Substituted bicyclic amide derivatives as herbicides
Substituted bicyclic amide derivatives address the limitations of existing herbicides by offering effective, safe, and cost-efficient herbicidal solutions for crop and noncrop weed control.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2025-09-16
- Publication Date
- 2026-03-26
AI Technical Summary
Existing herbicides are often costly, toxic, and environmentally harmful, lacking effectiveness and selectivity in controlling undesirable vegetation in crops and noncrop areas.
Development of substituted bicyclic amide derivatives, including stereoisomers, N-oxides, and salts, formulated into herbicidal compositions with surfactants and diluents, for targeted weed control in crops and noncrop areas.
The compounds provide effective, less toxic, and environmentally safer herbicidal solutions with improved selectivity and reduced costs for weed management in various crops and noncrop environments.
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Abstract
Description
[0001] SUBSTITUTED BICYCLIC AMIDE DERIVATIVES AS HERBICIDES CROSS-REFERENCE TO RELATED APPLICATION This application claims the benefit of U.S. Provisional Application No.63 / 698042, filed September 23, 2024, all of which is incorporated by reference herein in its entirety. FIELD OF THE INVENTION This invention relates to certain herbicidal compounds, including sterioisomers, their N-oxides, salts thereof, agricultural compositions, and methods of their use for controlling undesirable vegetation. BACKGROUND OF THE INVENTION The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, 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. SUMMARY OF THE INVENTION This invention is directed to a compound of Formula 1, including stereoisomers, N-oxides and salts thereof, agricultural compositions containing them, mixtures with other active ingredients and their method of use as herbicides: Q is N or C-X5; each X1, X2, X3, X4and X5is independently hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C1–C6haloalkyl, C2–C6alkenyl, C2–C6haloalkenyl, C2–C6alkynyl, C2–C6haloalkynyl, C3–C7cycloalkyl, C3–C7halocycloalkyl, C1–C6alkoxy, C1–C6haloalkoxy, each of which is substituted by m radicals selected from the group consisting of cyano, S(O)pR7or CO2R8; p is 0, 1 or 2; ; cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, each of which is optionally further substituted by at least one radical selected from the group consisting of halogen, cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, and hydroxy; V and W are each independently O or S; R1is independently hydrogen, C1–C6alkyl, C 11 13–C7cycloalkyl, C1–C6haloalkyl, C1–C3alkoxy, C –C3haloalkoxy; or W G ; W1is a direct bond, C1–C4alkanediyl or C1–C4alkenediyl; G1is S(O)pR7, SO2NR10R11, CO2R8, CONR10R11or COR12; Y1is selected from the group consisting of ; Y2 Z is CH2, CF2, CCl2, O or NR13; m is 0, 1 or 2; Rvis halogen, cyano, CO2R8, C1–C2or C1–C2alkoxy, each of which is substituted by n radicals selected from halogens; R2is hydrogen, C1–C12alkyl, NH2, N=CR8R12, C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 272 8H O (2O95 6S R H , C )122 8(C )q( )p, C )qR ( H2 qCOR , or oxetanyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C6alkyl, C1–C6alkoxy, hydroxy and an aromatic ring; q is 0, 1, 2, 3, 4 or 5; R6is hydrogen, cyano, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR12, 10 11 10R12p, NR102NR R , NR CO CONR10R11, NR102CO2R8, NR10SO 10 10 11 72R7, NR SO2NR R , C(R)=NOR9, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR12, NR10R1, 10p112 10210 112NR COR , NR CONR R , NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)=NOR9, an optionally substituted aromatic ring, optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R2and R6can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C–C alkyl, C–C haloalkyl, OR, p7 10 11 81O R106S1119126S( ) , O2NR R , CO2R, CONR R , COR , NR10R11, NR10COR12, R7, alkoxy, C1–C6haloalkyl, C3–C7cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C–C alkoxy or aromatic ring; and 131 2R is hydrogen, C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, S(O)R7, SONR10R112 12, COR8, C105ON R117r O122 12 p 2 2R o C R . More particularly, this invention to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt This invention also relates to a herbicidal composition comprising a compound of the invention (i.e., in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein). This invention 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 (b1) through (b18); and salts of compounds of (b1) through (b18), as described below. DETAILS OF THE INVENTION 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. 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, 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”. 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.” 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 , A is false (or not present) and B is true (or present), and both A and B are true (or . 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. 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. 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. In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene” denotes a straight-chain or branched alkanediyl. Examples of “alkylene” include CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH2CH(CH3) and the different butylene isomers. “Alkenylene” denotes a straight-chain or branched alkenediyl containing one olefinic bond. Examples of “alkenylene” include CH=CH, CH2CH=CH, CH=C(CH3) and the different butenylene isomers. “Alkynylene” denotes a straight-chain or branchedalkynediyl containing one triple bond. Examples of “alkynylene” include C C, CH2C C,C CCH2 and the different butynylene 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. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” H2C=CHCH2O, (CH3)2C=CHCH2O, (CH3)CH=CHCH2O, (CH3)CH=C(CH3) and CH2=CHCH2CH2O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” includeHC CCH2O, CH3C CCH2O and CH3C CCH2CH2O. “Alkylthio” includes branched orstraight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)- and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2and CH3CH2SCH2CH2. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. “Alkyldithio” denotes branched or straight-chain alkyldithio moieties. Examples of “alkyldithio” include CH3SS-, CH3CH2SS-, CH3CH2CH2SS-, (CH3)2CHSS- and the different butyldithio and pentyldithio isomers. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH2, NCCH2CH2and CH3CH(CN)CH2. “Alkylamino”, “dialkylamino”, “alkenylthio”, “alkenylsulfinyl”, “alkenylsulfonyl”, “alkynylthio”, “alkynylsulfinyl”, “alkynylsulfonyl”, and the like, are defined analogously to the above examples. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl (i.e., c-Pr-CH2-), cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “cycloalkoxy” denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy. “Cycloalkylalkoxy” denotes cycloalkylalkyl linked through an oxygen atom attached to the alkyl chain. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups. “Cyanocycloalkyl” denotes a cycloalkyl group substituted with one cyano group. Examples of “cyanocycloalkyl” include 4-cyanocyclohexyl and 3-cyanocyclopentyl. “Cycloalkenyl” includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl. The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted halogen” said alkyl may be partially or fully substituted with halogen atoms which may the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F3C, ClCH2, CF3CH2and CF3CCl2. The terms “halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, “haloalkenyl”, “haloalkynyl”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O-, CCl3CH2O-, HCF2CH2CH2O- and CF3CH2O-. Examples of “haloalkylthio” include CCl3S- , CF3S-, CCl3CH2S- and ClCH2CH2CH2S-. Examples of “haloalkylsulfinyl” include CF3S(O)-, CCl3S(O)-, CF3CH2S(O)- and CF3CF2S(O)-. Examples of “haloalkylsulfonyl” include CF3S(O)2-, CCl3S(O)2-, CF3CH2S(O)2- and CF3CF2S(O)2-. Examples of “haloalkenyl” include (Cl)2C=CHCH2- and CF3CH2CH=CHCH2-. Examples of“haloalkynyl” include HC CCHCl-, CF3C C-, CCl3C C- and FCH2C CCH2-. Examples of“haloalkoxyalkoxy” include CF3OCH2O-, ClCH2CH2OCH2CH2O-, Cl3CCH2OCH2O- as well as branched alkyl derivatives. “Alkylcarbonyl” denotes a straight-chain or branched alkyl moieties bonded to a C(=O) moiety. Examples of “alkylcarbonyl” include CH3C(=O)-, CH3CH2CH2C(=O)- and (CH ) CHC(=O)-. Examples of “alkoxycarbonyl” include CH OC(=O)-, CH CH OC(=O)-,CH33C2HCH OC(=O)-, (CH ) CHOC(=O)- and the different3butoxy- or pe3ntox22 2 3 2ycarbonylisomers. “Oxetanyl” denotes oxetane substitution on straight-chain or branched alkyl groups. Examples of “oxtetane” include . The total number is indicated by the “Ci–Cj” prefix where i and j are numbers from 1 to 12. For example, C1–C4alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C2alkoxyalkyl designates CH3OCH2-; C3alkoxyalkyl designates, for example, CH3CH(OCH3)-, CH3OCH2CH2- or CH3CH2OCH2-; and C4alkoxyalkyl 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-. A wavy line in a structure fragment denotes the attachment point of the fragment to the remainder of the molecule. For example, when the variable A in Formula 1 is defined as A-1, the wavy line bisecting the bond pointing to the left designages the attachment point of A-1 to the remainder of the structure of Formula 1 at said ring as shown below. When a that indicates the number of said they exceed 1) are independently selected from the group of defined substituents, e.g., ([R(v))n], n is 0, 1, 2, 3, 4 or 5; or m is 0, 1, 2, 3, 4 or 5). When a group contains a substituent which can be hydrogen, for example X1, X2, X3, X4, X5, R1, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12and R13then 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, then hydrogen is at the position even if it is not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency. The definitions within variables X1, X2, X3, X4and X5can be “substituted by m radicals selected from the group consisting of cyano, S(O)pR7or CO2R8”. This means that any moiety that is capable of being further substituted can be further subststituted by cyano, S(O) R7or CO R8p2may substituted “m” times with these variables, and “m” is 0, 1, 2 or 3; preferably 0 or 1. For example C1–C6alkyl may be substituted with cyano to yield form a “C1–C7cyanoalkyl” wherein the total number of carbon atoms is 7 (including the carbon forming the cyano substituent). One skilled in the art will recognize that hydrogen, halogen, cyano, nitro, hydroxy cannot be further substituted with the listed radicals. Likewise, the definitions within variable Rvcan be “substituted by n radicals independently selected from halogens.” This means that any moiety that is capable of being substituted can be further subststituted with a halogen “n” times, and “n” is 0, 1, 2, 3 or 4; preferably 0, 1, 2 or 3, more preferrable 0 or 3. For example C1–C6alkyl may be substituted with a halogen to form a “C1–C6haloalkyl” group. One skilled in the art will recognize that hydrogen and halogen cannot be further substituted with the halogen. Unless otherwise indicated, a “ring” as a component of Formula 1 (e.g., substituent [J]) is carbocyclic or heterocyclic. The term “ring member” refers to an atom or other moiety (e.g., C(=O), C(=S), S(O) or S(O)2) forming the backbone of a ring. The terms “carbocyclic ring”, “carbocycle” denote a ring wherein the atoms forming the ring backbone are selected only from carbon. Unless otherwise indicated, a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated carbocyclic ring satisfies Hückel’s rule, then said ring is also called an “aromatic ring”. “Saturated carbocyclic” refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms. The terms “heterocyclic ring” or denote a ring in which at least one atom forming the ring backbone is not 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 Hückel’s rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen. “Aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital 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 Hückel’s rule. 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 R2, R6, R7, R8, R9, R10, R11and R12are an aromatic ring theis includes the possibility of them being 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, R2, R6, R7, R8, R9, R10, R11and R12can 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-1 in Exhibit 1, wherein Rvis F, Cl, C –C alkoxy or another aromatic ring as defined in the Summary of the v1 2Invention for R and n is an integer (from 0 to 5). As noted above, R2, R6, R7, R8, R9, R10, R11and R12can be (among others) a 5- or 6-membered 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, 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.r5 , r 2 , r , r , r , r , v)r, , , , , and Note that when R6, R7, R8, R9, R10, R11and R12are a 5- or 6-membered saturated or unsaturated non-aromatic heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention (i.e., F, Cl or C1–C2alkoxy), one or two ring members of the heterocycle can optionally be in the oxidized form of a carbonyl Examples of a 5- or 6-membered saturated or non-aromatic unsaturated heterocyclic ring containing ring members selected from up to two O atoms and up to two S atoms, and optionally substituted on carbon atom ring members with up to five halogen atoms includes the rings G-1 through G-35 as illustrated in Exhibit 2. Note that when the attachment point on the G group is illustrated as floating, the G group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the G group by replacement of a hydrogen atom. The optional substituents corresponding to Rvcan be attached to any available carbon or nitrogen by replacing a hydrogen atom. For these G rings, r is typically an integer from 0 to 4, limited by the number of available positions on each G group. Note that when R6, R7, R8, R9, R10, R11and R12comprises a ring selected from G-28 through G-35, G2is selected from O, S or N. Note that when G2is N, the nitrogen atom can complete its valence by substitution with either H or the substituents corresponding to Rvas defined in the Summary of the Invention. Exhibit 2 )r, r , r , r , r, r O , O . 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) and the U group is illustrated as f o t n , Rvrl ai g ( )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-5, U-7 through U-48, and U-52 through U- 61). 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. 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 enough to permit isolation of the isomeric species. One skilled in the art will 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. For example, when R5is other than hydrogen, then Formula 1 possesses a chiral center at the carbon atom to which R5is bonded. The two enantiomers are depicted as Formula 1' and Formula 1" with the chiral center identified with an asterisk (*). For a comprehensive discussion of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994. for depicting stereochemistry. To indicate stereoconfiguration, bonds rising from the plane of the drawing and towards the viewer are denoted by solid wedges wherein the broad end of the wedge is attached to the atom rising from the plane of the drawing towards the viewer. Bonds going below the plane of the drawing and away from the viewer are denoted by dashed wedges wherein the broad end of the wedge is attached to the atom further away from the viewer. Constant width lines indicate bonds with a direction opposite or neutral relative to bonds shown with solid or dashed wedges; constant width lines also depict bonds in molecules or parts of molecules in which no particular stereoconfiguration is intended to be specified. When R5is other than H the more biologically active enantiomer is believed to be Formula 1'. When R1is CH , Formula 1' has the R configuration at the carbon atom to which R53is bonded. This invention comprises racemic mixtures, for example, equal amounts of the enantiomers of Formulae 1' and 1". In addition, this invention includes compounds that are enriched compared to the racemic mixture in an enantiomer of Formula 1. Also included are the essentially pure enantiomers of compounds of Formula 1, for example, Formula 1' and Formula 1". When enantiomerically enriched, one is present in greater amounts than the other, and the extent of enrichment can be by an expression of enantiomeric excess (“ee”), which is defined as (2x–1)·100%, where x is the mole fraction of the dominant enantiomer in the mixture (e.g., an ee of 20% corresponds to a 60:40 ratio of enantiomers). Preferably the compositions of this invention have at least a 50% enantiomeric excess; more preferably at least a 75% enantiomeric excess; still more preferably at least a 90% enantiomeric excess; and the most preferably at least a 94% enantiomeric excess of the more active isomer. Of particular note are enantiomerically pure embodiments of the more active isomer. Compounds of Formula 1 can comprise additional chiral centers. For example, substituents and other molecular constituents such as X1, X2, X3, X4, R1and R2may themselves contain chiral centers. This invention comprises racemic mixtures as well as enriched and essentially pure stereoconfigurations at these additional chiral centers. Compounds of this invention can exist as one or more conformational isomers due to restricted rotation about the amide bond (e.g., C(=V)–A) in Formula 1. This invention comprises mixtures of conformational isomers. In addition, this invention includes compounds that are enriched in one conformer relative to others. A compound of Formula 1 typically exists in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non- crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). 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. One skilled in the art will not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an 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. 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 a wide 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 (i.e. when W is O, Y2is O and R2is H) 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. Embodiments of the present invention as described in the Summary of the Invention include those described below. In the following Embodiments, Formula 1 includes stereoisomers, N-oxides and salts thereof, and reference to “a compound of Formula 1” includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments. Embodiment 1. A compound of 1, stereoisomers, N-oxides, and salts thereof, agricultural compositions them and their use as herbicides as described in the Summary of the Invention. Embodiment 2. A compound of Embodiment 1 wherein Q is N. Embodiment 3. A compound of Embodiment 2 wherein Q is C-X5. Embodiment 4. A compound of Embodiment 3 wherein X5is halogen. Embodiment 5. A compound of Embodiment 4 wherein X5is F or Cl. Embodiment 6. A compound of Embodiment 4 wherein X5is Cl. Embodiment 7. A compound of Embodiment 4 wherein X5is F. Embodiment 8. A compound of any one of Embodiments 1 through 7 wherein each X1, X2, X3, X4is independently hydrogen, halogen, cyano, C1–C6alkyl, C1–C6haloalkyl, C1–C6alkoxy or C1–C6haloalkoxy. Embodiment 9. A compound of Embodiment 8 wherein each X1, X2, X3, X4is independently hydrogen, F, Cl, Br, cyano, C1–C2alkyl, C1–C2haloalkyl, C1–C2alkoxy or C1–C2haloalkoxy. Embodiment 10. A compound of Embodiment 9 wherein each X1, X2, X3, X4is independently hydrogen, F, Cl, Me, CF3, OMe or OCF3. Embodiment 11. A compound of Embodiment 10 wherein each X1, X2and X4is hydrogen and X3is F or Cl. Embodiment 12. A compound of Embodiment 11 wherein X3is Cl. Embodiment 13. A compound of Embodiment 11 wherein X3is F. Embodiment 14. A compound of any one of Embodiments 1 through 13 wherein A is A-1 or A-2. Embodiment 15. A compound of any one of Embodiments 1 through 13 wherein A is A-3. Embodiment 16. A compound of Embodiment 14 wherein A is A-1. Embodiment 17. A compound of Embodiment 14 wherein A is A-2. Embodiment 18. A compound of any one of Embodiments 1 through 16 wherein R3and R4are each independently hydrogen, halogen, cyano, C1–C3alkyl, C1–C3haloalkyl, C1–C3cyanoalkyl, C1–C3alkoxy, C1–C3haloalkoxy or C1–C3cyanoalkoxy. Embodiment 19. A compound of Embodiment 18 wherein R3and R4are each independently hydrogen, halogen, cyano, C1–C2alkyl, C1–C2haloalkyl, C1–C2cyanoalkyl, C1–C2alkoxy, C1–C2haloalkoxy or C1–C cyanoalkoxy. b d m n 2 . c m o32Em o i e t 0 A o p und of Embodiment 19 wherein R and R4are each independently hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3or OCH2CN. Embodiment 21. A compound of 20 wherein R3and R4are each independently hydrogen, or cyano. Embodiment 22. A compound of Embodiment 21 wherein R3and R4are each independently hydrogen, F, Cl, Br or cyano. Embodiment 23. A compound of Embodiment 22 wherein R3and R4are each independently hydrogen or Me. Embodiment 24. A compound of Embodiment 23 wherein R3and R4are each hydrogen. Embodiment 25. A compound of any one of Embodiments 1 through 24 wherein R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, optionally each of which is further substituted by at least one radical selected from the group consisting of halogen, cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl and hydroxy. Embodiment 26. A compound of Embodiment 25 wherein R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl or C –C alkylsulfonyl. o i e51 4Emb d m nt 27. A compound of Embodiment 26 wherein R is hydrogen, halogen, cyano, hydroxy, C1–C3alkyl, C2–C3alkenyl, C2–C3alkynyl, C3–C5cycloalkoxy, C3–C5cycloalkoxyalkyl, C3–C5cycloalkyl, C4–C7cycloalkylalkyl, C1–C3haloalkyl, C2–C3alkoxyalkyl, C2–C3haloalkoxyalkyl, C1–C3alkoxy, C1–C3haloalkoxy, C1–C3alkylthio, C1–C3alkylsulfinyl or C1– C3alkylsulfonyl. Embodiment 28. A compound of Embodiment 27 wherein R5is hydrogen, C1–C3alkyl, C2–C3alkenyl, C2–C3alkynyl, C3–C5cycloalkyl, C4–C7cycloalkylalkyl, C1– C3haloalkyl, C2–C3alkoxyalkyl, C2–C3haloalkoxyalkyl, C1–C3alkoxy, C1–C3haloalkoxy. Embodiment 29. A compound of Embodiment 28 wherein R5is hydrogen, Me, Et, CH=CH2, C≡CH, cyclopropyl, cyclopropylmethyl, CF 53, OMe or OCF3. Embodiment 30. A compound of Embodiment 29 wherein R is hydrogen, Me, Et, CH=CH2, C≡CH, cyclopropyl, CF3, OMe or OCF3. Embodiment 31. A compound of 30 wherein R5is hydrogen, Me, Et, CH=CH2, C≡CH, cyclopropyl, OMe or OCF3. Embodiment 32. A compound of Embodiment 31 wherein R5is hydrogen, Me, Et, CH=CH2, C≡CH, cyclopropyl, CF3or Me. Embodiment 33. A compound of Embodiment 32 wherein R5is Me, CH=CH2or CF3. Embodiment 34. A compound of any one of Embodiments 1 through 33 wherein V is O and W is S. Embodiment 35. A compound of any one of Embodiments 1 through 33 wherein V is S and W is O. Embodiment 36. A compound of any one of Embodiments 1 through 33 wherein V and W are both S. Embodiment 37. A compound of any one of Embodiments 1 through 33 wherein V and W are both O. Embodiment 38. A compound of Embodiment 2 wherein R1is hydrogen, C1–C6alkyl, C3–C7cycloalkyl, C1–C6haloalkyl, C1–C3alkoxy or C –C haloalkoxy. o i e t 9 A o p11 3Emb d m n 3 . c m ound of Embodiment 38 wherein R is hydrogen or CH . Emb d m n 4 . c m o n o E13o i e t 0 A o p u d f mbodiment 39 wherein R is hydrogen. Embodiment 41. A compound of Embodiment 39 wherein R1is CH3. Embodiment 42. A compound of any one of Embodiments 1 through 41 wherein Y1is selected from the group consisting of Y1-1 and Y1-2. Embodiment 43. A compound of any one of Embodiments 1 through 41 wherein Y1is selected from the group consisting of Y1-1 and Y1-3. Embodiment 44. A compound of any one of Embodiments 1 through 41 wherein Y1is selected from the group consisting of Y1-2 and Y1-3. Embodiment 45. A compound of any one of Embodiments 1 through 41 wherein Y1is Y1-1. Embodiment 46. A compound of any one of Embodiments 1 through 41 wherein Y1is Y1-2. Embodiment 47. A compound of any one of Embodiments 1 through 41 wherein Y1is Y1-3. Embodiment 48. A compound of any one of Embodiments 1 through 47 wherein Y2is a direct bond, O or S. Embodiment 49. A compound of any one of Embodiments 1 through 47 wherein Y2is NR6. Embodiment 50. A compound of Embodiment 48 wherein Y2is O or S. Embodiment 51. A compound of Embodiment 48 wherein Y2is a direct bond. Embodiment 52. A compound of Embodiment 50 wherein Y2is O. Embodiment 53. A compound of Embodiment 50 wherein Y2is S. Embodiment 54. A compound of any of Embodiments 1 through 53 wherein Z is CH2, CF2, O or NR6. Embodiment 55. A compound of Embodiment 54 wherein Z is CH2or O. Embodiment 56. A compound of Embodiment 54 wherein Z is CH2. Embodiment 57. A compound of Embodiment 54 wherein Z is O. Embodiment 58. A compound of any one of Embodiments 1 through 57 wherein m is 0. Embodiment 59. A compound of any one of Embodiments 1 through 57 wherein m is 1. Embodiment 60. A compound of any one of Embodiments 1 through 57 wherein m is 2. Embodiment 61. A compound of any one of Embodiments 1 through 60 wherein Rvis halogen, cyano, CO2R8, C1–C2alkyl or C1–C2alkoxy. Embodiment 62. A compound of Embodiment 61 wherein Rvis halogen or C–C alkyl. v1 2Embodiment 63. A compound of Embodiment 62 wherein R is halogen or CH. Emb dmn 6. cv3oi et 4 A ompound of Embodiment 61 wherein R is halogen. Embodiment 65. A compound of Embodiment 61 wherein Rvis CH3. Embodiment 66. A compound of any one of Embodiments 1 through 65 wherein R2is hydrogen, C1–C12alkyl, NH2, N=CR8R12, C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 272 8H O95 6S122 8(C )q( )pR, (CH2)qOR, (CH2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C6alkyl, C1–C6alkoxy, hydroxy and an aromatic ring. Embodiment 67. A compound of Embodiment 66 wherein R2is hydrogen, C1–C7alkyl, C3–C7cycloalkyl, C3–C7cycloalkylalkyl, C 792–C5alkenyl, C C2–C alk125–C6cycloalkenyl, 5 ynyl, (CH2)qS(O)pR, (CH2)qOR, (CH2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and an aromatic ring. Embodiment 68. A compound of Embodiment 67 wherein R2is hydrogen, C–C alkyl, 371C C ylakl95–5ccoly, C 123–C7cycloalkylalkyl, (CH2)qS(O)pR, (CH2)qOR, (CH2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and an aromatic ring. Embodiment 69. A compound of Embodiment 68 wherein R2is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph. Embodiment 70. A compound of Embodiment 69 wherein R2is hydrogen, Me, Et, i-Pr, i-Bu, t-Bu, c-Pent, OMe, CH2CF3, CH2CN, (CH2)2OMe, CH2CO2Me, CH2CO2Et, CH2CO2(4-F-Ph), CH2SMe, CH2Ph, NCHPh, (CH2)2SO2Me, SO2Me, SO2Et, SO2(n-Pr), SO2(c-Pr), SO2(t-Bu), SO2CF3or SO2Ph. Embodiment 71. A compound of any of Embodiments 1 through 70 wherein R6is hydrogen, cyano, OR9, S(O) CO R8, CONR10R11, COR12, NR10R11, NR10COR12, NR10CONR10R11, NR102CO2R8, NR10SO 