FIELD OF THE INVENTION

This invention relates to certain saturated bicyclic pyridazinones, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, 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. Patent application publications WO 2015/168010 and WO 2017/074992, and patent application PCT/US18/24742 disclose substituted pyridazinones. The saturated bicyclic pyridazinones of the present invention are are not disclosed in these patent applications.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1, including all stereoisomers, N-oxides of such compounds, and salts of such compounds, and agricultural compositions containing such compounds, and the use of such compounds as herbicides:

[Image Omitted]

wherein

- W is —C(R⁷)(R⁸)— or —O—;
- R¹is H, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₄-C₇alkylcycloalkyl, C₂-C₇alkenyl, C₃-C₇alkynyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₅cyanoalkyl, C₁-C₄nitroalkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇haloalkenyl, C₂-C₇alkoxyalkyl, C₃-C₇alkylthioalkyl or C₁-C₇alkoxy;
- R²is H, halogen, cyano, —CHO, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₁-C₄alkylcarbonyl, C₂-C₇alkylcarbonyloxy, C₄-C₇alkylcycloalkyl, C₂-C₇alkenyl, C₃-C₇alkynyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₈dialkylamino, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₅cyanoalkyl, C₁-C₄nitroalkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇haloalkenyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy, C₁-C₅alkylthio or C₂-C₃alkoxycarbonyl;
- each R³is independently H, halogen, nitro, cyano, C₁-C₅alkyl, C₂-C₅alkenyl, C₂-C₅alkynyl, C₃-C₅cycloalkyl, C₄-C₅cycloalkylalkyl, C₁-C₅haloalkyl, C₂-C₅haloalkenyl, C₃-C₅haloalkynyl, C₂-C₅alkoxyalkyl, C₁-C₅alkoxy, C₁-C₅haloalkoxy, C₁-C₅alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio or C₂-C₅alkoxycarbonyl;
- n is 0 to 3;
- each R⁴is independently H, halogen, nitro, cyano, C₁-C₅alkyl, C₂-C₅alkenyl, C₂-C₅alkynyl, C₃-C₅cycloalkyl, C₄-C₅cycloalkylalkyl, C₁-C₅haloalkyl, C₂-C₅haloalkenyl, C₃-C₅haloalkynyl, C₂-C₅alkoxyalkyl, C₁-C₅alkoxy, C₁-C₅haloalkoxy, C₁-C₅alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio or C₂-C₅alkoxycarbonyl;
- R⁵is H or C₁-C₅alkyl;
- R⁶is H or C₁-C₅alkyl;
- R⁷is H or C₁-C₅alkyl;
- R⁸is H or C₁-C₅alkyl;
- L is a direct bond, C₁-C₄alkanediyl or C₂-C₄alkenediyl;
- G is H, C(═O)R⁹, C(═S)R⁹, CO₂R¹⁰, C(═O)SR¹⁰, S(O)₂R⁹, C(═O)N(R¹¹)(R¹²), S(═O)₂N(R¹¹)(R¹²) or P(═O)(R¹³)(R¹⁴); or C₁-C₇alkyl, C₂-C₅alkenyl, C₂-C₄alkynyl, C₁-C₇haloalkyl, C₂-C₅haloalkenyl, C₂-C₄haloalkynyl, C₂-C₄alkoxyalkyl, C₃-C₆cycloalkyl or C₄-C₇cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
- R⁹and R¹¹are independently H, C₁-C₇alkyl, C₃-C₇alkenyl, C₃-C₇alkynyl, C₃-C₇cycloalkyl, C₁-C₇haloalkyl, C₃-C₇haloalkenyl, C₂-C₇alkoxyalkyl or C₄-C₇cycloalkylalkyl; or phenyl, benzyl, or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
- R¹⁰is C₁-C₇alkyl, C₃-C₇alkenyl, C₃-C₇alkynyl, C₃-C₇cycloalkyl, C₂-C₇haloalkyl, C₃-C₇haloalkenyl, C₂-C₇alkoxyalkyl or C₄-C₇cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
- R¹²is H, C₁-C₇alkyl, C₂-C₇alkenyl, C₂-C₇alkynyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₁-C₇haloalkyl or C₂-C₇alkoxyalkyl;
- R¹³is C₁-C₇alkyl or C₁-C₇alkoxy; and
- R¹⁴is C₁-C₇alkyl or C₁-C₇alkoxy.

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

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 (b16); and salts of compounds of (b1) through (b16), 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 present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

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.

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.

“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. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂and CH₃CH₂SCH₂CH₂. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH₂and NCCH₂CH₂(alternatively identified as CH₂CH₂CN). The term “nitroalkyl” represents a nitro group bonded through an alkyl moiety. Examples of “nitroalkyl” include O₂NCH₂and O₂NCH₂CH₂(alternatively identified as CH₂CH₂NO₂). The terms “alkylamino” and “dialkylamino” refer to mono- and di-alkyl substitution on an amine moiety, respectively. Examples of “alkylamino” include CH₃NH—, (CH₃)₂CHNH— and CH₃CH₂CH₂NH—. Examples of “dialkylamino” include (CH₃)₂N—, (CH₃)₂N— and (CH₃)₂CH₂CH₂N—. “Alkylthio” includes branched or straight-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. “Alkylsulfonyl” indicates a sulfonyl moiety substituted with a straight-chain or branched alkyl group. 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—, CH₃CH₂CH₂CH₂SCH₂— and CH₃CH₂SCH₂CH₂—.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl.

The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F₃C, ClCH₂, CF₃CH₂and CF₃CCl₂. The terms “haloalkoxy”, “haloalkylthio”, “haloalkenyl”, “haloalkynyl”, “haloalkoxyalky”, and the like, are is 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 “haloalkenyl” include (Cl)₂C═CHCH₂— and CF₃CH₂CH═CHCH₂—. Examples of “haloalkynyl” include HC≡CCHCl—, CF₃C≡C—, CCl₃C≡C— and FCH₂C≡CCH₂—. Examples of “haloalkoxyalkyl” include CF₃OCH₂CH₂—, CCl₃CH₂OCH₂—, HCF₂CH₂CH₂OCH₂— and CF₃CH₂OCH₂—.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moiety bonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—, CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. “Alkoxycarbonyl” denotes a straight-chain or branched alkoxy moieties bonded to a C(═O) moiety. Examples of “alkoxycarbonyl” include CH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—, (CH₃)₂CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers. “Alkylcarbonylalkyl” denotes a straight-chain or branched chain alkyl group bonded to the carbon atom of to a carbonylalkyl moiety. “Alkoxycarbonylalkyl” denotes a straight-chain or branched alkoxycarbonyl moieties bonded to linear or branched a alkylene moiety. Examples of “alkoxycarbonylalkyl” include CH₃OC(═O)CH₂CH₂—, CH₃CH₂OC(═O)CH₂—, CH₃CH₂CH₂OC(═O)CH₂CH(CH₃)—, (CH₃)₂CHOC(═O)CH₂— and the different butoxy- or pentoxycarbonylalkyl isomers. “Alkylcarbonyloxy” denotes a straight-chain or branched-chain alkyl group bonded to the carbon atom of to a carbonyloxy moiety. Examples of “alkylcarbonyloxy” include (CH₃)C(═O)O— and (CH₃CH₂)C(═O)O—. The term alkanediyl or alkenediyl refers to a linear or branched alkane or alkene linking chain respectively. Examples of alkanediyl include —CH₂—, —CH₂CH(CH₃)— or —CH₂CH₂CH₂—. Examples of alkenediyl include —CH═CH—, —CH₂C═CH— or —CH═C(CH₃)—. The term “adjacent” in the context of locating a substituent means “next to” or “immediately next to”.

The total number of carbon atoms in a substituent group is indicated by the “C_i-C_j” prefix where i and j are numbers from 1 to 7. 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—.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, (e.g., (R³)_n, n is 0, 1, 2 or 3). When a group contains a substituent which can be hydrogen, for example R³or R⁴, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R³)_nwherein n may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.

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” or “carbocyclic ring system” 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 “heterocycle” denote a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies 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.

As noted above, G, R¹⁰or R¹¹can 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 R^vis as defined in the Summary of the Invention for G and r is an integer from 0 to 5. As noted above, G, R¹⁰or R¹¹can be (among others) 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 R^vis any substituent as defined in the Summary of the Invention for G, R¹⁰or R¹¹and r is an integer from 0 to 4, limited by the number of available positions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, for these U groups r is limited to the integers 0 or 1, and r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (R^v)_r.

[Image Omitted]

Note that when G, R¹⁰or R¹¹is 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 for G, R¹⁰or R¹¹, one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.

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 R^vcan 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 G, R¹⁰or R¹¹comprises 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 R^vas defined in the Summary of the Invention as halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.

[Image Omitted]

Although R^vgroups are shown in the structures U-1 through U-61, it is noted that they do not need to be present since they are optional substituents. Note that when R^vis H when attached to an atom, this is the same as if said atom is unsubstituted. The nitrogen atoms that require substitution to fill their valence are substituted with H or R^v. Note that when the attachment point between (R^v)_rand the U group is illustrated as floating, (R^v)_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 R^vgroups (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 is high enough to permit isolation of the isomeric species. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

For example, when R⁵or R⁶are dissimilar, then Formula 1 possesses a chiral center at the carbon atom to which R¹is 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.

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Note that when W is —C(R⁷)(R⁸)— and R⁷and R⁸are different, then the carbon atom to which they are both bonded will also possess a chiral center. In combination with R⁵or R⁶being different these two chiral centers are referred to as “diasteromers”. Molecular depictions drawn herein follow standard conventions for depicting stereochemistry. To indicate stereoconfiguration, bonds rising from the plane of the drawing and towards the viewer are denoted by solid wedges wherein the broad end of the wedge is attached to the atom rising from the plane of the drawing towards the viewer. Bonds going below the plane of the drawing and away from the viewer are denoted by dashed wedges wherein the 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.

This invention comprises racemic mixtures, for example, equal amounts of the enantiomers of Formulae 1′ and 1″, or when R⁷and R⁸are dissimilar. 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 enantiomer is present in greater amounts than the other, and the extent of enrichment can be defined by an expression of enantiomeric excess (“ee”), which is defined as (2x−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 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 Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. 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 appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

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 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 where Formula 1 including N-oxides, salts, compositions and use thereof are described as follows:

