HYDRAZINDERIVATE

Description

FIELD OF THE INVENTION

[0001] This invention relates to intermediates which can be used to prepare certain herbicidal pyridazinones. The invention also relates to methods as defined in claims 9 and 11 involving the intermediates of the invention.BACKGROUND OF THE INVENTION

[0002] The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.SUMMARY OF THE INVENTION

[0003] This invention relates to compounds of Formula 3 as defined in claim 1.

[0004] The compounds of Formula 3 are intermediates which may be used to prepare herbicidal compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof: wherein W is O or S; R 1< is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, benzyl or phenyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S; R 2< is H, halogen, -CN, -CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; X is O, S or NR 5< ; or X is -C(R 6< )=C(R 7< )-, wherein the carbon atom bonded to R 6< is also bonded to the carbon atom bonded to R 4< , and the carbon atom bonded to R 7< is also bonded to the phenyl ring moiety in Formula 1; each R 3< is independently halogen, -CN, nitro, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl; R 4< , R 6< and R 7< are independently H, halogen, nitro, -CN, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl; R 5< is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl; G is G 1< or W 1< G 1< ; G 1< is H, -C(=O)R 8< , -C(=S)R 8< , -CO 2 R 9< , -C(=O)SR 9< , -S(O) 2 R 8< , - CONR 10< R 11< , -S(O) 2 NR 10< R 11< , or P(=O)R 12< ; or C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 1 -C 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring; W 1< is C 1 -C 4 alkanediyl or C 2 -C 4 alkenediyl; R 8< and R 10< are independently C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl, or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 9< is C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocycling ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 11< is H, C 1 -C 7 alkyl, C 2 -C 7 alkenyl, C 2 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 1 -C 7 haloalkyl or C 2 -C 7 alkoxyalkyl; R 12< is C 1 -C 7 alkyl or C 1 -C 7 alkoxy; and n is 0, 1, 2, 3 or 4; provided that when R4 is H, then X is -C(R6)=C(R7)-.

[0005] The invention also provides a method for preparing a compound of Formula 1b from a compound of Formula 3 as defined in claim 9 and a method for preparing a compound of Formula 3 as defined in claim 11.DETAILS OF THE INVENTION

[0006] 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.

[0007] 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.

[0008] 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".

[0009] 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."

[0010] 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).

[0011] 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.

[0012] 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.

[0013] 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.

[0014] As used herein, the term "alkylating" refers reaction in which nucleophile displaces a leaving group such as halide or sulfonate from a carbon-containing radical. Unless otherwise indicated, the term "alkylating" does not limit the carbon-containing radical to alkyl.

[0015] 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.

[0016] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl" denotes alkoxy substitution on alkyl. Examples of "alkoxyalkyl" include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 . "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 CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 . "Cyanoalkyl" denotes an alkyl group substituted with one cyano group. Examples of "cyanoalkyl" include NCCH 2 and NCCH 2 CH 2 (alternatively identified as CH 2 CH 2 CN).

[0017] "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.

[0018] 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 F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 . The terms "haloalkoxy", "haloalkylthio", "haloalkenyl", "haloalkynyl", and the like, are defined analogously to the term "haloalkyl". Examples of "haloalkoxy" include CF 3 O-, CCl 3 CH 2 O-, HCF 2 CH 2 CH 2 O- and CF 3 CH 2 O-. Examples of "haloalkylthio" include CCl 3 S-, CF 3 S-, CCl 3 CH 2 S- and ClCH 2 CH 2 CH 2 S-. Examples of "haloalkenyl" include (Cl) 2 C=CHCH 2 - and CF 3 CH 2 CH=CHCH 2 -. Examples of "haloalkynyl" include HC≡CCHCl-, CF 3 C≡C-, CCl 3 C≡C- and FCH 2 C≡CCH 2 -.

[0019] "Alkoxycarbonyl" denotes a straight-chain or branched alkoxy moieties bonded to a C(=O) moiety. Examples of "alkoxycarbonyl" include CH 3 OC(=O)-, CH 3 CH 2 OC(=O)-, CH 3 CH 2 CH 2 OC(=O)-, (CH 3 ) 2 CHOC(=O)- and the different butoxy- or pentoxycarbonyl isomers.

[0020] 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, C 1 -C 4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C 2 alkoxyalkyl designates CH 3 OCH 2 -; C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 )-, CH 3 OCH 2 CH 2 - or CH 3 CH 2 OCH 2 -; and C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 - and CH 3 CH 2 OCH 2 CH 2 -.

[0021] When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R 3< ) n , wherein n is 1, 2, 3 or 4. When a group contains a substituent which can be hydrogen, for example R 2< or R 4< , then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R 3< ) n wherein n may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be "not substituted" or "unsubstituted", then hydrogen atoms are attached to take up any free valency.

[0022] The compounds of Formula 1 wherein G is H (i.e. a hydroxy function) are believed to be the compounds that bind to an active site on a plant enzyme or receptor causing herbicidal effect on the plant. Other compounds of Formula 1 wherein the substituent G is a group that can be transformed within plants or the environment to the hydroxy moiety provide similar herbicidal effects. Therefore, G can be any derivative known in the art which does not extinguish the herbicidal activity of the compound of Formula 1 and is or can be hydrolyzed, oxidized, reduced or otherwise metabolized in plants or soil to provide the carboxylic acid function, which depending upon pH, is in the dissociated or the undissociated form. The term "ring system" denotes two or more fused rings. The term "bicyclic ring system" denotes a ring system consisting of two fused rings.

[0023] 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.

[0024] Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus includes all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include those which are solids such as waxes and gums as well as those which are liquids such as solutions and melts. Crystalline forms include those which represent essentially a single crystal type and those 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.

[0025] 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.

[0026] 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 an enolic function (e.g., when G is H), 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.

[0027] Embodiments, including Embodiments 2-51 below as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments, including Embodiments 2-51 below as well as any other embodiments described herein, and any combination thereof, pertain to the methods of the present invention.

[0028] Embodiments of Formula 1 include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof): Embodiment 2. A compound of Formula 1 wherein X is O, S or -C(R 6< )=C(R 7< )-. Embodiment 3. A compound of Embodiment 2 wherein X is O or S. Embodiment 4. A compound of Embodiment 3 wherein X is O. Embodiment 5. A compound of Embodiment 3 wherein X is S. Embodiment 6. A compound of Embodiment 2 wherein X is -C(R 6< )=C(R 7< )-. Embodiment 7. A compound of Formula 1 wherein X is NR 5< . Embodiment 7a. A compound of Embodiment 2 wherein X is O, S, -CH=CH-, -C(CH 3 )=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH 3 )-. Embodiment 7b. A compound of Embodiment 2 wherein X is -CH=CH-, -C(CH 3 )=CH- , -CH=CF-, -CH=CCl- or -CH=C(CH 3 )-Embodiment 7c. A compound of Embodiment 2 wherein X is -CH=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH 3 )-. Embodiment 7d. A compound of Formula 1 or any one of Embodiments 2 through 7a wherein R 1< is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, benzyl or phenyl. Embodiment 7e. A compound of Formula 1 or any one of Embodiments 2 through 7a wherein R 1< is H, C 1 -C 7 alkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl. Embodiment 8. A compound of Formula 1 or any one of Embodiments 2 through 7 wherein R 1< is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl. Embodiment 9. A compound of Embodiment 8 wherein R 1< is C 1 -C 3 alkyl, allyl, propargyl, CH 2 CH 2 CN, C 1 -C 2 haloalkyl or 2-methoxyethyl. Embodiment 10. A compound of Embodiment 9 wherein R 1< is methyl, ethyl, n-propyl or 2-methoxyethyl. Embodiment 11. A compound of Embodiment 10 wherein R 1< is methyl or ethyl. Embodiment 12. A compound of Embodiment 11 wherein R 1< is methyl. Embodiment 12a. A compound of Formula 1 wherein R 1< is other than H. Embodiment 12b. A compound of Formula 1 wherein R 1< is other than phenyl. Embodiment 12c. A compound of Formula 1 wherein R 2< is H, halogen, -CN, -CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio. Embodiment 12d. A compound of Formula 1 wherein R 2< is H, halogen, -CN, -CHO, C 1 -C 7 alkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy. Embodiment 13. A compound of Formula 1 or any one of Embodiments 2 through 12 wherein R 2< is H, halogen, -CN, C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkoxyalkyl or C 1 -C 3 alkoxy. Embodiment 14. A compound of Embodiment 13 wherein R 2< is H, halogen, C 1 -C 3 alkyl, cyclopropyl, C 1 -C 2 haloalkyl, methoxy or ethoxy. Embodiment 15. A compound of Embodiment 14 wherein R 2< is H, methyl, ethyl, n-propyl, CF 3 or methoxy. Embodiment 16. A compound of Embodiment 15 wherein R 2< is methyl or ethyl. Embodiment 17. A compound of Embodiment 16 wherein R 2< is methyl. Embodiment 17a. A compound of Formula 1 wherein R 2< is other than phenyl. Embodiment 18. A compound of Formula 1 or any one of Embodiments 2 through 17 wherein each R 3< is independently halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio. Embodiment 19. A compound of Embodiment 18 wherein each R 3< is independently halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy. Embodiment 20. A compound of Embodiment 19 wherein each R 3< is independently halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy. Embodiment 21. A compound of Embodiment 20 wherein each R 3< is independently halogen, -CN, methyl, ethyl, methoxy or ethoxy. Embodiment 22. A compound of Embodiment 21 wherein each R 3< is independently F, Cl, Br, methyl, ethyl or methoxy. Embodiment 23. A compound of Formula 1 or any one of Embodiments 2 through 22 wherein R 4< is halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio. Embodiment 24. A compound of Embodiment 23 wherein R 4< is halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy. Embodiment 25. A compound of Embodiment 24 wherein R 4< is halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy. Embodiment 26. A compound of Embodiment 25 wherein R 4< is methyl or ethyl. Embodiment 27. A compound of Embodiment 26 wherein R 4< is methyl. Embodiment 28. A compound of Formula 1 or any one of Embodiments 2 through 27 wherein R 5< is C 1 -C 2 alkyl. Embodiment 29. A compound of Embodiment 28 wherein R 5< is methyl. Embodiment 30. A compound of Formula 1 or any one of Embodiments 2 through 29 wherein independently, R 6< and R 7< are H, halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio. Embodiment 31. A compound of Formula 1 or any one of Embodiments 2 through 30 wherein independently, R 6< and R 7< are H, halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy. Embodiment 32. A compound of Formula 1 or any one of Embodiments 2 through 31 wherein independently, R 6< and R 7< are H, halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy. Embodiment 34a. A compound of Formula 1 or any one of Embodiments 2 through 32 wherein independently, R 6< and R 7< are H, halogen or C 1 -C 2 alkyl. Embodiment 34b. A compound of Formula 1 or any one of Embodiments 2 through 32 wherein independently, R 6< and R 7< are H or halogen. Embodiment 34c. A compound of Formula 1 or any one of Embodiments 2 through 32 wherein R 6< is H and R 7< is halogen. Embodiment 34d. A compound of Formula 1 or any one of Embodiments 2 through 32 wherein R 6< is halogen and R 7< is H. Embodiment 33. A compound of Formula 1 or any one of Embodiments 2 through 32 wherein independently, R 6< and R 7< are H or C 1 -C 2 alkyl. Embodiment 34. A compound of Formula 1 or any one of Embodiments 2 through 33 wherein R 6< is H or methyl (i.e. CH 3 ). Embodiment 35. A compound of Formula 1 or any one of Embodiments 2 through 34 wherein R 7< is H or methyl (i.e. CH 3 ). Embodiment 36. A compound of Embodiment 34 or 35 wherein R 6< is H and R 7< is H, or R 6< is H and R 7< is CH 3 , or R 6< is CH 3 and R 7< is H. Embodiment 37. A compound of Embodiment 36 wherein R 6< is H and R 7< is H. Embodiment 48. A compound of Formula 1 or any one of Embodiments 2 through 47 wherein n is 0, 1, 2 or 3. Embodiment 49. A compound of Embodiment 48 wherein n is 0, 1 or 2. Embodiment 50. A compound of Embodiment 48 wherein n is 1, 2 or 3. Embodiment 51. A compound of Embodiment 49 or 50 wherein n is 1 or 2.

[0029] Combinations of Embodiments 2-51 are illustrated by: Embodiment A. A compound of Formula 1 wherein X is O, S, -CH=CH-, -C(CH 3 )=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH 3 )-; R 1< is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 5 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy, benzyl or phenyl; R 2< is H, halogen, -CN, -CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio; each R 3< is independently halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio; R 4< is halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio; and n is 0, 1, 2 or 3. Embodiment B. A compound of Embodiment A wherein X is -CH=CH-, -C(CH 3 )=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH 3 )-; R 1< is H, C 1 -C 7 alkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 5 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl; R 2< is H, halogen, -CN, -CHO, C 1 -C 7 alkyl, C 1 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy; each R 3< is independently halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy; and R 4< is halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy. Embodiment C. A compound of Embodiment B wherein X is -CH=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH 3 )- R 1< is methyl, ethyl, n-propyl or 2-methoxyethyl; R 2< is H, methyl, ethyl, n-propyl, CF 3 or methoxy; each R 3< is independently halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy; R 4< is halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy; and n is 1 or 2.

[0030] Compounds of Formula 1 can be used for weed control in a variety of crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops. Compounds of Formula 1 are particularly useful for selective control of weeds in cereal crops in the Family Poaceae such as maize, rice and wheat.

[0031] Further Embodiments of Formula 1 are illustrated below (the descriptions of variables in these embodiments pertain to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1): Embodiment PA. A compound of Formula 1 wherein X is O, S, -CH=CH-, -C(CH 3 )=CH- or -CH=C(CH 3 )-; R 1< is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 3 haloalkyl or C 2 -C 4 alkoxyalkyl; R 2< is H, halogen, -CN, C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkoxyalkyl or C 1 -C 3 alkoxy; each R 3< is independently halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio; R 4< is halogen, -CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio; and n is 0, 1, 2 or 3. Embodiment PB. A compound of Embodiment PA wherein R 1< is C 1 -C 3 alkyl, allyl, propargyl, CH 2 CH 2 CN, C 1 -C 2 haloalkyl or 2-methoxyethyl; R 2< is H, halogen, C 1 -C 3 alkyl, cyclopropyl, C 1 -C 2 haloalkyl, methoxy or ethoxy; each R 3< is independently halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy; and R 4< is halogen, -CN, C 1 -C 2 alkyl, -CH=CH 2 , -C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy. Embodiment PC. A compound of Embodiment PB wherein R 1< is methyl, ethyl, n-propyl or 2-methoxyethyl; R 2< is H, methyl, ethyl, n-propyl, CF 3 or methoxy; each R 3< is independently halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy; R 4< is halogen, -CN, methyl, ethyl, -CH=CH 2 , -C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy; and n is 1 or 2.

[0032] The compounds of Formula 1 can be prepared by general methods known in the art of synthetic organic chemistry. 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.

[0033] One or more of the following methods and variations as described in Schemes 1-22 can be used to prepare compounds of Formula 1. The definitions of groups R 1< , R 2< , R 3< , R 4< , W, X and G in the compounds of Formulae 1-24 are as defined above in the Summary of the Invention unless otherwise noted. Formulae 1a, 1b and 1c are subsets of compounds of Formula 1, and all substituents for Formulae 1a-1c are as defined above for Formula 1 unless otherwise noted. Formulae 6a, 6b and 6c are subsets of compounds of Formula 6, and all substituents for Formulae 6a-6c are as defined for Formula 6 unless otherwise noted.

[0034] As shown in Scheme 1, pyridazinones of Formula 1a (a subset of compounds of Formula 1 where W is O, and G is as defined above, but other than hydrogen) can be made by reacting substituted 5-hydroxy-3(2H)-pyridazinones of Formula 1b (i.e. Formula 1 wherein W is O and G is H) with a suitable electrophilic reagent of Formula 2 (i.e. Z 1< -G where Z 1< is a leaving group, alternatively known as a nucleofuge, such as a halogen) in the presence of base in an appropriate solvent. Some examples of reagent classes representing Formula 2 wherein Z 1< is Cl include acid chlorides (G is -(C=O)R 8< ), chloroformates (G is -CO 2 R 9< ), carbamoyl chlorides (G is -CONR 10< R 11< ), sulfonyl chlorides (G is -S(O) 2 R 8< ) and chlorosulfonamides (G is -S(O) 2 NR 10< R 11< ). 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 run under a range of temperatures, with temperatures typically ranging from 0 °C to the reflux temperature of the solvent.

[0035] Substituted 5-hydroxy-3(2H)-pyridazinones of Formula 1b can be prepared as outlined in Scheme 2 by cyclization of hydrazide esters of Formula 3 (where R 30< is alkyl, typically methyl or ethyl) in the presence of base and solvent. Suitable bases for this reaction include but are not limited to potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, potassium t-butoxide or 1,8-diazabicyclo[5.4.0]undec-7-ene. Depending on the specific base used, appropriate solvents can be protic or aprotic and used anhydrous or as aqueous mixtures. Solvents for this cyclization include acetonitrile, methanol, ethanol, tetrahydrofuran, diethyl ether, dioxane, 1,2-dimethoxyethane, dichloromethane or N,N-dimethylformamide. Temperatures for this cyclization generally range from 0 °C to the reflux temperature of the solvent. Literature methods for cyclizing hydrazide ester intermediates of formula CH 3 (CO 2 C 2 H 5 )C=NNCH 3 C(=O)CH 2 Ar (where Ar is a substituted phenyl instead of the bicyclic ring system shown in Formula 3 ) to the corresponding 4-aryl-5-hydroxy-pyridazinones are disclosed in U.S. Patents 8541414 and 8470738. The same conditions reported in these patents are applicable to cyclizing hydrazone esters of Formula 3 to pyridazinones of Formula 1b . The method of Scheme 2 is illustrated by Step F of Synthesis Example 1, Step H of Synthesis Example 2 and Step H of Synthesis Example 3.

[0036] Substituted hydrazide esters of Formula 3 can be prepared as outlined in Scheme 3 by coupling a hydrazone ester of Formula 4 (where R 30< is alkyl, typically methyl or ethyl) with an acid chloride of Formula 5 in the presence of base and solvent. Preferred bases for this reaction are usually tertiary amines such as triethylamine or Hunig's base, but other bases can also be used, including N,N-dimethylaminopyridine, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride or potassium t-butoxide. Depending on the specific base used, appropriate solvents can be protic or aprotic where the reaction takes place under anhydrous conditions or as aqueous mixtures under Schotten-Baumann conditions. Solvents that are used for this acylation on nitrogen include acetonitrile, tetrahydrofuran, diethyl ether, dioxane, toluene, 1,2-dimethoxyethane, dichloromethane or N,N-dimethylformamide. Temperatures for this reaction can range from 0 °C to the reflux temperature of the solvent. Methods to make related hydrazide ester intermediates of formula CH 3 (CO 2 C 2 H 5 )C=NNCH 3 C(=O)Ar (where Ar is a substituted phenyl) have been published in the patent literature, see U.S. Patents 8541414 and 8470738, and U.S. Patent Application Publication 2010 / 0267561. The procedures disclosed in these patent publications are directly applicable to making intermediates useful for preparing the present compounds as depicted in Scheme 3. The method of Scheme 3 is illustrated by Step E of Synthesis Example 1, Step G of Synthesis Example 2 and Step G of Synthesis Example 3.

[0037] Hydrazone esters of Formula 4 are readily accessible by reaction of an appropriately substituted hydrazine of formula R 1< NHNH 2 with a ketone or aldehyde ester of formula R 2< (C=O)CO 2 R 30< (where R 30< is typically methyl or ethyl) in a suitable solvent such as ethanol, methanol, acetonitrile or dioxane or dichloromethane at temperatures generally ranging from 0 to 80°C. U.S. Patent Application Publications 2007 / 0112038 and 2005 / 0256123 disclose procedures for forming the hydrazone from methylhydrazine and the keto ester CH 3 (C=O)CO 2 C 2 H 5 . Preparation of hydrazone esters of Formula 4 is illustrated by Step D of Synthesis Example 1.

[0038] As shown in Scheme 4, bicyclic acetyl chlorides of Formula 5 can be prepared from the corresponding bicyclic acetic acid esters of Formula 6 wherein R 31< is typically methyl or ethyl via ester hydrolysis and acid chloride formation. Standard methods for this transformation are known in the literature. For example, ester hydrolysis can be achieved by heating an alcoholic solution of an ester of Formula 6 with an aqueous solution of an alkali metal hydroxide, following by acidification with a mineral acid. The carboxylic acid of Formula 7 formed can then be converted to the corresponding acyl chloride of Formula 5 by treatment with oxalyl chloride and a catalytic amount of N,N-dimethylformamide in an inert solvent such as dichloromethane. J. Heterocyclic Chem. 1983, 20(6), 1697-1703; J. Med. Chem. 2007, 50(1), 40-64; and PCT Patent Publications WO 2005 / 012291, WO 98 / 49141 and WO 98 / 49158 disclose hydrolysis of benzofuran- and benzothiophene-acetate esters to the corresponding acetic acids. Monatshefte für Chemie 1968, 99(2) 715-720 and patent publications WO 2004046122, WO 2009 / 038974 and JP09077767 disclose conversion of benzofuran- and benzothiophene-acetic acids to the corresponding acid chlorides. The hydrolysis step of Scheme 4 is illustrated by Step C of Synthesis Example 1, Step F of Synthesis Example 2 and Step F of Synthesis Example 3. The acyl chloride formation step of Scheme 4 is illustrated by Step E of Synthesis Example 1, Step G of Synthesis Example 2 and Step G of Synthesis Example 3.

[0039] As shown in Scheme 5, benzofuran acetates of Formula 6a (i.e. Formula 6 wherein X is O) can be made from benzofuran-3-ones of Formula 8 via either a Wittig reaction with a (triphenylphosphoranylidine)acetate of Formula 9 wherein R 31< is typically methyl or ethyl in an inert solvent such as tetrahydrofuran or toluene or by a Wadsworth-Emmons reaction using a phosphonate acetate of Formula 10 wherein R 31< is typically methyl or ethyl in the presence of a base such as sodium hydride or potassium tert-butoxide in a suitable solvent that is generally anhydrous tetrahydrofuran or dioxane. This reaction involves migration of an initially formed exocyclic double bond (formation of a dihydrobenzofuran substituted unsaturated ester) to inside the benzofuran ring system, thereby giving rise to a benzofuran acetate of Formula 6a. Experimental conditions for a Wittig transformation are provided in PCT Patent Publication WO 2008 / 074752. Temperatures typically range from 0 °C to the reflux temperature of the solvent. In some cases, longer heating is required to drive migration of the exocyclic double bond in conjugation with the ester to the endocyclic position within the fully benzofuran ring system. The method of Scheme 5 is illustrated by Step E of Synthesis Example 2 and Step E of Synthesis Example 3.

[0040] As shown in Scheme 6, substituted benzofuran-3-ones of Formula 8 where R 4< is hydrogen or alkyl can be made by first alkylating a salicylate of Formula 11 with an α-bromo ester of Formula 12 (wherein R 32< is typically methyl or ethyl) in the presence of a base such as potassium carbonate or sodium hydride in an appropriate solvent, e.g., acetonitrile, methanol, ethanol, tetrahydrofuran, diethyl ether, 1,2-dimethoxyethane, dioxane or N,N-dimethylformamide, at temperatures ranging from 0 °C to the reflux temperature of the solvent. Next, the bis-ester of Formula 13 is treated with a metal halide or alkoxide, e.g., sodium hydride or potassium tert-butoxide, in an inert solvent such as tetrahydrofuran, dioxane, 1,2-dimethoxyethane or N,N-dimethylformamide to form the corresponding benzofuran-3-one of Formula 8. An alternative more stepwise process for converting diesters of Formula 13 to benzofuran-3-ones of Formula 8 has been reported in PCT Patent Publication WO 2008 / 074752 whereas the method in Scheme 5 allows for cyclization of diesters of Formula 13 followed by ester hydrolysis and decarboxylation to provide benzofuran-3-ones of Formula 8 in one convenient step. The first step of the method of Scheme 6 is illustrated by Step A of Synthesis Example 2.

[0041] As illustrated in Scheme 7, substituted benzothiophenes of Formula 6b (i.e. Formula 6 wherein X is S) where R 4< is hydrogen or alkyl are readily accessible by cyclization of appropriately substituted phenylthio ketoesters of Formula 14, generally under acidic conditions and preferably with polyphosphoric acid (PPA) neat or in an inert generally high boiling solvent, e.g., chlorobenzene, xylene or toluene. Chlorobenzene is usually the solvent of choice and for a literature example of this cyclization using PPA in chlorobenzene, see J. Heterocyclic Chem. 1988, 25, 1271-1272. Also see U.S. Patent 5376677 for published experimental detail for making benzothiophene acetates using this PPA-mediated cyclization. The method of Scheme 7 is illustrated by Step B of Synthesis Example 1.

[0042] As shown in Scheme 8, by methods also taught in J. Heterocyclic Chem. 1988, 25, 1271-1272 and U.S. Patent 5376677, substituted 4-phenylthio-1,3-ketoesters of Formula 14, can be readily made by alkylation of thiophenols of Formula 15 with 4-bromo-1,3-ketoesters of Formula 16 (i.e. R 4< CHBr(C=O)CH 2 CO 2 R where R is generally methyl or ethyl) in the presence of base in solvent. Alkylation with an alkali or alkaline carbonate such as potassium carbonate in a polar aprotic solvent such as acetonitrile or N,N-dimethylformamide is generally preferred. The method of Scheme 8 is illustrated by Step A of Synthesis Example 1.

[0043] As shown in Scheme 9, naphthalene acetic acid esters of Formula 6c (i.e. Formula 6 wherein X is -C(R 6< )=C(R 7< )-) can be prepared from appropriately substituted naphthalene amines of Formula 17. According to this method, amines of Formula 17 are diazotized (preferably with t-butyl nitrite in the presence of cupric chloride in acetonitrile) in the presence of 1,1-dichloroethene (18) to give the corresponding trichloroethylnaphthalenes of Formula 19. The trichloroethylnaphthalenes of Formula 19 are then heated with an appropriate alkali or alkaline earth alkoxide such as a sodium alkoxide of Formula 20, in a suitable solvent such as an alcohol of Formula 21, followed by acidification such as with concentrated sulfuric acid to provide the naphthalene acetic acid esters of Formula 6c. This method is taught in Pest. Manag. Sci. 2011, 67, 1499-1521 and U.S. Patent 5376677.

