LISTING OF THE CHALLENGED CLAIMS
`CLAIMS 1-7, 9-13, 21-31
`
`1. A compound selected from Formula 1, N-oxides and salts thereof:
`
`wherein
`
`Q1 is a phenyl ring optionally substituted with up to 5 substituents
`independently selected from R7; or a 5- to 6-membered heterocyclic ring or an 8- to
`10-membered heteroaromatic bicyclic ring system, each ring or ring system
`containing ring members selected from carbon atoms and 1 to 4 heteroatoms
`independently selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up
`to 3 carbon ring members are independently selected from C(═O) and C(═S), and
`the sulfur atom ring members are independently selected from S(═O)u(═NR8)v,
`each ring or ring system optionally substituted with up to 5 substituents
`independently selected from R7 on carbon atom ring members and selected from R9
`on nitrogen atom ring members;
`
`Q2 is a phenyl ring or a naphthalenyl ring system, each ring or ring system
`optionally substituted with up to 5 substituents independently selected from R10; or
`a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to 10-membered
`heteroaromatic bicyclic ring system, each ring or ring system containing ring
`members selected from carbon atoms and 1 to 4 heteroatoms independently
`selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring
`members are independently selected from C(═O) and C(═S), and the sulfur atom
`ring members are independently selected from S(═O)u(═NR8)v, each ring or ring
`system optionally substituted with up to 5 substituents independently selected from
`R10 on carbon atom ring members and selected from R11 on nitrogen atom ring
`members;
`
`Y1 and Y2 are each independently O, S or NR12;
`
`Page 1 of 9
`
`SYNGENTA EXHIBIT 1023
`Syngenta v. FMC, PGR2020-00028
`
`

`

`R1 is H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6
`alkynyl, C4-C8 cycloalkylalkyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8
`alkylthioalkyl, C2-C8 alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8
`alkylcarbonyl, C2-C8 haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8
`alkoxycarbonyl, C2-C8 haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8
`alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C4-C10
`cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-
`C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C3-C8
`cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C3-C8
`cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10
`trialkylsilyl or G1;
`
`R2 and R3 are each independently H, halogen or C1-C4 alkyl; or
`R2 and R3 are taken together with the carbon atom to which they are bonded to
`form a C3-C7 cycloalkyl ring;
`
`
`R4 and R5 are each independently H, halogen or C1-C4 alkyl;
`
`
`
`R6 is H, hydroxy, amino, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6
`alkynyl, C2-C8 alkoxyalkyl, C2-C8 haloalkoxyalkyl, C2-C8 alkylthioalkyl, C2-C8
`alkylsulfinylalkyl, C2-C8 alkylsulfonylalkyl, C2-C8 alkylcarbonyl, C2-C8
`haloalkylcarbonyl, C4-C10 cycloalkylcarbonyl, C2-C8 alkoxycarbonyl, C2-C8
`haloalkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C2-C8 alkylaminocarbonyl, C3-
`C10 dialkylaminocarbonyl, C4-C10 cycloalkylaminocarbonyl, C1-C6 alkoxy, C1-C6
`alkylthio, C1-C6 haloalkylthio, C3-C8 cycloalkylthio, C1-C6 alkylsulfinyl, C1-C6
`haloalkylsulfinyl, C3-C8 cycloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6
`haloalkylsulfonyl, C3-C8 cycloalkylsulfonyl, C1-C6 alkylaminosulfonyl, C2-C8
`dialkylaminosulfonyl, C3-C10 trialkylsilyl or G1;
`
`each R7 and R10 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4
`haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl C2-C4 alkynyl, C2-C4 haloalkynyl, C1-
`C4 nitroalkyl, C2-C4 nitroalkenyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C3-C4
`cycloalkyl, C3-C4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C1-C4
`alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4
`alkynyloxy, C3-C4 haloalkynyloxy, C3-C4 cycloalkoxy, C1-C4 alkylthio, C1-C4
`haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-
`C4 haloalkylsulfonyl, hydroxy, formyl, C2-C4 alkylcarbonyl, C2-C4
`alkylcarbonyloxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy,
`formylamino, C2-C4 alkylcarbonylamino, —SF5, —SCN, C3-C4 trialkylsilyl,
`trimethylsilylmethyl or trimethylsilylmethoxy;
`
`Page 2 of 9
`
`

