WO2005070889A1 - Herbicidal amides - Google Patents

Herbicidal amides Download PDF

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Publication number
WO2005070889A1
WO2005070889A1 PCT/US2005/002147 US2005002147W WO2005070889A1 WO 2005070889 A1 WO2005070889 A1 WO 2005070889A1 US 2005002147 W US2005002147 W US 2005002147W WO 2005070889 A1 WO2005070889 A1 WO 2005070889A1
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Prior art keywords
compound
och
alkyl
formula
methyl
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PCT/US2005/002147
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French (fr)
Inventor
Mary Ann Hanagan
Thomas Paul Selby
Paula Louise Sharpe
Ritesh B. Sheth
Thomas Martin Stevenson
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E.I. Dupont De Nemours And Company
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Publication of WO2005070889A1 publication Critical patent/WO2005070889A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/18—Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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

Definitions

  • This invention relates to certain carboxamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
  • BACKGROUND OF THE INVENTION 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, corn (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.
  • U.S. Patent 4,556,414 discloses herbicidal pyridinecarboxamides of Formula i.
  • R 1 , R 2 and R 3 are H, lower alkyl, alkoxy or alkoxyalkyl;
  • R 4 is a carboxyl radical, optionally in the form of a salt or ester, or a cyano, cyanoalkyl or alkoxyalkyl radical;
  • R 5 and R 6 are H, lower alkyl or cyano or together form a C 2 to C5 alkylene radical;
  • R 7 is halogen, lower alkyl, lower alkoxy, lower alkenyl, alkenyloxy, nitro, cyano or amino, alkylenedioxy, n is 0 to 5; and I in the nitrogen-containing heterocyclic ring indicates 2 or 3 units of unsaturation, This reference does not disclose the compounds of the present invention or their herbicidal utility.
  • This invention is directed to a compound of Formula I including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides: J-l J-2 J-3 J-4
  • Y is O, S(O) n or NR 8 ;
  • R is H, C2-C5 alkoxymethyl, C2-C5 alkylcarbonyl or C2-C5 alkoxycarbonyl;
  • R 1 is H or C1-C4 alkyl
  • R 2 is H, C!-C 4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C2-C4 alkoxymethyl, cyano, C1-C4 alkoxy or C 2 -C4 alkoxycarbonyl; each R 3 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C j - ⁇ hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C 2 -C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, hydroxy
  • R 5 is H, halogen, C ⁇ -Cg alkyl, C1-C4 haloalkyl, C 3 -Cg cycloalkyl, C 3 -C 6 halocycloalkyl, C2 ⁇ C 6 alkenyl, C 3 -Cg alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C j -04 alkylthio, C1-C4 haloalkylthio or C2-C5 alkoxycarbonyl;
  • R 6 is H, halogen, cyano, C ⁇ -Cg alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 haloalkylthio;
  • R 6a is C ⁇ -C 6 alkyl, C 2 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 4 -C 7 cycloalkylalkyl;
  • R 7 is H, C ⁇ -C 6 alkyl, C1-C4 haloalkyl, C ] - ⁇ cyanoalkyl, C 3 -C 6 alkenyl, C 2 -C 4 haloalkenyl, C 3 -Cg alkynyl, C 3 -C4 haloalkynyl, C3-C6 cycloalkyl or C 3 -C halocycloalkyl;
  • R 8 is H, C1-C4 alkyl, C 2 -C 4 alkylcarbonyl or C2-C4 alkoxycarbonyl; each R 9 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C 2 -Cg dialkylamino, C 2 -C4 alkylcarbonyl, C 2 -Cg alkoxycarbonyl, C 2 -C alkylaminocarbonyl, C 3 -Cg dialkylaminocarbonyl or C 3 -C6 trialkylsilyl;
  • R 10 is C-L-C4 alkyl; R 1 1 is H or C ⁇ -C 2 alkyl; or
  • R 10 and R 11 are taken together as -(CH 2 ) 3 -, -(CH 2 ) 4 -, -(CH 2 ) 5 - or -(CH 2 ) 6 -;
  • R 12 is H or C1-C4 alkyl
  • R 13 is H, C 1 -C 2 alkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 alkoxycarbonyl; or R 12 and R 13 are taken together as -(CH 2 ) 4 -, -(CH 2 ) 5 -, -CH 2 CH 2 OCH 2 CH 2 - or -CH 2 CH(CH 3 )OCH(CH 3 )CH 2 -;
  • R 14 is H, C1-C4 alkyl or Ci-C 4 alkoxy;
  • R 15 is H or C ⁇ -C 4 alkyl;
  • R 16 is H, C!-C 4 alkyl or C1-C4 alkoxy;
  • R 17 is H or Ci-C 4 alkyl;
  • R 18 is H, C j -C 2 alkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 alkoxycarbonyl; or RI 7 and R 18 are taken together as -(CH 2 ) 4 -
  • this invention pertains to a compound of Formula I, including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof.
  • This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula I and at least one of a surfactant, a solid diluent or a liquid diluent.
  • 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 Formula I (e.g., as a composition described herein).
  • This invention also relates to a herbicidal composition
  • a herbicidal composition comprising a herbicidally effective amount of a compound of Formula I, an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener, and at least one of a surfactant, a solid diluent or a liquid diluent.
  • composition, process, method, article, or apparatus 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, process, method, article, or apparatus.
  • "or” refers to an inclusive or and not to an exclusive or.
  • a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • the indefinite articles "a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component.
  • 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, f-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.
  • 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 .
  • Alkynyloxy includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylthioalkyl denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” 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 .
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • alkylsulfinyl examples include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • Cyanoalkyl denotes an alkyl group substituted with one cyano group.
  • Examples of “cyanoalkyl” include NCCH 2 , NCCH 2 CH 2 and CH 3 CH(CN)CH 2 .
  • Alkylamino dialkylamino
  • alkenylthio alkenylsulfinyl
  • alkenylsulfonyl alkynylthio
  • alkynylsulfinyl alkynylsulfonyl
  • alkynylsulfonyl and the like, are defined analogously to the above examples.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
  • Aromatic indicates that each of the ring atoms is essentially in the same plane and has a/7-orbital perpendicular to the ring plane, and in which (4n + 2) ⁇ electrons, when n is 0 or a positive integer, are associated with the ring to comply with Hiickel's rule.
  • heteroaromatic ring includes fully aromatic heterocycles.
  • the heteroaromatic rings can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • the 5- and 6-membered heteroaromatic rings described for R 3 typically comprise 1 to 4 heteroatom ring members, the heteroatom members selected from 0-4 N, 0-1 O and 0-1 S atoms.
  • Exhibit 1 shows examples of heteroaromatic rings; H-l through H-55 are to be construed as illustrative rather than limiting of the heteroaromatic rings within the scope of the present invention.
  • each R41 is independently R 9 ; R 41a , R 42 and R 43 are independently H or R 9 ; j is an integer from 0 to 3; and k is an integer from 0 to 2.
  • References herein to R 3 groups H-l through H-55 refer to those shown in Exhibit 1.
  • nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair of electrons for oxidation to the oxide; one skilled in the art will recognize those 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 dimethydioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethydioxirane
  • Constant width lines indicate bonds with a direction opposite or neutral relative to bonds shown with solid or dashed wedges; constant width lines also depict bonds in molecules or parts of molecules in which no particular stereoconfiguration is intended to be specified.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
  • 1-2 halogen indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl examples include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 G ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • haloalkylsulfinyl examples include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O).
  • haloalkylsulfonyl examples include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • C j -Cj The total number of carbon atoms in a substituent group is indicated by the "C j -Cj" prefix where i and j are numbers from 1 to 10.
  • C ⁇ -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • 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
  • C4 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 .
  • alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • alkylating agent refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R 4 and R 6a . "-CH (CH 2 ) p ⁇ " means 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 present invention comprises compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • Formula I when R 1 and R 2 of Formula I are different, then Formula I possesses a chiral center at the carbon atom to which they are commonly bonded.
  • This invention comprises racemic mixtures.
  • this invention includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula I' or I".
  • enantiomeric excess which is defined as (2x-l)T00%, 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).
  • ee enantiomeric excess
  • R 1 is H and R 2 is other than H, such as when R 2 is CH 3 , the more herbicidally active enantiomer is believed to be Formula I'.
  • Formula I 1 has the S configuration at the carbon atom to which R 1 and R 2 are commonly bonded.
  • the 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.
  • Compounds of Formula I can comprise additional chiral centers.
  • the substituents R 2 , R 3 , R , R 5 , R 6 , R 6a 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.
  • the agriculturally suitable salts of the compounds of the invention 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.
  • the agriculturally suitable salts of the compounds of the invention also include those formed with strong bases (e.g., hydrides or hydroxides of sodium, potassium or lithium).
  • strong bases e.g., hydrides or hydroxides of sodium, potassium or lithium.
  • Embodiments of the present invention include: Embodiment 1. A compound of Formula I wherein Y is O. Embodiment 2. A compound of Formula I wherein n is 0. Embodiment 3. A compound of Formula I wherein R is H. Embodiment 4. A compound of Formula I wherein q is 0. Embodiment 5. A compound of Formula I wherein R 1 is H. Embodiment 6.
  • Embodiment 7. A compound of Embodiment 6 wherein R 2 is H, cyano or CH 3 .
  • Embodiment 8. A compound of Embodiment 7 wherein R 2 is H or CH 3 .
  • Embodiment 9. A compound of Embodiment 7 wherein R 2 is H.
  • Embodiment 10. A compound of Embodiment 7 wherein R 2 is CH 3 .
  • Embodiment 11 A compound of Embodiment 7 wherein R 2 is cyano.
  • Embodiment 12 A compound of Formula I wherein when J is J-3, R 1 is H and R 2 is CH 3 , then the carbon atom to which R 1 and R 2 are attached is a stereocenter with the S configuration.
  • Embodiment 13 A compound of Formula I wherein when J is J-3, R 1 is H and R 2 is other than H, then the carbon atom to which R 1 and R 2 are attached is a stereocenter has a configuration described as S when R 2 is a methyl group.
  • Embodiment 14 A compound of Formula I wherein when R 1 is H and R 2 is CH 3 , then the carbon atom to which R 1 and R 2 are attached is a stereocenter with the S configuration.
  • Embodiment 16 A compound of Formula I wherein R 1 is.H, R 2 is other than H, and the carbon atom to which R 1 and R 2 are attached is a stereocenter having a configuration described as S when R 2 is a methyl group.
  • Embodiment 17 A compound of Embodiment 16 wherein R 2 is CH and the carbon atom to which R 1 and R 2 are attached is a stereocenter with the S configuration.
  • Embodiment 18 A compound of Formula I wherein m is an integer from 0 to 3.
  • Embodiment 19 A compound of Embodiment 18 wherein m is an integer from 0 to 2.
  • Embodiment 20 A compound of Embodiment 19 wherein m is 0 or 1.
  • Embodiment 21 A compound of Formula I wherein an R 3 substituent is attached at the position para to the connection of the phenyl ring to the remainder of Formula I.
  • Embodiment 22 A compound of Formula I wherein m is 1 and the R 3 substituent is attached at the position para position to the connection of the phenyl ring to the remainder of Formula I.
  • Embodiment 23 A compound of Formula I wherein each R 3 is independently halogen, cyano, nitro, C1-C 4 alkyl, C1-C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 1 -C 4 hydroxyalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 4 haloalkynyl, hydroxy, C 1 -C4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 2
  • Embodiment 24 A compound of Embodiment 23 wherein each R 3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, ⁇ -04 haloalkoxy, C 2 -C4 alkoxyalkoxy, C 3 -C4 alkynyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C 2 -Cg alkylcarbonyl, C 2 -C6 alkoxycarbonyl, C 3 -C 6 trialkylsilyl, R 25 (R 2 6)NS(O) 2 - or R 27 S(O) 2 N(R 28 )-; or two adjacent R 3 are taken together as -OCH2O- or -OCF2O-.
  • Embodiment 25 A compound of Embodiment 24 wherein each R 3 is independently halogen, cyano, nitro, C ⁇ -C 2 alkyl, Cj-C 2 haloalkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 3 alkynyloxy, C ⁇ -C 2 alkylthio, C j -C 2 alkylsulfinyl, C 1 -C 2 alkylsulfonyl, C 2 -C 3 alkylcarbonyl, C 2 -C 3 alkoxycarbonyl, trimethylsilyl, R 25 (R 26 )NS(O) 2 - or R 27 S(O) 2 N(R 28 )-; or two adjacent R 3 are taken together as -OCH 2 O- or -OCF 2 O-.
  • Embodiment 26 A compound of Formula I wherein each R 25 is independently H, C ⁇ -C 2 alkyl or C ⁇ -C 2 haloalkyl; and each R 26 is independently H or CH 3 ; Embodiment 27. A compound of Formula I wherein each R 27 is independently C ⁇ -C 2 alkyl, C ⁇ -C 2 haloalkyl or dimethylamino.
  • Embodiment 28 A compound of Formula I wherein each R 28 is independently H, C ⁇ -C 2 alkyl or C ⁇ -C 2 haloalkyl.
  • Embodiment 29 A compound of Embodiment 25 wherein each R 3 is independently halogen, cyano, methyl, Cj fluoroalkyl, methoxy or Ci fluoroalkoxy.
  • Embodiment 30 A compound of Embodiment 29 wherein each R 3 is independently F, Cl, Br, cyano, methyl or methoxy.
  • Embodiment 31 A compound of Embodiment 30 wherein each R 3 is independently F, Cl, Br, methyl or methoxy.
  • Embodiment 32 A compound of Formula I wherein R 4 is C j -Cy alkyl, C -C 7 cycloalkyl, C -C 7 cycloalkylalkyl, Cj-Cy haloalkyl, C2-C7 cyanoalkyl, C 2 -C 7 nitroalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 7 halocycloalkylalkyl, C 2 -C 7 alkenyl, C 2 -C 7 haloalkenyl, C 3 -C 7 alkynyl, C 3 -C 7 haloalkynyl, C 2 -C 7 alkoxyalkyl, C4-C7 (cycloalkyl)oxyalkyl, C 2 -C 7 haloalkoxyalkyl,
  • Embodiment 33 A compound of Embodiment 32 wherein R is C ⁇ -C 6 alkyl, C 3 -Cg cycloalkyl, C4-C7 cycloalkylalkyl, Cj-C ⁇ haloalkyl, C 2 -C 6 cyanoalkyl, C 3 -Cg alkenyl, C 3 -Cg haloalkenyl, C 3 -Cg alkynyl, C 3 -C 6 haloalkynyl, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl or C 2 -C 6 alkylthioalkyl.
  • Embodiment 34 A compound of Embodiment 33 wherein R is C j -Cg alkyl, CJ-C6 haloalkyl, C 3 -Cg cycloalkyl, cyclopropylmethyl, C 3 -C6 alkenyl, C 3 -C6 haloalkenyl or C 3 -Cg alkynyl.
  • Embodiment 35 A compound of Embodiment 34 wherein R is C 3 -C 4 alkyl, C -C4 haloalkyl, C 3 -C 4 cycloalkyl, C 3 -C4 alkenyl, C 3 -C 4 haloalkenyl or C 3 -C4 alkynyl.
  • Embodiment 36 A compound of Embodiment 35 wherein R is C 3 -C4 alkyl, C -C 4 alkenyl or C 3 -Q4 alkynyl.
  • Embodiment 37 A compound of Embodiment 36 wherein R 4 is C 3 -C 4 alkyl.
  • Embodiment 38. A compound of Embodiment 37 wherein R is CH(CH 3 ) 2 .
  • Embodiment 39 A compound of Formula I wherein R 5 is halogen, C j -C 2 haloalkyl, C ⁇ -C 2 alkoxy or C ⁇ -C 2 alkylthio.
  • Embodiment 40 A compound of Embodiment 39 wherein R 5 is halogen, CF 3 or methoxy.
  • Embodiment 41 A compound of Embodiment 40 wherein R 5 is halogen.
  • Embodiment 42 A compound of Embodiment 41 wherein R 5 is F, Cl or Br.
  • Embodiment 43 A compound of Embodiment 42 wherein R 5 is Cl or Br.
  • Embodiment 44 A compound of Formula I wherein R 6 is H, halogen, cyano, C -C 3 alkyl, C ⁇ -C 3 haloalkyl, C ⁇ -C 3 alkoxy or C j -C 3 alkylthio.
  • Embodiment 45 A compound of Embodiment 44 wherein R 6 is Ci -C 3 alkyl.
  • Embodiment 46 A compound of Embodiment 45 wherein R 6 is methyl.
  • Embodiment 47 A compound of Formula I wherein R 6a is C ⁇ -C 3 alkyl.
  • Embodiment 48 A compound of Embodiment 47 wherein R 6a is methyl.
  • Embodiment 49 A compound of Formula I wherein R 7 is C ⁇ -C alkyl or C 1 -C 2 fluoroalkyl.
  • Embodiment 50 A compound of Embodiment 49 wherein R 7 is C ⁇ -C 2 alkyl, CHF2 or CH 2 CF 3 .
  • Embodiment 51 A compound of Embodiment 50 wherein R 7 is methyl.
  • Embodiment 52 A compound of Formula I wherein J is J-l, J-2 or J-3.
  • Embodiment 53 A compound of Formula I wherein J is J-l, J-2 or J-4.
  • Embodiment 54 A compound of Formula I wherein J is J-l, J-3 or J-4.
  • Embodiment 55 A compound of Formula I wherein J is J-l or J-2.
  • Embodiment 56 A compound of Formula I wherein J is J-l or J-3.
  • Embodiment 57 A compound of Formula I wherein J is J-l or J-4.
  • Embodiment 58 A compound of Formula I wherein J is J-l.
  • Embodiment 59 A compound of Formula I wherein J is J-2.
  • Embodiment 60 A compound of Formula I wherein J is J-3.
  • Embodiment 61 A compound of Formula I wherein J is J-4.
  • Embodiment 62 A compound of Formula I wherein when J is J-3, then R 3 is other then optionally substituted phenoxy.
  • Embodiment 63 A compound of Formula I wherein R 3 is other than optionally substituted phenoxy.
  • Embodiment 64 A compound of Formula I wherein when J is J-3 and Y is NR 8 , then R is other than alkyl substituted with optionally substituted phenyl.
  • Embodiment 65 A compound of Formula I wherein when J is J-3, then Y is O or S(O) n .
  • Embodiment 66 A compound of Formula I wherein when J is J-l and R is optionally substituted phenyl, then Y is O or S(O) n .
  • Embodiment 67 A compound of Formula I wherein when R is optionally substituted phenyl, then Y is O or S(O) n .
  • Embodiment 68 A compound of Formula I wherein Y is O or S(O) n .
  • Embodiment 69. A compound of Formula I wherein when Y is NR 8 , then R 2 is other than cyano.
  • Embodiment 70 A compound of Formula I wherein when J is J-3, then R 4 is other than phenyl.
  • Embodiment 71 A compound of Formula I wherein when J is J-l or J-2, then R 4 is other than optionally substituted phenyl.
  • Embodiment 72 A compound of Formula I wherein when J is J-3, then R 4 is other than optionally substituted phenyl.
  • Embodiment 73 A compound of Formula I wherein R 4 is other than optionally substituted phenyl.
  • Embodiment 74 A compound of Formula I wherein when J is J-3 and Y is NR 8 , then R 4 is other than benzyl.
  • Embodiment 75 A compound of Formula I wherein when J is J-3 and Y is NR 8 , then R 4 is other than alkyl substituted with optionally substituted phenyl.
  • Embodiment 76 A compound of Formula I wherein when Y is NR 8 , then R is other than alkyl substituted with optionally substituted phenyl.
  • Embodiment 77 A compound of Formula I wherein when J is J-4, then Y is O or NR 8 .
  • Embodiment 78 A compound of Formula I wherein when J is J-4, then Y is O.
  • Embodiment 79 A compound of Formula I wherein R 3 is other than an optionally substituted 5-membered heteroaromatic ring or an optionally substituted 6-membered heteroaromatic ring. Combinations of Embodiments 1-79 are illustrated by: Embodiment A.
  • Embodiment B A compound of Embodiment A wherein Y is O and R is H.
  • Embodiment C A compound of Embodiment B wherein R 6 is H, halogen, cyano, C1-C3 alkyl, Ci-Gj haloalkyl, C!-C 3 alkoxy or C ⁇ -C 3 alkylthio.
  • Embodiment D A compound of Embodiment C wherein R 5 is halogen, C ⁇ -C 2 haloalkyl, ⁇ -C ⁇ alkoxy or C ⁇ -C 2 alkylthio; and R 7 is C ⁇ -C 2 alkyl, CHF 2 or CH 2 CF 3 .
  • Embodiment E Embodiment E.
  • each R 3 is independently halogen, cyano, nitro, alkyl, C 1 -C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C 2 -C alkoxyalkoxy, C3-C4 alkynyloxy, Cj-04 alkylthio, C 1 -C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 3 -C 6 trialkylsilyl, R 25 (R 2 6)NS(O) 2 - or R 7 S(O) 2 N(R 28 )-; or two adjacent R 3 are taken together as -OCH 2 O- or -OCF 2 O-.
  • Embodiment F A compound of Embodiment E wherein R 1 is H and R 2 is H, cyano or CH 3 .
  • Embodiment G A compound of Embodiment F wherein R 5 is halogen, CF or methoxy.
  • Embodiment H A compound of Embodiment G wherein J is J-l .
  • Embodiment I A compound of Embodiment H wherein R 5 is halogen.
  • Embodiment J A compound of Embodiment J.
  • Embodiment K A compound of Embodiment J wherein R 4 is Cj-Cg alkyl, Cj-Cg haloalkyl, C 3 -C 6 cycloalkyl, cyclopropylmethyl, C -Cg alkenyl, C 3 -Cg haloalkenyl or C 3 -Cg alkynyl.
  • Embodiment L A compound of Embodiment K wherein R 2 is CH 3 and the carbon atom to which R 1 and R 2 are attached is a stereocenter with the S configuration.
  • Specific embodiments include compounds of Formula I selected from the group consisting of: 2-chloro-N- [(IS)- 1 -(4-fluorophenyl)ethyl] -6-methyl-4-( 1 -methylethoxy)- 3-pyridinecarboxamide, 2-bromo-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-N-[(lS)-l-(4-methoxyphenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-6-methyl-4-(l-methylethoxy)-N-[(lS)-l-(4-methylphenyl)ethyl]- 3-pyridinecarboxamide, and 2-bromo-6-methyl-4-(l-methylethoxy)-N-[(lS)-l-(4-methylphen
  • herbicidal compositions of the present invention comprising the compounds of embodiments described above.
  • 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).
  • embodiments relating to methods of use are those involving the compounds of embodiments described above.
  • J is J-l, J-3 or J-4;
  • R 2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkoxymethyl, cyano or C 2 -C 4 alkoxycarbonyl;
  • each R 3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C6 halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C 2 -C4 haloalkenyl, C 3 -C
  • R 2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C6 cycloalkyl, C 2 -C alkoxymethyl, cyano, methoxy or C 2 -C 4 alkoxycarbonyl; and each R 3 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C!-C 4 hydroxyalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 2 -C4 alkenyl, C 2 -C 4 haloalkenyl
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1 through 33 and accompanying text.
  • R 42 , R 43 , R 50 , R 51 , R 52 , R 53 , R 60 , Y, j, k, m, n, p and q in the compounds of Formulae I through Id, and 2 through 69 below are as defined above in the Summary of the Invention and description of embodiments unless otherwise indicated.
  • Compounds of Formulae la through le are various subsets of the compounds of Formula I
  • compounds of Formulae 2a through 2d are subsets of compounds of Formula 2
  • compounds of Formulae 4a through 4d are subsets of the compounds of Formula 4
  • compounds of Formulae 18a and 18b are subsets of compounds of Formula 18.
  • compounds of Formula I are prepared by treating an amine of Formula 2 with an appropriate acid chloride of Formula 3 in an inert solvent with one molar equivalent of a base (e.g., triethylamine or potassium carbonate) present.
  • a base e.g., triethylamine or potassium carbonate
  • polymer-supported acid scavengers are useful such as polymer-bound equivalent of N,N-diisopropylethylamine and 4-(dimethylamino)pyridine, such as N-[(4-ethenylphenyl)- methyl] -N-methyl-4-pyridinamine polymer with diethenylbenzene and ethenylbenzene (CAS Registry Number 82942-26-5, hereafter identified as "PS-DMAP").
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; halocarbons such as dichloromethane or chloroform; and nitriles such as acetonitrile.
  • compounds of Formula I are prepared by treating the hydrochloride salts of amines of Formula 2 with an appropriate acid chloride or bromide of Formula 3 in an inert solvent with two molar equivalents of a base (e.g., triethylamine, potassium carbonate or PS-DMAP) present.
  • a base e.g., triethylamine, potassium carbonate or PS-DMAP
  • the method of Scheme 1 is illustrated in Step B of Example 1, Example 2, Step E of Example 5, Step B of Example 9, Step D of Example 11 and Step C of Example 12.
  • Compounds of Formula I can also be synthesized by reacting an amine of Formula 2 with an appropriate carboxylic acid of Formula 4 in the presence of an organic dehydrating reagent such as 1,3-dicyclohexylcarbodiimide (DCC) or l-[3-(dimethylamino)propyl]- 3-ethylcarbodiimide hydrochloride (EDC) as depicted in Scheme 2.
  • organic dehydrating reagent such as 1,3-dicyclohexylcarbodiimide (DCC) or l-[3-(dimethylamino)propyl]- 3-ethylcarbodiimide hydrochloride (EDC) as depicted in Scheme 2.
  • DCC 1,3-dicyclohexylcarbodiimide
  • EDC l-[3-(dimethylamino)propyl]- 3-ethylcarbodiimide hydrochloride
  • Polymer-supported reagents are again useful here
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • Step B of Example 1 This method is illustrated in Step B of Example 1, Example 2, Step E of Example 5, Step B of Example 9, Step D of Example 11 and Step C of Example 12.
  • Benzylamines of Formula 2 are commercially available or are readily prepared by numerous well known methods, several of which are described in Schemes 23-28.
  • compounds of Formulae la, lb, Ic or Id can also be prepared by treating amides of Formula 5a- 5d wherein X 1 is a leaving group such as halide, methyl sulfonate or p-toluenesulfonate with a nucleophile of Formula 6 and a strong base (e.g., sodium hydride or potassium t-butoxide) in a polar solvent at temperatures ranging from 0 to 150 °C; displacements with alkoxides and thiolates generally proceed at 0 to 80 °C, displacements with amines may require temperatures up to 150 °C.
  • a strong base e.g., sodium hydride or potassium t-butoxide
  • Suitable solvents are selected from the group consisting of amides such as N,N-dimethylformamide, lower alcohols such as ethanol, ethers such as tetrahydrofuran or dioxane, or sulfoxides or sulfones such as dimethylsulfoxide or sulfolane.
  • R 50 is ; and X 1 is a nucleophilic reaction leaving group such as halide, OS(O)2Me, OS(O) 2 -C 6 H 4 - -CH 3 or S(O) 2 CH 3 .
  • Compounds of Formulae 5a-5d can be prepared from the corresponding starting compounds using methods analogous to those of Schemes 1 and 2 as well as other methods.
  • the method of Scheme 3 is illustrated by Examples 3, 4, 8 and 10.
  • Compounds of Formulae la, lb, Ic or Id wherein Y is S(O) n and n is 1 can be prepared by oxidation of corresponding compounds of Formulae la, lb, Ic or Id wherein Y is S(O) n and n is 0 by contact with an appropriately stoichiometric amount of an oxidizing agent such as m-chloroperbenzoic acid in an inert solvent such as dichloromethane or 1,2-dichloroethane using reaction conditions well known in the art.
  • Carboxylic acids of Formulae 4a-d (Formula 4 wherein J is J-l, J-2, J-3 or J-4, respectively) can be prepared as depicted in Scheme 4.
  • R 51 is C ⁇ 2 H
  • R 51 is C0 2 H
  • R51 is C0 2 R52 C(0)NH 2 or CN
  • R 51 is C0 2 H
  • R51 is C0 2 H
  • R 51 is C0 2 R 52
  • R51 is C0 2 H
  • R 51 is C0 2 R52 C(0)NH 2 or CN
  • R511 i iss 'C0 2 H
  • R51 is C0 2 H
  • R 51 is C0 2 R 52 , C(0)NH 2 or CN wherein R 52 is carbon-based radical such as alkyl, preferably C j -Q ⁇ alkyl; and
  • X 1 is a nucleophilic reaction leaving group such as halide, OS (O) 2 CH 3 .
  • carboxylic acids of Formulae 4a-4d can be prepared from corresponding compounds of Formulae 7a- 7d wherein R 51 is CO 2 H and X 1 is a leaving group such as halide, methyl sulfonate or -toluenesulfonate by treatment with a compound of Formula 6 and 2.0 to 2.4 equivalents of a strong base (e.g., sodium hydride or potassium t-butoxide) in a polar solvent at temperatures ranging from 0 to 150 °C.
  • a strong base e.g., sodium hydride or potassium t-butoxide
  • Preferred temperatures range from room temperature to 100 °C.
  • Suitable solvents are selected from the group consisting of amides such as N,N-dimethylformamide (DMF), ethers such as tetrahydrofuran or sulfoxides or sulfones such as dimethylsulfoxide or sulfolane.
  • amides such as N,N-dimethylformamide (DMF)
  • ethers such as tetrahydrofuran or sulfoxides or sulfones such as dimethylsulfoxide or sulfolane.
  • Scheme 4 also shows that substituted esters, amides and nitriles of Formulae 8a-8d can be made from esters, amides and nitriles of Formulae 7a-7d (wherein R 51 is CO 2 R 52 , C(O) ⁇ H 2 or CN and X 1 is leaving group) via displacement by treatment with compounds of Formula 6 in the presence of base.
  • Suitable bases include alkali metal carbonates, hydroxides, alkoxides and hydrides (e.g., K 2 CO 3 , KO-t-Bu, NaH, NaOEt) and trialkylamine bases (e.g., triethylamine).
  • reaction is conducted in a suitable solvent such as N,N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran or excess compound of Formula 6 wherein Y is O (i.e. an alcohol) and at temperatures ranging from 0 °C to the reflux temperature of the solvent.
  • a suitable solvent such as N,N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran or excess compound of Formula 6 wherein Y is O (i.e. an alcohol) and at temperatures ranging from 0 °C to the reflux temperature of the solvent.
  • a suitable solvent such as N,N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran or excess compound of Formula 6 wherein Y is O (i.e. an alcohol) and at temperatures ranging from 0 °C to the reflux temperature of the solvent.
  • Substituted acids of Formulae 4a-4d can then be prepared by base or acid hydrolysis of the corresponding esters, amides and nitriles of Formulae 8a-8d (wherein R 52 is preferably methyl or ethyl).
  • Suitable bases include alkali metal hydroxides (e.g., NaOH, KOH).
  • the ester, amide or nitrile can be dissolved in a mixture of water and an alcohol such as ethanol and treated with base. The reaction mixture is stirred at temperatures ranging from 0 °C to the reflux temperature of the solvent. Hydrolysis of esters, amides or nitriles provides the corresponding carboxylic acids in the form of an alkali metal salt.
  • R 5 is halogen
  • compounds of Formulae 8a-8d can be converted to compounds of Formulae 8a-8d and Compounds of Formulae Ia-d respectively (wherein R 5 is alkoxy, haloalkoxy, alkylthio or haloalkylthio) by reacting with an alkyl alcohol, haloalkyl alcohol, alkylmercaptan or haloalkylmercaptan in the presence base such as an alkali metal base (e.g., potassium carbonate, sodium hydride or a sodium alkoxide) in a solvent such as N,N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran or an alkyl alcohol at temperatures ranging from 0 °C to the reflux temperature of the solvent.
  • an alkali metal base e.g., potassium carbonate, sodium hydride or a sodium alkoxide
  • a solvent such as N,N-dimethylformamide, acet
  • R 5 is Cl are described in World Patent Publications WO 02/22583 and WO 03/027112 respectively. Additional carboxylic acids of Formula 7a are described in Eur. J. Org. Chem. 2001, 1371.
  • the other compounds of Formulae 7a-7d can be prepared by the wide variety of methodologies known in the art of synthetic organic chemistry, including those shown in the following Schemes. For example as shown in Scheme 6, compounds of Formula 7a wherein R 51 is CO 2 H, CO 2 R 52 or C(O)NH 2 and X 1 is Cl or Br can be prepared from the corresponding acyl halides of Formula 18 by reaction with water, R 52 OH (19) or ammonia, respectively, according to standard methods.
  • Xi is Cl orBr.
  • R51 is C0 2 H, C0 2 R52 or C(0)NH 2 .
  • Compounds of Formula 18 wherein R 5 is X 1 (Formula 18a) or R 6 is X 1 (Formula 18b) can in turn be prepared by from the corresponding 4-hydroxy pyridones of Formulae 20a and 20b as shown in Scheme 7.
  • Scheme 7
  • Xi is Cl orBr.
  • 20b 18b R53 is Hor C r C2 alkyl.
  • a halogenating reagent such as phosphorus oxychloride or phosphorus oxybromide at reflux temperatures provides the corresponding dihalo acid halides of Formulae 18a or 18b.
  • a halogenating reagent such as phosphorus oxychloride or phosphorus oxybromide at reflux temperatures.
  • R 53 is methyl or ethyl (i.e. esters) it is not necessary to hydrolyze the esters to acids; the acid bromides are obtained directly from the esters under the reaction conditions.
  • the phosphorus oxyhalide can be used as the solvent, or another solvent can be added.
  • Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; halocarbons such as dichloromethane or chloroform; and nitriles or amines such as acetonitrile or N,N-diethylaniline.
  • a catalyst such as DMF can also be used.
  • Compounds of Formula 18a and 18b wherein X 1 is chloride are useful starting materials for preparing compounds of Formula 18a and 18b wherein X 1 is bromine or iodine by halogen exchange according to the general method described in Eur. J. Org. Chem.
  • Reflux or microwave 21 22 20a R53 is -C j alkyl.
  • Suitable solvents are selected from the group consisting of alcohols such as ethanol or isopropanol; and hydrocarbons such as toluene or benzene at temperatures ranging from 0 °C to the reflux temperature of the solvent.
  • the reaction can also be carried out at temperatures up to 250 °C using a microwave reactor.
  • ethers of Formula 8a wherein Y is O and R 51 is CO 2 R 52 can be prepared from compounds of Formula 23 by selective O-alkylation with compound of Formula 24 wherein X 2 is a nucleophilic reaction leaving group such as halide, tosylate or mesylate) in the presence of a base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide at temperatures ranging from room temperature to the reflux temperature of the solvent.
  • a base e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine
  • a solvent such as alcohol, acetonitrile or N,N-dimethylformamide
  • Suitable solvents include halocarbons such as dichloromethane or trichloromethane and hydrocarbons such as toluene or benzene.
  • Suitable reaction temperatures range from 0 °C to the reflux temperature of the solvent.
  • Step A of Example 11 illustrates the method of Scheme 10.
  • compounds of Formula 5b can be prepared by lithiation in the 4-position of a pyridine of Formula 27, followed by addition of an isocyanate of Formula 28. The reaction is conducted at low temperatures (e.g., 0 to -80 °C) in the presence of a lithium dialkylamide such as lithium diisopropylamide (LDA) in solvents such as ether or tetrahydrofuran.
  • LDA lithium diisopropylamide
  • Suitable acids for removal of the CH 2 OCH 3 group include trifluoroacetic acid, p-toluenesulfonic acid, hydrochloric acid and hydrobromic acid, as well as solid acid resins such as sulfonated polystyrene.
  • Suitable solvents for the removal of the CH 2 OCH 3 group include diethyl ether, tetrahydrofuran, dioxane, dichloromethane, dichloroethane and other solvents inert to the action of acids.
  • the hydroxypyridines of Formula 30 can be alkylated with an alkylating agent of Formula 24 wherein X 2 is a nucleophilic reaction leaving group such as halide, tosylate or mesylate.
  • Suitable acid acceptors include bases such as alkali hydroxides, alkali carbonates and alkali hydrides, as well as alkoxides and other strong bases.
  • Suitable solvents are stable in the presence of bases and include tetrahydrofuran, dioxane, dimethylsulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide. Lower alcohols are particularly useful as solvents for reactions involving alkoxides as acid acceptors. Preferred conditions involve the use of potassium carbonate as the acid acceptor and N,N-dimethylformamide as the solvent.
  • the method of Scheme 13 is illustrated in Example 15.
  • the alkylation involves contacting a compound of Formula le with an alkylating agent of Formula 31 wherein X 3 is a nucleophic reaction leaving group such as a halide (e.g., bromide, iodide), sulfonate (e.g., mesylate, triflate, -toluenesulfonate) or an ether (when , Formula 31 is, for example, a trialkyloxonium tetrafluoroborate).
  • This reaction can be carried out in excess alkylating agent (e.g., iodomethane) or using a variety of solvents such as ethers, acetonitrile or N,N-dimethylformamide.
  • pyridines of Formula 29 can be synthesized by nucleophilic displacement reactions on the corresponding 3-halopyridines or by alkylation of the corresponding 3-hydroxy- or 3-mercaptopyridines according to general methods described by Testaferri et al., Tetrahedron 1985, 41, 1373-1384; Harrowven et al., Tetrahedron 2001, 57, 4447_4454; U.S. Patent 5914328; and PCT Patent Publication WO2002/088114.
  • halogen substituted pyrazole esters of Formula 7c (wherein R 51 is CO 2 R 52 and X 1 is halogen) can be prepared from pyrazole aldehydes of Formula 33 by oxidation to the carboxylic acid followed by esterification.
  • aldehydes of Formulae 33 Treatment of aldehydes of Formulae 33 with an oxidizing reagent (such as potassium permanganate, potassium peroxymonosulfate (e.g., Oxone®), a sodium perchlorate/sodium chlorite mixture or manganese dioxide) in a suitable solvent or solvent mixture (e.g., comprised of one or more of the following solvents: alcohol, dioxane, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide or water) affords the carboxylic acids which can then be converted to esters 7c by treating with an alkyl alcohol, preferably methanol or ethanol, in the presence of an acid catalyst, e.g., hydrochloric acid, sulfuric acid or -toluenesulfonic acid at temperatures ranging from 0 °C to the reflux temperature of the solvent.
  • an oxidizing reagent such as potassium permanganate, potassium peroxymonosulf
  • Scheme 16 illustrates how pyrazole aldehydes of Formula .33 (wherein X 1 is halogen) can be made by chlorination and formylation of hydroxypyrazoles of Formula 34 in one step under Nilsmeier conditions using a mixture of a phosphorus oxyhalide and N,N-dimethyl- formamide.
  • substituted hydroxy pyrazoles of Formula 34 can be prepared by condensing a substituted hydrazine of Formula 36 with a beta-ketoester of Formula 35 or a methoxyacrylate of Formula 37. In some of these condensations, mixtures of Formula 34 with its isomer are obtained, from which the isomers can be separated by conventional techniques such as chromatography and crystallization.
  • the substituted methoxy acrylates of Formula 37 are made by methylation of the beta-ketoesters of Formula 35 with dimethyl sulfate or methyl iodide in the presence of base (e.g., a alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide.
  • base e.g., a alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine
  • Substituted pyrazole esters of Formula ,8c (wherein Y is oxygen and R 5 J is CO 2 R 52 ) can also be made from hydroxy pyrazole esters of Formula 39 via alkylation as shown in Scheme 18.
  • substituted hydroxy pyrazole esters of Formula 39 can be made by condensing a substituted hydrazine of Formula 36 with a substituted acylmalonate of Formula 41 (where Q is O or S, and R 5 is other than halogen) or a substituted malonate of Formula 42 (where Q is O or S, and R 5 is other than halogen).
  • a substituted acylmalonate of Formula 41 where Q is O or S, and R 5 is other than halogen
  • a substituted malonate of Formula 42 where Q is O or S, and R 5 is other than halogen
  • Substituted malonates of Formula 42 are made by alkylation of acyl or thioacyl malonates of Formula 41 with dimethyl sulfate or methyl iodide in the presence of base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide.
  • base e.g., an alkali metal acetate, or carbonate such as sodium acetate or potassium carbonate.
  • Substituted malonates of Formula 42 are made by alkylation of acyl or thioacyl malonates of Formula 41 with dimethyl sulfate or methyl iodide in the presence of base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-
  • This method uses a halogenating reagent such as a halogen (e.g., bromine, chlorine or chloroiodide) or a halosuccinimide neat or in an suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide at temperatures ranging from 0 to 150 °C.
  • a halogen e.g., bromine, chlorine or chloroiodide
  • a halosuccinimide neat or in an suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide
  • Halogen-substituted pyrazole nitriles of Formula 7c (wherein R 51 is C ⁇ and X 1 is halogen) can be made from corresponding amino pyrazole nitriles of Formula 43 via diazotization in the presence of a halogen source in an appropriate solvent as shown in Scheme 21.
  • Scheme 21
  • the usual diazotization method involves treating a stirred mixture of a compound of Formula 43 with an alkyl nitrite (e.g., iso-amyl or tert-butyl nitrite) and copper(I) or copper (11) halide in a solvent such as acetonitrile at temperatures ranging from 0 °C to the reflux temperature of the solvent to afford the corresponding pyrazole nitrile of Formula 7c.
  • an alkyl nitrite e.g., iso-amyl or tert-butyl nitrite
  • copper(I) or copper (11) halide in a solvent such as acetonitrile at temperatures ranging from 0 °C to the reflux temperature of the solvent to afford the corresponding pyrazole nitrile of Formula 7c.
  • substituted aminopyrazole nitriles of Formula 43 can be made by condensing a substituted hydrazine of Formula 36 with a substituted acyl or thioacyl malonitrile of Formula 44 (where Q is O or S, and R 5 is other than halogen) or a substituted malonitrile of Formula 45 (where Q is O or S, and R 5 is other than halogen).
  • a substituted hydrazine of Formula 36 with a substituted acyl or thioacyl malonitrile of Formula 44 (where Q is O or S, and R 5 is other than halogen) or a substituted malonitrile of Formula 45 (where Q is O or S, and R 5 is other than halogen).
  • mixtures of Formula 43 with its isomer are obtained, which can be separated by conventional techniques such 'as chromatography and crystallization.
  • condensations are generally carried out in a solvent such as alcohol, acetonitrile, toluene, xylene or glacial acetic acid, optionally in the presence of base (e.g., an alkali metal acetate or carbonate such as sodium acetate or potassium carbonate) or an acid catalyst (e.g., acetic acid).
  • a solvent such as alcohol, acetonitrile, toluene, xylene or glacial acetic acid
  • base e.g., an alkali metal acetate or carbonate such as sodium acetate or potassium carbonate
  • an acid catalyst e.g., acetic acid
  • Substituted malononitriles of Formula 45 can be made by alkylation of acyl or thioacyl malononitriles of Formula 44 with dimethyl sulfate or methyl iodide in the presence of base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide.
  • base e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine
  • Halogen-substituted aminopyrazole nitriles of Formula 43 can be made from aminopyrazole nitriles of Formula 43 (wherein R5 is H) via halogenation using conditions analogous to the halogenation method shown for Formulae 39 in Scheme 20.
  • compounds of Formulae 4d and 8d can also be prepared by first halogenating an isothiazole of Formula 46 to form a haloisothiazole intermediate of Formula 47.
  • the haloisothiazole intermediate of Formula 47 is subjected to a palladium- catalyzed carbonylation reaction to prepare a compound of Formula 4d (R 51 is CO 2 H) or Formula 8d (R 51 is CO 2 R 52 or C(O)NH 2 ), or a cyanation reation using either copper(I) cyanide or palladium catalysis to prepare a compound of Formula 8d wherein R 51 is CN.
  • an isothiazole of Formula 46 is treated with a halogenating agent such as a halosuccinimide or a halogen (e.g., bromine, chlorine or chloroiodide) neat or in a suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide at temperatures ranging from 0 to 150 °C to form the corresponding haloisothiazole of Formula 47.
  • a halogenating agent such as a halosuccinimide or a halogen (e.g., bromine, chlorine or chloroiodide) neat or in a suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide
  • the compound of Formula 47 can then be treated with carbon monoxide in the presence of palladium catalyst and also a base such as potassium carbonate or triethylamine in a solvent such as methanol or N,N-dimethylformamide selected in view of whether a carboxylic acid (R 51 is CO 2 H), an ester (R 51 is CO 2 R 52 ) or an amide (R 51 is C(O)R 52 is desired for Formula 4d/8d, according to general methods described by R. Skoda-Foldes and L. Kollar, Current Organic Chemistry 2002, 6(12), 1097-1119; E.-I. ⁇ egishi, Background for Part NI. Handbook of Organopalladium Chemistry for Organic Synthesis 2002, 2, 2309- 2311; M.
  • a base such as potassium carbonate or triethylamine
  • a solvent such as methanol or N,N-dimethylformamide
  • the intermediate of Formula 47 can also be converted by palladium-catalyzed cyanation to the corresponding compound of Formula 8d wherein R 51 is C ⁇ according to general methods described in Synthesis 2004, (1), 23-25; Synlett 2003, 14, 2237-239; and European Journal of Inorganic Chemistry 2003, 19, 3513-3526.
  • the catalyst system typically comprises tris(dibenzylideneacetone)dipalladium(0), tri-tert-butylphosphine or l,l'-bis(diphenylphosphino)ferrocene and zinc powder
  • zinc cyanide is used as the cyanide source
  • the solvent is N,N-dimethylformamide or N,N-dimethylacetamide
  • the reaction temperature ranges from 25 to 130 °C.
  • the intermediate of Formula 47 can be converted to the compound of Formula 8d wherein R 51 is CN by reaction with copper(I) cyanide at temperatures ranging from 185 to 250 °C according to a general method described in J. Heterocyclic Chem. 1988, 25, 235.
  • Isothiazoles of Formula 46 are known or can be prepared by a variety of methods known in the literature; see, for example, Rodd's Chemistry of Carbon Compounds, 2nd Ed., Vol. IN, Part C, Elsevier 1986, edited by S. Coffey and M. F. Ansell, pp. 356-376; Advances in Heterocyclic Chemistry, Nol. 14, Academic Press, 1972, edited by A. R. Katritzky and A. J. Boulton, pp. 2-43; Comprehensive Heterocyclic Chemistry II, First Ed., Nol. 3, Elsevier Science, 1996, edited by A. R. Katritzky et al., pp. 319-372; and U.S. Patent 6,083,879.
  • Compounds of Formulae 4d and 8d wherein R 51 is CO 2 H or CO 2 R 52 can also be prepared from corresponding haloisothiazoles of Formula 48 according to the method of Scheme 24.
  • a haloisothiazole of Formula 48 in an ethereal solvent such as ethyl ether or tetrahydrofuran is reacted with an alkylmagnesium halide, such as ethyl or methyl magnesium bromide or chloride, at temperatures not exceeding 5 °C or reacted with an organolithium reagent such as lithium diisopropylamide, n-butyllithium, sec-butyllithium or tert-butyllithium at temperatures typically below -70 °C to form a Grignard or lithio intermediate, respectively, according to the general methods of Synthetic Communications 1995, 25 ⁇ 9), 1383-89, U.S.
  • an alkylmagnesium halide such as ethyl or methyl magnesium bromide or chloride
  • an aminoisothiazole of Formula 50 is halogenated by contact with a halogen (e.g., bromine, chlorine or chloroiodide) or a halosuccinimide neat or in an suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide at temperatures ranging from 0 to 150 °C to provide the corresponding aminohalothiazole of Formula 51.
  • a halogen e.g., bromine, chlorine or chloroiodide
  • a halosuccinimide neat or in an suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide
  • the aminohalothiazole of Formula 51 is then diazotized using an alkyl nitrite (e.g., isoamyl nitrite or tert-butyl nitrite) and a copper(I) or copper(II) halide in a solvent such as acetonitrile at temperatures ranging from 0 °C to the reflux temperature of the solvent to provide the dihaloisothiazole of Formula 52 according to the general method of Synthetic Communications 1997, 27(12), 2181-2191. Then using reaction conditions analogous to the method of Scheme 4, the dihaloisothiazole of Formula 52 is contacted with a compound of Formula 6 in the presence of base and a solvent to provide the compound of Formula 48. As shown in Scheme 26, intermediates of Formula 52 can also be prepared from isothiazoles of Formula 53.
  • a isothiazole of Formula 53 is lithiated at or below -70 °C in an ethereal solvent such as ethyl ether or tetrahydrofuran by contact with an organolithium reagent such as lithium diisopropylamide, n-butyllithium or sec-butyllithium according to the general method of Heterocycles 1995, 41 ⁇ 3), 533-93.
  • organolithium reagent such as lithium diisopropylamide, n-butyllithium or sec-butyllithium according to the general method of Heterocycles 1995, 41 ⁇ 3), 533-93.
  • the resulting 5-lithio intermediate is then reacted with the appropriate halogen of Formula 54 to provide the haloisothiazole of Formula 55.
  • the haloisothiazole of Formula 55 is then halogenated to provide the compound of Formula 52 using conditions analogous to those described for the conversion of the compound of Formula 50 to the compound of Formula 51 in Scheme 25.
  • isothiazoles of Formula 7d wherein R 51 is CO 2 H or CO 2 R 52 and X 1 is S(O) 2 CH 3 can also be prepared from isothiazoles of Formula 53.
  • an isothiazole of Formula 53 is lithiated as described for the conversion of the compound of Formula 53 to the compound of Formula 55 in Scheme 26.
  • the resulting 5-lithio intermediate is then contacted with dimethyl disulfide to form the methylthioisothiazole of Formula 54.
  • the methylthioisothiazole of Formula 54 is then lithiated using lithium diisopropylamide, and the resulting 4-lithio intermediate is reacted with carbon dioxide or a chloroformate of Formula 49 to provide the methylthioisothiazole of Formula 55 wherein R 51 is CO 2 H or CO 2 R 52 , respectively.
  • the methylthio group of the compound of Formula 55 is then oxidized to methylsulfonyl to provide the compound of Formula 7d wherein R 51 is CO 2 H or CO 2 R 52 and X 1 is S(O) 2 CH 3 .
  • the oxidation is conducted using at least two equivalents of an oxidizing agent such as 3-chloroperoxybenzoic acid (MCPBA) or potassium peroxymonosulfate (e.g., Oxone®) in an inert solvent in which the oxidizing agent is soluble (e.g., dichloromethane for MCPBA, water for potassium peroxymonosulfate) at temperatures ranging from 0 °C to room temperature.
  • MCPBA 3-chloroperoxybenzoic acid
  • potassium peroxymonosulfate e.g., Oxone®
  • an inert solvent e.g., dichloromethane for MCPBA, water for potassium peroxymonosulfate
  • Benzylamines of Formula 2 that are not commercially available can be prepared by a wide variety methods known to those skilled in the art.
  • compounds of Formula 2a (hydrochloride salts of compounds of Formula 2 wherein R, R 1 and R 2 are hydrogen) can be prepared using the method described in J. Med. Chem. 1984, 27(9), 1111-1118.
  • compounds of Formula 60 are reacted with hexamethylenetetramine (61) in a suitable solvent such as dichloromethane or trichloromethane to provide compounds of Formula 2a after hydrolysis with aqueous acid.
  • X 8 is a nucleophilic reaction leaving group such as Cl, Br, -OS(0) CH 3 or -OS O ⁇ -p ⁇ Hg-CHg.
  • compounds of Formula 2b can be prepared by reacting compounds of Formula 60 with a potassium salt of phthalimide (62) followed by reaction with either aminoethanol or hydrazine in an alcohol solvent to provide the desired aminomethyl intermediates of Formula 2b.
  • X 9 is a nucleophilic reaction leaving group such as Cl, Br, -OS(0) Me or -OS(0) 2 -p-C4Hg-CH 3 .
  • Compounds of Formula 60 can be prepared from the corresponding benzyl alcohols by methods well known in the art (e.g., treatment with POCl 3 for X 9 being Cl, treatment with PBr 3 for X 9 being Br, treatment with ClS(O) 2 Me or ClS(O) 2 -p-C 4 H 6 -CH 3 for X 9 being the corresponding sulfonates).
  • the benzyl alcohols can be prepared by reduction of the corresponding carboxylic acids, carboxylic esters or carboxamides using methods well known in the art (e.g., treatment of carboxylic acids with diborane, treatment with esters or carboxamides with lithium aluminum hydride in ethereal solvents such as tetrahydrofuran, dimethoxyethane or diethyl ether).
  • compounds of Formula 2b can also be prepared by reacting nitriles of Formula 64 with a suitable reducing reagent such as diborane, lithium aluminum hydride or hydrogen with palladium on carbon at temperatures ranging from 0 to 100 °C.
  • Suitable solvents for the reaction are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and for hydrogenation, alcohols such as ethanol or isopropanol.
  • ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether
  • hydrocarbons such as toluene or benzene
  • alcohols such as ethanol or isopropanol.
  • substituted benzylamines of Formula 2c can be prepared from aldehydes by the method of Hart et al. as described in J. Org. Chem. 1983, 48(3), 289-298.
  • Lithium bis(trimethylsilyl)amide (66) which can be prepared by treatment of 1,1,1,3,3,3-hexamethyldisilazane with a strong base such as lithium diisopropylamide or 72-butyllithium, is reacted with an aldehyde of Formula 65 in a suitable solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from -78 °C to room temperature.
  • a Grignard reagent of Formula 67 then provides an amine of Formula 2c.
  • Benzylamines of Formula 2c wherein R 2 is CN can also be prepared from aldehydes of Formula 65 as described by M. Wakselman et al. in Bioorg. Med. Chem. 2001, 9(5), 1175— 1183.
  • benzylamines having a chiral center denoted by the asterisk (*) in Formula 2d can be prepared enantiomerically enriched with the depicted configuration by the reduction of chiral imines of Formula 68 using the methods analogous to those described U.S. Patent Application Publication 2002/103,400 or Organic Letters 2003, 5(7), 1007-1010.
  • Scheme 32
  • the chiral imine of Formula 68 comprises a chiral auxiliary group, which transfers chirality to the new chiral center created during reduction.
  • the chiral auxiliary is chosen to provide the new center with the absolute configuration depicted for Formula 2d, as this configuration provides greater herbicidal activity to the compounds of Formula I. As referred to in the context of the present disclosure and claims this configuration is identified as the S-configuration.
  • Examples of reducing reagents useful for reducing the imine include sodium borohydride and lithium aluminum hydride.
  • the chiral auxiliary is removed after the imine is reduced, either by reduction or hydrolysis depending on the choice of chiral auxiliary.
  • a chiral benzyl amine enriched with configuration shown in Formula 2d can be prepared by reducing an imine of Formula 69 with one of the many chiral reducing agents known in the art.
  • chiral reducing agents include enzymes (see, for example, PCT Patent Application Publication WO 03/048151) and chiral complexes (see, for example, J. Chem. Soc, Perkin Trans. 1, 1990, 7, 1859-63 and X. Zhang et al. J. Org. Chem. 2003, 68, 4120-22).
  • R 60 is H or groups such as OH, C ⁇ -C 3 alkoxy, C(O)CH 3 , SiMe 3 or optionally substituted phenyl.
  • the chiral reducing complex or enzyme is chosen to provide a benzylamine enriched with the absolute S-configuration depicted for Formula 2d.
  • Chiral amines of Formula 2d can also be prepared by additional methods taught by L. Storace et al. in Organic Process Research & Development 2002, 6, 54-63.
  • the benzylamines of Formula 2d are obtained enantiomerically pure, so coupling according to the methods of Schemes 1 and 2 provides the corresponding compounds of Formula I also in enantiomerically pure form. Methods are well known in the art for separating pure enantiomers of chiral amines from enantiomerically enriched or even racemic mixtures.
  • Step B Preparation of 2-chloro-N-[(4-fluorophenyl)methyl]-6-methyl-4-propoxy- 3-pyridinecarboxamide
  • 2-chloro-6-methyl-4-propoxy-3-pyridinecarboxylic acid i.e. product of Step A
  • thionyl chloride 2.5 mL
  • the excess thionyl chloride was evaporated in vacuo, and then dichloromethane was added and evaporated in vacuo.
  • the residual oil was dissolved in dichloromethane (approximately 3 mL) and added to a solution of 4-fluorobenzene- methanamine (0.193 g) in dichloromethane (10 mL). An molar excess of PS-DMAP was added, and the reaction mixture was shaken at room temperature overnight and filtered, and the solvent was evaporated in vacuo. The residual oil was triturated with 1-chlorobutane- hexanes (approximately 1:1) to provide the title product, a compound of the present invention, as a white solid (0.316 g).
  • the residual oil was dissolved in dichloromethane (approximately 2 mL) and added to a solution of ( ⁇ S)-4-methoxy- ⁇ -methylbenzenemethanamine (79.2 mg) in dichloromethane (3 mL). A molar excess of PS-DMAP was added, and the reaction mixture was shaken at room temperature overnight. The reaction mixture was then filtered, and the solvent was evaporated in vacuo. The residual oil was triturated with 1-chlorobutane-hexanes (approximately 1:1) to provide the title product, a compound of the present invention, as a white solid (92.3 mg) melting at 110-111 °C.
  • Step A Preparation of 2,4-dichloro-N-[(4-fluorophenyl)methyl]-6-methyl-3-pyridine- carboxamide
  • thionyl chloride 25 mL
  • dichloromethane was added and evaporated in vacuo.
  • Step B Preparation of 2-chloro-N-[(4-fluorophenyl)methyl]-6-methyl- 4-(l-methylethoxy)-3-pyridinecarboxamide To a solution of 2-propanol (81 ⁇ L) in DMF (2 mL) was added sodium hydride
  • Step A Preparation of 2,4-bromo-N-[(4-fluorophenyl)methyl]-6-methyl- 3-pyridinecarboxamide
  • phosphorus oxybromide 10.0 g
  • the reaction mixture was heated at reflux for 1.5 h.
  • the reaction mixture was cooled, carefully quenched with water and then extracted with dichloromethane (2x).
  • the combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried (MgSO 4 ) and filtered, and the solvent was evaporated in vacuo.
  • Step B Preparation of 2-bromo-N-[(4-fluoro ⁇ henyl)methyl]-6-methyl-4-propoxy- 3-pyridinecarboxamide
  • 2,4-dibromo-N-[(4-fluorophenyl)methyl]-6-methyl-3- ⁇ yridinecarboxamide i.e. the product of Step A
  • 1-propanol 0.10 mL was added, and the mixture was heated at 80 °C overnight.
  • the reaction mixture was cooled, poured into water and extracted with ethyl acetate (3x).
  • the combined ethyl acetate extracts were washed with water (3x), brine, and then dried (MgSO 4 ), and the solvent was evaporated in vacuo to leave the crude product as a brown oil.
  • the crude product was combined with the crude product from a second 500-mg run and purified by silica gel chromatography using as eluant a solvent varying from 1:1 ethyl acetate-hexanes to 100% ethyl acetate.
  • the product-containing fractions were combined and the solvent was evaporated in vacuo.
  • the residue was triturated with 1-chlorobutane-hexanes to provide the title compound as a light yellow solid (309 mg).
  • Step A Preparation of ethyl 2,5-dihydro-l-methyl-5-oxo-lH-pyrazole-4-carboxylate
  • Step B Preparation of ethyl 3-chloro-2,5-dihydro-l-methyl-5-oxo-lH-pyrazole- 4-carboxylate
  • ethyl 2,5-dihydro- l-methyl-5-oxo-lH-pyrazole-4-carboxylate i.e. the product of Step A
  • N-chlorosuccinimide (12.3 g, 92.5 mmol
  • Step C Preparation of ethyl 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylate To a stirred solution of ethyl 3-chloro-2,5-dihydro-l-methyl-5-oxo-lH-pyrazole-
  • Step D Preparation of 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylic acid
  • ethyl 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylate i.e. the product of Step C
  • aqueous sodium hydroxide 50 wt%, 1.3 g
  • Step E Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-l-methyl-5- propoxy- lH-pyrazole-4-carboxamide
  • 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylic acid i.e. the product of Step D
  • dichloromethane 20 mL
  • oxalyl chloride 1.5 g, 11.5 mmol
  • NN-dimethylformamide 2 drops
  • Step B Preparation of l-methyl-5-propoxy-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylic acid
  • sodium hydride (0.18 g, 4.5 mmol
  • N,N-dimethylformamide 10 mL
  • ⁇ -propyl alcohol 0.2 mL, 2.5 mmol
  • the resulting mixture was stirred for 0.5 hours, and then a solution of methyl 5-chloro-l-methyl-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylate (i.e.
  • Step A the product of Step A) (0.485 g, 2.0 mmol) in N,N-dimethylformamide (5 mL) was added slowly so that the temperature did not rise above 5 °C. The reaction was stirred overnight at room temperature. The solvent was removed in vacuo, and the resulting residue was added to a mixture of aqueous sodium hydroxide solution (2 ⁇ , 5 mL) and tetrahydrofuran (5 mL) and stirred for 2 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (15 mL).
  • Step C Preparation of N-[(2,4-difluorophenyl)methyl]-l-methyl-5-propoxy- 3-(trifluoromethyl)-lH-pyrazole-4-carboxamide To a solution of l-methyl-5-propoxy-3-(trifluoromethyl)-lH-pyrazole-4-carboxylic acid (i.e.
  • Step B) the product of Step B) (0.10 g, 0.4 mmol) in N,N-dimethylformamide (5 mL), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.084 g, 0.44 mmol), 1-hydroxybenzotriazole (0.059 g, 0.44 mmol) and N,N-diisopropylethylamine (0.129 g, 1.0 mmol) were added. The resulting reaction mixture was stirred at room temperature for 0.5 h.
  • Step A Preparation of l-methyl-5-(2-propynyloxy)-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylic acid
  • sodium hydride 0.18 g, 38.25 mmol
  • N,N-dimethylformamide 20 mL
  • propargyl alcohol 1.143 g, 20.4 mmol
  • the reaction mixture was stirred for 0.5 h, and then a solution of methyl 5-chloro-l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxylate (i.e.
  • Step B Preparation of N-[(lS)-l-(4-fluorophenyl)ethyl]-l-methyl-5-(2-propynyloxy)- 3-(trifluoromethyl)-lH-pyrazole-4-carboxamide To a solution of l-methyl-5-(2-propynyloxy)-3-(trifluoromethyl)-lH-pyrazole-
  • Step A Preparation of 3,5-dichloro-N-[(4-fluorophenyl)methyl]-4-isothiazole- carboxamide
  • 3,5-dichloro-4-isothiazolecarboxylic acid prepared according to the method of W.R. Hatchard, J. Org. Chem. 1964, 29, 660-665
  • thionyl chloride 3 mL
  • the reaction mixture was concentrated to leave the intermediate acid chloride as an oil.
  • the acid chloride was dissolved in dichloromethane (3 mL) under nitrogen atmosphere, and the solution was cooled to 0 °C.
  • Triethylamine (230 mg, 2.27 mmol) was added, followed by dropwise addition of a solution of 4-fluorobenzylamine (1 mL) in dichloromethane (1 mL) so that the temperature remained below 5 °C.
  • the stirred reaction mixture was maintained below 5 °C for 10 minutes more, and was then diluted with water and dichloromethane.
  • the layers were separated and the organic layer was washed with water, brine, dried (MgSO 4 ) and concentrated to provide the title compound as a yellow solid (0.6 g).
  • the solid was slurried in hexanes and collected under filtration to provide the title compound as a solid (215 mg) melting at 146-147 °C.
  • Step B Preparation of 3-chloro-N-[(4-fluorophenyl)methyl]-5-propoxy- 4-isothiazolecarboxamide Sodium hydride (55%, 51 mg, 1.18 mmol) was added to a stirred solution of 1-propanol (65 mg, 1.08 mmol) in N,N-dimethylformamide (2 mL) in a scintillation vial under nitrogen atmosphere. After 10 minutes hydrogen evolution was complete.
  • Step A Preparation of 5-(methylthio)-3-(trifluoromethyl)-4-isothiazolecarboxylic acid
  • Ethyl 5-(methylthio)-3-(trifluoromethyl)-4-isothiazolecarboxylate (prepared according to method of U.S. Patent 5,324,837, example 5A; 500 mg, 1.84 mmol) was stirred in mixture of ethanol (9 mL) and water (5 mL). Potassium carbonate (2.0 g, 14.56 mmol) was added, and the reaction mixture was stirred for 3 h. Then the pH was adjusted below 2 by addiing aqueous hydrochloric acid (1 ⁇ ).
  • Step B Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methylthio)-3-(trifluoro- methyl)-4-isothiazolecarboxamide
  • a mixture of 5-(methylthio)-3-(trifluoromethyl)-4-isothiazolecarboxylic acid (i.e. the product of Step A) (700 mg, 2.88 mmol) and thionyl chloride (9 mL) was heated at reflux under nitrogen atmosphere for 4 h. The reaction mixture was concentrated to leave the intermediate acid chloride as a solid. The acid chloride was dissolved in dichloromethane
  • Step A Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methylsulfonyl)- 3-(trifluoromethyl)-4-isothiazolecarboxamide N-[(lS)-l-(4-Chlorophenyl)ethyl]-5-(methylthio)-3-(trifluoromethyl)-4-isothiazole- carboxamide (i.e. the product of Example 9, Step B) (100 mg, 0.26 mmol) was dissolved in dichloromethane (4 mL) under nitrogen atmosphere.
  • the product was purified by flash column chromatography using a Supelco (division of Sigma-Aldrich Co., 595 North Harrison Road, Bellefonte, PA 16823, U.S.A.) DSC-Si SPE Tube prepacked with 5 g of silica gel (50 ⁇ m particle diameter, 70 A pore size) and as eluant 5% ethyl acetate - 95% hexanes, followed by 10% ethyl acetate - 90% hexanes, and then 20% ethyl acetate - 80% hexanes to obtain fractions containing the desired product (which is slightly more polar than the starting material).
  • Supelco division of Sigma-Aldrich Co., 595 North Harrison Road, Bellefonte, PA 16823, U.S.A.
  • Step B Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(l-methylethoxy)- 3-(1rifluoromethyl)-4-isothiazolecarboxamide
  • Sodium hydride 55%, 6 mg, 0.121 mmol
  • 2-propanol 0.1 mL, 1.3 mmole
  • N,N-dimethylformamide 0.5 mL
  • N-[(lS)-l-(4- chlorophenyl)ethyl]-5-(methylsulfonyl)-3-(trifluoromethyl)-4-isothiazolecarboxamide i.e. the product of Step A
  • 50 mg, 0.12 mmol dissolved in N,N-dimethylformamide (1.0 mL) was added to the reaction mixture.
  • the reaction mixture was stirred at room temperature for 20 minutes before being diluted with water and extracted with diethyl ether (2x).
  • the combined organic extracts were washed with water (3x), brine, dried ( ⁇ a 2 S ⁇ 4) and concentrated to leave the title product, a compound of the present invention, as as a solid (20 mg) melting at 144-145 °C.
  • bromotrimethylsilane (19.3 mL, 22.4 g, 146 mmol) was added dropwise while keeping the temperature of the reaction mixture below 10 °C. After warming to room temperature, the solution was heated at 30 °C overnight. The resulting precipitate was collected by filtration and dried to provide the title compound as a white solid (12.98 g), melting at 166-167 °C.
  • Step B Preparation of methyl 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridine- carboxylate
  • Step C Preparation of 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridinecarboxylic acid
  • Step D Preparation of 2-bromo-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl- 4-(l-methylethoxy)-3-pyridinecarboxamide) To 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridinecarboxylic acid (i.e.
  • reaction mixture was then filtered to remove the resin, and hydrochloric acid (1 N, 4 mL) was added.
  • the resulting mixture was dried by filtering through a Narian Chem Elut CE1010 column containing diatomaceous filter aid using dichloromethane as eluant, and the solvent was evaporated in vacuo.
  • Trituration with 7 ⁇ -BuCl provided a solid, which was collected by filtration, washed with a small amount of rc-BuCl, and dried to provide the title product, a compound of the present invention, as a white solid (86 mg) melting at 157- 159 °C.
  • Step A2 Alternative preparation of 3-chloro-5-propoxypyridine
  • a solution of 3,5-dichloropyridine (10 g, 67 mmol) in N,N-dimethylformamide (60 mL) was treated with sodium hydride (60% in mineral oil, 5.36 g, 130 mmol). After the reaction mixture was cooled to 0 °C, n-propanol (6.09 g, 100 mmol) was added. The mixture was heated at 60 °C for 1 h and then cooled to 23 °C. The mixture was quenched with water (100 mL) and extracted with ethyl acetate (3 x 100 mL).
  • Step B Preparation of 3-chloro-5-propoxy-4-pyridinecarboxylic acid To a solution of diisopropylamine (7.37 g, 72 mmol) in tetrahydrofuran cooled to
  • Step C Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-propoxy- 4-pyridinecarboxamide
  • 3-chloro-5-propoxy-4-pyridinecarboxylic acid i.e. the product of Step C
  • thionyl chloride 30 mL, 415 mmol
  • the resulting mixture was heated at 60 °C for 2 h.
  • the solution was cooled and evaporated under reduced pressure to leave an oil. This residue was dissolved in tetrahydrofuran (50 mL).
  • Step A Preparation of 3-chloro-5-(methoxymethoxy)pyridine
  • acetonitrile 60 mL
  • chloromethyl methyl ether 3.11 g, 39 mmol
  • potassium carbonate 10.78 g
  • the mixture was heated at 60 °C for 18 h and then diluted with water (100 mL).
  • the aqueous layer was extracted with ethyl acetate (4 x 100 mL).
  • the combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure to leave the title compound as a yellow oil (5.5 g).
  • !H ⁇ MR (CDC1 3 ) ⁇ 3.49 (s, 3H), 5.30 (s, 2H), 7.42 (s, IH), 8.26 (s, IH), 8.31 (s, IH).
  • Step B Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methoxy- methoxy)-4-pyridinecarboxamide
  • diisopropylamine 7.37 g, 72 mmol
  • tetrahydrofuran 30 mL
  • n-butyllithium 29.14 mL, 73 mmol
  • the mixture was stirred at this temperature for 30 minutes.
  • 3-chloro-5-(methoxymethoxy)pyridine i.e.
  • Step A the product of Step A) (5.5 g, 32 mmol) dissolved in tetrahydrofuran (10 mL) was added. After stirring at -70 °C for 1.5 h, l-chloro-4-[(lS)-l-isocyanatoethyl]benzene (5.7 g, 32 mmol) dissolved in tetrahydrofuran (10 ml) was added. The reaction mixture was allowed to warm to 23 °C and was then diluted with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried (MgSU4) and evaporated under reduced pressure.
  • Step A Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-hydroxy- 4-pyridinecarboxamide
  • 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methoxymethoxy)- 4-pyridinecarboxamide i.e. the product of Example 14, Step B
  • a solution of hydrochloric acid in ether (1 ⁇ , 45 mL).
  • Step B Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-[(2-chloro- 2-propenyl)oxy]-4-pyridinecarboxamide To a solution of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-hydroxy-4-pyridine- carboxamide (i.e.
  • Step A the product of Step A) (0.3 g, 1 mmol) in acetonitrile (10 mL) was added 2,3-dichloro-l-propene (0.106, 1 mmol) followed by potassium carbonate (0.251 g).
  • the mixture was treated with sodium iodide (30 mg) and stirred at 23 °C for 18 h.
  • the mixture was extracted with ethyl acetate (2 x 50 mL).
  • the combined organic layers were dried (MgSU4) and evaporated under reduced pressure.
  • the residue was subjected to flash chromatography on silica gel using as eluant a solvent gradient ranging from dichloromethane (100 %) to ethyl acetate-dichloromethane (50/50).
  • R is H; R 1 is H; R 2 is H; R 6 is CH 3 ; R 5 is Cl; Y is O.
  • R is H; R 1 is H; R 2 is H; R 6 is CH 3 ; R 5 is Cl; Y is 0.
  • R is H; R 1 is H; R 2 i s H; R 6 is CH 3 ; R 5 is Br; Y is O.
  • R is H; R 1 is H; R is H; R° is CH 3 ; R 3 is Br; Y is 0.
  • R is H; R 1 is H; R 2 is CH 3 ; R 5 is Cl; R 6 is CH 3 ; Y is 0.
  • R is H; R 1 is H; R 2 is CH 3 ; R 5 is Cl; R 6 is CH 3 ; Y is O.
  • R is H; R 1 is H; R 2 is CH 3 ; R 5 is Cl; R 6 is H; Y is 0.
  • R is H; R 1 is H; R 2 1 s CH 3 ; R 5 is Cl; R 6 ij H; Y is O.
  • R is H; R 1 is H; R 2 is CH 3 ; R 5 is Cl; R 6 is H; Y is 0.
  • R is H; R 1 is H; R 2 i s H; R 5 is Cl; R 6 is H , Y is 0.
