WO2011137088A1 - Uraciles herbicides - Google Patents

Uraciles herbicides Download PDF

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Publication number
WO2011137088A1
WO2011137088A1 PCT/US2011/033846 US2011033846W WO2011137088A1 WO 2011137088 A1 WO2011137088 A1 WO 2011137088A1 US 2011033846 W US2011033846 W US 2011033846W WO 2011137088 A1 WO2011137088 A1 WO 2011137088A1
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Prior art keywords
compound
methyl
pyrimidinyl
chloro
fluorophenoxy
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PCT/US2011/033846
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English (en)
Inventor
Wonpyo Hong
Thomas Paul Selby
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E. I. Du Pont De Nemours And Company
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Publication of WO2011137088A1 publication Critical patent/WO2011137088A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • This invention relates to certain herbicidal uracils, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.
  • the control of undesired vegetation is extremely important 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 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 purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.
  • This invention is directed to a compound of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:
  • R 1 is H, amino or C1-C3 alkyl
  • X 1 is H or halogen
  • W 1 is O or S
  • A is a phenyl, pyridinyl or pyrimidinyl ring, the ring optionally substituted with up to 4 substituents independently selected from R 2 ;
  • W 2 is O, S or N(R 9 );
  • each R 2 is independently halogen, cyano, C ⁇ -Cg alkyl, C ⁇ -Cg haloalkyl, C ⁇ -Cg alkoxy or C ⁇ -Cg haloalkoxy;
  • W 3 is O or S
  • R 4 is H, -OR 6 , -SR 6 , -NR 7 R 8 or -O M+;
  • M + is an agriculturally suitable alkali metal cation or ammonium cation
  • each R 5 is independently halogen, cyano, hydroxy, C j -Cg haloalkyl, C j -Cg alkoxy,
  • R 6 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 haloalkyl, C 2 -C 6
  • haloalkoxyalkyl C3-Cg haloalkoxycarbonylalkyl, C3-Cg alkylcarbonylalkyl, C3-Cg alkenyloxyalkyl, C3-Cg alkenyloxycarbonylalkyl, C3-Cg
  • haloalkenyloxyalkyl C 2 -Cg alkylaminoalkyl, C3-Cg dialkylaminoalkyl, C 2 -Cg aminocarbonylalkyl, C3-Cg alkylaminoalkylcarbonylalkyl or C3-Cg
  • R 6 is G A , -(CR 12 R 13 ) q TG A , G B or -(CR 14 R 15 ) U TG B ; or
  • R 5 and R 6 are taken together as C1-C3 alkylene to form, including the atoms to which said R 5 and R 6 are attached, a 4- to 7-membered ring, said ring optionally substituted with up to two substituents selected from halogen, C j -Cg alkyl or C j -Cg haloalkyl;
  • each q and u is independently an integer selected from 1 through 4;
  • each T is independently a direct bond, -0-, -S- or -N(R 18 )-;
  • G A is phenyl or benzyl; or a 5- or 6-membered heteroaromatic ring, each phenyl, benzyl or heteroaromatic ring optionally substituted with up to 4 substituents independently selected from R 16 on carbon ring members and R 17 on nitrogen ring members;
  • R 7 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8
  • alkoxycarbonylalkyl C ⁇ -Cg alkoxy or C 2 -Cg dialkylaminosulfonyl; or a phenyl ring or benzyl, each optionally substituted with up to five substituents selected from C1-C3 alkyl, -CF 3 and C1-C3 alkoxy on ring members;
  • R 8 is H or C r C 3 alkyl; or
  • R 9 is H or C r C 3 alkyl
  • R 10 and R 1 1 are each independently H or C ⁇ -C 3 alkyl
  • each R 12 , R 13 , R 14 and R 15 is independently H or C r C 3 alkyl; or
  • one R 12 and one R 13 are taken together as an oxygen atom to form, with the carbon
  • one R 14 and one R 15 are taken together as an oxygen atom to form, with the carbon
  • R 16 is halogen, C 1-C3 alkyl, -CF 3 or C j -C 3 alkoxy;
  • each R 17 is H or C ⁇ -C 3 alkyl
  • R 18 is H or C r C 3 alkyl.
  • 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 additional herbicide or herbcicide safener.
  • 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.
  • This invention further relates to 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 the invention (e.g., as a composition described herein).
  • This invention is also directed to a method for pre -plant burndown.
  • the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • a composition, 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 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.
  • transitional phrase consisting essentially of is used to define a composition or 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.
  • seedling used either alone or in a combination of words means a young plant developing from the embryo of a seed.
  • narrowleaf used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
  • 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 a halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom.
  • alkylating does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R 4 and R 5 .
  • 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, /-propyl, or the different butyl, pentyl or hexyl isomers.
  • Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, 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 and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkylene denotes a straight-chain or branched alkanediyl. Examples of “alkylene” include -CH , -CH 2 CH , -CH(CH 3 )-, -CH 2 CH 2 CH , -CH 2 CH(CH 3 )-.
  • Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • “Dialkoxyalkyl” denotes two independent alkoxy groups substituted on the same or different carbon of said alkyl group.
  • dialkoxyalkyl examples include (CH 3 0) 2 CH and CH 3 CH 2 0(CH 3 0)CH.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylamino “dialkylamino” and the like, are defined analogously to the above examples.
  • Alkylthioalkyl denotes alkylthio substitution on alkyl.
  • alkylthioalkyl examples include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
  • alkylsulfmylalkyl denotes alkylsulfmyl substitution on alkyl.
  • alkylsulfonylalkyl denotes alkylsulfonyl substitution on alkyl.
  • alkylsulfonylalkyl include CH 3 S(0) 2 CH 2 , CH 3 S(0) 2 CH 2 CH 2 , CH 3 CH 2 S(0) 2 CH 2 , CH 3 CH 2 CH 2 CH 2 S(0) 2 CH 2 and CH 3 CH 2 S(0) 2 CH 2 CH 2 .
  • Alkoxyalkoxyalkyl denotes at least one straight-chain or branched alkoxy moiety bonded to a straight-chain or branched alkoxyalkyl moiety.
  • alkoxyalkoxyalkyl examples include CH 3 OCH 2 OCH 2 -, CH 3 CH 2 OCH(CH 3 )OCH 2 - and (CH 3 0) 2 CHOCH 2 -.
  • alkenyloxyalkyl denotes an alkenyloxy moiety bonded through an alkyl group.
  • alkenyloxycarbonylalkyl denotes an alkenyloxy group bonded through a carbonyl alkyl group.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • 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.
  • alkylaminoalkyl denotes a straight-chain or branched alkyl moiety bonded to a nitrogen atom of amino(straight-chain or branched)alkyl moiety. Examples of “alkylaminoalkyl” include CH 3 NHCH , (CH 3 ) 2 CHNHCH 2 - and CH 3 NHCH(CH 3 )-.
  • dialkylaminoalkyl denotes two straight-chain or branched alkyl moieties bonded to a nitrogen atom of amino(straight-chain or branched)alkyl moiety.
  • dialkylaminoalkyl examples include (CH 3 ) 2 NCH , (CH 3 ) 2 CN(CH 3 )CH 2 - and CH 3 N(CH 3 )CH(CH 3 )-.
  • 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 substituted with halogen” include F 3 C-, C1CH 2 -, CF 3 CH 2 - and CF 3 CC1 2 -.
  • haloalkoxy haloalkenyl
  • haloalkynyl haloalkenyloxyalkyl
  • haloalkenyloxyalkyl haloakoxyalkyl
  • haloalkoxycarbonylalkyl haloalkyl
  • haloalkoxy examples include CF 3 0-, CC1 3 CH 2 0-, HCF 2 CH 2 CH 2 0- and CF 3 CH 2 0-.
  • haloalkynyl examples include HC ⁇ CCHC1-, CF 3 C ⁇ C-, CC1 3 C ⁇ C- and FCH 2 C ⁇ CCH 2 -.
  • halocycloalkyl examples include 2-chlorocyclopropyl, 2-fluorocyclobutyl, 3-bromocyclopentyl and 4-chorocyclohexyl.”
  • halocycloalkenyl denotes halogen substitution on cycloalkenyl.
  • Cyanoalkyl denotes an alkyl group substituted with one or more cyano group.
  • cyanoalkyl examples include NCCH 2 -, (NC) 2 CH-, NCCH 2 CH 2 - and CH 3 CH(CN)CH 2 -.
  • dialkylaminosulfonyl denotes two independent straight-chain or branched alkyl moieties bonded to a nitrogen atom of aminosulfonyl.
  • dialkylaminosulfonyl examples include (CH 3 ) 2 NS(0) 2 -, (CH 3 CH 2 CH 2 )(CH 3 )NS(0) 2 -, ((CH 3 ) 2 CH)(CH 3 )NS(0) 2 - and ((CH 3 ) 2 CH) 2 NS(0) 2 -.
  • alkoxycarbonylalkyl denotes alkoxycarbonyl substitution on a straight-chain or branched alkyl.
  • Trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom. Examples include as trimethylsilyl, triethylsilyl and tert- butyldimethylsilyl. When this term is followed by a group in paranthases (i.e. trialkylsilyl(alkyl), trialkylsilyl(alkenyl) trialkylsilyl(alkoxy alkyl) or trialkylsilyl(alkynyl)) the parenthetical group links the trialkylsilyl group to the described variable. The total number of carbon atoms preceeding the term trialkylsilyl includes the carbon atoms in both the trialkylsilyl moiety and the parenthetical group.
  • C1-C4 alkylamino designates methylamino through butylamino
  • C 2 alkoxyalkyl designates CH 3 OCH 2 -
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 )-, CH 3 OCH 2 CH 2 - or CH 3 CH 2 OCH 2 -
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 - and CH 3 CH 2 OCH 2 CH 2 -.
  • a "ring” as a component of Formula 1 is carbocyclic or heterocyclic.
  • the term “ring member” refers to an atom or other moiety (e.g., O, S or N) forming the backbone of a ring.
  • carbocyclic ring denotes a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon.
  • a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated 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.
  • heterocyclic ring denotes a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.
  • a heterocyclic ring contains no more than 2 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
  • 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”.
  • heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • optionally substituted in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated.
  • optionally substituted is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted”. Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.
  • R 3 is defined in the Summary of the Invention as C1-C 3 alkylene substituted with at least one R 5
  • R 3 is C ⁇ alkylene substituted with at least one R 5
  • the resulting compound is either Formula l la or l lb below wherein W 2 is attached to A in Formula 1).