[0044] An alternative method for making naphthalene acetic acid esters of Formula 6c is outlined in Scheme 10. As taught by the method in Pest. Manag. Sci. 2011, 67, 1499-1521, methyl naphthalenes of Formula 22 can be brominated with N-bromosuccinimide (NBS) under free radical conditions (e.g., benzoyl peroxide as catalyst) in an inert solvent such as dichloromethane, dichloromethane or tetrachloromethane to give naphthalene methyl bromides of Formula 23. Displacement of the bromine with cyanide by reacting compounds of Formula 23 with an alkali or alkaline cyanide (e.g., potassium cyanide) affords the naphthalene acetonitriles of Formula 24 that can be hydrolyzed with esterification to the acetates of Formula 6c by heating in acidic alcohol (e.g., HCl in methanol or ethanol), generally at reflux.

[0045] As shown in Scheme 23, pyridazinones of Formula 1a (a subset of compounds of Formula 1 where W is O) can be thionated to give the corresponding thiones of Formula 1c (i.e. Formula 1 wherein W is S) with a thionation reagent that is generally phosphorus pentasulfide in pyridine or Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide) in an appropriate solvent (e.g., toluene, tetrahydrofuran or dioxane) at temperatures generally ranging 0 °C to room temperature.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] Examples of intermediates useful in the preparation of compounds of this invention or compounds of Formula 1 are shown in Tables I-1a through I-1b. The position(s) of the R 3< group(s) in Tables I-1a through I-3d is(are) based on the locant numbering shown below. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, Pr means propyl, and Ph means phenyl. TABLE I-1a X is S, and R is CO 2 Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, and R is CO2Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, and R is CO2H. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, and R is C(O)Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, and R is CO2Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, and R is CO2Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, and R is CO2H. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, and R is C(O)Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CF-, and R is CO2Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CF-, and R is CO2Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CF-, and R is CO2H. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CF-, and R is C(O)Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt TABLE I-1b X is S, R1 is Me, and R2 is Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Me, and R2 is Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Me, and R2 is Br. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Me, and R2 is I. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Me, and R2 is Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Me, and R2 is OMe. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Et, and R2 is Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Et, and R2 is Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Et, and R2 is Br. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Et, and R2 is I. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Et, and R2 is Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is S, R1 is Et, and R2 is OMe. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Me, and R2 is Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Me, and R2 is Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Me, and R2 is Br. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Me, and R2 is I. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Me, and R2 is Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Me, and R2 is OMe. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Et, and R2 is Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Et, and R2 is Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Et, and R2 is Br. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Et, and R2 is I. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Et, and R2 is Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CH-, R1 is Et, and R2 is OMe. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CCl-, R1 is Et, and R2 is Me. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CCl-, R1 is Et, and R2 is Et. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CCl-, R1 is Et, and R2 is Br. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CCl-, R1 is Et, and R2 is I. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CCl-, R1 is Et, and R2 is Cl. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt X is -CH=CCl-, R1 is Et, and R2 is OMe. (R 3< ) n R 4< (R 3< ) n R 4< (R 3< ) n R 4< -H-Me-Et5-MeH5-MeMe5-MeEt4,6-di-MeH4,6-di-MeMe4,6-di-MeEt5,7-di-MeH5,7-di-MeMe5,7-di-MeEt

[0050] Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting Examples are illustrative of the invention. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1< H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCl 3 solution unless indicated otherwise; "s" means singlet, "d" means doublet, "t" means triplet, "q" means quartet, "m" means multiplet, and "br s" means broad singlet.SYNTHESIS EXAMPLE 1Preparation of 4-(2,5-dimethylbenzo[b]thien-3-yl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 1)Step A: Preparation of ethyl 4-[(4-methylphenyl)thio]-3-oxopentanoate

[0051] To a mixture of potassium carbonate (1.11 g, 8.03 mmol) in N,N-dimethylformamide (DMF) (27 mL) at room temperature under nitrogen (i.e. under a nitrogen atmosphere) was added 4-methylbenzenethiol (0.626 g, 5.04 mmol). The mixture was cooled to 0 °C, and then ethyl 4-bromo-3-oxopentanoate (1.25 g, 5.04 mmol) was added dropwise by syringe over 10 minutes. The mixture was allowed to warm to room temperature while being stirred for 16 h. Then the mixture was poured into aqueous hydrochloric acid (0.2 M, 80 mL) and extracted with diethyl ether (3 × 50 mL). The combined extracts were dried (MgSO 4 ) and concentrated. The crude residue was purified by flash chromatography (gradient of 0 to 10 % of ethyl acetate in hexanes) to yield the title product as a yellow oil (0.82 g).

[0052] 1< H NMR δ 7.27-7.31 (m, 2H), 7.12 (m, 2H), 4.18 (m, 2H), 3.82 (q, 1H), 3.64-3.77 (m, 2H), 2.33 (s, 3H), 1.38 (d, 3H), 1.24-1.30 (m, 3H).Step B: Preparation of ethyl 2,5-dimethylbenzo[b]thiophene-3-acetate

[0053] Polyphosphoric acid (1 mL) was added to chlorobenzene (anhydrous, 20 mL), and the mixture was heated to reflux under nitrogen. To the mixture was added ethyl 4-[(4-methylphenyl)thio]-3-oxopentanoate (i.e. the product of Step A) (0.82 g, 3.08 mmol) dropwise via syringe over about 30 minutes. The mixture was held at reflux for 16 h. The mixture was then cooled to room temperature, and the upper, chlorobenzene layer was decanted to a separate flask and concentrated. The crude residue was purified by flash chromatography (gradient of 0 to 10 % ethyl acetate in hexanes) to yield the title product as a white solid (0.33 g).

[0054] 1< H NMR δ 7.61 (d, 1H), 7.46 (s, 1H), 7.10-7.12 (m, 1H), 4.10-4.17 (m, 2H), 3.74 (s, 2H), 2.53 (s, 3H), 2.46 (s, 3H), 1.22-1.25 (m, 3H).Step C: Preparation of 2,5-dimethylbenzo[b]thiophene-3-acetic acid

[0055] Ethyl 2,5-dimethylbenzo[b]thiophene-3-acetate (i.e. the product of Step B) (0.33 g, 1.33 mmol) was dissolved in methanol (50 mL), and aqueous sodium hydroxide (2 M, 5 mL, 10 mmol) was added. The mixture was heated to reflux for 3 h. The mixture was then cooled, and the solvent was removed by rotary evaporation. To the residue was added water (50 mL), and the pH was brought to ~1 by the careful addition of concentrated hydrochloric acid. The mixture was then extracted with dichloromethane (3 × 50 mL), and the combined organic extracts were dried (MgSO 4 ), filtered and concentrated by rotary evaporation to yield the title product as a white solid (0.26 g).

[0056] 1< H NMR δ 7.62 (d, 1H), 7.43 (s, 1H), 7.11 (m, 1H), 3.78 (s, 2H), 2.53 (s, 3H), 2.46 (s, 3H).Step D: Preparation of methyl 2-(2-methylhydrazinylidene)propanoate

[0057] To a suspension of methyl 2-oxopropanoate (17.0 mL, 169 mmol) and magnesium sulfate (20.46 g, 170 mmol) in trichloromethane (250 mL) chilled to 0 °C was added a solution of methylhydrazine (9.0 mL, 166 mmol) in trichloromethane (50 mL). The reaction mixture was then warmed to room temperature. After stirring for 24 h at room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to give the title product as a yellow solid (21.16 g) that was used directly in the next step without further purification. A portion of this sample was later purified by flash chromatography to provide an off-white solid.

[0058] 1< H NMR δ 5.63 (br s, 1H), 3.82 (s, 3H), 3.22-3.24 (m, 3H), 1.93 (s, 3H).Step E: Preparation of methyl 2-[2-[2-(2,5-dimethylbenzo[b]thien-3yl)acetyl]-2-methylhydrazinylidene]propanoate

[0059] To a solution of 2,5-dimethylbenzo[b]thiophene-3-acetic acid (i.e. the product of Step C) (0.26 g, 1.2 mmol) in dichloromethane (40 mL) was added oxalyl chloride (0.25 mL, 3.0 mmol) followed by a catalytic amount of DMF (3 drops). This mixture is allowed to stir for 2 h under nitrogen and then concentrated by rotary evaporation. The residue, comprising the acid chloride, was dissolved in acetonitrile (25 mL) and added dropwise over 15 min. to a mixture of methyl 2-(2-methylhydrazinylidene)propanoate (i.e. the product of Step D) (0.20 g, 1.5 mmol) and potassium carbonate (0.28 g, 2.0 mmol) in acetonitrile (20 mL) cooled to 0 °C under nitrogen. The reaction mixture was then allowed to warm to room temperature and stirred for 64 h. The solvent was removed by rotary evaporation, and water (50 mL) was added to the residue. The aqueous phase was extracted with ethyl acetate (3 × 50 mL), and the combined organic extracts were washed with brine (i.e. saturated aqueous sodium chloride) (50 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography (gradient of 10 to 50 % ethyl acetate in hexanes) to yield a white solid (0.23 g).

[0060] 1< H NMR δ 7.55-7.61 (m, 1H), 7.45-7.46 (m, 1H), 7.04-7.09 (m, 1H), 4.08-4.17 (m, 2H), 3.88 (s, 3H), 3.34 (s, 3H), 2.51 (s, 3H), 2.42 (s, 3H), 2.20 (s, 3H).Step F: Preparation of 4-(2,5-dimethylbenzo[b]thien-3-yl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

[0061] A solution of methyl 2-[2-[2-(2,5-dimethylbenzo[b]thien-3yl)acetyl]-2-methyl-hydrazinylidene]propanoate (i.e. the product of Step E) (0.23 g, 0.69 mmol) in DMF (anhydrous, 3 mL) was added via syringe pump over a period of 30 minutes to a tetrahydrofuran solution of potassium tert-butoxide (3.0 mL, 3 mmol) cooled to 0 °C under nitrogen. The reaction mixture was then allowed to warm to room temperature while being stirred for 1 h. The reaction mixture was poured into aqueous hydrochloric acid (0.5 M, 100 mL) and extracted with ethyl acetate (3 × 50 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation to yield a crude residue (0.40 g), which was purified by flash chromatography (gradient of 0 to 40 % ethyl acetate in hexanes) to yield the title product as a white solid (118 mg).

[0062] 1< H NMR δ 7.60 (d, 1H), 7.09 (m, 1H), 7.02 (s, 1H), 6.91 (br s, 1H), 3.52 (s, 3H), 2.39 (s, 3H), 2.21 (s, 3H), 2.17 (s, 3H).SYNTHESIS EXAMPLE 2Preparation of 4-(2,5-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 7)Step A: Preparation of methyl 2-(2-methoxy-1-methyl-2-oxoethoxy)-5-methylbenzoate

[0063] A mixture of methyl 2-hydroxy-5-methylbenzoate (11.89 g, 71.5 mmol), methyl 2-bromopropanoate (13.03 g, 78.0 mmol) and potassium carbonate (29.71 g, 215 mmol) in acetone (300 mL) was heated under reflux for 18 h. The reaction mixture was then filtered, and the filtrate was concentrated by rotary evaporation to yield the title product as a white solid (18.9 g).

[0064] 1< H NMR δ 7.61 (s, 1H), 7.15-7.24 (m, 1H), 6.70-6.84 (m, 1H), 4.73 (m, 1H), 3.89 (s, 3H), 3.74 (s, 3H), 2.30 (s, 3H), 1.63-1.65 (d, 3H).Step B: Preparation of 2-(1-carboxyethoxy)-5-methylbenzoic acid

[0065] A solution of methyl 2-(2-methoxy-1-methyl-2-oxoethoxy)-5-methylbenzoate (i.e. the product of Step A) (18.9 g, 71.5 mmol) in a mixture of tetrahydrofuran (100 mL), methanol (100 mL) and aqueous NaOH solution (6 M, 100 mL) was heated to reflux for 16 h. Then the reaction mixture was cooled and concentrated by rotary evaporation. The residue was dissolved in water (150 mL) and acidified with aqueous concentrated hydrochloric acid to pH < 2. The aqueous phase was extracted with ethyl acetate (2 × 125 mL). The combined organic extracts were washed with brine, dried (MgSO 4 ), filtered and concentrated by rotary evaporation to yield the title product as a yellow solid (16.31 g), which was used in Step C without further purification.

[0066] 1< H NMR δ 7.91 (d, 1H), 7.36 (m, 1H), 6.90 (d, 1H), 4.99 (m, 1H), 2.34 (s, 3H), 1.75-1.80 (m, 3H).Step C: Preparation of 2,5-dimethyl-3-benzofuranyl acetate

[0067] A mixture of 2-(1-carboxyethoxy)-5-methylbenzoic acid (i.e. the product of Step B) (16.3 g, 71 mmol), acetic anhydride (145 mL) and sodium acetate (11.93 g, 145 mmol) was heated at reflux for 3 h. After cooling, the mixture was added to water (300 mL) and extracted with dichloromethane (2 × 150 mL). The organic extracts were dried (MgSO 4 ) and filtered, and the filtrate was concentrated by rotary evaporation to yield the title product as a light brown oil (14.43 g), which was used in Step D without further purification.

[0068] 1< H NMR δ 7.22-7.25 (m, 1H), 7.07-7.11 (m, 1H), 7.01-7.04 (m, 1H), 2.41 (s, 3H), 2.37 (s, 3H), 2.34 (s, 3H).Step D: Preparation of 2,5-dimethyl-3(2H)-benzofuranone

[0069] A mixture of 2,5-dimethyl-3-benzofuranyl acetate (i.e. the product of Step C) (14.40 g, 70.5 mmol), methanol (150 mL) and aqueous hydrochloric acid (1.0 M, 40 mL, 40 mmol) was heated at reflux under nitrogen. The reaction mixture was then concentrated by rotary evaporation. The residue was diluted with water and extracted with diethyl ether (2 × 100 mL). The combined organic extracts were washed with water and brine, dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (gradient of 0 to 15 % ethyl acetate in hexanes) to yield the title product as a white solid (7.47 g).

[0070] 1< H NMR δ 7.41-7.46 (m, 2H), 6.99-7.02 (m, 1H), 4.60-4.64 (q, 1H), 2.35 (s, 3H), 1.50-1.54 (d, 3H).Step E: Preparation of methyl 2,5-dimethyl-3-benzofuranacetate

[0071] A mixture of 2,5-dimethyl-3(2H)-benzofuranone (i.e. the product of Step D) (7.45 g, 45.9 mmol), methyl 2-(triphenylphosphoranylidine)acetate (20.43 g, 61.1 mmol) and toluene (300 mL) were heated at reflux for 66 h. The reaction mixture was then concentrated by rotary evaporation, and diethyl ether (200 mL) was added to the crude residue. This mixture was filtered to remove solids, and the filtrate was concentrated by rotary evaporation to leave an oily mixture (18 g). To this residue were added methanol (40 mL) and a methanolic hydrogen chloride solution (0.5 M, 60 mL, 30 mmol), and the mixture is heated to reflux for 16 h. Then the reaction mixture was cooled and concentrated by rotary evaporation. The residue was purified by flash chromatography (gradient of 0 to 10 % ethyl acetate in hexanes) to provide the title product as a yellow oil (6.75 g).

[0072] 1< H NMR δ 7.19-7.27 (m, 2H), 6.98-7.05 (m, 1H), 3.693 (s, 3H), 3.584 (s, 2H), 2.40-2.45 (m, 6H).Step F: Preparation of 2,5-dimethyl-3-benzofuranacetic acid

[0073] Aqueous sodium hydroxide (5 M, 33 mL, 165 mmol) was added to a solution of methyl 2,5-dimethyl-3-benzofuranacetate (i.e. the product of Step E) (6.75 g, 30.9 mmol) in methanol (120 mL). The mixture was heated to reflux for 16 h and then cooled. The solvent was removed by rotary evaporation. To the residue was added diethyl ether (100 mL), and the resultant mixture was extracted with aqueous sodium hydroxide (1 N, 2 × 100 mL). The ether layer is discarded, and the combined aqueous extracts were acidified with concentrated aqueous hydrochloric acid to pH 1. The acidic aqueous mixture obtained was extracted with dichloromethane (2 × 125 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation to yield the title product as a yellow solid (4.93 g), which was used in Step G without further purification.

[0074] 1< H NMR δ 7.22-7.28 (m, 2H), 6.99-7.05 (m, 1H), 3.61 (s, 2H), 2.42 (s, 3H), 2.41 (s, 3H).Step G: Preparation of methyl 2-[2-[2-(2,5-dimethyl-3-benzofuranyl)acetyl]-2-methylhydrazinylidene]propanoate

[0075] To a solution of 2,5-dimethyl-3-benzofuranacetic acid (i.e. the product of Step F) (4.14 g, 20.2 mmol) in dichloromethane (120 mL) was added oxalyl chloride (2.56 mL, 30.0 mmol) followed by a catalytic amount of DMF (5 drops). The resultant mixture was allowed to stir for 2 h under nitrogen and was then concentrated by rotary evaporation to leave a residue comprising the acid chloride. The residue was dissolved in acetonitrile (50 mL) and added dropwise over 25 min from an addition funnel to a mixture of methyl 2-(2-methylhydrazinylidene)propanoate (2.81 g, 21.6 mmol) and potassium carbonate (3.18 g, 23.0 mmol) in acetonitrile (30 mL) cooled to 0 °C under nitrogen. The reaction mixture was then allowed to warm to room temperature and stirred for 64 h. The solvent was removed by rotary evaporation, and water (150 mL) was added to the residue. The resultant mixture was extracted with ethyl acetate (3 × 80 mL), and the combined organic extracts were washed with brine (50 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography (gradient of 10 to 100 % ethyl acetate in hexanes) to yield the title product as a white solid (3.08 g).

[0076] 1< H NMR δ 7.32 (m, 1H), 7.22-7.24 (m, 1H), 6.98-6.99 (m, 1H), 3.96 (s, 2H), 3.90 (s, 3H), 3.35 (s, 3H), 2.40 (m, 6H), 2.20 (s, 3H).Step H: Preparation of 4-(2,5-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

[0077] A solution of methyl 2-[2-[2-(2,5-dimethyl-3-benzofuranyl)acetyl]-2-methyl-hydrazinylidene]propanoate (i.e. the product of Step G) (2.97 g, 9.39 mmol) anhydrous DMF (25 mL) was added over 30 min from an addition funnel to a tetrahydrofuran solution of potassium tert-butoxide (25.0 mL, 25.0 mmol) cooled to 0 °C under nitrogen. The reaction mixture was then allowed to warm to room temperature and stirred for 1 h. The reaction mixture was poured into aqueous hydrochloric acid (0.5 M, 150 mL) and extracted with ethyl acetate (3 × 90 mL). The combined organic extracts were washed with brine (100 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography (gradient of 10 to 75 % ethyl acetate in hexanes) to yield the title product as a white solid (790 mg).

[0078] 1< H NMR (DMSO-d 6 ) δ 10.29 (s, 1H), 7.39 (m, 1H), 7.04 (m, 1H), 6.95-7.01 (m, 1H), 3.60 (s, 3H), 2.32 (s, 3H), 2.25 (m, 6H).SYNTHESIS EXAMPLE 3Preparation of 5-hydroxy-2,6-dimethyl-4-(2,5,7-trimethyl-3-benzofuranyl)-3(2H)-pyridazinone (Compound 12)Step A: Preparation of 2,4-dimethylphenyl propanoate

[0079] Propanoyl chloride (2.44 g, 26.4 mmol) was added dropwise to a mixture of 2,4-dimethylphenol (3.26 g, 24 mmol) and triethylamine (3.51 mL, 25 mmol) in dichloromethane (35 mL) cooled to 0 °C under nitrogen. The mixture was stirred for 16 h, and then aqueous hydrochloric acid (0.2 M, 50 mL) was added. The organic phase was separated, and the aqueous phase was extracted with dichloromethane (50 mL). The combined organic phases were washed with brine, dried (MgSO 4 ), filtered and concentrated to yield the title product as a yellow oil (3.91 g), which was used directly in the next step without further purification.

[0080] 1< H NMR δ 7.03 (s, 1H), 6.99 (d, 1H), 6.87 (d, 1H), 2.56-2.62 (m, 2H), 2.30 (s, 3H), 2.14 (s, 3H), 1.26-1.31 (m, 3H).Step B: Preparation of 1-(2-hydroxy-3,5-dimethylphenyl)-1-propanone

[0081] Aluminum chloride (3.10 g, 23.2 mmol) was added to 2,4-dimethylphenyl propanoate (i.e. the product of Step A) (3.91 g, 21.9 mmol), and the mixture formed was heated to 130°C for 2 h. The mixture was then cooled to room temperature, and aqueous hydrochloric acid (1.0 M, 100 mL) was added, followed by diethyl ether (100 mL). The organic phase was separated, and the aqueous phase was extracted with diethyl ether (50 mL). The combined organic extracts were dried (MgSO 4 ), filtered and concentrated to yield the title product as a yellow crystalline solid (3.71 g), which was used directly in the next step without further purification.

[0082] 1< H NMR δ 12.49 (s, 1H), 7.40 (s, 1H), 7.16 (s, 1H), 3.03 (m, 2H), 2.29 (s, 3H), 2.23 (s, 3H), 1.22-1.25 (m, 3H).Step C: Preparation of 2-bromo-1-(2-hydroxy-3,5-methylphenyl)-1-propanone

[0083] To mixture of copper(II) bromide (9.30 g, 41.6 mmol) in ethyl acetate (30 mL) was added dropwise from an addition funnel a solution of 1-(2-hydroxy-3,5-dimethylphenyl)-1-propanone (i.e. the product of Step B) (3.71 g, 20.8 mmol) dissolved in trichloromethane (24 mL). The resultant mixture was heated to reflux for 16 h, then cooled to room temperature and filtered through a filter funnel packed with Celite ®< diatomaceous filter aid. The filtrate was concentrated, and the residue was diluted with diethyl ether (100 mL) and washed with saturated aqueous ethylenediaminetetraacetic acid disodium salt solution (100 mL). The organic phase was dried (MgSO 4 ), filtered and concentrated by rotary evaporation to yield the title product as a brown oil (5.33 g), which was used directly in the next step without further purification.

[0084] 1< H NMR δ 12.09 (s, 1H), 7.39-7.44 (m, 1H), 7.18-7.23 (m, 1H), 5.31-5.40 (m, 1H), 2.29 (s, 3H), 2.24 (s, 3H), 1.90 (d, 3H).Step D: Preparation of 2,5,7-trimethyl-3(2H)-benzofuranone

[0085] N,N-dimethylformamide (25 mL) and potassium carbonate (4.15 g, 30 mmol) were added to 2-bromo-1-(2-hydroxy-3,5-methylphenyl)-1-propanone (i.e. the product of Step C) (5.33 g, 20.7 mmol), and the resultant mixture was stirred at room temperature for 18 h. Then water (150 mL) was added, and the mixture was extracted with diethyl ether (3 × 80 mL). The combined organic extracts were washed with water, followed by brine, dried (MgSO 4 ), filtered and concentrated. The residue was purified by flash chromatography (eluted with gradient of 0 to 10 % ethyl acetate in hexanes) to yield the title product as a yellow oil (2.13 g).

[0086] 1< H NMR δ 7.26-7.28 (m, 1H), 7.24-7.26 (m, 1H), 4.59-4.64 (m, 1H), 2.32 (s, 3H), 2.29 (s, 3H), 1.52 (d, 3H).Step E: Preparation of methyl 2,5,7-trimethyl-3-benzofuranacetate

[0087] A mixture of 2,5,7-trimethyl-3(2H)-benzofuranone (i.e. the product of Step D) (2.07 g, 11.7 mmol), methyl 2-(triphenylphosphoranylidene)acetate (5.89 g, 17.6 mmol) and toluene (120 mL) were heated at reflux for 66 h. The reaction mixture was then concentrated by rotary evaporation, and to the residue was added diethyl ether (150 mL). The resultant mixture was filtered to remove solids, and the filtrate was concentrated by rotary evaporation to leave an oily mixture (6 g). To this residue were added methanol (100 mL) and a methanol solution of hydrogen chloride (0.5 M, 30 mL, 15 mmol). The resultant mixture was heated to reflux for 16 h and then cooled. The mixture was concentrated by rotary evaporation to leave a residue which was purified by flash chromatography (gradient of 0 to 5 % ethyl acetate in hexanes) to yield the title product as a yellow oil (0.59 g), with was used without further purification in the next step.

[0088] 1< H NMR δ 7.06 (s, 1H), 6.83 (s, 1H), 3.68 (s, 3H), 3.57 (s, 2H), 2.44 (s, 3H), 2.42 (s, 3H), 2.39 (s, 3H).Step F: Preparation of 2,5,7-trimethyl-3-benzofuranacetic acid

[0089] To a solution of methyl 2,5,7-trimethyl-3-benzofuranacetate (i.e. the product of Step E) (0.55 g, 2.37 mmol) in methanol (50 mL) was added aqueous sodium hydroxide (5 M, 2 mL, 10 mmol). The resultant mixture was heated to reflux for 16 h and then cooled. The solvent was removed by rotary evaporation. To the residue was added diethyl ether (100 mL), and the resultant mixture was extracted with aqueous sodium hydroxide (1 N, 2 × 100 mL). The ether layer was discarded, and the combined basic extracts were acidified with concentrated aqueous hydrochloric acid to a pH of 1. The acidic aqueous mixture was then extracted with dichloromethane (2 × 125 mL). The combined organic extracts were dried (MgSO 4 ), filtered and concentrated by rotary evaporation to yield the title product as a yellow solid (0.52 g), which was used in the next step without further purification.

[0090] 1< H NMR δ 7.05 (s, 1H), 6.84 (s, 1H), 3.60 (s, 2H), 2.43 (s, 3H), 2.41 (s, 3H), 2.38 (s, 3H).Step G: Preparation of 2,5,7-trimethyl-3-benzofuranacetic acid 2-(2-methoxy-1-methyl-2-oxoethylidene)-1-methylhydrazide

[0091] To a solution of 2,5,7-trimethyl-3-benzofuranacetic acid (i.e. the product of Step F) (0.52 g, 2.38 mmol) in dichloromethane (80 mL) was added oxalyl chloride (0.5 mL, 6.0 mmol), followed by a catalytic amount of DMF (3 drops). The resultant mixture was allowed to stir for 2 h under nitrogen and then was concentrated by rotary evaporation. The residue, which contained 2,5,7-trimethyl-3-benzofuranacetyl chloride, was dissolved in acetonitrile (50 mL) and added dropwise over 25 min from an addition funnel to a mixture of methyl 2-(2-methylhydrazinylidene)propanoate (0.35 g, 2.7 mmol) and potassium carbonate (0.69 g, 5.0 mmol) in acetonitrile (30 mL) cooled to 0 °C under nitrogen. Then the reaction mixture was allowed to warm to room temperature and stir for 18 h. The solvent was removed by rotary evaporation, and to the residue was added water (90 mL). The resultant mixture was extracted with ethyl acetate (3 × 50 mL), and the combined organic extracts were washed with brine (50 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography (gradient of 5 to 50 % ethyl acetate in hexanes) to yield the title product as a yellow solid (0.32 g).

