PYRIMIDINYLOXYBENZENE DERIVATIVES AS HERBICIDES

Abstract

Compounds of Formula (1), including all stereoisomers, N-oxides, and salts thereof, are described (see Formula), where Q, z, R2, R3, and m are as defined in the description. Compositions containing the compounds of Formula (1) and methods for controlling unwanted vegetation, comprising bringing the unwanted vegetation or its environment into contact with an effective amount of a compound or composition of the invention, are also described.

Description

[0001] TITLE

[0002] PYRIMIDINYLOXY BENZENE DERIVATIVES AS HERBICIDES

[0003] FIELD OF THE INVENTION

[0004] This invention relates to certain pyrimidinyloxy benzene derivatives, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.

[0005] BACKGROUND OF THE INVENTION

[0006] The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.

[0007] JP 61236766 A (Sumitomo, 1986) discloses certain carbon-linked pyrimidinyloxy benzene derivitaves as herbicides. WO 94 / 17059 (Nippon Soda, 1994) discloses certain carbon linked pyrimidinyloxy benzene derivative as herbicides.

[0008] SUMMARY OF THE INVENTION

[0009] This invention is directed to compounds of Formula 1 (including all stereoisomers),

[0010] (N-oxides, and salts thereof), agricultural compositions containing them and their use as herbicides:

[0012] Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of

[0013] Formula 1 through a carbon atom, and optionally substituted with 1 to 4 R1; Z is O or S;

[0014] each R1is independently halogen, cyano, nitro, SF5, CHO, C(=0)NH2, C(=S)NH2, S02NH2, CrC4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-Cg alkylcycloalkyl, C4-Cg cycloalkylalkyl, C2-Cg alkylcarbonyl, C2-Cghaloalkylcarbonyl, C2-Cg alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2~Cg alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6

[0015] alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, Ci -C4 hydroxyalkyl, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3or B(-OC(R1B)2C(R1B)20-); or a phenyl ring optionally substituted with up to 5 substituents independently selected from R1C; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R1Con carbon atom ring members and R1Don nitrogen atom ring members;

[0016] R2is halogen, cyano, nitro, C1 -C4 alkoxy, C 1 -C4 alkyl, C2-Cg alkenyl, C2-Cg alkynyl,

[0017] SOnR2A, C1-C4 haloalkyl or C3-C6cycloalkyl;

[0018] each R3is independently halogen, cyano, hydroxy, nitro, amino, CHO, C(=0)NH2, C(=S)NH2, S02NH2, CrC4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-Cg alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C 1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1 -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 alkoxyhaloalkyl, C2-C6 alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6 cyanoalkyl, C2-C6 cyanoalkoxy, C2-C4 alkylthioalkyl, Si(CH3)3, C≡CSi(CH3)3, C(=0)N(R3A)(R3B), C(=NOR3C)H, C(=NR3D)H, SOnRE; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from RFon carbon atom ring members and R3Gon nitrogen atom ring members; or pyrimidinyloxy;

[0019] m is 0, 1, 2 or 3;

[0020] each n is independently 0, 1 or 2;

[0021] each R1A, R2Aand R3Eis independently CrC4alkyl, CrC4haloalkyl, CrC4

[0022] alkylamino or C2-C6 dialkylamino;each R1Bis independently H or Ci -C4 alkyl;

[0023] each R1Cis independently hydroxy, halogen, cyano, nitro, C^-Cg alkyl, C^-Cg

[0024] haloalkyl, C^-Cg alkoxy or C^-Cg haloalkoxy;

[0025] each R1Dis independently cyano, C^-Cg alkyl, C^-Cg haloalkyl, C^-Cg alkoxy or C2

[0026] Cg alkylcarbonyl;

[0027] each R3Ais independently Ci -C4 alkyl or Ci -C4 haloalkyl;

[0028] each R3Bis independently H, Ci -C4 alkyl or Ci -C4 haloalkyl;

[0029] each R3Cis independently H or Ci -C4 alkyl;

[0030] each R3Dis independently H, amino, Ci -C4 alkyl or Ci -C4 alkylamino;

[0031] each RFis independently hydroxy, halogen, cyano, nitro, C^-Cg alkyl, C^-Cg

[0032] haloalkyl, C^-Cg alkoxy or C^-Cg haloalkoxy; and

[0033] each RGis independently cyano, C^-Cg alkyl, C^-Cg haloalkyl, C^-Cg alkoxy or C2

[0034] Cg alkylcarbonyl;

[0035] More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).

[0036] This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) through (b 16); and salts of compounds of (bl) through (bl6).

[0037] DETAILS OF THE INVENTION

[0038] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains", "containing," "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

[0039] The transitional phrase "consisting of excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.The transitional phrase "consisting essentially of is used to define a composition, process or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term "consisting essentially of occupies a middle ground between "comprising" and "consisting of.

[0040] Where applicants have defined an invention or a portion thereof with an open-ended term such as "comprising," it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms "consisting essentially of or "consisting of."

[0041] 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).

[0042] 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.

[0043] As referred to herein, the term "seedling", used either alone or in a combination of words means a young plant developing from the embryo of a seed.

[0044] As referred to herein, the term "broadleaf used either alone or in words such as "broadleaf weed" means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons. As used herein, the term "alkylating agent" refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a 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 Q, R1and R3.

[0045] 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, / -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."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, CH3CH2CH2CH2OCH2and CH3CH2OCH2CH2. "Alkenyloxy" includes straight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy" include H2C=CHCH20, (CH3)2C=CHCH20, (CH3)CH=CHCH20, (CH3)CH=C(CH3)CH20 and

[0046] CH2=CHCH2CH20. "Alkynyloxy" includes straight-chain or branched alkynyloxy moieties. Examples of "alkynyloxy" include HC≡CCH20, CH3C≡CCH20 and CH3C≡CCH2CH20. "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, CH3CH2CH2CH2SCH2and CH3CH2SCH2CH2. "Alkylthioalkoxy" denotes alkylthio substitution on alkoxy. "Cyanoalkyl" denotes an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH2, NCCH2CH2and CH3CH(CN)CH2. "Alkylamino", "dialkylamino", and the like, are defined analogously to the above examples.

[0047] "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "halogen", either alone or in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted with halogen" includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", or when used in descriptions such as "alkyl substituted with halogen" said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" or "alkyl substituted with halogen" include F3C, C1CH2, CF3CH2and CF3CC12. The terms "haloalkoxy", and the like, is defined analogously to the term "haloalkyl". Examples of "haloalkoxy" include CF30-, CC13CH20-, HCF2CH2CH20- and CF3CH20-. "Alkylcarbonyl" denotes a straight-chain or branched alkyl moieties bonded to a C(=0) moiety. Examples of "alkylcarbonyl" include CH3C(=0)-, CH3CH2CH2C(=0)- and (CH3)2CHC(=0)-. Examples of "alkoxycarbonyl" include CH3OC(=0)-, CH3CH2OC(=0)-, CH3CH2CH2OC(=0)-, (CH3)2CHOC(=0)- and the different butoxy- or pentoxycarbonyl isomers.

[0048] The total number of carbon atoms in a substituent group is indicated by the "C -Cj" prefix where i and j are numbers from 1 to 6. For example, C1-C4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C2alkoxyalkyl designates CH3OCH2-; C3alkoxyalkyl 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-.When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1 , said substituents (when they exceed 1) are independently selected from the group of defined substituents, (e.g., (R^)n, n is 0, 1 , 2 or 3). Further, when the subscript indicates a range, e.g. (R)i_j, then the number of substituents may be selected from the integers between i and j inclusive. When a group contains a substituent which can be hydrogen, for example (when m = 0), 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 (R^)nattached to Q wherein n may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be "not substituted" or "unsubstituted", then hydrogen atoms are attached to take up any free valency.

[0049] Unless otherwise indicated, a "ring" as a component of Formula 1 (e.g., substituent Q) is carbocyclic or heterocyclic. The term "ring member" refers to an atom or heteroatom forming the backbone of a ring. When a fully unsaturated carbocyclic ring satisfies Huckel's rule, then said ring is also called an "aromatic ring". "Saturated carbocyclic" refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.

[0050] The terms "heterocyclic ring", "heterocycle" denote a ring in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Huckel's rule, then said ring is also called a "heteroaromatic ring" or "aromatic heterocyclic ring". Unless otherwise indicated, heterocyclic rings can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

[0051] "Aromatic" indicates that each of the ring atoms is essentially in the same plane and has a / ^-orbital perpendicular to the ring plane, and that (4n + 2) π electrons, where n is a positive integer, are associated with the ring to comply with Huckel's rule.

[0052] The term "optionally substituted" in connection with the heterocyclic rings refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the biological activity possessed by the unsubstituted analog. As used herein, the following definitions shall apply unless otherwise indicated. The term "optionally substituted" is used interchangeably with the phrase "substituted or unsubstituted" or with the term "(un)substituted." Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.When Q is a 5- or 6-membered (nitrogen-containing) heterocyclic ring, it may be attached to the remainder of Formula 1 though any available carbon or nitrogen ring atom, unless otherwise described. As noted above, Q can be (among others) phenyl optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. An example of phenyl optionally substituted with one to five substituents is the ring illustrated as U-l in Exhibit 1, wherein Rvis R1as defined in the Summary of the Invention for Q and r is an integer (from 0 to 4).

[0053] As noted above, Q can be (among others) 5- or 6-membered aromatic heterocyclic ring, which may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention. Examples of a 5- or 6-membered unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings U-2 through U-61 illustrated in Exhibit 1 wherein Rvis any substituent as defined in the Summary of the Invention for Q (i.e. R1) and r is an integer from 0 to 4, limited by the number of available positions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, for these U groups r is limited to the integers 0 or 1 , and r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (Rv)r.

[0054] Exhibit 1

[0056] U-2 U-3 U-4 U-5

[0058] U-7 U-8 U-9 U-10 U-l l

[0060] U-12 U-13 U-14 U-16 U-17

[0061] U-18 U-20 U-21 U-22

[0062] U-23 U-24 U-26 U-27 U-28

[0063] U-29 U-30 U-32 U-33 U-34

[0064] -42 -43 -45 -46

[0065] U-58 U-59 U-60 U-61

[0066] Although Rvgroups are shown in the structures U-l through U-61, it is noted that they do not need to be present since they are optional substituents. Note that when Rvis H when attached to an atom, this is the same as if said atom is unsubstituted. The nitrogen atoms that require substitution to fill their valence are substituted with H or Rv. Note that when the attachment point between (Rv)rand the U group is illustrated as floating, (Rv)rcan be attached to any available carbon atom or nitrogen atom of the U group. Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom. Note that some U groups can only be substituted with less than 4 Rvgroups (e.g., U-2 through U-47 and U-52 through U-61).

[0067] A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

[0068] Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. Stereoisomers are isomers of identical constitution but differing in the arrangement of their atoms in space and include enantiomers, diastereomers, cis-trans isomers (also known as geometric isomers) and atropisomers. Atropisomers result from restricted rotation about single bonds where the rotational barrier is high enough to permit isolation of the isomeric species. 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. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

[0069] Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Noncrystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms includeembodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and / or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co- crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley- VCH, Weinheim, 2006.

[0070] 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 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 dimethyldioxirane. 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. V. 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.

[0071] One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus awide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid or phenol, salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.

[0072] Embodiments of the present invention as described in the Summary of the Invention include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):

[0073] Embodiment 1. A com ound of Formula 1 wherein Q is selected from

[0075] Q-l Q-2 Q-3 Q-4 Q-5

[0077] Q-16 Q-17 Q-18 Q-19 Q-20wherein r is 0, 1 , 2 or 3; and s is 0 or 1.

[0078] Embodiment 2. A compound of Embodiment 1 wherein Q is selected from Q-l

[0079] through Q-42.

[0080] Embodiment 3. A compound of Embodiment 2 wherein Q is selected from Q-7

[0081] through Q-24.

[0082] Embodiment 4. A compound of Embodiment 3 wherein Q is selected from Q-16 and Q-18.

[0083] Embodiment 5. A compound of Embodiment 4 wherein Q is Q-16.

[0084] Embodiment 6. A compound of Embodiment 4 wherein Q is Q-18.

[0085] Embodiment 7. A compound of Embodiment 1 wherein Q is selected from Q-43

[0086] through Q-55.

[0087] Embodiment 8. A compound of Embodiment 7 wherein Q is selected from Q-43, Q-

[0088] 44, Q-45, Q-48, Q-49 and Q-50.

[0089] Embodiment 9. A compound of Embodiment 8 wherein Q is selected from Q-43, Q- 44 and Q-45.

[0090] Embodiment 10. A compound of Embodiment 9 wherein Q is Q-43.

[0091] Embodiment 1 1. A compound of Embodiment 10 wherein Q is Q-45.

[0092] Embodiment 12. A compound of Formula 1 or any one of Embodiments 1 through 1 1 either alone or in combination, wherein Z is O.

[0093] Embodiment 13. A compound of Formula 1 or any one of Embodiments 1 through 12 either alone or in combination, wherein each R1is independently halogen, cyano,

[0094] SF5, CHO, CrC4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbonyl,

[0095] C2-Cg alkoxycarbonyl, Cj-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, C - C4haloalkoxy, C3-C4haloalkenyloxy, C3-C4haloalkynyloxy,

[0096] alkoxyalkyl,hydroxyalkyl, C2-

[0097] C4alkylthioalkyl or SOnR1A.

[0098] Embodiment 14. A compound of Embodiment 13 wherein each R1is independently halogen, cyano, CHO, Cj-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, Cj-C4haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C}-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, C}-C4haloalkoxy, C3-C4haloalkenyloxy, C3-C4haloalkynyloxy,

[0099] hydroxyalkyl, C2-C4alkylthioalkyl or SOnR1A.

[0100] Embodiment 15. A compound of Embodiment 14 wherein each R1is independently halogen, cyano, Cj-C4alkyl, Cj-C4haloalkyl, Cj-C4alkoxy, Cj-C4haloalkoxy or SOnR1A.

[0101] Embodiment 16. A compound of Embodiment 15 wherein each R1is independently halogen, C^-C4alkyl, C^-C4haloalkyl or C^-C4haloalkoxy.Embodiment 17. A compound of Embodiment 16 wherein each R1is independently halogen, C 1 -C4 haloalkyl or C1 -C4 haloalkoxy.

[0102] Embodiment 18. A compound of Embodiment 17 wherein each R1is independently halogen or Ci -C4 haloalkyl.

[0103] Embodiment 19. A compound of Embodiment 18 wherein each R1is independently F,

[0104] CI, Br, CF3, CHF2or CH2F.

[0105] Embodiment 20. A compound of Formula 1 or any one of Embodiments 1 through 19 either alone or in combination, wherein r is 0, 1 or 2.

[0106] Embodiment 20a. A compound of Embodiment 20 wherein r is 1.

[0107] Embodiment 21. A compound of Formula 1 or any one of Embodiments 1 through 19 either alone or in combination, wherein s is 1.

[0108] Embodiment 21a. A compound of Formula 1 or any one of Embodiments 1 through

[0109] 20a either alone or in combination, wherein when Q is Q-16 and r is 1 then R1is attached at the 5 position of the Q-16 ring.

[0110] Embodiment 21b. A compound of Formula 1 or any one of Embodiments 1 through

[0111] 20a either alone or in combination, wherein when Q is Q-18 and r is 1 then R1is attached at the 3 position of the Q-18 ring.

[0112] Embodiment 22. A compound of Formula 1 or any one of Embodiments 1 through

[0113] 21b either alone or in combination, wherein R2is halogen, Ci -C4 alkyl or Ci -C4 haloalkyl.

[0114] Embodiment 23. A compound of Embodiment 22 wherein R2is halogen or Ci -C4 alkyl.

[0115] Embodiment 24. A compound of Embodiment 23 wherein R2is halogen or CH3.

[0116] Embodiment 25. A compound of Embodiment 24 wherein R2is halogen.

[0117] Embodiment 26. A compound of Embodiment 25 wherein R2is F, CI or Br.

[0118] Embodiment 27. A compound of Formula 1 or any one of Embodiments 1 through 26 either alone or in combination, wherein m is 0, 1 or 2.

[0119] Embodiment 28. A compound of Embodiment 27 wherein m is 0 or 1.

[0120] Embodiment 29. A compound of Embodiment 28 wherein m is 1.

[0121] Embodiment 30. A compound of Embodiment 27 wherein m is 0 (i.e. the 3-, 4-, 5- and 6-positions are unsubtituted by R3).

[0122] Embodiment 31. A compound of Formula 1 or any one of Embodiments 1 through 30 either alone or in combination, wherein each R3is independently halogen, cyano, CHO, CrC4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyl, C2-C4haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1 -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy,C3-C6 halocycloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-C6cyanoalkyl, C(=0)N(R3A)(R3B), C(=NOR3C)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3Fon carbon atom ring members and R3Gon nitrogen atom ring members.

[0123] Embodiment 32. A compound of Embodiment 31 wherein each R3is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-C6 cyanoalkyl, SOnR3E; or a 5- or 6-membered

[0124] heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3Fon carbon atom ring members and R3Gon nitrogen atom ring members.

[0125] Embodiment 33. A compound of Embodiment 32 wherein each R3is independently halogen, cyano, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Ci -C4 haloalkyl, C2-C6 alkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl.

[0126] Embodiment 34. A compound of Embodiment 33 wherein each R3is independently halogen, cyano, Ci -C4 alkyl or Ci -C4 haloalkyl.

[0127] Embodiment 35. A compound of Embodiment 34 wherein each R3is independently halogen or cyano.

[0128] Embodiment 36. A compound of Embodiment 35 wherein each R3is independently halogen.

[0129] Embodiment 37. A compound of Formula 1 or any one of Embodiments 1 through 36 either alone or in combination, wherein R3is attached to the remainder of Formula 1 at the 3 -position.

[0130] Embodiment 38. A compound of Formula 1 or any one of Embodiments 1 through 37 either alone or in combination, wherein each R1Ais independently Ci -C4 alkyl or C1-C4 haloalkyl.

[0131] Embodiment 39. A compound of Embodiment 38 wherein each R1Ais independently C1-C4 haloalkyl.Embodiment 40. A compound of Formula 1 or any one of Embodiments 1 through 39 either alone or in combination, wherein each R3Eis independently Ci -C4 alkyl. Embodiment 41. A compound of Formula 1 or any one of Embodiments 1 through 40 either alone or in combination, wherein each R3Ais independently C i -C4 alkyl. Embodiment 42. A compound of Formula 1 or any one of Embodiments 1 through 41 either alone or in combination, wherein each R3Bis independently H or Ci -C4 alkyl.

[0132] Embodiment 43. A compound of Formula 1 or any one of Embodiments 1 through 42 either alone or in combination, wherein each R3Cis independently H or Ci -C4 alkyl.

[0133] Embodiment 44. A compound of Formula 1 or any one of Embodiments 1 through 43 either alone or in combination, wherein each R3Dis independently H or C 1-C4 alkyl.

[0134] Embodiment 45. A compound of Formula 1 or any one of Embodiments 1 through 44 either alone or in combination, wherein each n is independently 0 or 2.

[0135] Embodiment 46. A compound of Embodiment 45 wherein n is 2.

[0136] Embodiment 47. A compound of Embodiment 45 wherein n is 0.

[0137] Embodiment 48. A compound of Formula 1 or any one of Embodiments 1 through 47 either alone or in combination, provided that i) when Q is 5-chloro-2-pyridinyl; Z is O; and R3 is 4 chloro, then R2 is other than CI or Br; ii) when Q is 4-CF3-2- pyrimidinyl; Z is O; and m is 0, then R2 is other than CI or Br; and iii) when Q is 6-CF3-2-pyridinyl; Z is O; and m is 0, then R2 is other than Br.

[0138] Embodiments of the present invention as described in the Summary of the Invention and Embodiment AAA also include the following:

[0139] Embodiment IP. A compound of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Invention.

[0140] Embodiment 2P. A compound of Embodiment 1 wherein Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, and optionally substituted with 1 to 3 R1.

[0141] Embodiment 3P. A com ound of Embodiment 2 wherein Q is selected from

[0143] Q-1 Q-2 Q-3 Q-4 Q-5

[0144] Q-41 Q-43 Q-45

[0145] r is 0, 1, 2 or 3; and

[0146] s is 0 or 1.

[0147] Embodiment 4P. A compound of any one of Embodiments 1 through 3 wherein Q is a

[0148] 5- membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, optionally substituted with R1, and is selected from Q-1 through Q-41.

[0149] Embodiment 5P. A compound of Embodiment 4 wherein Q is selected from Q-7

[0150] through Q-24.

[0151] Embodiment 6P. A compound of Embodiment 5 wherein Q is selected from Q-9, Q- 11, Q-12, Q-16, Q-18, Q-22, Q-23, Q-24 and Q-25.

[0152] Embodiment 7P. A compound of Embodiment 6 wherein Q is selected from Q-11, Q- 18 and Q-22.

[0153] Embodiment 8P. A compound of any one of Embodiments 1 through 3 wherein Q is

[0154] 6- membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, optionally substituted with R1, and is selected from Q-42 through Q-54.

[0155] Embodiment 9P. A compound of Embodiment 8 wherein Q is selected from Q-42, Q-

[0156] 43, Q-44, Q-47, Q-48 and Q-49.

[0157] Embodiment 10P. A compound of Embodiment 9 wherein Q is selected from Q-42, Q- 43, Q-47 and Q-48.Embodiment 1 IP. A compound of Embodiment 10 wherein Q is selected from Q-42, Q-47 and Q-48.

[0158] Embodiment 12P. A compound of Embodiment 1 1 wherein Q is selected from Q-42. Embodiment 13P. A com ound of Embodiment 12 wherein Q is

[0160] Embodiment 14P. A compound of any one of Embodiments 1 through 3 wherein Q is selected from Q-7 through Q-24, Q-42, Q-43, Q-44, Q-47, Q-48 and Q-49.

[0161] Embodiment 15P. A compound of Embodiment 14 wherein Q is selected from Q-9, Q-l l , Q-12, Q-16, Q-18, Q-22, Q-23, Q-24, Q-25, Q-42, Q-43, Q-47 and Q-48.

[0162] Embodiment 16P. A compound of Embodiment 1 wherein Q is phenyl substituted with 1 to 3 Rl .

[0163] Embodiment 17P. A compound of Embodiment 16 whererin Q is phenyl substituted with 1 to 2 R! .

[0164] Embodiment 18P. A compound of Embodiment 17 wherein Q is phenyl substituted with 1 R1at the 3- or 4-positions (i.e. meta or para to the attachment of phenyl to the remainder of Formula 1).

[0165] Embodiment 19P. A compound of Embodiment 1 wherein when Q is phenyl

[0166] substituted with 1 to 3 R1, m is 1 , 2 or 3.

[0167] Embodiment 20P. A compound of Embodiment 1 wherein when Q is phenyl

[0168] substituted with 1 to 3 R1, m is 1 or 2.

[0169] Embodiment 2 IP. A compound of Embodiment 1 wherein Q is other than phenyl

[0170] substituted with 1 to 4 R1.

[0171] Embodiment 22P. A compound of any one of Embodiments 1 through 21 wherein R1is halogen, cyano, CHO, -C4 alkyl, C2-C4alkenyl, C2-C4alkynyl, -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl or SOnR1A.

[0172] Embodiment 23P. A compound of Embodiment 22 wherein R1is halogen, cyano, -C4 alkyl, C1-C4 alkoxy, -C4 haloalkyl, -C4 haloalkoxy, or SCF3.

[0173] Embodiment 24P. A compound of Embodiment 23 wherein R1is halogen, y-C^ alkyl or C1-C4 haloalkyl or y-C^ haloalkoxy.

[0174] Embodiment 25P. A compound of Embodiment 24 wherein R1is halogen y-C^

[0175] haloalkyl or y-C^ haloalkoxy.

[0176] Embodiment 26P. A compound of Embodiment 25 wherein R1is CI, Br, CF3or OCF3.Embodiment 27P. A compound of any one of Embodiments 1 through 22 wherein each n is independently 0, 1 or 2.

[0177] Embodiment 28P. A compound of Embodiment 27 wherein each n is independently 0. Embodiment 29P. A compound of Embodiment 28 wherein each n is independently 2. Embodiment 30P. A compound of any one of Embodiments 1 through 29 wherein R2is halogen, C1 -C4 alkyl or C 1 -C4 haloalkyl.

[0178] Embodiment 3 IP. A compound of Embodiment 30 wherein R2is halogen or C1 -C4 alkyl.

[0179] Embodiment 32P. A compound of Embodiment 31 wherein R2is halogen or CH3. Embodiment 33P. A compound of Embodiment 32 wherein R2is halogen.

[0180] Embodiment 34P. A compound of Embodiment 33 wherein R2is F, CI or Br.

[0181] Embodiment 35P. A compound of any one of Embodiments 1 through 34 wherein m is 0, 1 or 2.

[0182] Embodiment 36P. A compound of Embodiment 35 wherein m is 0 or 1.

[0183] Embodiment 37P. A compound of Embodiment 36 wherein m is 1.

[0184] Embodiment 38P. A compound of Embodiment 37 wherein m is 0 (i.e. the 3-, 4-, 5- and 6-positions of the benzene ring are unsubtituted by R3).

[0185] Embodiment 39P. A compound of any one of Embodiments 1 through 37 wherein each R3is independently halogen, cyano, hydroxy, nitro, amino, CHO, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4alkynyl, C(=0)N(R3A)(R3B), C(=NOR3C)H,

[0186] C(=N)(R3D)H, CrC4alkoxy, C2-C4cyanoalkoxy, C2-C4alkylcarbonyl, C2-C4alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl, C 1 -C4 haloalkyl, CrC4haloalkoxy, SOnR3Eor C3-C6cycloalkyl.

[0187] Embodiment 40P. A compound of Embodiment 39 wherein each R3is independently halogen, cyano, amino, C1 -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1 -C4 alkoxy, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl or C1 -C4 haloalkyl.

[0188] Embodiment 41P. A compound of Embodiment 40 wherein each R3is independently halogen, cyano, amino or C 1 -C4 alkyl.

[0189] Embodiment 42P. A compound of Embodiment 41 wherein each R3is independently cyano.

[0190] Embodiment 43P. A compound of any one of Embodiments 1 through 37 or 39

[0191] through 42 wherein each R3is attached to the remainder of Formula 1 at the 3-, 4- or 6-position.

[0192] Embodiment 44P. A compound of Embodiments 43 wherein each R3is attached to the remainder of Formula 1 at the 3- or 4-position.

[0193] Embodiment 45P. A compound of Embodiment 44 wherein R3is attached to the

[0194] remainder of Formula 1 at the 3 -position.Embodiment 46P. A compound of any one of Embodiments 1 through 22 or 27 or 29 through 45 wherein R1Ais Ci -C4 alkyl or Ci -C4 haloalkyl.

[0195] Embodiment 47P. A compound of Embodiment 46 wherein R1Ais Ci -C4 haloalkyl. Embodiment 48P. A compound of any one of Embodiments 1 through 37 or 39

[0196] wherein R3Eis Ci -C4 alkyl.

[0197] Embodiment 49P. A compound of any one of Embodiments 1 through 37 or 39

[0198] wherein R3Ais C 1 -C4 alkyl.

[0199] Embodiment 50P. A compound of any one of Embodiments 1 through 37 or 39

[0200] wherein R3Bis H or Ci -C4 alkyl.

[0201] Embodiment 5 IP. A compound of any one of Embodiments 1 through 37 or 39

[0202] wherein R3Cis H or Ci -C4 alkyl.

[0203] Embodiment 52P. A compound of any one of Embodiments 1 through 37 or 39

[0204] wherein R3Dis H or Ci -C4 alkyl.

[0205] Embodiment 53P. A compound of any one of Embodiments 1 through 52 wherein Z is

[0206] O.

[0207] Embodiment 54P. A compound of any one of Embodiments 1 through 53 wherein

[0208] when m is 1, R3is positioned at the 3-, 5- or 6-positions (i.e. the 3-, 5- and 6- positions of the benzene ring).

[0209] Embodiment 55P. A compound of any one of Embodiments 1 through 53 wherein

[0210] when m is 1, R3is other than CI at the 4-position.

[0211] Embodiments of this invention, including Embodiments 1-48 and 1P-55P above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the a compound of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments 1-48 and 1P-55P above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

[0212] Embodiment AAA. A compound of Formula 1 wherein

[0213] Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of

[0214] Formula 1 through a carbon atom, and optionally substituted with 1 to 4 R1; or Q is phenyl substituted with 1 to 4 R1;

[0215] Z is O or S;

[0216] R1is halogen, cyano, CHO, C1 -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci -C4 haloalkyl, Ci -C4 haloalkoxy, C2- C4 alkoxyalkyl, C2-C4 alkylthioalkyl, SOnR1A, C2-Cg dialkylamino, C1 -C4 cyanoalkyl, C 1 -C4 hydroxyalkyl, CH(=NOH) or C3-C6 cycloalkyl; or unsubstituted phenyl; or unsubstituted pyridyl;R2is halogen, cyano, nitro, C1 -C4 alkoxy, C 1 -C4 alkyl, C2-Cg alkenyl, C2-Cg alkynyl, SOnR2Aor C1-C4 haloalkyl;

[0217] each R3is independently halogen, cyano, hydroxy, nitro, amino, CHO, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4alkynyl, C(=0)N(R3A)(R3B), C(=NOR3C)H, C(=N)(R3D)H, CrC4alkoxy, C2-C4cyanoalkoxy, C2-C4alkylcarbonyl, C2-C4alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl, C 1 -C4 haloalkyl, Ci -C4 haloalkoxy, SOnREor C3-C6 cycloalkyl; or phenyl optionally substituted with cyano, halogen or Ci -C4 alkyl;

[0218] m is 0, 1, 2 or 3;

[0219] each R1A, R2Aand R3Eis independently CrC4alkyl, CrC4haloalkyl, CrC4

[0220] alkylamino ordialkylamino;

[0221] R3Ais C1-C4 alkyl or CrC4haloalkyl;

[0222] R3Bis H, CrC4alkyl or CrC4haloalkyl;

[0223] RCis independently H or Ci -C4 alkyl;

[0224] RDis independently H or C 1 -C4 alkyl; and

[0225] n is 0, 1, or 2;

[0226] provided the compound of Formula 1 is other than 5-chloro-2-[(4'-methyl[l,l'- biphenyl]2-yl)oxy]-pyrimidine (CAS # 107492-74-0), 5-chloro-2-[(4'- chloro[l,r-biphenyl]2-yl)oxy]-pyrimidine (CAS # 107492-72-8), 5-chloro-2- [(3*-chloro[l,r-biphenyl]2-yl)oxy]-pyrimidine (CAS # 107492-76-2) and 5-chloro-2-[[3'-(trifluoromethyl)[ 1 , 1 '-biphenyl]2-yl]oxy]-pyrimidine (CAS # 107492-75-1); and provided i) when Q is 5-chloro-2-pyridinyl; Z is O; and R3is 4-chloro, then R2is other than CI or Br; ii) when Q is 4-CF3-2-pyrimidinyl; Z is O; and m is 0, then R2is other than CI or Br; and iii) when Q is 6-CF3-2- pyridinyl; Z is O; and m is 0, then R2is other than Br.

[0227] Embodiment AA. A compound of Embodiment AAA or a compound of Formula 1 as described in the Summary of the Invention wherein

[0228] Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of

[0229] Formula 1 through a carbon atom, and optionally substituted with 1 to 4 R1; Z is O or S;

[0230] each R1is independently halogen, cyano, nitro, SF5, CHO, C(=0)NH2, C(=S)NH2, S02NH2, CrC4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyl, C2-C4haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2-Cg alkylaminocarbonyl, C3-C10 dialkylaminocarbonyl, C1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8cycloalkylalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg

[0231] alkoxyhaloalkyl, C2~Cg alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, Ci -C4 hydroxyalkyl, C2-C4 alkylthioalkyl, SOnR1A, Si(CH3)3or B(-OC(R1B)2C(R1B)20-); or a phenyl ring optionally substituted with up to 5 substituents independently selected from R1C; or a 5- or

[0232] 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R1Con carbon atom ring members and R1Don nitrogen atom ring members;

[0233] R2is halogen, cyano, nitro, C1 -C4 alkoxy, C 1 -C4 alkyl, C2-Cg alkenyl, C2-Cg alkynyl,

[0234] SOnR2A, C1-C4 haloalkyl or C3-C6cycloalkyl;

[0235] each R3is independently halogen, cyano, hydroxy, nitro, amino, CHO, C(=0)NH2, C(=S)NH2, S02NH2, CrC4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C4-C8 alkylcycloalkyl, C4-C8 cycloalkylalkyl, C2~Cg alkylcarbonyl, C2~Cg haloalkylcarbonyl, C2~Cg alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C 1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1 -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C3-C6 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C8 cycloalkylalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg alkoxyhaloalkyl, C2~Cg alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-Cg cyanoalkyl, C2-Cg cyanoalkoxy, C2-C4 alkylthioalkyl, Si(CH3)3, C≡CSi(CH3)3, C(=0)N(R3A)(R3B), C(=NOR3C)H, C(=NR3D)H, SOnRE; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from RFon carbon atom ring members and R3Gon nitrogen atom ring members; or pyrimidinyloxy;

[0236] m is 0, 1, 2 or 3;

[0237] each n is independently 0, 1 or 2;

[0238] each R1A, R2Aand R3Eis independently CrC4alkyl, CrC4haloalkyl, CrC4

[0239] alkylamino or C2-C6 dialkylamino;

[0240] each R1Bis independently H or Ci -C4 alkyl;

[0241] each R1Cis independently hydroxy, halogen, cyano, nitro, C^-Cg alkyl, C^-Cg

[0242] haloalkyl, C^-Cg alkoxy or C^-Cg haloalkoxy;each R1Dis independently cyano, C^-Cg alkyl, C^-Cg haloalkyl, C^-Cg alkoxy or C2-

[0243] Cg alkylcarbonyl;

[0244] each R3Ais independently Ci -C4 alkyl or Ci -C4 haloalkyl;

[0245] each R3Bis independently H, Ci -C4 alkyl or Ci -C4 haloalkyl;

[0246] each R3Cis independently H or Ci -C4 alkyl;

[0247] each R3Dis independently H, amino, Ci -C4 alkyl or Ci -C4 alkylamino;

[0248] each RFis independently hydroxy, halogen, cyano, nitro, C^-Cg alkyl, C^-Cg

[0249] haloalkyl, C^-Cg alkoxy or C^-Cg haloalkoxy; and

[0250] each RGis independently cyano, C^-Cg alkyl, C^-Cg haloalkyl, C^-Cg alkoxy or C2- Cg alkylcarbonyl;

[0251] Embodiment A. A compound of Embodiment AA wherein

[0252] Q is selected from Q-l through Q-55 wherein r is 0, 1, 2 or 3; and s is 0 or 1;

[0253] each R1is independently halogen, cyano, SF5, CHO, Ci -C4 alkyl, C2-C4 alkenyl,

[0254] C2-C4 alkynyl, Ci -C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C2~Cg alkylcarbonyl, C2~Cg haloalkylcarbonyl, C2~Cg alkoxycarbonyl, C1-C4 alkoxy,

[0255] C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-Cg cyanoalkyl, C1-C4 hydroxyalkyl, C2-C4 alkylthioalkyl or SOnR1A;

[0256] R3is independently halogen, cyano, CHO, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, i -C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-Cg cycloalkyl,

[0257] C3-Cg halocycloalkyl, C4-C8 alkylcycloalkyl, C2~Cg alkylcarbonyl, C2~Cg haloalkylcarbonyl, C2~Cg alkoxycarbonyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3- C4 alkynyloxy, Ci -C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4

[0258] haloalkynyloxy, C3~Cg cycloalkoxy, C3~Cg halocycloalkoxy, C2-Cg alkoxyalkyl, C2-Cg haloalkoxyalkyl, C2-C4 alkylcarbonyloxy, C2-Cg cyanoalkyl,

[0259] C(=0)N(R3A)(R3B), C(=NOR3C)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substituents independently selected from RF; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3Fon carbon atom ring members and R3Gon nitrogen atom ring members;

[0260] Z is O; and

[0261] m is 0, 1 or 2.

[0262] Embodiment B. A compound of Embodiment A wherein

[0263] each R1is independently halogen, cyano, CHO, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci -C4 haloalkoxy, C3-C4 haloalkenyloxy,C3-C4 haloalkynyloxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C1 -C4 hydroxyalkyl, C2-C4alkylthioalkyl or SOnR1A;

[0264] R2is halogen, Ci -C4 alkyl or Ci -C4 haloalkyl;

[0265] each R3is independently halogen, cyano, CHO, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1 -C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-Cg alkylcarbonyl, C2-Cg

[0266] haloalkylcarbonyl, C2-C6 alkoxycarbonyl, Ci -C4 alkoxy, Ci -C4 haloalkoxy, C2-C6 alkoxyalkyl, C2-C6 haloalkoxyalkyl, C2-C6 cyanoalkyl, SOnR3E; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R3Fon carbon atom ring members and R3Gon nitrogen atom ring members; and

[0267] m is 0 or 1.

[0268] Embodiment C 1. A compound of Embodiment B wherein

[0269] Q is selected from Q-7 through Q-24;

[0270] each R1is independently halogen, cyano, Ci -C4 alkyl, Ci -C4 haloalkyl, Ci -C4 alkoxy,

[0271] CrC4haloalkoxy or SOnR1A;

[0272] R2is halogen or Ci -C4 alkyl;

[0273] each R3is independently halogen, cyano, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl,

[0274] C1 -C4 haloalkyl, C2-Cg alkylcarbonyl, C2-Cg haloalkylcarbonyl, C2-Cg alkoxycarbonyl, C1 -C4 alkoxy, C 1 -C4 haloalkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl; and

[0275] each R1Ais independently Ci -C4 alkyl or Ci -C4 haloalkyl.

[0276] Embodiment C2. A compound of Embodiment B wherein

[0277] Q is selected from Q-43, Q-44, Q-45, Q-48, Q-49 and Q-50;

[0278] each R1is independently halogen, cyano, Ci -C4 alkyl, Ci -C4 haloalkyl, Ci -C4 alkoxy,

[0279] CrC4haloalkoxy or SOnR1A;

[0280] R2is halogen or Ci -C4 alkyl;

[0281] each R3is independently halogen, cyano, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl,

[0282] C1 -C4 haloalkyl, C2-C6 alkylcarbonyl, C2-C6 haloalkylcarbonyl, C2-C6 alkoxycarbonyl, C1 -C4 alkoxy, C 1 -C4 haloalkoxy, C2-C6 alkoxyalkyl or C2-C6 haloalkoxyalkyl; and

[0283] each R1Ais independently Ci -C4 alkyl or Ci -C4 haloalkyl.

[0284] Embodiment D 1. A compound of Embodiment C 1 wherein

[0285] Q is selected from Q-16 and Q-18;

[0286] each R1is independently halogen, Ci -C4 alkyl, Ci -C4 haloalkyl or Ci -C4 haloalkoxy; R2is halogen or CH3; andeach R3is independently halogen, cyano, Ci -C4 alkyl or C i -C4 haloalkyl.

[0287] Embodiment D2. A compound of Embodiment C2 wherein

[0288] Q is selected from Q-43, Q-44 and Q-45;

[0289] each R1is independently halogen, Ci -C4 alkyl, C i -C4 haloalkyl or Ci -C4 haloalkoxy; R2is halogen or CH3; and

[0290] each R3is independently halogen, cyano, Ci -C4 alkyl or C i -C4 haloalkyl.

[0291] Specific embodiments include compounds of Formula 1 selected from the group consisting of:

[0292] 5-chloro-2-[2-(5-chloro-2-pyridinyl)phenoxy]pyrimidine (Compound 1),

[0293] 5-chloro-2-[2-[5-(fluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine (Compound 32),

[0294] 2-[2-(3-bromo-5-isoxazolyl)phenoxy]-5-chloropyrimidine (Compound 12),

[0295] 5-chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine (Compound 27),

[0296] 5-chloro-2-[3-chloro-2-(5-chloro-2-pyridinyl)phenoxy]pyrimidine (Compound 23),

[0297] 4- [2-[(5-bromo-2-pyrimidinyl)oxy]phenyl]-2-(trifluoromethyl)pyrimidine

[0298] (Compound 21),

[0299] 2- [2-(2-bromo-5 -thiazolyl)phenoxy] -5 -(trifluoromethyl)pyrimidine (Compound 15),

[0300] 5- chloro-2-[4-methyl-2-[2-(trifluoromethyl)-4-pyridinyl]phenoxy]pyrimidine

[0301] (Compound 24),

[0302] 5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine (Compound 35),

[0303] 5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine (Compound 53),

[0304] 5 -chloro-2-[2- [5 -(difluoromethyl)-3 -isoxazolyl] -3 -fluorophenoxy]pyrimidine

[0305] (Compound 55),

[0306] 5-bromo-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine (Compound

[0307] 62) ,

[0308] 5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine (Compound

[0309] 63) ,

[0310] 5 -chloro-2-[2- [3 -(difluoromethyl)-5 -isoxazolyl] -3 -fluorophenoxy]pyrimidine

[0311] (Compound 144),

[0312] 5 -bromo-2- [2- [3 -(difluoromethyl)-5 -isoxazolyl]-3 -fluorophenoxy]pyrimidine

[0313] (Compound 145),

[0314] 5 -chloro-2-[2-[5 -(trifluoromethyl)-3 -isoxazolyl] -3 -fluorophenoxy]pyrimi dine

[0315] (Compound 168) and5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine (Compound 200).

[0316] Embodiments of the present invention as described in the Summary of the Invention and Embodiment AAA also include the following:

[0317] Embodiment Ap. A compound of the Summary of the Invention wherein

[0318] Q is a 5- or 6-membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, and optionally substituted with 1 to 3 R1; or

[0319] Q is phenyl substituted with 1 to 3 R1;

[0320] R1is halogen, cyano, CHO, C1 -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1 -C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, Ci -C4 haloalkyl, Ci -C4 haloalkoxy, C2- C4alkoxyalkyl, C2-C4alkylthioalkyl or SOnR1A;

[0321] each n is independently 0, 1 or 2

[0322] R2is halogen, Ci -C4 alkyl or Ci -C4 haloalkyl;

[0323] m is 0, 1 or 2;

[0324] each R3is independently halogen, cyano, hydroxy, nitro, amino, CHO, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4alkynyl, C(=0)N(R3A)(R3B), C(=NOR3C)H, C(=N)(R3D)H, CrC4alkoxy, C2-C4cyanoalkoxy, C2-C4alkylcarbonyl, C2-C4alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl, C 1 -C4 haloalkyl, CrC4haloalkoxy, SOnR3Eor C3-C6cycloalkyl;

[0325] each R3is attached to the remainder of Formula 1 at the 3-, 4- or 6-position;

[0326] R1Ais C1-C4 alkyl or CrC4haloalkyl;

[0327] R3Eis CrC4alkyl;

[0328] R3Ais C1-C4 alkyl;

[0329] R3Bis H or CrC4alkyl;

[0330] R3Cis H or CrC4alkyl; and

[0331] R3Dis H or CrC4alkyl.

[0332] Embodiment Bp. A compound of Embodiment A wherein

[0333] Q is selected from Q-l through Q-54 (i.e. as described in Embodiment 3);

[0334] Z is O;

[0335] R1is halogen, cyano, C 1 -C4 alkyl, C1 -C4 alkoxy, C 1 -C4 haloalkyl, C1 -C4 haloalkoxy, or SCF3;

[0336] R2is halogen or Ci -C4 alkyl;

[0337] m is 0 or 1 ;

[0338] each R3is independently halogen, cyano, amino, Ci -C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C 1 -C4 alkoxy, C2-C4 alkoxycarbonyl, C2-C4 alkylcarbonyloxy, C2-C4 alkoxyalkyl or Ci -C4 haloalkyl; and

[0339] each R3is attached to the remainder of Formula 1 at the 3- or 4-position.

[0340] Embodiment Cp. A compound of Embodiment B whereinQ is a 5-membered aromatic heterocylic ring, bound to the remainder of Formula 1 through a carbon atom, optionally substituted with R1, and is selected from Q-l through Q-41;

[0341] R1is halogen C1-C4 haloalkyl or C1-C4 haloalkoxy;

[0342] R2is halogen or CH3; and

[0343] each R3is independently halogen, cyano, amino or C1-C4 alkyl.