  • R 4 is defined in the Summary of the Invention particularly as -O M +
  • the 0 ⁇ in this term refers to the anion of oxygen.
  • M + as defined in the Summary of the Invention can be any agriculturally suitable alkali metal cation or ammonium cation which is associated with the 0 ⁇ anion.
  • Agriculturally suitiable alkali metal cations include lithium (Li + ), sodium (Na + ) or potassium (K + ).
  • Agriculturally suitable ammonium cations include trimethylammonium ((C ⁇ N "1" ), triethylammonium ((CH 3 CH 2 ) 3 N + ) and tributylammonium ((CH3CH2CH 2 CFl2)3N + ).
  • one R 12 and one R 13 can be together as an oxygen atom to form, with the carbon atom to which said one R 12 and one R 13 are attached, a carbonyl moiety.
  • R 4 is -OR 6 or -SR 6 ;
  • R 6 is -(CR 12 R 13 ) q TG A ;
  • q is 1, 2, 3 or 4 only one (CR 12 R 13 ) can be taken together to make a carbonyl.
  • compound 73 in Index Table A is a compound wherein R 4 is -OR 6 , R 6 is -(CR 12 R 13 )qTG A , G A is a phenyl ring; T is a direct bond; q is 2; one -(CR 12 R 13 ) moiety is -CH2 and the second -(CR 12 R 13 ) moiety is a carbonyl (i.e. one R 12 and one R 13 are taken together as an oxygen atom to form, with the carbon atom to which said one R 12 and one R 13 are attached, a carbonyl moiety).
  • one R 1 and one R 15 can be taken together as an oxygen atom to form, with the carbon atom to which said one R 12 and one R 13 are attached, a carbonyl moiety.
  • R 4 is -OR 6 or -SR 6 ;
  • R 6 is -(CR 14 R 15 ) U TG B ; and
  • u is 1, 2, 3 or 4
  • substituent A is a phenyl, pyridinyl or pyrimidinyl ring it may be attached to the remainder of Formula 1 though any available carbon atom, unless otherwise described.
  • A can be (among others) phenyl optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention.
  • An example of phenyl optionally substituted with up to four substituents is the ring illustrated as A-l through A-3 in Exhibit 1, wherein (R 2 ) n is as defined in the Summary of the Invention for R 2 (i.e. halogen or cyano) and n is an integer from 0 to 4.
  • n is an integer from 0 to 4, limited by the number of available positions on each A group.
  • a pyridinyl or pyrimidinyl ring optionally substituted with up to four substituents include the rings A-4 through A-20 illustrated in Exhibit 1 wherein (R 2 ) n is any substituent as defined in the Summary of the Invention for (R 2 ) (i.e. halogen or cyano etc.) and n is an integer from 0 to 4, limited by the number of available positions on each A group.
  • n is limited to the integers 0, 1 or 2, and n being 0 means that the A group is unsubstituted and a hydrogen is present at the position indicated by (R 2 ) n .
  • a pair of R 7 and R 8 attached to the same nitrogen atom can be taken together with the nitrogen atom to form a 3 - to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 2 N, the ring optionally substituted with up to 4 substituents independently selected from halogen, cyano, C1-C3 alkyl and C1-C3 alkoxy on carbon atom ring members and C1-C3 alkyl on nitrogen atom ring members.
  • the ring members selected from up to 2 O, up to 2 S and up to 2 N atom are optional, because the number of heteroatom ring members may be zero.
  • the ring is optionally substituted with up to 4 substituents independently independently selected from halogen, cyano, C1-C3 alkyl and C1-C3 alkoxy on carbon atom ring members and C1-C3 alkyl on nitrogen atom ring members. These optional substituents (when present) are attached to available carbon and nitrogen atom ring members in the portion of the ring provided by R 7 and R 8 .
  • G A can be a 5- or 6-membered heteroaromatic ring it may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention.
  • Examples of a 5- or 6-membered heteroaromatic ring optionally substituted with from one or more substituents include the rings B-l through B-60 illustrated in Exhibit 2 wherein R v is any substituent as defined in the Summary of the Invention for R 16 on carbon ring members or R 17 on nitrogen ring members, and r is an integer from 0 to 4, limited by the number of available positions on each B group.
  • B-29, B-30, B-32, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41, B-42, B-43, B-45, B-46 and B-47 have only one available position, for these B groups r is limited to the integers 0 or 1 , and r being 0 means that the B group is unsubstituted and a hydrogen is present at the position indicated by (R v ) r .
  • the ring is optionally substituted with up to 4 substituents selected from R 16 (wherein R 16 is defined in the Summary of the Invention) on carbon ring members and R 17 (wherein R 17 is defined in the Summary of the Invention) on nitrogen ring members when the ring includes -N(R 17 )-. Examples include C-1 through C-32 as shown in Exhibit 3 below.
  • the resulting 4- to 7-membered ring is optionally substituted with up to two substituents selected from halogen, Ci-C 6 alkyl or Ci ⁇ C 6 haloalkyl.
  • R 5 and R 6 taken together as C1-C3 alkylene to form a 4- to 7-membered ring include D-l through D-15 as shown in Exhibit 4 below wherein R* is selected from halogen, i-C ⁇ alkyl or Ci-Cfr haloalkyl and p is 0 to 2 as described above and wherein the bond projecting to the left is attached to the remainder of Formula 1 through W 2 .
  • Compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
  • Formula 1 when R 3 is C ⁇ alkylene substituted by one R 5 , then Formula 1 possesses a chiral center at the carbon atom to which R 5 is bonded.
  • the two enantiomers are depicted as Formula 1' and Formula 1" with the chiral center identified with an asterisk *).
  • This invention comprises racemic mixtures, for example, equal amounts of the enantiomers of Formulae 1' and 1".
  • this invention includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula 1. Also included are the essentially pure enantiomers of compounds of Formula 1, for example, Formula 1' and Formula 1".
  • enantiomeric excess which is defined as (2 ⁇ -1) ⁇ 100 %, where x is the mole fraction of the dominant enantiomer in the mixture (e.g., an ee of 20 % corresponds to a 60:40 ratio of enantiomers).
  • compositions of this invention have at least a 50 % enantiomeric excess; more preferably at least a 75 % enantiomeric excess; still more preferably at least a 90 % enantiomeric excess; and the most preferably at least a 94 % enantiomeric excess of the more active isomer.
  • enantiomerically pure embodiments of the more active isomer are enantiomerically pure embodiments of the more active isomer.
  • Compounds of Formula 1 can comprise additional chiral centers.
  • substituents and other molecular constituents such as R 2 , R 6 and R 7 may themselves contain chiral centers.
  • This invention comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers.
  • This invention comprises mixtures of conformational isomers.
  • this invention includes compounds that are enriched in one conformer relative to others.
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
  • polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1.
  • Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides.
  • nitrogen-containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane
  • salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms.
  • the salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium.
  • the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
  • Embodiments of the present invention as described in the Summary of the Invention include those below.
  • Formula 1 includes N-oxides and salts thereof, and reference to "a compound of Formula 1" includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.
  • Embodiment 1 A compound of Formula 1 wherein R 1 is amino or C 1-C3 alkyl.
  • Embodiment 2 A compound of Embodiment 1 wherein R 1 is Ci -C3 alkyl.
  • Embodiment 3 A compound of Embodiment 2 wherein R 1 is methyl or ethyl.
  • Embodiment 4 A compound of Embodiment 3 wherein R 1 is methyl.
  • Embodiment 5 A compound of Formula 1 or any one of Embodiments 1 through 4 wherein X 1 is H.
  • Embodiment 6 A compound of Formula 1 or any one of Embodiments 1 through 4 wherein X 1 is halogen.
  • Embodiment 7 A compound of Embodiment 6 wherein X 1 is F or CI.
  • Embodiment 8 A compound of Embodiment 7 wherein X 1 is F.
  • Embodiment 9 A compound of Formula 1 or any one of Embodiments 1 through 8 wherein X 2 is halogen, cyano, amino, nitro or -CF 3 .
  • Embodiment 10 A compound of Formula 1 or any one of Embodiments 1 through 9 wherein X 2 is halogen, cyano or -CF 3 .
  • Embodiment 11 A compound of Embodiment 10 wherein X 2 is halogen or cyano.
  • Embodiment 12 A compound of Embodiment 11 wherein X 2 is CI, F or cyano.
  • Embodiment 13 A compound of Embodiment 12 wherein X 2 is CI or F.
  • Embodiment 14 A compound of Embodiment 13 wherein X 2 is CI.
  • Embodiment 15 A compound of Embodiment 9 wherein X 2 is halogen or nitro.
  • Embodiment 16 A compound of Embodiment 15 wherein X 2 is CI, F or nitro.
  • Embodiment 17 A compound of Formula 1 or any one of Embodiments 1 through 16 wherein W 1 is S.
  • Embodiment 18 A compound of Formula 1 or any one of Embodiments 1 through 16 wherein W 1 is O.
  • Embodiment 19 A compound of Formula 1 or any one of Embodiments 1 through 18 wherein W 2 is O, S, N(H) or N(CH 3 ).
  • Embodiment 20 A compound of Embodiment 19 wherein W 2 is O, S or N(H).
  • Embodiment 21 A compound of Embodiment 20 wherein W 2 is O or S.
  • Embodiment 22 A compound of Embodiment 20 wherein W 2 is S.
  • Embodiment 23 A compound of Embodiment 20 wherein W 2 is O.
  • Embodiment 24 A compound of Formula 1 or any one of Embodiments 1 through 23 wherein A is a phenyl, pyridinyl or pyrimidinyl ring selected from
  • Embodiment 25 A compound of Embodiment 24 wherein A is selected from A-1, A-2,
  • Embodiment 26 A compound of Embodiment 25 wherein A is selected from A-1, A-2,
  • Embodiment 27 A compound of Embodiment 26 wherein A is selected from A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-14 and A-15.
  • Embodiment 28 A compound of Embodiment 27 wherein A is selected from A-1, A-2,
  • Embodiment 29 A compound of Embodiment 28 wherein A is selected from A-1, A-2,
  • Embodiment 30 A compound of Embodiment 29 wherein A is selected from A-1, A-2 and A-4.
  • Embodiment 31 A compound of Embodiment 30 wherein A is A- 1.