[0092] 1< H NMR δ 7.14 (s, 1H), 6.80 (s, 1H), 3.95 (s, 2H), 3.90 (s, 3H), 3.35 (s, 3H), 2.42 (s, 3H), 2.41 (s, 3H), 2.36 (s, 3H), 2.19 (s, 3H).Step H: Preparation of 5-hydroxy-2,6-dimethyl-4-(2,5,7-trimethyl-3-benzofuranyl)-3(2H)-pyridazinone

[0093] A solution of 2,5,7-trimethyl-3-benzofuranacetic acid 2-(2-methoxy-1-methyl-2-oxoethylidene)-1-methylhydrazide (i.e. the product of Step G) (0.31 g, 1.0 mmol) in N,N-dimethylformamide (anhydrous, 5 mL) was added by syringe pump over 1 h to a tetrahydrofuran solution of potassium tert-butoxide (1 M, 5.0 mL, 5.0 mmol) cooled to 0 °C under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was then poured into aqueous hydrochloric acid (0.5 M, 60 mL) and extracted with ethyl acetate (3 × 50 mL). The combined organic extracts were washed with brine (60 mL), dried (MgSO 4 ), filtered and concentrated by rotary evaporation. The resultant residue was purified by flash chromatography (gradient of 5 to 100 % ethyl acetate in hexanes) to yield the title product as a white solid (72.3 mg).

[0094] 1< H NMR δ 6.88 (s, 1H), 6.84 (s, 1H), 5.86 (br s, 1H), 3.74 (s, 3H), 2.48 (s, 3H), 2.38 (s, 3H), 2.36 (s, 3H), 2.34 (s, 3H).

[0095] By the procedures described herein together with methods known in the art, the following compounds of Formula 1 in Tables 1 to 619 can be prepared. The following abbreviations are used in the Tables which follow: t means tertiary, s means secondary, n means normal, i means iso, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, Bu means butyl, OMe means methoxy, CN means cyano, S(O) 2 Me means methylsulfonyl, and "-" means no substitution with R 3< .

[0096] Table 2 is constructed in the same manner except that the Row Heading "W is O, X is S, R 1< is Me, R 2< is Me, and G is H." is replaced with the Row Heading listed for Table 2 below (i.e. "W is O, X is S, R 1< is Me, R 2< is Me, and G is C(O)Me."). Therefore the first entry in Table 2 is a compound of Formula 1 wherein W is O, X is S, R 1< is Me, R 2< is Me, (R 3< ) n is "-" (i.e. n is 0; no substitution with R 3< ), R 4< is H, and G is C(O)Me. Tables 3 through 627 are constructed similarly. TableRow Heading2W is O, X is S, R 1< is Me, R 2< is Me, and G is C(O)Me.3W is O, X is S, R 1< is Me, R 2< is Me, and G is C(O)Et.4W is O, X is S, R 1< is Me, R 2< is Me, and G is C(O)-i-Pr.5W is O, X is S, R 1< is Me, R 2< is Me, and G is C(O)-t-Bu.6W is O, X is S, R 1< is Me, R 2< is Me, and G is CO 2 Me.7W is O, X is S, R 1< is Me, R 2< is Me, and G is CO 2 Et.8W is O, X is S, R 1< is Me, R 2< is Me, and G is CO 2 -i-Pr.9W is O, X is S, R 1< is Me, R 2< is Me, and G is CO 2 -t-Bu.10W is O, X is S, R 1< is Me, R 2< is Me, and G is SO 2 Me.11W is O, X is S, R 1< is Me, R 2< is H, and G is C(O)Me.12W is O, X is S, R 1< is Me, R 2< is H, and G is C(O)Et.13W is O, X is S, R 1< is Me, R 2< is H, and G is C(O)-i-Pr.14W is O, X is S, R 1< is Me, R 2< is H, and G is C(O)-t-Bu.15W is O, X is S, R 1< is Me, R 2< is H, and G is CO 2 Me.16W is O, X is S, R 1< is Me, R 2< is H, and G is CO 2 Et.17W is O, X is S, R 1< is Me, R 2< is H, and G is CO 2 -i-Pr.18W is O, X is S, R 1< is Me, R 2< is H, and G is CO 2 -t-Bu.19W is O, X is S, R 1< is Me, R 2< is H, and G is SO 2 Me.20W is O, X is S, R 1< is Me, R 2< is Et, and G is C(O)Me.21W is O, X is S, R 1< is Me, R 2< is Et, and G is C(O)Et.22W is O, X is S, R 1< is Me, R 2< is Et, and G is C(O)-i-Pr.23W is O, X is S, R 1< is Me, R 2< is Et, and G is C(O)-t-Bu.24W is O, X is S, R 1< is Me, R 2< is Et, and G is CO 2 Me.25W is O, X is S, R 1< is Me, R 2< is Et, and G is CO 2 Et.26W is O, X is S, R 1< is Me, R 2< is Et, and G is CO 2 -i-Pr.27W is O, X is S, R 1< is Me, R 2< is Et, and G is CO 2 -t-Bu.28W is O, X is S, R 1< is Me, R 2< is Et, and G is SO 2 Me.29W is O, X is S, R 1< is Me, R 2< is Pr, and G is C(O)Me.30W is O, X is S, R 1< is Me, R 2< is Pr, and G is C(O)Et.31W is O, X is S, R 1< is Me, R 2< is Pr, and G is C(O)-i-Pr.32W is O, X is S, R 1< is Me, R 2< is Pr, and G is C(O)-t-Bu.33W is O, X is S, R 1< is Me, R 2< is Pr, and G is CO 2 Me.34W is O, X is S, R 1< is Me, R 2< is Pr, and G is CO 2 Et.35W is O, X is S, R 1< is Me, R 2< is Pr, and G is CO 2 -i-Pr.36W is O, X is S, R 1< is Me, R 2< is Pr, and G is CO 2 -t-Bu.37W is O, X is S, R 1< is Me, R 2< is Pr, and G is SO 2 Me.38W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is C(O)Me.39W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is C(O)Et.40W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is C(O)-i-Pr.41W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is C(O)-t-Bu.42W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is CO 2 Me.43W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is CO 2 Et.44W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is CO 2 -i-Pr.45W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is CO 2 -t-Bu.46W is O, X is S, R 1< is Me, R 2< is CF 3 , and G is SO 2 Me.47W is O, X is S, R 1< is Me, R 2< is Cl, and G is C(O)Me.48W is O, X is S, R 1< is Me, R 2< is Cl, and G is C(O)Et.49W is O, X is S, R 1< is Me, R 2< is Cl, and G is C(O)-i-Pr.50W is O, X is S, R 1< is Me, R 2< is Cl, and G is C(O)-t-Bu.51W is O, X is S, R 1< is Me, R 2< is Cl, and G is CO 2 Me.52W is O, X is S, R 1< is Me, R 2< is Cl, and G is CO 2 Et.53W is O, X is S, R 1< is Me, R 2< is Cl, and G is CO 2 -i-Pr.54W is O, X is S, R 1< is Me, R 2< is Cl, and G is CO 2 -t-Bu.55W is O, X is S, R 1< is Me, R 2< is Cl, and G is SO 2 Me.56W is O, X is S, R 1< is Me, R 2< is Br, and G is C(O)Me.57W is O, X is S, R 1< is Me, R 2< is Br, and G is C(O)Et.58W is O, X is S, R 1< is Me, R 2< is Br, and G is C(O)-i-Pr.59W is O, X is S, R 1< is Me, R 2< is Br, and G is C(O)-t-Bu.60W is O, X is S, R 1< is Me, R 2< is Br, and G is CO 2 Me.61W is O, X is S, R 1< is Me, R 2< is Br, and G is CO 2 Et.62W is O, X is S, R 1< is Me, R 2< is Br, and G is CO 2 -i-Pr.63W is O, X is S, R 1< is Me, R 2< is Br, and G is CO 2 -t-Bu.64W is O, X is S, R 1< is Me, R 2< is Br, and G is SO 2 Me.65W is O, X is S, R 1< is Me, R 2< is I, and G is C(O)Me.66W is O, X is S, R 1< is Me, R 2< is I, and G is C(O)Et.67W is O, X is S, R 1< is Me, R 2< is I, and G is C(O)-i-Pr.68W is O, X is S, R 1< is Me, R 2< is I, and G is C(O)-t-Bu.69W is O, X is S, R 1< is Me, R 2< is I, and G is CO 2 Me.70W is O, X is S, R 1< is Me, R 2< is I, and G is CO 2 Et.71W is O, X is S, R 1< is Me, R 2< is I, and G is CO 2 -i-Pr.72W is O, X is S, R 1< is Me, R 2< is I, and G is CO 2 -t-Bu.73W is O, X is S, R 1< is Me, R 2< is I, and G is SO 2 Me.74W is O, X is S, R 1< is Me, R 2< is OMe, and G is C(O)Me.75W is O, X is S, R 1< is Me, R 2< is OMe, and G is C(O)Et.76W is O, X is S, R 1< is Me, R 2< is OMe, and G is C(O)-i-Pr.77W is O, X is S, R 1< is Me, R 2< is OMe, and G is C(O)-t-Bu.78W is O, X is S, R 1< is Me, R 2< is OMe, and G is CO 2 Me.79W is O, X is S, R 1< is Me, R 2< is OMe, and G is CO 2 Et.80W is O, X is S, R 1< is Me, R 2< is OMe, and G is CO 2 -i-Pr.81W is O, X is S, R 1< is Me, R 2< is OMe, and G is CO 2 -t-Bu.82W is O, X is S, R 1< is Me, R 2< is OMe, and G is SO 2 Me.83W is O, X is S, R 1< is Me, R 2< is OEt, and G is C(O)Me.84W is O, X is S, R 1< is Me, R 2< is OEt, and G is C(O)Et.85W is O, X is S, R 1< is Me, R 2< is OEt, and G is C(O)-i-Pr.86W is O, X is S, R 1< is Me, R 2< is OEt, and G is C(O)-t-Bu.87W is O, X is S, R 1< is Me, R 2< is OEt, and G is CO 2 Me.88W is O, X is S, R 1< is Me, R 2< is OEt, and G is CO 2 Et.89W is O, X is S, R 1< is Me, R 2< is OEt, and G is CO 2 -i-Pr.90W is O, X is S, R 1< is Me, R 2< is OEt, and G is CO 2 -t-Bu.91W is O, X is S, R 1< is Me, R 2< is OEt, and G is SO 2 Me.92W is O, X is S, R 1< is Et, R 2< is Me, and G is C(O)Me.93W is O, X is S, R 1< is Et, R 2< is Me, and G is C(O)Et.94W is O, X is S, R 1< is Et, R 2< is Me, and G is C(O)-i-Pr.95W is O, X is S, R 1< is Et, R 2< is Me, and G is C(O)-t-Bu.96W is O, X is S, R 1< is Et, R 2< is Me, and G is CO 2 Me.97W is O, X is S, R 1< is Et, R 2< is Me, and G is CO 2 Et.98W is O, X is S, R 1< is Et, R 2< is Me, and G is CO 2 -i-Pr.99W is O, X is S, R 1< is Et, R 2< is Me, and G is CO 2 -t-Bu.100W is O, X is S, R 1< is Et, R 2< is Me, and G is SO 2 Me.101W is O, X is S, R 1< is Et, R 2< is H, and G is C(O)Me.102W is O, X is S, R 1< is Et, R 2< is H, and G is C(O)Et.103W is O, X is S, R 1< is Et, R 2< is H, and G is C(O)-i-Pr.104W is O, X is S, R 1< is Et, R 2< is H, and G is C(O)-t-Bu.105W is O, X is S, R 1< is Et, R 2< is H, and G is CO 2 Me.106W is O, X is S, R 1< is Et, R 2< is H, and G is CO 2 Et.107W is O, X is S, R 1< is Et, R 2< is H, and G is CO 2 -i-Pr.108W is O, X is S, R 1< is Et, R 2< is H, and G is CO 2 -t-Bu.109W is O, X is S, R 1< is Et, R 2< is H, and G is SO 2 Me.110W is O, X is S, R 1< is Et, R 2< is Et, and G is C(O)Me.111W is O, X is S, R 1< is Et, R 2< is Et, and G is C(O)Et.112W is O, X is S, R 1< is Et, R 2< is Et, and G is C(O)-i-Pr.113W is O, X is S, R 1< is Et, R 2< is Et, and G is C(O)-t-Bu.114W is O, X is S, R 1< is Et, R 2< is Et, and G is CO 2 Me.115W is O, X is S, R 1< is Et, R 2< is Et, and G is CO 2 Et.116W is O, X is S, R 1< is Et, R 2< is Et, and G is CO 2 -i-Pr.117W is O, X is S, R 1< is Et, R 2< is Et, and G is CO 2 -t-Bu.118W is O, X is S, R 1< is Et, R 2< is Et, and G is SO 2 Me.119W is O, X is S, R 1< is Et, R 2< is Pr, and G is C(O)Me.120W is O, X is S, R 1< is Et, R 2< is Pr, and G is C(O)Et.121W is O, X is S, R 1< is Et, R 2< is Pr, and G is C(O)-i-Pr.122W is O, X is S, R 1< is Et, R 2< is Pr, and G is C(O)-t-Bu.123W is O, X is S, R 1< is Et, R 2< is Pr, and G is CO 2 Me.124W is O, X is S, R 1< is Et, R 2< is Pr, and G is CO 2 Et.125W is O, X is S, R 1< is Et, R 2< is Pr, and G is CO 2 -i-Pr.126W is O, X is S, R 1< is Et, R 2< is Pr, and G is CO 2 -t-Bu.127W is O, X is S, R 1< is Et, R 2< is Pr, and G is SO 2 Me.128W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is C(O)Me.129W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is C(O)Et.130W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is C(O)-i-Pr.131W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is C(O)-t-Bu.132W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is CO 2 Me.133W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is CO 2 Et.134W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is CO 2 -i-Pr.135W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is CO 2 -t-Bu.136W is O, X is S, R 1< is Et, R 2< is CF 3 , and G is SO 2 Me.137W is O, X is S, R 1< is Et, R 2< is Cl, and G is C(O)Me.138W is O, X is S, R 1< is Et, R 2< is Cl, and G is C(O)Et.139W is O, X is S, R 1< is Et, R 2< is Cl, and G is C(O)-i-Pr.140W is O, X is S, R 1< is Et, R 2< is Cl, and G is C(O)-t-Bu.141W is O, X is S, R 1< is Et, R 2< is Cl, and G is CO 2 Me.142W is O, X is S, R 1< is Et, R 2< is Cl, and G is CO 2 Et.143W is O, X is S, R 1< is Et, R 2< is Cl, and G is CO 2 -i-Pr.144W is O, X is S, R 1< is Et, R 2< is Cl, and G is CO 2 -t-Bu.145W is O, X is S, R 1< is Et, R 2< is Cl, and G is SO 2 Me.146W is O, X is S, R 1< is Et, R 2< is Br, and G is C(O)Me.147W is O, X is S, R 1< is Et, R 2< is Br, and G is C(O)Et.148W is O, X is S, R 1< is Et, R 2< is Br, and G is C(O)-i-Pr.149W is O, X is S, R 1< is Et, R 2< is Br, and G is C(O)-t-Bu.150W is O, X is S, R 1< is Et, R 2< is Br, and G is CO 2 Me.151W is O, X is S, R 1< is Et, R 2< is Br, and G is CO 2 Et.152W is O, X is S, R 1< is Et, R 2< is Br, and G is CO 2 -i-Pr.153W is O, X is S, R 1< is Et, R 2< is Br, and G is CO 2 -t-Bu.154W is O, X is S, R 1< is Et, R 2< is Br, and G is SO 2 Me.155W is O, X is S, R 1< is Et, R 2< is I, and G is C(O)Me.156W is O, X is S, R 1< is Et, R 2< is I, and G is C(O)Et.157W is O, X is S, R 1< is Et, R 2< is I, and G is C(O)-i-Pr.158W is O, X is S, R 1< is Et, R 2< is I, and G is C(O)-t-Bu.159W is O, X is S, R 1< is Et, R 2< is I, and G is CO 2 Me.160W is O, X is S, R 1< is Et, R 2< is I, and G is CO 2 Et.161W is O, X is S, R 1< is Et, R 2< is I, and G is CO 2 -i-Pr.162W is O, X is S, R 1< is Et, R 2< is I, and G is CO 2 -t-Bu.163W is O, X is S, R 1< is Et, R 2< is I, and G is SO 2 Me.164W is O, X is S, R 1< is Et, R 2< is OMe, and G is C(O)Me.165W is O, X is S, R 1< is Et, R 2< is OMe, and G is C(O)Et.166W is O, X is S, R 1< is Et, R 2< is OMe, and G is C(O)-i-Pr.167W is O, X is S, R 1< is Et, R 2< is OMe, and G is C(O)-t-Bu.168W is O, X is S, R 1< is Et, R 2< is OMe, and G is CO 2 Me.169W is O, X is S, R 1< is Et, R 2< is OMe, and G is CO 2 Et.170W is O, X is S, R 1< is Et, R 2< is OMe, and G is CO 2 -i-Pr.171W is O, X is S, R 1< is Et, R 2< is OMe, and G is CO 2 -t-Bu.172W is O, X is S, R 1< is Et, R 2< is OMe, and G is SO 2 Me.173W is O, X is S, R 1< is Et, R 2< is OEt, and G is C(O)Me.174W is O, X is S, R 1< is Et, R 2< is OEt, and G is C(O)Et.175W is O, X is S, R 1< is Et, R 2< is OEt, and G is C(O)-i-Pr.176W is O, X is S, R 1< is Et, R 2< is OEt, and G is C(O)-t-Bu.177W is O, X is S, R 1< is Et, R 2< is OEt, and G is CO 2 Me.178W is O, X is S, R 1< is Et, R 2< is OEt, and G is CO 2 Et.179W is O, X is S, R 1< is Et, R 2< is OEt, and G is CO 2 -i-Pr.180W is O, X is S, R 1< is Et, R 2< is OEt, and G is CO 2 -t-Bu.181W is O, X is S, R 1< is Et, R 2< is OEt, and G is SO 2 Me.182W is O, X is S, R 1< is Pr, R 2< is Me, and G is C(O)Me.183W is O, X is S, R 1< is Pr, R 2< is Me, and G is C(O)Et.184W is O, X is S, R 1< is Pr, R 2< is Me, and G is C(O)-i-Pr.185W is O, X is S, R 1< is Pr, R 2< is Me, and G is C(O)-t-Bu.186W is O, X is S, R 1< is Pr, R 2< is Me, and G is CO 2 Me.187W is O, X is S, R 1< is Pr, R 2< is Me, and G is CO 2 Et.188W is O, X is S, R 1< is Pr, R 2< is Me, and G is CO 2 -i-Pr.189W is O, X is S, R 1< is Pr, R 2< is Me, and G is CO 2 -t-Bu.190W is O, X is S, R 1< is Pr, R 2< is Me, and G is SO 2 Me.191W is O, X is S, R 1< is Pr, R 2< is H, and G is C(O)Me.192W is O, X is S, R 1< is Pr, R 2< is H, and G is C(O)Et.193W is O, X is S, R 1< is Pr, R 2< is H, and G is C(O)-i-Pr.194W is O, X is S, R 1< is Pr, R 2< is H, and G is C(O)-t-Bu.195W is O, X is S, R 1< is Pr, R 2< is H, and G is CO 2 Me.196W is O, X is S, R 1< is Pr, R 2< is H, and G is CO 2 Et.197W is O, X is S, R 1< is Pr, R 2< is H, and G is CO 2 -i-Pr.198W is O, X is S, R 1< is Pr, R 2< is H, and G is CO 2 -t-Bu.199W is O, X is S, R 1< is Pr, R 2< is H, and G is SO 2 Me.200W is O, X is S, R 1< is Pr, R 2< is Et, and G is C(O)Me.201W is O, X is S, R 1< is Pr, R 2< is Et, and G is C(O)Et.202W is O, X is S, R 1< is Pr, R 2< is Et, and G is C(O)-i-Pr.203W is O, X is S, R 1< is Pr, R 2< is Et, and G is C(O)-t-Bu.204W is O, X is S, R 1< is Pr, R 2< is Et, and G is CO 2 Me.205W is O, X is S, R 1< is Pr, R 2< is Et, and G is CO 2 Et.206W is O, X is S, R 1< is Pr, R 2< is Et, and G is CO 2 -i-Pr.207W is O, X is S, R 1< is Pr, R 2< is Et, and G is CO 2 -t-Bu.208W is O, X is S, R 1< is Pr, R 2< is Et, and G is SO 2 Me.209W is O, X is S, R 1< is Pr, R 2< is Pr, and G is C(O)Me.210W is O, X is S, R 1< is Pr, R 2< is Pr, and G is C(O)Et.211W is O, X is S, R 1< is Pr, R 2< is Pr, and G is C(O)-i-Pr.212W is O, X is S, R 1< is Pr, R 2< is Pr, and G is C(O)-t-Bu.213W is O, X is S, R 1< is Pr, R 2< is Pr, and G is CO 2 Me.214W is O, X is S, R 1< is Pr, R 2< is Pr, and G is CO 2 Et.215W is O, X is S, R 1< is Pr, R 2< is Pr, and G is CO 2 -i-Pr.216W is O, X is S, R 1< is Pr, R 2< is Pr, and G is CO 2 -t-Bu.217W is O, X is S, R 1< is Pr, R 2< is Pr, and G is SO 2 Me.218W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is C(O)Me.219W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is C(O)Et.220W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is C(O)-i-Pr.221W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is C(O)-t-Bu.222W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is CO 2 Me.223W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is CO 2 Et.224W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is CO 2 -i-Pr.225W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is CO 2 -t-Bu.226W is O, X is S, R 1< is Pr, R 2< is CF 3 , and G is SO 2 Me.227W is O, X is S, R 1< is Pr, R 2< is Cl, and G is C(O)Me.228W is O, X is S, R 1< is Pr, R 2< is Cl, and G is C(O)Et.229W is O, X is S, R 1< is Pr, R 2< is Cl, and G is C(O)-i-Pr.230W is O, X is S, R 1< is Pr, R 2< is Cl, and G is C(O)-t-Bu.231W is O, X is S, R 1< is Pr, R 2< is Cl, and G is CO 2 Me.232W is O, X is S, R 1< is Pr, R 2< is Cl, and G is CO 2 Et.233W is O, X is S, R 1< is Pr, R 2< is Cl, and G is CO 2 -i-Pr.234W is O, X is S, R 1< is Pr, R 2< is Cl, and G is CO 2 -t-Bu.235W is O, X is S, R 1< is Pr, R 2< is Cl, and G is SO 2 Me.236W is O, X is S, R 1< is Pr, R 2< is Br, and G is C(O)Me.237W is O, X is S, R 1< is Pr, R 2< is Br, and G is C(O)Et.238W is O, X is S, R 1< is Pr, R 2< is Br, and G is C(O)-i-Pr.239W is O, X is S, R 1< is Pr, R 2< is Br, and G is C(O)-t-Bu.240W is O, X is S, R 1< is Pr, R 2< is Br, and G is CO 2 Me.241W is O, X is S, R 1< is Pr, R 2< is Br, and G is CO 2 Et.242W is O, X is S, R 1< is Pr, R 2< is Br, and G is CO 2 -i-Pr.243W is O, X is S, R 1< is Pr, R 2< is Br, and G is CO 2 -t-Bu.244W is O, X is S, R 1< is Pr, R 2< is Br, and G is SO 2 Me.245W is O, X is S, R 1< is Pr, R 2< is I, and G is C(O)Me.246W is O, X is S, R 1< is Pr, R 2< is I, and G is C(O)Et.247W is O, X is S, R 1< is Pr, R 2< is I, and G is C(O)-i-Pr.248W is O, X is S, R 1< is Pr, R 2< is I, and G is C(O)-t-Bu.249W is O, X is S, R 1< is Pr, R 2< is I, and G is CO 2 Me.250W is O, X is S, R 1< is Pr, R 2< is I, and G is CO 2 Et.251W is O, X is S, R 1< is Pr, R 2< is I, and G is CO 2 -i-Pr.252W is O, X is S, R 1< is Pr, R 2< is I, and G is CO 2 -t-Bu.253W is O, X is S, R 1< is Pr, R 2< is I, and G is SO 2 Me.254W is O, X is S, R 1< is Pr, R 2< is OMe, and G is C(O)Me.255W is O, X is S, R 1< is Pr, R 2< is OMe, and G is C(O)Et.256W is O, X is S, R 1< is Pr, R 2< is OMe, and G is C(O)-i-Pr.257W is O, X is S, R 1< is Pr, R 2< is OMe, and G is C(O)-t-Bu.258W is O, X is S, R 1< is Pr, R 2< is OMe, and G is CO 2 Me.259W is O, X is S, R 1< is Pr, R 2< is OMe, and G is CO 2 Et.260W is O, X is S, R 1< is Pr, R 2< is OMe, and G is CO 2 -i-Pr.261W is O, X is S, R 1< is Pr, R 2< is OMe, and G is CO 2 -t-Bu.262W is O, X is S, R 1< is Pr, R 2< is OMe, and G is SO 2 Me.263W is O, X is S, R 1< is Pr, R 2< is OEt, and G is C(O)Me.264W is O, X is S, R 1< is Pr, R 2< is OEt, and G is C(O)Et.265W is O, X is S, R 1< is Pr, R 2< is OEt, and G is C(O)-i-Pr.266W is O, X is S, R 1< is Pr, R 2< is OEt, and G is C(O)-t-Bu.267W is O, X is S, R 1< is Pr, R 2< is OEt, and G is CO 2 Me.268W is O, X is S, R 1< is Pr, R 2< is OEt, and G is CO 2 Et.269W is O, X is S, R 1< is Pr, R 2< is OEt, and G is CO 2 -i-Pr.270W is O, X is S, R 1< is Pr, R 2< is OEt, and G is CO 2 -t-Bu.271W is O, X is S, R 1< is Pr, R 2< is OEt, and G is SO 2 Me.272W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is C(O)Me.273W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is C(O)Et.274W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is C(O)-i-Pr.275W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is C(O)-t-Bu.276W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is CO 2 Me.277W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is CO 2 Et.278W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is CO 2 -i-Pr.279W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is CO 2 -t-Bu.280W is O, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is SO 2 Me.281W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is C(O)Me.282W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is C(O)Et.283W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is C(O)-i-Pr.284W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is C(O)-t-Bu.285W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is CO 2 Me.286W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is CO 2 Et.287W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is CO 2 -i-Pr.288W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is CO 2 -t-Bu.289W is O, X is -CH=CH-, R 1< is Me, R 2< is H, and G is SO 2 Me.290W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is C(O)Me.291W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is C(O)Et.292W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is C(O)-i-Pr.293W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is C(O)-t-Bu.294W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is CO 2 Me.295W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is CO 2 Et.296W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is CO 2 -i-Pr.297W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is CO 2 -t-Bu.298W is O, X is -CH=CH-, R 1< is Me, R 2< is Et, and G is SO 2 Me.299W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is C(O)Me.300W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is C(O)Et.301W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is C(O)-i-Pr.302W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is C(O)-t-Bu.303W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is CO 2 Me.304W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is CO 2 Et.305W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is CO 2 -i-Pr.306W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is CO 2 -t-Bu.307W is O, X is -CH=CH-, R 1< is Me, R 2< is Pr, and G is SO 2 Me.308W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is C(O)Me.309W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is C(O)Et.310W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is C(O)-i-Pr.311W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is