[0344] Embodiment Dp. A compound of Embodiment C wherein

[0345] Q is 6-membered aromatic heterocylic ring, bound to the remainder of Formula 1

[0346] through a carbon atom, optionally substituted with R1, and is selected from Q-42 through Q-54;

[0347] R1is halogen C1-C4 haloalkyl or C1-C4 haloalkoxy;

[0348] R2is halogen or CH3; and

[0349] each R3is independently halogen, cyano, amino or C1-C4 alkyl.

[0350] Embodiment Ep. A compound of Embodiment D wherein

[0351] Q is selected from Q-42, Q-43, Q-44, Q-47, Q-48 and Q-49;

[0352] R1is CI, Br, CF3or OCF3;

[0353] R2is halogen; and

[0354] each R3is independently cyano.

[0355] Specific embodiments include a compound of Formula 1 selected from the group consisting of:

[0356] 5 -chloro-2- [2-(5 -chloro-2-pyridinyl)phenoxy]pyrimidine (Compound 1 );

[0357] 5-chloro-2-[2-[5-(fluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine (Compound 32); 2-[2-(3-bromo-5-isoxazolyl)phenoxy]-5-chloropyrimidine (Compound 12);

[0358] 5 -chloro-2- [[4'-(trifluoromethoxy) [1,1 '-biphenyl] -2-yl]oxy]pyrimidine (Compound 42);

[0359] 5 -chloro-2- [2- [5 -(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine (Compound 27); 5 -chloro-2- [3 -chloro-2-(5 -chloro-2 -pyridinyl)phenoxy]pyrimidine (Compound 23); 4- [2- [(5 -bromo-2-pyrimidinyl)oxy]phenyl] -2-(trifluoromethyl)pyrimidine (Compound

[0360] 21);

[0361] 2-[2-(2-bromo-5-thiazolyl)phenoxy]-5-(trifluoromethyl)pyrimidine (Compound 15); and

[0362] 5 -chloro-2- [4-methyl-2- [2-(trifluoromethyl)-4-pyridinyl]phenoxy]pyrimidine

[0363] (Compound 24).

[0364] 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. Compounds of the invention are particularly useful for selective control of weeds in cropssuch as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.

[0365] Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.

[0366] This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics and (b5) 5 -enol-pyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (blO) auxin transport inhibitors, (bl 1) phytoene desaturase (PDS) inhibitors, (bl2) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (bl3) homogentisate solenesyltransererase (HST) inhibitors, (bl4) cellulose biosynthesis inhibitors, (bl5) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (bl6) herbicide safeners; and salts of compounds of (bl) through (bl6).

[0367] "Photosystem II inhibitors" (bl) are chemical compounds that bind to the D-l protein at the Qfl-binding niche and thus block electron transport from to QB in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The QB-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine.

[0368] "AHAS inhibitors" (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants byinhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron- sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-l ,3,5-triazin-2- yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4- (5,6-dihydro-5-methyl-l,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]- 1 -methyl- lH-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2- pyrimidinyl)amino] carbonyl] -6-propylimidazo [ 1 ,2-¾]pyridazine-3 -sulfonamide),

[0369] prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-l,3,5-triazin-2-yl)carbonyl]-6- fluorophenyl] -1,1 -difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron.

[0370] "ACCase inhibitors" (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.

[0371] Auxin is a plant hormone that regulates growth in many plant tissues. "Auxin mimics" (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl- 4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba,2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro- 3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro- 6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.

[0372] "EPSP (5 -enol-pyruvylshikimate-3 -phosphate) synthase inhibitors" (b5) are chemical compounds that inhibit the enzyme, 5 -enol-pyruvylshikimate-3 -phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).

[0373] "Photosystem I electron diverters" (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles "leak", leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.

[0374] "PPO inhibitors" (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil (methyl N-[2- [[2-chloro-5-[3 ,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- 1 (2H)-pyrimidinyl]-4- fluorophenyl]thio]-l-oxopropyl]-P-alaninate) and 3-[7-fluoro-3,4-dihydro-3-oxo-4-(2- propyn- 1 -yl)-2H- 1 ,4-benzoxazin-6-yl] dihydro- 1 ,5 -dimethyl-6-thioxo- 1 ,3 ,5 -triazine- 2,4(lH,3H)-dione.

[0375] "GS (glutamine synthase) inhibitors" (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricinderivatives, glufosinate-P ((25)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.

[0376] "VLCFA (very long chain fatty acid) elongase inhibitors" (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro- 5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)-N,N-diethyl-2-(l- naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides.

[0377] "Auxin transport inhibitors" (blO) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(l-naphthyl)phthalamic acid and 2-[(l-naphthalenylamino)carbonyl]benzoic acid).

[0378] "PDS (phytoene desaturase inhibitors) (bl l) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone norflurzon and picolinafen.

[0379] "HPPD (4-hydroxyphenyl-pyruvate dioxygenase) inhibitors" (bl2) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3 -[ [2-[(2-methoxyethoxy)methyl] -6-(trifluoromethyl)-3 - pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro- 4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-l,3-cyclohexanedione),

[0380] isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 5-chloro-3-[(2-hydroxy-6-oxo-l- cyclohexen-l-yl)carbonyl]-l-(4-methoxyphenyl)-2(lH)-quinoxalinone, 4-(2,6-diethyl-4- methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2- hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-2-methyl-l,2,4-triazine-3,5(2H,4H)-dione, 5- [(2-hydroxy-6-oxo-l-cyclohexen-l-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)- 4(3H)-pyrimidinone, 2-methyl-N-(4-methyl- 1 ,2,5-oxadiazol-3-yl)-3-(methylsulfmyl)-4- (trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(l -methyl- lH-tetrazol-5-yl)- 4-(trifluoromethyl)benzamide.HST (homogentisate solenesyltransererase) inhibitors (bl3) disrupt a plant's ability to convert homogentisate to 2-methyl-6-solanyl-l ,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, 3-(2- chloro-3 ,6-difluorophenyl)-4-hydroxy- 1 -methyl- 1 ,5 -naphthyridin-2( lH)-one, 7-(3 ,5 - dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-¾]pyrazin-6(5H)-one and 4- (2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

[0381] HST inhibitors also include com ounds of Formulae A and B.

[0383] B

[0384] wherein Rdlis H, CI or CF3; Rd2is H, CI or Br; Rd3is H or CI; Rd4is H, CI or CF3; Rd5is CH3, CH2CH3or CH2CHF2; and Rd6is OH, or -OC(=0)-z-Pr; and Relis H, F, CI, CH3or CH2CH3; Re2is H or CF3; Re3is H, CH3or CH2CH3; Re4is H, F or Br; Re5is CI, CH3, CF3, OCF3or CH2CH3; Re6is H, CH3, CH2CHF2or C≡CH; Re7is

[0385] OH, -OC(=0)Et, -OC(=0)-z-Pr or -OC(=0)-t-Bu; and Ae8is N or CH.

[0386] Cellulose biosynthesis inhibitors (bl4) inhibit the biosynthesis of cellulose in certain plants. They are most effective when using a pre-aplication or early post-application on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N2-[(li?,25)-2,3-dihydro-2,6-dimethyl-lH- inden-l-yl]-6-(l-fluoroethyl)-l ,3,5-triazine-2,4-diamine), isoxaben and triaziflam.

[0387] Other herbicides (bl5) include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl) organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors. Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (bl) through (bl4) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, cyclopyrimorate (6-chloro-3-(2- cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone ( 1 -(2,4-dichlorophenyl)-N-(2,4-dif uorophenyl)- 1 ,5-dihydro-N-( 1 - methylethyl)-5-oxo-4H-l ,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid,oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]- 4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

[0388] "Herbicide safeners" (bl6) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N- (aminocarbonyl)-2-fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-l,3-dioxolane (MG 191), 4-(dichloroacetyl)-l-oxa- 4-azospiro[4.5]decane (MON 4660).

[0389] The compounds of Formula 1 can be prepared by general methods known in the art of synthetic organic chemistry. One or more of the following methods and variations as described in Schemes 1-9 can be used to prepare the compounds of Formula 1. The definitions of Q, R1, R2and R3in the compounds of Formulae 1-11 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1A-1C, 2A-2F, 4A and 8A are various subsets of the compounds of Formula 1, 2 4 and 8 and all substituents for Formulae 1A-1C, 2A-2F, 4A and 8A are as defined above for Formula 1 unless otherwise noted.

[0390] One or more of the following methods and variations as described in Schemes 1-9 can be used to prepare the compounds of Formula 1. The definitions of Q, R1, R2and R3in the compounds of Formulae 1-11 below are as defined above in the Summary of the Invention unless otherwise noted.

[0391] As shown in Scheme 1 a compound of Formula 1 can be prepared by nucleophilic substitution by heating a compound of Formula 2 in a suitable solvent, such as acetonitrile, tetrahydrofuran or N,N-dimethylformamide in the presence of a base such as potassium or cesium carbonate, at temperatures ranging from 50 to 110 °C, with a compound of Formula 3 (where LG is halogen or S02Me). The reaction is typically conducted at temperatures ranging from 50 to 110 °C.Scheme 1

[0393] LG is halogen or SO2CH3

[0394] Alternatively, as shown in Scheme 2, boron compounds of Formula 5 or tin compounds of Formula 6 can be coupled with intermediates of Formula 4 under Suzuki or Stille conditions to give compounds of Formula 1. Suzuki couplings typically are conducted in the presence of Pd(0) or Pd(II) salts, a suitable ligand, and a base. Suitable bases for this transformation include potassium carbonate or cesium carbonate, while Pd(II) salts such as Pd(OAc)2or PdCl2can be used in conjunction with ligands such as triphenylphosphine or l,l'-bis(diphenylphosphino)ferrocene (dppf). Conditions for Suzuki couplings are well documented in the literature (see for example Angewandte Chemie International Edition 2006, 45, 3484 and Tetrahedron Letters 2002, 55(14), 2885). Boron intermediates of Formula 5 are commercially available or can be prepared from the corresponding halides or trifluoromethanesulfonates by methods known in the literature (see for example PCT Patent Publication WO 2007 / 043278, US Pat. No. 8,080,566, Organic Letters 2011, 75(6), 1366 and Organic Letters 2012, 14(2), 600). Stille couplings typically can be conducted in the presence of Pd(0) or a Pd(II) salt, a ligand and a Cu(I) salt such as copper(I) iodide. The reaction can be run in a solvent such as dioxane, 1 ,2-dimethoxyethane or toluene at a temperature ranging from ambient to reflux. For conditions and reagents employed in Stille couplings see Chemical Reviews 2007, 107(1), 133-173.

[0395] Scheme 2

[0396] ,B(OR)2

[0397] palladium catalyst,

[0399] R = C , - C4alkyl

[0400] As shown in Scheme 3, a compound of Formula 2C (i.e. a compound of Formula 2 where Z is O) can be prepared by deprotection of a compound of Formula 2B (i.e. a compound of Formula 2A wherein Z is O; and R^ is CH3 or -C(=0)CH3) with a suitable deprotecting agent. Suitable methoxy (i.e. when RAis CH3) deprotecting reagents such as BBr3, AICI3 and HBr in acetic acid can be used in the presence of solvents such as toluene, dichloromethane and dichloroethane at a temperature of from -80 to 120 °C. Suitable acetoxy (i.e. when RAis -C(=0)CH3) deprotecting agents include potassium carbonate in methanol or ammonium acetate in aqueous methanol at room temperature can be used as discussed in Das, et al, Tetrahedron 2003, 59, 1049-1054 and methods cited therein. Alternatively, a compound of Formula 2B can be combined with Amberlyst 15® in methanol (as discussed in Das, et al. Tet. Lett. 2003, 44, 5465-5468) or combined with sodium acetate in ethanol (as discussed in Narender, T., et al. Synthetic Communications 2009, 39(11), 1949-1956) to obtain a compound of Formula 2C. Other useful phenolic protecting groups suitable for use in preparing a compound of Formula 2C can be found in Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, New Jersey, 1991.

[0401] Scheme 3

[0403] 2B

[0404] RA= CH3or -C(=0)CH32CAn intermediate of Formula 2B can be prepared as shown in Scheme 4 from an intermediate of Formula 7 by a variety of methods known to one skilled in the art. Compounds of Formula 2B can be accessed by coupling precursors of Formula 7 wherein J is Br, CI, I or trifluoromethanesulfonate with boronate or trialkyltin group-containing heterocycles (i.e compounds of Formula 5 or Formula 6 using the Suzuki conditions or the Stille conditions of Scheme 2). Alternatively, compounds of Formula 7 wherein J is a boronate or trialkyltin group may be coupled with halogen-substituted heterocycles Q-X using the methods shown in Scheme 2 to afford compounds of Formula 2B. The skilled chemist will realize that with the prudent choice of groups X and J in reactions involving compounds of Formula 7 and Q-X can synthesize the intermediate 2B utilizing various cross coupling procedures such as Kumada coupling, Hiyama coupling or Negishi coupling described in "Metal-Catalyzed Cross-Coupling Reactions", Eds. A. de Meijere and F. Diederich, Wiley- VCH, Weinheim, 2004, vols 1 and 2.

[0405] When J in Formula 7 is an alkene, alkyne, oxime, nitrile or ketone, various heterocycles can be prepared using methods described in Katritsky, Advances in Heterocyclic Chemistry, Vol. 1-104, Elsevier. In cases where regioisomeric mixtures are produced, the desired product can be isolated using routing separation techniques known in the art.

[0406] Scheme 4

[0407] 7 2B

[0408] RAis CH3or -C(=0)CH3

[0409] As shown in Scheme 5, a compound of Formula 4A can be prepared by coupling of phenols of Formula 9 with a compound of Formula 3 under the nucleophilic substitution conditions described in Scheme 1.

[0410] 5

[0412] 4A

[0413] or OS02CF3

[0414] As shown in Scheme 6, a compound of Formula IB, (i.e. a compound of Formula 1 where Z is O; and m is 1 at the 3-position) can be prepared by "C-H activation" of a compound of Formula 1A (a compound of Formula 1 wherein Z is O; and m is 0). Forexample, paladium(II) acetate along with either an N-halosuccinimide, PhI(OAc)2, N-fluoropyridinium tetrafluoroborate, or a lower alkyl boronic acid can be used to introduce the R3variable as I, Br, CI, -OAc, F, and lower alkyl substituents respectively. These methods are detailed in reviews of selective activation of C-H bonds in Chemical Reviews 2010, 110, 575-1211 and references cited therein. Methods for "C-H activation" can also be found in Wencel-Delord et al, Nature Chemistry 2013, 5, 369-375 and a series of reviews of "C-H activation" in Accounts of Chemical Research 2012, 45, 777-958 and references cited therein. Iodides and bromides of Formula IB can then be further functionalized by various cross coupling procedures described in "Metal-Catalyzed Cross-Coupling Reactions", Eds A. de Meijere and F. Diederich, Wiley- VCH, Weinheim, 2004, vols 1 and 2.

[0415] heme 6

[0417] Chemistry based on "C-H activation" can also be used to prepare a compound of Formula 2D (i.e. a compound of Formula 2 wherein Z is O; R is -C(0)CH3; and m is 1 at the 3 -position) as shown in Scheme 7 utilizing palladium(II) acetate and (diacetoxyiodo)benzene as described above for Scheme 6. A compound of Formula 2D can subsequently be converted via methods disclosed in Schemes 1 and 6 to provide a compound of Formula 1.

[0418] Scheme 7

[0420] Similarly, chemistry based on "C-H activation" can be used to prepare a compound of Formulae 2F (i.e. a compound of Formula 2A wherein Z is S) as shown in Scheme 8. A compound of Formula 8 can first be converted to a compound of Formula 8A (i.e. a compound of Formula 6 wherin the ortho "H" is X; and X is Br or I) by utilizing a stepwise introduction of substituents using "C-H activation". Iodides and bromides of Formula 8A can then be further functionalized by copper mediated cross-coupling with thiourea asdescribed in Qi, Junsheng, Chin. J. Chem. 2010, 28, 1441-1443 to provide the aryl thiol after acidic deprotection. Palladium catalyzed cross-coupling reactions of aryl halides can give protected thiols that can, in turn, be deprotected under either acidic conditions or basic conditions (e.g. cesium fluoride) to provide a compound of Formula 2F. These conditions are discussed in Organ, Michael G., Angew. Chem. Int. Ed. 2012, 51, 3314-3322 and the references cited therein. Also, relevant conditions can be found in Takashiro Itoh, J. Org. Chem. 2006, 71, 2203-2206. A compound of Formula 2F can then be converted via methods disclosed in Schemes 1 and 7 to provide a compound of Formula 1.

[0421] Scheme 8

[0422] C-H activation

[0423] (stepwise when

[0424] RJis other than H)

[0425] X is Br or I

[0426] 8 8A 2F

[0427] In Scheme 9, the phenol, 2E is reacted with N,N-dimethyl thiocarbamoyl chloride in N,N-dimethylformamide in the presence of a strong tertiary amine base such as l,4-diazabicyclo[2.2.2]octane or N-methylmorpholine for acidic phenols (for less-acidic phenols, prior deprotonation with sodium hydride may be advantageous) to form the O-aryl N,N-dimethylthiocarbamate of Formula 10. Newman-Kwart rearrangement of a compound of Formula 10 at temperatures ranging from 200 to 300 °C provides the intermediate S-aryl dimethylthiocarbamate of Formula 11. A one-pot deprotection of a compound of Formula 11 is readily achieved using 10% aqueous sodium hydroxide or methanolic potassium hydroxide to afford the corresponding aryl thiol. Subsequent reaction with a compound of Formula 3 at or slightly above room temperature provides the product 1C (i.e. a compound of Formula 1 wherein Z is S). Methods for Newman-Kwart rearrangements are found in Lloyd- Jones, Guy C, Synthesis 2008, 661-689.Scheme 9

[0429] It is recognized by one skilled in the art that various functional groups can be converted into others to provide different a compound of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley- VCH, New York, 1999. For example, intermediates for the preparation of a compound of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing a compound of Formula 1. The above reactions can also in many cases be performed in alternate order

[0430] It is recognized that some reagents and reaction conditions described above for preparing a compound of Formula 1 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, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley: Hoboken, New Jersey, 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 a compound of Formula 1. 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 presented to prepare a compound of Formula 1.

[0431] One skilled in the art will also recognize that a compound of Formula 1 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.

[0432] 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 chromatographic 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 in CDCI3; "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, "dd" means doublet of doublets, "dt" means doublet of triplets, and "bs" means broad singlet.

[0433] It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley- VCH, New York, 1999. For example, intermediates for the preparation of compounds of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing compounds of Formula 1. The above reactions can also in many cases be performed in alternate order

[0434] It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 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, Greene, T. W.; Wuts, P. G. M. 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 1. 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 presented to prepare the compounds of Formula 1.

[0435] One skilled in the art will also recognize that compounds of Formula 1 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.

[0436] 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 chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. ¾ NMR spectra are reported in ppm downfield from tetramethylsilane at 500 MHz in CDCI3 unless otherwise indicated; "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, "dd" means doublet of doublets and "dt" means doublet of triplets.

[0437] SYNTHESIS EXAMPLE 1

[0438] Synthesis of 3-[2-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-5-isoxazolemethanol

[0439] (Compound 31)

[0440] Step A: Synthesis of 5-chloro-2-[2-[5-[[[(l,l- dimethylethyl)diphenylsilyl]oxy]methyl]-3-isoxazolyl]phenoxy]pyrimidine To a solution of 3-(2-methoxyphenyl)-5-isoxazolemethanol (prepared as described in

[0441] Bioorganic Med. Chem. 2004, 12, 3965 (0.500 mg, 0.243 mmol) in tetrahydrofuran (25 mL) was added t-butyldiphenylsilyl chloride (0.804 mg, 2.92 mmol) followed by imidazole (0.199 mg, 2.92 mmol). After 2 h the solvent was removed under vacuum. Purification using chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to afford the intermediate 5-[[[(l,l-dimethylethyl)diphenylsilyl]oxy]methyl]-3-(2- methoxyphenyl)isoxazole and the material was taken on without further purification.

[0442] To a solution of 5-[[[(l,l-dimethylethyl)diphenylsilyl]oxy]methyl]-3-(2- methoxyphenyl)isoxazole (3.10 g, 0.699 mmol) in dichloromethane (35 mL) at 0 °C was added a 1.0 M solution of boron tribromide (34.9 mL) and the reaction was stirred at this temperature for 1 h. The reaction was quenched with a saturated solution of sodium bicarbonate. The phases were separated, and the aqueous layer was washed with additional dichloromethane. The combined organic phases were combined, dried with MgS04and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes afforded 2-[5-[[[(l,l- dimethylethyl)diphenylsilyl]oxy]methyl]-3-isoxazolyl]phenol which was taken taken to the next step withot further purification.To a solution of 2-[5-[[[(l,l-dimethylethyl)diphenylsilyl]oxy]methyl]-3- isoxazolyl]phenol (2.78 g, 6.47 mmol) in acetonitrile (60 mL) was added 2,5-dichloropyrimidine (1.15 g, 7.70 mmol) and potassium carbonate (2.24 g, 16.2 mmol) and the reaction was heated to 80 °C for 6 h. The reaction mixture was allowed to warm to room temperature and the solvent was removed under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes afforded the title product (2.27 g).

[0443] !H NMR δ 8.41 (s, 2H), 8.00-7.97 (m, 1H), 7.67-7.61 (m, 4H), 7.56-7.50 (m, 1H), 7.47- 7.36 (m, 7H), 7.28-7.26 (m, 1H), 6.56 (t, 1H), 1.05 (s, 9H). MS (AP+) = 542.

[0444] Step B: Synthesis of 3-[2-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-5-isoxazolemethanol

[0445] To a solution of 5-chloro-2-[5-[[[(l,l-dimethylethyl)diphenylsilyl]oxy]methyl]-3- isoxazolyl]phenoxy]pyrimidine (i.e. the product from Step A) (2.27 g, 4.19 mmol) in tetrahydrofuran (15 mL) was added acetic acid (0.50 mL) followed by a solution of 75% tetrabutylammonium fluoride in water (2.9 mL) and the reaction was allowed to stir for 2 h. The reaction was quenched with a saturated solution of sodium bicarbonate and the phases were partitioned and the aqueous phase was further washed with ethyl acetate. The combined organic phases were combined, dried over MgS04and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes afforded the title product, a compound of the present invention (1.21 g).

[0446] !H NMR δ 8.45 (s, 2H), 7.99-7.95 (m, 1H), 7.56-7.52 (m, 1H), 7.42-7.38 (m, 1H), 7.28- 7.25 (m, 1H), 6.64-6.61 (m, 1H), 4.77-4.73 (m, 2H).

[0447] SYNTHESIS EXAMPLE 2

[0448] Synthesis of 3-[2-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-5-isoxazolecarboxaldehyde

[0449] (Compound 33)

[0450] Step A: Synthesis of 3-[2-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-5- isoxazolecarboxaldehyde

[0451] Pyridinium chlorochromate (263 mg, 1.22 mmol) and silica gel (200 mg) were combined and mixed as solids. This mixture was then added to a stirring solution of 3-[2- [(5-chloro-2-pyrimidinyl)oxy]phenyl]-5-isoxazolemethanol (i.e. the product obtained in Step A of Example 1) (309 mg, 1.02 mmol) in dichloromethane (5.0 mL) and the reaction was allowed to stir for 18 h. The solution was filtered to remove the silica gel and the organic phase was washed with a 1 M hydrochloric acid solution. The organic phase was dried with MgSC"4 and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to afforded the title product, a compound of the present invention (0.307 g) .

[0452] !H NMR δ 9.95 (s, 1H), 8.46 (s, 2H), 8.06-8.01 (m, 1H), 7.61-7.56 (m, 1H), 7.47-7.41 (m, 1H), 7.38 (s, 1H), 7.32-7.29 (m, 1H). MS (AP+) = 302.SYNTHESIS EXAMPLE 3

[0453] Synthesis of 5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine

[0454] (Compound 35)

[0455] Step A Synthesis of 5-chloro-2-[2-[5-(difluoromethyl)-3- isoxazolyl]phenoxy]pyrimidine

[0456] To a stirred solution of 3-[2-[(5-chloro-2-pyrimidinyl)oxy]phenyl]-5- isoxazolecarboxaldehyde (i.e. the product from Step A of Example 2) (100 mg, 0.332 mmol) in dichloromethane (3.0 mL) at -78 °C was added Deoxo-Fluor®(161 mg, 0.729 mmol) and the reaction was allowed to return to ambient temperature. Upon consumption of the starting material as evidenced by thin-layer chromatography, the solvent was removed under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to afforded the title product, a compound of the present invention (36.3 mg). !H NMR δ 8.46 (s, 2H), 8.01-7.96 (m, 1H), 7.59-7.54 (m, 1H), 7.44-7.38 (m, 1H), 7.31- 7.27 (m, 1H), 6.98-6.96 (s, 1H), 6.83-6.60 (m, 1H). MS (EST ) = 324.

[0457] SYNTHESIS EXAMPLE 4

[0458] Synthesis of 2-[2-(3-bromo-5-isoxazolyl)phenoxy]-5-chloropyrimidine (Compound 12) Step A: Synthesis of 3-bromo-5-(2-methoxyphenyl)isoxazole

[0459] To a solution of l-ethynyl-2-methoxybenzene (0.78 g, 5.92 mmol) in dichloromethane (10 mL) was added dibromoformaldoxime (1.00 g, 4.93 mmol). The mixture was cooled to 0 °C and potassium bicarbonate (1.48 g, 14.8 mmol) was added, followed by heating to 40 °C for 18 h. Water was added to the reaction mixture, the phases separated, and the aqueous layer was again washed with dichloromethane. The combined organic phases were dried over MgS04, concentrated under vacuum, and purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to afford the title product, a compound of the present invention (1.04 g).

[0460] !H NMR δ 7.94 (dd, 1H), 7.47-7.42 (m, 1H), 7.09 (dd, 1H), 7.02 (dd, 1H), 6.85 (s, 1H), 3.97 (s, 3H). MS (AP+) = 254.

[0461] Step B: Synthesis of 2-(3-bromo-5-isoxazolyl)phenol

[0462] To a solution of 3-bromo-5-(2-methoxyphenyl)isoxazole (i.e. the product from Step A) (0.50 g, 1.97 mmol) in dichloromethane (20mL) was added a 1 M solution of boron tribromide in dichloromethane (9.86 mmol) at -78 °C and the solution was allowed to warm to room temperature and stir for 18 h. Dichloroethane (20 mL) was added, and reaction mixture was concentrated to remove the excess dichloromethane. Boron tribromide in dichloromethane (9.86 mmol) was again added and the reaction was heated to 80 °C until completion as evidenced by thin-layer chromatography. The reaction mixture was allowed to cool to ambient temperature and quenched with a saturated solution of sodium bicarbonate. The phases were separated and the aqueous layer was again washed withdichloromethane. The combined organic phases were dried with MgSC^, concentrated under vacuum, and purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to afford the title product (0.395 g).

[0463] !H NMR δ 7.76 (dd, 1H), 7.39-7.33 (m, 1H), 7.09-7.02 (m, 1H), 6.96-6.93 (m, 1H), 6.02 (s, 1H). MS (AP -) = 238.

[0464] Step C: 2-[2-(3-bromo-5-isoxazolyl)phenoxy]-5-chloropyrimidine

[0465] To a solution of 2-(3-bromo-5-isoxazolyl)phenol (i.e. the product from Step B) (100 mg, 0.417 mmol) in acetonitrile (5 mL) was added 2,5-dichloropyrimidine (75.0 mg, 0.503 mmol) and potassium carbonate (288 mg, 2.08mmol) then the solution was stirred at ambient temperature for 18 h. The reaction was then heated at 40 °C for 2 h followed by 80 °C for two hours. The solution was then cooled to ambient temperature, water was added, the phases were separated and the aqueous layer was again washed with dichloromethane. The combined organic phases were dried over MgS04, concentrated under vacuum, and purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to afford the title product, a compound of the present invention (122 mg). !H NMR δ 8.49 (s, 2H), 8.03 (dd, 1H), 7.58-7.53 (m, 1H), 7.43 (dt, 1H), 7.29 (dd, 1H), 6.74 (s, 1H). MS (AP+) = 352.

[0466] SYNTHESIS EXAMPLE 5

[0467] Synthesis of 5 -chloro-2- [2- [4-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine

[0468] (Compound 25)

[0469] Step A: Synthesis of 2-[4-(trifluoromethyl)-2-pyridinyl]phenol

[0470] 2-Chloro-4-trifluoromethylpyridine (1.0 g, 5.5 mmol) and 2-(4,4,5,5-tetramethyl- l ,3,2-dioxaborolan-2-yl)phenol (1.57 g, 7.16 mmol) were combined in dimethoxy ethane (18 mL) and water (1.8 mL). To this mixture were added sodium carbonate (2.28 g, 16.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.32 g, 0.27 mmol). The reaction was heated at 90 °C for 2.5 h and allowed to stir at 23 °C for 18 h. The mixture was diluted with water (20 mL) and dichloromethane (20 mL) and the layers separated. The aqueous layer was washed with dichloromethane (10 mL). The combined dichloromethane layers were washed with saturated aqueous sodium chloride solution (10 mL) and dried over sodium sulfate. After filtration the organic layer was evaporated and the solid thus obtained was triturated with hexanes (20 mL). The filtrate was concentrated to provide 1.18 g of the title compound as a yellow solid which was used in Step B without further purification.

[0471] !H NMR δ 13.61 (s, 1H), 8.72 (d, 1H), 8.12 (s, 1H), 7.83 (d, 1H), 7.47 (m, 1H), 7.36 (s, 1H), 7.06 (d, 1H), 6.96 (t, 1H).Step B Synthesis of 5-chloro-2-[2-[4-(trifluoromethyl)-2- pyridinyl]phenoxy]pyrimidine

[0472] 2-[4-(Trifiuoromethyl)-2-pyridinyl]phenol (i.e. the product from Step A) (0.20 g, 0.84 mmol) and 2,5-dichloropyrimidine (0.14 g, 0.92 mmol) were dissolved in acetonitrile (2 mL) and treated with powdered potassium carbonate (0.34 g, 2.5 mmol). The mixture was heated to 80 °C for 18 h. After cooling, the reaction mixture was diluted with water (10 mL) and ethyl acetate (10 mL) and the layers separated. The aqueous layer was washed with ethyl acetate (10 mL). The combined ethyl acetate solution was washed with saturated aqueous sodium chloride solution (10 mL) and dried over MgS04. The filtrate was evaporated under reduced pressure and subjected to chromatography through 12 g silica gel eluting with 10 to 20% ethyl acetate in hexanes. Appropriate fractions were pooled and evaporated to provide the title compound, a compound of the present invention (0.2 g) as a clear oil.

[0473] !H NMR δ 8.75 (d, 1H), 8.39 (s, 2H), 7.91 (s, 1H), 7.88 (m, 1H), 7.54 (m, 1H), 7.44 (m, 1H), 7.37 (d, 1H), 7.28 (m, 1H).

[0474] SYNTHESIS EXAMPLE 6

[0475] Synthesis of 5-chloro-2-[4-methyl-2-[6-(trifiuoromethyl)-3-pyridinyl]phenoxy]pyrimidine

[0476] (Compound 22)

[0477] Step A: Synthesis of 2-(2-bromo-4-methylphenoxy)-5-chloropyrimidine

[0478] 2-Bromo-4-methylphenol (280 mg, 1.5 mmol) and 2,5-dichloropyrimidine (246 mg, 1.65 mmol) were combined in 6 mL of acetonitrile under a nitrogen atmosphere. Powdered potassium carbonate (455 mg, 3.3 mmol) was added and the resulting mixture was heated at reflux for 6 h. The reaction mixture was cooled and diluted with de-ionized water and ethyl acetate. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The resulting residue was purified by medium pressure liquid chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes to yield the title compound (270 mg).

[0479] ¾ NMR δ 8.48 (s, 2H), 7.47 (d, 1H), 7.18 (m, 1H), 7.11 (m, 1H), 2.37 (s, 3H).

[0480] Step B Synthesis of 5-chloro-2-[4-methyl-2-[6-(trifluoromethyl)-3- pyridinyl]phenoxy]pyrimidine

[0481] A mixture of 2-(2-bromo-4-methylphenoxy)-5-chloropyrimidine (i.e. the product of Step A; 190 mg, 0.63 mmol), 5-[6-(trifluoromethyl)-3-pyridinyl]-boronic acid (133 mg, 0.70 mmol), sodium carbonate (0.6 mL of 2 M aqueous solution, 1.26 mmol) and tetrakis(triphenylphosphine)palladium(0) (73 mg, 0.06 mmol) in toluene (9 mL) and ethanol (1 mL) was heated at 90 °C for 2 h. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by medium pressure liquid chromatographyon silica gel eluted with 0 to 10% ethyl acetate in hexanes to yield the title compound, a compound of the present invention (190 mg).

[0482] ¾ NMR δ 8.77 (d, 1H), 8.36 (s, 2H), 8.02 (m, 1H), 7.64 (d, 1H), 7.31 (m, 2H), 7.15 (d, 1H), 2.45 (s, 3H).

[0483] SYNTHESIS EXAMPLE 7

[0484] Synthesis of 5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]pyrimidine

[0485] (Compound 53)

[0486] Step A: Synthesis of 2-(3-difluoromethyl-5-isoxazolyl)phenol

[0487] To a solution of 25% sodium methoxide in methanol (5 mL) and tetrahydrofuran (10 mL), acetophenone (1 g, 7.3 mmol) and difluoroacetate (1 g, 8.1 mmol) in tetrahydrofuran (2 mL) was added and heated at 60 °C for 5 h. The reaction was cooled to room temperature and treated with 36% aq hydrochloric acid (4 mL) and stirred at 60 °C for 2 h. The reaction was quenched by adding water (15 mL) and the organic solvent was removed under vacuum. The precipitated product 2-difluoromethyl-4-chromenone (1.4 g) was filtered and dissolved in ethanol (5 mL). To this solution, hydroxylamine acetate (22 mmol) in water (5 mL) was added and the mixture was heated at 60 °C for 3 h. After cooling the reaction to ambient temperature 4,4-difluoro-l-(2-hydroxyphenyl)-butane-l,3-dione 3-oxime was precipitated with the addition of water (20 mL). This product was collected by filtration and suspended in acetic acid (5 mL) and 36% aqueous hydrochloric acid (1.8 mL) at room temperature and stirred at 80 °C for 15 min to obtain the titile compound as a beige solid (800 mg).

[0488] !H NMR δ 7.82 (m,l H), 7.36 (s, 1 H), 7.07 (m, 1 H), 6.95 (m, 2H), 6.82 (t, 1H), 6.05 (s, 1H). MS (ESI+) = 212

[0489] Step B: Synthesis of 5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]phenoxy]- pyrimidine

[0490] To a solution of 2-(3-difluoromethyl-5-isoxazolyl)phenol (i.e. the product from Step

[0491] A) (2.1 g, 9.71 mmol) in anhydrous N,N-dimethylformamide (8 mL) was added 2,5- dichloropyrimidine (1.5 g, 10.2 mmol) and potassium carbonate (2.9 g, 21.3 mmol). The reaction was heated at 90 °C for 1 h. The solution was cooled to ambient temperature and diluted with water. The phases were separated and the aqueous phase was washed with additional ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes afforded the title compound, a compound of the present invention, as a solid (2.2 g).

[0492] !H NMR δ 8.49 (s, 2H), 8.06 (m, 1H), 7.57 (m, 1H), 7.44 (m, 1H), 7.31 (m, 1H), 6.88 (s, 1H), 6.74 (t, 1H). MS (ESI+) = 324SYNTHESIS EXAMPLE 8

[0493] Synthesis of 5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine

[0494] (Compound 144)

[0495] Step A: Synthesis of 4,4-difluoro- 1 -(2-fluoro-6-methoxyphenyl)butane- 1 ,3-dione To a solution of l-(2-fluoro-6-methoxyphenyl)ethanone (2.6 g, 15.5 mmol) and difluoroacetic acid ethyl ester (3.9 mL, 31.0 mmol) in anhydrous N,N-dimethylformamide at 0 °C was added sodium hydride (1.2 g, 31.0 mmol). The reaction mixture was heated at 80 °C for 1 h. The reaction was then cooled to 0 °C, diluted with ethyl acetate and acidified with 1 N aqueous hydrochloric acid. The phases were separated and the aqueous phase was washed with additional ethyl acetate. The organic phases were combined and dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes afforded the title compound (2.5 g). !H NMR δ 7.39 (m, 1H), 6.77 (m, 2H), 6.24 (s, 1H), 6.01 (t, 1 H), 3.87 (s, 3 H). MS (ESI+) = 247

[0496] Step B: Synthesis of 3-difluoromethyl-5-(2-fluoro-6-methoxyphenyl)isoxazole

[0497] A solution of 4,4-difluoro- l-(2-fluoro-6-methoxyphenyl)butane-l,3-dione (i.e. the product from Step A) (2.5 g, 10 mmol) and hydroxylamine hydrochloride (2.1 g, 30 mmol) in ethanol (25 mL) was stirred at 80 °C. After 1 h the solvent was removed under vacuum.

[0498] The resulting residue was diluted with water and extracted with dichloromethane. The organic phase was dried with magnesium sulfate and concentrated under vacuum.

[0499] Purification by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes afforded the title compound (1.5 g).

[0500] !H NMR δ 7.41 (m, 1 H), 6.69 - 6.98 (m, 4H), 3.93 (s, 3 H). MS (ESI+) = 244

[0501] Step C: Synthesis of 2-(3-difluoromethyl-5-isoxazolyl)-3-fluorophenol

[0502] To a solution of 3-difluoromethyl-5-(2-fluoro-6-methoxyphenyl)isoxazole (i.e. the product from Step B) (1.5 g, 6.2 mmol.) in dichloromethane (10 mL) at 0 °C was added a 1.0 M solution of boron tribromide in dichloromethane (31 mL, 31 mmol). The reaction mixture was warmed to ambient temperature and stirred for 6 h. The reaction was cooled to 0 °C and slowly quenched with a saturated aqueous solution of sodium bicarbonate. The biphasic mixture was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried and concentrated under vacuum. The crude residue was purified by chromatography on silica gel, eluting with 0 to 10%> ethyl acetate in hexanes, to afford the title compound (980 mg). !H NMR δ 7.33 (m, 1 H), 6.66 - 6.99 (m, 4 H). MS (ESI+) = 230Step D: Synthesis of 5-chloro-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3- fluorophenoxy]pyrimidine

[0503] To a solution of 2-(3-difluoromethyl-5-isoxazolyl)-3-fluorophenol (i.e. the product from Step C) (120 mg, 0.5 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added 2,5-dichloropyrimidine (85 mg, 0.57 mmol) and potassium carbonate (244 mg, 1.04 mmol). The reaction was heated at 80 °C for 4 h. The mixture was cooled to ambient temperature and diluted with water. The phases were separated and the aqueous phase was washed with additional ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes afforded the title compound, a compound of the present invention, as a solid (110 mg).

[0504] !H NMR δ 8.46 (s, 2H), 7.56 (m, 1H), 7.21 (m, 1H), 7.13 (m, 1H), 6.87 (m, 1 H), 6.74 (t, 1 H). MS (ESI+) = 342

[0505] SYNTHESIS EXAMPLE 9

[0506] Synthesis of 5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]-3-fluorophenoxy]pyrimidine

[0507] (Compound 55)

[0508] Step A: Synthesis of 4,4-difluoro- 1 -(2-fluoro-6-methoxyphenyl)butane- 1 ,3-dione

[0509] A solution of 2-fluoro-6-methoxyacetophenone (6.83 g, 40.6 mmol) and ethyl difluoroacetate (7.45g, 60 mmol) in tetrahydrofuran (35 mL) was added dropwise to a solution of tetrahydrofuran (20 mL) and 25% sodium methoxide (10.2g, 47.2 mmol) over 15 minutes. The reaction was complete in 3h as determined by high pressure liquid chromatography. The reaction was partially concentrated under vacuum to remove most of the tetrahydrofuran and methanol, and then diluted with toluene and water. The aqueous phase was acidified with 37% hydrochloric acid (5g), followed by extraction with toluene. The combined organic phases were concentrated under vacuum to provide title compound (7.98 g).

[0510] !H NMR δ 7.39 (td, 1 H) 6.72 - 6.81 (m, 2 H) 6.25 (d, 1 H) 5.87 - 6.14 (m, 1 H) 3.88 (s, 3 H).

[0511] Step B: Synthesis of 5-(difluoromethyl)-3-(2-fluoro-6-methoxyphenyl)-4H-isoxazol- 5-ol

[0512] To a solution of 4,4-difluoro- l-(2-fluoro-6-methoxyphenyl)butane-l,3-dione (i.e. the product from Step A) (7.98 g, 32.4 mmol) in 35 mL methanol at room temperature was added a 50% hydroxylamine solution (2.78g, 42.1 mmol) and IN sodium hydroxide solution (1.50 mL, 1.50 mmol) followed by heating to 65 °C for 2h. The reaction was cooled to room temperature and diluted with water and toluene. The phases were separated and the organic phase was concentrated under vacuum to provide the title compound (7.99 g).in NMR δ 7.36 (td, 1 H) 6.73 - 6.82 (m, 2 H) 5.79 - 6.05 (m, 1 H) 3.88 (s, 3 H) 3.67 - 3.73 (m, 1 H) 3.47 - 3.51 (m, 1 H) 3.34 - 3.42 (m, 1 H).

[0513] Step C: Synthesis of 5-(difluoromethyl)-3-(2-fluoro-6-methoxyphenyl)isoxazole

[0514] To toluene (80 mL) was added 5-(difluoromethyl)-3-(2-fluoro-6-methoxyphenyl)-4H- isoxazol-5-ol (i.e. the product from Step B) (7.99 g, 30.6 mmol) followed by / ?-toluenesulfonic acid monohydrate (0.700 g, 3.68 mmol). The mixture was heated to a vigorous reflux (107 - 111 °C) for two hours at which point high pressure liquid chromatography determined the reaction was complete. The cooled reaction mixture was washed with a saturated sodium bicarbonate solution, followed by water. The organic phase was concentrated under vacuum to provide the title compound (7.44 g).

[0515] in NMR δ 7.40 (td, 1 H) 6.69 - 6.94 (m, 4 H) 3.88 (s, 3 H).

[0516] Step D: Synthesis of 2-[5-(difluoromethyl)-3-isoxazolyl]-3-fluorophenol

[0517] To a solution of 5-(difluoromethyl)-3-(2-fluoro-6-methoxyphenyl)isoxazole (i.e. the product from Step C) (3.72 g, 15.3 mmol) in dichloromethane (15 mL) at 3 °C was added a 1M solution of boron tribromide in dichloromethane (18.0 mL, 18 mmol) over 5 min. The reaction was then allowed to warm to room temperature. After 90 minutes it was determined the reaction was complete using high pressure liquid chromatography and the reaction was treated with a 10% aqueous solution of potassium bicarbonate (10 mL). The phases were separated and the organic phase was concentrated under vacuum. The resulting brown solid was triturated with a water / methanol solution (~2 / l) providing the title compound (3.34 g). !H NMR δ 9.63 - 9.75 (m, 1 H) 7.33 (td, 1 H) 7.21 (ddd, 1 H) 6.71 - 6.96 (m, 3 H).

[0518] Step E: Synthesis of 5-chloro-2-[2-[5-(difluoromethyl)-3-isoxazolyl]-3- fluorophenoxy]pyrimidine

[0519] To a solution of 2-[5-(difluoromethyl)-3-isoxazolyl]-3-fluorophenol (i.e. the product from Step D) (1.61 g, 7.02 mmol) and 5-methyl-2-methylsulfonylpyrimidine (1.49 g, 7.72 mmol) in N,N-dimethylformamide (9 mL) was added potassium carbonate (4.24 g, 17.5 mmol) and the reaction was allowed to stir at room temperature for 24 h. The reaction was diluted with water and toluene, the phases were separated and the organic solvent was removed under vacuum. To the resulting oil was added 8 mL of methanol and a tan slurry formed, after further dilution with a methanol / water solution (20 mL), the precipitate was filtered providing the title compound, a compound of the present invention (2.24g).