  • Embodiment 32 A compound of Embodiment 30 wherein A is A-2.
  • Embodiment 33 A compound of Embodiment 30 wherein A is A-4.
  • Embodiment 34 A compound of any one of Embodiments 24 through 33 wherein n is 0 to 2.
  • Embodiment 35 A compound of Embodiment 34 wherein n is 1.
  • Embodiment 36 A compound of Embodiment 34 wherein n is 0.
  • Embodiment 37 A compound of Embodiment 35 wherein R 2 is attached at the 4- or 5 -position.
  • Embodiment 38 A compound of Embodiment 37 wherein R 2 is attached at the
  • Embodiment 39 A compound of Embodiment 37 wherein R 2 is attached at the
  • Embodiment 40 A compound of Formula 1 or any one of Embodiments 1 through 39 wherein R 2 is halogen, Ci ⁇ C 6 alkyl or Ci ⁇ C 6 alkoxy.
  • Embodiment 41 A compound of Embodiment 40 wherein R 2 is halogen, C1-C3 alkyl or methoxy.
  • Embodiment 42 A compound of Embodiment 41 wherein R 2 is halogen.
  • Embodiment 43 A compound of Embodiment 42 wherein R 2 is F or CI.
  • Embodiment 44 A compound of Embodiment 43 wherein R 2 is F.
  • Embodiment 45 A compound of Embodiment 41 wherein R 2 is methyl or methoxy.
  • Embodiment 46 A compound of Embodiment 45 wherein R 2 is methyl.
  • Embodiment 47 A compound of Embodiment 41 wherein R 2 is F or methyl.
  • Embodiment 48 A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R 3 is Ci -C3 alkylene substituted with two R 5 .
  • Embodiment 49 A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R 3 is Ci -C3 alkylene substituted with one R 5 .
  • Embodiment 50 A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R 3 is C1-C2 alkylene substituted with at least one R 5 .
  • Embodiment 51 A compound of Embodiment 50 wherein R 3 is C1-C2 alkylene
  • Embodiment 52 A compound of Embodiment 50 wherein R 3 is C1-C2 alkylene substituted with one R 5 .
  • Embodiment 53 A compound of Formula 1 or any one of Embodiments 1 through 47 wherein R 3 is C alkylene substituted with at least one R 5 .
  • Embodiment 54 A compound of Embodiment 53 wherein R 3 is C alkylene substituted with two R 5 .
  • Embodiment 55 A compound of Embodiment 53 wherein R 3 is C alkylene substituted with one R 5 .
  • Embodiment 56 A compound of Formula 1 or any one of Embodiments 1 through 48,
  • R 3 is C ⁇ alkylene substituted with two R 5 .
  • Embodiment 57 A compound of Formula 1 or any one of Embodiments 1 through 47,
  • R 3 is C ⁇ alkylene substituted with one R 5 .
  • Embodiment 59 A compound of Formula 1 or any one of Embodiments 1 through 58 wherein W 3 is S.
  • Embodiment 60 A compound of Formula 1 or any one of Embodiments 1 through 58 wherein W 3 is O.
  • Embodiment 61 A compound of Formula 1 or any one of Embodiments 1 through 60 wherein R 4 is -OR 6 , -SR 6 , -NR 7 R 8 or -O M+.
  • Embodiment 62 A compound of Embodiment 61 wherein R 4 is -OR 6 , -NR 7 R 8 or
  • Embodiment 63 A compound of Embodiment 62 wherein R 4 is -NH(OCH 3 ),
  • Embodiment 64 A compound of Embodiment 63 wherein R 4 is -NH(OCH 3 ) or
  • Embodiment 65 A compound of Embodiment 64 wherein R 4 is -NH(CH 3 ).
  • Embodiment 66 A compound of Embodiment 65 wherein R 4 is -NH(OCH 3 ).
  • Embodiment 67 A compound of Embodiment 61 wherein R 4 is -OR 6 or -0 ⁇ M + .
  • Embodiment 68 A compound of Embodiment 67 wherein R 4 is -0 ⁇ M + .
  • Embodiment 69 A compound of Embodiment 68 wherein M + is an agriculturally
  • suitable alkali metal cation selected from sodium and potassium.
  • Embodiment 70 A compound of Embodiment 69 wherein M + is sodium.
  • Embodiment 71 A compound of Embodiment 69 wherein M + is potassium.
  • Embodiment 72 A compound of Embodiment 69 wherein M + is an agriculturally
  • ammonium cation selected from trimethylammonium
  • Embodiment 73 A compound of Embodiment 72 wherein M + is triethylammonium.
  • Embodiment 74. A compound of Embodiment 72 wherein M + is trimethylammonium.
  • Embodiment 75. A compound of Embodiment 62 or 67 wherein R 4 is -OR 6 .
  • Embodiment 76 A compound of Formula 1 or any one of Embodiments 1 through 75 wherein each R 5 is independently halogen, cyano, hydroxy, -CF 3 , Ci ⁇ C 6 alkoxy,
  • Embodiment 77 A compound of Embodiment 76 wherein each R 5 is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or C2-C4 alkoxycarbonyl.
  • Embodiment 78 A compound of Embodiment 77 wherein each R 5 is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio.
  • Embodiment 79 A compound of Embodiment 78 wherein each R 5 is halogen, C1-C3 alkoxy or C1-C3 haloalkoxy.
  • Embodiment 80 A compound of Embodiment 79 wherein R 5 is halogen, C1-C2 alkoxy or C1-C2 haloalkoxy.
  • Embodiment 81 A compound of Embodiment 80 wherein R 5 is fluoro.
  • Embodiment 82 A compound of Embodiment 80 wherein R 5 is C1-C2 alkoxy.
  • Embodiment 83 A compound of Embodiment 82 wherein R 5 is ethoxy.
  • Embodiment 84 A compound of Embodiment 82 wherein R 5 is methoxy.
  • Embodiment 85 A compound of Formula 1 or any one of Embodiments 1 through 84 wherein R 5 and R 6 are taken together as C1-C3 alkylene to form, including the atoms to which said R 5 and R 6 are attached, a 5- to 6-membered ring, said ring optionally substituted with up to two substituents selected from halogen, Ci ⁇ C 6 alkyl or C ⁇ -C6 haloalkyl;.
  • Embodiment 86 A compound of Embodiment 85 wherein R 5 and R 6 are taken together to form a rin selected from
  • R* is selected from halogen, C1-C3 alkyl or -C ⁇ haloalkyl; and p is 0, 1 or 2.
  • Embodiment 87 A compound of Embodiment 86 wherein p is 0 or 1.
  • Embodiment 88 A compound of Embodiment 87 wherein R 5 and R 6 are taken together to form ring D-l .
  • Embodiment 89 A compound of Embodiment 88 wherein R* is methyl attached to the
  • Embodiment 90 A compound of Embodiment 88 wherein and p is 0.
  • Embodiment 91 A compound of Formula 1 or any one of Embodiments 1 through 84 wherein R 6 is H, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 3 -C 8
  • alkoxycarbonylalkyl C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 10 trialkylsilyl, C 2 -C 8
  • alkylcarbonylamino C 2 -C6 haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl or C3-Cg alkylcarbonylalkyl.
  • Embodiment 92 A compound of Embodiment 91 wherein R 6 is H, i-C ⁇ alkyl, C 2 -C6 alkenyl, C3-C6 alkynyl, C 2 -C6 haloalkyl, C 2 -C6 haloalkenyl, C3-C6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl or C 2 -C6 cyanoalkyl.
  • Embodiment 93 A compound of Embodiment 92 wherein R 6 is H, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C6 haloalkyl, C 2 -C6 alkoxyalkyl, C3-Cg alkoxycarbonylalkyl C3-C10 alkoxyalkoxyalkyl or C 2 -C6 cyanoalkyl.
  • Embodiment 94 A compound of Embodiment 93 wherein R 6 is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 ,
  • Embodiment 95 A compound of Embodiment 94 wherein R 6 is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CF 3 , CH 2 CH 2 CH 2 F, CH 2 OCH 3 , CH 2 OCH 2 CH 3 ,
  • Embodiment 96 A compound of Embodiment 95 wherein R 6 is H, CH 3 , CH 2 CH 3 ,
  • Embodiment 97 A compound of Embodiment 96 wherein R 6 is H, CH 3 , CH 2 CH 3 , CH 2 CF 3 , CH 2 CH 2 CH 2 F, CH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 CH 3 or
  • Embodiment 98 A compound of Embodiment 97 wherein R 6 is CH 3 .
  • Embodiment 99 A compound of Embodiment 97 wherein R 6 is CH 2 CH 3 .
  • Embodiment 100 A compound of Embodiment 97 wherein R 6 is CH 2 CH 2 CH 2 F.
  • Embodiment 101 A compound of Embodiment 97 wherein R 6 is CH 2 CH 2 OCH 3 .
  • Embodiment 102 A compound of Embodiment 97 wherein R 6 is CH 2 CH 2 OCH 2 CH 3 .
  • Embodiment 102A A compound of Embodiment 97 wherein R 6 is CH 2 OCH 2 CH 2 OMe.
  • Embodiment 103 A compound of Embodiment 97 wherein R 6 is H.
  • Embodiment 104 A compound of Formula 1 or any one of Embodiments 1 through 97 wherein R 6 is other than H.
  • Embodiment 105 A compound of Formula 1 or any one of Embodiments 1 through 62 or 67 or 75 through 84 wherein R 6 is G B or -(CR 14 R 15 ) U TG B .
  • Embodiment 106 A com ound of Embodiment 105 wherein G B is selected from
  • Embodiment 107 A compound of Embodiment 106 wherein u is 0 or 1; and m is 0.
  • Embodiment 108 A compound of Embodiment 107 wherein R 6 is G B ; and G B is selected from C-2, C-3, C-4 and C-8; and u is 0.
  • Embodiment 109 A compound of Embodiment 108 wherein R 6 is G B ; G B is selected from C-2, C-3 and C-4; and m is 0.
  • Embodiment 110 A compound of Embodiment 106 wherein u is 1; and T is a direct bond.
  • Embodiment 111 A compound of Embodiment 110 wherein R 6 is -(CR 14 R 15 ) U TG B and G B is selected from C-1 and C-2.
  • Embodiment 112 A compound of Embodiment 1 1 1 wherein T is a direct bond.
  • Embodiment 113 A compound of Embodiment 1 12 wherein G B is C-1; u is 1; and R 16 is attached at the 1 -position.