- Embodiment 1. A compound of Formula 1, including all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Invention.
- Embodiment 2. A compound of Embodiment 1 wherein W is —C(R⁷)(R⁸)—.
- Embodiment 3. A compound of Embodiment 1 wherein W is —O—.
- Embodiment 4. A compound of any one of Embodiments 1 through 3 wherein wherein R¹is H, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₁-C₇haloalkyl, C₂-C₇haloalkenyl, C₂-C₇alkoxyalkyl or C₁-C₇alkoxy.
- Embodiment 5. A compound of Embodiment 4 wherein R¹is H, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇alkoxyalkyl or C₁-C₇alkoxy.
- Embodiment 6. A compound of Embodiment 5 wherein R¹is H, C₁-C₇alkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl or C₂-C₇alkoxyalkyl.
- Embodiment 7. A compound of Embodiment 6 wherein R¹is H, C₁-C₇alkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl or C₂-C₇alkoxyalkyl.
- Embodiment 8. A compound of Embodiment 7 wherein R¹is H, C₁-C₇alkyl, C₃-C₇cycloalkyl or C₂-C₇alkoxyalkyl.
- Embodiment 9. A compound of Embodiment 8 wherein R¹is H or C₁-C₇alkyl.
- Embodiment 10. A compound of Embodiment 9 wherein R¹is H.
- Embodiment 11. A compound of Embodiment 9 wherein R¹is C₁-C₄alkyl.
- Embodiment 12. A compound of Embodiment 11 wherein R¹is C₂-C₄alkyl.
- Embodiment 13. A compound of Embodiment 11 wherein R¹is methyl or ethyl.
- Embodiment 14. A compound of Embodiment 13 wherein R¹is methyl.
- Embodiment 15. A compound of any one of Embodiments 1 through 9 wherein R¹is other than methyl.
- Embodiment 16. A compound of any one of Embodiments 1 through 10 wherein R¹is other than H.
- Embodiment 17. A compound of any one of Embodiments 1 through 16 wherein R²is H, halogen, cyano, —CHO, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₁-C₄alkylcarbonyl, C₂-C₇alkylcarbonyloxy, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy, C₁-C₅alkylthio or C₂-C₃alkoxycarbonyl.
- Embodiment 18. A compound of Embodiment 17 wherein R²is H, halogen, cyano, —CHO, C₁-C₇alkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy or C₁-C₅alkylthio.
- Embodiment 19. A compound of Embodiment 18 wherein R²is H, halogen, cyano, C₁-C₇alkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy or C₁-C₅alkylthio.
- Embodiment 20. A compound of Embodiment 19 wherein R²is H, halogen, cyano, C₁-C₇alkyl, C₁-C₇haloalkyl or C₁-C₇alkoxy.
- Embodiment 21. A compound of Embodiment 20 wherein R²is H, Cl, Br, I, cyano, methyl, CF₃or methoxy.
- Embodiment 22. A compound of Embodiment 21 wherein R²is H, Cl, methyl or methoxy.
- Embodiment 23. A compound of Embodiment 22 wherein R²is Cl or methyl.
- Embodiment 24. A compound of Embodiment 22 wherein R²is Cl.
- Embodiment 25. A compound of Embodiment 22 wherein R²is methyl.
- Embodiment 26. A compound of Embodiment 22 wherein R²is methoxy.
- Embodiment 27. A compound of any one of Embodiments 1 through 22 wherein R²is other than H.
- Embodiment 28. A compound of any one of Embodiments 1 through 27 wherein each R³is independently H, halogen, C₁-C₅alkyl, C₃-C₅cycloalkyl, C₁-C₅haloalkyl, C₁-C₅alkoxy or C₁-C₅haloalkoxy.
- Embodiment 29. A compound of Embodiment 28 wherein each R³is independently H, halogen, C₁-C₅alkyl, C₁-C₅haloalkyl, C₁-C₅alkoxy or C₁-C₅haloalkoxy.
- Embodiment 30. A compound of Embodiment 29 wherein each R³is independently H, halogen, methyl, ethyl, CF₃or —OCHF₂.
- Embodiment 31. A compound of Embodiment 30 wherein each R³is independently H, F, Cl, Br or methyl.
- Embodiment 32. A compound of Embodiment 31 wherein each R³is H.
- Embodiment 33. A compound of Embodiment 31 wherein each R³is independently H, Cl, Br or methyl.
- Embodiment 34. A compound of Embodiment 33 wherein each R³is independently H or methyl.
- Embodiment 35. A compound of any one of Embodiments 1 through 34 wherein n is 0 to 2.
- Embodiment 36. A compound of Embodiment 35 wherein n is 0 or 1.
- Embodiment 37. A compound of Embodiment 36 wherein n is 1.
- Embodiment 38. A compound of any one of Embodiments 1 through 37 wherein R³is located at the 7-position.
- Embodiment 39. A compound of any one of Embodiments 1 through 38 wherein R⁴is H, halogen, C₁-C₃alkyl, C₃-C₄cycloalkyl, C₁-C₃haloalkyl or C₁-C₃alkoxy.
- Embodiment 40. A compound of Embodiment 39 wherein R⁴is H, halogen, C₁-C₂alkyl, cyclopropyl or C₁-C₂haloalkyl.
- Embodiment 41. A compound of Embodiment 40 wherein R⁴is H, halogen, methyl, ethyl or CF₃.
- Embodiment 42. A compound of Embodiment 41 wherein R⁴is H, F, Cl, Br or methyl.
- Embodiment 43. A compound of Embodiment 42 wherein R⁴is methyl.
- Embodiment 44. A compound of Embodiment 42 wherein R⁴is H.
- Embodiment 45. A compound of any one of Embodiments 1 through 44 wherein R⁵is H or methyl.
- Embodiment 46. A compound of Embodiment 45 wherein R⁵is H.
- Embodiment 47. A compound of any one of Embodiments 1 through 46 wherein R⁶is H or methyl.
- Embodiment 48. A compound of Embodiment 47 wherein R⁶is H.
- Embodiment 49. A compound of any one of Embodiments 1 through 48 wherein R⁷is H or methyl.
- Embodiment 50. A compound of Embodiment 49 wherein R⁷is H.
- Embodiment 51. A compound of any one of Embodiments 1 through 50 wherein R⁸is H or methyl.
- Embodiment 52. A compound of Embodiment 51 wherein R⁸is H.
- Embodiment 53. A compound of any one of Embodiments 1 through 52 wherein L is a direct bond or C₁-C₂alkanediyl.
- Embodiment 54. A compound of Embodiment 53 wherein L is a direct bond.
- Embodiment 55. A compound of any one of Embodiments 1 through 52 wherein L is C₁-C₂alkanediyl or C₂-C₃alkenediyl.
- Embodiment 56. A compound of any one of Embodiments 1 though 53 or 55 wherein L is C₁-C₂alkanediyl.
- Embodiment 57. A compound of Embodiment 55 wherein L is —CH₂— or —CH═CH—.
- Embodiment 58. A compound of Embodiment 57 wherein L is —CH₂—.
- Embodiment 59. A compound of any one of Embodiments 1 through 58 wherein G is H, C(═O)R⁹, C(═S)R⁹, CO₂R¹⁰, C(═O)SR¹⁰, C(═O)N(R¹¹)(R¹²) or P(═O)(R¹³)(R¹⁴) or C₁-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₁-C₄haloalkyl, C₂-C₄haloalkenyl, C₂-C₄haloalkynyl, C₂-C₄alkoxyalkyl, C₃-C₆cycloalkyl or C₄-C₇cycloalkylalkyl.
- Embodiment 60. A compound of Embodiment 59 wherein G is H, C(═O)R⁹, CO₂R¹⁰, C(═O)N(R¹¹)(R¹²) or P(═O)(R¹³)(R¹⁴); or C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄haloalkyl, C₂-C₄haloalkenyl, C₂-C₄alkoxyalkyl, C₃-C₆cycloalkyl or C₄-C₇cycloalkylalkyl.
- Embodiment 61. A compound of Embodiment 60 wherein G is H, C(═O)R⁹, CO₂R¹⁰or P(═O)(R¹³)(R¹⁴); or C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkoxyalkyl or C₃-C₆cycloalkyl.
- Embodiment 62. A compound of Embodiment 61 wherein G is H, C(═O)R⁹or CO₂R¹⁰; or C₂-C₄alkoxyalkyl or C₃-C₆cycloalkyl.
- Embodiment 63. A compound of Embodiment 62 wherein G is H.
- Embodiment 64. A compound of Embodiment 62 wherein G is C(═O)R⁹.
- Embodiment 65. A compound of Embodiment 62 wherein G is CO₂R¹⁰.
- Embodiment 66. A compound of Embodiment 62 wherein G is C₂-C₄alkoxyalkyl.
- Embodiment 67. A compound of Embodiment 62 wherein G is C₃-C₆cycloalkyl.
- Embodiment 68. A compound of any one of Embodiments 1 through 62 or 64 wherein R⁹and R¹¹are independently H, C₁-C₇alkyl, C₃-C₇alkenyl, C₃-C₇alkynyl, C₃-C₇cycloalkyl or C₁-C₇haloalkyl; or phenyl, benzyl, or a 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 69. A compound of Embodiment 68 wherein R⁹and R¹¹are independently H, C₁-C₇alkyl or C₃-C₇alkenyl; or phenyl, benzyl, each phenyl or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 70. A compound of Embodiment 69 wherein R⁹is H or C₁-C₇alkyl; or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 71. A compound of Embodiment 70 wherein R⁹is C₁-C₇alkyl; or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 72. A compound of any one of Embodiments 1 through 62 or 65 wherein R¹⁰is C₁-C₇alkyl, C₃-C₇alkenyl, C₃-C₇cycloalkyl, C₂-C₇haloalkyl or C₃-C₇haloalkenyl; or phenyl, benzyl or a 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 73. A compound of Embodiment 72 wherein R¹⁰is C₁-C₇alkyl or C₃-C₇cycloalkyl; or phenyl or benzyl, each phenyl or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 74. A compound of Embodiment 73 wherein R¹⁰is C₁-C₇alkyl; or phenyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment 75. A compound of Embodiment 74 wherein R¹⁰is CH₃, CH₂CH₃, CH₂CH₂CH₃, Ph, Ph(4-Cl), Ph(3-CF₃) or Ph(4-CF₃).
- Embodiment 76. A compound of any one of Embodiments 1 through 75 wherein R¹²is H, C₁-C₇alkyl, C₂-C₇alkenyl, C₂-C₇alkynyl or C₃-C₇cycloalkyl.
- Embodiment 77. A compound of Embodiment 76 wherein R¹²is H, C₁-C₇alkyl or C₃-C₇cycloalkyl.
- Embodiment 78. A compound of any one of Embodiments 1 through 77 wherein R¹³is C₁-C₄alkyl or C₁-C₄alkoxy.
- Embodiment 79. A compound of Embodiment 78 wherein R¹³is C₁-C₂alkyl or C₁-C₂alkoxy.
- Embodiment 80. A compound of any one of Embodiments 1 through 79 wherein R¹⁴is C₁-C₄alkyl or C₁-C₄alkoxy.
- Embodiment 81. A compound of Embodiment 80 wherein R¹⁴is C₁-C₂alkyl or C₁-C₂alkoxy.

Embodiments of this invention, including Embodiments 1-81 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 1-81 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

- Embodiment A. A compound of Formula 1 wherein
  - R¹is H, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₁-C₇haloalkyl, C₂-C₇haloalkenyl, C₂-C₇alkoxyalkyl or C₁-C₇alkoxy;
  - R²is H, halogen, cyano, —CHO, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₁-C₄alkylcarbonyl, C₂-C₇alkylcarbonyloxy, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy, C₁-C₅alkylthio or C₂-C₃alkoxycarbonyl;
  - each R³is independently H, halogen, C₁-C₅alkyl, C₃-C₅cycloalkyl, C₁-C₅haloalkyl, C₁-C₅alkoxy or C₁-C₅haloalkoxy;
  - n is 0 to 2;
  - R⁴is H, halogen, C₁-C₃alkyl, C₃-C₄cycloalkyl, C₁-C₃haloalkyl or C₁-C₃alkoxy;
  - L is a direct bond or C₁-C₂alkanediyl;
  - G is H, C(═O)R⁹, C(═S)R⁹, CO₂R¹⁰, C(═O)SR¹⁰, CON(R¹¹)(R¹²) or P(═O)(R¹³)(R¹⁴); or C₁-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₁-C₄haloalkyl, C₂-C₄haloalkenyl, C₂-C₄haloalkynyl, C₂-C₄alkoxyalkyl, C₃-C₆cycloalkyl or C₄-C₇cycloalkylalkyl;
  - R⁹and R¹¹are independently H, C₁-C₇alkyl, C₃-C₇alkenyl, C₃-C₇alkynyl, C₃-C₇cycloalkyl or C₁-C₇haloalkyl; or phenyl, benzyl, or a 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
  - R¹⁰is C₁-C₇alkyl, C₃-C₇alkenyl, C₃-C₇cycloalkyl, C₂-C₇haloalkyl or C₃-C₇haloalkenyl; or phenyl, benzyl or a 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
  - R¹²is H, C₁-C₇alkyl, C₂-C₇alkenyl, C₂-C₇alkynyl or C₃-C₇cycloalkyl;
  - R¹³is C₁-C₄alkyl or C₁-C₄alkoxy; and
  - R¹⁴is C₁-C₄alkyl or C₁-C₄alkoxy.
- Embodiment B. A compound of Embodiment A wherein
  - R¹is H, C₁-C₇alkyl, C₃-C₈alkylcarbonylalkyl, C₃-C₈alkoxycarbonylalkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇alkoxyalkyl or C₁-C₇alkoxy;
  - R²is H, halogen, cyano, —CHO, C₁-C₇alkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy or C₁-C₅alkylthio;
  - each R³is independently H, halogen, C₁-C₅alkyl, C₁-C₅haloalkyl, C₁-C₅alkoxy or C₁-C₅haloalkoxy;
  - n is 0 or 1;
  - R⁴is H, halogen, C₁-C₂alkyl, cyclopropyl or C₁-C₂haloalkyl;
  - L is a direct bond;
  - G is H, C(═O)R⁹, CO₂R¹⁰, CON(R¹¹)(R¹²) or P(═O)(R¹³)(R¹⁴); or C₁-C₄alkyl, C₂-C₄alkenyl, C₁-C₄haloalkyl, C₂-C₄haloalkenyl, C₂-C₄alkoxyalkyl, C₃-C₆cycloalkyl or C₄-C₇cycloalkylalkyl;
  - R⁹and R¹¹are independently H, C₁-C₇alkyl or C₃-C₇alkenyl; or phenyl, benzyl, each phenyl or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
  - R¹⁰is C₁-C₇alkyl or C₃-C₇cycloalkyl; or phenyl or benzyl, each phenyl or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;
  - R¹²is H, C₁-C₇alkyl or C₃-C₇cycloalkyl;
  - R¹³is C₁-C₂alkyl or C₁-C₂alkoxy; and
  - R¹⁴is C₁-C₂alkyl or C₁-C₂alkoxy.
- Embodiment C. A compound of Embodiment B wherein
  - R¹is H, C₁-C₇alkyl, C₄-C₇alkylcycloalkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl or C₂-C₇alkoxyalkyl;
  - R²is H, halogen, cyano, C₁-C₇alkyl, C₂-C₇haloalkoxyalkyl, C₁-C₇haloalkyl, C₂-C₇alkoxyalkyl, C₁-C₇alkoxy or C₁-C₅alkylthio;
  - each R³is independently H, halogen, methyl, ethyl, CF₃or —OCHF₂;
  - R⁴is H, halogen, methyl, ethyl or CF₃;
  - G is H, C(═O)R⁹, CO₂R¹⁰or P(═O)(R¹³)(R¹⁴); or C₁-C₄alkyl, C₁-C₄haloalkyl, C₂-C₄alkoxyalkyl or C₃-C₆cycloalkyl;
  - R⁹is H or C₁-C₇alkyl; or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl; and
  - R¹⁰is C₁-C₇alkyl; or phenyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl.
- Embodiment D. A compound of Embodiment C wherein
  - R¹is H, C₁-C₇alkyl, C₃-C₇cycloalkyl, C₄-C₇cycloalkylalkyl or C₂-C₇alkoxyalkyl;
  - R²is H, halogen, cyano, C₁-C₇alkyl, C₁-C₇haloalkyl or C₁-C₇alkoxy;
  - each R³is independently H, F, Cl, Br or methyl;
  - R⁴is H, F, Cl, Br or methyl;
  - R⁵is H or methyl;
  - R⁶is H or methyl;
  - R⁷is H or methyl;
  - R⁸is H or methyl;
  - G is H, C(═O)R⁹or CO₂R¹⁰; or C₂-C₄alkoxyalkyl or C₃-C₆cycloalkyl;
  - R⁹is C₁-C₇alkyl; or benzyl optionally substituted by halogen, C₁-C₄alkyl or C₁-C₄haloalkyl; and
  - R¹⁰is CH₃, CH₂CH₃, CH₂CH₂CH₃, Ph, Ph(4-Cl), Ph(3-CF₃) or Ph(4-CF₃).
- Embodiment E. A compound of Embodiment D wherein
  - W is —C(R⁷)(R⁸)—;
  - R¹is H, C₁-C₇alkyl, C₃-C₇cycloalkyl or C₂-C₇alkoxyalkyl;
  - R²is H, Cl, Br, I, cyano, methyl, CF₃or methoxy;
  - n is 0;
  - R⁴is methyl;
  - R⁵is H;
  - R⁶is H;
  - R⁷is H;
  - R⁸is H; and
  - G is H.
- Embodiment F. A compound of Embodiment D wherein
  - W is —O—;
  - R¹is H or C₁-C₇alkyl;
  - R²is H, Cl, methyl or methoxy;
  - n is 0;
  - R⁴is methyl;
  - R⁵is H;
  - R⁶is H; and
  - G is H.