C(O)-t-Bu.312W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is CO 2 Me.313W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is CO 2 Et.314W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is CO 2 -i-Pr.315W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is CO 2 -t-Bu.316W is O, X is -CH=CH-, R 1< is Me, R 2< is CF 3 , and G is SO 2 Me.317W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is C(O)Me.318W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is C(O)Et.319W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is C(O)-i-Pr.320W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is C(O)-t-Bu.321W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is CO 2 Me.322W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is CO 2 Et.323W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is CO 2 -i-Pr.324W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is CO 2 -t-Bu.325W is O, X is -CH=CH-, R 1< is Me, R 2< is Cl, and G is SO 2 Me.326W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is C(O)Me.327W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is C(O)Et.328W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is C(O)-i-Pr.329W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is C(O)-t-Bu.330W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is CO 2 Me.331W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is CO 2 Et.332W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is CO 2 -i-Pr.333W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is CO 2 -t-Bu.334W is O, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is SO 2 Me.335W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is C(O)Me.336W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is C(O)Et.337W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is C(O)-i-Pr.338W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is C(O)-t-Bu.339W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is CO 2 Me.340W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is CO 2 Et.341W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is CO 2 -i-Pr.342W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is CO 2 -t-Bu.343W is O, X is -CH=CH-, R 1< is Me, R 2< is I, and G is SO 2 Me.344W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is C(O)Me.345W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is C(O)Et.346W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is C(O)-i-Pr.347W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is C(O)-t-Bu.348W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is CO 2 Me.349W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is CO 2 Et.350W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is CO 2 -i-Pr.351W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is CO 2 -t-Bu.352W is O, X is -CH=CH-, R 1< is Me, R 2< is OMe, and G is SO 2 Me.353W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is C(O)Me.354W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is C(O)Et.355W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is C(O)-i-Pr.356W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is C(O)-t-Bu.357W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is CO 2 Me.358W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is CO 2 Et.359W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is CO 2 -i-Pr.360W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is CO 2 -t-Bu.361W is O, X is -CH=CH-, R 1< is Me, R 2< is OEt, and G is SO 2 Me.362W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is C(O)Me.363W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is C(O)Et.364W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is C(O)-i-Pr.365W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is C(O)-t-Bu.366W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is CO 2 Me.367W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is CO 2 Et.368W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is CO 2 -i-Pr.369W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is CO 2 -t-Bu.370W is O, X is -CH=CH-, R 1< is Et, R 2< is Me, and G is SO 2 Me.371W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is C(O)Me.372W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is C(O)Et.373W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is C(O)-i-Pr.374W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is C(O)-t-Bu.375W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is CO 2 Me.376W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is CO 2 Et.377W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is CO 2 -i-Pr.378W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is CO 2 -t-Bu.379W is O, X is -CH=CH-, R 1< is Et, R 2< is H, and G is SO 2 Me.380W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is C(O)Me.381W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is C(O)Et.382W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is C(O)-i-Pr.383W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is C(O)-t-Bu.384W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is CO 2 Me.385W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is CO 2 Et.386W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is CO 2 -i-Pr.387W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is CO 2 -t-Bu.388W is O, X is -CH=CH-, R 1< is Et, R 2< is Et, and G is SO 2 Me.389W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is C(O)Me.390W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is C(O)Et.391W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is C(O)-i-Pr.392W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is C(O)-t-Bu.393W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is CO 2 Me.394W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is CO 2 Et.395W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is CO 2 -i-Pr.396W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is CO 2 -t-Bu.397W is O, X is -CH=CH-, R 1< is Et, R 2< is Pr, and G is SO 2 Me.398W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is C(O)Me.399W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is C(O)Et.400W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is C(O)-i-Pr.401W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is C(O)-t-Bu.402W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is CO 2 Me.403W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is CO 2 Et.404W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is CO 2 -i-Pr.405W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is CO 2 -t-Bu.406W is O, X is -CH=CH-, R 1< is Et, R 2< is CF 3 , and G is SO 2 Me.407W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is C(O)Me.408W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is C(O)Et.409W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is C(O)-i-Pr.410W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is C(O)-t-Bu.411W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is CO 2 Me.412W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is CO 2 Et.413W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is CO 2 -i-Pr.414W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is CO 2 -t-Bu.415W is O, X is -CH=CH-, R 1< is Et, R 2< is Cl, and G is SO 2 Me.416W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is C(O)Me.417W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is C(O)Et.418W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is C(O)-i-Pr.419W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is C(O)-t-Bu.420W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is CO 2 Me.421W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is CO 2 Et.422W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is CO 2 -i-Pr.423W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is CO 2 -t-Bu.424W is O, X is -CH=CH-, R 1< is Et, R 2< is Br, and G is SO 2 Me.425W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is C(O)Me.426W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is C(O)Et.427W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is C(O)-i-Pr.428W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is C(O)-t-Bu.429W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is CO 2 Me.430W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is CO 2 Et.431W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is CO 2 -i-Pr.432W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is CO 2 -t-Bu.433W is O, X is -CH=CH-, R 1< is Et, R 2< is I. and G is SO 2 Me.434W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is C(O)Me.435W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is C(O)Et.436W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is C(O)-i-Pr.437W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is C(O)-t-Bu.438W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is CO 2 Me.439W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is CO 2 Et.440W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is CO 2 -i-Pr.441W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is CO 2 -t-Bu.442W is O, X is -CH=CH-, R 1< is Et, R 2< is OMe, and G is SO 2 Me.443W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is C(O)Me.444W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is C(O)Et.445W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is C(O)-i-Pr.446W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is C(O)-t-Bu.447W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is CO 2 Me.448W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is CO 2 Et.449W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is CO 2 -i-Pr.450W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is CO 2 -t-Bu.451W is O, X is -CH=CH-, R 1< is Et, R 2< is OEt, and G is SO 2 Me.452W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is C(O)Me.453W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is C(O)Et.454W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is C(O)-i-Pr.455W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is C(O)-t-Bu.456W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is CO 2 Me.457W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is CO 2 Et.458W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is CO 2 -i-Pr.459W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is CO 2 -t-Bu.460W is O, X is -CH=CH-, R 1< is Pr, R 2< is Me, and G is SO 2 Me.461W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is C(O)Me.462W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is C(O)Et.463W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is C(O)-i-Pr.464W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is C(O)-t-Bu.465W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is CO 2 Me.466W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is CO 2 Et.467W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is CO 2 -i-Pr.468W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is CO 2 -t-Bu.469W is O, X is -CH=CH-, R 1< is Pr, R 2< is H, and G is SO 2 Me.470W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is C(O)Me.471W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is C(O)Et.472W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is C(O)-i-Pr.473W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is C(O)-t-Bu.474W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is CO 2 Me.475W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is CO 2 Et.476W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is CO 2 -i-Pr.477W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is CO 2 -t-Bu.478W is O, X is -CH=CH-, R 1< is Pr, R 2< is Et, and G is SO 2 Me.479W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is C(O)Me.480W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is C(O)Et.481W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is C(O)-i-Pr.482W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is C(O)-t-Bu.483W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is CO 2 Me.484W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is CO 2 Et.485W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is CO 2 -i-Pr.486W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is CO 2 -t-Bu.487W is O, X is -CH=CH-, R 1< is Pr, R 2< is Pr, and G is SO 2 Me.488W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is C(O)Me.489W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is C(O)Et.490W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is C(O)-i-Pr.491W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is C(O)-t-Bu.492W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is CO 2 Me.493W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is CO 2 Et.494W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is CO 2 -i-Pr.495W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is CO 2 -t-Bu.496W is O, X is -CH=CH-, R 1< is Pr, R 2< is CF 3 , and G is SO 2 Me.497W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is C(O)Me.498W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is C(O)Et.499W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is C(O)- i- Pr.500W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is C(O)-t-Bu.501W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is CO 2 Me.502W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is CO 2 Et.503W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is CO 2 -i-Pr.504W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is CO 2 -t-Bu.505W is O, X is -CH=CH-, R 1< is Pr, R 2< is Cl, and G is SO 2 Me.506W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is C(O)Me.507W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is C(O)Et.508W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is C(O)-i-Pr.509W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is C(O)-t-Bu.510W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is CO 2 Me.511W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is CO 2 Et.512W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is CO 2 -i-Pr.513W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is CO 2 -t-Bu.514W is O, X is -CH=CH-, R 1< is Pr, R 2< is Br, and G is SO 2 Me.515W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is C(O)Me.516W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is C(O)Et.517W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is C(O)-i-Pr.518W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is C(O)-t-Bu.519W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is CO 2 Me.520W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is CO 2 Et.521W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is CO 2 -i-Pr.522W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is CO 2 -t-Bu.523W is O, X is -CH=CH-, R 1< is Pr, R 2< is I. and G is SO 2 Me.524W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is C(O)Me.525W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is C(O)Et.526W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is C(O)-i-Pr.527W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is C(O)-t-Bu.528W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is CO 2 Me.529W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is CO 2 Et.530W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is CO 2 -i-Pr.531W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is CO 2 -t-Bu.532W is O, X is -CH=CH-, R 1< is Pr, R 2< is OMe, and G is SO 2 Me.533W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is C(O)Me.534W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is C(O)Et.535W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is C(O)-i-Pr.536W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is C(O)-t-Bu.537W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is CO 2 Me.538W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is CO 2 Et.539W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is CO 2 -i-Pr.540W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is CO 2 -t-Bu.541W is O, X is -CH=CH-, R 1< is Pr, R 2< is OEt, and G is SO 2 Me.542W is O, X is S, R 1< is CH 2 CF 3 , R 2< is Me, and G is H.543W is O, X is S, R 1< is CH 2 CF 3 , R 2< is Me, and G is C(O)Me.544W is O, X is S, R 1< is CH 2 CF 3 , R 2< is Me, and G is CO 2 Me.545W is O, X is S, R 1< is CH 2 CF 3 , R 2< is Br, and G is H.546W is O, X is S, R 1< is CH 2 CF 3 , R 2< is Br, and G is C(O)Me.547W is O, X is S, R 1< is CH 2 CF 3 , R 2< is Br, and G is CO 2 Me.548W is O, X is S, R 1< is CH 2 CH 2 CN, R 2< is Me, and G is H.549W is O, X is S, R 1< is CH 2 CH 2 CN, R 2< is Me, and G is C(O)Me.550W is O, X is S, R 1< is CH 2 CH 2 CN, R 2< is Me, and G is CO 2 Me.551W is O, X is S, R 1< is CH 2 CH 2 CN, R 2< is Br, and G is H.552W is O, X is S, R 1< is CH 2 CH 2 CN, R 2< is Br, and G is C(O)Me.553W is O, X is S, R 1< is CH 2 CH 2 CN, R 2< is Br, and G is CO 2 Me.554W is O, X is -CH=CH-, R 1< is CH 2 CF 3 , R 2< is Me, and G is H.555W is O, X is -CH=CH-, R 1< is CH 2 CF 3 , R 2< is Me, and G is C(O)Me.556W is O, X is -CH=CH-, R 1< is CH 2 CF 3 , R 2< is Me, and G is CO 2 Me.557W is O, X is -CH=CH-, R 1< is CH 2 CF 3 , R 2< is Br, and G is H.558W is O, X is -CH=CH-, R 1< is CH 2 CF 3 , R 2< is Br, and G is C(O)Me.559W is O, X is -CH=CH-, R 1< is CH 2 CF 3 , R 2< is Br, and G is CO 2 Me.560W is O, X is -CH=CH-, R 1< is CH 2 CH 2 CN, R 2< is Me, and G is H.561W is O, X is -CH=CH-, R 1< is CH 2 CH 2 CN, R 2< is Me, and G is C(O)Me.562W is O, X is -CH=CH-, R 1< is CH 2 CH 2 CN, R 2< is Me, and G is CO 2 Me.563W is O, X is -CH=CH-, R 1< is CH 2 CH 2 CN, R 2< is Br, and G is H.564W is O, X is -CH=CH-, R 1< is CH 2 CH 2 CN, R 2< is Br, and G is C(O)Me.565W is O, X is -CH=CH-, R 1< is CH 2 CH 2 CN, R 2< is Br, and G is CO 2 Me.566W is O, X is O, R 1< is Me, R 2< is Me, and G is H.567W is O, X is O, R 1< is Me, R 2< is Me, and G is C(O)Me.568W is O, X is O, R 1< is Me, R 2< is Me, and G is CO 2 Me.569W is O, X is O, R 1< is Me, R 2< is Br, and G is H.570W is O, X is O, R 1< is Me, R 2< is Br, and G is C(O)Me.571W is O, X is O, R 1< is Me, R 2< is Br, and G is CO 2 Me.572W is O, X is -CH=C(Me)-, R 1< is Me, R 2< is Me, and G is H.573W is O, X is -CH=C(Me)-, R 1< is Me, R 2< is Me, and G is C(O)Me.574W is O, X is -CH=C(Me)-, R 1< is Me, R 2< is Me, and G is CO 2 Me.575W is O, X is -CH=C(Me)-, R 1< is Me, R 2< is Br, and G is H.576W is O, X is -CH=C(Me)-, R 1< is Me, R 2< is Br, and G is C(O)Me.577W is O, X is -CH=C(Me)-, R 1< is Me, R 2< is Br, and G is CO 2 Me.578W is O, X is N(Me), R 1< is Me, R 2< is Me, and G is H.579W is O, X is N(Me), R 1< is Me, R 2< is Me, and G is C(O)Me.580W is O, X is N(Me), R 1< is Me, R 2< is Me, and G is CO 2 Me.581W is O, X is N(Me), R 1< is Me, R 2< is Br, and G is H.582W is O, X is N(Me), R 1< is Me, R 2< is Br, and G is C(O)Me.583W is O, X is N(Me), R 1< is Me, R 2< is Br, and G is CO 2 Me.584W is O, X is -CH=C(F)-, R 1< is Me, R 2< is Me, and G is H.585W is O, X is -CH=C(F)-, R 1< is Me, R 2< is Me, and G is C(O)Me.586W is O, X is -CH=C(F)-, R 1< is Me, R 2< is Me, and G is CO 2 Me.587W is O, X is -CH=C(F)-, R 1< is Me, R 2< is Br, and G is H.588W is O, X is -CH=C(F)-, R 1< is Me, R 2< is Br, and G is C(O)Me.589W is O, X is -CH=C(F)-, R 1< is Me, R 2< is Br, and G is CO 2 Me.590W is O, X is -CH=C(Cl)-, R 1< is Me, R 2< is Me, and G is H.591W is O, X is -CH=C(Cl)-, R 1< is Me, R 2< is Me, and G is C(O)Me.592W is O, X is -CH=C(Cl)-, R 1< is Me, R 2< is Me, and G is CO 2 Me.593W is O, X is -CH=C(Cl)-, R 1< is Me, R 2< is Br, and G is H.594W is O, X is -CH=C(Cl)-, R 1< is Me, R 2< is Br, and G is C(O)Me.595W is O, X is -CH=C(Cl)-, R 1< is Me, R 2< is Br, and G is CO 2 Me.596W is O, X is -CH=C(OMe)-, R 1< is Me, R 2< is Me, and G is H.597W is O, X is -CH=C(OMe)-, R 1< is Me, R 2< is Me, and G is C(O)Me.598W is O, X is -CH=C(OMe)-, R 1< is Me, R 2< is Me, and G is CO 2 Me.599W is O, X is -CH=C(OMe)-, R 1< is Me, R 2< is Br, and G is H.600W is O, X is -CH=C(OMe)-, R 1< is Me, R 2< is Br, and G is C(O)Me.601W is O, X is -CH=C(OMe)-, R 1< is Me, R 2< is Br, and G is CO 2 Me.602W is O, X is -CH=C(CN)-, R 1< is Me, R 2< is Me, and G is H.603W is O, X is -CH=C(CN)-, R 1< is Me, R 2< is Me, and G is C(O)Me.604W is O, X is -CH=C(CN)-, R 1< is Me, R 2< is Me, and G is CO 2 Me.605W is O, X is -CH=C(CN)-, R 1< is Me, R 2< is Br, and G is H.606W is O, X is -CH=C(CN)-, R 1< is Me, R 2< is Br, and G is C(O)Me.607W is O, X is -CH=C(CN)-, R 1< is Me, R 2< is Br, and G is CO 2 Me.608W is S, X is S, R 1< is Me, R 2< is Me, and G is H.609W is S, X is S, R 1< is Me, R 2< is Me, and G is C(O)Me.610W is S, X is S, R 1< is Me, R 2< is Me, and G is CO 2 Me.611W is S, X is S, R 1< is Me, R 2< is Br, and G is H.612W is S, X is S, R 1< is Me, R 2< is Br, and G is C(O)Me.613W is S, X is S, R 1< is Me, R 2< is Br, and G is CO 2 Me.614W is S, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is H.615W is S, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is C(O)Me.616W is S, X is -CH=CH-, R 1< is Me, R 2< is Me, and G is CO 2 Me.617W is S, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is H.618W is S, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is C(O)Me.619W is S, X is -CH=CH-, R 1< is Me, R 2< is Br, and G is CO 2 Me.620W is O, X is -CH=CH-, R 1< is CH 3 , R 2< is Me, and G is H.621W is S, X is -CH=CH-, R 1< is CH 3 , R 2< is Me, and G is H.622W is O, X is -CH=CH-, R 1< is CH 2 CH 3 , R 2< is Me, and G is H.623W is S, X is -CH=CH-, R 1< is CH 2 CH 3 , R 2< is Me, and G is H.624W is O, X is -CH=CH-, R 1< is CH 3 , R 2< is Et, and G is H.625W is S, X is -CH=CH-, R 1< is CH 3 , R 2< is Et, and G is H.626W is O, X is -CH=CH-, R 1< is CH 2 CH 3 , R 2< is Et, and G is H.627W is S, X is -CH=CH-, R 1< is CH 2 CH 3 , R 2< is Et, and G is H.