  • Embodiment 114 A compound of Embodiment 113 wherein G B is C-1; and m is 0.
  • Embodiment 115 A compound of Embodiment 110 wherein G B is selected from C-6 and C-7; and m is 0.
  • Embodiment 116 A compound of Embodiment 1 15 wherein G B is C-6.
  • Embodiment 117 A compound of Embodiment 1 15 wherein G B is C-7.
  • Embodiment 118 A compound of Formula 1 or any one of Embodiments 1 through 62 or 67 or 75 through 84 wherein R 6 is G A or -(CR 12 R 13 ) q TG A .
  • Embodiment 119 A compound of Embodiment 118 wherein R 6 is G A ; and G A is phenyl optionally substituted with up to 1 substituent selected from R 16 .
  • Embodiment 120 A compound of Embodiment 118 wherein R 6 is -(CR 12 R 13 ) q TG A ; and G A is selected from
  • Embodiment 121 A compound of Embodiment 120 wherein T is a direct bond; q is 0 or 1 ; and r is 0.
  • Embodiment 122 A compound of Embodiment 121 whereien G A is B-51 ; and q is 1.
  • Embodiment 123 A compound of Formula 1 or any one of Embodiments 1 through 122 wherein R 7 when taken alone (i.e. not taken together with R 8 ) is H, i-C ⁇ alkyl,
  • Embodiment 124 A compound Embodiment 123 wherein R 7 when taken alone is H,
  • Ci-Cfr alkyl C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl or C 3 -C 8 alkoxycarbonylalkyl .
  • Embodiment 127 A compound of Embodiment 126 wherein R 7 when taken alone is methyl.
  • Embodiment 128 A compound of Formula 1 or any one of Embodiments 1 through 127 wherein R 8 when taken alone (i.e. not taken together with R 7 ) is H, methyl or ethyl.
  • Embodiment 129 A compound of Embodiment 128 wherein R 8 when taken alone is H.
  • Embodiment 130 A compound of Embodiment 128 wherein R 8 when taken alone is methyl.
  • Embodiment 131 A compound of Formula 1 or any one of Embodiments 1 through 122 wherein a pair of R 7 and R 8 attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 2 heteroatoms selected from up to 2 O and up to 2 N, the ring optionally substituted with up to 2 substituents independently selected from halogen, cyano, Ci -C3 alkyl and Ci -C3 alkoxy on carbon atom ring members and methyl on nitrogen atom ring members.
  • Embodiment 132 Embodiment 132.
  • Embodiment 133 A compound of Embodiment 132 wherein a pair of R 7 and R 8
  • Embodiment 134 A compound of Embodiment 133 wherein a pair of R 7 and R 8
  • Embodiment 135. A compound of Formula 1 or any one of Embodiments 1 through 134 wherein R 9 is H or methyl.
  • Embodiment 136 A compound Embodiment 135 wherein R 9 is methyl.
  • Embodiment 137 A compound Embodiment 136 wherein R 9 is H.
  • Embodiment 138 A compound of Formula 1 or any one of Embodiments 1 through 137 wherein each R 12 , R 13 , R 14 and R 15 is independently H or methyl.
  • Embodiment 140 A compound of Embodiment 138 wherein each R 12 , R 13 , R 14 and R 15 is independently H.
  • Embodiment 141 A compound of Embodiment 140 wherein each R 1 and R 15 is
  • Embodiment 142 A compound of Formula 1 or any one of Embodiments 1 through 141 wherein each R 16 is H, halogen, C1-C3 alkyl or -CF 3 .
  • Embodiment 143 A compound of Embodiment 142 wherein each R 16 is H, halogen,
  • Embodiment 144 A compound of Embodiment 143 wherein each R 16 is CH 3 .
  • Embodiment Al A compound of Formula 1 as described in the Summary of the
  • R 1 is amino or C1-C3 alkyl
  • X 1 is halogen
  • X 2 is halogen, cyano or -CF 3 ;
  • W 1 is O
  • W 2 is O, S, N(H) or N(CH 3 );
  • A is a phenyl, pyridinyl or pyrimidinyl ring selected from A-l through A-20; n is 0 to 3;
  • R 2 is halogen, Ci ⁇ C 6 alkyl or Ci ⁇ C 6 alkoxy
  • R 3 is -C2 alkylene substituted with at least one R 5 ;
  • W 3 is O
  • R 4 is -OR 6 , -SR 6 , -NR 7 R 8 or -O M+;
  • M + is an agriculturally suitable alkali metal cation selected from sodium or potassium;
  • each R 5 is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio or
  • alkoxycarbonylalkyl C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 6 cyanoalkyl, C 3 -C 10 trialkylsilyl, C 2 -C 8 alkylcarbonylamino, C 2 -C6 haloalkoxyalkyl, C3-Cg haloalkoxycarbonylalkyl or C3-Cg alkylcarbonylalkyl; or
  • R 6 is G A , -(CR 12 R 1 ) q TG A , G B or -(CR 14 R 15 ) U TG B ; or
  • R 5 and R 6 are taken together to form a ring selected from D-1
  • D-1 Rt is selected from -C3 alkyl
  • p 0 or 1.
  • Embodiment A2 A compound of Embodiment Al wherein
  • R 1 is C r C 3 alkyl
  • X 1 is F or CI
  • X 2 is halogen or cyano
  • W 2 is O, S or N(H);
  • A is selected from A-l , A-2, A-3, A-4, A-5, A-6, A-7, A- 12, A- 13, A- 14,
  • n 0 to 2;
  • R 3 is Ci-C 2 alkylene substituted with one R 5 ;
  • R 4 is -OR 6 or -SR 6 ;
  • R 5 is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio;
  • R 6 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 2 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C3-C6 haloalkynyl, C 2 -C6 alkoxyalkyl, C3-Cg
  • alkoxycarbonylalkyl C3-C10 dialkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C 2 -C 6 cyanoalkyl; or
  • R 6 is G A , -(CR 12 R 13 ) q TG A , G B or -(CR 14 R 15 ) U TG B .
  • R 1 is methyl or ethyl
  • X 2 is CI or F
  • W 2 is O or S
  • A is selected from A-l , A-2, A-4 and A-l 5;
  • R 2 is halogen, Ci ⁇ C 6 alkyl or Ci ⁇ C 6 alkoxy
  • R 3 is C 1 -C 2 alkylene substituted with at least one R 5 ;
  • R 4 is -OR 6 ;
  • R 5 is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio;
  • R 6 is H, Ci-Cfr alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl,
  • G A is phenyl optionally substituted with up to 1 substituent selected from
  • G A is B-51 ;
  • r 0;
  • G B is selected from C-2, C-3, C-4 and C-8; u is 0 or 1 ; and
  • each T is a direct bond.
  • Embodiment A4 A compound of Embodiment A3 wherein
  • R 1 is methyl
  • X 2 is CI
  • W 2 is O
  • A is selected from A-l, A-2 and A-4;
  • n 0;
  • R 5 is halogen, C1-C2 alkoxy or C1-C2 haloalkoxy
  • R 6 is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 ,
  • G B is selected from C-2, C-3 and C-4;
  • Embodiment A5 A compound of Embodiment A3 wherein
  • X 2 is CI
  • A is selected from A-l;
  • R 5 is ethoxy or methoxy
  • R 6 is H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CF 3 , CH 2 CH 2 CH 2 F, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , CH 2 CH 2 OCH 3 , CH 2 CH 2 OCH 2 CH 3 , CH 2 OCH 2 CH 2 OMe or CH 2 CH 2 CN;
  • G B is C-l ;
  • u 1;
  • R 14 is H
  • R 15 is H
  • R 16 is CH 3 ;
  • R 16 is attached at the 1 -position.
  • Embodiment A6 A compound of Formula 1 as described in the Summary of the
  • R 1 is methyl
  • X 1 is F
  • X 2 is CI
  • W 1 is O
  • A is A-l
  • W 2 is O;
  • R 3 is Ci alkylene substituted with one R 5 ;
  • R 4 is -OR 6
  • R 5 is ethoxy or methoxy
  • R 6 is H, CH 3 , CH 2 CH 3 , CH 2 CF 3 , CH 2 CH 2 CH 2 F, CH 2 CH 2 OCH 3 or
  • Specific embodiments include compounds of Formula 1 selected from the group consisting of:
  • ote is a compound of Formula 1 selected from the group consisting of
  • This invention is also directed to a compound of Formula IP (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:
  • R 1 is ⁇ , amino or C1-C3 alkyl
  • X 1 is ⁇ or halogen
  • W 1 is O or S
  • A is a phenyl, pyridinyl or pyrimidinyl ring, the ring optionally substituted with up to 4 substituents independently selected from R 2 ;
  • W 2 is O, S or N(R 9 );
  • each R 2 is independently halogen, cyano, i ⁇ C 6 alkyl, Ci ⁇ C 6 haloalkyl, Ci ⁇ C 6 alkoxy or Ci-Cft haloalkoxy;
  • R 3 is C1-C3 alkylene substituted with at least one R 5 ;
  • W 3 is O or S
  • R 4 is H, -OR 6 , -SR 6 or -NR 7 R 8 ;
  • each R 5 is independently halogen, cyano, hydroxy, -CF 3 , Ci ⁇ C 6 alkoxy, i ⁇ C 6
  • R 6 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6
  • R 7 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8
  • alkoxycarbonylalkyl i-C ⁇ alkoxy or C 2 -C 8 dialkylaminosulfonyl
  • a phenyl ring or benzyl each optionally substituted with up to five substituents selected from C ⁇ -C 3 alkyl, -CF 3 and C ⁇ -C 3 alkoxy on ring members;
  • R 8 is H or C r C 3 alkyl
  • R 9 is H or C r C 3 alkyl
  • R 10 and R 1 1 are each independently H or C ⁇ -C 3 alkyl.
  • Embodiments of the present invention as described in the Summary of the Invention include those below.
  • Formula 1 includes N-oxides and salts thereof, and reference to "a compound of Formula 1" includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.
  • Embodiment IP A compound of Formula 1 wherein R 1 is amino or C ⁇ -C 3 alkyl.
  • Embodiment 2P A compound of Embodiment IP wherein R 1 is C ⁇ -C 3 alkyl.
  • Embodiment 3P A compound of Embodiment 2P wherein R 1 is methyl or ethyl.
  • Embodiment 4P A compound of Embodiment 3P wherein R 1 is methyl.
