I 1111111111111111 1111111111 111111111111111 1111111111 111111111111111 IIII IIII
`USO 10294202B2
`
`c12) United States Patent
`Satterfield et al.
`
`(IO) Patent No.: US 10,294,202 B2
`(45) Date of Patent:
`May 21, 2019
`
`(54) PYRROLIDINONES AS HERBICIDES
`
`(71) Applicant: FMC Corporation, Philadelphia, PA
`(US)
`
`(72)
`
`Inventors: Andrew Duncan Satterfield, Furlong,
`PA (US); Thomas Paul Selby,
`Hockessin, DE (US); David Andrew
`Travis, North East, MD (US); Kanu
`Maganbhai Patel, Sugarland, TX (US);
`Andrew Edmund Taggi, New Hope,
`PA (US)
`
`(73) Assignee: FMC CORPORATION, Philadelphia,
`PA (US)
`
`(2013.01); A0lN 47138 (2013.01); C07D
`401/04 (2013.01); C07D 401112 (2013.01);
`C07D 403/04 (2013.01); C07D 403112
`(2013.01); C07D 407104 (2013.01); C07D
`407112 (2013.01); C07D 409/04 (2013.01);
`C07D 413112 (2013.01); C07D 417112
`(2013.01)
`
`(58) Field of Classification Search
`CPC C07D 207/277; C07D 401/04; C07D 401/12;
`C07D 403/04; C07D 403/12; C07D
`407/04; C07D 407/12; C07D 409/04;
`C07D 413/12; C07D 417/12
`See application file for complete search history.
`
`( *) Notice:
`
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by O days.
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`(21) Appl. No.:
`
`15/101,615
`
`(22) PCT Filed:
`
`Dec. 2, 2014
`
`(86) PCT No.:
`
`PCT/US2014/068073
`
`§ 371 (c)(l),
`(2) Date:
`
`Jun.3, 2016
`
`(87) PCT Pub. No.: WO2015/084796
`
`PCT Pub. Date: Jun. 11, 2015
`
`(65)
`
`Prior Publication Data
`
`US 2016/0297756 Al
`
`Oct. 13, 2016
`
`3,741,989 A
`4,594,094 A
`
`6/ 1973 Zaugg
`6/1986 Kollmeyer
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`CN
`DE
`
`10/2013
`102531918 B
`3/1968
`1262277 B
`(Continued)
`
`OTHER PUBLICATIONS
`
`XP002734980.
`
`(Continued)
`
`Related U.S. Application Data
`
`(60) Provisional application No. 61/911,324, filed on Dec.
`3, 2013.
`
`Primary Examiner - Valerie Rodriguez-Garcia
`(74) Attorney, Agent, or Firm - Reed A Coats
`
`(57)
`
`ABSTRACT
`
`Disclosed are compounds of Formula 1, including all ste(cid:173)
`reoisomers, N-oxides, and salts thereof:
`
`(51)
`
`Int. Cl.
`C07D 2071277
`C07D 403112
`C07D 401/04
`C07D 401112
`C07D 403/04
`C07D 407104
`C07D 407112
`C07D 409/04
`C07D 413112
`C07D 417112
`A0lN 43108
`A0lN 43156
`A0lN 43182
`A0lN 47116
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(Continued)
`
`(52) U.S. Cl.
`CPC ......... C07D 2071277 (2013.01); A0lN 43108
`(2013.01); A0lN 43136 (2013.01); A0lN
`43140 (2013.01); A0lN 43150 (2013.01);
`A0lN 43154 (2013.01); A0lN 43156
`(2013.01); A0lN 43176 (2013.01); A0lN
`43178 (2013.01); A0lN 43182 (2013.01);
`A0lN 47116 (2013.01); A0lN 47136
`
`tty2 ✓Q2
`
`Q
`
`R3
`
`R2
`
`N
`I
`RI
`
`\
`
`R6
`
`yI
`
`, and Y 2 are as
`, Y 1
`, Q1, Q2
`, R6
`, R5
`, R4
`, R3
`wherein R1, R2
`defined in the disclosure. Also disclosed are compositions
`containing the compounds of Formula 1 and methods for
`controlling undesired vegetation comprising contacting the
`undesired vegetation or its environment with an effective
`amount of a compound or a composition of the invention.
`
`31 Claims, No Drawings
`
`SYNGENTA EXHIBIT 1001
`Syngenta v. FMC, PGR2020-00028
`
`

`

`US 10,294,202 B2
`Page 2
`
`(51)
`
`Int. Cl.
`A0JN 43154
`A0JN 47136
`A0JN 47138
`A0JN 43140
`A0JN 43136
`A0JN 43150
`A0JN 43176
`A0JN 43178
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`(56)
`
`References Cited
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`U.S. PATENT DOCUMENTS
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`4,874,422 A
`7,205,318 B2
`8,293,926 B2
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`5/2016 Kotoku ................ A61K 31/422
`514/210.18
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`2018/0215760 Al
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`10/2016 Defays et al.
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`3/2018 Stevenson et al.