12R7, NR0SO2NR10R11, C(R7)=NOR9, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O) R7, SO NR10R11, CO R8, CONR10R11, COR12, NR10R11, 10pCOR12, NR102CONR10R112NR , NR10CO R8, NR10SO R7, NR10SO NR10R11, 792 2 2C(R )=NOR , an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R2and R6can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C –C alkyl, C –C haloalkyl, OR9, 710 11 81O106111126S( )pR , SO2NR R , CO2R , CONR R , COR , NR10R11, NR10COR12, NR10CONR10R11, NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)=NOR9; or C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2– C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O) R7, SO NR10R11, CO R8, CONR10R11, COR12, NR10R11, NR10COR12p, NR102CONR10R11, NR120CO2R8, NR10SO2R7, S(O) S(O)pR7, SO2NR10R11, CO2R8, CONR10R11or COR12. Embodiment 75. A compound of 69 wherein R6is C1–C4alkyl, C3–C8cycloalkyl, C4–C8C2–C4alkenyl, C5–C7cycloalkenyl or C2– C6alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, OR9, S(O) R7, 210 11 8 10 11 12 10 11 1pSO NR R , CO2R , CONR R , COR , NR R or NR0COR12. Embodiment 76. A compound of Embodiment 69 wherein R6is hydrogen, OR9, S(O)pR7, SO2NR10R11, CO2R8or COR12. Embodiment 77. A compound of Embodiment 74 wherein R6is C1–C4alkyl, C3–C8cycloalkyl, C4–C8cycloalkylalkyl, C2–C4alkenyl, C5–C7cycloalkenyl or C2– C6alkynyl. Embodiment 78. A compound of Embodiment 74 wherein R6is hydrogen, OR9or S(O)pR7. Embodiment 79. A compound of Embodiment 75 wherein R6is C1–C4alkyl or C3–C8cycloalkyl. Embodiment 80. A compound of Embodiment 76 wherein R6is hydrogen, OMe or S(O)2R7. Embodiment 81. A compound of Embodiment 76 wherein R6is Me or c-Pr. Embodiment 82. A compound of Embodiment 71 wherein R2and R6are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, C –C alkyl, C –C haloalkyl, oxo, OR9, S(O) R7, CO R or 10 111 3 1 3 p 28NR R . Embodiment 83. A compound of Embodiment 81 wherein the 3- to 7-membered ring contains carbon atoms and optionally 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, C1–C3alkyl, C1–C3haloalkyl, oxo, OR9, S(O)pR7, CO2R8or NR10R11. Embodiment 84. A compound of Embodiment 83 wherein the 3- to 7-membered ring contains carbon atoms and optionally 1 to 2 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently from the group consisting of halogen, cyano, C1–C3alkyl, C1–C3haloalkyl. Embodiment 85. A compound of Embodiment 84 wherein the 3- to 7-membered ring is selected from the group of morpholinyl, thiomorpholinyl, oxazinyl, thiazinyl, piperidinyl, piperazinyl and isomers thereof, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, C1–C3alkyl, and C1–C3haloalkyl. Embodiment 86. A compound of any one of Embodiments 1 throuth 85 wherein R7, R8, R9, R10, R11and R12are each independently hydrogen, C1–C6alkyl, C1–C6haloalkyl, C3–C7cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring. Embodiment 87. A compound of Embodiment 86 wherein R7, R8, R9, R10, R11and R12are each independently hydrogen, C1–C3alkyl, C1–C3haloalkyl, C3–C5cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring. Embodiment 88. A compound of Embodiment 86 wherein R7, R8, R9, R10, R11and R12are each independently hydrogen, C1–C3alkyl, C1–C3haloalkyl, C3–C5cycloalkyl or phenyl, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring. Embodiment 89. A compound of Embodiment 86 wherein R7, R8, R9, R10, R11and R12are each independently hydrogen, Me, Et, Pr, i-pr, c-Pr, t-Bu, CF3, OMe, OEt, CF3, CH2CF3, CH2-c-Pr, Ph each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring. Embodiment 90. A compound of any one of Embodiments 1 through 89 wherein R13is hydrogen, C1–C12alkyl, S(O)pR7or CO2R8. Embodiment 91. A compound of Embodiment 90 wherein R13is hydrogen, CH3, S(O)2CH3or CO2(t-Bu). Embodiments of this invention, including Embodiments 1–91 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 compounds 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 1–91 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention. Combinations of Embodiments 1–91 illustrated by: Embodiment A. A compound of Formula 1 as defined in the Summary of the Invention wherein Y1is selected from the group consisting of Y1-1 and Y1-2. Embodiment A1. A compound of Formula 1 as defined in the Summary of the Invention wherein Q is N; each X1, X2, X3, X4is independently hydrogen, halogen, cyano, C1–C6alkyl, C1–C6haloalkyl, C1–C6alkoxy or C1–C6haloalkoxy; A is A-1 or A-2; R3and R4are each independently hydrogen, halogen, cyano, C1–C3alkyl, C1–C3haloalkyl, C1–C3cyanoalkyl, C1–C3alkoxy, C1–C3haloalkoxy or C1–C3cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, optionally each of which is further substituted by at least one radical selected from the group consisting of halogen, cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl and hydroxy; V and W are both O; R1is hydrogen, C1–C6alkyl, C3–C7cycloalkyl, C1–C6haloalkyl, C1–C3alkoxy or C1– C3haloalkoxy; Y1is selected from the group consisting of Y1-1 and Y1-2; Y2is a direct bond, O or S; Z is CH2, CF2, O or NR6; m is 0; Rvis halogen, cyano, CO2R8, C1–C2alkyl or C1–C alkoxy; R2is hydrogen, C–C alkyl, NH, N8 1221 12 2=CRR , C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 272 8H O ( O95 6S R H , C122 8(C )q( )p, C2)qR ( H2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C–C alkyl, C–C alkoxy, hydroxy and an aromatic ring; 61R96s71 6i hydrogen, cyano, OR, S(O)R, SONR10R11, COR8, CONR10R11, COR12, 10 11 10OR12p, NR102NR R , NR C CONR10R11, NR102CO2R8, NR10SO 10 10 12R7, NR SO2NR R1, C(R7)=NOR9, an optionally substituted aromatic ring, an optionally substituted ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR12, NR10R11, N10p12 10210 112R COR , NR CONR R , NR10COR8, NR10SOR7, NR10SONR10R11, 792 2 2C(R)=NOR, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or 26R and R can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O), said ring being optionally2substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C–C alkyl, C–C haloalkyl, OR, 710 11 8110611112691S(O)R, SONR R , COR, CONR R , COR , NR0R11, NR10COR12, 10p12011 102NR CONR R , NR COR8 10 7 10 10 11, NR SOR, NR SONR R ,2 2 279C(R)=NOR; 78 9 10 11 12R, R, R, R , R and R are each independently hydrogen, C–C alkyl, C–C1 6 1 6haloalkyl, C–C cycloalkyl or an aromatic ring, each of which is optionally3 7substituted by one or more radicals selected from the group consisting of F, Cl, C–C alkoxy and an aromatic ring; and1 213 7 8R is hydrogen, C–C alkyl, S(O)R or COR.1 12 p 2Embodiment B. A compound of Embodiment A wherein 12 3 4X, X, X, X is independently hydrogen, F, Cl, Br, cyano, C–C alkyl, C–C1 2 1 2haloalkyl, C–C alkoxy or C–C haloalkoxy;1 2 1 2A is A-1; 2 R is hydrogen, C–C alkyl, C–C cycloalkyl, C–C cycloalkylalkyl, C–C alkenyl,1 7 3 7 3 7 2 579C–C cycloalkenyl, C–C alkynyl, (CH)S(O)R, (CH)OR,5 6 2 5 2 q p 2 q12(CH)COR , each of which is optionally substituted by one or more radicals2 qselected from the group consisting of halogen, cyano, C–C alkyl, C–C1 3 1 3alkoxy, hydroxy and an aromatic ring; 34R and R are each independently hydrogen, halogen, cyano, C–C alkyl, C–C1 2 1 2haloalkyl, C–C cyanoalkyl, C–C alkoxy, C–C haloalkoxy or C–C1 2 1 2 1 2 1 2cyanoalkoxy; 5 R is hydrogen, halogen, cyano, nitro, hydroxy, C–C alkyl, C–C alkenyl, C–C1 6 2 5 2 5alkynyl, C–C alkenyloxy, C–C alkynyloxy, C–C cycloalkoxy, C–C2 5 2 5 3 7 3 7 cycloalkoxyalkyl, C3–C6C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl or C –C alkylsulfonyl; 11 4R is hydrogen or CH 1 Y13; Y is -1; Y2is O or S; Z is CH v2or O; R is halogen or C1–C2alkyl; R2is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, cyano, OR9, S(O) R7, SO NR10R11, CO R8, CONR10R11or COR12; R7, R8, R9, R10, R11an R12p 2 2d are each independently hydrogen, C1–C3alkyl, C1–C3haloalkyl, C3–C5cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C –C alkoxy and an aromatic ring; and 131 2R is hydrogen, CH3, S(O)2CH3or CO2(t-Bu). Embodiment C. A compound of Embodiment B wherein each X1, X2, X3, X4is independently hydrogen, F, Cl, Me, CF , OMe or OCF ; 343 3R and R are each independently hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3or OCH 52CN; R is hydrogen, halogen, cyano, hydroxy, C1–C3alkyl, C2–C3alkenyl, C2–C3alkynyl, C3–C5cycloalkoxy, C3–C5cycloalkoxyalkyl, C3–C5cycloalkyl, C4–C7cycloalkylalkyl, C1–C3haloalkyl, C2–C3alkoxyalkyl, C2–C3haloalkoxyalkyl, C1–C3alkoxy, C1–C3haloalkoxy, C1–C3alkylthio, C1–C3alkylsulfinyl or C1– C3alkylsulfonyl; R1is hydrogen; Y2is O; Rvis halogen or CH 23; R is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, OR9or S(O) 1pR7; and R7, R8, R9, R10, R11and R2are each independently hydrogen, Me, Et, Pr, i-pr, c-Pr, t- Bu, CF3, OMe, OEt, CF3, CH2CF3, CH2-c-Pr, Ph each of which is optionally substituted by one or more selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic Embodiment D. A compound of Formula 1 as defined in the Summary of the Invention wherein Q is C-X5; each X1, X2, X3, X4is independently hydrogen, halogen, cyano, C1–C6alkyl, C1–C6haloalkyl, C–C alkoxy or C–C haloalkoxy; 51 6 1 6X is halogen; A is A-1 or A-2; R3and R4are each independently hydrogen, halogen, cyano, C1–C3alkyl, C1–C3haloalkyl, C1–C3cyanoalkyl, C1–C3alkoxy, C1–C3haloalkoxy or C1–C3cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, optionally each of which is further substituted by at least one radical selected from the group consisting of halogen, cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl and hydroxy; V and W are both O; R1is hydrogen, C1–C6alkyl, C3–C7cycloalkyl, C1–C6haloalkyl, C1–C3alkoxy or C1– C3haloalkoxy; Y1is selected from the group consisting of Y1-1 and Y1-2; Y2is a direct bond, O or S; Z is CH2, CF2, O or NR6; m is 0; Rvis halogen, cyano, CO2R8, C–C alkyl or C–C alkoxy; 21 2R is hydrogen, C–C alkyl,28 121 21 12NH, N=CRR , C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 272 8H O ( O95 6S R H , C122 8(C )q( )p, C2)qR ( H2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C–C alkyl, C–C alkoxy, hydroxy and an aromatic ring; 61R , cyano, OR96s , S(O)R71 6i hydrogen , SONR10R11, COR8, CONR10R11, COR12, 10 11 10COR12p, NR102NR R , NR CONR10R11, NR102CO2R8, NR10SO 10 12R7, NR SO2NR0R11, C(R7)=NOR9, an optionally substituted aromatic ring, an optionally substituted ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR12, NR10R11, 10p12 10210 112NR COR , NR CONR R , NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)=NOR9, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R2and R6can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C–C alkyl, C–C haloalkyl, OR, p7 10 11 81O R106S1119126S( ) , O2NR R , COR, CONR R , COR , NR10R11, NR10COR12, NR10 10 11 102CONR R , NR CO2R8, NR10SO2R7, NR10SO10 117 92NR R , C(R)=NOR; R7, R8, R9, R10, R11and R12are each independently hydrogen, C1–C6alkyl, C1–C6haloalkyl, C3–C7cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C–C alkoxy and an aromatic ring; and 131 2R is hydrogen, C1–C12alkyl, S(O)pR7or CO2R8. Embodiment E. A compound of Embodiment D wherein X1, X2, X3, X4is independently hydrogen, F, Cl, Br, cyano, C1–C2alkyl, C1–C2haloalkyl, C–C alkoxy or C–C haloalkoxy; 51 2 1 2X is F or Cl; A is A-1; R2is hydrogen, C1–C7alkyl, C3–C7cycloalkyl, C3–C7cycloalkylalkyl, C–C alkenyl, 5C ylaknl C C l7 92 5C–6ccoley,2–5akynyl, (CH2)qS(O)pR, (CH2)OR, (CH2)qCOR12q, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and an aromatic ring; R3and R4are each independently hydrogen, halogen, cyano, C1–C2alkyl, C1–C2haloalkyl, C1–C2cyanoalkyl, C1–C2alkoxy, C1–C2haloalkoxy or C1–C2cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl or C –C alkylsulfonyl; 11 4R is hydrogen or CH 1 Y13; Y is -1; Y2is O or S; Z is CH Rv2or O; is halogen or C R21–C2alkyl; is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, cyano, OR9, S(O) R7, SO NR10R11, CO R8, CONR10R11or COR12; R7, R8, R9, R10, R11an R12p 2 2d are each independently hydrogen, C1–C3alkyl, C1–C3haloalkyl, C3–C5cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C –C alkoxy and an aromatic ring; and 131 2R is hydrogen, CH3, S(O)2CH3or CO2(t-Bu). Embodiment F. A compound of Embodiment E wherein X1, X2and X4is hydrogen; and X3is F or Cl; R3and R4are each independently hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3or OCH 52CN; R is hydrogen, halogen, cyano, hydroxy, C1–C3alkyl, C2–C3alkenyl, C2–C3alkynyl, C3–C5cycloalkoxy, C3–C5cycloalkoxyalkyl, C3–C5cycloalkyl, C4–C7cycloalkylalkyl, C1–C3haloalkyl, C2–C3alkoxyalkyl, C2–C3haloalkoxyalkyl, C1–C3alkoxy, C1–C3haloalkoxy, C1–C3alkylthio, C1–C3alkylsulfinyl or C1– C3alkylsulfonyl; R1is hydrogen; Y2is O; Rvis halogen or CH 23; R is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, OR9or S(O)pR7; and R7, R8, R9, R10, R11and R12are each hydrogen, Me, Et, Pr, i-pr, c-Pr, t- Bu, CF3, OMe, OEt, CF3, CH2-c-Pr, Ph each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring. Embodiment G. A compound of Embodiment F wherein X3is F; X5is F; X1, X2and X4is hydrogen; R3and R4are each independently hydrogen, halogen or cyano; R5is hydrogen, Me, Et, CH=CH , C≡CH, cyclopropyl, CF , OMe or OCF ; 12 3 3R is hydrogen; Rvis halogen; Z is CH2; R2is hydrogen, Me, Et, i-Pr, i-Bu, t-Bu, c-Pent, OMe, CH2CF3, CH2CN, (CH2)2OMe, CH2CO2Me, CH2CO2Et, CH2CO2(4-F-Ph), CH2SMe, CH2Ph, NCHPh, (CH2)2SO2Me, SO2Me, SO2Et, SO2(n-Pr), SO2(c-Pr), SO2(t-Bu), SO2CF3or SO2Ph; and R6is C1–C4alkyl or C3–C8cycloalkyl. Specific embodiments include compounds of Formula 1 selected from the group consisting of: methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 6); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 36); methyl (1S,2S,4R,5R)-4-[[(3E)-4-(3,5-difluorophenyl)-2,2-difluoro-1-oxo-3- buten-1-yl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 76); methyl (1S,2S,4R,5R)-4-[[[1-(3,5-dichlorophenyl)-3-methyl-2-oxo-3- azetidinyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 93); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-4,5-dihydro-5-methyl-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 109); and methyl (1S,2S,4R,5R)-4-[[[3-(3,5- -4,5-dihydro-5-methyl-5- isoxazolyl]carbonyl]amino]-6- [3.1.0]hexane-2-carboxylate (Compound 124). Other specific embodiments include compounds of Formula 1 selected from the group consisting of: methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-(chloromethyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 210); methyl (1S,2S,4R,5R)-4-[[[5-(chloromethyl)-3-(3,5-dichlorophenyl)-4,5-dihydro- 5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 194); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 113); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(R)- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(S)- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate; (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid (Compound 3); methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 6); (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)- 5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylic acid (Compound 7); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 124); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(R)-methyl-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(S)-methyl-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate; methyl (1S,2S,4R,5R)-4-[[[5- -3-(3,5-difluorophenyl)-4,5-dihydro- 5-isoxazolyl]carbonyl]amino]- [3.1.0]hexane-2-carboxylate (Compound 158); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-5-ethenyl-4,5-dihydro-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 121); cyanomethyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 151); 2-methoxy-2-oxoethyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 132); 2-oxopropyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 134); 3-(3,5-difluorophenyl)-5-ethenyl-N-[(1S,2R,4S,5R)-4- [[(ethylsulfonyl)amino]carbonyl]bicyclo[3.1.0]hex-2-yl]-4,5-dihydro-5- isoxazolecarboxamide (Compound 97); methyl (1S,2S,4R,5R)-4-[[[5-(difluoromethyl)-3-(3,5-difluorophenyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 196); methyl (2S,4R)-4-[[[3-(3,5-difluorophenyl)-5-(fluoromethyl)-4,5-dihydro-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 208); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-5-(fluoromethyl)-4,5-dihydro- 5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 155); methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-(fluoromethyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 175); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane- 2-carboxylate (Compound 36); and methyl (1S,2S,4R,5R)-4-[[[5-(1,1-difluoroethyl)-3-(3,5-difluorophenyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 179). This invention also relates to a controlling undesired vegetation comprising applying to the locus of the vegetation 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 crop such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops. Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above. 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 photosystem II inhibitors (b1), AHAS inhibitors (b2), ACCase inhibitors (b3), auxin mimics (b4), EPSP synthase inhibitors (b5), photosystem I electron diverters (b6), PPO inhibitors (b7), GS inhibitors (b8), VLCFA elongase inhibitors (b9), auxin transport inhibitors (b10), PDS inhibitors (b11), HPPD inhibitors (b12), DXP synthase inhibitors (b13), HST inhibitors (b14), cellulose biosynthesis inhibitors (b15), DHODH inhibitors (b16), other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinflubrolin, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb (b17), and herbicide safeners (b18); and salts of compounds of (b1) through (b18). “Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the QB-binding niche and thus block electron transport from QAto QBin 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. “AHAS inhibitors” (b2) are compounds that inhibit acetohydroxy acid synthase (AHAS), also known as synthase (ALS), and thus kill plants by inhibiting 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, iodosulfuron-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy- 2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-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-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6- fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron. “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, metproxybicyclone, 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. 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 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, fluchloraminopyr, fluchloraminopyr-tefuryl, flufenauxirim, flufenauxirim-metotyl, halauxifen, halauxifen-methyl, 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. “EPSP 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). “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, paraquat and 1-(2-carboxyethyl)-4-(2- pyrimidinyl)pyridazinium and salts and esters thereof. Of note is a photosystem I electron diverter selected from diquat and paraquat. “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, cyclopyranil, epyrifenacil, fendioxypyracil, fluazolate, flufenoximacil, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, trifludimoxazin (dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro- 3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)- dione), tiafenacil and methyl 2-[2-[2-bromo-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate, ethyl 3- [2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4- fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylate. “GS 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 derivatives, glufosinate-P ((2S)-2-amino- 4-(hydroxymethylphosphinyl)butanoic bilanaphos. “VLCFA 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-(1-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides. “Auxin transport inhibitors” (b10) 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-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid). “PDS inhibitors” (b11) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, flufenazopyr, fluridone, flurochloridone, flurtamone norflurzon and picolinafen. “HPPD inhibitors” (b12) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benquinotrione, benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2- methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2- one), bipyrazone, cyprafluone, fenpyrazone, fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4- methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), flusulfinam, iptriazopyrid, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyraquinate, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5- yl]oxy]ethyl methyl carbonate), topramezone, toxapyzone, 5-chloro-3-[(2-hydroxy-6-oxo-1- cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4- methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, tripyrasulfone, 4-(4- fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine- 3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)- 3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3- (methylsulfinyl)-4-(trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(1- methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide. “Deoxy-D-Xylulose Phosphate (DXP synthase) inhibitors” (b13) isoxazolidinone class of herbicides is according to its inhibition of the deoxy-d- xylulose phosphate synthase (DXP synthase) which is a component of the carotenoid biosynthetic pathway. Examples of DXP synthase inhibitors include bixlozone, broclozone and clomazone. Of note is a DXP synthase inhibitor selected from bixlozone and clomazone. “HST inhibitors” (b14) disrupt a plant’s ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include cyclopyrimorate, haloxydine, pyriclor, 3-(2-chloro-3,6- difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 7-(3,5-dichloro-4- pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one and 4-(2,6- diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone. Another example of an HST inhibitor is 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)- pyridazinone. “Cellulose biosynthesis inhibitors” (b15) inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied preemergence or early postemergence on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6- (1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben and triaziflam. “Dihydroorotate dehydrogenase (DHODH) inhibitors” (b16) inhibit dihydroorotate dehydrogenase of the de-novo pyrimidine biosynthetic pathway. The first two steps of de-novo pyrimidine biosynthesis occur in the chloroplast after which the product, N-carbamoyl aspartate, is shuttled to the cytoplasm where dihydroorotase resides, producing dihydroorotate, the DHODH substrate. Plant DHODH is a flavin-dependent enzyme residing on the outer surface of the inner mitochondrial membrane. Reducing equivalents pass from dihydroorotate via the tightly bound flavin cofactor to a ubiquinone acceptor molecule that subsequently exchanges with the ubiquinol pool of the membrane and ultimately links DHODH enzymatic activity with oxidative phosphorylation. The remaining steps of the pathway leading to pyrimidine nucleotides occur in the cytoplasm. DHODH inhibitors include a compound of Formula (b16A) wherein R12is H, C1–C6alkyl, C1–C6haloalkyl or C4–C8cycloalkyl; R13is H, C –C alkyl or 11 6C1–C6Q is an optionally substituted ring selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl and pyrazolyl, wherein when substituted said ring system is substituted by 1 to 3 R14; Q2is an optionally substituted ring system selected from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, wherein when substituted said ring system is substituted by 1 to 3 R15; each R14is independently halogen, C1–C6alkyl, C1–C6haloalkyl, C1–C6alkoxy, C1–C6haloalkoxy, C3–C8cyaloalkyl, cyano, C alk l u171–C6alkylthio, C1–C6y s lfinyl, C –C alkylsulfonyl, SF , NHR ; or phenyl optionally substituted 161 6 5by 1 to 3 R ; or pyrazolyl optionally substituted by 1 to 3 R16; each R15is independently halogen, C1–C6alkyl, C1–C6haloalkyl, C1–C6alkoxy, C1–C6haloalkoxy, cyano, nitro, C1–C6alkylthio, C1–C6alkylsulfinyl, C1–C6alkylsulfonyl; each R16is independently halogen, C –C alkyl or C –C haloalkyl; 171 6 1 6R is C1–C4alkoxycarbonyl. In one Embodiment wherein “DHODH inhbitors” (b16) also include a compound of Formula (b16A), it is preferred that R12is H or C –C alkyl; more preferably R12is H or methyl. Prefe13 11 6rrably R is H. Preferably Q is either a phenyl ring or a pyridinyl ring, each ring substituted by 1 to 3 R14; more preferably Q1is a phenyl ring substituted by 1 to 2 R14. Preferably Q2is a phenyl ring substituted by 1 to 3 R15; more preferably Q2is a phenyl ring substituted by 1 to 2 R15. Preferably each R14is independently halogen, C –C alkyl, C –C 141 4 1 3haloalkyl, C1–C3alkoxy or C1–C3haloalkoxy; more preferably each R is independently chloro, fluoro, bromo, C –C haloalkyl, C –C haloalkoxy or C –C alkoxy. Preferrably each 151 2 1 2 1 2R is independently halogen, C1–C4alkyl, C1–C3haloalkoxy; more preferably each R15is independently chloro, fluoro, bromo, C1–C2haloalkyl, C1–C2haloalkoxy or C1–C2alkoxy. Specifically preferred as “DHODH inhibitors” (b16) include any one of the following (b16A-1) through (b16A-17): N-(2-fluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (b-16A- 1); N-(2,3-difluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (b16A-2); 2-oxo-4-[3-(trifluoromethyl)phenyl]-N-(2,3,4-trifluorophenyl)-3-pyrrolidinecarboxamide (b16A-3); N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (b16A-4); N-(2-fluorophenyl)-2-oxo-4-[4- phenyl]-3-pyrrolidinecarboxamide (b16A- 5); N-(2-fluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (b16A-6); N-(2,3-difluorophenyl)-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide (b16A-7); N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3- pyrrolidinecarboxamide (b16A-8); 2-oxo-4-[4-(trifluoromethyl)phenyl]-N-(2,3,4-trifluorophenyl)-3-pyrrolidinecarboxamide (b16A-9); N-(2-fluorophenyl)-4-(4-fluorophenyl)-1-methyl-2-oxo-3-pyrrolidinecarboxamide (b16A- 10); N-(2,3-difluorophenyl)-4-(3,4-difluorophenyl)-2-oxo-3-pyrrolidinecarboxamide (b16A-11); 4-(3,4-difluorophenyl)-N-(2-fluorophenyl)-2-oxo-3-pyrrolidinecarboxamide (b16A-12); N-(2,4-difluorophenyl)-4-(3,5-difluorophenyl)-2-oxo-3-pyrrolidinecarboxamide (b16A-13); N-(2,3-difluorophenyl)-4-[3-(1-methylethyl)phenyl]-2-oxo-3-pyrrolidinecarboxamide (b16A-14); N-(2,3-difluorophenyl)-2-oxo-4-[6-(trifluoromethyl)-3-pyridinyl]-3-pyrrolidinecarboxamide (b16A-15); (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3- pyrrolidinecarboxamide (b16A-16); (3S,4R)-N-(2,3-difluorophenyl)-1-methyl-4-[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]- 2-oxo-3-pyrrolidinecaboxamide (b16A-17); (3S,4S)-N-(5-chloro-1-methyl-1H-pyrazol-4-yl)-4-(3,5-dimethylphenyl)-1-methyl-2-oxo-3- pyrrolidinecarboxamide (b16A-18); and N-(5-chloro-1-methyl-1H-pyrazol-4-yl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]-3- pyrrolidinecarboxamide (b16A-19). An example of a DHODH inhibitor is tetflupyrolimet. “Other herbicides” (b17) 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 (b1) through (b16) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, 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-difluorophenyl)- N-(1-methylethyl)-5-oxo-4H-1,2,4- triazole-4-carboxamide), metam, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3- methyl-2-thienyl)isoxazole. Other herbicides also include a compound of Formula (b17A), wherein R1 is Cl, Br or CH CH CH CH CF or 2 2 2 2 33-CHF2-isoxazol-5-yl. An is rimisoxafen. “Herbicide safeners” (b18) 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, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N- (aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2- methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5- pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, 3-oxo-1-cyclohexen-l-yl 1-(3,4-dimethylphenyl)-l,6-dihydro-6-oxo-2-phenyl-5- pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone, methyl [[5- (4-bromo-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy]acetate (CAS No. 3035714-96-3), methyl [[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4- triazol-3-yl]oxy]acetate (CAS No. 2647923-10-0), and 2-methoxy-N-[[4- [[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide. 