  • Embodiment 5P A compound of Formula 1 or any one of Embodiments 1 through 4 wherein X 1 is H.
  • Embodiment 6P A compound of Formula 1 or any one of Embodiments IP through 4P wherein X 1 is halogen.
  • Embodiment 7P A compound of Embodiment 6P wherein X 1 is F or CI.
  • Embodiment 8P A compound of Embodiment 7P wherein X 1 is F.
  • Embodiment 9P A compound of Formula 1 or any one of Embodiments IP through 8P wherein X 2 is halogen, cyano or -CF 3 .
  • Embodiment 10P A compound of Embodiment 9P wherein X 2 is halogen or cyano.
  • Embodiment 1 IP A compound of Embodiment 10P wherein X 2 is CI, F or cyano.
  • Embodiment 12P A compound of Embodiment I IP wherein X 2 is CI or F.
  • Embodiment 13P A compound of Embodiment 12P wherein X 2 is CI.
  • Embodiment 14P A compound of Formula 1 or any one of Embodiments IP through 13P wherein W 1 is S.
  • Embodiment 15P A compound of Formula 1 or any one of Embodiments IP through
  • Embodiment 16P A compound of Formula 1 or any one of Embodiments IP through
  • W 2 is O, S, N(H) or N(CH 3 ).
  • Embodiment 17P A compound of Embodiment 16P wherein W 2 is O, S or N(H).
  • Embodiment 18P A compound of Embodiment 17P wherein W 2 is O or S.
  • Embodiment 19P A compound of Embodiment 18P wherein W 2 is S.
  • Embodiment 20P A compound of Embodiment 18P wherein W 2 is O.
  • Embodiment 2 IP.
  • A is phenyl, pyridinyl or a 1 ,3-pyrimidinyl ring selected from A-l
  • Embodiment 22P A compound of Embodiment 21P wherein A is selected from A-l,
  • Embodiment 23P A compound of Embodiment 22P wherein A is selected from A-l,
  • Embodiment 24P A compound of Embodiment 23P wherein A is selected from A-l,
  • Embodiment 25P A compound of Embodiment 24P wherein A is selected from A-l,
  • Embodiment 26P A compound of Embodiment 25P wherein A is selected from A-l,
  • Embodiment 27P A compound of Embodiment 26P wherein A is selected from A-l and A-4.
  • Embodiment 28P A compound of Embodiment 27P wherein A is A-l .
  • Embodiment 29P A compound of Embodiment 27P wherein A is A-4.
  • Embodiment 3 OP.
  • Embodiment 3 IP A compound of Embodiment 3 OP wherein n is 0.
  • Embodiment 32P A compound of Formula 1 or any one of Embodiments IP through
  • R 2 is halogen, Q-C ⁇ alkyl or C j -C6 alkoxy.
  • Embodiment 33P A compound of Embodiment 32P wherein R 2 is halogen, -C3 alkyl or methoxy.
  • Embodiment 34P A compound of Embodiment 33P wherein R 2 is halogen.
  • Embodiment 35P A compound of Embodiment 34P wherein R 2 is F or CI.
  • Embodiment 36P A compound of Embodiment 33P wherein R 2 is methyl or methoxy.
  • Embodiment 37P A compound of Embodiment 36P wherein R 2 is methyl.
  • Embodiment 38P A compound of Formula 1 or any one of Embodiments IP through
  • R 3 is C1-C2 alkylene substituted with at least one R 5 .
  • Embodiment 40P A compound of Embodiment 38P wherein R 3 is C 2 alkylene
  • Embodiment 4 IP A compound of Embodiment 38P wherein R 3 is C ⁇ alkylene substituted with at least one R 5 .
  • Embodiment 42P A compound of Embodiment 4 IP wherein R 3 is C ⁇ alkylene
  • Embodiment 43P A compound of Formula 1 or any one of Embodiments IP through
  • Embodiment 44P A compound of Formula 1 or any one of Embodiments IP through
  • Embodiment 45P A compound of Formula 1 or any one of Embodiments IP through
  • R 4 is -OR 6 or -SR 6 , -NH 2 , -NH(CH 3 ) or -N(CH 3 ) 2 .
  • Embodiment 46P A compound of Embodiment 45P wherein R 4 is-OR 6 or -SR 6 .
  • Embodiment 48P A compound of Formula 1 or any one of Embodiments IP through
  • R 5 is halogen, hydroxy, Ci-C ⁇ alkoxy, Ci-C ⁇ haloalkoxy, Ci-C ⁇ alkylthio, Ci -C3 alkylamino or C 2 -C6 dialkylamino.
  • Embodiment 49P A compound of Embodiment 48P wherein R 5 is halogen, C1-C3 alkoxy, Ci -C3 haloalkoxy or C1-C3 alkylthio.
  • Embodiment 50P A compound of Embodiment 49P wherein R 5 is Ci -C3 alkoxy or Ci -
  • Embodiment 52P A compound of Embodiment 49P wherein R5 is halogen.
  • Embodiment 53P A compound of Embodiment 52P wherein R5 is F.
  • Embodiment 54P A compound of Embodiment 5 IP wherein R5 is methylthio.
  • Embodiment 55P A compound of Embodiment 5 IP wherein R5 is C 1 -C2 alkoxy.
  • Embodiment 56P A compound of Embodiment 55P wherein R5 is ethoxy.
  • Embodiment 57P A compound of Embodiment 55P wherein R5 is methoxy.
  • Embodiment 58P A compound of Formula 1 or any one of Embodiments 1 through 57 wherein R 6 is H, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 3 -C 8 cycloalkyl, C3-Cg halocycloalkyl, C3-Cg halocycloalkenyl or C3-C10 cycloalkenyl.
  • R 6 is H, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 2 -C 6
  • Embodiment 59P A compound of Embodiment 58P wherein R 6 is H, i-C ⁇ alkyl, C 2 - C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl or C 2 -C6 alkoxyalkyl.
  • Embodiment 60P A compound of Embodiment 59P wherein R 6 is H, i-C ⁇ alkyl, C 2 - C3 alkenyl, C1-C3 haloalkyl or C 2 -C3 alkoxyalkyl.
  • Embodiment 61P A compound of Embodiment 60P wherein R 6 is Ci-C ⁇ alkyl.
  • Embodiment 62P. A compound of Embodiment 6 IP wherein R 6 is methyl, ethyl, n- propyl, /-propyl or n-butyl.
  • Embodiment 63P A compound of Embodiment 62P wherein R 6 is methyl or ethyl.
  • Embodiment 64P A compound of Embodiment 62P wherein R 6 is ethyl.
  • Embodiment 65P A compound of Embodiment 62P wherein R 6 is methyl.
  • Embodiment 66P A compound of Formula 1 or any one of Embodiments 1 through 65 wherein R 9 is H or methyl.
  • Embodiment 67P A compound Embodiment 66P wherein R 9 is methyl.
  • Embodiment 68P A compound Embodiment 66P wherein R 9 is H.
  • Embodiment 69P A compound of Formula 1 or any one of Embodiments IP through
  • R 7 when taken alone (i.e. not taken together with R 8 ) is H, y-C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8
  • alkoxycarbonylalkyl y-C ⁇ alkoxy or C 2 -C 8 dialkylaminosulfonyl.
  • Embodiment 70P A compound Embodiment 69P wherein R 7 when taken alone is H, y-Cfr alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl C 3 -C 8 cycloalkyl or C 3 -C 8 alkoxycarbonylalkyl .
  • alkoxycarbonylalkyl alkoxycarbonylalkyl
  • Embodiment 73P A compound of Embodiment 72P wherein R 7 when taken alone is methyl.
  • Embodiment 74P A compound of Formula 1 or any one of Embodiments IP through 73P wherein R 8 when taken alone (i.e. not taken together with R 7 ) is H, methyl or ethyl.
  • Embodiment 75P A compound of Embodiment 74P wherein R 8 when taken alone is H.
  • Embodiment 76P. A compound of Embodiment 74P wherein R 8 when taken alone is methyl.
  • Embodiment 77P A compound of Formula 1 or any one of Embodiments IP through 76P wherein a pair of R 7 and R 8 attached to the same nitrogen atom are taken together with the nitrogen atom to form a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and optionally up to 2 heteroatoms selected from up to 2 O and up to 2 N, the ring optionally substituted with up to 2 substituents independently selected from halogen, cyano, C ⁇ -C 3 alkyl and C ⁇ -C 3 alkoxy on carbon atom ring members and methyl on nitrogen atom ring members.
  • Embodiment 78P Embodiment 78P.
  • Embodiment 79P A compound of Embodiment 78P wherein a pair of R 7 and R 8
  • Embodiment 80P A compound of Embodiment 78P wherein a pair of R 7 and R 8
  • Embodiments of this invention can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compositions comprising the compounds of Formula 1 but also to the compounds of Formula 1, the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1 unless further defined in the Embodiments.
  • embodiments of this invention including Embodiments 1-80 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention. Combinations of Embodiments 1-80 are illustrated by:
  • Embodiment Bl A compound of the Summary of the Invention wherein
  • R 1 is amino or C1-C3 alkyl
  • X 1 is halogen
  • X 2 is halogen, cyano or -CF 3 ;
  • W 1 is O
  • W 2 is O, S, N(H) or N(CH 3 );
  • A is phenyl, pyridinyl or a 1 ,3-pyrimidinyl ring selected from A-l through
  • n 0 to 4.
  • R 2 is halogen, Ci ⁇ C 6 alkyl or Ci ⁇ C 6 alkoxy
  • R 3 is Ci -C2 alkylene substituted with at least one R 5 ; W 3 is O;
  • R 4 is -OR 6 or -SR 6 , -NH 2 , -NH(CH 3 ) or -N(CH 3 ) 2 ;
  • R 5 is halogen, hydroxy, -C3 alkoxy, C1-C3 haloalkoxy, -C3 alkylthio, C1-C3 alkylamino or C 2 -C6 dialkylamino;
  • R 6 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C6 haloalkynyl, C 2 -C6 alkoxyalkyl, C3-Cg cycloalkyl, C3-Cg halocycloalkyl, C3-Cg halocycloalkenyl or C3-C10 cycloalkenyl.