`4/2018 Satterfield et al.
`5/2018 Campbell et al.
`8/2018 Satterfield et al.
`8/2018 Campbell et al.
`
`FOREIGN PATENT DOCUMENTS
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`EP
`IN
`JP
`JP
`JP
`KR
`RU
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`
`2336104 Al
`1462DEL08
`53-056288 A
`54-088114 A
`08-269145 A
`20130142477 A
`2555370 Cl
`2000/09481 Al
`2004/046081 Al
`2006/081562 A2
`2009/062371 Al
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`2016/094117 Al
`2016/164201 Al
`2016/176082 Al
`2016/182780 Al
`2016/196019 Al
`2016/196593 Al
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`2018/118384 Al
`2018/175226 Al
`2018/175231 Al
`
`6/2011
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`5/1978
`7 /1979
`10/1996
`12/2013
`7/2015
`2/2000
`6/2004
`8/2006
`5/2009
`1/2016
`6/2016
`10/2016
`11/2016
`11/2016
`12/2016
`12/2016
`2/2017
`6/2018
`9/2018
`9/2018
`
`OTHER PUBLICATIONS
`
`XP002734981.
`XP0027 59805.
`XP002759806.
`XP055297105.
`XP055297107.
`XP009191451.
`XP002278920.
`IPCOM000241978D.
`PubChem CID 29937915; May 28, 2009.
`
`* cited by examiner
`
`

`

`US 10,294,202 B2
`
`1
`PYRROLIDINONES AS HERBICIDES
`
`FIELD OF THE INVENTION
`
`This invention relates to certain pyrrolidinones, their 5
`N-oxides and salts, and compositions and methods of their
`use for controlling undesirable vegetation.
`
`BACKGROUND OF THE INVENTION
`
`10
`
`The control of undesired vegetation is extremely impor(cid:173)
`tant in achieving high crop efficiency. Achievement of
`selective control of the growth of weeds especially in such
`useful crops as rice, soybean, sugar beet, maize, potato,
`wheat, barley, tomato and plantation crops, among others, is 15
`very desirable. Unchecked weed growth in such useful crops
`can cause significant reduction in productivity and thereby
`result in increased costs to the consumer. The control of
`undesired vegetation in noncrop areas is also important.
`Many products are commercially available for these pur- 20
`poses, but the need continues for new compounds that are
`more effective, less costly, less toxic, environmentally safer
`or have different sites of action.
`
`SUMMARY OF THE INVENTION
`
`This invention is directed to compounds of Formula
`(including all stereoisomers), including N-oxides and salts
`thereof, agricultural compositions containing them and their
`use as herbicides:
`
`y2 ✓Q2
`
`Q
`
`R3
`
`R2
`
`N
`I
`RI
`
`\
`s R6
`
`yI
`
`25
`
`30
`
`35
`
`40
`
`wherein
`Q1 is a phenyl ring or a naphthalenyl ring system, each
`ring or ring system optionally substituted with up to 5 45
`substituents independently selected from R7
`; or a 5- to
`6-membered fully unsaturated heterocyclic ring or an
`8- to IO-membered heteroaromatic bicyclic ring sys(cid:173)
`tem, each ring or ring system containing ring members
`selected from carbon atoms and I to 4 heteroatoms 50
`independently selected from up to 2 0, 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( NRg)v, each ring or ring 55
`system optionally substituted with up to 5 substituents
`independently selected from R 7 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 60
`ring or ring system optionally substituted with up to 5
`substituents independently selected from R 10
`; or a 5- to
`6-membered fully unsaturated heterocyclic ring or an
`8- to IO-membered heteroaromatic bicyclic ring sys(cid:173)
`tem, each ring or ring system containing ring members 65
`selected from carbon atoms and I to 4 heteroatoms
`independently selected from up to 2 0, up to 2 S and
`
`2
`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)J NRg)v, each ring or ring
`system optionally substituted with up to 5 substituents
`independently selected from R 10 on carbon atom ring
`members and selected from R 11 on nitrogen atom ring
`members;
`Y1 and Y2 are each independently 0, Sor NR12;
`R 1 is H, hydroxy, amino, C1 -C6 alkyl, C1 -C6 haloalkyl,
`C2-C6 alkenyl, C3 -C6 alkynyl, C4 -Cg cycloalkylalkyl,
`C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alky(cid:173)