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 through 6B can be used to prepare the compounds of Formula 1. The definitions of Q, X1, X2, X3, X4and X5in the compounds of Formulae 1–13 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1a is a subset of the compounds of Formula 1, and all substituents for Formulae 3a is a subset of a compound of Formula 3, and all substituents for Formulae 4a, 4b and 4c are subsets of a compound of Formula 4, and all substituents for Formulae 11a, 11b, 11c and 11d are subsets of a compound of Formula are as defined above for Formula 1 unless otherwise noted. As shown in Scheme 1, a compound of Formula 1a (i.e. a compound of Formula 1 where V is O) can be prepared by reaction of acids of Formula 2 with an amine of Formula 3 in the presence of a dehydrative coupling reagent such as propylphosphonic anhydride, dicyclohexylcarbodiimide (DCC), N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide (EDC), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluoro- phosphate (HATU), benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP), N,N′-carbonyldiimidazo1e, 2-chloro-1,3-dimethylimidazolium chloride or 2- chloro-1-methylpyridinium iodide etc. These reactions are typically run at temperatures ranging from 0–60 °C in a solvent such as dichloromethane, acetonitrile, N,N- dimethylformamide or ethyl acetate in the presence of a base such as triethylamine, N,N- diisopropylethylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. See Org. Process Res. Dev. 2016, 20, 2, 140–177 for amide coupling conditions. Scheme 1 or 4-methoxy benzyl alcohol or dimethoxy benzyl alcohol) can be prepared by hydrolysis of an ester compound of Formula 4 under basic or acidic conditions. Hydrolysis is carried out in the presence of base (when R′ is C1–C6alkyl) typically in the presence of a solvent. The suitable bases for the reaction include, but are not limited to, lithium hydroxide, potassium hydroxide, potassium trimethylsilanoate. Hydrolysis is also can be carried out in acidic conditions (when R′ is 4-methoxy benzyl alcohol or dimethoxy benzyl alcohol) in presence of suitable solvent. Suitable acids for the reaction include trifluoro acetic acid, formic acid. A wide variety of solvents are suitable for the reaction including, but not limited to, methanol, ethanol, toluene, dichloroethane and tetrahydrofuran. The reaction is conducted at temperatures ranging from 0 °C to the boiling point of the solvent, and typically from 0 to100 °C. See Bioorganic & Medicinal Chemistry Letters 2013, 23, 1482-1485, Org. Letters,2004, 6, 4535 and WO2021236650 for hydrolysis conditions. Scheme 2 As of Formula 4 wherein compound of Formula 5 with an acrylate derivative of Formula 6 in presence of base and solvent. Chloro oximes of Formula 5 can be prepared by following procedures mentioned in Eur. J. Med.Chem. 2023, 246, 115007. The base can be selected from triethylamine (Et3N),diisopropylethylamine (DIPEA), 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU), sodium hydroxide (NaOH) potassium hydroxide (KOH), sodium bicarbonate (NaHCO3). A wide variety of co-solvents are suitable for the reaction including, but not limited to, methanol, ethanol, ethyl acetate, and tetrahydrofuran. The reaction is conducted at temperatures ranging from 0 °C to the boiling point of the solvent, and typically from 0 to 100 °C. For detailedprocedures, see Heterocycles 2005, 65, 2885–2892 and WO2005021516 for procedures.Scheme 3A (A is A-1) 4 wherein A is A-2) can be prepared by mixing of commercially available (or can be prepared by known methods) compound of Formula 7 and the commercially available compound of Formula 8, usually in the presence of a ligand, a catalyst, and a solvent. The catalyst may be one or more selected as appropriate from copper(I) chloride, copper(I) bromide, copper(II) bromide, copper iodide, copper(II) trifluoromethanesulfonate, etc. can be used in combination. The ligand may be selected from N,N,N′,N′′,N′′-pentamethyldiethylenetriamine, tris[2- (dimethylamino)ethyl]amine, 1,1,4,7,10,10-hexamethyltriethylenetetramine, and N,N,N′,N′- tetramethylethylenediamine. The solvent may be selected from but not limited to benzene, toluene, xylene, and chlorobenzene; carbon tetrachloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, ethers such as dioxane, tetrahydrofuran, diethyl ether, dimethoxyethane; acetonitrile, and The reaction is conducted at temperatures ranging from 0 °C to the boiling point of solvent, and typically from 0 to 100 °C. Fordetailed procedures, see Org. Lett. 2023, 25, 8883–8888.Scheme 3B (A is A-2) 4 9 with commercially available compound of Formula 10 in presence of base and solvent. The base can be selected from potassium carbonate (K2CO3), cesium carbonate (Cs2CO3), potassium tertiary butoxide (KO-t-Bu) and sodium hydride (NaH). For detailed procedures, see Angew.Chem. Int. Ed. 2017, 56, 12179–12183 and WO2021209268Scheme 3C (A is A3) As shown in Scheme 4, a compound of Formula 3a (i.e. a compound of Formula 3 where R1is H) can be prepared from removal of t-Boc protecting group on a compound of Formula 11 in the presence of an acid. Acids used in this reaction include trifluoracetic acid or any other inorganic acids. A compound of Formula 3c where X is X3, W and Y are O, R2is CH3is commercially available (CAS No.758684-88-7). As can be prepared from materials or those prepared by known methods of compound of Formulae 12 and 13 with dihalomethane in the presence of diethylzinc. The compounds of Formula 12 and 13 wherein W and Y are O are also either commercially available or can be prepared from commercially available Vince lactam, as described in Org. Process Res. Dev.2018, 22, 337–343, WO2017133667, Org. Lett. 2017, 19, 7, 1602–1605. The dihalomethane can be selected from CH2I2, CH2Br2, ClCH2I, BrCH2I. Alternatively, cyclopropanation reaction can also be carried out using trimethylsulfoxonium iodide in the presence of base. The base can be selected from sodium hydride, potassium tertiary butoxide, 1,8-diazabicyclo[5.4.0]undec-7-ene, potassium hydroxide and sodium hydroxide, or mixtures thereof. A wide variety of co-solvents are suitable for the reaction including, but not limited to the solvents can be selected form dichloromethane, chloroform, toluene, tetrahydrofuran. For detailed procedures, seeWO2017133667 and Advanced Synthesis & Catalysis 2024, 366, 1306–1314.Scheme 5A (Y1is Y1-1 and Z is CH2) synthesized from the corresponding compounds of Formulae 12 and 13 in the presence of an epoxidation reagent and solvent. The reagent can be selected from metachloroperbenzoic acid, hydrogen peroxide, tertiarybutyl hydrogen peroxide, oxone, and perbenzoicacid. A wide variety of co-solvents are suitable for the reaction including, but not limited to the solvents can be selected form dichloro methane, methanol, benzene. For detailed procedures, see Tetrahedron 2010, 66, Bioorg. & Med. Chem. 2010, 18, 6470–6479 and Helvetica Chimica Acta 2008, 91, 783–804.Scheme 6A (Y1is Y1-1 and Z is O) W epoxydation HNR2It is can be converted into others a 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. 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 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 presented to prepare the compounds of Formula 1. 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. 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 non-limiting Examples are illustrative of the invention. 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.1H NMR spectra are reported in ppm downfield from tetramethylsilane at 500 MHz in CDCl unless otherwise ind c t d13i ae . H NMR spectra are reported in ppm downfield from tetramethylsilane; “s” means singlet, “d” means doublet, “t” means triplet, “q” means quartet, “m” means multiplet, “dd” means doublet of doublets, “ddd” means doublet of double doublets, “dt” means doublet of triplets, and “br s” means broad singlet. Mass spectra (MS) 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, or (M–1) formed by the loss of H+ (molecular weight of 1) from the molecule, observed by using liquid chromatography coupled to a mass spectrometer (LCMS) using either atmospheric pressure chemical ionization (AP+) where “amu” stands for unified atomic mass units. SYNTHESIS EXAMPLE 1 Preparation of methyl (1S,2S,4R,5R)-4-[[3-(3,5-difluorophenyl)-5-methyl-4H-isoxazole-5- carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 124) Step A: Preparation of methyl 3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolecarboxylate To a stirred solution of (Z)-3,5-difluoro-N-hydroxybenzenecarbonimidoyl chloride (16 g, 83.525 mmol) prepared by following procedure described in Eur. J. Med. Chem.2023, 246, 115007 in ethyl acetate, methyl methacrylate (10.035 g, 100.23 mmol) and NaHCO3(10.525 g, 4.875 mL, 2.159 g / mL, 125.287 mmol) were added and stirred at room temperature for 16 h. Upon completion, the reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (2 × 100 mL). The combined organic layers were washed with water and brine solution, dried over anhydrous sodium sulphate, and concentrated to afford the title compound (14 g, 59% yield) as a white solid.1H NMR δ ppm 7.19–7.17 (m, 3H), (m, 1H), 3.84 (d, 1H), 3.82 (s, 3H), 3.17 (d, 1H, 1.73 (s, 3H). Step B: Preparation of 3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolecarboxylic acid To a stirred solution of methyl 3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolecarboxylate (13.5 g, 52.895 mmol), (i.e. the product of Step A) was taken in tetrahydrofuran (60 mL), methanol (20 mL) to this reaction mixture at 0 °C temperature LiOH^H2O (3.33 g, 2.205 mL, 1.51 g / mL, 79.343 mmol, dissolved in 10 mL of water) was added and stirred for 16 h by allowing the reaction mixture to assume ambient temperature. Tetrahydrofuran and methanol were removed under vacuum and the reaction mixture acidified to pH ~3 with 1 N aqueous hydrochloric acid and extracted with ethyl acetate (2 × 100 mL) and the combined organic layers were washed with water and brine solution, dried over anhydrous sodium sulphate, and concentrated to afford the title compiund as white solid (12 g, 89% yield).1H NMR δ ppm 9.16 (br s, 1H), 7.20–7.15 (m, 2H), 6.88 (tt, 1H), 3.83 (d, 1H), 3.23 (d, 1H), 1.78 (s, 3H). Step C: Preparation of methyl (1S,2S,4R,5R)-4-amino-6-oxabicyclo[3.1.0]hexane-2- carboxylate To a stirred solution of methyl (1S,2S,4R,5R)-4-[[(1,1- dimethylethoxy)carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (3 g, 11.6 mmol) prepared according to the procedure described in Tetrahedron 2010, 66, 3599-3607, in dichloromethane (30 mL), trifluoroacetic acid (5 mL) was added at 0 °C and stirred for 4 h at the same temperature. Then, the reaction mixture was allowed to warm to room temperature and concentrated to give crude compound. The crude mixture was triturated with hexanes to afford the title compound as the trifluoroacetic acid salt. MS [M+H]+: 158.06.1H NMR (400 MHz, DMSO-d6) δ 1.42–1.50 (m, 1H), 2.04–2.11 (m, 1H), 3.23 (t, 1H), 3.65– 3.72 (m, 5H), 3.83–3.84 (m, 1H), 8.16 (bs, 3H). Step D: Preparation of methyl (1S,2S,4R,5R)-4-[[3-(3,5-difluorophenyl)-5-methyl-4H- isoxazole-5-carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate To a stirred solution of 3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolecarboxylic acid (8.5 g, 35.241 mmol) (i.e. the product of Step B) in dichloromethane (100 mL) and methyl (1S,2S,4R,5R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (as the trifluoroacetic acid salt) (9.522 g, 35.241 mmol) (i.e. the product of Step C) and benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 25.675 g, 49.338 mmol), N,N-diisopropylamine (9.109 g, 12.277 mL, 0.742 g / mL, 70.483 mmol), were added at 0 °C and stirred for 14 to 16 h by allowing the reaction mixture to assume ambient temperature. The concentrated reaction was then mixture diluted with ethyl acetate (100 . The organic mixture was washed with water (50 mL) and brine (50 mL). The organic was separated, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to get crude as a residue. The crude was purified by column chromatography on silica gel by eluting with ethyl acetate in hexanes (0 to 40% gradient) to afford the title compound as a diastereomeric mixture (7 g, 47% yield).1H NMR δ ppm 7.21–7.13 (m, 2H), 7.12–7.02 (m, 1H), 6.93–6.84 (m, 1H), 4.43 (br dd, 1H), 3.82–3.70 (m, 5H), 3.59 (dd, 1H), 3.20 (dd, 1H), 3.00–2.90 (m, 1H), 2.29–2.10 (m, 1H), 1.65– 1.47 (m, 1H). SYNTHESIS EXAMPLE 2 Preparation of methyl (1R,2S,4R,5S)-4-[[3-(3,5-difluorophenyl)-5-methyl-4H-isoxazole-5- carbonyl]amino]bicyclo[3.1.0]hexane-2-carboxylate (Compound 112) To a stirred solution of 3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolecarboxylic acid (0.155 g, 0.644 mmol) (i.e the product of Example 1, Step B), methyl (1R,2S,4R,5S)-4-aminobicyclo[3.1.0]hexane-2-carboxylate (100 mg, 0.644 mmol, prepared according to the procedure described in WO2017133669) in dichloromethane (5 mL) triethylamine (0.196 g, 1.933 mmol), benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 0.503 g, 0.967 mmol) were added respectively at room temperature. The reaction mixture was stirred for 16 h at ambient temperature. After the completion of the reaction, the reaction mixture was diluted with water (20 mL), extracted with dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure to get crude residue. The crude product was purified by column chromatography on silica gel eluting with ethyl acetate in petroleum ether (0 to 50% gradient) to afford the title compound (160 mg, 62% yield) as a diastereomeric mixture. SYNTHESIS EXAMPLE 3 Preparation of methyl (3S)-3-[[3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5- carbonyl]amino]bicyclo[3.1.0]hexane-1-carboxylate (Compound 153) Step A: Preparation of methyl (1R,3R)-3-[[(1,1- dimethylethoxy)carbonyl]amino]bicyclo[3.1.0]hexane-1-carboxylate To a stirred solution of trimethylsulfoxonium iodide (TMSOI) (11.4 g, 51.8 mmol) in dimethylsulfoxide (50 mL) sodium hydride (2.24 g, 51.8 mmol, 60% in mineral oil) was added at 0 °C and stirred for 1 h at room temperature. Then, methyl (4R)-4-[[(1,1- dimethylethoxy)carbonyl]amino]-1-cyclopentene-1-carboxylate (5 g, 20 mmol) dissolved in dimethylsulfoxide (10 mL) (prepared by using the procedure described in Org. Lett.2017, 19, 1602−1605) was added and heated at 50 °C for 2 h. Cooled the reaction mixture poured into ice cold water and extracted with ethyl acetate (3 × 50 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to get the crude compound. The crude was purified by column by eluting with a gradient of 10 to 20% ethyl acetate in petroleum ether to afford the title (2.8 g, 36% yield) as an off white solid. MS [M+H]+: 256.31. Step B: Preparation of methyl (1S,3S,5S)-3-aminobicyclo[3.1.0]hexane-1-carboxylate To a stirred solution of methyl (1R,3R)-3-[[(1,1- dimethylethoxy)carbonyl]amino] hexane-1-carboxylate (i.e, product of Example 3, Step A) in cyclopentyl methyl ether (CPME, 10 mL), 4 M hydrochloric acid in dioxane (0.214 g, 1.469 mL, 4 M, 5.875 mmol) was added at 0 °C and stirred for 2 h at ambient temperature. The concentrated reaction mixture was triturated with hexane to afford the title compound as the hydrochloride salt (180 mg, 93% yield) as white solid. MS [M+H]+: 156.0.1H NMR (dmso-d6) δ ppm 8.22 (br s, 3H), 4.00–3.92 (m, 1H), 3.61 (s, 3H), 3.26 (br d, 1H), 2.26–2.15 (m, 2H), 2.12–2.07 (m, 1H), 1.95–1.82 (m, 2H), 1.22 (br dd, 1H). Step C: Preparation of methyl (3S)-3-[[3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole- 5-carbonyl]amino]bicyclo[3.1.0]hexane-1-carboxylate To a stirred solution of 3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carboxylic acid (500 mg, 1.9 mmol) and methyl (3S)-3-aminobicyclo[3.1.0]hexane-1-carboxylate hydrochloride (1:1) (370 mg, 2.3 mmol), were taken in N,N-dimethylformamide (5 mL), propylphosphonic anhydride (T3P) (2.5 mL, 3.8 mmol, 50% wt% in ethyl acetate) and triethylamine (0.8 mL, 6 mmol) were added at 0 °C and stirred for 16 h by allowing the reaction mixture to warm to ambient temperature. Water (10 mL) was then added to the reaction mixture and extracted with ethyl acetate (3 × 20 mL). The organic fractions were combined, filtered through sodium sulfate, concentrated to get crude compound. The crude was purified by column chromatography by eluting with a gradient of 20 to 40% ethyl acetate in petroleum ether to afford the title compound as off-white solid (250 mg, 33% yield, diastereomeric mixture). MS [M+H]+: 391.57.1H NMR (400 MHz, CDCl3) δ ppm 7.17–7.15 (m, 2H), 6.91–6.86 (m, 1H), 6.64–6.63 (m, 1H), 6.17–6.09 (m, 1H), 5.53–5.48 (m, 1H), 5.34–5.31 (m, 1H), 3.99–3.90 (m, 1H), 3.86–3.85 (m, 1H), 3.67–3.65 (m, 3H), 3.27–3.26 (m ,1H), 2.41–2.38 (m, 2H), 2.26–2.20 (m, 1H), 1.89– 1.86 (m, 1H), 1.69–1.67 (m, 1H), 1.39–1.36 (m, 1H), 0.89–0.87 (m, 1H). SYNTHESIS EXAMPLE 4 Preparation of methyl (1S,2S,4R,5R)-4-[[(E)-4-(3,5-difluorophenyl)-2,2-difluoro-but-3- enoyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 76) Step A: Preparation of ethyl (E)-4-(3,5-difluorophenyl)-2,2-difluoro-but-3-enoate To a stirred solution of 1-ethenyl-3,5-difluorobenzene (2.5 g, 17.85 mmol, prepared as described in WO2023135233), ethyl bromodifluoroacetate (5.41 g, 26.78 mmol) in acetonitrile (25 mL) was added N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMEDTA) (4.6 g, 26.77 mmol), followed by CuI (339 mg, 1.785 mmol) and degassed under argon gas for 10 min at ambient temperature. The mixture was heated to 80 °C in sealed tube. After 7 h, the reaction mixture was in ethyl acetate and filtered through Celite®diatomaceous earth filter aid. The obtained filtrate was dried over anhydrous Na2SO4and evaporated. The resulting crude compound was purified by silica gel column chromatography eluting with 15% ethyl acetate in petroleum ether to isolate the title compound as a liquid (570 mg).1H NMR (400 MHz, CDCl3) δ ppm 7.02–6.94 (m, 3H), 6.83–6.75 (m, 1H), 6.78–6.27 (m, 1H), 4.38–4.33 (q, 2H), 1.35 (t, 3H). Step B Preparation of (3E)-4-(3,5-difluorophenyl)-2,2-difluoro-3-butenoic acid At 0 °C, to a stirred solution of ethyl (E)-4-(3,5-difluorophenyl)-2,2-difluoro-but-3- enoate (570 mg, 2.1 mmol) (i.e., the product of Example 4, Step A) in tetrahydrofuran (10 mL) and water (5 mL) was added lithium hydroxide (267 mg, 6.52 mmol). After addition, the reaction mixture was allowed to stir at ambient temperature. After 3 h, the reaction mixture was quenched with a 1 N aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, evaporated to isolate a crude compound which was triturated with n-pentane to afford the title compound (200 mg) as an off-white solid.1H NMR (400 MHz, dmso-d6) δ ppm 7.50–7.28 (m, 2H), 7.27–7.23 (m, 1H), 7.11–7.08 (m, 1H), 6.87–6.79 (m, 1H). Step C: Preparation of methyl (1S,2S,4R,5R)-4-[[(E)-4-(3,5-difluorophenyl)-2,2- difluoro-but-3-enoyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate: To a stirred solution of (3E)-4-(3,5-difluorophenyl)-2,2-difluoro-3-butenoic acid (200 mg, 0.854 mmol) (i.e., the product of Example 4, Step B) was taken up in dichloromethane (5 mL) to this at ambient temperature was added methyl (1S,2S,4R,5R)-4- amino-6-oxabicyclo[3.1.0]hexane-2-carboxylate (0.134 g, 0.854 mmol) (i.e., the product of Example 1, Step C) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (0.408 g, 0.815 mL, 50 w / v %, 1.281 mmol), triethylamine (0.259 g, 2.562 mmol) were added and stirred at ambient temperature for 16 h. The reaction mixture was concentrated and diluted with ethyl acetate (30 mL), washed with water (10 mL) and brine (10 mL). The organic layer was separated and dried over sodium sulfate, filtered and concentrated to provide the desired product (250 mg, 75% yield).1H NMR δ ppm 7.02 (t, 1H), 7.01–6.95 (m, 2H), 6.81 (tt, 1H), 6.69 (br d, 1H), 6.38 (td, 1H), 4.54 (q, 1H), 3.85–3.72 (m, 4H), 3.62 (dd, 1H), 3.00 (ddd, 1H), 2.28 (td, 1H), 1.64–1.57 (m, 1H). EXAMPLE 5 Preparation of methyl (1R,2S,4R,5S)- [(E)-4-(3,5-difluorophenyl)-2,2-difluoro-but-3- enoyl]amino]bicyclo[3.1.0]hexane-2-carboxylate (Compound 77) To a stirred solution of (3E)-4-(3,5-difluorophenyl)-2,2-difluorobut-3-enoic acid (200 mg, 0.854 mmol) (i.e., the product of Step B from Example 4) was taken in dichloromethane (5 mL) to this at ambient temperature methyl (1R,2S,4R,5S)-4- aminobicyclo[3.1.0]hexane-2-carboxylate (133 mg, 0.854 mmol), prepared according to the procedure described in WO2017133669 and 2,4,6-tripropyl-1,3,5,2,4,6- trioxatriphosphorinane-2,4,6-trioxide (0.408 g, 0.815 mL, 50 w / v %, 1.281 mmol) triethylamine (0.259 g, 2.562 mmol) were added and stirred at ambient temperature for 16 h. The reaction mixture was concentrated and diluted with ethyl acetate (30 mL), washed with water (10 mL) and brine (10 mL). The organic layer was separated dried over sodium sulfate, filtered and concentrated to provide the title product (250 mg, 75% yield).1H NMR δ ppm 7.02–6.93 (m, 3H), 6.80 (tt, 1H), 6.48–6.44 (m, 1H), 6.38 (td, 4.64–4.54 (m, 1H), 3.71 (s, 3H), 3.10 (ddd, 10.8 Hz, 1H), 2.25 (td, 1H), 1.74–1.63 (m, 2H), 1.40 (td, 1H), 0.90–0.84 (m, 1H), 0.75 (td, 1H), 0.56–0.47 (m, 1H). SYNTHESIS EXAMPLE 6 Preparation of methyl (2S,4R)-4-[[1-(3,5-difluorophenyl)-3-methyl-2-oxo-azetidine-3- carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 74) To a stirred solution of 1-(3,5-difluorophenyl)-3-methyl-2-oxo-azetidine-3-carboxylic acid (300 mg, 1.24 mmol) (prepared as described in WO2021209268) in dichloromethane (6 mL), methyl (1S,2S,4R,5R)-4-amino-6-oxabicyclo[3.1.0]hexane-2-carboxylate, as the trifluoroacetic acid salt (0.472 g, 1.74 mmol) (i.e., the product of Example 1, Step C) and PyBOP (0.97 g, 1.86 mmol), triethylamine (0.38 g, 5.2 mL, 0.726 g / mL, 3.73 mmol), were added at 0 °C and stirred for 16 h by allowing the reaction mixture to warm to ambient temperature. The reaction mixture was then concentrated and diluted with ethyl acetate (100 mL). Washed with water (50 mL), brine (50 mL) and the organic layer was separated and dried over anhydrous sodium sulphate and filtered, then concentrated under reduced pressure to provide a crude residue. The crude residue was purified by column chromatography on silica gel by eluting with ethyl acetate in hexanes with a gradient of 0 to 40% ethyl acetate in hexanes to afford the title compound as a diastereomeric mixture (250 mg, 53% yield).1H NMR (500 MHz, dmso-d6) δ ppm 8.11–8.15 (m, 1H), 7.05–7.10 (m, 2H), 6.97–7.02 (m, 1H), 4.25–4.31 (m, 1H), 4.04–4.08 (s, 1H), 3.65–3.68 (m, 4H), 3.52–3.58 (m, 2H), 3.08–3.12 (m, 1H), 1.88–1.95 (m, 1H), 1.51–1.60 (m, 4H), 1.22–1.25 (m, 1H). EXAMPLE 7 Preparation of methyl (2S,4R)-4-[ difluorophenyl)-3-methyl-2-oxo-azetidine-3- carbonyl]amino]bicyclo[3.1.0]hexane-2-carboxylate (Compound 75) To a stirred solution of 1-(3,5-difluorophenyl)-3-methyl-2-oxo-azetidine-3-carboxylic acid (300 mg, 1.24 mmol) (prepared according to WO2021209268) in dichloromethane (6 mL) methyl (1S,2S,4R,5R)-4-amino-6-oxabicyclo[3.1.0]hexane-2-carboxylate (HCl salt) (0.261 g, 1.36 mmol) (i.e., the product of Example 1, Step C) and PyBOP (0.9 g, 1.74 mmol), triethylamine (0.38 g, 5.2 mL, 0.726 g / mL, 3.73 mmol), were added at 0 °C and stirred for 16 h by allowing the reaction mixture to warm to ambient temperature. The concentrated reaction mixture was then diluted with ethyl acetate (100 mL), washed with water (50 mL) and brine (50 mL). The organic layer was separated and dried over anhydrous sodium sulphate and filtered and concentrated under reduced pressure to get crude residue. The crude was purified by column chromatography on silica gel by eluting with ethyl acetate in hexanes with a gradient of 0 to 40% to afford the title compound as the diastereomeric mixture (220 mg, 47% yield).1H NMR (500 MHz, dmso-d6) δ ppm 7.74–7.55 (m, 1H), 6.97–7.08 (m, 3H), 4.42 (m, 1H), 4.04–4.06 (d, 1H), 3.61 (s, 3H), 3.54–3.55 (d, 1H), 3.03–3.04 (m, 1H), 1.81–1.83 (m, 1H), 1.47–1.59 (m, 6H), 0.73–0.74 (m, 1H), 0.31–033 (m, 1H). By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 6600 can be prepared. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, n-Pr means normal-propyl (i.e., n-propyl), i-Pr means isopropyl, i-Bu means isobutyl, t-Bu means tert-butyl, c-Pr means cyclopropyl, c-Bu means cyclobutyl, c-Pent means cyclopentyl, c-Hex means cyclohexyl, c-Hept means cycloheptyl, OMe means methoxy, SMe means methylthio, CN means cyano (i.e., C≡N), Ph means phenyl, cis means cis-isomer, and trans means trans-isomer. TABLE 1 X2is H, X3is F, X5is F, R5is Me, and R2is defined below.R2 R2 R2 R2 R2 R2 X2is H, X3is F, X5is F, R5is Me, and R2is below.R2R2R2R2R2R2Et c-Bu tetrahydrofuran-3-yl CH2Cl CH2C≡CH (CH2)2S(=O)2CH33cted t e sa e as a e aoe, ecep a e o ea g a e .e. s , s , X5is F, R5is Me”) is replaced with the respective row headings shown below. Table Row Heading Table Row Heading 2X2is H, X3is Cl, X5is Cl, R5is Me 3 X2is H, X3is F, X5is Cl, R5is Me4 X2is H, X3is F, X5is H, R5is Me 5 X2is H, X3is Cl, X5is H, R5is Me6 X2is H, X3is CN, X5is H, R5is Me 7 X2is H, X3is CN, X5is F, R5is Me8 X2is Cl, X3is F, X5is F, R5is Me 9 X2is F, X3is F, X5is F, R5is Me10 X2is F, X3is Cl, X5is Cl, R5is Me 11 X2is F, X3is F, X5is Cl, R5is Me12 X2is H, X3is F, X5is Br, R5is Me 13 X2is H, X3is Cl, X5is Br, R5is Me14 X2is H, X3is F, X5is CN, R5is Me 15 X2is H, X3is Cl, X5is CN, R5is Me16 X2is H, X3is F, X5is OMe, R5is Me 17 X2is H, X3is F, X5is OCF , R5is Me18 X2is H, X3is F, X5is CF , R5is Me 19 X2is H, X3is F, X53is CHF , R5is Me20 X2 3 53is H, X is F, X is O5 2 3 5 52CHF , R is Me 21 X is H, X is F, X is F, R is Et23 5 5222 X is H, X is Cl, X is Cl, R is Et 23 X2is H, X3is F, X5is Cl, R5is Et24 X2is H, X3is F, X5is H, R5is Et 25 X2is H, X3is Cl, X5is H, R5is Et26 X2is H, X3is CN, X5is H, R5is Et 27 X2is H, X3is CN, X5is F, R5is Et28 X2is Cl, X3is F, X5is F, R5is Et 29 X2is F, X3is F, X5is F, R5is Et30 X2is F, X3is Cl, X5is Cl, R5is Et 31 X2is F, X3is F, X5is Cl, R5is Et32 X2is H, X3is F, X5is Br, R5is Et 33 X2is H, X3is Cl, X5is Br, R5is Et34 X2is H, X3is F, X5is CN, R5is Et 35 X2is H, X3is Cl, X5is CN, R5is Et36 X2is H, X3is F, X5is OMe, R5is Et 37 X2is H, X3is F, X5is OCF , R5is Et38 X2is H, X3is F, X5is CF , R5is Et 39 X2is H, X3is F, X53is CHF , R5is Et40 X2 3 53is H, X is F, X is O5 2 3 5 52CHF , R is Et 41 X is H, X is F, X is F, R is OMe23 5 5242 X is H, X is Cl, X is Cl, R is OMe 43 X2is H, X3is F, X5is Cl, R5is OMe44 X2is H, X3is F, X5is H, R5is OMe 45 X2is H, X3is Cl, X5is H, R5is OMe46 X2is H, X3is CN, X5is H, R5is OMe 47 X2is H, X3is CN, X5is F, R5is OMe48 X2is Cl, X3is F, X5is F, R5is OMe 49 X2is F, X3is F, X5is F, R5is OMe50 X2is F, X3is Cl, X5is Cl, R5is OMe 51 X2is F, X3is F, X5is Cl, R5is OMe52 X2is H, X3is F, X5is Br, R5is OMe 53 X2is H, X3is Cl, X5is Br, R5is OMe Table Row Heading Table Row Heading 54 X2is H, X3is F, X5is CN, R5is OMe 55 X2is H, X3is Cl, X5is CN, R5is OMe56 X2is H, X3is F, X5is OMe, R5is OMe 57 X2is H, X3is F, X5is OCF , R5is OMe58 X2is H, X3is F, X5is CF3, R5is OMe 59 X2is H, X3is F, X53is CHF2, R5is OMe60 X2is H, X3is F, X5is OCHF2, R5is OMe 61 X2is H, X3is F, X5is F, R5is SMe62 X2is H, X3is Cl, X5is Cl, R5is SMe 63 X2is H, X3is F, X5is Cl, R5is SMe64 X2is H, X3is F, X5is H, R5is SMe 65 X2is H, X3is Cl, X5is H, R5is SMe66 X2is H, X3is CN, X5is H, R5is SMe 67 X2is H, X3is CN, X5is F, R5is SMe68 X2is Cl, X3is F, X5is F, R5is SMe 69 X2is F, X3is F, X5is F, R5is SMe70 X2is F, X3is Cl, X5is Cl, R5is SMe 71 X2is F, X3is F, X5is Cl, R5is SMe72 X2is H, X3is F, X5is Br, R5is SMe 73 X2is H, X3is Cl, X5is Br, R5is SMe74 X2is H, X3is F, X5is CN, R5is SMe 75 X2is H, X3is Cl, X5is CN, R5is SMe76 X2is H, X3is F, X5is OMe, R5is SMe 77 X2is H, X3is F, X5is OCF , R5is SMe78 X2is H, X3is F, X5is CF3, R5is SMe 79 X2is H, X3is F, X53is CHF2, R5is SMe80 X2is H, X3is F, X5is OCHF2, R5is SMe 81 X2is H, X3is F, X5is F, R5is CH23 5 52Cl82 X is H, X is Cl, X is Cl, R is CH2Cl 83 X2is H, X3is F, X5is Cl, R5is CH23 5 5 22Cl84 X is H, X is F, X is H, R is CH2Cl 85 X is H, X3is Cl, X5is H, R5is CH23 5 5 2 3 5 52Cl86 X is H, X is CN, X is H, R is CH Cl 87 X is H, X is CN, X is F, R is CH Cl82 3 5 528 X is Cl, X is F, X is F, R is2 3 5 52CH2Cl 89 X is F, X is F, X is F, R is CH22Cl90 X is F, X3is Cl, X5is Cl, R5is CH2Cl 91 X2is F, X3is F, X5is Cl, R5is CH232Cl92 X is H, X is F, X5is Br, R5is CH2Cl 93 X2is H, X3is Cl, X5is Br, R5is CH23 52Cl94 X is H, X is F, X is CN, R5is CH2Cl 95 X2is H, X3is Cl, X5is CN, R5is CH23 5 52Cl96 X is H, X is F, X is OMe, R is CH2Cl 97 X2is H, X3is F, X5is OCF3, R5is CH23 52Cl98 X is H, X is F, X is CF3, R5is CH2Cl 99 X2is H, X3is F, X5is CHF2, R5is CH232Cl100 X is H, X is F, X5is OCHF2, R5is CH2Cl 101 X2is H, X3is F, X5is F, R5is CH OCH102 X2is H, X3is Cl, X5is Cl, R5 2 3 5 52 3is CH OCH 103 X is H, X is F, X is Cl, R is Me23 5 52 3104 X is H, X is F, X is H, R is CH2OCH3 105 X2is H, X3is Cl, X5is H, R5is Me106 X2is H, X3is CN, X5is H, R5is CH2OCH3 107 X2is H, X3is CN, X5is F, R5isCH2OCH108 X2i C,3F X5,5 23s l X is , is F R is CH OCH 109 X is F, X3is F, X5is F, R5is CH OCH12 3 5 52 310 X is F, X is Cl, X is Cl2 3 5 52 3, R is CH OCH 111 X is F, X is F, X is Cl, R is CH OCH12 3 5 52 312 X is H, X is F, X is Br,2 3 5 52 3R is CH2OCH3 113 X is H, X is Cl, X is Br, R isCH2s ,3 52OCHiF X5 23114 X i H X s , is CN, R is CH2OCH3 115 X is H, X3is Cl, X5is CN, R5isCH2s ,3 52OCHiF X5 23116 X i H X s , is OMe, R is 117 X is H, X3is F, X5is OCF3, R5isCH2OCH3CH2OCH3 Table Row Heading Table Row Heading 118 X2is H, X3is F, X5is CF3, R5is 119 X2is H, X3is F, X5is CHF2, R5isCH22OCH3CH2OCH120 X is H, X3is F, X5is OCHF2, R5is 121 X23is H, X3is F, X5is F, R5is CH2CNCH22OCH3122 X is H, X3is Cl, X5is Cl, R5is CH CN 123 X2is H, X3is F, X5is Cl, R5is CH CN12 3 5 5224 X is H, X is F, X is H, R is C2 3 5 52H2CN 125 X is H, X is Cl, X is H, R is CH2CN126 X2is H, X3is CN, X5is H, R5is CH2CN 127 X2is H, X3is CN, X5is F, R5is CH128 X2is Cl, X32CNis F, X5is F, R5is CH2CN 129 X2is F, X3is F, X5is F, R5is CH130 X2is F, X3is Cl, X5is Cl, R5is CH2CN 131 X22CNis F, X3is F, X5is Cl, R5is CH132 X2is H, X3is F, X5is Br, R5is CH2CN 133 X2is H, X32CNis Cl, X5is Br, R5is CH134 X2is H, X3is F, X5is CN, R5is CH CN 135 X2is H, X3is Cl, X52CNis CN, R5is CH CN12 3 5 5236 X is H, X is F, X is OMe, R i2 3 5 52s CH2CN 137 X is H, X is F, X is OCF3, R isCH2CN138 X2is H, X3is F, X5is CF3, R5is CH2CN 139 X2is H, X3is F, X5is CHF2, R5isCH2CN140 X2is H, X3is F, X5is OCHF2, R5is 141 X2is H, X3is F, X5is F, R5is CH2BrCH2CN142 X2is H, X3is Cl, X5is Cl, R5is CH Br 143 X2is H, X3is F, X5is Cl, R5is CH Br12 3 5 5244 X is H, X is F, X is H, R is C2 3 5 52H2Br 145 X is H, X is Cl, X is H, R is CH2Br146 X2is H, X3is CN, X5is H, R5is CH2Br 147 X2is H, X3is CN, X5is F, R5is CH148 X2is Cl, X32Bris F, X5is F, R5is CH2Br 149 X2is F, X3is F, X5is F, R5is CH150 X2is F, X3is Cl, X5is Cl, R5is CH2Br 151 X22Bris F, X3is F, X5is Cl, R5is CH152 X2is H, X3is F, X5is Br, R5is CH2Br 153 X2is H, X32Bris Cl, X5is Br, R5is CH154 X2is H, X3is F, X5is CN, R5is CH Br 155 X2is H, X3is Cl, X52Bris CN, R5is CH Br12 3 5 5256 X is H, X is F, X is OMe, R i2 3 5 52s CH Br 157 X is H, X is F, X is OCF , R is CH Br15 X2s3 5 52H, is F X is F , R2 3 53528 i X , C is CH Br 159 X is H, X is F, X is CHF , R is CH Br23 5352160 X is H, X is F, X is OCHF2 3 5 52 2, R is CH Br 161 X is H, X is F, X is F, R is CH F23 5 52 2162 X is H, X is Cl, X is Cl, R2 3 5 52is CH2F 163 X is H, X is F, X is Cl, R is CH2F164 X2is H, X3is F, X5is H, R5is CH2F 165 X2is H, X3is Cl, X5is H, R5is CH166 X is H, X3is CN, X5is H, R52F2is CH2F 167 X2is H, X3is CN, X5is F, R5is CH163 5 5 2 3 5 52F8 X2is Cl, X is F, X is F, R is CH F 169 X is F, X is F, X is F, R is CH F12 3 5 5270 X is F, X is Cl, X is Cl, R i2 3 5 52s CH2F 171 X is F, X is F, X is Cl, R is CH22F172 X is H, X3is F, X5is Br, R5is CH2F 173 X2is H, X3is Cl, X5is Br, R5is CH174 X is H, X3is F, X52F2is CN, R5is CH2F 175 X2is H, X3is Cl, X5is CN, R5is CH176 X is H, X3is F, X5is OMe, R5is CH2F 177 X2is H, X32F2is F, X5is OCF5178 X is H, X is F, X is CF , R is CH F 179 X is H, X is F, X53, R is CH35 5 2 32F2is CHF , R5is CH F23 5352180 X is H, X is F, X is OCHF2 3 5 52 22, R is CH2F 181 X is H, X is F, X is F, R is CHF2 Table Row Heading Table Row Heading 182 X2is H, X3is Cl, X5is Cl, R5is CHF 183 X2is H, X3is F, X5is Cl, R5is CHF12 3 5 5284 X is H, X is2 3 5 52F, X is H, R is CHF 185 X is H, X is Cl, X is H, R is CHF12 3 5 5286 X is H, X is2 3 5 52CN, X is H, R is CHF 187 X is H, X is CN, X is F, R is CHF12 3 5 5288 X is Cl, X i2 3 5 52s F, X is F, R is CHF 189 X is F, X is F, X is F, R is CHF12 3 5 5290 X is F, X is2 3 5 52Cl, X is Cl, R is CHF 191 X is F, X is F, X is Cl, R is CHF12 3 5 5292 X is H, X is2 3 5 52F, X is Br, R is CHF 193 X is H, X is Cl, X is Br, R is CHF12 3 5 5294 X is H, X is2 3 5 52F, X is CN, R is CHF 195 X is H, X is Cl, X is CN, R is CHF12 3 5 5296 X is H, X is2 3 5 52F, X is OMe, R is CHF 197 X is H, X is F, X is OCF , R is CHF19 X2s3 5 52H, i2 3 53528 i X s F, X is CF , R is CHF 199 X is H, X is F, X is CHF , R is CHF23 5352200 X is H, X2 3 5 52 2is F, X is OCHF , R is CHF 201 X is H, X is F, X is F, R is CH=CH23 5 52 2202 X is H, X i2 3 5 52s Cl, X is Cl, R is CH=CH 203 X is H, X is F, X is Cl, R is CH=CH22 3 5 5204 X is H, X is2 3 5 52F, X is H, R is CH=CH 205 X is H, X is Cl, X is H, R is CH=CH22 3 5 5206 X is H, X is2 3 5 52CN, X is H, R is CH=CH 207 X is H, X is CN, X is F, R is CH=CH22 3 5 5208 X is Cl, X i2 3 5 52s F, X is F, R is CH=CH 209 X is F, X is F, X is F, R is CH=CH22 3 5 5210 X is F, X is2 3 5 52Cl, X is Cl, R is CH=CH 211 X is F, X is F, X is Cl, R is CH=CH22 3 5 5212 X is H, X is2 3 5 52F, X is Br, R is CH=CH 213 X is H, X is Cl, X is Br, R is CH=CH22 3 5 5214 X is H, X is2 3 5 52F, X is CN, R is CH=CH2 215 X is H, X is Cl, X is CN, R isCH=CH216 X2is3 5 5 22H, X is F, X is OMe, R is CH=CH2 217 X is H, X3is F, X5is OCF3, R5isCH=CH218 X2is H, X3is F, X5is CF3, R5is CH=CH2 219 X22is H, X3is F, X5is CHF2, R5isCH=CH220 X2is H, X3is F, X5is OCHF2, R5is 221 X22is H, X3is F, X5is F, R5is c-PrPrPr Table Row Heading Table Row Heading 248 X2is Cl, X3is F, X5is F, R5is CF 249 X2is F, X3is F, X5is F, R5is CF22 3 5 5350 X is F, X is Cl, X is2 3 5 53Cl, R is CF 251 X is F, X is F, X is Cl, R is CF22 3 5 5352 X is H, X is F, X is B2 3 5 53r, R is CF 253 X is H, X is Cl, X is Br, R is CF22 3 5 5354 X is H, X is F, X is C2 3 5 53N, R is CF 255 X is H, X is Cl, X is CN, R is CF22 3 5 5356 X is H, X is F, X is O2 3 5 53Me, R is CF 257 X is H, X is F, X is OCF , R is CF25 X2s3 5 53H, is F X is2 3 53538 i X , CF , R is CF 259 X is H, X is F, X is CHF , R is CF23 5353260 X is H, X is F, X i2 3 5 52 3s OCHF , R is CF 261 X is H, X is F, X is F, R is OCF23 5 52 3262 X is H, X is Cl, X i2 3 5 53s Cl, R is OCF 263 X is H, X is F, X is Cl, R is OCF22 3 5 5364 X is H, X is F, X is H2 3 5 53, R is OCF 265 X is H, X is Cl, X is H, R is OCF22 3 5 5366 X is H, X is CN, X is2 3 5 53H, R is OCF 267 X is H, X is CN, X is F, R is OCF22 3 5 5368 X is Cl, X is F, X is2 3 5 53F, R is OCF 269 X is F, X is F, X is F, R is OCF22 3 5 5370 X is F, X is Cl, X is2 3 5 53Cl, R is OCF 271 X is F, X is F, X is Cl, R is OCF22 3 5 5372 X is H, X is F, X is B2 3 5 53r, R is OCF 273 X is H, X is Cl, X is Br, R is OCF22 3 5 5374 X is H, X is F, X is C2 3 5 53N, R is OCF 275 X is H, X is Cl, X is CN, R is OCF22 3 5 5376 X is H, X is F, X is O2 3 5 53Me, R is OCF 277 X is H, X is F, X is OCF , R is OCF27 X2s3 5 53H, is F X is2 3 53538 i X , CF , R is OCF 279 X is H, X is F, X is CHF , R is OCF23 5353280 X is H, X is F, X i2 3 5 52 3s OCHF , R is OCF 281 X is H, X is F, X is F, R is OCHF23 5 52 3282 X is H, X is Cl, X i2 3 5 52s Cl, R is OCHF 283 X is H, X is F, X is Cl, R is OCHF22 3 5 5284 X is H, X is F, X is H2 3 5 52, R is OCHF 285 X is H, X is Cl, X is H, R is OCHF22 3 5 5286 X is H, X is CN, X is2 3 5 52H, R is OCHF 287 X is H, X is CN, X is F, R is OCHF22 3 5 5288 X is Cl, X is F, X is2 3 5 52F, R is OCHF 289 X is F, X is F, X is F, R is OCHF22 3 5 5290 X is F, X is Cl, X is2 3 5 52Cl, R is OCHF 291 X is F, X is F, X is Cl, R is OCHF22 3 5 5292 X is H, X is F, X is B2 3 5 52r, R is OCHF 293 X is H, X is Cl, X is Br, R is OCHF22 3 5 5294 X is H, X is F, X is C2 3 5 52N, R is OCHF 295 X is H, X is Cl, X is CN, R is OCHF22 3 5 5296 X is H, X is F, X is O2 3 5 52Me, R is OCHF2 297 X is H, X is F, X is OCF3, R isOCHF298 X2is H, X3is F, X5is CF3, R5is OCHF2 299 X22is H, X3is F, X5is CHF2, R5isOCHF300 X2is H, X3is F, X5is OCHF2, R5is 301 X22is H, X3is F, X5is F, R5is CF=CH2 Table Row Heading Table Row Heading 316 X2is H, X3is F, X5is OMe, R5is CF=CH2 317 X2is H, X3is F, X5is OCF3, R5isCF=CH318 X2is H, X3is F, X5is CF3, R5is CF=CH2 319 X22is H, X3is F, X5is CHF2, R5isCF=CH320 X2is H, X3is F, X5is OCHF2, R5is 321 X22is H, X3is F, X5is F, R5is CCl=CH2CF=CH22322 X is H, X3is Cl, X5is Cl, R5is CCl=CH 323 X2is H, X3is F, X5is Cl, R5is CCl=CH32 3 5 5224 X is H, X is F2 3 5 52, X is H, R is CCl=CH 325 X is H, X is Cl, X is H, R is CCl=CH32 3 5 5226 X is H, X is C2 3 5 52N, X is H, R is CCl=CH 327 X is H, X is CN, X is F, R is CCl=CH32 3 5 5228 X is Cl, X is2 3 5 52F, X is F, R is CCl=CH 329 X is F, X is F, X is F, R is CCl=CH32 3 5 5230 X is F, X is C2 3 5 52l, X is Cl, R is CCl=CH 331 X is F, X is F, X is Cl, R is CCl=CH32 3 5 5232 X is H, X is F2 3 5 52, X is Br, R is CCl=CH 333 X is H, X is Cl, X is Br, R is CCl=CH32 3 5 5234 X is H, X is F2 3 5 52, X is CN, R is CCl=CH2 335 X is H, X is Cl, X is CN, R isCCl=CH336 X2is H, X3is F, X5is OMe, R5is 337 X22is H, X3is F, X5is OCF3, R5isCCl=CH22CCl=CH338 X is H, X3is F, X5is CF3, R5is CCl=CH2 339 X22is H, X3is F, X5is CHF2, R5isCCl=CH340 X2is H, X3is F, X5is OCHF2, R5is 341 X22is H, X3is F, X5is F, R5is C(=O)CH3CCl=CH34 X222 is H, X3is Cl, X5is Cl, R5is C(=O)CH 343 X2is H, X3is F, X5is Cl, R5is C(=O)CH32 3 5 5344 X is H, X is F2 3 5 53, X is H, R is C(=O)CH3 345 X is H, X is Cl, X is H, R isC(=O)CH346 X2is H, X3is CN, X5is H, R5is C(=O)CH3 347 X23is H, X3is CN, X5is F, R5isC(=O)CH3 354 is H, is F, is CN, is C(=O)CH3 355 is H, is Cl, is CN, isC(=O)CH356 X2is H, X3is F, X5is OMe, R5is 357 X23is H, X3is F, X5is OCF3, R5isC(=O)CH23C(=O)CH3 5 5 23358 X is H, X is F, X is CF3, R is 359 X is H, X3is F, X5is CHF2, R5isC(=O)CH23C(=O)CH360 X is H, X3is F, X5is OCHF2, R5is 361 X23is H, X3is F, X5is F, R5is CF2CH3C(=O)CH3 Table Row Heading Table Row Heading 362 X2is H, X3is Cl, X5is Cl, R5is CF CH 363 X2is H, X3is F, X5is Cl, R5is CF CH32 3 5 52 364 X is H, X is F, X i2 3 5 52 3s H, R is CF CH 365 X is H, X is Cl, X is H, R is CF CH32 3 5 52 366 X is H, X is CN, X2 3 5 52 3is H, R is CF CH 367 X is H, X is CN, X is F, R is CF CH32 3 5 52 368 X is Cl, X is F, X2 3 5 52 3is F, R is CF CH 369 X is F, X is F, X is F, R is CF CH32 3 5 52 370 X is F, X is Cl, X2 3 5 52 3is Cl, R is CF CH 371 X is F, X is F, X is Cl, R is CF CH32 3 5 52 372 X is H, X is F, X i2 3 5 52 3s Br, R is CF CH 373 X is H, X is Cl, X is Br, R is CF CH32 3 5 52 374 X is H, X is F, X i2 3 5 52 3s CN, R is CF CH 375 X is H, X is Cl, X is CN, R is CF CH32 3 5 52 376 X is H, X is F, X i2 3 5 52 3s OMe, R is CF2CH3 377 X is H, X is F, X is OCF3, R isCFX,3 52CH2is F, X5is CF , R is CF CH 379 X23378 is H X 3 2 3 is H, X3is F, X5is CHF2, R5isCFHis F, X5is OCHF , R is 381 X22CH2X3 53380 X is , 2 is H, X3is F, X5is F, R5is CHFCH3CF22CH3382 X is H, X3is Cl, X5is Cl, R5is CHFCH 383 X2is H, X3is F, X5is Cl, R5is CHFCH3 323 5 5 2 3 5 5384 X is H, X is F, X is H, R is CHFCH 385 X is H, X is Cl, X is H, R is CHFCH3 323 5 5 2 3 5 5386 X is H, X is CN, X is H, R is CHFCH 387 X is H, X is CN, X is F, R is CHFCH3 323 5 5 2 3 5 5388 X is Cl, X is F, X is F, R is CHFCH 389 X is F, X is F, X is F, R is CHFCH3 323 5 5 2 3 5 5390 X is F, X is Cl, X is Cl, R is CHFCH 391 X is F, X is F, X is Cl, R is CHFCH3 323 5 5 2 3 5 5392 X is H, X is F, X is Br, R is CHFCH 393 X is H, X is Cl, X is Br, R is CHFCH3 323 5 5 2 3 5 5394 X is H, X is F, X is CN, R is CHFCH 395 X is H, X is Cl, X is CN, R is3CHFCH323 5 5 2 3 5 5396 X is H, X is F, X is OMe, R is CHFCH 397 X is H, X is F, X is OCF , R is3 3CHFCH323 5 5 2 3 5 5398 X is H, X is F, X is CF , R is CHFCH 399 X is H, X is F, X is CHF , R is3 3 2CHFCH323 5 5 2 3 5 5400 X is H, X is F, X is OCHF , R is 401 X is H, X is F, X is F, R is2CHFCH C(CH )=CH3 3 223 5 5 2 3 5 5402 X is H, X is Cl, X is Cl, R is 403 X is H, X is F, X is Cl, R isC(CH )=CH C(CH )=CH3 2 3 223 5 5 2 3 5 5404 X is H, X is F, X is H, R is 405 X is H, X is Cl, X is H, R isC(CH )=CH C(CH )=CH3 2 3 223 5 5 2 3 5 5406 X is H, X is CN, X is H, R is 407 X is H, X is CN, X is F, R isC(CH )=CH C(CH )=CH3 2 3 223 5 5 2 3 5 5408 X is Cl, X is F, X is F, R is 409 X is F, X is F, X is F, R isC(CH )=CH C(CH )=CH3 2 3 223 5 5 2 3 5 5410 X is F, X is Cl, X is Cl, R is 411 X is F, X is F, X is Cl, R isC(CH )=CH C(CH )=CH3 2 3 2 Table Row Heading Table Row Heading 412 X2is H, X3is F, X5is Br, R5is 413 X2is H, X3is Cl, X5is Br, R5isC(CH )=CH C(CH )=CH2332414 X is H X is , X5is CN, R5is 415 X23is H, X32, F is Cl, X5is CN, R5isC(CH )=CH C(CH )=CH2332416 X is H X is , X5is OMe, R5is 417 X23is H, X32, F is F, X5is OCF3, R5isis CN424 X2is H, X3is F, X5is H, R5is CN 425 X2is H, X3is Cl, X5is H, R5is CN426 X2is H, X3is CN, X5is H, R5is CN 427 X2is H, X3is CN, X5is F, R5is CN428 X2is Cl, X3is F, X5is F, R5is CN 429 X2is F, X3is F, X5is F, R5is CN430 X2is F, X3is Cl, X5is Cl, R5is CN 431 X2is F, X3is F, X5is Cl, R5is CN432 X2is H, X3is F, X5is Br, R5is CN 433 X2is H, X3is Cl, X5is Br, R5is CN434 X2is H, X3is F, X5is CN, R5is CN 435 X2is H, X3is Cl, X5is CN, R5is CN436 X2is H, X3is F, X5is OMe, R5is CN 437 X2is H, X3is F, X5is OCF , R is CN438 X2is H, X3is F, X5is CF , R5is CN 439 X2is H, X3is F, X535is CHF , R is CN4402 3 53X is H, X is F, X is O5 2 3 5 525CHF , R is CN 441 X is H, X is F, X is F, R is CF Cl42 3 5 5242 X is H, X is Cl, X is2 3 5 52Cl, R is CF Cl 443 X is H, X is F, X is Cl, R is CF Cl42 3 5 5244 X is H, X is F, X is H2 3 5 52, R is CF Cl 445 X is H, X is Cl, X is H, R is CF Cl42 3 5 5246 X is H, X is CN, X is2 3 5 52H, R is CF Cl 447 X is H, X is CN, X is F, R is CF Cl42 3 5 5248 X is Cl, X is F, X is2 3 5 52F, R is CF Cl 449 X is F, X is F, X is F, R is CF Cl42 3 5 5250 X is F, X is Cl, X is2 3 5 52Cl, R is CF Cl 451 X is F, X is F, X is Cl, R is CF Cl42 3 5 5252 X is H, X is F, X is B2 3 5 52r, R is CF Cl 453 X is H, X is Cl, X is Br, R is CF Cl42 3 5 5254 X is H, X is F, X is C2 3 5 52N, R is CF Cl 455 X is H, X is Cl, X is CN, R is CF Cl42 3 5 5256 X is H, X is F, X is O2 3 5 52Me, R is CF Cl 457 X is H, X is F, X is OCF , R is CF Cl45 X2s3 5 52H, is F X is2 3 53528 i X , CF , R is CF Cl 459 X is H, X is F, X is CHF , R is CF Cl23 5352460 X is H, X is F, X i2 3 5 52 2s OCHF , R is CF Cl 461 X is H, X is F, X is F, R is CH OCF42 3 5 52 262 X is H, X is Cl, X2 3 5 52 3is Cl, R is CH OCF 463 X is H, X is F, X is Cl, R is CH OCF42 3 5 52 364 X is H, X is F, X i2 3 5 52 3s H, R is CH OCF 465 X is H, X is Cl, X is H, R is CH OCF42 3 5 52 366 X is H, X is CN, X2 3 5 52 3is H, R is CH2OCF3 467 X is H, X is CN, X is F, R isCH2s l3 52OCFX5 23468 X i C, is F, X is F, R is CH OCF 469 X is F, X3is F, X5is F, R5is CH OCF42 3 5 52 370 X is F, X is Cl, X2 3 5 52 3is Cl, R is CH2OCF3 471 X is F, X is F, X is Cl, R is CH2OCF3 Table Row Heading Table Row Heading 472 X2is H, X3is F, X5is Br, R5is CH2OCF3 473 X2is H, X3is Cl, X5is Br, R5isCH2s , X3is F, X is CN, R52OCF5is CH2OCF 475 X23474 X i H 3 is H, X3is Cl, X5is CN, R5isCH2s3 52OCF5 23476 X i H, X is F, X is OMe, R is 477 X is H, X3is F, X5is OCF3, R5isCH22OCF3CH2OCF478 X is H, X3is F, X5is CF3, R5is CH2OCF3 479 X23is H, X3is F, X5is CHF2, R5isCH3 52OCF480 X2i5 23s H, X is F, X is OCHF2, R is 481 X is H, X3is F, X5is F, R5is CH2OHCH22OCF3482 X is H, X3is Cl, X5is Cl, R5is CH OH 483 X2is H, X3is F, X5is Cl, R5is CH OH42 3 5 5284 X is H, X is F, X2 3 5 52is H, R is CH OH 485 X is H, X is Cl, X is H, R is CH OH42 3 5 5286 X is H, X is CN,2 3 5 52X is H, R is CH OH 487 X is H, X is CN, X is F, R is CH OH42 3 5 5288 X is Cl, X is F,2 3 5 52X is F, R is CH OH 489 X is F, X is F, X is F, R is CH OH42 3 5 5290 X is F, X is Cl,2 3 5 52X is Cl, R is CH OH 491 X is F, X is F, X is Cl, R is CH OH42 3 5 5292 X is H, X is F, X2 3 5 52is Br, R is CH OH 493 X is H, X is Cl, X is Br, R is CH OH42 3 5 5294 X is H, X is F, X2 3 5 52is CN, R is CH OH 495 X is H, X is Cl, X is CN, R is CH OH42 3 5 5296 X is H, X is F, X2 3 5 52is OMe, R is CH2OH 497 X is H, X is F, X is OCF3, R isCH3 52OH498 X2is H, X is F, X5is CF3, R is CH2OH 499 X2is H, X3is F, X5is CHF2, R5isCH5 22OH500 X2is H, X3is F, X is OCHF2, R5is 501 X is H, X3is F, X5is F, R5isCH2OH C(CH23)=CF502 X2is H, X3is Cl, X5is Cl, R5is 503 X is H, X32is F, X5is Cl, R5isC(CH )=CF C(CH )=CF2332504 X is H X is , X5is H, R5is 505 X23is H, X32, F is Cl, X5is H, R5isC(CH )=CF C(CH )=CF2332506 X is H X is N, X5is H, R5is 507 X23is H, X32, C is CN, X5is F, R5isC(CH )=CF C(CH )=CF2332508 X is C, X i F, X5is F, R5is 509 X23is F, X32l s is F, X5is F, R5isC(CH )=CF C(CH )=CF2332510 X is F X is l, X5is Cl, R5is 511 X23is F, X32, C is F, X5is Cl, R5isC(CH )=CF C(CH )=CF2332512 X is H X is , X5is Br, R5is 513 X23is H, X32, F is Cl, X5is Br, R5isC(CH )=CF C(CH )=CF2332514 X is H X is , X5is CN, R5is 515 X23is H, X32, F is Cl, X5is CN, R5isC(CH3)=CF2C(CH3)=CF2 Table Row Heading Table Row Heading 516 X2is H, X3is F, X5is OMe, R5is 517 X2is H, X3is F, X5is OCF3, R5isC(CH3)=CF2C(CH3)=CF2 524 X2is H, X3is F, X5is H, R5is CH=CF 525 X2is H, X3is Cl, X5is H, R5is CH=CF52 3 5 5226 X is H, X is C2 3 5 52N, X is H, R is CH=CF 527 X is H, X is CN, X is F, R is CH=CF52 3 5 5228 X is Cl, X is2 3 5 52F, X is F, R is CH=CF 529 X is F, X is F, X is F, R is CH=CF52 3 5 5230 X is F, X is C2 3 5 52l, X is Cl, R is CH=CF 531 X is F, X is F, X is Cl, R is CH=CF52 3 5 5232 X is H, X is F2 3 5 52, X is Br, R is CH=CF 533 X is H, X is Cl, X is Br, R is CH=CF52 3 5 5234 X is H, X is F2 3 5 52, X is CN, R is CH=CF 535 X is H, X is Cl, X is CN, R is CH=CF52 3 5 5236 X is H, X is F2 3 5 52, X is OMe, R is CH=CF2 537 X is H, X is F, X is OCF3, R isCH=CF538 X2is H, X3is F, X5is CF3, R5is CH=CF2 539 X22is H, X3is F, X5is CHF2, R5isCH=CF540 X2is H, X3is F, X5is OCHF , R5is 541 X222 is H, X3is F, X5is F, R5isCH=CF2cis-CH=CHCH542 X2is H, X3is Cl, X5is Cl, R5is 543 X2is H, X33is F, X5is Cl, R5iscis-CH=CHCH cis-CH=CHCH2 33544 X is H, X is F, X5is H, R5is 545 X2is H, X33is Cl, X5is H, R5iscis-CH=CHCH cis-CH=CHCH2 33546 X is H, X is CN, X5is H, R5is 547 X2is H, X33is CN, X5is F, R5iscis-CH=CHCH cis-CH=CHCH2 33548 X is Cl, X is F, X5is F, R5is 549 X2is F, X33is F, X5is F, R5iscis-CH=CHCH cis-CH=CHCH2 33550 X is F, X is Cl, X5is Cl, R5is 551 X2is F, X33is F, X5is Cl, R5iscis-CH=CHCH cis-CH=CHCH2 33552 X is H, X is F, X5is Br, R5is 553 X2is H, X33is Cl, X5is Br, R5iscis-CH=CHCH cis-CH=CHCH2 33554 X is H, X is F, X5is CN, R5is 555 X2is H, X33is Cl, X5is CN, R5iscis-CH=CHCH cis-CH=CHCH2 33556 X is H, X is F, X5is OMe, R5is 557 X2is H, X33is F, X5is OCF3, R5iscis-CH=CHCH cis-CH=CHCH2 33558 X is H, X is F, X5is CF3, R5is 559 X2is H, X33is F, X5is CHF2, R5iscis-CH=CHCH3cis-CH=CHCH3 Table Row Heading Table Row Heading 560 X2is H, X3is F, X5is OCHF2, R5is 561 X2is H, X3is F, X5is F, R5iscis-CH=CHCH3trans-CH=CHCH3562 X5is Cl, R5is 564 X2is H, X3is F, X5is H, R5is 565 X2is H, X3is Cl, X5is H, R5istrans-CH=CHCH trans-CH=CHCH2X33566 X is H, is CN, X5is H, R5is 567 X2is H, X33is CN, X5is F, R5istrans-CH=CHCH trans-CH=CHCH2, X33568 X is Cl is F, X5is F, R5is 569 X2is F, X33is F, X5is F, R5istrans-CH=CHCH trans-CH=CHCH2 33570 X is F, X is Cl, X5is Cl, R5is 571 X2is F, X33is F, X5is Cl, R5istrans-CH=CHCH trans-CH=CHCH2X33572 X is H, is F, X5is Br, R5is 573 X2is H, X33is Cl, X5is Br, R5istrans-CH=CHCH trans-CH=CHCH2X33574 X is H, is F, X5is CN, R5is 575 X2is H, X33is Cl, X5is CN, R5istrans-CH=CHCH3576 X2is H, X3is F, X5is OMe, R5is 577 R5isis 584 is H, is F, is H, is CH2OCHF2 585 is H, is Cl, is H, isCH2OCHF2 3 5 5 2 32586 X is H, X is CN, X is H, R is 587 X is H, X is CN, X5is F, R5isCH OCHF CH OCHF22 2588 X is3 5 5 2232Cl, X is F, X is F, R is CH OCHF 589 X is F, X is F, X5is F, R5is CH OCHF52 3 5 52 290 X is2 3 5 52 2F, X is Cl, X is Cl, R is 591 X is F, X is F, X is Cl, R isCH OCHF CH OCHF2232592 X is5 5 2232H, X is F, X is Br, R is CH2OCHF2 593 X is H, X is Cl, X5is Br, R5isCH2OCHF594 X2is H, X3is F, X5is CN, R5is 595 X2is H, X32is Cl, X5is CN, R5isCH OCHF CH OCHF2232596 X is5 5 2232H, X is F, X is OMe, R is 597 X is H, X is F, X5is OCF3, R5isCH2OCHF2CH2OCHF2 Table Row Heading Table Row Heading 598 X2is H, X3is F, X5is CF3, R5is 599 X2is H, X3is F, X5is CHF2, R5isCH2OCHF2CH2OCHF2 CCl=CH CCl=CH22618 X is H X3,5C 3,5s CCl=CH 619 X22, is F X is F R i 2 is H, X3is F, X5is CHF2, R5isCCl=CH620 X2is H, X3is F, X5s OC52i HF2, R isCCl=CH2Table 621 Table 621 in Table 1 is replaced with the structure above for Table 621. Table 622 through Table 1220 Table 622 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 621. Tables 623 through 1220 are constructed in the same fashion as Tables 3 through 620. Table 1221 structure in Table 1 is replaced with the Table 1222 through Table 1820 Table 1222 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 1221. Tables 1223 through 1820 are constructed in the same fashion as Tables 3 through 620. Table 1821 in Table 1 is replaced with the structure above for Table 1821. Table 1822 through Table 2420 Table 1822 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 1821. Tables 1823 through 2420 are constructed in the same fashion as Tables 3 through 620. Table 2421 Table 2421 in Table 1 is replaced with the structure above for Table 2421. Table 2422 Table 3020 Table 2422 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 2421. Tables 2423 through 3020 are constructed in the same fashion as Tables 3 through 620. Table 3021 in Table 1 is Table 3022 through Table 3620 Table 3022 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 3021. Tables 3023 through 3620 are constructed in the same fashion as Tables 3 through 620. Table 3021 Table 3621 structure in Table 1 is replaced with the structure above for Table 3621. Table 3622 through Table 4220 Table 3622 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 3621. Tables 3623 through 4220 are constructed in the same fashion as Tables 3 through 620. Table 4221 Table 4221 structure in Table 1 is replaced with the Table 4222 through Table 4820 Table 4222 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 4221. Tables 4223 through 4820 are constructed in the same fashion as Tables 3 through 620. Table 4821 structure in Table 1 is replaced with the structure above for Table 4821. Table 4822 through Table 5420 Table 4822 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 4821. Tables 4823 through 5420 are constructed in the same fashion as Tables 3 through 620. Table 5401 Table 5421 structure in Table 1 is replaced with the structure above for Table 5421. Table 5422 Table 6020 Table 5422 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 5421. Tables 5423 through 6020 are constructed in the same fashion as Tables 3 through 620. Table 6021 Table 6021 structure in Table 1 is replaced with the Table 6022 through Table 6620 Table 6022 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 6021. Tables 6023 through 6620 are constructed in the same fashion as Tables 3 through 620. Table 6621 Table 6621 structure in Table 1 is replaced with the structure above for Table 6621. Table 6622 through Table 7220 Table 6622 is constructed the same as Table 2 except that the structure in Table 2 is replaced with the structure above for Table 6621. Tables 6623 through 7220 are constructed in the same fashion as Tables 3 through 620. 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 and solid compositions. Liquid compositions include solutions (including emulsifiable , 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. 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. 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 paraffinic 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. 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.