  • Embodiment B2 A compound of Embodiment Bl wherein
  • R 1 is C r C 3 alkyl
  • X 1 is F or CI
  • X 2 is halogen or cyano
  • W 2 is O, S or N(H);
  • A is selected from A-1, A-3, A-4, A-5, A-6, A-7, A-12, A-13, A-14, A-15,
  • n 0 to 2;
  • R 2 is halogen, C1-C3 alkyl or methoxy
  • R 4 is -OR 6 or -SR 6 ;
  • R 5 is halogen, C1-C3 alkoxy, C1-C3 haloalkoxy or C1-C3 alkylthio; and R 6 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C6 haloalkynyl or C 2 -C6 alkoxyalkyl.
  • Embodiment B3 A compound of Embodiment B2 wherein
  • R 1 is methyl or ethyl
  • X 1 is F
  • X 2 is CI, F or cyano
  • W 2 is O or S
  • A is A-1, A-3, A-4, A-5, A-6, A-7, A-14 and A-15;
  • R 2 is halogen
  • R 3 is Ci alkylene substituted with one R 5 ;
  • R 4 is -OR 6 ;
  • R 5 is C1-C3 alkoxy or C1-C3 alkylthio
  • R 6 is H, C r C 6 alkyl, C 2 -C 3 alkenyl, C r C 3 haloalkyl or C 2 -C 3 alkoxyalkyl.
  • Embodiment B4 A compound of Embodiment B3 wherein
  • R 1 is methyl
  • X 2 is CI or F
  • W 2 is O
  • A is selected from A-1, A-4 and A-15;
  • R 6 is methyl, ethyl, n-propyl, /-propyl or n-butyl.
  • Embodiment B5. A compound of Embodiment B4 wherein
  • X 2 is CI
  • A is selected from A-l and A-4;
  • R 5 is ethoxy or methoxy
  • R 6 is methyl or ethyl.
  • Specific embodiments include compounds of Formula 1 selected from the group consisting of:
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein).
  • the compounds of the invention e.g., as a composition described herein.
  • embodiments relating to methods of use are those involving the compounds of embodiments described above.
  • Compounds of the invention are particularly useful for selective control of weeds in perennial plantation crops such as sugarcane and citrus.
  • herbicidal compositions of the present invention comprising the compounds of embodiments described above.
  • This invention is also directed to a method for pre-plant burndown comprising the steps of (a) contacting a residually effective amount of a compound of Formula 1 with undesired vegetation (i.e. weeds) and its growing medium; and (b) planting desired vegetation (i.e. crops) in said growing medium characterized by providing preemergent control of undesired vegetation without causing injury to said desired vegetation.
  • undesired vegetation i.e. weeds
  • desired vegetation i.e. crops
  • This method provides control (both postemergent and preemergent) of undesired vegetation (i.e. weeds) in a growing medium intended to be planted with desired vegetation (i.e. crops). Planting of desired vegetation in said growing medium can be accomplished within hours or days of contacting the undesired vegetation and its growing medium with a residually effective amount of a compound of Formula 1.
  • the method is characterized by providing control of undesired vegetation until the desired vegetation establishes a weed- controlling canopy.
  • the method is also characterized by the absence of injury to said desired vegetation.
  • the method requires contacting a residually effective amount of a compound of Formula 1 with undesired vegetation and its growing medium.
  • a “residually effective amount” is the amount contacted to provide both postemergent and preemergent control of undesired vegetation (without causing injury to said desired vegetation) until the desired vegetation provides a weed-controlling canopy. Once formed, a weed controlling canopy intervenes to provide control of undesired vegetation such that a residually effective amount of a compound of Formula 1 is no longer needed.
  • One skilled in the art can easily determine the "residually effective amount” appropriate to control (both postemergent and preemergent) undesired vegetation so as not cause injury to the desired vegetation until the desired vegetation establishes a weed-controlling canopy.
  • the “residually effective amount” will depend on such factors as species of both undesired and desired vegetation, growing medium, weather conditions and the like.
  • a compound of Formula la (wherein R 4 is other than H) can be prepared by reacting a compound of Formula 2 wherein R 3a is C1-C3 alkylene and Y 1 is a leaving group such as chloride, bromide, iodide or an alkylsulfonate (such as mesylate (-OMs) or tosylate (-OTs)) with a compound of Formula 3 in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride.
  • the reaction can be performed in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide.
  • a compound of Formula 2 can be prepared by the reaction of a compound of Formula 4 with halogenating agents such as bromine, sodium bromite, N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) in a solvent such as acetic acid, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide or 1,4-dioxane, or a mixture of water with the aforementioned solvents.
  • halogenating agents such as bromine, sodium bromite, N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS)
  • a solvent such as acetic acid, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide or 1,4-dioxane, or a mixture of water with the aforementioned solvents.
  • the reaction can be performed at temperatures ranging from ambient to the boiling point of the
  • a compound of Formula lb (i.e. a compound of Formula 1 wherein A is A-l, A-2 or A-3) can be prepared by the reaction of a phenol, thiophenol or aniline of Formula 5 with various alkylating agents such as a compound of Formula 7 wherein Y 3 is a leaving group such as chloride, bromide, iodide or alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide.
  • a compound of Formula 7 is commercially available or its preparation is known.
  • a compound of Formula lc i.e. a compound of Formula 1 wherein A is pyridine or pyrimidine ring A-4 through A-20
  • a base such as l,8
  • a compound of Formula lc i.e. a compound of Formula 1 wherein Y 4 is in an ortho relationship with a ring nitrogen
  • a compound of Formula 10 in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene
  • potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide
  • a compound of Formula 10 is commercially available or its preparation is known.
  • a compound of Formula 9 wherein Y 4 is a leaving group such as a halogen can be prepared by reaction of a compound of Formula 11 with halogenating agents such as oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorous pentachloride or phosphorous oxybromide in solvents such as dichloromethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide or 1,4-dioxane, or without solvents at temperatures ranging from 0 °C to 150 °C.
  • a compound of Formula 9 can be prepared by reduction followed by halogenation of a compound of Formula 12.
  • Reduction of the nitro group on a compound of Formula 12 can be achieved by treatment with iron powder in acetic acid or by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.
  • a metal catalyst such as palladium supported on an inert carrier such as activated carbon
  • Halogenation of the resulting amine can be achieved by a Sandmeyer reaction by treatment with an alkyl nitrite (e.g., iso-amyl or tert-butyl nitrite) and copper (I) and/or copper (II) halide, hydrofluoric acid pyridine complex or tetrafluoroboric acid in a solvent such as acetonitrile and at temperatures ranging from 0 °C to the reflux temperature of the solvent to yield the corresponding compound of Formula 9.
  • an alkyl nitrite e.g., iso-amyl or tert-butyl nitrite
  • copper (I) and/or copper (II) halide, hydrofluoric acid pyridine complex or tetrafluoroboric acid in a solvent such as acetonitrile and at temperatures ranging from 0 °C to the reflux temperature of the solvent to yield the corresponding compound of Formula 9.
  • a compound of Formula 11 can be prepared by deprotection of a compound of Formula 13 wherein Y 5 is a protecting group.
  • Y 5 is a protecting group.
  • a compound of Formula 11 can be prepared by treatment with boron tribromide in a solvent such as dichloromethane, acetonitrile or 1,4-dioxane, or without a solvent at temperatures ranging from 0 °C to 150 °C.
  • a compound of Formula 11 can be prepared by deprotection of a compound of Formula 13 wherein Y 5 is a benzyl group by catalytic hydrogenation in a hydrogen gas atmosphere at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.
  • a metal catalyst such as palladium supported on an inert carrier such as activated carbon
  • a compound of Formula 13a (wherein W 1 is O or S, and W 2 is O, and X 2 is a halogen) can be prepared by reduction followed by a Sandmeyer reaction from a compound of Formula 14.
  • Reduction of the nitro group on a compound of Formula 14 can be achieved by treatment with iron powder in acetic acid at a temperature ranging from 0 °C to 100 °C as shown in Scheme 8
  • the reduction can be carried out by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.
  • Halogenation of the resulting amine is facilitated by diazotization with an alkyl nitrite (e.g., iso-amyl or tert-butyl nitrite) followed by treatment with a copper (I) and/or copper (II) halide in a solvent such as acetonitrile at a temperature ranging from 0 °C to the reflux temperature of the solvent to give the corresponding compound of Formula 13a wherein X 2 is a halogen such as chloride or bromide.
  • an alkyl nitrite e.g., iso-amyl or tert-butyl nitrite
  • a solvent such as acetonitrile
  • W 1 is O or S W 1 is O or S, W 2 is O W 2 is O and X is halogen
  • a compound of Formula 14a (wherein W 1 is O or S) can be prepared by the reaction of a compound of Formula 15 with a compound of Formula 16 (wherein W 1 is O or S, and W 2 is O) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide at temperatures ranging from 0 °C to 150 °C.
  • a base such as l,8-diazabicyclo[5.4.0]undec-7-ene
  • potassium carbonate potassium hydroxide
  • cesium carbonate or sodium hydride and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-
  • a compound of Formula 12 can be prepared by reaction of a compound of Formula 17 (wherein W 1 is O or S) with a compound of Formula 18 wherein Y 6 is a leaving group such as fluoride, chloride, bromide, iodide or alkylsulfonate (e.g., mesylate (-OMs) or tosylate (-OTs)) in the presence of a base such as l,8-diazabicyclo[5.4.0]undec-7-ene, potassium carbonate, potassium hydroxide, cesium carbonate or sodium hydride, and in a solvent such as acetonitrile or acetone or preferably in a polar aprotic solvent such as N,N-dimethylformamide or dimethyl sulfoxide.
  • a compound of Formula 18 is commercially available or its preparation is known.
  • W 1 is O or S
  • a compound of Formula Id (wherein W 1 is O or S) can be prepared by the reaction of a compound of Formula 17 (wherein W 1 is O or S) with a compound of Formula 20 wherein the A ring is substituted with an appropriate leaving group Y 7 .
  • the A ring in this Scheme is from Exhibit 1 wherein the bond projecting to the left is connected to Y 7 and the bond projecting to the right is connected to W 2 in Formula 20.
  • a compound of Formula 20 wherein the A ring is lacking sufficiently electron- withdrawing substituents i.e. R 2
  • the use of a metal catalyst e.g., metal or metal salt
  • a metal catalyst e.g., metal or metal salt
  • the leaving group Y 7 on a compound of Formula 20 is Br, I or a sulfonate such as OS(0) 2 CF 3 or OS(0)2(CF 2 )3CF 3 .
  • a sulfonate such as OS(0) 2 CF 3 or OS(0)2(CF 2 )3CF 3 .