  • CH(CH 3 ) 2 4-F CH(CH 3 ) 2 4-Cl CH(CH 3 ) 2 4-CN CH(CH 3 ) 2 4-SCH 3 CH(CH 3 ) 2 4-OCH3 CH(CH 3 ) 2 4-OCF 3 CH(CH 3 ) 2 3-OCH3 CH(CH 3 )CF 3 4-OCH3 CH(CH 3 )CF 3 3-OCH3 CH(CH 3 )CF 3 4-F
  • R is H; R 1 is H; R 2 i s CH 3 ; R 5 is F; R 6 is CH3; Y is 0.
  • R is H; R 1 is H; R 2 is H; R 5 is Cl; R 6 is CH 3 ; Y i 3 0.
  • CH 2 CH CH 2 2-F CH 2 CH 2 CH 2 CH 3 4-CH 2 OCH 3
  • CH 2 CH 2 SCH CH2 3-CF3 CH 2 CH 2 CH2CH 3 2-NHCH 3
  • CH 2 CH CHCH 2 OCH 3 2,3-di-Cl-4-OCH 3 CH 2 CH 2 CH3 4-NH-cyclopropyl
  • N C(H)CH 3 4-F CH 2 CH 2 CH 3 4-Si(CH 3 ) 3
  • N C(CH 3 ) 2 4-CN CH 2 CH(CH 3 ) 2 4-C 6 H 5
  • R is H; R 4 is CH 2 CH 2 CH 3 ; R 5 is Cl; R 6 is CH 3 ; Y is O.
  • R is H
  • R 4 is CH(CH 3 ) 2 ;
  • R 5 is Br;
  • R 6 is CH 3 ;
  • Y is O.
  • R is H; Rl is H; R 2 is CH 3 ; (R 3 ) m is 4-Cl; R 4 is CH 2 CH 2 CH 3 .
  • R5 R6 Y R R c
  • R is H; Rl is H; R 2 is CH 3 ; (R 3 ) m is 4-F; R 4 is CH 2 CH 2 CH 3 .
  • R is H; Rl is H; R 2 is CH 3 ; (R 3 ) m is 4-OCH 3 ; R 4 is CH 2 CH 2 CH 3 R 3 R6 R5 R6 s Cl CH 3 0 SCH 3 CH 3
  • R is H; R 1 is H; R 2 1 s CH 3 ; R 5 is Cl; R 6a is H; Y is O; q is 0.
  • R is H; Rl is H; R 2 is H; R 5 is Cl; R 6a is I I; Y is O; q is 0.
  • R is H; Rl is H; R 2 is H; R 5 is Cl; R ⁇ i s H; Y is O; q is 0.
  • R is H; Rl is H; R 2 i s CH 3 ; R 5 is Br; R 6a is H; Y is 0; q is 0.
  • R is H; Rl is H; R 2 i s CH 3 ; R 5 is Br; R 6a is H; Y is O; q is 0.
  • R is H; Rl is H; R 2 i s CH 3 ; R 5 is F; R 6a i£ > H; Y is O; q is 0.
  • R is H; Rl is H; R 2 is CH 3 ; R 5 is F; R 6a is H; Y i 3 O; q is 0.
  • R is H; Rl is H; R 2 is H; R 5 is Cl; R 6a is I 1; Y is 0; q is 0.
  • CH 2 CH CH 2 2-F CH 2 CH 2 CH 2 CH2 4-CH 2 OCH 3
  • R is H;
  • R 1 is H;
  • R 2 is H;
  • R 5 is Cl;
  • R 6a is H;
  • Y is 0;
  • q is 0.
  • CH 2 CH 2 SCH CH 2 3-CF 3 CH 2 CH 2 CH 2 CH 3 2-NHCH 3
  • CH 2 CH CHCH 2 OCH 3 2,3-di-Cl-4-OCH 3 CH 2 CH 2 CH 3 4-NH-cyclopropyl
  • N C(H)CH 3 4-F CH 2 CH 2 CH 3 4-Si(CH 3 ) 3
  • N C(CH 3 ) 2 4-CN CH 2 CH(CH 3 ) 2 4-C 6 H 5
  • R is H; Rl is H; R 2 is CH 3 ; R 5 is Cl; R 6a ⁇ s H; Y is S; q is O.

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Abstract

Compounds of Formula (I), and their N oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation. In Formula (I), J is (J-1), (J-2), (J-3) or (J-4); Y is O, S(O)n or NR8; and R, R1, R2, R3, R4, R5, R6, R6a, R7, R8, m, n and q are as defined in the disclosure. Also disclosed are compositions comprising the compounds of Formula (I) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (I). Also disclosed are compositions comprising a compound of Formula (I) and at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

Description

TITLE HERBICIDAL AMIDES FIELD OF THE INVENTION This invention relates to certain carboxamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation. BACKGROUND OF THE INVENTION 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, corn (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 which are more effective, less costly, less toxic, environmentally safer or have different modes of action. U.S. Patent 4,556,414 discloses herbicidal pyridinecarboxamides of Formula i.
Figure imgf000003_0001
wherein R1, R2 and R3 are H, lower alkyl, alkoxy or alkoxyalkyl; R4 is a carboxyl radical, optionally in the form of a salt or ester, or a cyano, cyanoalkyl or alkoxyalkyl radical; R5 and R6 are H, lower alkyl or cyano or together form a C2 to C5 alkylene radical; R7 is halogen, lower alkyl, lower alkoxy, lower alkenyl, alkenyloxy, nitro, cyano or amino, alkylenedioxy, n is 0 to 5; and I in the nitrogen-containing heterocyclic ring indicates 2 or 3 units of unsaturation, This reference does not disclose the compounds of the present invention or their herbicidal utility. SUMMARY OF THE INVENTION This invention is directed to a compound of Formula I including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides:
Figure imgf000004_0001
J-l J-2 J-3 J-4
Y is O, S(O)n or NR8;
R is H, C2-C5 alkoxymethyl, C2-C5 alkylcarbonyl or C2-C5 alkoxycarbonyl;
R1 is H or C1-C4 alkyl;
R2 is H, C!-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C2-C4 alkoxymethyl, cyano, C1-C4 alkoxy or C2-C4 alkoxycarbonyl; each R3 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, Cj-^ hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C -C4 alkynyloxy, C3-C4 haloalkynyl oxy, C2-C4 alkoxyalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, CJ-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, C1-C4 alkylamino, C2~Cg dialkylamino, C3-C6 cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C2-C6 alkylcarbonyl, C2-C5 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C -Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2-, R27S(O)2N(R28)-, phenyl, phenoxy, 5-membered heteroaromatic ring and 6-membered heteroaromatic ring, each phenyl, phenoxy, 5-membered heteroaromatic ring and 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R9; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -OCF2O-, -OCH2CH2O-, -OCF2CF2O- or -CH=CH-CH=CH-; R4 is Ci-Cjo ^Y1' C3-C7 cycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C5-C10 alkylcycloalkylalkyl, CJ-CJQ haloalkyl, C2-C1o cyanoalkyl, C2-C10 nitroalkyl, C3-C10 halocycloalkyl, C4-C10 halocycloalkylalkyl, C2-Cιn alkenyl, C2-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, C2-Cι0 alkoxyalkyl, C4-C10 (cycloalkyl)oxyalkyl, -CH (CH2)p}, C2-C10 haloalkoxyalkyl, C4-C10 alkenyloxyalkyl, C4-C10 haloalkenyloxyalkyl, C4-C10 alkynyloxyalkyl, C4-C10 haloalkynyloxyalkyl, C2-C10 alkylthioalkyl, C2-C10 alkylsulfinylalkyl, C2-C1() alkylsulfonylalkyl, C4-C10 (cycloalkyl)thioalkyl, Q -C10 alkenylthioalkyl, C4-C10 alkynylthioalkyl, C4-C10 alkoxyalkenyl, C4-C10 alkoxyalkynyl, C4-C10 alkylthioalkenyl, C4-C10 alkylthioalkynyl, C4-C10 trialkylsilylalkyl, -N=CR10R11 or -NR12R13; or R4 is C].-C6 alkyl substituted with C(O)R14, C(OR29)(OR30)R31, C(=NOR15)R16, NR1 R18 or phenyl optionally substituted with R19, R20 and R21; or R4 is phenyl optionally substituted with R22, R23 and R24;
R5 is H, halogen, C^-Cg alkyl, C1-C4 haloalkyl, C3-Cg cycloalkyl, C3-C6 halocycloalkyl, C2~C6 alkenyl, C3-Cg alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, Cj-04 alkylthio, C1-C4 haloalkylthio or C2-C5 alkoxycarbonyl;
R6 is H, halogen, cyano, C^-Cg alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 haloalkylthio;
R6a is Cι-C6 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl or C4-C7 cycloalkylalkyl; R7 is H, Cι-C6 alkyl, C1-C4 haloalkyl, C]-^ cyanoalkyl, C3-C6 alkenyl, C2-C4 haloalkenyl, C3-Cg alkynyl, C3-C4 haloalkynyl, C3-C6 cycloalkyl or C3-C halocycloalkyl;
R8 is H, C1-C4 alkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl; each R9 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C2-C4 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-C alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-C6 trialkylsilyl;
R10 is C-L-C4 alkyl; R11 is H or Cι-C2 alkyl; or
R10 and R11 are taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -(CH2)6-;
R12 is H or C1-C4 alkyl;
R13 is H, C1-C2 alkyl, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl; or R12 and R13 are taken together as -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- or -CH2CH(CH3)OCH(CH3)CH2-; R14 is H, C1-C4 alkyl or Ci-C4 alkoxy; R15 is H or Cι-C4 alkyl; R16 is H, C!-C4 alkyl or C1-C4 alkoxy; R17 is H or Ci-C4 alkyl; R18 is H, Cj-C2 alkyl, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl; or RI7 and R18 are taken together as -(CH2)4-, ~(CH2)5-, -CH2CH2OCH2CH2- or -CH2CH(CH3)OCH(CH3)CH2-; R19 and R22 are independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy; R20 and R23 are independently halogen, C]—C2 alkyl, C^fluoroalkyl, methoxy or methylthio; R21 and R24 are independently halogen; each R25 is independently H, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; each R26 is independently H or C]-C2 alkyl; or R .5 and R26 are taken together as ~(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- or -CH2CH(CH3)OCH(CH3)CH2-; each R27 is independently Cι-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl or C2-C4 ' dialkylamino; each R28 is independently H, C1-C4 alkyl, C1~C4 haloalkyl or C3-C6 cycloalkyl; R29 and R30 are independently C -C4 alkyl; or R29 and R3^ are taken together as -CH2CH2-, -CH(CH3)CH2- or -CH2CH2CH2-; RSMs H or Ci^ alkyl; m is 0, 1, 2, 3, 4 or 5; n is O or 1; p is 3 or 4; and q is O or 1; provided that: (a) the compound of Formula I is other than N-[[4-(4-ethoxyphenoxy)phenyl]methyl]- 5-methoxy-l,3-dimethyl-lH-pyrazole-4-carboxamide, N-[[4-(4-ethoxyphenoxy)- phenyl]methyl]-l,3-dimethyl-5-(l-methylethoxy)-lH-pyrazole-4-carboxamide, N-[[4-(4-ethoxyphenoxy)phenyl]methyl]-l,3-dimethyl-5-(2,2,2-trifluoroethoxy)- lH-pyrazole-4-carboxamide, 5-(cyclohexyloxy)-N-[[4-(4-ethoxyphenoxy)phenyl]- methyl]-l,3-dimethyl-lH-pyrazole-4-carboxamide, l-methyl-N-(phenylmethyl)- 5- [(phenylmethyl)amino] - lH-pyrazole-4-carboxamide, N- [ [4-( 1 , 1 -dimethylethyl)- phenyl]methyl]-l,3-dimethyl-5-phenoxy-lH-pyrazole-4-carboxamide, N-[(2-chlorophenyl)methyl-l,3-dimethyl-5-phenoxy-lH-ρyrazole-4-carboxamide, 1 , 1 -dimethylethyl 4- [ [ [(1 ,3 -dimethyl-5 -phenoxy- lH-pyrazol-4-yl)carbonyl] - amino]methyl]benzoate, N-(phenylmethyl)-4-[[3-(trifluoromethyl)phenyl]amino]- 3-pyridinecarboxamide, orN-(l,3-benzodioxol-5-ylmethyl)-3,5-bis(methylthio)-4- isothiazolecarboxamide; (b) when R4 is -Ν=CR1θR11 or -NR12R13, then Y is O or NR8; (c) when an R3 is CF3, then said CF3 is attached meta or para to the connection of the phenyl ring to the remainder of Formula I; (d) when an R3 is CF3 and attached meta to the connection of the phenyl ring to the remainder of Formula I, then the position on the phenyl ring ortho to both said CF3 and the connection of the phenyl ring to the remainder of Formula I is unsubstituted or substituted by R3 other than F, and the position on the phenyl ring meta to both said CF3 and the connection of the phenyl ring to the remainder of Formula I is unsubstituted or substituted by R3 other than F; and (e) when J is J-4, then R4 is other than phenyl optionally substituted with R22, R23 and R24. More particularly, this invention pertains to a compound of Formula I, including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof. This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula I and at least one of a surfactant, a solid diluent or a liquid diluent. 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 Formula I (e.g., as a composition described herein). This invention also relates to a herbicidal composition comprising a herbicidally effective amount of a compound of Formula I, an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener, and at least one of a surfactant, a solid diluent or a liquid diluent. DETAILS OF THE INVENTION As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having" or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus 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, process, method, article, or apparatus. Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, f-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. "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 CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH2O, (CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3)CH2O and CH2=CHCH2CH2O. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC≡CCH2O, CH3C≡CCH2O and CH3C≡CCH2CH2O. "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylthioalkyl" denotes alkylthio substitution on alkyl. Examples of "alkylthioalkyl" include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH3S(O), CH3CH2S(O), CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH3S(O)2, CH3CH2S(O)2, CH3CH2CH2S(O)2, (CH3)2CHS(O)2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Cyanoalkyl" denotes an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH2, NCCH2CH2 and CH3CH(CN)CH2. "Alkylamino", "dialkylamino", "alkenylthio", "alkenylsulfinyl", "alkenylsulfonyl", "alkynylthio", "alkynylsulfinyl", "alkynylsulfonyl", and the like, are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. Aromatic indicates that each of the ring atoms is essentially in the same plane and has a/7-orbital perpendicular to the ring plane, and in which (4n + 2) π electrons, when n is 0 or a positive integer, are associated with the ring to comply with Hiickel's rule. The term "heteroaromatic ring" includes fully aromatic heterocycles. The heteroaromatic rings can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. The 5- and 6-membered heteroaromatic rings described for R3 typically comprise 1 to 4 heteroatom ring members, the heteroatom members selected from 0-4 N, 0-1 O and 0-1 S atoms. Exhibit 1 shows examples of heteroaromatic rings; H-l through H-55 are to be construed as illustrative rather than limiting of the heteroaromatic rings within the scope of the present invention.
Figure imgf000009_0001
H-l H-2 H-3 H-4
Figure imgf000009_0002
H-5 H-6 H-7 H-8
Figure imgf000009_0003
H-9 H-10 H-l l H-12
Figure imgf000009_0004
H-13 H-14 H-15 H-16
Figure imgf000010_0001
-17 H-18 H-19 H-20
Figure imgf000010_0002
H-21 H-22 H-23 H-24
Figure imgf000010_0003
H-25 H-26 H-27 H-28
Figure imgf000010_0004
H-29 H-30 H-31 H-32
Figure imgf000010_0005
H-33 H-34 H-35 H-36
Figure imgf000010_0006
H-37 H-38 H-39 H-40
Figure imgf000011_0001
H-41 H-42 H-43 H-44
Figure imgf000011_0002
H-49 H-50 H-51 H-52
Figure imgf000011_0003
H-53 H-54 H-55 wherein each R41 is independently R9; R41a, R42 and R43 are independently H or R9; j is an integer from 0 to 3; and k is an integer from 0 to 2. References herein to R3 groups H-l through H-55 refer to those shown in Exhibit 1. One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair of electrons for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of 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 dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. N. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press. Molecular depictions drawn herein follow standard conventions for depicting stereochemistry. To indicate stereoconfiguration, bonds rising from the plane of the drawing and towards the viewer are denoted by solid wedges wherein the broad end of the wedge is attached to the atom rising from the plane of the drawing towards the viewer. Bonds going below the plane of the drawing and away from the viewer are denoted by dashed wedges wherein the narrow end of the wedge is attached to the atom further away from the viewer. Constant width lines indicate bonds with a direction opposite or neutral relative to bonds shown with solid or dashed wedges; constant width lines also depict bonds in molecules or parts of molecules in which no particular stereoconfiguration is intended to be specified. The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. The term "1-2 halogen" indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F3C, C1CH2, CF3CH2 and CF3CC12. The terms "haloalkenyl", "haloalkynyl", "haloalkoxy", "haloalkylthio", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkenyl" include (C1)2C=CHCH2 and CF3CH2CH=CHCH2. Examples of "haloalkynyl" include HC≡CCHCl, CF3C≡C, CC13G≡C and FCH2C≡CCH2. Examples of "haloalkoxy" include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O. Examples of "haloalkylthio" include CC13S, CF3S, CC13CH2S and C1CH2CH2CH2S. Examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of "haloalkylsulfonyl" include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2. The total number of carbon atoms in a substituent group is indicated by the "Cj-Cj" prefix where i and j are numbers from 1 to 10. For example, Cι-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. Examples of "alkylcarbonyl" include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH3)2CHOC(=O) and the different butoxy- or pentoxycarbonyl isomers. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can vary, when the number of said substituents is greater than 1, said substituents are independently selected from the group of defined substituents. When a group contains a substituent which can be hydrogen, for example R5 or R6, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R3)m wherein m may be 0, then hydrogen may be at the position even if not recited in the variable group definition. As used herein, the term "alkylating agent" refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term "alkylating" does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R4 and R6a. "-CH (CH2)p}" means
Figure imgf000013_0001
Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that 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. Accordingly, the present invention comprises compounds selected from Formula I, N-oxides and agriculturally suitable salts thereof. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form. In particular, when R1 and R2 of Formula I are different, then Formula I possesses a chiral center at the carbon atom to which they are commonly bonded. This invention comprises racemic mixtures. In addition, this invention includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula I' or I".
Figure imgf000014_0001
Included are the essentially pure enantiomers of Formula I' and Formula I". When enantiomerically enriched, one enantiomer is present in greater amounts than the other, and the extent of enrichment can be defined by an expression of enantiomeric excess ("ee"), which is defined as (2x-l)T00%, 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). When R1 is H and R2 is other than H, such as when R2 is CH3, the more herbicidally active enantiomer is believed to be Formula I'. When R1 is H and R2 is CH3, Formula I1 has the S configuration at the carbon atom to which R1 and R2 are commonly bonded. Preferably the 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. Of particular note are enantiomerically pure embodiments of the more active isomer. Compounds of Formula I can comprise additional chiral centers. For example, the substituents R2, R3, R , R5, R6, R6a and R7 may themselves contain chiral centers. This invention comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers. The agriculturally suitable salts of the compounds of the invention 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. The agriculturally suitable salts of the compounds of the invention also include those formed with strong bases (e.g., hydrides or hydroxides of sodium, potassium or lithium). One skilled in the art recognizes that because in the environment and under physiological conditions salts of the compounds of the invention are in equilibrium with their corresponding nonsalt forms, agriculturally suitable salts share the biological utility of the nonsalt forms. Embodiments of the present invention include: Embodiment 1. A compound of Formula I wherein Y is O. Embodiment 2. A compound of Formula I wherein n is 0. Embodiment 3. A compound of Formula I wherein R is H. Embodiment 4. A compound of Formula I wherein q is 0. Embodiment 5. A compound of Formula I wherein R1 is H. Embodiment 6. A compound of Formula I wherein R2 is H, cyano or C1-C4 alkyl. Embodiment 7. A compound of Embodiment 6 wherein R2 is H, cyano or CH3. Embodiment 8. A compound of Embodiment 7 wherein R2 is H or CH3. Embodiment 9. A compound of Embodiment 7 wherein R2 is H. Embodiment 10. A compound of Embodiment 7 wherein R2 is CH3. Embodiment 11. A compound of Embodiment 7 wherein R2 is cyano.
Embodiment 12. A compound of Formula I wherein when J is J-3, R1 is H and R2 is CH3, then the carbon atom to which R1 and R2 are attached is a stereocenter with the S configuration. Embodiment 13. A compound of Formula I wherein when J is J-3, R1 is H and R2 is other than H, then the carbon atom to which R1 and R2 are attached is a stereocenter has a configuration described as S when R2 is a methyl group. Embodiment 14. A compound of Formula I wherein when R1 is H and R2 is CH3, then the carbon atom to which R1 and R2 are attached is a stereocenter with the S configuration. Embodiment 15. A compound of Formula I wherein when R1 is H and R2 is other than H, then the carbon atom to which R1 and R2 are attached is a stereocenter has a configuration described as S when R2 is a methyl group. Embodiment 16. A compound of Formula I wherein R1 is.H, R2 is other than H, and the carbon atom to which R1 and R2 are attached is a stereocenter having a configuration described as S when R2 is a methyl group.
Embodiment 17. A compound of Embodiment 16 wherein R2 is CH and the carbon atom to which R1 and R2 are attached is a stereocenter with the S configuration. Embodiment 18. A compound of Formula I wherein m is an integer from 0 to 3. Embodiment 19. A compound of Embodiment 18 wherein m is an integer from 0 to 2. Embodiment 20. A compound of Embodiment 19 wherein m is 0 or 1.
Embodiment 21. A compound of Formula I wherein an R3 substituent is attached at the position para to the connection of the phenyl ring to the remainder of Formula I. Embodiment 22. A compound of Formula I wherein m is 1 and the R3 substituent is attached at the position para position to the connection of the phenyl ring to the remainder of Formula I.
Embodiment 23. A compound of Formula I wherein each R3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C4 alkoxyalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C2-C alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C haloalkynylsulfonyl, Cj-04 alkylamino, C2-Cg dialkylamino, C3-C6 cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)- ; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -OCF2O-, -OCH2CH2O-, -OCF2CF2O- or -CH=CH-CH=CH-.
Embodiment 24. A compound of Embodiment 23 wherein each R3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, ^-04 haloalkoxy, C2-C4 alkoxyalkoxy, C3-C4 alkynyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-Cg alkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O- or -OCF2O-.
Embodiment 25. A compound of Embodiment 24 wherein each R3 is independently halogen, cyano, nitro, Cι-C2 alkyl, Cj-C2 haloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, C3 alkynyloxy, C^-C2 alkylthio, Cj-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, trimethylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O- or -OCF2O-.
Embodiment 26. A compound of Formula I wherein each R25 is independently H, Cι-C2 alkyl or Cι-C2 haloalkyl; and each R26 is independently H or CH3; Embodiment 27. A compound of Formula I wherein each R27 is independently C^-C2 alkyl, C^-C2 haloalkyl or dimethylamino.
Embodiment 28. A compound of Formula I wherein each R28 is independently H, Cι-C2 alkyl or Cι-C2 haloalkyl.
Embodiment 29. A compound of Embodiment 25 wherein each R3 is independently halogen, cyano, methyl, Cj fluoroalkyl, methoxy or Ci fluoroalkoxy.
Embodiment 30. A compound of Embodiment 29 wherein each R3 is independently F, Cl, Br, cyano, methyl or methoxy.
Embodiment 31. A compound of Embodiment 30 wherein each R3 is independently F, Cl, Br, methyl or methoxy. Embodiment 32. A compound of Formula I wherein R4 is Cj-Cy alkyl, C -C7 cycloalkyl, C -C7 cycloalkylalkyl, Cj-Cy haloalkyl, C2-C7 cyanoalkyl, C2-C7 nitroalkyl, C3-C7 halocycloalkyl, C4-C7 halocycloalkylalkyl, C2-C7 alkenyl, C2-C7 haloalkenyl, C3-C7 alkynyl, C3-C7 haloalkynyl, C2-C7 alkoxyalkyl, C4-C7 (cycloalkyl)oxyalkyl, C2-C7 haloalkoxyalkyl, C -C7 alkenyloxyalkyl, C4-C7 haloalkenyloxyalkyl, C4-C7 alkynyloxyalkyl, C2-C7 alkylthioalkyl, C2-C7 alkylsulfinylalkyl, C2-C7 alkylsulfonylalkyl, C4-C7 (cycloalkyl)thioalkyl, C4-C7 alkenylthioalkyl, C4-C7 alkynylthioalkyl, C4-C7 alkoxyalkenyl, C -C7 alkoxyalkynyl, C4-C7 alkylthioalkenyl, C4-C7 alkylthioalkynyl or C4~C7 trialkylsilylalkyl. Embodiment 33. A compound of Embodiment 32 wherein R is Cι-C6 alkyl, C3-Cg cycloalkyl, C4-C7 cycloalkylalkyl, Cj-Cβ haloalkyl, C2-C6 cyanoalkyl, C3-Cg alkenyl, C3-Cg haloalkenyl, C3-Cg alkynyl, C3-C6 haloalkynyl, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl or C2-C6 alkylthioalkyl.
Embodiment 34. A compound of Embodiment 33 wherein R is Cj-Cg alkyl, CJ-C6 haloalkyl, C3-Cg cycloalkyl, cyclopropylmethyl, C3-C6 alkenyl, C3-C6 haloalkenyl or C3-Cg alkynyl. Embodiment 35. A compound of Embodiment 34 wherein R is C3-C4 alkyl, C -C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 alkenyl, C3-C4 haloalkenyl or C3-C4 alkynyl. Embodiment 36. A compound of Embodiment 35 wherein R is C3-C4 alkyl, C -C4 alkenyl or C3-Q4 alkynyl. Embodiment 37. A compound of Embodiment 36 wherein R4 is C3-C4 alkyl. Embodiment 38. A compound of Embodiment 37 wherein R is CH(CH3)2.
Embodiment 39. A compound of Formula I wherein R5 is halogen, Cj-C2 haloalkyl, Cχ-C2 alkoxy or Cι-C2 alkylthio. Embodiment 40. A compound of Embodiment 39 wherein R5 is halogen, CF3 or methoxy. Embodiment 41. A compound of Embodiment 40 wherein R5 is halogen.
Embodiment 42. A compound of Embodiment 41 wherein R5 is F, Cl or Br. Embodiment 43. A compound of Embodiment 42 wherein R5 is Cl or Br. Embodiment 44. A compound of Formula I wherein R6 is H, halogen, cyano, C -C3 alkyl, Cι-C3 haloalkyl, Cι-C3 alkoxy or Cj-C3 alkylthio. Embodiment 45. A compound of Embodiment 44 wherein R6 is Ci -C3 alkyl.
Embodiment 46. A compound of Embodiment 45 wherein R6 is methyl. Embodiment 47. A compound of Formula I wherein R6a is Cι-C3 alkyl. Embodiment 48. A compound of Embodiment 47 wherein R6a is methyl. Embodiment 49. A compound of Formula I wherein R7 is Cι-C alkyl or C1-C2 fluoroalkyl.
Embodiment 50. A compound of Embodiment 49 wherein R7 is Cι-C2 alkyl, CHF2 or CH2CF3. Embodiment 51. A compound of Embodiment 50 wherein R7 is methyl. Embodiment 52. A compound of Formula I wherein J is J-l, J-2 or J-3. Embodiment 53. A compound of Formula I wherein J is J-l, J-2 or J-4. Embodiment 54. A compound of Formula I wherein J is J-l, J-3 or J-4. Embodiment 55. A compound of Formula I wherein J is J-l or J-2. Embodiment 56. A compound of Formula I wherein J is J-l or J-3.
Embodiment 57. A compound of Formula I wherein J is J-l or J-4. Embodiment 58. A compound of Formula I wherein J is J-l. Embodiment 59. A compound of Formula I wherein J is J-2. Embodiment 60. A compound of Formula I wherein J is J-3. Embodiment 61. A compound of Formula I wherein J is J-4.
Embodiment 62. A compound of Formula I wherein when J is J-3, then R3 is other then optionally substituted phenoxy. Embodiment 63. A compound of Formula I wherein R3 is other than optionally substituted phenoxy. Embodiment 64. A compound of Formula I wherein when J is J-3 and Y is NR8, then R is other than alkyl substituted with optionally substituted phenyl. Embodiment 65. A compound of Formula I wherein when J is J-3, then Y is O or S(O)n. Embodiment 66. A compound of Formula I wherein when J is J-l and R is optionally substituted phenyl, then Y is O or S(O)n.
Embodiment 67. A compound of Formula I wherein when R is optionally substituted phenyl, then Y is O or S(O)n. Embodiment 68. A compound of Formula I wherein Y is O or S(O)n. Embodiment 69. A compound of Formula I wherein when Y is NR8, then R2 is other than cyano.
Embodiment 70. A compound of Formula I wherein when J is J-3, then R4 is other than phenyl. Embodiment 71. A compound of Formula I wherein when J is J-l or J-2, then R4 is other than optionally substituted phenyl. Embodiment 72. A compound of Formula I wherein when J is J-3, then R4 is other than optionally substituted phenyl. Embodiment 73. A compound of Formula I wherein R4 is other than optionally substituted phenyl. Embodiment 74. A compound of Formula I wherein when J is J-3 and Y is NR8, then R4 is other than benzyl.
Embodiment 75. A compound of Formula I wherein when J is J-3 and Y is NR8, then R4 is other than alkyl substituted with optionally substituted phenyl. Embodiment 76. A compound of Formula I wherein when Y is NR8, then R is other than alkyl substituted with optionally substituted phenyl.
Embodiment 77. A compound of Formula I wherein when J is J-4, then Y is O or NR8.
Embodiment 78. A compound of Formula I wherein when J is J-4, then Y is O. Embodiment 79. A compound of Formula I wherein R3 is other than an optionally substituted 5-membered heteroaromatic ring or an optionally substituted 6-membered heteroaromatic ring. Combinations of Embodiments 1-79 are illustrated by: Embodiment A. A compound of Formula I wherein m is an integer from 0 to 3; n is 0; q is 0; and each R3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C cycloalkyl, C3-Cg halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C4 alkoxyalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, C1-C4 alkylamino, C2-Cg dialkylamino, C3-Cg cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C2-Cg alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -OCF2O-, -OCH2CH2O-, -OCF2CF2O- or -CH=CH-CH=CH-. Embodiment B. A compound of Embodiment A wherein Y is O and R is H. Embodiment C. A compound of Embodiment B wherein R6 is H, halogen, cyano, C1-C3 alkyl, Ci-Gj haloalkyl, C!-C3 alkoxy or Cι-C3 alkylthio. Embodiment D. A compound of Embodiment C wherein R5 is halogen, Cι-C2 haloalkyl, ^-C^ alkoxy or Cι-C2 alkylthio; and R7 is Cι-C2 alkyl, CHF2 or CH2CF3. Embodiment E. A compound of Embodiment D wherein each R3 is independently halogen, cyano, nitro, alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C alkoxyalkoxy, C3-C4 alkynyloxy, Cj-04 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2- or R 7S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O- or -OCF2O-. Embodiment F. A compound of Embodiment E wherein R1 is H and R2 is H, cyano or CH3. Embodiment G. A compound of Embodiment F wherein R5 is halogen, CF or methoxy. Embodiment H. A compound of Embodiment G wherein J is J-l . Embodiment I. A compound of Embodiment H wherein R5 is halogen. Embodiment J. A compound of Embodiment I wherein each R3 is independently halogen, cyano, nitro, C ~C2 alkyl, Cι-C2 haloalkyl, Cι-C2 alkoxy, Cι-C2 haloalkoxy, C3 alkynyloxy, Cι-C2 alkylthio, Cι-C2 alkylsulfinyl, C]-C2 alkylsulfonyl, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, trimethylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O- or -OCF2O-; each R25 is independently H, - alkyl or Cι-C2 haloalkyl; each R26 is independently H or CH3; each R27 is independently Cι-C2 alkyl, Cχ-C2 haloalkyl or dimethylamino; and each R28 is independently H, Cι-C2 alkyl or Cι-C2 haloalkyl. Embodiment K. A compound of Embodiment J wherein R4 is Cj-Cg alkyl, Cj-Cg haloalkyl, C3-C6 cycloalkyl, cyclopropylmethyl, C -Cg alkenyl, C3-Cg haloalkenyl or C3-Cg alkynyl. Embodiment L. A compound of Embodiment K wherein R2 is CH3 and the carbon atom to which R1 and R2 are attached is a stereocenter with the S configuration. Specific embodiments include compounds of Formula I selected from the group consisting of: 2-chloro-N- [(IS)- 1 -(4-fluorophenyl)ethyl] -6-methyl-4-( 1 -methylethoxy)- 3-pyridinecarboxamide, 2-bromo-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-N-[(lS)-l-(4-methoxyphenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-6-methyl-4-(l-methylethoxy)-N-[(lS)-l-(4-methylphenyl)ethyl]- 3-pyridinecarboxamide, and 2-bromo-6-methyl-4-(l-methylethoxy)-N-[(lS)-l-phenylethyl]-3-ρyridine- carboxamide. Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above. 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). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Of note is a compound of Formula I, including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides wherein J is J-l, J-3 or J-4; R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C4 alkoxymethyl, cyano or C2-C4 alkoxycarbonyl; each R3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-U4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C4 alkylthio, C1-C4 haloalkylthio, C -C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C2-C4 alkylsulfonyl, C2-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C -C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, C1-C4 alkylamino, C2~C dialkylamino, C3-C6 cycloalkylamino, C4-C6 ' (alkyl)cycloalkylamino, C2-Cg alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl, phenyl, phenoxy and 5- or 6-membered heteroaromatic rings, each phenyl, phenoxy and 5- or 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R9; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O- or -CH=CH-CH=CH-; R4 is Cι-C10 alkyl, C3-C7 cycloalkyl, C4-C10 alkylcycloalkyl, C4-C o cycloalkylalkyl, C5-C10 alkylcycloalkylalkyl,
Figure imgf000021_0001
haloalkyl, C2-Ci0 cyanoalkyl, C2-C10 nitroalkyl, C3-C10 halocycloalkyl, C4-C10 halocycloalkylalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, C2-C10 alkoxyalkyl, C4-C10 (cycloalkyl)oxyalkyl, -CHf (CH2)p}, C2-C10 haloalkoxyalkyl, C4-C10 alkenyloxyalkyl, C4-C10 haloalkenyloxyalkyl, C4-C10 alkynyloxyalkyl, C4-C10 haloalkynyloxyalkyl, C2-C^o alkylthioalkyl, C2-Cιo alkylsulfinylalkyl, C2-CIQ alkylsulfonylalkyl, C4-C10 (cycloalkyl)thioalkyl, C4-C10 alkenylthioalkyl, C4-C^o alkynylthioalkyl, C4-C10 alkoxyalkenyl, C4-C10 alkoxyalkynyl, C4-C10 alkylthioalkenyl, C4-C10 alkylthioalkynyl, C4-C10 trialkylsilylalkyl, -Ν=CR10R or -NR12R13; or R4 is Ci-Cg alkyl substituted with C(O)R14, C(=NOR15)R16, NR17R18 or phenyl optionally substituted with R19, R20 and R21; or R4 is phenyl optionally substituted with R22, R23 and R24; R6 is H, halogen, cyano, Cι-C6 alkyl, C1-C4 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-Cg halocycloalkyl, C1-C4 alkoxy, 0^04 haloalkoxy, C1-C4 alkylthio or C!-C4 haloalkylthio; R7 is H, Cj-Cg alkyl, C1-C4 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-Cg cycloalkyl, C3-Cg halocycloalkyl or C1-C4 alkoxy or phenyl optionally substituted with 1-3 R26; R10 is H, C2-C4 alkyl or phenyl optionally substituted with 1-2 R27; R11 is H or C1-C2 alkyl; and R14 is H or Cj-^ alkyl. Also of note is a compound of Formula I, including all geometric and stereoisomers, N-oxides or agriculturally suitable salts thereof, agricultural compositions containing them and their use as herbicides wherein R2 is H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C alkoxymethyl, cyano, methoxy or C2-C4 alkoxycarbonyl; and each R3 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C!-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C3-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, Cj-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C4 alkoxyalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C]-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, ^-04 alkylamino, C2~Cg dialkylamino, C3-Cg cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C2-C alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-Cg trialkylsilyl, R25(R26)ΝS(O)2-, R27S(O)2N(R28)-, phenyl, phenoxy, 5-membered heteroaromatic ring and 6-membered heteroaromatic ring, each phenyl, phenoxy, 5-membered heteroaromatic ring and 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R9; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O- or -CH=CH-CH=CH-. The compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1 through 33 and accompanying text. The definitions of J, Q, R, Rl, R2, R3, R4, R5, R6, R6a, R7, R8> R9? R10; RII^ R12> RB RU 15, R16, RI7, RlS, RI9, R20, R21; R22, R23, R24, R25; R26> R27, R28, R29, R30; R31, R41, R41a,
R42, R43, R50, R51, R52, R53, R60, Y, j, k, m, n, p and q in the compounds of Formulae I through Id, and 2 through 69 below are as defined above in the Summary of the Invention and description of embodiments unless otherwise indicated. Compounds of Formulae la through le are various subsets of the compounds of Formula I, compounds of Formulae 2a through 2d are subsets of compounds of Formula 2, and compounds of Formulae 4a through 4d are subsets of the compounds of Formula 4, and compounds of Formulae 18a and 18b are subsets of compounds of Formula 18. As shown in Scheme 1, compounds of Formula I are prepared by treating an amine of Formula 2 with an appropriate acid chloride of Formula 3 in an inert solvent with one molar equivalent of a base (e.g., triethylamine or potassium carbonate) present. Alternatively, polymer-supported acid scavengers are useful such as polymer-bound equivalent of N,N-diisopropylethylamine and 4-(dimethylamino)pyridine, such as N-[(4-ethenylphenyl)- methyl] -N-methyl-4-pyridinamine polymer with diethenylbenzene and ethenylbenzene (CAS Registry Number 82942-26-5, hereafter identified as "PS-DMAP"). Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; halocarbons such as dichloromethane or chloroform; and nitriles such as acetonitrile. Scheme 1
Figure imgf000023_0001
wherein X is Cl or Br.
Alternatively, compounds of Formula I are prepared by treating the hydrochloride salts of amines of Formula 2 with an appropriate acid chloride or bromide of Formula 3 in an inert solvent with two molar equivalents of a base (e.g., triethylamine, potassium carbonate or PS-DMAP) present. The method of Scheme 1 is illustrated in Step B of Example 1, Example 2, Step E of Example 5, Step B of Example 9, Step D of Example 11 and Step C of Example 12. Compounds of Formula I can also be synthesized by reacting an amine of Formula 2 with an appropriate carboxylic acid of Formula 4 in the presence of an organic dehydrating reagent such as 1,3-dicyclohexylcarbodiimide (DCC) or l-[3-(dimethylamino)propyl]- 3-ethylcarbodiimide hydrochloride (EDC) as depicted in Scheme 2. Polymer-supported reagents are again useful here, such as polymer-bound equivalent of cyclohexylcarbodiimide (e.g., PS-CH2N=C=N-cyclohexyl wherein PS is a polystyrene backbone). Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform. Scheme 2 Dehydrating Reagent
Figure imgf000023_0002
The method of Scheme 2 is illustrated in Step C of Example 6 and Step B of Example 7. The synthetic methods illustrated by Schemes 1 and 2 should be merely regarded as representative of a wide variety of known general methods useful for preparing Formula I compounds, as the synthetic chemistry literature contains many examples of this type of condensation. One skilled in the art will also realize that acyl compounds of Formula 3 wherein X is Cl or Br can be prepared from corresponding carboxylic acids of Formula 4 by numerous well known methods, for example but not limited to, reaction of carboxylic acids with chlorinating reagents such as oxalyl chloride and thionyl chloride or brominating agents such as phosphorus oxybromide. This method is illustrated in Step B of Example 1, Example 2, Step E of Example 5, Step B of Example 9, Step D of Example 11 and Step C of Example 12. Benzylamines of Formula 2 are commercially available or are readily prepared by numerous well known methods, several of which are described in Schemes 23-28. As shown in Scheme 3, compounds of Formulae la, lb, Ic or Id (Formula I wherein J is J-l, J-2, J-3, or J-4 respectively) can also be prepared by treating amides of Formula 5a- 5d wherein X1 is a leaving group such as halide, methyl sulfonate or p-toluenesulfonate with a nucleophile of Formula 6 and a strong base (e.g., sodium hydride or potassium t-butoxide) in a polar solvent at temperatures ranging from 0 to 150 °C; displacements with alkoxides and thiolates generally proceed at 0 to 80 °C, displacements with amines may require temperatures up to 150 °C. Suitable solvents are selected from the group consisting of amides such as N,N-dimethylformamide, lower alcohols such as ethanol, ethers such as tetrahydrofuran or dioxane, or sulfoxides or sulfones such as dimethylsulfoxide or sulfolane. Scheme 3
Figure imgf000024_0001
5a la
Figure imgf000024_0002
Figure imgf000025_0001
wherein R50 is ; and
Figure imgf000025_0002
X1 is a nucleophilic reaction leaving group such as halide, OS(O)2Me, OS(O)2-C6H4- -CH3 or S(O)2CH3.
Compounds of Formulae 5a-5d can be prepared from the corresponding starting compounds using methods analogous to those of Schemes 1 and 2 as well as other methods. The method of Scheme 3 is illustrated by Examples 3, 4, 8 and 10. Compounds of Formulae la, lb, Ic or Id wherein Y is S(O)n and n is 1 can be prepared by oxidation of corresponding compounds of Formulae la, lb, Ic or Id wherein Y is S(O)n and n is 0 by contact with an appropriately stoichiometric amount of an oxidizing agent such as m-chloroperbenzoic acid in an inert solvent such as dichloromethane or 1,2-dichloroethane using reaction conditions well known in the art. Carboxylic acids of Formulae 4a-d (Formula 4 wherein J is J-l, J-2, J-3 or J-4, respectively) can be prepared as depicted in Scheme 4. Scheme 4
Figure imgf000025_0003
7a 4a R51 is Cθ2H R51 is C02H, C02R5 C(0)NH2 or CN 8a R51 is C02R52 C(0)NH2 or CN
Figure imgf000025_0004
7b 4b R51 is C02H R51 is C02H, C02R52 C(0)NH2 or CN 8b R51 is C02R52, C(0)NH2 or CN
Figure imgf000026_0001
R51 is C02H, C02R5 C(0)NH2 or CN 8c R51 is C02R52 C(0)NH2 or CN
Figure imgf000026_0002
7d 4d R511 iiss 'C02H R51 is C02H, C02R5 C(0)NH2 or CN 8d R51 is C02R52, C(0)NH2 or CN wherein R52 is carbon-based radical such as alkyl, preferably Cj-Qφ alkyl; and X1 is a nucleophilic reaction leaving group such as halide, OS (O)2CH3. OS(O)2CgH4- p-CH3 or S(O)2CH3.
For example, treatment of a pyridine of Formula 7a wherein R51 is CO2H with a compound of Formula 6 in the presence of a base affords good yields of the corresponding compound of Formula 4a with good specificity for the desired regiochemistry. Accordingly carboxylic acids of Formulae 4a-4d can be prepared from corresponding compounds of Formulae 7a- 7d wherein R51 is CO2H and X1 is a leaving group such as halide, methyl sulfonate or -toluenesulfonate by treatment with a compound of Formula 6 and 2.0 to 2.4 equivalents of a strong base (e.g., sodium hydride or potassium t-butoxide) in a polar solvent at temperatures ranging from 0 to 150 °C. Preferred temperatures range from room temperature to 100 °C. Suitable solvents are selected from the group consisting of amides such as N,N-dimethylformamide (DMF), ethers such as tetrahydrofuran or sulfoxides or sulfones such as dimethylsulfoxide or sulfolane. The method of Scheme 4 wherein R15 is CO2H is illustrated in Step A of Example 1. Scheme 4 also shows that substituted esters, amides and nitriles of Formulae 8a-8d can be made from esters, amides and nitriles of Formulae 7a-7d (wherein R51 is CO2R52, C(O)ΝH2 or CN and X1 is leaving group) via displacement by treatment with compounds of Formula 6 in the presence of base. Suitable bases include alkali metal carbonates, hydroxides, alkoxides and hydrides (e.g., K2CO3, KO-t-Bu, NaH, NaOEt) and trialkylamine bases (e.g., triethylamine). The reaction is conducted in a suitable solvent such as N,N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran or excess compound of Formula 6 wherein Y is O (i.e. an alcohol) and at temperatures ranging from 0 °C to the reflux temperature of the solvent. The method of Scheme 4 wherein R51 is CO2R52 is illustrated in Step B of Example 6 and Step A of Example 7. Nitriles of Formula 8d wherein R51 is CN can also be prepared as described in U.S. Patent 3,155,678. Substituted acids of Formulae 4a-4d can then be prepared by base or acid hydrolysis of the corresponding esters, amides and nitriles of Formulae 8a-8d (wherein R52 is preferably methyl or ethyl). Suitable bases include alkali metal hydroxides (e.g., NaOH, KOH). The ester, amide or nitrile can be dissolved in a mixture of water and an alcohol such as ethanol and treated with base. The reaction mixture is stirred at temperatures ranging from 0 °C to the reflux temperature of the solvent. Hydrolysis of esters, amides or nitriles provides the corresponding carboxylic acids in the form of an alkali metal salt. Acidification with a strong acid (e.g., HCl, H2SO4) then yields the corresponding carboxylic acids of Formulae 4a-4d. This method is illustrated in Step D of Example 5, Step B of Example 6, Step A of Example 7, Step A of Example 9 and Step C of Example 11. In some cases, nitriles of Formulae 8a-8d can be treated with acidic alcohol (e.g., HCl in methanol or ethanol) to. give esters of Formula 8a-8d wherein R51 is CO2R52, which in turn can be hydrolyzed under basic or acidic conditions as previous described to provide the corresponding carboxylic acids of Formulae 4a-4d. As shown in Scheme 5, compounds of Formulae 8a-8d and Compounds of Formulae
Ia-d (wherein R5 is halogen) can be converted to compounds of Formulae 8a-8d and Compounds of Formulae Ia-d respectively (wherein R5 is alkoxy, haloalkoxy, alkylthio or haloalkylthio) by reacting with an alkyl alcohol, haloalkyl alcohol, alkylmercaptan or haloalkylmercaptan in the presence base such as an alkali metal base (e.g., potassium carbonate, sodium hydride or a sodium alkoxide) in a solvent such as N,N-dimethylformamide, acetonitrile, dioxane, tetrahydrofuran or an alkyl alcohol at temperatures ranging from 0 °C to the reflux temperature of the solvent. Scheme 5 alkoxide, haloalkoxide, alkylthiolate or haloalkylthio late 8a-8d (R5 is halogen) - 8a-8d (R5 is alkoxy, haloalkoxy, base, solvent alkylthio, haloalkylthio) alkoxide, haloalkoxide, alkylthiolate or haloalkylthiolate la-Id (R5 is halogen) ■ la-Id (R5 is alkoxy, haloalkoxy, base, solvent alkylthio, haloalkylthio) Carboxylic acids of Formula 7a wherein R51 is CO2H, X1 is Cl, R6 is H or CH3 and
R5 is Cl are described in World Patent Publications WO 02/22583 and WO 03/027112 respectively. Additional carboxylic acids of Formula 7a are described in Eur. J. Org. Chem. 2001, 1371. The other compounds of Formulae 7a-7d can be prepared by the wide variety of methodologies known in the art of synthetic organic chemistry, including those shown in the following Schemes. For example as shown in Scheme 6, compounds of Formula 7a wherein R51 is CO2H, CO2R52 or C(O)NH2 and X1 is Cl or Br can be prepared from the corresponding acyl halides of Formula 18 by reaction with water, R52OH (19) or ammonia, respectively, according to standard methods. Scheme 6
Figure imgf000028_0001
18 7a Xi is Cl orBr. R51 is C02H, C02R52 or C(0)NH2. Compounds of Formula 18 wherein R5 is X1 (Formula 18a) or R6 is X1 (Formula 18b) can in turn be prepared by from the corresponding 4-hydroxy pyridones of Formulae 20a and 20b as shown in Scheme 7. Scheme 7
Figure imgf000028_0002
20a 18a
Figure imgf000028_0003
Xi is Cl orBr. 20b 18b R53 is Hor CrC2 alkyl.
Reaction with three equivalents or an excess of a halogenating reagent such as phosphorus oxychloride or phosphorus oxybromide at reflux temperatures provides the corresponding dihalo acid halides of Formulae 18a or 18b. In the reaction of phosphorus oxybromide with compounds of Formulae 20a wherein R53 is methyl or ethyl (i.e. esters) it is not necessary to hydrolyze the esters to acids; the acid bromides are obtained directly from the esters under the reaction conditions. The phosphorus oxyhalide can be used as the solvent, or another solvent can be added. Suitable solvents are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; halocarbons such as dichloromethane or chloroform; and nitriles or amines such as acetonitrile or N,N-diethylaniline. A catalyst such as DMF can also be used. Compounds of Formula 18a and 18b wherein X1 is chloride are useful starting materials for preparing compounds of Formula 18a and 18b wherein X1 is bromine or iodine by halogen exchange according to the general method described in Eur. J. Org. Chem. 2002, 4181-4184. Compounds of Formulae 18a and 18b are also useful starting materials for preparing compounds of Formula I according to the methods of Schemes 4, 5 and 6. Alternatively, compounds of Formula 18a and 18b can be coupled with amines of Formula 2 using methods analogous to Scheme 1 to form compounds of Formula 5a, which can then be further elaborated as shown in Scheme 3. Compounds of Formula 20a wherein R53 is methyl or ethyl can be prepared by reacting a maloήate of Formula 22 with a substituted aminocrotonate of Formula 21 as shown in Scheme 8. Scheme 8 Solvent
Reflux or microwave
Figure imgf000029_0002
Figure imgf000029_0001
21 22 20a R53 is -Cj alkyl.
Suitable solvents are selected from the group consisting of alcohols such as ethanol or isopropanol; and hydrocarbons such as toluene or benzene at temperatures ranging from 0 °C to the reflux temperature of the solvent. The reaction can also be carried out at temperatures up to 250 °C using a microwave reactor. As shown in Scheme 9, ethers of Formula 8a wherein Y is O and R51 is CO2R52 can be prepared from compounds of Formula 23 by selective O-alkylation with compound of Formula 24 wherein X2 is a nucleophilic reaction leaving group such as halide, tosylate or mesylate) in the presence of a base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide at temperatures ranging from room temperature to the reflux temperature of the solvent. When R4 is n-propyl, iodide is particularly useful as X2. Scheme 9
Figure imgf000030_0001
23
The method of Scheme 9 is illustrated in Step B of Example 11. As shown in Scheme 10, compounds of Formula 23 wherein R5 is F, Cl, Br or I can be prepared by treatment of compounds of Formula 25 described in German Patent Publication DE2726685 with from one to three equivalents of a Lewis acid such as a trimethylsilyl halide of Formula 26. Scheme 10
Figure imgf000030_0002
25
Suitable solvents include halocarbons such as dichloromethane or trichloromethane and hydrocarbons such as toluene or benzene. Suitable reaction temperatures range from 0 °C to the reflux temperature of the solvent. Step A of Example 11 illustrates the method of Scheme 10. As shown in Scheme 11, compounds of Formula 5b can be prepared by lithiation in the 4-position of a pyridine of Formula 27, followed by addition of an isocyanate of Formula 28. The reaction is conducted at low temperatures (e.g., 0 to -80 °C) in the presence of a lithium dialkylamide such as lithium diisopropylamide (LDA) in solvents such as ether or tetrahydrofuran. Scheme 11
Figure imgf000030_0003
As shown in Scheme 12, compounds of Formula 4b wherein R51 is CO2H can be prepared by analogous lithiation of compounds of Formula 29, followed by reaction with carbon dioxide according to the general method of Krapcho et al., J. Het. Chem. 1998, 35, 895-906. Scheme 12
Figure imgf000031_0001
29
The method of Scheme 12 is illustrated in Example B of Example 12. Compounds of Formula lb wherein Y is O or S can also be directly prepared by lithiation of the corresponding compound of Formula 29 followed by addition of the isocyanate of Formula 28 using conditions described for Scheme 11. This method is particularly useful for preparing compounds of Formula lb wherein Y is O and R is CH2OCH3. This method is illustrated in Example 14. As shown in Scheme 13, other compounds of Formula lb wherein Y is O can be prepared from the corresponding compounds of Formula lb wherein Y is O and R4 is CH2OCH3 by acidic removal of the CH2OCH3 group to form the alcohol of Formula 30, followed by alkylation with an alkylating agent in the presence of an acid acceptor. Scheme 13
R4χ2
Figure imgf000031_0002
Suitable acids for removal of the CH2OCH3 group include trifluoroacetic acid, p-toluenesulfonic acid, hydrochloric acid and hydrobromic acid, as well as solid acid resins such as sulfonated polystyrene. Suitable solvents for the removal of the CH2OCH3 group include diethyl ether, tetrahydrofuran, dioxane, dichloromethane, dichloroethane and other solvents inert to the action of acids. The hydroxypyridines of Formula 30 can be alkylated with an alkylating agent of Formula 24 wherein X2 is a nucleophilic reaction leaving group such as halide, tosylate or mesylate. Suitable acid acceptors include bases such as alkali hydroxides, alkali carbonates and alkali hydrides, as well as alkoxides and other strong bases. Suitable solvents are stable in the presence of bases and include tetrahydrofuran, dioxane, dimethylsulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide. Lower alcohols are particularly useful as solvents for reactions involving alkoxides as acid acceptors. Preferred conditions involve the use of potassium carbonate as the acid acceptor and N,N-dimethylformamide as the solvent. The method of Scheme 13 is illustrated in Example 15. As shown in Scheme 14, compounds of Formula le (i.e compounds of Formula I wherein J is J-2 and q is 1) can be prepared by alkylation of the pyridine nitrogen atom of the corresponding compounds of Formula lb (i.e. compounds of Formula I wherein J is J-2 and q is 0). Scheme 14
Figure imgf000032_0001
(X3) Θ le
The alkylation involves contacting a compound of Formula le with an alkylating agent of Formula 31 wherein X3 is a nucleophic reaction leaving group such as a halide (e.g., bromide, iodide), sulfonate (e.g., mesylate, triflate, -toluenesulfonate) or an ether (when , Formula 31 is, for example, a trialkyloxonium tetrafluoroborate). This reaction can be carried out in excess alkylating agent (e.g., iodomethane) or using a variety of solvents such as ethers, acetonitrile or N,N-dimethylformamide. The method of Scheme 14 is illustrated in Example 13. Pyridines of Formulae 27 and 29 and methods for their preparation are well known in the art. For example, pyridines of Formula 29 can be synthesized by nucleophilic displacement reactions on the corresponding 3-halopyridines or by alkylation of the corresponding 3-hydroxy- or 3-mercaptopyridines according to general methods described by Testaferri et al., Tetrahedron 1985, 41, 1373-1384; Harrowven et al., Tetrahedron 2001, 57, 4447_4454; U.S. Patent 5914328; and PCT Patent Publication WO2002/088114. As illustrated in Scheme 15, halogen substituted pyrazole esters of Formula 7c (wherein R51 is CO2R52 and X1 is halogen) can be prepared from pyrazole aldehydes of Formula 33 by oxidation to the carboxylic acid followed by esterification. Scheme 15
Figure imgf000033_0001
33
Treatment of aldehydes of Formulae 33 with an oxidizing reagent (such as potassium permanganate, potassium peroxymonosulfate (e.g., Oxone®), a sodium perchlorate/sodium chlorite mixture or manganese dioxide) in a suitable solvent or solvent mixture (e.g., comprised of one or more of the following solvents: alcohol, dioxane, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide or water) affords the carboxylic acids which can then be converted to esters 7c by treating with an alkyl alcohol, preferably methanol or ethanol, in the presence of an acid catalyst, e.g., hydrochloric acid, sulfuric acid or -toluenesulfonic acid at temperatures ranging from 0 °C to the reflux temperature of the solvent. Scheme 16 illustrates how pyrazole aldehydes of Formula .33 (wherein X1 is halogen) can be made by chlorination and formylation of hydroxypyrazoles of Formula 34 in one step under Nilsmeier conditions using a mixture of a phosphorus oxyhalide and N,N-dimethyl- formamide. Scheme 16
Figure imgf000033_0002
34
The reaction can be carried out neat or optionally with a solvent such as toluene, xylene or dichloromethane at a temperature ranging from 0 to 120 °C. As shown in Scheme 17, substituted hydroxy pyrazoles of Formula 34 can be prepared by condensing a substituted hydrazine of Formula 36 with a beta-ketoester of Formula 35 or a methoxyacrylate of Formula 37. In some of these condensations, mixtures of Formula 34 with its isomer are obtained, from which the isomers can be separated by conventional techniques such as chromatography and crystallization. Scheme 17
Figure imgf000034_0001
base, solvent R-^ 35 37
R7NHNH2 36 R7NHNH2 36 base (optional) base (optional) solvent f solvent 34 \ 34 R54is CrC2 alkyl.
These condensations are carried out in a solvent such as alcohol, acetonitrile, toluene, xylene or glacial acetic acid, optionally in the presence of base (e.g., an alkali metal acetate or carbonate such as sodium acetate or potassium carbonate). The substituted methoxy acrylates of Formula 37 are made by methylation of the beta-ketoesters of Formula 35 with dimethyl sulfate or methyl iodide in the presence of base (e.g., a alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide. Substituted pyrazole esters of Formula ,8c (wherein Y is oxygen and R5 J is CO2R52) can also be made from hydroxy pyrazole esters of Formula 39 via alkylation as shown in Scheme 18. Scheme 18
Figure imgf000034_0002
Treatment of a compound of Formula 39 with an alkylating agent of formula R4X2 (24) (wherein X2 is a nucleophilic reaction leaving group such as halide, tosylate, mesylate or methanesulfonyl) in the presence of base (e.g., an alkali metal carbonate such as potassium carbonate, an alkali metal hydride such as sodium hydride or a trialkylamine such as triethylamine) in a suitable solvent such as tetrahydrofuran, acetonitrile or N,N-dimethyl- formamide at temperatures ranging from 0 °C to the reflux temperature of the solvent. The method of Scheme 18 is illustrated in Step C of Example 5. As shown in Scheme 19, substituted hydroxy pyrazole esters of Formula 39 can be made by condensing a substituted hydrazine of Formula 36 with a substituted acylmalonate of Formula 41 (where Q is O or S, and R5 is other than halogen) or a substituted malonate of Formula 42 (where Q is O or S, and R5 is other than halogen). In some of these condensations, mixtures of Formula 39 with its isomer are obtained, from which the isomers can be separated by conventional techniques such as chromatography and crystallization. Scheme 19
Figure imgf000035_0001
39 39 Q is O or S; R54 is C1-C2 alkyl.
These condensations are carried out in a solvent such as alcohol, acetonitrile, toluene, xylene or glacial acetic acid, optionally in the presence of base (e.g., an alkali metal acetate, or carbonate such as sodium acetate or potassium carbonate). Substituted malonates of Formula 42 are made by alkylation of acyl or thioacyl malonates of Formula 41 with dimethyl sulfate or methyl iodide in the presence of base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide. The method of Scheme 19 is illustrated in Step A of Example 5. Halogen-substituted hydroxypyrazole esters of Formula 39 (wherein R5 is halogen) can be made from hydroxy pyrazole esters of Formula 39 (wherein R5 is H) via halogenation as shown in Scheme 20. Scheme 20 halogenating agent 39 (R5 is H) 39 (R5 is halogen) neat or in solvent
This method uses a halogenating reagent such as a halogen (e.g., bromine, chlorine or chloroiodide) or a halosuccinimide neat or in an suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide at temperatures ranging from 0 to 150 °C. The method of Scheme 20 is illustrated in Step B of Example 5. Halogen-substituted pyrazole nitriles of Formula 7c (wherein R51 is CΝ and X1 is halogen) can be made from corresponding amino pyrazole nitriles of Formula 43 via diazotization in the presence of a halogen source in an appropriate solvent as shown in Scheme 21. Scheme 21
Figure imgf000036_0001
The usual diazotization method involves treating a stirred mixture of a compound of Formula 43 with an alkyl nitrite (e.g., iso-amyl or tert-butyl nitrite) and copper(I) or copper (11) halide in a solvent such as acetonitrile at temperatures ranging from 0 °C to the reflux temperature of the solvent to afford the corresponding pyrazole nitrile of Formula 7c. As shown in Scheme 22, substituted aminopyrazole nitriles of Formula 43 can be made by condensing a substituted hydrazine of Formula 36 with a substituted acyl or thioacyl malonitrile of Formula 44 (where Q is O or S, and R5 is other than halogen) or a substituted malonitrile of Formula 45 (where Q is O or S, and R5 is other than halogen). In some of these condensations, mixtures of Formula 43 with its isomer are obtained, which can be separated by conventional techniques such 'as chromatography and crystallization. Scheme 22
Figure imgf000036_0002
43 43 Q is O or S.
These condensations are generally carried out in a solvent such as alcohol, acetonitrile, toluene, xylene or glacial acetic acid, optionally in the presence of base (e.g., an alkali metal acetate or carbonate such as sodium acetate or potassium carbonate) or an acid catalyst (e.g., acetic acid). Substituted malononitriles of Formula 45 can be made by alkylation of acyl or thioacyl malononitriles of Formula 44 with dimethyl sulfate or methyl iodide in the presence of base (e.g., an alkali metal carbonate such as potassium carbonate or a trialkylamine such as triethylamine) in a solvent such as alcohol, acetonitrile or N,N-dimethylformamide. Halogen-substituted aminopyrazole nitriles of Formula 43 (wherein R^ is halogen) can be made from aminopyrazole nitriles of Formula 43 (wherein R5 is H) via halogenation using conditions analogous to the halogenation method shown for Formulae 39 in Scheme 20. As shown in Scheme 23, compounds of Formulae 4d and 8d can also be prepared by first halogenating an isothiazole of Formula 46 to form a haloisothiazole intermediate of Formula 47. The haloisothiazole intermediate of Formula 47 is subjected to a palladium- catalyzed carbonylation reaction to prepare a compound of Formula 4d (R51 is CO2H) or Formula 8d (R51 is CO2R52 or C(O)NH2), or a cyanation reation using either copper(I) cyanide or palladium catalysis to prepare a compound of Formula 8d wherein R51 is CN. Scheme 23
Figure imgf000037_0001
In this method an isothiazole of Formula 46 is treated with a halogenating agent such as a halosuccinimide or a halogen (e.g., bromine, chlorine or chloroiodide) neat or in a suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide at temperatures ranging from 0 to 150 °C to form the corresponding haloisothiazole of Formula 47. The compound of Formula 47 can then be treated with carbon monoxide in the presence of palladium catalyst and also a base such as potassium carbonate or triethylamine in a solvent such as methanol or N,N-dimethylformamide selected in view of whether a carboxylic acid (R51 is CO2H), an ester (R51 is CO2R52) or an amide (R51 is C(O)R52 is desired for Formula 4d/8d, according to general methods described by R. Skoda-Foldes and L. Kollar, Current Organic Chemistry 2002, 6(12), 1097-1119; E.-I. Νegishi, Background for Part NI. Handbook of Organopalladium Chemistry for Organic Synthesis 2002, 2, 2309- 2311; M. Beller and A. F. Indolese, Chimia 2001, 55(9), 684-687; and U.S. Patent 5,922,870. The intermediate of Formula 47 can also be converted by palladium-catalyzed cyanation to the corresponding compound of Formula 8d wherein R51 is CΝ according to general methods described in Synthesis 2004, (1), 23-25; Synlett 2003, 14, 2237-239; and European Journal of Inorganic Chemistry 2003, 19, 3513-3526. In this reaction the catalyst system typically comprises tris(dibenzylideneacetone)dipalladium(0), tri-tert-butylphosphine or l,l'-bis(diphenylphosphino)ferrocene and zinc powder, zinc cyanide is used as the cyanide source, the solvent is N,N-dimethylformamide or N,N-dimethylacetamide, and the reaction temperature ranges from 25 to 130 °C. Alternatively, the intermediate of Formula 47 can be converted to the compound of Formula 8d wherein R51 is CN by reaction with copper(I) cyanide at temperatures ranging from 185 to 250 °C according to a general method described in J. Heterocyclic Chem. 1988, 25, 235. Isothiazoles of Formula 46 are known or can be prepared by a variety of methods known in the literature; see, for example, Rodd's Chemistry of Carbon Compounds, 2nd Ed., Vol. IN, Part C, Elsevier 1986, edited by S. Coffey and M. F. Ansell, pp. 356-376; Advances in Heterocyclic Chemistry, Nol. 14, Academic Press, 1972, edited by A. R. Katritzky and A. J. Boulton, pp. 2-43; Comprehensive Heterocyclic Chemistry II, First Ed., Nol. 3, Elsevier Science, 1996, edited by A. R. Katritzky et al., pp. 319-372; and U.S. Patent 6,083,879. Compounds of Formulae 4d and 8d wherein R51 is CO2H or CO2R52 can also be prepared from corresponding haloisothiazoles of Formula 48 according to the method of Scheme 24. Scheme 24
X4is
Figure imgf000038_0001
In this method, a haloisothiazole of Formula 48 in an ethereal solvent such as ethyl ether or tetrahydrofuran is reacted with an alkylmagnesium halide, such as ethyl or methyl magnesium bromide or chloride, at temperatures not exceeding 5 °C or reacted with an organolithium reagent such as lithium diisopropylamide, n-butyllithium, sec-butyllithium or tert-butyllithium at temperatures typically below -70 °C to form a Grignard or lithio intermediate, respectively, according to the general methods of Synthetic Communications 1995, 25{9), 1383-89, U.S. Patent 6,083,879, and Heterocycles 1995, 41(3), 533-93. The intermediate is then reacted with carbon dioxide to form a compound of Formula 4d wherein R51 is CO2H or with a chloroformate of Formula 49 to form a compound of Formula 8d wherein R51 is CO2R52. Alternatively, compounds of Formula Id can be directly prepared from corresponding compounds of Formula 48 by forming a Grignard or lithio intermediate as described for the method of Scheme 24 and then adding the appropriate isocyanate of Formula 28 analogous to the method of Scheme 11. Compounds of Formula 48 can be prepared from compounds of Formula 50 according to the method of Scheme 25. Scheme 25
Figure imgf000039_0001
In this method an aminoisothiazole of Formula 50 is halogenated by contact with a halogen (e.g., bromine, chlorine or chloroiodide) or a halosuccinimide neat or in an suitable solvent such as dichloromethane, tetrahydrofuran, acetonitrile or N,N-dimethylformamide at temperatures ranging from 0 to 150 °C to provide the corresponding aminohalothiazole of Formula 51. The aminohalothiazole of Formula 51 is then diazotized using an alkyl nitrite (e.g., isoamyl nitrite or tert-butyl nitrite) and a copper(I) or copper(II) halide in a solvent such as acetonitrile at temperatures ranging from 0 °C to the reflux temperature of the solvent to provide the dihaloisothiazole of Formula 52 according to the general method of Synthetic Communications 1997, 27(12), 2181-2191. Then using reaction conditions analogous to the method of Scheme 4, the dihaloisothiazole of Formula 52 is contacted with a compound of Formula 6 in the presence of base and a solvent to provide the compound of Formula 48. As shown in Scheme 26, intermediates of Formula 52 can also be prepared from isothiazoles of Formula 53. Scheme 26
Figure imgf000039_0002
In this method, a isothiazole of Formula 53 is lithiated at or below -70 °C in an ethereal solvent such as ethyl ether or tetrahydrofuran by contact with an organolithium reagent such as lithium diisopropylamide, n-butyllithium or sec-butyllithium according to the general method of Heterocycles 1995, 41 {3), 533-93. The resulting 5-lithio intermediate is then reacted with the appropriate halogen of Formula 54 to provide the haloisothiazole of Formula 55. The haloisothiazole of Formula 55 is then halogenated to provide the compound of Formula 52 using conditions analogous to those described for the conversion of the compound of Formula 50 to the compound of Formula 51 in Scheme 25. As shown in Scheme 27, isothiazoles of Formula 7d wherein R51 is CO2H or CO2R52 and X1 is S(O)2CH3 can also be prepared from isothiazoles of Formula 53. Scheme 27
Figure imgf000040_0001
C02R52 In this method an isothiazole of Formula 53 is lithiated as described for the conversion of the compound of Formula 53 to the compound of Formula 55 in Scheme 26. The resulting 5-lithio intermediate is then contacted with dimethyl disulfide to form the methylthioisothiazole of Formula 54. The methylthioisothiazole of Formula 54 is then lithiated using lithium diisopropylamide, and the resulting 4-lithio intermediate is reacted with carbon dioxide or a chloroformate of Formula 49 to provide the methylthioisothiazole of Formula 55 wherein R51 is CO2H or CO2R52, respectively. The methylthio group of the compound of Formula 55 is then oxidized to methylsulfonyl to provide the compound of Formula 7d wherein R51 is CO2H or CO2R52 and X1 is S(O)2CH3. The oxidation is conducted using at least two equivalents of an oxidizing agent such as 3-chloroperoxybenzoic acid (MCPBA) or potassium peroxymonosulfate (e.g., Oxone®) in an inert solvent in which the oxidizing agent is soluble (e.g., dichloromethane for MCPBA, water for potassium peroxymonosulfate) at temperatures ranging from 0 °C to room temperature. Many benzylamines of Formula 2 are commercially available. Even some benzylamines with chiral centers can be commercially obtained in enantiomerically pure form. Benzylamines of Formula 2 that are not commercially available can be prepared by a wide variety methods known to those skilled in the art. For example, compounds of Formula 2a (hydrochloride salts of compounds of Formula 2 wherein R, R1 and R2 are hydrogen) can be prepared using the method described in J. Med. Chem. 1984, 27(9), 1111-1118. As shown in Scheme 28, compounds of Formula 60 are reacted with hexamethylenetetramine (61) in a suitable solvent such as dichloromethane or trichloromethane to provide compounds of Formula 2a after hydrolysis with aqueous acid. Scheme 28
Figure imgf000041_0001
X8 is a nucleophilic reaction leaving group such as Cl, Br, -OS(0) CH3 or -OS O^-p^Hg-CHg. Alternatively as shown in Scheme 29, compounds of Formula 2b can be prepared by reacting compounds of Formula 60 with a potassium salt of phthalimide (62) followed by reaction with either aminoethanol or hydrazine in an alcohol solvent to provide the desired aminomethyl intermediates of Formula 2b. Scheme 29
Figure imgf000041_0002
2b X9 is a nucleophilic reaction leaving group such as Cl, Br, -OS(0) Me or -OS(0)2-p-C4Hg-CH3. Compounds of Formula 60 can be prepared from the corresponding benzyl alcohols by methods well known in the art (e.g., treatment with POCl3 for X9 being Cl, treatment with PBr3 for X9 being Br, treatment with ClS(O)2Me or ClS(O)2-p-C4H6-CH3 for X9 being the corresponding sulfonates). The benzyl alcohols can be prepared by reduction of the corresponding carboxylic acids, carboxylic esters or carboxamides using methods well known in the art (e.g., treatment of carboxylic acids with diborane, treatment with esters or carboxamides with lithium aluminum hydride in ethereal solvents such as tetrahydrofuran, dimethoxyethane or diethyl ether). As shown in Scheme 30, compounds of Formula 2b can also be prepared by reacting nitriles of Formula 64 with a suitable reducing reagent such as diborane, lithium aluminum hydride or hydrogen with palladium on carbon at temperatures ranging from 0 to 100 °C. Suitable solvents for the reaction are selected from the group consisting of ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; hydrocarbons such as toluene or benzene; and for hydrogenation, alcohols such as ethanol or isopropanol. This type of transformation has long been known (see, for example, W. H. Hartung, J. Am. Chem.. Soc. 1928, 50, 3370-3374; R. F. Nystrom and W. G. Brown, /. Am Chem. Soc. 1948, 70, 3738- 3740; W. G. Brown, Organic Reactions Vol. VI (Wiley, New York, 1951), Chapter 10, pp. 469-509; H. C. Brown and B. C. S. Rao, J. Am. Chem. Soc. 1956, 78, 2582-2588). Scheme 30
Figure imgf000042_0001
64 As shown in Scheme 31, substituted benzylamines of Formula 2c (Formula 2 wherein R1 is H) can be prepared from aldehydes by the method of Hart et al. as described in J. Org. Chem. 1983, 48(3), 289-298. Lithium bis(trimethylsilyl)amide (66), which can be prepared by treatment of 1,1,1,3,3,3-hexamethyldisilazane with a strong base such as lithium diisopropylamide or 72-butyllithium, is reacted with an aldehyde of Formula 65 in a suitable solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from -78 °C to room temperature. The addition of a Grignard reagent of Formula 67 then provides an amine of Formula 2c. Scheme 31
Figure imgf000042_0002
65 2c Benzylamines of Formula 2c wherein R2 is CN can also be prepared from aldehydes of Formula 65 as described by M. Wakselman et al. in Bioorg. Med. Chem. 2001, 9(5), 1175— 1183. As shown in Scheme 32, benzylamines having a chiral center denoted by the asterisk (*) in Formula 2d (Formula 2 wherein R1 is H and R2 is other than H) can be prepared enantiomerically enriched with the depicted configuration by the reduction of chiral imines of Formula 68 using the methods analogous to those described U.S. Patent Application Publication 2002/103,400 or Organic Letters 2003, 5(7), 1007-1010. Scheme 32
Figure imgf000043_0001
The chiral imine of Formula 68 comprises a chiral auxiliary group, which transfers chirality to the new chiral center created during reduction. The chiral auxiliary is chosen to provide the new center with the absolute configuration depicted for Formula 2d, as this configuration provides greater herbicidal activity to the compounds of Formula I. As referred to in the context of the present disclosure and claims this configuration is identified as the S-configuration. Examples of reducing reagents useful for reducing the imine include sodium borohydride and lithium aluminum hydride. The chiral auxiliary is removed after the imine is reduced, either by reduction or hydrolysis depending on the choice of chiral auxiliary. Alternatively as shown in Scheme 33, a chiral benzyl amine enriched with configuration shown in Formula 2d can be prepared by reducing an imine of Formula 69 with one of the many chiral reducing agents known in the art. Such chiral reducing agents include enzymes (see, for example, PCT Patent Application Publication WO 03/048151) and chiral complexes (see, for example, J. Chem. Soc, Perkin Trans. 1, 1990, 7, 1859-63 and X. Zhang et al. J. Org. Chem. 2003, 68, 4120-22). Scheme 33
Figure imgf000043_0002
wherein R60 is H or groups such as OH, Cι-C3 alkoxy, C(O)CH3, SiMe3 or optionally substituted phenyl.