[0002] Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001–90 0–99.999 0–15 soluble Granules, Tablets and Powders Oil Dispersions, Suspensions, 1–50 40–99 0–50 Emulsions, Solutions (including Emulsifiable Concentrates) Dusts 1–25 70–99 0–5 Granules and Pellets 0.001–99 5–99.999 0–15 High Strength Compositions 90–99 0–10 0–2 Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), 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 be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. The solid and liquid compositions of the present invention often include one or more surfactants. 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. 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. 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, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl salts. 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. 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. 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. The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. can be made into finished suspension concentrates (see, for example, 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 μm 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. 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. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A– G. 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 invention in any way whatsoever. Percentages are by weight except where otherwise indicated.
[0003] A High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% Example B Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% Example C Granule Compound 1 10.0% attapulgite granules (low volatile matter, 0.71 / 0.30 mm; 90.0% U.S.S. No.25–50 sieves) Example D Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium / magnesium bentonite 59.0% Example E Emulsifiable Concentrate Compound 1 10.0% polyoxyethylene sorbitol hexoleate 20.0% C6–C10fatty acid methyl ester 70.0% Example F Microemulsion Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkylpolyglycoside 30.0% glyceryl monooleate 15.0% Water 20.0% Example G Suspension Concentrate Compound 1 35% butyl 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% 1,2-benzisothiazolin-3-one 0.1% Water 53.7% Example H Emulsion in Water Compound 1 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% 1,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0 Water 58.7% Example I Oil Dispersion Compound 1 25% polyoxyethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5% 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 inention 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 placement on or within the environment of a mixture of crops and weeds, are useful for selective control of grass and broadleaf weeds within a crop / weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and / or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and / or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth. As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation. A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 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. In one common embodiment, a compound of the invention is applied, typically in a formulated composition, to a locus comprising desired vegetation (e.g., crops) and undesired vegetation (i.e., weeds), both of which may be seeds, seedlings and / or larger plants, in contact with a growth medium (e.g., soil). In this locus, a composition comprising a compound of the invention can be directly applied to a plant or a part thereof, particularly of the undesired vegetation, and / or to the growth medium in contact with the plant. Plant varieties and cultivars of the desired vegetation in the locus treated with a compound of the invention can be obtained by conventional propagation and breeding methods or by genetic engineering Genetically modified plants (transgenic plants) are those in which a heterologous gene 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. Genetically modified plant cultivars in the locus 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 noteworthy when the crop is genetically modified to resist the effectiveness of the compound of Formual 1. Although most typically, compounds of the invention are used to control undesired vegetation, contact of desired vegetation in the treated locus with compounds of the invention may result in super-additive or synergistic effects with genetic traits in the desired vegetation, including traits incorporated through genetic modification. For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic / abiotic stresses or storage stability may be greater than expected from the genetic traits in the desired vegetation. 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. A mixture of one or more of the herbicides with a compound of this invention may be particularly useful for weed Examples of additional active ingredients are allidochlor, acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bipyrazone, bispyribac and its sodium salt, bixlozone, broclozone, 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, cinflubrolin, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, cypyrafluone, 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, dimesulfazet, dimepiperate, dimepyrolimet, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, dioxopyritrione, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, epyrifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fendioxypyracil, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, feproxydim, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, fluchloraminopyr, fluchloraminopyr-tefuryl, flufenacet, flufenauxirim, flufenauxirim-metotyl, flufenazopyr, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, flusulfinam, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, L-glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named , halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, methyl, hexazinone, hydantocidin, icafolin, icafolin-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, indolauxipyr-cyanomethyl, iofensulfuron, iofensulfuron-sodium, iodosulfuron-methyl, iodosulfuron-sodium, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, iptriazopyrid, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lancotrione, 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, metproxybicyclone, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prochlorosulfone, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyraquinate, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriflubenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimisoxafen, rimsulfuron, saflufenacil, 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, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, toxapyzone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tripyrasulfone, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5- naphthyridin-2(1H)-one, 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl- 3(2H)-pyridazinone, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4- methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6- (trifluoromethyl)-3-pyridinecarboxamide, dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)- 8-hydroxypyrido[2,3-b]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), 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-(1-methyl-1H-tetrazol-5-yl)-4- (trifluoromethyl)benzamide, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)- 4-(trifluoromethyl)benzamide, methyl 2-[2-[2-bromo-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenoxy]phenoxy]-2-methoxyacetate, ethyl 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4- fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylate, 1-(2-carboxyethyl)-4-(2- pyrimidinyl)pyridazinium and its salts and esters. The compound of Formula 1 can also be mixed with a compound selected from the group consisting of N-[2,4-dimethyl-5-(1-piperidinylcarbonyl)phenyl]-1,1,1-trifluoromethanesulfonamide; N-[2-chloro-4-methyl-5-(4-morpholinylcarbonyl)phenyl]-1,1,1- trifluoromethanesulfonamide; N-[2,4-dimethyl-5-(4-morpholinylcarbonyl)phenyl]-1,1,1- trifluoromethanesulfonamide; N-[2-chloro-4-methyl-5-(1-piperidinylcarbonyl)phenyl]-1,1,1- trifluoromethanesulfonamide; 3-fluoro-N,N,2,4-tetramethyl-5-[[(trifluoromethyl)sulfonyl]amino]benzamide; 1,1,1-trifluoro-N-[3-fluoro-2,4-dimethyl-5-(4- morpholinylcarbonyl)phenyl]methanesulfonamide; N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.4]non-2-en-3-yl)phenyl]-1,1,1- trifluoromethanesulfonamide; N-[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazol-3- yl]phenyl]-1,1,1-trifluoromethanesulfonamide; N-[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3-yl)phenyl]-1,1,1- trifluoromethanesulfonamide; N-[2,4-dimethyl-5-(3a,4,7,7a-tetrahydro-5H-pyrano[4,3-d]isoxazol-3-yl)phenyl]-1,1,1- trifluoromethanesulfonamide; N-[2,4-dimethyl-5-(3a,6,7,7a-tetrahydro-4H-pyrano[3,4-d]isoxazol-3-yl)phenyl]-1,1,1- trifluoromethanesulfonamide; N-[2,4-dimethyl-5-(1-oxo-2-azaspiro[4.5]dec-2-yl)phenyl]-1,1,1-trifluoro-N- [(trifluoromethyl)sulfonyl]methanesulfonamide; [[2,4-dimethyl-5-(1-oxa-2-azaspiro non-2-en-3- yl)phenyl][(trifluoromethyl) amino]methyl 2,2-dimethylpropanoate; [[2,4-dimethyl-5-(1-oxa-2-azaspiro[4.5]dec-2-en-3- yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate; [[2,4-dimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H-cyclopent[d]isoxazol-3- yl]phenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate; [[2,4-dimethyl-5-(1-oxo-2-azaspiro[4.5]dec-2- yl)phenyl][(trifluoromethyl)sulfonyl]amino]methyl 2,2-dimethylpropanoate; [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-(4- morpholinylcarbonyl)phenyl]amino]methyl 2,2-dimethylpropanoate; ethyl N-[(trifluoromethyl)sulfonyl]-N-[2,3,4-trimethyl-5-(1- piperidinylcarbonyl)phenyl]carbamate; [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-(1- piperidinylcarbonyl)phenyl]amino]methyl 2,2-dimethylpropanoate; 1,1,1-trifluoro-N-[2,3,4-trimethyl-5-(4- morpholinylcarbonyl)phenyl]methanesulfonamide; and [[(trifluoromethyl)sulfonyl][2,3,4-trimethyl-5-[(3aR,6aR)-3a,5,6,6a-tetrahydro-4H- cyclopent[d]isoxazol-3-yl]phenyl]amino]methyl 2,2-dimethylpropanoate; The compound of Formula 1 can also be mixed with a compound selected from the group consisting of [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][2-methyl-5-[3-(1- methylethyl)-1H-1,2,4-triazol-1-yl]phenyl]methanone; [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][5-[3-(1,1- dimethylethyl)-1H-1,2,4-triazol-1-yl]-2-methylphenyl]methanone; [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][2-methoxy-5-[3- (1-methylethyl)-1H-1,2,4-triazol-1-yl]phenyl]methanone; [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][5-(3-ethyl-1H- 1,2,4-triazol-1-yl)-2-methoxyphenyl]methanone; [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][2-ethyl-5-[3-(1- methylethyl)-1H-1,2,4-triazol-1-yl]phenyl]methanone; [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][5-(3-cyclobutyl- 1H-1,2,4-triazol-1-yl)-2-methylphenyl]methanone; [(2S)-8-Chloro-2,3-dihydro-2-methyl-4H-1,4-benzoxazin-4-yl][3-(3-cyclobutyl- 1H-1,2,4-triazol-1-yl)phenyl]methanone; [(2S)-2,3-Dihydro-2,8-dimethyl-4H-1,4-benzoxazin-4-yl][2-methoxy-5-(1H- 1,2,4-triazol-1-yl)phenyl]methanone; The selected from the group consisting of 4-[(E)-(3-bromo-1-naphthalenyl)(methoxyimino)methyl]-5-hydroxy-2,6-dimethyl- 3(2H)-pyridazinone; 4-[(Z)-(3-bromo-1-naphthalenyl)(methoxyimino)methyl]-5-hydroxy-2,6-dimethyl- 3(2H)-pyridazinone; 4-[(E)-(3-bromo-1-naphthalenyl)[(2- 1-yloxy)imino]methyl]-5-hydroxy-2,6- dimethyl-3(2H)-pyridazinone; 4-[(E)-(3-bromo-1-naphthalenyl)(ethoxyimino)methyl]-5-hydroxy-2,6-dimethyl-3(2H)- pyridazinone; 4-[(Z)-(4-fluoro-1-naphthalenyl)[(2-propyn-1-yloxy)imino]methyl]-5-hydroxy-2,6- dimethyl-3(2H)-pyridazinone; and 4-[(E)-(4-fluoro-1-naphthalenyl)[(2-propyn-1-yloxy)imino]methyl]-5-hydroxy-2,6- dimethyl-3(2H)-pyridazinone. The compound of Formula 1 can also be mixed with a compound selected from the group consisting of 4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2- (trifluoromethyl)pyridine; 4-[[5-ethoxy-2-(4-fluorophenyl)-2H-1,2,3-triazol-4-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[5-ethoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[5-(2,2,2-trifluoroethoxy)-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4- yl]methyl]-2-(trifluoromethyl)pyridine; 4-[[5-ethyl-3-[4-(trifluoromethyl)phenyl]-1H-1,2,4-triazol-1-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[3-(4-fluorophenyl)-5-propyl-1H-1,2,4-triazol-1-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[5-ethoxy-3-(4-fluorophenyl)-1H-1,2,4-triazol-1-yl]methyl]-2- (trifluoromethyl)pyridine; 4-[[3-(4-fluorophenyl)-1-propyl-1H-1,2,4-triazol-5-yl]methyl]-2- (trifluoromethyl)pyridine; and 4-[[3-(4-fluorophenyl)-5-methoxy-1H-1,2,4-triazol-1-yl]methyl]-2- (trifluoromethyl)pyridine. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub. Compounds of this invention can be used in combination with plant growth regulators such as aviglycine, N- -1H-purin-6-amine, epocholeone, gibberellic acid, 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. 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. For embodiments where one or more of these various mixing partners are used, the mixing partners are typically used in the amounts similar to amounts customary when the mixture partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between one-half and the full application rate specified on product labels for use of active ingredient alone. These amounts are listed in references such as The Pesticide Manual and The BioPesticide Manual. 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. 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. 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 one other herbicidal active ingredient having a similar spectrum of control but a 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. Compounds of this invention can also be used in combination with herbicide safeners (e.g., such as those listed in (b18)) to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation. Compounds of the invention cans also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and / or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and / or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect. 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. Table A1 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 A1 lists the specific Component (b) compound (e.g., “2,4-D” in the first line). The third, fourth and fifth columns of Table A1 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 A1 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 1:192 – 6:1. The remaining lines of Table A1 are to be construed similarly. A1 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 2 4 2 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 0 3 2 0 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 2 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 5 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 6 0 6 7 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 2 2 Component (a) Typical More Typical Most Typical (Compound 1) Component (b) Weight Ratio Weight Ratio Weight Ratio 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 2” (i.e., Compound 2 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 2 with 2,4-D. Tables A3 through A150 are constructed similarly. Table Component (a) Table Component (a) Table Component (a) s es 4 5 6 7 8 9 0 1 2 3 4 Table Component (a) Table (a) Table Component (a) Number Column Entries Number Column Entries Number Column Entries 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 Table Component (a) Table (a) Number Column Entries Number Column Entries Preferred for better contro l 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 bixlozone, carfentrazone, carfentrazone-ethyl, clomazone, chlorimuron-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, tribenuron, pinoxaden, pyroxasulfone, pyroxsulam, rimisoxafen, tembotrione, tetflupyrolimet, metolachlor and S-metolachlor. The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables A through L for compound descriptions. The following abbreviations are used in the Index Tables which follow: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, i-Pr means isopropyl, Bu means butyl, c-Pr means cyclopropyl, t-Bu means tert-butyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, -CN means cyano, -NO2means nitro, TMS means trimethylsilyl, and naphthyl means naphthalenyl. The abbreviation “(d)” indicates that the compound appeared to decompose on melting. The abbreviation “Cmpd. No.” stands for “Compound Number”. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. The abbreviation “m.p.” stands for melting point. The numerical value reported in the column “MS” is the molecular weight of the highest isotopic abundance positively charged parent ion (M+1) formed by addition of H+(molecular weight of 1) to the molecule having the highest isotopic abundance, or the highest isotopic abundance negatively charged ion (M–1) formed by loss of H+(molecular weight of 1). “(M–1)” in the “MS” column indicates the value is a negatively charged ion. The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g.,37Cl,81Br) is not reported. The reported MS peaks were observed by mass spectrometry using electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI). Mass spectra are reported with an estimated precision within ±0.5 Da as the molecular weight of the highest isotopic abundance parent ion . The abbreviation “SC (*)” stands for “stereochemistry” wherein the chiral center is identified with an asterisk (*). (R) or (S) denotes the absolute chirality of the asymmetric carbon center. The abbreviation “rac” stands for “racemic”. The abbreviation “Enan” means “single enantiomer” represented by the Enantiomer (1′) or (1′′) as shown below. INDEX TABLE A Cmpd.3 5 5 2m.p. NX X R Y Z R2SC (*) MS C)– 5 – 3 – 0 Cmpd. NX3X5R5Y2o.Z R2SC (*) MSm.p. (C)– 5 – 7 Cmpd. oX3X5R5Y2NZ R2SC (*) MSm.p. .( C)– 0 – 0 – 5 – 5 – 8 – 5 – 5 – – 8 – 2 – 7 – 4 Cmpd. NX3X5R5Y2Z R2o.SC (*) MSm.p. (C)– 3 – 5 – – 4 – 0 – 4 – 4 Cmpd. NX3X5R5Y2Z R2o.SC (*) MSm.p. (C)– 6 – – – 0 – 0 Cmpd. NX3X5R5Y2Z R2o.SC (*) MSm.p. (C)– 0 – 3 – 7 – 3 – 7 – 8 – 1 Cmpd.X3X5R5Y2Z R2SC (*) MSm.p. No.( C)– 0 – 1 – 0 – 3 – 1 – 4 – 1 – 8 – 2 – 0 INDEX TABLE B Cmpd. No. X3R5Y2Z R2SC(*) MS125 F CF3 O O CH3 Enan 418 Cm d No X3 X5 R5 Y2 Z R2 SC(*)m.p. 75715 Cmpd. No. m.p. ( C) INDEX TABLE F Cmpd. No. X3 X5 R5 Y2 Z R2 m.p. ( C) INDEX TABLE G Cmpd. No. X3X5R5Y2R2SC(*) MS
[0004] MS8589715 Cmpd. (*) MS