`lthioalkyl, C2-Cg alkylsulfinylalkyl, C2-Cg alkylsulfo(cid:173)
`nylalkyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbo(cid:173)
`nyl, C4 -C10 cycloalkylcarbonyl, C2-Cg alkoxycarbonyl,
`C2-Cg haloalkoxycarbonyl, C4 -C 10 cycloalkoxycarbo(cid:173)
`nyl, C2-Cg alkylaminocarbonyl, C3-C 10 dialkylamin(cid:173)
`ocarbonyl, C4 -C 10 cycloalkylaminocarbonyl, C1-C6
`alkoxy, C1 -C6 alkylthio, C1 -C6 haloalkylthio, C3 -Cg
`cycloalkylthio, C1 -C6 alkylsulfinyl, C1-C6 haloalkyl(cid:173)
`sulfinyl, C3 -Cg cycloalkylsulfinyl, C1 -C6 alkylsulfonyl,
`C1 -C6 haloalkylsulfonyl, C3 -Cg cycloalkylsulfonyl,
`C1 -C 6 alkylaminosulfonyl, C2-Cg dialkylaminosulfo(cid:173)
`nyl, C3-C 10 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;
`R 6 is H, hydroxy, amino, C1 -C6 alkyl, C1 -C6 haloalkyl,
`C2-C6 alkenyl, C3 -C6 alkynyl, C2-Cg alkoxyalkyl,
`C2-Cg haloalkoxyalkyl, C2-Cg alkylthioalkyl, C2-Cg
`alkylsulfinylalkyl, C2-Cg alkylsulfonylalkyl, C2-Cg
`haloalkylcarbonyl, C4 -C 10
`alkylcarbonyl, C2-Cg
`cycloalkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg
`cycloalkoxycarbonyl,
`haloalkoxycarbonyl, C4 -C 10
`C2-Cg alkylaminocarbonyl, C3 -C 10 dialkylaminocarbo(cid:173)
`nyl, C4 -C 10 cycloalkylaminocarbonyl, C1-C6 alkoxy,
`C1-C6 alkylthio, C1 -C6 haloalkylthio, C3 -Cg cycloalky(cid:173)
`lthio, C1 -C6 alkylsulfinyl, C1 -C6 haloalkylsulfinyl,
`C3 -Cg cycloalkylsulfinyl, C1 -C6 alkylsulfonyl, C1 -C6
`haloalkylsulfonyl, C3 -Cg cycloalkylsulfonyl, C1-C6
`dialkylaminosulfonyl,
`alkylaminosulfonyl, C2-Cg
`C3-C 10 trialkylsilyl or G1;
`each R7 and R 10 is independently halogen, cyano, nitro,
`cl -Cg alkyl, cl -Cg haloalkyl, cl -Cg nitroalkyl, C2-Cg
`alkenyl, C2-Cg haloalkenyl, C2-Cg nitroalkenyl, C2-Cg
`alkynyl, C2-Cg haloalkynyl, C4 -C 10 cycloalkylalkyl,
`C4 -C 10 halocycloalkylalkyl, C5 -C 12 alkylcycloalkylal(cid:173)
`kyl, C5 -C 12 cycloalkylalkenyl, C5 -C 12 cycloalkylalky(cid:173)
`nyl, C3 -Cg cycloalkyl, C3 -Cg halocycloalkyl, C4 -C 10
`alkylcycloalkyl, CcC 12 cycloalkylcycloalkyl, C3-Cg
`cycloalkenyl, C3 -Cg halocycloalkenyl, C2-Cg alkoxy(cid:173)
`alkyl, C2-Cg haloalkoxyalkyl, C3-Cg haloalkoxyalkoxy,
`C3 -Cg alkoxyalkoxy, C4 -C 10 cycloalkoxyalkyl, C3 -C 10
`alkoxyalkoxyalkyl, C2-Cg alkylthioalkyl, C2-Cg alkyl(cid:173)
`sulfinylalkyl, C2-Cg alkylsulfonylalkyl, C2-Cg alkylam(cid:173)
`inoalkyl,
`haloalkylaminoalkyl,
`C4 -C 10
`C2-Cg
`cycloalkylaminoalkyl, C3 -C 10
`dialkylaminoalkyl,
`--CHO, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbo(cid:173)
`nyl, C4 -C 10 cycloalkylcarbonyl, -C(=O)OH, C2-Cg
`alkoxycarbonyl, C2-Cg haloalkoxycarbonyl, C4 -C 10
`cycloalkoxycarbonyl, C5 -C 12 cycloalkylalkoxycarbo(cid:173)
`nyl, ----C(=O)NH2, C2-Cg alkylaminocarbonyl, C4 -C 10
`cycloalkylaminocarbonyl, C3-C 10 dialkylaminocarbo(cid:173)
`nyl, C1 -Cg alkoxy, C1 -Cg haloalkoxy, C2-Cg alkoxy-
`
`

`

`US 10,294,202 B2
`
`5
`
`10
`
`3
`alkoxy, C2-Cg alkenyloxy, C2-Cg haloalkenyloxy,
`C3 -Cg alkynyloxy, C3 -Cg haloalkynyloxy, C3 -Cg
`cycloalkoxy,
`halocycloalkoxy,
`C3 -Cg
`C4 -C 10
`cycloalkylalkoxy, C3 -C 10 alkylcarbonylalkoxy, C2 -Cg
`alkylcarbonyloxy, C2 -Cg haloalkylcarbonyloxy, C4 -C 10
`cycloalkylcarbonyloxy, C 1 -Cg alkylsulfonyloxy, C 1 -Cg
`haloalkylsulfonyloxy, C 1 -Cg alkylthio, C1 -Cg haloalky(cid:173)
`lthio, C3 -Cg cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1-Cg
`haloalkylsulfinyl,
`alkylsulfonyl,
`C 1 -Cg
`C 1 -Cg
`haloalkylsulfonyl, C3 -Cg cycloalkylsulfonyl, fanny-
`!amino, C2-Cg alkylcarbonylamino, C2 -Cg haloalkyl(cid:173)
`carbonylamino, C2 -Cg alkoxycarbonylamino, C 1 -C6
`alkylsulfonylamino, C 1 -C6 haloalkylsulfonylamino,
`-SF5 , -SCN, SO2NH2 , C3 -C 12 trialkylsilyl, C4 -C 12 15
`trialkylsilylalkyl, C4 -C 12 trialkylsilylalkoxy or G2
`;
`each Rg is independently H, cyano, C2 -C3 alkylcarbonyl
`or C2 -C3 haloalkylcarbonyl;
`each R9 and R 11 is independently cyano, C 1-C3 alkyl,
`C2 -C3 alkenyl, C2 -C3 alkynyl, C3 -C6 cycloalkyl, C2 -C3 20
`alkoxyalkyl, C 1 -C3 alkoxy, C2 -C3 alkylcarbonyl, C2 -C3
`alkoxycarbonyl, C2 -C3 alkylaminoalkyl or C3 -C4