[0520] !H NMR δ 8.45 (s, 2 H) 7.54 (td, 1 H) 7.19 (ddd, 1 H) 7.14 (dt, 1 H) 6.88 (dt, 1 H) 6.61 - 6.85 (m, 1 H).SYNTHESIS EXAMPLE 10

[0521] Preparation of 5 -chloro-2- [3 -cyano-2- [4-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine

[0522] (Compound 158)

[0523] A solution of 5-chloro-2-[2-[4-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine (i.e. the product of example 5, step B) (0.30 g, 0.853 mmoles) in 4.27 mL of N,N- dimethylformamide under a nitrogen atmosphere was treated with copper(II) bromide (0.19 g, 0.853 mmoles), palladium(II) acetate (9 mg, 0.0426 mmoles) and potassium ferricyanide (0.06 g, 0.17 mmoles). The mixture was heated at 130°C for 18 hours. The mixture was then cooled, diluted with diethyl ether and water, filtered thru a celite pad and rinsed with ethyl acetate and water. The phases were separated and the aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed twice with water and saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated to provide 0.2 lg crude product. The crude product was purified with a 12 g Teledyne Isco silica gel column eluting with 10 to 30% EtOAc-Hexanes gradient to provide the title compound, a compound of the present invention as a solid (0.23 g).

[0524] !H NMR δ 8.86 (d, 1H), 8.40 (s, 2H), 7.78 (d&s, 2H), 7.62 (t, 1H), 7.52 (d, 1H), 7.50 (d, 1H).

[0525] SYNTHESIS EXAMPLE 11

[0526] Synthesis of 5-chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]phenoxy]pyrimidine (Compound

[0527] 27)

[0528] Step A: Synthesis of 2-[5-(trifluoromethyl)-2-pyridinyl]phenol

[0529] 2-Chloro-5-(trifluoromethyl)pyridine (1.0 g, 5.50 mmoles) and 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenol (1.57 g, 7.16 mmoles) were combined in 16 mL of 1,2- dimethoxyethane and 1.8 mL of de-ionized water under a nitrogen atmosphere. Solid sodium carbonate (2.28g, 16.5 mmoles) and then tetrakis(triphenylphosphine) palladium (0) (0.32g, 0.27 mmoles) were added. The reaction was heated at reflux approximately ninety minutes. The reaction was cooled, diluted with dichloromethane and filtered thru a celite pad, rinsing with dichloromethane and then de-ionized water. The phases were separated. The aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to give a solid. A solid was filtered from hexanes to give 34 mg. A second crop was obtained from the filtrate from hexanes to yield 506 mg of a light orange- brown solid of the title compound.

[0530] !H NMR δ 8.81 (s, 1H), 8.04 (m, 2H), 7.83 (d, 1H), 7.38 (t, 1H), 7.07 (d, 1H), 6.98 (t, 1H).Step B: Synthesis of 5-chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]phenoxy]- pyrimidine

[0531] A mixture of 2-[5-(trifluoromethyl)-2-pyridinyl]phenol (i.e. the product of step A) (0.20 g, 0.836 mmoles) and 2,5-dichloropyrimidine (0.14 g, 0.919 mmoles) in 2.0 mL of Ν,Ν-dimethylformamide was stirred under a nitrogen atmosphere. Powdered potassium carbonate (0.35 g, 2.51 mmoles) was added and the mixture was heated at 80 °C overnight. The reaction was cooled before diluting with de-ionized water and diethyl ether. The phases were separated. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed three times with de-ionized water, dried over sodium sulfate, filtered and concentrated to 0.37 g of solid. A solid was filtered from hexanes and some diethyl ether to give 103 mg of the title compound, a compound of the present invention. !H NMR δ 8.84 (s, 1H), 8.40 (s, 2H), 7.92(d, 1H), 7.87 (s&d, 2H), 7.54 (t, 1H), 7.45 (t, 1H), 7.27 (d,lH).

[0532] SYNTHESIS EXAMPLE 12

[0533] Preparation of 5-chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]-3-chlorophenoxy]pyrimidine

[0534] (Compound 160)

[0535] 5-Chloro-2-[2-[5-(trifluoromethyl)-2-pyridinyl]phenoxy]-pyrimidine (i.e. the product of example 11, step B) (0.14 g, 0.398 mmoles) was dissolved in 2 mL of acetic acid. Palladium acetate (0.01 g, 0.039 mmoles) and N-chlorosuccinimide (0.11 g, 0.796 mmoles) were added and the mixture was heated at 100 °C for three hours. The mixture was cooled to room temperature overnight and then diluted with toluene and ethyl acetate. The mixture was filtered thru a celite pad, rinsed with toluene and then ethyl acetate. The filtrate was washed twice with saturated aqueous sodium hydrogencarbonate, saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated to a crude product. The crude product was purified with a 12 g Teledyne Isco silica gel column eluting with 10 to 30% EtOAc-Hexanes gradient to provide the title compound, a compound of the present invention as a solid (40 mg).

[0536] !H NMR δ 8.82 (s, 1H), 8.41 (s, 2H), 7.93 (d, 1H), 7.52 (d, 1H), 7.47 (m, 2H), 7.19 (m, 1H).

[0537] SYNTHESIS EXAMPLE 13

[0538] Synthesis of 5-bromo-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine

[0539] (Compound 62)

[0540] Step A: Synthesis of 5-(difluoromethyl)-3-(2-methoxyphenyl)isoxazole

[0541] To a solution of acetophenone (3.0 g, 20 mmol) in methanol (15 mL) was added a 30% sodium methoxide in methanol solution (5.0 mL) and the reaction stirred for five minutes. Next ethyl difluoroacetate (2.97 g, 24 mmol) was added and the reaction was heated to reflux for 18 h. The reaction was allowed to cool to room temperature and the solvent was removed under vacuum. To the residue was added 1M hydrochloric acid and ethyl acetate,the phases were separated, the organic phase was dried using magnesium sulfate and the solvent was removed under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes afforded the desired product which was taken on directly. A solution of 4,4-difluoro-l-(2-methoxyphenyl)butane-l,3-dione from the previous step in ethanol (30 mL) was added dropwise to a solution of hydroxylamine hydrochloride (1.4 g, 20 mmol) in 1M sodium hydroxide (21 mL). The reaction was then heated to reflux for 2 h, followed by cooling to room temperature. The product was precipitated from solution by the addition of water and collected via vacuum filtration to afford the desired product which was taken on directly (AP+ 244, 1H NMR δ ppm 7.79 (d, 1 H) 7.38 - 7.46 (m, 1 H) 6.93 - 7.04 (m, 2 H) 5.76 - 6.04 (m, 1 H) 3.88 (s, 3 H) 3.67 - 3.80 (m, 1 H) 3.49 - 3.55 (m, 1 H)). Next, a solution of 5-(difluoromethyl)-3-(2-methoxyphenyl)-4H-isoxazol-5-ol from the previous step was taken up in trifluoroacetic acid (20 mL) and heated to 70 °C for 18 h. The reaction was cooled to room temperature and the solvent was removed under vacuum. The resulting residue was dissolved in dichloromethane and washed with a saturated solution of sodium bicarbonate. The phases were separated, the organic phase was dried using magnesium sulfate and the solvent was removed under vacuum. Purification by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes afforded the title compound (2.0 g, AP+ = 226).

[0542] lH NMR δ 7.91 (dd, 1 H) 7.42 - 7.50 (m, 1 H) 6.98 - 7.12 (m, 3 H) 6.66 - 6.93 (m, 1 H) 3.92 (s, 3 H).

[0543] Step B: Synthesis of 2-[5-(difluoromethyl)-3-isoxazolyl]phenol

[0544] To a solution of 5-(difluoromethyl)-3-(2-methoxyphenyl)isoxazole (i.e. the product of step A) (2.01 g, 8.92 mmol) in dichloromethane (50 mL) at 0 °C was added a 1M solution of boron tribromide in dichloromethane (13.3 mL, 13.3 mmol) and the reaction was allowed to warm to room temperature over three hours. The solvent was removed under vacuum and purified by chromatography on silica gel, eluting with 0 to 100% ethyl acetate in hexanes to afford the title compound (1.66g, AP- = 210).

[0545] !H NMR δ 9.14 (s, 1 H) 7.51 (dd, 1 H) 7.39 (ddd, 1 H) 7.11 (dd, 1 H) 6.97 - 7.04 (m, 2 H) 6.70 - 6.95 (m, 1 H).

[0546] Step C: Synthesis of 5-bromo-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]- pyrimidine

[0547] To a solution of 2-[5-(difluoromethyl)-3-isoxazolyl]phenol (i.e. the product of step B) (427 mg, 2.01 mmol) and 5-bromo-2-chloro-pyrimidine (468 mg, 2.42 mmol) in acetonitrile (10 mL) was added potassium carbonate (695 mg, 5.03 mmol) and the reaction was heated to 80 °C for 18 h. The solvent was removed under vacuum and purified by chromatography on silica gel, eluting with 0 to 100% ethyl acetate in hexanes to afford the title compound, a compound of the present invention, as a solid (555 mg, mp = 88.9-92.8 °C).in NMR δ 8.53 (s, 2 H) 7.98 (dd, 1 H) 7.53 - 7.60 (m, 1 H) 7.41 (td, 1 H) 7.28 (dd, 1 H) 6.97 (t, 1 H) 6.59 - 6.84 (m, 1 H).

[0548] SYNTHESIS EXAMPLE 14

[0549] Synthesis of 5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]-3-fluorophenoxy]pyrimidine

[0550] (Compound 168)

[0551] Step A: Synthesis of 5-(difluoromethyl)-3-(2-methoxyphenyl)-4H-isoxazol-5-ol

[0552] To a solution of 2-fluoro-6-methoxyacetophenone (1.0 g, 5.9 mmol) in tetrahydrofuran (2 mL) was added a 30% sodium methoxide in methanol solution (1.4 mL). To this mixture was added dropwise a solution of ethyl trifluoroacetate (0.805 g, 6.49 mmol) in tetrahydrofuran (1 mL) and the reaction stirred at room temperature for 2 h. To the reaction was added 1M hydrochloric acid solution and ethyl acetate, the phases were separated and the aqueous phase was again washed with ethyl acetate. The combined organic phases were dried with magnesium sulfate and concentrated under vacuum to provide the desired product (AP- = 263) which was taken onto the next step directly. Next, to a solution of 4,4,4- trifluoro-l-(2-fluoro-6-methoxyphenyl)butane-l,3-dione (from the previous step) in ethanol (14 mL) was added 1M sodium hydroxide solution (7 mL) followed by hydroxylamine hydrochloride (410 mg, 5.9 mmol) and the reaction stirred overnight at room temperature. The solvent was removed under vacuum and the residue was purified by chromatography on silica gel, eluting with 0 to 100% ethyl acetate in hexanes and 0 to 20% methanol in dichlromethane to afford the product (AP+ = 280, 1Η NMR δ ppm 7.37 (td, 1 Η) 6.74 - 6.83 (m, 2 Η) 3.89 (s, 3 Η) 3.79 (d, 1 Η) 3.50 (dd, 1 Η)) which was taken onto the next step directly To a solution of 3-(2-fluoro-6-methoxy-phenyl)-5-(trifluoromethyl)-4H-isoxazol-5- ol (from the previous step) in dichloromethane (20 mL) at 0 °C was added a 1M solution of boron tribromide in dichloromethane (11.8 mL, 11.8 mmol) and the reaction was allowed to warm to room temperature over 2 h. The solvent was removed under vacuum. The residue was dissolved in dichloromethane and washed with a saturated solution of sodium bicarbonate, the aqueous phase was washed with dichloromethane. The combined organic phases were dried with magnesium sulfate, concentrated under vacuum and purified by chromatography on silica gel, eluting with 0 to 100% ethyl acetate in hexanes, providing the title compound (606 mg, AP- = 264).

[0553] in NMR δ 9.86 (s, 1 H) 7.32 (td, 1 H) 6.84 - 6.90 (m, 1 H) 6.68 (ddd, 1 H) 3.86 - 3.94 (m, 1 H) 3.75 (dd, 1 H) 3.56 (s, 1 H).

[0554] Step B: Synthesis of 5-chloro-2-[2-[5-(trifluoromethyl)-3-isoxazolyl]-3- fluorophenoxy]pyrimidine

[0555] To a solution of 3-(2-fluoro-6-hydroxyphenyl)-5-(trifluoromethyl)-4H-isoxazol-5-ol

[0556] (i.e. the product of step A) (606 mg, 2.29 mmol) in dimethylsulfoxide (15 mL) was added 5- chloro-2-methylsulfonyl-pyrimidine (527mg, 2.74mmol) followed by cesium carbonate(l . lg, 3.43mmol) and the reaction stirred for 18 h. The reaction was partitioned between water and ethyl acetate, the phases were separated and the aqueous layer was again washed with ethyl acetate. The combined organic phases were dried with magnesium sulfate and concentrated under vacuum. The residue was purified by chromatography on silica gel, eluting with 0 to 100% ethyl acetate, to afford the title compound, a compound of the present invention, (198mg, AP+ = 360).

[0557] !H NMR δ 8.46 (s, 2 H) 7.56 (td, 1 H) 7.21 (ddd, 1 H) 7.15 (dt, 1 H) 7.02 (dd, 1 H).

[0558] SYNTHESIS EXAMPLE 15

[0559] Synthesis of 5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl)phenoxy]pyrimidine

[0560] (Compound 63)

[0561] Step A: Synthesis of 2-(trifluoromethyl)-4H- 1 -benzopyran-4-one

[0562] 2-Hydroxyacetophenone (10 g, 66.7 mmol) was dissolved in trifluoroacetic anhydride (19 ml, 133.3 mmol) and pyridine (10.8 mL, 133.3 mmol). The reaction mixture was heated at 70 °C and stirred for 12 h. After cooling the reaction mixture was diluted with 1 M hydrochloric acid and methylene chloride and washed with water. The organic phase was dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 5% ethyl acetate in hexanes afforded the title compound (10.5 g) as a pale yellow solid.

[0563] !H NMR δ 8.21 (m, 1 H), 7.76 (m, 1H), 7.77 (d, 1H), 7.46 (m, 1H), 6.73 (s, 1H). MS (ESI+) = 215

[0564] Step B: Synthesis of 2-[3-(trifluoromethyl)-5-isoxazolyl]phenol

[0565] To a solution of 2-(trifluoromethyl)-4H-l-benzopyran-4-one (i.e. the product of step A) (10.5 g, 48.8 mmol) in ethanol (50 mL), hydroxylamine acetate (146 mmol) in water (50 mL) was added. The mixture was heated at 60 °C for 4 h. After cooling the reaction to ambient temperature 4,4,4-trifluoro-l-(2-hydroxyphenyl)-butane-l,3-dione 3-oxime was precipitated with the addition of water (200 mL).

[0566] in NMR δ 9.30 (s, 1H), 7.37 (m, 1H), 7.19 (m, 1H), 7.06 (m, 1H), 6.94 (m, 1H), 3.87 (d, 1H), 3.69 (d, 1H).

[0567] This product was collected by filtration and suspended in acetic acid (30 mL) and 36 % aqueous hydrochloric acid (10.8 mL) at room temperature. The mixture was stirred at 80 °C for 30 min to afford the title compound as a white solid (4.6 g).

[0568] !H NMR δ 7.88 (m, 1H), 7.37 (m, 1H), 7.08 (m, 1H), 7.01 (s, 1H), 6.95 (m, 1H). MS (ESI+) = 230

[0569] Step C: Synthesis of 5-chloro-2-[2-[3-(trifluoromethyl)-5-isoxazolyl)phenoxy]- pyrimidine

[0570] To a solution of 2-[3-(trifluoromethyl)-5-isoxazolyl]phenol (i.e. the product of step B) (2.2 g, 9.4 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 2,5-dichloropyrimidine (1.5 g, 10.3 mmol) and potassium carbonate (2.9 g, 20.6 mmol). The reaction was heated at 80 °C for 2 h. The solution was cooled to ambient temperature and diluted with water. The phases were separated and the aqueous phase was washed with additional ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 5% ethyl acetate in hexanes afforded the title compound, a compound of the present invention, as a solid (2.1 g).

[0571] !H NMR δ 8.49 (s, 2H), 8.08 (m, 1H), 7.58 (m, 1H), 7.45 (m, 1H), 7.32 (m, 1H), 6.91 (s, 1H). MS (ESI+) = 342. Melting Point: 114-115 °C

[0572] SYNTHESIS EXAMPLE 16

[0573] Synthesis of 5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine

[0574] (Compound 145)

[0575] Step A: Synthesis of 4,4-difluoro- 1 -(2-fluoro-6-methoxyphenyl)butane- 1 ,3-dione

[0576] To a solution of l-(2-fluoro-6-methoxyphenyl)ethanone (2.6 g, 15.5 mmol) and difluoroacetic acid ethyl ester (3.9 mL, 31.0 mmol) in anhydrous N,N-dimethylformamide at 0 °C was added sodium hydride (1.2 g, 31.0 mmol). The reaction mixture was heated at 80 °C for 1 h. The reaction was then cooled down to 0 °C, diluted with ethyl acetate and acidified with 1 N aqueous hydrochloric acid. The phases were separated and the aqueous phase was washed with additional ethyl acetate. The organic phases were combined and dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes afforded the title compound (2.5 g).

[0577] !H NMR δ 7.39 (m, 1H), 6.77 (m, 2H), 6.24 (s, 1H), 6.01 (t, 1 H), 3.87 (s, 3 H). MS (ESI+) = 247

[0578] Step B: Synthesis of 3-(difluoromethyl)-5-(2-fluoro-6-methoxyphenyl)isoxazole

[0579] A solution of 4,4-difluoro- l-(2-fluoro-6-methoxyphenyl)butane-l,3-dione (i.e. the product of step A) (2.5 g, 10 mmol) and hydroxylamine hydrochloride (2.1 g, 30 mmol) in ethanol (25 mL) was stirred at 80 °C. After 1 h the solvent was removed under vacuum.

[0580] The resulting residue was diluted with water and extracted with dichloromethane. The organic phase was dried with magnesium sulfate and concentrated under vacuum.

[0581] Purification by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes afforded the title compound (1.5 g).

[0582] !H NMR δ 7.41 (m, 1 H), 6.69 - 6.98 (m, 4H), 3.93 (s, 3 H). MS (ESI+) = 244

[0583] Step C: Synthesis of 2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenol

[0584] To a solution of 3-(difluoromethyl)-5-(2-fluoro-6-methoxyphenyl)isoxazole (i.e. the product of step B) (1.5 g, 6.2 mmol.) in dichloromethane (10 mL) at 0 °C was added a 1.0 M solution of boron tribromide in dichloromethane (31 mL, 31 mmol). The reaction mixturewas warmed to ambient temperature and stirred for 6 h. The reaction was cooled to 0 °C and slowly treated with a saturated aqueous solution of sodium bicarbonate. The biphasic mixture was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried and concentrated under vacuum. The crude residue was purified by chromatography on silica gel, eluting with 0 to 10% ethyl acetate in hexanes, to afford the title compound (980 mg). !H NMR δ 7.33 (m, 1 H), 6.66 - 6.99 (m, 4 H). MS (ESI+) = 230

[0585] Step D: Synthesis of 5-bromo-2-[2-[3-(difluoromethyl)-5-isoxazolyl]-3- fluorophenoxy]pyrimidine

[0586] To a solution of 2-[3-(difluoromethyl)-5-isoxazolyl]-3-fluorophenol (i.e. the product of step C) (229 mg, 1 mmol) in anhydrous N,N-dimethylformamide (2.5 mL) was added 5- bromo-2-chloropyrimidine (212 mg, 1.1 mmol) and potassium carbonate (304 mg, 2.2 mmol). The reaction was heated at 80 °C for 1 h. The solution was cooled to ambient temperature and diluted with water. The phases were separated and the aqueous layer was washed with additional ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated under vacuum. Purification by chromatography on silica gel eluting with 0 to 15% ethyl acetate in hexanes afforded the title compound, a compound of the present invention, as a solid (320 mg).

[0587] !H NMR δ 8.54 (s, 2H), 7.54 (m, 1H), 7.20 (m, 1H), 7.13 (m, 1H), 6.86 (m, 1 H), 6.75 (t, 1 H). MS (ESI+) = 387

[0588] By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 1584 can be prepared. The following abbreviations are used in the 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, Bu means butyl, z'-Pr means isopropyl, Bu means butyl, c-Pr cyclopropyl, c-Bu means cyclobutyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, NHMe methylamino, -CN means cyano, Py means pyridinyl, -NO2 means nitro, tzl meand triazol, pzl means pyrazol, izl means imidazole, odzl means oxadiazol, tdzl means thiadiazol and SC^Me means methylsulfonyl.

[0589] Table 1

[0590] R2= CI; Z = O; and R3

[0591] and is:

[0592] 4-I-isothiazol-5-yl 4 -Me - isothiazol- 5 -y 1 4-Et-isothiazol-5-yl 4-CF3-isothiazol-5-yl 4-CHF2-isothiazol-5-yl 4-CHO-isothiazol-5-yl 4-CN-isothiazol-5-yl 4-OMe-isothiazol-5-yl

[0593] 4- OCF3-isothiazol-5-yl

[0594] 4 - Ph- isothiazol- 5 -yl Isothiazol-3-yl

[0595] 5- F-isothiazol-3-yl 5-Cl-isothiazol-3-yl 5-Br-isothiazol-3-yl

[0596] 5-I-isothiazol-3-yl 5 -Me - isothiazol- 3 -yl 5-Et-isothiazol-3-yl 5 -CF 3 -isothiazol- 3 -yl 5 -CHF2 -isothiazol-3 -yl

[0597] 5- CHO-isothiazol-3-yl 5-CN-isothiazol-3-yl

[0598] 5-CH2CN-isothiazol-3-yl 5-OMe-isothiazol-3-yl 5-OCF3-isothiazol-3-yl 5 -Ph-isothiazol-3 -yl 4-F-isothiazol-3-yl 4-Cl-isothiazol-3-yl 4-Br- isothiazol-3 -yl 4-I-isothiazol-3-yl 4-Me-isothiazol-3-yl 4-Et-isothiazol-3-yl 4-CF3 -isothiazol-3 -yl 4-CHF2-isothiazol-3-yl 4-CHO-isothiazol-3-yl 4-CN-isothiazol-3 -yl4-OMe-isothiazol-3-yl-OCF3 -isothiazol-3 -yl 4-Et-oxazol-2-yl

[0599] 4- Ph-isothiazol-3-yl 4-CF3-oxazol-2-yl

[0600] Isoxazol-4-yl 4-CHF2-oxazol-2-yl 3-F-isoxazol-4-yl 4-CHO-oxazol-2-yl 3 -Cl-isoxazol-4-yl 4-CN-oxazol-2-yl 3-Br-isoxazol-4-yl 4-OMe-oxazol-2-yl 3-I-isoxazol-4-yl 4- OCF3-oxazol-2-yl 3-Me-isoxazol-4-yl 4- Ph-oxazol-2-yl 3 -Et-isoxazol-4-yl Thiazol-2-yl 3 -CF3 -isoxazol-4-yl 5- F-thiazol-2-yl -CHF2-isoxazol-4-yl 5-Cl-thiazol-2-yl 3-CHO-isoxazol-4-yl 5-Br-thiazol-2-yl 3 -CN-isoxazol-4-yl 5-I-thiazol-2-yl 3-OMe-isoxazol-4-yl 5-Me-thiazol-2-yl -OCF3 -isoxazol-4-yl 5-Et-thiazol-2-yl 3 -Ph-isoxazol-4-yl 5-CF3-thiazol-2-yl 5-F-isoxazol-4-yl 5- CHF2-thiazol-2-yl 5-Cl-isoxazol-4-yl 5-CHO-thiazol-2-yl 5-Br-isoxazol-4-yl 5-CN-thiazol-2-yl 5-I-isoxazol-4-yl 5-CH2CN-thiazol-2-yl

[0601] 5- Me-isoxazol-4-yl 5-OMe-thiazol-2-yl 5-Et-isoxazol-4-yl 5-OCF3-thiazol-2-yl

[0602] 5-CF3-isoxazol-4-yl 5-Ph-thiazol-2-yl 5-CHF2-isoxazol-4-yl 4-F-thiazol-2-yl 5-CHO-isoxazol-4-yl 4-Cl-thiazol-2-yl 5-CN-isoxazol-4-yl 4-Br-thiazol-2-yl 5-OMe-isoxazol-4-yl 4-I-thiazol-2-yl 5-OCF3-isoxazol-4-yl 4-Me-thiazol-2-yl 5-Ph-isoxazol-4-yl 4-Et-thiazol-2-yl

[0603] Isothiazol-4-yl 4-CF3-thiazol-2-yl 3 -F-isothiazol-4-yl 4-CHF2-thiazol-2-yl 3-Cl-isothiazol-4-yl 4-CHO-thiazol-2-yl 3 -Br-isothiazol-4-yl 4-CN-t azol-2-yl 3 -I-isothiazol-4-yl 4-OMe-thiazol-2-yl 3 -Me-isothiazol-4-yl 4-OCF3-thiazol-2-yl 3-Et-isothiazol-4-yl 4-Ph-thiazol-2-yl 3 -CF3 -isothiazol-4-yl Oxazol-5-yl -CHF2-isothiazol-4-yl 2-F-oxazol-5-yl2-Cl-oxazol-5-yl

[0604] 2-Br-oxazol-5-yl

[0605] 2-Me-oxazol-5-yl

[0606] -CF3-oxazol-5-yl

[0607] -CHF2-oxazol-5-yl 2-CN-oxazol-5-yl

[0608] -OMe-oxazol-5-yl-OCF3-oxazol-5-yl 2-Ph-oxazol-5-yl

[0609] 4-F-oxazol-5-yl

[0610] 4-Cl-oxazol-5-yl

[0611] 4-Br-oxazol-5-yl

[0612] 4-Me-oxazol-5-yl

[0613] -CF3-oxazol-5-yl

[0614] -CHF2-oxazol-5-yl 4-CN-oxazol-5-yl

[0615] -OMe-oxazol-5-yl-OCF3-oxazol-5-yl 4-Ph-oxazol-5-yl

[0616] Thiazol-5-yl

[0617] 2-F-thiazol-5-yl

[0618] 2-Cl-thiazol-5-yl

[0619] 2-Br-thiazol-5-yl

[0620] 2-Me-thiazol-5-yl

[0621] 2-CF3-thiazol-5-yl-CHF2-thiazol-5-yl 2-CN-thiazol-5-yl

[0622] -OMe-thiazol-5-yl-OCF3-thiazol-5-yl 2-Ph-thiazol-5-yl

[0623] 4-F-thiazol-5-yl

[0624] 4-Cl-thiazol-5-yl

[0625] 4-Br-thiazol-5-yl

[0626] 4-Me-thiazol-5-yl

[0627] 4-CF3-thiazol-5-yl-CHF2-thiazol-5-yl 4-CN-thiazol-5-yl -OMe-thiazol-5-yl-OCF3-l-Me-l#-izl-4-yl 5-OCF3-l-Me-l -pzl-4-yl 2-Ph-l-Me-l#-izl-4-yl 5-Ph-l-Me-l / -pzl-4-yl 5-F-l-Me-l#-izl-4-yl l / -pzl-5-yl 5-Cl-l-Me-l / / -izl-4-yl l-Me-l / -pzl-5-yl 5-Br-l-Me-li / -izl-4-yl 3-F-l-Me-ltf-pzl-5-yl l,5-di-Me-l / / -izl-4-yl 3-Cl-l-Me-l / -pzl-5-yl 5-CF3-l-Me-l / -izl-4-yl 3-Br-l-Me-l / -pzl-5-yl-CHF2-l-Me-l / -izl-4-yl 1.3- di-Me-l / -pzl-5-yl 5-CN-l-Me-l#-izl-4-yl 3-CF3-l-Me-l#-pzl-5-yl -OMe-l-Me-l / / -izl-4-yl 3 -CHF2- 1 -Me- l / -pzl-5-yl-OCF3 - 1 -Me- l / f-izl-4-yl 3-CN-l-Me-l / -pzl-5-yl 5-Ph-l-Me-l / -izl-4-yl 3- OMe-l-Me-l / -pzl-5-yl l / -izl-5-yl 3 -OCF3- 1 -Me- l#-pzl-5-yl l-Me-l / -izl-5-yl 3- Ph-l-Me-l / / -pzl-5-yl 2-F-l-Me-l / -izl-5-yl 4- F-l-Me-l / -pzl-5-yl 2-Cl-l-Me-l / -izl-5-yl 4-Cl-l-Me-l / -pzl-5-yl 2-Br-l-Me-l#-izl-5-yl 4-Br-l-Me-l / -pzl-5-yl l,2-di-Me-l / -izl-5-yl 1.4- di-Me-l / -pzl-5-yl 2-CF3-l-Me-l -izl-5-yl 4- CF3-l-Me-l / -pzl-5-yl-CHF2-l-Me-l / -izl-5-yl 4-CHF2- 1 -Me- ltf-pzl-5-yl 2-CN-l-Me-l -izl-5-yl 4-CN-l-Me-l / -pzl-5-yl -OMe-l-Me-li-izl-5-yl 4-OMe-l-Me-l / / -pzl-5-yl-OCF3-l-Me-l / / -izl-5-yl 4-OCF3- 1 -Me- l / -pzl-5-yl 2-Ph-l-Me-l / -izl-5-yl 4-Ph-l-Me-l#-pzl-5-yl 4-F-l-Me-li-izl-5-yl Thiophene-2-yl 4-Cl-l-Me-l / -izl-5-yl Thiophene-3-yl 4-Br-l-Me-l / -izl-5-yl Furan-2-yl l,4-di-Me-l / -izl-5-yl Furan-3-yl 4-CF3-l-Me-l / -izl-5-yl l / -pyrrol-2-yl-CHF2-l-Me-ltf-izl-5-yl l-Me-l / -pyrrol-2-yl 4-CN-l-Me-l / -izl-5-yl l / -pyrrol-3-yl -OMe-l-Me-l / -izl-5-yl 1- Me-l / -pyrrol-3-yl-OCF3-l-Me-l / / -izl-5-yl [l,3,4]odzl-2-yl 4-Ph-l-Me-l / -izl-5-yl 2- F-[l,3,4]odzl-5-yl l / -pzl-3-yl 2-Cl-[l,3,4]odzl-5-yl l-Me-li -pzl-3-yl 2-Br-[l,3,4]odzl-5-yl 4-F-l-Me-l / -pzl-3-yl 2-Me-[l,3,4]odzl-5-yl 4-Cl-l-Me-l#-pzl-3-yl 2-CF3-[l,3,4]odzl-5-yl2-CHF2-[l,3,4]odzl-5-yl 5-Br-[l,2,4]odzl-3-yl 2-CN-[l,3,4]odzl-5-yl 5-Me-[l,2,4]odzl-3-yl 2-OMe-[l,3,4]odzl-5-yl 5-CF3-[l,2,4]odzl-3-yl 2-OCF3-[l,3,4]odzl-5-yl 5-CHF2-[l,2,4]odzl-3-yl [l,3,4]tdzl-2-yl 5-CN-[l,2,4]odzl-3-yl 2-F-[l,3,4]tdzl-5-yl 5-OMe-[l,2,4]odzl-3-yl 2-Cl-[l,3,4]tdzl-5-yl 5-OCF3-[l,2,4]odzl-3-yl 2-Br-[l,3,4]tdzl-5-yl 5-Ph-[l,2,4]odzl-3-yl 2-Me-[l,3,4]tdzl-5-yl [l,2,4]tdzl-5-yl 2-CF3-[l,3,4]tdzl-5-yl 3-F-[l,2,4]tdzl-5-yl 2-CHF2-[l ,3,4]tdzl-5-yl 3-Cl-[l,2,4]tdzl-5-yl 2-CN-[l,3,4]tdzl-5-yl 3-Br-[l,2,4]tdzl-5-yl 2-OMe-[l,3,4]tdzl-5-yl 3-Me-[l,2,4]tdzl-5-yl 2-OCF3-[l,3,4]tdzl-5-yl 3-CF3-[l,2,4]tdzl-5-yl

[0628] 4 / / -[l,2,4]tzl-3-yl 3-CHF2-[l,2,4]tdzl-5-yl 4-Me-4#-[l,2,4]tzl-3-yl 3-CN-[l,2,4]tdzl-5-yl 3-F-4-Me-4#-[l,2,4]tzl-5-yl 3- OMe-[l,2,4]tdzl-5-yl -Cl-4-Me-4tf-[l,2,4]tzl-5-yl 3- OCF3-[l,2,4]tdzl-5-yl -Br-4-Me-4#-[l,2,4]tzl-5-yl 3- Ph-[l,2,4]tdzl-5-yl

[0629] 3.4- di-Me-4#-[l,2,4]tzl-5-yl [l,2,4]tdzl-3-yl -CF3-4-Me-4#-[l,2,4]tzl-5- 5-F-[l,2,4]tdzl-3-yl yi 5-Cl-[l ,2,4]tdzl-3-yl-CHF2-4-Me-4#-[l ,2,4]tzl-5- 5-Br-[l,2,4]tdzl-3-yl yi 5-Me-[l,2,4]tdzl-3-yl-CN-4-Me-4#-[ l,2,4]tzl-5-yl 5-CF3-[l,2,4]tdzl-3-yl-OMe-4-Me-4i / -[l ,2,4]tzl-5- 5-CHF2-[l,2,4]tdzl-3-yl yi 5-CN-[l,2,4]tdzl-3-yl-OCF3-4-Me-4#-[ l,2,4]tzl-5- 5-OMe-[l,2,4]tdzl-3-yl yi 5-OCF3-[l,2,4]tdzl-3-yl -Ph-4-Me-4#-[l,2,4]tzl-5-yl 5-Ph-[l,2,4]tdzl-3-yl l#-[l,2,4]tzl-3-yl [l,2,3]odzl-5-yl l-Me-l#-[l,2,4]tzl-3-yl 4- F-[l,2,3]odzl-5-yl 5-F-l -Me-l#-[l ,2,4]tzl-3-yl 4-Cl-[l,2,3]odzl-5-yl 5-Cl-l-Me-l / -[l,2,4]tzl-3-yl 4-Br-[l,2,3]odzl-5-yl 5-Br-l-Me-l / -[l,2,4]tzl-3-yl 4-Me-[l,2,3]odzl-5-yl

[0630] 1.5- di-Me-l#-[ l,2,4]tzl-3-yl 4- CF3-[l,2,3]odzl-5-yl 5-CF3- 1 -Me- lH-[ 1 ,2,4]tzl-3- 4- CHF2-[l,2,3]odzl-5-yl yi 4-CN-[l,2,3]odzl-5-yl-OMe-[l,2,3]odzl-5-yl 4-CN-l#-[l,2,3]tzl-5-yl- OCF3-[l,2,3]odzl-5-yl 4-OMe-li / -[l,2,3]tzl-5-yl

[0631] 4- Ph-[l,2,3]odzl-5-yl 4-OCF3-l#-[l,2,3]tzl-5-yl

[0632] [l,2,3]odzl-4-yl 4-Ph-l#-[l,2,3]tzl-5-yl

[0633] 5- F-[l,2,3]odzl-4-yl 5-F-pyridin-2-yl 5-Cl-[l,2,3]odzl-4-yl 5-Cl-pyridin-2-yl 5-Br-[l,2,3]odzl-4-yl 5-Br-pyridin-2-yl 5-Me-[l,2,3]odzl-4-yl 5-I-pyridin-2-yl 5-CF3-[l,2,3]odzl-4-yl 5-Me-pyridin-2-yl- CHF2-[l,2,3]odzl-4-yl 5-Et-pyridin-2-yl 5-CN-[l,2,3]odzl-4-yl 5-CF3-pyridin-2-yl -OMe-[l,2,3]odzl-4-yl 5-CHF2-pyridin-2-yl-OCF3-[l,2,3]odzl-4-yl 5-CHO-pyridin-2-yl 5-Ph-[l,2,3]odzl-4-yl 5-CN-pyridin-2-yl

[0634] [l,2,3]tdzl-5-yl 5-OMe-pyridin-2-yl 4-F-[l,2,3]tdzl-5-yl 5- OCF3-pyridin-2-yl 4-Cl-[l,2,3]tdzl-5-yl 5 -N(Me)2-pyridin-2-yl 4-Br-[l,2,3]tdzl-5-yl 5- Ph-pyridin-2-yl 4-Me-[l,2,3]tdzl-5-yl 3,5-di-Cl-pyridin-2-yl 4-CF3-[l,2,3]tdzl-5-yl 3-Me-5-Cl-pyridin-2-yl -CHF2-[l,2,3]tdzl-5-yl 3-CN-5-Cl-pyridin-2-yl 4-CN-[l,2,3]tdzl-5-yl 6- F-pyridin-2-yl 4-OMe-[l,2,3]tdzl-5-yl 6-Cl-pyridin-2-yl - OCF3-[l,2,3]tdzl-5-yl 6-Br-pyridin-2-yl

[0635] 4- Ph-[l,2,3]tdzl-5-yl 6-I-pyridin-2-yl [l,2,3]tdzl-4-yl 6-Me-pyridin-2-yl

[0636] 5- F-[l,2,3]tdzl-4-yl 6-Et-pyridin-2-yl 5-Cl-[l,2,3]tdzl-4-yl 6-CF3-pyridin-2-yl 5-Br-[l,2,3]tdzl-4-yl 6- CHF2-pyridin-2-yl 5-Me-[l,2,3]tdzl-4-yl 6-CHO-pyridin-2-yl 5-CF3-[l,2,3]tdzl-4-yl 6-CN-pyridin-2-yl - CHF2-[l,2,3]tdzl-4-yl 6-OMe-pyridin-2-yl 5-CN-[l,2,3]tdzl-4-yl 6-OCF3-pyridin-2-yl

[0637] 5-OMe-[l,2,3]tdzl-4-yl 6-N(Me)2-pyridin-2-yl 5-OCF3-[l,2,3]tdzl-4-yl 6-Ph-pyridin-2-yl 5-Ph-[l,2,3]tdzl-4-yl 3-F-pyridin-2-yl

[0638] 3 -[l,2,4]tzl-3-yl 3-Cl-pyridin-2-yl 5-F-3 / / -[l,2,4]tzl-3-yl3-Br-pyridin-2-yl3-I-pyridin-2-yl 5 -F-pyridazin-2 -yl 3 -Me-pyridin-2 -yl 5-Cl-pyridazin-2-yl 3 -Et-pyridin-2-yl 5-Br-pyridazin-2-yl 3-CF3-pyridin-2-yl 5-I-pyridazin-2-yl -CHF2-pyridin-2-yl 5-Me-pyridazin-2-yl 3-CHO-pyridin-2-yl 5 -Et-pyridazin-2-yl 3-CN-pyridin-2-yl 5 -CF3 -pyridazin-2 -yl 3-OMe-pyridin-2-yl 5 -CHF2-pyridazin-2 -yl 3 -OCF3 -pyridin-2 -yl 5-CHO-pyridazin-2-yl -N(Me)2-pyridin-2-yl 5 -CN-pyridazin- 2 -yl

[0639] 3-Ph-pyridin-2-yl 5-OMe-pyridazin-2-yl,6-di-Cl-pyridin-2-yl 5-OCF3-pyridazin-2-yl 6-F-pyridin-3-yl 5-N(Me)2-pyridazin-2-yl 6-Cl-pyridin-3-yl 5 -Ph-pyridazin- 2 -yl 6-Br-pyridin-3-yl 5-F-pyrimidin-4-yl 6-I-pyridin-3-yl 5-Cl-pyrimidin-4-yl 6-Me-pyridin-3 -yl 5-Br-pyrimidin-4-yl 6-Et-pyridin-3-yl 5-I-pyrimidin-4-yl 6-CF3 -pyridin-3 -yl 5-Me-pyrimidin-4-yl 6-CHF2-pyridin-3 -yl 5-Et-pyrimidin-4-yl 6-CHO-pyridin-3-yl 5-CF3-pyrimidin-4-yl 6-C -pyridin-3 -yl 5-CHF2-pyrimidin-4-yl 6-OMe -pyridin-3 -yl 5 -CHO-pyrimidin-4-yl 6-OCF3 -pyridin-3 -yl 5-CN-pyrimidin-4-yl-N(Me)2-pyridin-3-yl 5-OMe-pyrimidin-4-yl

[0640] 6-Ph-pyridin-3 -yl 5-OCF3-pyrimidin-4-yl ,6-di-Cl-pyridin-3-yl 5-N(Me)2-pyrimidin-4-yl-CN-6-Cl-pyridin-3-yl 5-Ph-pyrimidin-4-yl 3-F-pyridin-4-yl 2-F-pyrimidin-5-yl 3-Cl-pyridin-4-yl 2-Cl-pyrimidin-5-yl 3 -Br-pyridin-4-yl 2-Br-pyrimidin-5-yl 3-I-pyridin-4-yl 2 -I-pyrimidin-5 -yl 3 -Me-pyridin-4-yl 2 -Me-pyrimidin-5 -yl 3-Et-pyridin-4-yl 2-Et-pyrimidin-5-yl 3 -CF3 -pyridin-4-yl 2 -CF3 -pyrimidin-5 -yl 3-CHF2-pyridin-4-yl 2-CHF2-pyrimidin-5-yl 3-CHO-pyridin-4-yl 2-CHO-pyrimidin-5-yl 3 -CN-pyridin-4-yl 2 -CN-pyrimidin- 5 -yl2 -OMe -pyrimidin- 5 -yl 6-CN-[l,2,4]triazin-3-yl

[0641] 2- OCF3-pyrimidin-5-yl 4-Cl-[l,3,5]triazin-2-yl 2-N(Me)2-pyrimidin-5-yl 4-CF3-phenyl

[0642] 2 -Ph-pyrimidin- 5 -yl 4-OCF3 -phenyl 3 -Cl-pyrazin-2-yl 3 -OCF3 -phenyl 3 -CN-pyrazin-2-yl 3,5-di-OCF3-phenyl

[0643] 3 -OMe-pyrazin-2-yl 3,5-di-Cl-phenyl

[0644] 3- Cl-[l,2,4]triazin-6-yl

[0645] 3-CN-[l,2,4]triazin-6-yl

[0646] The present disclosure also includes Tables 2 through 1584. Each Table is constructed in the the same manner as Table 1 above, except that the row heading in Table 1 (i.e. "R2= CI; Z = O; and R3= H (m = 0)") is replaced with the respective row heading shown below. For example, the first entry in Table 2 is a compound of Formula 1 wherein R1is H, R2is CI, Z is O, R3is H (m = 0), and Q is isoxazol-5-yl (i.e. unsubstituted isoxazole attached to the remainder of Formula 1 at the 5 -position). The remainder of Table 2 is constructed in the same way, and hence the remainder of Tables through 1584 is constructed the same way.