[0097] Test results indicate that the compounds of the Formula 1 are highly active preemergent and / or postemergent herbicides and / or plant growth regulants. The compounds of Formula 1 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 Formula 1, 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 Formula 1 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 Formula 1 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.

[0098] As the compounds of Formula 1 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 Formula 1, 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.

[0099] A herbicidally effective amount of the compounds of Formula 1 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 Formula 1 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.

[0100] A compound of Formula 1 may be 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 Formula 1 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.

[0101] The following Tests demonstrate the control efficacy of the compounds of Formula 1 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 following abbreviations are used in the Index Table which follows: t is tertiary, Me is methyl, morph is morpholinyl, Bn is benzyl and Bu is butyl. 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 Cmpd. No.R 1< R 2< X(R 3< )nR 4< Gm.p. (°C)M+1NMR1 (Ex. 1)MeMeS5-MeMeH301.5**2MeMeS5,7-di-MeMeH*3MeMeS4,6-di-MeMeH224-227315.5*4MeMeO-MeH238-240271.5*5MeMeO5-OMeMeH301.5*6MeMeO5-ClMeH*7 (Ex. 2)MeMeO5-MeMeH**8MeMeO4-MeMeH*9MeMeO7-MeMeH285.5*10MeMeO5-MeEtH299.5*11MeMe-CH=CH--HH267*12 (Ex. 3)MeMeO5,7-di-MeMeH**13MeMeO5-EtMeH*14MeMeO5-MeMe-C(=O)Me*15MeMeO7-MeMe-C(=O)Me*16MeMeO5,7-di-MeMe-C(=O)Me341.0*17MeMeO5-MeMe-C(=O)-t-Bu369.0*18MeMeO5,7-di-MeMe-C(=O)-t-Bu383.0*19MeMeS4,6-di-MeEtH*20MeBr-CH=CH--HH33221MeMe-CH=C(Me)--MeH*22MeMeS5-BrMeH36723MeBr-CH=CH--MeH34324MeH-CH=CF--HH*25MeMeS5-MeMe-C(=O)Me*26MeMeS5-MeMe-C(=O)-t-Bu385.427MeMeS5,7-di-MeMe-C(=O)Me140-14528MeMeS5,7-di-MeMe-C(=O)Et134-13729MeI-CH=CH--MeH39330MeOMe-CH=CH-5-MeMeH31131MeMeN(Me)5-MeMeH94-9832MeMe-CH=CH--EtH226-22933MeOMeS-MeH30334MeMe-C(Me)=CH--MeH29535MeMeS5-Cl, 7-MeMeH33536MeOMe-CH=CH--Me-C(=O)O-i-Pr*37MeMe-CH=CH--Et-C(=O)OEt367.638MeMe-CH=CH--Et-C(=O)-c-Pr363.639MeMe-CH=CH--Et-C(=O)O-i-Pr112-11640MeMe-CH=CH--OMeH29741MeMe-CH=CF--HH*42MeMeS5-MeMe-C(=O)Et125-13043MeMeS5,7-di-MeMe-C(=O)-t-Bu399.444MeMeS4,6-di-MeMe-C(=O)Me35745MeMeS4,6-di-MeMe-C(=O)-t-Bu39946MeOMe-C(Me)=CH--MeH31147MeMeS5-MeEtH203-20548MeHS-MeH27349MeH-CH=CH--HH251.5 #< 50MeH-CH=C(Me)--HH26751MeH-CH=C(Me)--MeH*52MeBr-CH=C(Me)--HH347.453MeMeS5-OMeMeH187-18954MeOMe-CH=CH--MeH29755MeOMe-CH=CH--HH28356MeH-CH=CH--MeH249-25157MeMeS5,7-di-MeEtH200-20258MeMeCH=C(OMe)--HH29759MeMe-CH=CH--MeH269-27360MeMe-CH=CH-5-MeMeH230-23361MePhO5-MeMeH259-26362MeMe-CH=C(Cl)--H-C(=O)Et*63MeMe-CH=C(Cl)--H-C(=O)OMe35964EtEtO5-MeMeH215-21965MeMeS-MeH225-22866MeMeS5-MeMe-C(=O)O-i-Pr128-12967MeMeS5,7-di-MeMe-C(=O)O-i-Pr123-12568MeMeO5-OEtEtH170-17469MeMe-CH=CH-5-MeHH28270MeMe-CH=CH-5-IHH39371MeMe-CH=CH-5-c-PrHH30772MeMe-CH=CH--Me-C(=O)O-i-Pr230-23573MeMe-CH=CH--Me-C(=O)OEt146-15074MeMeN(Me)5-ClMeH314-31875MeMe-CH=C(Br)--HH285-28976MeMe-CH=CH--Me-C(=O)-c-Pr34977MeEtO5-ClMeH242-24878MeMe-CH=CH--Me-C(=O)Et*79MeMeS5-MeBrH367.280MeMeS5-MeMe-C(=O)OMe359.581MeMeS5,7-di-MeMe-C(=O)OMe373.582MeMeS5-MeMe-C(=O)OEt373.583MeMeS5,7-di-MeMe-C(=O)OEt387.584MeMeS5-MeMeC(=O)OCH 2 CH 2 Cl407.485MeMeS5,7-di-MeMeC(=O)OCH 2 CH 2 Cl421.486MeOMe-CH=CH--CF 2 HH331#87MeMeS5-MeMeC(=O)OCH 2 C≡CH383.388MeMeS5,7-di-MeMeC(=O)OCH 2 C≡CH397.389MeClS-MeH30790MeMe-CH=CF--H-C(=O)Me*91MeClS5-ClMeH92MeMe-CH=CH-5-OEtHH30993MeMe-CH=CH-5-OCF 2 HHH33394MeClS-Me-C(=O)O-i-Pr*95MeMeNMe-ClH237-23996MeMe-CH=CH-5-OEtHH29797MeHS-Me-C(=O)OMe33198MeCN-CH=CH--Me-C(=O)Me*99MeMe-CH=CMe--Me-C(=O)Me*100MeOMeS5-ClMeH337101MeClS5-ClMe-C(=O)OMe*102MeCF 3 -CH=CH--MeH335103MeMe-CH=CH-5-MeEtH186-189104MeMeS5-ClMeH254-257105MeMeS5-MeMe-C(=O)-n-Pr115-117106MeMeS5,7-di-MeMe-C(=O)-n-Pr113-115107MeMeS5-MeEt-C(=O)-n-Pr80-82108MeMeS5-ClMe-C(=O)Me203-206109MeMeS5-ClMe-C(=O)Et125-127110MeMe-CH=CH-6-MeMeH295111MeClS5-ClMe-C(=O)Et*112MeOMeS5-ClMe-C(=O)OMe395113MeMe-CH=CF--H-C(=O)Et-*114MeClS5-ClMe-SO 2 Me*115MeMe-CF=CH--H-SO 2 Me363116MeClS5-ClMe-C(=O)Me*117MeEtO-MeH210-215118MeEtO5-MeMeH334-338119Mei-PrO5-MeMeH245-250120MeHS-Me-C(=O)Me*121MeMeS5-CF 3 MeH355122MeOMeS5-ClMe-C(=O)Me*123MeMe-CH=CF--H-C(=O)CH 2 CF 3 *124MeMe-CH=CH-5-OC(=O)MeH-C(=O)Me*125MeCl-CH=CH--MeH301126MeMe-CH=CH-5-BrHH347127MeMe-CH=CH-5-CNHH292128MeCN-CH=CH--Me-C(=O)-t-Bu*129MeBr-CH=CH--Me-C(=O)Me*130MeMe-CH=CF--H-C(=O)OMe*131MeOMeS5-ClMe-C(=O)Et*132MeMeS5-CF 3 Me-C(=O)Me*133MeMe-CH=CBr--H-C(=O)OEt117-120134MeMe-CH=CBr--H-C(=O)Et120-124135MeOMeS5-ClMe-SO 2 Me415136MeOMe-CH=CH--Me-C(=O)OMe355137MeBr-CH=CH--Me-C(=O)OMe*138MeOMe-CH=CH--Me-C(=O)Me*139MeMe-CH=CCl--HH301140MeClS5-CF 3 MeH375141MeOMeS-Me-C(=O)Me*142MeH-CH=CH--Me-SO 2 Me345143MeH-CH=CH--Me-C(=O)OMe325144MeMe-CH=CH-5-ClMeH280-284145MeMe-CH=CBr--H-C(=O)OMe403146MeMe-CH=CH--CF 3 -C(=O)OEt115-118147MeMe-CH=CH--CF 3 -C(=O)Et132-135148MeMe-CH=CH--CF 3 -C(=O)Me181-184149MeMe-CH=CH--CF 3 -C(=O)OMe130-133150MeMe-CH=CH-5-C≡CHHH291151MeMe-CH=CH-5-F,7-MeMeH319.1152MeClS5-CF 3 Me-C(=O)Me*153MeMe-CH=CMe--Me-C(=O)Me*154MeMe-CH=CMe--Me-SO 2 Me373155MeBr-CH=CH--Me-SO 2 Me*156MeBr-CH=CH--Me-C(=O)Et*157MeMe-CH=CCl--H-C(=O)Me343158MeMe-CH=CCl--H-SO 2 CF 3 ?433159MeMe-CH=CCl--H-C(=O)CF 3 *160MeMeS5-MeMe-CH 2 CN340161MeMe-CH=CH-5-NO 2 MeH312162MeMe-CH=CH--NO 2 -C(=O)OMe162-166163MeMe-CH=CH--NO 2 -C(=O)-t-Bu239-243164MeMe-CH=CH--NO 2 -C(=O)Me189-193165MeMe-CH=CH--NO 2 H264-268166MeMe-CH=CH--NO 2 -C(=O)OEt147-150167MeMe-CH=CH--NO 2 -C(=O)-c-Pr165-170168BnMe-CH=CH--HH343169HMe-CH=CH--HH253170MeMeS-Me-C(=O)-N-morph168-171171MeMe-CH=CH--H-C(=O)CH 2 SMe*172CH 2 CO 2 MeMe-CH=CH--HH325173HMe-CH=CH--H-CH 2 CF 2 H317174MeMeS5,7-di-MeMe-C(=O)-N-morph428175HMe-CH=CH--H-CF 2 H303176MeBr-CH=CH--Me-C(=O)-N-morph*177MeNO 2 -CH=CH--MeH312178MeMe-CH=CH--H-CH 2 C(=O)Me323179MeMe-CH=CH--H-CH 2 C≡CH305180MeMe-CH=CH--H-CH 2 CH=CHPh383181MeMe-CH=CH--H-CH 2 C(=O)-c-Pr349182MeMe-CH=CH--H-CH 2 C(=O)OMe339183MeMe-CH=CH--H-C(=O)CH=CHPh397184MeMe-CH=CH--H-CH 2 C(=O)Ph385185MeMe-CH=CCl--H-SO 2 N(Me) 2 408186MeMe-CH=CCl--H-P(=O)(OMe) 2 410187MeMe-CH=CCl--H-P(=O)(Me) 2 377188MeMeS5,7-di-MeMe-CH 2 CN354* See Index Table B for 1< H NMR data. ** See Synthesis Example for 1< H NMR data. # M-1 peak. INDEX TABLE B Cmpd. No. 1< H NMR Data (CDCl 3 solution unless indicated otherwise) a< 2δ 6.93 (s, 1H), 6.90 (s, 1H), 6.41 (br s, 1H), 3.60 (s, 3H), 2.47 (s, 3H), 2.36 (s, 3H), 2.25-2.29 (m, 6H)3δ 7.40 (s, 1H), 6.83 (s, 1H), 6.10 (br s, 1H), 3.66 (s, 3H), 2.38 (s, 3H), 2.28 (s, 3H), 2.21 (s, 3H), 2.13 (s, 3H).4(DMSO-d 6 ) δ 10.33 (s, 1H), 7.52 (d, 1H), 7.14-7.27 (m, 3H), 3.60 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H).5δ 7.34 (d, 1H), 6.84-6.87 (m, 1H), 6.65-6.66 (d, 1H), 3.79 (s, 3H), 3.75 (s, 3H), 2.36 (s, 3H), 2.35 (s, 3H).6δ 7.35-7.39 (m, 1H), 7.20-7.24 (m, 2H), 6.08 (br s, 1H), 3.72 (s, 3H), 2.36 (s, 3H), 2.32 (s, 3H).8δ 7.28-7.30 (d, 1H), 7.13-7.16 (m, 1H), 6.93-6.96 (m, 1H), 5.65-5.80 (br s, 1H), 3.77 (s, 3H), 2.35 (s, 3H), 2.31 (s, 3H), 2.23 (s, 3H).9(DMSO-d 6 ) δ 10.26 (s, 1H), 6.99-7.07 (m, 3H), 3.60 (s, 3H), 2.48 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H).10(DMSO-d 6 ) δ 10.28-10.30 (br s, 1H), 7.39-7.42 (m, 1H), 7.03-7.07 (m, 1H), 6.96-6.98 (m, 1H), 3.60 (s, 3H), 2.55-2.62 (m, 2H), 2.34 (s, 3H), 2.25 (s, 3H), 1.18-1.23 (m, 3H).11(DMSO-d 6 ) δ 10.11 (br s, 1H), 8.10-7.93 (m, 2H), 7.58-7.40 (m, 4H), 7.35-7.31 (m, 1H), 3.60 (s, 3H), 2.27 (s, 3H).13δ 7.35 (d, 1H), 7.08-7.13 (m, 1H), 7.00-7.05 (m, 1H), 5.99-6.03 (m, 1H), 3.72 (s, 3H), 2.70 (m, 2H), 2.35 (s, 3H), 2.32 (s, 3H), 1.17-1.29 (m, 3H).14δ 7.27-7.29 (m, 1H), 7.06-7.07 (m, 1H), 7.01 (m, 1H), 3.83 (s, 3H), 2.38-2.40 (m, 6H), 2.29 (s, 3H), 1.89 (s, 3H).15δ 7.07-7.11 (m, 2H), 7.00-7.02 (m, 1H), 3.84 (s, 3H), 2.50 (s, 3H), 2.42 (s, 3H), 2.29 (s, 3H), 1.89 (s, 3H).16δ 6.88 (s, 1H), 6.83 (s, 1H), 3.84 (s, 3H), 2.45 (s, 3H), 2.39 (s, 3H), 2.35 (s, 3H), 2.29 (s, 3H), 1.91 (s, 3H).17δ 7.26 (d, 1H), 7.02 (d, 1H), 7.00 (d, 1H), 3.84 (s, 3H), 2.37 (d, 6H), 2.26 (s, 3H) 0.93 (br s, 9H).18δ 6.83 (s, 1H), 6.81 (s, 1H), 3.83 (s, 3H), 2.44 (s, 3H), 2.37 (s, 3H), 2.34 (s, 3H), 2.25 (s, 3H), 0.94 (br s, 9H).19δ 7.45 (s, 1H), 6.86 (s, 1H), 5.62 (s, 1H), 3.74 (s, 3H), 2.55-2.71 (m, 2H), 2.39 (s, 3H), 2.32 (s, 3H), 2.18 (s, 3H), 1.20-1.29 (m, 3H).21δ 8.03 (m, 1H), 7.61-7.49 (m, 3H), 7.32 (s, 1H), 5.23 (br s, 1H), 3.79 (s, 1H), 2.71 (s, 1H), 2.36 (s, 3H), 2.26 (s, 3H).24δ 8.17 (m, 1H), 7.75 (s, 1H), 7.62-7.52 (m, 3H), 7.38 (m, 1H), 7.25 (m, 1H), 5.69 (br s, 1H), 3.81 (s, 3H).25δ 8.17 (m, 1H), 7.62-7.52 (m, 3H), 7.37 (m, 1H), 7.26 (m, 1H) 5.49 (s, 1H), 3.77 (s, 3H), 2.36 (s, 3H).36δ 7.82-7.78 (m, 2H), 7.45-7.35 (m, 4H), 4.72-4.64 (m, 1H), 3.97 (s, 3H), 3.78 (s, 3H), 2.30 (s, 3H), 1.10 (m, 3H), 1.03 (m, 3H).41δ 8.18 (m, 1H), 7.62-7.54 (m, 3H), 7.36 (m, 1H), 7.25 (m, 2H), 5.48 (s, 1H), 3.77 (s, 3H), 2.36 (s, 3H).51δ 8.04 (m, 2H), 7.73 (s, 1H), 7.53-7.45 (m, 2H), 7.31 (s, 1H), 5.60 (br s, 1H) 3.83 (s, 3H), 2.70 (s, 3H), 2.26 (s, 3H).62δ 8.28-8.35 (m, 1H), 7.57-7.65 (m, 2H), 7.47-7.56 (m, 2H), 7.20-7.29 (m, 1H), 3.85 (s, 3H), 2.29 (s, 3H), 1.96-2.19 (m, 2H), 0.62-0.85 (m, 3H).78(500MHz) δ 7.88 (s, 1H), 7.81 (s, 1H), 7.79 (s, 1H), 7.44-7.33 (m, 4H), 3.91-3.88 (m, 3H), 2.29 (s, 3H), 2.02 (m, 2H), 0.76 (s, 1H), 0.64 (m, 3H).90(500MHz) δ 8.15-8.14 (m, 1H), 7.65-7.51 (m, 4H), 7.29-7.27 (m, 1H), 7.20-7.16 (m, 1H), 3.85 (s, 3H), 2.31 (s, 3H), 1.84 (s, 3H).95(500MHz) δ 7.75-7.72 (m, 1H), 7.33-7.26 (m, 3H), 4.66-4.63 (m, 1H), 3.87 (s, 3H), 2.43 (s, 3H), 1.07-1.00 (m, 6H).99δ 7.81-7.87 (m, 2H), 7.38-7.45 (m, 3H), 7.30-7.34 (m, 1H), 3.96 (s, 3H), 2.28 (s, 3H), 1.85 (s, 3H).100(500MHz) δ 7.78-7.76 (m, 1H), 7.71 (s, 1H), 7.42-7.31 (m, 2H), 7.23-7.22 (m, 1H), 3.84 (s, 3H), 2.52 (s, 3H), 2.48 (s, 3H), 2.18 (s, 3H).102(500MHz) δ 7.67-7.66 (m, 1H), 7.27-7.24 (m, 2H), 3.88 (s, 3H), 3.69 (s, 3H), 2.43 (s, 3H).112(500MHz) δ 7.67-7.65 (m, 1H), 7.46-7.27 (m, 2H), 3.87 (s, 3H), 2.42 (s, 3H), 2.35-2.13 (m, 2H), 0.86-0.83 (m, 3H).114(500MHz) δ 8.15-8.13 (m, 1H), 7.60-7.49 (m, 3H), 7.33-7.27 (m, 1H), 7.21-7.16 (m, 1H), 3.85 (s, 3H), 2.29 (s, 3H), 2.13-2.02 (m, 2H), 0.78-0.75 (m, 3H).115(500MHz) δ 7.69-7.68 (m, 1H), 7.31-7.27 (m, 2H), 3.88 (s, 3H), 2.58 (s, 3H), 2.48 (s, 3H).117(500MHz) δ 7.67-7.65 (m, 1H), 7.26-7.24 (m, 2H), 3.87 (s, 3H), 2.42 (s, 3H), 1.96 (s, 3H).121(500MHz) δ 7.84 (s, 1H), 7.79-7.69 (m, 1H), 7.30-7.26 (m, 3H), 3.88 (s, 3H), 2.43 (s, 3H), 1.90 (s, 3H).123(500MHz) δ 7.65-7.64 (m, 1H), 7.28-7.27 (m, 1H), 7.24-7.22 (m, 1H), 3.93 (s, 3H), 3.77 (s, 3H), 2.42 (s, 3H), 1.98 (s, 3H).124(500MHz) δ 8.16-8.15 (m, 1H), 7.60-7.45 (m, 3H), 7.29-7.26 (m, 2H), 7.20-7.17 (m, 1H), 3.87 (s, 3H), 3.00-2.82 (m, 2H), 2.31 (s, 3H).125δ 7.84-7.94 (m, 2H), 7.46-7.55 (m, 1H), 7.33-7.40 (m, 1H), 7.23-7.30 (m, 1H), 7.16-7.21 (m, 1H), 3.85 (s, 3H), 2.31 (s, 3H), 2.29 (s, 3H), 1.82 (s, 3H).129δ 7.78-7.85 (m, 2H), 7.36-7.45 (m, 3H), 7.29-7.35 (m, 1H), 3.98 (s, 3H), 2.29 (s, 3H), 0.72 (s, 9H).130δ 7.82, (m, 2H), 7.29 (m, 4H), 3.88 (s, 1H), 2.30 (s, 3H) 1.80 (s, 3H).131(500MHz) δ 8.24-8.13 (m, 1H), 7.60-7.52 (m, 3H), 7.34-7.30 (m, 1H), 7.26-7.18 (m, 1H), 3.88 (s, 3H), 3.61 (s, 3H), 2.37 (s, 3H).132(500MHz) δ 7.65-7.63 (m, 1H), 7.35-7.27 (m, 1H), 7.26-7.19 (m, 1H), 3.93 (s, 3H), 3.77 (s, 3H), 2.42 (s, 3H), 2.29-2.19 (m, 2H), 0.89-0.86 (m, 3H).133(500MHz) δ 7.89-7.83 (m, 1H), 7.54-7.48 (m, 2H), 3.86 (s, 3H), 2.45 (s, 3H), 2.32 (s, 3H), 1.81 (s, 3H).138(500MHz) δ 7.84-7.82 (m, 2H), 7.45-7.35 (m, 4H), 3.90 (s, 3H), 3.58 (s, 3H), 2.30 (s, 3H).139(500MHz) δ 7.81-7.79 (m, 2H), 7.44-7.36 (m, 4H), 3.95 (s, 3H), 3.78 (s, 3H), 2.30 (s, 3H), 1.85 (s, 3H).142(500MHz) δ 7.75-7.73 (m, 1H), 7.29-7.23 (m, 3H), 3.93 (s, 3H), 3.76 (s, 3H), 2.42 (s, 3H), 1.94 (s, 3H).153(500MHz) δ 7.93-7.83 (m, 1H), 7.53-7.52 (m, 2H), 3.88 (s, 3H), 2.46 (s, 3H), 1.93 (s, 3H).154(500MHz) δ 7.97-7.95 (m, 1H), 7.48-7.34 (m, 3H), 7.29-7.26 (m, 1H), 3.85 (s, 3H), 2.74 (s, 3H), 2.30 (s, 3H), 2.24 (s, 3H), 1.71 (s, 3H).156(500MHz) δ 7.89-7.87 (m, 2H), 7.48-7.38 (m, 4H), 3.90 (s, 3H), 2.37 (s, 3H), 2.07 (s, 3H).157(500MHz) δ 7.86-7.76 (m, 2H), 7.44-7.35 (m, 4H), 3.90 (s, 3H), 2.30 (s, 3H), 2.09-2.03 (m, 2H), 0.65-0.62 (m, 3H).160δ 8.31-8.37 (m, 1H), 7.59-7.68 (m, 2H), 7.49-7.56 (m, 1H), 7.42-7.48 (m, 1H), 7.19-7.25 (m, 1H), 3.93 (s, 3H), 2.37 (s, 3H).175(500MHz) δ 8.17-8.10 (m, 1H), 7.59-7.45 (m, 3H), 7.31-7.27 (m, 1H), 7.23-7.14 (m, 1H), 3.86 (s, 3H), 2.95-2.88 (m, 2H), 2.33 (s, 3H), 1.67 (s, 3H).180(500MHz) δ 7.89-7.77 (m, 2H), 7.50-7.33 (m, 4H), 3.90 (s, 3H), 3.26-2.86 (m, 6H), 2.33 (s, 3H). a 1< H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet, (br s)-broad singlet. BIOLOGICAL EXAMPLESTEST A

[0102] Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii), morningglory (Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), and corn (Zea mays) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