`dialkylaminoalkyl;
`each R 12 is independently H, cyano, C 1-C4 alkyl, C 1-C4
`haloalkyl, -(C=O)CH3 or -(C=O)CF3 ;
`each G 1 is independently phenyl, phenylmethyl (i.e. ben(cid:173)
`zyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl),
`phenoxy, phenylethynyl, phenylsulfonyl or a 5- or
`6-membered heteroaromatic ring, each optionally sub(cid:173)
`stituted on ring members with up to 5 substituents 30
`independently selected from R13
`;
`each G2 is independently phenyl, phenylmethyl (i.e. ben(cid:173)
`zyl), pyridinylmethyl, phenylcarbonyl (i.e. benzoyl),
`phenoxy, phenylethynyl, phenylsulfonyl or a 5- or
`6-membered heteroaromatic ring, each optionally sub- 35
`stituted on ring members with up to 5 substituents
`independently selected from R14
`;
`each R 13 and R14 is independently halogen, cyano,
`hydroxy,
`amino, nitro,
`-CHO,
`----C(=O)OH,
`----C(=O)NH2 ,
`-SO2NH2 , C 1-C6 alkyl, C 1-C6 40
`haloalkyl, C2 -C6 alkenyl, C2 -C6 alkynyl, C2 -Cg alkyl(cid:173)
`carbonyl, C2 -Cg haloalkylcarbonyl, C2 -Cg alkoxycar(cid:173)
`bonyl, C4 -C 10 cycloalkoxycarbonyl, C5 -C 12 cycloalky(cid:173)
`lalkoxycarbonyl, C2 -Cg alkylaminocarbonyl, C3 -C 10
`dialkylaminocarbonyl,
`alkoxy,
`C 1 -C6
`C 1 -C6 45
`haloalkoxy, C2 -Cg alkylcarbonyloxy, C 1 -C6 alkylthio,
`cl -C6 haloalkylthio, cl -C6 alkylsulfinyl, cl -C6
`haloalkylsulfinyl,
`alkylsulfonyl,
`C 1 -C6
`C 1 -C6
`haloalkylsulfonyl, C 1 -C6 alkylaminosulfonyl, C2 -Cg
`dialkylaminosulfonyl, C3-C 10 trialkylsilyl, C 1 -C6 alky- 50
`!amino, C2-Cg dialkylamino, C2-Cg alkylcarbo(cid:173)
`nylamino, C 1 -C6 alkylsulfonylamino, phenyl, pyridinyl
`or thienyl; and
`each u and v are independently 0, 1 or 2 in each instance
`of S(=O)u( NRg)v, provided that the sum ofu and v 55
`is 0, 1 or 2;
`provided that
`(a) the compound of Formula 1 is other than N-lH(cid:173)
`benzotriazol-1-yl-2-oxo-4-phenyl-3-pyrrolidinecar-
`boxamide;
`(b) when Q 1 comprises a 3-furanyl or 3-pyridinyl ring
`directly bonded to the remainder of Formula 1, then
`said ring is substituted with at least one substituent
`selected from R 7
`;
`(c) when Q 1 is an unsubstituted phenyl ring, and Q2 65
`comprises a phenyl ring directly bonded to the remain(cid:173)
`der of Formula 1, then said Q2 ring is substituted with
`
`25
`
`60
`
`4
`R 10 other than optionally substituted phenoxy or F at a
`2-position, cyano or ----CF3 at the 4-position and R5 is
`H or halogen;
`( d) when Q 1 is unsubstituted phenyl, and Q2 comprises a
`pyridinyl ring directly bonded to the remainder of
`Formula 1, then said pyridinyl ring is substituted with
`at least one substituent selected from R10
`;
`(e) when Q 1 is a phenyl ring substituted with 4-phenyl or
`4-phenoxy, said Q 1 ring is further substituted with and
`R7 substituent;
`(f) when Q 1 comprises 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 addi(cid:173)
`tional position;
`(g) when Q 1 is other than unsubstituted 1-naphthalenyl,
`then Q2 is other than 2,3-di-fluorophenyl or 2-CF3 -
`phenyl;
`(h) Q2 is other than optionally substituted lH-pyrazol-5-
`yl; and
`(i) when Q2 comprises a lH-pyrazol-3-yl ring directly
`bonded to the remainder of Formula 1, said ring is
`substituted at the I-position with R9
`•
`More particularly, this invention pertains to a compound
`of Formula 1 (including all stereoisomers), an N-oxide or a
`salt thereof. This invention also relates to a herbicidal
`composition comprising a compound of the invention (i.e. in
`a herbicidally effective amount) and at least one component
`selected from the group consisting of surfactants, solid
`diluents and liquid diluents, the composition optionally
`further comprising at least one additional active ingredient
`selected from the group consisting of other herbicides and
`herbicide safeners. This invention further relates to a method
`for controlling the growth of undesired vegetation compris(cid:173)
`ing contacting the vegetation or its environment with a
`herbicidally effective amount of a compound of the inven(cid:173)
`tion (e.g., as a composition described herein).