Specific Embodiments of the Invention are the following compounds of the Summary of the Invention:

4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-hydroxy-2,6-dimethyl-3-(2H)-pyridazinone; and

5-hydroxy-2,6-dimethyl-4-(3-methyl-2H-1-benzopyran-4-yl)-3-(2H)-pyridazinone.

This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for selective control of weeds in crops 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 (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).

“Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the Q_B-binding niche and thus block electron transport from Q_Ato Q_Bin 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 Q_B-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 chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate 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 (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide), 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, 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 (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.

“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 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, fluazolate, 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-dimethyl-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) and tiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

“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 phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and 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, S-beflubutamid, diflufenican, 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 benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, 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, 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, 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.

“HST inhibitors” (b13) 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 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.

HST inhibitors also include compounds of Formulae A and B.

[Image Omitted]

wherein R^d1is H, Cl or CF₃; R^d2is H, Cl or Br; R^d3is H or Cl; R^d4is H, Cl or CF₃; R^d5is CH₃, CH₂CH₃or CH₂CHF₂; and R^d6is OH, or —OC(═O)-i-Pr; and R^e1is H, F, Cl, CH₃or CH₂CH₃; R^e2is H or CF₃; R^e3is H, CH₃or CH₂CH₃; R^e4is H, F or Br; R^e5is Cl, CH₃, CF₃, OCF₃or CH₂CH₃; R^e6is H, CH₃, CH₂CHF₂or C≡CH; R^e7is
- OH, —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and A^e8is N or CH.

“Cellulose biosynthesis inhibitors” (b14) 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, [3-(3,5-dichlorophenyl)-1H-pyrazol-4-yl]phenyl-methanone and triaziflam.

“Other herbicides” (b15) 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 (b14) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, daimuron, 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

“Other herbicides” (b15) also include a compound of Formula (b15A)

[Image Omitted]

- wherein
- R¹²is H, C₁-C₆alkyl, C₁-C₆haloalkyl or C₄-C₈cycloalkyl;
- R¹³is H, C₁-C₆alkyl or C₁-C₆alkoxy;
- Q¹is an optionally substituted ring system 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, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, SF₅, NHR¹⁷; or phenyl optionally substituted by 1 to 3 R¹⁶; 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, C₁-C₆alkyl or C₁-C₆haloalkyl;
- R¹⁷is C₁-C₄alkoxycarbonyl.
  
  In one Embodiment wherein “other herbicides” (b15) also include a compound of Formula (b15A), it is preferred that R¹²is H or C₁-C₆alkyl; more preferably R¹²is H or methyl. Preferrably R¹³is H. Preferably Q¹is 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, C₁-C₄alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy or C₁-C₃haloalkoxy; more preferably each R¹⁴is independently chloro, fluoro, bromo, C₁-C₂haloalkyl, C₁-C₂haloalkoxy or C₁-C₂alkoxy. Preferrably each R¹⁵is independently halogen, C₁-C₄alkyl, C₁-C₃haloalkoxy; more preferably each R¹⁵is independently chloro, fluoro, bromo, C₁-C₂haloalkyl, C₁-C₂haloalkoxy or C₁-C₂alkoxy. Specifically preferred as “other herbicides” (b15) include any one of the following (b15A-1) through (b15A-15) wherein the stereochemistry at the 3- and 4-positions of the pyrrolidinone ring are preferably in the trans configuration relative to each other:

[Image Omitted]

“Other herbicides” (b15) also include a compound of Formula (b15B)

[Image Omitted]

- wherein
- R¹⁸is H, C₁-C₆alkyl, C₁-C₆haloalkyl or C₄-C₈cycloalkyl;
- each R¹⁹is independently halogen, C₁-C₆haloalkyl or C₁-C₆haloalkoxy;
- p is an integer of 0, 1, 2 or 3;
- each R²⁰is independently halogen, C₁-C₆haloalkyl or C₁-C₆haloalkoxy; and
- q is an integer of 0, 1, 2 or 3.
  
  In one Embodiment wherein “other herbicides” (b15) also include a compound of Formula (b15B), it is preferred that R¹⁸is H, methyl, ethyl or propyl; more preferably R¹⁸is H or methyl; most preferably R¹⁸is H. Preferrably each R¹⁹is independently chloro, fluoro, C₁-C₃haloalkyl or C₁-C₃haloalkoxy; more preferably each R¹⁹is independently chloro, fluoro, C₁fluoroalkyl (i.e. fluoromethyl, difluoromethyl or trifluoromethyl) or C₁fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy). Preferably each R²⁰is independently chloro, fluoro, C₁haloalkyl or C₁haloalkoxy; more preferably each R²⁰is independently chloro, fluoro, C₁fluoroalkyl (i.e. fluoromethyl, difluorormethyl or trifluromethyl) or C₁fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy). Specifically preferred as “other herbicides” (b15) include any one of the following (b15B-1) through (b15B-19):

(b15B-1) 2-oxo-N-[2-(trifluoromethyl)phenyl]-4-(3,4-difluorophenyl)-3-piperidinecarboxamide,

(b15B-2) N-(2,3-difluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-3) 2-oxo-N-[2-(trifluoromethyl)phenyl)]-4-[3-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-4) N-(2-chlorophenyl)-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-5) N-(2-fluorophenyl)-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-6) (3R,4S)—N-(2,3-difluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-7) (3R,4S)—N-(2,3-difluorophenyl)-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-8) (3R,4S)—N-(3-chloro-2-fluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]-3-piperidinecarboxamide,

(b15B-9) (3R,4S)-2-oxo-4-[3-(trifluoromethyl)phenyl]-N-[2,3,4-trifluorophenyl]-3-piperidinecarboxamide,

[Image Omitted]

(b15B-14) (3R,4S)-4-(3-chlorophenyl)-N-(2,3-difluorophenyl)-2-oxo-3-piperidinecarboxamide,

(b15B-15) 4-[3-(difluoromethyl)phenyl]-N-(2,3,4-trifluorophenyl)-2-oxo-piperidinecarboxamide,

(b15B-16) 4-[3-(difluoromethyl)phenyl]-N-(2-fluorophenyl)-2-oxo-piperidinecarboxamide,

(b15B-17) 4-[3-(difluoromethyl)phenyl]-N-(2,3-difluorophenyl)-2-oxo-3-piperidinecarboxamide,

(b15B-18) (3S,4S)—N-(2,3-difluorophenyl)-4-(4-fluorophenyl)-1-methyl-2-oxo-3-piperidinecarboxamide and (b15B-19) (3R,4S)-2-oxo-N-[2-(trifluoromethyl)phenyl]-4-(4-fluorophenyl)-3-piperidinecarboxamide.

“Other herbicides” (b15) also include a compound of Formula (b15C),

[Image Omitted]

wherein R¹is Cl, Br or CN; and R²is C(═O)CH₂CH₂CF₃, CH₂CH₂CH₂CH₂CF₃or 3-CHF₂-isoxazol-5-yl.

“Other herbicides” (b15) also include a compound of Formula (b15D)

[Image Omitted]

wherein R¹is CH₃, R²is Me, R⁴is OCHF₂, G is H, and n is 0; R¹is CH₃, R²is Me, R³is 5-F, R⁴is Cl, G is H, and n is 1; R¹is CH₃, R²is Cl, R⁴is Me, G is H, and n is 0; R¹is CH₃, R²is Me, R⁴is Cl, G is H, and n is 0; R¹is CH₃, R²is Me, R³is 5-Me, R⁴is OCHF₂, G is H, and n is 1; R¹is CH₃, R²is Me, R³is 5-Br, R⁴is OCHF₂, G is H, and n is 1; R¹is CH₃, R²is Me, R³is 5-Cl, R⁴is Cl, G is H, and n is 1; and R¹is CH₃, R²is CH₃, R⁴is OCHF₂, G is C(O)Me, and n is 0.

“Other herbicides” (b15) also include a compound of Formula (b15E)

[Image Omitted]

wherein

- R¹is CH₃, R²is Cl, and G is H; and
- R¹is CH₃, R²is Cl, and G is C(O)Me.

“Herbicide safeners” (b16) 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 and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone 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 1-6 can be used to prepare a compound of Formula 1. The definitions of W, R¹, R², R³, n, R⁴, R⁵, R⁶, L and G in the compounds of Formulae 1-8 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1a and 1b are various subsets of the compounds of Formula 1, and all substituents for Formulae 1a and 1b are as defined above for Formula 1 unless otherwise noted.

As shown in Scheme 1, pyridazinones of Formula 1a can be made by reacting substituted 5-hydroxy-3(2H)-pyridazinones of Formula 1b with a suitable electrophilic reagent of Formula 2 in the presence of base in an appropriate solvent. Some examples of reagent classes representing Formula 2 wherein Z¹is Cl and L is a direct bond include acid chlorides (G is —(C═O)R⁵), carboxylates (G is —CO₂R⁶), carbamoyl chlorides (G is —CONR⁷R⁸), sulfonyl chlorides (G is —S(O)₂R⁵) and chlorosulfonamides (G is —S(O)₂NR⁷R⁸). Examples of suitable bases for this reaction include, but are not limited to, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride or potassium tert-butoxide and, depending on the specific base used, appropriate solvents can be protic or aprotic and used anhydrous or as aqueous mixtures. Preferred solvents for this reaction include acetonitrile, methanol, ethanol, tetrahydrofuran, diethyl ether, 1,2-dimethoxyethane, dioxane, dichloromethane or N,N-dimethylformamide. The reaction can be performed at a range of temperatures, typically ranging from 0° C. to the reflux temperature of the solvent.

[Image Omitted]

As shown in Scheme 2 compounds of the Formula 1b can be prepared via dealkylation of a compound of Formula 2, where R is a lower alkyl group. Dealkylation reagents such as boron tribromide, lithium chloride, or morpholine are suitable for this transformation (see, for example, WO 2009/086041, WO 2013/160126 and WO 2013/050421).

[Image Omitted]

A compound of Formula 2 can be prepared by coupling reactions of organometallic pyridazinone coupling partners of Formula 3 with a saturated bicyclic halide and sulfonate of Formula 4 as is shown in Scheme 3. The organometallic coupling partner can be, for example, an organozinc, organomagnesium, organotin, or organoboron reagent. Palladium catalysts such as palladium tetrakis (triphenylphosphine) and those generated from other palladium sources, such as Pd₂dba₃and Pd(OAc)₂, and a phosphine or N-heterocyclic carbene ligand can be used in the coupling procedures (Maes et al. J. Org. Chem. 2011, 76, 9648-9659). Palladium precatalysts based on dialkyl biarylphosphine ligands, such as X-Phos, S-Phos and Ru-Phos (Buchwald et al. Angew. Chem. Int. Ed. 2013, 52(2), 615-619.), or precatalysts derived from N-heterocyclic carbene ligands such as PEPPSI-i-Pr and PEPPSI-i-Pent (Organ et al. Eur. J. Org. Chem. 2010, 4343-4354) can affect this coupling as well. The reaction can be carried out in solvents such as tetrahydrofuran, dimethoxyethane, N-methyl-2-pyrrolidone and dioxane. Coupling partners may be either heterocyclic halides or sulfonates. A particularly useful class of coupling partners for the reaction are those based on nonaflates (—OSO₂C₄F₉) of saturated bicyclic compounds.

[Image Omitted]

As seen in Scheme 4 a compound of Formula 3 can be prepared by metalation at the 4-position of a pyridazinone of Formula 5. Zincation can be accomplished with reagents such as 2,2,6,6-bis(tetramethylpiperidine)zinc, magnesium chloride, lithium chloride complex in toluene/tetrahydrofuran (i.e. Zn(TMP)-LiCl or Zn(TMP)₂—MgCl₂—LiCl). Magnesiation of this position can also be accomplished by treatment with Mg(TMP)-LiCl. See Verhelst, T., Ph.D. thesis, University of Antwerp, 2012 for conditions for pyridazinone metallation and for palladium catalyzed cross-coupling of 4-zincated and 4-magnesiated pyridazinones. The synthesis and cross-coupling conditions for 4-stannylpyridazinones are known from Stevenson et. al. J. Het. Chem. 2005, 42, 427.

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Compounds of Formula 4 where X is a halide or sulfonate can be prepared from ketones of Formula 6 as shown in Scheme 5. Dehydration/halogenation can be accomplished with such reagents as phosphorous oxychloride, phosphorous oxybromide, phosphorous pentachloride, or phosphorous tribromide. These reactions can be performed neat or in a variety of solvents such as dichloromethane, dichloroethane or chlorobenzene at temperatures ranging from 0 to 120° C. See Organic Letters 2003, 5(19), 3387-3390 where the sulfonylation can be accomplished with such reagents as methanesulfonyl chloride, trifluoromethanesulfonic anhydride, or perflouro-1-butanesulfonyl fluoride. The reaction can be performed in the presence of a suitable base which includes but is not limited to, lithium diisopropylamide, lithium hexamethyldisilizide, sodium hydride, pyridine or triethylamine in an appropriate solvent such as N,N-dimethylformamide, tetrahydrofuran, dioxane, or dichloromethane. These reactions are performed at temperatures ranging from −78° C. to room temperature. See J. Org. Chem. 2015, 80(22), 11618-11623.