  • copper salt complexes e.g., Cul with NN- dimethylethylenediamine, proline, picolinic acid or bipyridyl
  • palladium complexes e.g., tris(dibenzylideneacetone)dipalladium(0) (i.e.
  • ligands such as 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (i.e. "Xantphos”), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (i.e
  • CyPFtBu "Joshphos" or 2,2'-bis(diphenylphosphino)-l, -binaphthalene (i.e. "BINAP")
  • a base such as potassium carbonate, potassium phosphate (K 3 P0 4 ), cesium carbonate, sodium phenoxide or sodium tert-butoxide, in a solvent such as N,N-dimethylformamide, 1 ,2-dimethoxy ethane, dimethyl sulfoxide, 1,4-dioxane or toluene, optionally mixed with alcohols such as ethanol, can be used.
  • a compound of Formula 20 is commercially available or its preparation is known. General methods useful for preparing a compound of Formula 17 are known. See, for example, WO 02/098227, US 7,548,072 or
  • a compound of Formula 21 wherein Y 8 is a sulfonate leaving group such as trifluoroethanesulfonyl or nonafluorobutylsulfonyl can be prepared by reaction of a phenol of Formula 17a with sulfonating agents such as trifluoromethanesulfonyl chloride trifluoromethanesulfonyl chloride or nonafluorobutylsulfonyl chloride in the presence of base such as triethylamine or pyridine.
  • a compound of Formula 1 can be prepared by a two-step procedure by first reacting a compound of Formula 22 (wherein W 1 is O or S) with a compound of Formula 21 containing a sulfonate leaving group Y 8 to give a compound of Formula 25 by the cross coupling methods previously described for Scheme 11.
  • W 1 is O or S
  • Y 8 a compound of Formula 21 containing a sulfonate leaving group
  • a compound of Formula 1 can be prepared by reaction of a compound of Formula 23 wherein W 1 is O or S with a compound of Formula 21 containing a sulfonate leaving group Y 8 using the cross coupling methods as previously described for Scheme 11.
  • a compound of Formula 23 is commercially available or its preparation is known.
  • W 1 is O or S
  • a compound of Formula 1 can also be prepared by the two-step procedure shown in Scheme 15.
  • a compound of Formula 26 can be prepared by reaction of a compound of Formula 21 containing a sulfonate leaving group Y 8 with a compound of Formula 24 wherein W 1 is O or S by the cross-coupling methods previously described for Scheme 11. Subsequent reaction of a compound of Formula 26 wherein Y 10 is a protecting group such as a methyl or benzyl group can be deprotected using methods described previously for Scheme 7.
  • a compound of Formula 26 wherein Y 10 is a protecting group such as an acetyl protecting group (wherein W 2 is NR 9 ) can be deprotected by boron trifluoride-methanol complex in solvents such as methanol or dichloromethane at a temperature ranging from 0 °C to 100 °C.
  • Reaction of a comound of Fomula 7 according to the conditions as described for Scheme 3 for a compound of Formula 5 or according to the conditions described for Scheme 4 for a comound of Forumla 5a can be employed to prepare a compound of Formulae lb or lc wherein W 2 is NR 9
  • a compound of Formula 24 is commercially available or its preparation is known.
  • a compound of Formula 1 can also be prepared by reacting a compound of Formula 30 wherein L 1 is amino or a protected amino (e.g., such as an amide, carbamate or nitro) group by methods known in the art. See, for example, WO 2007/083090, WO 2002/098227 or US 7,548,072.
  • a compound of Formula 30 can be prepared from a compound of Formula 28 (wherein Y 9 is the same as Y 9 in a compound of Formula 25 above) as shown in Scheme 17.
  • a compound of Formula 28 (wherein Y 9 is the same as Y 9 in a compound of Formula 25) can be prepared from a compound of Formula 27 (wherein Y 8 is the same as Y 8 in a compound of Formula 21) and a compound of Formula 22 as previously described in Scheme 13.
  • Note the A ring in this Scheme is from Exhibit 1 wherein the bond projecting to the left is connected to W 1 and the bond projecting to the right is connected to Y 9 in Formula 28.
  • a compound of Formula 27 is commercially available or its preparation is known in the art.
  • a compound of Formula 30 can also be prepared from a compound of Formula 29 (wherein Y 10 is the same as Y 10 in a compound of Formula 26) as shown in Scheme 18.
  • a compound of Formula 29 can be prepared by reaction of a compound of Formula 24 with a compound of Formula 27 (wherein Y 8 is same as Y 8 in a compound of Formula 21) using methods described previously for Scheme 15.
  • a compound of Formula 30 can be prepared directly from a compound of Formula 27 (wherein Y 8 is same as Y 8 in a compound of Formula 21) by reaction with a compound of Formula 23 as shown in Scheme 19 by the cross-coupling reactions as described previously for Schemes 11 and 14.
  • Reaction of a compound of Formula le wherein R ⁇ is benzyloxy can be hydrolyzed by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol or ethyl acetate at ambient temperature to prepare a compound of Formula If.
  • a metal catalyst such as palladium supported on an inert carrier such as activated carbon
  • a compound of Formula lg wherein R c is an alkoxy group or alkylamino group can be prepared from an acid of Formula If with the corresponding alcohol or amine by an esterification reaction in the presence of 0-(7- azabenzotriazol-l-y ⁇ -A .A .N' ⁇ N'-tetramethyluronium hexafluorophosphate (i.e. HATU) or 2-chloro-l-methylpyridinium iodide and a base such as triethylamine or N,N-diisopropylethylamine at a temperature ranging from 0 °C to 100 °C.
  • HATU 2-chloro-l-methylpyridinium iodide
  • a base such as triethylamine or N,N-diisopropylethylamine at a temperature ranging from 0 °C to 100 °C.
  • a compound of lg can be prepared from a compound of If using Mitsunobu conditions using triphenylphosphine in the presence of diisopropyl azodicarboxylate or diethyl azodicarboxylate.
  • a compound of Formula lg wherein R c is an alkoxy group can also be prepared from an acid of Formula If with an alkylating agent such as di-tert-butyl dicarbonate or R 4c 'OCH 2 Cl (wherein R c ' is for example a lower alkyl, lower alkylsilyl or phenyl) in the presence of base such as triethylamine, 4-dimethylaminopyridine or N,N-diisopropylethylamine.
  • an alkylating agent such as di-tert-butyl dicarbonate or R 4c 'OCH 2 Cl (wherein R c ' is for example a lower alkyl, lower alkylsilyl or phenyl) in the presence of base such as triethylamine, 4-dimethylaminopyridine or N,N-diisopropylethylamine.
  • Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H + (molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP + ).
  • 3 ⁇ 4 NMR spectra are reported at 400 MHz in ppm downfield from tetramethylsilane in CDCI 3 unless otherwise noted; “s” means singlet, “d” means doublet, “t” means triplet, “q” means quartet, “m” means multiplet and “br s” means broad singlet.
  • Step A Preparation of 3-[2-fluoro-5-[(2-methoxy-3-pyridinyl)oxy]-4-nitrophenyl]-l- methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione
  • the filtrate was diluted with ethyl acetate.
  • the mixture was neutralized with saturated aqueous sodium bicarbonate solution.
  • the organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated.
  • the residue was subjected to silica gel column chromatography to give the title compound as a light yellow foam (2.61 g).
  • Step C Preparation of 3-[4-chloro-2-fluoro-5-[(2-methoxy-3-pyridinyl)oxy]phenyl]- l-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione
  • reaction mixture was poured into 1 N hydrochloric acid, and extracted with ethyl acetate.
  • the organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated.
  • the residue was subjected to silica gel column chromatograpy eluting with ethyl acetate in hexanes to give the title compound as a light brown solid (1.60 g).
  • Step D Preparation of 3-[4-chloro-5-[(l ,2-dihydro-2-oxo-3-pyridinyl)oxy]-2- fluorophenyl]-l-methyl-6-(trifluoromethyl)-2,4(lH,3H)-pyrimidinedione
  • Step E Preparation of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
  • Step A Preparation of methyl 2-[[3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
  • reaction mixture was stirred for 6.5 h at room temperature and concentrated under reduced pressure.
  • the resulting reaction mixture was filtered and the potassium carbonate was rinsed with ethyl acetate.
  • the filtrate was concentrated in vacuo and the resulting residue was subjected to silica gel column chromatography eluting with ethyl acetate in hexanes to give the title compound as white foam (5.58 g).
  • Step A Preparation of 2-propen-l-yl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6- dioxo-4-(trifluoromethyl)-l(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2- methoxyacetate
  • Example 6 the product of Example 6) (5.42 g, 9.70 mmol) in 55 mL of a 3: 1 tetrahydrofuran/methanol solution at ambient temperature was added /?-toluenesulfinic acid sodium salt (2.37 g, 12.7 mmol) in 10 mL of a 1 : 1 tetrahydrofuran/methanol solution followed by tetrakis(triphenylphospine)palladium(0) (459 mg, 0.40 mmol). The reaction mixture was stirred for 6 h and concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate (90 mL), dichloromethane (30 mL) and water (15 mL), and the layers were separated.
  • ethyl acetate 90 mL
  • dichloromethane 30 mL
  • water 15 mL
  • Step A cyclobutyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
  • Example 7 the product of Example 7 (68.8 mg, 0.133 mmol), cyclobutanol (32 ⁇ , 29.4 mg, 0.408 mmol) and N,N-diisopropylethylamine (0.104 mL, 0.597 mmol) in tetrahydrofuran (3 mL) was added 2-chloro-l-methylpyridinium iodide (108 mg, 0.410 mmol) in 1 portion and the resulting mixture stirred at room temperature for 21 h, during which time a solid formed.
  • Step A 2-methoxyethyl 2-[2-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-
  • n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, z ' -Pr means isopropyl, Bu means butyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, -CN means cyano, and Ph means phenyl.
  • the present disclosure also includes Tables 1A through 1Q, each of which is constructed the same as Table 1 above except that the Table Header Row in Table 1 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row shown below.
  • Table 1 A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 1 above.
  • the first entry in Table 1A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables IB through 1Q are constructed similarly.