The chiral reducing complex or enzyme is chosen to provide a benzylamine enriched with the absolute S-configuration depicted for Formula 2d. Chiral amines of Formula 2d can also be prepared by additional methods taught by L. Storace et al. in Organic Process Research & Development 2002, 6, 54-63. Ideally the benzylamines of Formula 2d are obtained enantiomerically pure, so coupling according to the methods of Schemes 1 and 2 provides the corresponding compounds of Formula I also in enantiomerically pure form. Methods are well known in the art for separating pure enantiomers of chiral amines from enantiomerically enriched or even racemic mixtures. These methods include liquid chromatography on columns comprising a chiral support and recrystallization of salts of benzylamines with chiral carboxylic acids such as tartaric acid. It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula I may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula I. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula I. One skilled in the art will also recognize that compounds of Formula I and. the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromato graphic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. H NMR spectra are reported in ppm downfield from tetramethylsilane; "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, "dd" means doublet of doublets, "ddd" means doublet of doublets of doublets, "dt" means doublet of triplets, "dq" means doublet of quartets, "br s" means broad singlet, "br d" means broad doublet. EXAMPLE 1 Preparation of 2-chloro-N-[(4-fluorophenyl)methyl]-6-methyl-4-propoxy- 3-pyridinecarboxamide (Compound 29) Step A: Preparation of 2-chloro-6-methyl-4-propoxy-3-pyridinecarboxylic acid To 2,4-dichloro-6-methyl-3-pyridinecarboxylic acid (1 g) in N,N-dimethylformamide
(DMF) (10 mL) was added sodium hydride (0.43 g). After gas evolution ceased, 1-propanol (0.4 mL) was added, and the mixture heated at 80 °C overnight. The mixture was cooled and water added. The mixture was extracted with ether to remove any residual oil. The aqueous phase was adjusted to pH 2 using 1 Ν hydrochloric acid and then extracted with ethyl acetate (3x). The combined ethyl acetate extracts were washed with water (3x) then brine and dried (MgSO4). The solvent evaporated in vacuo to leave a solid, which was triturated with 1-chlorobutane-hexanes to provide the title compound as a yellow solid (0.55 g), melting 195-200 °C.
*H ΝMR (DMSO-J6, 300 MHz) 5 13.05 (br s, IH) 7.10 (s, IH), 4.09 (t, 2H), 2.42 (s, 3H), 1.60-1.80 (m, 2H), 0.94 (t, 3H).
Step B : Preparation of 2-chloro-N-[(4-fluorophenyl)methyl]-6-methyl-4-propoxy- 3-pyridinecarboxamide To 2-chloro-6-methyl-4-propoxy-3-pyridinecarboxylic acid (i.e. product of Step A) (0.285 g) was added thionyl chloride (2.5 mL), and the reaction mixture was stirred at room temperature for 1.5 h. The excess thionyl chloride was evaporated in vacuo, and then dichloromethane was added and evaporated in vacuo. The residual oil was dissolved in dichloromethane (approximately 3 mL) and added to a solution of 4-fluorobenzene- methanamine (0.193 g) in dichloromethane (10 mL). An molar excess of PS-DMAP was added, and the reaction mixture was shaken at room temperature overnight and filtered, and the solvent was evaporated in vacuo. The residual oil was triturated with 1-chlorobutane- hexanes (approximately 1:1) to provide the title product, a compound of the present invention, as a white solid (0.316 g). A sample purified by silica gel chromatography using ethyl acetate-hexanes (1:1) as eluant had a melting point of 147-148 °C. !H ΝMR (CDC13, 300 MHz) δ 7.30-7.40 (m, 2H), 7.02 (t, 2H), 6.62 (s, IH), 6.05 (br t, IH), 4.62 (d, 2H), 3.98 (t, 2H), 2.49 (s, 3H), 1.70-1.83 (m, 2H), 0.98 (t, 3H). EXAMPLE 2
Preparation of 2-chloro-N- [( IS)- 1 -(4-methoxyphenyl)ethyl] -6-methyl-4-propoxy-3~pyridine- carboxamide (Compound 103) To 2-chloro-6-methyl-4-propoxy-3-pyridinecarboxylic acid (i.e. product of Example 1, Step A) (100 mg) was added thionyl chloride (2 mL), and the reaction mixture was stirred at room temperature for 2 hours. The excess thionyl chloride was evaporated in vacuo, and dichloromethane was added and evaporated in vacuo. The residual oil was dissolved in dichloromethane (approximately 2 mL) and added to a solution of (αS)-4-methoxy- α-methylbenzenemethanamine (79.2 mg) in dichloromethane (3 mL). A molar excess of PS-DMAP was added, and the reaction mixture was shaken at room temperature overnight. The reaction mixture was then filtered, and the solvent was evaporated in vacuo. The residual oil was triturated with 1-chlorobutane-hexanes (approximately 1:1) to provide the title product, a compound of the present invention, as a white solid (92.3 mg) melting at 110-111 °C.
IH NMR (CDC13, 300 MHz) δ 7.33 (d, 2H), 6.87 (d, 2H), 6.61 (s, IH), 5.88 (br d, IH), 5.29-5.39 (m, IH), 3.96 (t, 2H), 3.80 (s, 3H), 2.48 (s, 3H), 1.73-1.84 (m, 2H), 1.59 (d, 3H), 0.98 (t, 3H). EXAMPLE 3 Preparation of 2-chloro-N-[(4-fluorophenyl)methyl]-6-methyl-4-(l -methylethoxy)- 3-pyridinecarboxamide (Compound 64)
Step A: Preparation of 2,4-dichloro-N-[(4-fluorophenyl)methyl]-6-methyl-3-pyridine- carboxamide To 2,4-dichloro-6-methyl-3-pyridinecarboxylic acid (3.0 g) was added thionyl chloride (25 mL), and the reaction mixture was heated at reflux for 1.5 h. The excess thionyl chloride was evaporated in vacuo, and dichloromethane was added and evaporated in vacuo. The residual brown oil was dissolved in dichloromethane (approximately 5 mL) and added to a solution of 4-fluorobenzenemethanamine (406 mg) and triethylamine (2.6 mL) in dichloromethane (10 mL) cooled to 0 °C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with dichloromethane (2x) with addition of ethyl acetate to keep solids in solution. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The resulting yellow solid was triturated with 1-chlorobutane-hexanes to provide the title compound as a tan solid (3.99 g). A sample purified by silica gel chromatography using ethyl acetate-hexanes (1:1) as eluant, followed by trituration with 1-chlorobutane-hexanes had a melting point of 150- 151 °C. iH ΝMR (CDC13, 300 MHz) δ 7.30-7.40 (m, 2H), 7.17 (s, IH), 7.05 (t, 2H), 6.03 (br t, IH), 4.64 (d, 2H), 2.53 (s, 3H).
Step B: Preparation of 2-chloro-N-[(4-fluorophenyl)methyl]-6-methyl- 4-(l-methylethoxy)-3-pyridinecarboxamide To a solution of 2-propanol (81 μL) in DMF (2 mL) was added sodium hydride
(46 mg). After gas evolution ceased, 2,4-dichloro-N-[(4-fluorophenyl)methyl]-6-methyl- 3-pyridinecarboxamide (i.e. the product of Step A) (324 mg) was added, and the reaction mixture was heated at 80 °C overnight. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate (3x). The combined ethyl acetate extracts were washed with water (3x) then brine and dried (MgSO4), and the solvent was evaporated in vacuo. The resulting oil was purified by silica gel chromatography using ethyl acetate- hexanes (1:1) as eluant to provide the title product, a compound of the present invention, as a white solid (46 mg) melting at 132-133 °C. IH NMR (CDC13, 300 MHz) δ 7.34 (d, 2H), 6.88 (d, 2H), 6.60 (s, IH), 5.82 (br d, IH), 5.27-5.39 (m, IH), 4.57-4.63 (m, IH), 3.80 (s, 3H), 2.48 (s, 3H), 1.59 (d, 3H), 1.33 (dd, 6H). EXAMPLE 4 Preparation of 2-bromo-N-[(4-fluorophenyl)methyl]-6-methyl-4-propoxy- 3-pyridinecarboxamide (Compound 87)
Step A: Preparation of 2,4-bromo-N-[(4-fluorophenyl)methyl]-6-methyl- 3-pyridinecarboxamide To ethyl l,2-dihydro-4-hydroxy-6-methyl-2-oxo-3-pyridinecarboxylate (2.0 g) was added phosphorus oxybromide (10.0 g), and the reaction mixture was heated at reflux for 1.5 h. The reaction mixture was cooled, carefully quenched with water and then extracted with dichloromethane (2x). The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried (MgSO4) and filtered, and the solvent was evaporated in vacuo. The orange tan solid obtained was dissolved in dichloromethane (approximately 10 mL) and added to a solution of 4-fluorobenzenemethanamine (1.21 g) and triethylamine (1.06 g) in dichloromethane (10 mL) cooled to 0 °C. The reaction mixture was stirred at room temperature overnight and then poured into water and extracted with dichloromethane (3x). The combined organic extracts were dried (MgSO4) and filtered, and the solvent was evaporated in vacuo. The resulting yellow foam was triturated with 1-chlorobutane- hexanes-ethyl acetate mixture to provide the title compound as a beige solid (2.13 g).
!H ΝMR (CDCI3, 300 MHz) δ 7.35-7.62 (m, 2H), 7.04 (t, 2H), 6.07 (br s, IH), 4.63 (d, 2H), 2.52 (s, 3H).
Step B: Preparation of 2-bromo-N-[(4-fluoroρhenyl)methyl]-6-methyl-4-propoxy- 3-pyridinecarboxamide To 2,4-dibromo-N-[(4-fluorophenyl)methyl]-6-methyl-3-ρyridinecarboxamide (i.e. the product of Step A) (500 mg) in 3 mL DMF was added 60 mg of sodium hydride. After gas evolution ceased, 1-propanol (0.10 mL) was added, and the mixture was heated at 80 °C overnight. The reaction mixture was cooled, poured into water and extracted with ethyl acetate (3x). The combined ethyl acetate extracts were washed with water (3x), brine, and then dried (MgSO4), and the solvent was evaporated in vacuo to leave the crude product as a brown oil. The crude product was combined with the crude product from a second 500-mg run and purified by silica gel chromatography using as eluant a solvent varying from 1:1 ethyl acetate-hexanes to 100% ethyl acetate. The product-containing fractions were combined and the solvent was evaporated in vacuo. The residue was triturated with 1-chlorobutane-hexanes to provide the title compound as a light yellow solid (309 mg). A sample prepared similarly had a melting point of 145-147 °C. 1H NMR (CDC13, 300 MHz) δ 7.34 (d, 2H), 6.88 (d, 2H), 6.60 (s, IH), 5.82 (br d, IH), 5.27-5.39 (m, IH), 4.57-4.63 (m, IH), 3.80 (s, 3H), 2.48 (s, 3H), 1.59 (d, 3H), 1.33 (dd, 6H). EXAMPLE 5 Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-l-methyl-5-propoxy-lH-pyrazole- 4-carboxamide (Compound 94)
Step A: Preparation of ethyl 2,5-dihydro-l-methyl-5-oxo-lH-pyrazole-4-carboxylate By a modification of a procedure described in World Patent Publication WO 01/23358 (p. 41) for making ethyl 2,3-dihydro-l-methyl-5-oxo-lH-pyrazole-4-carboxylate (a regioisomer of the title compound of Step A), an ethanolic solution of sodium ethoxide (21%, 22.1 g) was added to a stirred solution of methylhydrazine (5 g, 108.5 mmol) and diethyl (ethoxymethylene)propanedioate (23.5 g, 108.5 mmol) in ethanol (80 mL). The mixture was stirred at 60-70 °C under nitrogen for 2 h. After cooling, the mixture was partitioned between aqueous hydrochloric acid (1 Ν, 500 mL) and ethyl acetate (100 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers (400 mL total) were then washed with water (75 mL) and brine (75 mL), and dried (MgSO4). The solution was filtered and the solvent evaporated in vacuo to leave an orange oily residue. Trituration provided a yellowish solid, which was collected by filtration, washed with a small amount of water, and oven dried for several hours to provide the title product (10 g). !Η ΝMR (CDC13) δ 7.95 (s, 1Η), 4.32 (q, 2Η), 3.67(s, 3H), 1.35 (t, 3H).
Step B: Preparation of ethyl 3-chloro-2,5-dihydro-l-methyl-5-oxo-lH-pyrazole- 4-carboxylate By a procedure reported in J. Heterocyclic Chem. 1997, 34, 537, ethyl 2,5-dihydro- l-methyl-5-oxo-lH-pyrazole-4-carboxylate (i.e. the product of Step A) (6.3 g, 37.1 mmol) was combined with N-chlorosuccinimide (12.3 g, 92.5 mmol), and the mixture was heated neat at 80-85 °C overnight. The reaction temperature was lowered to 60 °C, and the mixture was taken up in tetrachloromethane (60 mL) and washed twice with saturated aqueous sodium carbonate (2 x 50 mL), followed by water (50 mL) and brine (50 mL). The organic layer was dried (MgSO4) and filtered, and the solvent was evaporated in vacuo to provide the title compound as an oil (6.0 g). lH ΝMR (CDC13) δ 4.35 (m, 2Η), 3.40 (s, 3H), 1.32 (t, 3H). Step C: Preparation of ethyl 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylate To a stirred solution of ethyl 3-chloro-2,5-dihydro-l-methyl-5-oxo-lH-pyrazole-
4-carboxylate (i.e. the product of Step B) (6 g, 29.3 mmol) and 1-iodopropane (5.5 g,
32.3 mmol) in N,N-dimethylformamide (20 mL) was added powdered potassium carbonate (12.1 g, 88 mmol). The reaction mixture was allowed to stir overnight under nitrogen at room temperature. The reaction mixture was then partitioned between water (50 mL) and ethyl acetate (100 mL). The organic layer was separated and washed with water (3 x 50 mL) and brine (50 mL). The organic layer was dried (MgSO ) and filtered, and the solvent was evaporated in vacuo to give a crude oil. Purification by flash column chromatography on silica gel (3:1 hexanes-ethyl acetate eluant) provided the title product as a clear yellow oil
(2.6 g).
!Η ΝMR (CDC13) δ 4.29 (m, 4Η), 3.65 (s, 3H), 1.82 (q, 2H), 1.37 (t, 3H), 1.04 (t, 3H).
Step D: Preparation of 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylic acid To a stirred solution of ethyl 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylate (i.e. the product of Step C) (2.6 g, 10.5 mmol) in methanol (20 mL) was added aqueous sodium hydroxide (50 wt%, 1.3 g). After stirring for 15 minutes at ambient temperature, water (10 mL) was added, and the resulting cloudy mixture was heated at reflux for 0.5 h. The resulting yellow solution was cooled, and water (20 mL) was added. The resulting mixture was extracted with diethyl ether; the ether- layer was discarded. The separated aqueous layer was acidified to pΗ 2 by adding concentrated hydrochloric acid and was then extracted with ethyl acetate (50 mL). The combined extracts were washed with water (50 mL) and brine (50 mL). After drying (M SO4) and filtering, the solvent was evaporated in vacuo. The remaining oily residue was triturated with a small amount of hexanes to provide a solid, which was collected by filtration. The title compound was isolated as a white solid (1.9 g) melting at 115-117 °C.
!Η ΝMR (CDC13) δ 4.32 (t, 2Η), 3.67 (s, 3H), 1.82 (q, 2H), 1.05 (t, 3H).
Step E: Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-l-methyl-5- propoxy- lH-pyrazole-4-carboxamide To a stirred solution of 3-chloro-l-methyl-5-propoxy-lH-pyrazole-4-carboxylic acid (i.e. the product of Step D) (0.5 g, 2.3 mmol) in dichloromethane (20 mL) was added oxalyl chloride (1.5 g, 11.5 mmol) followed by NN-dimethylformamide (2 drops). A slight exothermic reaction occurred with bubbling. The mixture was heated at reflux for 15 minutes. The solvent was evaporated in vacuo, and the residue was suspended in tetrahydrofuran (anhydrous, 20 mL). To the stirred solution under nitrogen was added (αS)-4-chloro-α-methylbenzenemethanamine (0.5 g, 3.2 mmol), followed by dropwise addition of NN-diisopropylethylamine (0.6 g, 4.6 mmol), causing a cloudy mixture to form. The reaction mixture was then stirred overnight at room temperature. Aqueous hydrochloric acid (1 N, 50 mL) was added, and the mixture was extracted with ethyl acetate (75 mL). The organic layer was separated and washed with IN hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine (50 mL each). The organic layer was dried (MgSO ) and filtered, and the solvent was evaporated in vacuo. The solid residue was suspended in a small amount of hexanes and collected by filtration to provide the title product, a compound of the present invention as a white solid (448 mg) melting at 96-98 °C. IH NMR (CDC13) δ 7.30 (s, 4H), 6.64 (d, IH), 5.24 (q, 2H), 3.64 (s, 3H), 1.76 (q, 2H), 1.54 (d, 3H), 0.99 (t, 3H). EXAMPLE 6 Preparation of N-[(2,4-difluorophenyl)methyl]-l-methyl-5-propoxy-3-(trifluoromethyl)- lH-pyrazole-4-carboxamide (Compound 78) Step A: Preparation of methyl 5-chloro-l-methyl-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylate To a saturated methanolic hydrogen chloride solution (100 mL) was added 5-chloro- l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxylic acid (prepared by the method reported in J. Heterocyclic Chem. 1990, 27, 243-245) (5.0 g, 21.87 mmol). The reaction mixture was then heated at reflux overnight. Evaporation of the solvent in vacuo left a whitesolid. The solid was taken up in ethyl acetate (150 mL), washed with saturated aqueous sodium bicarbonate, water, and brine, and then dried (MgSO4). Evaporation of the solvent in vacuo provided the title compound as a white solid (6.0 g) melting at 81-83 °C. !Η ΝMR (CDCI3) δ 3.94 (s, 3Η), 3.87 (s, 3H).
Step B: Preparation of l-methyl-5-propoxy-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylic acid To a well-stirred cold suspension of sodium hydride (0.18 g, 4.5 mmol) in N,N-dimethylformamide (10 mL) at 0 °C under nitrogen atmosphere, π-propyl alcohol (0.2 mL, 2.5 mmol) was added dropwise. The resulting mixture was stirred for 0.5 hours, and then a solution of methyl 5-chloro-l-methyl-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylate (i.e. the product of Step A) (0.485 g, 2.0 mmol) in N,N-dimethylformamide (5 mL) was added slowly so that the temperature did not rise above 5 °C. The reaction was stirred overnight at room temperature. The solvent was removed in vacuo, and the resulting residue was added to a mixture of aqueous sodium hydroxide solution (2 Ν, 5 mL) and tetrahydrofuran (5 mL) and stirred for 2 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (15 mL). Acidification of the separated aqueous layer with hydrochloric acide (2 Ν) gave a brown precipitate, which was extracted into ethyl acetate (50 mL) and separated. The organic solution was dried (MgSO4), and the solvent was evaporated in vacuo to leave a solid residue, which on purification by flash chromatography on silica gel (1:0 to 2:3 hexanes-ethyl acetate as eluant) afforded the title compound as a white solid (0.15 g) melting at 162-164 °C.
IH NMR (CDC13) δ 4.37 (t, 2H), 3.8 (s, 3H), 1.88 (m, 2H), 1.08 (t, 3H).
Step C: Preparation of N-[(2,4-difluorophenyl)methyl]-l-methyl-5-propoxy- 3-(trifluoromethyl)-lH-pyrazole-4-carboxamide To a solution of l-methyl-5-propoxy-3-(trifluoromethyl)-lH-pyrazole-4-carboxylic acid (i.e. the product of Step B) (0.10 g, 0.4 mmol) in N,N-dimethylformamide (5 mL), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.084 g, 0.44 mmol), 1-hydroxybenzotriazole (0.059 g, 0.44 mmol) and N,N-diisopropylethylamine (0.129 g, 1.0 mmol) were added. The resulting reaction mixture was stirred at room temperature for 0.5 h. Finally, 2,4-difluorobenzenemethanamine (0.063 g, 0.44 mmol) was added dropwise at 0 °C, and the reaction mixture was stirred overnight at room temperature. After evaporating the solvent in vacuo, the residue was partitioned between water (25 mL) and ethyl acetate (25 mL). The organic extract was washed with saturated aqueous bicarbonate solution, hydrochloric acid (2 Ν), and brine, and then dried (MgSO4). Evaporating the solvent in vacuo left a brown solid residue, which on purification by flash chromatography on silica gel (1:0 to 2:1 hexanes-ethyl acetate as eluant) afforded the title product, a compound of the present invention, as an orange solid (0.087 g) melting at 71-73 °C. IH ΝMR (CDC13) δ 7.40 (m, IH), 6.85 (m, 2H), 6.60 (br s, IH), 4.60 (d, 2H), 4.05 (t, 2H), 3.74 (s, 3H), 1.68 (m, 2H), 1.0 (t, 3H). EXAMPLE 7 Preparation of N-[(lS)-l-(4-fluorophenyl)ethyl]-l-methyl-5-(2-propynyloxy)- 3-(trifluoromethyl)-lH-pyrazole-4-carboxamide (Compound 99)
Step A: Preparation of l-methyl-5-(2-propynyloxy)-3-(trifluoromethyl)-lH-pyrazole- 4-carboxylic acid To a well-stirred cold suspension of sodium hydride (0.918 g, 38.25 mmol) in N,N-dimethylformamide (20 mL) at 0 °C under nitrogen atmosphere, propargyl alcohol (1.143 g, 20.4 mmol) was added dropwise. The reaction mixture was stirred for 0.5 h, and then a solution of methyl 5-chloro-l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxylate (i.e. the product of Example 6, Step A) (4.11 g, 17.0 mmol) in N,N-dimethylformamide (10 mL) was added slowly so that the temperature did not rise above 5 °C. The reaction mixture was stirred overnight at room temperature. The solvent was removed in vacuo, and the resulting residue was added to a mixture of aqueous sodium hydroxide solution (2 Ν, 20 mL) and tetrahydrofuran (20 mL) and stirred for 2 h. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (50 mL). Acidification of the separated aqueous layer with hydrochloric acid (2 Ν) gave a brown precipitate, which was extracted with ethyl acetate (200 mL). The separated organic layer was dried (MgSO ), and the solvent was removed in vacuo to leave a brown solid residue, which on purification by flash chromatography on silica gel (1:0 to 2:3 hexanes-ethyl acetate as eluant) afforded the title compound as a white solid (1.8 g) melting at 223-226 °C. 1H NMR (CDC13) δ 10.74 (br s, IH), 5.11 (s, 2H), 3.82 (s, 3H), 2.33 (s, IH). Step B: Preparation of N-[(lS)-l-(4-fluorophenyl)ethyl]-l-methyl-5-(2-propynyloxy)- 3-(trifluoromethyl)-lH-pyrazole-4-carboxamide To a solution of l-methyl-5-(2-propynyloxy)-3-(trifluoromethyl)-lH-pyrazole-
4-carboxylic acid (i.e. the product of Step A) (0.248 g, 1.0 mmol) in N,N-dimethyl- formamide (5 mL), l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.210 g, 1.1 mmol), 1-hydroxybenzotriazole (0.148 g, 1.1 mmol) and N,N-diisopropylethylamine
(0.323 g, 2.5 mmol) were added. The reaction mixture was stirred at room temperature for
0.5 h. Finally, (αS)-4-fluoro-α-methylbenzenemethanamine (0.153 g, 1.1 mmol) was added dropwise at 0 °C, and the reaction mixture was stirred at room temperature overnight. After evaporating the solvent in vacuo, the residue was partitioned between water (25 mL) and ethyl acetate (25 mL). The organic extract was washed with saturated aqueous bicarbonate, hydrochloric acid (2 Ν), and brine, and then dried (MgSO4). Evaporating in vacuo gave a brown oil residue, which on purification by flash chromatography on silica gel (1:0 to 2:1 hexanes-ethyl acetate as eluant) afforded the title product, a compound of the present invention, as a brown oil (0.073 g). The ΝMR spectrum was recorded for another sample of the title product.
*Η ΝMR (CDCI3) δ 7.38 (m, 2H), 7.05 (t, 2H), 6.27 (s, IH), 5.21 (t, IH), 5.01 (s, 2H), 3.80 (s, 3H), 2.57 (s, IH), 1.57 (d, 3H). EXAMPLE 8 Preparation of 3-chloro-N-[(4-fluorophenyl)methyl]-5-propoxy-4-isothiazolecarboxamide (Compound 119)
Step A: Preparation of 3,5-dichloro-N-[(4-fluorophenyl)methyl]-4-isothiazole- carboxamide A mixture of 3,5-dichloro-4-isothiazolecarboxylic acid (prepared according to the method of W.R. Hatchard, J. Org. Chem. 1964, 29, 660-665) (180 mg, 0.908 mmole) and thionyl chloride (3 mL) was heated at reflux for 2 h under nitrogen atmosphere. The reaction mixture was concentrated to leave the intermediate acid chloride as an oil. The acid chloride was dissolved in dichloromethane (3 mL) under nitrogen atmosphere, and the solution was cooled to 0 °C. Triethylamine (230 mg, 2.27 mmol) was added, followed by dropwise addition of a solution of 4-fluorobenzylamine (1 mL) in dichloromethane (1 mL) so that the temperature remained below 5 °C. The stirred reaction mixture was maintained below 5 °C for 10 minutes more, and was then diluted with water and dichloromethane. The layers were separated and the organic layer was washed with water, brine, dried (MgSO4) and concentrated to provide the title compound as a yellow solid (0.6 g). The solid was slurried in hexanes and collected under filtration to provide the title compound as a solid (215 mg) melting at 146-147 °C. !H NMR (CDC13) δ 7.3 (m, 2H), 7.0 (m, 2H), 6.3 (br s, IH, NH), 4.6 (d, 2H, CH2). Step B: Preparation of 3-chloro-N-[(4-fluorophenyl)methyl]-5-propoxy- 4-isothiazolecarboxamide Sodium hydride (55%, 51 mg, 1.18 mmol) was added to a stirred solution of 1-propanol (65 mg, 1.08 mmol) in N,N-dimethylformamide (2 mL) in a scintillation vial under nitrogen atmosphere. After 10 minutes hydrogen evolution was complete. 3,5-Dichloro-N-[(4-fluorophenyl)methyl]-4-isothiazolecarboxamide (i.e. the product of Step A) (300 mg, 0.983 mmol) was then added, and the reaction mixture was heated overnight at 80 °C using a scintillation vial heating block. The reaction mixture was then cooled to room temperature, diluted with water, and extracted with ethyl acetate (3x). The combined organic extracts were washed with water (3x), brine, dried (MgSU4) and concentrated to leave the crude product as as solid (0.350 mg). The product was purified by flash column chromatography using a Supelco (division of Sigma-Aldrich Co., 595 North Harrison Road,. Bellefonte, PA 16823, U.S.A.) DSC-Si SPE Tube prepacked with 5 g of silica gel (50:μm particle diameter, 70 A pore size) and as eluant 20% ethyl acetate - 80% hexanes to obtain fractions containing the desired product (which was more polar than starting material). The fractions were concentrated to leave an solid (170 mg), which was triturated with ether-hexanes and collected by filtration to provide the title product, a compound of the present invention, as a solid (81 mg) melting at 124-125 °C. lH NMR (CDC13) δ 7.29-7.34 (m,2H), 7.0-7.25 (m, 2H), 6.7 (br s, NH), 4.5 (d, 2H, CH2), 4.1 (t, 2H, OCH2), 1.88 (m, 2H, CH2), 0.96 (t, 3H, CH3). EXAMPLE 9 Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methylthio)-3-(trifluoromethyl)- 4-isothiazolecarboxamide (Compound 257)
Step A: Preparation of 5-(methylthio)-3-(trifluoromethyl)-4-isothiazolecarboxylic acid Ethyl 5-(methylthio)-3-(trifluoromethyl)-4-isothiazolecarboxylate (prepared according to method of U.S. Patent 5,324,837, example 5A; 500 mg, 1.84 mmol) was stirred in mixture of ethanol (9 mL) and water (5 mL). Potassium carbonate (2.0 g, 14.56 mmol) was added, and the reaction mixture was stirred for 3 h. Then the pH was adjusted below 2 by addiing aqueous hydrochloric acid (1 Ν). The aqueous layer was extracted with ethyl acetate (3x), and the combined organic layers were dried (MgSO4) and concentrated to leave a solid residue (0.46 g). The solid was slurried in hexanes and collected under filtration to provide the title compound as a solid (393 mg) melting at >225 °C. IH NMR (CDCI3) δ 2.67 (s, 3H), 13.8 (br s, IH).
Step B: Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methylthio)-3-(trifluoro- methyl)-4-isothiazolecarboxamide A mixture of 5-(methylthio)-3-(trifluoromethyl)-4-isothiazolecarboxylic acid (i.e. the product of Step A) (700 mg, 2.88 mmol) and thionyl chloride (9 mL) was heated at reflux under nitrogen atmosphere for 4 h. The reaction mixture was concentrated to leave the intermediate acid chloride as a solid. The acid chloride was dissolved in dichloromethane
(8 mL) under nitrogen atmosphere, and the solution was cooled to 0 °C. Triethylamine
(720 mg, 7.19 mmol) was added, followed by dropwise addition of a solution of (αS)-4-chloro-α-methylbenzenemethanamine (0.4 mL, 2.88 mmol) in dichloromethane
(3 mL) so that the temperature remained below 5 °C. The stirred reaction mixture was maintained below 5 °C for 15 minutes more, and was then diluted with water and dichloromethane. The layers were separated, and the organic layer was washed with water, brine, dried (MgSO4) and concentrated to provide the title compound as a yellow solid (1.25 g). The solid was slurried in hexanes and some diethyl ether and collected under filtration to provide the title product, a compound of the present invention, as a solid (1.0 g) melting at 125-126 °C.
IH ΝMR (CDCI3) δ 1.5 (d, 3H), 2.64 (s, 3H), 5.2 (m5 IH), 6.1 (br s, ΝH), 7.29 (s, 2H), 7.32 (s, 2H). EXAMPLE 10 Preparation of N- [( 1 S)- 1 -(4-chlorophenyl)ethyl]-5-(l -methylethoxy)-3-(trifluoromethyl)- 4-isothiazolecarboxamide (Compound 196)
Step A: Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methylsulfonyl)- 3-(trifluoromethyl)-4-isothiazolecarboxamide N-[(lS)-l-(4-Chlorophenyl)ethyl]-5-(methylthio)-3-(trifluoromethyl)-4-isothiazole- carboxamide (i.e. the product of Example 9, Step B) (100 mg, 0.26 mmol) was dissolved in dichloromethane (4 mL) under nitrogen atmosphere. 3-Chloroperoxybenzoic acid (MCPBA, 77%, 60 mg, 0.26 mmol) was added to the reaction mixture, which was then stirred 1 h at room temperature. More MCPBA (77%, 10 mg, 0.04 mmol) was added, and the reaction mixture was stirred a further 2 h at room temperature to complete the reaction. The reaction mixture was diluted with saturated aqueous sodium bisulfite solution and dichloromethane. After separating the layers, the organic layer was washed with saturated aqueous sodium bicarbonate solution (2x) and brine, and then dried (MgSO4) and concentrated to leave the crude product. The product was purified by flash column chromatography using a Supelco (division of Sigma-Aldrich Co., 595 North Harrison Road, Bellefonte, PA 16823, U.S.A.) DSC-Si SPE Tube prepacked with 5 g of silica gel (50 μm particle diameter, 70 A pore size) and as eluant 5% ethyl acetate - 95% hexanes, followed by 10% ethyl acetate - 90% hexanes, and then 20% ethyl acetate - 80% hexanes to obtain fractions containing the desired product (which is slightly more polar than the starting material). The fractions were concentrated to leave the title compound as a solid (70 mg) melting at 122-123 °C. IH NMR (CDC13) δ 1.6 (d, 3H), 3.3 (s, 3H), 5.3 (m, IH), 6.3 (IH, NH), 7.35 (s, 4H). Step B: Preparation of N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(l-methylethoxy)- 3-(1rifluoromethyl)-4-isothiazolecarboxamide Sodium hydride (55%, 6 mg, 0.121 mmol) was added to a stirred solution of 2-propanol (0.1 mL, 1.3 mmole) in N,N-dimethylformamide (0.5 mL) under nitrogen atmosphere. After 10 minutes hydrogen evolution was complete. Then N-[(lS)-l-(4- chlorophenyl)ethyl]-5-(methylsulfonyl)-3-(trifluoromethyl)-4-isothiazolecarboxamide (i.e. the product of Step A) (50 mg, 0.12 mmol) dissolved in N,N-dimethylformamide (1.0 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 20 minutes before being diluted with water and extracted with diethyl ether (2x). The combined organic extracts were washed with water (3x), brine, dried (Νa2Sθ4) and concentrated to leave the title product, a compound of the present invention, as as a solid (20 mg) melting at 144-145 °C. lΕL NMR (CDCI3) δ 1.49-1.52 (m, 6H), 1.55 (dτ 3H), 4.5 (m, IH), 5.2 (m, IH), 6.6 (IH, . NH), 7.3-7.34 (m, 4H). EXAMPLE 11 Preparation of 2-bromo-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide (Compound 236) Step A: Preparation of methyl 2-bromo-4-hydroxy-6-methylpyridine-3-carboxylate By a modification of the procedure described in Geman patent publication DE2726685 a mixture of methyl cyanoacetate (6.47 mL, 7.2 g, 73 mmol), triethylamine (9 mL, 6.54 g, 65 mmol) and dichloromethane (10 mL) was cooled to 0 °C under nitrogen. A solution of diketene (5 mL, 5.45 g, 65 mmol) in dichloromethane (10 mL) was added dropwise below 0 °C, and then the stirred reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was partitioned between water (20 mL) and dichloromethane (20 mL). The organic layer was separated and extracted with water (2 x 30 mL). The combined aqueous extracts were cooled to 0 °C and acidified to pH 2 by adding concentrated hydrochloric acid. The resulting yellow precipitate was collected by filtration and then dissolved in dichloromethane (150 mL). The solution was dried (MgSO4) and filtered. To the filtrate bromotrimethylsilane (19.3 mL, 22.4 g, 146 mmol) was added dropwise while keeping the temperature of the reaction mixture below 10 °C. After warming to room temperature, the solution was heated at 30 °C overnight. The resulting precipitate was collected by filtration and dried to provide the title compound as a white solid (12.98 g), melting at 166-167 °C.
1H NMR (DMSO- 6) δ 6.77 (s, IH), 3.81 (s, 3H), 2.35 (s, 3H).
Step B: Preparation of methyl 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridine- carboxylate A mixture of methyl 2-bromo-4-hydroxy-6-methylpyridine-3-carboxylate (i.e. the product of Step A) (1.2 g, 4.9 mmol), potassium carbonate (0.81 g, 5.9 mmol), 2-iodopropane (0.51 mL 0.91 g, 5.3 mmol) and N,N-dimethylformamide (7 mL) was heated at 80 °C overnight. After cooling, the reaction mixture was partitioned between water (15 mL) and ethyl acetate (15 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 15 mL). The combined organic extracts were washed with brine and dried (MgSO4). The solution was filtered, and the solvent was evaporated in vacuo to provide the title compound as an amber oil (1.05 g) . !H ΝMR (CDC13) δ 6.66 (s, IH), 4.60-4.75 (m, IH), 3.92 (s, 3H), 2.50 (s, 3H), 1.30- 1.40 (m, 6H).
Step C: Preparation of 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridinecarboxylic acid A mixture of methyl 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridinecarboxylate (i.e. the product of Step B) (1.0 g, 3.5 mmol), aqueous sodium hydroxide solution (50%, 3 mL, 2.3 g, 57.5 mmol) and ethanol (40 mL) was heated at reflux for 1 hour. After cooling, the solvent was evaporated in vacuo. The residue was dissolved in ice water (15 mL) and acidified to pH 1 by adding concentrated hydrochloric acid. Ethyl acetate (20 mL) was added, and the phases were separated. The aqueous phase was extracted with ethyl acetate (2 x 15 mL). The combined organic extracts were washed with brine and dried (MgSO4). The solution was filtered, and the solvent was evaporated in vacuo. The residue was triturated with 20% ethyl acetate/hexanes to provide the title compound as a tan solid (0.74 g) melting at 175-178 °C with apparent decomposition.
!H ΝMR (DMS -d6) δ 13.40 (br s, IH, CO2H), 7.14 (s, IH), 4.70^1.90 (m, IH), 2.42 (s, 3H), 1.26 (d, 6H). Step D: Preparation of 2-bromo-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl- 4-(l-methylethoxy)-3-pyridinecarboxamide) To 2-bromo-6-methyl-4-(l-methylethoxy)-3-pyridinecarboxylic acid (i.e. the product of Step C) (90 mg, 0.33 mmol) was added thionyl chloride (5 mL), and the reaction mixture was stirred at room temperature for 2 h. The excess thionyl chloride was evaporated in vacuo, and dichloromethane was added and evaporated in vacuo. The residual oil was dissolved in dichloromethane (2 mL) and added to a solution of (αS)-4-fluoro-α-methyl- benzenemethanamine (50.4 mg, 36 mmol) in dichloromethane (5 mL). A molar excess of PS-DMAP was added, and the reaction mixture was shaken at room temperature for 2 days. The reaction mixture was then filtered to remove the resin, and hydrochloric acid (1 N, 4 mL) was added. The resulting mixture was dried by filtering through a Narian Chem Elut CE1010 column containing diatomaceous filter aid using dichloromethane as eluant, and the solvent was evaporated in vacuo. Trituration with 7τ-BuCl provided a solid, which was collected by filtration, washed with a small amount of rc-BuCl, and dried to provide the title product, a compound of the present invention, as a white solid (86 mg) melting at 157- 159 °C.
!H ΝMR (CDC13, 300 MHz) δ 7.37-7.44 (m, 2H), 7.03 (d, 2H), 6.63 (s, IH), 5.83 (br d, IH), 5.31-5.43 (m, IH), 4.56-4.68 (m, IH), 2.49 (s, 3H), 1.60 (d, 3H), 1.32 (d, 3H), 1.34 (d, 3H). EXAMPLE 12 Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-propoxy-4-pyridinecarboxamide (Compound 140) Step Al: Preparation of 3-chloro-5-propoxypyridine To a solution of 5-chloro-3-hydroxypyridine (Aldrich, 5 g, 39 mmol) in N,N-dimethyl- formamide (DMF, 60 mL) was added potassium tert-butoxide (1 M in tetrahydrofuran, 43 mL).- After stirring for 20 minutes, 1-ipdopropane. (7.87 g, 46 mmol) was added. The reaction mixture was stirred at about 23 °C for 16 h. The mixture was then diluted with aqueous sodium hydroxide solution (1 M, 100 mL) and extracted with ether (3 x 100 mL) and ethyl acetate (1 x 100 mL). The combined organic layers were dried (MgSO4), and then the solvent was evaporated under reduced pressure. The remaining DMF was removed by drying under vacuum (1 mm Hg (130 Pa)) for several hours to afford the title compound as a tan oil (5.0 g). *H ΝMR (CDCI3) δ 1.03 (m, 3H), 1.84 (m, 2H), 3.95 ( , 2H), 7.19 (m, IH), 8.19 (m, 2H).
Step A2: Alternative preparation of 3-chloro-5-propoxypyridine A solution of 3,5-dichloropyridine (10 g, 67 mmol) in N,N-dimethylformamide (60 mL) was treated with sodium hydride (60% in mineral oil, 5.36 g, 130 mmol). After the reaction mixture was cooled to 0 °C, n-propanol (6.09 g, 100 mmol) was added. The mixture was heated at 60 °C for 1 h and then cooled to 23 °C. The mixture was quenched with water (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure to give the title compound as a tan oil (11.36 g). Step B: Preparation of 3-chloro-5-propoxy-4-pyridinecarboxylic acid To a solution of diisopropylamine (7.37 g, 72 mmol) in tetrahydrofuran cooled to
-70 °C was added n-butyllithium (29.14 mL, 73 mmol). The mixture was stirred at -70 °C for 30 minutes. Then 3-chloro-5-propoxypyridine (i.e. the product of Step Al or A2) (11.36 g, 66 mmol) was added. After stirring at -70 °C for 1.5 h, dry carbon dioxide was bubbled through the reaction mixture for 45 minutes. The mixture was allowed to warm to 23 °C and then diluted with aqueous sodium hydroxide solution (30 mL) and extracted with ether (3 x 50 mL). The mixture was then acidified to pH 2 by addition of 1 N hydrochoric acid. The mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure to leave the title compound as a pale yellow solid (10.87 g). iH NMR (DMSO-d6) δ 0.95 (m, 3H), 1.69 (m, 2H), 4.14 (m, 2H), 8.35 (s, IH), 8.43 (s, IH), 14.0 (br s, IH). Step C: Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-propoxy- 4-pyridinecarboxamide To a suspension of 3-chloro-5-propoxy-4-pyridinecarboxylic acid (i.e. the product of Step C) (5.0 g, 23 mmol) in toluene (20 ml) was added thionyl chloride (30 mL, 415 mmol). The resulting mixture was heated at 60 °C for 2 h. The solution was cooled and evaporated under reduced pressure to leave an oil. This residue was dissolved in tetrahydrofuran (50 mL). (αS)-4-Chloro-α-methylbenzenemethanamine (4.29 g, 28 mmol) and triethylamine (2.79 g, 28 , mmol) were added, and the mixture was stirred at 23 °C for 16 h. Then the reaction mixture was treated with hydrochloric acid (1 Ν, 100 mL). The mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was subjected to flash chromatography on silica gel using as eluant a solvent gradient ranging from dichloromethane (100 %) to ethyl acetate-dichloromethane (30/70). The appropriate fractions were combined and evaporated under reduced pressure to afford the title product, a compound of the present invention, as an oil (5.45 g) which crystallized to form a solid melting at 100-101 °C. lH ΝMR (DMSO-J6) δ 0.97 (m, 3H), 1.57 (d, 3H), 1.81 (m, 2H), 4.09 (m, 2H), 5.32 (m, IH), 6.31 (m, IH), 7.35 (m, 3H), 8.22 (m, 3H). EXAMPLE 13 Preparation of 3-chloiO-4-[[[(lS)-l-(4-chlorophenyl)ethyl]amino]carbonyl]-l-methyl- 5-propoxypyridinium iodide (Compound 189) 3 -Chloro-N- [( 1 S)- 1 -(4-chlorophenyl)ethyl] -5-propoxy-4-pyridinecarboxamide (i.e. the product of Example 12, Step C) (300 mg) was treated with iodomethane (2.5 mL) and stirred at 23 °C. After 1.5 h the reaction mixture was diluted with ether (10 mL) and filtered to isolate a solid. The solid was rinsed with ether and collected to give the title product, a compound of the present invention, as a yellow solid (160 mg) melting at 193-194 °C. 1H NMR (DMSO-d6) δ 0.89 (m, 3H), 1.43 (d, 3H), 1.72 (m, 2H), 4.21 (m, 2H), 4.34 (s, 3H), 5.19 (m, IH), 7.42 (m, 4H), 8.99 (s, IH), 9.13 (s, IH), 9.41 (d, IH). EXAMPLE 14 Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methoxymethoxy)-4-pyridine- carboxamide (Compound 179)
Step A: Preparation of 3-chloro-5-(methoxymethoxy)pyridine To a solution of 5-chloro-3-hydroxypyridine (Aldrich, 5 g, 39 mmol) in acetonitrile (60 mL) was added chloromethyl methyl ether (3.11 g, 39 mmol) followed by potassium carbonate (10.78 g). The mixture was heated at 60 °C for 18 h and then diluted with water (100 mL). The aqueous layer was extracted with ethyl acetate (4 x 100 mL). The combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure to leave the title compound as a yellow oil (5.5 g). !H ΝMR (CDC13) δ 3.49 (s, 3H), 5.30 (s, 2H), 7.42 (s, IH), 8.26 (s, IH), 8.31 (s, IH).
Step B : Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methoxy- methoxy)-4-pyridinecarboxamide To a solution of diisopropylamine (7.37 g, 72 mmol) in tetrahydrofuran (30 mL) cooled to -70 °C was added n-butyllithium (29.14 mL, 73 mmol). The mixture was stirred at this temperature for 30 minutes. Then 3-chloro-5-(methoxymethoxy)pyridine (i.e. the product of Step A) (5.5 g, 32 mmol) dissolved in tetrahydrofuran (10 mL) was added. After stirring at -70 °C for 1.5 h, l-chloro-4-[(lS)-l-isocyanatoethyl]benzene (5.7 g, 32 mmol) dissolved in tetrahydrofuran (10 ml) was added. The reaction mixture was allowed to warm to 23 °C and was then diluted with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried (MgSU4) and evaporated under reduced pressure. The residue was subjected to flash chromatography on silica gel using as eluant a solvent gradient ranging from dichloromethane (100 %) to ethyl acetate-dichloromethane (20/80). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to leave the title product, a compound of the present invention, as an oil (5.45 g). !H ΝMR (CDCI3) δ 1.61 (d, 3H), 3.45 (s, 3H), 5.20 (m, 2H), 5.35 (m,lH), 6.11 (d, IH), 7.34 (m, IH), 7.35 (m, 3H), 8.30 (s, IH), 8.40 (s, IH). EXAMPLE 15 Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-[(2-chloro-2-propenyl)oxy]- 4-pyridinecarboxamide (Compound 205)
Step A: Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-hydroxy- 4-pyridinecarboxamide To a solution of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-(methoxymethoxy)- 4-pyridinecarboxamide (i.e. the product of Example 14, Step B) (2.3 g, 6.5 mmol) in ether (20 mL) was added a solution of hydrochloric acid in ether (1 Ν, 45 mL). The mixture was stirred at ambient temperature for 55 h and was then treated with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried (MgSU4), and the solvent was evaporated under reduced pressure to leave the title compound (2.08 g).
*H ΝMR (CDC13) δ 1.62 (d, 3H), 5.26 (m, IH), 7.33 (m, 4H), 7.94 (br s, IH), 8.15 (s, IH), 8.35 (s, IH). Step B: Preparation of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-[(2-chloro- 2-propenyl)oxy]-4-pyridinecarboxamide To a solution of 3-chloro-N-[(lS)-l-(4-chlorophenyl)ethyl]-5-hydroxy-4-pyridine- carboxamide (i.e. the product of Step A) (0.3 g, 1 mmol) in acetonitrile (10 mL) was added 2,3-dichloro-l-propene (0.106, 1 mmol) followed by potassium carbonate (0.251 g). The mixture was treated with sodium iodide (30 mg) and stirred at 23 °C for 18 h. The mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were dried (MgSU4) and evaporated under reduced pressure. The residue was subjected to flash chromatography on silica gel using as eluant a solvent gradient ranging from dichloromethane (100 %) to ethyl acetate-dichloromethane (50/50). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to leave the title product, a compound of the present invention, as an oil (0.08 g). lH ΝMR (CDCI3) δ 8.31 (s, IH), 8.20 (s, IH), 7.34 (m, 4H), 6.12 (d, IH), 5.51 (d, 2H), 5.36 (m, IH), 4.68 (s, 2H), 1.61 (d, 3H). By the procedures described herein together with methods known in the art, the following compounds of Tables 1A to 4 can be prepared. In the Tables which follow, CΝ means cyano and ΝO2 means nitro, S(O) means sulfinyl, and S(O)2 means sulfonyl. TABLE 1A
Figure imgf000061_0001
R is H; R1 is H; R2 is H; R6 is CH3 ; R5 is Cl; Y is O.
R (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2.CH3 4-C1 CH2C≡CH 4-C1
CH2CH2CH3 .. 4-SCH3 CH2p≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡ CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡ CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡ CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡ CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡ CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)G≡ CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡ CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡ CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-C1 CH(CH3)C≡ CH 4-C1
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡ CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡ CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3 R is H; R1 is H; R2 is H; R6 is CH3; R5 is Cl; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CF3 4-C1 cyclopropylmethyl 4-C1
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-C1 CH2CH2CN 4-C1
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)CF3 4-F CH(CH3)2 4-CH3
CH(CH3)CF3 4-CN CH(CH3)2 2-F
CH(CH3)CF3 4-OCH3 CH(CH3)2 3-CF3
CH(CH3)CF3 4-CH3 CH(CH3)2 2,4-di-F
CH(CH3)CF3 2-F CH(CH3)2 2,3-di-Cl-4-OCH3
CH(CH3)2 4-F CH(CH3)2 4-C1
CH(CH3)2 4-CN CH(CH3)2 4-SCH3
CH(CH3)2 4-OCH3 CH(CH3)2 4-OCF3
CH(CH3)2 3-OCH3 CH(CH3)CF3 4-OCH3
CH(CH3)CF3 3-OCH3 CH(CH3)CF3 4-F
R is H; R1 is H; R2 i s H; R6 is CH3; R5 is Br; Y is O.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH(CH3)2 3-OCH3
CH2CH2CH3 4-CN CH(CH3)CF3 4-F
CH2CH2CH3 4-OCH3 CH(CH3)CF3 4-CN a
CH2CH2CH3 4-CH3 CH(CH3)CF3 4-OCH3
CH2CH2CH3 3-CF3 CH(CH3)CF3 4-CH3
CH2CH2CH3 4-C1 CH(CH3)CF3 3-CF3
CH2CH2CH3 4-SCH3 CH(CH3)CF3 4-C1
CH2CH2CH3 4-OCF3 CH(CH3)CF3 4-SCH3 R is H; R1 is H; R is H; R° is CH3; R3 is Br; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 3-OCH3 CH(CH3)CF3 4-OCF3 CH(CH3)2 4-F CH(CH3)CF3 3-OCH3 CH(CH3)2 4-CN CH2CH(CH3)2 4-F CH(CH3)2 4-OCH3 CH2CH2CF3 4-CN CH(CH3)2 4-CH3 CH2CH2CH2CH3 4-OCH3 CH(CH3)2 3-CF3 CH2C≡CH 4-CH3 CH(CH3)2 4-C1 CH(CH3)C≡CH 2-F CH(CH3)2 4-SCH3 cyclopropylmethyl 3-CF3 CH(CH3)2 4-OCF3 cyclopentyl 4-C1
R is H; R1 is H; R2 is CH3; R5 is Cl; R6 is CH3; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-C1 CH2C≡CH 4-C1
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-C1 CH(CH3)C≡CH 4-C1
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F R is H; R1 is H; R2 is CH3; R5 is Cl; R6 is CH3; Y is O.
R4 (R3)m R4 (R3)m
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-C1 cyclopropylmethyl 4-C1
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-C1 CH2CH2CN 4-C1
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)CF3 4-F CH(CH3)2 4-CH3
CH(CH3)CF3 4-CN CH(CH3)2 2-F
CH(CH3)CF3 4-OCH3 CH(CH3)2 3-CF3
CH(CH3)CF3 4-CH3 CH(CH3)2 2,4-di-F
CH(CH3)CF3 2-F CH(CH3)2 2,3-di-Cl-4-OCH3
CH(CH3)2 4-F CH(CH3)2 4-C1
CH(CH3)2 4-CN CH(CH3)2 4-SCH3
CH(CH3)2 4-OCH3 CH(CH3)2 4-OCF3
CH(CH3)2 3-OCH3 CH(CH3)CF3 4-OCH3
CH(CH3)CF3 3-OCH3 CH(CH3)CF3 4-F
R is H; R1 is H; R2 is CH3; R5 is Cl; R6 is H; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2G≡CH 4-CN R is H; R1 is H; R2 1 s CH3; R5 is Cl; R6 ij H; Y is O.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-C1 CH2C≡CH 4-C1
CH2CH2CH3 4-SCH3 CH C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CsCH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH -. 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH . 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-C1 CH(CH3)C≡CH 4-C1
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-C1 cyclopropylmethyl 4-C1
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F R is H; R1 is H; R2 is CH3; R5 is Cl; R6 is H; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-0CH3
CH2CH2CH2CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)CF3 4-F CH(CH3)2 4-CH3
CH(CH3)CF3 4-CN CH(CH3)2 2-F
CH(CH3)CF3 4-OCH3 CH(CH3)2 3-CF3
CH(CH3)CF3 4-CH3 CH(CH3)2 2,4-di-F
CH(CH3)CF3 2-F CH(CH3)2 2,3-di-Cl-4-0CH3
CH(CH3)2 4-F CH(CH3)2 4-Cl CH(CH3)2 4-CN CH(CH3)2 4-SCH3
CH(CH3)2 4-OCH3 CH(CH3)2 4-OCF3
R is H; R1 is H; R2 i s H; R5 is Cl; R6 is H , Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-0CH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)G≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F R is H; R1 is H; R2 is H; R5 is Cl; R6 is H; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)CaCH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylm ethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)CF3 4-F CH(CH3)2 4-CH3
CH(CH3)CF3 4-CN CH(CH3)2 2-F
CH(CH3)CF3 4-OCH3 CH(CH3)2 3-CF3
CH(CH3)CF3 4-CH3 CH(CH3)2 2,4-di-F
CH(CH3)CF3 2-F CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)2 4-F CH(CH3)2 4-Cl CH(CH3)2 4-CN CH(CH3)2 4-SCH3 CH(CH3)2 4-OCH3 CH(CH3)2 4-OCF3 R is H; R1 is H; R2 i s CH3; R5 is Br; R6 is CH3; Y is O.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2G≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2CsCH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CΞCH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN R is H; R1 is H; R2 is CH3; R5 is Br; R6 is CH3; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)CF3 4-F CH(CH3)2 4-CH3
CH(CH3)CF3 4-CN CH(CH3)2 2-F
CH(CH3)CF3 4-OCH3 CH(CH3)2 3-CF3
CH(CH3)CF3 4-CH3 CH(CH3)2 2,4-di-F
CH(CH3)CF3 2-F CH(CH3)2 2,3-di-Cl-4-OCH3
CH(CH3)2 4-F CH(CH3)2 4-Cl CH(CH3)2 4-CN CH(CH3)2 4-SCH3 CH(CH3)2 4-OCH3 CH(CH3)2 4-OCF3 CH(CH3)2 3-OCH3 CH(CH3)CF3 4-OCH3 CH(CH3)CF3 3-OCH3 CH(CH3)CF3 4-F
R is H; R1 is H; R2 i s CH3; R5 is F; R6 is CH3; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡CH 4-OCH3 R is H; R1 is H; R2 is CH3; R5 is F; R6 is CH3; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)CsCH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)CF3 4-F CH(CH3)2 4-CH3
CH(CH3)CF3 4-CN CH(CH3)2 2-F
CH(CH3)CF3 4-OCH3 CH(CH3)2 3-CF3
CH(CH3)CF3 4-CH3 CH(CH3)2 2,4-di-F
CH(CH3)CF3 2-F CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)2 4-F CH(CH3)2 4-Cl R is Hj R s Ht R^ is CHs; R-> is F; R° is CH3; Y is O.
R4 (R3)m R4 (R3)m
CH(CH3)2 4-CN CH(CH3)2 4-SCH3
CH(CH3)2 4-OCH3 CH(CH3)2 4-OCF3
CH(CH3)2 3-OCH3 CH(CH3)CF3 4-OCH3
CH(CH3)CF3 3-OCH3 CH(CH3)CF3 4-F
R is H; R1 is H; R2 is H; R5 is Cl; R6 is CH3; Y i 3 0.
R4 (R3)m R4 (R3)m
CH2CF3 4-F CH2C6H5 2,4-di-F
CH2CH2N02 4-CN p-C6H4OCH3 2,3-di-Cl-4-OCH3
2-Cl-cyclohexyl 4-OCH3 CH2CH2CH3 4-N02
CH2(2-Cl-cyclohexyl) 4-CH3 CH2CH(CH3)2 4-cyclopropyl
CH2CH=CH2 2-F CH2CH2CH2CH3 4-CH2OCH3
CH2C(C1)=CH2 3-CF3 CH2C≡CH 3-CH2OH
CH2CH(C1)CH2C≡CH 2,4-di-F CH2CH2CH3 3-CH=CH2
CH2OCH3 2,3-di-Cl-4-OCH3 CH2CH(CH3)2 3-CH2C≡H
CH2CH20(cyclohexyl) 4-Cl CH2CH2CH2CH3 2-OH tetrahydrofuran-2-yl 4-SCH3 CH2C≡CH 3-SCF3
CH2CH2OCH=CH2 4-OCF3 CH2CH2CH3 3-S(0)2CF3
CH2CH2OCH2CH2C≡CH 4-F CH2CH(CH3)2 4-S(0)CH3
CH2CH2SCH3 4-CN CH2CH2CH2CH3 4-S(0)2CH3
CH2CH2S(0)CH3 4-OCH3 CH2C≡CH 3-S(0)2CH2CH=CH2
CH2CH2S(0)2CH3 4-CH3 CH2CH2CH3 4-SCH2C≡CH
CH2CH2S(cyclopentyl) 2-F CH2CH(CH3)2 4-S(0)2CH2C≡CH
CH2CH2SCH=CH2 3-CF3 CH2CH2CH2CH3 2-NHCH3
CH2CH2SCH2C≡CH 2,4-di-F CH2C≡€H 3-N(CH3)2
CH2CH=CHCH2OCH3 2,3-di-Cl-4-OCH3 CH2CH2CH3 4-NH-cyclopropyl
CH2C≡CCH2OCH3 4-Cl CH2CH(CH3)2 3-C(=0)CH3
CH2CH=CHCH2SCH3 4-SCH3 CH2CH2CH2CH3 4-CONHCH3
CH2CH2Si(CH3)3 4-OCF3 CH2C≡CH 2-CON(CH3)2
N=C(H)CH3 4-F CH2CH2CH3 4-Si(CH3) 3
N=C(CH3)2 4-CN CH2CH(CH3)2 4-C6H5
N(CH3)2 4-OCH3 CH2CH2CH2CH3 3-OC6H5
CH2C(=0)CH3 4-CH3 CH2C≡CH 4- C6H4-p-Cl
CH2C(=NOCH3)CH3 2-F CH2CH2CH3 4-OC6H4-p-Cl
CH2N(CH3)2 3-CF3 CH2CH(CH3)2 4-(ρyrazol-l-yl)
CH2-(cyclopropyl-2-CH3) 4-F TABLE IB
Figure imgf000072_0001
R is H; R4 is CH2CH2CH3; R5 is Cl; R6 is CH3; Y is O.
Rl R2 (R3)m Rl R2 (R3)m
CH3 CH3 4-Cl H CH2OCH3 4-F
H CH2CH3 4-Cl H CN 4-F
H CF3 4-Cl H C02CH3 4-F
H cyclopropyl 4-Cl CH3 CH3 4-OCH3
H CH2OCH3 4-Cl H CH2CH3 4-OCH3
H CN 4-Cl H CF3 4-OCH3
H C02CH3 4-Cl H cyclopropyl 4-OCH3
CH3 CH3 4-F H CH2OCH3 4-OCH3
H CH2CH3 4-F H CN 4-OCH3
H CF3 4-F H C02CH3 4-OCH3
H cyclopropyl 4-F H OCH3 4-CH3
R is H R4 is CH(CH3)2; R5 is Br; R6 is CH 3; Y is O.
Rl R2 (R3)m Rl R2 (R3)m
CH3 CH3 4-Cl H CH2OCH3 4-F
H CH2CH3 4-Cl H CN 4-F
H CF3 4-Cl H C02CH3 4-F
H cyclopropyl 4-Cl CH3 CH3 4-OCH3
H CH2OCH3 4-Cl H CH2CH3 4-OCH3
H CN 4-Cl H CF3 4-OCH3
H C02CH3 4-Cl H cyclopropyl 4-OCH3
CH3 CH3 4-F H CH2OCH3 4-OCH3
H CH2CH3 4-F H CN 4-OCH3
H CF3 4-F H C02CH3 4-OCH3
H cyclopropyl 4-F H OCH3 4-CH3 TABLE IC
Figure imgf000073_0001
R is H; Rl is H; R2 is CH3; (R3)m is 4-Cl; R4 is CH2CH2CH3. R5 R6 Y R= Rc
S Cl CH3 0 SCH3 CH3 S(=0) Cl CH3 0 SCF3 CH3 s SCH3 CH3 0 C02CH3 CH3
NH Cl CH3 0 Cl Cl
NCH3 Cl CH3 0 Cl CN
O H CH3 0 Cl CF3 o CH2CH3 CH3 0 Br CF3 o CH3 CH3 0 Cl cyclopropyl o CF3 CH3 0 > CI OCH3 o cyclopropyl CH3 0 Cl OCF3 o OCH3 CH3 0 Cl SCH3 o OCF3 CH3 0 Cl SCF3
R is H; Rl is H; R2 is CH3; (R3)m is 4-F; R4 is CH2CH2CH3.
Y R= R6 R5 R6 s Cl CH3 0 SCH3 CH3
S(=0) Cl CH3 0 SCF3 CH3 s SCH3 CH3 0 C02CH3 CH3
NH Cl CH3 0 Cl Cl
NCH3 Cl CH3 0 Cl CN
0 H CH3 0 Cl CF3
0 CH2CH3 CH3 0 Br CF3
0 CH3 CH3 0 Cl cyclopropyl
0 CF3 CH3 0 Cl OCH3
0 cyclopropyl CH3 0 Cl OCF3
0 OCH3 CH3 0 Cl SCH3
0 OCF3 CH3 0 Cl SCF3 R is H; Rl is H; R2 is CH3; (R3)m is 4-OCH3; R4 is CH2CH2CH3 R3 R6 R5 R6 s Cl CH3 0 SCH3 CH3
S(=0) Cl CH3 0 SCF3 CH3 s SCH3 CH3 0 C02CH3 CH3
NH Cl CH3 0 Cl Cl
NCH3 Cl CH3 0 Cl CN
0 H CH3 0 Cl CF3
0 CH2CH3 CH3 0 Br CF3
0 CH3 CH3 0 Cl cyclopropyl
0 CF3 CH3 0 Cl OCH3
0 cyclopropyl CH3 0 Cl OCF3
0 OCH3 CH3 0 Cl SCH3
0 OCF3 CH3 0 Cl SCF3 TABLE 2A
Figure imgf000074_0001
R is H; R1 is H; R2 1 s CH3; R5 is Cl; R6a is H; Y is O; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)CF3 4-F
CH2CH(CH3)2 4-CN CH(CH3)CF3 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CF3 4-OCH3 R is H; Rl is H; R2 i s CH3; R5 is Cl; R6a s H; Y is 0; q is 0.
R4 (R3)m R4 (R3)m
CH2CH(CH3)2 4-CH3 CH(CH3)CF3 4-CH3
CH2CH(CH3)2 2-F CH(CH3)CF3 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F CH(CH3)2 4-F
CH2CH2CH2CH3 4-CN CH(CH3)2 4-CN
CH2CH2CH2CH3 4-OCH3 CH(CH3)2 4-OCH3
CH2CH2CH2CH3 4-CH3 CH(CH3)2 4-CH3
CH2CH2CH2CH3 2-F CH(CH3)2 2-F
CH2CFI2CH2CH3 3-CF3 CH(CH3)2 3-CF3
CH2CH2CH2CH3 2,4-di-F CH(CH3)2 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH(CH3)2 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH(CH3)2 4-Cl
CH2CH2CH2CH3 4-SCH3 CH(CH3)2 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH(CH3)2 4-OCF3
R is H; Rl is H; R2 is H; R5 is Cl; R6a is I I; Y is O; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN R is H; Rl is H; R2 is H; R5 is Cl; R6a is H; Y is 0; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)CF3 4-F
CH2CH(CH3)2 4-CN CH(CH3)CF3 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CF3 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)CF3 4-CH3
CH2CH(CH3)2 2-F CH(CH3)CF3 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)G≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl ' 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F CH(CH3)2 4-F
CH2CH2CH2CH3 4-CN CH(CH3)2 4-CN
CH2CH2CH2CH3 4-OCH3 CH(CH3)2 4-OCH3
CH2CH2CH2CH3 4-CH3 CH(CH3)2 4-CH3
CH2CH2CH2CH3 2-F CH(CH3)2 2-F R is H; Rl is H; R2 is H; R5 is Cl; R^ is H; Y is O; q is 0.
R (R3)m (R3)m
CH2CH2CH2CH3 3-CF3 CH(CH3)2 3-CF3
CH2CH2CH2CH3 2,4-di-F CH(CH3)2 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH(CH3)2 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH(CH3)2 4-Cl
CH2CH2CH2CH3 4-SCH3 CH(CH3)2 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH(CH3)2 4-OCF3
R is H; Rl is H; R2 i s CH3; R5 is Br; R6a is H; Y is 0; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)CF3 4-F
CH2CH(CH3)2 4-CN CH(CH3)CF3 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CF3 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)CF3 4-CH3
CH2CH(CH3)2 2-F CH(CH3)CF3 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F R is H; Rl is H; R2 is CH3; R5 is Br; R6a is H; Y is O; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F CH(CH3)2 4-F
CH2CH2CH2CH3 4-CN CH(CH3)2 4-CN
CH2CH2CH2CH3 4-OCH3 CH(CH3)2 4-OCH3
CH2CH2CH2CH3 4-CH3 CH(CH3)2 4-CH3
CH2CH2CH2CH3 2-F CH(CH3)2 2-F
CH2CH2CH2CH3 3-CF3 CH(CH3)2 3-CF3
CH2CH2CH2CH3 2,4-di-F CH(CH3)2 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH(CH3)2 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH(CH3)2 . 4-Cl
CH2CH2CH2CH3 4-SCH3 CH(CH3)2 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH(CH3)2 4-OCF3
R is H; Rl is H; R2 i s CH3; R5 is F; R6a i£ > H; Y is O; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)CF3 4-F
CH2CH(CH3)2 4-CN CH(CH3)CF3 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CF3 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)CF3 4-CH3
CH2CH(CH3)2 2-F CH(CH3)CF3 2-F R is H; Rl is H; R2 is CH3; R5 is F; R6a is H; Y i 3 O; q is 0.
R4 (R3)m R4 (R3)m
CH2CH(CH3)2 3-CF3 CH(C H3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡€H 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F CH(CH3)2 4-F
CH2CH2CH2CH3 4-CN CH(CH3)2 4-CN
CH2CH2CH2CH3 4-OCH3 CH(CH3)2 4-OCH3
CH2CH2CH2CH3 4-CH3 CH(CH3)2 4-CH3
CH2CH2CH2CH3 2-F CH(CH3)2 2-F
CH2CH2CH2CH3 3-CF3 CH(CH3)2 3-CF3
CH2CH2CH2CH3 2,4-di-F CH(CH3)2 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH(CH3)2 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH(CH3)2 4-Cl
CH2CH2CH2CH3 4-SCH3 CH(CH3)2 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH(CH3)2 4-OCF3
R is H; Rl is H; R2 is H; R5 is Cl; R6a is I 1; Y is 0; q is 0.
R4 (R3)m R (R3)m
CH2CF3 4-F CH2C6H5 2,4-di-F
CH2CH2N02 4-CN p-C6H4OCH3 2,3-di-Cl-4-OCH3
2-Cl-cyclohexyl 4-OCH3 CH2CH2CH3 4-N02
CH2(2-Cl-cyclohexyl) 4-CH3 CH2CH(CH3)2 4-cyclopropyl
CH2CH=CH2 2-F CH2CH2CH2CH2 4-CH2OCH3 R is H; R1 is H; R2 is H; R5 is Cl; R6a is H; Y is 0; q is 0.
R4 (R3)m R4 (R3)m
CH2C(C1)=CH2 3-CF3 CH2CsCH 3-CH2OH
CH2CH(C1)CH2C≡CH 2,4-di-F CH2CH2CH3 3-CH=CH2
CH2OCH3 2,3-di-Cl-4-OCH3 CH2CH(CH3)2 3-CH2C≡H
CH2CH20(cyclohexyl) 4-Cl CH2CH2CH2CH3 2-OH tetrahydrofuran-2-yl 4-SCH3 CH2C≡CH 3-SCF3
CH2CH2OCH=CH2 4-OCF3 CH2CH2CH3 3-S(0)2CF3
CH2CH2OCH2CH2C≡CH 4-F CH2CH(CH3)2 4-S(0)CH3
CH2CH2SCH3 4-CN CH2CH2CH2CH3 4-S(0)2CH3
CH2CH2S(0)CH3 4-OCH3 CH2C≡CH 3-S(0)2CH2CH=CH2
CH2CH2S(0)2CH3 4-CH3 CH2CH2CH3 4-SCH2C≡CH
CH2CH2S(cyclopentyl) 2-F CH2CH(CH3)2 4-S(0)2CH2C≡CH
CH2CH2SCH=CH2 3-CF3 CH2CH2CH2CH3 2-NHCH3
CH2CH2SCH2C≡CH 2,4-di-F CH2C≡CH 3-N(CH3)2
CH2CH=CHCH2OCH3 2,3-di-Cl-4-OCH3 CH2CH2CH3 4-NH-cyclopropyl
CH2C≡CCH2OCH3 4-Cl CH2CH(CH3)2 3-C(=0)CH3
CH2CH=CHCH2SCH3 4-SCH3 CH2CH2CH2CH3 4-CONHCH3
CH2CH2Si(CH3)3 4-OCF3 CH2C≡CH 2-CON(CH3)2
N=C(H)CH3 4-F CH2CH2CH3 4-Si(CH3) 3
N=C(CH3)2 4-CN CH2CH(CH3)2 4-C6H5
N(CH3)2 4-OCH3 CH2CH2CH2CH3 3-OC6H5
CH2C(=0)CH3 4-CH3 CH2C≡CH 4- C6H4-p-Cl
CH2C(=NOCH3)CH3 2-F CH2CH2CH3 4-OC6H4-p-Cl
CH2N(CH3)2 3-CF3 CH2CH(CH3)2 4-(pyrazol-l-yl)
CH2-(cyclopropyl-2-CH3) 4-F
R is H; Rl is H; R2 is CH3; R5 is Cl; R6a ιs H; Y is S; q is O.
R4 (R3)r n R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C :≡CH 4-Cl R is H; Rl is H; R2 is CH3; R5 is Cl; R6a i s H; Y is S; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)CF3 4-F
CH2CH(CH3)2 4-CN CH(CH3)CF3 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CF3 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)CF3 4-CH3
CH2CH(CH3)2 2-F CH(CH3)CF3 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F CH(CH3)2 4-F
CH2CH2CH2CH3 4-CN CH(CH3)2 4-CN
CH2CH2CH2CH3 4-OCH3 CH(CH3)2 4-OCH3
CH2CH2CH2CH3 4-CH3 CH(CH3)2 4-CH3
CH2CH2CH2CH3 2-F CH(CH3)2 2-F
CH2CH2CH2CH3 3-CF3 CH(CH3)2 3-CF3
CH2CH2CH2CH3 2,4-di-F CH(CH3)2 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH(CH3)2 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH(CH3)2 4-Cl
CH2CH2CH2CH3 4-SCH3 CH(CH3)2 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH(CH3)2 4-OCF3 R is H; Rl is H; R2 i s CH3; R5 is Cl; R6a is H; Y is NH; q is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡€H 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)CF3 4-F
CH2CH(CH3)2 4-CN CH(CH3)CF3 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)CF3 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)CF3 4-CH3
CH2CH(CH3)2 2-F CH(CH3)CF3 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F CH(CH3)2 4-F
CH2CH2CH2CH3 4-CN CH(CH3)2 4-CN
CH2CH2CH2CH3 4-OCH3 CH(CH3)2 4-OCH3 R is H; R1 is H; R2 is CH3; R5 is Cl; R6a is H; Y is NH; q is 0.