[Image Omitted]

The R²substitutent of compounds of Formula 5, wherein R²is alkyl, cycloalkyl or substituted alkyl can be prepared by transition metal catalyzed reactions with a compound of Formula 7 as shown in Scheme 6. For reviews of these types of reactions, see: E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley and Sons, Inc., New York, 2002, N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Springer, New York, 2002, H. C. Brown et al., Organic Synthesis via Boranes, Aldrich Chemical Co., Milwaukee, Vol. 3, 2002, Suzuki et al., Chemical Reviews 1995, 95, 2457-2483 and Molander et al., Accounts of Chemical Research 2007, 40, 275-286. Also see Tetrahedron Organic Chemistry Series Vol. 26: Palladium in Heterocyclic Chemistry, 2^ndEd., Gribble and Li, editors, Elsevier, Amsterdam, 2007. For a review of Buchwald-Hartwig chemistry see Yudin and Hartwig, Catalyzed Carbon-Heteroatom Bond Formation, 2010, Wiley, New York. Related synthetic methods for the introduction of other functional groups at the R²position of Formula 5 are known in the art. Copper catalyzed reactions are useful for introducing the CF₃group. For a comprehensive recent review of reagents for this reaction see Wu, Neumann and Beller in Chemistry: An Asian Journal 2012, ASAP, and references cited therein. For the introduction of a sulfur-containing substitutent at this position, see methods disclosed in WO 2013/160126. For the introduction of a cyano group at this position, see WO 2014/031971. For the introduction of a nitro group, see J. Am. Chem. Soc. 2009, 12898. For introduction of a fluoro substituent, see J. Am. Chem. Soc. 2014, 3792.

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

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 particular 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. ¹H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCl₃; “s” means singlet, “d” means doublet, and “m” means multiplet.

EXAMPLE 1
Synthesis of 4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-methoxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 1)
Step A: Preparation of 3,4-dihydro-2-methyl-1-naphthalenyl-1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate

To a solution of 2-methyl-1-tetralone (0.5 g, 3.1 mmol) in tetrahydrofuran (15 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1 M in tetrahydrofuran 3.7 mL, 3.7 mmol). The reaction mixture was stirred for 30 min. then perflouro-1-butanesulfonyl fluoride (1.2 g, 4.0 mmol) was added, and the resulting solution was allowed to warm to ambient temperature. After 30 min. the mixture was concentrated onto Celite® diatomaceaous earth filter aid and purified via silica gel chromatography using a gradient of ethyl acetate in hexanes as eluent to provide 0.97 g of the title compound.

¹H NMR δ 7.30-7.34 (m, 1H), 7.17-7.29 (m, 2H), 7.12-7.17 (m, 1H), 2.85 (m, 2H), 2.44 (m, 2H), 2.00 (s, 3H).

Step B: Preparation of 4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-methoxy-2,6-dimethyl-3(2H)-pyridazinone

A reaction vessel was purged with nitrogen and charged with 5-methoxy-2,6-dimethyl-3(2H)-pyridazinone (0.2 g, 1.3 mmol), 3,4-dihydro-2-methyl-1-naphthalenyl-1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate (i.e. the compound from Step A) (0.57 g, 1.3 mmol), SPhos pre-catalyst-G2 (chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl) [2-(2′-amino-1,1′-biphenyl)]palladium(II), (0.05 g, 0.07 mmol), and tetrahydrofuran (5 mL). Bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex (1.6 mL, 1.6 mmol) was added and the solution was heated at 50° C. overnight. The resulting mixture was concentrated onto Celite® diatomaceaous earth filter aid and purified via silica gel chromatography eluting with a gradient of ethyl acetate in hexanes to provide 0.32 g of the title compound, a compound of the invention.

¹H NMR δ 7.11-7.15 (m, 1H), 7.06-7.11 (m, 2H), 6.71-6.76 (m, 1H), 3.71 (d, 6H), 2.99-3.04 (m, 1H), 2.78-2.83 (m, 1H), 2.34-2.48 (m, 2H), 2.28 (s, 3H), 1.77 (s, 3H).

EXAMPLE 2
Synthesis of 4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 2)
Step A: Preparation of 4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

A solution of the 4-(3,4-dihydro-2-methyl-1-naphthalenyl)-5-methoxy-2,6-dimethyl-3(2H)-pyridazinone (i.e. the product from Step B above) (0.2 g, 0.68 mmol) and morpholine (2 mL) were heated at 120° C. for 40 min. The resulting solution was cooled to ambient temperature and 1 N aqueous hydrochloric acid (50 mL) and isopropanol (0.5 mL) were added. The resulting mixture was stirred for 10 min and the resulting solid that formed was filtered and washed with water. The solid was dried under vacuum to give 0.16 g of the title compound, a compound of the invention.

¹H NMR δ 7.03-7.17 (m, 3H), 6.66-6.75 (m, 1H), 5.50 (s, 1H), 3.75 (s, 3H), 2.94-3.05 (m, 1H), 2.79-2.90 (m, 1H), 2.39-2.56 (m, 2H), 2.33 (s, 3H), 1.80 (s, 3H).

EXAMPLE 3
Synthesis of 5-hydroxy-2,6-dimethyl-4-(3-methyl-2H-1-benzopyran-4-yl)-3(2H)-pyridazinone (Compound 3)
Step A: Preparation of 3-methyl-2H-1-benzopyran-4-yl 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate

To a solution of 3-methyl-4-chromanone (1.0 g, 6.2 mmol) in tetrahydrofuran (12 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1 M in tetrahydrofuran, 3.7 mL, 3.7 mmol). The reaction was stirred for 10 min then perflouro-1-butanesulfonyl fluoride (2.6 g, 8.7 mmol) was added, and the resulting mixture was allowed to warm to ambient temperature. After 30 min the mixture was concentrated onto Celite® diatomaceaous earth filter aid, and purified via silica gel chromatography with ethyl acetate in hexanes as eluent to provide 1.2 g of the title compound.

¹H NMR δ 7.16-7.24 (m, 2H), 6.93-7.00 (m, 1H), 6.81-6.86 (m, 1H), 4.81 (s, 2H), 1.86-1.92 (m, 3H).

Step B: Preparation of 5-methoxy-2,6-dimethyl-4-(3-methyl-2H-1-benzopyran-4-yl)-3(2H)-pyridazinone

A reaction vessel was purged with nitrogen and charged with 5-methoxy-2,6-dimethyl-3(2H)-pyridazinone (0.2 g, 1.3 mmol), 3-methyl-2H-1-benzopyran-4-yl 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonate (i.e. the product from Step A) (0.58 g, 1.3 mmol), SPhos pre-catalyst-G2 (chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), 0.05 g, 0.07 mmol), and tetrahydrofuran (5 mL). Bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex (1.6 mL, 1.6 mmol) was added and the solution was heated at 50° C. overnight. The resulting mixture was concentrated onto Celite® diatomaceaous earth filter aid and purified via silica gel chromatography eluting with ethyl acetate in hexanes to provide 0.40 g of the title compound.

¹H NMR δ 7.04-7.11 (m, 1H), 6.80-6.86 (m, 2H), 6.67-6.72 (m, 1H), 4.87 (d, 1H), 4.71 (d, 1H), 3.71-3.78 (m, 6H), 2.28 (s, 3H), 1.67 (s, 3H).

Step C: Preparation of 5-hydroxy-2,6-dimethyl-4-(3-methyl-2H-1-benzopyran-4-yl)-3(2H)-pyridazinone

A solution of 5-methoxy-2,6-dimethyl-4-(3-methyl-2H-1-benzopyran-4-yl)-3(2H)-pyridazinone (i.e. the product from Step B) (0.25 g, 0.88 mmol) and morpholine (2 mL) were heated at 120° C. for 30 min. The solution was concentrated to dryness in vacuo and 1 N aqueous hydrochloric acid (50 mL) and isopropanol (0.5 mL) were added. The resulting mixture was stirred for 10 min and the solid was filtered and washed with water. The solid was dried under vacuum to give 0.20 g of the title compound, a compound of the invention.

¹H NMR δ 7.03-7.11 (m, 1H), 6.76-6.83 (m, 2H), 6.63-6.68 (m, 1H), 4.82 (d, 1H), 4.64 (d, 1H), 3.70 (s, 3H), 2.31 (s, 3H), 1.60 (s, 3H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 959 can be prepared. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, Pr means propyl, i-Pr means isopropyl, t-Bu means tertiarybutyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEt means ethylthio, —CN means cyano, and SO₂Me means methylsulfonyl. A “-” in the (R³)_ncolumn means n=0.