`
`DETAILS OF THE INVENTION
`
`As used herein, the terms "comprises," "comprising,"
`"includes," "including," "has," "having," "contains", "con(cid:173)
`taining," "characterized by" or any other variation thereof,
`are intended to cover a non-exclusive inclusion, subject to
`any limitation explicitly indicated. For example, a compo(cid:173)
`sition, mixture, process or method that comprises a list of
`elements is not necessarily limited to only those elements
`but may include other elements not expressly listed or
`inherent to such composition, mixture, process, or method.
`The transitional phrase "consisting of' excludes any ele(cid:173)
`ment, step, or ingredient not specified. If in the claim, such
`would close the claim to the inclusion of materials other than
`those recited except for impurities ordinarily associated
`therewith. When the phrase "consisting of' appears in a
`clause of the body of a claim, rather than immediately
`following the preamble, it limits only the element set forth
`in that clause; other elements are not excluded from the
`claim as a whole.
`The transitional phrase "consisting essentially of' is used
`to define a composition, method that includes materials,
`steps, features, components, or elements, in addition to those
`literally disclosed, provided that these additional materials,
`steps, features, components, or elements do not materially
`affect the basic and novel characteristic(s) of the claimed
`invention. The term "consisting essentially of' occupies a
`middle ground between "comprising" and "consisting of'.
`
`

`

`US 10,294,202 B2
`
`5
`Where applicants have defined an invention or a portion
`thereof with an open-ended term such as "comprising," it
`should be readily understood that (unless otherwise stated)
`the description should be interpreted to also describe such an
`invention using the terms "consisting essentially of' or 5
`"consisting of'.
`Further, unless expressly stated to the contrary, "or" refers
`to an inclusive or and not to an exclusive or. For example,
`a condition A or B is satisfied by any one of the following:
`Ais true (or present) and Bis false (or not present), Ais false 10
`( or not present) and B is true ( or present), and both A and B
`are true ( or present).
`Also, the indefinite articles "a" and "an" preceding an
`element or component of the invention are intended to be
`nonrestrictive regarding the number of instances (i.e. occur- 15
`rences) of the element or component. Therefore "a" or "an"
`should be read to include one or at least one, and the singular
`word form of the element or component also includes the
`plural unless the number is obviously meant to be singular.
`As referred to herein, the term "seedling", used either 20
`alone or in a combination of words means a young plant
`developing from the embryo of a seed.
`As referred to herein, the term "broadleaf' used either
`alone or in words such as "broadleaf weed" means dicot or
`dicotyledon, a term used to describe a group of angiosperms 25
`characterized by embryos having two cotyledons.
`As used herein, the term "alkylating agent" refers to a
`chemical compound in which a carbon-containing radical is
`bound through a carbon atom to a leaving group such as
`halide or sulfonate, which is displaceable by bonding of a 30
`nucleophile to said carbon atom. Unless otherwise indicated,
`the term "alkylating" does not limit the carbon-containing
`radical to alkyl; the carbon-containing radicals in alkylating
`agents include the variety of carbon-bound substituent radi(cid:173)
`cals specified for R 1
`.
`In the above recitations, the term "alkyl", used either
`alone or in compound words such as "alkylthio" or
`"haloalkyl" includes straight-chain or branched alkyl, such
`as, methyl, ethyl, n-propyl, i-propyl, or the different butyl,
`pentyl or hexyl isomers. "Alkenyl" includes straight-chain 40
`or branched alkenes such as ethenyl, 1-propenyl, 2-prope(cid:173)
`nyl, and the different butenyl, pentenyl and hexenyl isomers.