[0647] Table Header Row Table Header Row

[0648] 2 R2= F, Z = O, R3= H (m = 0) 23 R2= F, Z = 0, R3= 3-Ph

[0649] 3 R2= F, Z = O, R3= 3-F 24 R2= F, Z = S, R3= 3-F

[0650] 4 R2= F, Z = O, R3= 3-Cl 25 R2= F, Z = S, R3= 3 -CI

[0651] 5 R2= F, Z = O, R3= 3-Br 26 R2= F, Z = S, R3= 3-Br

[0652] 6 R2= F, Z = 0, R3= 3-I 27 R2= F, Z = S, R3= 3-1

[0653] 7 R2= F, Z = 0, R3= 3-CN 28 R2= F, Z = S, R3= 3-CN

[0654] 8 R2= F, Z = O, R3= 3-N0229 R2= F, Z = S, R3= 3-N02

[0655] 9 R2= F, Z = O, R3= 3-OMe 30 R2= F, Z = S, R3= 3-OMe

[0656] 10 R2= F, Z = 0, R3= 3-OCF331 R2= F, Z = S, R3= 3-OCF3

[0657] 11 R2= F, Z = O, R3= 3-CF3 32 R2= F, Z = S, R3= 3-CF3

[0658] 12 R2= F, Z = 0, R3= 3-CHF233 R2= F, Z = S, R3= 3-CHF2

[0659] 13 R2= F, Z = 0, R3= 3-CH2F 34 R2= F, Z = S, R3= 3-CH2F

[0660] 14 R2= F, Z = 0, R3= 3-CHO 35 R2= F, Z = S, R3= 3-CHO

[0661] 15 R2= F, Z = O, R3= 3-Me 36 R2= F, Z = S, R3= 3-Me

[0662] 16 R2= F, Z = O, R3= 3-Et 37 R2= F, Z = S, R3= 3-Et

[0663] 17 R2= F, Z = O, R3= 3-Ethynyl 38 R2= F, Z = S, R3= 3-Ethynyl

[0664] 18 R2= F, Z = O, R3= 3-Ethenyl 39 R2= F, Z = S, R3= 3-Ethenyl

[0665] 19 R2= F, Z = O, R3= 3-S02Me 40 R2= F, Z = S, R3= 3-S02Me

[0666] 20 R2= F, Z = O, R3= 3-OAc 41 R2= F, Z = S, R3= 3-OAc

[0667] 21 R2= F, Z = O, R3= 3-c-Pr 42 R2= F, Z = S, R3= 3-c-Pr

[0668] 22 R2= F, Z = O, R3= 3-z-Pr 43 R2= F, Z = S, R3= 3-z-Pr

[0669] Table Header Row Table Header Row

[0670] 44 R2= F, Z = S, R3= 3-Ph 81 R2= F, Z = O, R3= 5-Ethenyl

[0671] 45 R2= F, Z = O, R3= 4-F 82 R2= F, Z = O, R3= 5-S02Me

[0672] 46 R2= F, Z = O, R3= 4-Cl 83 R2= F, Z = O, R3= 5-OAc

[0673] 47 R2= F, Z = O, R3= 4-Br 84 R2= F, Z = O, R3= 5-c-Pr

[0674] 48 R2= F, Z = O, R3= 4-1 85 R2= F, Z = O, R3= 5- -Pr

[0675] 49 R2= F, Z = O, R3= 4-CN 86 R2= F, Z = O, R3= 5-Ph

[0676] 50 R2= F, Z = O, R3= 4-N0287 R2= F, Z = O, R3= 6-F

[0677] 51 R2= F, Z = O, R3= 4-OMe 88 R2= F, Z = O, R3= 6-Cl

[0678] 52 R2= F, Z = O, R3= 4-OCF389 R2= F, Z = O, R3= 6-Br

[0679] 53 R2= F, Z = O, R3= 4-CF3 90 R2= F, Z = O, R3= 6-1

[0680] 54 R2= F, Z = O, R3= 4-CHF291 R2= F, Z = O, R3= 6-CN

[0681] 55 R2= F, Z = O, R3= 4-CH2F 92 R2= F, Z = O, R3= 6-N02

[0682] 56 R2= F, Z = O, R3= 4-CHO 93 R2= F, Z = O, R3= 6-OMe

[0683] 57 R2= F, Z = O, R3= 4-Me 94 R2= F, Z = O, R3= 6-OCF3

[0684] 58 R2= F, Z = O, R3= 4-Et 95 R2= F, Z = O, R3= 6-CF3

[0685] 59 R2= F, Z = O, R3= 4-Ethynyl 96 R2= F, Z = O, R3= 6-CHF2

[0686] 60 R2= F, Z = O, R3= 4-Ethenyl 97 R2= F, Z = O, R3= 6-CH2F

[0687] 61 R2= F, Z = O, R3= 4-S02Me 98 R2= F, Z = O, R3= 6-CHO

[0688] 62 R2= F, Z = O, R3= 4-OAc 99 R2= F, Z = O, R3= 6-Me

[0689] 63 R2= F, Z = O, R3= 4-c-Pr 100 R2= F, Z = O, R3= 6-Et

[0690] 64 R2= F, Z = O, R3= 4-z-Pr 101 R2= F, Z = O, R3= 6-Ethynyl

[0691] 65 R2= F, Z = O, R3= 4-Ph 102 R2= F, Z = O, R3= 6-Ethenyl

[0692] 66 R2= F, Z = O, R3= 5-F 103 R2= F, Z = O, R3= 6-S02Me

[0693] 67 R2= F, Z = O, R3= 5-Cl 104 R2= F, Z = O, R3= 6-OAc

[0694] 68 R2= F, Z = O, R3= 5-Br 105 R2= F, Z = O, R3= 6-c-Pr

[0695] 69 R2= F, Z = O, R3= 5-1 106 R2= F, Z = O, R3= 6-z-Pr

[0696] 70 R2= F, Z = O, R3= 5-CN 107 R2= F, Z = O, R3= 6-Ph

[0697] 71 R2= F, Z = O, R3= 5-N02108 R2= F, Z = O, R3= 3,4-di-F

[0698] 72 R2= F, Z = O, R3= 5-OMe 109 R2= F, Z = O, R3= 3,5-di-F

[0699] 73 R2= F, Z = O, R3= 5-OCF3 110 R2= F, Z = O, R3= 3,6-di-F

[0700] 74 R2= F, Z = O, R3= 5-CF3 111 R2= F, Z = O, R3= 4,5-di-F

[0701] 75 R2= F, Z = O, R3= 5-CHF2112 R2= F, Z = O, R3= 3,4-di-Cl

[0702] 76 R2= F, Z = O, R3= 5-CH2F 113 R2= F, Z = O, R3= 3,5-di-Cl

[0703] 77 R2= F, Z = O, R3= 5-CHO 114 R2= F, Z = O, R3= 3,6-di-Cl

[0704] 78 R2= F, Z = O, R3=5-Me 115 R2= F, Z = O, R3= 4,5-di-Cl

[0705] 79 R2= F, Z = O, R3= 5-Et 1 16 R2= F, Z = O, R3= 3,4-di-Br

[0706] 80 R2= F, Z = O, R3= 5-Ethynyl 1 17 R2= F, Z = O, R3= 3,5-di-BrTable Header Row Table Header Row

[0707] 118 R2= F, Z = O, R3= 3,6-di-Br 155 R2= Br, Z = O, R3= 3-CF3

[0708] 119 R2= F, Z = O, R3= 4,5-di-Br 156 R2= Br, Z = O, R3= 3-CHF2

[0709] 120 R2= F, Z = O, R3= 3,4-di-CN 157 R2= Br, Z = O, R3= 3-CH2F

[0710] 121 R2= F, Z = O, R3= 3,5-di-CN 158 R2= Br, Z = O, R3= 3-CHO

[0711] 122 R2= F, Z = O, R3= 3,6-di-CN 159 R2= Br, Z = O, R3= 3-Me

[0712] 123 R2= F, Z = O, R3= 4,5-di-CN 160 R2= Br, Z = O, R3= 3-Et

[0713] 124 R2= F, Z = O, R3= 3,4-di-Me 161 R2= Br, Z = O, R3= 3-Ethynyl

[0714] 125 R2= F, Z = O, R3= 3,5-di-Me 162 R2= Br, Z = O, R3= 3-Ethenyl

[0715] 126 R2= F, Z = O, R3= 3,6-di-Me 163 R2= Br, Z = O, R3= 3-S02Me

[0716] 127 R2= F, Z = O, R3= 4,5-di-Me 164 R2= Br, Z = O, R3= 3-OAc

[0717] 128 R2= F, Z = O, R3= 3,4-di-OMe 165 R2= Br, Z = O, R3= 3-c-Pr

[0718] 129 R2= F, Z = O, R3= 3,5-di-OMe 166 R2= Br, Z = O, R3= 3-z-Pr

[0719] 130 R2= F, Z = O, R3= 3,6-di-OMe 167 R2= Br, Z = O, R3= 3-Ph

[0720] 131 R2= F, Z = O, R3= 4,5-di-OMe 168 R2= Br, Z = S, R3= 3-F

[0721] 132 R2= F, Z = O, R3= 3,4-di-CF3169 R2= Br, Z = S, R3= 3 -CI

[0722] 133 R2= F, Z = O, R3= 3,5-di-CF3170 R2= Br, Z = S, R3= 3-Br

[0723] 134 R2= F, Z = O, R3= 3,6-di-CF3171 R2= Br, Z = S, R3= 3-1

[0724] 135 R2= F, Z = O, R3= 4,5-di-CF3172 R2= Br, Z = S, R3= 3-CN

[0725] 136 R2= F, Z = O, R3= 3-CN, 4-Me 173 R2= Br, Z = S, R3= 3-N02

[0726] 137 R2= F, Z = O, R3= 3-CN, 4-F 174 R2= Br, Z = S, R3= 3-OMe

[0727] 138 R2= F, Z = O, R3= 3-CN, 4-Br 175 R2= Br, Z = S, R3= 3-OCF3

[0728] 139 R2= F, Z = O, R3= 3-CN, 4-OMe 176 R2= Br, Z = S, R3= 3-CF3

[0729] 140 R2= F, Z = O, R3= 3-CN, 4-CF3177 R2= Br, Z = S, R3= 3-CHF2

[0730] 141 R2= F, Z = O, R3= 3-CN, 6-Me 178 R2= Br, Z = S, R3= 3-CH2F

[0731] 142 R2= F, Z = O, R3= 3-CN, 6-F 179 R2= Br, Z = S, R3= 3-CHO

[0732] 143 R2= F, Z = O, R3= 3-CN, 6-Br 180 R2= Br, Z = S, R3= 3-Me

[0733] 144 R2= F, Z = O, R3= 3-CN, 6-OMe 181 R2= Br, Z = S, R3= 3-Et

[0734] 145 R2= F, Z = O, R3= 3-CN, 6-CF3182 R2= Br, Z = S, R3= 3-Ethynyl

[0735] 146 R2= Br, Z = O, R3= H (m = 0) 183 R2= Br, Z = S, R3= 3-Ethenyl

[0736] 147 R2= Br, Z = O, R3= 3-F 184 R2= Br, Z = S, R3= 3-S02Me

[0737] 148 R2= Br, Z = O, R3= 3 -CI 185 R2= Br, Z = S, R3= 3-OAc

[0738] 149 R2= Br, Z = O, R3= 3-Br 186 R2= Br, Z = S, R3= 3-c-Pr

[0739] 150 R2= Br, Z = O, R3= 3-1 187 R2= Br, Z = S, R3= 3-z-Pr

[0740] 151 R2= Br, Z = O, R3= 3-CN 188 R2= Br, Z = S, R3= 3-Ph

[0741] 152 R2= Br, Z = O, R3= 3-N02189 R2= Br, Z = O, R3= 4-F

[0742] 153 R2= Br, Z = O, R3= 3-OMe 190 R2= Br, Z = O, R3= 4-Cl

[0743] 154 R2= Br, Z = O, R3= 3-OCF3191 R2= Br, Z = O, R3= 4-BrTable Header Row Table Header Row

[0744] 192 R2= Br, Z = O, R3= 4-1 229 R2= Br, Z = O, R3= 5-z-Pr

[0745] 193 R2= Br, Z = O, R3= 4-CN 230 R2= Br, Z = O, R3= 5-Ph

[0746] 194 R2= Br, Z = O, R3= 4-N02231 R2= Br, Z = O, R3= 6-F

[0747] 195 R2= Br, Z = O, R3= 4-OMe 232 R2= Br, Z = O, R3= 6-Cl

[0748] 196 R2= Br, Z = O, R3= 4-OCF3233 R2= Br, Z = O, R3= 6-Br

[0749] 197 R2= Br, Z = O, R3= 4-CF3 234 R2= Br, Z = O, R3= 6-1

[0750] 198 R2= Br, Z = O, R3= 4-CHF2235 R2= Br, Z = O, R3= 6-CN

[0751] 199 R2= Br, Z = O, R3= 4-CH2F 236 R2= Br, Z = O, R3= 6-N02

[0752] 200 R2= Br, Z = O, R3= 4-CHO 237 R2= Br, Z = O, R3= 6-OMe

[0753] 201 R2= Br, Z = O, R3= 4-Me 238 R2= Br, Z = O, R3= 6-OCF3

[0754] 202 R2= Br, Z = O, R3= 4-Et 239 R2= Br, Z = O, R3= 6-CF3

[0755] 203 R2= Br, Z = O, R3= 4-Ethynyl 240 R2= Br, Z = O, R3= 6-CHF2

[0756] 204 R2= Br, Z = O, R3= 4-Ethenyl 241 R2= Br, Z = O, R3= 6-CH2F

[0757] 205 R2= Br, Z = O, R3= 4-S02Me 242 R2= Br, Z = O, R3= 6-CHO

[0758] 206 R2= Br, Z = O, R3= 4-OAc 243 R2= Br, Z = O, R3= 6-Me

[0759] 207 R2= Br, Z = O, R3= 4-c-Pr 244 R2= Br, Z = O, R3= 6-Et

[0760] 208 R2= Br, Z = O, R3= 4-z-Pr 245 R2= Br, Z = O, R3= 6-Ethynyl

[0761] 209 R2= Br, Z = O, R3= 4-Ph 246 R2= Br, Z = O, R3= 6-Ethenyl

[0762] 210 R2= Br, Z = O, R3= 5-F 247 R2= Br, Z = O, R3= 6-S02Me

[0763] 211 R2= Br, Z = O, R3= 5-Cl 248 R2= Br, Z = O, R3= 6-OAc

[0764] 212 R2= Br, Z = O, R3= 5-Br 249 R2= Br, Z = O, R3= 6-c-Pr

[0765] 213 R2= Br, Z = O, R3= 5-1 250 R2= Br, Z = O, R3= 6-z-Pr

[0766] 214 R2= Br, Z = O, R3= 5-CN 251 R2= Br, Z = O, R3= 6-Ph

[0767] 215 R2= Br, Z = O, R3= 5-N02252 R2= Br, Z = O, R3= 3,4-di-F

[0768] 216 R2= Br, Z = O, R3= 5-OMe 253 R2= Br, Z = O, R3= 3,5-di-F

[0769] 217 R2= Br, Z = O, R3= 5-OCF3 254 R2= Br, Z = O, R3= 3,6-di-F

[0770] 218 R2= Br, Z = O, R3= 5-CF3 255 R2= Br, Z = O, R3= 4,5-di-F

[0771] 219 R2= Br, Z = O, R3= 5-CHF2256 R2= Br, Z = O, R3= 3,4-di-Cl

[0772] 220 R2= Br, Z = O, R3= 5-CH2F 257 R2= Br, Z = O, R3= 3,5-di-Cl

[0773] 221 R2= Br, Z = O, R3= 5-CHO 258 R2= Br, Z = O, R3= 3,6-di-Cl

[0774] 222 R2= Br, Z = O, R3=5-Me 259 R2= Br, Z = O, R3= 4,5-di-Cl

[0775] 223 R2= Br, Z = O, R3= 5-Et 260 R2= Br, Z = O, R3= 3,4-di-Br

[0776] 224 R2= Br, Z = O, R3= 5-Ethynyl 261 R2= Br, Z = O, R3= 3,5-di-Br

[0777] 225 R2= Br, Z = O, R3= 5-Ethenyl 262 R2= Br, Z = O, R3= 3,6-di-Br

[0778] 226 R2= Br, Z = O, R3= 5-S02Me 263 R2= Br, Z = O, R3= 4,5-di-Br

[0779] 227 R2= Br, Z = O, R3= 5-OAc 264 R2= Br, Z = O, R3= 3,4-di-CN

[0780] 228 R2= Br, Z = O, R3= 5-c-Pr 265 R2= Br, Z = O, R3= 3,5-di-CNTable Header Row Table Header Row

[0781] 266 R2= Br, Z = O, R3= 3,6-di-CN 303 R2= CI, Z = O, R3= 3-Me

[0782] 267 R2= Br, Z = O, R3= 4,5-di-CN 304 R2= CI, Z = O, R3= 3-Et

[0783] 268 R2= Br, Z = O, R3= 3,4-di-Me 305 R2= CI, Z = O, R3= 3-Ethynyl

[0784] 269 R2= Br, Z = O, R3= 3,5-di-Me 306 R2= CI, Z = O, R3= 3-Ethenyl

[0785] 270 R2= Br, Z = O, R3= 3,6-di-Me 307 R2= CI, Z = O, R3= 3-S02Me

[0786] 271 R2= Br, Z = O, R3= 4,5-di-Me 308 R2= CI, Z = O, R3= 3-OAc

[0787] 272 R2= Br, Z = O, R3= 3,4-di-OMe 309 R2= CI, Z = O, R3= 3-c-Pr

[0788] 273 R2= Br, Z = O, R3= 3,5-di-OMe 310 R2= C1, Z = 0, R3= 3-z-Pr

[0789] 274 R2= Br, Z = O, R3= 3,6-di-OMe 311 R2= CI, Z = O, R3= 3-Ph

[0790] 275 R2= Br, Z = O, R3= 4,5-di-OMe 312 R2= CI, Z = S, R3= 3-F

[0791] 276 R2= Br, Z = O, R3= 3,4-di-CF3313 R2= CI, Z = S, R3= 3 -CI

[0792] 277 R2= Br, Z = O, R3= 3,5-di-CF3314 R2= CI, Z = S, R3= 3-Br

[0793] 278 R2= Br, Z = O, R3= 3,6-di-CF3315 R2= CI, Z = S, R3= 3-1

[0794] 279 R2= Br, Z = O, R3= 4,5-di-CF3316 R2= CI, Z = S, R3= 3-CN

[0795] 280 R2= Br, Z = O, R3= 3-CN, 4-Me 317 R2= CI, Z = S, R3= 3-N02

[0796] 281 R2= Br, Z = O, R3= 3-CN, 4-F 318 R2= CI, Z = S, R3= 3-OMe

[0797] 282 R2= Br, Z = O, R3= 3-CN, 4-Br 319 R2= CI, Z = S, R3= 3-OCF3

[0798] 283 R2= Br, Z = O, R3= 3-CN, 4-OMe 320 R2= CI, Z = S, R3= 3-CF3

[0799] 284 R2= Br, Z = O, R3= 3-CN, 4-CF3321 R2= CI, Z = S, R3= 3-CHF2

[0800] 285 R2= Br, Z = O, R3= 3-CN, 6-Me 322 R2= CI, Z = S, R3= 3-CH2F

[0801] 286 R2= Br, Z = O, R3= 3-CN, 6-F 323 R2= CI, Z = S, R3= 3-CHO

[0802] 287 R2= Br, Z = O, R3= 3-CN, 6-Br 324 R2= CI, Z = S, R3= 3-Me

[0803] 288 R2= Br, Z = O, R3= 3-CN, 6-OMe 325 R2= CI, Z = S, R3= 3-Et

[0804] 289 R2= Br, Z = O, R3= 3-CN, 6-CF3326 R2= CI, Z = S, R3= 3-Ethynyl

[0805] 290 R2= CI, Z = O, R3= H (m = 0) 327 R2= CI, Z = S, R3= 3-Ethenyl

[0806] 291 R2= CI, Z = O, R3= 3-F 328 R2= CI, Z = S, R3= 3-S02Me

[0807] 292 R2= CI, Z = O, R3= 3-Cl 329 R2= CI, Z = S, R3= 3-OAc

[0808] 293 R2= CI, Z = O, R3= 3-Br 330 R2= CI, Z = S, R3= 3-c-Pr

[0809] 294 R2= CI, Z = O, R3= 3-1 331 R2= CI, Z = S, R3= 3-z-Pr

[0810] 295 R2= CI, Z = O, R3= 3-CN 332 R2= CI, Z = S, R3= 3-Ph

[0811] 296 R2= CI, Z = O, R3= 3-N02333 R2= CI, Z = O, R3= 4-F

[0812] 297 R2= CI, Z = O, R3= 3-OMe 334 R2= CI, Z = O, R3= 4-Cl

[0813] 298 R2= CI, Z = O, R3= 3-OCF3335 R2= CI, Z = O, R3= 4-Br

[0814] 299 R2= CI, Z = O, R3= 3-CF3336 R2= CI, Z = O, R3= 4-1

[0815] 300 R2= CI, Z = O, R3= 3-CHF2337 R2= CI, Z = O, R3= 4-CN

[0816] 301 R2= CI, Z = O, R3= 3-CH2F 338 R2= CI, Z = O, R3= 4-N02

[0817] 302 R2= CI, Z = O, R3= 3-CHO339 R2= CI, Z = O, R3= 4-OMeTable Header Row Table Header Row

[0818] 340 R2= CI, Z = O, R3= 4-OCF3377 R2= CI, Z = O, R3= 6-Br

[0819] 341 R2= CI, Z = O, R3= 4-CF3 378 R2= CI, Z = O, R3= 6-1

[0820] 342 R2= CI, Z = O, R3= 4-CHF2379 R2= CI, Z = O, R3= 6-CN

[0821] 343 R2= CI, Z = O, R3= 4-CH2F 380 R2= CI, Z = O, R3= 6-N02

[0822] 344 R2= CI, Z = O, R3= 4-CHO 381 R2= CI, Z = O, R3= 6-OMe

[0823] 345 R2= CI, Z = O, R3= 4-Me 382 R2= CI, Z = O, R3= 6-OCF3

[0824] 346 R2= CI, Z = O, R3= 4-Et 383 R2= CI, Z = O, R3= 6-CF3

[0825] 347 R2= CI, Z = O, R3= 4-Ethynyl 384 R2= CI, Z = O, R3= 6-CHF2

[0826] 348 R2= CI, Z = O, R3= 4-Ethenyl 385 R2= CI, Z = O, R3= 6-CH2F

[0827] 349 R2= CI, Z = O, R3= 4-S02Me 386 R2= CI, Z = O, R3= 6-CHO

[0828] 350 R2= CI, Z = O, R3= 4-OAc 387 R2= CI, Z = O, R3= 6-Me

[0829] 351 R2= CI, Z = O, R3= 4-c-Pr 388 R2= CI, Z = O, R3= 6-Et

[0830] 352 R2= CI, Z = O, R3= 4-z-Pr 389 R2= CI, Z = O, R3= 6-Ethynyl

[0831] 353 R2= CI, Z = O, R3= 4-Ph 390 R2= CI, Z = O, R3= 6-Ethenyl

[0832] 354 R2= CI, Z = O, R3= 5-F 391 R2= CI, Z = O, R3= 6-S02Me

[0833] 355 R2= CI, Z = O, R3= 5-Cl 392 R2= CI, Z = O, R3= 6-OAc

[0834] 356 R2= CI, Z = O, R3= 5-Br 393 R2= CI, Z = O, R3= 6-c-Pr

[0835] 357 R2= CI, Z = O, R3= 5-1 394 R2= CI, Z = O, R3= 6-z-Pr

[0836] 358 R2= CI, Z = O, R3= 5-CN 395 R2= CI, Z = O, R3= 6-Ph

[0837] 359 R2= CI, Z = O, R3= 5-N02396 R2= CI, Z = O, R3= 3,4-di-F

[0838] 360 R2= CI, Z = O, R3= 5-OMe 397 R2= CI, Z = O, R3= 3,5-di-F

[0839] 361 R2= CI, Z = O, R3= 5-OCF3 398 R2= CI, Z = O, R3= 3,6-di-F

[0840] 362 R2= CI, Z = O, R3= 5-CF3 399 R2= CI, Z = O, R3= 4,5-di-F

[0841] 363 R2= CI, Z = O, R3= 5-CHF2400 R2= CI, Z = O, R3= 3,4-di-Cl

[0842] 364 R2= CI, Z = O, R3= 5-CH2F 401 R2= CI, Z = O, R3= 3,5-di-Cl

[0843] 365 R2= CI, Z = O, R3= 5-CHO 402 R2= CI, Z = O, R3= 3,6-di-Cl

[0844] 366 R2= CI, Z = O, R3=5-Me 403 R2= CI, Z = O, R3= 4,5-di-Cl

[0845] 367 R2= CI, Z = O, R3= 5-Et 404 R2= CI, Z = O, R3= 3,4-di-Br

[0846] 368 R2= CI, Z = O, R3= 5-Ethynyl 405 R2= CI, Z = O, R3= 3,5-di-Br

[0847] 369 R2= CI, Z = O, R3= 5-Ethenyl 406 R2= CI, Z = O, R3= 3,6-di-Br

[0848] 370 R2= CI, Z = O, R3= 5-S02Me 407 R2= CI, Z = O, R3= 4,5-di-Br

[0849] 371 R2= CI, Z = O, R3= 5-OAc 408 R2= CI, Z = O, R3= 3,4-di-CN

[0850] 372 R2= CI, Z = O, R3= 5-c-Pr 409 R2= CI, Z = O, R3= 3,5-di-CN

[0851] 373 R2= CI, Z = O, R3= 5-z-Pr 410 R2= CI, Z = O, R3= 3,6-di-CN

[0852] 374 R2= CI, Z = O, R3= 5-Ph 411 R2= CI, Z = O, R3= 4,5-di-CN

[0853] 375 R2= CI, Z = O, R3= 6-F 412 R2= CI, Z = O, R3= 3,4-di-Me

[0854] 376 R2= CI, Z = O, R3= 6-Cl 413

[0855] R2= CI, Z = O, R3= 3,5-di-MeTable Header Row Table Header Row

[0856] 414 R2= CI, Z = O, R3= 3,6-di-Me 451 R2= I, Z = O, R3= 3-S02Me

[0857] 415 R2= CI, Z = O, R3= 4,5-di-Me 452 R2= I, Z = 0, R3= 3-OAc

[0858] 416 R2= CI, Z = O, R3= 3,4-di-OMe 453 R2= I, Z = O, R3= 3-c-Pr

[0859] 417 R2= CI, Z = O, R3= 3,5-di-OMe 454 R2= I, Z = 0, R3= 3-z-Pr

[0860] 418 R2= CI, Z = O, R3= 3,6-di-OMe 455 R2= I, Z = O, R3= 3-Ph

[0861] 419 R2= CI, Z = O, R3= 4,5-di-OMe 456 R2= I, Z = S, R3= 3-F

[0862] 420 R2= CI, Z = O, R3= 3,4-di-CF3457 R2= I, Z = S, R3= 3-Cl

[0863] 421 R2= CI, Z = O, R3= 3,5-di-CF3458 R2= I, Z = S, R3= 3-Br

[0864] 422 R2= CI, Z = O, R3= 3,6-di-CF3459 R2= I, Z = S, R3= 3-1

[0865] 423 R2= CI, Z = O, R3= 4,5-di-CF3460 R2= I, Z = S, R3= 3-CN

[0866] 424 R2= CI, Z = O, R3= 3-CN, 4-Me 461 R2= I, Z = S, R3= 3-N02

[0867] 425 R2= CI, Z = O, R3= 3-CN, 4-F 462 R2= I, Z = S, R3= 3-OMe

[0868] 426 R2= CI, Z = O, R3= 3-CN, 4-Br 463 R2= I, Z = S, R3= 3-OCF3

[0869] 427 R2= CI, Z = O, R3= 3-CN, 4-OMe 464 R2= I, Z = S, R3= 3-CF3

[0870] 428 R2= CI, Z = O, R3= 3-CN, 4-CF3465 R2= I, Z = S, R3= 3-CHF2

[0871] 429 R2= CI, Z = O, R3= 3-CN, 6-Me 466 R2= I, Z = S, R3= 3-CH2F

[0872] 430 R2= CI, Z = O, R3= 3-CN, 6-F 467 R2= I, Z = S, R3= 3-CHO

[0873] 431 R2= CI, Z = O, R3= 3-CN, 6-Br 468 R2= I, Z = S, R3= 3-Me

[0874] 432 R2= CI, Z = O, R3= 3-CN, 6-OMe 469 R2= I, Z = S, R3= 3-Et

[0875] 433 R2= CI, Z = O, R3= 3-CN, 6-CF3470 R2= I, Z = S, R3= 3-Ethynyl

[0876] 434 R2= I, Z = O, R3= H (m = 0) 471 R2= I, Z = S, R3= 3-Ethenyl

[0877] 435 R2= I, Z = O, R3= 3-F 472 R2= I, Z = S, R3= 3-S02Me

[0878] 436 R2= I, Z = O, R3= 3 -CI 473 R2= I, Z = S, R3= 3-OAc

[0879] 437 R2= I, Z = O, R3= 3-Br 474 R2= I, Z = S, R3= 3-c-Pr

[0880] 438 R2= I, Z = O, R3= 3-1 475 R2= I, Z = S, R3= 3-z-Pr

[0881] 439 R2= I, Z = 0, R3= 3-CN 476 R2= I, Z = S, R3= 3-Ph

[0882] 440 R2= I, Z = O, R3= 3-N02477 R2= I, Z = O, R3= 4-F

[0883] 441 R2= I, Z = O, R3= 3-OMe 478 R2= I, Z = O, R3= 4-Cl

[0884] 442 R2= I, Z = O, R3= 3-OCF3479 R2= I, Z = O, R3= 4-Br

[0885] 443 R2= I, Z = O, R3= 3-CF3480 R2= I, Z = O, R3= 4-1

[0886] 444 R2= I, Z = O, R3= 3-CHF2481 R2= I, Z = O, R3= 4-CN

[0887] 445 R2= I, Z = O, R3= 3-CH2F 482 R2= I, Z = O, R3= 4-N02

[0888] 446 R2= I, Z = O, R3= 3-CHO 483 R2= I, Z = O, R3= 4-OMe

[0889] 447 R2= I, Z = O, R3= 3-Me 484 R2= I, Z = O, R3= 4-OCF3

[0890] 448 R2= I, Z = O, R3= 3-Et 485 R2= I, Z = O, R3= 4-CF3

[0891] 449 R2= I, Z = O, R3= 3-Ethynyl 486 R2= I, Z = O, R3= 4-CHF2

[0892] 450 R2= I, Z = O, R3= 3-Ethenyl487 R2= I, Z = O, R3= 4-CH2FTable Header Row Table Header Row

[0893] 488 R2= I, Z = O, R3= 4-CHO 525 R2= I, Z = O, R3= 6-OMe

[0894] 489 R2= I, Z = O, R3= 4-Me 526 R2= I, Z = O, R3= 6-OCF3

[0895] 490 R2= I, Z = O, R3= 4-Et 527 R2= I, Z = O, R3= 6-CF3

[0896] 491 R2= I, Z = O, R3= 4-Ethynyl 528 R2= I, Z = O, R3= 6-CHF2

[0897] 492 R2= I, Z = O, R3= 4-Ethenyl 529 R2= I, Z = O, R3= 6-CH2F

[0898] 493 R2= I, Z = O, R3= 4-S02Me 530 R2= I, Z = O, R3= 6-CHO

[0899] 494 R2= I, Z = O, R3= 4-OAc 531 R2= I, Z = O, R3= 6-Me

[0900] 495 R2= I, Z = O, R3= 4-c-Pr 532 R2= I, Z = O, R3= 6-Et

[0901] 496 R2= I, Z = O, R3= 4-z-Pr 533 R2= I, Z = O, R3= 6-Ethynyl

[0902] 497 R2= I, Z = O, R3= 4-Ph 534 R2= I, Z = O, R3= 6-Ethenyl

[0903] 498 R2= I, Z = O, R3= 5-F 535 R2= I, Z = O, R3= 6-S02Me

[0904] 499 R2= I, Z = O, R3= 5-Cl 536 R2= I, Z = O, R3= 6-OAc

[0905] 500 R2= I, Z = O, R3= 5-Br 537 R2= I, Z = O, R3= 6-c-Pr

[0906] 501 R2= I, Z = O, R3= 5-1 538 R2= I, Z = O, R3= 6-z-Pr

[0907] 502 R2= I, Z = O, R3= 5-CN 539 R2= I, Z = O, R3= 6-Ph

[0908] 503 R2= I, Z = O, R3= 5-N02540 R2= I, Z = 0, R3= 3,4-di-F

[0909] 504 R2= I, Z = O, R3= 5-OMe 541 R2= I, Z = 0, R3= 3,5-di-F

[0910] 505 R2= I, Z = O, R3= 5-OCF3542 R2= I, Z = 0, R3= 3,6-di-F

[0911] 506 R2= I, Z = O, R3= 5-CF3 543 R2= I, Z = O, R3= 4,5-di-F

[0912] 507 R2= I, Z = O, R3= 5-CHF2544 R2= I, Z = O, R3= 3,4-di-Cl

[0913] 508 R2= I, Z = O, R3= 5-CH2F 545 R2= I, Z = O, R3= 3,5-di-Cl

[0914] 509 R2= I, Z = O, R3= 5-CHO 546 R2= I, Z = O, R3= 3,6-di-Cl

[0915] 510 R2= I, Z = O, R3=5-Me 547 R2= I, Z = O, R3= 4,5-di-Cl

[0916] 51 1 R2= I, Z = O, R3= 5-Et 548 R2= I, Z = O, R3= 3,4-di-Br

[0917] 512 R2= I, Z = O, R3= 5-Ethynyl 549 R2= I, Z = O, R3= 3,5-di-Br

[0918] 513 R2= I, Z = O, R3= 5-Ethenyl 550 R2= I, Z = O, R3= 3,6-di-Br

[0919] 514 R2= I, Z = O, R3= 5-S02Me 551 R2= I, Z = O, R3= 4,5-di-Br

[0920] 515 R2= I, Z = O, R3= 5-OAc 552 R2= I, Z = O, R3= 3,4-di-CN

[0921] 516 R2= I, Z = O, R3= 5-c-Pr 553 R2= I, Z = O, R3= 3,5-di-CN

[0922] 517 R2= I, Z = O, R3= 5-z-Pr 554 R2= I, Z = O, R3= 3,6-di-CN

[0923] 518 R2= I, Z = O, R3= 5-Ph 555 R2= I, Z = O, R3= 4,5-di-CN

[0924] 519 R2= I, Z = O, R3= 6-F 556 R2= I, Z = O, R3= 3,4-di-Me

[0925] 520 R2= I, Z = O, R3= 6-Cl 557 R2= I, Z = O, R3= 3,5-di-Me

[0926] 521 R2= I, Z = O, R3= 6-Br 558 R2= I, Z = O, R3= 3,6-di-Me

[0927] 522 R2= I, Z = O, R3= 6-1 559 R2= I, Z = O, R3= 4,5-di-Me

[0928] 523 R2= I, Z = O, R3= 6-CN 560 R2= I, Z = O, R3= 3,4-di-OMe

[0929] 524 R2= I, Z = O, R3= 6-N02561 R2= I, Z = O, R3= 3,5-di-OMeTable Header Row Table Header Row

[0930] 562 R2= I, Z = O, R3= 3,6-di-OMe 599 R2= Me, Z = O, R3= 3-Ph

[0931] 563 R2= I, Z = O, R3= 4,5-di-OMe 600 R2= Me, Z = S, R3= 3-F

[0932] 564 R2= I, Z = O, R3= 3,4-di-CF3601 R2= Me, Z = S, R3= 3 -CI

[0933] 565 R2= I, Z = O, R3= 3,5-di-CF3602 R2= Me, Z = S, R3= 3-Br

[0934] 566 R2= I, Z = O, R3= 3,6-di-CF3603 R2= Me, Z = S, R3= 3-1

[0935] 567 R2= I, Z = O, R3= 4,5-di-CF3604 R2= Me, Z = S, R3= 3-CN

[0936] 568 R2= I, Z = O, R3= 3-CN, 4-Me 605 R2= Me, Z = S, R3= 3-N02

[0937] 569 R2= I, Z = O, R3= 3-CN, 4-F 606 R2= Me, Z = S, R3= 3-OMe

[0938] 570 R2= I, Z = O, R3= 3-CN, 4-Br 607 R2= Me, Z = S, R3= 3-OCF3

[0939] 571 R2= I, Z = O, R3= 3-CN, 4-OMe 608 R2= Me, Z = S, R3= 3-CF3

[0940] 572 R2= I, Z = O, R3= 3-CN, 4-CF3609 R2= Me, Z = S, R3= 3-CHF2

[0941] 573 R2= I, Z = O, R3= 3-CN, 6-Me 610 R2= Me, Z = S, R3= 3-CH2F

[0942] 574 R2= I, Z = O, R3= 3-CN, 6-F 611 R2= Me, Z = S, R3= 3-CHO

[0943] 575 R2= I, Z = O, R3= 3-CN, 6-Br 612 R2= Me, Z = S, R3= 3-Me

[0944] 576 R2= I, Z = O, R3= 3-CN, 6-OMe 613 R2= Me, Z = S, R3= 3-Et

[0945] 577 R2= I, Z = O, R3= 3-CN, 6-CF3614 R2= Me, Z = S, R3= 3-Ethynyl

[0946] 578 R2= Me, Z = O, R3= H (m = 0) 615 R2= Me, Z = S, R3= 3-Ethenyl

[0947] 579 R2= Me, Z = O, R3= 3-F 616 R2= Me, Z = S, R3= 3-S02Me

[0948] 580 R2= Me, Z = O, R3= 3 -CI 617 R2= Me, Z = S, R3= 3-OAc

[0949] 581 R2= Me, Z = O, R3= 3-Br 618 R2= Me, Z = S, R3= 3-c-Pr

[0950] 582 R2= Me, Z = O, R3= 3-1 619 R2= Me, Z = S, R3= 3-z-Pr

[0951] 583 R2= Me, Z = O, R3= 3-CN 620 R2= Me, Z = S, R3= 3-Ph

[0952] 584 R2= Me, Z = O, R3= 3-N02621 R2= Me, Z = O, R3= 4-F

[0953] 585 R2= Me, Z = O, R3= 3-OMe 622 R2= Me, Z = O, R3= 4-Cl

[0954] 586 R2= Me, Z = O, R3= 3-OCF3623 R2= Me, Z = O, R3= 4-Br

[0955] 587 R2= Me, Z = O, R3= 3-CF3624 R2= Me, Z = O, R3= 4-1

[0956] 588 R2= Me, Z = O, R3= 3-CHF2625 R2= Me, Z = O, R3= 4-CN

[0957] 589 R2= Me, Z = O, R3= 3-CH2F 626 R2= Me, Z = O, R3= 4-N02

[0958] 590 R2= Me, Z = O, R3= 3-CHO 627 R2= Me, Z = O, R3= 4-OMe

[0959] 591 R2= Me, Z = O, R3= 3-Me 628 R2= Me, Z = O, R3= 4-OCF3

[0960] 592 R2= Me, Z = O, R3= 3-Et 629 R2= Me, Z = O, R3= 4-CF3

[0961] 593 R2= Me, Z = O, R3= 3-Ethynyl 630 R2= Me, Z = O, R3= 4-CHF2

[0962] 594 R2= Me, Z = O, R3= 3-Ethenyl 631 R2= Me, Z = O, R3= 4-CH2F

[0963] 595 R2= Me, Z = O, R3= 3-S02Me 632 R2= Me, Z = O, R3= 4-CHO

[0964] 596 R2= Me, Z = O, R3= 3-OAc 633 R2= Me, Z = O, R3= 4-Me

[0965] 597 R2= Me, Z = O, R3= 3-c-Pr 634 R2= Me, Z = O, R3= 4-Et

[0966] 598 R2= Me, Z = O, R3= 3-z-Pr 635 R2= Me, Z = O, R3= 4-EthynylTable Header Row Table Header Row

[0967] 636 R2= Me, Z = O, R3= 4-Ethenyl 673 R2= Me, Z = O, R3= 6-CH2F

[0968] 637 R2= Me, Z = O, R3= 4-S02Me 674 R2= Me, Z = O, R3= 6-CHO

[0969] 638 R2= Me, Z = O, R3= 4-OAc 675 R2= Me, Z = O, R3= 6-Me

[0970] 639 R2= Me, Z = O, R3= 4-c-Pr 676 R2= Me, Z = O, R3= 6-Et

[0971] 640 R2= Me, Z = O, R3= 4-z-Pr 677 R2= Me, Z = O, R3= 6-Ethynyl

[0972] 641 R2= Me, Z = O, R3= 4-Ph 678 R2= Me, Z = O, R3= 6-Ethenyl

[0973] 642 R2= Me, Z = O, R3= 5-F 679 R2= Me, Z = O, R3= 6-S02Me

[0974] 643 R2= Me, Z = O, R3= 5-Cl 680 R2= Me, Z = O, R3= 6-OAc

[0975] 644 R2= Me, Z = O, R3= 5-Br 681 R2= Me, Z = O, R3= 6-c-Pr

[0976] 645 R2= Me, Z = O, R3= 5-1 682 R2= Me, Z = O, R3= 6-z-Pr

[0977] 646 R2= Me, Z = O, R3= 5-CN 683 R2= Me, Z = O, R3= 6-Ph

[0978] 647 R2= Me, Z = O, R3= 5-N02684 R2= Me, Z = O, R3= 3,4-di-F

[0979] 648 R2= Me, Z = O, R3= 5-OMe 685 R2= Me, Z = O, R3= 3,5-di-F

[0980] 649 R2= Me, Z = O, R3= 5-OCF3686 R2= Me, Z = O, R3= 3,6-di-F

[0981] 650 R2= Me, Z = O, R3= 5-CF3 687 R2= Me, Z = O, R3= 4,5-di-F

[0982] 651 R2= Me, Z = O, R3= 5-CHF2688 R2= Me, Z = O, R3= 3,4-di-Cl

[0983] 652 R2= Me, Z = O, R3= 5-CH2F 689 R2= Me, Z = O, R3= 3,5-di-Cl

[0984] 653 R2= Me, Z = O, R3= 5-CHO 690 R2= Me, Z = O, R3= 3,6-di-Cl

[0985] 654 R2= Me, Z = O, R3=5-Me 691 R2= Me, Z = O, R3= 4,5-di-Cl

[0986] 655 R2= Me, Z = O, R3= 5-Et 692 R2= Me, Z = O, R3= 3,4-di-Br

[0987] 656 R2= Me, Z = O, R3= 5-Ethynyl 693 R2= Me, Z = O, R3= 3,5-di-Br

[0988] 657 R2= Me, Z = O, R3= 5-Ethenyl 694 R2= Me, Z = O, R3= 3,6-di-Br

[0989] 658 R2= Me, Z = O, R3= 5-S02Me 695 R2= Me, Z = O, R3= 4,5-di-Br

[0990] 659 R2= Me, Z = O, R3= 5-OAc 696 R2= Me, Z = O, R3= 3,4-di-CN

[0991] 660 R2= Me, Z = O, R3= 5-c-Pr 697 R2= Me, Z = O, R3= 3,5-di-CN

[0992] 661 R2= Me, Z = O, R3= 5-z-Pr 698 R2= Me, Z = O, R3= 3,6-di-CN

[0993] 662 R2= Me, Z = O, R3= 5-Ph 699 R2= Me, Z = O, R3= 4,5-di-CN

[0994] 663 R2= Me, Z = O, R3= 6-F 700 R2= Me, Z = O, R3= 3,4-di-Me

[0995] 664 R2= Me, Z = O, R3= 6-Cl 701 R2= Me, Z = O, R3= 3,5-di-Me

[0996] 665 R2= Me, Z = O, R3= 6-Br 702 R2= Me, Z = O, R3= 3,6-di-Me

[0997] 666 R2= Me, Z = O, R3= 6-1 703 R2= Me, Z = O, R3= 4,5-di-Me

[0998] 667 R2= Me, Z = O, R3= 6-CN 704 R2= Me, Z = O, R3= 3,4-di-OMe

[0999] 668 R2= Me, Z = O, R3= 6-N02705 R2= Me, Z = O, R3= 3,5-di-OMe

[1000] 669 R2= Me, Z = O, R3= 6-OMe 706 R2= Me, Z = O, R3= 3,6-di-OMe

[1001] 670 R2= Me, Z = O, R3= 6-OCF3 707 R2= Me, Z = O, R3= 4,5-di-OMe

[1002] 671 R2= Me, Z = O, R3= 6-CF3 708 R2= Me, Z = O, R3= 3,4-di-CF3

[1003] 672 R2= Me, Z = O, R3= 6-CHF2709 R2= Me, Z = O, R3= 3,5-di-CF3Table Header Row Table Header Row