TABLE 1

W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L—G is H and

(R³)_n
R⁴
(R³)_n
R⁴
(R³)_n
R⁴

—
H
5-Pr
H
6-CN
H

5-Me
H
6-Pr
H
7-CN
H

6-Me
H
7-Pr
H
5-CF₃
H

7-Me
H
5-OMe
H
6-CF₃
H

5-Et
H
6-OMe
H
7-CF₃
H

6-Et
H
7-OMe
H
5-F
H

7-Et
H
5-CN
H
6-F
H

7-F
H
7-CN
Pr
7-Pr
Br

5-Cl
H
5-CF₃
Pr
5-OMe
Br

6-Cl
H
6-CF₃
Pr
6-OMe
Br

7-Cl
H
7-CF₃
Pr
7-OMe
Br

5-Br
H
5-F
Pr
5-CN
Br

6-Br
H
6-F
Pr
6-CN
Br

7-Br
H
7-F
Pr
7-CN
Br

5-OCHF₂
H
5-Cl
Pr
5-CF₃
Br

6-OCHF₂
H
6-Cl
Pr
6-CF₃
Br

7-OCHF₂
H
7-Cl
Pr
7-CF₃
Br

6,7-di-Me
H
5-Br
Pr
5-F
Br

5,7-di-Me
H
6-Br
Pr
6-F
Br

5-Cl, 7-Me
H
7-Br
Pr
7-F
Br

5-Cl, 7-OMe
H
5-OCHF₂
Pr
5-Cl
Br

5-F, 7-Me
H
6-OCHF₂
Pr
6-Cl
Br

5-Me, 7-F
H
7-OCHF₂
Pr
7-Cl
Br

5-Me, 7-Cl
H
6,7-di-Me
Pr
5-Br
Br

5-Me, 7-CN
H
5,7-di-Me
Pr
6-Br
Br

5-Me, 7-OMe
H
5-Cl, 7-Me
Pr
7-Br
Br

5,7-di-F
H
5-Cl, 7-OMe
Pr
5-OCHF₂
Br

5,7-di-Cl
H
5-F, 7-Me
Pr
6-OCHF₂
Br

5,7-di-Br
H
5-Me, 7-F
Pr
7-OCHF₂
Br

—
Pr
5-Me, 7-Cl
Pr
6,7-di-Me
Br

5-Me
Pr
5-Me, 7-CN
Pr
5,7-di-Me
Br

6-Me
Pr
5-Me, 7-OMe
Pr
5-Cl, 7-Me
Br

7-Me
Pr
5,7-di-F
Pr
5-Cl, 7-OMe
Br

5-Et
Pr
5,7-di-Cl
Pr
5-F, 7-Me
Br

6-Et
Pr
5,7-di-Br
Pr
5-Me, 7-F
Br

7-Et
Pr
—
Br
5-Me, 7-Cl
Br

5-Pr
Pr
5-Me
Br
5-Me, 7-CN
Br

6-Pr
Pr
6-Me
Br
5-Me, 7-OMe
Br

7-Pr
Pr
7-Me
Br
5,7-di-F
Br

5-OMe
Pr
5-Et
Br
5,7-di-Cl
Br

6-OMe
Pr
6-Et
Br
5,7-di-Br
Br

7-OMe
Pr
7-Et
Br
—
OMe

5-CN
Pr
5-Pr
Br
5-Me
OMe

6-CN
Pr
6-Pr
Br
6-Me
OMe

7-Me
OMe
5,7-di-F
OMe
5-Cl, 7-OMe
SCHF₂

5-Et
OMe
5,7-di-Cl
OMe
5-F, 7-Me
SCHF₂

6-Et
OMe
5,7-di-Br
OMe
5-Me, 7-F
SCHF₂

7-Et
OMe
—
SCHF₂
5-Me, 7-Cl
SCHF₂

5-Pr
OMe
5-Me
SCHF₂
5-Me, 7-CN
SCHF₂

6-Pr
OMe
6-Me
SCHF₂
5-Me, 7-OMe
SCHF₂

7-Pr
OMe
7-Me
SCHF₂
5,7-di-F
SCHF₂

5-OMe
OMe
5-Et
SCHF₂
5,7-di-Cl
SCHF₂

6-OMe
OMe
6-Et
SCHF₂
5,7-di-Br
SCHF₂

7-OMe
OMe
7-Et
SCHF₂
—
Me

5-CN
OMe
5-Pr
SCHF₂
5-Me
Me

6-CN
OMe
6-Pr
SCHF₂
6-Me
Me

7-CN
OMe
7-Pr
SCHF₂
7-Me
Me

5-CF₃
OMe
5-OMe
SCHF₂
5-Et
Me

6-CF₃
OMe
6-OMe
SCHF₂
6-Et
Me

7-CF₃
OMe
7-OMe
SCHF₂
7-Et
Me

5-F
OMe
5-CN
SCHF₂
5-Pr
Me

6-F
OMe
6-CN
SCHF₂
6-Pr
Me

7-F
OMe
7-CN
SCHF₂
7-Pr
Me

5-Cl
OMe
5-CF₃
SCHF₂
5-OMe
Me

6-Cl
OMe
6-CF₃
SCHF₂
6-OMe
Me

7-Cl
OMe
7-CF₃
SCHF₂
7-OMe
Me

5-Br
OMe
5-F
SCHF₂
5-CN
Me

6-Br
OMe
6-F
SCHF₂
6-CN
Me

7-Br
OMe
7-F
SCHF₂
7-CN
Me

5-OCHF₂
OMe
5-Cl
SCHF₂
5-CF₃
Me

6-OCHF₂
OMe
6-Cl
SCHF₂
6-CF₃
Me

7-OCHF₂
OMe
7-Cl
SCHF₂
7-CF₃
Me

6,7-di-Me
OMe
5-Br
SCHF₂
5-F
Me

5,7-di-Me
OMe
6-Br
SCHF₂
6-F
Me

5-Cl, 7-Me
OMe
7-Br
SCHF₂
7-F
Me

5-Cl, 7-OMe
OMe
5-OCHF₂
SCHF₂
5-Cl
Me

5-F, 7-Me
OMe
6-OCHF₂
SCHF₂
6-Cl
Me

5-Me, 7-F
OMe
7-OCHF₂
SCHF₂
7-Cl
Me

5-Me, 7-Cl
OMe
6,7-di-Me
SCHF₂
5-Br
Me

5-Me, 7-CN
OMe
5,7-di-Me
SCHF₂
6-Br
Me

5-Me, 7-OMe
OMe
5-Cl, 7-Me
SCHF₂
7-Br
Me

5-OCHF₂
Me
5-Cl
F
5-CF₃
CN

6-OCHF₂
Me
6-Cl
F
6-CF₃
CN

7-OCHF₂
Me
7-Cl
F
7-CF₃
CN

6,7-di-Me
Me
5-Br
F
5-F
CN

5,7-di-Me
Me
6-Br
F
6-F
CN

5-Cl, 7-Me
Me
7-Br
F
7-F
CN

5-Cl, 7-OMe
Me
5-OCHF₂
F
5-Cl
CN

5-F, 7-Me
Me
6-OCHF₂
F
6-Cl
CN

5-Me, 7-F
Me
7-OCHF₂
F
7-Cl
CN

5-Me, 7-Cl
Me
6,7-di-Me
F
5-Br
CN

5-Me, 7-CN
Me
5,7-di-Me
F
6-Br
CN

5-Me, 7-OMe
Me
5-Cl, 7-Me
F
7-Br
CN

5,7-di-F
Me
5-Cl, 7-OMe
F
5-OCHF₂
CN

5,7-di-Cl
Me
5-F, 7-Me
F
6-OCHF₂
CN

5,7-di-Br
Me
5-Me, 7-F
F
7-OCHF₂
CN

—
F
5-Me, 7-Cl
F
6,7-di-Me
CN

5-Me
F
5-Me, 7-CN
F
5,7-di-Me
CN

6-Me
F
5-Me, 7-OMe
F
5-Cl, 7-Me
CN

7-Me
F
5,7-di-F
F
5-Cl, 7-OMe
CN

5-Et
F
5,7-di-Cl
F
5-F, 7-Me
CN

6-Et
F
5,7-di-Br
F
5-Me, 7-F
CN

7-Et
F
—
CN
5-Me, 7-Cl
CN

5-Pr
F
5-Me
CN
5-Me, 7-CN
CN

6-Pr
F
6-Me
CN
5-Me, 7-OMe
CN

7-Pr
F
7-Me
CN
5,7-di-F
CN

5-OMe
F
5-Et
CN
5,7-di-Cl
CN

6-OMe
F
6-Et
CN
5,7-di-Br
CN

7-OMe
F
7-Et
CN
—
OCHF₂

5-CN
F
5-Pr
CN
5-Me
OCHF₂

6-CN
F
6-Pr
CN
6-Me
OCHF₂

7-CN
F
7-Pr
CN
7-Me
OCHF₂

5-CF₃
F
5-OMe
CN
5-Et
OCHF₂

6-CF₃
F
6-OMe
CN
6-Et
OCHF₂

7-CF₃
F
7-OMe
CN
7-Et
OCHF₂

5-F
F
5-CN
CN
5-Pr
OCHF₂

6-F
F
6-CN
CN
6-Pr
OCHF₂

7-F
F
7-CN
CN
7-Pr
OCHF₂

5-OMe
OCHF₂
5-Et
SCF₃
5,7-di-Cl
SCF₃

6-OMe
OCHF₂
6-Et
SCF₃
5,7-di-Br
SCF₃

7-OMe
OCHF₂
7-Et
SCF₃
—
Et

5-CN
OCHF₂
5-Pr
SCF₃
5-Me
Et

6-CN
OCHF₂
6-Pr
SCF₃
6-Me
Et

7-CN
OCHF₂
7-Pr
SCF₃
7-Me
Et

5-CF₃
OCHF₂
5-OMe
SCF₃
5-Et
Et

6-CF₃
OCHF₂
6-OMe
SCF₃
6-Et
Et

7-CF₃
OCHF₂
7-OMe
SCF₃
7-Et
Et

5-F
OCHF₂
5-CN
SCF₃
5-Pr
Et

6-F
OCHF₂
6-CN
SCF₃
6-Pr
Et

7-F
OCHF₂
7-CN
SCF₃
7-Pr
Et

5-Cl
OCHF₂
5-CF₃
SCF₃
5-OMe
Et

6-Cl
OCHF₂
6-CF₃
SCF₃
6-OMe
Et

7-Cl
OCHF₂
7-CF₃
SCF₃
7-OMe
Et

5-Br
OCHF₂
5-F
SCF₃
5-CN
Et

6-Br
OCHF₂
6-F
SCF₃
6-CN
Et

7-Br
OCHF₂
7-F
SCF₃
7-CN
Et

5-OCHF₂
OCHF₂
5-Cl
SCF₃
5-CF₃
Et

6-OCHF₂
OCHF₂
6-Cl
SCF₃
6-CF₃
Et

7-OCHF₂
OCHF₂
7-Cl
SCF₃
7-CF₃
Et

6,7-di-Me
OCHF₂
5-Br
SCF₃
5-F
Et

5,7-di-Me
OCHF₂
6-Br
SCF₃
6-F
Et

5-Cl, 7-Me
OCHF₂
7-Br
SCF₃
7-F
Et

5-Cl, 7-OMe
OCHF₂
5-OOCHF₂
SCF₃
5-Cl
Et

5-F, 7-Me
OCHF₂
6-OCHF₂
SCF₃
6-Cl
Et

5-Me, 7-F
OCHF₂
7-OCHF₂
SCF₃
7-Cl
Et

5-Me, 7-Cl
OCHF₂
6,7-di-Me
SCF₃
5-Br
Et

5-Me, 7-CN
OCHF₂
5,7-di-Me
SCF₃
6-Br
Et

5-Me, 7-OMe
OCHF₂
5-Cl, 7-Me
SCF₃
7-Br
Et

5,7-di-F
OCHF₂
5-Cl, 7-OMe
SCF₃
5-OCHF₂
Et

5,7-di-Cl
OCHF₂
5-F, 7-Me
SCF₃
6-OCHF₂
Et

5,7-di-Br
OCHF₂
5-Me, 7-F
SCF₃
7-OCHF₂
Et

—
SCF₃
5-Me, 7-Cl
SCF₃
6,7-di-Me
Et

5-Me
SCF₃
5-Me, 7-CN
SCF₃
5,7-di-Me
Et

6-Me
SCF₃
5-Me, 7-OMe
SCF₃
5-Cl, 7-Me
Et

7-Me
SCF₃
5,7-di-F
SCF₃
5-Cl, 7-OMe
Et

5-F, 7-Me
Et
6-OCHF₂
Cl
6-Cl
C≡CH

5-Me, 7-F
Et
7-OCHF₂
Cl
7-Cl
C≡CH

5-Me, 7-Cl
Et
6,7-di-Me
Cl
5-Br
C≡CH

5-Me, 7-CN
Et
5,7-di-Me
Cl
6-Br
C≡CH

5-Me, 7-OMe
Et
5-Cl, 7-Me
Cl
7-Br
C≡CH

5,7-di-F
Et
5-Cl, 7-OMe
Cl
5-OCHF₂
C≡CH

5,7-di-Cl
Et
5-F, 7-Me
Cl
6-OCHF₂
C≡CH

5,7-di-Br
Et
5-Me, 7-F
Cl
7-OCHF₂
C≡CH

—
Cl
5-Me, 7-Cl
Cl
6,7-di-Me
C≡CH

5-Me
Cl
5-Me, 7-CN
Cl
5,7-di-Me
C≡CH

6-Me
Cl
5-Me, 7-OMe
Cl
5-Cl, 7-Me
C≡CH

7-Me
Cl
5,7-di-F
Cl
5-Cl, 7-OMe
C≡CH

5-Et
Cl
5,7-di-Cl
Cl
5-F, 7-Me
C≡CH

6-Et
Cl
5,7-di-Br
Cl
5-Me, 7-F
C≡CH

7-Et
Cl
—
C≡CH
5-Me, 7-Cl
C≡CH

5-Pr
Cl
5-Me
C≡CH
5-Me, 7-CN
C≡CH

6-Pr
Cl
6-Me
C≡CH
5-Me, 7-OMe
C≡CH

7-Pr
Cl
7-Me
C≡CH
5,7-di-F
C≡CH

5-OMe
Cl
5-Et
C≡CH
5,7-di-Cl
C≡CH

6-OMe
Cl
6-Et
C≡CH
5,7-di-Br
C≡CH

7-OMe
Cl
7-Et
C≡CH
—
SMe

5-CN
Cl
5-Pr
C≡CH
5-Me
SMe

6-CN
Cl
6-Pr
C≡CH
6-Me
SMe

7-CN
Cl
7-Pr
C≡CH
7-Me
SMe

5-CF₃
Cl
5-OMe
C≡CH
5-Et
SMe

6-CF₃
Cl
6-OMe
C≡CH
6-Et
SMe

7-CF₃
Cl
7-OMe
C≡CH
7-Et
SMe

5-F
Cl
5-CN
C≡CH
5-Pr
SMe

6-F
Cl
6-CN
C≡CH
6-Pr
SMe

7-F
Cl
7-CN
C≡CH
7-Pr
SMe

5-Cl
Cl
5-CF₃
C≡CH
5-OMe
SMe

6-Cl
Cl
6-CF₃
C≡CH
6-OMe
SMe

7-Cl
Cl
7-CF₃
C≡CH
7-OMe
SMe

5-Br
Cl
5-F
C≡CH
5-CN
SMe

6-Br
Cl
6-F
C≡CH
6-CN
SMe

7-Br
Cl
7-F
C≡CH
7-CN
SMe

5OCHF₂
Cl
5-Cl
C≡CH
5-CF₃
SMe

6-CF₃
SMe
6-Br
SMe
5-F, 7-Me
SMe

7-CF₃
SMe
7-Br
SMe
5-Me, 7-F
SMe

5-F
SMe
5-OCHF₂
SMe
5-Me, 7-Cl
SMe

6-F
SMe
6-OCHF₂
SMe
5-Me, 7-CN
SMe

7-F
SMe
7-OCHF₂
SMe
5-Me, 7-OMe
SMe

5-Cl
SMe
6,7-di-Me
SMe
5,7-di-F
SMe

6-Cl
SMe
5,7-di-Me
SMe
5,7-di-Cl
SMe

7-Cl
SMe
5-Cl, 7-Me
SMe
5,7-di-Br
SMe

5-Br
SMe
5-Cl, 7-OMe
SMe

Table 2 is constructed in the same manner as Table 1 except that the Row Heading “W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is H and” is replaced with the Row Heading listed for Table 2 below (i.e. “W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, and L-G is C(O)Et.”). Therefore the first entry in Table 2 is a compound of Formula 1 wherein W is —CH₂—, R¹is Me, R²is Me, (R³)_nis “-” (i.e. n is 0; no substitution with R³), R⁵is H, R⁶is H, and L-G is C(O)Et. Tables 3 through 959 are constructed similarly.