  • R 5 is OEt 1G
  • R 5 is S-z-Pr 1M
  • R 5 is F
  • R 5 is O-z ' -Pr 11
  • R 5 is NHEt lO
  • R 5 is Br
  • R 5 is SMe 1J
  • R 5 is NMe IP
  • R 5 is CF 3
  • R 5 is SEt IK R 5 is NH- «-Pr iQ R 5 is CN
  • R 5 is S-n-Pr 1L
  • R 5 is OH
  • Table 1.1 is constructed the same way as Table 1 except the structure below repl the header structure in Table 1.
  • the present disclosure also includes Tables 1.1 A through 1.1Q, each of which is constructed the same as Table 1.1 above except that the Table Header Row in Table 1.1 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 1.1 A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 1.1 above.
  • the first entry in Table 1.1 A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables L IB through 1.1Q are constructed similarly. TABLE 1.2
  • Table 1.2 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 1.2A through 1.2Q, each of which is constructed the same as Table 1.2 above except that the Table Header Row in Table 1.2 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 1.2A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 1.2 above.
  • the first entry in Table 1.2A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 1.2B through 1.2Q are constructed similarly.
  • Table 2 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 2A through 2Q, each of which is constructed the same as Table 2 above except that the Table Header Row in Table 2 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 2A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 2 above.
  • the first entry in Table 2A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 2B through 2Q are constructed similarly.
  • Table 3 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 3A through 3Q, each of which is constructed the same as Table 3 above except that the Table Header Row in Table 3 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 3 A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 3 above.
  • the first entry in Table 2A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 3B through 3Q are constructed similarly.
  • Table 4 is constructed the same way as Table 1 except the structure below replaces the header structure in Ta le 1.
  • the present disclosure also includes Tables 4A through 4Q, each of which is constructed the same as Table 4 above except that the Table Row Header in Table 4 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 4A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 4 above.
  • the first entry in Table 4A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 4B through 4Q are constructed similarly.
  • Table 5 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 5A through 5Q, each of which is constructed the same as Table 5 above except that the Table Header Row in Table 5 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 5 A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 5 above.
  • the first entry in Table 5A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 5B through 5Q are constructed similarly.
  • Table 6 is constructed the same way as Table 1 except the structure below replaces the header structure in Ta le 1.
  • the present disclosure also includes Tables 6A through 6Q, each of which is constructed the same as Table 6 above except that the Table Header Row in Table 6 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 6A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 6 above.
  • the first entry in Table 6A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 6B through 6Q are constructed similarly.
  • Table 7 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 7A through 7Q, each of which is constructed the same as Table 7 above except that the Table Header Row Table 7 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 7A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 7 above.
  • the first entry in Table 7A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 7B through 7Q are constructed similarly.
  • Table 8 is constructed the same way as Table 1 except the structure below replaces the header structure in Ta le 1.
  • the present disclosure also includes Tables 8A through 8Q, each of which is constructed the same as Table 8 above except that the Table Header Row in Table 8 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1A through 1Q above.
  • Table 8A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 8 above.
  • the first entry in Table 8A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 8B through 8Q are constructed similarly.
  • Table 9 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 9A through 9Q, each of which is constructed the same as Table 9 above except that the Table Header Row in Table 9 (i.e. "R 5 is OMe") is replaced with the respective r Table Header Row defined in Tables 1 A through 1Q above.
  • Table 9A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 9 above.
  • the first entry in Table 9A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 9B through 9Q are constructed similarly.
  • Table 10 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 10A through 10Q, each of which is constructed the same as Table 10 above except that the Table Header Row in Table 10 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1 A through 1Q above.
  • Table 10A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 10 above.
  • the first entry in Table 10A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 10B through 10Q are constructed similarly.
  • Table 10.1 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 10.1 A through 10.1Q, each of which is constructed the same as Table 10.1 above except that the Table Header Row in Table 10.1 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1 A through 1Q above.
  • Table 10.1 A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 10.1 above.
  • the first entry in Table 10.1 A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 10. IB through 10.1Q are constructed similarly.
  • Table 11 is constructed the same way as Table 1 except the structure below replaces the header structure in Table 1.
  • the present disclosure also includes Tables 11A through HQ, each of which is constructed the same as Table 11 above except that the Table Header Row in Table 11 (i.e. "R 5 is OMe") is replaced with the respective Table Header Row defined in Tables 1 A through 1Q above.
  • Table 11A the Table Header Row is "R 5 is OEt” and R 4 is as defined in Table 11 above.
  • the first entry in Table 11 A specifically discloses a compound of Formula 1 wherein R 4 is OH and R 5 is OEt.
  • Tables 1 IB through HQ are constructed similarly.
  • a compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • a composition i.e. formulation
  • additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels.
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
  • Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
  • Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy- 4-methyl-2-pentan
  • Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C 6 -C 2 2), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof.
  • plant seed and fruit oils e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
  • animal-sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
  • Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
  • alkylated fatty acids e.g., methylated, ethylated, butylated
  • Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
  • the solid and liquid compositions of the present invention often include one or more surfactants.
  • surfactants also known as “surface-active agents”
  • surface-active agents generally modify, most often reduce, the surface tension of the liquid.
  • surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
  • Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene
  • Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
  • Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
  • amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amine
  • Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon 's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
  • compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
  • formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes.
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent.
  • Solutions, including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water.
  • Active ingredient slurries, with particle diameters of up to 2,000 ⁇ can be wet milled using media mills to obtain particles with average diameters below 3 ⁇ .
  • Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 ⁇ range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques.
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
  • Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
  • Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Compound 55 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0%> sodium silicoaluminate 6.0%> montmorillonite (calcined) 23.0%
  • Compound 126 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0%> sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%
  • Compound 24 10.0% polyoxyethylene sorbitol hexoleate 20.0% C 6 -C 10 fatty acid methyl ester 70.0%>
  • Compound 5 5.0%> polyvinylpyrrolidone -vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0%> glyceryl monooleate 15.0% water 20.0%
  • Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
  • important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa
  • Compounds of the invention are particularly useful for selective control of weeds in perennial plantation crops such as sugarcane and citrus.
  • Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits.
  • plants genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits.
  • proteins toxic to invertebrate pests such as Bacillus thuringiensis toxin
  • the subject compounds are useful to modify plant growth.
  • the compounds of the invention have both postemergent and preemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth
  • the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
  • a herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.00025 to 20 kg/ha with a preferred range of about 0.002 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes.
  • the present invention also pertains to a composition
  • a composition comprising a herbicidally effective amount of a compound of Formula 1 and a biologicially effective amount of at least one additional biologically active compound or agent and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent.
  • the other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent.
  • one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
  • a mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminopyralid, aminocyclopyrachlor and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyri
  • herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-
  • the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1 :3000 and about 3000: 1. Of note are weight ratios between about 1 :300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1).
  • weight ratios between about 1 :300 and about 300: 1 for example ratios between about 1 :30 and about 30: 1).
  • One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.
  • combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable.
  • synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.
  • safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
  • a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
  • herbicide safeners such as allidochlor, benoxacor, l-bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, diamuron, dichlormid, dicyclonon, 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2 -methyl- 1, 3 -dioxolane (MG 191), dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, H-31868, isoxadifen-ethyl, LAB 147886, M-32988, mefenpyr-diethyl, mephenate, methoxyphenone,
  • herbicide safeners such as allidoch
  • Antido tally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
  • Preferred for better control of undesired vegetation e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety
  • a herbicide selected from the group consisting of ametryn, aminocyclopyrachlor, aminopyralid, atrazine, bromacil, chlorsulfuron, clomazone, diuron, glufosinate, glufosinate ammonium, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate -potassium, glyphosate -trimesium), hexazinone, imazapic, imazapyr, metsulfuron-methyl, norflurazon oryzalin, paraquat dichloride, pendimethalin, rimsulfuron, simazine, sulfometuron-methyl, triclopyr, triclopyr-but
  • Tables A2 through A12 are each constructed the same as Table Al above except that entries below the "Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below.
  • Table A2 the entries below the "Component (a)” column heading all recite “Compound 2”, and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 2 with ametryn.
  • Tables A3 through A12 are constructed similarly.
  • Table Bl lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention.
  • the second column of Table Bl lists the specific Component (b) compound (e.g., "ametryn" in the first entry).
  • the third, fourth and fifth columns of Table Bl lists ranges of weight ratios for rates at which the Component (b) compound is typically applied to a field-grown crop relative to Component (a).
  • the first line of Table Bl below the column headings specifically discloses the combination of Compound 5 with ametryn is typically applied in a weight ratio between 1 :364 to 3: 1, more typically applied in a weight ratio between 1 : 121 to 1 :2 and most typically applied in a weight ratio between 1 :22 to 1 :4.
  • the remaining lines of Table Bl are constructed similarly.
  • Compound 5 metsulfuron-methyl 1:4 to 1120:1 1:1 to 374:1 7:1 to 70:1
  • Compound 5 triclopyr 1:45 to 3:1 1:15 to 1:2 1:15 to 1:2
  • Tables B2 through B17 are each constructed the same as Table Bl above except that entries below the "Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below.
  • Table B2 the entries below the "Component (a)” column heading all recite “Compound 13”
  • the first entry below the column headings in Table B2 specifically discloses a mixture of Compound 13 with ametryne is typically applied in a weight ratio between 1:364 to 3:1, more typically applied in a weight ratio between 1:121 to 1:2 and most typically applied in a weight ratio between 1 :22 to 1 :4.
  • Tables B3 through B17 e constructed similarly.
  • Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-
  • Example stands for “Example” and is followed by a number indicating in which example the compound is prepared. Unless otherwise noted, mass spectra are reported in the following tables as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H + (molecular weight of 1) to the molecule, observed by mass spectrometry using either atmospheric pressure chemical ionization (AP + ) or electro-spray ionization (ESI).
  • AP + atmospheric pressure chemical ionization
  • ESI electro-spray ionization

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Abstract

L'invention concerne des composés de la Formule 1, y compris tous les stéréoisomères, les N-oxydes et les sels de ceux-ci, (I) dans laquelle R1, X1, X2, W1, A, W2, R3, W3 et R4 sont tels que définis dans la présente demande. L'invention concerne également des compositions contenant les composés de la Formule 1 et des procédés pour lutter contre une végétation indésirable, comprenant la mise en contact de la végétation indésirable ou de son environnement avec une quantité efficace d'un composé ou d'une composition de l'invention.
PCT/US2011/033846 2010-04-27 2011-04-26 Uraciles herbicides WO2011137088A1 (fr)

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WO2020057391A1 (fr) * 2018-09-20 2020-03-26 周银平 Préparation d'un composé pyridazinyl amine et utilisation associée
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