[1004] 710 R2= Me, Z = O, R3= 3,6-di-CF3747 R2= CN, Z = S, R3= 3-1

[1005] 711 R2= Me, Z = O, R3= 4,5-di-CF3748 R2= CN, Z = S, R3= 3-CN

[1006] 712 R2= Me, Z = O, R3= 3-CN, 4-Me 749 R2= CN, Z = S, R3= 3-N02

[1007] 713 R2= Me, Z = O, R3= 3-CN, 4-F 750 R2= CN, Z = S, R3= 3-OMe

[1008] 714 R2= Me, Z = O, R3= 3-CN, 4-Br 751 R2= CN, Z = S, R3= 3-OCF3

[1009] 715 R2= Me, Z = O, R3= 3-CN, 4-OMe 752 R2= CN, Z = S, R3= 3-CF3

[1010] 716 R2= Me, Z = O, R3= 3-CN, 4-CF3753 R2= CN, Z = S, R3= 3-CHF2

[1011] 717 R2= Me, Z = O, R3= 3-CN, 6-Me 754 R2= CN, Z = S, R3= 3-CH2F

[1012] 718 R2= Me, Z = O, R3= 3-CN, 6-F 755 R2= CN, Z = S, R3= 3-CHO

[1013] 719 R2= Me, Z = O, R3= 3-CN, 6-Br 756 R2= CN, Z = S, R3= 3-Me

[1014] 720 R2= Me, Z = O, R3= 3-CN, 6-OMe 757 R2= CN, Z = S, R3= 3-Et

[1015] 721 R2= Me, Z = O, R3= 3-CN, 6-CF3 758 R2= CN, Z = S, R3= 3-Ethynyl

[1016] 722 R2= CN, Z = O, R3= H (m = 0) 759 R2= CN, Z = S, R3= 3-Ethenyl

[1017] 723 R2= CN, Z = O, R3= 3-F 760 R2= CN, Z = S, R3= 3-S02Me

[1018] 724 R2= CN, Z = O, R3= 3 -CI 761 R2= CN, Z = S, R3= 3-OAc

[1019] 725 R2= CN, Z = O, R3= 3-Br 762 R2= CN, Z = S, R3= 3-c-Pr

[1020] 726 R2= CN, Z = O, R3= 3-1 763 R2= CN, Z = S, R3= 3-z-Pr

[1021] 727 R2= CN, Z = O, R3= 3-CN 764 R2= CN, Z = S, R3= 3-Ph

[1022] 728 R2= CN, Z = O, R3= 3-N02765 R2= CN, Z = O, R3= 4-F

[1023] 729 R2= CN, Z = O, R3= 3-OMe 766 R2= CN, Z = O, R3= 4-Cl

[1024] 730 R2= CN, Z = O, R3= 3-OCF3 767 R2= CN, Z = O, R3= 4-Br

[1025] 731 R2= CN, Z = O, R3= 3-CF3 768 R2= CN, Z = O, R3= 4-1

[1026] 732 R2= CN, Z = O, R3= 3-CHF2769 R2= CN, Z = O, R3= 4-CN

[1027] 733 R2= CN, Z = O, R3= 3-CH2F 770 R2= CN, Z = O, R3= 4-N02

[1028] 734 R2= CN, Z = O, R3= 3-CHO 771 R2= CN, Z = O, R3= 4-OMe

[1029] 735 R2= CN, Z = O, R3= 3-Me 772 R2= CN, Z = O, R3= 4-OCF3

[1030] 736 R2= CN, Z = O, R3= 3-Et 773 R2= CN, Z = O, R3= 4-CF3

[1031] 737 R2= CN, Z = O, R3= 3-Ethynyl 774 R2= CN, Z = O, R3= 4-CHF2

[1032] 738 R2= CN, Z = O, R3= 3-Ethenyl 775 R2= CN, Z = O, R3= 4-CH2F

[1033] 739 R2= CN, Z = O, R3= 3-S02Me 776 R2= CN, Z = O, R3= 4-CHO

[1034] 740 R2= CN, Z = 0, R3= 3-OAc 777 R2= CN, Z = O, R3= 4-Me

[1035] 741 R2= CN, Z = O, R3= 3-c-Pr 778 R2= CN, Z = O, R3= 4-Et

[1036] 742 R2= CN, Z = O, R3= 3-z-Pr 779 R2= CN, Z = O, R3= 4-Ethynyl

[1037] 743 R2= CN, Z = O, R3= 3-Ph 780 R2= CN, Z = O, R3= 4-Ethenyl

[1038] 744 R2= CN, Z = S, R3= 3-F 781 R2= CN, Z = O, R3= 4-S02Me

[1039] 745 R2= CN, Z = S, R3= 3-Cl 782 R2= CN, Z = O, R3= 4-OAc

[1040] 746 R2= CN, Z = S, R3= 3-Br 783 R2= CN, Z = O, R3= 4-c-PrTable Header Row Table Header Row

[1041] 784 R2= CN, Z = O, R3= 4-z-Pr 821 R2= CN, Z = O, R3= 6-Ethynyl

[1042] 785 R2= CN, Z = O, R3= 4-Ph 822 R2= CN, Z = O, R3= 6-Ethenyl

[1043] 786 R2= CN, Z = O, R3= 5-F 823 R2= CN, Z = O, R3= 6-S02Me

[1044] 787 R2= CN, Z = O, R3= 5-Cl 824 R2= CN, Z = O, R3= 6-OAc

[1045] 788 R2= CN, Z = O, R3= 5-Br 825 R2= CN, Z = O, R3= 6-c-Pr

[1046] 789 R2= CN, Z = O, R3= 5-1 826 R2= CN, Z = O, R3= 6-z-Pr

[1047] 790 R2= CN, Z = O, R3= 5-CN 827 R2= CN, Z = O, R3= 6-Ph

[1048] 791 R2= CN, Z = O, R3= 5-N02828 R2= CN, Z = O, R3= 3,4-di-F

[1049] 792 R2= CN, Z = O, R3= 5-OMe 829 R2= CN, Z = O, R3= 3,5-di-F

[1050] 793 R2= CN, Z = O, R3= 5-OCF3830 R2= CN, Z = O, R3= 3,6-di-F

[1051] 794 R2= CN, Z = O, R3= 5-CF3 831 R2= CN, Z = O, R3= 4,5-di-F

[1052] 795 R2= CN, Z = O, R3= 5-CHF2832 R2= CN, Z = O, R3= 3,4-di-Cl

[1053] 796 R2= CN, Z = O, R3= 5-CH2F 833 R2= CN, Z = O, R3= 3,5-di-Cl

[1054] 797 R2= CN, Z = O, R3= 5-CHO 834 R2= CN, Z = O, R3= 3,6-di-Cl

[1055] 798 R2= CN, Z = O, R3=5-Me 835 R2= CN, Z = O, R3= 4,5-di-Cl

[1056] 799 R2= CN, Z = O, R3= 5-Et 836 R2= CN, Z = O, R3= 3,4-di-Br

[1057] 800 R2= CN, Z = O, R3= 5-Ethynyl 837 R2= CN, Z = O, R3= 3,5-di-Br

[1058] 801 R2= CN, Z = O, R3= 5-Ethenyl 838 R2= CN, Z = O, R3= 3,6-di-Br

[1059] 802 R2= CN, Z = O, R3= 5-S02Me 839 R2= CN, Z = O, R3= 4,5-di-Br

[1060] 803 R2= CN, Z = O, R3= 5-OAc 840 R2= CN, Z = O, R3= 3,4-di-CN

[1061] 804 R2= CN, Z = O, R3= 5-c-Pr 841 R2= CN, Z = O, R3= 3,5-di-CN

[1062] 805 R2= CN, Z = O, R3= 5-z-Pr 842 R2= CN, Z = O, R3= 3,6-di-CN

[1063] 806 R2= CN, Z = O, R3= 5-Ph 843 R2= CN, Z = O, R3= 4,5-di-CN

[1064] 807 R2= CN, Z = O, R3= 6-F 844 R2= CN, Z = O, R3= 3,4-di-Me

[1065] 808 R2= CN, Z = O, R3= 6-Cl 845 R2= CN, Z = O, R3= 3,5-di-Me

[1066] 809 R2= CN, Z = O, R3= 6-Br 846 R2= CN, Z = O, R3= 3,6-di-Me

[1067] 810 R2= CN, Z = O, R3= 6-1 847 R2= CN, Z = O, R3= 4,5-di-Me

[1068] 811 R2= CN, Z = O, R3= 6-CN 848 R2= CN, Z = O, R3= 3,4-di-OMe

[1069] 812 R2= CN, Z = O, R3= 6-N02849 R2= CN, Z = O, R3= 3,5-di-OMe

[1070] 813 R2= CN, Z = O, R3= 6-OMe 850 R2= CN, Z = O, R3= 3,6-di-OMe

[1071] 814 R2= CN, Z = O, R3= 6-OCF3 851 R2= CN, Z = O, R3= 4,5-di-OMe

[1072] 815 R2= CN, Z = O, R3= 6-CF3 852 R2= CN, Z = O, R3= 3,4-di-CF3

[1073] 816 R2= CN, Z = O, R3= 6-CHF2853 R2= CN, Z = O, R3= 3,5-di-CF3

[1074] 817 R2= CN, Z = O, R3= 6-CH2F 854 R2= CN, Z = O, R3= 3,6-di-CF3

[1075] 818 R2= CN, Z = O, R3= 6-CHO 855 R2= CN, Z = O, R3= 4,5-di-CF3

[1076] 819 R2= CN, Z = O, R3= 6-Me 856 R2= CN, Z = O, R3= 3-CN, 4-Me

[1077] 820 R2= CN, Z = O, R3= 6-Et 857 R2= CN, Z = O, R3= 3-CN, 4-FTable Header Row Table Header Row

[1078] 858 R2= CN, Z = O, R3= 3-CN, 4-Br 895 R2= N02, Z = S, R3= 3-OCF3

[1079] 859 R2= CN, Z = 0, R3= 3-CN, 4-OMe 896 R2= N02, Z = S, R3= 3-CF3

[1080] 860 R2= CN, Z = 0, R3= 3-CN, 4-CF3897 R2= NOo, Z = S, R3= 3-CHF2

[1081] 861 R2= CN, Z = O, R3= 3-CN, 6-Me 898 R2= NOo, Z = S, R3= 3-CH2F

[1082] 862 R2= CN, Z = O, R3= 3-CN, 6-F 899 R2= N02, Z = S, R3= 3-CHO

[1083] 863 R2= CN, Z = O, R3= 3-CN, 6-Br 900 R2= N02, Z = S, R3= 3-Me

[1084] 864 R2= CN, Z = O, R3= 3-CN, 6-OMe 901 R2= N02, Z = S, R3= 3-Et

[1085] 865 R2= CN, Z = O, R3= 3-CN, 6-CF3 902 R2= N02, Z = S, R3= 3-Ethynyl

[1086] 866 R2= N02, Z = O, R3= H (m = 0) 903 R2= N02, Z = S, R3= 3-Ethenyl

[1087] 867 R2= N02, Z = 0, R3= 3-F 904 R2= N02, Z = S, R3= 3-S02Me

[1088] 868 R2= N02, Z = O, R3= 3-Cl 905 R2= N02, Z = S, R3= 3-OAc

[1089] 869 R2= N02, Z = 0, R3= 3-Br 906 R2= N02, Z = S, R3= 3-c-Pr

[1090] 870 R2= N02, Z = 0, R3= 3-I 907 R2= N02, Z = S, R3= 3-z-Pr

[1091] 871 R2= N02, Z = 0, R3= 3-CN 908 R2= N02, Z = S, R3= 3-Ph

[1092] 872 R2= N02, Z = O, R3= 3-N02909 R2= N02, Z = O, R3= 4-F

[1093] 873 R2= N02, Z = O, R3= 3-OMe 910 R2= NOo, Z = O, R3= 4-Cl

[1094] 874 R2= N02, Z = O, R3= 3-OCF3 911 R2= NOo, Z = O, R3= 4-Br

[1095] 875 R2= N02, Z = O, R3= 3-CF3 912 R2= N02, Z = 0, R3= 4-I

[1096] 876 R2= N02, Z = O, R3= 3-CHF2913 R2= N02, Z = 0, R3= 4-CN

[1097] 877 R2= N02, Z = O, R3= 3-CH2F 914 R2= N02, Z = O, R3= 4-N02

[1098] 878 R2= N02, Z = O, R3= 3-CHO 915 R2= N02, Z = O, R3= 4-OMe

[1099] 879 R2= N02, Z = O, R3= 3-Me 916 R2= NOo, Z = O, R3= 4-OCF3

[1100] 880 R2= N02, Z = O, R3= 3-Et 917 R2= NOo, Z = O, R3= 4-CF3

[1101] 881 R2= N02, Z = O, R3= 3-Ethynyl 918 R2= N02, Z = O, R3= 4-CHF2

[1102] 882 R2= N02, Z = O, R3= 3-Ethenyl 919 R2= N02, Z = O, R3= 4-CH2F

[1103] 883 R2= N02, Z = O, R3= 3-S02Me 920 R2= N02, Z = O, R3= 4-CHO

[1104] 884 R2= N02, Z = O, R3= 3-0 Ac 921 R2= N02, Z = 0, R3= 4-Me

[1105] 885 R2= N02, Z = O, R3= 3-c-Pr 922 R2= NOo, Z = O, R3= 4-Et

[1106] 886 R2= N02, Z = O, R3= 3-z-Pr 923 R2= N02, Z = O, R3= 4-Ethynyl

[1107] 887 R2= N02, Z = 0, R3= 3-Ph 924 R2= N02, Z = O, R3= 4-Ethenyl

[1108] 888 R2= N02, Z = S, R3= 3-F 925 R2= N02, Z = O, R3= 4-S02Me

[1109] 889 R2= N02, Z = S, R3= 3-C1 926 R2= N02, Z = O, R3= 4-0 Ac

[1110] 890 R2= N02, Z = S, R3= 3-Br 927 R2= N02, Z = O, R3= 4-c-Pr

[1111] 891 R2= N02, Z = S, R3= 3-1 928 R2= NOo, Z = O, R3= 4-z-Pr

[1112] 892 R2= N02, Z = S, R3= 3-CN 929 R2= NOo, Z = O, R3= 4-Ph

[1113] 893 R2= N02, Z = S, R3= 3-N02930 R2= N02, Z = O, R3= 5-F

[1114] 894 R2= N02, Z = S, R3= 3-OMe 931 R2= N02, Z = O, R3= 5-ClTable Header Row Table Header Row

[1115] 932 R2= N02, Z = O, R3= 5-Br 969 R2= N02, Z = O, R3= 6-c-Pr

[1116] 933 R2= N02, Z = 0, R3= 5-I 970 R2= N02, Z = O, R3= 6-z-Pr

[1117] 934 R2= N02, Z = 0, R3= 5-CN 971 R2= N02, Z = O, R3= 6-Ph

[1118] 935 R2= N02, Z = O, R3= 5-N02972 R2= N02, Z = O, R3= 3,4-di-F

[1119] 936 R2= N02, Z = O, R3= 5-OMe 973 R2= N02, Z = O, R3= 3,5-di-F

[1120] 937 R2= N02, Z = O, R3= 5-OCF3974 R2= N02, Z = O, R3= 3,6-di-F

[1121] 938 R2= N02, Z = O, R3= 5-CF3 975 R2= N02, Z = O, R3= 4,5-di-F

[1122] 939 R2= N02, Z = O, R3= 5-CHF2976 R2= N02, Z = O, R3= 3,4-di-Cl

[1123] 940 R2= N02, Z = O, R3= 5-CH2F 977 R2= N02, Z = O, R3= 3,5-di-Cl

[1124] 941 R2= N02, Z = O, R3= 5-CHO 978 R2= N02, Z = O, R3= 3,6-di-Cl

[1125] 942 R2= N02, Z = O, R3=5-Me 979 R2= N02, Z = O, R3= 4,5-di-Cl

[1126] 943 R2= N02, Z = O, R3= 5-Et 980 R2= N02, Z = O, R3= 3,4-di-Br

[1127] 944 R2= N02, Z = O, R3= 5-Ethynyl 981 R2= N02, Z = O, R3= 3,5-di-Br

[1128] 945 R2= N02, Z = O, R3= 5-Ethenyl 982 R2= N02, Z = O, R3= 3,6-di-Br

[1129] 946 R2= N02, Z = O, R3= 5-S02Me 983 R2= N02, Z = O, R3= 4,5-di-Br

[1130] 947 R2= N02, Z = O, R3= 5-0 Ac 984 R2= N02, Z = O, R3= 3,4-di-CN

[1131] 948 R2= N02, Z = O, R3= 5-c-Pr 985 R2= N02, Z = O, R3= 3,5-di-CN

[1132] 949 R2= N02, Z = O, R3= 5-z-Pr 986 R2= N02, Z = O, R3= 3,6-di-CN

[1133] 950 R2= N02, Z = O, R3= 5-Ph 987 R2= N02, Z = O, R3= 4,5-di-CN

[1134] 951 R2= N02, Z = O, R3= 6-F 988 R2= N02, Z = O, R3= 3,4-di-Me

[1135] 952 R2= N02, Z = O, R3= 6-Cl 989 R2= N02, Z = O, R3= 3,5-di-Me

[1136] 953 R2= N02, Z = O, R3= 6-Br 990 R2= N02, Z = O, R3= 3,6-di-Me

[1137] 954 R2= N02, Z = 0, R3= 6-I 991 R2= N02, Z = O, R3= 4,5-di-Me

[1138] 955 R2= N02, Z = 0, R3= 6-CN 992 R2= N02, Z = O, R3= 3,4-di-OMe

[1139] 956 R2= N02, Z = O, R3= 6-N02993 R2= N02, Z = O, R3= 3,5-di-OMe

[1140] 957 R2= N02, Z = O, R3= 6-OMe 994 R2= N02, Z = O, R3= 3,6-di-OMe

[1141] 958 R2= N02, Z = O, R3= 6-OCF3 995 R2= N02, Z = O, R3= 4,5-di-OMe

[1142] 959 R2= N02, Z = O, R3= 6-CF3 996 R2= N02, Z = O, R3= 3,4-di-CF3

[1143] 960 R2= N02, Z = O, R3= 6-CHF2997 R2= N02, Z = O, R3= 3,5-di-CF3

[1144] 961 R2= N02, Z = O, R3= 6-CH2F 998 R2= N02, Z = O, R3= 3,6-di-CF3

[1145] 962 R2= N02, Z = O, R3= 6-CHO 999 R2= N02, Z = O, R3= 4,5-di-CF3

[1146] 963 R2= N02, Z = O, R3= 6-Me 1000 R2= N02, Z = O, R3= 3-CN, 4-Me

[1147] 964 R2= N02, Z = O, R3= 6-Et 1001 R2= N02, Z = O, R3= 3-CN, 4-F

[1148] 965 R2= N02, Z = O, R3= 6-Ethynyl 1002 R2= N02, Z = O, R3= 3-CN, 4-Br

[1149] 966 R2= N02, Z = O, R3= 6-Ethenyl 1003 R2= N02, Z = O, R3= 3-CN, 4-OMe

[1150] 967 R2= N02, Z = O, R3= 6-S02Me 1004 R2= N02, Z = O, R3= 3-CN, 4-CF3

[1151] 968 R2= N02, Z = O, R3= 6-0 Ac 1005

[1152] R2= N02, Z = O, R3= 3-CN, 6-MeTable Header Row Table Header Row

[1153] 1006 R2= N02, Z = O, R3= 3-CN, 6-F 1043 R2= OMe, Z = S, R3= 3-CHO

[1154] 1007 R2= N02, Z = O, R3= 3-CN, 6-Br 1044 R2= OMe, Z = S, R3= 3-Me

[1155] 1008 R2= N02, Z = O, R3= 3-CN, 6-OMe 1045 R2= OMe, Z = S, R3= 3-Et

[1156] 1009 R2= N02, Z = O, R3= 3-CN, 6-CF3 1046 R2= OMe, Z = S, R3= 3-Ethynyl

[1157] 1010 R2= OMe, Z = O, R3= H (m = 0) 1047 R2= OMe, Z = S, R3= 3-Ethenyl

[1158] 1011 R2= OMe, Z = O, R3= 3-F 1048 R2= OMe, Z = S, R3= 3-S02Me

[1159] 1012 R2= OMe, Z = O, R3= 3 -CI 1049 R2= OMe, Z = S, R3= 3-OAc

[1160] 1013 R2= OMe, Z = O, R3= 3-Br 1050 R2= OMe, Z = S, R3= 3-c-Pr

[1161] 1014 R2= OMe, Z = O, R3= 3-1 1051 R2= OMe, Z = S, R3= 3-z-Pr

[1162] 1015 R2= OMe, Z = O, R3= 3-CN 1052 R2= OMe, Z = S, R3= 3-Ph

[1163] 1016 R2= OMe, Z = O, R3= 3-N021053 R2= OMe, Z = O, R3= 4-F

[1164] 1017 R2= OMe, Z = O, R3= 3 -OMe 1054 R2= OMe, Z = O, R3= 4-Cl

[1165] 1018 R2= OMe, Z = O, R3= 3-OCF3 1055 R2= OMe, Z = O, R3= 4-Br

[1166] 1019 R2= OMe, Z = O, R3= 3-CF3 1056 R2= OMe, Z = O, R3= 4-1

[1167] 1020 R2= OMe, Z = O, R3= 3-CHF21057 R2= OMe, Z = O, R3= 4-CN

[1168] 1021 R2= OMe, Z = O, R3= 3-CH2F 1058 R2= OMe, Z = O, R3= 4-N02

[1169] 1022 R2= OMe, Z = O, R3= 3-CHO 1059 R2= OMe, Z = O, R3= 4-OMe

[1170] 1023 R2= OMe, Z = O, R3= 3-Me 1060 R2= OMe, Z = O, R3= 4-OCF3

[1171] 1024 R2= OMe, Z = O, R3= 3-Et 1061 R2= OMe, Z = O, R3= 4-CF3

[1172] 1025 R2= OMe, Z = O, R3= 3-Ethynyl 1062 R2= OMe, Z = O, R3= 4-CHF2

[1173] 1026 R2= OMe, Z = O, R3= 3-Ethenyl 1063 R2= OMe, Z = O, R3= 4-CH2F

[1174] 1027 R2= OMe, Z = O, R3= 3-S02Me 1064 R2= OMe, Z = O, R3= 4-CHO

[1175] 1028 R2= OMe, Z = O, R3= 3-OAc 1065 R2= OMe, Z = O, R3= 4-Me

[1176] 1029 R2= OMe, Z = O, R3= 3-c-Pr 1066 R2= OMe, Z = O, R3= 4-Et

[1177] 1030 R2= OMe, Z = O, R3= 3-z-Pr 1067 R2= OMe, Z = O, R3= 4-Ethynyl

[1178] 1031 R2= OMe, Z = 0, R3= 3-Ph 1068 R2= OMe, Z = O, R3= 4-Ethenyl

[1179] 1032 R2= OMe, Z = S, R3= 3-F 1069 R2= OMe, Z = O, R3= 4-S02Me

[1180] 1033 R2= OMe, Z = S, R3= 3 -CI 1070 R2= OMe, Z = O, R3= 4-OAc

[1181] 1034 R2= OMe, Z = S, R3= 3-Br 1071 R2= OMe, Z = O, R3= 4-c-Pr

[1182] 1035 R2= OMe, Z = S, R3= 3-1 1072 R2= OMe, Z = O, R3= 4-z-Pr

[1183] 1036 R2= OMe, Z = S, R3= 3-CN 1073 R2= OMe, Z = O, R3= 4-Ph

[1184] 1037 R2= OMe, Z = S, R3= 3-N021074 R2= OMe, Z = O, R3= 5-F

[1185] 1038 R2= OMe, Z = S, R3= 3 -OMe 1075 R2= OMe, Z = O, R3= 5-Cl

[1186] 1039 R2= OMe, Z = S, R3= 3-OCF31076 R2= OMe, Z = O, R3= 5-Br

[1187] 1040 R2= OMe, Z = S, R3= 3-CF31077 R2= OMe, Z = O, R3= 5-1

[1188] 1041 R2= OMe, Z = S, R3= 3-CHF21078 R2= OMe, Z = O, R3= 5-CN

[1189] 1042 R2= OMe, Z = S, R3= 3-CH2F1079 R2= OMe, Z = O, R3= 5-N02Table Header Row

[1190] 1080 R2= OMe, Z = O, R3= 5-OMe

[1191] 1081 R2= OMe, Z = O, R3= 5-OCF3

[1192] 1082 R2= OMe, Z = O, R3= 5-CF3

[1193] 1083 R2= OMe, Z = O, R3= 5-CHF2

[1194] 1084 R2= OMe, Z = O, R3= 5-CH2F

[1195] 1085 R2= OMe, Z = O, R3= 5-CHO

[1196] 1086 R2= OMe, Z = O, R3=5-Me

[1197] 1087 R2= OMe, Z = O, R3= 5-Et

[1198] 1088 R2= OMe, Z = O, R3= 5-Ethynyl

[1199] 1089 R2= OMe, Z = O, R3= 5-Ethenyl

[1200] 1090 R2= OMe, Z = O, R3= 5-S02Me

[1201] 1091 R2= OMe, Z = O, R3= 5-OAc

[1202] 1092 R2= OMe, Z = O, R3= 5-c-Pr

[1203] 1093 R2= OMe, Z = O, R3= 5-z-Pr

[1204] 1094 R2= OMe, Z = O, R3= 5-Ph

[1205] 1095 R2= OMe, Z = O, R3= 6-F

[1206] 1096 R2= OMe, Z = O, R3= 6-Cl

[1207] 1097 R2= OMe, Z = O, R3= 6-Br

[1208] 1098 R2= OMe, Z = O, R3= 6-1

[1209] 1099 R2= OMe, Z = O, R3= 6-CN

[1210] 1100 R2= OMe, Z = O, R3= 6-N02

[1211] 1101 R2= OMe, Z = O, R3= 6-OMe

[1212] 1102 R2= OMe, Z = O, R3= 6-OCF3

[1213] 1103 R2= OMe, Z = O, R3= 6-CF3

[1214] 1104 R2= OMe, Z = O, R3= 6-CHF2

[1215] 1105 R2= OMe, Z = O, R3= 6-CH2F

[1216] 1106 R2= OMe, Z = O, R3= 6-CHO

[1217] 1107 R2= OMe, Z = O, R3= 6-Me

[1218] 1108 R2= OMe, Z = O, R3= 6-Et

[1219] 1109 R2= OMe, Z = O, R3= 6-Ethynyl

[1220] 1110 R2= OMe, Z = O, R3= 6-Ethenyl

[1221] 1111 R2= OMe, Z = O, R3= 6-S02Me

[1222] 1112 R2= OMe, Z = O, R3= 6-OAc

[1223] 1113 R2= OMe, Z = O, R3= 6-c-Pr

[1224] 1114 R2= OMe, Z = O, R3= 6-z-Pr

[1225] 1115 R2= OMe, Z = O, R3= 6-Ph

[1226] 1116 R2= OMe, Z = O, R3= 3,4-di-FTable Header Row Table Header Row

[1227] 1154 R2= CF3, Z = O, R3= H (m = 0) 1191 R2= CF3, Z = S, R3= 3-Ethenyl

[1228] 1155 R2= CF3, Z = O, R3= 3-F 1192 R2= CF3, Z = S, R3= 3-S02Me

[1229] 1156 R2= CF3, Z = O, R3= 3 -CI 1193 R2= CF3, Z = S, R3= 3-OAc

[1230] 1157 R2= CF3, Z = O, R3= 3-Br 1194 R2= CF3, Z = S, R3= 3-c-Pr

[1231] 1158 R2= CF3, Z = 0, R3= 3-1 1195 R2= CF3, Z = S, R3= 3-z-Pr

[1232] 1159 R2= CF3, Z = O, R3= 3-CN 1196 R2= CF3, Z = S, R3= 3-Ph

[1233] 1160 R2= CF3, Z = O, R3= 3-N021197 R2= CF3, Z = O, R3= 4-F

[1234] 1161 R2= CF3, Z = O, R3= 3-OMe 1198 R2= CF3, Z = O, R3= 4-Cl

[1235] 1162 R2= CF3, Z = O, R3= 3-OCF31199 R2= CF3, Z = O, R3= 4-Br

[1236] 1163 R2= CF3, Z = O, R3= 3-CF31200 R2= CF3, Z = 0, R3= 4-1

[1237] 1164 R2= CF3, Z = O, R3= 3-CHF21201 R2= CF3, Z = O, R3= 4-CN

[1238] 1165 R2= CF3, Z = O, R3= 3-CH2F 1202 R2= CF3, Z = O, R3= 4-N02

[1239] 1166 R2= CF3, Z = O, R3= 3-CHO 1203 R2= CF3, Z = O, R3= 4-OMe

[1240] 1167 R2= CF3, Z = O, R3= 3-Me 1204 R2= CF3, Z = O, R3= 4-OCF3

[1241] 1168 R2= CF3, Z = O, R3= 3-Et 1205 R2= CF3, Z = O, R3= 4-CF3

[1242] 1169 R2= CF3, Z = O, R3= 3-Ethynyl 1206 R2= CF3, Z = O, R3= 4-CHF2

[1243] 1170 R2= CF3, Z = O, R3= 3-Ethenyl 1207 R2= CF3, Z = O, R3= 4-CH2F

[1244] 1171 R2= CF3, Z = O, R3= 3-S02Me 1208 R2= CF3, Z = O, R3= 4-CHO

[1245] 1172 R2= CF3, Z = 0, R3= 3-OAc 1209 R2= CF3, Z = O, R3= 4-Me

[1246] 1173 R2= CF3, Z = O, R3= 3-c-Pr 1210 R2= CF3, Z = O, R3= 4-Et

[1247] 1174 R2= CF3, Z = 0, R3= 3-z-Pr 1211 R2= CF3, Z = O, R3= 4-Ethynyl

[1248] 1175 R2= CF3, Z = O, R3= 3-Ph 1212 R2= CF3, Z = O, R3= 4-Ethenyl

[1249] 1176 R2= CF3, Z = S, R3= 3-F 1213 R2= CF3, Z = O, R3= 4-S02Me

[1250] 1177 R2= CF3, Z = S, R3= 3 -CI 1214 R2= CF3, Z = O, R3= 4-OAc

[1251] 1178 R2= CF3, Z = S, R3= 3-Br 1215 R2= CF3, Z = O, R3= 4-c-Pr

[1252] 1179 R2= CF3, Z = S, R3= 3-1 1216 R2= CF3, Z = 0, R3= 4-z-Pr

[1253] 1180 R2= CF3, Z = S, R3= 3-CN 1217 R2= CF3, Z = O, R3= 4-Ph

[1254] 1181 R2= CF3, Z = S, R3= 3-N021218 R2= CF3, Z = O, R3= 5-F

[1255] 1182 R2= CF3, Z = S, R3= 3-OMe 1219 R2= CF3, Z = O, R3= 5-Cl

[1256] 1183 R2= CF3, Z = S, R3= 3-OCF31220 R2= CF3, Z = O, R3= 5-Br

[1257] 1184 R2= CF3, Z = S, R3= 3-CF31221 R2= CF3, Z = 0, R3= 5-1

[1258] 1185 R2= CF3, Z = S, R3= 3-CHF21222 R2= CF3, Z = O, R3= 5-CN

[1259] 1186 R2= CF3, Z = S, R3= 3-CH2F 1223 R2= CF3, Z = O, R3= 5-N02

[1260] 1187 R2= CF3, Z = S, R3= 3-CHO 1224 R2= CF3, Z = O, R3= 5-OMe

[1261] 1188 R2= CF3, Z = S, R3= 3-Me 1225 R2= CF3, Z = O, R3= 5-OCF3

[1262] 1189 R2= CF3, Z = S, R3= 3-Et 1226 R2= CF3, Z = O, R3= 5-CF3

[1263] 1190 R2= CF3, Z = S, R3= 3-Ethynyl 1227 R2= CF3, Z = O, R3= 5-CHF2Table Header Row Table Header Row

[1264] 1228 R2= CF3, Z = O, R3= 5-CH2F 1265 R2= CF3, Z = O, R3= 3,5-di-Cl

[1265] 1229 R2= CF3, Z = O, R3= 5-CHO 1266 R2= CF3, Z = O, R3= 3,6-di-Cl

[1266] 1230 R2= CF3, Z = O, R3=5-Me 1267 R2= CF3, Z = O, R3= 4,5-di-Cl

[1267] 1231 R2= CF3, Z = O, R3= 5-Et 1268 R2= CF3, Z = O, R3= 3,4-di-Br

[1268] 1232 R2= CF3, Z = O, R3= 5-Ethynyl 1269 R2= CF3, Z = O, R3= 3,5-di-Br

[1269] 1233 R2= CF3, Z = O, R3= 5-Ethenyl 1270 R2= CF3, Z = O, R3= 3,6-di-Br

[1270] 1234 R2= CF3, Z = O, R3= 5-S02Me 1271 R2= CF3, Z = O, R3= 4,5-di-Br

[1271] 1235 R2= CF3, Z = 0, R3= 5-OAc 1272 R2= CF3, Z = O, R3= 3,4-di-CN

[1272] 1236 R2= CF3, Z = O, R3= 5-c-Pr 1273 R2= CF3, Z = O, R3= 3,5-di-CN

[1273] 1237 R2= CF3, Z = 0, R3= 5-z-Pr 1274 R2= CF3, Z = O, R3= 3,6-di-CN

[1274] 1238 R2= CF3, Z = O, R3= 5-Ph 1275 R2= CF3, Z = O, R3= 4,5-di-CN

[1275] 1239 R2= CF3, Z = O, R3= 6-F 1276 R2= CF3, Z = O, R3= 3,4-di-Me

[1276] 1240 R2= CF3, Z = O, R3= 6-Cl 1277 R2= CF3, Z = O, R3= 3,5-di-Me

[1277] 1241 R2= CF3, Z = O, R3= 6-Br 1278 R2= CF3, Z = O, R3= 3,6-di-Me

[1278] 1242 R2= CF3, Z = 0, R3= 6-1 1279 R2= CF3, Z = O, R3= 4,5-di-Me

[1279] 1243 R2= CF3, Z = O, R3= 6-CN 1280 R2= CF3, Z = O, R3= 3,4-di-OMe

[1280] 1244 R2= CF3, Z = O, R3= 6-N021281 R2= CF3, Z = O, R3= 3,5-di-OMe

[1281] 1245 R2= CF3, Z = O, R3= 6-OMe 1282 R2= CF3, Z = O, R3= 3,6-di-OMe

[1282] 1246 R2= CF3, Z = O, R3= 6-OCF31283 R2= CF3, Z = O, R3= 4,5-di-OMe

[1283] 1247 R2= CF3, Z = O, R3= 6-CF31284 R2= CF3, Z = O, R3= 3,4-di-CF3

[1284] 1248 R2= CF3, Z = O, R3= 6-CHF21285 R2= CF3, Z = O, R3= 3,5-di-CF3

[1285] 1249 R2= CF3, Z = O, R3= 6-CH2F 1286 R2= CF3, Z = O, R3= 3,6-di-CF3

[1286] 1250 R2= CF3, Z = O, R3= 6-CHO 1287 R2= CF3, Z = O, R3= 4,5-di-CF3

[1287] 1251 R2= CF3, Z = O, R3= 6-Me 1288 R2= CF3, Z = O, R3= 3-CN, 4-Me

[1288] 1252 R2= CF3, Z = O, R3= 6-Et 1289 R2= CF3, Z = O, R3= 3-CN, 4-F

[1289] 1253 R2= CF3, Z = O, R3= 6-Ethynyl 1290 R2= CF3, Z = O, R3= 3-CN, 4-Br

[1290] 1254 R2= CF3, Z = O, R3= 6-Ethenyl 1291 R2= CF3, Z = O, R3= 3-CN, 4-OMe

[1291] 1255 R2= CF3, Z = O, R3= 6-S02Me 1292 R2= CF3, Z = O, R3= 3-CN, 4-CF3

[1292] 1256 R2= CF3, Z = O, R3= 6-OAc 1293 R2= CF3, Z = O, R3= 3-CN, 6-Me

[1293] 1257 R2= CF3, Z = O, R3= 6-c-Pr 1294 R2= CF3, Z = O, R3= 3-CN, 6-F

[1294] 1258 R2= CF3, Z = 0, R3= 6-z-Pr 1295 R2= CF3, Z = O, R3= 3-CN, 6-Br

[1295] 1259 R2= CF3, Z = O, R3= 6-Ph 1296 R2= CF3, Z = O, R3= 3-CN, 6-OMe

[1296] 1260 R2= CF3, Z = O, R3= 3,4-di-F 1297 R2= CF3, Z = O, R3= 3-CN, 6-CF3

[1297] 1261 R2= CF3, Z = O, R3= 3,5-di-F 1298 R2= CHF2, Z = O, R3= H (m = 0)

[1298] 1262 R2= CF3, Z = O, R3= 3,6-di-F 1299 R2= CHF2, Z = O, R3= 3-F

[1299] 1263 R2= CF3, Z = O, R3= 4,5-di-F 1300 R2= CHF2, Z = O, R3= 3 -CI

[1300] 1264 R2= CF3, Z = O, R3= 3,4-di-Cl 1301 R2= CHF2, Z = O, R3= 3-BrTable Header Row Table Header Row

[1301] 1302 R2= CHF2, Z = O, R3= 3-1 1339 R2= CHF2, Z = S, R3= 3-Ph

[1302] 1303 R2= CHF2, Z = O, R3= 3-CN 1340 R2= CHF2, Z = O, R3= 4-F

[1303] 1304 R2= CHF2, Z = O, R3= 3-N021341 R2= CHF2, Z = O, R3= 4-Cl

[1304] 1305 R2= CHF2, Z = O, R3= 3-OMe 1342 R2= CHF2, Z = O, R3= 4-Br

[1305] 1306 R2= CHF2, Z = O, R3= 3-OCF31343 R2= CHF2, Z = O, R3= 4-1

[1306] 1307 R2= CHF2, Z = O, R3= 3-CF3 1344 R2= CHF2, Z = O, R3= 4-CN

[1307] 1308 R2= CHF2, Z = O, R3= 3-CHF21345 R2= CHF2, Z = O, R3= 4-N02

[1308] 1309 R2= CHF2, Z = O, R3= 3-CH2F 1346 R2= CHF2, Z = O, R3= 4-OMe

[1309] 1310 R2= CHF2, Z = O, R3= 3-CHO 1347 R2= CHF2, Z = O, R3= 4-OCF3

[1310] 1311 R2= CHF2, Z = O, R3= 3 -Me 1348 R2= CHF2, Z = O, R3= 4-CF3

[1311] 1312 R2= CHF2, Z = O, R3= 3-Et 1349 R2= CHF2, Z = O, R3= 4-CHF2

[1312] 1313 R2= CHF2, Z = O, R3= 3-Ethynyl 1350 R2= CHF2, Z = O, R3= 4-CH2F

[1313] 1314 R2= CHF2, Z = O, R3= 3-Ethenyl 1351 R2= CHF2, Z = O, R3= 4-CHO

[1314] 1315 R2= CHF2, Z = O, R3= 3-S02Me 1352 R2= CHF2, Z = O, R3= 4-Me

[1315] 1316 R2= CHF2, Z = O, R3= 3-OAc 1353 R2= CHF2, Z = O, R3= 4-Et

[1316] 1317 R2= CHF2, Z = O, R3= 3-c-Pr 1354 R2= CHF2, Z = O, R3= 4-Ethynyl

[1317] 1318 R2= CHF2, Z = O, R3= 3-z-Pr 1355 R2= CHF2, Z = O, R3= 4-Ethenyl

[1318] 1319 R2= CHF2, Z = O, R3= 3-Ph 1356 R2= CHF2, Z = O, R3= 4-S02Me

[1319] 1320 R2= CHF2, Z = S, R3= 3-F 1357 R2= CHF2, Z = O, R3= 4-OAc

[1320] 1321 R2= CHF2, Z = S, R3= 3-Cl 1358 R2= CHF2, Z = O, R3= 4-c-Pr

[1321] 1322 R2= CHF2, Z = S, R3= 3-Br 1359 R2= CHF2, Z = O, R3= 4-z-Pr

[1322] 1323 R2= CHF2, Z = S, R3= 3-1 1360 R2= CHF2, Z = O, R3= 4-Ph

[1323] 1324 R2= CHF2, Z = S, R3= 3-CN 1361 R2= CHF2, Z = O, R3= 5-F

[1324] 1325 R2= CHF2, Z = S, R3= 3-N021362 R2= CHF2, Z = O, R3= 5-Cl

[1325] 1326 R2= CHF2, Z = S, R3= 3-OMe 1363 R2= CHF2, Z = O, R3= 5-Br

[1326] 1327 R2= CHF2, Z = S, R3= 3-OCF3 1364 R2= CHF2, Z = O, R3= 5-1

[1327] 1328 R2= CHF2, Z = S, R3= 3-CHF21365 R2= CHF2, Z = O, R3= 5-CN

[1328] 1329 R2= CHF2, Z = S, R3= 3-CH2F 1366 R2= CHF2, Z = O, R3= 5-N02

[1329] 1330 R2= CHF2, Z = S, R3= 3-CHO 1367 R2= CHF2, Z = O, R3= 5-OMe

[1330] 1331 R2= CHF2, Z = S, R3= 3 -Me 1368 R2= CHF2, Z = O, R3= 5-OCF3

[1331] 1332 R2= CHF2, Z = S, R3= 3-Et 1369 R2= CHF2, Z = O, R3= 5-CF3

[1332] 1333 R2= CHF2, Z = S, R3= 3-Ethynyl 1370 R2= CHF2, Z = O, R3= 5-CHF2

[1333] 1334 R2= CHF2, Z = S, R3= 3-Ethenyl 1371 R2= CHF2, Z = O, R3= 5-CH2F

[1334] 1335 R2= CHF2, Z = S, R3= 3-S02Me 1372 R2= CHF2, Z = O, R3= 5-CHO

[1335] 1336 R2= CHF2, Z = S, R3= 3-OAc 1373 R2= CHF2, Z = O, R3=5-Me

[1336] 1337 R2= CHF2, Z = S, R3= 3-c-Pr 1374 R2= CHF2, Z = O, R3= 5-Et

[1337] 1338 R2= CHF2, Z = S, R3= 3-z-Pr 1375 R2= CHF2, Z = O, R3= 5-EthynylTable Header Row Table Header Row

[1338] 1376 R2= CHF2, Z = O, R3= 5-Ethenyl 1413 R2= CHF2, Z = O, R3= 3,6-di-Br

[1339] 1377 R2= CHF2, Z = O, R3= 5-S02Me 1414 R2= CHF2, Z = O, R3= 4,5-di-Br

[1340] 1378 R2= CHF2, Z = O, R3= 5-OAc 1415 R2= CHF2, Z = O, R3= 3,4-di-CN

[1341] 1379 R2= CHF2, Z = O, R3= 5-c-Pr 1416 R2= CHF2, Z = O, R3= 3,5-di-CN

[1342] 1380 R2= CHF2, Z = O, R3= 5-z-Pr 1417 R2= CHF2, Z = O, R3= 3,6-di-CN

[1343] 1381 R2= CHF2, Z = O, R3= 5-Ph 1418 R2= CHF2, Z = O, R3= 4,5-di-CN

[1344] 1382 R2= CHF2, Z = O, R3= 6-F 1419 R2= CHF2, Z = O, R3= 3,4-di-Me

[1345] 1383 R2= CHF2, Z = O, R3= 6-Cl 1420 R2= CHF2, Z = O, R3= 3,5-di-Me

[1346] 1384 R2= CHF2, Z = O, R3= 6-Br 1421 R2= CHF2, Z = O, R3= 3,6-di-Me

[1347] 1385 R2= CHF2, Z = O, R3= 6-1 1422 R2= CHF2, Z = O, R3= 4,5-di-Me

[1348] 1386 R2= CHF2, Z = O, R3= 6-CN 1423 R2= CHF2, Z = O, R3= 3,4-di-OMe

[1349] 1387 R2= CHF2, Z = O, R3= 6-N021424 R2= CHF2, Z = O, R3= 3,5-di-OMe

[1350] 1388 R2= CHF2, Z = O, R3= 6-OMe 1425 R2= CHF2, Z = O, R3= 3,6-di-OMe

[1351] 1389 R2= CHF2, Z = O, R3= 6-OCF3 1426 R2= CHF2, Z = O, R3= 4,5-di-OMe

[1352] 1390 R2= CHF2, Z = O, R3= 6-CF3 1427 R2= CHF2, Z = O, R3= 3,4-di-CF3

[1353] 1391 R2= CHF2, Z = O, R3= 6-CHF21428 R2= CHF2, Z = O, R3= 3,5-di-CF3

[1354] 1392 R2= CHF2, Z = O, R3= 6-CH2F 1429 R2= CHF2, Z = O, R3= 3,6-di-CF3

[1355] 1393 R2= CHF2, Z = O, R3= 6-CHO 1430 R2= CHF2, Z = O, R3= 4,5-di-CF3

[1356] 1394 R2= CHF2, Z = O, R3= 6-Me 1431 R2= CHF2, Z = O, R3= 3-CN, 4-Me

[1357] 1395 R2= CHF2, Z = O, R3= 6-Et 1432 R2= CHF2, Z = O, R3= 3-CN, 4-F

[1358] 1396 R2= CHF2, Z = O, R3= 6-Ethynyl 1433 R2= CHF2, Z = O, R3= 3-CN, 4-Br

[1359] 1397 R2= CHF2, Z = O, R3= 6-Ethenyl 1434 R2= CHF2, Z = O, R3= 3-CN, 4-OMe

[1360] 1398 R2= CHF2, Z = O, R3= 6-S02Me 1435 R2= CHF2, Z = O, R3= 3-CN, 4-CF3

[1361] 1399 R2= CHF2, Z = O, R3= 6-OAc 1436 R2= CHF2, Z = O, R3= 3-CN, 6-Me

[1362] 1400 R2= CHF2, Z = O, R3= 6-c-Pr 1437 R2= CHF2, Z = O, R3= 3-CN, 6-F

[1363] 1401 R2= CHF2, Z = O, R3= 6-i-Pr 1438 R2= CHF2, Z = O, R3= 3-CN, 6-Br

[1364] 1402 R2= CHF2, Z = O, R3= 6-Ph 1439 R2= CHF2, Z = O, R3= 3-CN, 6-OMe

[1365] 1403 R2= CHF2, Z = O, R3= 3,4-di-F 1440 R2= CHF2, Z = O, R3= 3-CN, 6-CF3

[1366] 1404 R2= CHF2, Z = O, R3= 3,5-di-F 1441 R2= S02Me, Z = O, R3= H (m = 0)