Table
Row Heading

2
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

3
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

4
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

5
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

6
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

7
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

8
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

9
W is —CH₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

10
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is H, and

11
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

12
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

13
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

14
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

15
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

16
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

17
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

18
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

19
W is —CH₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

20
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

21
W is —CH₂—, R¹is Me, R²is CF_3,R⁵is H, R⁶is H, L-G is C(O)Me, and

22
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

23
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

24
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

25
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

26
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

27
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

28
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

29
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

30
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

31
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

32
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

33
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

34
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

35
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

36
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

37
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

38
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

39
W is —CH₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

40
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is H, and

41
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

42
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

43
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

44
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

45
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

46
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

47
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

48
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

49
W is —CH₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

50
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is H, and

51
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

52
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

53
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

54
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

55
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

56
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

57
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

58
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

59
W is —CH₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

60
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

61
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

62
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

63
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

64
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

65
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

66
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

67
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

68
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

69
W is —CH₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

70
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is H, and

71
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

72
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

73
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

74
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

75
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

76
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

77
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

78
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

79
W is —CH₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

80
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is H, and

81
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

82
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

83
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

84
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

85
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

86
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

87
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

88
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

89
W is —CH₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

90
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is H, and

91
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

92
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

93
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

94
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

95
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

96
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

97
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

98
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

99
W is —CH₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

100
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

101
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

102
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

103
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

104
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

105
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

106
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

107
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

108
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

109
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

110
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

111
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

112
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

113
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

114
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

115
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

116
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

117
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

118
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

119
W is —CH₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

120
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is H, and

121
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

122
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

123
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

124
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

125
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

126
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

127
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

128
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

129
W is —CH₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

130
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is H, and

131
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

132
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

133
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

134
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

135
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

136
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

137
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

138
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

139
W is —CH₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

140
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

141
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

142
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

143
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

144
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

145
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

146
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

147
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

148
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

149
W is —CH₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

150
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is H, and

151
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

152
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

153
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

154
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

155
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

156
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

157
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

158
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

159
W is —CH₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

160
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is H, and

161
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

162
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

163
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

164
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

165
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

166
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

167
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

168
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

169
W is —C(CH₃)₂—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

170
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is H, and

171
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

172
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

173
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

174
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

175
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

176
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

177
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

178
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

179
W is —C(CH₃)₂—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

180
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

181
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

182
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

183
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

184
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

185
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

186
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

187
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

188
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

189
W is —C(CH₃)₂—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

190
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

191
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

192
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

193
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

194
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

195
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

196
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

197
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

198
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

199
W is —C(CH₃)₂—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

200
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is H, and

201
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

202
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

203
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

204
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

205
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

206
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

207
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

208
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

209
W is —C(CH₃)₂—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

210
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is H, and

211
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

212
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

213
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

214
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

215
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

216
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

217
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

218
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

219
W is —C(CH₃)₂—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

220
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

221
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

222
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

223
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

224
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

225
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

226
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

227
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

228
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

229
W is —C(CH₃)₂—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

230
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is H, and

231
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

232
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

233
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

234
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

235
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

236
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

237
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

238
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

239
W is —C(CH₃)₂—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

240
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is H, and

241
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

242
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

243
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

244
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

245
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

246
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

247
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

248
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

249
W is —C(CH₃)₂—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

250
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is H, and

251
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

252
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

253
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

254
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

255
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

256
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

257
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

258
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

259
W is —C(CH₃)₂—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

260
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

261
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

262
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

263
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

264
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

265
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

266
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

267
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

268
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

269
W is —C(CH₃)₂—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

270
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

271
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

272
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

273
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

274
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

275
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

276
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

277
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

278
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

279
W is —C(CH₃)₂—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

280
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is H, and

281
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

282
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

283
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

284
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

285
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

286
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

287
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

288
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

289
W is —C(CH₃)₂—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

290
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is H, and

291
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

292
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

293
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

294
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

295
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

296
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

297
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

298
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

299
W is —C(CH₃)₂—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

300
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

301
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

302
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

303
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

304
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

305
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

306
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

307
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

308
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

309
W is —C(CH₃)₂—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

310
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is H, and

311
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

312
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

313
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

314
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

315
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

316
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

317
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

318
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

319
W is —C(CH₃)₂—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

320
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is H, and

321
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

322
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

323
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

324
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

325
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

326
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

327
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

328
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

329
W is —O—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

330
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is H, and

331
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

332
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

333
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

334
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

335
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

336
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

337
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

338
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

339
W is —O—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

340
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is H

341
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

342
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

343
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

344
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

345
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

346
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

347
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

348
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

349
W is —O—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

350
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

351
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

352
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

353
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

354
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

355
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

356
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

357
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

358
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

359
W is —O—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

360
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is H, and

361
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

362
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

363
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

364
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

365
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

366
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

367
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

368
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

369
W is —O—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

370
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is H, and

371
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

372
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

373
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

374
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

375
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

376
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

377
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

378
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

379
W is —O—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

380
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

381
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

382
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

383
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

384
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

385
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

386
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

387
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

388
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

389
W is —O—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

390
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is H, and

391
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

392
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

393
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

394
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

395
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

396
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

397
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

398
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

399
W is —O—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

400
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is H, and

401
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

402
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

403
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

404
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

405
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

406
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

407
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

408
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

409
W is —O—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

410
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is H, and

411
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

412
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

413
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

414
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

415
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

416
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

417
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

418
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

419
W is —O—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

420
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

421
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

422
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

423
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

424
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

425
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

426
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

427
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

428
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

429
W is —O—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

430
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

431
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

432
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

433
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

434
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

435
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

436
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

437
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

438
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

439
W is —O—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

440
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is H, and

441
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

442
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

443
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

444
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

445
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

446
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

447
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

448
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

449
W is —O—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

450
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is H, and

451
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

452
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

453
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

454
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

455
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

456
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

457
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

458
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

459
W is —O—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

460
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

461
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

462
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

463
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

464
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

465
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

466
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

467
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

468
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

469
W is —O—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

470
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is H, and

471
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

472
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

473
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

474
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

475
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

476
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

477
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

478
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

479
W is —O—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

480
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is H, and

481
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

482
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

483
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

484
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

485
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

486
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

487
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

488
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

489
W is —CH(CH₃)—, R¹is Me, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

490
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is H, and

491
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

492
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

493
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

494
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

495
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

496
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

497
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

498
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

499
W is —CH(CH₃)—, R¹is Me, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

500
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

501
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

502
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

503
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

504
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

505
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

506
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

507
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

508
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

509
W is —CH(CH₃)—, R¹is Me, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

510
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

511
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

512
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

513
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

514
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

515
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

516
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

517
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

518
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

519
W is —CH(CH₃)—, R¹is Me, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

520
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is H, and

521
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

522
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

523
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

524
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

525
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

526
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

527
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

528
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

529
W is —CH(CH₃)—, R¹is Me, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

530
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is H, and

531
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

532
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

533
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

534
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

535
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

536
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

537
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

538
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

539
W is —CH(CH₃)—, R¹is Me, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

540
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

541
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

542
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

543
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

544
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

545
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

546
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

547
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

548
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

549
W is —CH(CH₃)—, R¹is Me, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

550
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is H, and

551
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

552
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

553
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

554
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

555
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

556
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

557
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

558
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

559
W is —CH(CH₃)—, R¹is Me, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

560
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is H, and

561
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Me, and

562
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)Et, and

563
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

564
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

565
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Me, and

566
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂Et, and

567
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

568
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

569
W is —CH(CH₃)—, R¹is Et, R²is Me, R⁵is H, R⁶is H, L-G is SO₂Me, and

570
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is H, and

571
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Me, and

572
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)Et, and

573
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

574
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

575
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Me, and

576
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂Et, and

577
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

578
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

579
W is —CH(CH₃)—, R¹is Et, R²is H, R⁵is H, R⁶is H, L-G is SO₂Me, and

580
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is H, and

581
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Me, and

582
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)Et, and

583
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

584
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

585
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Me, and

586
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂Et, and

587
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

588
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

589
W is —CH(CH₃)—, R¹is Et, R²is CF₃, R⁵is H, R⁶is H, L-G is SO₂Me, and

590
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is H, and

591
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Me, and

592
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)Et, and

593
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

594
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

595
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Me, and

596
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂Et, and

597
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

598
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

599
W is —CH(CH₃)—, R¹is Et, R²is Cl, R⁵is H, R⁶is H, L-G is SO₂Me, and

600
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is H, and

601
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Me, and

602
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)Et, and

603
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

604
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

605
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Me, and

606
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂Et, and

607
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

608
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

609
W is —CH(CH₃)—, R¹is Et, R²is Br, R⁵is H, R⁶is H, L-G is SO₂Me, and

610
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is H, and

611
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Me, and

612
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)Et, and

613
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

614
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

615
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Me, and

616
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂Et, and

617
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

618
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

619
W is —CH(CH₃)—, R¹is Et, R²is I, R⁵is H, R⁶is H, L-G is SO₂Me, and

620
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is H, and

621
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Me, and

622
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)Et, and

623
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

624
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

625
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Me, and

626
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂Et, and

627
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

628
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

629
W is —CH(CH₃)—, R¹is Et, R²is OMe, R⁵is H, R⁶is H, L-G is SO₂Me, and

630
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is H, and

631
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Me, and

632
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)Et, and

633
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—i-Pr, and

634
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is C(O)—t-Bu, and

635
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Me, and

636
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂Et, and

637
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—i-Pr, and

638
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is CO₂—t-Bu, and

639
W is —CH(CH₃)—, R¹is Et, R²is CN, R⁵is H, R⁶is H, L-G is SO₂Me, and

640
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is H, and

641
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

642
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

643
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

644
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

645
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

646
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

647
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

648
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

649
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

650
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is H, and

651
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

652
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

653
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

654
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

655
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

656
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

657
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

658
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

659
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

660
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is H, and

661
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

662
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

663
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

664
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

665
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

666
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

667
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

668
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

669
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

670
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is H, and

671
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

672
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

673
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

674
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

675
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

676
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

677
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

678
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

679
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

680
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is H, and

681
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

682
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

683
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

684
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

685
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

686
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

687
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

688
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

689
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

690
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is H, and

691
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

692
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

693
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

694
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

695
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

696
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

697
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

698
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

699
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

700
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is H, and

701
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

702
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

703
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

704
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

705
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

706
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

707
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

708
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

709
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

710
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is H, and

711
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

712
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

713
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

714
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

715
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

716
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

717
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

718
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

719
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

720
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is H, and

721
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

722
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

723
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

724
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

725
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

726
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

727
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

728
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

729
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

730
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is H, and

731
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

732
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

733
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

734
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

735
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

736
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

737
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

738
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

739
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

740
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is H, and

741
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

742
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

743
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

744
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

745
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

746
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

747
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

748
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

749
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

750
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is H, and

751
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

752
W is —CH₂—, R¹is Et, R²is Cl, R5 is CH₃, R⁶is H, L-G is C(O)Et, and

753
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

754
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

755
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

756
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

757
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

758
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

759
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

760
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is H, and

761
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

762
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

763
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

764
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

765
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

766
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

767
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

768
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

769
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

770
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is H, and

771
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

772
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

773
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

774
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

775
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

776
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

777
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

778
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

779
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

780
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is H, and

781
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

782
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

783
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

784
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

785
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

786
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

787
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

788
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

789
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

790
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is H, and

791
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)Me, and

792
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)Et, and

793
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)—i-Pr, and

794
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is C(O)—t-Bu, and

795
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂Me, and

796
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂Et, and

797
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂—i-Pr, and

798
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is CO₂—t-Bu, and

799
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶is H, L-G is SO₂Me, and

800
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is H, and

801
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

802
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

803
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

804
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

805
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

806
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

807
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

808
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

809
W is —CH₂—, R¹is Me, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

810
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is H, and

811
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

812
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

813
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

814
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

815
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

816
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

817
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

818
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

819
W is —CH₂—, R¹is Me, R²is H, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

820
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is H, and

821
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

822
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

823
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

824
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

825
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

826
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

827
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

828
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

829
W is —CH₂—, R¹is Me, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

830
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is H, and

831
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

832
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

833
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

834
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

835
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

836
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

837
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

838
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

839
W is —CH₂—, R¹is Me, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

840
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is H, and

841
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

842
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

843
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

844
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

845
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

846
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

847
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

848
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

849
W is —CH₂—, R¹is Me, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

850
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is H, and

851
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

852
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

853
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

854
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

855
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

856
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

857
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

858
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

859
W is —CH₂—, R¹is Me, R²is I, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

860
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is H, and

861
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

862
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

863
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

864
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

865
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

866
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

867
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

868
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

869
W is —CH₂—, R¹is Me, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

870
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is H, and

871
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

872
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

873
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

874
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

875
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

876
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

877
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

878
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

879
W is —CH₂—, R¹is Me, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

880
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is H, and

881
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

882
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

883
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

884
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

885
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

886
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

887
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

888
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

889
W is —CH₂—, R¹is Et, R²is Me, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

890
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is H, and

891
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

892
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

893
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

894
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

895
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

896
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

897
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

898
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

899
W is —CH₂—, R¹is Et, R²is H, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

900
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is H, and

901
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

902
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

903
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

904
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

905
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

906
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

907
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

908
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

909
W is —CH₂—, R¹is Et, R²is CF₃, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

910
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is H, and

911
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

912
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

913
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

914
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

915
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

916
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

917
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

918
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

919
W is —CH₂—, R¹is Et, R²is Cl, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

920
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is H, and

921
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

922
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

923
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

924
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

925
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

926
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

927
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

928
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

929
W is —CH₂—, R¹is Et, R²is Br, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

930
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is H, and

931
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

932
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

933
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

934
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

935
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

936
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

937
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

938
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

939
W is —CH₂—, R¹is Et, R²is I, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

940
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is H, and

941
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

942
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

943
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

944
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

945
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

946
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

947
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

948
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

949
W is —CH₂—, R¹is Et, R²is OMe, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

950
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is H, and

951
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)Me, and

952
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)Et, and

953
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)—i-Pr, and

954
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is C(O)—t-Bu, and

955
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂Me, and

956
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂Et, and

957
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂—i-Pr, and

958
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is CO₂—t-Bu, and

959
W is —CH₂—, R¹is Et, R²is CN, R⁵is CH₃, R⁶CH₃, L-G is SO₂Me, and

A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

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.

Weight 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, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C₆-C₂₂), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

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 petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate 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. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 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, Dec. 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. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 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. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 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. Pat. No. 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, U K, 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 Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.

EXAMPLE A

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 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%

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%

The present disclosure also includes Examples A through I above except “Compound 1” is replaced with “Compound 2” and “Compound 3”. “Compound 4”, “Compound 5”, “Compound 6”, Compound 7” or “Compound 8” above as described in Index Table A. 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 invention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.

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. Undesired vegetation includes at least one selected from the group consisting of grass weeds and broadleaf weeds. Undesired vegetation is selected from the group consisting of annual bluegrass (Poa annua), Benghal dayflower, blackgrass (Alopecurus myosuroides), black nightshade (eastern black nightshade, Solanum ptycanthum), broadleaf signalgrass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum or Xanthium strumarium), corn poppies, field violet (Viola arvensis), goosegrass (Eleusine indica), guinea grass, hairy beggarticks (Bidens pilosa), herbicide-resistant blackgrass, horseweed, Italian rye grass, jimsonweed, Johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), little seed canary grass, morning glory, Pennsylvania smartweed, ladysthumb smartweed (Polygonum Persicaria), pitted morning glory, prickly sida, quackgrass, redroot pigweed, palmer pigweed (Amaranthus palmeri), shattercane, shepherd's purse, windgrass, silky windgrass (Apera spica-venti), sunflower (Helianthus annuus, as a weed in a potato crop), wild buckwheat (Polygonum convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), wild pointsettia, yellow foxtail, yellow nutsedge (Cyperus esculentus), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), common waterhemp (Amaranthus rudis), surinam grass (Brachiaria decumbens), downy bromegrass (Bromus tectorum), woolly cupgrass (Eriochloa villosa), bermudagrass (Cynodon dactylon), Russian thistle (Salsola kali), velvetleaf (Abutilon theophrasti), common chickweed (Stellaria media), henbit deadnettle (Lamium amplexicaule), littleseed canarygrass (Phalaris minor), field poppy (Papaver rhoeas), scentless chamomile (Matricaria inodora), bird's-eye speedwell (Veronica persica), wild radish (Raphanus raphanistrum), wild poinsettia (Euphorbia heterophylla), Brazilian crabgrass (Digitaria horizontalis), fall panicum (Panicum dichotomiflorum), southern sandbur (Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), Virginia dayflower (Commelina virginica), field bindweed (Convolvulus arvensis), monochoria (Monochoria vaginalis), hardstem bulrush (Scirpus juncoides), purple redstem (Ammannia coccinea), bearded sprangletop (Leptochloa fascicularis), common waterplantain (Alisma plantago-aquatica), and late watergrass (Echinochloa oryzicola).