`"Alkenyl" also includes polyenes such as 1,2-propadienyl
`and 2,4-hexadienyl. "Alkynyl" includes straight-chain or
`branched alkynes such as ethynyl, 1-propynyl, 2-propynyl 45
`and the different butynyl, pentynyl and hexynyl isomers.
`"Alkynyl" can also include moieties comprised of multiple
`triple bonds such as 2,5-hexadiynyl.
`"Alkoxy" includes, for example, methoxy, ethoxy, n-pro(cid:173)
`pyloxy, isopropyloxy and the different butoxy, pentoxy and 50
`hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitu(cid:173)
`tion on alkyl. Examples of "alkoxyalkyl"
`include
`CH3 OCH2 ,
`CH3OCH2 CH2 ,
`CH3 CH2OCH2 ,
`CH3 CH2CH2 CH2OCH2 and CH3CH2 OCH2CH2 . "Alkoxy(cid:173)
`alkoxyalkyl" denotes at least alkoxy substitution on the 55
`alkoxy moiety of alkoxyalkyl moiety. Examples of"alkoxy(cid:173)
`alkoxyalkyl" include CH3 OCH2OCH2 - , CH3CH2 O(CH3 )
`CHOCH2 -
`and (CH3 O) 2CHOCH2 - . "Alkoxyalkoxy"
`denotes alkoxy substitution on alkoxy. "Alkenyloxy"
`includes straight-chain or branched alkenyloxy moieties. 60
`Examples of "alkenyloxy"
`include H2C=CHCH2O,
`(CH3 ) 2C=CHCH2 O, (CH3 )CH=CHCH2O, (CH3)CH=C
`"Alkynyloxy"
`(CH3)CH2O
`and CH2=CHCH2 CH2O.
`includes straight-chain or branched alkynyloxy moieties.
`Examples
`of
`"alkynyloxy"
`include HC .. CCH2O, 65
`CH3 C .. CCH2 O
`and CH3C .. CCH2CH2 O.
`"Alkylthio"
`includes branched or straight-chain alkylthio moieties such
`
`6
`as methylthio, ethylthio, and the different propylthio, butyl(cid:173)
`thio, pentylthio and hexylthio isomers. "Alkylsulfinyl"
`includes both enantiomers of an alkylsulfinyl group.
`Examples of"alkylsulfinyl" include CH3 S(O)-, CH3 CH2S
`(0)-, CH3 CH2CH2 S(O)-, (CH3 ) 2CHS(O)- and the dif(cid:173)
`ferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl iso-
`mers. Examples of "alkylsulfonyl" include CH3S(O)2- ,
`CH3CH2 S(O)2- ,
`CH3CH2 CH2S(O)2 - ,
`(CH 3 ) 2
`CHS(O) 2- , and the different butylsulfonyl, pentylsulfonyl
`and hexylsulfonyl isomers. "Alkylthioalkyl" denotes alkyl(cid:173)
`thio substitution on alkyl. Examples of "alkylthioalkyl"
`include CH3 SCH2 ,
`CH3 SCH2CH2 ,
`CH3 CH2SCH2 ,
`CH3CH2 CH2 CH2 SCH2 and CH3CH2 SCH2CH2 . "Alkyl(cid:173)
`sulfinylalkyl" denotes alkylsulfinyl substitution on alkyl.
`Examples of "alkylsulfinylalkyl" include CH3S(=O)CH2 ,
`CH3S(=O)CH2CH2 , CH3 CH2 S(=O)CH2 and CH3 CH2S
`(=O)CH2CH2 . "Alkylsulfonylalkyl" denotes alkylsulfinyl
`substitution on alkyl. Examples of "alkylsulfinylalkyl"
`include CH3 S(=O)2CH2 , CH3 S(=O)2 CH2CH2 , CH3 CH2S
`(=O)2 CH2 and CH3 CH2S(=O)2 CH2CH2 . "Alkylamino",
`"dialkylamino", and the like, are defined analogously to the
`above examples. Examples of "alkylaminoalkyl" include
`CH3NHCH2 - , (CH3 ) 2CHNHCH2 -
`and CH3NHCH
`(CH3 ) - . Examples of "dialkylaminoalkyl"
`include
`(CH3 ) 2NCH2- , (CH3 ) 2NC(CH3 )H- and
`(CH3)(CH3 )
`NCH2- . Examples of "dialkylaminocarbonyl" include
`(CH3 ) 2NC(O)-. Examples of "dialkylaminosulfonyl"
`include (CH3 ) 2NS(O) 2- . The term "alkoxycarbonylamino"
`denotes a straight-chain or branched alkoxy moieties bonded
`to a C(=O) moiety of carbonylamino group. Examples of
`"alkoxycarbonylamino" include CH3OC(=O)NH- and
`CH3CH2 OC(=O)NH-.