[1367] 1405 R2= CHF2, Z = O, R3= 3,6-di-F 1442 R2= S02Me, Z = O, R3= 3-F

[1368] 1406 R2= CHF2, Z = O, R3= 4,5-di-F 1443 R2= S02Me, Z = O, R3= 3 -CI

[1369] 1407 R2= CHF2, Z = O, R3= 3,4-di-Cl 1444 R2= SOoMe, Z = O, R3= 3 -Br

[1370] 1408 R2= CHF2, Z = O, R3= 3,5-di-Cl 1445 R2= S02Me, Z = O, R3= 3-1

[1371] 1409 R2= CHF2, Z = O, R3= 3,6-di-Cl 1446 R2= S02Me, Z = O, R3= 3-CN

[1372] 1410 R2= CHF2, Z = O, R3= 4,5-di-Cl 1447 R2= S02Me, Z = O, R3= 3-N02

[1373] 1411 R2= CHF2, Z = O, R3= 3,4-di-Br 1448 R2= S02Me, Z = O, R3= 3-OMe

[1374] 1412 R2= CHF2, Z = O, R3= 3,5-di-Br 1449 R2= S02Me, Z = O, R3= 3-OCF3Table Header Row Table Header Row

[1375] 1450 R2= S02Me, Z = O, R3= 3-CF31487 R2= S02Me, Z = O, R3= 4-1

[1376] 1451 R2= S02Me, Z = O, R3= 3-CHF21488 R2= S02Me, Z = O, R3= 4-CN

[1377] 1452 R2= S02Me, Z = O, R3= 3-CH2F 1489 R2= S02Me, Z = O, R3= 4-N02

[1378] 1453 R2= S02Me, Z = O, R3= 3-CHO 1490 R2= S02Me, Z = O, R3= 4-OMe

[1379] 1454 R2= S02Me, Z = O, R3= 3 -Me 1491 R2= S02Me, Z = O, R3= 4-OCF3

[1380] 1455 R2= S02Me, Z = O, R3= 3-Et 1492 R2= S02Me, Z = O, R3= 4-CF3

[1381] 1456 R2= S02Me, Z = O, R3= 3-Ethynyl 1493 R2= S02Me, Z = O, R3= 4-CHF2

[1382] 1457 R2= S02Me, Z = O, R3= 3-Ethenyl 1494 R2= S02Me, Z = O, R3= 4-CH2F

[1383] 1458 R2= S02Me, Z = O, R3= 3-S02Me 1495 R2= S02Me, Z = O, R3= 4-CHO

[1384] 1459 R2= S02Me, Z = O, R3= 3-OAc 1496 R2= S02Me, Z = O, R3= 4-Me

[1385] 1460 R2= S02Me, Z = O, R3= 3-c-Pr 1497 R2= S02Me, Z = O, R3= 4-Et

[1386] 1461 R2= S02Me, Z = O, R3= 3-z-Pr 1498 R2= S02Me, Z = O, R3= 4-Ethynyl

[1387] 1462 R2= S02Me, Z = O, R3= 3-Ph 1499 R2= S02Me, Z = O, R3= 4-Ethenyl

[1388] 1463 R2= S02Me, Z = S, R3= 3-F 1500 R2= S02Me, Z = O, R3= 4-S02Me

[1389] 1464 R2= S02Me, Z = S, R3= 3 -CI 1501 R2= S02Me, Z = O, R3= 4-OAc

[1390] 1465 R2= S02Me, Z = S, R3= 3 -Br 1502 R2= S02Me, Z = O, R3= 4-c-Pr

[1391] 1466 R2= S02Me, Z = S, R3= 3-1 1503 R2= S02Me, Z = O, R3= 4-z-Pr

[1392] 1467 R2= S02Me, Z = S, R3= 3-CN 1504 R2= S02Me, Z = O, R3= 4-Ph

[1393] 1468 R2= S02Me, Z = S, R3= 3-N021505 R2= S02Me, Z = O, R3= 5-F

[1394] 1469 R2= S02Me, Z = S, R3= 3-OMe 1506 R2= S02Me, Z = O, R3= 5-Cl

[1395] 1470 R2= S02Me, Z = S, R3= 3-OCF31507 R2= S02Me, Z = O, R3= 5-Br

[1396] 1471 R2= S02Me, Z = S, R3= 3-CF31508 R2= S02Me, Z = O, R3= 5-1

[1397] 1472 R2= S02Me, Z = S, R3= 3-CHF21509 R2= S02Me, Z = O, R3= 5-CN

[1398] 1473 R2= S02Me, Z = S, R3= 3-CH2F 1510 R2= S02Me, Z = O, R3= 5-N02

[1399] 1474 R2= S02Me, Z = S, R3= 3-CHO 1511 R2= S02Me, Z = O, R3= 5-OMe

[1400] 1475 R2= S02Me, Z = S, R3= 3 -Me 1512 R2= S02Me, Z = O, R3= 5-OCF3

[1401] 1476 R2= S02Me, Z = S, R3= 3-Et 1513 R2= S02Me, Z = O, R3= 5-CF3

[1402] 1477 R2= S02Me, Z = S, R3= 3-Ethynyl 1514 R2= S02Me, Z = O, R3= 5-CHF2

[1403] 1478 R2= S02Me, Z = S, R3= 3-Ethenyl 1515 R2= S02Me, Z = O, R3= 5-CH2F

[1404] 1479 R2= S02Me, Z = S, R3= 3-S02Me 1516 R2= S02Me, Z = O, R3= 5-CHO

[1405] 1480 R2= S02Me, Z = S, R3= 3-OAc 1517 R2= S02Me, Z = O, R3=5-Me

[1406] 1481 R2= S02Me, Z = S, R3= 3-c-Pr 1518 R2= S02Me, Z = O, R3= 5-Et

[1407] 1482 R2= S02Me, Z = S, R3= 3-z-Pr 1519 R2= S02Me, Z = O, R3= 5-Ethynyl

[1408] 1483 R2= S02Me, Z = S, R3= 3-Ph 1520 R2= S02Me, Z = O, R3= 5-Ethenyl

[1409] 1484 R2= S02Me, Z = O, R3= 4-F 1521 R2= S02Me, Z = O, R3= 5-S02Me

[1410] 1485 R2= S02Me, Z = O, R3= 4-Cl 1522 R2= S02Me, Z = O, R3= 5-OAc

[1411] 1486 R2= S02Me, Z = O, R3= 4-Br 1523

[1412] R2= S02Me, Z = O, R3= 5-c-PrTable Header Row

[1413] 1524 R2= S02Me, Z = O, R3= 5-z-Pr

[1414] 1525 R2= S02Me, Z = O, R3= 5-Ph

[1415] 1526 R2= S02Me, Z = O, R:!= 6-F

[1416] 1527 R2= S02Me, Z = O, R3= 6-Cl

[1417] 1528 R2= S02Me, Z = O, R3= 6-Br

[1418] 1529 R2= S02Me, Z = O, R 5 = 6-1

[1419] 1530 R2= S02Me, Z = O, R3= 6-CN

[1420] 1531 R2= S02Me, Z = O, R3= = 6-N02

[1421] 1532 R2= S02Me, Z = O, R3= = 6-OMe

[1422] 1533 R2= S02Me, Z = O, R3= 6-OCF3

[1423] 1534 R2= S02Me, Z = O, R3= 6-CF3

[1424] 1535 R2= S02Me, Z = O, R3= 6-CHF2

[1425] 1536 R2= S02Me, Z = O, R3= 6-CH2F

[1426] 1537 R2= S02Me, Z = O, R3= = 6-CHO

[1427] 1538 R2= S02Me, Z = O, R3= 6-Me

[1428] 1539 R2= S02Me, Z = O, R3= 6-Et

[1429] 1540 R2= S02Me, Z = O, R3= 6-Ethynyl

[1430] 1541 R2= S02Me, Z = O, R3= 6-Ethenyl

[1431] 1542 R2= S02Me, Z = O, R3= 6-S02Me

[1432] 1543 R2= S02Me, Z = O, R3= = 6-OAc

[1433] 1544 R2= S02Me, Z = O, R3= 6-c-Pr

[1434] 1545 R2= S02Me, Z = O, R3= 6-z-Pr

[1435] 1546 R2= S02Me, Z = O, R3= 6-Ph

[1436] 1547 R2= S02Me, Z = O, R3= 3,4-di-F

[1437] 1548 R2= S02Me, Z = O, R3= 3,5-di-F

[1438] 1549 R2= S02Me, Z = O, R3= 3,6-di-F

[1439] 1550 R2= S02Me, Z = O, R3= 4,5-di-F

[1440] 1551 R2= S02Me, Z = O, R3= 3,4-di-Cl

[1441] 1552 R2= S02Me, Z = O, R3= 3,5-di-Cl

[1442] 1553 R2= S02Me, Z = O, R3= 3,6-di-Cl

[1443] 1554 R2= S02Me, Z = O, R3= 4,5-di-Cl

[1444] A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. 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 both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in -water emulsions, flowable concentrates and / or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

[1445] The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated"). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.

[1446] Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffmic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.

[1447] 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

[1448] Active

[1449] Ingredient Diluent Surfactant

[1450] Water-Dispersible and Water-soluble 0.001-90 0-99.999 0-15

[1451] Granules, Tablets and Powders

[1452] Oil Dispersions, Suspensions, 1-50 40-99 0-50

[1453] Emulsions, Solutions (including

[1454] Emulsifiable Concentrates)

[1455] Dusts 1-25 70 -99 0- -5

[1456] Granules and Pellets 0.001-99 5- 99.999 0- -15

[1457] High Strength Compositions 90-99 0- 10 0- -2

[1458] Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[1459] Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g.,methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[1460] The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as "surface-active agents") generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.

[1461] Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.

[1462] Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.

[1463] Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[1464] Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon 's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[1465] Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes / pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222.

[1466] The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added toemulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μιη can be wet milled using media mills to obtain particles with average diameters below 3 μιη. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μιη range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. 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.

[1467] 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 10-41; 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.

[1468] In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A. 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. Percentages are by weight except where otherwise indicated.Example A

[1469] High Strength Concentrate

[1470] Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%

[1471] Example B

[1472] Wettable Powder

[1473] Compound 12 65.0% dodecylphenol polyethylene glycol ether 2.0%> sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%

[1474] Example C

[1475] Granule

[1476] Compound 15 10.0% attapulgite granules (low volatile matter, 0.71 / 0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

[1477] Example D

[1478] Extruded Pellet

[1479] Compound 21 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0%> sodium alkylnaphthalenesulfonate 1.0% calcium / magnesium bentonite 59.0%

[1480] Example E

[1481] Emulsifiable Concentrate

[1482] Compound 23 10.0% polyoxyethylene sorbitol hexoleate 20.0%

[1483] C^-Cio fatty acid methyl ester 70.0%>

[1484] Example F

[1485] Microemulsion

[1486] Compound 24 5.0% polyvinylpyrrolidone -vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0%> glyceryl monooleate 15.0% water 20.0%Example G

[1487] Suspension Concentrate

[1488] Compound 27 35% butyl polyoxyethylene / polypropylene block copolymer 4.0% stearic acid / polyethylene glycol copolymer 1.0%> styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1 % l,2-benzisothiazolin-3-one 0.1% water 53.7%

[1489] Example H

[1490] Emulsion in Water

[1491] Compound 32 10.0% butyl polyoxyethylene / polypropylene block copolymer 4.0% stearic acid / polyethylene glycol copolymer 1.0%) styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0%> silicone based defoamer 0.1 % l,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0 water 58.7%

[1492] Example I

[1493] Oil Dispersion

[1494] Compound 42 25% polyoxy ethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5%

[1495] Example J

[1496] Suspoemulsion

[1497] Compound 1 10.0% imidacloprid 5.0%> butyl polyoxyethylene / polypropylene block copolymer 4.0%> stearic acid / polyethylene glycol copolymer 1.0%) styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0%>silicone based defoamer 0.1% l,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0% water 53.7%

[1498] Test results indicate that the compounds of the present invention are highly active preemergent and / or postemergent herbicides and / or plant growth regulants. The compounds of the mention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). 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.

[1499] 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 environmentof 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.

[1500] 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 0.001 to 20 kg / ha with a preferred range of about 0.004 to 1 kg / ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.

[1501] Compounds of the invention are useful in treating all plants and plant parts. Plant varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

[1502] Genetically modified plant cultivars which can be treated according to the invention include those that are resistant against one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperature, soil salinity, etc.), or that contain other desirable characteristics. Plants can be genetically modified to exhibit traits of, for example, herbicide tolerance, insect-resistance, modified oil profiles or drought tolerance. Useful genetically modified plants containing single gene transformation events or combinations of transformation events are listed in Exhibit C. Additional information for the genetic modifications listed in Exhibit C can be obtained from publicly available databases maintained, for example, by the U.S. Department of Agriculture.

[1503] The following abbreviations, 1 through 37, are used in Exhibit C for traits. A "-" means the entry is not available.

[1504] Trait Description Trait Description Trait Description

[1505] 1 Glyphosate tolerance 15 Cold tolerance 27 High tryptophan

[1506] 2 High lauric acid oil 16 Imidazolinone herb. tol. 28 Erect leaves semidwarf

[1507] 3 Glufosinate tolerance 17 Modified alpha-amylase 29 Semidwarf

[1508] 4 Phytate breakdown 18 Pollination control 30 Low iron tolerance

[1509] 5 Oxynil tolerance 19 2,4-D tolerance 31 Modified oil / fatty acid

[1510] 6 Disease resistance 20 Increased lysine 32 HPPD tolerance

[1511] 7 Insect resistance 21 Drought tolerance 33 High oil

[1512] 9 Modified flower color 22 Delayed ripening / senescence 34 Aryloxyalkanoate tol.

[1513] 11 ALS Herbicide Tol. 23 Modified product quality 35 Mesotrione tolerance

[1514] 12 Dicamba Tolerance 24 High cellulose 36 Reduced nicotine

[1515] 13 Anti- allergy 25 Modified starch / carbohydrate 37 Modified product

[1516] 14 Salt tolerance 26 Insect & disease resist.

[1517] Exhibit CCrop Trait(s) Gene(s)

[1518] Alfalfa 1 cp4 epsps (aroA:CP4)

[1519] Alfalfa 1 cp4 epsps (aroA:CP4)

[1520] Canola* 2 te

[1521] Canola* 2 te

[1522] Canola* 1 gat4621

[1523] Canola* 1 gat4621

[1524] Canola* 1 cp4 epsps (aroA:CP4); goxv247

[1525] Canola* 1 cp4 epsps (aroA:CP4); goxv247

[1526] Canola* 3 bar

[1527] Canola* 3 pat (syn)

[1528] Canola* 3 bar

[1529] Canola* 1 cp4 epsps (aroA:CP4)

[1530] Canola* 4 phyA

[1531] Canola* 4 phyA

[1532] Canola* 4 phyA

[1533] Canola* 4 phyA

[1534] Canola* 4 phyA

[1535] Canola* 3 bar

[1536] Canola* 3 bar

[1537] Canola* 5 bxn

[1538] Canola* 3 bar

[1539] Canola* 3 bar

[1540] Canola* 3 bar

[1541] Canola* 3 bar

[1542] Canola* 3 bar

[1543] Canola* 3 bar

[1544] Canola* 3 bar

[1545] Bean 6 acl (sense and antisense)

[1546] Brinjal # 7 cry 1 Ac

[1547] Cotton 11 S4-HrA

[1548] Cotton 3,7 pat (syn); cry IF

[1549] Cotton 3,7 pat (syn); cry 1 Ac

[1550] Cotton 5,7 bxn; crylAc

[1551] Cotton 5,7 bxn; crylAc

[1552] Cotton 5,7 bxn; crylAc

[1553] Cotton 5,7 bxn; crylAc

[1554] Cotton 5,7 bxn; crylAc

[1555] Cotton 7 crylAc

[1556] Cotton 5 bxn; crylAc

[1557] Cotton5 bxn; crylAcCotton bxn; crylAc

[1558] Cotton bxn; crylAc

[1559] Cotton vip3A(a)

[1560] Cotton crylAb

[1561] Cotton vip3A

[1562] Cotton crylAc

[1563] Cotton crylAb-Ac

[1564] Cotton cry2Ae

[1565] Cotton 2mepsps

[1566] Cotton crylAb-Ac

[1567] Cotton bar

[1568] Cotton crylC

[1569] Cotton crylAc

[1570] Cotton cp4 epsps (aroA:CP4)

[1571] Cotton crylAc; cry2Ab2

[1572] Cotton cp4 epsps (aroA:CP4)

[1573] Cotton crylAc

[1574] Cotton crylAc

[1575] Cotton cp4 epsps (aroA:CP4)

[1576] Cotton

[1577] Cotton crylA; CpTI

[1578] Cotton crylAb; bar

[1579] Cotton crylAb; bar

[1580] Cotton crylAb

[1581] Cotton crylAb

[1582] Cotton crylAb

[1583] Cotton crylAb

[1584] Cotton crylAb

[1585] Cotton crylAb

[1586] Cotton cp4 epsps (aroA:CP4)

[1587] Cotton mepsps

[1588] Cotton crylAb

[1589] Cotton Modified dmo; bar

[1590] Cotton Modified Cryj

[1591] Flax als

[1592] Lentil als

[1593] Maize amy797E

[1594] Maize ecry3.1Ab

[1595] Maize cry34Abl ; cry35Abl ; pat

[1596] Maize pat; dam

[1597] Maize pat; dam

[1598] Maize

[1599] Maize

[1600] Maize

[1601] Maize

[1602] Maize

[1603] Maize

[1604] Maize

[1605] Maize

[1606] Maize

[1607] Maize

[1608] Maize

[1609] Maize

[1610] Maize

[1611] Maize

[1612] Maize

[1613] Maize

[1614] Maize

[1615] Maize

[1616] Maize

[1617] Maize

[1618] Maize

[1619] Maize

[1620] Maize

[1621] Maize

[1622] Maize

[1623] Maize

[1624] Maize

[1625] Maize

[1626] Maize

[1627] Maize

[1628] Maize

[1629] Maize

[1630] Maize

[1631] Maize

[1632] Maize

[1633] Maize

[1634] Maize

[1635] Maize

[1636] Maize

[1637] MelonRice

[1638] Rice

[1639] Rice

[1640] Rice

[1641] Rice

[1642] Rice

[1643] Rose

[1644] Rose

[1645] Soybean

[1646] Soybean

[1647] Soybean

[1648] Soybean

[1649] Soybean

[1650] Soybean

[1651] Soybean

[1652] Soybean

[1653] Soybean

[1654] Soybean

[1655] Soybean

[1656] Soybean

[1657] Soybean

[1658] Soybean

[1659] Soybean

[1660] Soybean

[1661] Soybean

[1662] Soybean

[1663] Soybean

[1664] Soybean

[1665] Soybean

[1666] Soybean

[1667] Soybean

[1668] Soybean

[1669] Squash

[1670] Squash

[1671] Sugar Beet

[1672] Sugar Beet

[1673] Sugar Beet

[1674] Sugar Beet

[1675] SugarcaneSunflower X81359 16 als Pepper PK-SP01 6 cmv cp

[1676] Tobacco C / F / 93 / 08-02 5 bxn

[1677] Tobacco Vector 21-41 36 NtQPTl (antisense) Wheat MON71800 MON-71800-3 1 cp4 epsps (aroA:CP4) * Argentine (Brassica napus), ** Polish (B. rapa), # Eggplant

[1678] Treatment of genetically modified plants with compounds of the invention may result in super-additive or synergistic effects. For example, reduction in application rates, broadening of the activity spectrum, increased tolerance to biotic / abiotic stresses or enhanced storage stability may be greater than expected from just simple additive effects of the application of compounds of the invention on genetically modified plants.

[1679] Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.

[1680] 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, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, 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, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam- methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, 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, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, 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, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam,metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfiuorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyrafiufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, safiufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6- TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-l- methyl- 1 ,5-naphthyridin-2(lH)-one, 5-chloro-3-[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 - yl)carbonyl]- 1 -(4-methoxyphenyl)-2( lH)-quinoxalinone, 2-chloro-N-( 1 -methyl- lH-tetrazol- 5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2- difluoroethyl)-8-hydroxypyrido[2,3-¾]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)- 5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5- dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 3-[7-fluoro-3,4- dihydro-3-oxo-4-(2-propyn- 1 -yl)-2H- 1 ,4-benzoxazin-6-yl]dihydro- 1 ,5-dimethyl-6-thioxo- 1 ,3,5-triazine-2,4(lH,3H)-dione, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo- 1 -cyclohexen- 1 - yl)carbonyl] -2 -methyl- 1 ,2,4-triazine-3,5(2H,4H)-dione, methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3- (methylsulfonyl)-N-(l -methyl- lH-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 2-methyl- N-(4-methyl-l,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, CoUetotrichum gloeosporiodes (Penz.) Penz. & Sacc, Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.

[1681] Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-lH-purin-6-amine, epocholeone, gibberellicacid, gibberellin A4and A7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.

[1682] General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001.

[1683] For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1 :3000 and about 3000: 1. Of note are weight ratios between about 1 :300 and about 300: 1 (for example ratios between about 1 :30 and about 30: 1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.

[1684] In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and / or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.

[1685] Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.

[1686] Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil,cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr- diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)- 2-fluorobenzenesulfonamide, l-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4- (dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl- 1,3-dioxolane (MG 191), ethyl l,6-dihydro-l-(2-methoxyphenyl)-6-oxo-2-phenyl-5- pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3- carboxamide, and 3-oxo-l-cyclohexen-l-yl l-(3,4-dimethylphenyl)-l,6-dihydro-6-oxo-2- phenyl-5-pyrimidinecarboxylate 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.

[1687] Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

[1688] Table Al lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound 1 in the Component (a) column is identified in Index Table A. The second column of Table Al lists the specific Component (b) compound (e.g., "2,4-D" in the first line). The third, fourth and fifth columns of Table Al lists ranges of weight ratios for rates at which the Component (a) compound is typically applied to a field-grown crop relative to Component (b) (i.e. (a):(b)). Thus, for example, the first line of Table Al specifically discloses the combination of Component (a) (i.e. Compound 1 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1 : 168 - 6: 1. The remaining lines of Table Al are to be construed similarly.TABLE Al

[1689] Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1690] 1 2,4-D 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1691] 1 Acetochlor 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1692] 1 Acifluorfen 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1693] 1 Aclonifen 1:750 to 2:1 1:250 to 1:3 1:75 to 1:9

[1694] 1 Alachlor 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1695] 1 Ametryn 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1696] 1 Amicarbazone 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1697] 1 Amidosulfuron 1:6 to 150:1 1:2 to 50:1 1:1 to 15:1

[1698] 1 Aminocyclopyrachlor 1:42 to 22:1 1:14 to 8:1 1:4 to 3:1

[1699] 1 Aminopyralid 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1700] 1 Amitrole 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1701] 1 Anilofos 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1702] 1 Asulam 1:840 to 2:1 1:280 to 1:3 1:84 to 1:10

[1703] 1 Atrazine 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1704] 1 Azimsulfuron 1:6 to 150:1 1:2 to 50:1 1:1 to 15:1

[1705] 1 Beflubutamid 1:300 to 3:1 1:100 to 1:1 1:30 to 1:4

[1706] 1 Benfuresate 1:540 to 2:1 1:180 to 1:2 1:54 to 1:6

[1707] 1 Bensulfuron-methyl 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1708] 1 Bentazon 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1709] 1 Benzobicyclon 1:75 to 12:1 1:25 to 4:1 1:7 to 2:1

[1710] 1 Benzofenap 1:225 to 4:1 1:75 to 2:1 1:22 to 1:3

[1711] 1 Bicyclopyrone 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1712] 1 Bifenox 1:225 to 4:1 1:75 to 2:1 1:22 to 1:3

[1713] 1 Bispyribac-sodium 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1714] 1 Bromacil 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1715] 1 Bromobutide 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1716] 1 Bromoxynil 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1717] 1 Butachlor 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1718] 1 Butafenacil 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1719] 1 Butylate 1:1350 to 1:2 1:450 to 1:5 1:135 to 1:15

[1720] 1 Carfenstrole 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1721] 1 Carfentrazone-ethyl 1:112 to 8:1 1:37 to 3:1 1:11 to 1:2

[1722] 1 Chlorimuron-ethyl 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1723] 1 Chlorotoluron 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1724] 1 Chlorsulfuron 1:6 to 150:1 1:2 to 50:1 1:1 to 15:1

[1725] 1 Cincosulfuron 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1726] 1 Cinidon-ethyl 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1727] 1 Cinmethylin 1:30 to 30:1 l:10to 10:1 1:3 to 3:1

[1728] 1 Clacyfos 1:84 to 6:1 1:28 to 2:1 1:16 to 1:2

[1729] 1 Clethodim 1:42 to 22:1 1:14 to 8:1 1:4 to 3:1

[1730] 1 Clodinafop-propargyl 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1731] 1 Clomazone 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1732] 1 Clomeprop 1:150 to 6:1 1:50 to 2:1 1:15 to 1:2

[1733] 1 Clopyralid 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1734] 1 Cloransulam-methyl 1:10 to 86:1 1:3 to 29:1 1:1 to 9:1

[1735] 1 Cumyluron 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1736] 1 Cyanazine 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1737] 1 Cyclopyrimorate 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1738] 1 Cyclosulfamuron 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1739] 1 Cycloxydim 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1740] 1 Cyhalofop 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1741] 1 Daimuron 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1742] 1 Desmedipham 1:282 to 4:1 1:94 to 2:1 1:28 to 1:4

[1743] 1 Dicamba 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1744] 1 Dichlobenil 1:1200 to 1:2 1:400 to 1:4 1:120 to 1:14

[1745] 1 Dichlorprop 1:810 to 2:1 1:270 to 1:3 1:81 to 1:9

[1746] 1 Diclofop-methyl 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1747] 1 Diclosulam 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1748] 1 Difenzoquat 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1749] 1 Diflufenican 1:750 to 2:1 1:250 to 1:3 1:75 to 1:9

[1750] 1 Diflufenzopyr 1:10 to 86:1 1:3 to 29:1 1:1 to 9:1

[1751] 1 Dimethachlor 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1752] 1 Dimethametryn 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1753] 1 Dimethenamid-p 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1754] 1 Dithiopyr 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1755] 1 Diuron 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1756] 1 EPTC 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1757] 1 Esprocarb 1:1200 to 1:2 1:400 to 1:4 1:120 to 1:14

[1758] 1 Ethalfluralin 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1759] 1 Ethametsulfuron-methyl 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1760] 1 Ethoxyfen 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1761] 1 Ethoxysulfuron 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1762] 1 Etobenzanid 1:225 to 4:1 1:75 to 2:1 1:22 to 1:3

[1763] 1 Fenoxaprop-ethyl 1:105 to 9:1 1:35 to 3:1 1:10 to 1:2

[1764] 1 Fenoxasulfone 1:75 to 12:1 1:25 to 4:1 1:7 to 2:1

[1765] 1 Fenquinotrione 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1766] 1 Fentrazamide 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1767] 1 Flazasulfuron 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1768] 1 Florasulam 1:2 to 375:1 1:1 to 125:1 4:1 to 38:1

[1769] 1 Fluazifop-butyl 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1770] 1 Flucarbazone 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1771] 1 Flucetosulfuron 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1772] 1 Flufenacet 1:225 to 4:1 1:75 to 2:1 1:22 to 1:3

[1773] 1 Flumetsulam 1:21 to 43:1 1:7 to 15:1 1:2 to 5:1

[1774] 1 Flumiclorac-pentyl 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1775] 1 Flumioxazin 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1776] 1 Fluometuron 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1777] 1 Flupyrsulfuron-methyl 1:3 to 300:1 1:1 to 100:1 3:1 to 30:1

[1778] 1 Fluridone 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1779] 1 Fluroxypyr-meptyl 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1780] 1 Flurtamone 1:750 to 2:1 1:250 to 1:3 1:75 to 1:9

[1781] 1 Fluthiacet-methyl 1:42 to 38:1 1:14 to 13:1 1:2 to 5:1

[1782] 1 Fomesafen 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1783] 1 Foramsulfuron 1:12 to 75:1 1:4 to 25:1 1:1 to 8:1

[1784] 1 Glufosinate 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1785] 1 Glyphosate 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1786] 1 Halauxifen 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1787] 1 Halauxifen-methyl 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1788] 1 Halosulfuron-methyl 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1789] 1 Haloxyfop-methyl 1:30 to 30:1 l:10to 10:1 1:3 to 3:1

[1790] 1 Hexazinone 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1791] 1 Imazamox 1:12 to 75:1 1:4 to 25:1 1:1 to 8:1

[1792] 1 Imazapic 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1793] 1 Imazapyr 1:75 to 12:1 1:25 to 4:1 1:7 to 2:1Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1794] 1 Imazaquin 1:30 to 30:1 1:10 to 10:1 1:3 to 3:1

[1795] 1 Imazethabenz-methyl 1:150 to 6:1 1:50 to 2:1 1:15 to 1:2

[1796] 1 Imazethapyr 1:21 to 43:1 1:7 to 15:1 1:2 to 5:1

[1797] 1 Imazosulfuron 1:24 to 38:1 1:8 to 13:1 1:2 to 4:1

[1798] 1 Indanofan 1:300 to 3:1 1:100 to 1:1 1:30 to 1:4

[1799] 1 Indaziflam 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1800] 1 lodosulfuron-methyl 1:3 to 300:1 1:1 to 100:1 3:1 to 30:1

[1801] 1 Ioxynil 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1802] 1 Ipfencarbazone 1:75 to 12:1 1:25 to 4:1 1:7 to 2:1

[1803] 1 Isoproturon 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1804] 1 Isoxaben 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1805] 1 Isoxaflutole 1:52 to 18:1 1:17 to 6:1 1:5 to 2:1

[1806] 1 Lactofen 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1807] 1 Lenacil 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1808] 1 Linuron 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1809] 1 MCPA 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1810] 1 MCPB 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1811] 1 Mecoprop 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1812] 1 Mefenacet 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1813] 1 Mefluidide 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1814] 1 Mesosulfuron-methyl 1:4 to 200:1 1:1 to 67:1 2:1 to 20:1

[1815] 1 Mesotrione 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1816] 1 Metamifop 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1817] 1 Metazachlor 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1818] 1 Metazosulfuron 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1819] 1 Methabenzthiazuron 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1820] 1 Metolachlor 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1821] 1 Metosulam 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1822] 1 Metribuzin 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1823] 1 Metsulfuron-methyl 1:1 to 500:1 1:1 to 167:1 5:1 to 50:1

[1824] 1 Molinate 1:900 to 1:1 1:300 to 1:3 1:90 to 1:10

[1825] 1 Napropamide 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1826] 1 Napropamide-M 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1827] 1 Naptalam 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1828] 1 Nicosulfuron 1:10 to 86:1 1:3 to 29:1 1:1 to 9:1Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1829] 1 Norflurazon 1:1008 to 1:2 1:336 to 1:4 1:100 to 1:12

[1830] 1 Orbencarb 1:1200 to 1:2 1:400 to 1:4 1:120 to 1:14

[1831] 1 Orthosulfamuron 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1832] 1 Oryzalin 1:450 to 2:1 1:150 to 1:2 1:45 to 1:5

[1833] 1 Oxadiargyl 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1834] 1 Oxadiazon 1:480 to 2:1 1:160 to 1:2 1:48 to 1:6

[1835] 1 Oxasulfuron 1:24 to 38:1 1:8 to 13:1 1:2 to 4:1

[1836] 1 Oxaziclomefone 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1837] 1 Oxyfluorfen 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1838] 1 Paraquat 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1839] 1 Pendimethalin 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1840] 1 Penoxsulam 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1841] 1 Penthoxamid 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1842] 1 Pentoxazone 1:90 to 10:1 1:30 to 4:1 1:9 to 1:1

[1843] 1 Phenmedipham 1:90 to 10:1 1:30 to 4:1 1:9 to 1:1

[1844] 1 Picloram 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1845] 1 Picolinafen 1:30 to 30:1 l:10to 10:1 1:3 to 3:1

[1846] 1 Pinoxaden 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1847] 1 Pretilachlor 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1848] 1 Primisulfuron-methyl 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1849] 1 Prodiamine 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1850] 1 Profoxydim 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1851] 1 Prometryn 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1852] 1 Propachlor 1:1008 to 1:2 1:336 to 1:4 1:100 to 1:12

[1853] 1 Propanil 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1854] 1 Propaquizafop 1:42 to 22:1 1:14 to 8:1 1:4 to 3:1

[1855] 1 Propoxycarbazone 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1856] 1 Propyrisulfuron 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1857] 1 Propyzamide 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1858] 1 Prosulfocarb 1:1050 to 1:2 1:350 to 1:4 1:105 to 1:12

[1859] 1 Prosulfuron 1:6 to 150:1 1:2 to 50:1 1:1 to 15:1

[1860] 1 Pyraclonil 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1861] 1 Pyraflufen-ethyl 1:4 to 200:1 1:1 to 67:1 2:1 to 20:1

[1862] 1 Pyrasulfotole 1:12 to 75:1 1:4 to 25:1 1:1 to 8:1

[1863] 1 Pyrazolynate 1:750 to 2:1 1:250 to 1:3 1:75 to 1:9Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1864] 1 Pyrazosulfuron-ethyl 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1865] 1 Pyrazoxyfen 1:4 to 200:1 1:1 to 67:1 2:1 to 20:1

[1866] 1 Pyribenzoxim 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1867] 1 Pyributicarb 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1868] 1 Pyridate 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1869] 1 Pyriftalid 1:9 to 100:1 1:3 to 34:1 1:1 to 10:1

[1870] 1 Pyriminobac -methyl 1:18 to 50:1 1:6 to 17:1 1:1 to 5:1

[1871] 1 Pyrimisulfan 1:15 to 60:1 1:5 to 20:1 1:1 to 6:1

[1872] 1 Pyrithiobac 1:21 to 43:1 1:7 to 15:1 1:2 to 5:1

[1873] 1 Pyroxasulfone 1:75 to 12:1 1:25 to 4:1 1:7 to 2:1

[1874] 1 Pyroxsulam 1:4 to 200:1 1:1 to 67:1 2:1 to 20:1

[1875] 1 Quinclorac 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1876] 1 Quizalofop-ethyl 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1877] 1 Rimsulfuron 1:12 to 75:1 1:4 to 25:1 1:1 to 8:1

[1878] 1 Saflufenacil 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1879] 1 Sethoxydim 1:84 to 11:1 1:28 to 4:1 1:8 to 2:1

[1880] 1 Simazine 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1881] 1 Sulcotrione 1:105 to 9:1 1:35 to 3:1 1:10 to 1:2

[1882] 1 Sulfentrazone 1:129 to 7:1 1:43 to 3:1 1:12 to 1:2

[1883] 1 Sulfometuron-methyl 1:30 to 30:1 1:10 to 10:1 1:3 to 3:1

[1884] 1 Sulfosulfuron 1:7 to 120:1 1:2 to 40:1 1:1 to 12:1

[1885] 1 Tebuthiuron 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1886] 1 Tefuryltrione 1:37 to 24:1 1:12 to 8:1 1:3 to 3:1

[1887] 1 Tembotrione 1:27 to 33:1 1:9 to 11:1 1:2 to 4:1

[1888] 1 Tepraloxydim 1:22 to 40:1 1:7 to 14:1 1:2 to 4:1

[1889] 1 Terbacil 1:252 to 4:1 1:84 to 2:1 1:25 to 1:3

[1890] 1 Terbuthylatrazine 1:750 to 2:1 1:250 to 1:3 1:75 to 1:9

[1891] 1 Terbutryn 1:168 to 6:1 1:56 to 2:1 1:16 to 1:2

[1892] 1 Thenylchlor 1:75 to 12:1 1:25 to 4:1 1:7 to 2:1

[1893] 1 Thiazopyr 1:336 to 3:1 1:112 to 1:2 1:33 to 1:4

[1894] 1 Thiencarbazone 1:3 to 300:1 1:1 to 100:1 3:1 to 30:1

[1895] 1 Thifensulfuron-methyl 1:4 to 200:1 1:1 to 67:1 2:1 to 20:1

[1896] 1 Thiobencarb 1:672 to 2:1 1:224 to 1:3 1:67 to 1:8

[1897] 1 Topramazone 1:6 to 150:1 1:2 to 50:1 1:1 to 15:1

[1898] 1 Tralkoxydim 1:60 to 15:1 1:20 to 5:1 1:6 to 2:1Component (a) Typical More Typical Most Typical (Compound #) Component (b) Weight Ratio Weight Ratio Weight Ratio

[1899] 1 Triafamone 1:3 to 38:1 1:1 to 13:1 1: 1 to 8:1

[1900] 1 Triallate 1:672 to 2: 1 1:224 to 1:3 1:67 to 1:8

[1901] 1 Triasulfuron 1:4 to 200: 1 1:1 to 67:1 2:1 to 20:1

[1902] 1 Triaziflam 1:150 to 6: 1 1:50 to 2:1 1: 15 to 1:2

[1903] 1 Tribenuron-methyl 1:3 to 300: 1 1: 1 to 100: 1 3:1 to 30: 1

[1904] 1 Triclopyr 1:168 to 6: 1 1:56 to 2:1 1:16 to 1:2

[1905] 1 Trifloxysulfuron 1:2 to 375: 1 1: 1 to 125: 1 4:1 to 38: 1

[1906] 1 Trifluralin 1:252 to 4: 1 1:84 to 2: 1 1:25 to 1:3

[1907] 1 Triflusulfuron-methyl 1: 15 to 60: 1 1:5 to 20:1 1: 1 to 6:1

[1908] 1 Tritosulfuron 1: 12 to 75: 1 1:4 to 25:1 1: 1 to 8:1

[1909] Table A2 is constructed the same as Table Al above except that entries below the "Component (a)" column heading are replaced with the respective Component (a) Column Entry shown below. Compound 1 in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the "Component (a)" column heading all recite "Compound 12" (i.e. Compound 12 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 12 with 2,4-D. Tables A3 through A9 are constructed similarly.

[1910] Table Number Component (a) Column Entries Table Number Component (a) Column Entries

[1911] A2 Compound 12 Al l Compound 53

[1912] A3 Compound 15 A12 Compound 55

[1913] A4 Compound 21 A13 Compound 62

[1914] A5 Compound 23 A14 Compound 63

[1915] A6 Compound 24 A15 Compound 144

[1916] A7 Compound 27 A16 Compound 145

[1917] A8 Compound 32 A17 Compound 168

[1918] A9 Compound 42 A18 Compound 200

[1919] A10 Compound 35

[1920] Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism, 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 chlorimuron-ethyl, nicosulfuron, diuron, hexazinoe, thifensulfuron-methyl and S-metolachlor.

[1921] The compounds of the present invention are useful for the control of weed species that are resistant to herbicides with the AHAS-inhibitor or (b2) [chemical compound that inhibitsacetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS)] mode of action.

[1922] 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 Table A for compound descriptions. Mass spectra are reported as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H+(molecular weight of 1) to the molecule, observed by mass spectrometry using atmospheric pressure chemical ionization (AP+) or electrospray ionization (ESI). The following abbreviations are used in the Index Table A which follow: Ph is phenyl, pyridyl is pyridinyl, OEt is ethoxy, CN is cyano, , CHO is formyl, t-Bu is tertiary-butyl, z'-Pr is z'so-propyl, c-Pr is cyclopropyl, Me is methyl, Et is ethyl and C(=0)CH3 is acyl. The abbreviation "Ex." stands for "Example" and is followed by a number indicating in which example the compound is prepared.

[1923] INDEX TABLE A

[1925] M.S.(AP+)

[1926] No. Q (R3)mor m.p.

[1927] 1 5-Cl-2-pyridyl CI m = 0

[1928] 2 6-N(CH3)2-3 -pyridyl CI m = 0 327a

[1929] 3 5-Cl-2-pyrimidinyl CI m = 0 320a

[1930] 4 3 -pyridyl CI m = 0 285a

[1931] 5 l,3,4-oxadiazol-2-yl Br m = 0 319

[1932] 6 l,3,4-oxadiazol-2-yl CI m = 0 275

[1933] 7 5-oxazolyl CI m = 0 274a

[1934] 8 4- thiazolyl CI m = 0 290

[1935] 9 5- thiazolyl CI m = 0 290

[1936] 10 l-CH3-l#-pyrazol-3-yl CI m = 0

[1937] 11 l-CH3-l#-pyrazol-4-yl CI m = 0

[1938] 12 3 -Br-5 -isoxazolyl CI m = 0 352

[1939] 13 5-thiazolyl CF3m = 0 324

[1940] 14 4-thiazolyl CF3m = 0 324

[1941] 15 2-Br-5-thiazolyl CF3m = 0 402M.S.(AP+)

[1942] No. Q R2 (R3)m or m.p.

[1943] 16 6-Cl-2-pyridyl CI m = 0 319a *

[1944] 17 6-Cl-2-pyridyl Br m = 0 363a*

[1945] 18 4-Cl-2-pyrimidinyl CI m = 0 320a*

[1946] 19 6-CF3-2-pyridyl CI m = 0 352a*

[1947] 20 2-CF3 -4-pyrmidinyl CI m = 0 353a*

[1948] 21 2-CF3 -4-pyrmidinyl Br m = 0 398a*

[1949] 22 6-CF3-3-pyridyl CI 4-CH3 366a

[1950] 23 5-Cl-2-pyidyl CI 3 -CI *

[1951] 24 2-CF3-4-pyridyl CI 4-CH3 366

[1952] 25 4-CF3-2-pyridyl CI m = 0 352

[1953] 26 4-CF3-2-pyridyl Br m = 0 397

[1954] 27 5-CF3-2-pyridyl CI m = 0 352

[1955] 28 5-CF3-2-pyridyl Br m = 0 397

[1956] 29 l-CH3-3-CF3-l / -pyrazol-5-yl CI m = 0 355

[1957] 30 1 -CH3-3 -CF3- l#-pyrazol-5-yl Br m = 0 399

[1958] 31 5-CH2OH-3-isoxazolyl CI m = 0 304

[1959] 32 5-CH2F-3-isoxazolyl CI m = 0 306

[1960] 33 5 -CHO-3 -isoxazolyl CI m = 0 302

[1961] 34 5-CH2Cl-3-isoxazolyl CI m = 0 322

[1962] 35 5-CF2H-3-isoxazolyl CI m = 0 324

[1963] 36 5-CH2CN-3-isoxazolyl CI m = 0 31 1b

[1964] 37 5-CH=NOH-3-isoxazolyl CI m = 0 317

[1965] 38 5-CN-3-isoxazolyl CI m = 0 299a

[1966] 39 3-CF3-PI1 CI 4-CH3 365

[1967] 40 3-OCF3-PI1 CI m = 0 367a*

[1968] 41 3,5-di-Cl-Ph CI m = 0 352a

[1969] 42 4-OCF3-PI1 CI m = 0 367a

[1970] 44 3-OCF3-PI1 CI 4-CH3 381a*

[1971] 45 3-OCF3-PI1 CI 6-OCF3 397a

[1972] 46 3-OCF3-PI1 CI 3-F 385a*

[1973] 47 1 -methyl- l / -tetrazol-5-yl CI m = 0 289

[1974] 48 2-methyl-2 / -tetrazol-5-yl CI m = 0 289

[1975] 49 1 -methyl- l / -tetrazol-5-yl Br m = 0 334

[1976] 50 2-methyl-2 / -tetrazol-5-yl Br m = 0 334

[1977] 51 1 -methyl- IH- 1 ,2,3 -triazol-4-yl CI m = 0 288M.S.(AP+)

[1978] No. Q R2 (R3)m or m.p.