[0103] At the same time, plants selected from these crop and weed species and also blackgrass (Alopecurus myosuroides), and galium (catchweed bedstraw, Galium aparine) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 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 ACompounds1000 g ai / ha1345671011133260178179180PostemergenceBarnyardgrass90507040709090808090900100Blackgrass-------309090304030Corn4000001020502050500100Crabgrass, Large9010508050507070----Foxtail, Giant80108080709080908090900100Galium--------70100100709080Kochia--------30100100101040Morningglory1009070704010010090------Pigweed100050105010090902010010070050Ragweed--------3010010060400Ryegrass, Italian--------70100100707070Velvetleaf1007060--100100100------Wheat000020200602010070000 Table ACompounds1000 g ai / ha181182183184PostemergenceBarnyardgrass004020Blackgrass20108030Corn00100Crabgrass, Large----Foxtail, Giant007020Galium80509090Kochia009080Morningglory----Pigweed3009080Ragweed30307030Ryegrass, Italian80010080Velvetleaf----Wheat0000 Table ACompounds500 g ai / ha2891214151617181920212223PostemergenceBarnyardgrass800904070909004080100905090Blackgrass---503050304020040907080Corn200002020002003060050Crabgrass, Large703050-----------Foxtail, Giant90309070709080020601001009090Galium----909090100606080100100100100Kochia---60905060000100100100100Morningglory1001080-----------Pigweed1008005080040000100100100100Ragweed---70905070000100100100100Ryegrass, Italian---7080908060500100100100100Velvetleaf1006010-----------Wheat200000000003060080 Table ACompounds500 g ai / ha2425262728293031333435363738PostemergenceBarnyardgrass5090309090803010909090809040Blackgrass50907090908060204090808010060Corn02002020400010030404010Crabgrass, Large--------------Foxtail, Giant6090609090906010909090909050Galium10010090100100909070100100100100100100Kochia8010090909090800100801001009080Morningglory--------------Pigweed90100901009010090407090909010050Ragweed601009010010010070209010080909070Ryegrass, Italian9010090100100100600701001008010050Velvetleaf--------------Wheat7000006010004040308020 Table ACompounds500 g ai / ha3940414243444546474849505152PostemergenceBarnyardgrass1060909030008080502008050Blackgrass70809090800070703030106030Corn0107020000010000020Crabgrass, Large--------------Foxtail, Giant608010010070008080602008050Galium1001001001009070090100908080100100Kochia30901001001000409080102090100Morningglory--------------Pigweed80100901001000901007040509030Ragweed90901001000009010020102070100Ryegrass, Italian6090100100600080806050409080Velvetleaf--------------Wheat1050802000020000000 Table ACompounds500 g ai / ha5354555657585961626364656667PostemergenceBarnyardgrass20909060100090090900909070Blackgrass304080506050100080800708080Corn030201030060030400000Crabgrass, Large--------------Foxtail, Giant309090609010100090900909090Galium80100100100100100100010010001009090Kochia801001001001009010001001000909030Morningglory--------------Pigweed7010090901002010001001000909020Ragweed70100100901006010001001000909070Ryegrass, Italian7010010010090801000100100010010090Velvetleaf--------------Wheat20200501020100050400000 Table ACompounds500 g ai / ha6869707172737475767778798081PostemergenceBarnyardgrass804010206090106030030808090Blackgrass104030409090407010080808090Corn000204060020000000Crabgrass, Large--------------Foxtail, Giant50402520901002050200708080100Galium09090901001002010080601009090100Kochia08060709010030904010909090100Morningglory--------------Pigweed0908080901005050200909090100Ragweed0807070901001090200809090100Ryegrass, Italian0908090100100010080601009090100Velvetleaf--------------Wheat0002070900200060000 Table ACompounds500 g ai / ha8283848586878889909192939495PostemergenceBarnyardgrass5090408010809080100900204010Blackgrass7010080903080906090602003010Corn00000000303003000Crabgrass, Large--------------Foxtail, Giant701008090708010080100100010500Galium9010090100100901009010010030909060Kochia8010080708090100901009070306010Morningglory--------------Pigweed80100901009090100901001003060700Ragweed7010090908090100901001000506010Ryegrass, Italian8010080905080100901001000905050Velvetleaf--------------Wheat0200000003030020200 Table ACompounds500 g ai / ha96979899100101102103104105106107108109PostemergenceBarnyardgrass209090903030909010090901009090Blackgrass2090308070407090909090909090Corn07020402020206020302030030Crabgrass, Large--------------Foxtail, Giant2010010090805090901009090909090Galium5010010010010090100100100100100100100100Kochia70100607010030409010090909010090Morningglory--------------Pigweed70100100909070901009090909010090Ragweed5010010010090801001001001009090100100Ryegrass, Italian60100100100100508010010010010090100100Velvetleaf--------------Wheat080303020202020202020202030 Table ACompounds500 g ai / ha110111112113114115116117118119120121122123PostemergenceBarnyardgrass10902090909090400010503070Blackgrass6070809060707000010504050Corn202030703020300000202020Crabgrass, Large--------------Foxtail, Giant1010050909090100200010806060Galium901009010010010010000070907090Kochia709030100609060100030807070Morningglory--------------Pigweed90100301009090100200050907070Ragweed100100801008010010000010906090Ryegrass, Italian90100100100901001000008010070100Velvetleaf-----------Wheat40303070403050000020020 Table ACompounds500 g ai / ha124125126127128129130131132133134135136137PostemergenceBarnyardgrass309060508010090203090600100100Blackgrass08070502010070505060703090100Corn03020100803010105050203070Crabgrass, Large--------------Foxtail, Giant09060607010090808090800100100Galium30901001007010010010010010010090100100Kochia0100908009010080801001000100100Morningglory--------------Pigweed010010010090100100909010010020100100Ragweed01009080301001009010010010060100100Ryegrass, Italian010010090501001009010010010070100100Velvetleaf--------------Wheat0802020080302020303003090 Table ACompounds500 g ai / ha138139140141142143144145146147148149150151PostemergenceBarnyardgrass1001009050206010090304030203090Blackgrass90905050206010080709080705090Corn20403000209060300030030Crabgrass, Large--------------Foxtail, Giant1001009070206010080708070803090Galium100100909080100100100901009010080100Kochia100100703020901001001001009010070100Morningglory--------------Pigweed1001009030509010010090909010080100Ragweed1001001004020701001001009090903090Ryegrass, Italian10010010090901001001001001009010090100Velvetleaf--------------Wheat203070005010030708060702020 Table ACompounds500 g ai / ha152153154155156157158159160161162163164165PostemergenceBarnyardgrass409090809080508020805002030Blackgrass3090907090706070209040204050Corn08040203040040003002020Crabgrass, Large--------------Foxtail, Giant509090909080608020804003050Galium7010010090100100901009010010060100100Kochia40905080100100100100609090209090Morningglory--------------Pigweed601009010010010010080909090208080Ragweed9090801001001001001008090100010090Ryegrass, Italian90100100901001001001009010090709090Velvetleaf--------------Wheat50302050605003002020000 Table ACompounds500 g ai / ha166167168169170171172173174175176177185186PostemergenceBarnyardgrass20204020109070010010030100Blackgrass3040302010903000203002080Corn2020203004000020003030Crabgrass, Large--------------Foxtail, Giant4040403010908001001002090Galium9090307080100400800100090100Kochia7070201007010020000700100100Morningglory--------------Pigweed808040708010030060090090100Ragweed70700808010000200100050100Ryegrass, Italian908060100501006004030100080100Velvetleaf--------------Wheat200203007020002000040 Table ACompoundsTable ACompounds500 g ai / ha187 188500 g ai / ha187 188PostemergencePostemergenceBarnyardgrass8020Morningglory--Blackgrass7060Pigweed9080Corn300Ragweed10050Crabgrass, Large--Ryegrass, Italian10080Foxtail, Giant8080Velvetleaf--Galium10090Wheat300Kochia10020 Table ACompounds125 g ai / ha2891214151617181920212223PostemergenceBarnyardgrass300100107020002030903080Blackgrass---2020010100030905070Corn00000000002050040Crabgrass, Large50010-----------Foxtail, Giant80010101070200020301006090Galium---608070905040309010090100Kochia---080505000090100100100Morningglory100040-----------Pigweed1007003060030000100100100100Ragweed---10705030000801009090Ryegrass, Italian---606050505010010010080100Velvetleaf100600-----------Wheat200000000002010050 Table ACompounds125 g ai / ha2425262728293031333435363738PostemergenceBarnyardgrass4020109080700040305050600Blackgrass306030909070200108070606050Corn0000010000002000Crabgrass, Large--------------Foxtail, Giant1090109090800040309080800Galium8010070100100907020909010010010080Kochia7010080707080600907080906030Morningglory--------------Pigweed70908090909090204090809010050Ragweed30100601008090400909050909040Ryegrass, Italian70100601009090700501008070900Velvetleaf--------------Wheat3000004010002020204010 Table ACompounds125 g ai / ha3940414243444546474849505152PostemergenceBarnyardgrass0103030000204010002010Blackgrass306070803000206001003020Corn002000000000000Crabgrass, Large--------------Foxtail, Giant0607090000508050005040Galium90908010050300709090506090100Kochia3080100100000309070007040Morningglory--------------Pigweed50806090000701006020207010Ragweed507070100000801000007090Ryegrass, Italian9090100100400030705030206070Velvetleaf--------------Wheat00000000000000 Table ACompounds125 g ai / ha5354555657585961626364656667PostemergenceBarnyardgrass030601090080070600202020Blackgrass0207030302090070700206070Corn020002002001000000Crabgrass, Large--------------Foxtail, Giant060702080090080700207080Galium60100100901007010001001000909080Kochia701009090802010001001000909020Morningglory--------------Pigweed60907080100010001001000808020Ragweed60100907010009001001000507050Ryegrass, Italian406010090706010001001000909070Velvetleaf--------------Wheat02001000500000000 Table ACompounds125 g ai / ha6869707172737475767778798081PostemergenceBarnyardgrass7010002040000020507030Blackgrass0301030709020500030708090Corn0000202000000000Crabgrass, Large--------------Foxtail, Giant101030030900500020708090Galium08070709010010907020809090100Kochia06050506090308020050809060Morningglory--------------Pigweed0808070901004030100609090100Ragweed080407070900600040908090Ryegrass, Italian08060301001000904020808080100Velvetleaf--------------Wheat0000204000000000125 g ai / ha8283848586878889909192939495PostemergenceBarnyardgrass304020303040304080900000Blackgrass709070901080903070300000Corn0000000020200000Crabgrass, Large--------------Foxtail, Giant5090509050709070809000300Galium90100909090901009010010010708020Kochia3070703070907080100706020300Morningglory--------------Pigweed601008090908010080100902030300Ragweed709080908080908010010000100Ryegrass, Italian7090709008010080100900403010Velvetleaf--------------Wheat0000000020200000125 g ai / ha96979899100101102103104105106107108109PostemergenceBarnyardgrass03090203004040705070603030Blackgrass090306040202070908090808080Corn0102020002020000000Crabgrass, Large--------------Foxtail, Giant080904080307090807090706070Galium201001001009070100100100100100100100100Kochia6090303070202050909070809090Morningglory--------------Pigweed60901007080309090909090909090Ragweed09010010090601001001009090907080Ryegrass, Italian20100901009030201001001009060100100Velvetleaf--------------Wheat020302000200200030020 Table ACompounds125 g ai / ha110111112113114115116117118119120121122123PostemergenceBarnyardgrass04020402020200000302040Blackgrass203040902020300000203030Corn0002000000002000Crabgrass, Large--------------Foxtail, Giant07020407020700000604050Galium70907010090807000040706080Kochia5040201003070300000704070Morningglory--------------Pigweed70100209090707000020903060Ragweed607060907080700000905050Ryegrass, Italian709080100901009000020905090Velvetleaf--------------Wheat02020302020200000000 Table ACompounds125 g ai / ha124125126127128129130131132133134135136137PostemergenceBarnyardgrass2090301050906000202002070Blackgrass0706020060603030606006090Corn02000010000102003030Crabgrass, Large--------------Foxtail, Giant090201050907050602020090100Galium0901009040100100708010010060100100Kochia010090700701006050901000100100Morningglory--------------Pigweed01009090709010060609090090100Ragweed0909060101007010010010010030100100Ryegrass, Italian0100908020100100901001001004090100Velvetleaf--------------Wheat0500002000020300050 Table ACompounds125 g ai / ha138139140141142143144145146147148149150151PostemergenceBarnyardgrass202050201020100200101020070Blackgrass80603001040904020606030090Corn0302000060200002000Crabgrass, Large--------------Foxtail, Giant9070402010201002010303040080Galium100100707070901001008090909030100Kochia1001003010070100100708080804070Morningglory--------------Pigweed90607002090100100909090904090Ragweed100100906007010010090909090090Ryegrass, Italian90100707080801001007090907040100Velvetleaf--------------Wheat030200009020020202000 Table ACompounds125 g ai / ha152153154155156157158159160161162163164165PostemergenceBarnyardgrass209090307050104010202002020Blackgrass209070606060507010802002020Corn0000000200020000Crabgrass, Large--------------Foxtail, Giant309090809060305010802002020Galium6010010090100100801007080903080100Kochia30402070801009010030607006060Morningglory--------------Pigweed508090909090806080508008080Ragweed708080100901009010070808007090Ryegrass, Italian30100909090100901003010060207080Velvetleaf--------------Wheat30003030000000000 Table ACompounds125 g ai / ha166167168169170171172173174175176177185186PostemergenceBarnyardgrass10200004040000001070Blackgrass1020201008020000300040Corn20000020000000020Crabgrass, Large--------------Foxtail, Giant10203000404000000070Galium7070030409020030090070100Kochia505020400100000030070100Morningglory--------------Pigweed407002070900040030050100Ragweed306000401000020040010100Ryegrass, Italian407060700100200102030070100Velvetleaf--------------Wheat0000030200000000 Table ACompoundsTable ACompounds125 g ai / ha1871881000 g ai / ha181182183184PostemergencePreemergenceBarnyardgrass3010Barnyardgrass004010Blackgrass4010Corn----Corn00Crabgrass, Large----Crabgrass, Large--Foxtail, Giant006030Foxtail, Giant5020Kochia1007020Galium9070Morningglory----Kochia9010Pigweed3009090Morningglory--Ragweed1008070Pigweed7050Ryegrass, Italian6009090Ragweed10020Velvetleaf----Ryegrass, Italian10020Wheat----Velvetleaf--Wheat00 Table ACompounds1000 g ai / ha1345671011133260178179180PreemergenceBarnyardgrass908010090100100100906010080000Corn0010030301020------Crabgrass, Large90808090-909080------Foxtail, Giant100608080509010090501009003010Kochia--------20100800300Morningglory908060010809090------Pigweed1000700100100100010010008040Ragweed--------09010005040Ryegrass, Italian--------60100100603050Velvetleaf1007040020809080------Wheat000000050------ Table ACompounds500 g ai / ha2891214151617181920212223PreemergenceBarnyardgrass800100804090700090901007090Corn1000-----------Crabgrass, Large1006090-----------Foxtail, Giant1006010090107030000901009090Kochia---105003000010090100 1100Morningglory10000----------Pigweed10010006090070000100100100 1100Ragweed---303030010020901009090Ryegrass, Italian---50-100804020010010010090Velvetleaf90300----------Wheat000---------- Table ACompounds500 g ai / ha2425262728293031333435363738PreemergenceBarnyardgrass6090101009090100908090309010Corn--------------Crabgrass, Large--------------Foxtail, Giant809050100100906007090100909040Kochia50100309090100400806070808040Morningglory--------------Pigweed90100100100100100900201009010010080Ragweed010040100909070301009080909070Ryegrass, Italian80100701001009050060100907010070Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha3940414243444546474849505152PreemergenceBarnyardgrass105090100100060900009070Corn-------------Crabgrass, Large-------------Foxtail, Giant60709010050009080101009060Kochia0801001002000309010003080Morningglory-------------Pigweed8010010010010001001003040010060Ragweed708090100101008090601008080Ryegrass, Italian50100100100700050906030109080Velvetleaf-------------Wheat------------- Table ACompounds500 g ai / ha5354555657585961626364656667PreemergenceBarnyardgrass2090905010020100090900907090Corn--------------Crabgrass, Large--------------Foxtail, Giant501001007010001000907009090100Kochia701001009010080900901000907020Morningglory--------------Pigweed701001001001002010001001000100100100Ragweed501001009010080100090900809080Ryegrass, Italian5010010010010010010001001000100100100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha6869707172737475767778798081PreemergenceBarnyardgrass406030201001000803010707090100Corn--------------Crabgrass, Large--------------Foxtail, Giant505030501001000902010609090100Kochia0904020100100090001009090100Morningglory--------------Pigweed010010010010010050100500100100100100Ragweed208080209090090500908090100Ryegrass, Italian0100907010010001007040100100100100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha8283848586878889909192939495PreemergenceBarnyardgrass701006010040801006010010000400Corn--------------Crabgrass, Large--------------Foxtail, Giant9010090100701001008010010000500Kochia90100803040901009010010020307010Morningglory--------------Pigweed100100901001001001001001001000909020Ragweed80100909090809090100900208020Ryegrass, Italian90100901004010010090100900405060Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha96979899100101102103104105106107108109PreemergenceBarnyardgrass01001009020306090100100100100100100Corn--------------Crabgrass, Large--------------Foxtail, Giant010010080906090100100100100100100100Kochia301004070704030401001009090100100Morningglory--------------Pigweed9010010010010090100100100100100100100100Ragweed01009080804090100100100100100100100Ryegrass, Italian401009010010010060100100100100100100100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha110111112113114115116117118119120121122123PreemergenceBarnyardgrass201002010080501005030030503080Corn--------------Crabgrass, Large--------------Foxtail, Giant401006010090501003020020807070Kochia100100801001009010000003070100Morningglory--------------Pigweed100100100100100100903010070100100100Ragweed4090809090909000030808070Ryegrass, Italian8010010010090100100000309090100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha124125126127128129130131132133134135136137PreemergenceBarnyardgrass09080409010010040705090080100Corn--------------Crabgrass, Large--------------Foxtail, Giant0100706090100909090709030100100Kochia209090900901002090100100090100Morningglory--------------Pigweed010010010010010010010010010010070100100Ragweed09080707090906090100906090100Ryegrass, Italian301001009030100100909010010060100100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha138139140141142143144145146147148149150151PreemergenceBarnyardgrass10010070907080100905060607010100Corn--------------Crabgrass, Large--------------Foxtail, Giant10010080706070100905040509030100Kochia10010030600701001007080909020100Morningglory--------------Pigweed1001001006050100100100100100100100100100Ragweed10010090604090100100809080903090Ryegrass, Italian100100908080100100100801001009070100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha152153154155156157158159160161162163164165PreemergenceBarnyardgrass401001008010090608010602002030Corn--------------Crabgrass, Large--------------Foxtail, Giant90100100909080408030704004040Kochia70902090100100401002030900100100Morningglory--------------Pigweed90100100100100100100100100100907010090Ragweed1009090909090808080909009090Ryegrass, Italian10010010090100100801008010010050100100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha166167168169170171172173174175176177185186PreemergenceBarnyardgrass102020300100500001005080Corn--------------Crabgrass, Large--------------Foxtail, Giant3020403001009001001003070Kochia9010009001000002020010100Morningglory--------------Pigweed90100010010010000206090060100Ragweed90800202090000207004080Ryegrass, Italian90100401004010020002090040100Velvetleaf--------------Wheat-------------- Table ACompounds500 g ai / ha187188PreemergenceBarnyardgrass9030Corn--Crabgrass, Large--Foxtail, Giant7090Kochia10020Morningglory--Pigweed10090Ragweed8030Ryegrass, Italian10080Velvetleaf--Wheat-- Table ACompounds125 g ai / ha187188PreemergenceBarnyardgrass7010Corn--Crabgrass, Large--Foxtail, Giant2010Kochia6020Morningglory--Pigweed9060Ragweed7010Ryegrass, Italian10020Velvetleaf--Wheat-- Table ACompounds125 g ai / ha2891214151617181920212223PreemergenceBarnyardgrass500502002010003030901090Corn000-----------Crabgrass, Large901020----------Foxtail, Giant100407020010000040907090Kochia---0100000080307080Morningglory8000-----------Pigweed10070010700000080100100100Ragweed---0000000301009090Ryegrass, Italian---2030503010009010010080Velvetleaf8000-----------Wheat000----------- Table ACompounds125 g ai / ha2425262728293031333435363738PreemergenceBarnyardgrass30300909070002020600300Corn--------------Crabgrass, Large--------------Foxtail, Giant60903090100800050409080700Kochia30903040506000303040103040Morningglory-------------Pigweed70 1100801001001008002090601001000Ragweed090209090900080807080800Ryegrass, Italian80 110030100100803002010090709040Velvetleaf-------------Wheat------------- Table ACompounds125 g ai / ha3940414243444546474849505152PreemergenceBarnyardgrass010208000020700003050Corn--------------Crabgrass, Large--------------Foxtail, Giant040708000050700005040Kochia05090805000301000000Morningglory--------------Pigweed8090100100000307030007010Ragweed10308090000508010003020Ryegrass, Italian40601001001000306020005080Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha5354555657585961626364656667PreemergenceBarnyardgrass0409010100080050800602030Corn--------------Crabgrass, Large--------------Foxtail, Giant50608030100090050400606080Kochia5050704010020900901000606020Morningglory--------------Pigweed50100706010001000100100010010090Ragweed0909080907090070800708080Ryegrass, Italian103010010090709001001000909090Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha6869707172737475767778798081PreemergenceBarnyardgrass1010001040040000507090Corn--------------Crabgrass, Large--------------Foxtail, Giant101000709005000209080100Kochia02010050500800020709030Morningglory--------------Pigweed0906030100100301002006010090100Ragweed08070090900700060808090Ryegrass, Italian070600100100010050101008090100Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha8283848586878889909192939495PreemergenceBarnyardgrass40702070050905060900000Corn--------------Crabgrass, Large--------------Foxtail, Giant7010070100208010050508000200Kochia70307000806070706000300Morningglory--------------Pigweed1001009010080100100100100100020700Ragweed8090809040709080908000500Ryegrass, Italian801007010009010080100900202010Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha96979899100101102103104105106107108109PreemergenceBarnyardgrass02040602004040802080702020Corn--------------Crabgrass, Large--------------Foxtail, Giant0609050703070807090100709090Kochia08020203001020100100202090100Morningglory--------------Pigweed301001001001009080100100100100100100100Ragweed09060804040909090100909090100Ryegrass, Italian0100201009060609010010010080100100Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha110111112113114115116117118119120121122123PreemergenceBarnyardgrass070107030107000002000Corn--------------Crabgrass, Large--------------Foxtail, Giant108050704030800000803070Kochia0602090303030000003050Morningglory--------------Pigweed90909010010070900000100100100Ragweed30804070804090000060-60Ryegrass, Italian209090100801008000030807090Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha124125126127128129130131132133134135136137PreemergenceBarnyardgrass070401050903000202001090Corn--------------Crabgrass, Large--------------Foxtail, Giant090105080903080704050208090Kochia06050007060060407006030Morningglory--------------Pigweed010010070901009080908010030100100Ragweed080703070906040809080308090Ryegrass, Italian010090601010010090901001002090100Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha138139140141142143144145146147148149150151PreemergenceBarnyardgrass1020505010209020030100090Corn--------------Crabgrass, Large--------------Foxtail, Giant906050301020100300102030090Kochia40100000101009020503040030Morningglory--------------Pigweed10010050406080100901009010010080100Ragweed909070602010908080808080090Ryegrass, Italian100100707050701001008070809020100Velvetleaf--------------Wheat-------------- Table ACompounds125 g ai / ha152153154155156157158159160161162163164165PreemergenceBarnyardgrass4010070507070105010101001010Corn--------------Crabgrass, Large--------------Foxtail, Giant4010090608050106010101001010Kochia308002050100301002006006060Morningglory-------------Pigweed901001001001001001010050 1100803080100Ragweed808080909060508030905005050Ryegrass, Italian901009070901008010020 110040106040Velvetleaf-------------Wheat------------- Table ACompounds125 g ai / ha166167168169170171172173174175176177185186PreemergenceBarnyardgrass1010000702000000040Corn--------------Crabgrass, Large--------------Foxtail, Giant1010000506000000050Kochia30600200100000000080Morningglory--------------Pigweed80100050309000000020100Ragweed7070000700000200070Ryegrass, Italian4080080010000020000100Velvetleaf--------------Wheat-------------- TEST B

[0104] 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 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 BCompounds250 g ai / ha12345789101112131415FloodBarnyardgrass03000020300000000Ducksalad20802004560200300300020Rice035000000000000Sedge, Umbrella085007560700000000 Table BCompounds250 g ai / ha1617181920212223242526272829FloodBarnyardgrass000007000030030600Ducksalad3003005000750200308055Rice00000550000040400Sedge, Umbrella000050650950600809560 Table BCompounds250 g ai / ha3132333435364142434445464748FloodBarnyardgrass000000300000000Ducksalad00007530400000000Rice000002000000000Sedge, Umbrella00006570400000000 Table BCompounds250 g ai / ha4950515354555657585960626365FloodBarnyardgrass0000000000352000Ducksalad00000000002020300Rice000000000035000Sedge, Umbrella00000000003075650 Table BCompounds250 g ai / ha6667687273747579818283848586FloodBarnyardgrass00000000600600500Ducksalad000000007007005020Rice0000001506003005015Sedge, Umbrella0030000008009008060 Table BCompounds250 g ai / ha878889919293949899100101102103110FloodBarnyardgrass05000000450000300Ducksalad05065000075000000Rice0400000030000000Sedge, Umbrella0804040405006000050500 Table BCompounds250 g ai / ha111112113114115116117118119121122123124125FloodBarnyardgrass000000000002000Ducksalad7500500500000030080Rice000000000001500Sedge, Umbrella7500700700000070075 Table BCompounds250 g ai / ha126127128130131132133134135136137138139143FloodBarnyardgrass000000000025000Ducksalad30030000000040000Rice000000200000000Sedge, Umbrella000000000065000 Table BCompounds250 g ai / ha144145146147148149150151152153154155156157FloodBarnyardgrass300000004500500020Ducksalad4000000040006050600Rice300000002000502000Sedge, Umbrella0000000700080657575 Table BCompounds250 g ai / ha158159160162163164165166167168169170171172FloodBarnyardgrass00000000000000Ducksalad000000000400000Rice200000000000000Sedge, Umbrella655000000000060600 Table BCompounds250 g ai / ha173174175176177179180181183184185186187188FloodBarnyardgrass000000000001500Ducksalad00000000000000Rice000000000000200Sedge, Umbrella000000000004000 TEST C

[0105] Seeds of plant species selected from blackgrass (Alopecurus myosuroides), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), wheat (winter wheat, Triticum aestivum), galium (catchweed bedstraw, Galium aparine), corn (Zea mays), large crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii), johnsongrass (Sorghum halepense), lambsquarters (Chenopodium album), morningglory (Ipomoea coccinea), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), pigweed (Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior), soybean (Glycine max), barnyardgrass (Echinochloa crus-galli), oilseed rape (Brassica napus), waterhemp (common waterhemp, Amaranthus rudis), and velvetleaf (Abutilon theophrasti) were planted into a blend of loam soil and sand and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

