogen, cyano andnitro;
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`R*is hydrogen or C1-Ce alkyl;
`
`R”° is hydrogen or C1-Ce alkyl;
`
`G is selected from the group consisting of hydrogen,
`-(CH2)n-R’,
`(CRSR®)n-O-R®, -C(O)NR°R®, -S(O)2-R? and C1-Csalkoxy-C1-Caalkyl-;
`
`-C(O)-R*, -C(O)-
`
`R®* is independently selected from the group consisting of hydrogen, Ci-Cealkyl, Ci-
`
`Cshaloalkyl, C2-Csalkenyl, C2-Csalkynyl, 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 Ci-Csalkyl, Ci-
`
`Cshaloalkyl, Ci-Csalkoxy, Co-Csalkenyl, C2-Csalkynyl, halogen, cyano andnitro;
`
`R° is selected from the group consisting of C1-Csalkyl, Ci-Cshaloalkyl, C2-Csalkenyl, 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 Ci-Cs3alkyl, Ci-Cshaloalkyl, Ci-Csalkoxy, Co-Csalkenyl, C2-
`
`Csalkynyl, halogen, cyano andnitro;
`
`R‘ is hydrogen or Ci-C3 alkyl;
`
`R¢is hydrogen or C1-C3 alkyl; and
`
`nis independently 0, 1 or 2;
`
`or an agriculturally acceptable salt thereof.
`
`2.
`
`(Currently Amended) The[[A]] compound according to claim 1, which is a compound of
`
`Formula (Ia)
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`wherein
`
`R’is methyl or methoxy;
`
`R? is methyl or methoxy;
`
`R‘is selected from the group consisting of Ci-Caalkyl, C1-Caalkoxy-, C1-Cshaloalkyl, -
`
`C(O)Ci-Caalkyl, -C(O)Ci-Cshaloalkyl, -S(O)nCi-Cealkyl, -S(O)nCi-Cohaloalkyl, -S(O)n-
`(CH2)n-C3-Cecycloalkyl, -S(O)nC(R'RVR, -C(O)H, -C(O)-(CH2)n-C3-Cocycloalkyl,
`-
`C(O)C(RE)RVRE,
`-C(O)C2-Caalkenyl,
`-C(O)(CR°R™)CN,
`-C(O)OC1-Cealkyl,
`
`C(O)OCi-Cehaloalkyl,
`
`-C(OQ)(CH2)nS(O)nCi-Coalkyl,
`
`-C(O)Ci-CsalkoxyC1-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)-(CHz2)n-heterocyclyl, -S(O)n-(CH2)n-
`
`heterocyclyl, wherein each heterocyclyl is a 5- or 6- membered heterocyclyl which may be
`
`aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each
`
`independently selected from the group consisting of oxygen, nitrogen and sulphur, and
`
`wherein said heterocyclyl or phenyl groups are optionally substituted by one, two or three
`
`substituents independently selected from the group consisting of Ci-Csalkyl, Ci-
`
`Cshaloalkyl, Ci-Csalkoxy, Co-Csalkenyl, C2-Csalkynyl, halogen, cyano andnitro;
`
`R°is selected from the group consisting of hydrogen and C1-Ce alkyl;
`
`R° is selected from the group consisting of hydrogen, C1-Co alkyl, Ci-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 Ci-C3
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`alkyl, Ci-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and
`
`nitro; or
`
`R° and R° together form —CH2CH2O0CH2CH>-; and
`
`R/is selected from the group consisting of hydrogen and C1-Ce alkyl;
`
`R®is selected from the group consisting of hydrogen, C1-Co alkyl, Ci-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 Ci-C3
`
`alkyl, Ci-C3 haloalkyl, Ci-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and
`
`nitro;
`
`R?is hydrogen or methyl,
`
`R!° is hydrogen or methyl; or
`
`R’ and R™®together form —CH2CH?-; and
`
`R!' is hydrogen or methy];
`