[1979] 52 1 -methyl- \H- l,2,3-triazol-5-yl CI m = 0 288

[1980] 53 3-CHF2-5-isoxazolyl CI m = 0 324

[1981] 54 6-CF3 -4-pyrimidinyl CI m = 0 *

[1982] 55 5 -CHF2 -3 -isoxazolyl CI 3-F 96-98

[1983] 56 5-CHO-3-isoxazolyl CI 3-F 137-139

[1984] 57 5-CH2F-3-isoxazolyl CI 3-F 324

[1985] 58 3 -CH3 -5 - isoxazolyl CI m = 0 288

[1986] 59 5 - ( / -Bu) - 3 -i sox azolyl CI m = 0 330

[1987] 60 5 -CH 3 -3 -isoxazolyl CI m = 0 288

[1988] 61 2-oxazolyl CI m = 0 274

[1989] 62 5-CHF2-3-isoxazolyl Br m = 0 89-93

[1990] 63 3-CF3-5-isoxazolyl CI m = 0 342

[1991] 64 3 -CF3 -5-isoxazolyl Br m = 0 388

[1992] 65 3-CHF2-5-isoxazolyl CI 5-F 342

[1993] 66 3-CHF2-5-isoxazolyl Br 5-F 387

[1994] 67 3-CClF2-5-isoxazolyl CI m = 0 359

[1995] 68 3-CHF2-5-isoxazolyl CI 6-F 342

[1996] 69 3-CHF2-5-isoxazolyl Br 6-F 387

[1997] 70 2-CH3-4-oxazolyl CI m = 0 288

[1998] 71 2-CF3-4-pyridinyl CI m = 0 352

[1999] 72 2-CF3 -4-pyridinyl Br m = 0 396

[2000] 73 1 -(z-Pr)- IH- 1 ,2,4-triazol-3 -yl CI m = 0 316

[2001] 74 3-(c-Pr)-5-isoxazolyl CI m = 0 314

[2002] 75 3-CHF2-5-isoxazolyl CI 4-F 342

[2003] 76 3-CHF2-5-isoxazolyl Br 4-F 387

[2004] 77 3,5-di-Me-4-isoxazolyl CI 3-F 320

[2005] 78 3 , 5 -di-Me-4-isoxazolyl CI m = 0 302

[2006] 79 2-CH2CF3-2 / / -l,2,4-triazol-3-yl CI m = 0 102-106

[2007] 80 2-CF3 -4-pyridinyl F m = 0 336

[2008] 81 2-CF3 -4-pyridinyl CI 3-F 370

[2009] 82 2-CF3-4-pyridinyl Br 3-F 414

[2010] 83 2-CF3 -4-pyridinyl CH33-F 350

[2011] 84 3-CF3-5-isoxazolyl CI 4-F 360

[2012] 85 3 -CF3 -5 -isoxazolyl Br 4-F 405

[2013] 86 5-(C≡CH)-3-isoxazolyl CI m = 0 156-160

[2014] 87 2-CF3 -4-pyridinyl F 3-F 354M.S.(AP+) o. Q R2 (R3)m or m.p.

[2015] 88 5-(OCH2CF2H)-3-isoxazolyl CI m = 0 352

[2016] 89 1 -Et-3-CF3- l#-pyrazol-5-yl CI 3-CN 394

[2017] 90 l-( / -Pr)-3-CF3-l / / -pyrazol-5-yl CI 3-CN 408

[2018] 91 5-(CH=CF2)-3-isoxazolyl CI 3-F 354

[2019] 92 3-(c-Pr)-5-isoxazolyl Br m = 0 359

[2020] 93 1 -CH2CF3- IH- 1 ,2,4-triazol-3 -yl CI m = 0 155-158

[2021] 94 5-(OCH2CF3)-3-isoxazolyl CI m = 0 85-89

[2022] 95 3-CHF2-5-isoxazolyl CF33-F 376

[2023] 96 5-CHF2-3-isoxazolyl CI 3-Cl, 4-F 376

[2024] 97 5-CHCl2-3-isoxazolyl CI m = 0 88-91

[2025] 98 3-CHF2-5-isoxazolyl CF3m = 0 358

[2026] 99 5-(C≡CCF3)-3-isoxazolyl CI m = 0 63-65

[2027] 100 3 -CHF2- 1 ,2,4-oxadiazol-5-yl CI m = 0 107-109

[2028] 101 3-CHF2-5-isoxazolyl CI 3-CH3338

[2029] 102 3-CHF2-5-isoxazolyl Br 3-CH3383

[2030] 103 3-CHF2-5-isoxazolyl CI 3-OMe 354

[2031] 104 3 -CF3-5-isoxazolyl CI 3-OMe 372

[2032] 105 5 -CF3-3 -isoxazolyl CI 3-OMe 372

[2033] 106 5-CH3-l,3,4-oxadiazol-2-yl CI m = 0 289

[2034] 107 3-CHF2-5-isoxazolyl CI 3,5-di-F 358

[2035] 108 3-CH(OEt)2-5-isoxazolyl CI m = 0 398c

[2036] 109 5-CHF2-3-isoxazolyl CI 3-OMe 354

[2037] 1 10 3-CH3-5-isoxazolyl CI 3-OMe 318

[2038] 1 1 1 3-CH3-5-isoxazolyl F 3-OMe 302

[2039] 1 12 3-thienyl CI 3-CN 103-105

[2040] 1 13 5-CHF2-3-isoxazolyl CI 3,4-di-F 102-105

[2041] 1 14 5-CHF2-3-isoxazolyl CI 3 -Br, 4-F 420

[2042] 1 15 l-CH3-l#-l,2,4-triazol-3-yl CI m = 0 1 19-122

[2043] 1 16 5-CHClF-3-isoxazolyl CI m = 0 108-1 12

[2044] 1 17 1 -CH3- IH- 1 ,2,4-triazol-5-yl CI m = 0 134-138

[2045] 1 18 5-CHF2-3-isoxazolyl Br 3-F 386

[2046] 1 19 3 -Br-5 -isoxazolyl Br m = 0 398

[2047] 120 3-CHF2-5-isoxazolyl CI 3-Cl 359

[2048] 121 3-CHF2-5-isoxazolyl Br 3-Cl 403

[2049] 122 5-(c-Pr)- 1 ,3 ,4-oxadiazol-2-yl CI m = 0 315

[2050] 123 1 -(z'-Pr)- IH- 1 ,2,4-triazol-5-yl CI m = 0 316M.S.(AP+) o. Q 2 (R3)m or m.p.

[2051] 124 3-CF3-5-isoxazolyl CI 5-F 360

[2052] 125 3-CF3-5-isoxazolyl Br 5-F 405

[2053] 126 3 -CF3 -5 -isoxazolyl CI 3 -CI 377

[2054] 127 3 -CF3 -5 -isoxazolyl Br 3 -CI 421

[2055] 128 3 -(CH2OCH2CF3)-5-isoxazolyl CI m = 0 386

[2056] 129 3-(CH2OCH2CF3)-5-isoxazolyl Br m = 0 430a

[2057] 130 5-(c-Pr)-3-isoxazolyl CI 3-F 332

[2058] 131 5 -CHF2-3 -isoxazolyl CI 3-OCHF2390

[2059] 132 3-CHF2-5-isoxazolyl CI 3-OCHF2390

[2060] 133 5-CHFCF3-3-isoxazolyl CI m = 0 374

[2061] 134 3,5-di-Me-4-isoxazolyl CI 3-CN *

[2062] 135 5-Cl-2-pyridinyl CI 3 -Br *

[2063] 136 2-Me-5-CF3-2 / -pyrazol-3-yl CI 3-CN 380

[2064] 137 4-CF3-2-thiazolyl CI m = 0 358

[2065] 138 4-CF3-2-thiazolyl I m = 0 450

[2066] 139 4-CF3-2-thiazolyl Br m = 0 403

[2067] 140 5-CHO-3-furanyl CI m = 0 *

[2068] 141 5-CHF2-3-furanyl CI m = 0 *

[2069] 142 5-CF2CF3 -3 -isoxazolyl CI m = 0 392

[2070] 143 5-CF2Cl-3-isoxazolyl CI m = 0 358

[2071] 144 3-CHF2-5-isoxazolyl CI 3-F 342

[2072] 145 3-CHF2-5-isoxazolyl Br 3-F 387

[2073] 146 l-Me-5-CF3-l#-pyrazol-3-yl CI 3-CN 380

[2074] 147 1 -Me-5-CF3- l / -pyrazol-3 -yl CI 3 -Br 434

[2075] 148 5-C02Et-3-isoxazolyl CI m = 0 346

[2076] 149 5-CF2CH3-3-isoxazolyl Br m = 0 *

[2077] 150 5-C(=0)CH3-3-isoxazolyl Br m = 0 360

[2078] 151 1 -Me- l / / -imidazol-2-yl CI m = 0 287

[2079] 152 1 -Me- li / -imidazol-2-yl Br m = 0 332

[2080] 153 5-CH3-3-isoxazolyl CI m = 0 288

[2081] 154 5-isoxazolyl CI m = 0 274

[2082] 155 5-isoxazolyl Br m = 0 319

[2083] 156 5-CF3-3-isoxazolyl CI 3-1 *

[2084] 157 5-CF3-3-isoxazolyl CI 3-CN 367

[2085] 158 4-CF3 -2-pyridinyl CI 3-CN 377

[2086] 159 4-CF3-2-pyridinyl CI 3 -CI 386M.S.(AP+) o. Q R2 (R3)m or m.p.

[2087] 160 5-CF3-2-pyridinyl CI 3 -CI 386

[2088] 161 1 -CH2CF3- l#-imidazol-4-yl CI m = 0 *

[2089] 162 5-CBrF2-3-isoxazolyl CI m = 0 402

[2090] 163 2-pyrazinyl CI m = 0 79-82

[2091] 164 2-pyrazinyl F m = 0 95-97

[2092] 165 2-pyrazinyl CI 3-F 303

[2093] 166 2-pyrazinyl F 3-F 287

[2094] 167 4-Me-5-CF3-3-isoxazolyl CI m = 0 356

[2095] 168 5 -CF3 -3 -isoxazolyl CI 3-F 360

[2096] 169 5 -CF3 -3 -isoxazolyl CI 3 -CI 376

[2097] 170 5 -CF3 -3 -isoxazolyl CI 3 -Br 420

[2098] 171 3 -CH3 -5-isothiazolyl CI m = 0 304

[2099] 172 1 ,2,4-thiadiazol-5-yl CI m = 0 132-135

[2100] 173 5 -CF2CH3 -3 -isoxazolyl CH3m = 0 *

[2101] 174 4-Cl-2-pyridinyl CI m = 0 319

[2102] 175 4-F-2-pyridinyl CI m = 0 302

[2103] 176 3-(OCH2CF3)-5-isoxazolyl CI m = 0 372

[2104] 177 3-Et-5-isoxazolyl CI m = 0 318

[2105] 178 3 -CF2CH3 -5 -isoxazolyl CI m = 0 338

[2106] 179 5-CHF2-3-isoxazolyl CI 3 -CI 358

[2107] 180 5-CHF2-3-isoxazolyl CI 3-CN 349

[2108] 181 5-Br-2-thienyl CI m = 0 368

[2109] 182 2-thienyl CI m = 0 290

[2110] 183 5-(c-Pr)-3-isoxazolyl CI m = 0 314

[2111] 184 6-CHF2-4-pyrimidinyl CI m = 0 334

[2112] 185 3 -isoxazolyl CI m = 0 274

[2113] 186 6-C1-3 -pyridazinyl CI m = 0 319

[2114] 187 4-Me-2-pyridinyl CI m = 0 298

[2115] 188 4-CN-2-pyridinyl CI m = 0 309

[2116] 189 5-Cl-3-pyridazinyl CI m = 0 320

[2117] 190 6-Cl-4-pyrimidinyl CI m = 0 320

[2118] 191 5 -CH2F-3 -isoxazolyl CI 3 -Br 384

[2119] 192 5-Cl-3-isothiazolyl CI m = 0 86-88

[2120] 193 5-Cl-3-isothiazolyl F m = 0 100-102

[2121] 194 5-Cl-3-isothiazolyl CH3m = 0 78-82

[2122] 195 5-CHO-3-isoxazolyl CI 3 -Br 379M.S.(AP+)

[2123] No. Q R2 (R3)m or m.p.

[2124] 196 3-C(CH3)=CH2-5-isoxazolyl CI m = 0 314

[2125] 197 3-C(CH3)=CH2-5-isoxazolyl Br m = 0 359

[2126] 198 5-CFCl2-3-isoxazolyl CI m = 0 374

[2127] 199 2-thiazolyl CI m = 0 290

[2128] 200 5 -CF3 -3 -isoxazolyl CI m = 0 342

[2129] 201 3-N02,5-Cl-2-pyridinyl CI m = 0 363a

[2130] 202 5-Cl-2-pyridinyl CI 3-CN 344

[2131] 203 5-Cl-2-pyridinyl CI 5-Br 398

[2132] 204 5-Cl-2-pyridinyl Br 3-CN 388

[2133] 205 5-Cl-2-pyridinyl CI 3-1 445

[2134] 206 5-CF3-3-isoxazolyl F m = 0 326

[2135] 207 5-Cl-2-pyridinyl F 3-CN 327

[2136] 208 5-Cl-2-pyridinyl CI 3-& 464

[2137] 209 4-Br- l / -pyrazol- 1 -yl CI 6-CN 377

[2138] 210 3-CHF2-5-isoxazolyl F m = 0 308

[2139] 21 1 3-CHF2-5-isoxazolyl CH3m = 0 304

[2140] 212 3-CHF2-5-isoxazolyl Br m = 0 369

[2141] 213 3 -CHF2-5-isoxazolyl OMe m = 0 320

[2142] 214 4-oxazolyl CI m = 0 274

[2143] 215 5-C(=0)CH3-3 -isoxazolyl CI m = 0 316

[2144] 216 4-CH3-2-thienyl CI m = 0 303

[2145] 217 1 -CH2CF3- l^-imidazol-4-yl CI 3-F 373

[2146] 218 3 -C(=0)CH3-5-isoxazolyl CI m = 0 316

[2147] 219 4-OMe-2-pyridinyl CI m = 0 314

[2148] 220 5 -CF2CH3 -3 -isoxazolyl CI m = 0 338

[2149] 221 5-CFCl2-3-isoxazolyl CI 4-F 129-132

[2150] 222 5-CN-3-isoxazolyl CI 3-F 317

[2151] 223 3-CN-5-isoxazolyl CI m = 0 297

[2152] 224 3 -CH2F -5 -isoxazolyl CI m = 0 306

[2153] 225 3-C02Et-5-isoxazolyl CI m = 0 346

[2154] 226 5-CFH2-3-isoxazolyl CI m = 0 320

[2155] 227 6-OCH2CF3-4-pyrimidinyl CI m = 0 383

[2156] 228 3 -CF3 -5 -isoxazolyl CI 3-F 360

[2157] 229 3 -CH3 -5 -isoxazolyl CI 3-F 306

[2158] 230 3 -CH3 -5-isoxazolyl Br 3-F 351

[2159] 231 3-thienyl CI m = 0 289M.S.(AP+)

[2160] No. Q R2 (R3)m or m.p.

[2161] 232 3-thienyl Br m = 0 334

[2162] 233 5-isothiazolyl CI m = 0 290

[2163] 234 5-isothiazolyl Br m = 0 335

[2164] 235 5-C02 e-3-isoxazolyl CI m = 0 332

[2165] 236 5-CF(CH3)2-3-isoxazolyl CI m = 0 334

[2166] 237 1 -Me-5-CF3- l#-pyrazol-3 -yl CI m = 0 355

[2167] a ES+bAP-,CM+Na.

[2168] * See Index Table B forlR NMR data.

[2169] & 4-Br-l / -pyrazol-l-yl

[2170] INDEX TABLE B

[2171] Cmpd ^H NMR (CDCI3 solution unless indicated otherwise)2

[2172] I 8.54 (d, IH), 8.39 (s, 2H), 7.87 (d, IH), 7.69 (d, IH), 7.60 (m, IH), 7.50 (m, IH), 7.42 (m, IH), 7.24 (d, IH)

[2173] 10 8.43 (s, 2H), 8.03 (m, 2H), 7.36 (m, 2H), 7.26 (m, IH), 7.19 (m, IH), 6.56 (s, IH), 3.85 (s, 3H)

[2174] I I 8.45 (s, 2H), 7.77 (s, IH), 7.72 (s, IH), 7.62 (m, IH), 7.32 (m, 2H), 7.18 (m, IH), 3.86 (s, 3H)

[2175] 16 8.41 (s, 2H), 7.88 (m, IH), 7.64 (m, IH), 7.59 (m, IH), 7.50 (m, IH), 7.40 (m, IH), 7.24 (m, IH), 7.18 (m, IH)

[2176] 17 8.49 (s, 2H), 7.88 (m, IH), 7.64 (m, IH), 7.58 (m, IH), 7.50 (m, IH), 7.41 (m, IH), 7.25 (m, IH), 7.17 (m, IH)

[2177] 18 8.55 (m, IH), 8.43 (s, 2H), 8.05 (m, IH), 7.75 (m, IH), 7.58 (m, IH), 7.45 (m, IH), 7.26 (m, IH)

[2178] 19 8.41 (s, 2H), 7.89 (m, 2H), 7.82 (m, IH), 7.54 (m, 2H), 7.43 (m, lH), 7.26 (m, IH)

[2179] 20 8.82 (m, IH), 8.52 (s, 2H), 8.06 (m, IH), 7.96 (m, IH), 7.61 (m, IH), 7.48 (m, IH), 7.30 (m, IH)

[2180] 21 8.83 (d, IH), 8.52 (s, 2H), 8.08 (m, IH), 7.97 (d, IH), 7.62 (m,lH), 7.47 (m, IH), 7.30 (m, IH) 23 8.52 (m, IH), 8.40 (s, 2H), 7.66 (m, IH), 7.43 (m, 2H), 7.33 (m, IH), 7.18 (m, IH)

[2181] 40 8.26 (s, 2H), 7.39 (m, 2H), 7.32 (m, 2H), 7.27 (m, IH), 7.24 (s, IH), 7.17 (m, IH), 7.02 (d, IH)

[2182] 44 8.33 (s, 2H), 7.39 (s, IH), 7.28-7.34 (m, 2H), 7.25 (m, 2H), 7.12 (d, IH), 7.07 (m, IH), 2.43 (s, 3H)

[2183] 46 (300 MHz) 8.33 (S, 2H), 7.43 (m, IH), 7.34 (m, 2H), 7.22 (s, IH), 7.10 (m, 3H)

[2184] 54 9.42 (s, lH), 8.43 (s,2H), 8.12 (s,lH), 8.05 (d, lH), 7.72 (m,lH), 7.53 (m, lH), 7.32 (m,lH)

[2185] 134 8.36 (s, 2 H), 7.74 (m, 1 H), 7.62 (m, 1 H), 7.48 - 7.56 (m, 1 H), 2.33 (s, 3 H), 2.22 (s, 3 H)

[2186] 135 7.22 (m, IH), 7.31 (m, IH), 7.36 (m, IH), 7.65 (m, 2H), 8.40 (s, 2H), 8.52 (m, IH)

[2187] 140 9.60 (s, lH), 8.44 (s,2H), 8.05 (s,lH), 7.59 (d, lH), 7.54 (s,lH), 7.43 (t,lH), 7.37 (t,lH), 7.23 (d,lH)

[2188] 141 8.43 (s,2H), 7.86 (s,lH), 7.57 (d,lH), 7.37 (t,lH), 7.34 (t,lH), 7.22 (d,lH), 6.98 (s, lH), 6.57 (t,lH)149 8.54 (2, 2H), 7.96 (dd, 1H), 7.49-7.63 (m, 1H), 7.42 (t, 1H), 7.26-7.29 (m, 1H), 6.86 (t, 1H), 2.00 (t, 3H)

[2189] 156 7.06 - 7.08 (m, 1 H) 7.18 (s, 1 H) 7.93 (s, 1 H) 8.01 - 8.06 (m, 1 H) 8.46 (s, 2 H)

[2190] 161 8.34 (s,2H), 6.59 (s,lH), 6.56 (t,lH), 6.40-6.48 (m,2H), 7.28 (d, lH), 6.92 (s,lH), 6.55 (q,2H)

[2191] 173 8.34 (s, 2H), 7.99 (dd, 1H), 7.51-7.59 (m, 1H), 7.38 (dt, 1H), 7.26-7.31 (m, 1H), 6.90 (t, 1H), 2.25 (s, 3H), 1.99 (t, 3H)

[2192] z NMR data are in ppm downfield from tetramethylsilane at 500 MHz unless otherwise indicated.

[2193] Couplings are designated by (s)-singlet, (d)-doublet and (m)-multiplet.

[2194] BIOLOGICAL EXAMPLES OF THE INVENTION

[2195] TEST A

[2196] Seeds of plant species selected from downy bromegrass (Bromus tectorum), cocklebur (common cocklebur, Xanthium strumarium), wild oat (Avena fatua), barnyardgrass (Echinochloa crus-galli), large (Lg) crabgrass {Digitaria sanguinalis), giant foxtail {Setaria faberii), morningglory {Ipomoea spp.), velvetleaf {Abutilon theophrasti), and sorghum {Sorghum vulgare) were planted into a sandy loam soil and treated preemergence by soil drench using test a chemical formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time these species were also treated postemergence sprayed to runoff using a test chemical formulated in the same manner.

[2197] Plants ranged in height from 2 to 18 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 11 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

[2198] Table A Compound Table A Compo"

[2199] 1000 g ai / ha 39 2000 g ai / ha 39

[2200] Post Sprayed to Runoff Pre Soil Drench

[2201] Barnyardgrass 50 Barnyardgrass 90

[2202] Bromegrass, Downy 20 Bromegrass, Downy 70

[2203] Cocklebur 40 Cocklebur 0

[2204] Crabgrass, Large 50 Crabgrass, Large 90

[2205] Foxtail, Giant 30 Foxtail, Giant 100

[2206] Morningglory 30 Morningglory 0

[2207] Oat, Wild 20 Oat, Wild 90

[2208] Sorghum 30 Sorghum 50

[2209] Velvetleaf 60 Velvetleaf 70TEST B

[2210] Seeds of plant species selected from barnyardgrass {Echinochloa crus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), Italian ryegrass (Lolium multiflorum), large (Lg) crabgrass (Digitaria sanguinalis), giant foxtail (Setaria faberii), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and corn (Zea mays) 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.

[2211] At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), and galium (catchweed bedstraw, Galium aparine) were planted in pots containing the same blend of loam soil and sand and 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 one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table B, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (-) response means no test result.

[2212] Table B Compounds

[2213] 1000 g ai / ha 1 2 3 5 6 7 8 9 10 12 23 31 33 34

[2214] Postemergence

[2215] Barnyardgrass 70 0 50 20 0 10 0 10 10 40 50 10 0 0

[2216] Blackgrass

[2217] Corn 10 0 10 0 0 10 0 10 0 0 20 0 0 0

[2218] Crabgrass, Large 70 0 10 0 20 20 10 50 10 30 60 50 10 10

[2219] Foxtail, Giant 80 0 20 0 0 20 0 20 10 40 70 30 10 0

[2220] Galium

[2221] Kochia

[2222] Morningglory 60 40 60 20 20 40 10 50 10 30 70 30 10 0

[2223] Pigweed 100 70 70 70 70 20 70 60 50 100 100 30 10 40

[2224] Ragweed

[2225] Ryegrass, Italian

[2226] Velvetleaf 100 50 100 30 30 10 30 40 20 90 70 30 0 20

[2227] Wheat 0 0 10 0 0 10 0 10 0 10 0 0 0 0

[2228] Table B Compounds

[2229] 1000 g ai / ha 35 36 40 46 55 57 61 148 171 172 186 191 192 193

[2230] PostemergenceBarnyardgrass 100 90 30 90 100 100 10 10 30 10 0 100 100 90

[2231] Blackgrass - - - - 100 90 10 80 0 20 100 90 90

[2232] Corn 90 50 20 20 100 90 0 10 10 0 60 30 10

[2233] Crabgrass, Large 100 80 50 100

[2234] Foxtail, Giant 90 90 50 100 100 100 10 100 10 30 100 90 90

[2235] Galium - - - - 100 90 0 100 10 20 100 100 100

[2236] Kochia - - - - 100 90 0 100 30 30 100 100 100

[2237] Morningglory 100 20 100 70

[2238] Pigweed 100 90 100 100 100 100 0 100 80 20 100 100

[2239] Ragweed - - - - 100 100 0 30 10 50 90 60

[2240] Ryegrass, Italian - - - - 100 80 0 10 0 0 100 50 30

[2241] Velvetleaf 100 100 100 100

[2242] Wheat 80 50 10 20 100 90 0 30 0 0 30 30 20

[2243] Table B Compounds Table B Compounds

[2244] 1000 g ai / ha 194 195 235 1000 g ai / ha 194 195 235

[2245] Postemergence Postemergence

[2246] Barnyardgrass 100 10 0 Morningglory

[2247] Blackgrass 90 0 0 Pigweed 90 50 0

[2248] Corn 60 10 0 Ragweed 80 10 0

[2249] Crabgrass, Large - - - Ryegrass, Itali 50 10 0

[2250] Foxtail, Giant 90 10 0 Velvetleaf

[2251] Galium 100 10 0 Wheat 20 0 0

[2252] Kochia 100 10 0

[2253] Table B Compounds

[2254] 500 g ai / ha 4 10 11 13 14 16 17 18 19 20 21 22 23 24 Postemergence

[2255] Barnyardgrass 10 0 10 0 0 0 0 0 0 0 60 0 50 60

[2256] Blackgrass

[2257] Corn - 0 0 10 30 0 0 0 0 0 40 0 20 40

[2258] Crabgrass, Large 50 0 10 10 10 0 0 0 0 20 30 10 50 90

[2259] Foxtail, Giant 30 0 0 0 10 0 0 0 0 20 60 0 70 90

[2260] Galium

[2261] Kochia

[2262] Morningglory 30 30 20 10 0 - - 0 0 50 90 10 40 100

[2263] Pigweed 100 20 20 40 50 30 10 0 0 90 100 0 100 40

[2264] Ragweed

[2265] Ryegrass, ItalianVelvetleaf 60 20 20 60 30 20 20 0 0 30 40 60 70 70

[2266] Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2267] Table B Compounds

[2268] 500 g ai / ha 25 26 27 28 29 30 32 37 41 42 43 44 45 47

[2269] Postemergence

[2270] Barnyardgrass 30 20 50 50 0 0 90 0 20 30 20 20 20 0

[2271] Blackgrass - - - - - - - 0 - - - - - 0

[2272] Corn 30 20 30 20 0 0 50 0 10 20 10 20 10 0

[2273] Crabgrass, Large 50 30 90 40 10 10 90 - 20 50 20 20 40 -

[2274] Foxtail, Giant 60 30 70 40 0 10 90 10 20 30 20 10 20 50

[2275] Galium - - - - - - - 0 - - - - - 60

[2276] Kochia - - - - - - - 0 - - - - - 80

[2277] Morningglory 70 50 50 30 0 10 90 - 10 60 20 30 30 -

[2278] Pigweed 90 80 100 100 10 10 100 20 70 80 70 50 60 70

[2279] Ragweed - - - - - - - 0 - - - - - 30

[2280] Ryegrass, Italian - - - - - - - 0 - - - - - 0

[2281] Velvetleaf 80 80 100 100 0 30 100 - 30 100 70 70 60 -

[2282] Wheat 10 10 0 0 0 0 60 0 0 0 0 0 0 10

[2283] Table B Compounds

[2284] 500 g ai / ha 48 49 50 51 52 53 54 58 59 60 62 63 64 123

[2285] Postemergence

[2286] Barnyardgrass 0 10 0 0 10 100 100 90 10 100 100 100 100 0

[2287] Blackgrass 60 10 60 50 10 100 80 90 40 100 - - - 0

[2288] Corn 10 10 0 0 10 70 0 50 10 90 50 20 30 0

[2289] Crabgrass, Large 90 90 90 -

[2290] Foxtail, Giant 40 10 10 50 0 100 100 90 50 100 90 80 80 0

[2291] Galium 100 60 100 90 50 100 100 100 90 100 - - - 0

[2292] Kochia 100 30 80 100 50 100 100 100 20 100 - - - 0

[2293] Morningglory 100 100 100 -

[2294] Pigweed 100 30 100 80 60 100 100 100 50 100 100 100 100 0

[2295] Ragweed 70 30 60 60 20 90 60 100 0 90 - - - 0

[2296] Ryegrass, Italian 0 0 50 0 0 100 60 80 0 80 - - - 0

[2297] Velvetleaf 100 100 100 -

[2298] Wheat 0 20 20 10 20 80 0 50 10 90 30 50 10 0

[2299] Table B Compounds

[2300] 500 g ai / ha 134 135 136 137 138 139 151 152 153 156 157 158 159 160

[2301] PostemergenceBarnyardgrass 90 40 90 10 0 0 0 0 70 20 60 100 20 80

[2302] Blackgrass - - - 0 0 0 0 0 90 40 90 90 30 90

[2303] Corn 80 30 70 20 0 0 0 0 40 40 40 90 30 90

[2304] Crabgrass, Large 100 50 90

[2305] Foxtail, Giant 90 60 80 20 0 0 0 0 90 90 80 100 70 100

[2306] Galium - - - 20 0 0 0 0 100 100 100 100 100 100

[2307] Kochia - - - 60 0 0 0 0 90 90 100 90 80 90

[2308] Morningglory 90 50 90

[2309] Pigweed 100 100 100 90 0 0 0 0 100 100 100 100 100 100

[2310] Ragweed - - - 0 0 0 0 0 100 40 50 30 0 30

[2311] Ryegrass, Italian - - - 0 0 0 0 0 60 70 100 70 0 90

[2312] Velvetleaf 90 80 100

[2313] Wheat 30 10 40 0 0 0 0 0 50 30 70 70 20 80

[2314] Table B Compounds

[2315] 500 g ai / ha 161 167 168 169 170 179 180 181 182 183 184 185 190 199

[2316] Postemergence

[2317] Barnyardgrass 0 10 100 30 20 80 90 20 10 70 50 40 0 0

[2318] Blackgrass 0 10 90 90 60 100 90 10 10 90 60 50 0 -

[2319] Corn 0 20 100 20 20 40 70 10 20 30 20 10 0 0

[2320] Crabgrass, Large 10

[2321] Foxtail, Giant 0 10 100 60 50 80 100 20 50 80 70 70 0 0

[2322] Galium 0 60 100 100 100 100 100 50 50 100 100 70 10 -

[2323] Kochia 0 60 90 90 100 100 100 50 80 100 100 100 0 -

[2324] Morningglory 10

[2325] Pigweed 0 70 100 100 100 100 100 90 80 100 100 100 20 30

[2326] Ragweed 0 0 90 30 50 30 70 10 10 30 40 100 10 -

[2327] Ryegrass, Italian 0 0 90 50 20 100 100 0 0 70 20 0 0 -

[2328] Velvetleaf 10

[2329] Wheat 0 20 100 0 30 90 90 0 0 60 10 0 0 0

[2330] Table B Compounds

[2331] 500 g ai / ha 200 201 202 203 204 205 206 207 208 209 215 217

[2332] Postemergence

[2333] Barnyardgrass 100 0 40 0 10 10 10 70 20 0 90 0

[2334] Blackgrass 40 0

[2335] Corn 90 0 30 0 0 10 0 0 0 0 40 0

[2336] Crabgrass, Large 100 0 70 0 40 20 20 30 0 30 - -

[2337] Foxtail, Giant 100 0 80 0 30 20 20 30 0 30 80 0Galium 70 30

[2338] Kochia 10 30

[2339] Morningglory 100 0 40 0 10 10 30 30 0 30 - -

[2340] Pigweed 100 0 100 0 90 90 70 100 60 100 100 60

[2341] Ragweed 20 30

[2342] Ryegrass, Italian 50 0

[2343] Velvetleaf 100 0 30 0 10 10 60 60 30 30 - -

[2344] Wheat 100 0 0 0 0 0 0 0 0 0 20 0

[2345] Table B Compounds

[2346] 125 g ai / ha 4 10 11 13 14 15 16 17 18 19 20 21 22 23

[2347] Postemergence

[2348] Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2349] Blackgrass

[2350] Corn - 0 0 0 0 0 0 0 0 0 0 0 0 10

[2351] Crabgrass, Large 20 0 10 0 0 10 0 0 0 0 0 0 0 10

[2352] Foxtail, Giant 0 0 0 0 0 0 0 0 0 0 0 0 0 10

[2353] Galium

[2354] Kochia

[2355] Morningglory 0 20 10 0 0 10 - - 0 0 0 20 0 20

[2356] Pigweed 30 0 10 0 0 70 0 0 0 0 40 80 0 70

[2357] Ragweed

[2358] Ryegrass, Italian

[2359] Velvetleaf 30 0 10 30 20 0 0 0 0 0 0 20 50 40

[2360] Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2361] Table B Compounds

[2362] 125 g ai / ha 24 25 26 27 28 29 30 32 38 41 42 43 44 45

[2363] Postemergence

[2364] Barnyardgrass 0 0 0 20 0 0 0 70 0 0 20 0 10 0

[2365] Blackgrass - - - - - - - - 0 - - - - -

[2366] Corn 0 10 10 0 0 0 0 10 0 0 20 0 0 0

[2367] Crabgrass, Large 80 10 10 20 20 0 0 60 - 10 30 0 10 10

[2368] Foxtail, Giant 30 0 0 20 20 0 0 70 0 10 10 0 0 10

[2369] Galium - - - - - - - - 30 - - - - -

[2370] Kochia - - - - - - - - 30 - - - - -

[2371] Morningglory 50 10 10 10 0 0 0 70 - 0 20 0 20 30

[2372] Pigweed 20 30 30 50 30 0 0 100 20 40 60 30 20 10

[2373] Ragweed - - - - - - - - 0 - - - - -Ryegrass, Italian - - - - - - - - 0 - - - - -

[2374] Velvetleaf 40 20 10 70 40 0 10 90 - 10 100 20 30 50

[2375] Wheat 0 0 0 0 0 0 0 30 0 0 0 0 0 0

[2376] Table B Compounds

[2377] 125 g ai / ha 47 48 49 50 51 52 53 54 58 59 60 62 63 64

[2378] Postemergence

[2379] Barnyardgrass 0 0 0 0 0 0 100 20 70 10 50 90 80 90

[2380] Blackgrass 0 40 0 40 0 0 100 70 70 0 50 - - -

[2381] Corn 0 0 0 0 0 0 10 0 0 0 30 10 20 20

[2382] Crabgrass, Large 70 80 60

[2383] Foxtail, Giant 0 0 0 0 10 0 100 80 70 10 50 80 70 60

[2384] Galium 30 70 20 90 60 40 100 100 100 40 100 - - -

[2385] Kochia 60 50 30 60 70 20 100 100 100 0 90 - - -

[2386] Morningglory 90 100 70

[2387] Pigweed 50 70 10 70 70 30 100 100 100 40 100 100 100 100

[2388] Ragweed 20 50 30 20 20 20 60 50 100 0 60 - - -

[2389] Ryegrass, Italian 0 0 0 0 0 0 80 30 20 0 0 - - -

[2390] Velvetleaf 100 100 100

[2391] Wheat 0 0 10 0 0 0 40 0 0 0 30 0 0 0

[2392] Table B Compounds

[2393] 125 g ai / ha 70 73 89 90 91 96 97 103 104 105 106 107 108 109

[2394] Postemergence

[2395] Barnyardgrass 0 0 30 0 0 30 20 40 60 70 0 0 0 90

[2396] Blackgrass 0 0 20 0 0 70 0 90 100 100 0 0 0 90

[2397] Corn 0 0 30 0 0 20 20 30 30 20 0 0 10 60

[2398] Crabgrass, Large

[2399] Foxtail, Giant 0 0 40 0 0 50 30 70 80 80 0 0 0 90

[2400] Galium 0 10 50 30 0 100 50 100 100 100 0 0 50 100

[2401] Kochia 0 0 70 10 0 100 90 30 80 70 0 0 0 30

[2402] Morningglory

[2403] Pigweed 20 10 90 10 0 100 90 80 90 100 0 0 0 100

[2404] Ragweed 0 0 10 0 0 60 50 60 10 30 0 0 0 90

[2405] Ryegrass, Italian 0 0 0 0 0 60 0 10 30 10 0 0 0 50

[2406] Velvetleaf

[2407] Wheat 0 0 0 0 0 0 0 0 10 10 0 0 0 10

[2408] Table B Compounds

[2409] 125 g ai / ha 110 111 112 113 114 115 116 117 118 119 120 121 122 123Postemergence

[2410] Barnyardgrass 50 10 30 90 20 0 30 0 100 0 90 90 0 0

[2411] Blackgrass 40 40 20 90 40 0 30 0 100 0 90 80 0 0

[2412] Corn 10 10 20 30 50 0 40 0 100 0 40 40 0 0

[2413] Crabgrass, Large

[2414] Foxtail, Giant 70 60 60 90 60 0 90 0 100 10 90 90 0 0

[2415] Galium 70 20 50 100 100 0 70 0 100 60 100 100 20 0

[2416] Kochia 50 30 70 100 90 0 90 0 100 30 90 90 20 0

[2417] Morningglory

[2418] Pigweed 30 20 30 100 100 0 100 0 100 80 100 100 20 0

[2419] Ragweed 40 20 30 80 20 0 40 0 50 10 70 60 10 0

[2420] Ryegrass, Italian 0 0 0 70 60 0 30 0 80 0 90 70 0 0

[2421] Velvetleaf

[2422] Wheat 0 0 0 10 20 0 20 0 60 0 40 30 20 0

[2423] Table B Compounds

[2424] 125 g ai / ha 124 125 126 127 128 129 130 131 132 133 134 135 137 138

[2425] Postemergence

[2426] Barnyardgrass 20 30 100 100 10 10 100 90 50 60 20 10 0 0

[2427] Blackgrass 30 30 90 90 20 0 80 80 50 70 - - 0 0

[2428] Corn 10 10 70 50 10 10 40 40 30 30 10 10 0 0

[2429] Crabgrass, Large 10 10 - -

[2430] Foxtail, Giant 20 20 90 90 10 10 80 90 70 50 10 10 0 0

[2431] Galium 100 100 100 100 30 10 90 90 90 100 - - 0 0

[2432] Kochia 80 80 90 90 50 10 90 70 60 90 - - 0 0

[2433] Morningglory 10 20 - -

[2434] Pigweed 90 90 100 100 60 30 100 100 100 100 60 100 30 0

[2435] Ragweed 20 20 40 50 10 0 60 70 30 30 - - 0 0

[2436] Ryegrass, Italian 0 10 100 90 0 0 60 70 40 30 - - 0 0

[2437] Velvetleaf 40 40 - -

[2438] Wheat 0 0 40 20 0 0 40 30 10 10 10 0 0 0

[2439] Table B Compounds

[2440] 125 g ai / ha 139 140 141 142 143 144 145 146 147 149 150 151 152 153

[2441] Postemergence

[2442] Barnyardgrass 0 0 0 0 90 100 100 20 0 40 20 0 0 0

[2443] Blackgrass 0 0 0 0 60 90 90 30 0 60 10 0 0 40

[2444] Corn 0 0 30 20 30 90 70 0 0 20 10 0 0 30

[2445] Crabgrass, LargeFoxtail, Giant 0 0 0 0 80 100 90 20 0 60 10 0 0 20

[2446] Galium 0 0 0 10 100 100 100 50 0 90 10 0 0 90

[2447] Kochia 0 0 0 20 100 100 100 60 0 100 0 0 0 90

[2448] Morningglory

[2449] Pigweed 0 0 20 20 100 100 100 60 0 100 20 0 0 100

[2450] Ragweed 0 0 0 0 20 60 50 0 0 20 0 0 0 20

[2451] Ryegrass, Italian 0 0 0 0 50 100 80 0 0 20 0 0 0 30

[2452] Velvetleaf

[2453] Wheat 0 0 0 0 30 90 70 0 0 10 0 0 0 30

[2454] Table B Compounds

[2455] 125 g ai / ha 154 155 156 157 158 159 160 161 162 163 164 165 166 167

[2456] Postemergence

[2457] Barnyardgrass 0 0 0 20 60 0 0 0 90 0 0 20 0 0

[2458] Blackgrass 0 0 20 70 30 0 50 0 30 20 0 30 0 0

[2459] Corn 0 0 20 0 30 20 30 0 40 10 0 0 10 0

[2460] Crabgrass, Large

[2461] Foxtail, Giant 0 0 20 70 50 0 30 0 90 10 0 20 0 0

[2462] Galium 0 0 90 100 30 70 70 0 90 30 30 40 30 10

[2463] Kochia 0 0 90 90 70 20 40 0 100 50 0 40 0 10

[2464] Morningglory

[2465] Pigweed 0 0 90 100 80 90 90 0 100 30 30 50 30 10

[2466] Ragweed 0 0 20 10 0 0 0 0 40 30 30 60 30 0

[2467] Ryegrass, Italian 0 0 30 90 0 0 0 0 50 0 0 0 0 0

[2468] Velvetleaf

[2469] Wheat 0 0 20 50 20 20 20 0 30 0 0 0 0 10

[2470] Table B Compounds

[2471] 125 g ai / ha 168 169 170 173 174 175 176 177 178 179 180 181 182 183

[2472] Postemergence

[2473] Barnyardgrass 100 10 0 70 10 10 30 30 40 10 50 10 0 40

[2474] Blackgrass 90 50 50 70 50 0 30 30 40 80 90 0 0 80

[2475] Corn 100 10 20 40 0 0 30 10 20 10 20 10 10 10

[2476] Crabgrass, Large

[2477] Foxtail, Giant 100 30 30 90 0 0 50 40 60 40 80 0 0 60

[2478] Galium 100 100 80 90 70 40 90 100 100 100 100 10 30 100

[2479] Kochia 90 90 70 100 70 30 100 70 100 90 100 30 30 100

[2480] Morningglory

[2481] Pigweed 100 100 100 80 50 60 100 100 100 100 100 50 40 100Ragweed 90 20 10 60 30 30 20 20 10 10 50 10 0 20