R4 (R3) m R4 (R3). m
CH2CH2CH2CH3 4-CH3 CH(CH3)2 4-CH3 CH2CH2CH2CH3 2-F CH(CH3)2 2-F CH2CH2CH2CH3 3-CF3 CH(CH3)2 3-CF3 CH2CH2CH2CH3 2,4-di-F CH(CH3)2 2,4-di-F CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH(CH3)2 2,3-di-Cl-4-OCH3 CH2CH2CH2CH3 4-Cl CH(CH3)2 4-Cl CH2CH2CH2CH3 4-SCH3 CH(CH3)2 4-SCH3 CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3 TABLE 2B
Figure imgf000083_0001
R is H; R4 is CH(CH3)2; R5 is Br; R6a is H; Y is O; q is 0.
R_ R _ (R3) m R1 R^ (R3) m CH3 CH3 4-Cl H CH2OCH3 4-F
H CH2CH3 4-Cl H CN 4-F
H CF3 4-Cl H C02CH3 4-F
H cyclopropyl 4-Cl CH3 CH3 4-OCH3
H CH2OCH3 4-Cl H CH2CH3 4-OCH3
H CN 4-Cl H CF3 4-OCH3
H C02CH3 4-Cl H cyclopropyl 4-OCH3
CH3 CH3 4-F H CH2OCH3 4-OCH3
H CH2CH3 4-F H CN 4-OCH3
H CF3 4-F H C02CH3 4-OCH3
H cyclopropyl 4-F H OCH3 4-CH3 TABLE 2C
Figure imgf000083_0002
R is H; Rl is H, R2 is Me, R4 is CH2CH2CH3; R5 is Cl; (R3)m is 4-Cl; Y is O; q is 1.
R6a Example Counter Ion Rba Example Counter Ion
Me Clθ Et I©
Me Brθ Et BF4 Θ
Me Iθ CH2CF3 Iθ
Me BF4 Θ CH2CF3 OS(0)2CF3 θ
Me PF6© propargyl Brθ
Me OS(0)2CF3 θ allyl Brθ
Me OS(0)2(CF2)3CF3 θ c-pentyl Tθ TABLE 3
Figure imgf000084_0001
R is H; Rl is H; R2 is H; R5 is CF3 R7 is CH3; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2G≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4 -OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡ CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡ CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡ CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡ CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡ -CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡ CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡ CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4 -OCH3 CH(CH3)C≡ -CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(C] Eϊ3)0 CH 4-Cl R is H; Rl is H; R2 iε H; R5 is CF3; R7 is CH3; Y is 0.
R4 (R3)m R (R3)m
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)2 4-F CH(CH3)2 2,4-di-F
CH(CH3)2 4-CN CH(CH3)2 2,3-di-Cl-4-OCH3
CH(CH3)2 4-OCH3 CH(CH3)2 4-Cl
CH(CH3)2 4-CH3 CH(CH3)2 4-SCH3
CH(CH3)2 2-F CH(CH3)2 4-OCF3
CH(CH3)2 3-CF3
R is H; Rl is H; R2 is CH3; R5 is CF3; R7 is CH3; Y is O.
R4 (Rj) m R4 (R ): m
CH2CH2CH3 4-F CH2C≡CH 4-F CH2CH2CH3 4-CN CH2C≡CH 4-CN R is H; Rl is H; R2 is CH3; R5 is CF3; R7 is CH3; Y is O.
R (R3)m R4 (R3)m
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
Figure imgf000087_0001
a u a u a
Figure imgf000087_0002
u
R is H; R1 is H; R2 is , H; R7 is CH3; R5 is Cl; Y is 0
R4 (R3)m R4 (R3)m
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡C H 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylm ethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3 CH(CH3)2 4-F CH(CH3)2 2,4-di-F CH(CH3)2 4-CN CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)2 4-OCH3 CH(CH3)2 4-Cl CH(CH3)2 4-CH3 CH(CH3)2 4-SCH3 CH(CH3)2 2-F CH(CH3)2 4-OCF3 CH(CH3)2 3-CF3
R is H; Rl is H; R2 is CH3; R5 is Cl; R7 is CH3; Y is O.
R (R3)m R (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F CH2CH2CH3 4-CN CH2C≡CH 4-CN CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3 CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3 R is H; Rl is H; R2 13 CH3; R5 is Cl; R7 is CH3; Y is , 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-0CH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-0CH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
Figure imgf000090_0001
U
R is H; Rl is H; R2 is H; R5 is Cl; Y is O.
R4 (R3)m R4 (R3)m
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C=CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH2CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH2CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3 CH(CH3)2 4-F CH(CH3)2 2,4-di-F CH(CH3)2 4-CN CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)2 4-OCH3 CH(CH3)2 4-Cl CH(CH3)2 4-CH3 CH(CH3)2 4-SCH3 CH(CH3)2 2-F CH(CH3)2 4-OCF3 CH(CH3)2 3-CF3 R is H; Rl is H; R2 is C ; R5 is Cl; Y is O.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH2CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH CH3 4-SCH3 CH C≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH(CH3)C≡CH 4-F
CH2CH(CH3)2 4-CN CH(CH3)C≡CH 4-CN
CH2CH(CH3)2 4-OCH3 CH(CH3)C≡CH 4-OCH3
CH2CH(CH3)2 4-CH3 CH(CH3)C≡CH 4-CH3
CH2CH(CH3)2 2-F CH(CH3)C≡CH 2-F
CH2CH(CH3)2 3-CF3 CH(CH3)C≡CH 3-CF3
CH2CH(CH3)2 2,4-di-F CH(CH3)C≡CH 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH(CH3)C≡CH 2,3-di-Cl-4-OCH3
CH2CH(CH3)2 4-Cl CH(CH3)C≡CH 4-Cl
CH2CH(CH3)2 4-SCH3 CH(CH3)C≡CH 4-SCH3
CH2CH(CH3)2 4-OCF3 CH(CH3)C≡CH 4-OCF3
CH2CH2CF3 4-F cyclopropylmethyl 4-F
CH2CH2CF3 4-CN cyclopropylmethyl 4-CN
CH2CH2CF3 4-OCH3 cyclopropylmethyl 4-OCH3
CH2CH2CF3 4-CH3 cyclopropylmethyl 4-CH3
CH CH2CF3 2-F cyclopropylmethyl 2-F
CH2CH2CF3 3-CF3 cyclopropylmethyl 3-CF3
CH2CH2CF3 2,4-di-F cyclopropylmethyl 2,4-di-F
CH2CH2CF3 2,3-di-Cl-4-OCH3 cyclopropylmethyl 2,3-di-Cl-4-OCH3
CH2CH2CF3 4-Cl cyclopropylmethyl 4-Cl
CH2CH2CF3 4-SCH3 cyclopropylmethyl 4-SCH3
CH2CH2CF3 4-OCF3 cyclopropylmethyl 4-OCF3
CH2CH2CH2CH3 4-F cyclopentyl 4-F
CH2CH2CH2CH3 4-CN cyclopentyl 4-CN
CH2CH2CH2CH3 4-OCH3 cyclopentyl 4-OCH3 R is H; Rl is H; R2 is CH3; R5 is Cl; Y is O.
R4 (R3)m R4 (R3)m
CH2CH2CH2CH3 4-CH3 cyclopentyl 4-CH3
CH2CH2CH2CH3 2-F cyclopentyl 2-F
CH2CH2CH2CH3 3-CF3 CH2CH2CN 3-CF3
CH2CH2CH2CH3 2,4-di-F CH2CH2CN 2,4-di-F
CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH2CN 2,3-di-Cl-4-OCH3
CH2CH2CH CH3 4-Cl CH2CH2CN 4-Cl
CH2CH2CH2CH3 4-SCH3 CH2CH2CN 4-SCH3
CH2CH2CH2CH3 4-OCF3 CH2CH2CN 4-OCF3
CH(CH3)2 4-F CH(CH3)2 2,4-di-F
CH(CH3)2 4-CN CH(CH3)2 2,3-di-Cl-4-OCH3
CH(CH3)2 4-OCH3 CH(CH3)2 4-Cl
CH(CH3)2 4-CH3 CH(CH3)2 4-SCH3
CH(CH3)2 2-F CH(CH3)2 4-OCF3
CH(CH3)2 3-CF3
R is H; R! is H; R2 is H; R5 is CF3; Y is 0.
R4 (R3)m R4 (R3)m
CH2CH2CH3 4-F CH2C≡CH 4-F
CH2CH2CH3 4-CN CH2C≡CH 4-CN
CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3
CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3
CH2CH2CH3 2-F CH2C≡CH 2-F
CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3
CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F
CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3
CH CH2CH3 4-Cl CH2C≡CH 4-Cl
CH2CH2CH3 4-SCH3 CH2G≡CH 4-SCH3
CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3
CH2CH(CH3)2 4-F CH2CH2CH2CH3 4-F
CH2CH(CH3)2 4-CN CH2CH2CH2CH3 4-CN
CH2CH(CH3)2 4-OCH3 CH2CH2CH2CH3 4-OCH3
CH2CH(CH3)2 4-CH3 CH2CH2CH2CH3 4-CH3
CH2CH(CH3)2 2-F CH2CH2CH2CH3 2-F
CH2CH(CH3)2 3-CF3 CH2CH2CH2CH3 3-CF3
CH2CH(CH3)2 2,4-di-F CH2CH2CH2CH3 2,4-di-F
CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 R is H; Rl is H; R2 is H; R5 is CF3; Y is O. R4 (R3)m R4 (R3)m CH2CH(CH3)2 4-Cl CH2CH2CH2CH3 4-Cl CH2CH(CH3)2 4-SCH3 CH2CH2CH2CH3 4-SCH3 CH2CH(CH3)2 4-OCF3 CH2CH2CH2CH3 4-OCF3
R is H; Rl is H; R2 is CH3; R5 is CF3; Y is O. R4 (R3)m R4 (R3)m CH2CH2CH3 4-F CH2C≡CH 4-F CH2CH2CH3 4-CN CH2C≡CH 4-CN CH2CH2CH3 4-OCH3 CH2C≡CH 4-OCH3 CH2CH2CH3 4-CH3 CH2C≡CH 4-CH3 CH2CH2CH3 2-F CH2C≡CH 2-F CH2CH2CH3 3-CF3 CH2C≡CH 3-CF3 CH2CH2CH3 2,4-di-F CH2C≡CH 2,4-di-F CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2C≡CH 2,3-di-Cl-4-OCH3 CH2CH2CH3 4-Cl CH2C≡CH 4-Cl CH2CH2CH3 4-SCH3 CH2C≡CH 4-SCH3 CH2CH2CH3 4-OCF3 CH2C≡CH 4-OCF3 CH2CH(CH3)2 4-F CH2CH2CH2CH3 4-F CH2CH(CH3)2 4-CN CH2CH2CH2CH3 4-CN CH2CH(CH3)2 4-OCH3 CH2CH2CH2CH3 4-OCH3 CH2CH(CH3)2 4-CH3 CH2CH2CH2CH3 4-CH3 CH2CH(CH3)2 2-F CH2CH2CH2CH3 2-F CH2CH(CH3)2 3-CF3 CH2CH2CH2CH3 3-CF3 CH2CH(CH3)2 2,4-di-F CH2CH2CH2CH3 2,4-di-F CH2CH(CH3)2 2,3-di-Cl-4-OCH3 CH2CH2CH2CH3 2,3-di-Cl-4-OCH3 CH2CH(CH3)2 4-Cl CH2CH2CH2CH3 4-Cl CH2CH(CH3)2 4-SCH3 CH2CH2CH2CH3 4-SCH3 CH2CH(CH3)2 4-OCF3 CH2CH2CH2CH3 4-OCF3
Formulation/Utilitv Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. 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. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films (including seed coatings), and the like which can be water-dispersible ("wettable") or water-soluble. 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. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation. 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. Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and Powders. Suspensions, Emulsions, 1-50 40-99 0-50 Solutions (including Emulsifiable Concentrates) Dusts 1-25 70-99 0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions 90-99 0-10 0-2 Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New
Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ.
Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity. Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, glycerol esters, poly- oxyethylene/polyoxypropylene block copolymers, and alkylpolyglycosides where the number of glucose units, referred to as degree of polymerization (D.P.), can range from 1 to 3 and the alkyl units can range from Cg to C14 (see Pure and Applied Chemistry 72, 1255- 1264). Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, glycerine, triacetine, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as hexyl acetate, heptyl acetate and octyl acetate, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol. Useful formulations of this invention may also contain materials well known to those skilled in the art as formulation aids such as antifoams, film formers and dyes. Antifoams can include water dispersible liquids comprising polyorganosiloxanes like Rhodorsil® 416. The film formers can include polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Dyes can include water dispersible liquid colorant compositions like Pro-lzed® Colorant Red. One skilled in the ait will appreciate that this is a non-exhaustive list of formulation aids. Suitable examples of formulation aids include those listed herein and those listed in McCutcheon's 2001, Volume 2: Functional Materials published by MC Publishing Company and PCT Publication WO 03/024222. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. 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. For further information regarding the art of formulation, see T. S. Woods, "The
Formulator's Toolbox - Product Forms for Modern Agriculture" in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10^11; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A- H. Example A High Strength Concentrate Compound 186 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%. Example B Wettable Powder Compound 236 65.0%> dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example C
Granule Compound 237 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example D Aqueous Suspension Compound 238 25.0% hydrated attapulgite ' 3.0% crude calcium ligninsulfonate 10.0% sodium dihydrogen phosphate 0.5% water 61.5%. Example E Extruded Pellet Compound 94 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%. Example F Microemulsion Compound 122 1.0% triacetine 30.0% C8-C10 alkylpolyglycoside 30.0% glyceryl monooleate 19.0% water 20.0%. Example G
High Strength Concentrate Compound 140 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%. Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. 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). 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. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth. As the compounds of the invention have both preemergent and postemergent 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 0.0001 to 20 kg/ha with a preferred range of about 0.001 to 5 kg/ha and a more preferred range of about 0.004 to 3 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 be used alone or in combination with other herbicides, insecticides and fungicides, and other agricultural chemicals such as fertilizers. 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. 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, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, copper sulfate, CUH-35 (2-methoxyethyl 2-[[[4-chloro-2-fluoro-5-[(l-methyl-2-propynyl)oxy]phenyl](3-fluoro- benzoyl)amino]carbonyl]-l-cyclohexene-l-carboxylate), cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluπdone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate. glufosinate-ammonium, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, HOK-201 (N-(2,4- difluorophenyl)-l,5-dihydro-N-(l-methylethyl)-5-oxo-l-[(tetrahydro-2H-pyran-2-yl)- methyl]-4H-l,2,4-triazole-4-carboxamide), imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, isoxadifen, KUΗ-021 (N-[2- [(4,6-dimethoxy-2-pyrimidinyl)hydiOxymethyl] -6-(methoxymethyl)phenyl] -1,1 -difluoro- methanesulfonamide), lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium), esters (e.g., MCPA-2- ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metholachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperofos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrazogyl, pyrazolate, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thifensulfuron-methyl, thiobencarb, tiocarbazil, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron and vernolate. Other 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.) Bαtl. and Puccinia thlaspeos Schub. Combinations of compounds of the invention with other herbicides 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. In certain instances, combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds. Herbicidally effective amounts of compounds of the invention as well as herbicidally effective amounts of other herbicides can be easily deteπnined 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) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of mefluidide, diquat dibromide, diuron, hexazinone, terbacil, glyphosate (particularly glyphosate-isopropylammonium, glyphosate-sodium, glyphosate- potassium, glyphosate-trimesium), glufosinate (particularly glufosinate-ammonium), rimsulfuron, sulfometuron-methyl, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron-methyl, sulfosulfuron, imazapyr, isoproturon, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, ametryn, and paraquat. Specifically preferred mixtures (compound numbers refer to compounds in Index Tables A-H) are selected from the group: compound 105 and mefluidide; compound 106 and mefluidide; compound 107 and mefluidide; compound 186 and mefluidide; compound 236 and mefluidide; compound 237 and mefluidide; compound 238 and mefluidide; compound 251 and mefluidide; compound 105 and diquat dibromide; compound 106 and diquat dibromide; compound 107 and diquat dibromide; compound 186 and diquat dibromide; compound 236 and diquat dibromide; compound 237 and diquat dibromide; compound 238 and diquat dibromide; compound 251 and diquat dibromide; compound 105 and diuron; compound 106 and diuron; compound 107 and diuron; compound 186 and diuron; compound 236 and diuron; compound 237 and diuron; compound 238 and diuron; compound 251 and diuron; compound 105 and hexazinone; compound 106 and hexazinone; compound 107 and hexazinone; compound 186 and hexazinone; compound 236 and hexazinone; compound 237 and hexazinone; compound 238 and hexazinone; compound 251 and hexazinone; compound 105 and terbacil; compound 106 and terbacil; compound 107 and terbacil; compound 186 and terbacil; compound 236 and terbacil; compound 237 and terbacil; compound 238 and terbacil; compound 251 and terbacil; compound 105 and glyphosate; compound 106 and glyphosate; compound 107 and glyphosate; compound 186 and glyphosate; compound 236 and glyphosate; compound 237 and glyphosate; compound 238 and glyphosate; compound 251 and glyphosate; compound 105 and glufosinate; compound 106 and glufosinate; compound 107 and glufosinate; compound 186 and glufosinate; compound 236 and glufosinate; compound 237 and glufosinate; compound.238 and glufosinate; compound 251 and . glufosinate; compound 105 and rimsulfuron; compound 106 and rimsulfuron; compound 107 and rimsulfuron; compound 186 and rimsulfuron; compound 236 and rimsulfuron; compound 237 and rimsulfuron; compound 238 and rimsulfuron; compound 251 and rimsulfuron; compound 105 and sulfometuron-methyl compound 106 and sulfometuron-methyl compound 107 and sulfometuron-methyl compound 186 and sulfometuron-methyl compound 236 and sulfometuron-methyl compound 237 and sulfometuron-methyl compound 238 and sulfometuron-methyl compound 251 and sulfometuron-methyl compound 105 and mesosulfuron-methyl compound 106 and mesosulfuron-methyl compound 107 and mesosulfuron-methyl compound 186 and mesosulfuron-methyl compound 236 and mesosulfuron-methyl compound 237 and mesosulfuron-methyl compound 238 and mesosulfuron-methyl compound 251 and mesosulfuron-methyl compound 105 and metsulfuron-methyl compound 106 and metsulfuron-methyl; compound 107 and metsulfuron-methyl compound 186 and metsulfuron-methyl; compound 236 and metsulfuron-methyl compound 237 and metsulfuron-methyl; compound 238 and metsulfuron-methyl compound 251 and metsulfuron-methyl; compound 105 and nicosulfuron; compound 106 and nicosulfuron; compound 107 and nicosulfuron; compound 186 and nicosulfuron; compound 236 and nicosulfuron; compound 237 and nicosulfuron; compound 238 and nicosulfuron; compound 251 and nicosulfuron; compound 105 and primisulfuron-methyl; compound 106 and primisulfuron-methyl; compound 107 and primisulfuron-methyl; compound 186 and primisulfuron-methyl compound 236 and primisulfuron-methyl; compound 237 and primisulfuron-methyl compound 238 and primisulfuron-methyl; compound 251 and primisulfuron-methyl compound 105 and sulfosulfuron; compound 106 and sulfosulfuron; compound 107 and sulfosulfuron; compound 186 and sulfosulfuron; compound 236 and sulfosulfuron; compound 237 and sulfosulfuron; compound 238 and sulfosulfuron; compound 251 and sulfosulfuron; compound 105 and imazapyr; compound 106 and imazapyr; compound 107 and imazapyr; compound 186 and imazapyr; compound 236 and imazapyr; compound 237 and imazapyr; compound 238 and imazapyr; compound 251 and imazapyr; compound 105 and isoproturon; compound 106 and isoproturon; compound 107 and isoproturon; compound 186 and isoproturon; compound 236 and isoproturon; compound 237 and isoproturon; compound 238 and isoproturon; compound 251 and isoproturon; compound 105 and flupyrsulfuron-methyl; compound 106 and flupyrsulfuron-methyl; compound 107 and flupyrsulfuron-methyl; compound 186 and flupyrsulfuron-methyl; compound 236 and flupyrsulfuron-methyl; compound 237 and flupyrsulfuron-methyl; compound 238 and flupyrsulfuron-methyl; compound 251 and flupyrsulfuron-methyl; compound 105 and flupyrsulfuron-methyl-sodium; compound 106 and flupyrsulfuron-methyl-sodium; compound 107 and flupyrsulfuron-methyl-sodium; compound 186 and flupyrsulfuron- methyl-sodium; compound 236 and flupyrsulfuron-methyl-sodium; compound 237 and flupyrsulfuron-methyl-sodium; compound 238 and flupyrsulfuron-methyl-sodium; compound 251 and flupyrsulfuron-methyl-sodium; compound 105 and ametryn; compound 106 and ametryn; compound 107 and ametryn; compound 186 and ametryn; compound 236 and ametryn; compound 237 and ametryn; compound 238 and ametryn; compound 251 and ametryn; compound 105 and paraquat; compound 106 and paraquat; compound 107 and paraquat; compound 186 and paraquat; compound 236 and paraquat; compound 237 and paraquat; compound 238 and paraquat; compound 251 and paraquat. The proportions of the compounds of the invention with other herbicidal active ingredients in herbicidal compositions are generally in the ratio of 100:1 to 1:100, more commonly 10:1 to 1:10 and most commonly 5:1 to 1:5 by weight. The optimum ratios can be easily determined by those skilled in the art based on the weed control spectrum desired. Compounds of this invention can also be used in combination with herbicide safeners such as benoxacor, BCS (l-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl, cyometrinil, dichlormid, 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadif en-ethyl, mefenpyr- ethyl, methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone), naphthalic anhydride (1,8-naphthalic anhydride) and oxabetrinil to increase safety to certain crops. Antidotally 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. 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 A4 and A7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01. The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-H for compound descriptions. The following abbreviations are used in the Index Tables which follow: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, c-Pr means cyclopropyl, z'-Pr means isopropyl, Bu means butyl, Ph means phenyl, MeO means methoxy, EtO means ethoxy, and CΝ means cyano. "θ" means negative formal charge, and "θ" means positive formal charge. The abbreviation "dec" indicates that the compound appeared to decompose on melting. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared. INDEX TABLE A
Figure imgf000104_0001
Compound (R3): m Y R4 R5 R6 m.p. (°C) 1 2-F-4-CF3 O CH2CH2CH3 Cl H 119-120 2 2-F-4-CF3 O CH2CF3 Cl H 144-146 3 2-F-4-CF3 O CH2CH2CH2CH3 Cl H 114-116 4 3,4-di-OCH3 O CH2CH2CH3 Cl H 124-125 5 3,4-fOCH20} O CH2CH2CH3 Cl H 147-149 Compound (R3)m Y R4 R5 R6 m.p. (°C) 6 2-F-4-CF3 0 CH2CH2CF3 Cl H 130- -131 7 2-F-4-CF3 NMe CH3 Cl H : i: 8 2,3-di-CH3 0 CH2CH2CH3 Cl H 164-165 9 4-OCH3 O CH2CH2CH3 Cl H 147- -148 10 4-F 0 CH2CH2CH3 Cl H 115- -116 11 2,3-di-F 0 CH2CH2CH3 Cl H 119- -121 12 3,4-di-F 0 CH2CH2CH3 Cl H 107- -108 13 2,5-di-Cl 0 CH2CH2CH3 Cl H 146- -147 14 3-F-4-CF3 0 CH2CH2CH3 Cl H 111- -112 15 3-CI-4-CH3 0 CH2CH2CH3 Cl H 129- -131 16 2,6-di-OCH3 0 CH2CH2CH3 Cl H 101- -103 17 2,5-di-OCH3 0 CH2CH2CH3 Cl H 117- -118 18 2-F 0 CH2CH2CH3 Cl H 134- -135 19 2-F-4-CF3 0 CH2CH(CH3)2 Cl H 157- -158 20 2-F-4-CF3 0 (CH2)4CH3 Cl H 131- -132 21 4-CF3 0 CH2CH2CH3 Cl H 129- -131 22 4-OCF3 0 CH2CH2CH3 CI H 113- -114 23 2-C1 0 CH2CH2CH3 Cl H 119- -121 24 2,6-di-F 0 CH2CH2CH3 Cl H 135- -137 25 2-F-4-CF3 0 CH2C≡CH Cl H 127- -128 26 2-F-4-CF3 0 (CH2)2OCH2CH3 Cl H 125- -127 27 2-F-4-CF3 0 CH(CH3)(CH2)4CH3 Cl H 86- -87 28 2-F-4-CF3 0 CH2CH2CH2CH3 Cl CH3 136- -137
29 (Ex. 1) 4-F 0 CH2CH2CH3 Cl CH3 147- -148 30 2-F 0 CH2CH2CH3 Cl CH3 112- -114 31 3,4-di-F 0 CH2CH2CH3 Cl CH3 139- -141 33 2,4-di-Cl 0 CH2CH2CH3 Cl H 132- -133 34 2,4-di-F 0 CH2CH2CH3 Cl H 116- -117 35 2-CI-6-CH3 0 CH2CH2CH3 Cl H 157- -159 36 4-Cl 0 CH2CH2CH3 Cl H 133- -135 37 2-F-4-CF3 0 (CH2)2CH(CH3)2 Cl H 140-142 38 2-F-4-CF3 0 CH2-(tetrahydrofuran-2-yl) Cl H 115- -119 39 2-F-4-CF3 NH CH2CH2CH3 Cl H 97- -98 40 2-F-4-CF3 0 CH2CH2CH3 Cl CH3 161- -162 41 3-CN 0 CH2CH2CH3 Cl CH3 102- -103 42 4-N(CH3)2 0 CH2CH2CH3 Cl CH3 111- -112 43 2,4,6-tri-OCH3 0 CH2CH2CH3 Cl CH3 119- -120 Compound (R3); m R« R5 R6 m.p. (°C) 44 2-F-4-CF3 NEt CH2CH2CH3 Cl H ' l! 45 4-Cl O CH2CH2CH3 Cl CH3 148- -149 46 3,4,5-tri-OCH3 O CH2CH2CH3 Cl CH3 111- -114 49 4-F 0 CH2CH2CH3 Cl Cl 139- -141 51 3-C1-4-F 0 CH2CH2CH3 Cl CH3 116- -117 52 3,4,5-tri-F 0 CH2CH2CH3 Cl CH3 142- -144 53 4-j-Pr 0 CH2CH2CH3 Cl CH3 136- -138 54 4-f-Bu 0 CH2CH2CH3 Cl CH3 147- -148 55 3-CF3 0 CH2CH2CH3 Cl CH3 104- -105 58 4-N02 0 CH2CH2CH3 Cl CH3 175- -178 62 4-F S CH2CH2CH3 Cl CH3 N 63 4-F s CH2CH2CH3 S(CH2)2CH3 CH3 78- -85
64 (Ex. 3) 4-F 0 CH(CH3)2 Cl CH3 176- -178 65 4-S(0)2CH3 0 CH2CH2CH3 Cl CH3 122- -123 66 4-1 0 CH2CH2CH3 Cl CH3 148- -151 67 3-C1 0 CH2CH2CH3 Cl CH3 101- -102 68 3-OCF3 0 CH2CH2CH3 Cl CH3 92- -93 69 2-OCH3 0 CH2CH2CH3 Cl CH3 103- -104 70 2-F-4-CF3 0 CH2CH2CF3 0(CH2)2CF3 H 146- -148 71 4-Br 0 CH2CH2CH3 Cl CH3 150- -151 72 3-F 0 CH2CH2CH3 Cl CH3 126- -128 73 3-CH3 0 CH2CH2CH3 Cl CH3 95- -96 74 3-OCH3 0 CH2CH2CH3 Cl CH3 84- -85 75 4-SCH3 0 CH2CH2CH3 Cl CH3 136- -137 76 3-OCF3 0 CH2CH2CH3 Cl CH3 * 77 4-F 0 CH2CH2CH3 SCH3 CH3 150-152 84 4-F 0 CH2CH2CH3 CH3 CH3 56- -58
87 (Ex. 4) 4-F 0 CH2CH2CH3 Br CH3 145- -147 88 4-F 0 CH2CH2CF3 Cl CH3 128- -131 89 4-F 0 c-pentyl Cl CH3 141- -144 90 4-F 0 CH2CH2CH3 0CH3 CH3 100- -103 92 4-F 0 CH2CH2CH3 H H 59- -61 93 4-CN 0 CH2CH2CH3 Cl CH3 125- -126 109 2,4-di-F 0 CH2CH2CH3 0(CH2)2CH3 H 101- -102 114 4-N02 0 CH(CH3)2 Cl CH3 181- -183 116 2,3-di-Cl-4-OCH3 0 CH2CH2CH3 Cl CH3 116- -117 125 2,3-di-Cl-4-OCH3 0 CH(CH3)2 Cl CH3 167- -172 Compound (R3)m Y R4 R5 R6 m.p. (°C) 128 4-CN O CH(CH3)2 Cl CH3 183- -185 147 4-F 0 CH2-c-Pr Cl CH3 136- -137 221 4-F 0 CH(CH3)2 Br CH3 172- -175 235 3-C1-4-F 0 CH2CH2CH3 Br CH3 ϋ 240 3-C1-4-F 0 CH(CH3)2 Br CH3 167- -168 243 2-F-4-Cl-5-OCH3 0 CH2CH2CH3 Cl CH3 244 2-F-4-Cl-5-0(CH2)2CH3 0 CH2CH2CH3 Br CH3 123- -125 245 2-F-4-Cl-5-OCH3 0 CH(CH3)2 Cl CH3 171- -172 249 3-F 0 CH(CH3)2 Br CH3 155- -157 250 3-CH3 0 CH(CH3)2 Br CH3 123- -127 252 2-F-4-Cl-5-OCH(CH3)2 0 CH2CH2CH3 Cl CH3 120-122 253 2-F-4-Cl-5-OCH2C==CH 0 CH2CH2CH3 Cl CH3 142- -145 254 2,5-di-F-4-CN 0 CH2CH2CH3 Cl CH3 183- -185 255 2,4,5-tri-F 0 CH2CH2CH3 Cl CH3 122- -125 256 2-F-4-CF3-5-Br 0 CH2CH2CH3 Cl CH3 121- -123 256 2-F-4-CF3-5-Br 0 CH2CH2CH3 Cl CH3 121- -123 258 2,5-di-Me-4-0-(3-t-Bu-Ph) 0 CH2CH2CH3 Cl CH3 *, 259 2-F-4-C1 0 CH2CH2CH3 Cl CH3 i != 260 2-F-4-Br 0 CH2CH2CH3 Cl CH3 * 262 2,5-di-F-4-Cl 0 CH2CH2CH3 Cl CH3 ^ f 263 2-F-4-Cl-5-CH3 0 CH2CH2CH3 Cl CH3 ϊ f 264 4-F 0 CH(CH3)CF3 Br CH3 177- -181 265 2-F-4-CN 0 CH2CH2CH3 Cl CH3 1 ϋ 266 2,4-di-F-5-0CH3 0 CH2CH2CH3 Cl CH3 133- -135 267 2,4-di-F-5-0CH3 0 CH2CH2CH3 Cl CH3 90- -92 268 2-F-4-Br-5-0CH3 0 CH2CH2CH3 Cl CH3 92-95 269 2-F-4-Br-5-CH3 0 CH2CH2CH3 Cl CH3 130- -132 270 2-F-4-CI-5-CH3 0 CH(CH3)2 Br CH3 136- -138 271 2-F-4-CF3-5-Br 0 CH(CH3)2 Br CH3 153- -155 272 2,4-di-F-5-CH3 0 CH(CH3)2 Br CH3 128- -130 273 2-F-4-Br-5-0CH3 0 CH(CH3)2 Br CH3 165- -167 274 3-C1 0 CH(CH3)2 Br CH3 136- -137 279 2,4-di-F-5-0CH3 0 CH(CH3)2 Br CH3 137- -139 280 2-F-4-Cl-5-0CH(CH3)2 0 CH(CH3)2 Br CH3 141- -143 281 2-F-4-Br-5-CH3 0 CH(CH3)2 Br CH3 157- -159 282 2,5-di-F-4-Cl 0 CH(CH3)2 Br CH3 182- -184 287 2-F-4-Cl-5-0CH2C≡CH 0 CH(CH3)2 Br CH3 197- -199 Compound (R )m Y R4 R5 R6 m.p. (°C) 288 2,4,5-tri-F 0 CH(CH3)2 Br CH3 158-160 296 2,4-di-F 0 OCH(CH3)CF3 Cl H 146-147 * See Index Table H for IH NMR data. INDEX TABLE B
Figure imgf000108_0001
In the column "Chirality" R and S indicate isomeric configuration at the carbon denoted with an asterisk (*) above, RS indicates a racemate consisting of equal amounts of the R and S enantiomers, and a dash ("-") indicates no stereochemistry. In the column "(R )m" a dash ("-") indicates no substituents. Y is O. Compound Chirality Rl R2 (R3)m R4 R3 Rc m.p.(°C) 32 RS H CH3 4-F CH2CH2CH3 Cl H 108- -110 50 RS H CH3 4-F CH2CH2CH3 Cl CH3 142- -143 56 ' R H CH3 4-Cl CH2CH2CH3 Cl CH3 132- -134 57 S H CH3 4-Cl CH2CH2CH3 Cl CH3 131- -132 101 S H CH3 4-CH3 CH2CH2CH3 Cl CH3 124- -130 102 s H CH3 3-OCH3 CH2CH2CH3 Cl CH3 107- -108 103 (Ex. 2) s H CH3 4-OCH3 CH2CH2CH3 Cl CH3 110- -111 105 l s H CH3 4-CH3 CH(CH3)2 Cl CH3 149- -150 106 s H CH3 3-OCH3 CH(CH3)2 Cl CH3 122- -124 107 s H CH3 4-Cl CH(CH3)2 Cl CH3 154- -155 108 s H CH3 4-OCH3 CH(CH3)2 Cl CH3 132- -133 110 s H CH3 4-N02 CH2CH2CH3 Cl CH3 184- -186 112 - CH3 CH3 3,5-di-Cl CH(CH3)2 Cl CH3 161- -162 113 s H CH3 4-N02 CH(CH3)2 Cl CH3 160- -161 115 s H CH3 4-Br CH2CH2CH3 Cl CH3 144-145 117 - CH3 CH3 3,5-di-Cl CH2CH2CH3 Cl CH3 221- -223 120 s H CH3 4-Br CH(CH3)2 Cl CH3 142- -143 152 RS H CH2CH3 4-OCH3 CH2CH2CH3 Cl CH3 n 153 S H CH3 4-OCH3 CH2-c-Pr Cl CH3 147- -148 154 s H CH3 4-OCH3 N=C(CH3)2 Cl CH3 138- -139 155 s H CH3 4-OCH3 CH(CH3)C≡CH Cl CH3 149- -150 156 s H CH3 4-OCH3 CH2C≡CH Cl CH3 91- -94 Compound Chirality R R2 (R^)m R4 R5 R6 m.p.(°C) 157 5 H CH3 4-OCH3 CH2CH2CH3 Br CF3 161- -163 168 S H CH3 4-OCH3 CH2CF3 Cl CH3 190-191 181 s H CH3 4-OCH3 ### Cl CH3 103- -104 182 s H CH3 4-OCH3 CH2CH=CH2 Cl CH3 116- -117 183 s H CH3 4-OCH3 CH2CH2CF3 Cl CH3 160- -161 184 - CH3 CH3 4-F CH2CH2CH3 Cl CH3 188- -189 185 s H CH3 4-F CH2CH2CH3 Cl CH3 144-146 186 s H CH3 4-F CH(CH3)2 Cl CH3 155- -160 187 RS H CH2CH(CH3)2 4-OCH3 CH2CH2CH3 Cl CH3 :: N 202 RS H CN 4-F CH2CH2CH3 Cl CH3 * 1= 211 RS H CN 4-OCF3 CH2CH2CH3 Cl CH3 > |: 212 RS H CN 4-CF3 CH2CH2CH3 Cl CH3 M 1: 217 s H CH3 4-F CH2-c-Pr Cl CH3 162- -165 218 s H CH3 4-F CH2CH=CH2 Cl CH3 152- -153 219 s H CH3 4-F CH2G≡CH Cl CH3 146- -148 220 s H CH3 4-F CH2CH2CH3 Cl Cl 166- -173 222 s , H CH3 4-F CH2CH2CH3 Cl CH2SCH3 ^ Is 223 ■ s H CH3 4-OCH3 CH2CH2CH3 Cl CH2SCH3 228 s H CH3 4-F CH2CH2CH3 SCH3 Cl 146- -148 229 s H CH3 4-F CH2CH2CH3 Br CH3 153- -154 230 s H CH3 4-OCH3 CH2CH2CH3 Br CH3 143- -144 231 s H CH3 4-CH3 CH2CH2CH3 Br CH3 165- -166 232 s H CH3 4-Cl CH2CH2CH3 Br CH3 148- -149 233 RS H CH3 2,4-di-Cl-5-F CH2CH2CH3 Cl CH3 99- 104 234 RS H CH3 2,5-di-F-4-Cl CH2CH2CH3 Cl CH3 104- -105
236 (Ex. 11) S H CH3 4-F CH(CH3)2 Br CH3 157- -159 237 S H CH3 4-OCH3 CH(CH3)2 Br CH3 130- -131 238 S H CH3 4-CH3 CH(CH3)2 Br CH3 150- -151 239 S H CH3 4-Cl CH(CH3)2 Br CH3 157- -158 241 RS H CN 4-Cl CH2CH2CH3 Cl CH3 H s 242 RS H CN 4-Br CH2CH2CH3 Cl CH3 =1 246 S H CH3 4-F CH2CH2CH3 F CH3 127- -128 247 S H CH3 4-F CH3 OCH3 Cl 137- -141 248 S H CH3 4-F CH(CH3)2 F CH3 112- -117 251 S H CH3 3-OCH3 CH(CH3)2 Br CH3 =1 261 RS H CN 4-OCF2CHF2 CH2CH2CH3 Cl CH3 !| 275 S H CH3 - CH(CH3)2 Br CH3 149- -150 Compound Chirality Rl R2 (R3) m R4 R5 R6 m.p.(°C) 276 RS H CH3 3-Si(CH3)3 CH(CH3)2 Br CH3 75-78 277 RS H CN 4-F CH(CH3)2 Br CH3 * 278 RS H CN 4-Br CH(CH3)2 Br CH3 * 283 RS H CN 3-Br-4-F CH(CH3)2 Br CH3 * 284 RS H CN 3-0-CF3 CH(CH3)2 Br CH3 * 286 RS H CN 3-Br-4,5-di-OMe CH(CH3)2 Br CH3 * 289 RS H CN 2,3-di-F CHCH3CH3 Br CH3 * 290 RS H CN 4-OCF3 CH(CH3)2 Br CH3 * 291 RS H CN 4-Cl CH(CH3)2 Br CH3 * 292 RS H C02H 4-F CH(CH3)2 Br CH3 * 293 S H CH3 4-CH3 CH(CH3)CF3 Cl CH3 139-140 294 s H CH3 3-OCH3 CH(CH3)CF3 Cl CH3 * 295 s H CH3 4-OCH3 CH(CH3)CF3 Cl CH3 126-128 297 RS H C02CH3 4-F CH(CH3)2 Br CH3 * 298 RS H C(0)NH2 4-F CH(CH3)2 Br CH3 * 299 S H CH3 3-OCH3 CH(CH3)CF3 Br CH3 * * See Index Table H for *H NMR data. *** In Compound 181, R4 is CH2C(CH3)=NOCH3. INDEX TABLE C
Figure imgf000110_0001
In the column "Chirality" R and S indicate isomeric configuration at the carbon denoted with an asterisk (*) above, RS indicates a racemate consisting of equal amounts of the R and S enantiomers, and a dash ("-") indicates no stereochemistry. Y is O.
Compound Chirality Rl R2 (R3)m R4 R5 R7 m.p. (°C) 47 H H 2-F-5-CF3 CH2CH2CH3 CF3 CH3 67-69 48 - H H 2,6-di-Cl CH2CH2CH3 CF3 CH3 88-90 59 - H H 2,3-di-Cl CH2CH2CH3 CF3 CH3 82-84 60 - H H 2,5-di-Cl CH2CH2CH3 CF3 CH3 104-106 61 - H H 2-F-5-C1 CH2CH2CH3 CF3 CH3 67-69 78 (Ex. 6) - H H 2,4-di-F CH2CH2CH3 CF3 CH3 71-73 79 - H H 4-Cl CH2CH2CH3 CF3 CH3 98-100 Compound Chirality Rl R2 (R3)m R4 R5 R7 m.p. (°C) 80 H H 4-F CH2CH2CH3 CF3 CH3 78-80 81 - H H 2,3-di-F CH2CH2CH3 CF3 CH3 67-69 82 - H H 2-C1 CH2CH2CH3 CF3 CH3 * 83 - H H 2-F-4-C1 CH2CH2CH3 CF3 CH3 78-80 85 - H H 2,5-di-F CH2CH2CH3 CF3 CH3 74-76 86 - H H 3-C1 CH2CH2CH3 CF3 CH3 * 91 - H H 4-F CH2CH2CH3 Cl CH3 52-54 94 (Ex. 5) S H CH3 4-Cl CH2CH2CH3 Cl CH3 96-98 95 RS H CH3 4-Br CH2CH2CH3 Cl CH3 62-64 96 - H H 2,4-di-F CH2CH2CH3 Cl CH3 74-75 97 R H CH3 4-Cl CH2C≡CH CF3 CH3 * 98 R H CH3 4-F CH2CsCH CF3 CH3 * 99 (Ex. 7) S H CH3 4-F CH2C≡CH CF3 CH3 ** 100 R H CH3 4-Cl CH2CH2CH3 Cl CH3 98-100 104 - H H 4-F CH2CH2CH3 H CH3 * 111 S H CH3 4-Cl CH2CH2CH3 H CH3 ❖ * See Index Table H for lR NMR data. ** See synthesis example for 1H NMR data. INDEX TABLE D
Figure imgf000111_0001
In the column "Chirality" R and S indicate isomeric configuration at the carbon denoted with an asterisk (*) above, RS indicates a racemate consisting of equal amounts of the R and S enantiomers, and a dash ("-") indicates no stereochemistry. In the column "(R3)m" a dash ("-") indicates no substituents. Compound Chirality Rl R2 (R3)m Y R4 R5 m.p. (°C) 118 H H 4-F O CH(CH3)2 Cl 95-96 119 (Ex. 8) - H H 4-F O CH2CH2CH3 Cl 124-125 121 S H CH3 4-Cl O CH(CH3)2 Cl 125-126 122 S H CH3 4-Cl O CH2CH2CH3 Cl 145-146 123 s H CH3 4-OCH3 0 CH(CH3)2 Cl 114-115 124 s H CH3 4-OCH3 O CH2CH2CH3 Cl 108-109 126 s H CH3 4-CH3 0 CH(CH3)2 Cl 125-126 127 s H CH3 4-CH3 O CH2CH2CH3 Cl 129-130 Compound Chirality Rl R2 (R3)m Y R4 R5 m.p. (°C) 129 S H CH3 4-Cl 0 CH2C≡CH Cl 136-137 130 S H CH3 4-Cl 0 CH2-c-Pr Cl 163-164 131 S H CH3 4-OCH3 0 CH2-c-Pr Cl 122-123 132 S H CH3 4-CH3 0 CH2-c-Pr Cl 126-127 158 S H CH3 4-Br 0 CH(CH3)2 Cl 133-135 159 S H CH3 4-Br 0 CH2CH2CH3 Cl 140-142 160 - H H 2-F-4-CF3 0 CH(CH3)2 Cl 117-118 161 - H H 2_F-4-CF3 0 CH(CH3)2 Cl 124-126 162 - H H 2-F-4-CF3 0 CH2CH2CH3 Cl 125-129 163 S H CH3 4-Cl 0 CH2CF3 Cl 142-143 195 s H CH3 4-Cl 0 CH2CH2CH3 CF3 140-142
196 (Ex. 10) s H CH3 4-Cl 0 CH(CH3)2 CF3 144-145 197 s H CH3 4-OCH3 0 CH2CH2CH3 CF3 115-116 198 s H CH3 4-OCH3 0 CH2CH2CH3 CF3 115-116 199 s H CH3 4-OCH3 0 CH(CH3)2 CF3 106-107 200 s H CH3 4-CH3 0 CH2CH2CH3 CF3 119-120 201 s H CH3 4-CH3 0 CH(CH3)2 CF3 103-108 206 s H CH3 4-F 0 CH2CH2CH3 Cl 125-126 207 s H CH3 2,3-tCH=CH-CH= =CH} O CH2CH2CH3 Cl 119-120 208 s H CH3 - 0 CH2CH2CH3 Cl 118-119 209 s H CH3 3-OCH3 0 CH2CH2CH3 Cl 79-81 210 s H CH3 4-F 0 CH2CH2CH3 CF3 111-113 224 s H CH3 4-Cl 0 (CH2)3CH3 CF3 161-162 225 s H CH3 4-Cl 0 CH2C(=CH2)C1 CF3 122-123 226 s H CH3 4-Cl 0 CH2CH=CH2 CF3 110-111 227 s H CH3 4-Cl 0 CH2CH2CF3 CF3 123-124 257 (Ex. 9) s H CH3 4-Cl s CH3 CF3 125-126 INDEX TABLE E
Figure imgf000112_0001
In the column "Chirality" R and S indicate isomeric configuration at the carbon denoted with an asterisk (*) above, RS indicates a racemate consisting of equal amounts of the R and S enantiomers, and a dash ("-") indicates no stereochemistry. Compound Chirality Rl R2 (R3)m Y R4 R5 m.p. (°C) 135 H H 4-F 0 CH2CH2CH3 Cl 116-117 136 S H CH3 4-OCH3 0 CH2CH2CH3 Cl 138-140 137 S H CH3 4-OCH3 0 CH(CH3)2 Cl 108-109 138 S H CH3 4-Cl 0 CH(CH3)2 Cl 134-135 139 - H H 4-F 0 CH(CH3)2 Cl 147-148
140 (Ex. 12) S H CH3 4-Cl 0 CH2CH2CH3 Cl 100-101 164 s H CH3 4-Cl 0 (CH2)3CH3 Cl * 165 RS H CH3 4-F 0 (CH2)3CH3 Cl * 166 s H CH3 4-Cl 0 CH2-c-Pr Cl 155-156 167 s H CH3 4-CH3 0 CH2-c-Pr Cl 176-177 169 s H CH3 4-Cl 0 CH2CH=CH2 Cl * 170 s H CH3 4-CH3 0 CH2CH=CH2 Cl * 171 s H CH3 4-OCH3 0 CH2CH=CH2 Cl * 172 s H CH3 4-Cl 0 CH2CH(CH3)2 Cl 114-115 173 s H CH3 4-CH3 0 CH2CH(CH3)2 Cl 104-105 174 - H H 4-F 0 CH2CH(CH3)2 Cl 158-159 177 - H H 3-C1-4-F 0 CH2CH2CH3 Cl * 178 ' s H CH3 4-CH3 0 CH2CH2CH3 Cl *
179 (Ex. 14) s H CH3 4-Cl 0 CH2OCH3 Cl ** 180 RS H CH3 4-Br 0 CH2CH2CH3 Cl * 188*** s H CH3 4-Cl 0 CH2CH2CH3 Cl 178-179 191 s H CH3 4-F 0 CH2CH2CH3 Cl * 203 s H CH3 4-Cl 0 CH2CH3 Cl * 204 s H CH3 4-Cl 0 CH2C≡N Cl *
205 (Ex. 15) s H CH3 4-Cl 0 CH2C(=CH2)C1 Cl ** 213 s H CH3 4-Cl 0 CH2CH2CH3 F * 214 s H CH3 4-F 0 CH2CH2CH3 F * 215 s H CH3 4-OCH3 0 CH2CH2CH3 F * 216 s H CH3 4-Cl 0 CH2CF3 Cl 154-155 * See Index Table H for IH NMR data. ** See synthesis example for 1H NMR data. *** Compound 188 is an HCl salt. INDEX TABLE F
Figure imgf000114_0001
In the column "Chirality" R and S indicate isomeric configuration at the carbon denoted with an asterisk (*) above, RS indicates a racemate consisting of equal amounts of the 7? and S enantiomers, and a dash ("-") indicates no stereochemistry. R5 is Cl; and Y is O. Compound Chirality R R2 (R3)m R4 R6a Counterion m.p.(°C)
189 (Ex. 13) S H CH3 4-Cl CH2CH2CH3 CH3 Iθ 193-194 192 S H CH3 4-Cl CH2CH2CH3 CH3 θOS(0)2CF3 * 193 S H CH3 4-Cl CH2CH2CH3 CH2CH3 BF4 Θ * 194 S H CH3 4-Cl CH2CH2CH3 CH2CH3 Iθ 194-195 * See Index Table H for NMR data. INDEX TABLE G
Figure imgf000114_0002
In the column "Chirality" R and S indicate isomeric configuration at the carbon denoted with an asterisk (*) above, RS indicates a racemate consisting of equal amounts of the R and S enantiomers, and a dash ("-") indicates no stereochemistry.
Compound Chirality Rl R2 (R3)m Y R4 R5 m.p.(°C) 190 S H CH3 4-Cl O CH2CH2CH3 Cl 186-187 INDEX TABLE H Compound 1H NMR Data (CDCI3 solution unless indicated otherwise)3 δ 7.85 (d, IH), 7.66 (t, IH), 7.29-7.43 (m, 2H), 6.80 (br t, IH, NH), 6.45 (d, IH), 4.68 (d, 2H), 2.94 (s, 6H). 44 δ 7.85 (d, 2H), 6.95-7.10 (m, 2H), 6.88 (s, IH), 6.22 (br t, IH, NH), 4.61 (d, 2H), 2.93 (t, 2H), 2.48 (t, 2H), 2.48 (s, 3H), 1.63-1.80 (m, 2H), 1.06 (t, 3H). 62 δ 7.30-7.42 (m, IH), 7.68 (t, IH), 7.27-7.43 (m, 2H), 6.63 (br s, IH, NH), 6.51 (d, IH), 4.68 (d, 2H), 3.28 (q, 4H), 1.07 (t, 6H). Compound 1H NMR Data (CDCI3 solution unless indicated otherwise)3 76 δ 7.10-7.33 (m, 4H), 6.64 (s, IH), 6.10 (br t, IH, NH), 4.68 (d, 2H), 4.00 (t, 2H), 2.50 (s, 3H), 1.70-1.90 (m, 2H), 0.97 (t, 3H). 82 δ 7.46 (m, IH), 7.39 (m, IH), 7.26 (m, 2H), 6.69 (s, IH), 4.70 (d, 2H), 4.09 (t, 2H), 3.76 (s, 3H), 1.70 (q, 2H), 0.98 (t, 3H). 86 δ 7.30 (t, 3H), 7.25 (s, IH), 6.50 (s, IH), 4.60 (s, 2H), 4.16 (s, 2H), 3.78 (s, 3H), 1.77 (m, 2H), 1.00 (m, 3H). 97 δ 7.30 (m, 4H), 6.27 (s, IH), 5.20 (t, IH), 5.02 (s, 2H), 3.80 (s, 3H), 2.58 (s, IH), 1.57 (d, 3H). 98 δ 7.37 (m, 2H), 7.05 (t, 2H), 6.15 (s, IH), 5.15 (m, IH), 5.02 (s, 2H), 3.81 (s, 3H), 2.60 (s, IH), 1.57 (d, 3H). 104 δ 7.73 (s, IH), 7.27 (m, 2H), 7.01 (t, 2H), 6.43 (s, IH), 4.53 (d, 2H), 4.10 (t, 2H), 3.69 (s, 3H), 1.71 (q, 2H), 0.95 (t, 3H). Ill δ 7.71 (s, IH), 7.30 (s, 4H), 6.31 (d, IH), 5.26 (q, IH), 4.10 (m, 2H), 3.69 (s, 3H), 1.76, (q, 2H), 1.53 (d, 2H), 0.99 (t, 3H). 152 δ 7.29 (d, 2H), 6.87 (d, 2H), 6.59 (s, IH), 5.93 (br d, IH, NH), 5.08 (q, IH), 3.93 (t, 2H), 3.80 (s, 3H), 2.47 (s, 3H), 1.65-1.95 (m, 4H), 1.01 (t, 3H), 0.92 (t, 3H). 164 δ 8.245 (s, IH), 8.188 (s, IH), 7.33 (m, 3H), 6.01 (d, IH), 5.37 (m, IH), 4.072 (q, 2H), 1.78 (m, 2H), 1.59 (d, 3H), 1.42 (m, 3H), 0.919 (t, 3H). 165 δ 8.221 (s, IH), 8.163 (s, IH), 7.391 (m, 2H), 7.037 (m, 2H), 6.11 (d, IH), 5.37 (m, IH), 4.062 (q, 2H), 1.75 (m, 2H), 1.59 (d, 3H), 1.42 (m, 2H), 0.939 (t, 3H). 169 δ 8.348 (s, IH), 8.273 (s, IH), 7.345 (m, 4H), 6.21 (d, IH), 6.01 (d, IH), 5.38 (m, IH), 5.08 (m, IH), 1.65 (d, 2H), 1.63 (d, 2H), 1.61 (d, 3H). 170 δ 8.228 (br s, 2H), 7.335 (m, 2H), 7.144 (m, 2H), 6.01 (d, IH), 5.38 (m, IH), 5.08 (m, IH), 2.33 (s, 3H), 1.65 (d, 2H), 1.63 (d, 2H), 1.61 (d, 3H). 171 δ 8.233 (s, IH), 8.199 (s, IH), 7.345 (m, 2H), 6.98 (m, 2H), 6.11 (d, IH), 6.01 (d, IH), 5.37 (m, IH), 5.02 (m, IH), 3.81 (s, 3H), 1.65 (d, 2H), 1.63 (d, 2H), 1.61 (d, 3H). 177 δ 8.255 (s, IH), 8.197 (s, IH), 7.276 (m, 2H), 6.811 (d, IH), 6.010 (d, IH), 5.373 (m, IH), 4.04 (m, 2H), 3.81 (s, 2H), 1.81 ( , 2H), 0.980 (m, 3H). 178 δ 8.254 (s, IH), 8.202 (s, IH), 7.345 (m, 2H), 7.145 (m, 2H), 6.01 (d, IH), 5.38 (m, IH), 4.04 ( , 2H), 2.33 (s, 3H), 1.81 (m, 2H),1.601 (d, 3H), 0.980 (m, 3H). 180 δ 8.224 (s, IH), 8.199 (s, IH), 7.460 (m, 2H), 7.322 (m, 2H), 6.20 (d, IH), 5.37 (m, IH), 4.04 (m, 2H), 1.81 (m, 2H), 1.601 (d, 3H), 0.978 (m, 3H). 187 δ 7.31 (d, 2H), 6.86 (d, 2H), 6.59 (s, IH), 5.90 (br d, IH, NH), 5.18-5.30 (m, IH), 3.92 (t, 2H), 3.80 (s, 3H), 2.47 (s, 3H), 1.60-1.83 (m, 5H), 0.83-1.03 (m, 9H). 191 δ 8.263 (s, IH), 8.213 (s, IH), 7.402 (m, 2H), 7.041 (m, 2H), 6.02 (d, IH), 5.38 (m, IH), 4.108 (m, 2H), 1.81 (m, 2H), 1.616 (d, 3H), 0.978 (m, 3H). 192 δ 9.19 (s, IH), 9.106 (s, IH), 8.963 (s, IH), 7.405 (m, 4H), 5.128 (m, IH), 4.318 (s, 3H), 4.151 (m, 2H), 1.775 (m, 2H), 1.435 (d, 3H), 0.883 (m, 3H). Compound 1H NMR Data (CDCI3 solution unless indicated otherwise)3 193 δ 9.37 (d, IH), 9.199 (s, IH), 9.024 (s, IH), 7.405 (m, 4H), 5.158 (m, IH), 4.604 (m, 2H), 4.208 (s, 2H), 1.775 (m, 2H), 1.558 (m, 3H), 1.435 (d, 3H), 0.883 (m, 3H). 202 δ 7.56 (m, 2H), 7.14 (dd, 2H), 6.64 (s, IH), 6.39 (m, 2H), 3.99 (t, 2H), 2.50 (s, 3H), 1.79 (m, 2H), 0.99 (t, 3H). 203 δ 8!236 (s, IH), 8.172 (s, IH), 7.347 (m, 4H), 6.12 (d, IH), 5.38 (m, IH), 4.145 (m, 2H), 1.594 (d, 3H), 1.392 (m, 3H). 204 δ 8.406 (s, IH), 8.313 (s, IH), 7.347 (m, 4H), 6.18 (d, IH), 5.309 (m, IH), 4.838 (s, 2H), 1.595 (d, 3H). 211 δ 7.60 (d, 2H), 7.28 (d, 2H), 6.61 (s, IH), 6.36 (s, IH), 3.96 (t, 2H), 2.45 (s, 3H), 1.75 (m, 2H), 0.96 (t, 3H). 212 δ 7.73 (m, 4H), 6.66 (s, IH), 6.47 (m, 2H), 4.00 (t, 2H), 2.51 (s, 3H), 1.78 (m, 2H), 0.98 (t, 3H). 213 δ 8.217 (s, IH), 8.182 (s, IH), 7.332 (m, 4H), 6.376 (d, IH), 5.38 (m, IH), 4.088 (m, 2H), 1.807 (m, 2H), 1.592 (d, 3H), 0.986 (m, 3H). 214 δ 8.196 (s, IH), 8.193 (s, IH), 7.398 (m, 2H), 7.038 (m, 2H), 6.422 (d, IH), 5.38 (m, IH), 4.070 (m, 2H), 1.799 (m, 2H), 1.596 (d, 3H), 0.978 (m, 3H). 215 δ 8.175 (s, IH), 8.135 (s, IH), 7.334 (m, 2H), 6.896 (m, 2H), 6.381 (d, IH), 5.354 (m, IH), 4.056 (m, 2H), 3.804 (s, 3H), 1.802 (m, 2H), 1.588 (d, 3H), 0.988 (m, 3H). 222 δ 7.39 (m, 2H), 7.03 (m, 2H), 6.91 (s, IH), 5.94 (br d, IH), 5.36 (t, 3H), 4.00 (t, 2H), 2.07 (s, 3H), 3.69 (s, 2H), 1.77 (m, 2H), 1.59 (d, 3H), 0.98 (t, 3H). 223 δ 7.33 (m, 2H), 6.87 (m, 3H), 6.03 (br d, IH), 5.33 (t, 3H), 3.99 (t, 2H), 3.79 (s, 3H), 3.67 (s, 2H), 2.05 (s, 3H), 1.77 (m, 2H), 1.59 (d, 3H), 0.98 (t, 3H). 235 δ 7.47 (dd, IH), 7.26 (IH), 7.10 (t, IH), 6.65 (s, IH), 6.05 (br t, IH, NH), 4.61 (d, 2H), 3.99 (t, 2H), 2.51 (s, 3H), 1.73-1.87 (m, 2H), 0.97 (t, 3H). 241 (CD3OD) δ 7.57 (d, 2H), 7.48 (d, 2H), 7.00 (s, IH), 6.36 (s, IH), 4.06 (t, 2H), 2.47 (s, 3H), 1.74 (m, 2H), 0.96 (t, 3H). 242 (CD3OD) δ 7.62 (dd, 2H), 7.49 (dd, 2H), 6.98 (s, IH), 6.34 (s, IH), 4.09 (m, 2H), 2.46 (s, 3H), 1.77 (m, 2H), 0.95 (t, 3H). 243 δ 7.13 (s, IH), 7.10 (s, IH), 6.61 (s, IH), 6.17 (br t, IH, NH), 4.63 (d, 2H), 3.95 (t, 2H), 3.88 (s, 3H), 2.49 (s, 3H), 1.64-1.77 (m, 2H), 0.90 (t, 3H). 251 δ 7.26 (m, IH), 6.96-7.04 (m, 2H), 6.81 (dd, IH), 6.64 (s, IH), 6.09 (br s, IH, NH), 5.30- 5.43 (m, IH), 4.56-4.70 (m, IH), 3.81 (s, 3H), 2.52 (s, 3H), 1.60 (d, 3H), 1.34 (t, 6H). 258 δ 7.00-7.26 (m, 4H), 6.72 (s, IH), 6.58-6.63 (m, 2H), 5.77 (br t, 1, NH), 4.60 (d, 2H), 3.99 (t, 2H), 2.49 (s, 3H), 2.30 (s, 3H), 2.21 (s, 3H), 1.73-1.87 (m, 2H), 1.31 (s, 9H), 0.98 (t, 3H). 259 δ 7.42 (t, IH) , 7.08 (m, 2H), 6.58 (s, IH), 6.52 (t, IH, NH), 4.60 (d, 2H), 3.93 (t, 2H), 2.45 (s, 2H), 1.62 (m, 2H), 0.94 (t, 3H). 260 δ 7.40 (t, IH) , 7.16 (m, 2H), 6.62 (t, IH, NH), 6.57 (s, IH), 4.58 (d, 2H), 3.93 (t, 2H), 2.45 (s, 2H), 1.64 (m, 2H), 0.94 (t, 3H). Compound IH NMR Data (CDCI3 solution unless indicated otherwise)3 261 δ 7.59 (d, 2H), 7.28 (d, 2H), 7.00 (br d, IH), 6.60 (s, IH), 6.34 (d, IH), 5.78-6.10 (t, IH), 3.96 (t, 2H), 2.44 (s, 3H), 1.72 (m, 2H), 0.96 (t, 3H). 262 δ 7.28-7.38 (m, IH), 7.09-7.16 (m, IH), 6.61 (s, IH), 6.38 (br s, IH, NH), 4.61 (d, 2H), 3.97 (t, 2H), 2.48 (s, 3H), 1.73-1.87 (m, 2H), 0.95 (t, 3H). 263 δ 7.00-7.40 (m, 2H), 6.60 (s, IH), 6.40 (br s, IH, NH), 4.60 (d, 2H), 3.94 (t, 2H), 2.49 (s, 3H), 2.31 (s, 3H), 1.73-1.87 (m, 2H), 0.93 (t, 3H). 265 δ 7.30-7.73 (m, 3H), 6.63 (s, IH), 6.41 (br t, IH, NH), 4.70 (d, 2H), 3.98 (t, 2H), 2.49 (s, 3H), 1.73-1.87 (m, 2H), 0.93 (t, 3H). 277 (CD3OD) δ 7.61 (m, 2H), 7.20 (m, 2H), 7.02 (s, IH), 6.34 (s, IH), 4.75 (septet, IH), 2.46 (s, 3H), 1.32 (d, 3H), 1.28 (d, 3H). 278 (CD3OD) δ 7.63 (d, 2H), 7.53 (d, 2H), 7.02 (s, IH), 6.34 (s, IH), 4.77 (septet, IH), 2.47 (s, 3H), 1.32 (d, 3H), 1.28 (d, 3H). 283 (CD3OD) δ 7.81 (m, IH), 7.60 (m, IH), 7.32 (m, IH), 7.02 (s, IH), 6.38 (s, IH), 4.78 (septet, IH), 2.47 (s, 3H), 1.32 (d, 3H), 1.29 (d, 3H). 284 (CD3OD) δ 7.60 (m, 2H), 7.32-7.50 (m, 2H), 7.01 (s, IH), 6.42 (s, IH), 4.78 (septet, IH), 2.47 (s, 3H), 1.32 (d, 3H), 1.29 (d, 3H). 286 (CD3OD) δ 7.33 (s, IH), 7.19 (s, IH), 7.00 (s, IH), 6.32 (s, IH), 4.78 (septet, IH), 3.91 (s, 3H), 3.82 (s, 3H), 1.38 (m, 6H). ' 289 (CD3OD) δ 7.28-7.46 (m, 3H), 7.00 (m, IH), 6.46 (s, IH), 4.78 (septet, IH), 2.46. (s, 3H), 1.26 (m, 6H). 290 (CD3OD) δ 7.70 (d, 2H), 7.38 (d, 2H), 7.00 (m, IH), 6.41 (s, IH), 4.78 (septet, IH), 2.50 (s, 3H), 1.36 (m, 6H). 291 (CD3OD) δ 7.56 (d, 2H), 7.46 (d, 2H), 7.05 (d, IH), 6.38 (s, IH), 4.78 (septet, IH), 2.48 (s, 3H), 1.27 (m, 6H). 292 (CD3OD) δ 7.51 (m, 2H), 7.09 (m, 2H), 6.98 (s, IH), 5.68 (s, IH), 4.72 (septet, IH), 2.48 (s, 3H), 1.25 (d, 6H). 294 δ 7.26 (dt, IH), 6.78-7.01 (m, 3H), 6.66 (s, IH), 5.94-6.12 (m, IH), 5.24-5.39 (m, IH), 4.64^1.86 (m, IH), 3.80 (s, 3H), 2.51 (s, 3H), 1.44-1.62 (m, 6H). 297 δ 7.44 (m, 2H), 7.05 (m, 2H), 6.64 (s, IH), 5.78 (d, IH), 4.61 (septet, IH), 3.78 (s, 3H), 2.50 (s, 3H), 1.30 (m, 6H). 298 δ 7.98 (d, IH), 7.75 (m, 2H), 7.03 (m, 2H), 6.62 (d, IH), 5.39 (s, IH), 4.68 (septet, IH), 2.50 (s, 3H), 1.46 (d, 3H), 1.37 (d, 3H). 299 δ 7.22-7.31 (m, IH), 6.79-7.03 (m, 3H), 6.67 (s, IH), 5.86-6.05 (m, IH), 5.25-5.40 (m, IH), 4.67^.82 (m, IH), 3.81 (s, 3H), 2.52 (s, 3H), 1.45-1.64 (m, 6H). a IH NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (dq)-doublet of quartets, (br s)-broad singlet, (br d)-broad d, (br m)-broad multiplet. BIOLOGICAL EXAMPLES OF THE TNVENTION
TEST A Seeds of barnyardgrass (Echinochloa crus-gallϊ), large crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberi), momingglory (Ipomoea spp.), redroot pigweed (Amaranthus retroflexus) and velvetleaf (Abutilon theophrasti) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time these species were also treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the 1- to 2-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately ten days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, were calculated as the means of the two replicates and are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test results.