[0005] Cmpd. N.X1MSm.p. o ( C)725490 Cmpd.R3R4R5Y2Z R2SC* MS BIOLOGICAL OF THE INVENTION TEST A Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), blackgrass(Alopecurus myosuroides), corn (Zea mays), green foxtail (Setaria viridis), kochia (Bassia scoparia), wild oat (Avena fatua), Palmer amaranth (Palmer pigweed, Amaranthus palmeri), ragweed (common ragweed, Ambrosia artemisiifolia), Italian ryegrass (Lolium multiflorum), soybean (Glycine max) and wheat (Triticum aestivum) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crops and weed species and galium (catchweed bedstraw, Galium aparine) and horseweed (Erigeron canadensis) 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 10 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. Table A Compounds 62 g ai / ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Preemergence Barnyardgrass 80 90 90 40 90 100 80 30 90 90 90 100 100 100 Blackgrass 80 90 90 40 80 90 90 80 80 90 90 90 90 90 Corn 50 70 80 40 60 40 50 30 60 70 70 70 30 20 Foxtail, Green 100 90 100 80 90 100 90 100 90 90 90 90 100 100 Kochia 70 70 100 90 80 100 90 80 70 100 100 80 90 90 Oat, Wild 90 90 90 50 30 80 80 50 50 50 80 60 80 80 Pigweed, Palmer 80 80 100 100 90 100 100 60 90 100 90 100 100 80 Ragweed 10 0 90 80 0 100 90 80 60 20 10 0 80 80 Ryegrass, Italian 90 100 90 90 90 90 90 90 90 90 90 90 100 90 Soybean 60 50 40 0 50 60 0 40 90 20 40 50 40 50 Wheat 90 90 90 80 90 90 90 90 90 90 90 90 90 80 Table A Compounds 62 g ai / ha 15 16 17 19 20 22 24 25 26 27 28 29 30 31 Preemergence Barnyardgrass 100 0 60 90 80 90 90 90 90 90 90 90 0 80 Blackgrass 90 40 60 90 90 90 90 90 90 90 90 80 60 90 Corn 20 0 40 80 80 80 70 20 50 40 20 30 Foxtail, Green 90 40 70 90 90 90 90 100 100 100 90 90 60 90 Kochia 90 40 60 90 100 90 100 90 90 90 100 70 80 40 Oat, Wild 80 0 40 30 40 90 90 80 90 90 80 50 30 80 Pigweed, Palmer 100 10 50 80 100 90 100 90 90 100 90 100 80 90 Ragweed 90 0 50 80 80 40 0 0 40 0 90 90 70 80 Ryegrass, Italian 100 80 80 90 90 90 90 90 90 90 90 90 70 90 Soybean 60 0 0 0 20 70 30 20 50 70 40 0 0 30 Wheat 90 80 80 30 80 90 90 90 90 90 90 90 20 90 Table A Compounds 62 g ai / ha 32 33 36 37 38 39 40 41 42 43 44 45 46 47 Preemergence 90 Blackgrass 90 90 80 90 90 20 80 20 40 90 90 0 90 60 Corn 50 70 30 20 30 20 30 40 0 40 40 10 60 50 Foxtail, Green 90 100 90 90 80 0 70 0 0 60 90 0 90 50 Kochia 80 90 100 90 90 0 100 90 30 100 100 70 100 100 Oat, Wild 60 70 30 40 90 50 90 50 0 90 90 20 100 90 Pigweed, Palmer 100 90 100 100 100 0 100 50 20 100 100 10 100 100 Ragweed 90 90 90 90 90 0 90 0 0 90 80 0 90 70 Ryegrass, Italian 90 90 90 90 90 0 100 80 0 90 90 0 90 90 Soybean 0 0 0 0 50 0 80 0 0 70 70 50 60 70 Wheat 80 80 80 90 90 30 90 80 0 90 90 50 90 90 Table A Compounds 62 g ai / ha 48 49 50 52 53 54 56 57 58 60 67 74 75 76 Preemergence Barnyardgrass 90 90 90 70 90 90 90 70 90 90 80 40 60 70 Blackgrass 80 90 90 70 80 90 70 60 90 90 90 80 100 70 Corn 50 30 20 10 50 60 20 0 90 90 30 30 20 30 Foxtail, Green 90 100 100 60 100 90 90 30 100 100 90 60 100 90 Kochia 90 90 60 60 100 100 - 20 90 100 90 60 50 50 Oat, Wild 90 50 40 80 40 30 50 10 100 100 30 50 100 90 Pigweed, Palmer - 100 100 20 90 90 70 0 100 100 100 50 40 80 Ragweed 90 80 90 0 90 60 0 0 100 90 90 0 0 0 Ryegrass, Italian 90 90 90 70 90 90 80 60 100 100 80 90 90 90 Soybean 0 0 0 0 0 60 0 0 50 0 0 0 0 0 Wheat 90 70 40 90 80 90 90 90 100 100 80 90 90 90 Table A Compounds 62 g ai / ha 77 82 83 84 85 86 87 88 93 94 95 96 97 98 Preemergence Barnyardgrass 90 70 80 100 0 100 90 0 80 30 100 0 100 70 Blackgrass 90 70 90 90 0 90 90 10 80 80 90 20 90 80 Corn 40 80 30 70 0 90 70 10 50 10 30 10 30 30 Foxtail, Green 90 90 80 100 40 100 90 0 90 40 90 30 90 90 Kochia 50 40 40 90 0 100 100 - 100 70 90 90 90 60 Oat, Wild 90 80 70 90 0 90 90 0 30 0 90 30 90 50 Pigweed, Palmer 90 50 70 100 0 100 100 60 90 30 90 50 100 80 Ragweed 0 0 0 90 0 90 90 0 0 0 20 0 90 10 Ryegrass, Italian 90 90 90 90 0 100 100 0 90 80 100 90 90 90 Soybean 0 0 20 80 0 30 60 0 80 0 30 0 50 0 Wheat 80 90 90 100 0 100 100 0 90 60 90 60 90 50 Table A Compounds 62 g ai / ha 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Preemergence Barnyardgrass 90 90 90 70 60 50 70 90 90 20 90 90 100 100 Blackgrass 90 90 80 80 80 70 90 80 90 20 90 90 90 100 Corn 80 60 70 20 30 50 50 - 80 30 10 40 70 60 Foxtail, Green 100 90 100 100 90 90 100 100 100 0 100 90 100 100 Kochia 100 100 100 100 60 50 80 80 90 0 90 80 100 90 Oat, Wild 90 90 90 60 50 50 70 70 90 0 60 50 90 80 Pigweed, Palmer 100 90 100 100 90 90 90 90 100 60 100 90 100 100 Ragweed 90 50 90 90 0 20 20 - 90 0 90 70 90 80 Ryegrass, Italian 90 90 90 80 90 80 90 90 90 0 90 90 90 90 Soybean 0 60 0 20 0 0 0 0 0 0 50 0 60 70 Wheat 90 90 100 90 40 40 80 80 100 10 80 50 100 100 Table A Compounds 62 g ai / ha 113 114 115 116 117 118 119 120 121 122 123 124 125 126 Preemergence Barnyardgrass 90 100 70 80 80 80 90 90 90 0 20 100 90 80 Blackgrass 100 100 80 90 90 90 90 90 90 0 80 100 100 90 Corn 40 50 40 40 30 80 80 20 50 0 20 80 40 50 Foxtail, Green 100 100 90 90 90 100 100 90 90 0 70 100 90 80 Kochia 100 90 100 90 100 90 100 80 90 0 0 90 90 80 Oat, Wild 90 90 70 90 80 90 90 80 80 0 90 90 90 90 Pigweed, Palmer 100 100 100 100 100 100 100 90 100 0 10 100 100 90 Ragweed 80 90 90 90 90 90 0 0 0 0 90 80 90 Ryegrass, Italian 90 100 80 90 90 90 90 90 90 0 60 90 100 100 Soybean 0 80 0 0 0 0 0 50 40 0 0 70 0 0 Wheat 100 100 80 90 90 90 100 90 90 0 90 100 100 100 Table A Compounds 62 g ai / ha 127 128 129 130 131 132 133 134 138 139 140 141 148 149 Preemergence Barnyardgrass 40 90 90 40 90 90 90 90 40 100 90 0 90 0 Blackgrass 70 90 90 90 90 90 90 90 0 90 70 0 90 90 Corn 40 70 80 20 90 70 90 80 0 50 30 50 50 0 Foxtail, Green 90 100 100 90 100 90 100 90 0 90 90 0 100 90 Kochia 0 100 100 90 90 100 100 100 0 0 50 0 90 30 Oat, Wild 50 90 90 70 90 90 90 90 70 0 10 0 80 50 Pigweed, Palmer 20 100 100 90 100 100 100 100 20 100 90 0 90 70 Ragweed 0 80 90 10 90 90 90 90 0 60 0 0 20 0 Ryegrass, Italian 90 100 90 80 100 90 100 90 90 90 90 0 90 80 Soybean 0 30 50 0 20 0 50 0 0 30 0 20 70 40 Wheat 90 90 90 60 90 90 100 100 90 90 100 70 90 90 Table A Compounds 62 g ai / ha 150 151 152 153 168 170 190 198 215 216 Preemergence Barnyardgrass 60 90 80 60 90 0 0 100 0 20 Blackgrass 80 90 80 90 80 0 0 90 50 60 Corn 10 90 20 10 20 0 0 80 0 20 Foxtail, Green 90 100 90 90 90 0 0 100 0 90 Kochia 70 90 60 90 80 0 0 90 70 100 Oat, Wild 70 90 50 80 80 0 0 90 70 30 Pigweed, Palmer 90 90 90 90 90 0 0 100 70 40 Ragweed 0 90 70 0 60 0 0 30 0 10 Ryegrass, Italian 80 90 80 90 90 0 0 90 10 10 Soybean 0 30 0 20 0 0 0 60 0 30 Wheat 90 90 80 50 90 0 0 90 80 90 Table A Compounds 14 Barnyardgrass 0 60 80 0 30 30 20 0 60 40 50 40 50 0 Blackgrass 70 60 50 0 70 70 40 10 70 60 50 50 20 20 Corn 0 30 30 20 0 20 10 20 20 10 50 10 0 0 Foxtail, Green 20 50 90 40 60 90 80 50 50 70 70 50 90 90 Kochia 0 20 90 40 60 90 90 30 70 70 50 70 20 - Oat, Wild 80 80 80 30 30 50 20 20 30 50 30 20 0 60 Pigweed, Palmer 20 40 90 80 30 90 80 0 30 90 60 60 80 90 Ragweed 0 0 90 0 0 80 0 0 0 0 0 0 40 10 Ryegrass, Italian 80 90 90 0 90 90 60 0 80 80 80 90 90 80 Soybean 0 20 0 0 20 40 0 0 0 0 0 30 20 70 Wheat 90 90 90 20 60 90 80 10 60 30 80 80 70 70 Table A Compounds 16 g ai / ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Preemergence Barnyardgrass 60 0 0 50 50 60 90 50 0 60 70 60 40 80 Blackgrass 20 0 20 90 30 30 90 70 0 60 70 60 60 30 Corn 0 0 0 20 20 20 10 50 0 30 30 10 10 20 Foxtail, Green 70 0 0 0 0 70 90 80 0 90 90 50 80 80 Kochia 20 0 0 60 40 30 80 80 0 50 70 20 30 60 Oat, Wild 60 0 10 20 0 20 90 90 0 70 70 80 30 20 Pigweed, Palmer 90 0 0 80 50 70 90 60 0 50 60 30 20 80 Ragweed 20 0 0 10 0 0 10 0 0 0 0 0 0 0 Ryegrass, Italian 70 10 0 80 60 50 90 60 0 90 90 80 20 60 Soybean 30 0 0 0 0 0 50 0 0 0 0 0 0 0 Wheat 70 10 30 40 10 50 90 80 20 80 90 80 60 80 Table A Compounds 16 g ai / ha 29 30 31 32 33 34 35 36 37 38 39 40 41 42 Preemergence Barnyardgrass 50 0 60 0 60 20 0 0 20 30 0 80 0 0 Blackgrass 70 20 70 70 70 0 30 60 40 30 0 50 0 0 Corn 0 0 10 10 0 0 0 0 10 30 0 30 30 0 Foxtail, Green 80 0 90 80 90 0 0 70 70 20 0 50 0 0 Kochia 50 20 30 60 20 0 0 100 50 90 0 100 20 0 Oat, Wild 20 0 50 0 50 0 0 20 30 50 20 60 30 0 Pigweed, Palmer 90 0 60 70 30 0 0 90 90 50 0 100 - 0 Ragweed 0 0 10 80 10 0 0 0 70 10 0 30 0 0 Ryegrass, Italian 80 0 60 80 70 0 0 20 70 90 0 80 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 10 0 30 30 50 0 10 40 80 80 0 80 70 0 Table A Compounds 16 g ai / ha 43 44 45 46 47 48 49 50 51 52 53 54 55 56 Preemergence Barnyardgrass 90 30 0 30 30 20 60 30 60 20 80 60 0 0 Blackgrass 70 50 0 50 0 50 70 70 80 30 40 40 0 20 Corn 20 0 0 40 30 30 20 20 0 0 40 30 0 20 Foxtail, Green 0 50 0 70 0 90 90 80 90 30 70 90 0 20 Kochia 90 80 0 50 80 80 10 40 70 0 70 30 10 0 Oat, Wild 60 70 0 80 80 80 20 30 20 20 0 0 0 0 Pigweed, Palmer 100 90 0 80 70 - 80 70 70 0 80 70 0 0 Ragweed 10 0 0 10 0 0 0 0 50 0 0 0 0 0 Ryegrass, Italian 90 90 0 80 90 80 80 80 80 0 0 20 0 0 Soybean 0 0 0 60 30 0 0 0 0 0 0 0 0 0 Wheat 80 80 0 80 90 90 20 30 20 30 20 20 0 30 Table A Compounds 16 g ai / ha 57 58 59 60 61 62 63 65 66 67 68 69 72 73 Preemergence Barnyardgrass 0 80 50 90 50 0 0 70 60 0 0 90 90 80 Blackgrass 0 50 50 70 20 20 50 60 80 60 70 80 90 80 Corn 0 80 20 60 20 0 0 10 20 0 0 20 20 30 Foxtail, Green 0 90 0 90 0 30 50 90 90 70 90 100 100 100 Kochia - 90 0 90 20 20 40 90 90 50 80 90 90 90 Oat, Wild 0 90 10 90 0 0 0 20 30 30 0 80 50 80 Pigweed, Palmer 0 100 0 100 90 50 90 90 90 50 90 100 100 90 Ragweed 0 80 0 20 0 20 0 30 50 0 30 50 90 80 Ryegrass, Italian 0 100 0 90 10 0 10 80 80 70 70 90 90 90 Soybean 0 20 0 0 0 0 0 0 0 0 50 0 50 50 Wheat 0 90 20 90 20 0 0 10 30 80 30 90 80 90 Table A Compounds 16 g ai / ha 74 75 76 77 78 79 80 81 82 83 84 85 86 87 Preemergence Barnyardgrass 0 30 20 40 70 90 90 90 0 0 90 0 90 90 Blackgrass 30 50 30 70 90 70 90 90 30 40 90 0 80 80 Corn 10 20 10 30 40 20 0 20 10 0 50 0 60 40 Foxtail, Green 0 30 70 60 90 100 90 90 30 10 80 0 90 80 Kochia 10 0 0 30 90 90 80 80 10 30 90 0 100 90 Oat, Wild 30 70 0 20 90 80 20 60 20 20 90 0 80 80 Pigweed, Palmer 0 0 10 50 90 90 80 90 10 20 90 0 100 90 Ragweed 0 0 0 0 90 80 70 0 0 90 0 70 60 Ryegrass, Italian 10 10 10 80 90 90 90 80 0 40 90 0 90 90 Soybean 0 0 0 0 50 60 0 40 0 0 60 0 30 0 Wheat 30 80 80 50 90 90 40 80 70 70 90 0 90 90 Table A Compounds 16 g ai / ha 88 89 90 91 92 93 94 95 96 97 98 99 100 101 Preemergence Barnyardgrass 0 80 60 90 90 20 0 80 0 20 30 50 80 60 Blackgrass 0 90 80 80 90 40 20 70 0 40 50 70 60 60 Corn 0 10 10 10 0 0 0 20 0 10 20 30 10 40 Foxtail, Green 0 90 100 90 90 40 0 80 0 50 50 80 80 90 Kochia - 90 90 90 90 70 0 30 70 70 60 60 50 80 Oat, Wild 0 90 70 80 80 0 0 70 0 30 20 80 70 80 Pigweed, Palmer 0 90 100 90 100 30 20 70 20 50 80 100 80 90 Ragweed 0 50 40 60 40 0 0 0 0 10 10 60 10 70 Ryegrass, Italian 0 90 90 90 90 10 30 90 10 80 60 70 40 70 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 90 90 90 90 10 0 90 0 80 10 80 80 90 Table A Compounds 16 g ai / ha 102 103 104 105 106 107 108 109 110 111 112 113 114 115 Preemergence Barnyardgrass 10 0 0 0 0 60 0 80 60 90 90 80 90 0 Blackgrass 30 30 0 60 20 60 0 70 50 70 90 80 90 50 Corn 0 0 0 30 30 30 0 0 0 10 30 30 40 30 Foxtail, Green 90 0 50 70 70 80 0 90 70 90 90 90 90 70 Kochia 70 20 20 30 0 90 0 50 0 90 60 100 30 50 Oat, Wild 30 30 20 60 30 70 0 20 0 80 0 70 50 40 Pigweed, Palmer 70 20 0 30 20 90 0 90 100 90 90 100 100 90 Ragweed 10 0 0 0 50 20 0 60 0 50 0 80 80 30 Ryegrass, Italian 50 10 10 40 10 70 0 80 60 90 90 90 90 50 Soybean 0 0 0 0 0 0 0 0 0 20 20 0 30 0 Wheat 40 30 10 10 10 90 0 60 10 90 70 90 80 30 Table A Compounds 16 g ai / ha 116 117 118 119 120 121 122 123 124 125 126 127 128 129 Preemergence Barnyardgrass 0 0 0 30 50 80 0 0 100 60 20 0 60 80 Blackgrass 70 60 50 50 70 50 0 0 80 50 20 0 80 70 Corn 20 20 30 30 10 10 0 10 10 0 0 20 40 50 Foxtail, Green 80 70 70 90 90 0 0 90 70 30 0 80 90 Kochia 60 30 60 30 30 80 0 0 70 60 80 0 90 90 Oat, Wild 50 60 40 40 50 70 0 50 80 60 60 30 80 80 Pigweed, Palmer 90 90 70 90 20 90 0 0 90 20 0 0 90 90 Ragweed 30 60 40 80 0 0 0 0 0 10 0 0 60 30 Ryegrass, Italian 60 60 60 80 80 90 0 0 90 90 80 0 70 60 Soybean 0 0 0 0 0 0 0 0 40 0 0 0 0 0 Wheat 80 70 80 80 90 90 0 80 90 90 80 0 90 90 Table A Compounds 16 g ai / ha 130 131 132 133 134 136 137 138 139 140 141 142 143 144 Preemergence Barnyardgrass 0 90 80 90 80 40 50 0 30 20 0 0 0 0 Blackgrass 10 70 70 70 80 50 60 0 50 0 0 0 50 80 Corn 0 60 70 40 60 0 0 0 40 0 30 0 0 10 Foxtail, Green 30 90 90 90 90 0 50 0 10 20 0 0 0 90 Kochia 20 90 80 90 70 70 70 0 0 0 0 0 10 0 Oat, Wild 60 80 80 80 90 20 50 20 0 0 0 0 0 40 Pigweed, Palmer 30 90 90 100 90 90 90 10 70 0 0 0 0 70 Ragweed 10 70 30 50 50 30 40 0 0 0 0 0 100 10 Ryegrass, Italian 20 80 70 80 70 40 40 0 90 30 0 0 0 90 Soybean 0 0 0 0 0 0 0 0 20 0 0 0 0 0 Wheat 60 90 90 90 90 50 80 50 70 80 0 0 40 80 Table A Compounds 16 g ai / ha 145 146 147 148 149 150 151 152 153 154 155 156 157 158 Preemergence Barnyardgrass 0 0 40 60 0 0 80 50 20 0 80 90 90 70 Blackgrass 80 70 70 70 20 20 60 50 40 0 50 - - 80 Corn 40 0 10 30 0 0 40 0 0 0 30 20 60 20 Foxtail, Green 40 40 80 80 30 0 90 70 30 0 70 90 90 0 Kochia 40 10 30 70 0 0 80 0 0 0 90 100 100 70 Oat, Wild 60 10 10 80 20 30 80 0 20 0 20 80 20 70 Pigweed, Palmer 30 60 70 70 20 30 80 30 0 0 90 70 100 70 Ragweed 30 0 10 0 0 0 10 20 0 0 0 0 90 10 Ryegrass, Italian 50 50 90 90 60 40 80 50 40 0 70 - - 90 Soybean 50 0 0 40 0 0 0 0 20 0 0 0 10 0 Wheat 80 0 20 80 50 60 80 10 40 0 40 90 80 90 Table A Compounds 16 g ai / ha 159 161 162 163 164 165 166 167 168 169 170 171 172 173 Preemergence Barnyardgrass 0 20 40 20 0 0 90 30 0 100 0 60 90 0 Blackgrass 0 50 60 30 - - - 30 30 90 0 30 - 60 Corn 0 0 30 30 0 0 10 10 20 60 0 10 10 10 Foxtail, Green 0 90 90 50 0 0 90 40 0 100 0 90 20 0 Kochia 0 30 80 20 20 0 100 20 40 100 0 60 0 0 Oat, Wild 0 0 30 30 0 0 90 20 20 90 0 80 70 20 Pigweed, Palmer 0 60 100 30 0 0 90 90 60 100 0 50 0 20 Ragweed 0 0 70 50 20 20 90 40 0 0 0 0 0 0 Ryegrass, Italian 0 0 80 90 - - - 0 80 90 0 90 - 20 Soybean 0 0 0 0 0 0 0 0 0 30 0 0 0 0 Wheat 0 20 80 70 0 0 90 80 80 100 0 80 90 80 Table A Compounds 16 g ai / ha 174 175 177 178 179 180 181 183 184 185 186 187 188 189 Preemergence Barnyardgrass 0 70 20 70 60 40 0 0 80 0 40 100 30 40 Blackgrass 70 60 60 50 70 40 0 50 0 80 80 80 60 - Corn 0 10 0 20 40 0 0 10 0 30 0 60 30 30 Foxtail, Green 0 70 0 80 100 40 0 70 0 70 90 90 70 10 Kochia 60 90 0 0 60 40 0 60 0 100 30 0 40 100 Oat, Wild 80 30 60 70 90 20 0 30 0 60 10 70 20 70 Pigweed, Palmer 20 90 20 50 100 90 0 30 0 100 90 100 90 20 Ragweed 0 20 0 80 80 40 0 30 0 90 0 80 40 90 Ryegrass, Italian 90 90 90 70 90 10 0 80 0 90 40 90 60 - Soybean 0 0 0 0 60 0 0 0 0 0 0 40 0 0 Wheat 90 70 70 80 90 80 30 20 0 80 30 90 20 90 Table A Compounds 16 g ai / ha 190 191 192 193 194 195 196 197 198 200 201 202 203 204 Preemergence Barnyardgrass 0 90 70 90 70 80 70 0 90 70 90 0 70 0 Blackgrass 0 - 70 90 30 30 90 0 80 90 70 0 60 0 Corn 0 20 30 40 10 20 20 0 60 30 10 0 0 0 Foxtail, Green 0 70 50 90 0 70 90 0 90 80 90 0 90 0 Kochia 0 100 40 80 30 40 90 0 70 40 100 0 80 0 Oat, Wild 0 10 90 90 30 70 80 0 70 50 10 0 10 0 Pigweed, Palmer 0 90 70 60 80 80 80 0 90 70 80 60 100 0 Ragweed 0 50 0 0 10 10 0 20 10 0 0 60 0 Ryegrass, Italian 0 - 90 90 80 90 90 0 90 90 30 0 80 10 Soybean 0 0 0 80 0 0 30 0 70 0 0 0 0 0 Wheat 0 90 90 90 90 90 90 0 90 80 90 0 70 10 Table A Compounds 16 g ai / ha 205 206 207 208 209 210 211 215 216 217 218 219 220 221 Preemergence Barnyardgrass 0 50 0 80 30 80 0 0 0 0 90 50 80 90 Blackgrass 40 70 0 80 60 70 70 0 30 0 90 60 90 90 Corn 0 30 0 30 0 30 0 0 10 0 40 10 20 10 Foxtail, Green 50 90 30 90 80 70 20 0 20 0 100 90 90 100 Kochia 80 0 20 90 80 40 20 - 40 0 90 40 90 90 Oat, Wild 20 50 0 60 20 20 0 20 0 0 90 0 80 90 Pigweed, Palmer 90 80 20 100 40 90 30 30 0 0 90 90 90 100 Ragweed 10 20 0 0 0 80 30 0 0 60 0 0 0 40 Ryegrass, Italian 90 80 0 90 50 90 20 10 0 0 100 10 90 90 Soybean 0 0 0 0 30 0 0 0 0 10 0 0 0 0 Wheat 30 60 0 80 20 60 10 0 50 0 100 0 80 80 Table A Compounds 16 g ai / ha 222 223 224 225 226 227 228 229 230 231 232 233 234 235 Preemergence Barnyardgrass 40 20 80 50 0 0 0 0 0 0 70 0 20 90 Blackgrass 90 80 80 90 0 30 0 20 0 0 - - 0 80 Corn 0 0 30 60 0 0 0 0 0 0 0 0 0 30 Foxtail, Green 80 60 0 80 0 0 0 0 0 0 50 0 0 100 Kochia 0 0 10 60 0 0 0 0 20 0 100 80 0 50 Oat, Wild 80 50 100 90 0 60 0 20 0 0 70 30 0 90 Pigweed, Palmer 90 90 0 90 0 0 0 0 0 0 20 80 0 90 Ragweed 0 0 0 0 0 0 0 0 0 0 0 70 0 0 Ryegrass, Italian 90 90 90 90 0 0 0 90 0 0 - - 0 90 Soybean 0 0 0 0 0 0 0 0 0 0 30 0 10 0 Wheat 70 0 90 100 0 80 0 80 0 0 80 - 0 90 Table A Compounds 16 g ai / ha 236 237 238 240 241 242 Preemergence Barnyardgrass 90 10 0 0 0 0 Blackgrass 80 30 50 0 20 0 Corn 20 0 0 0 0 0 Foxtail, Green 90 70 60 40 0 Kochia 90 20 40 20 30 0 Oat, Wild 90 0 30 0 0 10 Pigweed, Palmer 100 90 90 30 - 0 Ragweed 20 0 0 0 0 0 Ryegrass, Italian 90 70 70 0 10 0 Soybean 0 0 0 0 0 0 Wheat 90 0 20 0 10 0 Table A Compounds 4 g ai / ha 18 21 23 34 35 51 55 59 61 62 63 65 66 68 Preemergence Barnyardgrass 20 20 0 0 0 30 0 0 10 0 0 20 0 0 Blackgrass 0 30 0 0 0 20 0 50 0 0 0 10 30 0 Corn 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Foxtail, Green 0 0 0 0 0 20 0 0 0 0 0 30 20 0 Kochia 30 30 0 0 0 30 0 0 0 0 0 50 40 20 Oat, Wild 0 70 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed, Palmer 10 20 0 0 0 40 0 0 0 0 0 90 30 10 Ragweed 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian 0 80 0 0 0 10 0 0 0 0 10 10 20 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Wheat 0 90 0 0 0 0 0 0 0 0 0 0 0 0 Table A Compounds 4 g ai / ha 69 72 73 78 79 80 81 89 90 91 92 136 137 142 Preemergence Barnyardgrass 0 50 0 40 20 0 0 0 20 20 30 0 20 0 Blackgrass 30 70 50 80 60 40 70 20 30 20 30 0 0 0 Corn 0 0 0 10 20 0 0 0 0 0 0 0 0 0 Foxtail, Green 90 50 60 70 80 70 70 0 0 0 60 0 0 0 Kochia 90 40 50 70 30 20 20 20 20 40 60 20 40 0 Oat, Wild 50 20 10 0 30 20 20 30 30 30 60 0 0 0 Pigweed, Palmer 90 50 40 60 60 40 40 80 70 30 60 0 30 0 Ragweed 0 10 30 0 20 50 0 0 20 10 0 0 0 0 Ryegrass, Italian 80 10 40 40 70 60 50 20 20 40 0 0 0 0 Soybean 0 0 0 0 0 0 40 0 0 0 0 0 0 0 0 Table A Compounds 4 g ai / ha 143 144 145 146 147 154 155 156 157 158 159 161 162 163 Preemergence Barnyardgrass 0 0 0 0 0 0 0 70 10 0 0 0 20 20 Blackgrass 0 0 20 0 0 0 0 - - 20 0 20 10 0 Corn 0 0 0 0 0 0 0 10 30 0 0 0 0 0 Foxtail, Green 0 0 0 0 0 0 0 0 20 0 0 20 20 30 Kochia 0 0 10 0 0 0 70 50 90 10 0 0 0 0 Oat, Wild 0 0 10 0 0 0 0 50 20 0 0 0 0 0 Pigweed, Palmer 0 50 10 0 0 0 60 10 70 10 0 20 10 10 Ragweed 40 0 - 0 0 0 0 0 10 0 0 0 0 30 Ryegrass, Italian 0 0 10 0 0 0 20 - - 50 0 0 0 0 Soybean 0 0 50 0 0 0 0 0 0 0 0 0 0 0 Wheat 0 0 0 0 0 0 10 70 70 30 0 0 10 10 Table A Compounds 4 g ai / ha 164 165 166 167 169 171 172 173 174 175 177 178 179 180 Preemergence Barnyardgrass 0 0 20 0 0 0 60 0 0 0 0 20 0 0 Blackgrass - - - 0 60 0 - 0 20 20 0 0 30 0 Corn 0 0 10 0 0 0 0 0 0 10 0 10 0 0 Foxtail, Green 0 0 0 0 20 0 0 0 0 20 0 0 20 0 Kochia 0 0 90 10 20 20 0 0 10 30 0 0 30 40 Oat, Wild 0 0 60 0 70 10 0 0 30 30 0 0 80 0 Pigweed, Palmer 0 0 20 20 30 0 0 0 0 50 0 0 20 50 Ragweed 0 20 30 0 0 0 0 0 0 0 90 0 0 0 Ryegrass, Italian - - - 0 80 20 - 0 70 10 30 0 80 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 40 0 Wheat 0 0 90 0 90 10 0 0 80 30 0 30 80 0 Table A Compounds 181 183 184 185 186 187 188 189 191 192 193 194 195 196 Preemergence Barnyardgrass 0 0 0 0 30 40 30 0 80 0 0 0 20 0 Blackgrass 0 0 0 20 30 20 0 - - 20 30 0 0 60 Corn 0 0 0 0 0 30 0 0 10 0 10 0 0 0 Foxtail, Green 0 0 0 0 0 60 0 0 0 0 0 0 0 0 Kochia 0 20 0 80 0 20 0 0 0 20 0 0 0 30 Oat, Wild 0 0 0 0 0 40 0 0 0 40 70 0 0 20 Pigweed, Palmer 0 0 0 50 40 90 40 0 20 0 0 0 0 30 Ragweed 0 0 0 0 0 0 80 50 0 0 0 0 0 Ryegrass, Italian 0 10 0 0 0 0 0 - - 40 80 0 20 60 Soybean 0 0 0 0 0 0 0 0 0 0 50 0 0 0 Wheat 0 10 0 80 0 60 0 20 10 50 80 10 30 80 Table A Compounds 4 g ai / ha 197 200 201 202 203 204 205 206 207 208 209 210 211 217 Preemergence Barnyardgrass 0 0 0 0 20 0 0 10 0 0 0 60 0 0 Blackgrass 0 20 30 0 0 0 0 30 0 30 10 10 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Foxtail, Green 0 0 0 0 30 0 0 10 0 60 10 0 0 0 Kochia 0 0 40 0 10 0 20 0 0 20 0 10 0 60 Oat, Wild 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed, Palmer 0 0 10 20 20 0 - 70 0 30 0 40 0 0 Ragweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian 0 0 0 0 0 0 0 50 0 60 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 10 0 0 0 Wheat 0 0 60 0 0 0 0 10 0 50 0 20 0 0 Table A Compounds 4 g ai / ha 218 219 220 221 222 223 224 225 226 227 228 229 230 231 Preemergence Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Blackgrass 80 20 40 30 30 20 20 20 0 0 0 0 0 0 Corn 10 0 0 10 0 0 0 20 0 0 0 0 0 0 Foxtail, Green 90 0 0 70 0 0 0 0 0 0 0 0 0 0 Kochia 30 20 0 30 0 0 0 0 0 0 0 0 0 0 Oat, Wild 70 0 10 40 10 0 50 90 0 0 0 0 0 0 Pigweed, Palmer 60 50 30 50 50 40 0 20 0 0 0 0 0 0 Ragweed 0 0 0 0 - 0 0 0 0 0 0 0 0 0 Ryegrass, Italian 90 0 80 70 30 0 0 90 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Wheat 80 0 10 0 0 0 70 90 0 0 0 0 0 0 Table A Compounds 4 g ai / ha 232 233 234 235 236 237 238 240 241 242 Preemergence Barnyardgrass 10 0 0 0 0 0 0 0 0 0 Blackgrass - - 0 60 20 0 0 0 0 0 Corn 0 0 0 0 10 0 0 0 0 0 Foxtail, Green 0 0 0 70 0 60 0 0 0 Kochia 0 30 0 20 20 0 0 0 0 0 Oat, Wild 0 0 0 30 60 0 0 0 0 0 Pigweed, Palmer 0 0 0 0 60 40 40 0 0 0 Ragweed 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian - - 0 80 90 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 0 0 Wheat 60 - 0 50 80 0 0 0 0 0 Table A Compounds 62 g ai / ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Postemergence Barnyardgrass 80 90 90 80 80 90 90 30 90 90 90 90 90 80 Blackgrass 100 100 100 100 90 100 100 90 100 100 100 100 90 80 Corn 100 100 100 100 80 60 90 30 100 100 100 100 30 40 Foxtail, Green 90 90 80 80 90 90 90 0 90 90 90 90 90 80 Galium 90 90 90 90 80 80 70 70 80 80 80 80 80 80 Horseweed 0 10 80 90 30 80 80 20 40 20 40 50 0 0 Kochia 80 90 80 80 - - - - - - - - 80 80 Oat, Wild 90 90 100 90 90 90 100 60 90 100 90 - 80 90 Pigweed, Palmer 80 90 90 90 90 90 90 90 90 90 90 90 90 90 Ragweed 20 40 80 80 60 90 90 70 80 80 70 70 80 90 Ryegrass, Italian 90 90 90 90 - - - - - - - - 80 90 Soybean 50 70 40 40 60 40 40 20 60 70 70 70 60 60 Wheat 90 90 80 80 60 60 70 30 60 60 40 50 50 50 Table A Compounds 62 g ai / ha 15 16 17 19 20 22 24 25 26 27 28 29 30 31 Postemergence Barnyardgrass 80 60 70 90 90 80 80 90 90 80 90 80 40 70 Blackgrass 70 70 60 90 90 90 90 90 90 100 90 90 90 90 Corn 70 10 20 90 100 100 100 100 100 20 100 60 20 70 Foxtail, Green 70 60 80 90 90 90 80 90 90 90 90 80 70 90 Galium 80 70 80 80 90 80 90 90 80 90 80 90 80 80 Horseweed 0 20 20 30 80 80 80 70 80 - 80 70 20 30 Kochia 80 80 80 80 80 80 80 80 80 70 80 80 80 90 Oat, Wild 90 70 70 90 90 100 100 100 100 90 100 90 60 90 Pigweed, Palmer 80 60 70 90 90 90 90 90 90 90 90 100 90 90 Ragweed 80 0 40 70 80 80 80 90 90 70 70 60 60 80 Ryegrass, Italian 80 80 90 90 90 90 90 90 90 90 100 90 80 80 Soybean 80 40 40 60 70 60 70 70 50 70 80 30 70 Wheat 50 60 70 40 70 80 60 50 90 70 60 60 10 70 Table A Compounds 62 g ai / ha 32 33 36 37 38 39 40 41 42 43 44 45 46 47 Postemergence Barnyardgrass 90 80 80 80 80 80 80 70 80 80 80 70 70 80 Blackgrass 90 90 90 90 100 80 90 100 90 90 90 90 90 90 Corn 60 60 60 90 100 60 100 100 0 100 100 40 100 100 Foxtail, Green 80 80 80 80 90 80 90 70 80 80 80 70 80 90 Galium 90 80 80 80 90 80 90 90 60 80 80 80 90 90 Horseweed 60 40 80 80 90 50 80 90 50 90 90 20 90 90 Kochia 80 80 80 80 80 80 80 80 80 80 80 80 80 80 Oat, Wild 90 80 20 40 100 80 100 90 30 100 100 30 90 100 Pigweed, Palmer 90 90 90 90 90 90 90 90 90 90 90 90 90 90 Ragweed 80 80 80 90 90 80 80 80 70 90 80 80 90 90 Ryegrass, Italian 90 90 90 90 100 80 100 90 60 100 100 90 100 100 Soybean 60 60 40 40 70 40 70 70 40 60 70 40 70 60 Wheat 50 70 50 60 70 80 80 80 70 80 70 60 80 70 Table A Compounds 62 g ai / ha 48 49 50 52 53 54 56 57 