`cyclopropyl,
`example,
`for
`"Cycloalkyl"
`includes,
`cyclobutyl, cyclopentyl and cyclohexyl. The term "alkylcy(cid:173)
`cloalkyl" denotes alkyl substitution on a cycloalkyl moiety
`35 and includes, for example, ethylcyclopropyl, i-propylcy(cid:173)
`clobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The
`term "cycloalkylalkyl" denotes cycloalkyl substitution on an
`alkyl moiety. Examples of "cycloalkylalkyl" include cyclo-
`propylmethyl, cyclopentylethyl, and other cycloalkyl moi(cid:173)
`eties bonded to straight-chain or branched alkyl groups. The
`term "cycloalkoxy" denotes cycloalkyl linked through an
`oxygen atom such as cyclopentyloxy and cyclohexyloxy.
`"Cycloalkylalkoxy" denotes cycloalkylalkyl linked through
`an oxygen atom attached to the alkyl chain. Examples of
`"cycloalkylalkoxy" include cyclopropylmethoxy, cyclopen(cid:173)
`tylethoxy, and other cycloalkyl moieties bonded to straight-
`chain or branched alkoxy groups. "Cycloalkenyl" includes
`groups such as cyclopentenyl and cyclohexenyl as well as
`groups with more than one double bond such as 1,3- and
`1,4-cyclohexadienyl.
`The term "halogen", either alone or in compound words
`such as "haloalkyl", or when used in descriptions such as
`"alkyl substituted with halogen" includes fluorine, chlorine,
`bromine or iodine. Further, when used in compound words
`such as "haloalkyl", or when used in descriptions such as
`"alkyl substituted with halogen" said alkyl may be partially
`or fully substituted with halogen atoms which may be the
`same or different. Examples of "haloalkyl" or "alkyl sub(cid:173)
`stituted with halogen" include F3 C, ClCH2 , CF3CH2 and
`terms "halocycloalkyl", "haloalkoxy",
`CF3CC1 2 . The
`"haloalkylthio", "haloalkenyl", "haloalkynyl", "haloalkeny-
`loxy",
`"haloalkylcarbonylamino",
`"haloalkylsulfo(cid:173)
`nylamino",
`"haloalky lsulfonyl-oxy",
`"haloalkoxyalky l",
`"haloalkylcarbonyloxy", "haloalkylaminoalkyl" and the
`like, are defined analogously to the term "haloalkyl".
`Examples of "haloalkoxy" include CF3 O-, CC13 CH2O-,
`HCF 2CH2 CH2O-
`and CF3 CH2 O-. Examples of
`
`

`

`US 10,294,202 B2
`
`10
`
`7
`"haloalkylthio" include CCl3S-, CF3S-, CCl3CH2S(cid:173)
`and CICH2CH2CH2S-. Examples of "haloalkylsulfinyl"
`include CF3S(O)-, CCl3S(O)-, CF3 CH2S(O)- and
`CF 3CF2S(O)-. Examples of "haloalkylsulfonyl" include
`CF3 S(O)2-, CCl3 S(O)2-, CF3 CH2S(O)2-
`and CF3CF2S 5
`Examples
`of
`"haloalkenyl"
`(0)2-.
`include
`(Cl)2C=CHCH2-
`and
`CF3CH2CH=CHCH2-.
`Examples
`of
`"haloalkenyloxy"
`include
`(Cl)2C=CHCH2O-
`and
`CF3CH2CH=CHCH2O-.
`Examples of "haloalkynyl"
`include HC .. CCHCI-,
`CF3C=C-, CCl3 C=C- and FCH2C .. CCH2-. Examples
`of
`"haloalkoxyalkyl"
`include
`CF3OCH2-,
`CICH2CH2OCH2CH2-, Cl3CCH2OCH2-
`as well as
`branched alkyl derivatives. Examples of "haloalkoxycarbo(cid:173)
`nyl"
`include CF 3OC(O)-, CICH2CH2OCH2CH2-,
`Cl3CCH2OCH2OC(O)- as well as branched alkyl deriva- 15
`tives.
`"Alkylcarbonyl" denotes a straight-chain or branched
`alkyl moieties bonded to a C(=O) moiety. Examples of
`"alkylcarbonyl"
`include CH3C(=O)-, CH3CH2CH2C
`(=0)- and (CH3 ) 2CHC(=O)-. Examples of"alkoxycar- 20
`bony!"
`include CH3OC(=O)-, CH3 CH2OC(=O)-,
`CH3 CH2CH2OC(=O)-, (CH3 ) 2CHOC(=O)- and the
`different butoxy- or pentoxycarbonyl isomers. "Cycloalky(cid:173)
`lalkoxycarbonyl" denotes a cycloalkylalkyl moieties bonded
`to an oxygen atom of alkoxycarbonyl moiety. Examples of 25
`"cycloalkylalkoxycarbonyl" include cyclopropyl-CH2OC
`(=0)-, cyclopropyl-CH(CH3)OC(=O)- and cyclopen(cid:173)
`tyl-CH2OC(=O)-.