Table A Comj >ounds
2000 g ai/ha 4 5 8 9 10 11 12 13 14 15 16 17 18 47
Postemergence
Barnyardgrass 60 80 40 80 100 35 85 30 60 40 30 35 80 20
Crabgrass, Large 35 45 20 75 95 45 95 30 60 30 25 25 85 20
Foxtail, Giant 55 60 30 70 100 40 90 30 45 35 25 25 90 20
Momingglory 20 60 25 95 65 60 70 30 50 50 65 45 80 20
Pigweed 35 90 10 100 100 30 100 25 85 0 35 80 100 25
Velvetleaf 35 40 30 100 100 30 100 35 50 100 35 25 100 20
Table A Compounds
2000 g ai/ha 48 59 60 61 78 79 80 81 82 83 85 86 97 98
Postemergence
Barnyardgrass 30 30 20 20 45 30 20 0 10 90 20 20 20 20
Crabgrass, Large 50 10 10 0 25 20 10 5 10 50 30 20 20 10
Foxtail, Giant 50 25 20 25 65 25 10 0 10 90 40 30 20 20
Momingglory 60 15 10 5 15 5 0 10 20 90 20 20 0 0
Pigweed 45 15 30 15 45 30 10 20 10 90 20 5 50 55
Velvetleaf 55 20 0 20 40 15 10 5 20 95 30 20 20 20
Table A Compounds Table A Compounds
2000 g ai/ha 99 135 136 137 138 140 1000 g ai/ha 202 262
Postemergence Postemergence
Barnyardgrass 60 65 30 30 90 100 Barnyardgra SS 95 95 Crabgrass, Large 20 25 10 10 70 90 Crabgrass, Large 85 65 Foxtail, Giant 45 65 40 40 95 100 Foxtail, Giant 100 85 Momingglory 65 75 50 75 85 90 Momingglory 80 100 Pigweed 100 90 40 80 95 100 Pigweed 100 100 Velvetleaf 100 50 30 40 60 100 Velvetleaf 100 100
Table A Compounds 500 g ai/ha 5 6 7 8 10 11 12 13 14 Postemergence Barnyardgrass 70 45 65 30 55 60 30 30 55 70 30 60 30 35 Crabgrass, Large 50 45 70 20 30 55 20 0 55 75 20 65 30 10 Foxtail, Giant 60 65 65 25 50 80 40 30 55 80 30 75 30 30 Momingglory 75 65 70 30 40 85 70 30 100 75 35 45 30 75 Pigweed 95 100 100 25 70 100 100 0 60 95 20 95 15 30 Velvetleaf 100 95 100 20 50 100 100 25 100 100 30 100 30 35
Table A Compounds 500 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Postemergence Barnyardgrass 35 20 30 55 65 30 60 35 40 25 20 30 20 60 Crabgrass, Large 10 0 20 75 45 20 45 30 40 10 20 15 10 55 Foxtail, Giant 30 10 30 80 60 30 50 40 65 20 25 20 10 55 Momingglory 60 50 65 90 50 40 85 85 85 30 45 55 10 55 Pigweed 0 10 35 90 80 100 95 70 90 25 65 30 15 100 Velvetleaf 100 40 35 85 100 45 100 85 90 25 40 65 10 100
Table A Compounds 500 g ai/ha 29 30 31 32 33 34 35 36 37 38 39 40 41 42 Postemergence Barnyardgrass 100 85 85 55 75 85 20 90 25 20 30 75 45 30 Crabgrass, Large 95 100 90 50 80 80 0 90 40 20 35 65 35 20 Foxtail, Giant 100 100 90 70 95 95 0 70 50 55 60 70 85 40 Mo ingglory 100 100 100 95 100 100 0 100 65 55 60 100 70 50 Pigweed 100 100 100 100 100 100 0 100 75 90 40 100 100 95 Velvetleaf 100 100 100 100 100 100 10 100 65 80 80 100 100 85
Table A Compounds 500 g ai/ha 43 44 45 46 47 48 49 50 51 52 53 54 55 56 Postemergence Barnyardgrass 20 40 90 40 20 30 70 100 85 75 35 10 85 15 Crabgrass, Large 20 40 75 50 20 25 45 85 60 45 15 10 50 15 Foxtail, Giant 25 45 85 50 20 45 85 85 85 60 20 10 80 10 Momingglory 25 50 100 55 20 30 100 100 100 50 75 30 100 30 Pigweed 60 60 100 100 20 35 100 100 100 100 50 20 100 50 Velvetleaf 25 75 100 85 20 40 100 100 100 75 90 15 100 20
Table A Compounds 500 g ai/ha 57 58 59 60 61 62 63 64 65 66 67 68 69 70 Postemergence Barnyardgrass 100 50 20 10 20 30 20 90 30 30 85 65 40 20 Crabgrass, Large 100 25 10 0 0 20 20 85 20 10 40 30 10 10 Foxtail, Giant 100 65 20 10 10 30 20 100 40 45 70 70 30 20 Momingglory 100 65 20 20 0 65 20 100 85 100 100 95 50 20 Pigweed 100 100 10 15 15 30 25 95 90 100 100 100 45 15 Velvetleaf 100 100 15 0 15 40 25 100 85 100 100 100 40 10
Table A Compounds 500 g ai/ha 71 72 73 74 75 76 77 78 79 80 82 83 84 Postemergence Barnyardgrass 75 95 100 100 90 65 30 25 10 10 0 10 65 20 Crabgrass, Large 20 85 75 85 35 30 30 10 10 0 10 5 10 25 Foxtail, Giant 75 100 90 95 80 70 40 20 10 10 0 10 80 30 Momingglory 100 100 100 100 100 100 25 10 0 0 0 5 60 30 Pigweed 100 100 100 100 100 100 30 20 20 10 10 0 85 50 Velvetleaf 100 100 100 100 100 100 45 20 20 10 0 20 70 80
Table A Compounds 500 g ai/ha 85 86 87 88 89 90 91 92 93 94 95 96 97 98 Postemergence Barnyardgr ss 20 10 95 100 90 65 15 10 95 35 30 20 0 10 Crabgrass, Large 0 10 90 100 70 20 10 10 80 20 20 10 0 10 Foxtail, Giant 0 20 100 95 90 85 10 10 90 75 30 25 0 10 Momingglory 0 10 100 80 100 40 0 0 100 45 25 40 0 0 Pigweed 0 0 100 100 100 80 5 35 100 80 80 15 25 0 Velvetleaf 20 20 100 100 100 55 10 20 100 80 70 40 20 10
Table A Compounds 500 g ai/ha 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Postemergence Barnyardgrass 30 0 100 100 100 20 100 100 100 100 65 95 25 20 Crabgrass, Large 20 0 90 75 90 0 100 95 95 100 80 65 35 10 Foxtail, Giant 20 0 100 100 100 0 100 100 100 100 100 100 75 20 Momingglory 40 0 100 100 100 25 100 100 100 100 75 70 55 35 Pigweed 80 0 100 100 100 10 100 100 100 100 100 100 100 100 Velvetleaf 50 0 100 100 100 30 100 100 100 100 70 100 60 30
Table A Compounds 500 g ai/ha 114 116 117 135 136 137 138 140 147 152 170 171 172 173 Postemergence Barnyardgrass 75 70 10 40 30 30 35 65 75 100 30 20 60 40 Crabgrass, Large 40 30 10 15 10 10 10 45 60 90 20 10 10 15 Foxtail, Giant 100 75 10 80 20 20 70 80 85 95 50 20 70 50 Momingglory 90 95 10 75 45 70 70 85 70 95 15 10 60 80 Pigweed 100 100 50 80 30 60 85 90 100 100 55 50 100 100 Velvetleaf 100 100 20 50 30 35 55 90 100 100 50 15 100 85
Table A Compounds 500 g ai/ha 174 177 178 179 180 185 186 187 188 189 190 191 192 193 Postemergence Barnyardgrass 20 50 30 25 50 100 100 35 60 30 60 20 20 20 Crabgrass, Large 25 20 25 10 10 100 100 10 80 10 40 10 10 10 Foxtail, Giant 20 50 50 50 60 100 100 45 95 45 80 90 40 20 Momingglory 0 0 10 15 55 95 100 50 95 55 90 80 50 45 Pigweed 20 30 80 95 100 100 100 70 100 30 100 100 50 35 Velvetleaf 25 25 80 15 100 100 100 65 100 100 100 100 100 60
Table A Compounds
500 g ai/ha 194 195 196 197 199 200 201 203 204 205 206 207 208 209
Postemergence
Barnyardgrass 10 55 55 50 20 70 15 20 10 35 55 10 15 15
Crabgrass, Large 10 10 10 10 10 10 0 0 0 10 10 0 0 5
Foxtail, Giant 20 70 70 50 30 55 45 55 20 85 75 15 65 40
Momingglory 15 10 15 0 0 15 10 35 70 100 10 10 0 10
Pigweed 65 90 90 - 60 30 10 100 40 95 100 20 20 95
Velvetleaf 75 70 45 10 10 70 20 65 100 90 15 20 15 55
Table A Compounds 500 g ai/ha 210 211 213 214 215 216 217 218 219 220 221 222 223 224 Postemergence Barnyardgrass 50 55 60 55 40 85 100 100 100 95 100 20 20 10 Crabgrass, Large 50 25 10 35 10 55 80 95 90 75 95 10 10 5 Foxtail, Giant 60 60 65 80 65 85 95 100 100 95 100 50 65 10 Momingglory 0 95 80 40 20 95 75 100 100 95 100 55 60 10 igweed 85 100 60 50 35 100 100 100 100 100 100 100 90 15
Velvetleaf 25 100 90 75 65 100 100 100 100 100 100 100 100 20
Table A Compounds
500 g ai/ha 225 226 227 228 229 230 231 232 233 234 235 236 237 238
Postemergence
Barnyardgrass 20 35 50 60 100 100 100 95 60 85 85 100 100 100
Crabgrass, Large 20 10 20 60 95 85 85 85 30 70 60 95 100 95
Foxtail, Giant 40 40 45 60 100 100 100 100 85 100 85 100 100 100
Momingglory 60 65 15 35 100 100 100 100 80 100 100 100 100 100
Pigweed 55 80 65 65 100 100 100 100 100 100 100 100 100 100
Velvetleaf 40 65 75 85 100 100 100 100 100 100 100 100 100 100
Table A Compounds 500 g ai/ha 239 240 241 242 243 244 245 246 247 248 249 250 251 252 Postemergence Barnyardgrass 95 85 70 55 85 35 95 95 85 85 90 95 90 75 Crabgrass, Large 95 65 55 10 50 15 50 75 .35 60 80 85 80 80 Foxtail, Giant 100 100 90 75 90 90 95 90 90 90 80 90 95' 90 Momingglory 100 100 95 100 100 100 100 100 80 75 90 90 100 100 Pigweed 100 100 100 100 100 100 100 100 100 100 100 65 100 100 Velvetleaf , 100 100 100 100 100 100 100 100 100 100 70 75 100 100
Table A Compounds 500 g ai/ha 253 254 255 256 257 258 259 260 261 263 264 265 266 267 Postemergence Barnyardgrass 60 70 95 30 15 20 95 90 10 85 100 80 100 95 Crabgrass, Large 65 50 80 20 5 10 55 30 20 25 85 70 85 65 Foxtail, Giant 85 65 95 55 20 15 95 95 20 90 95 90 90 95 Morningglory 100 70 100 70 0 30 100 100 25 100 95 100 100 100 Pigweed 100 100 100 100 10 75 100 100 25 100 100 100 100 100 Velvetleaf 100 100 100 100 0 40 100 100 35 100 100 100 100 100
Table A Compounds 500 g ai/ha 268 269 270 271 272 273 274 275 276 277 278 279 280 281 Postemergence Barnyardgrass 95 65 90 45 95 80 85 100 25 75 30 100 65 55 Crabgrass, Large 80 20 70 55 85 65 75 90 20 75 10 75 45 30 Foxtail, Giant 95 55 95 55 100 95 100 100 50 90 25 100 100 80 Mo ingglory 100 100 100 100 100 100 100 100 100 100 95 100 100 100 pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Table A Compounds 500 g ai/ha 282 283 284 286 287 288 289 290 291 292 293 294 295 296 Postemergence Barnyardgrass 85 25 45 20 20 95 50 25 50 15 90 100 95 30 Crabgrass, Large 55 20 15 10 20 60 45 20 25 10 50 70 60 10 Foxtail, Giant 90 55 65 40 60 95 40 35 55 10 90 90 90 25 Momingglory 100 75 100 95 75 100 85 100 80 0 100 100 100 45 Pigweed 100 100 100 100 100 100 100 100 100 0 100 100 100 45 Velvetleaf 100 100 100 100 100 100 100 100 100 10 100 100 100 40
Table A Compounds 250 g ai/ha 297 169 181 182 183 184 202 262 Postemergence Barnyardgrass 20 35 45 100 90 30 75 75 Crabgrass, Large 10 10 20 90- 75 20 65 35 Foxtail, Giant 30 50 55 95 100 20 95 90 Momingglory 95 55 50 100 60 65 65 100 Pigweed 100 100 100 100 100 100 100 100 Velvetleaf 100 40 50 100 100 45 100 100
Table A Compounds
125 g ai/ha 1 2 3 6 7 19 20 21 22 23 24 25 26 27
Postemergence
Barnyardgrass 40 30 40 30 20 40 20 30 35 30 10 20 20 10
Crabgrass, Large 25 30 20 30 20 20 10 15 30 20 10 10 10 10
Foxtail, Giant 35 45 45 50 30 40 20 30 25 40 10 20 20 10
Momingglory 50 60 40 55 50 50 25 50 40 40 10 20 45 10
Pigweed 70 75 90 100 55 60 95 45 35 55 10 30 20 10
Velvetleaf 100 40 100 100 85 100 45 90 40 40 10 30 30 10
Table A Compounds 125 g ai/ha 28 29 30 31 32 33 34 35 36 37 38 39 40 41 Postemergence Barnyardgrass 20 65 55 50 40 55 55 0 55 20 20 20 65 35 Crabgrass, Large 30 75 60 50 40 60 60 0 60 25 20 10 55 20 Foxtail, Giant 30 75 75 75 45 80 75 0 55 25 40 35 65 45 Momingglory 50 100 100 100 60 70 70 0 95 65 35 20 95 40 Pigweed 100 100 85 55 65 100 70 0 100 50 60 20 100 90 Velvetleaf 100 100 100 100 100 100 100 0 100 40 40 40 100 100
Table A Compounds 125 g ai/ha 42 43 44 45 46 49 50 51 52 53 54 55 56 57 Postemergence Barnyardgrass 35 20 30 60 30 35 70 60 25 10 10 50 10 75 Crabgrass, Large 20 15 30 70 30 10 40 35 10 10 10 20 10 75 Foxtail, Giant 30 15 35 60 40 50 60 50 20 10 10 35 10 85 Morningglory 20 15 40 100 25 100 85 90 45 75 30 90 15 100 Pigweed 55 20 45 100 50 95 100 100 75 25 10 80 20 100 Velvetleaf 35 10 40 100 45 95 100 100 65 55 10 100 20 100
Table A Compounds 125 g ai/ha 58 62 63 64 65 66 67 68 69 70 71 72 73 74 Postemergence Barnyardgrass 25 30 20 75 20 20 60 40 20 15 35 80 90 100 Crabgrass, Large 20 20 20 30 20 10 10 10 10 10 10 60 40 35 Foxtail, Giant 50 20 20. 55 20 35- 45 30 20 10 35 90 75 75 Momingglory 65 40 20 100 50 95 90 80 40 15 100 100 100 100 Pigweed 90 20 20 30 60 100 100 100 30 10 100 100 100 100 Velvetleaf 100 30 20 75 25 100 100 90 30 5 100 100 100 100
Table A Compounds
125 g ai/ha 75 76 77 84 87 88 89 90 91 92 93 94 95 96
Postemergence
Barnyardgrass 30 40 20 20 90 90 50 20 0 0 60 20 10 10
Crabgrass, Large 10 10 15 20 60 55 50 20 0 5 20 10 10 10
Foxtail, Giant 45 55 20 25 100 80 70 55 0 10 70 45 10 5
Momingglory 100 100 10 20 100 60 100 45 0 0 95 25 20 15
Pigweed 90 90 20 45 100 100 100 20 0 20 100 65 30 10
Velvetleaf 100 100 30 50 100 100 100 20 5 0 100 55 50 20
Table A Compounds
125 g ai/ha 100 101 102 103 104 105 106 107 108 109 110 111 112 114
Postemergence
Barnyardgrass 0 95 85 95 0 100 90 90 90 25 80 20 20 20
Crabgrass , Large 0 65 70 80 0 80 60 85 60 40 35 10 10 20
Foxtail, Giant 0 85 95 95 0 95 90 95 100 65 75 35 10 70
Momingglory 0 75 85 90 15 100 90 100 100 70 70 40 30 80
Pigweed 0 100 100 100 5 100 100 100 100 65 95 80 100 100
Velvetleaf 0 100 100 100 10 100 100 100 100 65 100 40 20 100 Table A Compounds 125 g ai/ha 116 117 147 152 170 171 172 173 174 177 178 179 180 185 Postemergence Barnyardgrass 45 0 70 60 10 10 50 20 25 25 20 10 30 85 Crabgrass, Large 30 0 45 70 10 20 10 0 15 20 10 10 60 Foxtail, Giant 70 0 80 90 10 10 55 30 20 25 30 25 25 95 Momingglory 90 0 50 80 0 45 40 5 20 100 Pigweed 100 10 100 100 10 10 100 60 40 20 25 30 100 100 Velvetleaf 100 0 55 100 10 0 85 75 30 20 25 10 20 100
Table A Compounds 125 g ai/ha 186 187 188 189 190 191 192 193 194 195 196 197 199 200 Postemergence Barnyardgrass 100 20 55 20 25 5 10 10 10 25 10 10 10 10 Crabgrass, Large 85 10 50 10 15 0 10 10 0 10 10 10 5 0 Foxtail, Giant 95 20 75 10 70 30 10 15 10 45 25 15 10 10 Momingglory 100 25 90 30 95 0 25 5 0 45 15 0 0 25 Pigweed 100 40 95 20 95 10. 5 10 5 95 90 - 50 10 Velvetleaf 100 40 90 60 95 15 65 65 35 75 15 10 10 70
Table A Compounds 125 g ai/ha 201 203 204 205 206 207 208 209 210 211 213 214 215. 216 Postemergence Barnyardgrass 0 10 10 10 10 10 10 10 10 25 35 10 10 30 Crabgrass, Large 0 0 0 10 0 0 0 0 10 10 10 10 10 20 Foxtail, Giant 10 20 10 50 15 10 10 10 35 35 70 30 20 65 Momingglory 0 10 10 35 10 0 10 10 0 75 60 10 15 45 Pigweed 0 15 10 95 85 20 10 10 95 100 30 35 20 50 Velvetleaf 15 10 20 100 20 20 20 25 70 100 70 45 35 55
Table A Compounds
125 g ai/ha 217 218 219 220 221 222 223 224 225 226 227 228 229 230
Postemergence
Barnyardgrass 95 95 100 70 85 10 10 10 10 10 35 25 95 80
Crabgrass, Large 65 65 70 45 50 10 10 10 10 10 10 10 85 45
Foxtail, Giant 85 100 100 75 100 30 25 10 10 15 25 35 95 80
Momingglory 65 100 100 35 100 15 30 10 50 45 30 15 100 100
Pigweed 100 100 100 95 100 75 35 10 45 65 75 30 100 100
Velvetleaf 100 100 100 100 100 75 80 15 15 45 75 100 100 100 Table A Compounds
125 g ai/ha 231 232 233 234 235 236 237 238 239 240 241 242 243 244
Postemergence
Barnyardgrass 100 100 35 90 55 90 90 95 90 60 45 25 75 40
Crabgrass, Large 70 80 20 60 35 90 70 65 90 30 10 10 10 10
Foxtail, Giant 90 95 55 100 65 100 95 85 95 70 75 40 75 85
Momingglory 100 100 80 100 100 100 100 100 100 100 95 85 100 100
Pigweed 100 100 100 100 100 100 100 100 100 100 100 90 100 100
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Table A Compounds
125 g ai/ha 245 246 247 248 249 250 251 252 253 254 255 256 257 258
Postemergence
Barnyardgrass 75 85 45 55 65 65 75 60 55 40 80 20 10 10
Crabgrass, Large 50 30 30 15 50 25 50 40 30 25 50 20 0 10
Foxtail, Giant 85 90 65 65 65 60 75 85 65 35 70 30 10 10
Momingglory 100 90 65 70 80 85 100 100 80 70 85 65 0 25
Pigweed 100 90 100 95 45 45 100 100 100 100 100 100 10 65
Velvetleaf 100 100 65 100 55 40 100 100 100 100 100 100 0 30
Table A Compounds
125 g ai/ha 259 260 261 263 264 265 266 267 268 269 270 271 272 273
Postemergence
Barnyardgrass 70 55 10 80 75 60 70 85 60 45 55 35 80 70
Crabgrass, Large 10 10 0 20 40 45 55 50 25 10 40 35 55 35
Foxtail, Giant 60 75 10 75 65 85 80 75 70 50 80 55 100 70
Momingglory 100 100 10 100 90 100 100 95 100 100 100 80 100 100
Pigweed 100 100 20 100 100 100 100 100 100 100 100 100 100 100
Velvetleaf 100 100 25 100 100 100 100 100 100 100 100 100 100 100
Table A Compounds
125 g ai/ha 274 275 276 277 278 279 280 281 282 283 284 286 287 288
Postemergence
Barnyardgrass 50 100 15 55 15 70 35 40 65 20 10 20 20 70
Crabgrass, Large 20 70 10 15 10 25 25 20 20 10 10 10 10 25
Foxtail, Giant 80 95 25 55 20 90 80 30 90 20 35 20 30 65
Momingglory 100 100 100 100 70 100 100 100 100 65 90 65 45 95
Pigweed 100 100 100 100 100 100 100 100 100 100 100 95 100 100
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 95 100 100 Table A Compounds 125 g ai/ha 289 290 291 292 293 294 295 296 297 Postemergence Barnyardgrass 25 20 15 0 60 65 50 10 20 Crabgrass, Large 25 25 20 0 25 35 15 10 10 Foxtail, Giant 35 40 45 0 55 60 50 20 25 Momingglory 75 80 90 0 100 90 90 50 55 Pigweed 100 100 100 0 100 100 100 20 95 Velvetleaf 100 100 100 10 100 100 100 20 100
Table A Compounds
62 g ai/ha 169 181 182 183 184
Postemergence
Barnyardgrass 20 20 75 85 20
Crabgrass, Large 10 10 75 65 10
Foxtail, Giant 20 30 85 85 20
Momingglory 20 20 95 65 20
Pigweed 50 75 100 100 85
Velvetleaf 25 30 100 100 25
Table A Compounds
2000 g ai/ha 4 5 8 9 10 11 12 13 14 15 16 17 18 47
Preemergence
Barnyardgrass 80 80 60 95 100 65 100 30 60 30 20 20 85 0
Crabgrass, Large 85 70 40 85 100 50 100 10 30 10 0 30 100 0
Foxtail, Giant 80 90 55 75 100 65 90 15 55 10 20 40 100 40
Momingglory 30 55 10 80 85 20 65 0 45 10 0 10 75 0
Pigweed 100 100 50 100 100 80 100 60 95 65 80 70 100 55
Velvetleaf 100 90 90 100 100 40 100 45 85 100 40 30 90 20
Table A Compounds 2000 g ai/ha 48 59 60 61 78 79 80 81 82 83 85 86 97 98 Preemergence Barnyardgrass 45 25 20 20 80 75 65 0 40 90 0 0 0 0 Crabgrass, Large 70 35 95 0 90 40 35 75 80 90 80 10 0 0 Foxtail, Giant 95 55 95 65 90 80 85 55 95 100 60 10 0 0 Momingglory 0 0 5 0 20 10 10 0 0 50 20 0 0 0 Pigweed 50 5 50 0 55 30 25 70 10 90 35 15 15 30 Velvetleaf 40 10 5 5 50 0 10 0 0 65 25 0 0 10 Table A Compounds Table A Compounds
2000 g ai/ha 99 135 136 137 138 140 1000 g ai/ha 202 262
Preemergence Preemergence
Barnyardgrass 30 95 90 90 95 95 Barnyardgrass 90 100
Crabgrass, Large 20 75 40 55 90 90 Crabgrass, Large 90 95
Foxtail, Giant 85 90 85 85 100 100 Foxtail , Giant 95 100
Momingglory 40 65 0 35 75 75 Momingglory 80 100
Pigweed 95 95 90 25 100 100 Pigweed 100 100
Velvetleaf 85 75 65 35 100 100 Velvetleaf 100 100
Table A Compounds
500 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14
Preemergence
Barnyardgrass 75 70 70 50 70 85 55 35 70 95 20 85 10 35
Crabgrass, Large 40 70 70 40 85 85 50 25 60 85 10 70 10 10
Foxtail, Giant 40 75 60 50 65 85 30 55 25 90 10 85 0 15
Momingglory 30 25 40 10 25 20 20 10 45 55 20 20 0 10
Pigweed 100 95 100 95 90 95 90 30 95 : 100 0 100 40 50
Velvetleaf 100 70 100 10 25 100 95 60 70 80 0 80 30 25
Table A Compounds
500 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28
Preemergence
Barnyardgrass 15 0 0 60 65 0 75 45 75 10 35 60 0 70
Crabgrass, Large 0 0 0 80 75 0 75 50 80 0 5 35 0 30
Foxtail, Giant 0 0 0 85 60 0 55 5 40 0 30 65 0 70
Momingglory 0 10 0 70 35 0 45 0 15 0 15 40 0 5
Pigweed 65 0 0 95 90 50 90 85 100 0 70 75 30 95
Velvetleaf 80 15 0 75 100 5 100 55 40 10 20 50 0 75
Table A Compounds
500 g ai/ha 29 30 31 32 33 34 35 36 37 38 39 40 41 42
Preemergence
Barnyardgrass 100 100 100 95 60 90 0 90 15 0 20 90 35 0
Crabgrass, Large 100 100 100 95 80 100 0 90 30 30 10 75 55 0
Foxtail, Giant 100 100 90 95 85 100 0 80 15 45 5 95 55 0
Mo ingglory 80 80 70 45 0 55 0 60 10 20 0 50 20 0
Pigweed 100 100 100 100 95 100 0 100 45 35 25 100 100 0
Velvetleaf 100 100 100 100 100 100 0 100 20 25 35 100 100 0 Table A Compounds
500 g ai/ha 43 44 45 46 47 48 49 50 51 52 53 54 55 56
Preemergence
Barnyardgrass 0 0 95 0 0 0 70 100 75 60 35 0 65 0
Crabgrass, Large 0 0 95 0 0 20 75 100 85 85 10 0 70 0
Foxtail, Giant 0 0 90 0 10 85 80 100 90 70 10 0 85 0
Momingglory 0 0 70 0 0 0 60 75 40 25 0 0 40 0
Pigweed 0 20 100 0 30 15 100 100 100 90 55 0 95 0
Velvetleaf 0 0 100 0 0 20 100 95 100 50 10 0 100 0
Table A Compounds
500 g ai/ha 57 58 59 60 61 62 63 64 65 66 67 68 69 70
Preemergence
Barnyardgrass 90 60 0 0 0 35 0 100 40 70 95 85 60 30
Crabgrass, Large 100 85 0 35 0 25 0 80 20 35 65 50 35 * 5
Foxtail, Giant 100 90 20 90 0 65 0 100 30 65 80 80 65 35
Mo ingglory 75 30 0 0 0 20 0 75 30 75 50 35 25 0
Pigweed 100 100 0 0 0 85 0 100 70 100 100 100 70 20
Velvetleaf 100 85 0 0 0 20 0 100 20 100 100 100 20 15
Table A Compounds 500 g ai/ha 71 72 73 74 75 76 77 7! 79 80 81 82 84 Preemergence Barnyardgrass 95 80 100 100 65 65 30 20 45 0 0 0 75 0 Crabgrass, Large 70 95 90 90 50 55 50 30 0 5 10 5 50 0 Foxtail, Giant 90 100 100 95 55 65 35 90 65 0 0 15 90 0 Momingglory 95 85 70 90 25 20 20 5 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 40 20 20 0 10 0 60 0 Velvetleaf 100 100 100 100 60 90 25 10 0 0 0 0 5 0
Table A Compounds
500 g ai/ha 85 86 87 $8 89 90 91 92 93 94 95 96 97 98
Preemergence
Barnyardgrass 0 0 100 100 100 65 0 0 70 20 0 5 0 0
Crabgrass, Large 15 5 95 100 95 90 0 0 65 60 5 15 0 0
Foxtail, Giant 0 0 100 100 90 90 10 0 90 65 10 55 0 0
Momingglory 0 0 80 75 40 0 0 0 70 10 0 0 0 0
Pigweed 10 0 100 100 100 80 40 0 95 80 70 45 0 0
Velvetleaf 0 0 100 100 100 60 0 0 100 70 25 20 0 0 Table A Compounds
500 g ai/ha 99 100 101 102 103 104 105 106 107 108 109 110 111 112
Preemergence
Barnyardgrass 0 0 100 100 100 0 100 100 100 100 70 85 55 20
Crabgrass, Large 0 0 90 90 95 0 100 100 100 100 85 80 40 0
Foxtail, Giant 15 0 100 100 100 0 100 100 100 100 100 100 80 30
Momingglory 10 0 100 90 85 0 80 90 85 85 0 40 0 60
Pigweed 75 0 100 100 100 25 100 100 100 100 55 100 90 90
Velvetleaf 15 0 100 100 95 0 100 100 100 100 40 100 0 0
Table A Compounds 500 g ai/ha 114 116 117 135 136 137 138 140 147 152 170 171 172 173 Preemergence Barnyardgrass 55 25 0 90 20 20 80 90 75 90 0 0 60 85 Crabgrass, Large 60 20 0 5 0 0 20 75 75 80 0 0 50 50 Foxtail, Giant 95 25 0 80 10 ,'15 50 95 90 90 10 10 70 60 Mo ingglory 35 15 0 20 0 10 0 40 50 85 0 0 0 20 Pigweed 100 95 55 90 10 0 90 95 100 95 0 0 80 50 Velvetleaf 95 90 0 30 0 0 50 95 100 100 0 20 10 70
Table A Compounds
500 g ai/ha 174 177 178 179 180 185 186 187 188 189 190 191 192 193
Preemergence
Barnyardgrass 50 35 80 10 80 100 100 45 35 0 60 75 0 0
Crabgrass, Large 40 25 80 80 70 100 100 40 10 0 20 45 0 0
Foxtail, Giant 40 0 55 70 85 100 100 50 50 0 75 85 0 0
Momingglory 0 0 0 10 0 90 95 0 15 0 10 0 0 0
Pigweed 75 40 25 85 85 100 100 95 50 0 60 70 0 0
Velvetleaf 0 0 0 20 45 100 100 55 25 0 25 10 0 0
Table A Compounds
500 g ai/ha 194 195 196 197 199 200 201 203 204 205 206 207 208 209
Preemergence
Barnyardgrass 0 80 60 60 35 55 0 45 0 50 70 0 15 20
Crabgrass, Large 0 60 45 5 20 15 0 10 0 5 45 10 15 0
Foxtail, Giant 0 85 65 40 60 40 0 60 10 85 90 15 85 15
Momingglory 0 0 5 0 0 5 0 0 0 0 0 0 0 0
Pigweed 0 75 100 80 20 60 0 15 0 60 100 0 70 0
Velvetleaf 0 45 10 0 0 20 0 0 0 0 10 10 0 0 Table A Compounds
500 g ai/ha 210 211 213 214 215 216 217 218 219 220 221 222 223 224
Preemergence
Barnyardgrass 70 60 80 90 50 90 100 100 100 100 100 10 0 0
Crabgrass, Large 75 70 30 45 20 85 95 100 95 90 90 10 ' 5 30
Foxtail, Giant 90 50 50 65 80 90 100 90 90 100 100 10 10 50
Momingglory 0 15 5 20 5 5 75 85 80 60 85 0 0 0
Pigweed 90 100 90 65 5 100 100 100 100 100 100 10 60 25
Velvetleaf 45 100 20 5 0 50 100 100 90 100 100 0 0 45
Table A Compounds
500 g ai/ha 225 226 227 228 229 230 231 232 233 234 235 236 237 238
Preemergence
Barnyardgrass 10 40 65 55 100 100 50 95 80 95 90 100 100 100
Crabgrass, Large 55 50 70 35 95 90 100 95 75 95 80 100 100 95
Foxtail, Giant 60 60 65 90 100 100 100 100 95 100 90 100 100 100
Mo ingglory 0 0 5 0 75 90 85 85 0 60 75 85 95 95
Pigweed 65 55 80 90 100 100 100 100 100 100 100 100 100 100
Velvetleaf 0 5 50 100 100 100 100 100 80 100 100 100 100 100
Table A Compounds
500 g ai/ha 239 240 241 242 243 244 245 246 247 248 249 250 251 252
Preemergence
Barnyardgrass 100 90 90 70 70 85 90 90 95 100 100 100 100 90
Crabgrass, Large 100 90 75 75 80 85 90 95 85 90 90 95 95 95
Foxtail, Giant 100 95 85 80 90 100 95 100 90 100 95 95 100 100
Momingglory 85 85 35 25 55 45 80 80 70 80 100 85 100 95
Pigweed 100 100 95 90 100 100 100 90 90 100 100 100 100 100
Velvetleaf 100 95 100 100 100 100 100 100 65 95 90 95 100 100
Table A Compounds 500 g ai/ha 253 254 255 256 257 258 259 260 261 263 264 265 266 267 Preemergence Barnyardgrass 100 95 100 70 0 0 100 90 60 85 95 100 100 95 Crabgrass, Large 85 90 95 50 0 0 90 70 40 80 90 100 100 90 Foxtail, Giant 95 90 100 60 0 0 95 90 60 100 95 100 100 100 Momingglory 95 65 90 25 0 0 65 70 0 100 75 95 85 90 Pigweed 95 100 100 100 0 35 100 100 85 100 100 100 100 100 Velvetleaf 100 100 100 100 0 15 100 100 80 100 80 100 100 100 Table A Comr.jouncIs
500 g ai/ha 268 269 270 271 272 273 274 275 276 277 278 279 280 281
Preemergence
Barnyardgr ss 100 90 100 60 100 100 100 100 50 100 75 100 95 90
Crabgrass, Large 90 80 90 80 90 90 95 100 30 100 75 100 95 65
Foxtail, Giant 100 90 95 75 100 95 100 100 35 100 80 100 100 75
Momingglory 95 80 95 70 95 50 100 100 60 95 100 100 90 90
Pigweed 100 100 100 100 100 100 100 100 95 100 100 100 100 100
Velvetleaf 100 100 100 100 100 100 90 100 75 100 100 100 100 100
Table A Compounds
500 g ai/ha 282 283 284 286 287 288 289 290 291 292 293 294 295 296
Preemergence
Barnyardgrass 95 30 40 0 35 100 65 40 75 0 100 100 90 65
Crabgrass, Large 85 65 75 10 30 100 75 30 70 0 100 100 100 75
Foxtail, Giant 95 70 75 15 65 100 85 55 70 0 100 100 100 80
Momingglory 95 20 55 5 10 100 85 0 85 0 100 100 100 70
Pigweed 100 95 100 55 90 100 85 100 100 0 100 100 100 80
Velvetleaf 100 100 100 50 65 100 100 85 100 0 100 100 100 50
Table A Compound Table A Compounds
500 g ai/ha 297 250i g ai/ha 169 181 182 183 184 202 262
Preemergence Preemergence
Barnyardgrass 0 Barnyardgrass 30 5 90 90 60 80 95
Crabgrass, Large 0 Crabgrass, Large 0 60 95 95 70 85 75
Foxtail, Giant 15 Foxtail . , Giant 50 10 95 100 50 85 95
Momingglory 10 Momingglory 0 0 75 50 15 40 60
Pigweed 75 Pigweed 0 75 100 90 90 95 100
Velvetleaf 25 Velvetleaf 5 0 95 100 55 100 100
Table A Compounds
125 g ai/ha 1 2 3 6 7 19 20 21 22 23 24 25 26 27
Preemergence
Barnyardgrass 50 45 30 40 30 40 0 50 35 25 0 5 30 0
Crabgrass, Large 10 40 25 65 20 10 0 50 50 55 0 0 0 0
Foxtail, Giant 20 35 10 45 0 10 0 10 0 10 0 0 10 0
Momingglory 10 20 0 10 10 5 0 0 0 0 0 0 5 0
Pigweed 90 100 85 95 0 70 10 75 60 65 0 25 25 15
Velvetleaf 80 50 0 95 20 40 0 40 0 25 0 5 15 0 Table A Compoundi
125 g ai/ha 28 29 30 31 32 33 34 35 36 37 38 39 40 41
Preemergence
Barnyardgrass 45 100 80 80 55 65 75 0 70 0 0 0 70 10
Crabgrass, Large 20 90 80 90 70 30 85 0 45 0 15 0 25 0
Foxtail, Giant 40 90 90 80 60 60 80 0 40 0 5 0 65 0
Momingglory 0 65 60 55 30 0 25 0 15 0 0 0 20 0
Pigweed 80 100 85 90 75 70 100 0 85 0 5 0 100 10
Velvetleaf 75 90 85 100 45 80 80 0 70 0 10 0 100 20
Table A Compounds
125 g ai/ha 42 43 44 45 46 49 50 51 52 53 54 55 56 57
Preemergence
Barnyardgrass 0 0 0 65 0 50 80 50 30 10 0 40 0 80
Crabgrass, Large 0 0 0 60 0 15 80 35 50 5 0 45 0 90
Foxtail, Giant 0 0 0 60 0 50 90 50 20 0 0 50 0 95
Momingglory 0 0 0 60 0 20 45 20 10 0 0 0 0 30
Pigweed 0 0 0 95 0 85 95 90 70 20 0 85 0 100
Velvetleaf 0 0 0 100 0 60 90 50 10 0 0 10 0 100
Table A Compounds
125 g ai/ha 58 62 63 64 65 66 67 68 69 70 71 72 73 74
Preemergence
Barnyardgrass 25 15 0 90 0 20 50 60 30 5 65 75 75 85
Crabgrass, Large 15 0 0 80 0 0 40 15 0 0 25 70 65 70
Foxtail, Giant 60 10 0 95 0 10 35 30 15 10 50 85 75 75
Momingglory 5 0 0 70 0 20 30 20 5 0 30 60 40 60
Pigweed 50 25 0 70 0 100 100 95 50 10 100 100 95 100
Velvetleaf 15 0 0 40 0 40 85 80 0 10 100 85 75 95
Table A Compounds
125 g ai/ha 75 76 77 84 87 88 89 90 91 92 93 94 95 96
Preemergence
Barnyardgrass 25 45 0 0 75 90 60 0 0 0 60 0 0 0
Crabgrass, Large 30 10 0 0 80 95 55 25 0 0 20 5 0 0
Foxtail, Giant 25 45 0 0 90 90 55 35 0 0 45 30 0 0
Momingglory 5 0 0 0 65 40 25 0 0 0 10 0 0 0
Pigweed 20 90 0 0 95 100 75 50 10 0 75 80 5 15
Velvetleaf 35 20 5 0 100 100 90 0 0 0 75 20 0 0 Table A ComplouncLs
125 g ai/ha 100 101 102 103 104 105 106 107 108 109 110 111 112 114
Preemergence
Barnyardgrass 0 95 90 100 0 100 90 90 90 0 60 0 0 5
Crabgrass, Large 0 90 80 90 0 95 100 90 100 0 60 0 0 20
Foxtail, Giant 0 90 90 90 0 90 90 90 95 55 70 0 0 15
Momingglory 0 75 65 100 0 75 65 70 65 0 15 0 0 20
Pigweed 0 100 100 100 0 100 100 100 100 10 90 30 85 60
Velvetleaf 0 100 100 100 0 100 100 100 100 0 75 0 0 40
Table A Compounds
125 g ai/ha 116 117 147 152 170 171 172 173 174 177 178 179 180 185
Preemergence
Barnyardgrass 0 0 45 80 0 0 15 10 10 0 0 0 0 95
Crabgrass, Large 0 0 40 55 0 0 20 5 30 0 60 0 50 90
Foxtail, Giant 0 0 50 60 0 0 15 35 25 0 0 15 0 90
Momingglory 0 0 25 40 0 0 0 0 0 0 0 0 0 55
Pigweed 70 10 100 80 0 0 15 10 30 0 0 70 0 100
Velvetleaf 20 0 100 60 0 0 0 10 0 0 10 0 0 100
Table A Compounds
125 g ai/ha 186 187 188 189 190 191 192 193 194 195 196 197 199 200
Preemergence
Barnyardgrass 95 0 5 0 0 0 0 0 0 15 0 0 0 5
Crabgrass, Large 100 0 0 0 0 10 0 0 0 10 0 0 0 0
Foxtail, Giant 95 0 20 0 10 35 0 0 0 10 20 5 0 0
Momingglory 80 0 0 0 0 0 0 0 0 0 0 0 0 0
Pigweed 100 25 0 0 10 0 0 0 0 15 0 10 0 10
Velvetleaf 100 0 0 0 15 20 0 0 0 0 0 0 0 0
Table A Compounds
125 g ai/ha 201 203 204 205 206 207 208 209 210 211 213 214 215 216
Preemergence
Barnyardgrass 0 0 0 0 0 0 0 0 10 40 5 15 10 55
Crabgrass, Large 0 0 0 0 20 0 0 0 15 30 0 0 15 20
Foxtail, Giant 0 0 0 0 0 0 0 0 15 5 15 10 20 60
Mo ingglory 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Pigweed 0 0 0 0 45 0 0 0 35 100 15 10 0 75
Velvetleaf 0 0 0 0 0 0 0 0 0 90 0 0 0 0 Table A Compounds
125 g ai/ha 217 218 219 220 221 222 223 224 225 226 227 228 229 230
Preemergence
Barnyardgrass 90 100 80 90 90 0 0 0 0 0 20 10 100 95
Crabgrass, Large 75 85 80 55 85 0 0 0 55 40 60 0 85 85
Foxtail, Giant 95 90 85 90 90 0 0 30 25 25 50 0 95 100
Momingglory 30 65 20 25 70 0 0 0 0 0 0 0 70 85
Pigweed 100 100 95 95 90 0 00 40 65 50 60 15 100 95
Velvetleaf 100 100 75 85 60 0 0 0 0 5 45 0 100 100
Table A Compounds 125 g ai/ha 231 232 233 234 235 236 237 238 239 240 241 242 243 244 Preemergence Barnyardgrass 100 100 25 90 60 100 100 100 95 65 70 40 65 60 Crabgrass, Large 90 85 45 80 50 90 90 90 90 75 35 60 70 75 Foxtail, Giant 90 95 55 90 65 90 95 90 90 70 45 55 80 80 Momingglory 95 60 0 40 40 90 95 85 80 35 10 0 15 0 Pigweed 100 100 85 100 90 100 100 100 100 100 80 85 95 100 Velvetleaf 100 95 70 100 80 95 90 100 100 80 100 95 75 100
Table A Compounds 125 g ai/ha 245 246 247 248 249 250 251 252 253 254 255 256 257 258 Preemergence Barnyardgrass 65 85 55 80 85 90 95 75 80 55 90 35 0 0 Crabgrass, Large 80 90 55 65 80 85 85 80 75 55 80 10 0 0 Foxtail, Giant 90 90 70 80 55 80 95 85 90 60 90 40 0 0 Momingglory 15 60 40 50 50 40 85 25 55 10 60 5 0 0 Pigweed 100 90 85 60 95 100 100 90 95 80 100 90 0 10 Velvetleaf 100 100 35 50 60 80 100 95 85 65 100 50 0 0
Table A Compounds 125 g ai/ha 259 260 261 263 264 265 266 267 268 269 270 271 272 273 Preemergence Barnyardgrass 90 80 0 80 85 80 100 95 90 80 75 20 85 75 Crabgrass, Large 20 30 0 55 85 80 95 70 70 25 70 50 80 80 Foxtail, Giant 75 75 25 65 90 95 95 90 90 80 75 25 95 80 Momingglory 45 65 0 0 55 50 80 55 60 30 100 25 85 70 Pigweed 85 95 35 100 95 100 100 100 100 95 100 95 100 100 Velvetleaf 85 85 25 100 45 95 100 100 100 95 100 75 90 100 Table A Compounds
125 g ai/ha 274 275 276 277 278 279 280 281 282 283 284 286 287 288
Preemergence
Barnyardgrass 85 100 0 85 70 80 70 63 80 10 15 0 5 70
Crabgrass, Large 75 100 5 85 60 85 60 30 55 25 40 0 20 85
Foxtail, Giant 90 100 20 90 70 95 95 45 90 40 40 0 30 90
Momingglory 55 90 20 75 25 90 75 85 85 0 5 0 0 75
Pigweed 100 95 80 100 100 100 100 100 100 95 100 5 65 100
Velvetleaf 70 100 65 100 100 100 95 90 95 70 80 0 20 100
Table A Compounds
125 g ai/ha 289 290 291 292 293 294 295 296 297
Preemergence
Barnyardgrass 40 0 40 0 85 95 95 40 0
Crabgrass, Large 45 0 30 0 90 95 90 20 0
Foxtail, Giant 45 0 55 0 95 95 90 25 10
Momingglory 20 0 35 0 85 100 95 20 0
Pigweed 40 55 95 0 100 100 95 40 70
Velvetleaf 70 5 '70 0 100 100 90 15 5
Table A Compounds
62 g ai/ha 169 181 182 183 184
Preemergence
Barnyardgrass 0 0 70 70 0
Crabgrass, Large 0 0 90 90 50
Foxtail, Giant 0 0 85 90 15
Momingglory 0 0 35 10 0
Pigweed 0 50 50 90 75
Velvetleaf 0 0 95 80 0
TESTB Seeds selected from barnyardgrass (Echinochloa crus-galli), Surinam grass (Brachiaria decumbens), cocklebur (Xanthium strumarium), corn (Zea mays), large crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), momingglory (Ipomoea coccinea), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), rice (Oryza sativa), and wheat (Triticum aestivum) were planted and treated preemergence with test chemicals formulated in a non- phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides) and wild oat (Avena fatua) were treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Plant species in the flooded paddy test consisted of rice (Oryza sativd), smallflower umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-gallϊ) grown to the 2-leaf stage for testing. Treated plants and controls were maintained in a greenhouse for 13 to 15 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table B Compounds
1000 g ai/ha 1 2 3 4 6 7 9 10 12 14 15 18 19 21
Flood
Barnyardgrass 90 90 80 80 70 90 90 90 90 40 70 90 80 80
Duc salad 80 0 80 50 70 90 40 30 60 0 80 0 70 70
Rice 70 70 30 50 70 80 70 90 80 30 20 70 70 70
Sedge, Umbrella 90 80 80 50 80 90 70 50 60 0 30 30 30 70
Table B Compounds
1000 g ai/ha 22 23 28 29 30 31 32 33 34 36 38 40 41' 42
Flood
Barnyardgrass 40 70 70 100 100 100 100 90 100 100 30 100 90 20
Ducksalad 40 40 70 100 90 90 0 90 80 90 0 90 80 0
Rice 50 60 70 100 90 90 90 90 90 90 40 90 70 30
Sedge, Umbrella 40 90 80 90 90 90 90 100 80 90 0 90 60 20
Table B Compounds
1000 g ai/ha 45 46 48 49 50 51 52 53 55 57 60 64 65 66
Flood
Barnyardgrass 90 0 0 90 100 60 60 40 80 100 30 100 30 70
Ducksalad 90 0 0 90 90 80 0 0 80 100 0 80 40 90
Rice 90 0 0 80 80 80 60 60 80 100 30 90 70 80
Sedge, Umbrella 80 0 20 80 100 90 0 0 80 100 40 80 50 70
Table B Compounds
1000 g ai/ha 67 68 69 71 72 73 74 75 76 78 79 80 81 82
Flood
Barnyardgrass 70 60 80 90 100 100 100 60 90 40 30 20 0 0
Ducksalad 70 50 0 90 90 90 90 60 80 0 20 0 0 0
Rice 80 70 70 90 90 90 90 70 70 40 40 20 10 0
Sedge, Umbrella 60 40 30 90 90 70 80 20 70 20 30 0 0 30 Table B Compounds
1000 g ai/ha 83 87 8E 89 90 93 94 95 97 99 101 102 103 105
Flood
Barnyardgrass 60 100 90 100 70 90 60 20 40 80 100 100 100 100
Ducksalad 30 90 90 90 80 80 0 0 0 80 90 90 100 90
Rice 70 100 90 90 90 80 70 40 30 50 100 100 90 100
Sedge, Umbrella 60 90 90 90 80 80 60 70 0 80 100 90 90 80
Table B Compounds
1000 g ai/ha 106 107 108 109 110 111 112 113 114 115 116 117 118 119
Flood
Barnyardgrass 100 100 100 90 100 70 30 100 100 100 100 0 0 20
Ducksalad 90 90 90 70 80 30 60 80 90 100 100 0 0 60
Rice 100 100 100 80 90 80 50 90 90 100 90 30 0 20
Sedge, Umbrella 90 90 80 80 80 80 60 80 90 100 90 0 0 60
Table B Compounds
1000 g ai/ha 120 121 122 123 124 125 126 127 128 129 130 131 132 139
Flood
Barnyardgrass 100 70 90 70 70 100 50 80 90 0 70 60, 40
Ducksalad 100 80 80 50 80 80 50 70 90 20 60 70 30
Rice 100 60 60 40 60 40 30 40 90 0 0 30 0
Sedge, Umbrella 100 80 80 50 80 50 70 80 80 30 90 80. 80
Table B Compounds
500 g ai/ha 172 178 179 185 186 188 190 191 195 202 205 206 208 211
Flood
Barnyardgrass 60 20 10 100 100 60 50 50 50 100 50 80 30 80
Ducksalad 10 0 0 80 80 80 0 0 - 80 30 70 0 50
Rice 70 40 30 100 100 70 80 70 60 90 60 80 50 70
Sedge, Umbrella 70 20 0 100 90 90 90 70 90 90 90 80 0 80
Table B Compounds
500 g ai/ha 217 218 219 220 221 229 230 231 232 233 234 235 236 237
Flood
Barnyardgrass 100 100 90 100 100 100 100 100 100 40 100 80 100 100
Ducksalad 70 80 30 70 70 30 40 30 30 40 10 40 40 50
Rice 100 100 100 90 100 100 100 90 80 50 90 40 100 100
Sedge, Umbrella 100 100 90 100 90 100 90 90 100 90 100 70 90 80 Table B Compounds
500 g ai/ha 238 239 240 241 242 243 244 245 246 248 249 250 251 252
Flood
Barnyardgrass 100 100 50 50 90 100 100 100 100 90 80 100 100 100
Ducksalad 60 40 30 50 60 90 70 80 60 60 60 70 90 100
Rice 100 90 90 50 60 80 50 90 90 70 70 100 100 80
Sedge, Umbrella 70 100 70 100 100 100 100 90 90 90 60 70 90 100
Table B Compounds
500 g ai/ha 253 254 255 256 259 260 262 263 264 270 271 272 273
Flood
Barnyardgrass 100 70 100 20 100 100 100 100 100 100 100 100 100
Ducksalad 100 20 90 30 90 80 100 100 70 80 40 90 70
Rice 100 60 90 30 100 90 80 70 100 90 50 100 80
Sedge, Umbrella 100 90 100 80 100 100 100 100 90 100 80 90 100
Table B Compounds
125 g ai/ha 135 136 137 138 140 152 155 158 159 160 162 163 164 165
Flood
Barnyardgras-.' 0 0 0 10 30 30 60 0 0 0 0 10 0 0
Ducksalad 0 0 0 10 10 0 0 0 20 80 0 0 0 0
Rice 0 0 0 20 50 60 40 0 0 0 0 0 0 0
Sedge, Umbrella 0 0 0 30 80 30 0 30 20 10 0 0 0 0
Table B Compounds
125 g ai/ha 166 167 172 173 178 179 180 182 183 185 186 188 190 191
Flood
Barnyardgrass 0 0 20 0 0 0 0 100 90 100 100 10 0 0
Ducksalad 0 0 0 0 0 0 70 60 70 70 10 0 0
Rice 0 0 20 0 10 10 0 100 100 100 100 30 30 20
Sedge, Umbrella 0 0 0 0 0 0 0 70 60 100 90 70 10 30
Table B Compounds
125 g ai/ha 195 202 205 206 208 211 217 218 219 220 221 229 230 231
Flood
Barnyardgrass 10 60 0 20 0 50 90 80 50 60 80 70 70 80
Ducksalad 0 60 0 0 0 30 40 30 0 50 60 10 0 0
Rice 30 80 10 30 0 50 80 80 70 70 90 90 70 80
Sedge, Umbrella 10 80 40 20 0 60 90 80 60 90 40 90 60 70 Table B Compounds
125 g ai/ha 232 233 234 235 236 237 238 239 240 241 242 243 244 245
Flood
Barnyardgrass 80 0 60 20 50 40 100 40 40 30 30 90 80 60
Ducksalad 0 0 0 0 0 10 20 0 0 10 10 50 30 60
Rice 70 20 50 10 90 80 100 90 70 30 40 60 20 80
Sedge, Umbrella 100 60 100 10 70 50 60 90 30 80 90 90 80 70
Table B Compounds
125 g ai/ha 246 248 249 250 251 252 253 254 255 256 259 260 262 263
Flood
Barnyardgrass 60 30 30 70 80 90 80 10 90 10 60 70 100 80
Ducksalad 10 20 10 60 80 80 90 0 70 10 60 30 80 80
Rice 50 30 50 80 90 50 50 20 80 10 80 70 50 50
Sedge, Umbrella 80 30 30 60 80 100 90 70 90 60 90 80 90 100
Table B Compounds
125 g ai/ha 264 270 271 272 273
Flood
Barnyardgrass 100 90 50 100 90
Ducksalad 50 70 10 80 50
Rice 90 50 30 80 70
Sedge, Umbrella 70 90 70 80 90
Table B Compounds
500 g ai/ha 9 10 12 18 21 23 29 30 31 32
Postemergence
Barnyardgrass 90 60 20 30 40 50 50 50 50 30 100 90 90 60
Blackgrass 50 40 40 60 20 60 50 40 30 80 100 100 90 90
Cocklebur 50 70 10 40 30 30 10 10 30 20 80 80 60 30
Corn 20 - 60 40 20 30 20 30 40 40 90 90 70 30
Crabgrass, Large 100 90 60 30 60 90 80 80 80 50 100 100 100 50
Foxtail, Giant 60 80 .30 40 50 80 70 70 50 50 100 90 60 60
Lambsquarters 90 90 80 90 100 90 90 100 90 80 100 100 100 100
Momingglory 100 100 90 100 100 100 90 100 90 80 100 100 100 100
Oat, Wild 40 40 40 40 30 40 40 50 30 40 70 80 40 50
Pigweed 100 100 100 90 100 100 100 100 90 90 100 100 100 90
Surinam Grass 90 60 30 30 70 90 70 60 40 30 100 90 100 50
Velvetleaf 100 100 100 100 100 100 100 100 100 60 100 100 100 100
Wheat 30 30 30 40 30 30 30 30 30 30 50 50 30 40 Table B Compounds
500 g ai/ha 33 34 36 40 45 49 50 51 55 57 64 66 67 68
Postemergence
Barnyardgrass 100 80 90 90 50 30 50 50 20 80 70 50 50 50
Blackgrass 80 90 80 40 90 80 100 50 60 90 100 60 50 60
Cocklebur 60 30 50 100 80 40 50 50 20 - 60 50 90 50
Corn 40 60 50 60 60 40 50 30 20 80 80 20 40 30
Crabgrass, Large 100 100 90 90 60 70 100 90 90 100 80 40 50 70
Foxtail, Giant 70 60 60 90 50 40 100 80 90 100 80 50 60 70
Lambsquarters 90 90 100 100 100 90 100 100 100 100 100 100 100 100
Momingglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Oat, Wild 60 40 40 40 50 40 60 40 40 80 50 50 40 40
Pigweed 100 90 100 100 100 100 100 100 100 100 100 100 100 100
Surinam Grass 80 90 70 90 100 60 100 90 80 100 100 80 70 80
'Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 50 40 40 30 50 30 40 40 30 50 30 30 40 30
Table B Compounds
500 g ai/ha 71 72 73 74 75 76 87 88 89 90 101 102 103 105
Postemergence
Barnyardgrass 90 50 40 30 30 50 100 60 50 0 90 90 100 100
Blackgrass 100 70 50 60 60 70 100 70 80 80 100 80 100 90
Cocklebur 90 50 50 100 60 50 100 70 90 0 100 100 100 100
Corn 60 50 40 20 60 - 100 70 60 0 80 90 100 100
Crabgrass, Large 80 100 100 100 60 70 100 100 100 0 100 80 100 100
Foxtail, Giant 90 70 30 40 50 80 100 80 80 0 90 80 90 90
Lambsquarters 100 100 100 100 100 100 100 100 100 50 100 100 100 100
Momingglory 100 60 100 60 100 80 100 90 100 50 100 100 100 100
Oat, Wild 40 40 40 60 50 50 80 40 60 60 60 50 80 70
Pigweed 100 100 90 100 100 100 100 100 100 20 100 100 100 100
Surinam Grass 100 100 100 100 60 80 100 100 100 0 100 100 100 100
Velvetleaf 100 100 100 100 100 100 100 100 100 50 100 100 100 100
Wheat 40 40 40 40 30 30 40 40 40 30 30 30 50 50
Table B Compounds
500 g ai/ha 106 107 108 118 119 121 122 123 124 126 127 129 130 131
Postemergence
Barnyardgrass 100 100 100 20 10 50 70 20 70 60 50 40 20 20
Blackgrass 90 90 90 30 30 70 60 60 60 50 30 60 70 70 Cocklebur 100 100 100 10 0 20 20 0 20 0 10 0 20 0
Com 90 100 100 10 10 20 50 20 10 10 20 30 30 20
Crabgrass, Large 100 90 100 40 30 40 40 0 70 20 40 20 30 30
Foxtail, Giant 90 100 90 40 40 60 80 30 50 60 40 40 40 40
Lambsquarters 100 100 100 60 60 100 90 90 90 80 80 60 80 70
Momingglory 100 100 100 70 10 100 100 90 80 90 90 0 10 10
Oat, Wild 70 60 70 30 30 60 60 50 50 60 50 60 60 60
Pigweed 100 100 100 50 60 100 100 90 80 50 70 50 90 70
Surinam Grass 100 100 100 30 30 40 80 40 60 30 40 20 30 30
Velvetleaf 100 100 100 50 60 70 100 40 60 20 50 10 30 40
Wheat 50 50 60 20 20 50 50 50 50 50 40 60 60 60
Table B Compounds
500 g ai/ha 132 139 140 147 158 159 160 162 163 164 165 166 167
Postemergence
Barnyardgrass 20 0 80 50 60 70 30 40 40 70 40 70 70
Blackgrass 60 40 70 60 70 70 40 30 40 60 50 60 50
Cocklebur 30 0 70 80 30 20 0 20 50 30 20 40 30
Corn 50 30 80 60 50 6.0 30 30 60 60 70 50 40
Crabgrass, Large 20 30 30 90 30 10 10 10 20 30 40 30 10
Foxtail, Giant 30 30 50 70 60 40 20 20 30 40 30 40 40
Lambsquarters 70 60 80 100 70 80 20 60 30 80 30 70 40
Momingglory 30 70 100 100 90 90 60 60 50 100 80 100 100
Oat, Wild 70 60 60 60 50 60 40 60 50 50 50 50 50
Pigweed 60 50 90 100 100 100 30 60 60 100 60 70 30
Surinam Grass 10 20 60 70 40 40 20 40 70 70 30 30 40
Velvetleaf 40 20 70 100 60 50 10 30 20 100 40 70 60
Wheat 60 50 50 60 60 40 40 50 40 50 50 50 50
Table B Compounds
250 g ai/ha 41 93 110 112 113 114 115 116 117 120 125 128 153 154
Postemergence
Barnyardgrass 30 20 40 20 30 30 60 50 20 70 80 60 70 50
Blackgrass 60 70 80 70 90 70 80 60 60 80 60 70 70 60
Cocklebur 30 60 40 30 50 40 100 40 70 100 80 90 80 20
Corn 20 30 30 30 30 30 50 30 30 40 30 30 60 30
Crabgrass, Large 80 30 30 30 20 30 60 50 30 80 70 50 100 50
Foxtail, Giant 60 40 40 40 40 50 60 50 30 80 40 50 70 60
Lambsquarters 100 90 90 90 90 90 100 100 90 100 90 80 100 80 Momingglory 100 100 80 80 100 100 100 90 100 100 100 100 100 70 Oat, Wild 40 60 60 50 60 60 70 50 40 60 50 70 70 70 Pigweed 100 100 90 100 90 100 100 100 100 100 90 80 100 100 Surinam Grass 30 50 30 20 20 30 70 60 20 90 70 50 70 40 Velvetleaf 100 100 100 30 100 100 100 100 50 100 100 100 100 100 Wheat 30 30 60 50 50 40 60 40 30 40 60 60 60 60
Table B Compounds Table B Compounds
250 g ai/ha 155 156 157 168 250 g ai/ha 155 156 157 158
Postemergence Postemergence
Barnyardgrass 70 40 40 70 Momingglory '100 100 70 100
Blackgrass 70 60 70 80 Oat, Wild 60 70 60 70
Cocklebur 70 10 10 100 Pigweed 100 100 60 100
Corn 60 30 40 70 Surinam Grass 30 90 40 100
Crabgrass, Large 30 80 40 100 Velvetleaf 80 100 80 100
Foxtail, Giant 30 70 50 80 Wheat 50 50 60 60
Lambsquarters 70 100 60 100
Table B Compounds
125 g ai/ha 9 10 12 18 21 23 29 30 31 32
Postemergence
Barnyardgrass 40 0 10 20 10 20 10 30 20 10 50 50 70 30
Blackgrass 30 30 30 40 10 30 20 30 30 60 90 90 70 60
Cocklebur 30 30 10 20 10 20 10 0 20 10 30 30 50 20
Corn 20 0 30 30 10 20 20 10 10 10 30 20 40 20
Crabgrass, Large 80 30 60 10 40 70 30 40 30 20 50 60 50 10
Foxtail, Giant 20 40 20 30 30 30 30 30 30 30 30 30 30 30
Lambsquarters 80 90 80 70 80 90 90 90 70 70 100 90 100 80
Momingglory 90 20 60 40 70 90 90 70 70 40 100 90 100 80
Oat, Wild 30 30 30 30 20 30 30 30 30 30 40 50 30 30
Pigweed 90 80 70 60 90 100 100 100 70 50 100 70 90 70
Surinam Grass 30 0 10 10 40 50 40 30 10 20 50 60 50 20
Velvetleaf 100 60 50 100 100 100 100 100 30 30 100 100 90 100
Wheat 20 20 30 30 20 30 20 20 20 20 30 40 20 30
Table B Compounds
125 g ai/ha 33 34 36 40 45 49 50 51 55 57 64 66 67 68
Postemergence
Barnyardgrass 50 20 60 40 30 20 10 10 10 70 20 20 10 10
Blackgrass 70 50 70 20 70 40 70 30 30 70 70 50 30 40 Cocklebur 30 20 30 60 40 20 50 50 20 100 20 30 50 30
Corn 30 20 30 10 20 10 20 20 10 60 30 10 10 10
Crabgrass, Large 50 30 30 40 40 20 60 20 20 90 60 10 10 30
Foxtail, Giant 30 30 20 70 40 40 50 50 50 70 50 30 30 40
Lambsquarters 90 80 70 100 90 90 100 100 100 100 90 100 100 100
Momingglory 100 80 80 100 100 20 100 100 100 100 100 100 90 100
Oat, Wild 40 30 30 20 40 30 50 40 30 60 30 30 30 30
Pigweed 100 70 80 100 100 80 100 100 100 100 70 100 90 90
Surinam Grass 50 20 30 80 30 20 60 20 30 100 40 60 30 40
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 30 30 30 20 30 20 - 30 20 40 20 30 30 20
Table B Compounds
125 g ai/ha 71 72 73 74 75 76 87 88 89 90 101 102 103 105
Postemergence
Barnyardgrass 20 10 10 10 10 20 30 30 30 0 80 40 50 70
Blackgrass 70 40 20 30 50 60 80 40 60 60 50 40 100 60
Cocklebur 50 40 50 50 10 10 60 40 60 0 50 60 90 100
Corn 40 10 0 10 20 - 30 20 20 0 20 40 30 30
Crabgrass, Large 50 20 20 30 20 - 60 30 20 0 60 40 70 70
Foxtail, Giant 40 30 20 20 20 - 50 40 40 0 60 60 70 70
Lambsquarters 100 90 100 100 90 90 100 100 100 0 100 100 100 100
Momingglory 100 30 100 - 80 60 80 50 100 20 100 100 100 100
Oat, Wild 30 30 20 30 30 40 40 30 40 50 40 30 50 30
Pigweed 100 80 80 80 90 80 100 100 100 0 100 100 100 100
Surinam Grass 60 20 30 20 20 - 90 40 20 0 100 80 70 90
Velvetleaf 100 100 100 100 100 100 100 100 100 0 100 100 100 100
Wheat 20 30 20 20 10 30 30 30 30 20 30 30 40 30
Table B Compounds 125 g ai/ha 106 107 108 119 121 122 123 124 126 127 129 130 131 132 Postemergence Barnyardgrass 60 60 50 0 20 30 20 20 30 20 10 20 10 10Blackgrass 50 80 70 0 60 60 40 50 40 30 50 50 60 50 Cocklebur 100 100 100 0 10 20 0 10 0 0 0 10 0 10 Corn 20 20 30 0 20 20 0 10 10 10 10 30 10 20
Crabgrass, Large 80 90 70 20 30 40 0 0 20 0 10 20 20 20 Foxtail, Giant 60 70 60 30 30 30 0 30 0 0 20 30 30 20 Lambsquarters 100 100 100 40 70 90 40 40 40 50 30 70 50 60 Morningglory 100 100 100 10 80 80 70 80 70 20 0 10 10 10 Oat, Wild 60 50 40 0 60 50 50 30 50 40 50 60 60 50 Pigweed 100 100 100 50 60 70 70 60 30 30 30 80 60 50 Surinam Grass 70 100 70 20 20 50 30 30 0 0 10 10 10 10 Velvetleaf 100 100 100 50 50 90 20 60 20 40 0 30 30 30 Wheat 30 40 30 0 50 50 40 40 50 40 50 60 60 50
Table B Compounds
125 g ai/ha 140 147 152 158 159 160 162 163 164 165 166 167 182 183
Postemergenee
Barnyardgrass 50 40 20 30 60 20 40 40 20 30 20 30 60 50
Blackgrass 70 40 50 60 50 30 30 40 60 40 50 40 80 50
Cocklebur 30 40 30 20 10 0 20 50 30 0 40 30 90 100
Corn 50 30 30 30 30 30 30 30 30 30 20 20 40 40
Crabgrass, Large 30 70 30 10 10 10 10 10 10 0 20 10 30 30
Foxtail, Giant 20 30 30 20 30 10 20 20 30 20 20 20 70 60
Lambsquarters 60 100 100 70 70 20 30 30 50 10 50 30 100 100
Momingglory 80 90 100 70 80 60 50 40 70 80 100 90 100 100
Oat, Wild 40 50 50 40 40 40 50 40 40 40 40 50 60 50
Pigweed 40 100 100 100 70 30 50. 50 80 30 40 30 100 100
Surinam Grass 20 30 30 20 20 20 10 30 20 10 20 30 50 60
Velvetleaf 60 100 90 40 30 10 30 20 60 30 60 30 100 100
Wheat 40 50 60 40 40 40 40 40 50 50 50 50 50 50
Table B Compounds
125 g ai/ha 185 186 188 190 202 217 218 219 220 221 229 230 231 232
Postemergence
Barnyardgrass 30 80 20 30 20 20 20 40 - 20 70 80 90 90
Blackgrass 60 60 60 60 50 60 70 50 60 60 50 50 50 50
Cocklebur 60 100 30 10 20 60 70 30 - 50 100 100 100 100
Corn 40 60 20 30 30 40 40 30 - 40 60 50 40 70
Crabgrass, Large 30 20 10 10 0 30 10 10 - 20 20 10 30 10
Foxtail, Giant 40 30 30 10 30 30 40 50 - 40 30 30 30 30
Lambsquarters 100 100 70 70 90 100 90 90 - 90 100 100 90 100
Morningglory 100 100 70 70 90 70 100 100 - 90 100 100 100 100
Oat, Wild 60 50 50 60 40 60 60 60 60 60 50 50 60 60
Pigweed 100 100 50 20 90 100 100 100 - 90 100 100 100 100
Surinam Grass 60 70 30 40 30 20 60 30 - 70 90 70 80 70
Velvetleaf 100 100 50 0 100 100 100 100 - 70 100 100 100 100 Wheat 60 60 50 50 50 50 60 60 60 60 50 50 50 50
Table B Compounds
125 g ai/ha 234 235 236 237 238 239 240 241 242 243 244 245 246 249
Postemergence
Barnyardgrass 80 80 40 80 50 40 40 20 0 80 60 30 10 30
Blackgrass 60 60 70 60 60 60 50 70 60 80 70 70 70 60