`

`
`each R8 is independently H, cyano, C2-C3 alkylcarbonyl or C2-C3
`haloalkylcarbonyl;
`
`each R9 and R11 is independently cyano, C1-C3 alkyl, C2-C3 alkenyl, C2-C3
`alkynyl, C3-C6 cycloalkyl, C2-C3 alkoxyalkyl, C1-C3 alkoxy, C2-C3 alkylcarbonyl,
`C2-C3 alkoxycarbonyl, C2-C3 alkylaminoalkyl or C3-C4 dialkylaminoalkyl;
`each R12 is independently H, cyano, C1-C4 alkyl, C1-C4 haloalkyl, —(C═O)CH3 or
`—(C═O)CF3;
`
`
`each G1 is independently phenyl, phenylmethyl, pyridinylmethyl,
`phenylcarbonyl, phenoxy, phenylethynyl, phenylsulfonyl or a 5- or 6-membered
`heteroaromatic ring, each optionally substituted on ring members with up to 5
`substituents independently selected from R13;
`
`
`each R13 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —
`C(═O)OH, —C(═O)NH2, —SO2NH2, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl,
`C2-C6 alkynyl, C2-C8 alkylcarbonyl, C2-C8 haloalkylcarbonyl, C2-C8
`alkoxycarbonyl, C4-C10 cycloalkoxycarbonyl, C5-C12 cycloalkylalkoxycarbonyl, C2-
`C8 alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1-C6 alkoxy, C1-C6
`haloalkoxy, C2-C8 alkylcarbonyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6
`alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl,
`C1-C6 alkylaminosulfonyl, C2-C8 dialkylaminosulfonyl, C3-C10 trialkylsilyl, C1-C6
`alkylamino, C2-C8 dialkylamino, C2-C8 alkylcarbonylamino, C1-C6
`alkylsulfonylamino, phenyl, pyridinyl or thienyl; and
`each u and v are independently 0, 1 or 2 in each instance of S(═O)u(═NR8)v,
`provided that the sum of u and v is 0, 1 or 2;
`
`provided that
`(a) the compound of Formula 1 is other than N-1H-benzotriazol-1-yl-2-oxo-
`4-phenyl-3-pyrrolidinecarboxamide;
`(b) when Q1 is a 3-furanyl or 3-pyridinyl ring, then said ring is substituted
`with at least one substituent selected from R7;
`(c) when Q1 is unsubstituted phenyl, and Q2 is a phenyl or pyridyl ring, then
`said Q2 ring is substituted with R10 other than optionally substituted phenoxy at a 2-
`position (relative to the bond of the Q2 ring to the remainder of Formula 1), and
`unsubstituted at the 5- and 6-positions (with respect to the 2-position), and R5 is H
`or halogen;
`
`Page 3 of 9
`
`

`

`(d) when Q1 is a phenyl ring and said ring is substituted with R7 at both ortho
`positions (relative to the bond to the remainder of Formula 1), then said ring is also
`independently substituted with R7 on at least one additional position;
`(e) Q2 is other than optionally substituted 1H-pyrazol-5-yl; and
`(f) when Q2 is a 1H-pyrazol-3-yl ring, said ring is substituted at the 1-
`position with R11.
`
`2. The compound of claim 1 wherein
`
`each R9 and R11 is independently C1-C2 alkyl.
`
`
`3. The compound of claim 2 wherein
`
`
`Y1 and Y2 are each O;
`
`R2, R3, R4, R5 and R6 are each H; and
`
`
`
`
`
`R1 is H, C1-C6 alkyl, C1-C6 haloalkyl or C4-C8 cycloalkylalkyl.
`
`
`4. The compound of claim 3 wherein
`
`
`Q1 is a phenyl ring substituted with 1 to 3 substituents independently
`selected from R7;
`
`Q2 is a phenyl ring substituted with 1 to 3 substituents independently
`selected from R10; and
`
`
`R1 is H, C1-C6 alkyl or C1-C6 haloalkyl.
`
`
`5. The compound of claim 4 wherein
`
`
`each R7 is independently halogen, cyano, C1-C2 alkyl, C1-C3 haloalkyl or C1-
`C3 alkylsulfonyl;
`
`each R10 is independently halogen, cyano, nitro, C1-C2 alkyl, C1-C3 haloalkyl
`or C1-C3 alkylsulfonyl; and
`
`
`R1 is H, Me, Et or CHF2.
`
`
`6. The compound of claim 5 wherein
`
`Page 4 of 9
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`

`
`Q1 is a phenyl ring substituted with 1 substituent selected from R7 at the para
`position or substituted with 2 substituents independently selected from R7 wherein
`one substituent is at the para position and the other substituent is at a meta position;
`
`
`Q2 is a phenyl ring substituted with 1 substituent selected from R10 at an
`ortho position or substituted with 2 substituents independently selected from R10
`wherein one substituent is at an ortho position and the other substituent is at the
`adjacent meta position; and
`
`
`R1 is H, Me or Et.
`
`
`7. The compound of claim 6 wherein
`
`
`each R7 is independently F or CF3;
`
`
`
`each R10 is F; and
`
`R1 is H or CH3.
`
`
`9. A herbicidal composition comprising a compound of claim 1 and at least one
`component selected from the group consisting of surfactants, solid diluents and
`liquid diluents.
`
`10. The herbicidal composition of claim 9 further comprising at least one
`additional active ingredient selected from the group consisting of other herbicides
`and herbicide safeners.
`
`11. A herbicidal mixture comprising
`
`(a) a compound of claim 1, and
`
`(b) at least one additional active ingredient selected from (b1) photosystem
`II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA
`carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-
`pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I
`electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8)
`glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA)
`elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase
`(PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors,
`
`Page 5 of 9
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`