`The total number of carbon atoms in a substituent group
`is indicated by the "C,-C/ prefix where i and j are numbers 30
`from 1 to 12. For example, C 1-C4 alkylsulfonyl designates
`methylsulfonyl through butylsulfonyl; C2 alkoxyalkyl des(cid:173)
`for
`ignates CH3OCH2-; C3 alkoxyalkyl designates,
`example,
`CH3 CH(OCH3 ) - , CH3 OCH2CH2-
`or
`CH3 CH2OCH2-; and C4 alkoxyalkyl designates the vari- 35
`ous isomers of an alkyl group substituted with an alkoxy
`group containing a total of four carbon atoms, examples
`including CH3 CH2CH2OCH2-
`and CH3 CH2OCH2CH2-.
`When a compound is substituted with a substituent bear(cid:173)
`ing a subscript that indicates the number of said substituents 40
`can exceed 1, said substituents (when they exceed 1) are
`independently selected from the group of defined substitu(cid:173)
`ents, e.g., [R7)nL n is 1, 2, 3, 4 or 5). Further, when the
`subscript indicates a range, e.g. (R),_1, then the number of
`substituents may be selected from the integers between i and 45
`j inclusive. When a group contains a substituent which can
`be hydrogen, for example R 1 or R2, then when this substitu(cid:173)
`ent is taken as hydrogen, it is recognized that this is
`equivalent to said group being unsubstituted. When a vari(cid:173)
`able group is shown to be optionally attached to a position, 50
`for example [R C7 l nl wherein n may be 0, then hydrogen may
`be at the position even if not recited in the variable group
`definition. When one or more positions on a group are said
`to be "not substituted" or "unsubstituted", then hydrogen
`atoms are attached to take up any free valency.
`The expression "fully saturated" in relation to a ring of
`atoms means that the bonds between the atoms of the ring
`are all single. The expression "fully unsaturated" in relation
`to a ring means that the bonds between the atoms in the ring
`are single or double bonds according to valence bond theory 60
`and furthermore the bonds between the atoms in the ring
`include as many double bonds as possible without double
`bonds being cumulative (i.e. no C=C=C, N=C=C, etc.).
`The term "partially unsaturated" in relation to a ring denotes
`a ring comprising at least one ring member bonded to an
`adjacent ring member though a double bond and which
`conceptually potentially accommodates a number of non-
`
`8
`cumulated double bonds through adjacent ring members (i.e.
`in its fully unsaturated counterpart form) greater than the
`number of double bonds present (i.e. in its partially unsatu-
`rated form). When a fully unsaturated ring satisfies Huckel's
`rule then it can also be described as aromatic.
`Unless otherwise indicated, a "ring" or "ring system" as
`a component of Formula 1 (e.g., substituent Q1
`) is carbo(cid:173)
`cyclic or heterocyclic. The term "ring system" denotes two
`or more fused rings. The terms "bicyclic ring system" and
`"fused bicyclic ring system" denote a ring system consisting
`of two fused rings, in which either ring can be saturated,
`partially unsaturated, or fully unsaturated unless otherwise
`indicated. The term "fused heterobicyclic ring system"
`denotes a fused bicyclic ring system in which at least one
`ring atom is not carbon. A "bridged bicyclic ring system" is
`formed by bonding a segment of one or more atoms to
`nonadjacent ring members of a ring. The term "ring mem(cid:173)
`ber" refers to an atom or other moiety ( e.g., C(=O), C(=S),
`S(O) or S(O)2) forming the backbone of a ring or ring
`system.
`The terms "carbocyclic ring", "carbocycle" or "carbocy(cid:173)
`clic ring system" denote a ring or ring system wherein the
`atoms forming the ring backbone are selected only from
`carbon. Unless otherwise indicated, a carbocyclic ring can
`be a saturated, partially unsaturated, or fully unsaturated
`ring. When a fully unsaturated carbocyclic ring satisfies
`Huckel's rule, then said ring is also called an "aromatic
`ring". "Saturated carbocyclic" refers to a ring having a
`backbone consisting of carbon atoms linked to one another
`by single bonds; unless otherwise specified, the remaining
`carbon valences are occupied by hydrogen atoms.
`The terms "heterocyclic ring", "heterocycle" or "hetero-
`cyclic ring system" denote a ring or ring system in which at
`least one atom forming the ring backbone is not carbon, e.g.,
`nitrogen, oxygen or sulfur. Typically a heterocyclic ring
`contains no more than 4 nitrogens, no more than 2 oxygens
`and no more than 2 sulfurs. Unless otherwise indicated, a
`heterocyclic ring can be a saturated, partially unsaturated, or
`fully unsaturated ring. When a fully unsaturated heterocyclic
`ring satisfies Huckel's rule, then said ring is also called a
`"heteroaromatic ring" or "aromatic heterocyclic ring".
`Unless otherwise indicated, heterocyclic rings and ring
`systems can be attached through any available carbon or
`nitrogen by replacement of a hydrogen on said carbon or
`nitrogen.
`"Aromatic" indicates that each of the ring atoms is
`essentially in the same plane and has a p-orbital perpen(cid:173)
`dicular to the ring plane, and that (4n+2) it electrons, where
`n is a positive integer, are associated with the ring to comply
`with Huckel's rule. The term "aromatic ring system" denotes
`a carbocyclic or heterocyclic ring system in which at least
`one ring