[0106] At the same time, plants selected from these crop and weed species and also chickweed (common chickweed, Stellaria media), kochia (Kochia scoparia), and oat, wild (wild oat, Avena fatua), were planted in pots containing Redi-Earth ®< planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments. 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 C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table CCompounds250 g ai / ha12101114162021222325262728PostemergenceBarnyardgrass520981560904590158525355040Blackgrass7580157520404595208580759090Chickweed10098909090901001009810010010010095Corn4010505010205251051515Crabgrass, Large351075103530305554520254545Foxtail, Giant9095903050808095359085659595Galium959885909080100100951009595100100Johnsongrass1552555510355401051030Kochia100759510090251001009510010010090100Lambsquarters10010098909020100989098989898100Morningglory1001001009810040100100100100100100100100Nutsedge, Yellow-98-45--9590658590259590Oat, Wild100852570454040100801009590100100Oilseed Rape40750000251007510557070Pigweed100989595905010098989898959090Ragweed959898959830100951009895909090Ryegrass, Italian9890559085709095909595909095Soybean550050020015101005Velvetleaf1001007080403510090809098709590Waterhemp10010090954059080909898959085Wheat15505500350305555 Table CCompounds250 g ai / ha2932333436374142475152545657PostemergenceBarnyardgrass4090803540906040902010201098Blackgrass7580106020856070301030404025Chickweed10010095959595100100989010010070100Corn204020553020550010010Crabgrass, Large4070252535353520351010552035Foxtail, Giant8090703580856580853535905095Galium100100959595951009590951009890100Johnsongrass2535405535352525015101010Kochia8595508590801001009875709510095Lambsquarters90100100100100100989885-981008590Morningglory100100989810098981001007510010050100Nutsedge, Yellow7585658565608095909095706090Oat, Wild9510045908590959550100854060Oilseed Rape090502090500010507005Pigweed9895809810095959898855510090100Ragweed9598989595981001001002598986095Ryegrass, Italian9595759080909095307060809060Soybean2535051525151515001005Velvetleaf9085859095909095957010010070100Waterhemp9898759898988595100-559590100Wheat10400053550000055 Table CCompounds250 g ai / ha5960656667697273757879808182PostemergenceBarnyardgrass7065503545556560202540356030Blackgrass9090406080709090353050509040Chickweed98989095951009095958090989598Corn50355252010256010035505Crabgrass, Large6065254540306075201035355530Foxtail, Giant9090608085258585102590909080Galium98100909590989595909595959595Johnsongrass35455151015455010510157010Kochia9010010098809890100959090908090Lambsquarters98100100100100989598100100100100100100Morningglory1001009510010098100957565989898100Nutsedge, Yellow9595658585658590706085959085Oat, Wild98957090100859595356090959590Oilseed Rape558050750858580580804575Pigweed989810010085959898988098959090Ragweed9810090100959890901007598988595Ryegrass, Italian9595858585959090859085859085Soybean2550105103530451020520010Velvetleaf9595759598989590856090909090Waterhemp100988510070100851001009095958098Wheat15150000354001001505 Table CCompounds250 g ai / ha8384858788899091979899100102104PostemergenceBarnyardgrass4540504560407065359835404055Blackgrass90609065905403007065251055Chickweed100100100981001009810060100909598100Corn101055155252051510101030Crabgrass, Large5530453555107540257050151555Foxtail, Giant9085908590307580510050907585Galium1009510098100959598909898959598Johnsongrass10202510552010510510105Kochia8095709585100100988580959550100Lambsquarters989810010098100100100601009898100100Morningglory98100100100989810010030100100100100100Nutsedge, Yellow909090858575858556085507575Oat, Wild959090901004095901010095952590Oilseed Rape70501520800590352555903098Pigweed90100909890951001007510095100100100Ragweed85959010090981001003510010098100100Ryegrass, Italian9585958590809095558595953090Soybean1051552507020525551010Velvetleaf90989590908098100301001006510090Waterhemp809085909050100801010098988595Wheat000000305030105510 Table CCompounds250 g ai / ha105106107108109111113114115121123125126127PostemergenceBarnyardgrass2040906065404540453070705025Blackgrass6075305580356015355045804035Chickweed10098989810098100989098989510095Corn3010153050101501552052510Crabgrass, Large3030654060257025254075603025Foxtail, Giant8595758585857085358580982540Galium1001009895100959595959595959890Johnsongrass010205510201520525202515Kochia10080901001009510095909598909590Lambsquarters100989898100100100100981001001009598Morningglory10098100100100100100100100981001009898Nutsedge, Yellow9080857580759535807590908570Oat, Wild9090359090989085909095958560Oilseed Rape759545959510008005551085100Pigweed98909898100989895909898989595Ragweed1009898100100100100100989898989590Ryegrass, Italian8035909090959595959095959090Soybean40101015251055565065103535Velvetleaf100100100100100909885658095989555Waterhemp988090981007010045907010010010095Wheat5501035251515502035530 Table CCo mpou nds250 g ai / ha129130132133134136137138139145153154161162PostemergenceBarnyardgrass8555253555406540607090955525Blackgrass806045309845080109090856540Chickweed10010095-------98958095Corn3015105151020151510105400Crabgrass, Large6060252040353525402075752010Foxtail, Giant9570755545909580605595953540Galium100989510010095959510010098959598Johnsongrass252010102551520252015202510Kochia951009510010010010010010010085809090Lambsquarters981001001001001001009810010095958595Morningglory10010098951001001001001001001001009890Nutsedge, Yellow9585859890859080859590805030Oat, Wild98959095959090909010095909070Oilseed Rape50409810098989895909095900Pigweed9890659510098100989810085859890Ragweed959898530540502590908590Ryegrass, Italian959595540356070604095959080Soybean25502040851520256070525400Velvetleaf1009875100100989598100100959010070Waterhemp9898751001001009010010010090709565Wheat55150809090959090901051510 Table CCompoundsTable CCompounds250 g ai / ha Postemergence164165171176250 g ai / ha Postemergence164165171176Barnyardgrass35256020Nutsedge, Yellow4035-5Blackgrass4525550Oat, Wild80709535Chickweed989895-Oilseed Rape053095Corn55205Pigweed858510075Crabgrass, Large10205530Ragweed90851000Foxtail, Giant30257540Ryegrass, Italian85709510Galium1001009560Soybean5155010Johnsongrass10152010Velvetleaf705010080Kochia959098100Waterhemp757510055Lambsquarters989810090Wheat20152040Morningglory9095100100 Table CCompounds125 g ai / ha12101114162021222325262728PostemergenceBarnyardgrass51590555703075107520302535Blackgrass60851030551090207060608580Chickweed9895908590901001009510010010010098Corn5550005205105505Crabgrass, Large25156503020104053520203040Foxtail, Giant6090501050704590408570409085Galium9598709080851001009510010095100100Johnsongrass055500102051055--Kochia9565951009020909595100100909095Lambsquarters1009865908040100959095989090100Morningglory1001001009010060100100100100100100100100Nutsedge, Yellow-98-30--859065859020-85Oat, Wild85905604010259880100909595100Oilseed Rape5700001051009045205805Pigweed9890709070309895909895988590Ragweed959570955009590909595858585Ryegrass, Italian9585209065608095909590909090Soybean55000503510010101000Velvetleaf95100404540208585808585609085Waterhemp1008550955056085758595851085Wheat10505500355350050 Table CCompounds125 g ai / ha2932333436374041424751525456PostemergenceBarnyardgrass40655035356025403085105555Blackgrass608053558045506030030605Chickweed1001009090959090901009870989555Corn30305552020105100050Crabgrass, Large50752020252510252040105355Foxtail, Giant608060257060203035751510750Galium100100959595959010010090901009890Johnsongrass-155555510-20010105Kochia759040605550100100955059090Lambsquarters859898959895809510098657510085Morningglory1001009595989880100100100751009850Nutsedge, Yellow-80458555652065-8085905550Oat, Wild851004090659060909030506020Oilseed Rape560305050405510550400Pigweed9890658095958575989870109885Ragweed959890959598859598985809560Ryegrass, Italian8590709060908090902560458565Soybean20300155153020101000100Velvetleaf85857510095852085859550559815Waterhemp80856590958080909810080109595Wheat30250100301030000005 Table CCompounds125 g ai / ha5759606566676972737578798081PostemergenceBarnyardgrass9555353530353550551530303535Blackgrass58585104065308090205354090Chickweed9598959095959590959570909595Corn56530551052020101025510Crabgrass, Large302550203535253560510303040Foxtail, Giant858570356580107575520757090Galium95981009095959895959080959595Johnsongrass5255555510540551055Kochia70851009090359590909585909080Lambsquarters9598959510090100909510075989898Morningglory1001001009510010095959510065100100100Nutsedge, Yellow9095906085807070805035808590Oat, Wild4590955090908090954060859095Oilseed Rape0408501075502070900706085Pigweed859595981008090959510075989585Ragweed85959880909895959010060989870Ryegrass, Italian5090958585859590908585858590Soybean010405105201525355555Velvetleaf10090906585858585858535905590Waterhemp85989875907595858510080808585Wheat010300000535050100 Table CCompounds125 g ai / ha828384858788899091979899100102PostemergenceBarnyardgrass2530254035402050451598353035Blackgrass359055906090025100505055Chickweed90959595951001009510015100909595Corn1010300302010101001510510Crabgrass, Large204020402555535251045302520Foxtail, Giant608565907590205575598307560Galium9510095100951009595988598989595Johnsongrass10510505501050101050Kochia906590609010090100907060909520Lambsquarters98859810098951009810050100859870Morningglory10010098100100989810010030100100100100Nutsedge, Yellow858585958080709045050752060Oat, Wild9090909585100309090595908510Oilseed Rape504550105060009501060105Pigweed9090958590908095100601009810095Ragweed95909885958590959525989595100Ryegrass, Italian8590859085907590955065959025Soybean50100105055105255510Velvetleaf95908585908575989810759840100Waterhemp90609585908550100755100959580Wheat505000010100151005 Table CCompounds125 g ai / ha104105106107108109111113114115121123125126PostemergenceBarnyardgrass4525204040554535403525408035Blackgrass50506053550204552015456010Chickweed100989595959510098989090909595Corn503010202535151005520520Crabgrass, Large3520303525602525202020304030Foxtail, Giant7575907075807030502070359515Galium989595100951009595959595959598Johnsongrass501005515105105202015Kochia95958090951009095909095959095Lambsquarters10010095909810010010010090981009895Morningglory1001001009898100100100100951009810098Nutsedge, Yellow6075907570806585256585858570Oat, Wild9090904090909090658080909590Oilseed Rape956085808595950400850560Pigweed1001009098981009095957090809895Ragweed98987598981009898989595959895Ryegrass, Italian9090906090909595809590909590Soybean101002015305400200201020Velvetleaf98909095100989890557075859598Waterhemp1001007595909055905590751009895Wheat5500510155502515300 Table CCompounds125 g ai / ha127129130132133134136137138139143145153154PostemergenceBarnyardgrass2570352545403550304030307090Blackgrass56055257050300506020309060Chickweed901009895------80-9890Corn530555101010151555255Crabgrass, Large103515105152535203030105070Foxtail, Giant2585406040357080653020259095Galium8510095959810090909510090989895Johnsongrass101555205515201520201020Kochia959010095100100100100100100601008060Lambsquarters8595100100100100959895100751009590Morningglory85100859510010010010098100701009898Nutsedge, Yellow6085807595957585757035859585Oat, Wild55100857095958590809060959590Oilseed Rape2550598100989898985959098Pigweed909890701001008598909875758590Ragweed6095989555030507059585Ryegrass, Italian8095959535203030103590309590Soybean302025075701015106520551020Velvetleaf259598651001009090959550989085Waterhemp85858080100100958598100901009085Wheat54010055654590806015851010 Table CCompounds125 g ai / ha161162164165171176PostemergenceBarnyardgrass452530254010Blackgrass60304020400Chickweed7095959590-Corn15050100Crabgrass, Large51010204020Foxtail, Giant101515155035Galium9595100989560Johnsongrass205510155Kochia809090859895Lambsquarters809085859880Morningglory9585908510098Nutsedge, Yellow20302525755Oat, Wild807070659010Oilseed Rape95000095Pigweed908585759050Ragweed957585751000Ryegrass, Italian90708055950Soybean40010156015Velvetleaf9030252010075Waterhemp857070759860Wheat10510103010 Table CCompounds62 g ai / ha12101114162021222325262728PostemergenceBarnyardgrass510900570104556020252025Blackgrass506501505109006055557070Chickweed9595906590809810090100989510095Corn255000056553051055Crabgrass, Large1015300520103552015202520Foxtail, Giant156560545602580156535257580Galium959550905580100100901009595100100Johnsongrass0500001020555505Kochia955585958508090959595708070Lambsquarters10085809080608590859595858598Morningglory1001009080855010010010010010010010098Nutsedge, Yellow-95-15--6590507075108085Oat, Wild7080545305598509570809595Oilseed Rape07000000801515007060Pigweed9560609070309095759890858085Ragweed958030409008590759085707575Ryegrass, Italian907557060506095709085908585Soybean000000000100500Velvetleaf851004552052585508580308585Waterhemp956545801054075705595856075Wheat000000050300000 Table CCompounds62 g ai / ha2932333435363740414247515254PostemergenceBarnyardgrass25302525202520153530555530Blackgrass506001045540153535200105Chickweed95959090959590609510090559095Corn10205550100555000Crabgrass, Large2030201020302051015305025Foxtail, Giant35504020755535151530655555Galium9510090959595958510090909010098Johnsongrass5255520555105100105Kochia605054540550801001009015090Lambsquarters8590959070989070959585506095Morningglory1001009598100989565951001005510098Nutsedge, Yellow3580156085404015657570708035Oat, Wild55903085606080509090105050Oilseed Rape0605530104020300505080Pigweed9590508555851006575959065595Ragweed909095984090957585859856595Ryegrass, Italian8090458055608565909010504080Soybean1025055056015510005Velvetleaf80706080100857010658590202590Waterhemp8080308545958065758575501090Wheat51505500100000050 Table CCompounds62 g ai / ha5657596065666769727375787980PostemergenceBarnyardgrass595302515203535404025252530Blackgrass55806051560207085551035Chickweed1095989590959590909090609095Corn054525505010205005Crabgrass, Large52020352030352525351052525Foxtail, Giant0706060205575107065556055Galium85959810085959595959090809595Johnsongrass0553555510555555Kochia9065859090903090859085709090Lambsquarters507095909510095908595100709595Morningglory501001009885959595909010040100100Nutsedge, Yellow590858550707065608020258080Oat, Wild1035759535808560959035506090Oilseed Rape00505010501035707002550Pigweed7580958590988585908595609890Ragweed090959085857590909085209590Ryegrass, Italian6030909080808090909080656085Soybean0015205105251515350015Velvetleaf095858520758580858550108590Waterhemp75659090759070906575100909080Wheat00205000030300505 Table CCompounds62 g ai / ha81828384858788899091979899100PostemergenceBarnyardgrass352525204525401535305852525Blackgrass853580358035800155030305Chickweed90909590959010095909801009090Corn530520050510000510Crabgrass, Large35202510301020515205252015Foxtail, Giant852585558555851025455951545Galium959590951009510095959080 20959595Johnsongrass55551555010505100Kochia7590609070905090100900208590Lambsquarters9598859098988590981001007590Morningglory10010090989898100951001004010095100Nutsedge, Yellow858080858580856080400155525Oat, Wild908590909090951070705807070Oilseed Rape654004510505009000560Pigweed85908590859085758090501007585Ragweed7598859085958590859810989095Ryegrass, Italian8585908090809075908030459090Soybean01005000050501055Velvetleaf8580909085858575757520708550Waterhemp60988585658085401005051007590Wheat0000000010501000 Table CCompounds62 g ai / ha102104105106107108109111113114115121123125PostemergenceBarnyardgrass2035251550353030353520202540Blackgrass535405053525525010153545Chickweed9598959890909598909575909095Corn08015101040151010055150Crabgrass, Large103030402010402015202053535Foxtail, Giant3570507555405045252015502090Galium95959895959810095959590909595Johnsongrass0501000510105105105Kochia095958585959585989090909590Lambsquarters709885909095100100989590959898Morningglory1001009898981009810010010085989095Nutsedge, Yellow5545708580605040701060407585Oat, Wild590609020908070906060908590Oilseed Rape07030805590901008506000Pigweed8098988095959590758570858095Ragweed9590958590959590959085909098Ryegrass, Italian590909050909090957090909090Soybean1000055155300200105Velvetleaf7585858598858080955525357590Waterhemp60901008085858545905575659095Wheat05000551015555515 Table CCompounds62 g ai / ha126127129130132133134136137138139143145151PostemergenceBarnyardgrass3020653030302025402520251550Blackgrass55403553545505505035Chickweed9090989590------70-98Corn1002055510515000525Crabgrass, Large20530151551020302010101040Foxtail, Giant15575204025254560603052575Galium95801009595959590909095909595Johnsongrass10515551010510105251020Kochia90856095901001009510095100609830Lambsquarters9580959890989890909095609898Morningglory957510080801001009898100100659898Nutsedge, Yellow6035757555908055856575409085Oat, Wild8020908060909075708090559590Oilseed Rape8000010981009898989509820Pigweed908595705598100809885956510070Ragweed9055909095050200030085Ryegrass, Italian857590908510151030510601585Soybean101010150407010101055154025Velvetleaf8530957040909095909080259065Waterhemp90857085601001008065951005510075Wheat05355035504590405535500 Table CCompounds62 g ai / ha153154161162164165171176PostemergenceBarnyardgrass608535202515355Blackgrass856540151515300Chickweed95907090909090-Corn3555000010Crabgrass, Large50705555205Foxtail, Giant85905151052515Galium959580909585955Johnsongrass55555555Kochia7050708085409590Lambsquarters9085909585759580Morningglory100989085857010085Nutsedge, Yellow906010252030755Oat, Wild958050604545905Oilseed Rape909070000095Pigweed7585808080708030Ragweed9075808580551000Ryegrass, Italian959080706050950Soybean10203000103010Velvetleaf8585651560257025Waterhemp6580906570709540Wheat20501055155 Table CCompounds31 g ai / ha12101114162021222325262728PostemergenceBarnyardgrass0103505553554015201520Blackgrass2045050058005030505050Chickweed95959060907590959010090959595Corn000000550105005Crabgrass, Large2010100555300555525Foxtail, Giant35207052055055103035156060Galium90955755060989890959090100100Johnsongrass0500005105505105Kochia955060858505080909595807570Lambsquarters8585508080108085708590758585Morningglory10010055706545100851001001009810095Nutsedge, Yellow-80-5--458535606558575Oat, Wild5075540105090408560608595Oilseed Rape0650000065550055Pigweed9580555055407570859090755560Ragweed9080501508085708590157065Ryegrass, Italian806057040105590608570858080Soybean00000000050500Velvetleaf80100400105257520707058070Waterhemp95654080557040758075756560Wheat000000000100000 Table CCompounds31 g ai / ha2932333435363740414247515254PostemergenceBarnyardgrass1510252020152552520155515Blackgrass4030010155355303000015Chickweed9590859095809055959090509595Corn00005000500000Crabgrass, Large10101052025105510200020Foxtail, Giant3015201050302551525505020Galium909090909090908010095809095Johnsongrass0505200005510055Kochia605020103050070100907585 0050Lambsquarters808590908090907090858555595Morningglory85908585100909055957510059895Nutsedge, Yellow25555457520200656540356010Oat, Wild6070358040506035557550045Oilseed Rape0104030-404050000070Pigweed9575309060708535658590603085Ragweed8085858525909045709080105590Ryegrass, Italian708530803555805080650351050Soybean01505001051500005Velvetleaf35101050100652053045705545Waterhemp7070258525858565757590301085Wheat55050030101000000 Table CCompounds31 g ai / ha5657596065666769727375787980PostemergenceBarnyardgrass090202010152525352525152025Blackgrass0565505104015604050515Chickweed590909055909090909095309090Corn005105050555000Crabgrass, Large01015155253551030552010Foxtail, Giant0704545104070550405153525Galium80959510085909090809090709590Johnsongrass05555555555555Kochia705095909090090609090455090Lambsquarters0709085909085858590100408595Morningglory359595907590959080759820100100Nutsedge, Yellow09065852565654030802508565Oat, Wild520808525558045857540355090Oilseed Rape00550040404010700205Pigweed80609085909510070858085509085Ragweed060908555857070808595109098Ryegrass, Italian25859065608085858580555080Soybean000155051010020000Velvetleaf40 09080401055704045407007570Waterhemp55508565609860857075100758585Wheat0005000030100000 Table CCompounds31 g ai / ha81828384858788899091979899100PostemergenceBarnyardgrass25202510252535530250602510Blackgrass60104010701040010005205Chickweed909090909090959090950959090Corn035500505500505Crabgrass, Large2510205355250515010205Foxtail, Giant8035754075358052010590520Galium9090909095909590909045959090Johnsongrass55505050500050Kochia40904085309030859575002080Lambsquarters959095908595858595980987580Morningglory951009890989895901001001010075100Nutsedge, Yellow70658580757065407020010305Oat, Wild85559085908590570505706050Oilseed Rape453550551020006000030Pigweed80858085857565807598201007575Ragweed7090708575908080857501007098Ryegrass, Italian8580808085808045856010408565Soybean0100000004000500Velvetleaf757085607575752535500553520Waterhemp608585808585603085505987585Wheat000000005001000 Table CCompounds31 g ai / ha102104105106107108109111113114115121123125PostemergenceBarnyardgrass2020101535202510253010202035Blackgrass0151545015200150001520Chickweed9590909590908095909080909095Corn0510055055050105Crabgrass, Large5202025155351051010101025Foxtail, Giant205040701530451520105202070Galium9095959595909895959585909595Johnsongrass0105500010055055Kochia095957070909580953070909585Lambsquarters7590858585909590989570909590Morningglory10098100100959895100989555989595Nutsedge, Yellow2055556580304535701040455535Oat, Wild580605020808055904055657085Oilseed Rape0855602580708001507000Pigweed7595857085909585658030756595Ragweed9585908085908098909060757595Ryegrass, Italian090858540909085906090859085Soybean005001000150100100Velvetleaf3050758075707540702515106585Waterhemp2570806575858040852565608085Wheat000000010500550 Table CCompounds31 g ai / ha126127129130132133134136137138139143144145PostemergenceBarnyardgrass2510503015151015252525206520Blackgrass503530545501005205355Chickweed9050989090------45--Corn10005055050553010Crabgrass, Large1002010150510301520103015Foxtail, Giant5560203025153545352057020Galium9075959590909590859095659590Johnsongrass1051050510510105101010Kochia90405095859895951009095309895Lambsquarters80709590909510090909098509098Morningglory956598756510098981009898509895Nutsedge, Yellow3510605530757515654555107570Oat, Wild6010856040909050705090409095Oilseed Rape60000595959595959509598Pigweed8570955050808075908080509070Ragweed851090856500010000350Ryegrass, Italian8050709080555105555705Soybean5001005575510104502540Velvetleaf3020857530858075858570208585Waterhemp7570757040959880859098409595Wheat00100025303575604559540 Table CCompounds31 g ai / ha151153154161162164165171176PostemergenceBarnyardgrass40407020101010155Blackgrass45806010105550Chickweed9590906590807090-Corn202015000000Crabgrass, Large3555650000510Foxtail, Giant6080850550105Galium95959580909085950Johnsongrass101051055055Kochia604050707060459590Lambsquarters958590808570709060Morningglory989895906080759085Nutsedge, Yellow8085705202020505Oat, Wild70905560503540650Oilseed Rape65907550000095Pigweed758565807570756020Ragweed60707070707040750Ryegrass, Italian60908070605040900Soybean5510150010105Velvetleaf6085704552520350Waterhemp557075854560657520Wheat0150005500 Table CCompounds16 g ai / ha3540143144151PostemergenceBarnyardgrass105153530Blackgrass5502040Chickweed905030-95Corn000525Crabgrass, Large5552530Foxtail, Giant35556040Galium9030609095Johnsongrass15010105Kochia302009810Lambsquarters7550109080Morningglory1005309898Nutsedge, Yellow600106055Oat, Wild305309050Oilseed Rape00609550Pigweed2515508555Ragweed02503535Ryegrass, Italian3010454540Soybean0350255Velvetleaf755309060Waterhemp3020259055Wheat000950 Table CCompounds8 g ai / ha35144151PostemergenceBarnyardgrass102525Blackgrass03010Chickweed90-90Corn0020Crabgrass, Large5205Foxtail, Giant255020Galium909095Johnsongrass10105Kochia-900Lambsquarters359080Morningglory1009595Nutsedge, Yellow456055Oat, Wild109035Oilseed Rape09530Pigweed358565Ragweed01010Ryegrass, Italian103540Soybean0400Velvetleaf607015Waterhemp09030Wheat0900 Table CCompound4 g ai / ha144PostemergenceBarnyardgrass15Blackgrass30Corn0Crabgrass, Large20Foxtail, Giant45Galium80Johnsongrass20Kochia90Lambsquarters80Morningglory90 Table CCompound4 g ai / ha144PostemergenceNutsedge, Yellow10Oat, Wild80Oilseed Rape85Pigweed80Ragweed10Ryegrass, Italian20Soybean45Velvetleaf50Waterhemp90Wheat90 Table CCompounds250 g ai / ha12101120212223252728293234PreemergenceBarnyardgrass90985808510060858590959010075Blackgrass909508580904590909090859090Corn51050356535651001545350Crabgrass, Large100950406010035959098859010030Foxtail, Giant1001000908510085100100100100958570Galium1001009595100951009895959898100Johnsongrass5545 001050035202510204520Lambsquarters10010030100901009095959890909075Morningglory1001005510010010010098100100100989895Nutsedge, Yellow759503095857090809570856065Oilseed Rape20650020100801003598907010090Pigweed10010030100100100100100100100100100100100Ragweed98985907510010090959590909895Ryegrass, Italian100988010095959595959595909595Soybean0000302055550500555Velvetleaf98100509010098981009898951009098Waterhemp10010090100100100100100100100100100100100Wheat2010010304009051010507025 Table CCompounds250 g ai / ha3637414247545759606667697273PreemergenceBarnyardgrass708095801008510095907080758085Blackgrass3090909090808098903060359090Corn0204035503565450052025Crabgrass, Large652570859560100100958565108575Foxtail, Giant8585851001009010010010085100608595Galium10010098989810098981009890989598Johnsongrass503530010065606530358555Lambsquarters809090901008010095909885959090Morningglory9598989895981001001009090909095Nutsedge, Yellow6560808085709590856570907095Oilseed Rape95901002010100609590520408085Pigweed1001001001001001001001001001001008510098Ragweed9598100100100100100100959598959598Ryegrass, Italian85959590509085100959090909090Soybean206555530200257500500Velvetleaf9090989810095100100988575908585Waterhemp10010010010010010010010010010085959095Wheat045655005857040054060 Table CCompounds250 g ai / ha7579808182838485878889909197PreemergenceBarnyardgrass85858598909085908510065959535Blackgrass308590908090859090904555605Corn105253025100101020030250Crabgrass, Large5030759880858585858075858560Foxtail, Giant7595981001001001001009510075959855Galium9898959595959895989898-9890Johnsongrass10303598407030404060565250Lambsquarters90100989598100100100100909010010025Morningglory100989895959895989510090989830Nutsedge, Yellow759080959095808080959090900Oilseed Rape983009585508090803090901000Pigweed1001001001001001001001001009510010010065Ragweed10010010098959598989098909510010Ryegrass, Italian9090909090909590909090959530Soybean550000000010051002020Velvetleaf98959598909090909085859510030Waterhemp10010010010010010010010010098751008520Wheat50000005010040400 Table CCompounds250 g ai / ha99102104105106107108109111113114116121125PreemergenceBarnyardgrass8585809095988580859595956098Blackgrass9070609085108590206010356090Corn3030102520151501535525555Crabgrass, Large8055608080857080809080903598Foxtail, Giant9090100100100989590----95100Galium989598989595959010098100100100100Johnsongrass20030601520206520300101070Lambsquarters95100959510095100100951009595100100Morningglory95989895989898989810090989098Nutsedge, Yellow9075858590908080908595955090Oilseed Rape98359510908090901009010010085100Pigweed100100100100100100100100100100100100100100Ragweed95100100100951009810098959810098100Ryegrass, Italian100709595903095959595959010095Soybean2050001500080-5035Velvetleaf9510090959090909010010010010095100Waterhemp100851001009098100100859880100100100Wheat652505051015405035151590 Table CCompounds250 g ai / ha129131132133134136137138139145152153154161PreemergenceBarnyardgrass903545959095100989595701009530Blackgrass8090505075909090906035959045Corn401510105555151515156555Crabgrass, Large858040656095808050551010010040Foxtail, Giant98989890809810010095959010010080Galium98959810098100100981009810010010095Johnsongrass2520254051020202555707510Lambsquarters909510095100100951009810098989580Morningglory989590951009898989810090989085Nutsedge, Yellow9575759590809590909085958560Oilseed Rape908090909810090100100981001009890Pigweed100100100100100100100100100100100100100100Ragweed959810098981001009510090901009585Ryegrass, Italian959595100100901009510010090959085Soybean200080752030158080104520100Velvetleaf98959510010010010010010010075908580Waterhemp10010098100100100981001001007510010095Wheat8520504040459051058550300 Table CCompound250 g ai / ha171PreemergenceBarnyardgrass95Blackgrass90Corn40Crabgrass, Large80Foxtail, Giant-Galium100Johnsongrass35Lambsquarters100Morningglory98 Table CCompound250 g ai / ha171PreemergenceNutsedge, Yellow90Oilseed Rape90Pigweed100Ragweed98Ryegrass, Italian95Soybean70Velvetleaf100Waterhemp100Wheat70 Table CCompounds125 g ai / ha12101120212223252728293234PreemergenceBarnyardgrass259551060100585709090808565Blackgrass909505040904090909090859085Corn000054003005300010Crabgrass, Large80980401585075959580557025Foxtail, Giant1009805065100558590100100908575Galium951005909598951009595959810090Johnsongrass550003503555525100Lambsquarters100100-10085989095859585808580Morningglory100982510098100100959510098959885Nutsedge, Yellow707001095857085709085854535Oilseed Rape-650001005905988559090Pigweed1001001010010010010010010098100100100100Ragweed1001000807010090959810095859590Ryegrass, Italian100982510095909595959095909585Soybean00003000501000400Velvetleaf1001001009010098751009085901008585Waterhemp10010010010010010010010010010085100100100Wheat5000353009000045505 Table CCompounds125 g ai / ha3637414247545759606667697273PreemergenceBarnyardgrass65708560856510090854040205570Blackgrass2090859040557090903540607085Corn005100100503000005Crabgrass, Large2020658060759885857510106575Foxtail, Giant85858590857590981008098258585Galium100959895981009598989590909595Johnsongrass5535505045405510308035Lambsquarters8585100851008010095958585908580Morningglory9090959810095100100988080859090Nutsedge, Yellow2040754075259085853055256050Oilseed Rape60604050903095900008090Pigweed1001001001001001001001001001009510098100Ragweed95959595989510010095901009010095Ryegrass, Italian35909590458070100958085909090Soybean30205001000156500500Velvetleaf85859590100909598957060758085Waterhemp10095100100100100100100100100651009090Wheat0550000075450003035 Table CCompounds125 g ai / ha7579808182838485878889909197PreemergenceBarnyardgrass506575807085608065852575200Blackgrass306080906580909085904050600Corn051020200000005100Crabgrass, Large252040907070708080802575500Foxtail, Giant70858598901009010090986590905Galium9095959590959595989898-980Johnsongrass204030456060565406006000Lambsquarters851009085989510090859098858020Morningglory9598909095959595959585989020Nutsedge, Yellow659080806085707585958085800Oilseed Rape903050400508040851030501000Pigweed100100100951001001001001009510010010065Ragweed909895959095959895958085900Ryegrass, Italian9090909085908590909090959530Soybean45500000010000101010Velvetleaf9095908585858585908590958520Waterhemp100100100901001001009010095401006510Wheat10000000000035300 Table CCompounds125 g ai / ha99102104105106107108109111113114116121125PreemergenceBarnyardgrass5530406085803570556560705590Blackgrass90453055901060855555304555Corn1020155101050020560020Crabgrass, Large6030557575756570857575501075Foxtail, Giant65857590100858585----9098Galium98959095959095901009810010098100Johnsongrass002020510304002000060Lambsquarters1008595901009590909090909098100Morningglory908510010098959890959875858595Nutsedge, Yellow6075754080707090758565852095Oilseed Rape901085103020908510060100953085Pigweed100981001001001001001009810010010090100Ragweed9590959895859895908595959898Ryegrass, Italian10050909085359090859090709595Soybean55000000065200030Velvetleaf908590908585858095988510085100Waterhemp987510010080951001007598658085100Wheat30-5100015102035551090 Table CCompounds125 g ai / ha129131132133134136137138139145152153154161PreemergenceBarnyardgrass100103550709090907575301009010Blackgrass704040504070304060603095855Corn155010100105100104055Crabgrass, Large7560103540607070205510989020Foxtail, Giant95908575701009510085756510010025Galium1009590100981009898100100951009895Johnsongrass10055305202030355065500Lambsquarters8585859510010010010095100901008565Morningglory9085959095989098959875988575Nutsedge, Yellow9065457095709095859555807055Oilseed Rape9085309090905090989095989890Pigweed9810010010010010010010010010010010010098Ragweed95989595951009598958575989030Ryegrass, Italian959595100100851009010010090909085Soybean5006565104020607552050Velvetleaf9885909090100100981009565958550Waterhemp100989595989895981009885959575Wheat552020101545905150253000 Table CCompoundTable CCompound125 g ai / ha171125 g ai / ha171PreemergencePreemergenceBarnyardgrass75Nutsedge, Yellow70Blackgrass45Oilseed Rape50Corn0Pigweed100Crabgrass, Large60Ragweed95Foxtail, GiantRyegrass, Italian95Galium98Soybean55Johnsongrass10Velvetleaf95Lambsquarters95Waterhemp100Morningglory95Wheat45 Table CCompounds62 g ai / ha12101120212223252728293234PreemergenceBarnyardgrass5705030100585308075356555Blackgrass90900405902085859090509050Corn000001500000000Crabgrass, Large405500158504575806053510Foxtail, Giant7510003530100158585100100758065Galium1001005901009890100959595959595Johnsongrass500001005050500Lambsquarters95100010085984585859585807090Morningglory100100010098988590959898959080Nutsedge, Yellow35450585854590309075804525Oilseed Rape5200001005900952009025Pigweed1001000100100100100100100100100100100100Ragweed801000504510075859510090859080Ryegrass, Italian1009809595909090959090909085Soybean000020000002501010Velvetleaf909501090906090858585908580Waterhemp100100010010095801001008575100100100Wheat0000050850005450 Table CCompounds62 g ai / ha3536374142475457596066676972PreemergenceBarnyardgrass252530403020359070402020520Blackgrass5530308085305560909030303050Corn00000010-20100000Crabgrass, Large5205357030403570756570580Foxtail, Giant857575808050808095857580570Galium951009010090959590959590909090Johnsongrass1050500000252025201025Lambsquarters10080609080100851009085858010065Morningglory9880809598100901001009885808585Nutsedge, Yellow402020756045530804535203510Oilseed Rape9060405000900808500035Pigweed80100981001001001001001001001009010098Ragweed4090908590859095959085857090Ryegrass, Italian70308595902050651009550409090Soybean003020009000450000Velvetleaf8580809090908580908560355545Waterhemp50100959598981009810010090809590Wheat5005000060400000 Table CCompounds62 g ai / ha7375798081828384858788899091PreemergenceBarnyardgrass2525156570557025603540156515Blackgrass8030508080608060853090404030Corn0501010000101000010Crabgrass, Large301025157520651085658007020Foxtail, Giant70458585988510075988090607565Galium989095959590909590959898-98Johnsongrass102035556575530257075550Lambsquarters70100959090908585908085858025Morningglory9085959085909090909090858585Nutsedge, Yellow3540452570609040853575754545Oilseed Rape85703530500085302003598Pigweed1001001001009510010010010010010010010098Ragweed95859595959010095909085809075Ryegrass, Italian9090907090859085859090809570Soybean020001001000000100010Velvetleaf8085858565807065808570809070Waterhemp90100100100851009010080100100509060Wheat200000000000005 Table CCompounds62 g ai / ha9799102104105106107108109111113114116121PreemergenceBarnyardgrass015102530454535352035103010Blackgrass0705015505050305505545Corn02010000010000500Crabgrass, Large035555507030706553552010Foxtail, Giant53575858095808585----55Galium0--8590909090908090988590Johnsongrass000202050530010000Lambsquarters0808585859010090909585989880Morningglory3085759590908590857095558055Nutsedge, Yellow070704545705080702070403525Oilseed Rape04010305009085980988085Pigweed35100851001009810010010090759010098Ragweed090759090909090907595759095Ryegrass, Italian590258590703585909095853090Soybean1005000000-45000Velvetleaf075858085606075757095608575Waterhemp101006590957575909065100757095Wheat005510001010530000 Table CCompounds62 g ai / ha125129131132133134136137138139145151152153PreemergenceBarnyardgrass70700540405085555535855100Blackgrass553040456040804055553065590Corn05005051050010100Crabgrass, Large45252003030520403050700100Foxtail, Giant100908570657585858565609835100Galium10098909095989898989098954598Johnsongrass555010355551535525050Lambsquarters1008070609090901009590908575100Morningglory9590556585909585909080984090Nutsedge, Yellow9585353555453585606085952085Oilseed Rape0504085859030909098909885100Pigweed10098100100100100100100989898100100100Ragweed100859585759598951009065854095Ryegrass, Italian9590809095100559590100100905095Soybean5000554510200355510510Velvetleaf100855560909095100908585754090Waterhemp100959885100981009810010098458595Wheat45500400010803510001010 Table CCompounds62 g ai / ha154161171PreemergenceBarnyardgrass80035Blackgrass50040Corn550Crabgrass, Large853045Foxtail, Giant9525-Galium957090Johnsongrass4505Lambsquarters604095Morningglory854090 Table CCompounds62 g ai / ha154161171PreemergenceNutsedge, Yellow202055Oilseed Rape85205Pigweed959860Ragweed951580Ryegrass, Italian554095Soybean500Velvetleaf604090Waterhemp857095Wheat005 Table CCompounds31 g ai / ha12101120212223252728293234PreemergenceBarnyardgrass5350058051005545102060Blackgrass608503509054585858550705Corn00000000000000Crabgrass, Large355500103505705525500Foxtail, Giant5580005100530751008575550Galium909508590989098909095959095Johnsongrass0000010050001000Lambsquarters8010007080902585807065758080Morningglory9598010085953085858580808070Nutsedge, Yellow40300080755540407050152525Oilseed Rape000009005005002510Pigweed100100001001006010010098100100100100Ragweed906501535953085808070808580Ryegrass, Italian959509075909085908585908545Soybean000000000000010Velvetleaf70750060851085807055857570Waterhemp100759090907510010080701009885Wheat0000000750000150 Table CCompounds31 g ai / ha3536374142475457596066676972PreemergenceBarnyardgrass51010100155301005010Blackgrass5001070405 05030859010603040Corn00000000000000Crabgrass, Large57053055040025207510060Foxtail, Giant607565457515704580757075060Galium901001009090909580989090705090Johnsongrass100000000551010200Lambsquarters207085758510080100708080801060Morningglory25807085859080100988580707075Nutsedge, Yellow2010060553551080453510510Oilseed Rape90500500700653000030Pigweed759098751001001001001001001007510090Ragweed585858590509070908075606085Ryegrass, Italian6530509585055451009055308590Soybean010000350000000080Velvetleaf4055258585658050857515103530Waterhemp4010090858010098909510085708575Wheat0000000060100000 Table CCompounds31 g ai / ha7375798081828384858788899091PreemergenceBarnyardgrass10510103010505355355350Blackgrass50202070605070605040555250Corn00000000000000Crabgrass, Large07525109025751080105520350Foxtail, Giant55565708060857090708510755Galium909095909090909090959095-95Johnsongrass001052545655405500500Lambsquarters75651009075858060855560407510Morningglory8570908580858585858585808525Nutsedge, Yellow015252060358515701040605510Oilseed Rape90300000005302003080Pigweed9585100100989510010010075909510070Ragweed8580909085858585809090308035Ryegrass, Italian7590203580809080853585209030Soybean000000300000000Velvetleaf2535805535653540505510708555Waterhemp85100100100851006010060100100757525Wheat00000000000050 Table CCompounds31 g ai / ha9799102104105106107108109111113114116121PreemergenceBarnyardgrass0551002515510101055Blackgrass0500520100103501005 010Corn55550005500000Crabgrass, Large03004020703054050000Foxtail, Giant04030756085606565----20Galium0--90859090909080100986090Johnsongrass0001010500000000Lambsquarters025708595909085809090906560Morningglory2580458085858080855085255525Nutsedge, Yellow0201530406030354005510010Oilseed Rape0005000550030850Pigweed5 159575100989810010010098709895100Ragweed070708590857575956065558535Ryegrass, Italian59015554050156070109540575Soybean000007500-00-0Velvetleaf060654060403050606560457060Waterhemp085757590707575805085505570Wheat000501500000000 Table CCompounds31 g ai / ha125129131132133134136137138139144145151152PreemergenceBarnyardgrass55150005253530203510705Blackgrass5050203020703045509010605Corn0000500050001015Crabgrass, Large405000502005605300Foxtail, Giant958535403025756580359035850Galium1009585909510090989590100909550Johnsongrass4050155050105601000Lambsquarters908560509075959095100100908050Morningglory9085354045758070808590759010Nutsedge, Yellow6555101020305555654035705Oilseed Rape855207055510085207059850Pigweed1001006010010075100100100701007010080Ragweed9570657070709580957598559085Ryegrass, Italian859010459098508555951001009010Soybean0000540103002550200Velvetleaf957006055757580856090406015Waterhemp989095908090988595100100853520Wheat4035025000150090000 Table CCompounds31 g ai / ha153154161171PreemergenceBarnyardgrass856505Blackgrass905530Corn0500Crabgrass, Large8070300Foxtail, Giant988510-Galium95988090Johnsongrass251000Lambsquarters9515098Morningglory95451085Nutsedge, Yellow800045Oilseed Rape9580100Pigweed100557570Ragweed95804065Ryegrass, Italian9040590Soybean2000-Velvetleaf8540070Waterhemp80302085Wheat0000 Table CCompounds16 g ai / ha35144151PreemergenceBarnyardgrass5520Blackgrass407060Corn0030Crabgrass, Large02510Foxtail, Giant257575Galium909595Johnsongrass0250Lambsquarters56580Morningglory258090Nutsedge, Yellow202530Oilseed Rape5585Pigweed7510095Ragweed09585Ryegrass, Italian5010050Soybean000Velvetleaf08555Waterhemp4010010Wheat0700 Table CCompoundsTable CCompound8 g ai / ha35 144 1514 g ai / ha144PreemergencePreemergenceBarnyardgrass005Barnyardgrass0Blackgrass55530Blackgrass30Corn0020Corn0Crabgrass, Large050Crabgrass, Large0Foxtail, Giant56040Foxtail, Giant30Galium909598Galium90Johnsongrass0250Johnsongrass0Lambsquarters5 403560Lambsquarters25Morningglory106080Morningglory25Nutsedge, Yellow0540Nutsedge, Yellow5Oilseed Rape0085Oilseed Rape0Pigweed10070Pigweed75Ragweed09055Ragweed70Ryegrass, Italian409515Ryegrass, Italian80Soybean000Soybean10Velvetleaf07040Velvetleaf25Waterhemp-1005Waterhemp80Wheat0550Wheat0 TEST D