58 60 67 74 75 76 Postemergence Barnyardgrass 100 90 80 80 90 80 80 90 80 80 80 80 80 90 Blackgrass 100 90 90 90 100 100 90 90 100 100 90 90 90 90 Corn 90 70 10 100 100 100 100 90 100 100 50 90 100 100 Foxtail, Green 90 90 90 80 90 90 80 90 80 80 90 80 80 90 Galium 80 90 80 50 90 80 80 40 80 80 90 80 70 80 Horseweed - 80 30 0 80 80 20 50 90 80 30 40 0 - Kochia 70 80 80 80 90 80 80 70 70 80 80 80 80 70 Oat, Wild 90 50 90 80 90 90 90 60 100 90 70 100 100 90 Pigweed, Palmer 90 100 90 60 100 100 90 70 100 90 90 90 90 - Ragweed 90 80 70 40 80 90 60 40 90 80 80 20 30 20 Ryegrass, Italian 100 90 90 90 90 90 90 60 90 90 90 90 90 90 Soybean 80 70 40 30 70 60 40 40 60 50 50 50 50 60 Wheat 80 50 30 60 80 80 50 60 40 60 30 70 80 90 Table A Compounds 62 g ai / ha 77 82 83 84 85 86 87 88 93 94 95 96 97 98 Postemergence Barnyardgrass 90 90 70 80 30 90 90 60 90 80 90 20 90 80 Blackgrass 90 90 100 100 100 90 70 90 90 90 30 100 90 Corn 100 100 100 100 0 90 90 30 100 100 100 70 100 50 Foxtail, Green 90 90 90 80 0 90 90 50 90 90 90 70 90 90 Galium 90 70 80 90 30 90 80 60 80 80 80 60 80 80 Horseweed - 60 70 70 80 80 80 0 90 10 30 - 10 20 Kochia 70 80 90 80 10 80 80 80 80 80 80 60 80 90 Oat, Wild 90 90 90 100 10 100 100 30 90 90 90 60 90 90 Pigweed, Palmer - 90 60 90 40 100 90 90 90 90 - - - 90 Ragweed 30 10 10 90 0 90 80 30 70 0 80 10 30 40 Ryegrass, Italian 90 90 90 90 0 80 100 50 90 80 90 70 80 80 Soybean 60 50 50 60 30 40 50 30 50 40 60 30 30 60 Wheat 90 90 90 80 0 80 60 20 80 80 90 60 90 70 Table A Compounds 62 g ai / ha 99 100 101 102 103 104 105 106 107 108 109 110 111 112 Postemergence Barnyardgrass 70 90 90 80 70 80 80 70 90 70 80 80 80 80 Blackgrass 90 90 100 90 90 90 90 90 90 90 90 90 90 90 Corn 80 90 100 100 90 100 100 100 100 30 100 90 100 100 Foxtail, Green 80 90 90 80 80 80 80 80 90 90 90 90 90 90 Galium 80 80 80 80 80 90 80 80 80 90 90 90 80 90 Horseweed 80 80 80 80 10 80 20 70 80 70 90 20 90 20 Kochia 80 80 80 80 80 80 80 - 80 70 90 90 90 80 Oat, Wild 70 90 90 90 90 90 90 100 90 40 90 90 90 90 Pigweed, Palmer 90 100 90 90 70 90 80 90 90 - - - - - Ragweed 90 90 90 80 30 50 20 30 90 60 80 80 80 70 Ryegrass, Italian 90 90 90 80 80 80 100 100 90 70 90 80 80 90 Soybean 40 60 60 50 50 50 60 60 60 60 60 60 60 60 Wheat 30 60 50 80 80 80 90 80 50 80 100 90 90 90 Table A Compounds 62 g ai / ha 113 114 115 116 117 118 119 120 121 122 123 124 125 126 Postemergence Barnyardgrass 80 90 90 80 50 90 90 90 80 30 80 80 70 60 Blackgrass 90 90 90 90 90 90 90 100 100 60 90 100 80 80 Corn 90 90 100 80 80 100 100 100 100 10 100 100 40 20 Foxtail, Green 90 90 90 80 90 90 90 90 90 0 70 90 70 60 Galium 90 80 80 80 80 80 80 80 90 60 80 80 80 80 Horseweed 90 50 80 80 80 80 80 - - 0 10 90 0 0 Kochia 90 80 80 80 80 80 80 70 80 0 0 80 50 80 90 90 80 90 30 40 80 Blackgrass 80 90 90 60 90 90 90 90 80 90 90 70 90 100 Corn 50 100 90 20 90 100 90 100 30 90 40 30 100 90 Foxtail, Green 60 90 90 30 90 90 90 90 90 80 80 80 90 90 Galium 70 80 80 80 80 80 80 80 60 80 70 60 90 60 Horseweed 0 80 90 30 80 80 90 80 0 0 0 0 60 10 Kochia 70 80 80 80 80 80 80 80 80 90 70 70 80 80 Oat, Wild 90 90 90 0 90 100 100 90 90 90 90 90 90 90 Pigweed, Palmer 50 100 90 90 90 100 90 90 70 80 70 30 90 90 Ragweed 30 90 80 50 80 80 90 80 10 80 50 0 80 20 Ryegrass, Italian 90 90 90 30 80 90 90 90 70 100 90 60 90 80 Soybean 40 40 50 40 50 50 40 50 50 60 30 40 70 20 Wheat 60 40 50 40 40 50 50 50 60 60 50 70 - 80 Table A Compounds 62 g ai / ha 150 151 152 153 168 170 190 198 215 216 Postemergence Barnyardgrass 80 90 80 70 90 20 0 80 40 80 Blackgrass 100 90 90 90 90 0 0 100 60 100 Corn 100 100 100 20 20 0 0 100 20 100 Foxtail, Green 90 90 90 70 90 0 0 80 50 90 Galium 90 80 80 90 90 0 0 80 80 80 Horseweed 10 80 80 10 - - - 80 0 80 Kochia 80 80 80 80 80 0 0 80 80 80 Oat, Wild 90 100 90 80 90 0 0 100 70 90 Pigweed, Palmer 90 100 90 60 90 0 0 - - 90 Ragweed 30 80 90 20 80 0 0 90 0 80 Ryegrass, Italian 80 90 90 90 90 0 0 100 80 90 Soybean 40 50 70 30 20 0 0 70 70 70 Wheat 80 70 70 - 60 0 0 90 80 80 Table A Compounds 16 g ai / ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Postemergence Barnyardgrass 70 80 80 20 50 30 40 20 70 90 80 90 70 60 Blackgrass 90 90 90 90 90 90 90 70 90 100 90 80 70 50 Corn 70 80 90 40 30 10 10 0 80 80 80 90 0 10 Foxtail, Green 50 30 80 70 60 40 80 0 80 80 70 60 70 40 Galium 10 60 80 50 80 80 50 70 80 80 80 80 70 80 Horseweed 0 0 70 70 10 70 50 20 0 10 10 30 0 0 Kochia 60 70 80 80 - 90 80 60 - 90 - - 70 70 Oat, Wild 90 90 90 50 80 80 90 30 70 90 90 80 80 80 Pigweed, Palmer 10 50 90 90 60 90 80 50 80 80 80 90 80 70 Ragweed 20 10 80 70 0 80 70 10 0 20 0 50 60 50 Ryegrass, Italian 70 80 90 60 20 70 80 80 50 30 20 20 60 60 Soybean 20 0 30 30 30 30 30 0 40 50 30 50 40 30 Wheat 90 80 70 50 40 40 70 0 50 40 40 40 50 40 Table A Compounds 16 g ai / ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Postemergence Barnyardgrass 80 0 0 80 80 90 80 70 40 80 90 80 70 90 Blackgrass 60 20 20 90 90 90 100 90 50 90 90 90 90 90 Corn 20 0 0 90 90 100 100 90 0 100 100 100 20 90 Foxtail, Green 40 0 0 60 60 80 80 80 30 80 80 80 30 80 Galium 80 40 30 - 80 90 - 80 - 90 90 80 90 80 Horseweed 0 0 0 20 10 80 60 40 10 60 60 40 10 80 Kochia 80 60 30 80 80 80 80 80 20 80 80 80 70 80 Oat, Wild 80 40 70 90 60 80 100 90 60 100 100 100 90 90 Pigweed, Palmer 80 20 30 90 90 90 90 90 20 90 90 90 20 90 Ragweed 60 0 0 20 20 80 80 70 0 70 70 70 50 70 Ryegrass, Italian 80 70 0 90 50 80 90 80 0 80 80 90 80 80 Soybean 30 0 30 50 20 70 80 60 0 60 50 60 40 60 Wheat 40 70 60 90 40 70 90 80 0 50 60 80 60 50 Table A Compounds 16 g ai / ha 29 30 31 32 33 34 35 36 37 38 39 40 41 42 Postemergence Barnyardgrass 60 0 40 60 60 30 90 40 40 80 60 80 70 20 Blackgrass 80 60 80 80 90 30 80 90 90 100 60 90 90 40 Corn 10 0 0 10 30 0 10 30 50 100 10 100 70 0 Foxtail, Green 80 10 80 70 30 90 20 70 80 70 80 70 50 Galium 80 70 60 80 50 0 90 80 80 90 10 90 70 40 Horseweed 20 10 10 10 10 0 - 60 80 80 0 80 70 20 Kochia 80 80 80 80 80 30 90 80 80 80 70 80 80 40 Oat, Wild 40 0 80 30 70 0 80 0 30 90 10 100 90 0 Pigweed, Palmer 90 80 90 80 90 80 90 90 100 90 80 90 90 30 Ragweed 60 10 70 70 80 0 70 70 80 80 0 90 70 10 Ryegrass, Italian 70 20 70 90 70 0 70 80 80 100 0 100 90 0 Soybean 40 20 40 30 40 0 0 20 20 70 30 60 70 0 Wheat 30 0 70 60 60 0 60 40 50 70 10 80 70 30 Table A Compounds 16 g ai / ha 43 44 45 46 47 48 49 50 51 52 53 54 55 56 Postemergence Barnyardgrass 70 70 20 60 80 100 70 50 50 50 80 70 10 80 Blackgrass 90 90 70 90 90 100 70 80 100 90 90 90 0 80 Corn 100 100 10 100 100 80 20 0 10 90 100 100 0 100 Foxtail, Green 80 80 0 80 80 90 70 70 70 70 90 90 0 40 Galium 80 80 30 80 90 50 80 80 80 20 90 80 - 20 Horseweed 80 80 0 80 70 50 30 10 10 0 80 80 0 0 50 Oat, Wild 90 90 0 90 90 90 50 60 50 40 80 70 10 70 Pigweed, Palmer 100 90 70 90 90 90 90 90 90 50 100 90 20 10 Ragweed 70 80 0 80 80 80 50 10 20 10 80 80 0 0 Ryegrass, Italian 90 100 60 100 80 80 80 70 70 40 90 90 0 60 Soybean 40 60 0 60 50 70 40 40 30 20 60 60 0 40 Wheat 70 70 50 80 70 70 50 30 0 50 80 70 0 50 Table A Compounds 16 g ai / ha 57 58 59 60 61 62 63 65 66 67 68 69 72 73 Postemergence Barnyardgrass 80 80 80 80 80 90 80 80 80 50 70 90 80 80 Blackgrass 80 100 90 100 100 90 90 90 100 80 90 90 100 90 Corn 80 100 90 100 90 90 30 10 20 20 0 90 50 80 Foxtail, Green 80 80 80 80 70 90 90 80 80 60 70 90 80 80 Galium 20 80 - 80 - 90 90 90 90 90 70 90 90 90 Horseweed 0 80 0 80 80 - - 20 0 10 0 - 30 30 Kochia 20 70 60 80 80 80 80 90 90 80 90 80 80 80 Oat, Wild 20 90 90 90 80 70 60 20 60 40 70 90 90 90 Pigweed, Palmer 20 90 10 90 90 90 90 90 90 90 90 90 80 90 Ragweed 0 80 0 90 80 80 70 40 40 20 80 80 80 Ryegrass, Italian 30 90 80 90 60 60 40 50 70 50 50 80 80 80 Soybean 30 60 30 40 80 50 0 30 40 30 30 60 50 50 Wheat 60 40 70 60 70 30 70 40 10 30 20 70 90 80 Table A Compounds 16 g ai / ha 74 75 76 77 78 79 80 81 82 83 84 85 86 87 Postemergence Barnyardgrass 70 40 80 80 80 80 80 80 80 60 80 0 80 90 Blackgrass 90 90 90 90 90 90 90 90 90 100 90 0 90 90 Corn 60 80 80 90 60 60 60 50 90 100 70 0 90 90 Foxtail, Green 70 50 90 90 80 80 80 80 90 50 80 0 80 90 Galium 30 30 60 80 90 90 90 90 70 70 90 0 90 80 Horseweed 0 0 - - 30 30 10 20 20 10 30 80 70 70 Kochia 80 50 60 70 80 80 80 80 70 70 80 0 80 80 Oat, Wild 100 90 90 90 100 90 90 90 90 90 90 0 90 100 Pigweed, Palmer 80 20 - - 90 90 90 90 80 20 90 0 90 90 Ragweed 0 0 40 20 80 90 90 90 0 10 80 0 80 80 Ryegrass, Italian 60 80 90 80 90 90 90 90 80 90 90 0 80 80 Soybean 30 30 50 50 60 50 60 60 40 40 60 0 20 50 Wheat 60 60 90 90 80 80 80 80 90 90 70 0 80 80 Table A Compounds 16 g ai / ha 88 89 90 91 92 93 94 95 96 97 98 99 100 101 Postemergence Barnyardgrass 30 80 80 80 70 80 50 80 0 90 70 60 90 90 Blackgrass 20 90 90 90 90 90 80 90 0 90 90 80 90 90 Corn 0 90 90 90 100 100 90 70 10 50 20 60 50 90 Foxtail, Green 0 80 80 80 70 80 30 90 10 90 80 90 90 90 Galium 30 - - - - 80 40 80 40 80 80 80 80 80 Horseweed 0 90 80 90 90 60 10 30 - 10 0 70 20 80 Kochia 50 80 80 80 80 80 50 80 0 80 80 80 80 80 Oat, Wild 30 90 90 90 90 80 60 90 0 90 70 60 80 80 Pigweed, Palmer 50 90 90 90 90 90 30 - - - 90 100 90 90 Ragweed 20 80 90 80 80 20 0 70 0 10 40 90 60 80 Ryegrass, Italian 0 90 90 90 90 70 40 80 0 80 80 70 80 80 Soybean 30 50 50 50 50 50 20 50 30 10 0 20 50 50 Wheat 0 20 50 40 50 40 40 90 0 90 60 30 40 40 Table A Compounds 16 g ai / ha 102 103 104 105 106 107 108 109 110 111 112 113 114 115 Postemergence Barnyardgrass 70 70 80 80 70 80 30 80 80 80 80 70 80 30 Blackgrass 90 80 80 80 90 90 30 100 90 90 90 90 90 90 Corn 70 70 90 90 100 70 10 90 70 90 100 60 30 60 Foxtail, Green 80 60 80 80 80 90 50 90 90 90 90 90 90 90 Galium 80 70 80 80 80 80 70 80 90 90 80 80 90 80 Horseweed 80 0 30 10 0 50 10 90 10 70 0 70 20 80 80 70 70 60 60 80 60 90 90 90 80 90 80 80 Oat, Wild 80 80 90 90 90 80 10 90 90 90 90 90 90 50 Pigweed, Palmer 90 20 80 10 70 90 - - - - - - - 90 Ragweed 80 0 10 20 30 80 0 70 0 70 10 80 70 80 Ryegrass, Italian 80 50 80 90 80 90 0 80 80 70 90 80 80 60 Soybean 40 0 30 40 40 50 20 60 50 60 50 30 50 30 Wheat 80 50 80 80 80 40 0 90 80 90 90 90 90 30 Table A Compounds 16 ai / ha 116 117 118 119 120 121 122 123 124 125 126 127 128 129 90 Blackgrass 70 80 90 90 100 100 0 80 100 70 70 60 90 90 Corn 50 60 80 70 50 40 0 40 90 10 0 20 80 70 Foxtail, Green 60 60 80 80 80 90 0 10 90 30 0 20 90 90 Galium 80 80 80 80 80 90 0 70 80 80 80 50 80 80 Horseweed 70 50 70 70 0 - 0 10 80 0 0 0 80 80 Kochia 80 80 80 80 70 70 0 0 80 30 80 20 80 80 Oat, Wild 50 60 80 80 90 90 0 90 90 90 70 80 90 80 Pigweed, Palmer 90 80 90 90 80 90 0 - 90 40 50 0 90 90 Ragweed 90 80 80 90 60 80 0 0 80 20 40 0 80 80 Ryegrass, Italian 70 80 70 90 80 90 0 80 90 90 80 60 90 90 Soybean 30 30 20 40 50 50 0 0 50 0 20 0 30 30 Wheat 20 30 40 60 60 70 0 90 90 50 40 70 30 40 Table A Compounds 16 g ai / ha 130 131 132 133 134 136 137 138 139 140 141 142 143 144 Postemergence Barnyardgrass 0 50 90 90 90 80 80 60 80 20 20 70 0 90 Blackgrass 10 90 90 90 90 90 90 30 80 70 20 80 80 90 Corn 0 70 90 90 80 90 90 0 90 0 10 20 0 70 Foxtail, Green 30 90 90 90 80 80 40 70 30 30 90 40 90 Galium 60 80 80 80 80 - - 40 80 60 50 30 40 90 Horseweed 0 80 70 80 80 80 80 0 0 0 0 - 0 - Kochia 50 80 80 80 80 80 80 10 20 0 10 40 80 80 Oat, Wild 0 90 100 90 90 90 80 80 90 50 40 30 0 90 Pigweed, Palmer 70 90 100 90 90 90 90 20 70 40 0 60 60 90 Ragweed 0 80 80 90 90 90 90 0 30 10 0 10 0 40 Ryegrass, Italian 10 80 80 90 80 80 80 20 90 70 10 10 50 60 Soybean 0 30 30 30 30 40 40 20 40 0 0 0 0 40 Wheat 20 40 40 40 40 60 50 50 50 40 20 10 50 70 Table A Compounds 16 g ai / ha 145 146 147 148 149 150 151 152 153 154 155 156 157 158 Postemergence Barnyardgrass 80 70 80 70 50 50 90 70 0 0 90 90 100 80 Blackgrass 90 90 100 90 70 90 90 90 80 0 100 100 100 100 Corn 90 20 40 90 20 70 70 60 10 0 60 50 10 0 Foxtail, Green 80 80 80 90 0 60 90 80 20 0 90 90 100 80 Galium 90 90 90 90 10 20 80 80 90 - 90 90 70 - Horseweed 0 40 0 10 0 0 60 10 0 0 90 40 70 20 Kochia 80 60 80 80 10 70 80 80 60 0 90 90 90 80 Oat, Wild 80 60 80 90 80 80 90 60 70 0 50 100 90 90 Pigweed, Palmer 90 90 90 90 30 60 90 90 20 0 90 90 90 80 Ragweed 80 80 60 60 10 10 70 80 0 0 70 80 90 80 Ryegrass, Italian 90 90 90 80 70 60 80 80 90 0 80 90 80 90 Soybean 20 10 30 60 0 0 50 60 0 0 40 10 40 0 Wheat 90 80 90 - 70 70 40 70 - 0 70 70 80 80 Table A Compounds 16 g ai / ha 159 161 162 163 164 165 166 167 168 169 170 171 172 173 Postemergence Barnyardgrass 0 90 30 20 0 0 90 80 70 60 0 80 100 0 Blackgrass 0 90 90 80 0 0 100 90 90 100 0 80 60 100 Corn 0 60 40 40 0 0 20 90 10 80 0 10 80 0 Foxtail, Green 0 90 40 60 0 0 90 70 60 80 0 70 90 0 Galium 10 90 90 80 0 0 90 - 80 90 0 - 90 90 Horseweed 0 - 50 0 0 0 50 90 30 40 0 30 10 20 Kochia 0 80 80 80 0 0 90 80 60 80 0 80 80 50 Oat, Wild 0 90 80 90 0 20 100 80 80 90 0 90 100 20 Pigweed, Palmer 0 90 80 70 0 0 90 90 80 90 0 90 90 80 Ragweed 0 10 90 40 0 80 80 60 70 0 70 0 20 Ryegrass, Italian 0 80 80 80 0 0 90 80 80 90 0 80 80 80 Soybean 20 20 10 70 0 0 10 40 0 40 0 30 30 0 Wheat 0 70 90 70 0 0 70 40 60 90 0 60 80 70 Table A Compounds 16 g ai / ha 174 175 177 178 179 180 181 183 184 185 186 187 188 189 Postemergence Barnyardgrass 30 90 20 90 80 80 0 90 70 20 30 90 20 50 Blackgrass 100 100 70 90 100 90 70 90 100 100 90 90 80 50 Corn 30 70 50 90 70 90 0 50 100 10 0 100 20 10 Foxtail, Green 50 80 60 90 90 80 0 90 70 40 10 90 10 50 Galium 90 90 80 90 90 - - 90 50 90 90 90 90 90 Horseweed 0 80 10 0 80 80 0 - 20 70 30 50 80 0 Kochia 80 90 50 80 80 80 60 80 20 80 80 80 80 80 Oat, Wild 60 90 100 90 90 90 30 80 70 60 0 90 30 40 Pigweed, Palmer 70 90 60 90 90 90 20 50 20 90 90 90 70 70 Ragweed 10 70 20 60 80 70 0 10 10 90 90 80 90 50 Ryegrass, Italian 90 80 90 90 90 70 20 80 90 90 80 80 70 80 Soybean 0 40 80 60 20 30 0 0 40 20 30 80 30 10 Wheat 80 70 70 80 80 20 30 70 80 60 30 70 70 80 Table A Compounds 16 g ai / ha 190 191 192 193 194 195 196 197 198 200 201 202 203 204 Postemergence Barnyardgrass 0 80 90 80 70 80 80 0 80 90 70 20 90 50 Blackgrass 0 100 100 100 90 90 100 0 100 90 90 60 100 90 Corn 0 40 80 100 70 10 70 0 100 90 90 0 60 0 Foxtail, Green 0 30 90 80 70 70 80 0 80 90 80 70 90 0 Galium 0 90 90 - - - - 0 90 90 90 0 90 0 Horseweed 0 20 20 0 50 30 50 0 10 - 30 0 80 0 Kochia 0 90 80 80 80 80 80 0 80 80 80 0 80 0 Oat, Wild 0 70 90 90 80 90 90 0 90 90 100 10 90 0 Pigweed, Palmer 0 90 70 80 90 80 90 0 90 90 90 10 90 10 Ragweed 0 80 80 0 80 60 70 0 80 10 70 0 80 0 Ryegrass, Italian 0 80 90 90 80 80 90 0 80 90 80 0 90 0 Soybean 0 20 30 70 0 20 10 0 70 30 60 30 70 0 Wheat 0 70 90 80 80 50 60 0 80 70 70 0 80 0 Table A Compounds 16 g ai / ha 205 206 207 208 209 210 211 215 216 217 218 219 220 221 Postemergence Barnyardgrass 80 40 80 90 90 80 90 20 80 0 90 80 0 90 Blackgrass 70 90 90 90 90 100 80 20 90 20 90 90 90 90 Corn 50 70 100 10 70 70 60 0 100 0 90 10 10 60 Foxtail, Green 70 80 80 90 80 70 90 50 80 0 90 90 50 90 Galium 90 90 - 90 90 - 90 80 80 90 90 90 90 90 Horseweed - 10 0 - 50 70 - 0 80 0 - - - - Kochia 80 80 30 80 80 80 70 70 80 70 80 80 80 80 Oat, Wild 80 60 90 90 90 90 90 50 90 0 90 70 90 90 Pigweed, Palmer 90 90 10 90 80 90 80 90 90 60 90 90 90 90 Ragweed 70 80 10 70 70 90 10 0 70 20 40 30 30 40 Ryegrass, Italian 70 80 60 80 80 80 80 0 90 50 80 90 90 90 Soybean 0 10 20 0 70 0 0 60 70 20 60 40 70 70 Wheat 50 30 50 90 80 70 70 0 80 0 80 70 60 80 Table A Compounds 16 g ai / ha 222 223 224 225 226 227 228 229 230 231 232 233 234 235 Postemergence Barnyardgrass 70 20 90 60 0 0 0 0 0 0 90 10 0 90 Blackgrass 100 100 100 100 90 90 0 80 0 0 100 100 20 100 Corn 50 20 90 90 0 0 0 0 0 0 0 0 0 90 Foxtail, Green 80 30 90 50 0 0 0 0 0 0 60 20 0 90 Galium 90 90 90 90 30 50 0 30 0 0 70 80 0 90 Horseweed 20 0 10 30 0 0 0 0 0 0 10 20 0 - Kochia 80 80 80 80 0 20 0 30 0 0 80 60 0 80 Oat, Wild 80 80 90 90 50 60 0 90 0 0 80 0 40 90 Pigweed, Palmer 80 90 90 90 0 - 0 20 0 0 80 90 0 90 Ragweed 10 10 10 40 0 0 0 10 0 0 10 10 0 40 Ryegrass, Italian 90 80 90 90 70 90 0 90 0 0 80 70 50 90 Soybean 50 50 30 40 0 0 0 0 0 0 20 10 0 70 Wheat 60 30 90 80 70 80 0 80 0 0 80 70 0 80 Table A Compounds 16 g ai / ha 236 237 238 240 241 242 Postemergence Barnyardgrass 80 90 10 60 60 0 Blackgrass 90 90 90 70 80 30 Corn 50 30 10 10 10 0 Foxtail, Green 90 90 70 40 0 Galium 80 90 90 70 80 20 Horseweed - - - - - 0 Kochia 80 80 80 20 20 20 Oat, Wild 80 30 0 60 70 40 Pigweed, Palmer 90 90 90 10 60 20 Ragweed 80 80 80 20 0 0 Ryegrass, Italian 90 70 70 50 70 0 Soybean 0 70 0 0 0 0 Wheat 80 60 60 0 40 0 Table A Compounds 4 g ai / ha 18 21 23 34 35 51 55 59 61 62 63 65 66 68 Postemergence Barnyardgrass 80 80 0 30 60 30 0 30 50 50 0 0 30 40 Blackgrass 60 50 0 0 70 50 0 70 20 50 10 40 60 60 Corn 40 10 0 0 0 0 0 30 40 30 0 0 0 0 Foxtail, Green 0 80 0 0 80 20 0 0 30 70 40 50 20 40 Galium 80 80 0 0 40 30 0 50 60 70 30 20 50 60 Horseweed 0 20 0 0 0 0 0 0 0 10 10 0 0 0 Kochia 70 80 0 0 30 40 0 0 60 80 50 70 80 30 Oat, Wild 70 90 30 0 60 0 0 30 30 10 10 0 0 0 Pigweed, Palmer 80 90 0 10 20 90 0 10 70 90 90 90 90 70 Ragweed 10 0 0 0 10 0 0 0 0 70 40 0 0 0 Ryegrass, Italian 40 80 0 0 40 0 0 0 0 20 0 0 0 0 Soybean 0 50 0 0 0 0 0 0 50 50 0 0 0 0 Wheat 20 70 0 0 0 0 0 40 0 0 30 0 0 0 Table A Compounds 4 g ai / ha 69 72 73 78 79 80 81 89 90 91 92 136 137 142 Postemergence Barnyardgrass 90 50 60 50 60 60 40 80 80 80 70 60 60 0 Blackgrass 90 90 80 90 60 80 80 80 90 80 80 10 40 0 Corn 70 20 30 40 10 30 20 60 40 70 60 40 40 0 Foxtail, Green 90 70 70 70 70 70 70 70 70 70 70 40 60 50 Galium 90 90 90 90 90 90 80 90 80 90 80 50 60 0 Horseweed 60 0 0 0 0 0 0 30 20 20 30 0 20 0 Kochia 80 80 80 70 70 50 80 80 80 80 80 80 80 0 Oat, Wild 90 90 80 40 80 90 80 90 90 90 90 20 20 10 Pigweed, Palmer 90 60 80 90 90 90 90 90 90 90 90 90 90 10 Ragweed 80 10 40 40 40 50 70 70 70 60 80 70 10 Ryegrass, Italian 80 70 50 70 70 80 50 70 70 70 80 30 30 0 Soybean 40 0 30 60 30 50 60 30 10 20 20 0 0 0 Wheat 70 50 50 70 40 60 60 20 50 40 40 40 40 10 Table A Compounds 4 g ai / ha 143 144 145 146 147 154 155 156 157 158 159 161 162 163 Postemergence Barnyardgrass 0 60 70 20 30 0 30 30 90 20 0 90 0 0 Blackgrass 0 70 70 60 60 0 80 90 100 60 0 60 70 40 Corn 0 0 50 0 10 0 40 10 10 0 0 0 0 0 0 30 0 20 70 10 Ragweed 0 10 0 0 0 0 20 0 60 0 0 0 0 30 Ryegrass, Italian 0 20 40 20 90 0 10 90 80 70 0 20 70 30 Soybean 0 0 0 0 0 0 0 0 10 0 0 0 0 0 Wheat 0 20 50 10 40 0 70 70 70 70 0 20 60 40 Table A Compounds 4 g ai / ha 164 165 166 167 169 171 172 173 174 175 177 178 179 180 Postemergence Barnyardgrass 0 0 30 60 0 0 60 0 0 60 10 90 0 60 Blackgrass 0 0 90 10 90 50 40 70 100 90 40 80 100 20 60 Foxtail, Green 0 0 10 40 30 0 30 0 0 70 0 90 20 60 Galium 0 0 90 70 80 40 80 80 60 90 60 90 90 80 Horseweed 0 0 30 10 0 0 0 0 0 10 0 0 0 30 Kochia 0 0 60 80 70 70 10 10 10 90 30 80 70 80 Oat, Wild 0 0 90 20 90 50 50 0 40 70 90 90 90 60 Pigweed, Palmer 0 0 90 90 50 30 30 20 20 90 10 70 90 90 Ragweed 0 0 50 40 30 30 0 10 0 40 0 30 70 60 Ryegrass, Italian 0 0 70 10 80 80 70 20 80 80 70 80 90 20 Soybean 0 0 0 10 10 0 10 0 0 30 10 10 0 20 Wheat 0 0 70 10 80 30 80 0 70 70 40 70 80 10 Table A Compounds 4 g ai / ha 181 183 184 185 186 187 188 189 191 192 193 194 195 196 Postemergence Barnyardgrass 0 90 0 0 0 80 0 0 20 20 80 0 0 20 Blackgrass 20 60 80 90 70 90 70 20 90 80 70 50 50 100 Corn 0 20 0 0 0 100 0 0 0 30 50 10 0 10 Foxtail, Green 0 80 0 30 0 90 0 0 20 40 70 0 20 30 Galium 0 50 30 80 90 90 90 0 90 80 80 60 10 90 Horseweed 0 10 0 0 0 0 10 0 0 0 0 0 0 0 Kochia 0 60 0 80 70 80 80 30 80 50 40 50 70 80 Oat, Wild 0 50 20 50 0 90 20 30 20 70 90 20 60 80 Pigweed, Palmer 0 20 0 70 60 90 40 20 70 20 70 50 40 70 Ragweed 0 10 0 80 50 50 50 0 70 20 0 70 20 0 Ryegrass, Italian 0 60 0 80 20 70 40 70 50 80 80 70 60 80 Soybean 0 0 0 0 10 60 10 0 0 0 0 0 0 0 Wheat 0 30 20 10 0 90 10 60 0 80 90 70 40 40 Table A Compounds 4 g ai / ha 197 200 201 202 203 204 205 206 207 208 209 210 211 217 Postemergence Barnyardgrass 0 50 0 20 70 30 30 20 0 90 90 70 80 0 Blackgrass 0 50 70 0 90 0 30 70 90 80 80 50 40 0 Corn 0 10 0 0 50 0 0 10 50 0 20 60 10 0 Foxtail, Green 0 40 0 20 90 0 50 0 20 90 80 0 60 0 Galium 0 60 80 0 90 0 50 50 0 90 80 70 90 40 Horseweed 0 0 20 0 20 0 10 0 0 30 0 0 0 0 Kochia 0 30 80 0 80 0 50 70 0 80 60 80 20 0 Oat, Wild 0 70 60 0 60 0 60 0 40 60 80 20 40 0 Pigweed, Palmer 0 40 60 0 80 0 80 10 0 90 60 80 20 0 Ragweed 0 0 30 0 10 0 0 60 0 10 30 80 20 0 Ryegrass, Italian 0 60 60 0 90 0 10 30 20 80 40 80 10 20 Soybean 0 0 10 30 40 0 0 0 0 0 40 0 0 0 Wheat 0 20 60 0 80 0 30 0 30 80 70 70 20 0 Table A Compounds 4 g ai / ha 218 219 220 221 222 223 224 225 226 227 228 229 230 231 Postemergence Barnyardgrass 40 0 0 40 20 0 60 0 0 0 0 0 0 0 Blackgrass 90 80 80 70 90 90 100 90 50 50 0 50 0 0 Corn 20 0 10 20 0 0 50 20 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 TEST B Plant species in the flooded paddy test selected from barnyardgrass (Echinochloa crus- galli), ducksalad (Heteranthera limosa), rice (Oryza sativa), and sedge, umbrella (small- flower umbrella sedge, Cyperus difformis) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (–) response means no test result. Table B Compounds 250 g ai / ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Flood Barnyardgrass 65 65 100 45 95 45 50 0 60 90 90 55 65 80 Ducksalad 40 20 95 90 70 75 75 70 75 75 85 85 90 95 Rice 30 40 90 65 85 35 25 10 85 55 95 55 85 90 Sedge, Umbrella 90 70 100 95 90 85 90 55 65 70 100 80 95 100 Table B Compounds 250 g ai / ha 15 16 17 19 20 22 24 25 26 