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 methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

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 (enhanced) 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 following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, S-beflubutamide, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, 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, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron, vernolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 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, 7-(3,5-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 and 2-methyl-N-(4-methyl-1,2,55-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. 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.

Preferred for better control of undesired vegetation (e.g., lower use rate such as from greater-than-additive effects, 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 atrazine, azimsulfuron, beflubutamid, S-beflubutamide, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, ethametsulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-i 1,2,4-triazine-3,5-(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, pethoxamid, picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl and tribenuron-methyl.

Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-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 or (enhanced)) 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 (enhancement) 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 least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.

Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 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, and 3-oxo-1-cyclohexen-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide 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 can 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.

TABLE A1

Component (a)

Typical
More Typical
Most Typical

(Compound #)
Component (b)
Weight Ratio
Weight Ratio
Weight Ratio

1
2,4-D
1:192-6:1
1:64-2:1
1:24-1:3

1
Acetochlor
1:768-2:1
1:256-1:2
1:96-1:11

1
Acifluorfen
1:96-12:1
1:32-4:1
1:12-1:2

1
Aclonifen
1:857-2:1
1:285-1:3
1:107-1:12

1
Alachlor
1:768-2:1
1:256-1:2
1:96-1:11

1
Ametryn
1:384-3:1
1:128-1:1
1:48-1:6

1
Amicarbazone
1:192-6:1
1:64-2:1
1:24-1:3

1
Amidosulfuron
1:6-168:1
1:2-56:1
1:1-11:1

1
Aminocyclopyrachlor
1:48-24:1
1:16-8:1
1:6-2:1

1
Aminopyralid
1:20-56:1
1:6-19:1
1:2-4:1

1
Amitrole
1:768-2:1
1:256-1:2
1:96-1:11

1
Anilofos
1:96-12:1
1:32-4:1
1:12-1:2

1
Asulam
1:960-2:1
1:320-1:3
1:120-1:14

1
Atrazine
1:192-6:1
1:64-2:1
1:24-1:3

1
Azimsulfuron
1:6-168:1
1:2-56:1
1:1-11:1

1
Beflubutamid
1:342-4:1
1:114-2:1
1:42-1:5

1
S-Beflubutamid
1:171-4:0.5
1:57-2:0.5
1:21-1:2.5

1
Benfuresate
1:617-2:1
1:205-1:2
1:77-1:9

1
Bensulfuron-methyl
1:25-45:1
1:8-15:1
1:3-3:1

1
Bentazone
1:192-6:1
1:64-2:1
1:24-1:3

1
Benzobicyclon
1:85-14:1
1:28-5:1
1:10-1:2

1
Benzofenap
1:257-5:1
1:85-2:1
1:32-1:4

1
Bicyclopyrone
1:42-27:1
1:14-9:1
1:5-2:1

1
Bifenox
1:257-5:1
1:85-2:1
1:32-1:4

1
Bispyribac-sodium
1:10-112:1
1:3-38:1
1:1-7:1

1
Bromacil
1:384-3:1
1:128-1:1
1:48-1:6

1
Bromobutide
1:384-3:1
1:128-1:1
1:48-1:6

1
Bromoxynil
1:96-12:1
1:32-4:1
1:12-1:2

1
Butachlor
1:768-2:1
1:256-1:2
1:96-1:11

1
Butafenacil
1:42-27:1
1:14-9:1
1:5-2:1

1
Butylate
1:1542-1:2
1:514-1:5
1:192-1:22

1
Carfenstrole
1:192-6:1
1:64-2:1
1:24-1:3

1
Carfentrazone-ethyl
1:128-9:1
1:42-3:1
1:16-1:2

1
Chlorimuron-ethyl
1:8-135:1
1:2-45:1
1:1-9:1

1
Chlorotoluron
1:768-2:1
1:256-1:2
1:96-1:11

1
Chlorsulfuron
1:6-168:1
1:2-56:1
1:1-11:1

1
Cincosulfuron
1:17-68:1
1:5-23:1
1:2-5:1

1
Cinidon-ethyl
1:384-3:1
1:128-1:1
1:48-1:6

1
Cinmethylin
1:34-34:1
1:11-12:1
1:4-3:1

1
Clacyfos
1:34-34:1
1:11-12:1
1:4-3:1

1
Clethodim
1:48-24:1
1:16-8:1
1:6-2:1

1
Clodinafop-propargyl
1:20-56:1
1:6-19:1
1:2-4:1

1
Clomazone
1:384-3:1
1:128-1:1
1:48-1:6

1
Clomeprop
1:171-7:1
1:57-3:1
1:21-1:3

1
Clopyralid
1:192-6:1
1:64-2:1
1:24-1:3

1
Cloransulam-methyl
1:12-96:1
1:4-32:1
1:1-6:1

1
Cumyluron
1:384-3:1
1:128-1:1
1:48-1:6

1
Cyanazine
1:384-3:1
1:128-1:1
1:48-1:6

1
Cyclopyrimorate
1:17-68:1
1:5-23:1
1:2-5:1

1
Cyclosulfamuron
1:17-68:1
1:5-23:1
1:2-5:1

1
Cycloxydim
1:96-12:1
1:32-4:1
1:12-1:2

1
Cyhalofop
1:25-45:1
1:8-15:1
1:3-3:1

1
Daimuron
1:192-6:1
1:64-2:1
1:24-1:3

1
Desmedipham
1:322-4:1
1:107-2:1
1:40-1:5

1
Dicamba
1:192-6:1
1:64-2:1
1:24-1:3

1
Dichlobenil
1:1371-1:2
1:457-1:4
1:171-1:20

1
Dichlorprop
1:925-2:1
1:308-1:3
1:115-1:13

1
Diclofop-methyl
1:384-3:1
1:128-1:1
1:48-1:6

1
Diclosulam
1:10-112:1
1:3-38:1
1:1-7:1

1
Difenzoquat
1:288-4:1
1:96-2:1
1:36-1:4

1
Diflufenican
1:857-2:1
1:285-1:3
1:107-1:12

1
Diflufenzopyr
1:12-96:1
1:4-32:1
1:1-6:1

1
Dimethachlor
1:768-2:1
1:256-1:2
1:96-1:11

1
Dimethametryn
1:192-6:1
1:64-2:1
1:24-1:3

1
Dimethenamid-P
1:384-3:1
1:128-1:1
1:48-1:6

1
Dithiopyr
1:192-6:1
1:64-2:1
1:24-1:3

1
Diuron
1:384-3:1
1:128-1:1
1:48-1:6

1
EPTC
1:768-2:1
1:256-1:2
1:96-1:11

1
Esprocarb
1:1371-1:2
1:457-1:4
1:171-1:20

1
Ethalfluralin
1:384-3:1
1:128-1:1
1:48-1:6

1
Ethametsulfuron-methyl
1:17-68:1
1:5-23:1
1:2-5:1

1
Ethoxyfen
1:8-135:1
1:2-45:1
1:1-9:1

1
Ethoxysulfuron
1:20-56:1
1:6-19:1
1:2-4:1

1
Etobenzanid
1:257-5:1
1:85-2:1
1:32-1:4

1
Fenoxaprop-ethyl
1:120-10:1
1:40-4:1
1:15-1:2

1
Fenoxasulfone
1:85-14:1
1:28-5:1
1:10-1:2

1
Fenquinotrione
1:17-68:1
1:5-23:1
1:2-5:1

1
Fentrazamide
1:17-68:1
1:5-23:1
1:2-5:1

1
Flazasulfuron
1:17-68:1
1:5-23:1
1:2-5:1

1
Florasulam
1:2-420:1
1:1-140:1
2:1-27:1

1
Fluazifop-butyl
1:192-6:1
1:64-2:1
1:24-1:3

1
Flucarbazone
1:8-135:1
1:2-45:1
1:1-9:1

1
Flucetosulfuron
1:8-135:1
1:2-45:1
1:1-9:1

1
Flufenacet
1:257-5:1
1:85-2:1
1:32-1:4

1
Flumetsulam
1:24-48:1
1:8-16:1
1:3-3:1

1
Flumiclorac-pentyl
1:10-112:1
1:3-38:1
1:1-7:1

1
Flumioxazin
1:25-45:1
1:8-15:1
1:3-3:1

1
Fluometuron
1:384-3:1
1:128-1:1
1:48-1:6

1
Flupyrsulfuron-methyl
1:3-336:1
1:1-112:1
2:1-21:1

1
Fluridone
1:384-3:1
1:128-1:1
1:48-1:6

1
Fluroxypyr
1:96-12:1
1:32-4:1
1:12-1:2

1
Flurtamone
1:857-2:1
1:285-1:3
1:107-1:12

1
Fluthiacet-methyl
1:48-42:1
1:16-14:1
1:3-3:1

1
Fomesafen
1:96-12:1
1:32-4:1
1:12-1:2

1
Foramsulfuron
1:13-84:1
1:4-28:1
1:1-6:1

1
Glufosinate
1:288-4:1
1:96-2:1
1:36-1:4

1
Glyphosate
1:288-4:1
1:96-2:1
1:36-1:4

1
Halosulfuron-methyl
1:17-68:1
1:5-23:1
1:2-5:1

1
Halauxifen
1:20-56:1
1:6-19:1
1:2-4:1

1
Halauxifen methyl
1:20-56:1
1:6-19:1
1:2-4:1

1
Haloxyfop-methyl
1:34-34:1
1:11-12:1
1:4-3:1

1
Hexazinone
1:192-6:1
1:64-2:1
1:24-1:3

1
Hydantocidin
1:1100-16:1
1:385-8:1
1:144-4:1

1
Imazamox
1:13-84:1
1:4-28:1
1:1-6:1

1
Imazapic
1:20-56:1
1:6-19:1
1:2-4:1

1
Imazapyr
1:85-14:1
1:28-5:1
1:10-1:2

1
Imazaquin
1:34-34:1
1:11-12:1
1:4-3:1

1
Imazethabenz-methyl
1:171-7:1
1:57-3:1
1:21-1:3

1
Imazethapyr
1:24-48:1
1:8-16:1
1:3-3:1

1
Imazosulfuron
1:27-42:1
1:9-14:1
1:3-3:1

1
Indanofan
1:342-4:1
1:114-2:1
1:42-1:5

1
Indaziflam
1:25-45:1
1:8-15:1
1:3-3:1

1
Iodosulfuron-methyl
1:3-336:1
1:1-112:1
2:1-21:1

1
Ioxynil
1:192-6:1
1:64-2:1
1:24-1:3

1
Ipfencarbazone
1:85-14:1
1:28-5:1
1:10-1:2

1
Isoproturon
1:384-3:1
1:128-1:1
1:48-1:6

1
Isoxaben
1:288-4:1
1:96-2:1
1:36-1:4

1
Isoxaflutole
1:60-20:1
1:20-7:1
1:7-2:1

1
Lactofen
1:42-27:1
1:14-9:1
1:5-2:1

1
Lenacil
1:384-3:1
1:128-1:1
1:48-1:6

1
Linuron
1:384-3:1
1:128-1:1
1:48-1:6

1
MCPA
1:192-6:1
1:64-2:1
1:24-1:3

1
MCPB
1:288-4:1
1:96-2:1
1:36-1:4

1
Mecoprop
1:768-2:1
1:256-1:2
1:96-1:11

1
Mefenacet
1:384-3:1
1:128-1:1
1:48-1:6

1
Mefluidide
1:192-6:1
1:64-2:1
1:24-1:3

1
Mesosulfuron-methyl
1:5-224:1
1:1-75:1
1:1-14:1

1
Mesotrione
1:42-27:1
1:14-9:1
1:5-2:1

1
Metamifop
1:42-27:1
1:14-9:1
1:5-2:1

1
Metazachlor
1:384-3:1
1:128-1:1
1:48-1:6

1
Metazosulfuron
1:25-45:1
1:8-15:1
1:3-3:1

1
Methabenzthiazuron
1:768-2:1
1:256-1:2
1:96-1:11

1
Metolachlor
1:768-2:1
1:256-1:2
1:96-1:11

1
Metosulam
1:8-135:1
1:2-45:1
1:1-9:1

1
Metribuzin
1:192-6:1
1:64-2:1
1:24-1:3

1
Metsulfuron-methyl
1:2-560:1
1:1-187:1
3:1-35:1

1
Molinate
1:1028-2:1
1:342-1:3
1:128-1:15

1
Napropamide
1:384-3:1
1:128-1:1
1:48-1:6

1
Napropamide-M
1:192-6:1
1:64-2:1
1:24-1:3

1
Naptalam
1:192-6:1
1:64-2:1
1:24-1:3

1
Nicosulfuron
1:12-96:1
1:4-32:1
1:1-6:1

1
Norflurazon
1:1152-1:1
1:384-1:3
1:144-1:16

1
Orbencarb
1:1371-1:2
1:457-1:4
1:171-1:20

1
Orthosulfamuron
1:20-56:1
1:6-19:1
1:2-4:1

1
Oryzalin
1:514-3:1
1:171-1:2
1:64-1:8

1
Oxadiargyl
1:384-3:1
1:128-1:1
1:48-1:6

1
Oxadiazon
1:548-3:1
1:182-1:2
1:68-1:8

1
Oxasulfuron
1:27-42:1
1:9-14:1