Cocklebur 90 100 20 100 80 100 100 60 30 70 100 100 20 50
Corn 50 40 30 60 80 60 60 40 30 100 60 60 20 10
Crabgrass, Large 10 10 10 20 20 20 10 10 20 40 0 30 30 10
Foxtail, Giant 30 40 10 20 30 100 30 30 30 40 50 60 30 10
Lambsquarters 90 100 90 100 90 100 100 80 90 90 100 90 70 80
Momingglory 100 100 90 100 100 100 100 100 100 100 100 100 80 70
Oat, Wild 50 50 60 50 50 60 50 60 60 70 70 60 60 40
Pigweed 100 100 100 100 100 100 100 90 70 70 100 100 50 70
Surinam Grass 80 40 20 70 70 80 50 20 40 70 70 60 40 40
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 50
Wheat 60 60 60 50 50 50 50 60 50 60 60 60 60 60
Table B Compounds
125 g ai/ha 250 251 252 253 255 259 260 262 263 264 265 266 267 268
Postemergence
Barnyardgrass 20 20 30 20 40 10 20 40 0 0 20 40 60 60
Blackgrass 70 70 100 70 70 100 80 70 70 60 90 90 80 100
Cocklebur 50 100 100 30 80 90 50 80 40 10 50 70 50 100
Corn 10 30 30 40 40 50 40 20 30 30 50 40 60 90
Crabgrass, Large 10 20 30 30 50 30 30 40 30 30 10 30 30 20
Foxtail, Giant 40 40 60 50 40 60 50 50 40 50 50 40 50 90
Lambsquarters 100 100 100 100 90 100 100 100 100 90 100 100 100 100
Momingglory 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Oat, Wild 50 70 80 70 70 60 60 70 70 60 60 70 60 60
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Surinam Grass 20 40 90 50 40 60 40 50 50 20 60 60 80 70
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 50 60 60 90 60 60 60 60 60 50 60 70 70 60
Table B Compounds
125 g ai/ha 269 270 272 273 274 275 276 277 279 280 281 282 288
Postemergence
Barnyardgrass 50 40 40 60 10 70 40 60 70 70 70 70 60 Blackgrass 80 70 70 70 60 100 70 50 90 80 80 80 70
Cocklebur 100 100 100 100 20 90 30 100 90 100 - 100 100
Corn 50 70 40 40 30 70 60 40 80 40 50 40 70
Crabgrass, Large 30 40 40 30 10 50 30 50 60 50 40 60 30
Foxtail, Giant 60 40 60 30 30 60 50 60 80 70 50 60 60
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100
Morningglory 100 100 100 100 100 100 100 100 100 100 100 100 100
Oat, Wild 60 60 60 50 60 60 60 50 60 60 70 70 70
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100
Surinam Grass 80 50 90 50 30 60 30 50 90 60 40 70 70
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 60 60 60 50 60 60 60 60 60 60 60 60 60
Table B Compounds
62 g ai/ha 41 58 93 110 112 113 114 115 116 117 118 120 125 128
Postemergence
Barnyardgrass 20 20 10 20 20 20 10 40 10 10 0 20 30 30
Blackgrass 20 50 50 70 50 60 60 70 60 50 0 70 40 60
Cocklebur 30 20 50 40 30 40 40 40 30 60 0 100 • 70 50
Corn 10 30 10 30 20 20 20 20 3.0 20 10 30 20 20
Crabgrass, Large 40 20 10 20 20 20 20 30 20 30 30 30 40 50
Foxtail, Giant 50 40 20 30 30 30 30 40 30 20 30 40 30 40
Lambsquarters 100 80 80 70 70 70 80 90 80 80 30 100 90 70
Mo ingglory 100 60 80 60 50 80 70 100 50 40 60 100 90 100
Oat, Wild 20 40 30 60 50 50 30 60 40 40 0 60 50 60
Pigweed 100 90 100 70 100 70 80 100 100 90 30 90 60 60
Surinam Grass 20 30 20 10 10 10 20 30 20 10 20 50 40 40
Velvetleaf 100 70 100 90 20 60 50 100 100 30 30 100 100 100
Wheat 20 30 20 60 30 50 30 40 40 30 0 40 50 50
Table B Compounds
62 g ai/ha 139 152 153 154 155 156 157 168 182 183 185 186 202 217
Postemergence
Barnyardgrass 0 20 50 30 30 20 40 50 30 30 20 20 0 20
Blackgrass 20 40 50 50 60 50 60 50 60 50 50 50 30 50
Cocklebur 0 30 30 10 70 10 0 100 50 40 30 80 20 40
Corn 20 30 20 20 40 20 30 30 30 30 40 40 20 30
Crabgrass, Large 0 30 60 20 10 60 0 80 30 30 0 0 0 20
Foxtail, Giant 10 30 60 10 30 30 10 40 40 30 30 20 30 30 Lambsquarters 40 100 100 30 70 100 0 υu ιυυ 100 90 80 yo 80
Momingglory 0 90 100 50 90 100 70 100 100 100 100 100 70 70
Oat, Wild 50 50 50 40 50 50 50 50 50 50 60 50 40 50
Pigweed 40 60 90 50 80 100 30 100 100 100 90 100 80 90
Surinam Grass 0 20 70 20 10 40 0 60 30 30 40 70 30 20
Velvetleaf 0 60 100 40 70 100 30 100 100 100 100 100 70 100
Wheat 30 50 40 50 40 50 60 50 50 50 60 50 50 50
Table B Compounds
62 g ai/ha 218 219 220 221 229 230 231 232 234 236 237 238 239 240
Postemergence
Barnyardgrass 20 30 30 0 30 60 40 50 40 30 20 50 30 30
Blackgrass 40 40 50 40 40 50 40 50 40 50 50 50 40 40
Cocklebur 60 30 40 20 60 90 70 100 90 20 50 70 100 40
Corn 20 20 30 20 30 30 20 30 50 30 30 40 60 30
Crabgrass, Large 10 10 0 0 10 10 10 10 10 10 10 10 10 10
Foxtail, Giant 30 40 30 40 30 20 30 20 30 10 10 30 30 30
Lambsquarters . 80 90 70 90 90 90 90 90 70 90 90 90 100 100
Momingglory 90 100 70 90 100 90 100 100 90 90 100 90 100 100
Oat,' Wild 50 50 6'0 60 50 50 50 50 40 60 40 50 50 50
Pigweed 100 100 100 90 100 100 100 100 100 100 100 100 100 100
Surinam Grass 20 30 30 0 40 30 20 40 20 10 10 10 10 10
Velvetleaf 90 90 100 50 100 100 100 100 100 100 70 100 100 100
Wheat 50 60 60 60 50 50 50 50 50 60 50 50 50 50
Table B Compounds
62 g ai/ha 241 243 244 245 246 249 250 251 252 253 255 259 260 262
Postemergence
Barnyardgrass 0 0 20 0 10 10 10 10 10 0 0 10 10 20
Blackgrass 40 50 60 60 60 50 50 50 70 40 60 80 70 70
Cocklebur 50 70 70 70 10 40 40 100 20 30 10 20 20 20
Corn 30 30 30 30 20 0 10 10 10 0 10 20 40 10
Crabgrass, Large 10 10 0 10 20 10 0 10 10 10 20 20 30 20
Foxtail, Giant 20 30 40 30 20 10 30 30 30 40 30 40 50 30
Lambsquarters 80 90 100 90 60 70 0 100 100 100 80 90 100 90
Momingglory 90 100 100 100 80 70 100 100 100 100 70 100 100 70
Oat, Wild 50 60 60 50 60 40 40 50 60 70 50 40 50 60
Pigweed 40 70 100 70 50 70 0 100 100 100 80 100 100 100
Surinam Grass 10 70 70 60 20 10 0 10 30 10 10 20 20 20 Velvetleaf 100 100 100 100 60 50 100 100 100 100 100 100 100 100
Wheat 50 50 50 50 60 50 40 50 60 60 50 50 60 50
Table B Compounds
62 g ai/ha 263 264 265 266 267 268 269 270 272 273 274 275 275 277
Postemergence
Barnyardgrass 0 0 '10 10 10 20 20 20 30 20 0 60 30 40
Blackgrass 50 60 80 90 80 80 70 60 40 60 60 70 60 40
Cocklebur 10 10 40 30 30 100 40 100 100 100 20 30 20 50
Corn 10 10 20 20 20 30 20 20 30 20 10 30 30 30
Crabgrass, Large 30 20 10 10 20 10 20 20 10 10 10 20 0 20
Foxtail, Giant 30 30 30 30 20 40 30 30 60 20 20 50 30 30
Lambsquarters 100 60 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 100 100 90 100 100 100 70 100 100 100 80 100 90 100
Oat, Wild 60 50 50 60 60 60 40 50 50 40 60 60 40 50
Pigweed 100 80 100 100 100 100 100 100 100 100 70 100 100 100
Surinam Grass 10 10 20 30 50 30 40 50 40 40 10 60 20 30
Velvetleaf 100 70 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 50 50 50 40 50 50 40 50 50 50 60 50 50 40
Table B Compounds
62 g ai/ha 279 280 281 282 288
Postemergence
Barnyardgrass 40 60 30 40 30
Blackgrass 80 70 70 80 70
Cocklebur 80 90 100 100 90
Corn 30 30 30 30 30
Crabgrass, Large 30 30 40 30 30
Foxtail, Giant 50 50 40 40 40
Lambsquarters 100 100 100 100 100
Morningglory 100 100 100 100 90
Oat, Wild 50 50 50 60 60
Pigweed 100 100 100 100 100
Surinam Grass 70 40 40 30 40
Velvetleaf 100 100 100 100 100
Wheat 40 50 40 50 40 Table B Compounds Table B Compound
31 g ai/ha 188 190 235 242 16 g ai/ha 58
Postemergence Postemergence
Barnyardgrass 0 0 50 0 Barnyardgrass 20
Blackgrass 40 40 40 50 Blackgrass 30
Cocklebur 10 10 30 10 Cocklebur 0
Corn 10 20 30 10 Corn 0
Crabgrass, Large 10 10 10 0 Crabgrass, Large 10
Foxtail, Giant 0 10 30 0 Foxtail, Giant 30
Lambsquarters 60 60 100 90 Lambsquarters 50
Momingglory 20 40 100 100 Mo ingglory 30
Oat, Wild 40 40 40 50 Oat, Wild 0
Pigweed 10 0 100 40 Pigweed 70
Surinam Grass 10 10 10 10 Surinam Grass 20
Velvetleaf 40 0 70 70 Velvetleaf 20
Wheat 40 40 50 50 Wheat 0
Table B Compounds
500 g ai/ha 1 2 3 6 9 10 12 18 21 23 29 30 31 32
Preemergence
Barnyardgrass 90 80 80 90 100 100 100 100 80 80 100 100 100 100
Cocklebur 0 80 0 70 30 60 30 40 10 0 90 90 80 70
Corn 80 80 90 90 90 100 90 70 60 30 100 100 100 100
Crabgrass, Large 100 90 80 100 90 100 100 100 90 100 100 100 100 100
Foxtail, Giant 80 70 80 100 80 100 100 90 80 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 0 0 70 80 70 80 70 70 50 20 100 100 80 80
Pigweed 100 100 100 100 100 100 100 100 - 100 100 100 100 100
Rice 80 70 80 - - - - - - - - - - -
Surinam Grass 80 80 80 100 90 100 100 100 60 60 100 100 100 100
Velvetleaf 100 100 100 100 60 100 100 60 100 80 100 100 100 100
Wheat - 90 80 100 100 100 50 40 100 100 100 100
Table B Compounds 500 g ai/ha 33 34 36 40 45 49 50 51 55 57 64 66 67 68 Preemergence Barnyardgrass 80 100 100 100 100 100 100 100 100 100 100 100 90 90 Cocklebur 50 60 60 90 80 70 90 40 40 70 90 20 40 10 Corn 70 100 100 100 100 90 100 90 80 100 100 80 90 90 Crabgrass, Large 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Foxtail, Giant 100 100 90 100 100 100 100 100 100 100 100 100 90 90
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 50 100 70 80 80 70 100 90 60 90 100 40 70 60
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Surinam Grass 90 100 100 100 100 100 100 100 100 100 100 90 100 100
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 50 100 90 80 100 80 90 60 80 100 100 80 70 60
Table B Compounds
500 g ai/ha 71 72 73 74 75 76 87 88 89 90 101 102 103 105
Preemergence
Barnyardgrass 100 100 100 100 80 100 100 100 100 90 100 100 100 100
Cocklebur 60 80 70 80 60 30 100 90 90 0 80 80 100 90
Corn 90 100 100 100 70 100 100 100 100 90 100 100 100 100
Crabgrass, Large 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Foxtail, Giant 100 100 100 100 80 90 100 100 100 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 60 90 90 100 60 80 100 100 100 50 100 100 100 100
■Pigweed 100 100 100 100 100 100 100 100 100 90 100 100 100 100
Surinam Grass 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Velvetleaf 100 100 100 100 100 100 100 100 100 90 100 100 100 100
Wheat 70 100 100 100 70 100 100 100 100 90 100 100 100 100
Table B Compounds
500 g ai/ha 106 107 108 118 119 121 122 123 124 126 127 129 130 131
Preemergence
Barnyardgrass 100 100 100 50 60 60 80 80 80 60 90 0 60 80
Cocklebur 90 80 80 0 0 0 0 0 0 0 0 0 0 0
Corn 100 100 100 0 0 30 60 0 70 30 30 0 0 0
Crabgrass, Large 100 100 100 80 90 100 100 100 90 90 50 0 - 50
Foxtail, Giant 100 100 100 80 90 100 100 100 90 80 70 0 50 50
Lambsquarters 100 100 100 80 90 100 100 100 100 100 90 0 100 100
Momingglory 100 100 100 0 30 0 40 0 30 70 20 0 0 0
Pigweed 100 100 100 90 100 100 100 100 90 90 90 0 100 70
Surinam Grass 100 100 100 60 60 60 90 70 90 20 60 0 0 30
Velvetleaf 100 100 100 60 10 10 90 30 50 0 70 0 90 40
Wheat 100 100 100 20 40 50 60 30 60 70 40 0 0 0 Table B Compounds
500 g ai/ha 132 139 140 147 158 159 160 162 163 164 165 166 167
Preemergence
Barnyardgrass 40 0 70 100 20 70 0 0 70 60 40 70 70
Cocklebur 0 0 0 80 0 0 0 0 0 0 0 0 0
Corn 0 0 80 80 20 0 0 0 0 60 0 70 80
Crabgrass, Large - 0 90 90 70 70 20 50 80 50 50 30 30
Foxtail, Giant 20 0 90 100 70 90 10 0 70 60 40 80 70
Lambsquarters 100 0
Momingglory 0 0 0 90 0 0 0 0 0 0 100 50 20
Pigweed 70 0 100 100 60 100 0 0 90 100 100 100 100
Surinam Grass 20 0 90 90 30 30 0 10 10 20 70 60 50
Velvetleaf 70 0 100 100 10 80 10 10 40 70 0 50 30
Wheat 0 0 90 90 20 10 10 10 10 60 30 50 70
Table B Compounds
250 g ai/ha 41 93 110 112 113 114 115 116 117 120 125 128 153 154
Preemergence
Barnyardgrass 90 90 100 20 100 90 100 70 10 100 80 90 100 90
Cocklebur 10 60 50 0 70 60 50 10 0 40 0 70 50 30
Corn 70 90 90 0 100 70 90 0 0 100 0 80 100 80
Crabgrass, Large 90 100 100 0 100 100 100 70 0 100 100 100 100
Foxtail, Giant 90 90 100 0 100 90 100 50 0 100 80 100 100 90
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 -
Momingglory 30 60 50 0 80 70 80 10 0 70 60 90 70 50
Pigweed 100 100 100 100 100 90 100 100 90 100 100 100 100 100
Surinam Grass 90 90 100 0 90 60 100 50 0 100 90 100 90 90
Velvetleaf 40 100 100 0 100 80 100 60 10 100 100 90 100 80
Wheat 50 90 100 30 100 70 100 0 20 90 50 100 90 80
Table B Compounds Table 2 B Compounds
250 g ai/ha 155 156 157 168 250 g ai> /ha 155 156 157 168
Preemergence : Preemergence
Barnyardgrass 90 100 100 100 ] Momingglory ! 30 ! 30 20 90
Cocklebur 30 50 20 70 Pigweed 100 100 100 100
Corn 90 90 90 100 Surinam Grass ( 30 ! 30 i 30 100
Crabgrass, Large 100 - 90 100 Velvetleaf 100 100 100 100
Foxtail, Giant 90 90 90 100 1 Wheat 70 90 70 100 Table B Compounds
125 g ai/ha 9 10 12 18 21 23 29 30 31 32
Preemergence
Barnyardgrass 70 50 0 80 70 90 90 80 60 30 100 100 80 80
Cocklebur 0 0 0 30 0 30 0 10 0 0 80 70 70 50
Corn 0 0 0 50 10 50 30 30 30 0 100 100 90 80
Crabgrass, Large 90 80 10 90 70 100 100 100 60 80 100 100 100 100
Foxtail, Giant 30 50 20 80 0 90 80 80 40 40 100 100 100 80
Lambsquarters 100 100 100 90 90 100 90 90 90 80 100 100 100 100
Momingglory 0 0 0 50 40 40 30 50 20 0 80 80 70 70
Pigweed 100 100 100 100 100 100 80 100 90 80 100 100 100 100
Rice 60 50 50
Surinam Grass 10 10 0 80 10 100 90 90 30 30 100 100 90 100
Velvetleaf 100 0 100 80 40 90 60 30 20 100 100 100 100
Wheat - 40 0 90 50 50 30 0 100 90 90 60
Table B Compounds
125 g ai/ha 33 34 36 40 45 49 50 51 55 57 64 66 67 68
Preemergence
Barnyardgrass 50 90 70 80 90 80 0 80 90 100 100 70 90 60
Cocklebur 30 30 30 0 70 40 60 0 30 30 80 0 10 0
Corn 30 - 70 90 90 80 0 60 50 90 90 60 50 40
Crabgrass, Large 90 100 100 90 100 100 100 90 90 100 100 70 90 80
Foxtail, Giant 50 80 60 80 90 80 100 80 80 100 100 70 90 70
Lambsquarters 100 100 100 100 100 100 0 100 100 100 100 100 100 100
Momingglory 40 70 50 20 70 50 0 40 30 70 80 20 40 30
Pigweed 90 100 100 100 100 100 0 100 100 100 100 100 100 100
Surinam Grass 60 100 60 80 80 80 100 80 80 100 100 40 70 80
Velvetleaf 90 90 100 90 100 100 100 30 100 100 100 10 60 90
Wheat 40 100 20 70 80 40 90 60 60 90 100 20 40 40
Table B Compounds
125 g ai/ha 71 72 73 74 75 76 87 88 89 90 101 102 103 105
Preemergence
Barnyardgrass 100 100 90 90 30 90 100 100 100 0 100 100 100 100
Cocklebur 40 60 50 60 20 0 90 80 70 0 40 40 100 70
Corn 70 80 90 80 30 50 100 90 80 0 100 100 100 100
Crabgrass, Large 80 100 90 90 50 80 100 100 100 90 100 90 100 100
Foxtail, Giant 80 80 80 80 20 70 100 100 90 60 100 90 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 90 100 100 100 100
Momingglory 60 70 60 70 0 0 100 70 70 0 70 60 90 90
Pigweed 100 100 100 100 90 100 100 100 100 70 100 100 100 100
Surinam Grass 70 100 90 100 60 80 100 100 90 20 100 100 100 100
Velvetleaf 100 80 100 100 30 80 100 100 100 0 100 100 100 100
Wheat 50 60 50 60 20 100 100 100 60 50 100 100 100 100
Table B Compounds
125 g ai/ha 106 107 108 119 121 122 123 124 126 127 129 130 131 132
Preemergence
Barnyardgrass 100 100 100 0 10 20 0 0 0 0 0 0 0 0
Cocklebur 70 50 60 0 0 0 0 0 0 0 0 0 0 0
Corn 100 100 100 0 0 0 0 0 0 0 0 0 0 0
Crabgrass, Large 100 100 100 30 60 90 80 50 0 50 0 50 20 0
Foxtail, Giant 100 100 100 10 20 90 30 40 0 20 0 20 0 0
Lambsquarters 100 100 100 70 80 100 0 0 100 90 0 90 100 40
Momingglory 90 80 90 0 0 0 0 0 60 0 0 0 0 0
Pigweed 100 100 100 70 100 90 0 0 80 90 0 100 30 70
Surinam Grass 100 100 100 0 - 80 50 50 0 0 0 0 0 0
Velvetleaf 100 100 100 0 0 30 0 0 0 0 0 20 0 0
Wheat 100 100 100 10 50 0 0 0 0 0 0 0 0 0
Table B Compounds
125 g ai/ha 140 147 152 158 159 160 162 163 164 165 166 167 182 183
Preemergence
Barnyardgrass 60 70 90 0 0 0 0 0 0 0 0 0 100 100
Cocklebur 0 30 20 0 0 0 0 0 0 0 0 0 50 50
Com 60 30 80 0 0 0 0 0 0 0 10 0 100 100
Crabgrass, Large 30 90 90 0 40 0 20 0 0 0 30 0 100 100
Foxtail, Giant 50 90 90 0 0 0 0 0 0 0 30 0 100 100
Lambsquarters - - 100 - - 0 - 0 0 - - - 100 100
Momingglory 0 90 40 0 0 0 0 0 0 0 0 0 70 40
Pigweed 100 100 100 60 100 - - 0 - - - - 100 100
Surinam Grass 30 90 70 20 20 0 10 0 0 0 20 0 100 100
Velvetleaf 20 100 100 0 20 0 0 0 10 0 0 0 100 100
Wheat 50 70 50 0 10 0 0 0 0 0 30 0 100 100 Table B Compounds
125 g ai/ha 185 186 188 190 202 217 218 219 221 229 230 231 232 234
Preemergence
Barnyardgrass 100 100 70 40 60 100 100 100 100 100 100 100 100 100
Cocklebur 90 90 0 0 30 80 90 90 90 90 70 80 60 70
Corn 100 100 40 60 60 90 100 90 90 100 100 100 90 90
Crabgrass, Large 100 100 70 60 90 100 100 100 100 100 100 100 100 100
Foxtail, Giant 100 100 70 30 70 100 100 100 100 100 100 90 100 100
Lambsquarters 100 100 - 100 100 100 100 100 100 100 100 100 100 100
Momingglory 90 100 0 10 50 80 100 100 100 100 100 90 100 70
Pigweed 100 100 90 100 100 100 100 100 100 100 100 100 100 100
Surinam Grass 90 100 20 50 80 90 100 100 100 100 100 100 100 90
Velvetleaf 100 100 50 20 100 100 100 100 100 100 100 100 100 100
Wheat 100 100 70 90 70 100 100 100 100 100 100 90 100 90
Table B Compounds
125 g ai/ha 235 236 237 238 239 240 241 242 243 244 245 246 249 250
Preemergence
Barnyardg ass 90 100 100 100 100 100 80 90 100 90 100 100 - 90
Cocklebur 70 90 80 80 80 70 20 20 40 30 70 40 40 50
Corn 80 100 100 100 100 90 70 80 90 70 90 100 80 100
Crabgrass, Large 90 100 100 100 100 100 90 90 100 90 100 100 100 100
Foxtail, Giant 80 100 100 100 100 100 80 80 100 90 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 - 100
Momingglory 100 100 100 100 100 60 0 0 30 0 90 70 - 100
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 - 100
Surinam Grass 70 100 100 100 100 80 70 60 90 80 90 90 90 100
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 70 70
Wheat 70 100 100 100 100 90 40 30 90 40 100 90 100 100
Table B Compounds
125 g ai/ha 251 252 253 255 259 260 262 263 264 265 266 267 268 269
Preemergence
Barnyardgrass 100 100 90 100 100 100 100 90 100 90 100 100 100 90
Cocklebur 90 0 0 30 50 20 0 0 90 50 60 30 20 0
Corn 100 90 80 90 90 90 80 80 100 80 80 80 - 20
Crabgrass, Large 100 100 100 100 100 100 90 90 100 100 100 100 90 80
Foxtail, Giant 100 100 90 100 100 90 100 90 100 90 100 100 100 80
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Momingglory 100 0 20 70 60 70 30 30 80 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Surinam Grass 100 100 90 100 100 100 90 80 100 80 100 90 80 50 Velvetleaf 100 90 50 100 100 100 100 100 100 100 100 100 70 100 Wheat 100 70 40 90 90 50 80 60 100 50 90 80 50 20
Table B Compounds
125 g ai/ha 270 272 273 274 275 276 277 279 280 281 282 288
Preemergence
Barnyardgrass 100 100 100 90 100 30 100 100 100 100 100 100
Cocklebur 50 50 40 40 90 0 70 80 70 50 70 80
Corn 80 80 70 60 100 30 90 100 90 90 90 100
Crabgrass , Large 90 100 100 100 100 20 100 100 100 90 100 100
Foxtail , Giant 90 100 100 90 100 30 100 100 100 90 100 100
Lambsquarters 100 100 100 100 100 70 100 100 100 100 100 100
Momingglory - - - - 100 0 100 100 100 70 90 100
Pigweed 100 100 100 100 100 80 100 100 100 100 100 100
Surinam Grass 70 100 80 90 100 20 100 100 100 80 100 100
Velvetleaf 100 100 100 90 100 0 100 100 100 100 100 100
Wheat 50 90 70 80 100 0 90 100 90 50 90 100
Table B Compounds
62 g ai/ha 41 58 93 110 112 113 114 115 116 117 118 120 125 128
Preemergence
Barnyardgrass 70 0 60 50 0 60 20 90 30 0 0 100 20 60
Cocklebur 0 0 20 10 0 40 30 10 0 0 0 0 0 20
Corn 10 0 40 50 0 70 10 80 0 0 0 90 0 70
Crabgrass, Large 90 50 80 80 0 80 60 100 30 0 10 100 90 80
Foxtail, Giant 50 50 50 70 0 60 40 90 0 0 0 100 40 80
Lambsquarters 100 100 100 100 90 100 100 100 90 80 0 100 100 100
Momingglory 0 0 20 20 0 30 30 40 0 0 0 60 50 70
Pigweed 70 100 100 90 100 70 10 100 70 80 0 100 100 60
Surinam Grass 70 50 50 30 0 70 20 70 0 0 0 100 90 50
Velvetleaf 40 60 100 60 0 80 40 100 10 0 10 100 0 50
Wheat 10 0 60 70 0 80 40 80 0 0 0 80 40 50
Table B Compounds 62 g ai/ha 139 152 153 154 155 156 157 168 182 183 185 186 202 217 Preemergence Barnyardgrass 0 70 80 30 50 50 30 100 100 100 90 100 10 90 Cocklebur 0 0 20 0 10 0 30 0 20 70 80 0 60
Corn 0 40 70 0 60 30 0 90 100 70 80 90 50 90
Crabgrass , Large 0 90 100 - 100 50 100 100 100 100 100 80 100
Foxtail , Giant 0 70 90 0 80 70 0 100 90 70 90 100 20 100
Lambsquarters 0 - - - 100 100 100 100 100 100
Momingglory 0 20 70 0 70 0 90 60 20 80 100 0 60
Pigweed 0 100 90 100 100 100 0 100 100 100 100 100 100 100
Surinam Grass 0 50 50 0 60 80 0 90 100 100 90 100 60 90
Velvetleaf 0 100 100 60 100 90 70 100 100 100 100 100 100 100
Wheat 0 40 80 0 40 70 30 90 90 80 100 100 40 90
Table B Compounds
62 g ai/ha 218 219 220 221 229 230 231 232 234 236 237 238 239 240
Preemergence
Barnyardgrass 90 80 80 100 100 100 100 100 100 100 100 100 100 90
Cocklebur 80 60 30 70 70 30 40 20 50 80 60 70 60 20
Corn 90 70 80 90 100 100 100 90 90 90 100 100 90 80
Crabgrass, Large 100 100 100 100 100 100 100 100 90 100 100 100 100 100
Foxtail, Giant 100 90 90 90 100 90 90 100 90 100 100 90 100 90
Lambsquarters 100 100 100 100 100 100 100 100 90 100 100 100 100 100
Momingglory 90 80 70 100 80 90 90 60 - 100 100 100 100 40
Pigweed 100 100 100 100 100 100 100 100 90 100 100 100 100 100
Surinam Grass 100 90 80 90 100 90 90 90 70 90 100 100 100 70
Velvetleaf 100 100 100 100 100 100 100 100 80 100 100 100 100 70
Wheat 100 100 70 100 90 90 90 90 60 100 100 100 90 70
Table B Compounds
62 g ai/ha 241 243 244 245 246 249 250 251 252 253 255 259 260 262
Preemergence
Barnyardgrass 60 100 80 100 100 - - 100 90 90 90 100 100 90
Cocklebur 0 10 0 40 20 20 20 60 0 0 30 30 10 0
Corn 60 90 40 90 90 40 70 100 80 60 90 80 80 70
Crabgrass, Large 70 100 90 100 100 80 80 100 100 100 90 90 90 90
Foxtail, Giant 60 90 90 100 90 80 90 100 90 90 90 90 80 90
Lambsquarters 90 100 100 100 100 - - 100 100 100 100 100 100 100
Momingglory 0 0 0 50 50 - - 100 0 20 50 60 50 20
Pigweed 100 100 100 100 100 - - 100 100 90 100 100 100 100
Surinam Grass 60 80 70 80 90 70 90 100 90 80 90 80 70 80
Velvetleaf 80 100 100 100 100 30 30 100 0 50 100 100 100 90 Wheat 30 70 20 70 90 90 70 100 60 20 70 50 50 60
Table B Compounds
62 g ai/ha 263 264 265 266 267 268 269 270 272 273 274 275 276 277
Preemergence
Barnyardgrass 90 100 50 90 90 80 60 90 90 90 70 100 0 90
Cocklebur 0 70 50 20 30 20 0 30 40 30 20 90 0 40
Corn 70 90 30 50 70 30 0 40 80 60 30 90 0 70
Crabgrass, Large 80 100 100 100 90 90 70 90 100 100 90 100 0 100
Foxtail, Giant 80 100 60 80 90 90 60 70 90 90 80 100 0 90
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 50 100
Momingglory 0 70 - - - - - - - - - 100 0 60
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 30 100
Surinam Grass 70 100 70 80 80 70 20 60 90 70 70 100 0 90
Velvetleaf 70 90 100 100 100 - 60 100 100 100 80 100 0 100
Wheat 20 100 - 60 60 30 20 40 70 - 60 100 0 80
Table B Compounds
62 g ai/ha 279 280 281 282 288
Preemergence
Barnyardgrass 100 90 90 90 100
Cocklebur 70 50 50 40 60
Corn 90 90 70 70 90
Crabgrass, Large 100 90 90 100 100
Foxtail, Giant 100 100 80 90 100
Lambsquarters 100 100 100 100 100
Momingglory 90 30 20 80 70
Pigweed 100 100 100 100 100
Surinam Grass 100 90 70 90 100
Velvetleaf 100 100 100 100 100
Wheat 90 - - 80 90
Table B Compounds Table B Compound
31 g ai/ha 188 190 235 242 16 g ai/ha 58
Preemergence Preemergence
Barnyardgrass 0 0 60 30 Barnyardgrass
Cocklebur 0 0 70 0 Cocklebur
Corn 0 0 50 0 Com
Crabgrass, Large 40 30 80 30 Crabgrass, Large
Foxtail, Giant 0 0 60 10 Foxtail, Giant Lambsquarters - 0 100 100 Momingglory 0
Momingglory 0 0 90 0 Pigweed 0
Pigweed 0 40 100 60 Surinam Grass 0
Surinam Grass 0 0 40 20 Velvetleaf 0
Velvetleaf 0 0 30 80 Wheat 0
Wheat 10 10 20 0
TESTC Seeds or nutlets of plant species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), catchweed bedstraw (Galium aparine), cocklebur (Xanthium strumarium), corn (Zea mays), large crabgrass (Digitaria sanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail (Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album), momingglory (Ipomoea coccinea), eastern black nightshade (Solanum ptycanthum), yellow nutsedge (Cyperus esculentus), redroot pigweed (Amaranthus retroflexus), common ragweed (Ambrosia elatior), Russian thistle (Salsola kali), soybean (Glycine max), common (oilseed) sunflower (Helianthus annuus), velvetleaf (Abutilon theophrasti), and wheat (Triticum aestivum), were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crop and weed species and also winter barley (Hordeum vulgare), blackgrass (Alopecurus myosuroides), canarygrass (Phalaris minor), chickweed (Stellaria media), downy brome (Bromus tectorum), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum), wild oat (Avena fatua) and windgrass (Apera spica-venti) were treated with postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4- leaf stage) for postemergence treatments. Plant species in the flooded paddy test consisted of rice (Oryza sativa), smallflower umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing. Treated plants and controls were maintained in a greenhouse for 12 to 14 days, after which time all species were compared to controls and catchweed bedstraw (Galium aparine), visually evaluated. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table C Compounds 500 g ai/ha 1 2 3 4 7 9 10 12 15 18 19 21 23 28 Flood
Barnyardgrass 95 85 55 75 70 90 95 90 70 90 65 80 80 90 Ducksalad 65 90 20 85 0 60 15 25 0 0 25 0 15 0 Rice 65 75 65 70 75 70 80 75 20 75 70 70 60 50
Sedge, Umbrella 90 90 75 50 0 75 35 55 0 35 60 30 45 50
Table C Compounds
500 g ai/ha 30 31 32 34 40 41 45 49 50 55 64 66 69 71
Flood
Barnyardgrass 100 90 95 90 80 90 80 95 100 75 100 70 70 95
Ducksalad 85 90 20 80 55 45 75 95 55 60 95 75 0 90
Rice 90 95 95 80 75 75 85 85 95 75 95 80 70 95
Sedge, Umbrella 90 90 75 85 85 35 85 95 95 15 90 95 25 95
Table C Compounds
500 g ai/ha 72 73 74 76 87 88 89 90 99 101 102 103
Flood
Barnyardgrass 100 100 100 80 100 95 75 75 0 100 90 70
Ducksalad 70 85 95 65 85 75 85 45 0 85 95 85
Rice 95 95 95 75 95 95 95 65 10 100 90 60
Sedge, Umbrella 75 85 85 55 85 75 70 75 0 95 95 85
Table C Compounds
250 g ai/ha 1 2 3 4 7 ' 9 10 12 15 18 19 21 23 28
Flood
Barnyardgrass 80 55 40 25 35 45 90 70 45 75 45 60 25 55
Ducksalad 45 0 0 0 0 20 15 0 0 0 20 0 0 0
Rice 55 55 25 45 75 50 60 50 0 55 65 30 30 40
Sedge, Umbrella 65 0 50 0 0 30 30 35 0 25 50 25 0 40
Table C Compounds
250 g ai/ha 30 31 32 34 40 41 45 49 50 55 64 66 69 71
Flood
Barnyardgrass 95 75 90 80 55 75 80 90 95 75 100 65 40 75
Ducksalad 75 80 20 70 45 0 60 95 50 0 95 75 0 85
Rice 85 90 85 70 60 70 75 80 90 65 90 65 40 95
Sedge, Umbrella 80 60 70 60 75 35 85 85 95 0 75 95 - 90
Table C Compounds
250 g ai/ha 72 73 74 76 87 88 89 90 99 101 102 103
Flood
Barnyardgrass 95 90 95 75 100 90 - 35 0 100 90 65
Ducksalad 70 65 85 20 80 60 85 15 0 70 95 80
Rice 95 95 75 70 95 95 95 45 0 95 75 25 Sedge, Umbrella 70 20 75 45 85 70 60 15 0 90 95 65
Table C Compounds
125 g ai/ha 1 2 3 4 7 9 10 12 15 18 19 21 23 28
Flood
Barnyardgrass 70 30 0 5 20 25 60 30 15 25 35 30 0 30
Ducksalad - 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 50 25 25 25 35 25 45 25 0 30 25 15 0 30
Sedge, Umbrella 50 0 50 0 0 0 15 0 0 0 30 0 0 25
Table C Compounds
125 g ai/ha 30 31 32 34 40 41 45 49 50 55 64 66 69 71
Flood
Barnyardgrass 75 55 85 50 45 40 60 65 90 25 95 35 0 55
Ducksalad 55 60 20 0 0 0 20 75 15 0 90 40 0 80
Rice 75 65 60 35 40 65 65 60 65 65 90 55 30 85
Sedge, Umbrella 70 45 70 10 65 25 85 45 85 0 70 80 0 80
Table C Compounds
125 g ai/ha 72 73 74 76 87 88 89 90 99 101 102 103
Flood
Barnyardgrass 65 90 65 35 100 85 65 10 0 100 80 60
Ducksalad 65 15 60 0 75 50 65 0 0 65 85 70
I
Rice 75 75 75 50 95 95 60 20 0 90 75 25
Sedge, Umbrella 70 20 50 0 80 55 45 0 0 90 85 60
Table C Compounds
62 g ai/ha 7 9 10 12 15 18 19 21 23 28
Flood
Barnyardgrass 25 20 0 0 10 20 30 25 0 15 20 0 0 0
Ducksalad 15 0 0 0 0 0 0 0 0 0 0 0 0 0
Rice 50 20 10 10 25 20 40 10 0 20 25 10 0 20
Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 25 0 0 0
Table C Compounds
62 g ai/ha 30 31 32 10 41 45 49 500 5555 64 66 69 71
Flood
Barnyardgrass 60 20 70 25 0 20 35 40 65 0 70 20 0 35
Ducksalad 15 0 0 0 0 0 20 65 0 0 70 30 0 75
Rice 65 25 50 35 30 50 40 15 55 30 75 10 20 85
Sedge, Umbrella 25 0 0 0 30 20 70 45 45 0 30 65 0 70 Table C Comp.)ouncIs
62 g ai/ha 72 73 74 76 87 88 89 90 99 101 102 103
Flood
Barnyardgrass 60 55 65 0 75 50 45 0 0 100 60 60
Ducksalad 15 0 35 0 75 25 45 0 0 65 80 40
Rice 70 70 60 30 95 65 60 0 0 85 60 25
Sedge, Umbrella 0 15 20 0 80 20 0 0 0 80 80 20
Table C Compounds
500 g ai/ha 1 3 9 12 21 29 30 31 32 33 34 36 40 41
Postemergence
Barley 65 50 - 45 - 60 60 50 60 60 75 45 45 50
Bermudagrass 5 20 60 60 10 85 100 85 70 80 60 65 60 40
Blackgrass 75 65 - 65 - 85 75 65 70 65 90 70 65 70
Bromegrass, Downy 70 45 - 70 - 70 80 65 65 75 65 55 50 65
Canarygrass 75 45 - 55 - 55 55 65 75 90 75 45 50 65
Chickweed - - 100 100 100
Cocklebur 50 5 10 5 5 10 5 - 45 55 50 10 20 45
Corn - 15 10 20 0 15 5 60 40 15 70 30 20 15
Crabgrass, Large 30 5 60 100 20 100 100 100 90 100 100 90 80 70
Cupgrass, Woolly 45 20 30 60 5 85 40 90 90 70 90 80 80 70
Foxtail, Giant 35 20 30 70 15 100 95 98 85 90 90 80 85 75
Foxtail , Green 95 65 - 65 - 80 75 70 65 95 90 80 75 65
Goosegrass 10 0 20 50 5 100 75 100 85 80 85 80 60 65
Johnsongrass 15 0 20 20 0 60 0 70 70 50 45 45 20 50
Kochia 100 95 85 30 85 100 100 100 95 100 100 100 100 100
Lambsquarters 100 100 100 60 80 100 100 100 100 100 100 100 100 100
Momingglory 100 20 90 80 10 100 100 100 100 100 100 100 100 100
Nutsedge, Yellow 0 0 0 0 0 0 0 15 5 10 10 10 5 0
Oat, Wild 55 50 - 60 - 50 55 60 65 60 65 45 55 65
Pigweed 100 100 100 100 80 100 100 100 100 100 100 100 100 100
Ragweed 80 45 80 50 50 100 100 100 100 100 98 100 100 90
Ryegrass, Italian 70 60 - 65 - 90 75 90 75 65 90 80 60 65
Soybean 80 50 80 100 30 100 90 100 90 100 100 100 100 85
Surinam Grass - 30 20 45 0 100 80 100 85 100 95 100 85 55
Velvetleaf 100 100 100 100 80 100 100 100 100 100 100 100 100 100
Wheat 40 45 - 45 - 50 50 45 45 55 50 50 45 45
Windgrass 100 60 - 70 - 100 100 100 70 100 100 100 100 65 Table C Compounds
500 g ai/ha 45 50 51 55 64 66 67 68 71 72 73 74 76 87
Postemergence
Barley 60 85 50 50 60 45 45 40 65 55 60 60 60 65
Bermudagrass 70 85 60 100 100 30 20 40 90 50 80 60 45 100
Blackgrass 100 100 65 70 90 65 45 50 65 60 65 70 60 100
Bromegrass, Downy 75 90 55 50 80 55 60 65 55 65 65 60 60 70
Canarygrass 65 90 60 60 65 55 60 50 60 65 65 75 60 65
Chickweed - 100 100 85 100 100 100 100 100 100 100 100 100 100
Cocklebur 100 60 55 10 85 25 35 80 25 20 60 30 20 100
Corn 20 5 35 100 60 10 25 15 25 35 85 45 40 95
Crabgrass, Large 100 100 90 60 100 20 65 70 80 100 75 85 80 100
Cupgrass, Woolly 90 90 55 55 95 65 60 95 75 85 80 90 80 100
Foxtail, Giant 90 98 90 80 95 60 75 85 80 90 90 90 80 100
Foxtail, Green 75 90 80 65 90 70 75 70 75 65 85 75 75 98
Goosegrass 85 - 60 95 95 65 65 50 95 70 80 70 70 100
Johnsongrass 50 85 30 5 60 20 20 25 70 60 50 80 80 100
Kochia 100 100 100 85 100 100 100 100 100 100 100 100 100 100
Lambsquarters 100 100 100 70 100 100 100 100 100 100 100 100 100 100
Momingglory 100 100 100 5 100 100 95 100 100 100 100 100 100 100
Nutsedge, Yellow 10 10 10 60 5 0 0 0 0 10 - 25 15 15
Oat, Wild 70 70 45 65 60 65 45 60 60 65 65 65 60 70
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 100 100 100 100 100 100 100 90 100 90 100 100 95 100
Ryegrass, Italian 70 100 50 60 80 45 55 45 65 75 65 65 60 75
Soybean 100 100 85 100 100 100 95 90 100 90 100 100 95 100
Surinam Grass 100 100 100 5 100 85 70 75 100 100 100 90 80 100
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 65 70 55 50 60 50 45 45 55 50 50 50 45 70
Windgrass 100 100 80 - 95 60 60 60 90 75 65 65 65 100
Table C Compounds
500 g ai/ha 89 102 103 105 125
Postemergence
Barley 75 65 90 - -
Bermudagrass 70 100 100 100 70
Blackgrass 65 75 95 - -
Bromegrass, Downy 60 85 85 - -
Canarygrass 100 100 100 - - Chickweed 100 100 100 100 100
Cocklebur 100 80 100 100 15
Corn 60 45 - 95 35
Crabgrass, Large 80 95 100 100 50
Cupgrass, Woolly 80 100 90 100 30
Foxtail, Giant 85 95 100 100 40
Foxtail, Green 65 100 100 - -
Goosegrass 95 90 - 100 50
Johnsongrass 85 100 100 100 10
Kochia 100 100 100 100 100
Lambsquarters 100 100 100 100 100
Morningglory 100 100 100 100 95
Nutsedge, Yellow 0 30 40 60 10
Oat, Wild 50 70 85 - -
Pigweed 100 100 100 100 100
Ragweed 100 100 100 100 100
Ryegrass, Italian 70 75 100 - -
Soybean 95 100 100 100 -
Surinam Grass 85 90 100 100 30
Velvetleaf 100 100 100 100 100
Wheat 45 65 70 - -
Windgrass 75 95 100 _ _
Table C Compounds
250 g ai/ha 9 10 12 18 21 29 30 31 32 33
Postemergence
Barley 45 45 40 55 - 45 40 40 - 55 50 50 50 50
Bermudagrass 0 0 0 40 50 50 20 10 0 80 30 50 60 80
Blackgrass 65 60 65 55 - 60 60 65 - 80 65 65 65 60
Bromegrass, Downy 65 60 45 40 - 65 60 45 - 65 70 55 55 75
Canarygrass 70 60 35 70 - 50 40 45 - 50 50 65 65 85
Chickweed - 100 - 100 100 100 100 100
Cocklebur 15 0 5 5 5 5 5 10 5 10 - 50 40 50
Corn 0 5 10 10 10 15 15 20 0 10 5 50 15 10
Crabgrass, Large - 65 0 60 10 85 70 30 0 100 60 100 80 80
Cupgrass, Woolly 40 10 0 50 15 80 10 50 0 80 40 80 70 60
Foxtail, Giant 20 60 0 60 25 50 30 50 5 90 85 90 65 80
Foxtail, Green 70 60 65 55 - 70 45 50 - 70 50 70 55 85
Goosegrass 0 20 0 45 15 25 5 30 0 100 60 60 45 50 Johnsongrass 0 0 0 5 10 50 10 10 0 10 0 45 10 40
Kochia 100 100 95 95 70 10 20 40 80 100 100 100 90 100
Lambsquarters 100 50 100 85 85 85 45 70 50 100 90 100 100 100
Momingglory 100 30 10 60 90 85 55 80 5 100 100 100 100 100
Nutsedge, Ye11ow 0 0 0 5 0 0 0 5 0 0 0 10 5 10
Oat, Wild 45 65 45 50 - 70 60 65 - 45 50 60 65 60
Pigweed 100 95 100 100 65 100 100 100 60 100 100 100 100 100
Ragweed 55 60 20 90 40 50 30 10 5 100 90 100 100 100
Ryegrass, Italian 70 50 60 40 - 80 65 65 - 90 70 70 65 65
Soybean 50 55 45 50 70 80 50 60 15 85 85 90 80 70
Surinam Grass 10 15 0 35 5 10 10 20 0 85 80 85 80 90
Velvetleaf 100 70 80 100 90 100 100 95 80 100 100 100 100 100
Wheat 35 40 40 45 - 40 35 40 - 50 40 45 40 45
Windgrass 75 40 60 35 - 100 65 - - 100 75 80 65 70
Table C Compounds
250 g ai/ha 34 36 40 41 45 50 51 55 57 64 66 67 68 71
Postemergence
Barley 55 45 45 45 60 80 50 45 55 55 45 40 40 65
Bermudagrass 60 60 40 35 10 60 '45 100 100 70 20 0 0 20
Blackgrass 85 60 65 70 65 100 65 50 100 75 65 45 40 65
Bromegrass, Downy 65 55 50 65 70 75 50 50 65 70 45 40 55 55
Canarygrass 45 45 50 65 60 75 55 55 100 60 45 60 40 60
Chickweed - - - 100 - 100 100 50 100 100 100 100 100 100
Cocklebur 20 10 20 45 100 60 55 10 15 85 20 20 75 25
Corn 10 15 10 15 15 5 35 100 100 60 10 10 15 15
Crabgrass, Large 100 80 60 35 90 100 70 0 100 100 0 20 35 75
Cupgrass, Woolly 70 60 70 60 70 90 50 50 100 90 0 20 50 65
Foxtail, Giant 80 50 70 60 65 70 60 50 80 95 20 60 65 65
Foxtail, Green 75 65 70 60 75 80 70 60 95 75 65 60 65 75
Goosegrass 70 55 40 50 50 80 60 90 100 90 60 25 40 65
Johnsongrass 40 40 15 0 50 20 10 5 15 40 0 0 20 20
Kochia 90 100 100 85 100 100 100 75 100 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 30 90 100 100 100 100 100
Momingglory 100 100 100 95 100 100 100 5 30 100 100 95 100 100
Nutsedge, Yellow 5 5 5 0 10 10 5 60 75 5 0 0 0 0
Oat, Wild 60 45 55 65 65 60 45 65 100 55 60 45 60 60
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 95 100 100 85 100 100 100 100 100 100 100 100 85 100 Ryegrass, Italian 70 80 60 65 70 85 50 55 70 80 40 45 45 50
Soybean 100 100 100 75 100 85 80 100 100 85 95 90 85 100
Surinam Grass 55 70 60 40 100 100 50 5 5 100 80 20 45 65
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat 50 45 45 45 60 55 55 45 70 55 50 45 45 45
Windgrass 80 65 70 65 75 95 65 - - 75 45 60 40 70
Table C Compounds
250 g ai/ha 72 73 74 75 76 87 89 101 102 103 105 122 125
Postemergence
Barley 50 45 45 50 45 65 65 50 60 75
Bermudagrass 50 80 50 15 30 70 65 100 100 80 100 15 50
Blackgrass 60 60 65 65 60 85 55 85 70 75
Bromegrass, Downy 65 60 55 60 60 70 60 75 75 85
Canarygrass 65 45 65 65 55 65 70 90 95 95
Chickweed 100 100 100 100 100 100 100 100 100 100 100 100 100
Cocklebur 15 20 20 10 10 100 100 55 70 100 100 15 10
Corn 30 20 30 30 15 60 15 40 45 50 90 20 35
Crabgrass, Large 80 75 80 50 60 85 65 95 80 90 95 20 10
Cupgrass, Woolly 60 50 75 60 50 95 50 80 90 80 95 35 30
Foxtail, Giant 60 80 60 40 60 85 70 80 90 95 95 30 30
Foxtail, Green 65 70 70 65 65 75 65 95 85 100
Goosegrass 65 80 60 55 60 100 60 85 70 100 90 40 50
Johnsongrass 25 40 40 25 10 95 30 90 85 100 90 20 10
Kochia 95 95 100 100 100 100 100 100 95 100 95 10 100
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 70 100
Momingglory 100 100 100 90 100 100 100 95 100 100 85 95
Nutsedge, Yellow 10 10 20 5 10 10 0 30 20 30 0 10 10
Oat, Wild 60 60 60 60 60 70 50 70 65 70
Pigweed 100 100 100 100 100 100 100 100 90 100 100 100 95
Ragweed 85 100 100 100 85 100 100 100 95 100 100 10 70
Ryegrass, Italian 65 45 55 60 55 70 65 85 75 70
Soybean 80 90 95 85 70 100 95 100 90 100 100 70 85
Surinam Grass 100 80 90 60 55 95 65 85 85 85 95 50 20
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 80 100
Wheat 45 50 50 45 45 65 45 55 65 65
Windgrass 65 45 65 70 65 100 70 90 90 100 Table C Compounds
125 g ai/ha 1 2 3 6 9 10 12 18 21 29 30 31 32 33
Postemergence
Barley 40 40 40 50 - 40 35 25 - 50 50 45 45 50
Bermudagrass 0 0 0 20 5 5 5 10 0 10 20 10 60 50
Blackgrass 65 60 60 50 - 60 40 45 - 70 - 60 45 60
Bromegrass, Downy 55 40 35 40 - 50 40 40 - 55 60 55 40 65
Canarygrass 60 60 35 40 - 45 35 40 - 45 45 55 50 75
Chickweed - 80 - 100 100 100 100 100
Cocklebur 10 0 5 0 5 5 0 0 0 10 5 50 5 10
Com 0 5 5 5 5 15 10 10 0 5 5 10 10 5
Crabgrass, Large 0 65 0 40 0 50 60 10 0 60 45 70 50 80
Cupgrass, Woolly 20 5 0 - 10 45 5 5 0 35 30 60 50 40
Foxtail, Giant 15 40 0 10 20 40 15 35 0 55 60 70 60 40
Foxtail, Green 60 60 60 40 - 45 40 40 - 45 45 55 55 70
Goosegrass 0 5 0 45 5 10 5 5 0 100 30 50 40 45
Johnsongrass 0 0 0 0 10 30 10 5 0 0 0 40 5 5
Kochia 100 90 85 90 60 10 5 5 60 100 90 100 80 100
Lambsquarters 100 50 70 85 80 55 5 10 50 100 80 100 100 100
Momingglory 80 30 10 40 80 80 55 80 0 100 100 100 100 100
Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 5 5 10
Oat, Wild 40 60 40 45 - 65 60 65 - 45 45 55 45 60
Pigweed 80 75 90 95 60 100 75 100 45 100 100 100 100 100
Ragweed 55 40 10 80 0 30 5 5 5 100 85 100 90 85
Ryegrass, Italian 65 50 60 35 - 65 65 65 - 60 60 70 60 65
Soybean 45 50 40 45 60 60 35 30 10 80 80 85 80 70
Surinam Grass 10 5 0 30 5 5 5 5 0 60 80 60 60 50
Velvetleaf 50 40 80 100 60 100 80 50 80 100 100 100 100 100
Wheat 35 40 40 40 - 35 30 35 - 45 35 40 40 45
Windgrass 65 40 60 30 - 60 40 40 - 70 65 80 60 65
Table C Compounds
125 g ai/ha 34 36 40 41 45 50 51 55 57 64 66 67 68 71
Postemergence
Barley 55 45 45 45 50 70 45 40 50 50 45 40 35 65
Bermudagrass 50 0 5 20 0 45 40 100 100 55 0 0 0 0
Blackgrass 65 55 65 70 65 70 50 45 100 70 60 40 40 60
Bromegrass, Downy 60 45 50 60 65 70 40 45 60 50 45 40 45 55
Canarygrass 45 45 50 65 50 70 40 55 80 50 45 55 40 60 Chickweed - - - 100 - 100 100 45 85 100 100 100 100 100
Cocklebur 20 5 15 40 20 50 50 5 15 5 20 20 70 25
Corn 10 15 5 10 10 5 10 70 100 15 10 0 10 10
Crabgrass, Large 80 55 50 20 15 90 40 0 60 50 0 0 20 20
Cupgrass, Woolly 50 40 70 40 60 50 40 45 85 50 0 0 0 55
Foxtail , Giant 75 45 50 20 30 50 50 50 45 90 0 0 0 35
Foxtail, Green 65 65 65 60 65 65 45 60 80 55 60 55 45 70
Goosegrass 30 50 30 35 10 60 55 70 100 60 0 15 20 45
Johnsongrass 40 25 10 0 0 5 5 5 15 0 0 0 0 20
Kochia 85 100 100 80 100 100 100 70 90 100 100 100 100 100
Lambsquarters 100 100 100 95 100 100 100 30 90 100 100 100 100 100
Momingglory 95 100 100 85 100 100 100 5 0 65 100 95 90 100
Nutsedge, Yellow 5 5 5 0 5 5 5 45 65 5 0 0 0 0
Oat, Wild 50 45 55 65 55 60 40 60 100 50 60 40 60 60
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 85 90 95 65 100 100 100 100 100 100 100 95 70 100
Ryegrass, Italian 65 65 55 60 65 65 45 45 65 60 40 45 40 45
Soybean 100 85 100 70 100 85 80 100 100 80 95 80 80 100
Surinam Grass 50 55 60 0 25 80 30 5 5 - 0 0 0 55
Velvetleaf 100 100 100 100 100 100 100 - 100 100 100 100 100 100
Wheat 50 45 45 40 50 55 45 45 65 45 50 40 45 45
Windgrass 65 65 55 60 75 - 40 - - 65 45 60 40 65
Table C Compounds
125 g ai/ha 72 73 74 75 76 87 88 89 90 101 102 103 105 106
Postemergence
Barley 45 45 45 40 45 60 45 65 60 50 45 65 - 65
Bermudagrass 20 70 20 10 5 65 - 55 - 100 80 - 80 60
Blackgrass 45 55 60 65 60 75 65 55 70 65 65 75 - 45
Bromegrass, Downy 55 45 55 50 55 70 60 60 65 65 55 70 - 65
Canarygrass 60 45 45 60 55 60 65 70 70 75 65 90 - 65
Chickweed 100 100 100 100 100 100 - 100 - 100 100 100 100 -
Cocklebur 10 10 5 10 10 100 - 80 - 55 55 65 100 80
Corn 10 10 10 15 15 25 - 15 - 35 40 30 65 45
Crabgrass, Large 30 70 50 20 20 75 - 55 - 70 40 70 45 40
Cupgrass, Woolly 40 50 45 50 30 75 - 20 - 80 80 70 75 55
Foxtail, Giant 40 40 40 30 40 65 - 55 - 75 60 90 60 55
Foxtail, Green 45 45 60 55 55 75 60 60 65 90 80 100 - 65
Goosegrass 40 50 35 55 60 70 - 55 - 55 70 50 65 60 Johnsongrass 10 5 15 20 10 70 - 0 - 80 80 95 85 45
Kochia 90 95 100 100 100 100 - 100 - 100 95 95 90 100
Lambsquarters 100 100 100 100 100 100 - 100 - 100 80 100 100 100
Momingglory 70 100 80 100 60 100 - 100 - 80 85 100 100 100
Nutsedge, Yellow 5 10 5 5 10 0 - 0 - 20 20 25 0 20
Oat, Wild 45 40 50 60 55 65 65 45 65 65 65 65 - 65
Pigweed 100 100 100 100 100 100 - 100 - 100 85 100 100 100
Ragweed 80 85 100 80 55 100 - 100 - 90 85 90 95 100
Ryegrass, Italian 55 40 45 50 55 65 70 65 70 80 70 65 - 60
Soybean 50 70 80 80 65 100 - 85 - 100 85 100 100 100
Surinam Grass 55 50 45 60 50 50 - 60 - 85 85 60 80 55
Velvetleaf 100 100 100 100 100 100 - 100 - 100 100 100 100 100
Wheat 40 45 45 40 40 45 45 40 65 45 50 50 - 65
Windgrass 45 45 55 65 50 70 65 65 65 70 70 70 - 55
Table C Compounds
125 g ai/ha 107 108 115 120 122 125 153 168 182 183 185 218 219 229
Postemergence
Barley 65 70 60 65 - - 45
Bermudagrass 60 60 - 55 15 35 55 60 70 - 80 60 60 15
Blackgrass 70 65 80 80 - - 70 - - - - - - -
Bromegrass, Downy 60 75 60 60 - - 65 - - - - - - -
Canarygrass 65 65 80 75 - - 65 - - - - - - -
Chickweed - 100 100 100 100 100 100 100 100 100 100 100 100 100
Cocklebur 100 65 85 100 10 10 50 85 85 60 100 65 60 -
Corn 65 40 30 40 20 30 10 50 10 10 85 50 20 50
Crabgrass, Large 70 20 70 55 15 10 35 80 10 40 60 35 55 20
Cupgrass, Woolly 65 70 60 65 30 25 60 55 55 70 75 75 25 55
Foxtail, Giant 75 45 70 60 20 20 65 90 50 80 90 55 55 50
Foxtail, Green 70 65 95 85 - - 65 - - - - - - -
Goosegrass 75 35 75 85 35 30 90 70 75 60 55 60 50 35
Johnsongrass 20 45 50 25 15 0 5 85 10 15 100 20 30 10
Kochia 100 100 100 100 5 95 95 95 100 90 100 100 90 100
Lambsquarters 100 100 100 100 65 100 100 100 100 90 100 100 100 100
Momingglory 100 100 100 100 50 95 95 100 100 65 100 100 100 100
Nutsedge, Yellow 25 10 75 15 10 5 10 30 10 5 35 15 10 10
Oat, Wild 60 65 65 70 - - 65 - - - - - - -
Pigweed 100 100 100 100 100 95 - 100 100 100 100 100 100 100
Ragweed 100 100 95 100 10 50 100 100 100 95 100 100 90 100 Ryegrass, Italian 70 65 85 80 - - 55
Soybean 100 95 100 100 40 85 80 95 95 95 95 100
Surinam Grass 65 90 70 75 15 10 60 90 55 40 100 100 55 60
Velvetleaf 100 100 100 100 80 100 100 100 100 100 100 100 100 100
Wheat 65 60 65 65 - - 60
Windgrass 95 70 100 go - - 90 - - - - - - -
Table C Compounds
125 g ai/ha 230 231 232 234 238 239 244 259
Postemergence
Barley _ _ _ _ _ 50
Bermudagrass 70 80 5 55 60 0 35 50
Blackgrass
Bromegrass, Downy _ _ _ _ _ 40
Canarygrass _ _ _ _ _ _ _ 40
Chickweed 100 - 100 100 100 100
Cocklebur 100 - 100 60 100 100 100 100
Corn 40 45 60 50 70 35 15 10
Crabgrass, Large 50 75 60 50 65 70 40 60
Cupgrass, Woolly 55 65 60 60 50 65 70 35
Foxtail, Giant 60 70 60 60 90 55 55 50
Foxtail, Green _ _ _ _ _ _ _ 80
Goosegrass 90 75 45 60 95 10 65 60
Johnsongrass 40 40 65 60 45 45 10 25
Kochia 100 100 100 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100
Momingglory 100 100 100 100 100 100 100 100
Nutsedge, Yellow 15 25 10 60 5 10 10 10
Oat, Wild - 50
Pigweed 100 100 100 100 100 100 100 100
Ragweed 100 100 100 90 100 100 100 100
Ryegrass, Italian _ _ _ _ _ _ _ 70
Soybean 100 100 100 100 100 100 100 95
Surinam Grass 95 80 80 55 90 70 50 45
Velvetleaf 100 100 100 100 100 100 100 100
Wheat _ _ _ _ _ _ _ 50
Windgrass _ 70 Table C Compounds
62 g ai/ha 1 2 3 6 9 10 12 18 21 29 30 31 32 33
Postemergence
Barley 40 35 40 40 - 30 35 15 - 40 45 40 40 45
Bermudagrass 0 - 0 0 0 0 5 5 0 0 0 10 10 50
Blackgrass 60 60 45 45 - 40 30 35 - 50 55 60 35 60
Bromegrass, Downy 40 40 35 30 - 50 30 35 - 40 40 40 35 60
Canarygrass 50 50 35 40 - 40 30 35 - 35 40 55 40 70
Chickweed - 0 - 100 100 100 80 100
Cocklebur 10 0 5 0 0 0 0 0 0 10 5 30 5 5
Corn 0 5 0 5 5 10 10 5 0 5 5 10 5 5
Crabgrass, Large 0 - 0 5 0 50 10 5 0 40 30 45 40 50
Cupgrass, Woolly 0 5 0 0 5 40 5 5 0 30 20 30 50 40
Foxtail, Giant 5 5 0 10 10 15 10 20 0 45 30 55 40 40
Foxtail, Green 55 60 50 25 - 45 30 35 - 35 45 55 45 65
Goosegrass 0 5 0 40 5 5 5 5 0 50 30 40 40 45
Johnsongrass 0 0 0 0 0 30 10 5 0 0 0 20 0 5
Kochia 70 - 40 70 45 5 5 5 50 100 80 100 60 80
Lambsquarters 60 15 70 10 60 55 - 0 0 100 0 100 80 100
Morningglory 80 15 5 20 80 70 50 25 0 85 90 100 95 100
Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 5 5 5
Oat, Wild 35 50 40 40 - 60 45 60 - 35 45 45 45 55
Pigweed 80 60 60 50. 50 80 75 65 40 100 100 100 100 100
Ragweed 45 - 5 80 0 10 0 0 5 85 80 100 10 40
Ryegrass, Italian 60 40 60 35 - 60 40 60 - 50 60 65 60 65
Soybean 30 15 20 35 60 60 30 - 10 70 80 85 80 70
Surinam Grass 0 5 0 0 5 5 5 5 0 60 10 10 50 50
Velvetleaf 20 5 55 100 50 50 55 0 50 100 100 100 100 100
Wheat 35 30 35 35 - 30 30 25 - 40 35 35 35 40
Windgrass 65 40 35 25 - 40 30 40 - 45 35 60 40 60
Table C Compounds
62 g ai/ha 34 36 40 41 45 50 51 55 57 64 66 67 68 71
Postemergence
Barley 45 40 45 45 50 70 45 40 45 45 40 35 30 65
Bermudagrass 50 0 5 15 0 40 40 100 100 50 0 0 0 0
Blackgrass 35 40 60 65 60 70 30 35 65 50 60 35 35 60
Bromegrass, Downy 60 45 50 35 55 70 40 40 60 35 45 35 30 45
Canarygrass 35 40 50 60 45 65 35 55 70 50 45 40 40 40 Chickweed - - - 95 - 100 100 30 50 100 100 100 100 100
Cocklebur 15 5 15 35 - 50 50 5 15 0 20 20 20 20
Corn 5 10 - 5 10 0 0 60 100 5 10 0 10 5
Crabgrass, Large 60 50 5 20 5 45 0 0 50 40 0 0 0 0
Cupgrass, Woolly 40 20 30 0 20 40 30 40 60 - 0 0 0 0
Foxtail , Giant 40 40 20 15 10 45 50 45 40 40 0 0 0 20
Foxtail, Green 60 60 65 60 60 40 35 30 75 45 60 45 45 60
Goosegrass 10 40 30 20 5 55 50 45 100 50 0 0 0 40
Johnsongrass 5 20 0 0 0 5 0 5 10 0 0 0 0 0
Kochia 50 85 100 35 100 95 100 40 85 100 100 95 100 100
Lambsquarters 100 100 100 95 100 100 100 30 55 95 100 90 100 100
Mo ingglory 60 100 100 75 100 100 100 5 0 60 100 20 90 100
Nutsedge, Yellow 5 5 5 0 5 5 0 35 45 0 0 0 0 0
Oat, Wild 45 35 55 65 45 50 35 45 100 45 60 35 55 60
Pigweed 100 100 100 85 100 100 100 100 100 90 100 100 100 100
Ragweed 80 70 95 45 70 100 98 100 100 90 100 65 65 90
Ryegrass, Italian 60 40 55 55 60 50 30 45 65 50 35 40 40 45
Soybean 80 70 85 60 100 70 60 100 100 80 90 75 75 95
Surinam Grass 50 50 40 0 20 80 5 0 - 80 0 0 0 50
Velvetleaf 100 100 100 60 100 100 100 - 100 100 100 100 55 100
Wheat 35 40 45 35 45 45 40 45 65 40 40 40 45 40
Windgrass 65 60 - 40 40 70 40 - - 60 45 60 40 65
Table C Compounds
62 g ai/ha 72 73 74 75 76 87 88 89 90 101 102 103 105 106
Postemergence
Barley 45 45 45 40 45 60 45 60 45 45 45 45 - 50
Bermudagrass 5 50 - 10 5 20 - 15 - 100 70 - 75 45
Blackgrass 40 35 50 60 55 65 55 40 65 65 60 60 - 45
Bromegrass, Downy 55 45 45 45 45 65 45 55 65 60 45 65 - 65
Canarygrass 45 45 40 45 55 45 60 65 70 75 65 70 - 65
Chickweed 100 100 100 100 100 100 - 100 - 100 100 100 100 100
Cocklebur 10 5 5 10 5 100 - 75 - 55 50 60 100 75
Corn 5 5 10 10 10 10 - 10 - 30 30 20 40 45
Crabgrass, Large 5 50 10 5 5 40 - 40 - 60 20 60 40 20
Cupgrass, Woolly 30 40 40 50 30 70 - 15 - 80 65 50 55 30
Foxtail, Giant 20 35 - 30 30 55 - 15 - 60 50 60 55 40
Foxtail, Green 40 45 50 45 45 65 60 55 65 80 65 80 - 50
Goosegrass 40 40 30 50 30 65 - 0 - 50 60 50 25 50 Johnsongrass 10 5 10 20 10 55 - 0 - 80 50 60 45 15
Kochia 85 95 100 100 95 100 - 95 - 80 35 95 85 95
Lambsquarters 100 95 100 100 100 100 - 100 - 85 50 95 95 95
Mo ingglory 60 90 70 100 - 100 - 80 - 80 85 100 100 100