27 28 29 30 31 Flood Barnyardgrass 90 15 0 95 95 95 98 98 90 65 95 65 35 65 Ducksalad 95 85 0 100 100 98 100 100 95 70 100 90 70 90 Rice 90 50 0 90 85 85 90 95 90 90 90 90 50 85 Sedge, Umbrella 100 45 0 100 100 100 100 100 95 90 100 90 80 98 Table B Compounds 250 g ai / ha 32 33 35 36 37 38 39 40 41 42 43 44 45 46 Flood Barnyardgrass 65 55 85 40 30 75 0 90 50 0 90 85 0 95 Ducksalad 85 80 85 80 85 95 0 98 70 0 95 90 0 95 Rice 90 65 70 65 85 70 0 95 35 0 95 55 0 95 Sedge, Umbrella 90 95 90 80 85 95 0 100 90 0 90 90 0 95 Table B Compounds 250 g ai / ha 47 48 49 50 52 53 54 56 57 58 60 62 63 67 Flood Barnyardgrass 90 95 65 65 50 95 90 0 0 95 95 70 35 25 Ducksalad 98 90 90 80 85 100 95 45 0 88 75 85 80 85 Rice 55 95 55 80 10 85 25 0 0 90 85 45 0 85 Sedge, Umbrella 90 100 95 80 0 100 98 0 0 95 85 95 95 90 Table B Compounds 250 g ai / ha 69 71 72 73 74 75 76 77 78 79 80 81 82 83 Flood Barnyardgrass 95 95 98 95 30 45 85 85 98 98 95 95 90 70 Ducksalad 100 100 98 95 75 45 70 85 95 90 90 95 50 25 Rice 95 95 95 98 15 75 95 80 95 95 95 95 65 70 Sedge, Umbrella 100 100 100 100 0 50 90 95 100 100 100 100 80 0 Table B Compounds 250 g ai / ha 84 85 86 87 88 93 94 95 96 97 98 99 100 101 Flood Barnyardgrass 90 0 95 90 0 95 98 95 25 90 85 90 90 75 Ducksalad 95 0 98 90 0 70 85 90 70 80 65 80 90 75 Rice 85 0 100 95 0 15 55 90 45 50 25 70 75 80 Sedge, Umbrella 100 0 100 98 0 70 90 100 65 90 90 98 98 95 Table B Compounds 250 g ai / ha 102 103 104 105 106 107 108 109 110 111 112 113 114 115 Flood Barnyardgrass 90 70 65 85 95 65 25 95 90 90 95 65 95 55 Ducksalad 70 70 80 65 70 85 70 80 60 85 85 70 70 95 Rice 65 35 20 75 75 75 35 98 90 95 98 95 95 65 Sedge, Umbrella 98 98 98 100 98 98 98 95 80 95 85 85 98 98 Table B Compounds 250 g ai / ha 116 117 118 119 120 121 122 123 124 125 126 127 128 129 Flood Barnyardgrass 55 50 65 70 95 95 0 0 90 85 35 15 80 100 Ducksalad 95 90 90 80 70 75 0 0 80 95 95 90 95 90 Rice 55 30 65 80 95 100 0 0 90 85 20 10 75 85 Sedge, Umbrella 98 95 95 98 100 100 0 0 85 95 70 25 95 98 Table B Compounds 250 g ai / ha 130 131 132 133 134 138 139 140 141 142 143 144 145 146 Flood Barnyardgrass 45 90 85 95 95 20 98 30 0 45 70 90 95 40 Ducksalad 95 85 85 80 95 20 95 80 0 70 98 98 95 95 Rice 55 90 95 85 95 0 95 60 0 60 65 95 80 65 Sedge, Umbrella 98 98 98 98 98 0 100 0 0 90 100 100 100 98 Table B Compounds 250 g ai / ha 147 148 149 150 151 152 153 161 162 163 168 170 177 178 Flood Barnyardgrass 98 95 30 30 95 90 55 95 65 65 80 0 75 90 Ducksalad 95 70 30 30 100 95 25 95 75 85 75 0 85 95 Rice 70 70 10 30 85 25 80 55 80 75 50 0 90 85 Sedge, Umbrella 98 75 15 30 100 100 45 90 98 98 85 0 98 98 Table B Compounds 250 g ai / ha 183 186 187 188 190 198 200 201 202 205 206 208 209 211 Flood Barnyardgrass 0 80 85 70 0 70 95 75 0 90 80 95 90 85 Ducksalad 30 70 90 75 0 70 95 75 0 90 90 90 90 70 Rice 0 20 80 85 0 75 95 25 0 50 80 95 90 45 Sedge, Umbrella 25 95 95 95 0 98 100 75 0 90 98 100 95 80 Table B Compounds 250 g ai / ha 215 216 217 218 219 220 221 222 223 234 235 236 237 238 Flood Barnyardgrass 25 95 15 95 65 30 85 80 35 0 95 90 75 25 Ducksalad 65 65 75 95 98 80 95 90 80 0 90 90 90 95 Rice 25 80 0 85 40 70 70 55 60 0 90 95 70 60 Sedge, Umbrella 45 98 60 98 98 100 98 95 90 0 95 90 100 95 Table B Compounds 250 g ai / ha 240 241 Flood Barnyardgrass 50 65 Ducksalad 30 40 Rice 50 40 Sedge, Umbrella 80 85 Table B Compounds 62 g ai / ha 18 21 23 34 51 55 59 61 65 66 68 89 90 91 Flood Barnyardgrass 25 75 0 0 15 0 0 55 25 0 25 70 85 70 Ducksalad 75 70 0 0 40 0 0 90 80 25 60 80 75 90 Rice 20 70 0 0 20 0 0 10 50 30 15 55 85 80 Sedge, Umbrella 50 65 0 0 55 0 0 95 90 40 50 100 100 100 Table B Compounds 92 136 137 154 155 156 157 158 159 164 165 166 167 169 Flood Barnyardgrass 65 50 55 0 70 25 85 50 0 0 0 25 65 60 Ducksalad 80 70 70 0 90 80 80 50 0 0 0 60 75 70 Rice 60 15 15 0 45 0 60 25 0 0 0 10 20 90 Sedge, Umbrella 100 80 85 0 90 30 95 25 0 0 0 35 90 50 65 40 20 45 0 0 0 0
Claims
1. What is claimed is:
1. A compound of Formula 1, stereoisomers, N-oxides and salts thereof: Q is N or C-X5; eac1 2 3 4h X , X , X , X and is independently hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C1–C6haloalkyl, C2–C6alkenyl, C2–C6haloalkenyl, C2–C6alkynyl, C2–C6haloalkynyl, C3–C7cycloalkyl, C3–C7halocycloalkyl, C1–C6alkoxy, C1–C6haloalkoxy, each of which is substituted by m radicals selected from the group consisting of cyano, S(O)pR7or CO2R8; p is 0, 1 or 2; A is selected from ;haloalkyl, C1–C6cyanoalkyl, C1–C6alkoxy, C1–C6haloalkoxy or C1–C6cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, each of which is optionally further substituted by at least one radical selected from the group consisting of halogen, cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, and hydroxy;V and W are each independently O or R1is independently hydrogen, C1–C6C 11 13–C7cycloalkyl, C1–C6haloalkyl, C1–C3alkoxy, C–C3haloalkoxy; or WG; W1is a direct bond, C–C alkanediyl or C–C alkenediyl; 171G i S )R, SONR104s (O R11, COR81, CONR104R11or COR1; 1p 2 22Y is selected from the group consisting of ;Z is CH2, CF2, CCl2, O or m is 0, 1 or 2; Rvis halogen, cyano, CO2R8, C1–C2alkyl or C1–C2alkoxy, each of which is substituted by n radicals independently selected from halogens; R2is hydrogen, C1–C12alkyl, NH2, N=CR8R12, C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 72 8H O (95 6S R H122 8(C2)q( )p, C2)qOR, (CH2)qCOR , or oxetanyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C6alkyl, C1–C6alkoxy, hydroxy and an aromatic ring; q is 0, 1, 2, 3, 4 or 5; R6is hydrogen, cyano, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR1, NR10R11, NR10COR12p, NR102CONR10R11, NR1022CO2R8, NR10SOR7, NR10SO2NR10R11, C(R7)=N92OR, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, 97 10 11 8 10 11 12 10 11OR, S(O)R, SONR R , COR, CONR R , COR , NR R , 10p12 10210 112NR COR , NR CONR R , NR10COR8, N10 7 10 10 11R SOR, NR SONR R ,2 2 279C(R)=NOR, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; orR2and R6can be taken together with atom to which they are attached to form a 3- to 7-membered ring, carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C–C alkyl, C–C haloalkyl, OR9, 710 11 81O R, SONR R , COR, CONR106R111, COR126S( ) , NR10R11, NR10COR12, 10p12011 102NR CONR R , NR CO2R8, NR10SO2R7, NR10SO2NR10R11, and R7,is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C–C alkoxy or an aromatic ring; and 131 2R is hydrogen, C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, S(O)R7, SONR10R112 12, COR8, C105ON R117r O122 12 p 2 2R o C R .
2. The compound of Claim 1 wherein Q is N; each X1, X2, X3, X4is independently hydrogen, halogen, cyano, C1–C6alkyl, C1–C6haloalkyl, C1–C6alkoxy or C1–C6haloalkoxy; A is A-1 or A-2; R3and R4are each independently hydrogen, halogen, cyano, C1–C3alkyl, C1–C3haloalkyl, C1–C3cyanoalkyl, C1–C3alkoxy, C1–C3haloalkoxy or C1–C3cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, optionally each of which is further substituted by at least one radical selected from the group consisting of halogen, cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl and hydroxy; V and W are both O;R1is hydrogen, C1–C6alkyl, C3–C7C1–C6haloalkyl, C1–C3alkoxy or C1– C3haloalkoxy; Y1is selected from the group consisting of Y1-1 and Y1-2; Y2is a direct bond, O or S; Z is CH2, CF2, O or NR6; m is 0; Rvis halogen, cyano, CO2R8, C1–C2alkyl or C R2is hd8 21–C2alkoxy; yrogen, C1–C12alkyl, NH2, N=CRR1, C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 272 8H O ( O95 6S R H , C )122 8(C )q( )p, C2)qR ( H2 qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C–C alkyl, C–C alkoxy, hydroxy and an aromatic ring; 61R96s71 6i hydrogen, cyano, OR, S(O)R, SONR10R11, COR8, CONR10R11, COR12, 10 11 10 12p102NR R , NR COR , NR CONR10R11, NR102CO8 10N0 1 92R, NR SO 10 1 1 72R7, R SO2NR R , C(R)=NOR, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR12, NR10R11, 10p12 10210 112NR COR , NR CONR R , NR10CO2R8, NR10SO2R7, NR10SO2NR10R11, C(R7)=NOR9, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R2and R6can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C–C alkyl, C–C haloalkyl, OR9, p7 10 11 81O R106S111126S( ) , O2NR R , CO2R, CONR R , COR , NR10R11, NR10COR12, C(R7)=NOR9; R7, R8, R9, R10 11, R and R12are each independently hydrogen, C1–C6alkyl, C1–C6haloalkyl, C3–C7cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring; andR13is hydrogen, C1–C12alkyl, S(O) CO2R8.
3. The compound of Claim 2 which is wherein X1, X2, X3, X4is independently hydrogen, F, Cl, Br, cyano, C1–C2alkyl, C1–C2haloalkyl, C1–C2alkoxy or C1–C2haloalkoxy; A is A-1; R2is hydrogen, C1–C7alkyl, C3–C7cycloalkyl, C3–C7cycloalkylalkyl, C 5 C y l a k n l7 92–C5alkenyl, C –6c c o l e y , C 122–C5alkynyl, (CH2)qS(O)pR , (CH2)qOR , (CH2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and an aromatic ring; R3and R4are each independently hydrogen, halogen, cyano, C1–C2alkyl, C1–C2haloalkyl, C1–C2cyanoalkyl, C1–C2alkoxy, C1–C2haloalkoxy or C1–C2cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl or C –C alkylsulfonyl; 11 4R is hydrogen or CH 1 Y13; Y is -1; Y2is O or S; Z is CH Rv2or O; is halogen or C R21–C2alkyl; is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, cyano, OR9, S(O) R7, SO NR10R11, CO R8, CONR10R11or COR12; R7, R8, R9, R10, R11an R12p 2 2d are each independently hydrogen, C1–C3alkyl, C1–C3haloalkyl, C3–C5cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C –C alkoxy and an aromatic ring; and 131 2R is hydrogen, CH3, S(O)2CH3or CO2(t-Bu).
4. The compound of Claim 3 wherein each X1, X2, X3, X4is independently hydrogen, F, Cl, Me, CF3, OMe or OCF3;R3and R4are each independently halogen, cyano, Me, CF3, CH2CN, OMe, OCF3or OCH 52CN; R is hydrogen, halogen, cyano, hydroxy, C1–C3alkyl, C2–C3alkenyl, C2–C3alkynyl, C3–C5cycloalkoxy, C3–C5cycloalkoxyalkyl, C3–C5cycloalkyl, C4–C7cycloalkylalkyl, C1–C3haloalkyl, C2–C3alkoxyalkyl, C2–C3haloalkoxyalkyl, C1–C3alkoxy, C1–C3haloalkoxy, C1–C3alkylthio, C1–C3alkylsulfinyl or C1– C3alkylsulfonyl; R1is hydrogen; Y2is O; Rvis halogen or CH 23; R is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, OR9or S(O) 1pR7; and R7, R8, R9, R10, R11and R2are each independently hydrogen, Me, Et, Pr, i-pr, c-Pr, t- Bu, CF3, OMe, OEt, CF3, CH2CF3, CH2-c-Pr, Ph each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring.
5. The compound of Claim 1 wherein Q is C-X5; each X1, X2, X3, X4is independently hydrogen, halogen, cyano, C1–C6alkyl, C1–C6haloalkyl, C –C alkoxy or C –C haloalkoxy; 51 6 1 6X is halogen; A is A-1 or A-2; R3and R4are each independently hydrogen, halogen, cyano, C1–C3alkyl, C1–C3haloalkyl, C1–C3cyanoalkyl, C1–C3alkoxy, C1–C3haloalkoxy or C1–C3cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4alkylsulfonyl, C1–C4alkylsulfonate, C1–C4haloalkylthio, C1–C4haloalkylsulfinyl, C1–C4haloalkylsulfonyl or C2–C5alkoxycarbonyl, optionally each of which is further substituted by at least one radical selectedfrom the group consisting of cyano, C1–C4alkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl, C1–C4and hydroxy; V and W are both O; R1is hydrogen, C1–C6alkyl, C3–C7cycloalkyl, C1–C6haloalkyl, C1–C3alkoxy or C1– C3haloalkoxy; Y1is selected from the group consisting of Y1-1 and Y1-2; Y2is a direct bond, O or S; Z is CH2, CF2, O or NR6; m is 0; Rvis halogen, cyano, CO2R8, C1–C2alkyl or C1–C alkoxy; R2is hydrogen, C–C alkyl, NH, N8 1221 12 2=CRR , C3–C7cycloalkyl, C3–C12cycloalkylalkyl, C–C alkenyl, C–C cycloalkenyl, C–C alkynyl, 272 8H Op( O95 6S R H , C122 8(C )q( ) , C2)qR ( H2)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C–C alkyl, C–C alkoxy, hydroxy and an aromatic ring; 61R cyano, OR96s , S(O)R71 6i hydrogen, , SONR10R11, COR8, CONR10R11, COR12, 10 11 10OR12p, NR102NR R , NR C CONR10R11, NR102CO2R8, NR10SO 10 10 12R7, NR SO2NR R1, C(R7)=NOR9, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R6is C1–C12alkyl, C3–C8cycloalkyl, C4–C12cycloalkylalkyl, C2–C12alkenyl, C5–C7cycloalkenyl or C2–C12alkynyl, each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, OR9, S(O)R7, SONR10R11, COR8, CONR10R11, COR12, NR10R1, 10p12 10210 1121NR COR , NR CONR R , NR10CO2R8, NR10SOR7, NR10SONR10R11, 792 2C(R)=NOR, an optionally substituted aromatic ring, an optionally substituted heteroaromatic ring or an optionally substituted heterocyclic ring; or R2and R6can be taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring, containing carbon atoms and optionally 1 to 3 oxygen, sulfur or nitrogen atoms as ring members, wherein up to 2 carbon atom ring members are independently selected from C(=O) and C(=S), and the sulfur atom ring member is selected from S, S(O) or S(O)2, said ring being optionally substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, C–C alkyl, C–C haloalkyl, OR, p7SO2NR10R11, CO2R81O R , CONR106R1119, COR126S( ) , , NR10R11, NR10COR12,R7, R8, R9, R10, R11and R12are each hydrogen, C1–C6alkyl, C1–C6haloalkyl, C3–C7cycloalkyl or an aromatic ring, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C–C alkoxy and an aromatic ring; and 131 2R is hydrogen, C1–C12alkyl, S(O)pR7or CO2R8.
6. The compound of Claim 5 wherein X1, X2, X3, X4is independently hydrogen, F, Cl, Br, cyano, C1–C2alkyl, C1–C2haloalkyl, C–C alkoxy or C–C haloalkoxy; 51 2 1 2X is F or Cl; A is A-1; R2is hydrogen, C1–C7alkyl, C3–C7cycloalkyl, C3–C7cycloalkylalkyl, C–C alkenyl, 5C ylaknl7 92 5C–6ccoley, C 2122–C5alkynyl, (CH2)qS(O)pR, (CH2)qOR, (CH)qCOR , each of which is optionally substituted by one or more radicals selected from the group consisting of halogen, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and an aromatic ring; R3and R4are each independently hydrogen, halogen, cyano, C1–C2alkyl, C1–C2haloalkyl, C1–C2cyanoalkyl, C1–C2alkoxy, C1–C2haloalkoxy or C1–C2cyanoalkoxy; R5is hydrogen, halogen, cyano, nitro, hydroxy, C1–C6alkyl, C2–C5alkenyl, C2–C5alkynyl, C2–C5alkenyloxy, C2–C5alkynyloxy, C3–C7cycloalkoxy, C3–C7cycloalkoxyalkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C1–C6haloalkyl, C2–C5haloalkenyl, C2–C5haloalkynyl, C2–C5alkoxyalkyl, C2–C5haloalkoxyalkyl, C1–C5alkoxy, C1–C6haloalkoxy, C1–C5alkylthio, C1–C4alkylsulfinyl or C–C alkylsulfonyl; 11 4R is hydrogen or CH 1 Y13; Y is -1; Y2is O or S; Z is CH Rv2or O; is halogen or C R21–C2alkyl; is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, cyano, OR9, S(O)R7, SONR10R11, COR8, CONR10R11or COR12; R7, R8, R9, R10, R11an R12p 2 2d are each independently hydrogen, C1–C3alkyl, C1–C3haloalkyl, C3–C5cycloalkyl or an aromatic ring, each of which is optionallysubstituted by one or more selected from the group consisting of F, Cl, C –C alkoxy and an aromatic and 131 2R is hydrogen, CH3, S(O)2CH3or CO2(t-Bu).
7. The compound of Claim 6 wherein X1, X2and X4is hydrogen; and X3is F or Cl; R3and R4are each independently hydrogen, halogen, cyano, Me, CF3, CH2CN, OMe, OCF3or OCH 52CN; R is hydrogen, halogen, cyano, hydroxy, C1–C3alkyl, C2–C3alkenyl, C2–C3alkynyl, C3–C5cycloalkoxy, C3–C5cycloalkoxyalkyl, C3–C5cycloalkyl, C4–C7cycloalkylalkyl, C1–C3haloalkyl, C2–C3alkoxyalkyl, C2–C3haloalkoxyalkyl, C1–C3alkoxy, C1–C3haloalkoxy, C1–C3alkylthio, C1–C3alkylsulfinyl or C1– C alkylsulfonyl; R13is hydrogen; Y2is O; Rvis halogen or CH3; R2is hydrogen, Me, Et, c-Pr, c-Bu, CH2-c-Pr, (CH2)qS(O)pMe, (CH2)qOMe, (CH2)qCOMe, each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, cyano, C1–C3alkyl, C1–C3alkoxy, hydroxy and Ph; R6is hydrogen, OR9or S(O)pR7; and R7, R8, R9, R10, R11and R12are each independently hydrogen, Me, Et, Pr, i-pr, c-Pr, t- Bu, CF3, OMe, OEt, CF3, CH2CF3, CH2-c-Pr, Ph each of which is optionally substituted by one or more radicals selected from the group consisting of F, Cl, C1–C2alkoxy and an aromatic ring.
8. The compound of Claim 7 wherein X3is F; X5is F; X1, X2and X4is hydrogen; R3and R4are each independently hydrogen, halogen or cyano; R5is hydrogen, Me, Et, CH=CH , C≡CH, cyclopropyl, CF , OMe or OCF ; 12 3 3R is hydrogen; Rvis halogen; Z is CH2; R2is hydrogen, Me, Et, i-Pr, i-Bu, t-Bu, c-Pent, OMe, CH2CF3, CH2CN, (CH2)2OMe, CH2CO2Me, CH2CO2Et, CH2CO2(4-F-Ph), CH2SMe, CH2Ph, NCHPh, (CH2)2SO2Me, SO2Me, SO2Et, SO2(n-Pr), SO2(c-Pr), SO2(t-Bu), SO2CF3or SO2Ph; andR6is C1–C4alkyl or C3–C89. The compound of Claim 1 selected from the group consisting of methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate; methyl (1S,2S,4R,5R)-4-[[(3E)-4-(3,5-difluorophenyl)-2,2-difluoro-1-oxo- 3-buten-1-yl]amino]-6-oxabicyclo[3.1.0]hexane-2-carboxylate; methyl (1S,2S,4R,5R)-4-[[[1-(3,5-dichlorophenyl)-3-methyl-2-oxo-3- azetidinyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-4,5-dihydro-5-methyl- 5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-(chloromethyl)- 4,5-dihydro-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 210); methyl (1S,2S,4R,5R)-4-[[[5-(chloromethyl)-3-(3,5-dichlorophenyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 194); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 113); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(R)- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(S)- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate; (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylic acid (Compound 3);methyl (1S,2S,4R,5R)-4-[[[3- 5-fluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5- carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 6); (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylic acid (Compound 7); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5-methyl-5- isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 124); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(R)- methyl-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate; methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5(S)- methyl-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate; methyl (1S,2S,4R,5R)-4-[[[5-(chloromethyl)-3-(3,5-difluorophenyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 158); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-5-ethenyl-4,5-dihydro- 5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 121); cyanomethyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 151); 2-methoxy-2-oxoethyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5- dihydro-5-(trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 132); 2-oxopropyl (1S,2S,4R,5R)-4-[[[3-(3,5-difluorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 134); 3-(3,5-difluorophenyl)-5-ethenyl-N-[(1S,2R,4S,5R)-4- [[(ethylsulfonyl)amino]carbonyl]bicyclo[3.1.0]hex-2-yl]-4,5- dihydro-5-isoxazolecarboxamide (Compound 97); methyl (1S,2S,4R,5R)-4-[[[5-(difluoromethyl)-3-(3,5-difluorophenyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 196);methyl (2S,4R)-4-[[[3-(3,5- -5-(fluoromethyl)-4,5-dihydro- 5-isoxazolyl]carbonyl] -6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 208); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-5-(fluoromethyl)-4,5- dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-2- carboxylate (Compound 155); methyl (1S,2S,4R,5R)-4-[[[3-(3-chloro-5-fluorophenyl)-5-(fluoromethyl)- 4,5-dihydro-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 175); methyl (1S,2S,4R,5R)-4-[[[3-(3,5-dichlorophenyl)-4,5-dihydro-5- (trifluoromethyl)-5-isoxazolyl]carbonyl]amino]-6- oxabicyclo[3.1.0]hexane-2-carboxylate (Compound 36); and methyl (1S,2S,4R,5R)-4-[[[5-(1,1-difluoroethyl)-3-(3,5-difluorophenyl)- 4,5-dihydro-5-isoxazolyl]carbonyl]amino]-6-oxabicyclo[3.1.0]- hexane-2-carboxylate (Compound 179).
10. 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.
11. A herbicidal composition comprising a compound of Claim 1, at least one additional active 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.
12. A herbicidal mixture comprising (a) a compound of Claim 1, and (b) at least one additional active ingredient selected from (b) at least one additional active ingredient selected from photosystem II inhibitors (b1), AHAS inhibitors (b2), ACCase inhibitors (b3), auxin mimics (b4), EPSP synthase inhibitors (b5), photosystem I electron diverters (b6), PPO inhibitors (b7), GS inhibitors (b8), VLCFA elongase inhibitors (b9), auxin transport inhibitors (b10), PDS inhibitors (b11), HPPD inhibitors (b12), DXP synthase inhibitors (b13), HST inhibitors (b14), cellulose biosynthesis inhibitors (b15), DHODH inhibitors (b16), other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinflubrolin, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb (b17), and herbicide safeners (b18); and salts of compounds of (b1) through (b18).
13. A herbicidal mixture comprising (a) a compound of Claim 1, and (b) at least one additional active ingredient selected from bixlozone, carfentrazone, carfentrazone-ethyl,clomazone, chlorimuron-ethyl, thifensulfuron-methyl, tribenuron, pinoxaden, pyroxasulfone, pyroxsulam, tembotrione, tetflupyrolimet, metolachlor and S-metolachlor.
14. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.
15. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a composition of Claim 11.
Citation Information
Patent Citations
process for the production of water-dispersible granules
DE3246493A1
Formulation of agricultural chemicals
GB2095558A
Compositions and methods for influencing the growth of plants
US2891855A
Improved homogeneous, readily dispersed, pesticidal concentrate
US3060084A
Method for the control of undesirable vegetation
US3235361A