`R” and R®together form —CH2-X-CH?-;
`
`X is selected from the group consisting of O, S and N-R";
`
`Ris selected from the group consisting of hydrogen, C1-C3alkyl and C1-C3 alkoxy-;
`
`G is selected from the group consisting of hydrogen,
`-(CH2)n-R*,
`(CRSR*)n-O-R°, -C(O)YNR?R?, -S(O)2-R? and C1-Csalkoxy-C1-Csalkyl-;
`
`-C(O)-R*, -C(O)-
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`R®* is independently selected from the group consisting of hydrogen, Ci-Cealkyl, Ci-
`
`Cshaloalkyl, C2-Csalkenyl, C2-Csalkynyl, 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 Ci-Csalkyl, Ci-
`
`Cshaloalkyl, Ci-Csalkoxy, Co-Csalkenyl, C2-Csalkynyl, halogen, cyano andnitro;
`
`R° is selected from the group consisting of C1-Csalkyl, Ci-Cshaloalkyl, C2-Csalkenyl, 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 Ci-Cs3alkyl, Ci-Cshaloalkyl, Ci-Csalkoxy, Co-Csalkenyl, C2-
`
`Csalkynyl, halogen, cyano andnitro;
`
`RS is hydrogen or Ci-C3 alkyl;
`
`R¢is hydrogen or C1-C3 alkyl; and
`
`nis independently 0, 1 or 2;
`
`or an agriculturally acceptable salt thereof.
`
`3.
`
`(Currently Amended) The[[A]] compoundaccording to claim 1-cr-elaim-2, wherein R?is
`
`methyl.
`
`4.
`
`(Currently Amended) The[[A]] compound according to amy—ene—efthe—previeus
`
`elaimsclaim 1, wherein R? is methyl.
`
`5.
`
`6.
`
`(Currently Amended) [[A]]The compoundaccording to anyere-efthe-previeus-claims—.
`2er3claim 1, wherein R? is methoxy.
`
`(Currently Amended) The[[A]] compound according to amy—ene—ef+the—previeus
`elaimsclaim 1, wherein R* is -C(O)OC1-Cealkyl.
`
`10
`
`
`
`Application No. Not Yet Assigned
`Preliminary Amendment submitted April 6, 2021
`
`Docket No.: SYG-451PA (115479.0004 14)
`
`(Currently Amended) The[[A]] compoundaccording to any-erne-ofthe-clatmstteSclaim
`1, wherein R* is -C(O)NR°R®.
`
`(Currently Amended) The[[A]] compound according to amy—ene—efthe—previeus
`
`elaimsclaim 1, wherein Gis hydrogen.
`
`
`
`
`
`(Currently Amended) The[[A]] compound according toany-one-ofclatms—tte—claim 1,
`
`wherein G is -C(O)C1-Cealkyl.
`
`10.
`
`(Currently Amended) The[[A]] compound according to anyerne-ofelatmstte—claim 1,
`
`wherein G is -C(O)-O-C1-Cealkyl.
`
`11.
`
`(Currently Amended) A herbicidal composition comprising a compound of Formula (1) ef
`
`
`
`Formulate}-accordinete—any_erneofthe_previeus_claimsaccording to claim 1 and an
`
`agriculturally acceptable formulation adjuvant.
`
`12.
`
`(Currently Amended) The[[A]] herbicidal composition according to claim 11, further
`
`comprising at least one additional pesticide.
`
`13.
`
`(Currently Amended) The[[A]] herbicidal composition according to claim 12, wherein the
`
`additional pesticide is a herbicide or herbicide safener.
`
`14.
`
`(Currently Amended) A method of controlling weeds at a locus comprising application to
`
`
`
`the locus of a weed controlling amount of a composition according to any-erne-efclaims
`
`te-Kclaim 11.
`
`15.
`
`(Original) Use of a compoundof Formula(I) as defined in claim 1 as a herbicide.
`
`11
`
`
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