Nutsedge, Yellow 5 10 5 5 5 0 - 0 - 20 10 20 0 10
Oat, Wild 45 40 45 60 45 65 65 45 65 55 60 65 - 65
Pigweed 100 95 100 100 100 100 - 100 - 80 80 70 95 100
Ragweed 60 80 100 60 55 100 - 95 - 80 80 80 90 95
Ryegrass, Italian 45 40 45 45 55 65 60 60 70 60 55 65 - 55
Soybean 30 70 80 60 60 95 - 80 - 80 70 85 100 90
Surinam Grass 50 40 40 60 40 45 - 20 - 60 40 40 20 55
Velvetleaf 100 100 100 100 100 100 - 100 - 100 100 100 100 100
Wheat 40 45 35 40 35 40 40 40 60 45 45 45 - 45
Windgrass 40 35 40 60 50 65 60 45 65 65 65 60 - 45
Table C Compounds
62 g ai/ha 107 108 115 120 122 125 153 168 182 183 185 218 219 229
Postemergence
Barley 65 70 60 60 - - 45 - - - - - - -
Bermudagrass 55 50 85 50 10 30 40 40 - 60 50 30 40 10
Blackgrass 70 65 70 80 - - 65 - - - - - - -
Bromegrass, Downy 45 55 55 55 - - 45 - - - - - - -
Canarygrass 65 65 75 70 - - 65 - - - - - - -
Chickweed 100 100 100 - 100 100 100 100 - - 100 100 100 100
Cocklebur 70 60 65 100 10 10 50 55 65 45 50 55 50 100
Corn - 40 15 15 15 30 10 30 5 10 20 25 - 20
Crabgrass, Large 45 15 45 20 15 5 20 50 10 30 25 15 20 15
Cupgrass, Woolly 65 50 50 55 15 20 35 - - 25 - 45 25 35
Foxtail, Giant 50 35 55 55 10 20 50 65 45 45 55 45 35 30
Foxtail, Green 70 65 90 70 - - 55 - - - - - - -
Goosegrass 60 30 65 75 30 30 75 70 65 55 40 - 40 35
Johnsongrass 15 45 10 10 10 0 0 10 10 0 15 20 10 5
Kochia 100 100 95 100 5 85 95 95 100 85 80 95 90 100
Lambsquarters 100 100 100 100 60 85 80 100 95 85 100 100 70 100
Momingglory 100 100 100 100 15 80 - 95 100 50 100 100 100 100
Nutsedge, Yellow 5 5 25 10 10 5 5 30 10 0 10 5 10 10
Oat, Wild 60 65 65 55 - - 60 - - - - - - -
Pigweed 100 100 100 100 60 60 90 100 100 100 100 100 100 100
Ragweed 100 100 95 95 5 50 85 100 90 60 90 90 80 100 Ryegrass, Italian 55 60 85 70 - - 45
Soybean 100 95 95 95 40 70 80 90 95 95 95 - 95 80
Surinam Grass 55 45 50 50 10 10 - 80 50 25 65 45 30
Velvetleaf 100 100 100 100 40 100 100 100 100 100 100 100 100 100
Wheat 65 55 60 65 - - 55
Windgrass 60 70 100 90 - - 75
Table C Compounds
62 g ai/ha 230 231 232 234 238 239 244 252 253 259 263
Postemergence
Barley _ 50 -
Bermudagrass 50 60 0 50 15 0 30 50 85 15 15
Blackgrass _ _ _ _ _ _ 70 -
Bromegrass, Downy _ 0
Canarygrass _ _ _ _ _ _ _ _ _ 40 -
Chickweed 100 100 100 100 100 100 100 100 100 100 100
Cocklebur 100 100 100 50 - 100 55 35 0 50 35
Corn 30 10 15 40 10 25 10 20 10 10 20
Crabgrass, Large 20 50 40 45 25 55 30 55 55 35 40
Cupgrass, Woolly 45 60 50 50 20 50 45 75 - 30 50
Foxtail, Giant 45 50 50 45 20 45 40 65 55 35 55
Foxtail, Green _ _ _ _ _ _ _ _ 70 -
Goosegrass 60 70 25 50 - - 55 65 75 50 10
Johnsongrass 5 40 35 20 10 45 5 55 50 20 15
Kochia 100 100 100 100 100 100 100 100 100 100 100
Lambsquarters 100 100 100 95 95 100 100 100 100 100 100
Momingglory 100 100 100 100 - 100 95 100 100 100 100
Nutsedge, Yellow 15 10 10 25 5 10 5 40 45 5 15
Oat, Wild _ _ _ _ _ _ 50 -
Pigweed 100 100 100 100 - 100 100 100 100 100 100
Ragweed 100 95 100 75 - 100 100 90 100 100 85
Ryegrass, Italian _ _ _ _ _ _ _ 55
Soybean 95 100 100 95 95 100 100 100 100 95 100
Surinam Grass 55 70 50 45 - 60 45 55 35 40 45
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100
Wheat _ _ _ _ _ _ _ _ 45
Windgrass _ _ _ _ _ _ 65 - Table C ComplounάIs
31 g ai/ha 2 6 10 18 57 75 88 90 101 106 107 108 115 120
Postemergence
Barley 30 30 25 15 45 40 45 40 45 45 65 55 60 60
Bermudagrass 0 0 0 5 100 5 - - 60 45 55 40 70 35
Blackgrass 60 45 40 30 65 60 55 55 55 45 65 50 70 75
Bromegrass, Downy 40 25 50 30 50 45 40 55 55 45 45 55 45 45
Canarygrass 45 35 30 35 65 45 45 65 60 45 65 60 70 60
Chickweed 0 100 100 75 40 100 - - 100 100 100 80 - 100
Cocklebur 0 0 0 0 10 5 - - 50 60 65 50 40 -
Corn 5 5 10 5 100 10 - - 25 40 55 15 15 15
Crabgrass, Large 30 0 0 0 0 5 - - 40 10 25 5 35 20
Cupgrass, Woolly 5 0 20 5 50 40 - - 50 25 55 35 50 50
Foxtail, Giant 5 0 10 10 20 25 - - 20 30 45 30 50 50
Foxtail, Green 50 20 40 30 60 40 60 60 65 45 60 60 65 65
Goosegrass 5 40 5 5 80 10 - - 30 50 60 - 55 65
Johnsongrass 0 0 0 5 10 20 - - 40 0 10 40 5 0
Kochia 50 40 5 5 50 80 - - 50 90 100 100 90 95
Lambsquarters 10 10 50 0 50 90 - - 45 95 100 75 100 100
Momingglory 10 10 70 20 0 70 - - - 100 100 100 100 -
Nutsedge, Yellow 0 0 0 0 45 0 - - 15 5 5 5 15 10
Oat, Wild 45 35 45 50 65 45 60 65 55 45 55 65 60 55
Pigweed 50 50 50 5 100 100 - - 60 95 100 100 100 100
Ragweed 5 40 0 0 100 50 - - 70 90 100 85 55 75
Ryegrass, Italian 35 30 45 60 60 40 60 60 50 45 45 55 70 65
Soybean 10 30 40 15 100 40 - - 80 60 90 75 95 95
Surinam Grass 0 0 0 0 - 5 - - 50 30 50 30 50 -
Velvetleaf 0 95 50 0 100 100 - - 100 100 100 100 100 100
Wheat 25 25 25 25 60 40 40 40 45 45 65 50 55 60
Windgrass 25 25 40 30 - 60 60 65 60 45 45 40 85 85
Table C Compounds
31 g ai/ha 122 153 168 182 183 185 218 219 229 230 231 232 234 238
Postemergence
Barley - 45
Bermudagrass 10 35 35 35 60 10 30 - 10 35 30 0 50 0
Blackgrass - 60
Bromegrass, Downy - 45
Canarygrass - 50 Chickweed 60 100 100 100 95 100 100 100 100 100 100 100 100 100
Cocklebur 5 50 50 55 15 45 55 50 100 - 65 65 10 90
Corn 15 10 10 5 10 10 15 10 20 5 10 0 20 5
Crabgrass, Large 10 15 30 10 30 10 15 15 15 20 25 25 20 20
Cupgrass, Woolly 10 25 45 50 20 30 30 25 30 40 55 20 35 15
Foxtail, Giant 10 35 50 35 35 40 40 30 20 35 40 30 40 20
Foxtail, Green - 55
Goosegrass 30 60 45 - 50 20 35 30 15 55 55 20 50 30
Johnsongrass 10 0 5 10 0 10 15 0 5 0 20 10 5 0
Kochia 0 70 95 95 75 75 90 60 100 100 95 100 95 100
Lambsquarters 60 - 100 75 60 80 100 65 100 95 100 100 65 95
Momingglory 10 95 90 95 30 95 95 - 95 100 100 100 50 100
Nutsedge, Yellow 5 5 5 10 0 5 5 0 0 5 10 5 10 5
Oat, Wild - 50
Pigweed 60 80 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 5 70 85 80 50 80 80 60 100 95 90 90 60 90
Ryegrass, Italian - 40 - -
Soybean 30 65 60 90 75 95 100 85 55 90 100 100 85 90
Surinam Grass 10 45 40 20 25 10 30 20 20 45 50 45 40 35
Velvetleaf 40 100 100 100 100 100 100 100 100 100 100 100 100 100
Wheat - 50 - -
Windgrass _ 75 _, _
Table C Compounds
31 g ai/ha 239 244 252 253 259 263
Postemergence
Barley - 45
Bermudagrass 0 25 45 20 10 10
Blackgrass - 60
Bromegrass, Downy - 35
Canarygrass - 35
Chickweed 100 - 100 85 100 100
Cocklebur 100 55 15 0 50 30
Corn 10 10 20 5 10 15
Crabgrass, Large 50 30 50 40 30 30
Cupgrass, Woolly 40 35 55 65 30 40
Foxtail, Giant 40 35 55 50 30 45
Foxtail, Green - 70
Goosegrass 10 50 55 60 10 10 Johnsongrass 10 5 50 45 20 10
Kochia 100 100 100 100 100 50
Lambsquarters 100 100 95 100 100 -
Momingglory 100 95 90 100 100 55
Nutsedge, Yellow 5 0 25 30 5 5
Oat, Wild - - - - 45 -
Pigweed 100 100 100 100 100 90
Ragweed 100 65 75 90 85 70
Ryegrass, Italian - - - - 50 -
Soybean 100 100 100 100 80 90
Surinam Grass 30 30 40 30 30 20
Velvetleaf 100 100 100 100 100 100
Wheat - - - - 45 -
Windgrass - - - - 65 -
Table C Comj: >oun
16 g ai/ha 88 90 106 107 108 115 120
Postemergence
Barley 40 40 45 65 45 55 50 45 -
Bermudagrass - - 40 50 40 50 25 35 25 40 - 35
Blackgrass 40 45 45 65 45 55 65 50 -
Bromegrass, Downy 30 45 40 40 45 30 40 35 -
Canarygrass 40 65 40 60 50 60 60 45 -
Chickweed - - 100 100 - 100 100 100 100 90 95 - 100 100
Cocklebur - - 50 60 - 10 75 45 50 35 10 35 50 45
Corn - - 35 35 10 10 10 5 10 5 5 - 10 10
Crabgrass, Large - - 10 10 5 30 15 10 15 5 15 5 5 15
Cupgrass, Woolly - - 10 40 30 45 50 20 45 15 10 20 25 15
Foxtail, Giant - - 25 35 30 50 45 30 45 30 25 30 25 30
Foxtail, Green 40 60 45 45 40 60 60 45
Goosegrass - - 50 50 20 50 60 50 30 50 25 20 10 25
Johnsongrass - - 0 0 35 5 0 0 0 5 0 0 10 0
Kochia - - 65 85 85 70 95 65 95 65 35 65 60 35
Lambsquarters - - 85 80 75 90 100 75 55 55 50 75 75 65
Momingglory - - 100 100 100 70 100 80 75 70 30 90 80 75
Nutsedge, Yellow - - 5 5 0 5 5 0 5 0 0 0 0 0
Oat, Wild 40 60 45 55 50 55 55 45
Pigweed - - 65 100 100 95 100 75 95 70 75 100 100 100
Ragweed - - 80 90 60 50 75 65 70 50 10 50 70 45 Ryegrass, Italian 45 55 40 45 55 45 45 35
Soybean - 60 75 60 60 80 50 55 60 55 55 45 50
Surinam Grass - 25 40 - 45 45 30 40 15 - 10 10 15
Velvetleaf - 100 100 100 100 100 95 100 100 100 100 100 100
Wheat 30 35 45 65 45 50 55 45
Windgrass 30 60 40 45 40 65 65 60
Table C Compounds
16 g ai/ha 229 230 231 232 234 238 239 244 252 253 259 263
Postemergence
Barley _ _ _ _ _ _ _ _ 40 -
Bermudagrass 10 25 10 0 40 0 0 10 45 10 0 0
Blackgrass _ _ _ _ _ _ 40 -
Bromegrass, Downy _ _ _ _ _ _ _ _ _ 35 -
Canarygrass _ _ _ _ 35 _
Chickweed 95 - 100 95 100 100 100 100 100 80 100 95
Cocklebur 50 65 65 45 10 50 55 50 15 0 5 20
Corn 5 5 5 0 10 5 10 5 15 5 5 15
Crabgrass, Large 10 15 10 15 15 10 40 10 35 30 10 20
Cupgrass, Woolly 25 25 50 10 25 15 20 25 45 50 20 30
Foxtail, Giant 15 30 35 25 30 15 30 25 50 40 30 35
Foxtail, Green _ _ _ _ _ _ _ _ _ _ 50 -
Goosegrass 5 50 40 5 50 20 5 50 55 50 5 5
Johnsongrass 5 0 15 0 0 0 0 0 20 10 20 10
Kochia 75 95 85 90 90 85 80 100 95 95 60 40
Lambsquarters 75 95 90 95 50 70 95 100 95 95 100 95
Momingglory 90 100 100 100 45 100 100 90 100 40
Nutsedge, Yellow 0 0 10 5 10 0 5 0 25 15 5 5
Oat, Wild _ _ _ _ _ _ _ _ _ _ 45 _
Pigweed 100 100 100 100 100 100 100 100 100 100 100 80
Ragweed 80 70 75 75 40 65 75 45 75 80 50 50
Ryegrass, Italian _ •_ _ _ _ _ _ _ _ 50 -
Soybean 40 85 90 100 65 75 100 80 100 75 70 90
Surinam Grass 10 40 35 30 30 20 10 30 40 20 30 20
Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100
Wheat _ _ _ _ _ _ _ _ _ _ 40 -
Windgrass _ _ _ _ _ _ _ _ _ 50 - Table c Compounds Tabli_ c Compounds
8 g ai/ha 252 253 263 8 g iai/ha 252 253 263
Postemergence Postemergence
Bermudagrass 30 10 0 Kochia 50 55 15
Chickweed 40 60 75 Lambsquarters 60 85 60
Cocklebur 15 0 0 Mo ingglory 90 100 20
Corn 10 5 5 Nutsedge , Yellow 10 5 5
Crabgrass, Large 35 30 5 Pigweed 60 90 55
Cupgrass, Woolly - 30 25 Ragweed 65 55 30
Foxtail, Giant 50 40 20 Soybisan 70 75 25
Goosegrass 50 45 0 Surinam ( 3rass 15 15 10
Johnsongrass 15 0 10 Velvetleaf 100 50 100
Table C Compounds
500 g ai/ha 3 9 12 23 29 30 31 32 33 34 36 40 45 50
Preemergence
Bermudagrass 100 95 100 100 100 100 100 100 100 100 100 100 100 100
Cocklebur 0 40 20 0 85 100 100 30 0 60 50 65 90 85
Corn 55 60 70 30 100 100 95 95 95 95 95 100 100 100
Crabgrass, Large 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Cupgrass, Woolly 60 70 85 80 100 90 100 100 85 98 80 95 100 100
Foxtail, Giant 70 80 100 90 100 100 100 100 - 100 90 100 100 100
Goosegrass 70 95 100 75 100 100 100 100 100 100 100 100 100 100
Johnsongrass 85 90 95 85 100 100 100 100 90 100 100 100 100 100
Kochia 100 60 40 0 100 100 100 80 100 90 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 70 60 80 40 100 100 85 100 0 90 70 100 100 95
Nightshade 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Nutsedge, Yellow 0 40 10 0 55 70 40 30 40 20 5 40 30 50
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 55 80 70 10 100 100 100 90 0 85 45 90 100 100
Soybean 60 95 80 50 100 100 100 100 50 100 85 100 100 100
Sunflower 40 40 40 10 85 85 80 60 5 60 50 85 85 100
Surinam Grass 65 90 100 85 100 100 100 100 100 100 100 100 100 100
Velvetleaf 100 100 100 100 100 100 100 100 50 100 100 100 100 100 Table C Compounds
500 g ai/ha 51 55 64 66 67 68 71 72 73 74 76 87 89 102
Preemergence
Bermudagrass 100 80 100 100 100 100 100 100 100 100 100 100 100 100
Cocklebur 40 100 85 75 70 100 95 70 30 80 5 95 90 100
Corn 85 0 100 95 95 95 100 95 95 100 50 100 100 100
Crabgrass, Large 100 98 100 100 100 100 100 100 100 100 100 100 100 100
Cupgrass, Woolly 95 90 100 85 95 85 100 95 100 100 95 100 100 100
Foxtail, Giant 100 10 100 100 100 95 100 100 90 100 100 100 100 100
Goosegrass 100 100 100 100 100 95 100 95 95 100 100 100 100 100
Johnsongrass 100 50 100 100 100 100 100 100 100 100 80 100 100 100
Kochia 100 100 100 100 100 100 100 100 90 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Mo ingglory 50 10 100 100 85 100 100 80 100 100 - 100 100 100
Nightshade 100 70 100 100 100 100 100 100 100 100 100 - - 100
Nutsedge, Yellow 0 100 40 15 20 0 30 0 0 50 0 35 100 100
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 100 100 100 100 100 95 100 90 95 100 100 100 100 100
Soybean 60 80 100 100 100 100 100 100 100 100 60 100 100 -
Sunflower 65 100 90 65 65 20 100 80 70 100 10 100 95 95
Surinam Grass 90 100 100 100 95 95 100 100 100 100 100 100 100 -
Velvetleaf 100 40 100 100 100 100 100 100 100 100 100 100 100 100
Table C Compounds
500 g ai/ha 103 105 110 113 125
Preemergence
Bermudagrass 100 100 100 - 100
Cocklebur 100 90 10 5 0
Corn 100 100 90 - -
Crabgrass, Large 100 100 - 100 100
Cupgrass, Woolly 100 100 100 - 80
Foxtail, Giant 100 100 100 - 100
Goosegrass 100 100 100 80 100
Johnsongrass 100 100 100 100 95
Kochia 100 100 - - -
Lambsquarters 100 100 100 100 100
Momingglory 100 100 40 100 100
Nightshade 100 100 100 100 100
Nutsedge, Yellow 100 85 50 0 100 Pigweed 100 100 100 100 100
Ragweed 100 100 60 80 100
Soybean - 100 100 80 100
Sunflower 100 100 80 - 5
Surinam Grass - 100 50 - 90
Velvetleaf 100 100 100 100 100
Table C Compounds
250 g ai/ha 2 3 6 9 10 12 18 23 29 30 31 32 33 34
Preemergence
Bermudagrass 90 80 100 95 100 90 100 80 100 100 100 100 100 100
Cocklebur 0 0 10 5 30 10 10 0 85 85 50 10 0 20
Corn 60 20 60 30 85 50 50 5 100 100 90 90 20 95
Crabgrass, Large 100 80 100 90 100 100 100 85 100 100 100 100 100 100
Cupgrass, Woolly 85 50 90 50 90 70 85 65 90 90 90 90 60 90
Foxtail, Giant 100 50 100 60 95 80 100 70 100 100 100 100 90 100
Goosegrass 100 60 90 90 100 100 100 20 100 100 100 100 90 100
Johnsongrass 100 80 100 80 100 95 90 60 100 100 100 100 90 100
Kochia 95 100 100 60 50 5 0 0 100 100 100 60 80 90
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 80 30 10 55 85 50 50 5' 100 100 80 85 0 80
Nightshade 100 100 100 100 100 100 100 80 100 100 100 100 100 100
Nutsedge, Yellow 5 0 0 10 5 0 20 0 40 50 5 30 5 5
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 80 50 95 60 80 50 60 0 100 100 85 85 0 55
Soybean 50 50 35 60 50 40 40 5 100 100 70 50 10 85
Sunflower 35 0 40 10 45 20 15 5 85 85 50 45 0 60
Surinam Grass 85 40 90 80 100 100 85 70 100 100 100 100 80 100
Velvetleaf 100 55 100 60 100 100 50 5 100 100 100 100 50 80
Table C Compounds
250 g ai/ha 36 40 45 50 51 55 57 64 66 67 68 71 72 73
Preemergence
Bermudagrass 100 100 100 100 100 70 100 100 100 100 95 100 100 100
Cocklebur 30 60 60 80 5 100 100 75 0 20 0 90 60 20
Corn 60 95 100 100 85 0 50 100 90 95 85 100 90 85
Crabgrass, Large 100 100 100 100 100 95 100 100 100 100 100 100 100 100
Cupgrass, Woolly 65 90 90 100 85 70 100 100 75 80 75 90 95 95
Foxtail, Giant 75 100 100 100 100 0 50 100 100 95 90 100 100 90 Goosegrass 100 100 100 100 100 100 100 100 100 100 95 100 90 95
Johnsongrass 95 100 100 100 100 50 50 100 100 100 100 100 100 90
Kochia 80 100 100 100 100 100 100 - 100 100 100 100 90 90
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 35 95 100 95 20 0 70 100 100 70 100 100 60 90
Nightshade 100 100 100 100 100 - 100 100 100 100 100 100 100 100
Nutsedge, Yellow 5 20 10 45 0 100 100 30 0 0 0 0 0 0
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 20 80 85 100 70 100 100 100 100 100 80 100 90 60
Soybean 85 100 100 100 - 70 100 100 100 100 100 100 100 70
Sunflower 30 80 85 80 20 85 100 85 35 30 0 100 50 50
Surinam Grass 100 100 100 100 80 100 100 100 85 95 85 100 100 100
Velvetleaf 100 100 100 100 80 10 100 100 100 100 100 100 100 100
Table C Compounds
250 g ai/ha 74 75 76 87 89 101 102 103 .105 110 113 122 125 128
Preemergence
Bermudagrass 100 85 100 100 100 100 100 100 100 100 95 100 100 100
Cocklebur 60 0 0 90 .80 100 60 100 80 5 5 0 0 35
Corn 100 - 10 100 90 98 98 100 100 20 5 50 - 30
Crabgrass, Large 100 100 100 100 100 100 100 100 100 - 100 - 100 100
Cupgrass, Woolly 95 60 85 100 100 100 100 100 100 85 90 70 75 90
Foxtail, Giant 95 95 95 100 100 100 100 90 100 90 100 85 80 90
Goosegrass 100 80 100 100 100 100 100 100 100 80 80 100 100 100
Johnsongrass 100 30 70 100 100 100 100 100 100 100 100 100 80 100
Kochia 100 90 100 100 100 - 100 100 100 - - - - -
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 80 10 20 100 95 100 100 100 100 0 10 - 100 70
Nightshade 100 100 100 - - 100 100 100 100 100 100 100 100 100
Nutsedge, Yellow 5 0 0 25 80 100 100 100 60 0 0 0 0 0
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 100 100 75 100 100 100 100 90 100 10 80 0 70 85
Soybean 100 - 60 100 100 - - - 100 35 80 30 70 70
Sunflower 70 5 5 100 80 95 90 90 95 30 60 0 0 60
Surinam Grass 100 100 90 100 100 - - - 100 30 85 100 - 95
Velvetleaf 100 30 100 100 100 100 100 100 100 100 100 _ 100 100 Table C Comr.>ouncIs
125 g ai/ha 2 3 6 9 10 12 18 23 29 30 31 32 33 34
Preemergence
Bermudagrass 85 60 85 85 85 85 80 60 100 100 100 90 60 100
Cocklebur 0 0 5 0 10 5 5 0 80 60 45 5 0 10
Corn - 5 30 5 45 20 10 0 85 100 90 70 10 70
Crabgrass, Large 95 75 100 80 100 100 100 70 100 100 100 100 100 100
Cupgrass, Woolly 80 45 90 20 75 - 60 30 85 80 85 85 50 90
Foxtail, Giant 95 40 100 20 95 70 70 25 100 98 80 80 85 100
Goosegrass 90 50 90 80 100 80 80 0 100 100 100 85 70 95
Johnsongrass 70 65 95 60 90 90 80 30 100 100 100 100 60 85
Kochia 80 80 50 10 - - 0 0 100 70 100 50 0 50
Lambsquarters 100 100 100 85 100 100 70 50 100 100 100 100 100 100
Momingglory 20 0 5 5 60 40 40 0 100 100 70 60 0 60
Nightshade 100 85 100 60 100 100 100 70 100 100 100 100 100 100
Nutsedge, Yellow 0 0 0 0 0 0 0 0 10 50 0 5 0 0
Pigweed 100 100 100 80 100 100 90 100 100 100 100 100 100 100
Ragweed 60 50 70 10 60 30 60 0 100 100 55 50 0 50
Soybean 20 0 30 20 40 10 20 0 100 100 70 - 0 80
Sunflower 20 0 20 5 30 5 10 0 60 55 50 45 0 20
Surinam Grass 80 20 85 5 100 100 85 50 100 100 85 95 50 100
Velvetleaf 100 50 100 0 80 5 40 0 100 100 100 100 5 -
Table C Compounds
125 g ai/ha 36 40 45 50 51 55 57 64 66 67 68 71 72 73
Preemergence
Bermudagrass 100 100 100 100 100 60 100 100 100 100 95 100 100 100
Cocklebur 0 60 55 50 0 100 100 70 0 - 0 75 50 10
Corn 40 90 90 95 10 0 50 95 45 75 80 95 60 50
Crabgrass, Large 95 100 100 100 90 75 100 100 95 95 95 100 100 100
Cupgrass, Woolly 65 90 90 100 70 60 100 100 70 70 75 85 85 85
Foxtail, Giant 70 95 90 100 95 0 45 100 70 85 75 95 100 35
Goosegrass 95 100 100 100 85 90 100 100 100 95 85 100 90 80
Johnsongrass 85 100 100 100 85 20 45 100 95 100 95 100 100 85
Kochia 0 100 100 100 100 100 100 100 100 65 100 100 80 30
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 20 90 80 80 0 0 70 100 90 65 0 100 20 65
Nightshade 100 100 100 100 100 35 80 100 100 100 100 100 100 100
Nutsedge, Yellow 0 10 0 30 0 100 100 10 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 10 - 60 100 70 90 100 100 70 100 65 100 85 60
Soybean 20 100 100 100 20 60 95 - 100 95 65 100 100 50
Sunflower 0 40 75 80 10 85 100 85 15 15 0 45 50 20
Surinam Grass 85 80 90 90 50 80 100 100 40 90 80 100 100 95
Velvetleaf 20 100 100 100 50 0 45 100 100 100 100 100 100 85
Table C Compounds
125 g ai/ha 74 75 76 87 88 89 90 101 102 103 105 106 107 108
Preemergence
Bermudagrass 100 60 100 100 100 100 90 100 100 90 100 100 100 100
Cocklebur 45 0 0 75 100 40 0 60 50 70 70 85 75 75
Corn 50 5 100 95 60 10 95 95 98 95 100 100 100
Crabgrass, Large 100 85 100 100 100 100 90 100 95 100 100 100 100 100
Cupgrass, Woolly 95 ,10 80 100 100 100 60 100 100 100 100 90 100 85
Foxtail, Giant 90 75 80 100 100 100 85 100 100 90 100 100 100 100
Goosegrass 100 80 100 100 100 100 70 100 95 95 100 100 100 100
Johnsongrass 100 0 55 100 100 95 90 100 100 100 100 100 100 100
Kochia 100 90 90 100 100 100 50 100 70 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 95 100 100 100 100
Momingglory 50 5 20 100 100 80 5 100 100 100 100 100 100 100
Nightshade 100 90 100 5 100 100 100 100 100 100 100
Nutsedge, Yellow 0 0 0 20 0 40 0 100 50 100 50 20 20 20
Pigweed 100 100 100 100 100 100 85 100 100 100 100 100 100 100
Ragweed 100 60 70 100 100 100 5 95 90 90 100 100 100 100
Soybean 95 10 100 95 95 100 100 100 100
Sunflower 30 5 0 80 85 75 90 95 85 85 85 100 85 90
Surinam Grass 95 65 90 100 100 100 5 100 90 100 100
Velvetleaf 100 5 100 100 100 100 70 100 100 100 100 100 100 100
Table C Compounds
125 g ai/ha 110 113 115 120 122 125 128 168 182 185 218 219 229 230
Preemergence
Bermudagrass 90 90 100 100 95 95 100 95 100 100 100 100 80 100
Cocklebur 0 5 50 50 0 0 30 95 10 80 85 55 95 70
Corn 0 0 100 100 45 50 20 100 100 100 100 90 90 100
Crabgrass , Large - 100 100 100 - 90 100 100 100 100 100 100 100 100
Cupgrass, Woolly 85 60 100 100 70 60 80 100 100 90 100 90 100 100
Foxtail, Giant 75 80 100 100 85 50 80 100 100 100 100 100 100 100 Goosegrass 80 60 100 100 95 80 80 100 100 100 100 100 80 100
Johnsongrass 100 100 100 100 90 - 100 100 100 100 100 100 100 100
Kochia - - 100 100 - - - 100 100 100 100 85 100 100
Lambsejuarters 90 100 100 100 100 100 100 100 100 - 100 - 100 100
Momingglory ' 0 5 40 95 100 90 5 100 100 85 100 80 95 100
Nightshade 100 100 100 100 100 80 100 100 100 100 100 100 100 100
Nutsedge, Yellow 0 0 40 45 0 0 0 70 70 30 70 0 30 45
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 0 80 100 100 0 50 65 100 100 90 100 85 100 100
Soybean 30 5 100 100 10 0 50 100 100 80 100 75 80 100
Sunflower 30 40 55 80 0 0 15 100 85 85 85 70 80 -
Surinam Grass 5 85 100 100 90 10 95 100 100 100 100 100 100 100
Velvetleaf 100 100 100 100 - 100 95 100 100 100 100 100 100 100
Table C Compounds
125 g ai/ha 231 232 234 238 239 244 250 251 259
Preemergence
Bermudagrass 100 100 85 100 100 100 100 100 100
Blackgrass 80
Bromegrass, Downy 80
Cocklebur 80 10 50 85 80 0 55 90 25
Corn 100 100 90 100 100 100 95 100 100 l
Crabgrass, Large 100 100 100 100 100 100 100 100 100
Cupgrass, Woolly 100 100 80 100 100 95 95 100 100
Foxtail, Giant 100 100 80 100 100 100 100 100 100
Foxtail, Green 100
Galium 100
Goosegrass 100 100 100 100 100 100 100 100 100
Johnsongrass 100 100 100 100 100 100 100 100 100
Kochia 100 100 100 100 100 100 100 100 100
Lambsquarters 100 100 - 100 100 100 100 100 100
Momingglory 100 85 20 100 100 0 100 100 100
Nightshade 100 100 100 100 100 100 100 100 100
Nutsedge, Yellow 60 80 0 55 75 0 50 65 70
Oat, Wild 70
Pigweed 100 100 100 100 100 100 100 100 100
Ragweed 100 100 50 100 100 100 100 100 100
Russian Thistle 0
Ryegrass, Italian - - - - - - - - 85 Soybean 100 100 100 100 100 70 90 100 100
Sunflower 85 80 20 100 100 5 85 100 55
Surinam Grass 100 100 65 100 100 70 100 100 100
Velvetleaf 100 100 100 100 100 100 100 100 100
Wheat - - - - - - - - 65
Table C Compounds
62 g ai/ha 2 3 6 9 10 12 18 23 29 30 31 32 33 34
Preemergence
Bermudagrass 70 40 60 80 85 85 30 10 95 98 100 75 40 90
Cocklebur 0 0 0 0 0 0 0 0 60 50 40 0 0 5
Corn 15 0 5 0 45 20 5 0 70 75 60 25 0 25
Crabgrass, Large 80 60 80 50 100 95 90 30 85 85 100 100 60 100
Cupgrass, Woolly 50 40 70 0 70 50 10 0 70 65 70 65 40 70
Foxtail, Giant 80 5 85 10 80 50 30 0 98 80 75 50 20 60
Goosegrass 40 10 80 50 80 55 60 0 90 80 90 80 20 80
Johnsongrass 70 25 90 30 85 60 60 5 100 100 98 70 10 80
Kochia 0 50 0 10 0 0 0 0 85 5 40 0 0 20
Lambsquarters 100 70 100 70 95 100 65 40 100 100 100 100 100 100
Momingglory 10 0 5 0 20 5 20 0 80 100 70 30 0 0
Nightshade 85 85 100 0 100 80 50 0 100 100 100 100 100 100
Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Pigweed 85 90 100 10 95 90 90 80 100 100 100 100 100 100
Ragweed 5 0 5 5 40 10 10 0 90 98 40 40 0 20
Soybean 0 0 0 5 30 0 10 0 100 98 70 10 0 10
Sunflower 10 0 0 0 0 0 0 0 45 40 30 10 0 5
Surinam Grass 50 20 85 0 100 60 10 0 100 100 60 80 0 70
Velvetleaf 10 0 100 0 60 0 10 0 100 100 60 100 5 0
Table C Compounds
62 g ai/ha 36 40 45 50 51 55 57 64 66 67 68 71 72 73
Preemergence
Bermudagrass 70 100 95 100 85 45 90 100 80 95 80 100 100 100
Cocklebur 0 30 50 5 0 70 60 30 0 0 0 20 20 5
Corn 10 85 40 70 10 0 30 85 15 40 70 75 45 30
Crabgrass, Large 90 100 100 100 85 60 85 100 70 65 90 85 95 70
Cupgrass, Woolly 30 80 75 85 70 50 80 100 60 60 60 70 80 80
Foxtail, Giant 55 95 70 100 85 0 5 100 65 70 65 65 90 30
Goosegrass 70 85 100 90 70 80 100 100 70 75 70 95 90 55 Johnsongrass 60 100 95 100 85 5 40 100 80 85 90 95 100 60
Kochia 0 100 100 80 100 100 100 10 75 50 100 100 75 0
Lambsquarters 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 10 80 60 55 0 0 15 80 20 60 0 100 20 20
Nightshade 100 100 100 100 100 30 70 100 100 100 100 100 100 0
Nutsedge, Yellow 0 0 0 5 0 90 100 5 0 0 0 0 0 0
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 0 80 - 85 70 80 100 100 65 60 20 100 70 55
Soybean 0 100 100 100 0 30 90 100 0 20 - 100 70 10
Sunflower 0 - 30 55 0 10 100 65 0 0 0 0 5 0
Surinam Grass 30 65 75 90 - 70 100 100 40 90 75 100 85 80
Velvetleaf - 100 100 100 0 0 40 60 100 100 100 100 100 50
Table C Compounds
62 g ai/ha 74 75 76 87 88 89 90 101 102 103 105 106 107 108 Preemergence
Bermudagrass 100 10 90 100 100 100 70 100 95 - 100 100 100 100
Cocklebur 40 0 0 55 80 0 0 30 20 - 65 75 70 60
Corn 40 - 5 85 -80 40 0 95 95 90 80 100 100 100
Crabgrass, Large 95 10 95 100 100 95 60 100 90 95 100 95 100 100
Cupgrass, Woolly 85 5 40 100 100 90 40 70 85 90 95 80 100 80
Foxtail, Giant 80 0 60 100 100 95 30 90 90 85 100 85 100 80
Goosegrass • 100 70 80 100 100 95 40 95 95 85 100 95 100 100
Johnsongrass 100 0 50 100 100 85 40 100 100 95 100 100 100 100
Kochia 100 30 - 100 100 95 0 100 60 60 85 100 100 100
Lambsquarters 100 100 100 100 100 100 5 100 100 100 100 -
Momingglory - 0 5 100 75 75 0 85 100 100 100 100 95 100
Nightshade 100 90 100 - - - 5 100 100 100 95 100 100 100
Nutsedge, Yellow 0 0 0 15 0 25 0 60 - 50 20 5 5 5
Pigweed 100 90 100 100 100 100 10 100 100 100 100 100 100 100
Ragweed 85 10 - 100 100 100 0 90 85 85 95 100 100 100
Soybean 90 0 0 100 95 85 0 - - - 100 100 100 90
Sunflower - 5 0 55 80 70 0 90 80 80 75 85 80 85
Surinam Grass 85 0 90 100 100 100 0 - - - 100 90 100 90
Velvetleaf 100 0 100 100 100 100 40 100 100 100 100 100 100 100 Table C Compounds
62 g ai/ha 110 113 115 120 122 125 128 168 182 185 186 217 218 219
Preemergence
Bermudagrass 90 50 100 100 95 90 95 90 90 100 100 100 100 100
Cocklebur 0 0 0 40 0 0 20 80 10 70 100 15 60 55
Corn 0 0 95 95 30 0 0 100 100 95 100 - 95 70
Crabgrass, Large - 95 100 100 - 80 95 100 100 100 100 100 100 100
Cupgrass, Woolly 10 5 85 100 0 0 40 80 90 85 100 95 80 85
Foxtail, Giant 60 50 100 100 80 10 45 85 90 95 95 90 100 100
Goosegrass 75 40 100 100 90 0 0 95 100 95 90 100 100 85
Johnsongrass 90 100 100 100 90 0 100 100 100 100 100 - 100 100
Kochia - - 100 100 - - - 100 100 100 100 100 100 85
Lambsquarters - 100 100 100 100 100 80 100 100 - 100 100 100 -
Momingglory 0 0 40 60 80 90 5 95 100 60 100 60 95 40
Nightshade 100 100 100 100 100 80 100 100 100 100 100 100 100 95
Nutsedge, Yellow 0 0 40 40 0 0 0 50 50 0 45 - 30 0
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 0 0 100 100 0 50 60 100 100 85 100 100 100 80
Soybean - 0 100 95 5 0 25 100 100 80 100 - 100 60
Sunflower 5 20 55 75 0 0 10 95 80 60 100 70 75 10
Surinam Grass 5 30 85 100 90 - 95 100 100 95 100 85 100 85
Velvetleaf 80 80 100 100 - 100 5 100 100 100 100 100 100 100
Table C Compounds
62 g ai/ha 221 229 230 231 232 234 236 237 238 239 244 245 246 250
Preemergence
Bermudagrass 95 65 95 100 100 60 100 100 100 100 100 100 90 100
Cocklebur 60 80 10 30 5 0 85 60 80 65 0 60 0 5
Corn 95 45 100 100 95 85 100 100 100 100 50 95 95 45
Crabgrass, Large 100 100 100 100 100 100 100 100 90 100 100 100 95 100
Cupgrass, Woolly 80 80 100 80 85 70 80 80 90 100 80 90 90 75
Foxtail, Giant 90 100 95 90 100 80 90 85 90 100 85 95 80 100
Goosegrass 100 70 100 100 100 90 90 100 100 100 85 95 95 70
Johnsongrass 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Kochia 85 100 100 100 100 100 100 100 100 100 100 100 40 50
Lambsquarters - 100 100 100 100 - - - 100 100 100 - 100 100
Momingglory 80 95 100 100 85 0 100 100 100 100 0 95 70 100
Nightshade 85 90 100 100 100 100 90 95 100 100 100 100 90 100
Nutsedge, Yellow 5 5 40 5 40 0 10 0 40 40 0 0 30 0 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 100 90 100 100 100 0 100 100 100 100 100 100 80 95
Soybean 100 45 100 100 100 100 100 100 100 100 25 100 100
Sunflower 85 20 100 65 80 0 95 85 100 100 0 80 40 65
Surinam Grass 95 100 100 100 100 65 100 95 100 100 10 100 90 90
Velvetleaf 100 100 100 100 100 100 100 100 100 100 - 100 100 55
Table C Compounds
62 g ai/ha 251 252 253 255 259 260 262 263 264
Preemergence
Bermudagrass 100 100 100 100 100 85 95 100 90
Blackgrass 60 60
Bromegrass, Downy 70
Cocklebur 60 40 50 50 10 30 0 0 80
Corn 100 100 20 90 100 90 90 60 90
Crabgrass, Large 100 100 100 100 100 100 100 95 100
Cupgrass, Woolly 100 100 100 90 98 95 65 85
Foxtail, Giant 100 100 100 90 100 100 100 80 100
Foxtail , Green 95 85
Galium 100 70
Goosegrass 100 100 90 100 100 95 95 85 90
Johnsongrass 100 100 100 90 100 100 90 80 100
Kochia 100 100 100 100 100 100 100 100 100
Lambsquarters 100 100 100 100 100 100 100 100 100
Momingglory 100 0 0 10 60 5 0 0 80
Nightshade 100 100 100 100 100 100 100 100 100
Nutsedge, Yellow 50 50 0 0 0 0 0 0 0
Oat, Wild 0 50
Pigweed 100 100 100 100 100 100 100 100 100
Ragweed 100 100 100 100 100 80 - 100
Russian Thistle 60 0
Ryegrass, Italian 40 60
Soybean 100 90 10 75 100 40 100
Sunflower 100 50 0 75 50 40 5 60 70
Surinam Grass 100 100 80 85 100 80 85 75 100
Velvetleaf 100 100 100 100 100 100 100 100 100
Wheat 0 60 Table C Comr.>ouncIs
31 g ai/ha 2 6 10 18 57 75 88 90 101 106 107 108 115 120
Preemergence
Bermudagrass 10 30 80 10 85 0 100 10 100 85 100 85 100 100
Cocklebur 0 0 0 0 0 0 15 0 5 40 50 10 0 40
Corn - 0 0 0 0 - 65 - - 95 95 85 95 90
Crabgrass, Large 40 65 85 70 70 - 100 0 100 75 100 80 100 100
Cupgrass, Woolly 5 50 50 5 75 0 100 0 65 75 85 70 80 70
Foxtail, Giant 70 70 40 5 0 0 100 0 80 80 85 75 85 80
Goosegrass 5 60 60 0 100 70 100 0 85 85 95 85 95 90
Johnsongrass 20 40 50 0 5 0 95 0 95 100 100 100 100 100
Kochia 0 0 0 0 100 0 85 0 50 90 100 100 100 100
Lambsquarters 70 100 85 20 100 80 100 5 100 - - - 100 100
Momingglory 0 0 0 0 - 0 20 - 80 80 95 95 40 50
Nightshade 80 85 100 30 70 0 - 0 100 90 95 100 100 100
Nutsedge, Yellow 0 0 0 0 100 0 0 0 - 0 0 0 0 0
Pigweed 60 90 60 20 100 0 100 0 100 100 100 100 100 100
Ragweed 0 0 5 5 100 - 100 - 90 100 100 80 100 100
Soybean 0 0 5 5 90 0 45 - - 100 100 80 100 85
Sunflower 0 0 0 0 50 0 20 0 85 70 65 70 50 60
Surinam Grass 40 30 100 - 65 0 100 0 - 80 90 85 80 80
Velvetleaf 5 0 0 0 30 0 100 0 100 100 100 100 100 100
Table C Compounds
31 g ai/ha 122 128 168 182 185 186 217 218 219 221 229 230 231 232
Preemergence
Bermudagrass 0 90 90 90 85 85 85 85 95 90 0 95 100 100
Cocklebur 0 0 40 0 0 70 0 15 0 55 40 0 10 0
Corn 0 0 100 90 95 100 - 90 50 60 20 90 90 95
Crabgrass, Large 0 50 100 100 95 100 85 95 80 90 100 100 100 100
Cupgrass, Woolly 0 30 60 65 80 70 90 75 80 80 65 70 70 80
Foxtail, Giant 0 0 70 60 75 85 75 70 50 85 85 70 80 100
Goosegrass 80 0 85 100 80 85 90 100 65 85 10 100 100 100
Johnsongrass - 0 95 100 100 100 - 100 70 100 100 100 100 100
Kochia - - 100 100 50 85 100 100 80 65 100 100 100 100
Lambsquarters 100 - 100 100 - 100 100 100 - - 100 100 100 100
Momingglory 80 0 85 50 60 90 5 75 5 80 50 50 60 50
Nightshade 80 85 100 100 100 90 95 100 90 75 80 100 100 100
Nutsedge, Yellow 0 0 0 0 0 40 - 5 0 0 0 0 0 0 Pigweed 80 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 0 50 100 100 70 100 70 100 60 100 80 100 100 100
Soybean 0 0 80 100 50 100 - 100 45 100 100 100
Sunflower 0 10 80 80 60 95 10 70 10 70 20 55 60 45
Surinam Grass - 5 95 100 90 100 80 100 60 90 90 100 90 95
Velvetleaf 0 100 100 100 100 100 100 100 80 100 100 100 100
Table C Compounds
31 g ai/ha 234 236 237 238 239 244 245 246 250 251 252 253 255 259
Preemergence
Bermudagrass - 80 85 100 100 70 100 85 85 100 100 100 90 90
Blackgrass _ _ _ _ _ _ 45 _ 55
Bromegrass, Downy _ _ _ _ _ _ _ _ 40
Cocklebur 0 80 30 60 5 0 45 0 - 60 10 0 0 0
Corn 85 95 95 95 100 50 60 60 45 95 40 5 60 90
Crabgrass, Large 100 90 95 80 90 100 100 70 100 100 100 100 100 100
Cupgrass, Woolly 60 75 80 80 85 60 85 80 60 100 100 100 80 90
Foxtail, Giant 60 80 70 80 80 85 85 60 90 100 100 95 80 100
Foxtail, Green _ _ _ _ _ _ _ _ 80 - 75
Galium
Goosegrass 65 85 90 85 100 60 85 60 65 100 95 70 85 100
Johnsongrass 100 100 100 100 100 80 100 75 100 100 100 80 85 100
Kochia 0 90 100 100 100 100 100 5 0 100 100 90 85 100
Lambsquarters - 100 100 100 - 100 100 100 100 100 100 100
Momingglory 0 100 100 100 85 0 20 - 0 100 0 0 5 60
Nightshade 50 85 65 95 100 100 100 80 90 100 100 100 100 100
Nutsedge, Yellow 0 5 0 5 0 0 0 0 0 0 0 0 0 0
Oat, Wild _ _ _ _ _ _ _ _ 5
Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Ragweed 0 100 95 100 100 100 100 65 80 100 95 100 80 100
Russian Thistle _ _ _ _ _ _ _ _ _ _ _ 60 - 0
Ryegrass, Italian _ _ _ _ _ _ _ _ _ _ 35 - 10
Soybean 100 100 100 100 100 0 100 100 90 100 50 0 50 95
Sunflower 0 70 70 100 80 0 5 0 10 80 0 0 55 20
Surinam Grass 60 100 95 100 95 5 85 85 65 95 100 80 80 85
Velvetleaf 100 100 100 100 100 100 100 95 50 100 100 100 100 100
Wheat _ _ _ - _ _ _ _ 0 - 10 Table C Compounds Table C Compounds
31 g ai/ha 260 262 263 264 31 g ai/ha 260 262 263 264
Preemergence Preemergence
Bermudagrass 70 95 85 90 Momingglory 5 0 o ■ 75
Cocklebur 0 0 0 45 Nightshade 100 100 100 100
Corn 45 50 20 60 Nutsedge, , Yellow 0 0 0 0
Crabgrass, Large 98 90 85 100 Pigweed 100 100 100 100
Cupgrass, Woolly 70 55 65 80 Ragweed ! 80 ' 70 80 100
Foxtail, Giant 80 90 80 100 Soybean : 85 ! 80 0 100
Goosegrass 70 75 80 80 Sunflower 0 0 0 ' 70
Johnsongrass 100 80 80 80 Surinam Grass ! 80 ! B0 ' 70 ! 35
Kochia 100 100 100 65 Velvetleaf 100 100 100 100
Lambsquarters 100 100 100 100
Table C Compounds
16 g ai/ha 88 90 106 107 108 115 120 168 182 185 186 217 218 219
Preemergence
Bermudagrass 100 0 80 80 70 100 80 60 50 80 70 80 35 40
Cocklebur 0 0 5 0 0 0 0 0 0 0 50 0 5 0
Com 60 0 60 50 60 60 50 95 40 55 90 - 55 0
Crabgrass, Large 60 0 70 80 70 80 85 70 65 70 70 70 60 50
Cupgrass, Woolly 75 0 60 80 40 65 65 45 30 65 60 70 55 0
Foxtail, Giant 60 0 70 70 60 75 60 40 55 60 80 55 65 10
Goosegrass 50 0 80 85 65 85 80 80 70 65 80 80 80 40
Johnsongrass 75 0 85 90 70 100 100 60 80 85 100 - 100 60
Kochia 0 0 60 90 70 90 90 100 40 0 70 90 10 0
Lambsquarters 100 0 - - - 100 100 100 100 - 100 100 100 70
Momingglory 15 0 80 50 95 20 30 85 30 0 80 0 75 0
Nightshade - 0 70 90 100 100 100 100 100 100 70 95 100 50
Nutsedge, Yellow - 0 0 0 0 0 0 0 0 0 0 - 0 0
Pigweed 100 0 95 100 100 100 100 100 100 100 100 100 100 70
Ragweed 100 - 100 100 - 70 100 70 70 60 85 70 100 0
Soybean 40 - 80 100 - 75 70 80 10 50 100 - 95 60
Sunflower 15 - 70 40 50 50 50 70 50 30 80 0 55 0
Surinam Grass 100 0 80 65 80 10 60 70 60 60 85 50 85 20
Velvetleaf 100 0 100 100 100 100 100 100 100 100 90 70 100 0 Table C ComplouncIs
16 g ai/ha 221 229 230 231 232 234 236 237 238 239 244 245 246 250
Preemergence
Bermudagrass 65 0 70 95 95 50 80 70 90 80 25 80 50 45
Cocklebur 55 0 0 0 0 0 60 5 10 0 0 0 0 0
Corn 40 0 50 85 60 50 90 60 85 95 40 15 35 0
Crabgrass, Large 80 60 80 85 90 80 70 60 80 90 60 80 55 85
Cupgrass, Woolly 60 60 55 65 70 30 70 60 65 70 20 80 15 45
Foxtail, Giant 70 70 50 50 75 35 70 55 60 70 65 60 40 60
Goosegrass 65 0 85 80 85 65 70 70 80 80 50 75 50 40
Johnsongrass 80 100 70 80 85 80 100 80 80 90 55 85 40 70
Kochia 65 100 100 100 95 0 65 75 100 100 100 80 0 -
Lambsquarters - 100 100 100 100 - - - 100 100 100 - 100 -
Momingglory 80 0 10 60 10 0 80 100 100 - 0 0 5 0
Nightshade 50 80 100 100 100 - 70 60 70 100 100 100 70 -
Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Pigweed 85 100 100 100 100 50 100 100 100 100 100 100 90 -
Ragweed - - 85 100 100 0 - - 95 100 10 100 60 80
Soybean 60 40 100 100 100 0 80 100 100 100 0 60 0 0
Sunflower 20 10 55 60 30 0 65 60, 100 65 0 0 0 0
Surinam Grass 80 50 60 80 80 0 80 10 80 70 0 85 40 65
Velvetleaf 55 100 100 100 100 100 100 100 100 100 100 100 40 0
Table C Compounds
16 g ai/ha 251 252 253 255 259 260 262 263 264
Preemergence
Bermudagrass 85 100 85 50 80 0 30 70 60
Blackgrass - - 45 - 55 - - - -
Bromegrass, Downy - - - - 0 - - - -
Cocklebur 10 0 0 0 0 0 0 0 40
Corn 70 30 0 5 15 5 0 0 15
Crabgrass, Large 90 100 100 70 80 70 60 80 75
Cupgrass, Woolly 90 95 80 70 70 60 55 40 50
Foxtail, Giant 95 95 95 60 70 55 60 60 55
Foxtail, Green - - 65 - 70 - - - -
Galium - - 20 - 0 - - - -
Goosegrass 90 60 70 70 80 65 55 50 70
Johnsongrass 95 80 50 70 80 95 60 60 55
Kochia 95 90 50 85 100 95 95 80 60 Lambsquarters 100 100 100 100 100 100 100 100 100
Momingglory 30 0 0 5 0 0 0 0 60
Nightshade 100 100 100 100 100 100 100 100 70
Nutsedge, Yellow 0 0 0 0 0 0 0 0 0
Oat, Wild - - 0 - 0 - - - -
Pigweed 100 100 100 100 100 100 100 100 90
Ragweed 100 70 70 60 85 70 45 80 80
Russian Thistle - - 20 - 0 - - - -
Ryegrass, Italian - - 35 - 5 - - - -
Soybean 60 0 0 50 0 45 0 0 30
Sunflower 70 0 0 50 0 0 0 0 30
Surinam Grass 80 70 5 55 65 50 30 5 95
Velvetleaf 100 100 0 100 100 40 100 0 10
Wheat - - 0 - 0 - - - -
Table C Compounds
8 g ai/ha 186 217 221 236 237 245 246 252 253 255 260 262 263 264
Preemergence
Bermudagrass 60 55 60 60 50 70 0 95 80 50 0 0 50 40
Blackgrass - - - - - - - - 45 - - - - -
Cocklebur 10 0 0 5 5 0 0 0 0 0 0 0 0 0
Corn 60 10 5 70 30 5 0 0 0 - 0 0 0 0
Crabgrass, Large 60 50 50 60 55 50 30 95 80 5 60 5 5 5
Cupgrass, Woolly 40 40 45 60 60 70 0 95 80 40 50 20 40 40
Foxtail, Giant 50 55 30 50 40 30 0 80 85 45 20 20 30 30
Foxtail, Green - - - - - - - - 35 - - - - -
Galium - - - - - - - - 20 - - - - -
Goosegrass 60 60 40 50 50 35 0 60 40 50 50 50 40 50
Johnsongrass 50 60 20 90 50 60 20 60 40 50 60 40 10 50
Kochia 5 0 60 - - 80 0 0 50 60 70 30 0 40
Lambsquarters 80 100 - - - - 50 100 90 100 100 100 100 100
Momingglory 50 0 50 60 70 - 0 0 0 0 0 0 0 0
Nightshade 60 95 5 70 10 80 20 100 70 80 90 95 90 60
Nutsedge, Yellow 0 0 0 0 0 0 0 0 0 0 0 0 0 0
Oat, Wild - - - - - - - - 0 - - - - -
Pigweed 100 100 60 95 70 95 40 100 100 100 100 100 100 60
Ragweed 80 65 10 - - - - - 0 55 50 40 0 50
Russian Thistle - - - - - - - - 20 - - - - -
Ryegrass, Italian - - - - - - - - 35 - _ _ _ _ Soybean 95 5 5 - 80 60 - 0 0 0 0 0 0 0 Sunflower 70 0 5 60 50 0 0 0 0 0 0 0 0 10 Surinam Grass 70 10 40 70 0 _ 0 50 0 10 20 5 - 35 Velvetleaf 80 0 50 95 100 100 30 50 0 100 - 100 - 10 Wheat 0
TEST D Three plastic pots (ca. 16-cm diameter) per rate were partially filled with sterilized Tama silt loam soil comprising a 35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separate plantings for each of the three pots were as follows. Seeds from the U.S. of ducksalad (Heteranthera limosa), smallflower umbrella sedge (Cyperus difformis) and purple redstem (Ammannia coccinea), were planted into one 16-cm pot for each rate. Seeds from the U.S. of rice flatsedge (Cyperus iria), bearded (brdd.) sprangletop (Leptochloa fusca ssp. fascicularis), one stand of 9 or 10 water seeded rice seedlings (Oryza sativa cv. 'Japonica - M202'), and one stand of 6 transplanted rice seedlings (Oryza sativa cv. 'Japonica - M202') were planted into one 16-cm pot for each rate. Seeds from the U.S. of barnyardgrass (Echinochloa crus-galli), late watergrass (Echinochloa oryzicola), early watergrass (Echinochloa oryzoides) and junglerice (Echinochloa colona) were planted into one 16-cm pot for each rate. Plantings were sequential so that crop and weed species were at the 2.0 to 2.5-leaf stage at time of treatment. Potted plants were grown in a greenhouse with day/night temperature settings of
29.5/26.7 °C, and supplemental balanced lighting was provided to maintain a 16-hour photoperiod. Test pots were maintained in the greenhouse until test completion. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of the test compound directly to the paddy water, and then maintained at that water depth for the duration of the test. Effects of treatments on rice and weeds were visually evaluated by comparison to untreated controls after 21 days. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table D Compound Table D Compound Table D Compound
500 g ai/ha 244 250 g ai/ha 244 125 g ai/ha 244
Flood Flood Flood
Barnyardgrass 100 Barnyardgrass 95 Barnyardgrass 75
Ducksalad 95 Ducksalad 65 Ducksalad 60
Flatsedge, Rice 100 Flatsedge, Rice 90 Flatsedge, Rice > 60
Junglerice 65 Junglerice 40 Junglerice 40
Redstem 100 Redstem 100 Redstem 100
Rice, Transplanted 50 Rice, Transplanted 45 Rice, Transplanted 40 Rice, Water Seeded 85 Rice, Water Seeded 65 Rice, Water Seeded 45
Sedge, Umbrella 100 Sedge, Umbrella 80 Sedge, Umbrella 60
Sprangletop, Brdd. 100 Sprang1etop, Brdd. 100 Sprangletop, Brdd. 85
Watergrass, Early 100 Watergrass, Early 70 Watergrass, Early 60
Watergrass, Late 100 Watergrass, Late 100 Watergrass, Late 100
Table D Compound Table D Compound
64 g ai/ha 244 32 g ai/ha 244
Flood Flood
Ducksalad 60 Barnyardgrass 0
Flatsedge, Rice 30 Ducksalad 50
Junglerice 40 Flatsedge, Rice 0
Redstem 100 Junglerice 0
Rice, Transplanted 20 Redstem 20
Rice, Water Seeded 40 Rice, Transplanted 10
Sedge, Umbrella 60 Rice, Water Seeded 35
Sprangletop, Brdd. 85 Sedge, Umbrella 60
Watergrass, Late 100 Sprangletop, Brdd. 85 Watergrass, Early 0 Watergrass, Late 20
TEST E Seeds or nutlets of plant species selected from (turf) bermudagrass (Cynodon dactylon), Kentucky (KY) bluegrass (Poa pratensis), bentgrass (Agrostis palustris), hard fescue (Festuca ovina), large crabgrass (Digitaria sanguinalis), goosegrass (Eleusine indica), dallisgrass (Paspalum dilatatum), annual bluegrass (Poa annua), common chickweed (Stellaria media), dandelion (Taraxacum officinale), white clover (Trifolium repens), and yellow nutsedge (Cyperus esculentus) were planted and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crop and weed species were treated with postemergence applications of these same test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 12 to 14 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table E Compounds Table E Compounds
500 g ai/ha 29 30 250 g ai/ha 29 30
Postemergence Postemergence
Bentgrass 80 60 Bentgrass 50 20
Bermudagrass, Turf 70 30 Bermudagrass, Turf 30 0
Bluegrass 100 100 Bluegrass 100 75
Bluegrass, KY 90 80 Bluegrass, KY 20 40
Chickweed 100 100 Chickweed 100 100
Clover, White 100 100 Clover, White 100 65
Crabgrass, Large 40 20 Crabgrass, Large 20 0
Dallisgrass 35 15 Dallisgrass 20 0
Dandelion 100 90 Dandelion 100 75
Fescue, Hard 40 0 Fescue, Hard 20 0
Goosegrass 70 20 Goosegrass 20 0
Nutsedge, Yellow 0 0 Nutsedge, Yellow 0 0
Table Ξ Compounds Table E Compounds
125 g ai/ha 29 30 62 g ai/ha 29 30
Postemergence Postemergence
Bentgrass 0 0 Bentgrass 0 0
Bermudagrass , Turf 0 0 Bermudagrass, Turf 0 0
Bluegrass 90 65 Bluegrass 75 65
Bluegrass, KY 0 40 Bluegrass, KY 0 30
Chickweed 100 100 Chickweed 100 90
Clover, White 100 60 Clover, White 80 60
Crabgrass, Large 0 0 Crabgrass, Large 0 0
Dallisgrass 0 0 Dallisgrass 0 0
Dandelion 75 45 Dandelion 75 45
Fescue, Hard 0 0 Fescue, Hard 0 0
Goosegrass 0 0 Goosegrass 0 0
Nutsedge, Yell .ow 0 0 Nutsedge, Yellow 0 0
Table E Compounds Table E Compounds
31 g ai/ha 29 30 500 g ai/ha 29 30
Postemergence Preemergence
Bentgrass 0 0 Bentgrass 100 100
Bermudagrass , Turf 0 0 Bermudagrass, Turf 100 100
Bluegrass 20 25 Bluegrass 100 100
Bluegrass, KY 0 30 Bluegrass, KY 100 100 Chickweed 100 85 Chickweed 100 100
Clover, White 45 20 Clover, White 100 100
Crabgrass, Large 0 0 Crabgrass, Large 100 100
Dallisgrass 0 0 Dallisgrass 100 100
Dandelion 0 0 Dandelion 100 100
Fescue, Hard 0 0 Fescue, Hard 100 100
Goosegrass 0 0 Goosegrass 100 100
Nutsedge, Yell .ow 0 90 Nutsedge, Yellow 45 65
Table E Compounds Table E Compounds
250 g ai/ha 29 30 125 g ai/ha 29 30
Preemergence Preemergence
Bentgrass 100 100 Bentgrass 100 100
Bermudagrass , Turf 100 100 Bermudagrass, Turf 100 100
Bluegrass 100 100 Bluegrass 95 75
Bluegrass, KY 100 100 Bluegrass, KY 100 100
Chickweed 100 100 Chickweed 100 100
Clover, White 100 100 Clover, White 100 100
Crabgrass, Large 100 100 Crabgrass, Large 100 100
Dallisgrass 100 90 Dallisgrass 95 75
Dandelion 100 100 Dandelion 95 100
Fescue, Hard 100 100 Fescue, Hard 100 100
Goosegrass 100 100 Goosegrass 100 100
Nutsedge, Yellow 45 35 Nutsedge, Yellow 0 25
Table E Compounds Table E Compounds
62 g ai/ha 29 30 31 g ai/ha 29 30
Preemergence Preemergence
Bentgrass 100 100 Bentgrass 100 90
Bermudagrass, Turf 100 100 Bermudagrass, Turf 90 70
Bluegrass 65 70 Bluegrass 50 90
Bluegrass, KY 90 80 Bluegrass, KY 70 30
Chickweed 100 100 Chickweed 100 100
Clover, White 100 95 Clover, White 0 20
Crabgrass, Large 100 95 Crabgrass, Large 80 75
Dallisgrass 80 65 Dallisgrass 70 25
Dandelion 95 95 Dandelion 40 0
Fescue, Hard 90 100 Fescue, Hard 80 50
Goosegrass 95 100 Goosegrass 70 20 Nutsedge, Yellow 0 15 Nutsedge, Yellow 0 0
TESTF Seeds or nutlets of weed species selected from bermudagrass (Cynodon dactylon), Surinam grass (Brachiaria decumbens), large crabgrass (Digitaria sanguinalis), green foxtail (Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia), pitted momingglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), common ragweed (Ambrosia elatior), black mustard (Brassica nigra), guineagrass (Panicum maximum), dallisgrass (Paspalum dilatatum), barnyardgrass (Echinochloa crus-galli), southern sandbur (Cenchrus echinatus), common sowthistle (Sonchus oleraceous), prickly sida (Sida spinosa), Italian ryegrass (Lolium multiflorum), common purslane (Portulaca oleracea), broadleaf signalgrass (Brachiaria platyphylla), common groundsel (Senecio vulgaris), common chickweed (Stellaria media), tropical spiderwort (Commelina benghalensis), annual bluegrass (Poa annua), downy bromegrass (Bromus tectorum), itchgrass (Rottboellia cochinchinensis), quackgrass (Elytrigia repens), Canada horseweed (Conyza canadensis), field bindweed (Convolvulus arvensis), spanishneedles (Bidens bipinnata), common mallow (Malva sylvestris), and Russian thistle (Salsola kali) were planted into a blend of non-sterile loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these weed species were treated with early postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 1 to 10 cm (1- to 2-leaf stage) for early postemergence treatments. Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were compared to controls and visually evaluated. Weed response ratings, summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. At a different time, established container-grown grape (Vitus vinifera) vines, and olive (Olea europaea) and orange (Citrus sinensis) trees were treated with one of the test chemicals formulated in the same manner and applied to the soil surface and the lower 5 cm of the plant vines or trunks (post-directed application). Plants ranged in height from 30 to 100 cm. The applications were made using a hand sprayer delivering a volume of 990 L/ha. Treated plants and controls were maintained in a greenhouse for 28 to 56 days, after which time the treated plants were compared to controls and visually evaluated. Nine and tree crop response ratings, summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Also at a different time, seed pieces (nodes) of sugarcane (Saccharum officinarum) were planted and treated preemergence with some of the test chemicals formulated in the same manner. Each treatment was replicated three times. Treated plants and controls were maintained in a greenhouse for 14 to 28 days, after which time the treated plants were compared to controls and visually evaluated. Sugarcane response ratings, summarized in Table F, were calculated as the means of the three replicates and are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test results.