`

`(b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose
`biosynthesis inhibitors, (b15) other herbicides selected from mitotic disruptors,
`organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet,
`difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium,
`metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and
`pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through
`(b16).
`
`12. A herbicidal mixture comprising
`(a) a compound of claim 1, and
`
`(b) at least one additional active ingredient selected from (b2) acetohydroxy
`acid synthase (AHAS) inhibitors, (b9) very long chain fatty acid (VLCFA)
`elongase inhibitors, and (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD)
`inhibitors; and salts of compounds of (b2), (b9) and (b12).
`
`
`13. A method for controlling the growth of undesired vegetation comprising
`contacting the vegetation or its environment with a herbicidally effective amount
`of a compound of claim 1.
`
`21. A mixture comprising
`a compound of claim 1 and
`
` a
`
` compound selected from benzobicyclon, bromobutide, fenquinotrione,
`metazosulfuron, pethoxamid, pretilachlor, pyrazolynate, pyrazosulfuron-ethyl,
`pyrimisulfan and triafamone.
`
`22. The compound of claim 1 wherein
`
`
`Q1 is a phenyl ring optionally substituted with up to 5 substituents
`independently selected from R7.
`
`23. The compound of claim 1 wherein
`
`
`Q1 is a 5- to 6-membered fully unsaturated heterocyclic ring, each ring
`optionally substituted with up to 5 substituents independently selected from R7 on
`carbon atom ring members and selected from R9 on nitrogen atom ring members.
`
`24. The compound of claim 1 wherein
`
`
`Page 6 of 9
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`

`

`Q1 is selected from
`
`
`
`
`25. The compound of claim 1 wherein
`
`
`Q1 is selected from
`
`
`
`and r is 0 to 4.
`
`26. The compound of claim 1 wherein
`Q1 is
`
`
`
`
`
`and r is 0 to 4.
`27. The compound of claim 1 wherein
`
`
`Q2 is a phenyl ring optionally substituted with up to 5 substituents
`independently selected from R10.
`
`Page 7 of 9
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`

`
`28. The compound of claim 1 wherein
`
`
`Q2 is an 8- to 10-membered heteroaromatic bicyclic ring system optionally
`substituted with up to 5 substituents independently selected from R10 on carbon
`atom ring members and selected from R11 on nitrogen atom ring members.
`
`29. The compound of claim 1 wherein
`
`
`Q2 is selected from
`
`
`
`
`30. The compound of claim 1 wherein
`
`Q2 is selected from
`
`
`
`
`
`
`
`and r is 0 to 4.
`
`Page 8 of 9
`
`

`

`31. A compound selected from Formula 1, N-oxides and salts thereof:
`
`wherein
`
`
`
`
`Q1 is a phenyl ring substituted with 1 to 3 substituents independently
`selected from R7;
`
`
`Q2 is a phenyl ring substituted with 1 to 3 substituents independently
`selected from R10;
`
`
`Y1 and Y2 are each O;
`
`R1 is H, C1-C6 alkyl, C1-C6 haloalkyl or C4-C8 cycloalkylalkyl;
`
`R2, R3, R4, R5 and R6 are each H;
`
`
`
`
`
`
`
`each R7 and R10 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4
`haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl C2-C4 alkynyl, C2-C4 haloalkynyl, C1-
`C4 nitroalkyl, C2-C4 nitroalkenyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C3-C4
`cycloalkyl, C3-C4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C1-C4
`alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4
`alkynyloxy, C3-C4 haloalkynyloxy, C3-C4 cycloalkoxy, C1-C4 alkylthio, C1-C4
`haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-
`C4 haloalkylsulfonyl, hydroxy, formyl, C2-C4 alkylcarbonyl, C2-C4
`alkylcarbonyloxy, C1-C4 alkylsulfonyloxy, C1-C4 haloalkylsulfonyloxy,
`formylamino, C2-C4 alkylcarbonylamino, —SF5, —SCN, C3-C4 trialkylsilyl,
`trimethylsilylmethyl or trimethylsilylmethoxy;
`
`
`provided that
`
`
`
`when Q1 is a phenyl ring directly bonded to the remainder of Formula 1 and
`said ring is substituted with R7 at both ortho positions relative to the bond to the
`remainder of Formula 1, then said ring is also independently substituted with R7 on
`at least one additional position.
`
`
`Page 9 of 9
`
`