[2482] Ryegrass, Italian 90 20 0 20 0 0 10 0 30 90 100 0 0 40

[2483] Velvetleaf

[2484] Wheat 100 0 0 0 0 0 0 0 10 40 60 0 0 10

[2485] Table B Compounds

[2486] 125 g ai / ha 184 185 187 188 189 190 196 197 198 199 200 201 202 203

[2487] Postemergence

[2488] Barnyardgrass 0 10 0 20 0 0 10 0 50 0 90 0 10 0

[2489] Blackgrass 10 0 0 20 0 0 0 0 40 - - - - -

[2490] Corn 10 0 0 30 0 0 0 0 20 0 50 0 0 0

[2491] Crabgrass, Large 0 100 0 10 0

[2492] Foxtail, Giant 10 10 0 20 0 0 10 0 90 0 100 0 30 0

[2493] Galium 70 40 0 50 0 0 100 50 100 - - - - -

[2494] Kochia 70 90 0 90 0 0 40 0 80 - - - - -

[2495] Morningglory 0 90 0 10 0

[2496] Pigweed 90 90 0 60 0 0 60 10 100 10 100 0 90 0

[2497] Ragweed 20 70 0 20 0 10 20 0 20 - - - - -

[2498] Ryegrass, Italian 0 0 0 0 0 0 0 0 50 - - - - -

[2499] Velvetleaf 0 100 0 10 0

[2500] Wheat 0 0 0 20 0 0 0 0 10 0 60 0 0 0

[2501] Table B Compounds

[2502] 125 g ai / ha 204 205 206 207 208 209 210 211 212 213 214 215 216 217

[2503] Postemergence

[2504] Barnyardgrass 0 0 0 0 0 0 0 10 30 0 0 20 10 0

[2505] Blackgrass - - - - - - 30 50 50 10 0 0 10 0

[2506] Corn 0 0 0 0 0 0 10 10 20 10 0 20 10 0

[2507] Crabgrass, Large 10 10 10 0 0 10

[2508] Foxtail, Giant 0 0 0 0 0 0 40 50 70 20 0 20 0 0

[2509] Galium - - - - - - 90 100 100 80 10 20 50 10

[2510] Kochia - - - - - - 80 90 100 100 0 0 20 10

[2511] Morningglory 0 0 20 10 0 30

[2512] Pigweed 50 60 40 70 20 90 80 50 100 80 10 20 30 10

[2513] Ragweed - - - - - - 30 30 60 60 0 0 0 10

[2514] Ryegrass, Italian - - - - - - 0 0 20 0 0 0 0 0

[2515] Velvetleaf 0 0 30 10 20 30

[2516] Wheat 0 0 0 0 0 0 20 0 10 10 0 0 0 0Table B Compounds

[2517] 125 g ai / ha 218 219 220 221 222 223 224 225 226 227 228 229 230 231

[2518] Postemergence

[2519] Barnyardgrass 0 0 40 90 0 10 50 0 70 60 70 70 60 10

[2520] Blackgrass 0 0 90 60 10 0 70 0 70 70 100 80 70 0

[2521] Corn 0 0 20 50 30 0 20 0 30 20 30 30 10 0

[2522] Crabgrass, Large

[2523] Foxtail, Giant 0 0 80 90 0 10 50 0 70 60 90 80 70 10

[2524] Galium 10 30 100 100 90 50 100 0 100 80 100 100 100 20

[2525] Kochia 0 0 100 100 30 10 100 0 100 80 100 100 100 40

[2526] Morningglory

[2527] Pigweed 40 10 100 90 100 60 100 0 100 90 100 100 90 40

[2528] Ragweed 0 30 10 50 20 10 100 0 40 30 40 100 100 0

[2529] Ryegrass, Italian 0 0 40 40 0 0 0 0 50 30 90 20 0 0

[2530] Velvetleaf

[2531] Wheat 0 0 50 30 20 0 0 0 50 20 50 40 10 0

[2532] Table B Compounds

[2533] 125 g ai / ha 232 233 234 236 237 238 239

[2534] Postemergence

[2535] Barnyardgrass 0 10 0 30 0 30 0

[2536] Blackgrass 0 10 10 40 0 0 0

[2537] Corn 0 10 10 30 0 20 20

[2538] Crabgrass, Large - - - - - - -

[2539] Foxtail, Giant 0 0 0 30 0 10 0

[2540] Galium 0 0 0 100 0 40 0

[2541] Kochia 0 0 0 90 0 80 0

[2542] Morningglory - - - - - - -

[2543] Pigweed 40 20 20 70 0 20 20

[2544] Ragweed 0 0 10 20 0 0 0

[2545] Ryegrass, Italian 0 0 0 20 0 0 0

[2546] Velvetleaf - - - - - - -

[2547] Wheat 0 0 0 20 0 0 0

[2548] Table B Compounds

[2549] 31 g ai / ha 15 38 70 73 89 90 91 96 97 103 104 105 106 107

[2550] Postemergence

[2551] Barnyardgrass 0 0 0 0 10 0 0 10 0 0 10 10 0 0

[2552] Blackgrass - 0 0 0 10 0 0 10 0 30 70 70 0 0Corn 0 0 0 0 10 0 0 0 0 0 10 10 0 0

[2553] Crabgrass, Large 0

[2554] Foxtail, Giant 0 0 0 0 10 0 0 0 0 40 20 40 0 0

[2555] Galium - 20 0 0 10 0 0 100 10 90 90 70 0 0

[2556] Kochia - 0 0 0 50 0 0 70 60 0 50 30 0 0

[2557] Morningglory 0

[2558] Pigweed 60 0 10 0 60 0 0 100 60 30 90 90 0 0

[2559] Ragweed - 0 0 0 10 0 0 50 20 20 10 10 0 0

[2560] Ryegrass, Italian - 0 0 0 0 0 0 30 0 0 0 0 0 0

[2561] Velvetleaf 0

[2562] Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2563] Table B Compounds

[2564] 31 g ai / ha 108 109 110 111 112 113 114 115 116 117 118 119 120 121

[2565] Postemergence

[2566] Barnyardgrass 0 60 0 0 10 60 10 0 10 0 70 0 50 50

[2567] Blackgrass 0 50 0 0 0 60 10 0 20 0 60 0 70 50

[2568] Corn 0 10 0 0 10 10 30 0 20 0 50 0 30 20

[2569] Crabgrass, Large

[2570] Foxtail, Giant 0 60 0 0 10 60 20 0 20 0 90 0 40 70

[2571] Galium 30 50 20 10 30 90 70 0 60 0 100 30 100 100

[2572] Kochia 0 0 10 20 60 100 70 0 90 0 100 0 90 90

[2573] Morningglory

[2574] Pigweed 0 80 10 0 30 100 100 0 100 0 100 40 100 100

[2575] Ragweed 0 60 30 10 20 50 0 0 20 0 30 10 40 50

[2576] Ryegrass, Italian 0 10 0 0 0 20 10 0 0 0 20 0 30 50

[2577] Velvetleaf

[2578] Wheat 0 0 0 0 0 0 10 0 10 0 20 0 0 0

[2579] Table B Compounds

[2580] 31 g ai / ha 122 124 125 126 127 128 129 130 131 132 133 140 141 142

[2581] Postemergence

[2582] Barnyardgrass 0 0 10 80 30 0 0 40 50 20 20 0 0 0

[2583] Blackgrass 0 0 10 60 30 0 0 50 50 20 30 0 0 0

[2584] Corn 0 0 0 20 20 0 0 20 20 10 10 0 0 0

[2585] Crabgrass, Large

[2586] Foxtail, Giant 0 0 0 60 50 0 0 50 50 30 20 0 0 0

[2587] Galium 10 60 50 90 80 10 10 80 80 80 70 0 0 0

[2588] Kochia 10 40 60 90 90 20 0 90 60 30 90 0 0 0Morningglory

[2589] Pigweed 20 70 70 100 100 20 10 90 100 70 90 0 0 10

[2590] Ragweed 0 10 0 30 20 0 0 40 40 20 20 0 0 0

[2591] Ryegrass, Italian 0 0 0 40 30 0 0 30 40 10 10 0 0 0

[2592] Velvetleaf

[2593] Wheat 0 0 0 10 10 0 0 30 0 0 0 0 0 0

[2594] Table B Compounds

[2595] 31 g ai / ha 143 144 145 146 147 149 150 154 155 162 163 164 165 166

[2596] Postemergence

[2597] Barnyardgrass 10 30 40 0 0 10 0 0 0 10 0 0 0 0

[2598] Blackgrass 30 80 70 0 0 10 0 0 0 30 20 0 20 0

[2599] Corn 40 30 30 0 0 10 0 0 0 20 0 0 0 0

[2600] Crabgrass, Large

[2601] Foxtail, Giant 10 80 70 0 0 10 0 0 0 10 0 0 10 0

[2602] Galium 50 100 100 30 0 90 0 0 0 90 20 10 20 20

[2603] Kochia 100 100 100 50 0 90 0 0 0 90 10 0 20 0

[2604] Morningglory

[2605] Pigweed 90 100 100 30 0 90 10 0 0 100 20 0 30 20

[2606] Ragweed 0 20 20 0 0 10 0 0 0 0 30 20 30 10

[2607] Ryegrass, Italian 0 20 20 0 0 0 0 0 0 0 0 0 0 0

[2608] Velvetleaf

[2609] Wheat 20 30 20 0 0 0 0 0 0 20 0 0 0 0

[2610] Table B Compounds

[2611] 31 g ai / ha 173 174 175 176 177 178 187 188 189 196 197 198 210 211

[2612] Postemergence

[2613] Barnyardgrass 30 0 0 10 10 0 0 0 0 0 0 10 0 0

[2614] Blackgrass 30 40 0 0 0 10 0 0 0 0 0 10 10 10

[2615] Corn 10 0 0 10 0 0 0 0 0 0 0 10 0 0

[2616] Crabgrass, Large

[2617] Foxtail, Giant 30 0 0 20 10 10 0 0 0 0 0 30 0 10

[2618] Galium 50 60 20 30 50 80 0 0 0 60 10 100 50 60

[2619] Kochia 70 60 0 30 30 80 0 0 0 0 0 80 50 40

[2620] Morningglory

[2621] Pigweed 60 50 50 90 50 100 0 0 0 20 10 100 50 20

[2622] Ragweed 40 20 20 10 10 10 0 0 0 10 0 10 10 0

[2623] Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 10 0 0Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2624] Table B Compounds

[2625] 31 g ai / ha 212 213 214 216 218 219 220 221 222 223 224 225 226 227

[2626] Postemergence

[2627] Barnyardgrass 0 0 0 10 0 0 10 10 0 0 30 0 10 10

[2628] Blackgrass 10 0 0 0 0 0 60 30 0 0 40 0 10 10

[2629] Corn 10 0 0 0 0 0 10 20 0 0 0 0 20 10

[2630] Crabgrass, Large

[2631] Foxtail, Giant 10 0 0 0 0 0 30 10 0 0 20 0 10 10

[2632] Galium 60 50 0 20 0 20 90 90 30 30 80 0 60 70

[2633] Kochia 90 60 0 10 0 0 90 80 20 0 70 0 100 40

[2634] Morningglory

[2635] Pigweed 90 30 0 10 0 10 100 90 30 20 70 0 50 60

[2636] Ragweed 20 10 0 0 0 20 0 10 0 0 50 0 10 10

[2637] Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 10 0

[2638] Velvetleaf

[2639] Wheat 0 0 0 0 0 0 10 20 0 0 0 0 0 0

[2640] Table B Compounds

[2641] 31 g ai / ha 228 229 230 231 232 233 234 236 237 238 239

[2642] Postemergence

[2643] Barnyardgrass 30 20 0 0 0 0 0 0 0 0 0

[2644] Blackgrass 60 30 20 0 0 0 0 20 0 0 0

[2645] Corn 20 0 0 0 0 0 0 0 0 0 0

[2646] Crabgrass, Large

[2647] Foxtail, Giant 40 50 0 0 0 0 0 0 0 0 0

[2648] Galium 100 80 80 0 0 0 0 30 0 0 0

[2649] Kochia 100 90 80 20 0 0 0 20 0 20 0

[2650] Morningglory

[2651] Pigweed 100 70 60 20 10 0 0 30 0 10 0

[2652] Ragweed 30 100 70 0 0 0 0 0 0 0 0

[2653] Ryegrass, Italian 20 0 0 0 0 0 0 0 0 0 0

[2654] Velvetleaf

[2655] Wheat 0 0 0 0 0 0 0 0 0 0 0

[2656] Table B Compounds

[2657] 1000 g ai / ha 1 2 3 5 6 7 8 9 10 12 23 31 33 34

[2658] Preemergence

[2659] Barnyardgrass 80 0 60 0 0 10 30 20 0 20 40 0 0 0Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2660] Crabgrass, Large 100 10 40 0 0 40 80 70 10 80 100 80 80 10

[2661] Foxtail, Giant 100 10 70 0 0 20 60 60 0 90 100 30 10 10

[2662] Kochia

[2663] Morningglory 20 0 0 0 0 0 0 0 0 0 0 0 0 0

[2664] Pigweed 100 100 50 90 70 40 100 90 10 90 100 0 40 100

[2665] Ragweed

[2666] Ryegrass, Italian

[2667] Velvetleaf 80 20 90 20 20 10 30 10 0 70 80 0 0 10

[2668] Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2669] Table B Compounds

[2670] 1000 g ai / ha 35 36 40 46 55 57 61 148 171 172 186 191 192 193

[2671] Preemergence

[2672] Barnyardgrass 100 30 50 80 100 100 20 0 70 0 20 100 100 100

[2673] Corn 30 0 0 0 - - 0 - - - - - - -

[2674] Crabgrass, Large 100 100 70 100 - - 50 - - - - - - -

[2675] Foxtail, Giant 100 90 100 100 100 100 40 0 100 30 100 100 100 100

[2676] Kochia - - - - 100 100 - 0 90 20 100 100 100 100

[2677] Morningglory 90 10 0 10 - - 0 - - - - - - -

[2678] Pigweed 10 100 100 100 100 90 90 0 100 90 100 100 100 100

[2679] Ragweed - - - - 100 90 - - 0 0 70 90 20 80

[2680] Ryegrass, Italian - - - - 100 80 - 0 10 0 0 90 50 0

[2681] Velvetleaf 100 - 90 20 - - 50 - - - - - - -

[2682] Wheat 60 0 0 10 - - 0 - - - - - - -

[2683] Table B Compounds Table B Compounds

[2684] 1000 g ai / ha 194 195 235 1000 g ai / ha 194 195 235 Preemergence Preemergence

[2685] Barnyardgrass 100 40 0 Pigweed 100 60 0 Corn Ragweed 30 10 0

[2686] Crabgrass, Large Ryegrass, Italian 50 0 0 Foxtail, Giant 100 30 Velvetleaf

[2687] Kochia 100 0 Wheat

[2688] Morningglory

[2689] Table B Compounds

[2690] 500 g ai / ha 10 11 13 14 16 17 18 19 20 21 22 23 24 Preemergence

[2691] Barnyardgrass 0 0 0 0 0 0 0 50 0 30 80Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 40

[2692] Crabgrass, Large 80 0 0 10 20 10 10 20 50 70 100 0 80 100

[2693] Foxtail, Giant 50 0 0 10 30 10 0 10 70 60 100 0 70 90

[2694] Kochia

[2695] Morningglory 0 0 - 0 0 - - 0 0 0 0 0 0 0

[2696] Pigweed 70 30 30 80 100 20 0 30 20 20 90 0 90 40

[2697] Ragweed

[2698] Ryegrass, Italian

[2699] Velvetleaf 30 0 10 10 20 20 10 0 0 20 20 0 50 0

[2700] Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2701] Table B Compounds

[2702] 500 g ai / ha 25 26 27 28 29 30 32 37 41 42 43 44 45 47

[2703] Preemergence

[2704] Barnyardgrass 70 30 80 60 0 0 90 0 0 70 20 10 0 0

[2705] Corn 0 0 0 0 0 0 0 - 0 0 0 0 0 -

[2706] Crabgrass, Large 100 100 100 100 30 20 100 - 10 90 30 70 20 -

[2707] Foxtail, Giant 90 90 90 90 10 10 100 0 20 100 70 10 20 30

[2708] Kochia - - - - - - - 0 - - - - - 70

[2709] Morningglory 10 0 0 0 0 0 30 - 0 0 10 0 0 -

[2710] Pigweed 100 100 100 80 50 30 100 40 0 90 0 10 0 60

[2711] Ragweed - - - - - - - 0 - - - - - 60

[2712] Ryegrass, Italian - - - - - - - 0 - - - - - 0

[2713] Velvetleaf 100 80 60 60 0 0 100 - 0 70 10 20 0 -

[2714] Wheat 0 0 0 0 0 0 10 - 0 0 0 0 0 -

[2715] Table B Compounds

[2716] 500 g ai / ha 48 49 50 51 52 53 54 58 59 60 62 63 64 123

[2717] Preemergence

[2718] Barnyardgrass 40 0 10 10 0 100 100 100 10 100 100 100 100 0

[2719] Corn 20 30 20 -

[2720] Crabgrass, Large 100 100 100 -

[2721] Foxtail, Giant 50 20 50 60 0 100 100 100 60 100 100 100 100 0

[2722] Kochia 80 70 60 70 30 100 100 100 0 100 - - - 0

[2723] Morningglory 90 60 60 -

[2724] Pigweed 100 30 100 100 50 100 100 100 30 100 100 100 100 0

[2725] Ragweed 60 0 50 50 0 50 70 80 0 50 - - - 0

[2726] Ryegrass, Italian 50 0 50 0 0 40 60 20 0 30 - - - 0

[2727] Velvetleaf 100 90 90 -Wheat 30 40 30 -

[2728] Table B Compounds

[2729] 500 g ai / ha 134 135 136 137 138 139 151 152 153 156 157 158 159 160

[2730] Preemergence

[2731] Barnyardgrass 90 60 100 10 0 0 0 0 100 20 80 100 60 80

[2732] Corn 60 0 40

[2733] Crabgrass, Large 100 100 100

[2734] Foxtail, Giant 100 100 100 0 0 0 0 0 100 80 100 100 90 100

[2735] Kochia - - - 10 0 0 0 0 100 40 100 100 30 90

[2736] Morningglory 80 10 90

[2737] Pigweed 100 100 100 20 0 0 0 0 100 100 100 100 100 100

[2738] Ragweed - - - 0 0 0 0 0 40 0 70 20 0 0

[2739] Ryegrass, Italian - - - 0 0 0 0 0 20 0 90 20 0 0

[2740] Velvetleaf 100 60 100

[2741] Wheat 20 0 30

[2742] Table B Compounds

[2743] 500 g ai / ha 161 167 168 169 170 179 180 181 182 183 184 185 190 199

[2744] Preemergence

[2745] Barnyardgrass 0 10 100 30 20 90 80 10 20 80 90 70 0 0

[2746] Corn 0

[2747] Crabgrass, Large 10

[2748] Foxtail, Giant 0 30 100 90 90 100 100 40 40 90 90 90 10 0

[2749] Kochia 0 30 100 90 80 100 100 0 30 100 100 100 0 -

[2750] Morningglory 0

[2751] Pigweed 0 20 100 100 100 100 100 80 40 100 100 100 10 30

[2752] Ragweed 0 10 80 20 60 40 70 0 10 60 50 90 0 -

[2753] Ryegrass, Italian 0 0 100 20 20 40 70 0 10 40 10 0 0 -

[2754] Velvetleaf 10

[2755] Wheat 0

[2756] Table B Compounds

[2757] 500 g ai / ha 200 201 202 203 204 205 206 207 208 209 215 217

[2758] Preemergence

[2759] Barnyardgrass 100 0 80 0 30 10 30 90 0 10 90 10

[2760] Corn 100 0 0 0 0 0 0 0 0 0 - -

[2761] Crabgrass, Large 100 0 100 0 100 70 60 100 0 100 - -

[2762] Foxtail, Giant 100 0 100 0 100 70 60 100 0 100 90 30Morningglory 100 0 20 0 10 0 0 30 0 0 - -

[2763] Pigweed 100 0 100 0 100 90 80 100 90 100 90 70

[2764] Ragweed 0 0

[2765] Ryegrass, Italian 0 10

[2766] Velvetleaf 90 0 60 0 60 0 40 30 10 0 - -

[2767] Wheat 90 0 20 0 0 0 0 0 0 0 - -

[2768] Table B Compounds

[2769] 125 g ai / ha 4 10 11 13 14 15 16 17 18 19 20 21 22 23

[2770] Preeraergence

[2771] Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2772] Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2773] Crabgrass, Large 10 0 0 0 0 0 0 0 0 0 10 60 0 40

[2774] Foxtail, Giant 10 0 0 0 0 0 0 0 0 0 10 70 0 20

[2775] Kochia

[2776] Morningglory 0 0 0 0 0 0 - - 0 0 0 0 0 0

[2777] Pigweed 30 0 0 0 0 0 0 0 0 0 0 30 0 50

[2778] Ragweed

[2779] Ryegrass, Italian

[2780] Velvetleaf 0 0 10 0 0 0 0 0 0 0 0 0 0 10

[2781] Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0

[2782] Table B Compounds

[2783] 125 g ai / ha 24 25 26 27 28 29 30 32 38 41 42 43 44 45

[2784] Preeraergence

[2785] Barnyardgrass 10 10 0 10 0 0 0 90 0 0 20 0 0 0

[2786] Corn 0 0 0 0 0 0 0 0 - 0 0 0 0 0

[2787] Crabgrass, Large 100 50 10 80 40 10 0 100 - 0 50 0 10 0

[2788] Foxtail, Giant 20 40 0 60 30 0 0 90 0 0 70 0 0 0

[2789] Kochia - - - - - - - - 0 - - - - -

[2790] Morningglory 0 0 0 0 0 0 0 0 - 0 0 0 0 0

[2791] Pigweed 0 60 0 80 40 20 0 100 40 0 50 0 0 0

[2792] Ragweed - - - - - - - - 0 - - - - -

[2793] Ryegrass, Italian - - - - - - - - 0 - - - - -

[2794] Velvetleaf 0 10 10 20 0 0 0 90 - 0 50 0 0 0

[2795] Wheat 0 0 0 0 0 0 0 0 - 0 0 0 0 0

[2796] Table B Compounds

[2797] 125 g ai / ha 47 48 49 50 51 52 53 54 58 59 60 62 63 64

[2798] PreemergenceBarnyardgrass 0 0 0 0 0 0 90 60 60 0 80 80 90 60

[2799] Corn 0 10 0

[2800] Crabgrass, Large 100 100 100

[2801] Foxtail, Giant 10 10 0 0 10 0 90 100 90 10 80 100 100 90

[2802] Kochia 60 60 0 10 10 0 100 80 80 0 90 - - -

[2803] Morningglory 60 30 0

[2804] Pigweed 30 80 20 60 50 40 100 100 100 0 100 100 100 100

[2805] Ragweed 10 50 0 0 50 0 10 60 70 0 20 - - -

[2806] Ryegrass, Italian 0 40 0 20 0 0 10 30 0 0 0 - - -

[2807] Velvetleaf 90 70 80

[2808] Wheat 20 20 0

[2809] Table B Compounds

[2810] 125 g ai / ha 70 73 89 90 91 96 97 103 104 105 106 107 108 109

[2811] Preemergence

[2812] Barnyardgrass 0 0 70 0 0 20 0 50 80 90 0 0 0 100

[2813] Corn

[2814] Crabgrass, Large

[2815] Foxtail, Giant 0 0 90 0 0 40 30 90 100 100 0 0 0 100

[2816] Kochia 0 0 0 0 0 70 30 10 10 10 0 0 0 30

[2817] Morningglory

[2818] Pigweed 0 0 100 20 0 100 50 100 100 100 0 0 0 100

[2819] Ragweed 0 0 0 0 0 0 0 10 0 0 0 0 0 70

[2820] Ryegrass, Italian 0 0 0 0 0 0 0 0 10 20 0 0 0 10

[2821] Velvetleaf

[2822] Wheat

[2823] Table B Compounds

[2824] 125 g ai / ha 110 111 112 113 114 115 116 117 118 119 120 121 122 123

[2825] Preemergence

[2826] Barnyardgrass 40 20 30 100 20 0 30 0 100 0 100 90 0 0

[2827] Corn

[2828] Crabgrass, Large

[2829] Foxtail, Giant 70 50 70 100 30 0 90 0 100 50 100 100 0 0

[2830] Kochia 0 10 50 100 20 0 60 0 100 10 90 100 10 0

[2831] Morningglory

[2832] Pigweed 70 80 70 100 80 0 100 0 100 50 100 100 50 0

[2833] Ragweed 0 10 0 70 20 0 20 0 30 0 30 20 0 0

[2834] Ryegrass, Italian 0 0 10 60 20 0 20 0 80 0 90 80 0 0Compounds

[2835] 125 g ai / ha 124 125 126 127 128 129 130 131 132 133 134 135 137 138

[2836] Preemergence

[2837] Barnyardgrass 30 50 100 90 0 0 90 100 60 70 70 10 0 0

[2838] Corn 20 0 - -

[2839] Crabgrass, Large 100 80 - -

[2840] Foxtail, Giant 100 90 100 100 10 0 100 100 90 90 90 60 0 0

[2841] Kochia 60 40 90 90 0 0 70 10 0 90 - - 0 0

[2842] Morningglory 10 0 - -

[2843] Pigweed 100 80 100 100 40 0 100 100 100 100 100 90 0 0

[2844] Ragweed 10 0 10 30 0 0 20 60 40 10 - - 0 0

[2845] Ryegrass, Italian 10 10 100 90 0 0 50 90 30 50 - - 0 0

[2846] Velvetleaf 40 20 - -

[2847] Wheat 20 0 - -

[2848] Table B Compounds

[2849] 125 g ai / ha 139 140 141 142 143 144 145 146 147 149 150 151 152 153

[2850] Preemergence

[2851] Barnyardgrass 0 0 0 0 90 100 100 30 0 70 20 0 0 0

[2852] Corn

[2853] Crabgrass, Large

[2854] Foxtail, Giant 0 0 0 20 100 100 100 20 0 100 20 0 0 30

[2855] Kochia 0 0 0 0 90 100 100 0 0 80 0 0 0 20

[2856] Morningglory

[2857] Pigweed 0 0 0 0 100 100 100 70 0 100 20 0 0 100

[2858] Ragweed 0 0 0 0 30 50 20 0 0 0 0 0 0 0

[2859] Ryegrass, Italian 0 0 0 0 60 90 40 0 0 10 0 0 0 0

[2860] Velvetleaf

[2861] Wheat

[2862] Table B Compounds

[2863] 125 g ai / ha 154 155 156 157 158 159 160 161 162 163 164 165 166 167

[2864] Preemergence

[2865] Barnyardgrass 0 0 0 20 90 0 0 0 100 0 0 10 0 0

[2866] Corn

[2867] Crabgrass, Large

[2868] Foxtail, Giant 0 0 20 80 90 20 50 0 100 0 0 10 0 0Kochia 0 0 20 100 100 0 30 0 70 0 0 60 0 0

[2869] Morningglory

[2870] Pigweed 0 0 80 100 90 40 90 0 100 30 30 80 60 0

[2871] Ragweed 0 0 0 20 0 0 0 0 20 40 0 50 20 0

[2872] Ryegrass, Italian 0 0 0 20 0 0 0 0 40 0 0 0 0 0

[2873] Velvetleaf

[2874] Wheat

[2875] Table B Compounds

[2876] 125 g ai / ha 168 169 170 173 174 175 176 177 178 179 180 181 182 183 Preemergence

[2877] Barnyardgrass 100 20 0 90 0 0 50 50 70 10 20 0 0 30 Corn

[2878] Crabgrass, Large

[2879] Foxtail, Giant 100 50 60 100 40 0 90 70 90 80 90 0 0 80 Kochia 100 70 30 100 0 0 20 20 20 100 100 0 0 80

[2880] Morningglory

[2881] Pigweed 100 100 100 100 80 70 90 90 100 100 100 10 0 90

[2882] Ragweed 70 10 20 70 0 0 0 0 0 10 50 0 0 0

[2883] Ryegrass, Italian 80 0 0 20 0 0 10 0 10 20 20 0 0 20

[2884] Velvetleaf

[2885] Wheat

[2886] Table B Compounds

[2887] 125 g ai / ha 184 185 187 188 189 190 196 197 198 199 200 201 202 203 Preemergence

[2888] Barnyardgrass 10 20 0 20 0 0 10 0 40 0 100 0 10 0 Corn - - - - - - - - - 0 20 0 0 0

[2889] Crabgrass, Large - - - - - - - - - 0 100 0 90 0 Foxtail, Giant 20 30 0 40 0 0 20 0 90 0 100 0 70 0 Kochia 20 40 0 30 0 0 0 0 30 - - - - -

[2890] Morningglory - - - - - - - - - 0 20 0 0 0

[2891] Pigweed 80 90 0 100 0 0 10 0 100 0 100 0 100 0

[2892] Ragweed 0 10 0 0 0 0 0 0 10 - - - - -

[2893] Ryegrass, Italian 0 0 0 0 0 0 0 0 20 - - - - -

[2894] Velvetleaf - - - - - - - - - 0 80 0 0 0

[2895] Wheat - - - - - - - - 0 20 0 0 0

[2896] Table B Compounds

[2897] 125 g ai / ha 204 205 206 207 208 209 210 211 212 213 214 215 216 217Preemergence

[2898] Barnyardgrass 0 0 0 10 0 0 80 50 60 40 0 40 10 0

[2899] Corn 0 0 0 0 0 0

[2900] Crabgrass, Large 90 30 10 100 0 70

[2901] Foxtail, Giant 60 20 10 70 0 30 90 100 100 80 0 20 0 0

[2902] Kochia - - - - - - 90 80 90 50 0 0 0 0

[2903] Morningglory 0 0 0 0 0 0

[2904] Pigweed 100 10 50 90 0 90 100 100 100 100 0 20 0 10

[2905] Ragweed - - - - - - 20 30 40 0 0 0 0 0

[2906] Ryegrass, Italian - - - - - - 10 0 40 0 0 0 0 0

[2907] Velvetleaf 0 0 30 0 0 0

[2908] Wheat 0 0 0 0 0 0

[2909] Table B Compounds

[2910] 125 g ai / ha 218 219 220 221 222 223 224 225 226 227 228 229 230 231

[2911] Preemergence

[2912] Barnyardgrass 50 0 100 90 0 0 50 0 100 50 100 90 70 10

[2913] Corn

[2914] Crabgrass, Large

[2915] Foxtail, Giant 60 0 100 90 0 0 90 0 100 90 100 90 90 10

[2916] Kochia 0 0 90 70 0 0 90 0 90 50 100 100 100 0

[2917] Morningglory

[2918] Pigweed 90 0 100 100 90 10 100 0 100 80 100 100 100 20

[2919] Ragweed 0 0 10 0 0 0 - 0 20 0 30 90 80 0

[2920] Ryegrass, Italian 0 0 30 40 0 0 0 0 20 10 70 30 0 0

[2921] Velvetleaf

[2922] Wheat

[2923] Table B Compounds

[2924] 125 g ai / ha 232 233 234 236 237 238 239

[2925] Preemergence

[2926] Barnyardgrass 20 0 0 80 0 40 0

[2927] Corn - - - - - - -

[2928] Crabgrass, Large - - - - - - -

[2929] Foxtail, Giant 10 0 0 90 0 20 0

[2930] Kochia 0 0 0 100 0 0 0

[2931] Morningglory - - - - - - -

[2932] Pigweed 30 0 0 100 0 10 0

[2933] Ragweed 0 0 - 0 0 0 0Ryegrass, Italian 0 0 0 30 0 0 0

[2934] Velvetleaf - - - - - - -

[2935] Wheat - - - - - - -

[2936] Table B Compounds

[2937] 31 g ai / ha 15 38 70 73 89 90 91 96 97 103 104 105 106 107

[2938] Preemergence

[2939] Barnyardgrass 0 0 0 0 10 0 0 0 0 0 20 20 0 0

[2940] Corn 0

[2941] Crabgrass, Large 0

[2942] Foxtail, Giant 0 0 0 0 40 0 0 10 10 50 40 70 0 0

[2943] Kochia - 0 0 0 0 0 0 50 0 0 0 0 0 0

[2944] Morningglory 0

[2945] Pigweed 0 0 0 0 100 0 0 90 20 100 80 100 0 0

[2946] Ragweed - 0 0 0 0 0 0 0 0 0 0 0 0 0

[2947] Ryegrass, Italian - 0 0 0 0 0 0 0 0 0 0 0 0 0

[2948] Velvetleaf 0

[2949] Wheat 0

[2950] Table B Compounds

[2951] 31 g ai / ha 108 109 110 111 112 113 114 115 116 117 118 119 120 121

[2952] Preemergence

[2953] Barnyardgrass 0 40 0 0 10 70 0 0 0 0 70 0 90 70

[2954] Corn

[2955] Crabgrass, La...

Claims

AMENDED CLAIMSreceived by the International Bureau on 20 April 2015 (20.04.2015)CLAIMSWhat is claimed is:l . A compound selected from Formula 1, N-oxides and salts thereof,Q is a 5- or 6-membered aromatic heterocylie ring, bound to the remainder ofFormula 1 through a carbon atom, and optionally substituted with 1 to 4 R1; Z is O or S;each R1is independently halogen, cyano, nitro, SF5, CHO, C(=0)NH2, C(=S)NII2, S02NH2, Cj-C4alkyl, C2-C4alkenyl, C C4alkynyl, CrC4haloalkyl, C2-C4aloalkenyl, C2-C4haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C4-C8alkylcycloalkyl, C4C8cycloalkylalkyl, C2-C6alkylcarbonyl, C -C6haloalkylcarbonyl, C2--C6alkoxycarbonyl, C3-C7 cycloalkylcarbonyl, C2-C8alkylaminocarbonyl, Cj-C^ dialkylaitunocatbonyl, CrC4alkoxy, C3-C4 alkenyloxy, C3-C4alkynyloxy, Cj-C4haloalkoxy, C3-C4 haloalkenyloxy, C3-C4haloalkynyloxy, cycloalkoxy, C3-C6halocycloalkoxy, C4- Cgcycloalkylaikoxy, C2-C6alkoxyalkyl, C -C6haloalkoxyalkyl, C2-C6alkoxyhaloalkyl, C2-C6alkoxyalkoxy, C2-C4 alkylcarbonyloxy, C2-C6cyanoalkyl, C2-C6cyanoalkoxy, C\-C hydroxyalkyl, C2-C4alkylfhioalkyl, SOnR1A, Si(CH3)3oror a phenyl ring optionally substituted with up to 5 substituents independently selected from R1 Cor a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R1C011 carbon atom ring members and R1Don nitrogen atom ring members;R2is halogen, cyano, nitro, C [ -C4alkoxy, C1 -C4 allcyl, C2-C6alkenyl, C2-C6alkynyl, SOuR2A, C1 -C4 haloalkyl or C3-C6cycloalkyl;each R3is independently halogen, cyano, hydroxy, nitro, amino, CHO, C(-0)NH2, C(=S)NH2, S02NH2, C 1 -C4 alkyl, C2-C4alkenyl, C2-C4alkynyl, C,-C4haloall yl, C2-C haloalkenyl, C2-C haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C -C8alkylcycloalkyl, C4-C3cycloall ylallcyl, C -C6alkylcarbonyl, C2-C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C3-C7cycloalkylcarbonyl, CrC4alkoxy, C3-C4 alkenyloxy, C3-C4 alkytiyloxy, C^ haloalkoxy, C3-C4 haloalkenyloxy, C3-C4haloall ynyloxy, C3--C6cycloalkoxy, C3C6halocycloalkoxy, C4 Cg cycloallcyl alkoxy, C2-C6alkoxyalkyl, C2-C6haloalkoxyalkyl, C2-C¾ alkoxyhaloalkyl, C2-C6alkoxyalkoxy, C2-C4alkylcarbonyloxy, C2-C6cyanoalkyl, C2-Cg cyanoalkoxy, C2-C4alkylthioalkyl, Si(CH3)3)OCSi(CH3)3, C(-0)N(R3A)(R3B))C(=NOR3C)H, C(=NR3D)H, SOnR3E; or a phenyl ring optionally substituted with up to 5 substitiients independently selected from R3F; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substitiients independently selected from R3Fon carbon atom ring members and R3Gon nitrogen atom ring members; or pyrimidinyloxy;m is O, 1, 2 or 3;each n is independently 0, 1 or 2;each R1A, R2Aand R3Eis independently CrC4alkyl, CrC4haloalkyl, C C4alkylamino or C2-C6dialkylamino;each R1Bis independently H or C1 -C4 alkyl;each R1Cis independently hydroxy, halogen, cyano, nitro, C]-C6alkyl, C]-C6haloalkyl, Cj C6alkoxy or haloalkoxy;each R1Dis independently cyano, Cj- C6alkyl, C|-Cg haloallcy], Ci~C^ alkoxy or C2-C6alkylcarbonyl;each R3Ais independently C1-C4 alkyl or CJ-C4 haloalkyl;each R3Bis independently H, C]-C4alkyl or C C4haloalkyl;each R3Cis independently H or[-C^ alkyl;each R3Dis independently II, amino, C^C^ alkyl or C]-C4all ylamino;each R3Fis independently hydroxy, halogen, cyano, nitro, Cj-Cg alkyl, Cj-C6haloalkyl, C|C6alkoxy or Cj-C6haloalkoxy; andeach R3Gis independently cyano, Cj- C6alkyl, Cj-C6haloalkyl, Cj-Cg alkoxy or C2-C(5 alkylcarbonyl;2. A compound of Claim 1 whereinQ is selected fromQ-l Q-2 Q-3 Q-4 Q-5190Q-41 Q-42 Q-44wherein r is 0, 1 , 2 or 3; and s is 0 or I;each R1is independently halogen, cyano, SF5, CHO, CJ-C alkyl, C2-C4alkenyl, C2-C4 allcynyl, C^ haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C2-C6alkylcarbonyl, C2C6haloalkylcarbonyl, C2-C<5 alkoxycarbonyl, C^C^ alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6alkoxyalkyl, C2-C6haloallcoxyalkyl, C2-C6cyanoalkyl, CrC4hydroxyalkyl, C2-C4alkylthioalkyl or SOnR!A;R3is independently halogen, cyano, CHO, C C4alkyl, C2-C4alkenyl, C2-C4allcynyl, C]-C4 haloalkyl, C2-C4haloalkenyl, C2-C4haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C^-Cg alkylcycloalkyl, C2- ; alkylcarbonyl, C2-Q, haloalkylcarbonyl, C2-C6alkoxycarbonyl, Q -C4 alkoxy, C3-C4alkenyloxy, C3- C4alkynyloxy, C]-C4haloalkoxy, C3-C4haloalkenyloxy, C3-C4haloalkynyloxy, C3-C6cycloalkoxy, C3-C6halocycloalkoxy, C2-C6alkoxyalkyl, C -C6haloalkoxyalkyl, C2-C4alkylcarbonyloxy, C2-C6cyanoalkyl, C(=0)N(R3A)(R3B)>C(=NOR3C)H, SOnR E;0r a phenyl ring optionally substituted with up to 5 substituents independently selected from R3F; or a 5- or 6-membered heteroaroniatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituentsindependently selected from R3Fon carbon atom ring members and R3Gon nitrogen atom ring members;Z is O; andm is 0, 1 or 2.

3. A compound of Claim 2 whereineach R1is independently halogen, cyano, CHO, C1-C4 alkyl, C2-C4 alkenyl, C2-C4alkynyl, C1-C4 haloalkyl, C2-C4haloalkenyl, C2-C4 haloalkynyl, C C4alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, C1-C4 haloalkoxy, C3-C4 haloalkenyloxy, C3-C4 haloalkynyloxy, C2-C6alkoxyalkyl, C2-C6haloalkoxyalkyl, Cj-C4hydroxyalkyl, C2-C4alkylthioalkyl or SOnRlA;R2is halogen, Cj-C4alkyl or Cj -C4haloalkyl;each R3is independently halogen, cyano, CHO, Cj-C4alkyl, C2-C4 alkenyl, C2-C4alkynyl, ^-C^ haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C2-Cg alkylcarbonyl, C2-C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C]-C4alkoxy, C]-C4 haloalkoxy, C2-C(ialkoxyalkyl, C2-C6haloalkoxyalkyl, C2-C6cyanoalkyl, SOnR3E; or a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R31*on carbon atom ring members and R3Gon nitrogen atom ring members; andm is 0 or 1.

4. A compound of Claim 3 whereinQ is selected from Q-7 through Q-24;each R1is independently halogen, cyano, Cj-C4alkyl, C1-C4 haloallcyl, Cj-C4alkoxy,CrC haloalkoxy or SOnRIA;R2is halogen or CJ-C4 alkyl;each R3is independently halogen, cyano, CJ-C4 alkyl, C2-C4alkenyl, C2-C4 allcynyl, C]-C4haloalkyl, C2-C6alkylcarbonyl, C2-C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C[-C^ alkoxy, Cj-C4haloalkoxy, C2-C6alkoxyalkyl or C2-C6haloalkoxyalkyl; andeach R1Ais independently CpC4alkyl or ^ -C^ haloalkyl.

5. A compound of Clai m 4 whereinQ is selected from Q-16 and Q-18;each R1is independently halogen, Cj-C^ alkyl, C - ^ haloalkyl or C]-C4 haloalkoxy; R2is halogen or CH3; andeach R3is independently halogen, cyano, -C alkyl or Cj-C4 haloalkyl.

6. A compound of Claim 3 whereinQ is selected from Q-43, Q-44, Q-45, Q-48, Q-4 and Q-50;each R1is independently halogen, cyano, Cj -C4 alkyl, C1 -C4 haloaJkyl, C C alkoxy, Cj-C4haloalkoxy or SOnR1A;R2is halogen or C1-C4 alkyl;each R3is independently halogen, cyano,alkyl, C2-C4alkenyl, C2-C4 alkynyl, C C4haloalkyl, C2-C6alkylcarbonyl, C2C6haloalkylcarbonyl, C2-C6alkoxycavbonyl, Cj-C4alkoxy, C1-C4 haloalkoxy, C2-Cg alkoxyalkyl or C2-Cg haloalkoxyalkyl; andeach RIAis independently CrC4all y] or Cj-C4haloalkyl.

7. A compound of Claim 6 whereinQ is selected from Q-43, Q-44 and Q-45;each R1is independently halogen, Cj-C4alkyl, -C4 haloalkyl or C1-C4 haloalkoxy; R2is halogen or CH3; andeach R3is independently halogen, cyano, C1-C4 alkyl or Cj-C4haloalkyl.

8. A compound of Claim 1 selected from the group consisting of5-chloro-2-[2-(5-chloro-2-pyridinyl)phenoxy]pyrimidine,5-chloro-2-t2-[5-(fluot iuethyl)-3-isoxazolyl]phenoxy]pyrimidiiie,2-[2-(3-biOmo-5-isoxazolyl)phenoxy]-5-chloiOpyrimicline,5-c oro-2-[2-(5-(lrilluoiOmethyl)-2-pyridinyl]phenoxy]pyrimidine,5-chloro-2-r3-chloiO-2-(5-chloro-2-pyridinyl)phenoxy]pyrimidiiie,4- t2-[(5-bromo-2-pyrimidinyl)oxy]phenylj-2-(UittuoromethyI)pyrimidine!2-[2-(2-biOmo-5-thiazolyl)phenoxy]-5-(trifluoi mcthyl)pyrimidine,5- chloro-2-[4-inethyl-2-[2-(triiliiot methyl)-4-pyridinyI]phenoxy]pyrimidine,5-chloiO-2-[2-[5-(difluoi methyl)-3-isoxazolyl]phenoxy]pyriniidine,5-chloiO-2-[2-[3-(dinuoromethyl)-5-isoxazolyl]phenoxy]pyrimidine.5-chloi -2-[2-[5-(difluoromethyI)-3-isoxa* / x)lyl]-3-iluoropheiioxy]pyrimtdine, 5-bromo-2-[2-[5-(difluoromethyl)-3-isoxazolyl]phenoxy]pyrimidine,5-cliloro-2-[2-[3-(ti iflvxoromethyl)-5-isoxazolyl]phenoxy]pyrimidine,5-chloro-2-[2-[3-(difluoiOmethyl)-5-isoxazolyl]-3-fluorophenoxy]pyrimidine, 5-bromo-2-[2-f3-(difluoiOmethyl)-5-isoxazolyl]-3-iluorophcnoxy]pyrimidine, 5-chloro-2-f2-[5-(trifluoromethyl)-3-isoxa2:olyI]-3-iluoiOphenoxy]pyrimidine and 5-chloiO-2-[2-[5-(trinuoromethyl)-3-isoxazolyl]phenoxy]pymnidhie.

9. A herbicidal composition comprising a compound of Claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

10. A herbicidal composition comprising a compound of Claim 1, at least one additional acti ve ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.

11. A herbicidal mixture comprising (a) a compound of Claim 1, and (b) at least one additional active ingredient selected from (bl) through (bl6) and salts of compounds of (bl) through (b 16).

12. 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.

13. A method for controlling the growth of undesired vegetation in a genetically modified plants that exhibit traits of glyphosate tolerance, glufosinate tolerance, ALS herbicide tolerance, dicamba tolerance, imidazolinone herbicide tolerance, 2,4-D tolerance, liPPD tolerance and mesotrione tolerance, comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.

14. A herbicidal mixture comprising (a) a compound of Claim I , and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b4) auxin mimics, (b5) 5-enol-py vylshikimate-3- phosphate (EPSP) synthase inhibitors, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors and (bl 2)4-hydroxyphenyl-pyrtivate dioxygenase (I1PPD) inhibitors.

15. A herbicidal mixture comprising (a) a compound of Claim 1, and (b) at least one additional active ingi'edient selected from the group consisting of 2,4-D}acetochloi, alachlor, atrazine, bromoxynil, bentazon, bicyclopyrone, carfentrazone-ethyl, cloransulam-methyl, dicamba, dimethenamid-p, florasulam, flufenacet, flumioxazin, flupyrsulfuron-methyl, fluroxypyr-meptyl, glyphosate, halauxifen-mefhyl, isoxafliitole, MC A, mesotrione, metolachlor, metsulfiiron-methyl, nicosulfuron, pyrasulfotole, pyroxasulfone, pyroxsulam, vimsulfuron, saflufenacil, tcmbotrione, thifcnsulfuron-methyl, topramazone and tribenuron.