Table F Compounds
500 g ai/ha 2 29 30 31 32 40 45 57 Early Postemergence
Barnyardgrass 40 100 95 70 30 90 100 100
Bermudagrass 70 85 60 80 50 75 100 100
Bindweed, Field 30 100 95 70 70 60 95 95
Black Mustard 80 100 100 - - 100 100 100
Bluegrass 60 100 100 95 80 90 100 100
Bromegrass, Downy 30 100 100 80 80 70 95 100
Chickweed - - - - - 100
Crabgrass, Large 90 100 100 50 50 80 100 100
Dallisgrass 40 100 60 40 20 60 90 100
Foxtail, Green 80 100 100 80 70 95 95 100
Goosegrass 60 100 100 100 80 60 100 100
Groundsel - 100 100 100 95 95
Guineagrass - 100 80 75 80 70 100 100
Horseweed - 100 80 100 50 60
Itchgrass 50 100 100 20 20 50 90 100
Johnsongrass 80 100 100 90 70 100 95 100
Kochia - - 95 100 60 100
Mallow 60 100 100 100 100 100 100 100
Momingglory - 95 95 70 50 75
Nutsedge, Purple - 80 70 60 50
Prickly Sida - 100 100 100 95
Purslane - 100 100 100 20 100
Quackgrass 80 100 100 90 80 80 100 100
Ragweed 30 100 100 70 40 60 95 95
Russian Thistle - 100 - 70 30
Ryegrass, Italian 60 100 100 100 95 80 100 100
Sandbur 90 100 100 100 100 100 100 100
Signalgrass 70 100 100 75 50 90 100 100
Sowthistle - 100 100 100 100 80 - - Spanishneedles 30 100 100 80 60 70 100 100
Spiderwort 60 100 100 95 80 90 100 100
Surinam Grass 80 100 100 90 80 90 100 100
Table F Compounds
250 g ai/ha 2 10 29 30 31 32 34 40 45 50 57 64 67 72 Early Postemergence
Barnyardgrass 30 50 80 85 60 30 85 90 100 100 100 100 90 80
Bermudagrass 50 30 20 30 50 50 90 50 95 100 100 100 65 40
Bindweed, Field 30 30 100 90 40 50 85 50 75 100 95 100 100 30
Black Mustard 80 60 100 100 100 95 95 80 100 100 100 100 100 100
Bluegrass 50 80 100 100 70 60 98 50 70 95 100 95 60 70
Bromegrass, Downy 10 60 100 100 70 50 90 70 75 100 100 100 50 70
Chickweed 80 100 - - 100 - 100 100
Crabgrass, Large 75 80 100 100 40 30 100 80 100 100 100 100 90 95
Dallisgrass 30 30 50 60 20 20 90 50 80 100 100 100 95 30
Foxtail, Green 70 30 100 100 60 60 100 80 95 100 100 100 75 70
Goosegrass 50 60 100 100 70 60 100 50 90 100 95 100 95 70
Groundsel 30 70 100 100 100 95 95 95 100 100 - 100 95
Guineagrass 75 85 95 80 .50 70 100 60 100 100 100 100 98 70
Horseweed 60 30 100 75 - - 75 30* 100 90 - 70 50 30
Itchgrass 40 40 100 70 10 10 60 40 80 95 90 100 60 40
Johnsongrass 70 70 100 100 70 70 100 100 95 100 100 100 75 80
Kochia - 40 - 95 100 - 75 95 - - 100 100 85 100
Mallow 60 70 100 100 100 100 95 100 100 100 100 100 90 100
Momingglory 20 10 75 95 60 30 30 50 80 100 - 100 25 50
Nutsedge, Purple - 30 70 60 40 30 - 30 - - - - 0
Prickly Sida - 70 100 100 95 70 95 - 100 100 - 100 - 100
Purslane 80 60 100 100 70 20 - 100 100 - 100 - 100
Quackgrass 60 60 95 100 70 50 85 30 95 98 - 100 30 50
Ragweed 30 30 100 100 70 30 75 50 70 95 80 95 80 50
Russian Thistle - 30 100 - 50 30 60 - 100 100 - 100 65
Ryegrass, Italian 50 85 100 100 80 75 95 50 95 100 100 98 50 75
Sandbur 60 60 70 100 80 95 90 75 95 100 - 100 65 100
Signalgrass 50 80 100 100 75 40 80 80 95 100 100 100 - 100
Sowthistle 20 20 100 100 100 100 75 70 100 100 - 100 95 70
Spanishneedles 30 20 100 100 75 40 65 60 100 98 100 90 100 60
Spiderwort 50 80 100 100 80 80 - 90 100 - 100 - - 90
Surinam Grass 70 70 100 100 75 80 100 75 95 100 100 100 50 75 Table F Compounds
250 g ai/ha 73 74 87 88 102 Early Postemergence
Barnyardgrass 75 95 100 90 100
Bermudagrass 70 60 100 95 100
Bindweed, Field 30 60 100 90 100
Black Mustard 100 100 100 100 100
Bluegrass 60 80 100 98 100
Bromegrass, Downy 90 100 100 95 100
Chickweed 100 100 100 100 100
Crabgrass, Large 75 90
Dallisgrass 40 40 95 95 100
Foxtail, Green 75 100 100 95 100
Goosegrass 80 75 100 95 100
Groundsel 70 100 100 95 100
Guineagrass 70 80 100 100 100
Horseweed 30 40 100 100 95
Itchgrass 60 50 100 100 100
Johnsongrass 80 90 100
Kochia 100 100 -
Mallow 100 100 100 100 100
Momingglory 60 60 100 80 75
Nutsedge, Purple _ _ _ _ _
Prickly Sida 100 80 100 95 95
Purslane 95 80
Quackgrass 40 80 100 100 100
Ragweed 70 70 100 90 98
Russian Thistle _ _ _ _ _
Ryegrass, Italian 40 70 100 95 100
Sandbur 70 90
Signalgrass 80 100 - 90 95
Sowthistle 80 90 100 98 95
Spanishneedles 60 60 100 100 95
Spiderwort 90 100
Surinam Grass 80 95 100 100 100 Table F CompoundIs
125 g ai/ha 2 10 29 30 31 32 34 40 45 50 57 64 67 72
Early Postemergence
Barnyardgrass 20 30 80 30 30 20 50 50 80 70 100 95 35 60
Bermudagrass 20 30 20 10 30 30 70 40 90 90 100 75 65 40
Bindweed, Field 20 30 70 60 40 40 75 30 70 100 95 100 75 20
Black Mustard 60 50 100 80 95 50 85 - 100 100 100 98 50 80
Bluegrass 20 60 100 85 70 50 98 50 30 80 95 75 60 70
Bromegrass, Downy 10 30 100 60 70 30 80 70 50 90 100 95 30 60
Chickweed - - - - - - 100 100 100 100 100 100 100 -
Crabgrass, Large 30 50 95 100 30 20 95 50 95 100 100 100 65 95
Dallisgrass 10 20 30 10 10 10 60 30 60 - 80 65 80 20
Foxtail, Green 40 30 100 70 50 20 95 50 70 100 95 - 65 70
Goosegrass 30 50 100 85 60 10 98 40 50 100 80 90 65 40
Groundsel 30 30 - 100 95 95 85 95 100 98 100 100 50 100
Guineagrass 40 70 95 20 30 60 - 40 70 100 100 - 35 50
Horseweed 10 20 100 60 50 - 35 - 40 65 70 40 10 20
Itchgrass 40 - 70 60 10 10 60 30 70 80 80 85 40 30
Johnsongrass 20 50 100 60 50 40 90 85 95 95 100 95 65 80
Kochia - 30 - 95 100 10 50 - - - - 80 80 100
Mallow 20 60 100 100 100 80 90 90 100 - 100 95 90 100
Momingglory 10 10 70 40 20 20 - 40 60 80 50 90 - 40
Nutsedge, Purple - 10 70 50 20 20 - 20 - - - - - -
Prickly Sida 50 50 100 100 95 30 90 - - 100 100 98 100 70
Purslane 30 60 100 100 60 10 - 100 100 - 100 - - 100
Quackgrass 30 40 95 100 60 40 65 30 95 65 100 95 25 40
Ragweed 20 20 100 75 40 30 65 40 70 90 70 95 10 30
Russian Thistle 10 30 30 - 20 10 - - - 100 - 90 - -
Ryegrass, Italian 20 60 100 90 70 60 50 40 60 95 80 98 50 75
Sandbur 60 10 - 30 80 40 90 30 95 70 100 50 - 100
Signalgrass 30 50 100 95 30 40 80 80 70 95 100 98 65 80
Sowthistle - 10 - 60 80 70 40 30 100 90 100 100 20 60
Spanishneedles 20 20 100 100 60 30 15 60 60 90 70 75 50 40
Spiderwort 30 50 100 100 70 70 - 40 80 - 100 - - 90
Surinam Grass 40 60 100 60 70 20 90 60 80 98 95 98 40 75 Table F Compounds
125 g ai/ha 73 74 87 88 102
Early Postemergence
Barnyardgrass 60 50 80 80 100
Bermudagrass 40 40 100 95 100
Bindweed, Field 20 60 100 90 100
Black Mustard 70 100 100 100 100
Bluegrass 25 60 100 98 95
Bromegrass, Downy 70 80 100 75 98
Chickweed 100
Crabgrass, Large 70 70
Dallisgrass 10 30 95 95 100
Foxtail, Green 70 70 100 90 100
Goosegrass 30 30 100 95 98
Groundsel 40 90 100 95 100
Guineagrass 40 60 100 95 100
Horseweed 10 30 100 100 95
Itchgrass 30 30 95 98 98
Johnsongrass 70 80 100
Kochia 100 85
Mallow 100 100 100 100 100
Momingglory 40 50 65 40 75
Nutsedge, Purple 10
Prickly Sida - - 100 95 95
Purslane 95 70
Quackgrass 30 70 100 98 100
Ragweed 40 50 100 85 95
Russian Thistle _ _ _ _ _
Ryegrass, Italian 40 30 100 85 95
Sandbur 70 75
Signalgrass 75 85
Sowthistle 30 80 100 98 90
Spanishneedles 40 60 100 90 80
Spiderwort 90 95
Surinam Grass 60 - 90 80 95 Table F Compιound.s
62 g ai/ha 2 10 29 30 31 32 34 40 45 50 57 64 67 72
Early Postemergence
Barnyardgrass 10 10 40 30 10 20 20 20 20 30 50 85 0 20
Bermudagrass 10 10 10 10 10 10 25 20 50 85 80 75 20 30
Bindweed, Field 10 10 70 50 20 20 - 30 30 - 95 100 - 20
Black Mustard 30 10 100 60 60 30 65 60 100 90 100 98 10 60
Bluegrass 10 30 90 70 30 10 50 30 30 65 70 75 50 70
Bromegrass, Downy 10 20 80 60 10 10 50 10 20 50 70 90 20 40
Chickweed - - - - - - 100 100 - 100 100 100 100 -
Crabgrass, Large 30 20 50 60 10 10 90 40 70 100 95 100 65 20
Dallisgrass 10 0 20 0 10 10 - 10 30 100 40 - 50 20
Foxtail, Green 20 10 60 20 10 20 70 40 50 85 95 98 65 70
Goosegrass 10 30 50 40 20 10 90 20 40 100 70 90 65 30
Groundsel 20 30 - 95 95 70 40 95 10 90 100 90 - 100
Guineagrass 40 20 60 10 20 20 100 30 20 95 75 100 - 20
Horseweed 0 20 100 30 - 0 35 10 - 65 30 40 10 10
Itchgrass 10 10 60 20 0 0 20 10 70 40 60 85 20 10
Johnsongrass 10 20 95 50 20 10 50 70 40 - 85 90 - 80
Kochia - 20 - 85 50 - 20 95 - - - - 65 10
Mallow 10 60 100 100 100 50 90 90 - 100 80 80 80 100
Momingglory 10 10 20 10 20 10 20 30 - - 40 - 10 10
Nutsedge, Purple - 0 70 50 10 10 - 10 - - - - 0 -
Prickly Sida 50 30 100 100 70 30 75 80 - 100 - 98 100 10
Purslane - 60 100 100 60 10 - 95 95 - 100 - - 70
Quackgrass 30 10 95 80 10 10 35 20 20 65 75 80 25 40
Ragweed 10 20 80 75 20 10 50 40 70 85 70 80 - 20
Russian Thistle - 20 10 - 10 0 50 - - - 95 - 60 -
Ryegrass, Italian 0 30 70 60 30 40 - 30 60 80 75 90 35 75
Sandbur 30 0 20 10 20 20 30 10 60 - 85 - 35 10
Signalgrass 20 20 95 95 20 10 30 50 50 75 70 98 20 50
Sowthistle 0 10 - 50 20 70 10 30 40 75 30 85 10 30
Spanishneedles 10 10 95 95 30 20 10 50 60 90 70 75 50 20
Spiderwort 10 30 100 100 60 20 - 10 70 - 85 - 100 -
Surinam Grass 10 30 100 60 70 20 90 30 50 95 70 98 _ 40 Table F Compounds
62 g ai/ha 73 74 87 88 102 Early Postemergence
Barnyardgrass 60 50 80 80 95
Bermudagrass 20 40 98 95 95
Bindweed, Field 10 20 - 65
Black Mustard 20 100 100 100 95
Bluegrass 25 60 85 60 70
Bromegrass, Downy 40 50 65 35 70
Chickweed 90 - 100 100 100
Crabgrass, Large 30 30 100 100
Dallisgrass 10 20 90 75 90
Foxtail, Green 70 40 100 80 95
Goosegrass 10 20 100 65 98
Groundsel 30 90 100 90 100
Guineagrass 30 50 100 75 80
Horseweed 10 10 80 90 80
Itchgrass 20 10 80 90 95
Johnsongrass 40 60 80 50 -
Kochia 10 80
Mallow 90 60 100 100 100
Momingglory 30 20 20 30 60
Nutsedge, Purple 10
Prickly Sida 95 80 100 90 95
Purslane 95 30
Quackgrass 30 10 100 75 80
Ragweed 20 40 95 70 90
Russian Thistle - 100 _ _ _
Ryegrass, Italian 20 30 75 - 50
Sandbur 70 40
Signalgrass 75 60 - 75
Sowthistle 20 60 80 75 75
Spanishneedles 20 50 65 60 75
Spiderwort 30 20 100
Surinam Grass 40 60 90 80 95 Table F Compounds
31 g ai/ha 10 34 50 64 67 87 88 102
Early Postemergence
Barnyardgrass 0 20 30 50 0 80 80 95
Bermudagrass 0 20 75 65 20 75 75 80
Bindweed, Field 10 35 - - 35 100 65 100
Black Mustard 10 65 75 90 10 95 100 95
Bluegrass 10 35 65 40 25 75 30 20
Bromegrass, Downy 10 35 30 65 20 30 10 20
Chickweed - 100 - - 100 100 100 100
Crabgrass, Large 10 75 100 98 50 100 100 90
Dallisgrass 0 20 40 - 40 90 75 90
Foxtail, Green 0 35 30 90 10 100 80 75
Goosegrass 20 70 100 80 0 90 50 75
Groundsel 20 20 75 90 10 100 90 80
Guineagrass 0 30 80 95 - 90 75 80
Horseweed 0 20 0 10 10 75 - 70
Itchgrass 0 20 25 35 20 80 20 65
Johnsongrass 10 50 - 70 35 80 35 65
Kochia 10 0 - - 0 - - -
Mallow 60 75 90 75 40 90 80 80
Momingglory 10 10 50 - 0 - - 40
Nutsedge, Purple 0
Prickly Sida 20 75 95 90 80 100 50 80
Purslane 20 0
Quackgrass 0 35 50 65 0 50 75 70
Ragweed 10 20 75 80 10 90 65 65
Russian Thistle 0 0 - - 40 25 - -
Ryegrass, Italian 10 30 70 90 20 70 75 20
Sandbur 0 0 30 - - - - -
Signalgrass 0 0 - 50 20 85 70 80
Sowthistle 0 0 35 75 10 80 50 50
Spanishneedles 0 0 35 40 10' 50 40 50
Spiderwort 0 - - - - 100 95 -
Surinam Grass 10 35 75 98 _ 65 80 65 Table F Compound 1500 g ai/ha 236 Post-Directed
Grape 75
Olive 0
Orange 20
Table F Compounds
500 g ai/ha 2 29 30 31 32 40 45 57 66 68 71
Preemergence
Barnyardgrass 40 100 100 100 100 95 85 95 70 70 95
Bermudagrass 30 100 100 100 100 100 95 100 95 85 100
Bindweed, Field 10 100 95 70 80 60 60 70 60 40 70
Black Mustard 70 100 100 95 100 90 100 100 80 85 100
Bluegrass 50 100 100 100 100 100 95 100 100 95 95
Bromegrass, Downy 20 100 95 100 95 95 60 80 60 60 90
Chickweed 60 100 100 - - 100 100 100 - - -
Crabgrass, Large 95 100 100 100 100 95 100 100 100 85 100
Dallisgrass 70 100 100 95 100 70 85 100 40 30 80
Foxtail, Green 60 100 100 100 95 95 100 100 50 75 75
Goosegrass 80 100 100 100 100 90 95 100 95 75 100
Groundsel 100 100 95 100 100 95 95 100 100 90 100
Guineagrass 95 100 100 100 100 100 100 100 100 95 100
Horseweed 50 95 100 100 90 95 100 100 100 90 95
Itchgrass 40 100 100 95 75 75 80 95 60 80 80
Johnsongrass 40 100 100 95 100 95 80 100 60 75 90
Kochia 95 90 95 95 50 100 100 90 100 80 70
Mallow 85 100 100 100 100 100 95 100 100 100 100
Momingglory - 70 70 50 50 50 80 70 20 20 40
Nutsedge, Purple 10 75 100 100 70 100 100 70 10 100 100
Prickly Sida 70 100 100 100 100 100 100 100 100 85 100
Purslane 100 100 100 95 20 100 100 100 95 70 100
Quackgrass 95 100 100 100 95 75 95 95 60 90 95
Ragweed 50 95 100 85 75 95 70 75 70 30 70
Russian Thistle 100 80 90 95 100 100 85 70 - 100 100
Ryegrass, Italian 80 100 100 100 95 70 100 95 85 60 95
Sandbur 75 85 95 90 100 80 80 100 60 85 80
Signalgrass 70 100 95 80 85 70 95 - 60 60 70
Sowthistle 40 100 100 100 95 95 100 100 100 90 100 Spanishneedles 50 100 95 75 80 70 85 95 30 10 70
Spiderwort 100 100 100 100 100 100 100 100 100 75 100
Surinam Grass 80 100 100 95 100 85 50 95 70 85 70
Table F Compounds
250 g ai/ha 2 10 29 30 31 32 34 40 45 50 57 64 66 67
Preemergence
Barnyardgrass 20 70 100 100 95 80 98 95 40 100 95 95 40 80
Bermudagrass 10 95 100 100 100 95 100 100 90 100 100 100 95 100
Bindweed, Field 0 60 100 95 70 70 30 50 30 80 70 95 50 75
Black Mustard 70 60 100 100 90 85 75 85 40 - 100 100 60 60
Bluegrass 20 80 100 100 100 85 85 95 75 98 100 95 95 0
Bromegrass, Downy 20 60 100 95 95 80 60 80 30 95 60 65 60 20
Chickweed 30 100 100 100 - - 100 95 95 100 95 100 ' - 100
Crabgrass, Large 85 95 100 100 100 100 98 90 95 100 100 100 100 100
Dallisgrass 50 60 95 95 85 75 - 70 70 100 95 95 30 90
Foxtail, Green 60 90 100 100 100 95 70 95 60 100 100 100 30 20
Goosegrass 60 100 100 100 100 95 90 80 85 95 95 100 80 50
Groundsel •95 70 100 95 100 100 100 95 95 100 95 100 10.0 50
Guineagrass 80 90 100 100 100 100 100 100 100 100 100 100 95 90
Horseweed 30 40 95 90 100 75 - 95 95 - 100 - 85 -
Itchgrass 30 75 100 100 85 75 98 60 80 100 50 - 50 -
Johnsongrass 30 70 100 95 95 75 100 85 40 - 100 98 30 95
Kochia - 100 85 50 95 50 - 100 100 - 90 - 100 -
Mallow 70 85 95 100 95 95 100 100 95 100 100 100 100 100
Momingglory 75 30 60 60 30 50 100 40 40 100 60 - 20 100
Nutsedge, Purple - 30 - 50 - 70 - 100 100 95 70 - - -
Prickly Sida 30 50 100 100 95 100 100 100 95 90 95 95 100 100
Purslane 100 80 100 95 60 10 - 100 100 - 50 - 95 -
Quackgrass 70 80 100 100 95 80 50 70 80 80 95 100 30 50
Ragweed 30 60 95 100 80 60 50 70 60 65 70 80 30 20
Russian Thistle 70 10 80 60 95 75 0 50 50 40 - - 95 -
Ryegrass, Italian 60 90 100 95 95 80 60 60 95 95 95 100 60 40
Sandbur 50 60 85 95 90 95 80 80 10 98 100 65 30 -
Signalgrass 70 60 100 95 75 70 90 60 80 95 100 98 60 50
Sowthistle 20 70 100 100 100 95 100 95 100 100 100 90 95 -
Spanishneedles 50 10 100 95 60 70 40 60 60 100 95 95 30 60
Spiderwort 70 95 100 100 95 100 98 80 80 100 95 90 70 90
Surinam Grass 80 100 100 100 95 100 80 70 20 98 70 75 _ 0 Table F Compounds
250 g ai/ha 68 71 72 73 74 87 88 102
Preemergence
Barnyardgrass 60 95 95 95 80 50 40 80
Bermudagrass 70 100 100 100 100 100 100 100
Bindweed, Field 20 - 70 60 80 90 35 90
Black Mustard 85 100 100 80 100 - 95 -
Bluegrass 90 95 95 90 95 95 65 95
Bromegrass, Downy 30 90 60 75 100 75 65 80
Chickweed - - 95 100 100 - 100 100
Crabgrass, Large 85 100 95 90 95 100 100 100
Dallisgrass 20 60 85 80 40 90 - 98
Foxtail , Green 75 75 100 95 100 95 40 100
Goosegrass 70 95 95 95 95 100 98 100
Groundsel 80 100 80 90 100 100 100 -
Guineagrass 85 100 95 95 95 95 95 100
Horseweed 50 80 100 95 100 100. 100 100
Itchgrass 75 80 90 85 85 90 50 90
Johnsongrass 75 90 80 100 95 - 75 90
Kochia 70 - 100 20 100 - 80 -
Mallow 100 100 100 100 95 - - -
Momingglory 20 30 50 20 70 65 0 35
Nutsedge, Purple 100 100 100 60 30 - - -
Prickly Sida 80 100 100 95 100 - 100 100
Purslane 60 95 100 100 100 - - -
Quackgrass 90 70 85 100 60 98 85 80
Ragweed 20 70 70 60 70 70 75 80
Russian Thistle 100 10 30 20 90 35 0 -
Ryegrass, Italian 60 85 80 60 70 98 95 98
Sandbur 60 80 75 90 85 - - 90
Signalgrass 50 60 70 70 70 80 90 98
Sowthistle 90 100 100 100 100 - - -
Spanishneedles 10 40 60 70 80 90 65 90
Spiderwort 75 100 100 100 100 - - -
Surinam Grass 80 _ 95 70 75 40 50 _ Table F ComplouncIs
125 g ai/ha 2 10 29 30 31 32 34 40 45 50 57 64 66 67
Preemergence
Barnyardgrass 10 60 100 100 50 50 80 75 30 - 80 - 10 65
Bermudagrass - 30 100 100 95 90 98 100 90 100 95 100 80 100
Bindweed, Field 0 20 100 70 60 60 30 30 10 70 50 50 50 0
Black Mustard 60 50 100 100 80 80 70 80 - 100 100 70 60 35
Bluegrass 10 50 100 100 90 80 70 90 50 80 95 95 80 0
Bromegrass, Downy 20 60 100 40 50 70 25 - 30 - 30 50 30 20
Chickweed 20 100 100 100 - - 100 95 95 100 90 100 - 100
Crabgrass, Large 60 50 100 100 95 100 50 75 80 100 100 100 30 50
Dallisgrass 10 30 95 80 60 50 - 20 70 100 90 70 0 0
Foxtail, Green 40 50 100 100 80 70 70 80 40 - 100 80 10 20
Goosegrass 20 40 100 100 95 80 50 80 80 85 90 90 50 20
Groundsel 90 20 95 95 100 95 95 95 95 100 95 100 100 0
Guineagrass 30 60 95 95 95 100 95 95 85 100 100 - 95 90
Horseweed 20 40 95 - 100 70 - 95 70 - 100 - 85 -
Itchgrass 10 40 100 95 30 50 98 60 60 - 30 95 30 95
Johnsongrass 10 60 100 50 80 75 - 80 30 95 80 98 30 35
Kochia 60 10 40 20 95 - 0 100 40 0 75 - 30 -
Mallow 40 70 95 100 95 95 95 100 95 100 95 - 100 85
Morningglory 60 10 30 30 10 20 20 20 20 40 30 10 10 0
Nutsedge, Purple - 10 60 50 40 30 - 100 10 35 - 50 10 -
Prickly Sida - 20 85 85 60 80 90 100 95 - 95 90 80 100
Purslane 100 20 80 95 50 10 - 100 100 - 10 - 70 -
Quackgrass 30 30 95 100 80 40 0 70 80 50 95 80 30 0
Ragweed 30 30 85 70 75 40 50 40 40 65 60 70 10 20
Russian Thistle - 10 80 30 95 10 - 30 10 - 60 0 95 -
Ryegrass, Italian 10 60 100 85 70 50 - 40 40 40 80 65 20 20
Sandbur 50 30 80 60 70 75 65 60 0 95 100 65 30 0
Signalgrass 40 40 90 90 70 60 70 40 30 95 95 65 10 10
Sowthistle 20 10 95 100 95 75 100 95 100 50 100 - 20 -
Spanishneedles 30 10 85 70 30 40 30 30 30 95 60 75 0 -
Spiderwort 70 95 100 100 95 90 - 80 80 95 95 80 20 20
Surinam Grass 40 60 100 100 95 80 40 70 20 _ 60 65 50 0 Table F Compounds
125 g ai/ha 68 71 72 73 74 87 88 102
Preemergence
Barnyardgrass 30 60 50 70 60 50 - 75
Bermudagrass 60 85 95 100 100 100 100 100
Bindweed, Field 10 10 60 50 60 - 35 65
Black Mustard 50 50 85 80 85 - - -
Bluegrass 85 85 90 90 90 ' 95 65 95
Bromegrass, Downy 20 50 50 70 50 35 40 35
Chickweed - - 95 95 100 - 100 100
Crabgrass, Large 60 85 95 90 90 100 100 100
Dallisgrass 10 10 20 30 20 90 90 98
Foxtail, Green - 40 90 90 90 65 40 90
Goosegrass 30 85 95 85 95 98 95 100
Groundsel 80 100 70 90 70 100 75 -
Guineagrass 80 95 95 80 95 95 95 95
Horseweed 50 80 95 95 95 100 100 100
Itchgrass 40 65 90 75 80 90 - 90
Johnsongrass 50 80 80 80 80 - - -
Kochia 20 10 100 - 100 - 20 -
Mallow 100 100 85 100 80 - - -
Momingglory 10 20 50 10 20 - 0 25
Nutsedge, Purple 100 100 100 - - - - -
Prickly Sida 80 100 80 95 100 - 100 100
Purslane 10 80 100 100 80 - - -
Quackgrass 30 30 75 60 20 90 80 -
Ragweed 10 30 60 60 70 65 65 80
Russian Thistle 100 - - - 90 - 0 -
Ryegrass, Italian 30 85 60 10 30 98 90 98
Sandbur 20 80 60 50 70 - - 90
Signalgrass 30 30 60 30 50 - 75 98
Sowthistle 80 95 100 95 100 - - -
Spanishneedles 10 10 30 20 70 65 65 90
Spiderwort 10 80 100 95 95 - - -
Surinam Grass 60 40 95 70 70 40 50 95 Table F Compιound.s
62 g ai/ha 2 .10 29 30 31 32 34 40 45 50 57 64 66 67
Preemergence
Barnyardgrass 0 20 95 70 50 20 65 20 20 100 75 95 0 -
Bermudagrass 10 20 95 100 85 75 98 90 75 98 95 100 10 98
Bindweed, Field 0 0 60 20 10 20 30 10 - 0 10 0 0 0
Black Mustard - 20 100 100 60 40 65 60 10 100 30 50 10 0
Bluegrass 0 50 95 70 80 70 20 70 20 30 70 40 30 0
Bromegrass, Downy 0 30 30 10 40 10 0 10 10 80 30 20 0 10
Chickweed 10 10 100 100 - - 100 - 95 100 60 100 - 100
Crabgrass, Large 20 40 95 95 95 70 - 60 75 75 85 95 0 20
Dallisgrass 0 10 60 20 50 10 20 10 10 - 80 50 0 0
Foxtail, Green 0 30 95 95 60 60 20 30 10 85 75 40 0 20
Goosegrass 0 10 100 95 70 70 35 20 30 40 60 70 10 0
Groundsel 10 10 90 95 100 95 95 95 70 100 95 100 95 0
Guineagrass 0 10 85 80 90 90 90 70 70 100 80 100 60 -
Horseweed 20 - - 50 40 70 - 95 50 - 95 - 40 -
Itchgrass 0 10 70 70 30 30 65 20 10 95 20 - 30 85
Johnsongrass - 30 50 30 70 20 30 50 10 - 70 - 10 0
Kochia 60 0 40 10 95 - - - 10 0 0 - 0 0
Mallow 20 50 95 100 95 80 90 75 95 100 90 100 40 -
Momingglory 10 0 20 20 10 10 0 0 0 30 10 0 0 0
Nutsedge, Purple - 0 - 20 20 - 0 75 10 - - - 0 -
Prickly Sida 20 10 80 40 10 80 80 95 60 85 70 70 80 100
Purslane - 10 - 75 50 0 - 30 - - - - 0 -
Quackgrass 30 30 50 10 70 20 0 50 30 20 60 65 10 0
Ragweed 0 20 75 60 60 30 30 10 10 20 30 70 0 0
Russian Thistle 20 10 10 10 90 - - 30 0 0 40 0 10 -
Ryegrass, Italian 0 50 80 40 50 30 60 10 30 30 70 - 10 0
Sandbur 10 0 40 40 60 40 0 50 0 - 20 - 0 -
Signalgrass 0 30 70 60 70 30 50 20 30 80 80 - 0 10
Sowthistle 0 0 95 100 40 75 0 90 10 - 90 90 20 -
Spanishneedles 30 0 50 40 20 20 0 10 10 35 20 65 0 0
Spiderwort 70 40 75 90 50 40 - 10 - 90 10 65 0 20
Surinam Grass 0 60 85 70 70 60 20 10 0 80 60 65 10 0 Table F CompouncIs
62 g ai/ha 68 71 72 73 74 87 88 102
Preemergence
Barnyardgrass 10 20 20 30 10 20 0 10
Bermudagrass 20 85 95 95 80 100 100 100
Bindweed, Field 0 0 10 50 30 0 0 0
Black Mustard 10 10 40 40 80 - 0 -
Bluegrass 20 60 80 70 40 20 40 35
Bromegrass, Downy 10 20 10 0 20 20 40 0
Chickweed - - - 95 - 35 100 100
Crabgrass, Large 30 60 80 70 60 95 100 100
Dallisgrass 0 10 10 10 0 75 75 65
Foxtail, Green 20 20 50 50 30 35 20 20
Goosegrass 10 60 60 70 40 90 20 98
Groundsel - 95 70 50 60 100 - 0
Guineagrass 20 75 90 50 70 35 40 65
Horseweed 0 60 - 60 95 100 100 100
Itchgrass 20 60 60 20 20 0 - 35
Johnsongrass 30 30 50 50 70 - 25 -
Kochia 10 10 - 20 80 0 0 -
Mallow 75 80 80 80 80 - - -
Momingglory 10 10 0 0 0 0 0 0
Nutsedge, Purple 85 100 30 - - - - -
Prickly Sida 0 100 20 - 100 - 0 100
Purslane 0 10 - 10 0 - - -
Quackgrass 0 10 10 40 0 90 20 40
Ragweed 0 30 40 40 40 65 65 30
Russian Thistle 0 0 - - 10 - 0 -
Ryegrass, Italian 0 60 60 0 10 90 20 35
Sandbur 10 20 20 10 30 - 0 -
Signalgrass 20 20 20 10 10 75 65 75
Sowthistle 0 40 70 95 100 - - -
Spanishneedles 0 10 20 10 40 20 20 65
Spiderwort 0 60 30 20 20 - - -
Surinam Grass 30 40 50 10 30 0 0 35 Table F Compounds
31 g ai/ha 10 34 50 64 67 87 88 102
Preemergence
Barnyardgrass 0 50 60 70 65 - - 0
Bermudagrass 0 80 95 75 80 100 100 100
Bindweed, Field 0 20 0 0 0 0 0 0
Black Mustard 0 50 65 0 0 - - -
Bluegrass 0 0 20 30 0 20 20 30
Bromegrass, Downy 10 0 20 0 0 0 20 0
Chickweed 0 50 100 90 90 - 90 100
Crabgrass, Large 10 20 50 80 0 90 90 95
Dallisgrass 0 0 - 20 0 40 65 40
Foxtail, Green 10 20 20 35 20 0 0 10
Goosegrass 0 0 40 65 0 65 20 90
Groundsel 0 95 100 65 0 0 0 0
Guineagrass 10 65 100 70 50 - 0 0
Horseweed - - - - - 80 65 75
Itchgrass 0 65 95 30 50 - - -
Johnsongrass 10 0 75 60 - - - -
Kochia 0 - 0 - - - - -
Mallow 10 60 90 80 80 - - -
Momingglory 0 0 0 0 0 0 0 0
Nutsedge, Purple 0 - - - 0 - - -
Prickly Sida 0 40 75 50 90 - - 25
Purslane 0 - - 0 - - - -
Quackgrass 0 0 0 20 0 35 10 -
Ragweed 10 10 10 70 0 25 20 0
Russian Thistle 0 - - 0 - 0 - -
Ryegrass, Italian 10 0 0 0 0 30 0 35
Sandbur 0 0 0 - 0 - 0 20
Signalgrass 10 0 0 0 0 - 65 30
Sowthistle 0 0 0 0 - - 0 -
Spanishneedles 0 0 20 30 0 0 0 0
Spiderwort - 0 0 0 0 - - -
Surinam Grass 0 0 40 30 0 0 0 35 Table F Compounds Table F Compounds 500 g ai/ha 186 236 125 g ai/ha 186 236 237 238 Preemergence Preemergence Sugarcane 95 83 Sugarcane 77 80 50 70
Table F Compounds Table F Compounds 375 g ai/ha 186 236 237 238 62 g ai/ha 186 236 238 Preemergence Preemergence Sugarcane 88 77 83 78 Sugarcane 45 47 60
Table F Compounds 250 g ai/ha 186 236 237 238 Preemergence Sugarcane 87 80 58 83
TESTG Plants selected from weed species in Test F were planted into a blend of sterile loam soil and sand and treated preemergence with some of the test chemicals formulated in a non- phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from weed species in Test F were treated with either early postemergence or postemergence applications of some of the test chemicals formulated in the same manner. Plants ranged in height from 1 to 10 cm (1- to 2-leaf stage) for early postemergence treatments or 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for 14 to 21 days, after which time all species were compared to controls and visually evaluated. Weed response ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
Table G Compounds
250 g ai/ha 186 218 236 237 238 239
Early Postemergence
Barnyardgra s s 100 100 100 100 100 100 Bermudagrass 90 75 100 90 80 98 Bindweed, Field - 100 - - 100 Black Mustard - 100 - - 100 Bluegrass _ 100 - - 100
Bromegrass , Downy 100 100 100 100 100 100 Chickweed - - 100
Crabgrass , Large 100 100 100 100 100 100
Dallisgrass - - 100 - - 100 Foxtail, Green 100 100 100 100 100 100
Goosegrass - - 100 - - 100
Groundsel 100 100 100 100 100 -
Guineagrass - - 100 - - -
Itchgrass 100 100 100 100 100 100
Johnsongrass 100 100 100 100 100 100
Kochia 100 95 100 100 100 100
Mallow 100 100 100 100 100 100
Momingglory 98 100 100 100 100 100
Nutsedge, Purple 90 90 98 90 90 -
Prickly Sida - - 100 - - 100
Purslane 98 80 100 100 100 100
Quackgrass 100 100 100 100 100 -
Ragweed - - 100 - - 100
Russian Thistle 100 100 100 100 100 100
Ryegrass, Italian - - 100 - - 100
Sandbur 75 80 100 90 90 100
Signalgrass 100 100 100 100 100 100
Sowthistle 100 100 100 100 100 100
Spanishneedles 100 100 100 100 100 100
Spiderwort - - 100 - - 100
Surinam Grass 100 100 100 100 100 100
Table G Compounds
125 g ai/ha 186 218 236 237 238 239
Early Postemergence
Barnyardgrass 100 75 100 80 100 90
Bermudagrass 90 50 75 75 80 70
Bindweed, Field - - 100 - - 100
Black Mustard - - 100 - - 100
Bluegrass - - 100 - - 100
Bromegrass, Downy 100 100 100 100 100 95
Crabgrass, Large 100 100 100 100 100 100
Dallisgrass - - 100 - - 100
Foxtail, Green 100 100 100 100 100 100
Goosegrass - - 100 - - 95
Groundsel 100 100 100 100 100 -
Guineagrass - - 100 - - 98
Itchgrass 95 95 100 100 100 95 Johnsongrass 100 100 100 100 100 100
Kochia 100 95 100 100 100 100
Mallow 100 100 100 100 100 100
Momingglory 90 80 100 - 100 100
Nutsedge, Purple 90 70 95 50 80 65
Prickly Sida - - 100 - - 100
Purslane 95 80 100 100 100 100
Quackgrass 98 98 100 100 100 98
Ragweed - - 100 - - 100
Russian Thistle 100 95 100 100 100 100
Ryegrass, Italian - - 100 - - 100
Sandbur 75 80 85 40 80 65
Signalgrass 100 95 100 95 100 95
Sowthistle 100 100 100 100 100 100
Spanishneedles 100 100 100 100 100 100
Spiderwort - - 100 - - 100
Surinam Grass 98 100 100 95 100 80
Table G Compounds
62 g ai/ha 186 218 236 237 238 239 Early Postemergence
Barnyardgrass 75 30 80 40 100 60
Bermudagrass 40 35 60 60 75 60
Bindweed, Field - - 100 - - 100
Black Mustard - - 100 - - 80
Bluegrass - - 100 - - 98
Bromegrass, Downy 100 100 100 100 100 95
Chickweed - - 100 - - 100
Crabgrass, Large 95 80 100 95 95 95
Dallisgrass - - 80 - - 65
Foxtail, Green 100 100 100 100 98 100
Goosegrass - - 95 - - 90
Groundsel 100 100 100 100 - 100
Guineagrass - - 95 - - 75
Horseweed - - 100
Itchgrass 75 50 98 90 90 85
Johnsongrass 100 100 100 100 100 100
Kochia 90 80 100 98 85 100
Mallow 100 100 100 100 100 100 Momingglory 75 75 100 100 100 100
Nutsedge, Purple 60 40 75 40 50 50
Prickly Sida - - 100 - - 100
Purslane 80 60 95 100 95 100
Quackgrass 95 98 98 90 100 70
Ragweed - - 100 - - 100
Russian Thistle 100 75 100 100 95 100
Ryegrass, Italian - - 100 - - 85
Sandbur 40 60 75 35 40 40
Signalgrass 75 90 95 80 95 90
Sowthistle 100 100 100 100 100 100
Spanishneedles 100 100 100 100 100 100
Spiderwort - - 100 - - 100
Surinam Grass 90 80 100 90 95 70
Table G Compounds
31 g ai/ha 186 218 236 237 238 239
Early Postemergence
Barnyardgrass 75 30 50 30 80 50
Bermudagrass 40 35 50 30 75 50
Bindweed, Field - - 100 - - 90
Black Mustard - - 95 - - 60
Bluegrass - - 100 - - 80
Bromegrass, Downy 100 60 98 100 100 90
Chickweed - - 100 - - 100
Crabgrass, Large 80 80 98 70 80 80
Dallisgrass - - 60 - - 60
Foxtail, Green 80 50 100 80 90 80
Goosegrass - - 80 - - 75
Groundsel 100 100 100 100 100 100
Guineagrass - - 65 - - 65
Horseweed - - 100 - - 100
Itchgrass 50 35 90 30 70 80
Johnsongrass 100 90 100 90 100 98
Kochia 75 75 90 95 75 90
Mallow 100 100 100 100 100 100
Momingglory 50 75 90 100 100 100
Nutsedge, Purple 50 10 50 10 35 40
Prickly Sida - - 98 - - 80 Purslane 80 60 - 80 80 100
Quackgrass 95 75 95 75 100 70
Ragweed - - 100 - - 100
Russian Thistle 65 75 100 80 70 100
Ryegrass, Italian - - 98 - - 80
Sandbur 40 35 40 30 35 35
Signalgrass 65 40 95 40 75 65
Sowthistle 100 80 95 100 95
Spanishneedles 100 100 100 100 100 100
Spiderwort - - 100 - - 100
Surinam Grass 90 30 80 35 75 70
Table G Compounds
16 g ai/ha 186 218 236 237 238 239
Early Postemergence
Barnyardgrass 20 20 35 10 20 40
Bermudagrass 20 35 35 0 50 50
Bindweed, Field - - 100 - - 90
Black Mustard - - 50 - - -
Bluegrass - - 80 - - 60
Bromegrass, Downy 80 30 75 75 100 40
Chickweed - - 100 - - 100
Crabgrass, Large 65 30 60 35 70 50
Dallisgrass - - 30 - - -
Foxtail, Green 65 20 50 20 75 40
Goosegrass - - 40 - - 65
Groundsel 100 90 100 90 80 95
Guineagrass - - 30 - - 65
Horseweed - - 100 - - 50
Itchgrass 35 20 30 30 35 50
Johnsongrass 80 75 90 35 95 80
Kochia 75 75 80 75 75 80
Mallow 100 90 100 100 100 100
Momingglory 35 65 70 50 75 100
Nutsedge, Purple 30 0 10 10 20 20
Prickly Sida - - 90 - - 80
Purslane 65 50 90 - 80 90
Quackgrass 60 50 60 75 50 40
Ragweed - - 95 - - 80 Russian Thistle 65 35 100 70 65 100 Ryegrass, Italian - 80 - - 65 Sandbur 35 35 10 0 20 35 Signalgrass 35 20 65 20 70 60 Sowthistle 100 - 75 90 90 100 Spanishneedles 100 80 100 100 100 100 Spiderwort - 75 - - 75 Surinam Grass 60 - 65 10 75 65
Table G Comp; >oun Is
62 g ai/ha 50 87 101 103 105 106 108 115 120 168 182 230 231 232
Postemergence
Barnyardgrass 0 60 40 20 35 20 40 75 98 20 10 95 40 30
Bermudagrass 35 35 35 35 35 30 10 40 65 20 20 75 20 30
Bindweed, Field 75 95 85 90 - 95 100 80 100 75 80 100 98 90
Black Mustard 50 65 40 90 70 65 50 100 100 65 80 100 50 100
Bluegrass 40 85 100 40 70 50 100 75 60 60 75 - 70 80
Bromegrass, Downy 40 95 90 75 80 65 80 75 80 50 70 100 85 90
Chickweed
Crabgrass, Large 40 60 65 80 80 75 60 80 98 80 75 98 80 80
Dallisgrass 35 30 40 50 20 20 30 75 90 10 40 70 0 35
Foxtail, Green 90 85 90 90 75 80 98 80 95 95 75 90 80 90
Goosegrass 15 40 40 75 50 30 40 75 90 50 60 90 65 50
Groundsel 65 100 35 - - - 80 - - - - - - -
Guineagrass 20 20 30 50 40 40 20 70 65 20 0 80 40 50
Horseweed 50 65 65 - - - 65 - - - 100 100 - -
Itchgrass 50 90 70 75 40 35 50 75 80 30 75 95 65 65
Johnsongrass 20 70 65 98 95 80 35 98 100 95 90 98 95 90
Kochia 98 98 98 95 95 98 95 95 95 90 95 100 95 98
Mallow 95 100 100 100 100 - 95 98 - 98 - - 100 98
Morningglory 50 80 40 60 - 98 80 20 100 75 35 - 80 85
Nutsedge, Purple 0 20 10 10 30 25 0 20 50 35 10 30 0 50
Prickly Sida 100 100 100 100 98 100 100 100 100 90 100 - 100 100
Purslane 80 100 85 100 95 95 - 80 100 90 95 100 95 100
Quackgrass 40 65 70 60 60 35 50 75 70 50 60 80 40 60
Ragweed 80 100 90 95 - 90 95 90 100 95 90 100 - 100
Russian Thistle - - - 100 - - - 100 - - - - 100 -
Ryegrass, Italian 75 80 75 90 65 65 50 80 80 40 50 98 70 80
Sandbur 25 25 20 10 30 20 20 20 75 20 5 65 10 20 Signalgrass 65 65 70 40 50 50 80 65 90 50 20 90 65 80 Sowthistle 40 80 90 100 80 85 90 100 100 90 100 - 80 90 Spanishneedles 100 100 95 95 - 100 100 90 98 - 90 100 Spiderwort 80 100 0 100 100 98 100 100 100 90 98 Surinam Grass 25 20 20 40 75 40 20 75 100 80 5 98 60 90
Table G Compounds Table G Compounds
62 g ai/ha 245 250 251 62 g ai/ha 245 250 251
Postemergence Postemergence
Barnyardgrass 60 35 35 Kochia 100 75 95
Bermudagrass 20 20 30 Mallow 95 70 98
Bindweed, Field 95. 85 100 Momingglory 35 35 75
Black Mustard 65 75 95 Nutsedge, Purple e50 20 80
Bluegrass 75 40 80 Prickly Sida 100 60 100
Bromegrass, Downy 90 75 85 Purslane 100 90 95
Chickweed - 100 100 Quackgrass 65 65 75
Crabgrass, Large 65 5 75 Ragweed 100 80 100
Dallisgrass 40 50 35 Russian Thistle
Foxtail, Green 75 70 100 Ryegrass, Italian 75 25 95
Goosegrass 40 20 85 Sandbur 20 40 70
Groundsel 100 30 75 Signalgrass 75 75 90
Guineagrass 20 50 50 Sowthistle 100 50 100
Horseweed 75 5 50 Spanishneedles 100 75 100
Itchgrass 65 35 85 Spiderwort 100 95 100
Johnsongrass 35 75 98 Surinam Grass 30 90 80
Table G Compounds 31 g ai/ha 50 87 101 103 105 106 108 115 120 168 182 230 231 232 Postemergence Barnyardgrass 0 40 40 10 20 10 10 10 20 10 10 10 20 20 Bermudagrass 10 35 20 20 20 30 5 20 30 20 5 35 20 20 Bindweed, Field 50 80 65 90 100 90 95 80 95 65 80 - 80 80 Black Mustard 40 20 10 50 70 65 15 95 80 65 - - 50 60 Bluegrass 40 10 80 40 60 25 90 50 40 50 50 60 65 80 Bromegrass, Downy 30 30 40 35 75 40 20 75 50 50 50 80 75 80 Chickweed Crabgrass, Large 25 35 40 65 60 40 35 65 90 40 20 80 65 75 Dallisgrass 0 0 20 20 0 0 10 50 20 10 0 10 0 10 Foxtail, Green 25 35 35 40 65 65 50 70 90 80 20 40 60 80 Goosegrass 0 20 10 65 30 30 10 60 70 30 40 35 25 30
Groundsel 30 75 0 60
Guineagrass 0 0 20 0 30 40 0 20 40 20 0 35 35 20
Horseweed 50 60 65 60 - - 50 - - - 100 100 - -
Itchgrass 20 35 35 35 35 30 35 65 40 30 20 60 50 50
Johnsongrass 20 20 15 90 50 40 0 95 75 95 90 75 75 90
Kochia 90 98 95 90 95 90 95 90 95 90 95 95 95 95
Mallow 95 100 100 98 98 100 90 98 - 98 - - 98 95
Momingglory 0 30 30 50 100 80 10 10 65 65 35 - 65 75
Nutsedge, Purple 0 10 0 10 20 10 0 10 10 10 10 10 0 10
Prickly Sida 70 75 100 100 98 100 100 100 100 90 100 - 100 100
Purslane 0 95 80 80 85 90 - 80 100 90 80 - 90 100
Quackgrass 0 20 35 50 50 10 30 75 60 50 60 40 40 50
Ragweed 75 80 80 90 - 80 95 80 90 90 90 98 95 100
Russian Thistle 100 - - - 100 - 100 - - 100 -
Ryegrass, Italian 40 35 40 80 25 40 40 60 80 25 35 90 20 50
Sandbur 0 25 10 5 10 0 0 10 20 10 5 10 10 10
Signalgrass 10 10 10 35 40 40 10 35 30 35 0 30 40 40
Sowthistle 35 0 90 100 70 85 - - 100 90 - - 80 90
Spanishneedles 80 90 95 95 100 100 100 80 80 - 75 98 - -
Spiderwort 50 70 0 90 90 95 100 100 100 90 98 - - -
Surinam Grass 10 20 20 35 65 10 10 5 5 30 5 _ 20 65
Table G Compounds Table G Compounds
31 g ai/ha 245 250 251 31 g ai/ha 245 250 251
Postemergence Postemergence
Barnyardgrass 40 5 10 Kochia - 75 90
Bermudagrass 20 5 10 Mallow 95 70 85
Bindweed, Field 75 30 98 Momingglory 20 5 5
Black Mustard - 10 35 Nutsedge, Purple - 10
Bluegrass 70 20 65 Prickly Sida 100 20 50
Bromegrass, Downy 60 40 75 Purslane 100 70 90
Chickweed - 85 100 Quackgrass 65 30 30
Crabgrass, Large 50 5 20 Ragweed 100 75 75
Dallisgrass 35 15 20 Russian Thistle
Foxtail, Green 35 5 10 Ryegrass, Italian 70 10 40
Goosegrass 40 15 20 Sandbur 20 5 15
Groundsel 80 5 50 Signalgrass 35 5 10
Guineagrass 20 20 35 Sowthistle - 5 5 Horseweed - 5 25 Spanishneedles 100 35 95
Itchgrass 40 5 40 Spiderwort - 20 90
Johnsongrass 20 35 35 Surinam Grass 30 5 25
Table G Compounds
16 g ai/ha 50 87 101 103 105 106 107 108 115 120 168 182 230 231
Postemergence
Barnyardgrass 0 30 35 0 10 10 10 10 10 0 10 0 0 10
Bermudagrass 0 10 0 20 10 10 10 0 10 10 10 5 10 10
Bindweed, Field 35 75 65 80 - 90 90 75 60 90 50 50 - 80
Black Mustard 0 20 10 35 60 65 35 10 50 50 - 50 - 50
Bluegrass 10 10 - 35 10 20 25 10 50 35 20 30 60 35
Bromegrass, Downy 10 20 20 0 75 20 40 10 35 10 35 50 70 75
Chickweed
Crabgrass, Large 20 30 25 30 40 20 40 30 30 65 30 20 65 50
Dallisgrass 0 0 20 20 0 0 0 0 0 10 0 0 0 0
Foxtail, Green 10 20 20 20 40 35 40 10 35 30 30 10 10 60
Goosegrass 0 20 0 50 20 10 10 0 10 20 10 40 5 10
Groundsel 30 75 0 - - - - 35 - - - - - -
Guineagrass 0 0 0 0 30 30 20 0 10 20 20 0 0 30
Horseweed 20 0 65 - - - - 30 65 - - 100 100 -
Itchgrass 20 30 20 5 20 20 20 20 30 20 10 10 50 35
Johnsongrass 0 20 10 10 40 35 40 0 75 40 10 5 75 40
Kochia 75 95 90 90 95 65 90 90 90 90 90 90 90 95
Mallow 80 100 90 95 98 95 100 65 98 - 95 - - 98
Momingglory 0 20 10 35 80 60 80 10 10 65 40 5 - 40
Nutsedge, Purple 0 0 - 10 - 0 0 0 10 10 0 0 10 0
Prickly Sida 35 75 100 90 65 80 100 50 100 100 65 75 - 85
Purslane 0 90 75 70 80 80 80 100 80 100 90 50 - 85
Quackgrass 0 20 35 30 35 0 20 20 60 60 10 40 35 30
Ragweed 60 80 75 75 75 75 90 80 75 80 75 90 80 80
Russian Thistle - - - 100 - - - - 100 - - - - -
Ryegrass, Italian 35 35 30 50 10 10 10 35 40 40 10 20 50 20
Sandbur 0 20 0 5 0 0 0 0 5 5 0 5 5 0
Signalgrass 0 10 0 35 10 30 20 10 0 20 20 0 10 20
Sowthistle 0 0 - 100 30 40 85 90 100 98 85 - - 80
Spanishneedles 40 75 75 60 100 100 - 75 65 75 - 35 80 -
Spiderwort 40 70 0 75 - - 100 75 80 75 90 90 - - Surinam Grass 10 20 0 35 10 10 10 5 0 5 -
Table G Compounds Table G Compounds
16 g ai/ha 232 245 250 251 16 g ai/ha 232 245 250 251
Postemergence Postemergence
Barnyardgrass 20 30 0 10 Kochia 95 90 40 90
Bermudagrass 20 10 5 10 Mallow 90 80 20 50
Bindweed, Field 60 65 5 80 Momingglory 40 20 5 5
Black Mustard 40 20 0 20 Nutsedge, Purple 0 0 0 0
Bluegrass 35 10 20 65 Prickly Sida 90 100 20 50
Bromegrass, Downy 60 20 10 70 Purslane 90 100 35 90
Chickweed 75 100 Quackgrass 35 0 0 30
Crabgrass, Large 60 35 5 5 Ragweed 80 80 35 75
Dallisgrass 0 20 5 20 Russian Thistle 80
Foxtail, Green 50 20 5 10 Ryegrass, Italian 30 65 10 20
Goosegrass 20 10 10 10 Sandbur 0 0 5 5
Groundsel - 50 5 20 Signalgrass 35 0 5 10
Guineagrass 10 0 5 15 Sowthistle - 50 0 5
Horseweed - 40 5 Spanishneedles - 80 20 75
Itchgrass 35 10 5 10 Spiderwort - 50 10 10
Johnsongrass 65 10 20 35 Surinam Grass 35 10 5 15
Table G Compounds
8 g ai/ha 87 101 103 105 106 107 108 115 120 168 182 230 231 232
Postemergence
Barnyardgrass 0 20 0 10 10 0 0 0 0 0 0 0 10 10
Bermudagrass 10 0 10 10 10 10 0 5 5 10 0 10 10 20
Bindweed, Field 75 65 75 75 50 80 75 50 70 35 50 70 65 40
Black Mustard 10 0 35 30 50 35 10 20 30 35 50 30 30 35
Bluegrass 10 65 0 10 10 25 10 10 30 20 0 35 10 20
Bromegrass, Downy 0 0 0 10 10 35 0 35 0 20 35 70 35 35
Chickweed
Crabgrass, Large 30 0 0 30 10 40 20 0 - 30 0 35 60
Dallisgrass 0 0 0 0 0 0 0 0 0 0 0 0 0
Foxtail, Green 0 10 10 20 10 30 0 10 10 10 5 20 20
Goosegrass 0 0 20 0 10 10 0 10 10 0 5 0 0
Groundsel 35 0 100 35
Guineagrass 0 0 0 10 0 10 0 0 0 10 0 0 30 0
Horseweed 0 0 - - - - 90 )5 __ _ Itchgrass 20 0 0 10 10 10 0 5 5 10 5 20 20 20
Johnsongrass 10 0 10 10 10 35 0 0 10 0 0 0 20 40
Kochia 80 80 90 90 - 80 80 90 90 80 75 90 80 90
Mallow 90 70 90 90 80 95 65 90 90 90 - - 95 90
Momingglory 10 10 35 25 35 20 0 0 5 35 5 35 30 30
Nutsedge, Purple 0 0 10 0 - 0 0 0 10 0 0 10 0 0
Prickly Sida 35 75 75 65 65 20 30 75 80 65 75 - 75 75
Purslane 75 60 50 65 75 65 0 70 80 90 35 65 80 75
Quackgrass 0 35 30 0 0 20 20 60 50 10 35 20 20
Ragweed 65 40 50 75 75 80 80 70 65 75 40 65 75 75
Russian Thistle - 30 - - - - 100 100 -
Ryegrass, Italian 30 20 35 0 0 10 20 40 35 0 0 20 10 10
Sandbur 20 0 5 0 0 0 0 0 5 0 5 5 0 0
Signalgrass 10 0 30 10 0 10 0 0 0 20 0 10 10 0
Sowthistle 0 90 95 20 40 65 90 90 80 80 - 80 10
Spanishneedles 40 65 30 - 100 - 50 35 60 20 30
Spiderwort 35 0 75 65 - 100 60 20 75 60 80 90 100
Surinam Grass 20 0 0 10 10 10 0 5 5 0 5 5 - 20
Table G Compounds Table G Compounds
8 g ai/ha 245 250 251 8 g ai/ha 245 250 251
Postemergence Postemergence
Barnyardgrass 20 0 5 Kochia 80 10 90
Bermudagrass 10 0 5 Mallow 70 10 20
Bindweed, Field 65 5 40 Momingglory 0 5 5
Black Mustard 20 0 10 Nutsedge, Purple 0 0 0
Bluegrass 0 0 65 Prickly Sida 80 10 30
Bromegrass, Downy 0 10 10 Purslane 95 30 80
Chickweed - 20 100 Quackgrass 0 0 20
Crabgrass, Large 30 5 5 Ragweed 75 10 50
Dallisgrass 0 0 5 Russian Thistle - - -
Foxtail, Green 0 5 5 Ryegrass, Italian 20 5 10
Goosegrass 10 10 5 Sandbur 0 5 5
Groundsel 50 0 10 Signalgrass 0 5 5
Guineagrass 0 5 5 Sowthistle 20 0 0
Horseweed 40 0 5 Spanishneedles 60 10 20
Itchgrass 10 0 5 Spiderwort - 0 5
Johnsongrass 0 20 30 Surinam Grass 0 5 10 Table G Compounds
250 g ai/ha 186 218 236 237 238 239 Preemergence
Barnyardgrass 100 100 100 100 100 100
Bermudagrass 100 100 100 100 100 100
Bindweed, Field 100 100 100 100 100 100
Black Mustard 100 100 100 100 100 100
Bluegrass 100 100 100 100 100 100
Bromegrass, Downy 100 100 100 100 100 100
Chickweed 100 100 - 100 100
Crabgrass, Large 100 100 100 100 100 100
Dallisgrass 100 100 100 100 100 100
Foxtail, Green 100 100 100 100 100 100
Goosegrass 100 100 100 100 100 100
Groundsel 100 100 100 100 100 100
Guineagrass 100 100 100 100 100 100
Itchgrass 100 100 100 100 100 100
Johnsongrass 100 100 100 100 100 100
Kochia 100 100 100 100 100 100
Mallow 100 100 100 100 100 100
Momingglory 100 100 100 95 100 85
Nutsedge, Purple 90 90 100 85 90 80
Prickly Sida 100 100 100 100 100 100
Purslane 100 80 100 100 100 100
Quackgrass 100 100 100 100 100 100
Ragweed 100 100 100 100 100 100
Russian Thistle 100 100 100 100 100 100
Ryegrass, Italian 100 100 100 100 100 100
Sandbur 100 100 100 100 100 100
Signalgrass 100 100 100 100 100 100
Sowthistle 100 100 100 100 100 100
Spanishneedles 100 100 100 100 100 100
Spiderwort 100 100 100 100 100 100
Surinam Grass 100 100 100 100 100 100
Table G Compounds
125 g ai/ha 186 218 236 237 238 239
Preemergence
Barnyardgrass 100 100 100 100 100 100 Bermudagrass 100 100 100 100 100 100
Bindweed, Field 100 95 100 100 100 100
Black Mustard 100 100 100 100 100 100
Bluegrass 98 100 100 100 100 100
Bromegrass, Downy 100 100 100 100 100 100
Chickweed 100 100 - 100 100
Crabgrass, Large 100 100 100 100 100 100
Dallisgrass 100 100 100 100 98 100
Foxtail, Green 100 100 100 100 100 100
Goosegrass 98 100 100 100 100 95
Groundsel 100 100 100 100 100 100
Guineagrass 100 100 100 100 100 100
Itchgrass 100 98 100 100 100 100
Johnsongrass 100 100 100 100 100 100
Kochia 100 100 98 100 100 100
Mallow 100 100 100 100 100 100
Momingglory 100 90 100 90 100 75
Nutsedge, Purple 80 75 95 75 75 70
Prickly Sida 100 100 100 100 100 100
Purslane 100 80 100 100 100 100
Quackgrass 100 100 100 100 100 100
Ragweed 100 98 100 100 100 100
Russian Thistle 100 100 100 100 95 100
Ryegrass, Italian 100 98 100 100 100 100
Sandbur 100 100 100 100 100 100
Signalgrass 100 100 100 100 100 98
Sowthistle 100 100 100 100 100 100
Spanishneedles 100 100 100 100 100 100
Spiderwort 100 100 100 100 100 98
Surinam Grass 100 100 100 100 100 100
Table G Compounds
62 g ai/ha 50 87 101 103 105 106 108 115 120 168 182 186 218 230
Preemergence
Barnyardgrass 98 98 95 100 100 100 98 95 100 95 100 100 98 100
Bermudagrass 100 100 98 95 95 100 100 95 100 100 100 100 100 100
Bindweed, Field 80 90 75 95 95 95 100 95 80 85 100 100 90 100
Black Mustard 100 - 100 100 100 100 100 100 100 100 100 100 100 100
Bluegrass 80 95 65 95 90 100 100 60 100 100 90 98 100 100 Bromegrass, Downy 0 30 20 25 50 100 35 0 45 15 20 100 100 30
Chickweed 98 100 100 100 95 100 100 100 100 100 100 100 100 100
Crabgrass, Large 98 100 90 100 100 95 98 95 100 95 100 100 100 100
Dallisgrass 80 85 90 85 95 100 95 85 95 100 95 95 98 100
Foxtail, Green 90 100 80 100 95 100 100 85 100 100 95 100 98 100
Goosegrass 90 95 90 100 95 95 90 90 90 95 85 98 100 100
Groundsel 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Guineagrass 100 100 100 100 100 90 100 100 100 100 95 100 100 100
Horseweed 100 100 100 100 100 100 100 100 100 100 100 - - 100
Itchgrass 80 95 80 75 85 100 85 75 85 90 85 100 90 100
Johnsongrass 100 100 100 100 100 95 100 100 100 100 100 100 100 100
Kochia 60 90 70 100 95 100 100 100 100 100 100 90 65 100
Mallow 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Momingglory 60 70 50 75 100 100 85 75 70 90 70 90 75 80
Nutsedge, Purple 50 50 70 65 80 80 75 50 50 80 50 75 65 55
Prickly Sida 100 100 100 100 100 100 100 100 100 100 100 98 90 100
Purslane 0 90 20 70 80 100 98 50 100 90 65 90 40 100
Quackgrass 80 90 90 90 100 100 98 80 85 100 85 100 100 95
Ragweed 85 100 90 100 100 100 100 75 100 100 100 100 98 100
Russian Thistle - - 100 100 100 100 - 100 100 100 100 100 100 100
Ryegrass, Italian 85 90 90 90 95 - 90 75 100 95 100 90 98 100
Sandbur 80 90 100 90 80 .95 85 85 100 100 100 100 100 100
Signalgrass 85 95 90 95 90 100 95 90 95 90 95 100 90 100
Sowthistle 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Spanishneedles 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Spiderwort 95 100 100 95 100 100 98 100 100 95 100 100 100 100
Surinam Grass 100 98 95 100 95 100 100 100 100 95 100 100 100 100
Table G Compounds
62 g ai/ha 231 232 236 237 238 239 245 250 251
Preemergence
Barnyardgrass 100 95 100 100 100 95 95 85 100
Bermudagrass 95 100 100 100 100 100 90 75 100
Bindweed, Field 90 60 100 100 100 98 60 65 100
Black Mustard 100 100 100 100 100 100 95 85 100
Bluegrass 100 100 100 100 90 100 60 50 100
Bromegrass, Downy 10 50 100 100 80 98 0 15 50
Chickweed 100 100 - 100 100 - 100 100 100
Crabgrass, Large 95 90 100 100 100 100 95 100 100 Dallisgrass 90 85 100 98 95 90 85 60 100
Foxtail, Green 85 90 100 100 100 98 95 100 100
Goosegrass 90 85 98 98 95 95 85 65 95
Groundsel 100 100 100 100 100 100 100 95 100
Guineagrass 100 100 100 100 100 100 85 95 100
Horseweed 100 100 _ _ _ _ 100 80 100
Itchgrass 80 85 100 100 100 95 85 95 100
Johnsongrass 95 100 100 100 100 100 90 95 100
Kochia 90 95 95 98 98 80 98 25 100
Mallow 100 100 100 100 100 100 100 85 100
Momingglory 75 65 100 90 90 65 20 75 100
Nutsedge, Purple 50 60 75 75 60 50 35 100 85
Prickly Sida 100 100 100 100 100 100 100 95 100
Purslane 100 100 100 100 95 85 100 25 95
Quackgrass 90 80 100 100 100 95 65 70 95
Ragweed 90 80 100 100 100 90 75 70 100
Russian Thistle 100 100 100 100 - 90 100 100 100
Ryegrass, Italian 75 80 100 100 98 98 90 75 100
Sandbur 75 85 100 98 100 100 95 95 100
Signalgrass 85 85 100 85 100 98 90 75 100
Sowthistle 100 100 100 100 100 100 100 95 100
Spanishneedles 100 100 100 100 100 100 100
Spiderwort 100 100 95 100 100 90 100 85 95
Surinam Grass 95 85 100 95 100 100 95 100 100
Table G Compounds
31 g ai/ha 50 87 101 103 105 106 108 115 120 168 182 186 218 230
Preemergence
Barnyardgrass 90 90 95 100 95 90 90 95 100 90 90 75 80 100
Bermudagrass 65 60 80 75 95 95 100 65 100 95 90 90 100 95
Bindweed, Field 50 65 65 80 75 85 100 45 60 75 85 100 90 100
Black Mustard 80 100 75 85 100 90 90 100 100 100 100 100 100 100
Bluegrass 65 50 40 75 85 95 75 30 50 100 90 98 80 100
Bromegrass, Downy 0 0 20 5 50 - 20 0 5 0 15 90 80 20
Chickweed 98 100 98 100 95 100 100 100 100 100 95 100 100 100
Crabgrass, Large 80 80 80 80 100 95 80 80 95 95 80 95 95 85
Dallisgrass 65 75 85 75 80 85 90 70 75 90 50 85 75 80
Foxtail, Green 75 75 75 70 90 100 75 80 80 95 75 100 95 70
Goosegrass 70 80 75 85 85 80 75 70 80 90 80 95 85 90 Groundsel 100 100 100 100 100 100 100 100 100 100 100 100 100 100
Guineagrass 90 80 90 100 100 90 80 90 100 100 85 100 100 100
Horseweed 100 98 95 100 100 100 100 90 100 100 60 - - 100
Itchgrass 70 90 65 60 85 90 80 60 70 75 65 100 80 85
Johnsongrass 95 95 95 95 95 95 75 95 100 95 90 100 95 100
Kochia 10 80 35 70 90 - 80 95 95 100 75 80 40 95
Mallow 100 100 100 95 80 100 100 100 100 100 90 100 98 100
Momingglory 50 60 50 55 90 85 80 60 60 70 60 90 75 70
Nutsedge, Purple 35 20 30 50 65 50 - - 45 55 45 50 35 50
Prickly Sida 100 100 100 100 100 100 100 100 100 100 100 98 90 100
Purslane 0 40 10 10 - 100 90 50 60 - 15 50 20 70
Quackgrass 60 65 65 65 85 90 65 55 75 95 60 80 60 80
Ragweed - 90 80 70 100 85 80 50 80 100 85 95 80 100
Russian Thistle - - 100 50 100 100 - 100 100 100 100 80 100 100
Ryegrass, Italian 70 85 75 80 85 90 75 65 70 75 80 90 95 85
Sandbur 65 80 65 65 70 95 80 75 65 75 100 90 100 65
Signalgrass 70 90 80 70 80 85 75 80 90 85 80 95 75 90
Sowthistle 100 100 100 100 100 100 100 100 100 100 100 98 100 100
Spanishneedles 75 80 100 100 90 90 100 100 100 100 100 100 100 100
Spiderwort 75 80 80 80 95 95 70 100 100 95 60 100 100 100
Surinam Grass 65 90 90 95 90 95 90 90 100 95 100 95 80 100
Table G Compounds
31 g ai/ha 231 232 236 237 238 239 245 250 251
Preemergence
Barnyardgrass 85 85 100 80 95 90 70 55 85
Bermudagrass 80 80 100 80 100 75 40 40 90
Bindweed, Field 90 55 100 100 100 80 40 20 100
Black Mustard 85 100 100 100 100 100 65 65 100
Bluegrass - 90 10 80 80 90 35 10 85
Bromegrass, Downy 10 0 100 100 - 90 0 10 35
Chickweed 100 100 - 100 100 - 100 55 100
Crabgrass, Large 85 80 100 95 98 98 60 80 95
Dallisgrass 75 75 100 75 90 80 75 20 85
Foxtail, Green 80 80 100 90 85 90 80 90 100
Goosegrass 80 70 98 75 90 90 50 30 80
Groundsel 100 100 100 100 100 100 100 10 100
Guineagrass 100 85 100 100 100 100 80 70 100
Horseweed 100 100 — _ _ _ 100 15 100 Itchgrass 80 80 100 90 98 85 75 55 95
Johnsongrass 90 95 100 100 90 100 80 50 95
Kochia 90 90 80 95 75 35 65 10 95
Mallow - 100 100 100 100 100 100 30 100
Momingglory 70 60 90 80 75 65 20 60 80
Nutsedge, Purple 25 35 40 50 60 35 - 5 55
Prickly Sida 100 100 100 80 98 100 100 20 100
Purslane 100 35 70 100 90 80 75 0 75
Quackgrass 90 75 98 80 100 75 40 45 80
Ragweed 90 70 100 80 90 80 65 45 80
Russian Thistle 100 100 90 100 95 80 100 30 100
Ryegrass, Italian 75 70 100 100 90 90 65 40 95
Sandbur 75 70 100 80 75 65 65 50 75
Signalgrass 85 75 100 85 90 85 50 50 80
Sowthistle 100 95 100 100 100 100 100 90 100
Spanishneedles 90 95 100 100 100 100 100 - -
Spiderwort 100 50 80 0 100 35 65 60 90
Surinam Grass 90 75 100 80 90 100 80 80 100
Table G Compounds
16 g ai/ha 50 87 101 103 105 106 107 108 115 120 168 182 186 218
Preemergence
Barnyardgrass 40 65 80 65 85 70 80 40 75 50 75 45 50 20
Bermudagrass 0 50 35 50 95 75 70 75 10 55 95 70 75 40
Bindweed, Field 40 40 40 40 75 80 60 75 35 30 60 45 80 50
Black Mustard 50 75 50 75 65 80 90 80 50 90 75 55 100 75
Bluegrass 0 35 40 30 55 95 75 20 5 50 85 85 70 70
Bromegrass, Downy 0 0 0 0 40 90 0 0 0 0 0 0 50 50
Chickweed 95 100 90 100 95 95 95 100 100 95 95 95 100 100
Crabgrass, Large 15 75 40 40 90 90 75 70 55 70 80 45 90 30
Dallisgrass 35 25 75 40 70 80 70 85 60 65 75 40 75 0
Foxtail, Green 40 40 65 45 80 75 90 65 65 60 75 45 80 60
Goosegrass 0 15 65 40 75 80 70 60 40 70 75 50 75 70
Groundsel 95 100 80 95 100 100 100 95 100 100 100 100 100 100
Guineagrass 40 60 75 50 100 90 90 65 75 85 100 60 90 80
Horseweed 35 30 65 80 100 98 100 98 90 95 100 60 - -
Itchgrass 20 70 65 40 75 50 75 40 50 50 70 35 70 30
Johnsongrass 50 65 80 60 90 75 95 35 95 90 85 80 98 90
Kochia 0 70 0 45 10 95 0 20 _ 95 95 20 50 0 Mallow 95 98 95 95 20 90 100 90 90 100 100 70 100 98
Momingglory 10 20 10 50 70 75 55 50 40 40 50 - 75 40
Nutsedge, Purple 10 0 30 40 40 35 35 0 30 25 45 15 35 0
Prickly Sida 100 100 100 100 90 95 100 100 100 100 95 100 80 65
Purslane 0 20 0 - 40 55 50 - 0 30 50 0 0 0
Quackgrass 35 65 35 30 85 80 30 40 30 55 85 30 60 50
Ragweed 50 65 50 70 95 85 60 80 15 55 95 40 90 50
Russian Thistle - - 0 - 100 - - - - 100 100 100 80 50
Ryegrass, Italian 40 50 40 35 45 65 55 - 50 60 70 65 75 40
Sandbur 10 20 40 30 60 80 70 40 50 50 55 10 75 40
Signalgrass 15 40 50 50 80 60 80 30 55 60 65 50 80 60
Sowthistle 0 60 90 95 70 100 90 90 95 100 95 100 98 90
Spanishneedles 65 80 65 100 80 70 90 85 100 100 100 100 100 100
Spiderwort 75 70 75 50 90 95 0 70 80 100 95 60 0 0
Surinam Grass 40 50 80 80 80 90 75 75 80 85 95 85 80 70
Table G Compounds
16 g ai/ha 230 231 232 236 237 238 239 245 250 251
Preemergence
Barnyardgrass 65 75 75 100 20 75 90 25 30 55
Bermudagrass 5 70 65 75 30 85 65 10 10 75
Bindweed, Field 65 50 5 95 75 60 50 35 0 70
Black Mustard 70 50 35 100 90 100 90 30 45 75
Bluegrass 85 100 70 100 65 40 35 0 0 40
Bromegrass, Downy 0 0 0 95 60 30 75 0 0 0
Chickweed 100 95 95 - 98 100 - 100 - 80
Crabgrass, Large 65 85 80 95 65 80 80 30 45 75
Dallisgrass 80 70 55 65 35 40 70 35 0 65
Foxtail, Green 55 70 75 75 70 75 75 65 55 85
Goosegrass 75 70 60 75 65 75 65 10 5 55
Groundsel 100 100 100 100 0 100 100 98 0 95
Guineagrass 80 85 75 100 80 90 80 40 10 80
Horseweed 80 100 - - - - - 95 5 85
Itchgrass 70 70 60 98 75 75 75 60 35 80
Johnsongrass 100 85 90 100 85 90 95 70 25 70
Kochia 95 80 80 30 50 50 20 65 10 15
Mallow 80 95 85 98 100 98 100 20 0 100
Momingglory 55 40 35 65 40 50 60 10 50 40
Nutsedge, Purple 20 20 10 30 30 30 20 20 0 40 Prickly Sida 100 90 100 80 65 75 70 100 10 85
Purslane 55 100 0 65 40 35 35 35 0 50
Quackgrass 65 80 35 60 60 70 50 35 35 55
Ragweed 75 70 40 90 70 75 60 50 15 30
Russian Thistle 100 95 - 75 65 - 65 50 30 95
Ryegrass, Italian 75 60 70 98 80 75 75 50 40 60
Sandbur 50 60 55 60 50 40 50 10 15 65
Signalgrass 70 75 75 75 50 70 75 30 30 65
Sowthistle 100 100 95 0 100 95 100 100 80 95
Spanishneedles 100 80 70 100 100 100 100 20 - -
Spiderwort 65 100 45 80 0 0 35 50 35 30
Surinam Grass 1,00 90 70 95 75 90 75 50 60 95
Table G Compounds
8 g ai/ha 87 101 103 105 106 107 108 115 120 168 182 230 231 232
Preemergence
Barnyardgrass 30 20 10 50 40 55 20 30 20 50 20 35 40 60
Bermudagrass 0 0 40 65 60 50 0 10 50 75 55 0 60 50
Bindweed, Field 40 20 20 20 50 10 20 15 15 15 35 10 10 0
Black Mustard 20 20 40 55 65 60 65 15 40 50 40 30 25 15
Bluegrass 0 0 5 20 65 35 0 5 10 75 50 10 95 25
Bromegrass, Downy 0 0 0 30 75 0 0 0 0 0 0 0 0 0
Chickweed 98 65 65 95 95 90 90 60 30 95 10 95 95 95
Crabgrass, Large 30 20 25 45 55 60 30 20 30 70 15 30 70 70
Dallisgrass 10 10 30 45 50 50 85 25 45 60 5 10 5 10
Foxtail, Green 10 0 20 60 55 75 0 15 20 60 15 10 65 55
Goosegrass 0 0 10 55 50 35 20 15 10 50 10 10 60 40
Groundsel 90 0 90 0 95 100 80 100 100 0 75 100 100 95
Guineagrass 20 0 40 65 60 70 20 10 85 65 25 40 85 45
Horseweed 0 0 15 0 - 100 0 80 95 0 50 70 0 -
Itchgrass 20 20 5 50 50 40 10 10 15 45 10 20 30 45
Johnsongrass 20 20 35 35 45 75 10 55 60 55 30 30 70 65
Kochia 0 0 20 0 75 0 0 50 10 80 10 25 75 50
Mallow 90 90 60 0 60 85 35 75 80 70 55 50 65 75
Momingglory 0 0 45 60 5 45 0 25 30 50 30 30 10 15
Nutsedge, Purple 0 0 5 10 5 10 0 0 5 0 0 0 0 0
Prickly Sida 40 85 80 80 80 55 40 80 85 80 85 100 90 75
Purslane 0 0 0 0 50 0 0 0 0 25 0 5 100 -
Quackgrass 0 10 10 30 60 10 20 10 15 75 5 50 80 30 Ragweed 35 10 50 60 65 10 0 15 0 65 15 40 50 10
Russian Thistle - 0 0 100 _ _ - 0 100 - - - 30 -
Ryegrass, Italian 0 0 15 10 60 30 30 10 30 60 45 30 60 15
Sandbur 0 0 0 35 55 15 0 10 0 50 0 10 45 20
Signalgrass 20 10 25 35 50 65 0 20 30 45 15 25 50 60
Sowthistle 0 35 65 70 85 90 35 90 100 95 85 90 95 95
Spanishneedles 40 10 100 55 40 75 75 100 100 80 100 100 70 60
Spiderwort 0 75 10 80 95 0 65 80 55 35 - 45 100 -
Surinam Grass 20 20 60 75 70 65 20 15 60 60 10 80 70 40
Table G Compounds Table G Compounds
8 g ai/ha 245 250 251 8 g ai/ha 245 250 251
Preemergence Preemergence
Barnyardgrass 20 0 30 Kochia 0 0 10
Bermudagrass 0 0 40 Mallow 20 0 55
Bindweed, Field 0 0 5 Morninggl'ory 0 35 15
Black Mustard 20 10 60 Nutsedge, Purple - 0 15
Bluegrass 0 0 0 Prickly Sida 75 0 85
Bromegrass, Downy 0 0 0 Purslane - 0 40
Chickweed 100 0 - ' Quackgrass 0 10 30
Crabgrass, Large 10 5 50 Ragweed 10 0 0
Dallisgrass 0 0 15 Russian Thistle 0 0 80
Foxtail, Green 10 5 40 Ryegrass, Italian 0 15 20
Goosegrass 0 0 20 Sandbur 10 0 15
Groundsel 95 0 80 Signalgrass 0 5 20
Guineagrass 0 0 65 Sowthistle 50 70 90
Horseweed 50 0 40 Spanishneedles 0 - -
Itchgrass 20 15 50 Spiderwort 0 35 30
Johnsongrass 30 10 50 Surinam Grass 5 25 65
TESTH This test evaluated the effect of mixtures of compound 237 with mefluidide on two plant species. Seeds of test plants consisting of large crabgrass (DIGSA, Digitaria sanguinalis (L.) Scop.) and cocklebur (XANST, Xanthium strumarium L.), were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients. Seeds of large crabgrass were planted about 1 cm deep; cocklebur seeds were planted about 2.5 cm deep. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of about 14 hours; daytime and nighttime temperatures were about 24-28 °C and 20-24 °C, respectively. Balanced fertilizer was applied through the watering system. The plants were grown for 9 to 14 days so that at time of treatment the plants ranged in height from 2 to 18 cm (1- to 4-leaf stage). Treatments consisted of Compound 237 and mefluidide alone and in combination, suspended or dissolved in a non- phytotoxic solvent mixture which included a surfactant and applied as a foliage spray using a volume of 457 L/ha. Each treatment was replicated one time. The application solvent was observed to have no effect compared to untreated check plants. Treated plants and controls were maintained in the greenhouse and watered as needed with care to not wet the foliage for the first 24 hours after treatment. The effects on the plants approximately two weeks after treatment were visually compared to untreated controls. Plant response ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15(1), pp 20- 22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form: Pa+b = Pa + Pb - (PaPb / ιoo) wherein Pa+b *s ^e percentage effect of the mixture expected from additive contribution of the individual components, Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and Ptø is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.
The results and additive effects expected from Colby's Equation are listed in Table H. Table H - Observed and Expected Results from Compound 237 Alone and in Combination with Mefluidide*
Figure imgf000236_0001
* Application rates are grams of active ingredient per hectare (g a /ha). "Obsd." is observed effect. "Exp." is expected effect calculated from Colby's Equation. As can be seen from the results listed in Table H, most of the observed results were greater than expected from the Colby Equation, and in one case much greater. Most notable was the greater than additive effect observed on cocklebur (XANST).

Claims

What is claimed is: 1. A compound selected from Formula I, an N-oxide or an agriculturally suitable salt thereof,
Figure imgf000238_0001
J-l J-2 J-3 J-4 Y is O, S(O)n or ΝR8; R is H, C2-C5 alkoxymethyl, C2-C5 alkylcarbonyl or C2-C5 alkoxycarbonyl; R1 is H or C!-C4 alkyl; R2 is H, C!-C4 alkyl, C,-C4 haloalkyl, C3-C6 cycloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C2-C4 alkoxymethyl, cyano, C1-C4 alkoxy or C2-C4 alkoxycarbonyl; each R3 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-Q alkynyl, C2-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C4 alkoxyalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, Cγ-C^ alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C -C alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C4 alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, Cγ-Q.4 alkylamino, C2-C8 dialkylamino, C3-Cg cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C^-C^ alkylcarbonyl, C2-Cg alkoxycarbonyl, C^-C^ alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl, C3-C6 trialkylsilyl, R25(R 6)NS(O)2-, R27S(O)2N(R28)-, phenyl, phenoxy, 5-membered heteroaromatic ring and 6-membered heteroaromatic ring, each phenyl, phenoxy, 5-membered heteroaromatic ring and 6-membered heteroaromatic ring optionally substituted with one to three substituents independently selected from R9; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -OCF2O-, -OCH2CH2O-, -OCF2CF2O- or -CH=CH-CH=CH-; R4 is Ci-Cio alkyl, C3-C7 cycloalkyl, C4-C10 alkylcycloalkyl, C4-C10 cycloalkylalkyl, C5-C10 alkylcycloalkylalkyl, CJ-CJQ haloalkyl, C2-C10 cyanoalkyl, C2-C10 nitroalkyl, C3-C10 halocycloalkyl, C4-C10 halocycloalkylalkyl, C2-C10 alkenyl, C2-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, C2-C10 alkoxyalkyl, C4-C10 (cycloalkyl)oxyalkyl, -CHf;O(CH2)p}, C2-C10 haloalkoxyalkyl, C4-C10 alkenyloxyalkyl, C4-C10 haloalkenyloxyalkyl, C4-C10 alkynyloxyalkyl, C4-C1Q haloalkynyloxyalkyl, C2-C10 alkylthioalkyl, C2-C1() alkylsulfinylalkyl, C2-C10 alkylsulfonylalkyl, 4-C10 (cycloalkyl)thioalkyl, C -C10 alkenylthioalkyl, C4-C10 alkynylthioalkyl, C4-C10 alkoxyalkenyl, C4-C10 alkoxyalkynyl, C4-C10 alkylthioalkenyl, C4-C10 alkylthioalkynyl, C4-C10 trialkylsilylalkyl, -N=CR10R or -NR12R13; or R4 is Cι-C6 alkyl substituted with C(O)R14, C(OR29)(OR30)R3l5 C(=NORl5)Rl6; NR^R18 or phenyl optionally substituted with R19, R20 and R21; or R4 is phenyl optionally substituted with R22, R23 and R24; R5 is H, halogen, C1-C6 alkyl, C]-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, ^-04 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio or C2-C5 alkoxycarbonyl; R6 is H, halogen, cyano, C1-C5 alkyl, C1-C4 haloalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, C2-Cg alkenyl, C3-Cg alkynyl, C3-Cg cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 haloalkylthio; R6a is Cj-Cg alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl or C4-C7 cycloalkylalkyl; R7 is H, Cι-C6 alkyl, C!-C4 haloalkyl, C1-C5 cyanoalkyl, C3-C6 alkenyl, C2-C4 haloalkenyl, C3-Cg alkynyl, C3-C haloalkynyl, C3-Cg cycloalkyl or C3-C6 halocycloalkyl; R8 is H, C1-C4 alkyl, C2-C4 alkylcarbonyl or C2-C4 alkoxycarbonyl; each R9 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, ^-04 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2~Cg dialkylamino, C2-C4 alkylcarbonyl, C2~Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-Cg dialkylaminocarbonyl or C3-Cg trialkylsilyl; R10 is C1-C4 alkyl; R11 is H or Cι-C2 alkyl; or R10 and R11 are taken together as -(CH2)3-, -(CH2)4-, -(CH2)5- or -(CH2)6-; R12 is H or C!-C4 alkyl; R13 is H, Cι~C2 alkyl, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl; or R12 and R13 are taken together as -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- or -CH2CH(CH3)OCH(CH3)CH2-; R14 is H, C!-C4 alkyl or C1-C4 alkoxy; R15 is H or CJ-C4 alkyl; R16 is H, C1-C4 alkyl or C1-C4 alkoxy; R17 is H or C1-C4 alkyl; R18 is H, C]-C2 alkyl, C2-C3 alkylcarbonyl or C2-C3 alkoxycarbonyl; or R17 and R18 are taken together as -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- or -CH2CH(CH3)OCH(CH3)CH2-; R19 and R22 are independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy; R20 and R23 are independently halogen, Cι-C2 alkyl, Ci fluoroalkyl, methoxy or methylthio; R21 and R24 are independently halogen; each R25 is independently H, C1-C4 alkyl, C1-C4 haloalkyl or C3-Cg cycloalkyl; each R26 is independently H or C1-C2 alkyl; or R25 and R26 are taken together as -(CH2)4-, -(CH2)5-, -CH2CH2OCH2CH2- or -CH2CH(CH3)OCH(CH3)CH2-; each R27 is independently C -[-C4 alkyl, C1-C4 haloalkyl, C3-Cg cycloalkyl or C2-C4 dialkylamino; each R28 is independently H, C1-C4 alkyl, C1-C4 haloalkyl or C3-Cg cycloalkyl; R29 and R30 are independently C1-C4 alkyl; or R29 and R30 are taken together as -CH2CH2-, -CH(CH3)CH2- or -CH2CH2CH2-; R31 is H or C1-C4 alkyl; m is O, 1, 2, 3, 4 or 5; n is O or l; p is 3 or 4; and q is 0 or 1; provided that: (a) the compound of Formula I is other than N-[[4-(4-ethoxyphenoxy)phenyl]methyl]- 5-methoxy- 1,3 -dimethyl- lH-pyrazole-4-carboxamide, N-[[4-(4-ethoxyphenoxy)- phenyl]methyl]-l,3-dimethyl-5-(l-methylethoxy)-lH-pyrazole-4-carboxamide, N-[[4-(4-ethoxyphenoxy)ρhenyl]methyl]-l,3-dimethyl-5-(2,2,2-trifluoroethoxy)- lH-pyrazole-4-carboxamide, 5-(cyclohexyloxy)-N-[[4-(4-ethoxyphenoxy)phenyl]- methyl] -l,3-dimethyl-lH-pyrazole-4-carboxamide, l-methyl-N-(phenylmethyl)- 5-[(phenylmethyl)amino]-lH-pyrazole-4-carboxamide, N-[[4-(l,l-dimethylethyl)- phenyl]methyl] - 1 ,3-dimethyl-5-phenoxy- lH-pyrazole-4-carboxamide, N-[(2-chlorophenyl)methyl-l,3-dimethyl-5-phenoxy-lH-pyrazole-4-carboxamide, 1 , 1-dimethylethyl 4-[[[(l ,3-dimethyl-5-phenoxy- lH-pyrazol-4-yl)carbonyl]- amino] methyl]benzoate, N-(phenylmethyl)-4- [ [3 -(trifluoromethyl)phenyl] amino] - 3-pyridinecarboxamide, or N-(l ,3-benzodioxol-5-ylmethyl)-3,5-bis(methylthio)-4- isothiazolecarboxamide; (b) when R4 is -Ν=CR10RU or -NR12R13, then Y is O or NR8; (c) when an R3 is CF3, then said CF3 is attached meta or para to the connection of the phenyl ring to the remainder of Formula I;
(d) when an R3 is CF3 and attached meta to the connection of the phenyl ring to the remainder of Formula I, then the position on the phenyl ring ortho to both said CF3 and the connection of the phenyl ring to the remainder of Formula I is unsubstituted or substituted by R3 other than F, and the position on the phenyl ring meta to both said CF3 and the connection of the phenyl ring to the remainder of Formula I is unsubstituted or substituted by R3 other than F; and
(e) when J is J-4, then R4 is other than phenyl optionally substituted with R22, R23 and R24. 2. A compound of Claim 1 wherein m is an integer from 0 to 3; n is 0; q is 0; and each R3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C3-Cg cycloalkyl, C3-Cg halocycloalkyl, C1-C4 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 haloalkoxyalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C3-C4 haloalkynyl, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 haloalkenyloxy, C3-C4 alkynyloxy, C3-C4 haloalkynyloxy, C2-C alkoxyalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C1-C4 alkylsulfonyl, C.-C4 haloalkylsulfonyl, C2-C4 alkenylthio, C2-C4 haloalkenylthio, C2-C4 alkenylsulfinyl, C2-C4 haloalkenylsulfinyl, C2-C4 alkenylsulfonyl, C2-C4 haloalkenylsulfonyl, C3-C4 alkynylthio, C3-C4 haloalkynylthio, C3-C4 alkynylsulfinyl, C3-C4 haloalkynylsulfinyl, C3-C alkynylsulfonyl, C3-C4 haloalkynylsulfonyl, C1-C4 alkylamino, C -C8 dialkylamino, C3-Cg cycloalkylamino, C4-C6 (alkyl)cycloalkylamino, C2-C6 alkylcarbonyl, C2-Cg alkoxycarbonyl, C2-Cg alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -OCF2O-, -OCH2CH2O-, -OCF2CF2O- or -CH=CH-CH=CH-. 3. The compound of Claim 2 wherein Y is O and R is H. 4. The compound of Claim 3 wherein R6 is H, halogen, cyano, Cι-C3 alkyl, Cι-C3 haloalkyl, C1-C3 alkoxy or C1-C3 alkylthio. 5. The compound of Claim 4 wherein R5 is halogen, Cι-C2 haloalkyl, Cι-C2 alkoxy or Cι-C2 alkylthio; and R7 is Cj-C^ alkyl, CHF2 or CH2CF3. 6. The compound of Claim 5 wherein each R3 is independently halogen, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkoxyalkoxy, C3-C4 alkynyloxy, C]-C4 alkylthio, C1-C4 alkylsulfinyl, CJ-C4 alkylsulfonyl, C2-C alkylcarbonyl, C2-Cg alkoxycarbonyl, C3-C6 trialkylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O- or -OCF2O-. 7. The compound of Claim 6 wherein R1 is H and R2 is H, cyano or CH3. 8. The compound of Claim 7 wherein R5 is halogen, CF3 or methoxy. 9. The compound of Claim 8 wherein J is J-l and R5 is halogen. 10. The compound of Claim 9 wherein each R3 is independently halogen, cyano, nitro, Cι-C2 alkyl, Cι-C2 haloalkyl, Cι-C2 alkoxy, Cj-C2 haloalkoxy, C3 alkynyloxy, Cι~C2 alkylthio, Cι~C2 alkylsulfinyl, Cι-C2 alkylsulfonyl, C2-C3 alkylcarbonyl, C2-C3 alkoxycarbonyl, trimethylsilyl, R25(R26)NS(O)2- or R27S(O)2N(R28)-; or two adjacent R3 are taken together as -OCH2O- or -OCF2O-; each R25 is independently H, C1-C2 alkyl or Cι-C2 haloalkyl; each R26 is independently H or CH3; each R27 is independently C^-C2 alkyl, C^-C2 haloalkyl or dimethylamino; and each R28 is independently H, Cj-C2 alkyl or Cι-C2 haloalkyl. 11. The compound of Claim 10 wherein R2 is CH3; R4 is Cj-Cg alkyl, C^-Cg haloalkyl, C3-C6 cycloalkyl, cyclopropylmethyl, C3-C alkenyl, C3-C6 haloalkenyl or C3- alkynyl; and the carbon atom to which R1 and R2 are attached is a stereocenter with the S configuration. 12. The compound of Claim 1 selected from the group consisting of: 2-chloro-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-N-[(lS)-l-(4-fluorophenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-N-[(lS)-l-(4-methoxyphenyl)ethyl]-6-methyl-4-(l-methylethoxy)- 3-pyridinecarboxamide, 2-bromo-6-methyl-4-(l-methylethoxy)-N-[(lS)-l-(4-methylρhenyl)ethyl]- 3-pyridinecarboxamide, and 2-bromo-6-methyl-4-(l-methylethoxy)-N-[(lS)-l-phenylethyl]-3-pyridine- carboxamide. 13. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1 and at least one of a surfactant, a solid diluent or a liquid diluent. 14. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1. 15. A herbicidal composition comprising a herbicidally effective amount of a compound of Claim 1, an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener, and at least one of a surfactant, a solid diluent or a liquid diluent.
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