1:3-3:1

1
Oxaziclomefone
1:42-27:1
1:14-9:1
1:5-2:1

1
Oxyfluorfen
1:384-3:1
1:128-1:1
1:48-1:6

1
Paraquat
1:192-6:1
1:64-2:1
1:24-1:3

1
Pendimethalin
1:384-3:1
1:128-1:1
1:48-1:6

1
Penoxsulam
1:10-112:1
1:3-38:1
1:1-7:1

1
Penthoxamid
1:384-3:1
1:128-1:1
1:48-1:6

1
Pentoxazone
1:102-12:1
1:34-4:1
1:12-1:2

1
Phenmedipham
1:102-12:1
1:34-4:1
1:12-1:2

1
Picloram
1:96-12:1
1:32-4:1
1:12-1:2

1
Picolinafen
1:34-34:1
1:11-12:1
1:4-3:1

1
Pinoxaden
1:25-45:1
1:8-15:1
1:3-3:1

1
Pretilachlor
1:192-6:1
1:64-2:1
1:24-1:3

1
Primisulfuron-methyl
1:8-135:1
1:2-45:1
1:1-9:1

1
Prodiamine
1:384-3:1
1:128-1:1
1:48-1:6

1
Profoxydim
1:42-27:1
1:14-9:1
1:5-2:1

1
Prometryn
1:384-3:1
1:128-1:1
1:48-1:6

1
Propachlor
1:1152-1:1
1:384-1:3
1:144-1:16

1
Propanil
1:384-3:1
1:128-1:1
1:48-1:6

1
Propaquizafop
1:48-24:1
1:16-8:1
1:6-2:1

1
Propoxycarbazone
1:17-68:1
1:5-23:1
1:2-5:1

1
Propyrisulfuron
1:17-68:1
1:5-23:1
1:2-5:1

1
Propyzamide
1:384-3:1
1:128-1:1
1:48-1:6

1
Prosulfocarb
1:1200-1:2
1:400-1:4
1:150-1:17

1
Prosulfuron
1:6-168:1
1:2-56:1
1:1-11:1

1
Pyraclonil
1:42-27:1
1:14-9:1
1:5-2:1

1
Pyraflufen-ethyl
1:5-224:1
1:1-75:1
1:1-14:1

1
Pyrasulfotole
1:13-84:1
1:4-28:1
1:1-6:1

1
Pyrazolynate
1:857-2:1
1:285-1:3
1:107-1:12

1
Pyrazosulfuron-ethyl
1:10-112:1
1:3-38:1
1:1-7:1

1
Pyrazoxyfen
1:5-224:1
1:1-75:1
1:1-14:1

1
Pyribenzoxim
1:10-112:1
1:3-38:1
1:1-7:1

1
Pyributicarb
1:384-3:1
1:128-1:1
1:48-1:6

1
Pyridate
1:288-4:1
1:96-2:1
1:36-1:4

1
Pyriftalid
1:10-112:1
1:3-38:1
1:1-7:1

1
Pyriminobac-methyl
1:20-56:1
1:6-19:1
1:2-4:1

1
Pyrimisulfan
1:17-68:1
1:5-23:1
1:2-5:1

1
Pyrithiobac
1:24-48:1
1:8-16:1
1:3-3:1

1
Pyroxasulfone
1:85-14:1
1:28-5:1
1:10-1:2

1
Pyroxsulam
1:5-224:1
1:1-75:1
1:1-14:1

1
Quinclorac
1:192-6:1
1:64-2:1
1:24-1:3

1
Quizalofop-ethyl
1:42-27:1
1:14-9:1
1:5-2:1

1
Rimsulfuron
1:13-84:1
1:4-28:1
1:1-6:1

1
Saflufenacil
1:25-45:1
1:8-15:1
1:3-3:1

1
Sethoxydim
1:96-12:1
1:32-4:1
1:12-1:2

1
Simazine
1:384-3:1
1:128-1:1
1:48-1:6

1
Sulcotrione
1:120-10:1
1:40-4:1
1:15-1:2

1
Sulfentrazone
1:147-8:1
1:49-3:1
1:18-1:3

1
Sulfometuron-methyl
1:34-34:1
1:11-12:1
1:4-3:1

1
Sulfosulfuron
1:8-135:1
1:2-45:1
1:1-9:1

1
Tebuthiuron
1:384-3:1
1:128-1:1
1:48-1:6

1
Tefuryltrione
1:42-27:1
1:14-9:1
1:5-2:1

1
Tembotrione
1:31-37:1
1:10-13:1
1:3-3:1

1
Tepraloxydim
1:25-45:1
1:8-15:1
1:3-3:1

1
Terbacil
1:288-4:1
1:96-2:1
1:36-1:4

1
Terbuthylazine
1:857-2:1
1:285-1:3
1:107-1:12

1
Terbutryn
1:192-6:1
1:64-2:1
1:24-1:3

1
Thenylchlor
1:85-14:1
1:28-5:1
1:10-1:2

1
Thiazopyr
1:384-3:1
1:128-1:1
1:48-1:6

1
Thiencarbazone
1:3-336:1
1:1-112:1
2:1-21:1

1
Thifensulfuron-methyl
1:5-224:1
1:1-75:1
1:1-14:1

1
Tiafenacil
1:17-68:1
1:5-23:1
1:2-5:1

1
Thiobencarb
1:768-2:1
1:256-1:2
1:96-1:11

1
Tolpyralate
1:31-37:1
1:10-13:1
1:3-3:1

1
Topramzone
1:6-168:1
1:2-56:1
1:1-11:1

1
Tralkoxydim
1:68-17:1
1:22-6:1
1:8-2:1

1
Triafamone
1:2-420:1
1:1-140:1
2:1-27:1

1
Triallate
1:768-2:1
1:256-1:2
1:96-1:11

1
Triasulfuron
1:5-224:1
1:1-75:1
1:1-14:1

1
Triaziflam
1:171-7:1
1:57-3:1
1:21-1:3

1
Tribenuron-methyl
1:3-336:1
1:1-112:1
2:1-21:1

1
Triclopyr
1:192-6:1
1:64-2:1
1:24-1:3

1
Trifloxysulfuron
1:2-420:1
1:1-140:1
2:1-27:1

1
Trifludimoxazin
1:25-45:1
1:8-15:1
1:3-3:1

1
Trifluralin
1:288-4:1
1:96-2:1
1:36-1:4

1
Triflusulfuron-methyl
1:17-68:1
1:5-23:1
1:2-5:1

1
Tritosulfuron
1:13-84:1
1:4-28:1
1:1-6:1

Table A2 is constructed the same as Table A1 above except that entries below the “Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below. Compound 1 in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 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 A7 are constructed similarly.

Table Number
Component (a) Column Entries

A2
Compound 2

A3
Compound 3

A4
Compound 4

A5
Compound 5

A6
Compound 6

A7
Compound 7

A8
Compound 8

Preferred for better control of undesired vegetation (e.g., lower use rate such as from synergism (enhancement), 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 chlorsulfuron, ethametsulfuron, chlorimuron-ethyl, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron-methyl, metsulfuron-methyl, triflusulfuron-methyl, pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, 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 Table A for compound descriptions. The abbreviation Me means methyl. 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. Mass spectra are reported with an estimated precision within ±0.5 Da as the molecular weight of the highest isotopic abundance parent ion (M+1) formed by addition of H⁺(molecular weight of 1) to the molecule observed by using atmospheric pressure chemical ionization (AP+).

INDEX TABLE A

[Image Omitted]

Cmpd. No.
R¹
R²
(R³)n
R⁴
R⁵/R⁶
W
L—G
Mass (AP⁺)

1 (Ex. 1)
CH₃
CH₃
H
CH₃
H/H
—CH₂—
CH₃
297 *

2 (Ex. 2)
CH₃
CH₃
H
CH₃
H/H
—CH₂—
H
283 *

3 (Ex. 3)
CH₃
CH₃
H
CH₃
H/H
—O—
H
285 *

4
CH₃
CH₃
7-CH₃
CH₃
H/H
—CH₂—
H
297

5
CH₃
CH₃
H
CH₃
H/H
—CH₂—
—C(═O)CH₃
325

6
CH₃
CH₃
H
H
H/H
—C(CH₃)₂—
CH₃
311

7
CH₃
CH₃
H
H
H/H
—C(CH₃)₂—
H
297

8
CH₃
Cl
7-CH₃
CH₃
H/H
—CH₂—
H
**

* See Synthesis Example for 1H NMR data.

** M.P. = 204-229° C.

BIOLOGICAL EXAMPLES OF THE INVENTION
Test A

Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), ryegrass, It. (Italian ryegrass, Lolium multiflorum), foxtail, green (green foxtail, Setaria viridis), and pigweed (Amaranthus retroflexus) 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 weed species and also wheat (Triticum aestivum), corn (Zea mays), blackgrass (Alopecurus myosuroides), and galium (catchweed bedstraw, Galium aparine) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 d, 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

1000 g ai/ha
Compound
1000 g ai/ha
Compound

Postemergence
1
Postemergence
1

Barnyardgrass
60
Kochia
20

Blackgrass
70
Pigweed
80

Corn
10
Ragweed
90

Foxtail, Green
60
Ryegrass, Italian
90

Galium
100
Wheat
0

500 g ai/ha
Compounds
500 g ai/ha
Compounds

Postemergence
2
3
6
7
Postemergence
2
3
6
7

Barnyardgrass
20
10
0
30
Kochia
90
90
0
70

Blackgrass
20
10
20
10
Pigweed
90
100
0
90

Corn
10
10
0
10
Ragweed
90
90
20
70

Foxtail, Giant
—
—
0
10
Ryegrass, Italian
100
60
0
80

Foxtail, Green
70
20
—
—
Wheat
0
0
0
0

Galium
100
—
0
70

125 g ai/ha
Compounds
31 g ai/ha
Compounds

Postemergence
2
3
4
5
6
7
8
Postemergence
4
5
8

Barnyardgrass
0
0
10
30
0
10
80
Barnyardgrass
10
20
50

Blackgrass
0
0
0
30
0
10
30
Blackgrass
0
0
20

Corn
10
0
0
20
0
0
20
Corn
0
20
0

Foxtail, Giant
—
—
—
—
0
0
80
Foxtail, Giant
—
—
60

Foxtail, Green
10
0
20
40
—
—
—
Foxtail, Green
10
20
—

Galium
90
—
70
90
0
50
90
Galium
40
90
90

Kochia
80
70
20
80
0
30
50
Kochia
0
70
40

Pigweed
80
80
70
100
0
80
100
Pigweed
50
70
90

Ragweed
80
60
20
80
0
0
100
Ragweed
0
30
80

Ryegrass, It.
60
10
20
80
—
30
80
Ryegrass, It.
0
70
40

Wheat
0
0
0
0
0
0
0
Wheat
0
0
0

1000 g ai/ha
Compound
1000 g ai/ha
Compound

Preemergence
1
Preemergence
1

Barnyardgrass
80
Pigweed
60

Foxtail, Green
70
Ragweed
100

Kochia
70
Ryegrass, It.
100

500 g ai/ha
Compounds
125 g ai/ha
Compounds

Preemergence
2
3
6
7
Preemergence
2
3
4
5
6
7
8

Barnyardgrass
0
0
30
0
Barnyardgrass
0
0
0
0
0
0
60

Foxtail, Giant
—
—
0
0
Foxtail, Giant
—
—
—
—
0
0
70

Foxtail, Green
0
0
—
—
Foxtail, Green
0
0
0
0
—
—
—

Kochia
80
30
40
0
Kochia
0
10
0
10
0
0
10

Pigweed
80
60
0
10
Pigweed
0
10
0
100
0
0
100

Ragweed
90
50
0
0
Ragweed
40
0
0
80
0
0
30

Ryegrass, It.
50
10
0
10
Ryegrass, It.
40
0
0
70
0
0
10

500 g ai/ha
Compounds
125 g ai/ha
Compounds

Preemergence
2
3
7
Preemergence
2
3
4
5
7

Barnyardgrass
0
0
0
Barnyardgrass
0
0
0
0
0

Foxtail, Giant
—
—
0
Foxtail, Giant
—
—
—
—
0

Foxtail, Green
0
0
—
Foxtail, Green
0
0
0
0
—

Kochia
80
30
0
Kochia
0
10
0
10
0

Pigweed
80
60
10
Pigweed
0
10
0
100
0

Ragweed
90
50
0
Ragweed
40
0
0
80
0

Ryegrass, It.
50
10
10
Ryegrass, It.
40
0
0
70
0

31 g ai/ha
Compounds
31 g ai/ha
Compounds

Preemergence
4
5
8
Preemergence
4
5
8

Barnyardgrass
0
20
0
Pigweed
0
20
10

Foxtail, Green
0
0
0
Ragweed
0
20
0

Kochia
0
0
—
Ryegrass, It.
0
40
0

Test B

Plant species in the flooded paddy test selected from rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), ducksalad (Heteranthera limosa), and barnyardgrass (Echinochloa crus-galli) were grown to the 2-leaf stage for testing. At the 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 to 15 d, 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

250 g ai/ha
Compounds

Flood
2
3
4
5
6
7
8

Barnyardgrass
0
0
0
0
0
0
60

Ducksalad
0
0
0
0
0
0
90

Rice
0
0
0
0
0
0
0

Sedge, Umbrella
0
50
0
0
0
0
95