[0107] Seeds of plant species selected from bluegrass (annual bluegrass, Poa annua), blackgrass (Alopecurus myosuroides), Canada thistle (Cirsium arvense), canarygrass (Phalaris minor), chickweed (common chickweed, Stellaria media), geranium, cutleaf (cutleaf geranium, Geranium dissectum), galium (catchweed bedstraw, Galium aparine), bromegrass, downy (downy bromegrass, Bromus tectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis), foxtail, green (green foxtail, Setaria viridis), deadnettle (henbit deadnettle, Lamium amplexicaule), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), kochia (Kochia scoparia), lambsquarters (Chenopodium album), oilseed rape (Brassica napus), pigweed (Amaranthus retroflexus), chamomile (scentless chamomile, Matricaria inodora), Russian thistle (Salsola kali), speedwell (bird's-eye speedwell, Veronica persica), barley, spring (spring barley, Hordeum vulgare), wheat, spring (spring wheat, Triticum aestivum), buckwheat, wild (wild buckwheat, Polygonum convolvulus), mustard, wild (wild mustard, Sinapis arvensis), oat, wild (wild oat, Avena fatua), radish, wild (wild radish, Raphanus raphanistrum), windgrass (Apera spica-venti), barley, winter (winter barley, Hordeum vulgare), and wheat, winter (winter wheat, Triticum aestivum) were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

[0108] At the same time, these species were planted in pots containing Redi-Earth ®< planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients and treated with postemergence applications of the test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage). Treated plants and controls were maintained in a controlled growth environment for 14 to 21 d after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table DCompounds250 g ai / ha12112021222325272834353641PostemergenceBarley, Spring1051003015301010105151020Barley, Winter101040040530105520151035Blackgrass8090706090708080908575857075Bluegrass515154050254040405020403535Bromegrass, Downy2020501580257565707070306545Buckwheat, Wild10010095100100100100100100100100100100100Canada Thistle--------------Canarygrass7075555595659085908585808080Chamomile1001009010010010010010010095100100100100Chickweed100100100100100100100100100100100100100100Deadnettle706010065100708545607010080100100Field Poppy9510010010010010010010010010010010010095Field Violet958090451009575958590959890100Foxtail, Green85100707095759075809070959065Galium1001009010010098100100100100100100100100Geranium, Cutleaf--------------Kochia10070100100851008010075759570100100Lambsquarters10010085959598809585901009810085Mustard, Wild655595100100100100857570100100100100Oat, Wild9510098751001009590989595989585Oilseed Rape6070555100100856085859010010055Pigweed100951001009810010010095901009810085Radish, Wild60608565100851007590959510010095Russian Thistle---9885858090708585959075Ryegrass, Italian8590909080908590858595909090Speedwell70901001001001009580100100100100100100Wheat, Spring1525252050156020202045301040Wheat, Winter510252540157020101525201535Windgrass7070204085558585908575857575 Table DCompounds250 g ai / ha4247525457596066676972737579PostemergenceBarley, Spring100010106050152051540010Barley, Winter10150302560505105353555Blackgrass8565407575859075956580907050Bluegrass3515303515756035302555651515Bromegrass, Downy705107535858070704075853020Buckwheat, Wild10010010010010010010010010098100100100100Canada Thistle---------98----Canarygrass80007525909085957585905045Chamomile100-10010010010010010010080100100100100Chickweed10010010010010010010010010098100100100100Deadnettle5530351001001009540608010010010040Field Poppy100100100100100100100951008010010010098Field Violet90-7590859585959598959010095Foxtail, Green80804080908575981001575806080Galium1008010010098100100100100100100100100100Geranium, Cutleaf---------65----Kochia100100651007510095100509810010010095Lambsquarters907090100859580100100100100100100100Mustard, Wild80251001004010010070658010010010050Oat, Wild95401590859810010010085981008085Oilseed Rape707080100659080759020909510030Pigweed10010080100100100100100100100100100100100Radish, Wild65208510090100954595759510010065Russian Thistle90-55100-858580857085858565Ryegrass, Italian854580958590959810085100989890Speedwell4550100100100100100751001008010010065Wheat, Spring20155251080555507085155Wheat, Winter1551530158040000607500Windgrass9815575158598100905585856565 Table DCompounds250 g ai / ha808182838485878890104105108109126PostemergenceBarley, Spring25105101020515401515202510Barley, Winter151001501051035151515200Blackgrass9085808085909095657065757545Bluegrass4540352535404535303025354515Bromegrass, Downy7575607075606565556565657525Buckwheat, Wild100100100100100100100100100100100100100100Canada Thistle--------98---100Canarygrass90100859080909095758580809075Chamomile1001001001001008510095100100100100100100Chickweed100100100100100100100100100100100100100100Deadnettle50603560404560451008530909585Field Poppy10010010010010095100100908080758585Field Violet100100100100100901008010098100100100100Foxtail, Green951009010095859080759080958525Galium100100100100100100100100100100100100100100Geranium, Cutleaf--------95----90Kochia1009510090100759570100100100100100100Lambsquarters100100100100100951009010010095100100100Mustard, Wild100807070758060751009075100100100Oat, Wild10098959510010010010010010010010010090Oilseed Rape75858095758075807095601008585Pigweed100100100100100851009010010010010010098Radish, Wild6510060100458060859595709010095Russian Thistle8090858585907585908550909085Ryegrass, Italian100959090100909895100959510010090Speedwell80100851008010080100100707580100100Wheat, Spring30205201020103550302530305Wheat, Winter1550100105540252020350Windgrass98958595858510085908585859055 Table DCompounds250 g ai / ha129153PostemergenceBarley, Spring3030Barley, Winter3525Blackgrass7580Bluegrass3040Bromegrass, Downy8070Buckwheat, Wild100100Canada Thistle100100Canarygrass8085Chamomile100100Chickweed100100Deadnettle9590Field Poppy98100Field Violet75100Foxtail, Green9585Galium100100 Table DCompounds250 g ai / ha129153PostemergenceGeranium, Cutleaf7598Kochia8535Lambsquarters10075Mustard, Wild100100Oat, Wild10098Oilseed Rape7098Pigweed10085Radish, Wild98100Russian Thistle9055Ryegrass, Italian9090Speedwell75100Wheat, Spring7050Wheat, Winter5535Windgrass9075 Table DCompounds125 g ai / ha12112021222325272834353641PostemergenceBarley, Spring55100101525055010010Barley, Winter515250300250550055Blackgrass7080705085457580908570754570Bluegrass5553035253530303515354025Bromegrass, Downy1010251075256050554040255535Buckwheat, Wild1001006010010010010010010010010010010095Canada Thistle--------------Canarygrass5055304585408580858075705580Chamomile8590751001008585100959010010010080Chickweed90100801001009810010010010010010010095Deadnettle3560100559545752030351002010080Field Poppy100100801001001001001001001001001009075Field Violet90757525100757585758595759090Foxtail, Green7595654085708070808555958050Galium95100901001009810010010010010095100100Geranium, Cutleaf--------------Kochia9565858575100751005550856510085Lambsquarters909580909095759085901009810075Mustard, Wild404075100100100100703070100100100100Oat, Wild8090856085859590909095858585Oilseed Rape35552051009565457065751009525Pigweed100859510090988595951001008510080Radish, Wild306560701001001006585859010010090Russian Thistle---8080757580708080858575Ryegrass, Italian8585858085858585858095809085Speedwell608010010010065752510010010080100100Wheat, Spring101025154010601510101525030Wheat, Winter0515153515555551515525Windgrass5055153085357585808565707060 Table DCompounds125 g ai / ha4247525457596066676972737579PostemergenceBarley, Spring50501040405100103005Barley, Winter01505254540055302000Blackgrass8035157055858575853575806540Bluegrass2010302515553530201540551510Bromegrass, Downy40505525706565652065701510Buckwheat, Wild100901001008510010010010095100100100100Canada Thistle---------100----Canarygrass80006515908570857080803040Chamomile100-1001001008510010010080859085100Chickweed100959010010010010010010090100100100100Deadnettle3530351008590953540751001009520Field Poppy100100901001009585951007010010010095Field Violet90-7595759510095908595909585Foxtail, Green65701070757565901001570755575Galium1007598100901001001001009010010095100Geranium, Cutleaf---------55----Kochia959555100659590100409510010010085Lambsquarters85707595759080100100959010010090Mustard, Wild701590100301009855408010010010040Oat, Wild85205906595951001008095958580Oilseed Rape60556510065857565851080759520Pigweed90100751001001001001008598100100100100Radish, Wild2058010010010095307060901001000Russian Thistle85-4590-858075755080808555Ryegrass, Italian8530759075909095988095959585Speedwell45401001002510090707510010010010035Wheat, Spring1515015107040000607050Wheat, Winter10101525105535000506500Windgrass901557010809085903580754035 Table DCompounds125 g ai / ha808182838485878890104105108109126PostemergenceBarley, Spring1500551505351010151010Barley, Winter500055552510101050Blackgrass9080757585908590556565656530Bluegrass3530301530254530252020252515Bromegrass, Downy7065605065356535405525406020Buckwheat, Wild100100100100100100100100100100100100100100Canada Thistle--------100----98Canarygrass8595758080858585758075808045Chamomile10010010010010090100959895100959598Chickweed100100951009010010010098100100100100100Deadnettle35352555204035351007020757080Field Poppy10010095100908085100757580657575Field Violet951001001001007510080100959510010090Foxtail, Green9095859085858080708575757525Galium9510010010010010010010010010095100100100Geranium, Cutleaf--------75----80Kochia10090100801007090601001009510010095Lambsquarters100100951009595100901001009010095100Mustard, Wild70604065703025251008540959090Oat, Wild1009595909895981009895951009580Oilseed Rape6575607570706575159025757575Pigweed1001001001009585100759510010010010098Radish, Wild50955010055753085759020859075Russian Thistle8090758075806580756550757580Ryegrass, Italian9895909098859590959590959590Speedwell859585757580758510055657075100Wheat, Spring150050155540202020250Wheat, Winter5505000540201020250Windgrass9590809080808585708580758030 Table DCompounds125 g ai / ha129153PostemergenceBarley, Spring3015Barley, Winter3010Blackgrass6075Bluegrass2030Bromegrass, Downy6565Buckwheat, Wild100100Canada Thistle100100Canarygrass7580Chamomile100100Chickweed10085Deadnettle7080Field Poppy80100Field Violet7095Foxtail, Green8585Galium100100 Table DCompounds125 g ai / ha129153PostemergenceGeranium, Cutleaf7590Kochia8030Lambsquarters9565Mustard, Wild98100Oat, Wild9590Oilseed Rape1585Pigweed10080Radish, Wild80100Russian Thistle8545Ryegrass, Italian9090Speedwell6590Wheat, Spring5040Wheat, Winter4025Windgrass5565 Table DCompounds62 g ai / ha12112021222325272834353641PostemergenceBarley, Spring500050150050005Barley, Winter510200100150000005Blackgrass5070404085207075808040653565Bluegrass51052530153520253015251530Bromegrass, Downy1010151060104525252530252020Buckwheat, Wild7595451001009810010010010010010010090Canada Thistle--------------Canarygrass3540203080357580807565304070Chamomile75806595958085959090801009575Chickweed809590100100951009810010010010010098Deadnettle35601003510010651053510020100100Field Poppy959585601008510080100901001007080Field Violet75856515957045757075100758590Foxtail, Green6580253580457565807545904555Galium9010085751009010010010010010098100100Geranium, Cutleaf--------------Kochia8560756545957595554085209595Lambsquarters90908085858575908585951009565Mustard, Wild303570100100959540404585100100100Oat, Wild7080752585857580858585908080Oilseed Rape154515010030603065657098855Pigweed90806510085957510085901008010080Radish, Wild2055304010075753575100851009080Russian Thistle---7575707575757580758570Ryegrass, Italian7580857080808085858095758085Speedwell55651001510060100157085757590100Wheat, Spring0015153010500551020020Wheat, Winter001510255400552515020Windgrass2525103080207075758050655055 Table DCompounds62 g ai / ha4247525457596066676972737579PostemergenceBarley, Spring000010302505052505Barley, Winter01000303025000201500Blackgrass7525154045808070753070702020Bluegrass201051515402525151535301010Bromegrass, Downy200055207055606015555505Buckwheat, Wild9575100100851009510010070100100100100Canada Thistle---------100----Canarygrass7500555808065852550701520Chamomile70-1001001008080901007080859095Chickweed100951001001009810085100801009510095Deadnettle25202510090807515306590909015Field Poppy8510080100100757585100709010010085Field Violet80-6575708095958080959510075Foxtail, Green506056575704080901065702570Galium1007595100901001001001008510010095100Geranium, Cutleaf---------30----Kochia90702095559585953585958010080Lambsquarters855075957585809510095959510080Mustard, Wild70075100301007540353510010010020Oat, Wild851558525909095987585957070Oilseed Rape50205952570702080107070955Pigweed9075401008585951008080100100100100Radish, Wild101065100100957525652080951000Russian Thistle75-3580-808080602075808055Ryegrass, Italian8010508550909095907595859575Speedwell50108510015100807075857510010030Wheat, Spring101000104535000505500Wheat, Winter55105104030000353500Windgrass751054510808580851575701520 Table DCompounds62 g ai / ha808182838485878890104105108109126PostemergenceBarley, Spring100550000251051050Barley, Winter00000000151010505Blackgrass8075707075807585354025453020Bluegrass3520201020202525151010101510Bromegrass, Downy6535453565306525303020303010Buckwheat, Wild100100100100801001008590959510095100Canada Thistle--------100----100Canarygrass8085557565858080456550505535Chamomile951001001009875100100758585858595Chickweed10010090100901009095901009010010098Deadnettle2535102510151515805010505070Field Poppy801008510080908585706575555055Field Violet858510080100658575989090959585Foxtail, Green9095809080807575557070706510Galium9510010010010095100100100909595100100Geranium, Cutleaf--------65----40Kochia10085957595659055100959510010080Lambsquarters100100951009085100809010095959598Mustard, Wild5060352550253520957525758580Oat, Wild9890908595859595909085959570Oilseed Rape557045704570406557515707065Pigweed1001001001009580100759010010010085100Radish, Wild5090209040652060757515757570Russian Thistle7085758070756575756045707540Ryegrass, Italian9590858595859590909585908590Speedwell75807570707075651003550656065Wheat, Spring10000000035151020150Wheat, Winter0000000103515515150Windgrass9080758575708580507570706520 Table DCompounds62 g ai / ha129153PostemergenceBarley, Spring255Barley, Winter205Blackgrass4570Bluegrass1515Bromegrass, Downy4035Buckwheat, Wild10095Canada Thistle10098Canarygrass5575Chamomile9895Chickweed10085Deadnettle4075Field Poppy7595Field Violet7090Foxtail, Green8080Galium100100 Table DCompounds62 g ai / ha129153PostemergenceGeranium, Cutleaf7090Kochia7015Lambsquarters9065Mustard, Wild8098Oat, Wild9085Oilseed Rape585Pigweed9875Radish, Wild7585Russian Thistle8020Ryegrass, Italian8590Speedwell6075Wheat, Spring3530Wheat, Winter3515Windgrass3530 Table DCompounds31 g ai / ha12112021222527283435364142PostemergenceBarley, Spring00000000500000Barley, Winter5102000000000000Blackgrass4065251580156575752530255575Bluegrass0551020101015201035101515Bromegrass, Downy01015045105151520510100Buckwheat, Wild708545801009080100100100951008080Canada Thistle--------------Canarygrass2025101080207075753020155550Chamomile65704070908075808575100957575Chickweed808545909085989510095901009895Deadnettle3560752590105510951580855Field Poppy957535308575708580100100605565Field Violet8560655957065758075657010070Foxtail, Green507051570156070654075354535Galium80858570100901001001009598100100100Geranium, Cutleaf--------------Kochia7050603535809045356025858570Lambsquarters7590608580809080809075957080Mustard, Wild252565751009020153580981009025Oat, Wild4055402080657575757585357075Oilseed Rape02000803055565659575010Pigweed807035808085807575100801007585Radish, Wild102550509585156585658580905Russian Thistle---7070657065707070807070Ryegrass, Italian6570805580757580759065758075Speedwell2550051006010356065706010010Wheat, Spring001502050000150150Wheat, Winter001002050055100100Windgrass1010102570157075704025404070 Table DCompounds31 g ai / ha4752545759606667697273757980PostemergenceBarley, Spring000102515000510000Barley, Winter10002020100001015000Blackgrass2510251570756570204065151075Bluegrass551052515050201510515Bromegrass, Downy50101535305060045250555Buckwheat, Wild601001008065909510060959510070100Canada Thistle--------85-----Canarygrass003557580557525406015555Chamomile-859010080758595657570808580Chickweed90901001001008575857598901009590Deadnettle2035100708070154020857575535Field Poppy808570100706070806580751007560Field Violet-35858075808580759090957590Foxtail, Green50555756535758010606502070Galium6590100901001008590759595909590Geranium, Cutleaf--------15-----Kochia45015409570851060801009570100Lambsquarters45759575908095907580951008595Mustard, Wild02010030907510252085851002035Oat, Wild105751580858595708585507095Oilseed Rape200752060650700656570015Pigweed753510085807595758095100100100100Radish, Wild535804095655550757595010Russian Thistle-2080-80807555157075805070Ryegrass, Italian1040802580808585759570907085Speedwell10707510065855570707570802565Wheat, Spring1000040300004045000Wheat, Winter500535250002525000Windgrass100351075807585156570101575 Table DCompounds31 g ai / ha8182838485878890104105108109126129PostemergenceBarley, Spring0000000100000020Barley, Winter000000000055010Blackgrass6545656575657515351520201535Bluegrass5100201025105101055010Bromegrass, Downy155525403045152020102530525Buckwheat, Wild1008510085958580809065909570100Canada Thistle-------98----98100Canarygrass7550505075556525454040402030Chamomile100909595759085708080758070100Chickweed10080100859085858095909010080100Deadnettle15101551010570451035204035Field Poppy100701007070707065157020452570Field Violet7595908565807590858590908565Foxtail, Green8075757575707025307065551080Galium10090100908585100988585901009090Geranium, Cutleaf-------45----3060Kochia6090708540854585958590957560Lambsquarters9595959080958090958590909075Mustard, Wild502525251010108070570608080Oat, Wild8590808575858075858085956090Oilseed Rape7025651065156507004565605Pigweed1009010095759575801008595859898Radish, Wild752575206015356570575754060Russian Thistle7565757065607530554065603070Ryegrass, Italian8585808080908075907590858580Speedwell75706570357025100304560506035Wheat, Spring000000025100155025Wheat, Winter000000020501010030Windgrass707075756080653055606560020 Table DCompoundTable DCompound31 g ai / ha15331 g ai / ha153PostemergencePostemergenceBarley, Spring5Geranium, Cutleaf75Barley, Winter0Kochia20Blackgrass65Lambsquarters75Bluegrass15Mustard, Wild98Bromegrass, Downy25Oat, Wild85Buckwheat, Wild95Oilseed Rape70Canada Thistle98Pigweed80Canarygrass75Radish, Wild80Chamomile70Russian Thistle25Chickweed80Ryegrass, Italian80Deadnettle70Speedwell75Field Poppy75Wheat, Spring20Field Violet85Wheat, Winter10Foxtail, Green80Windgrass25Galium100 Table DCompounds250 g ai / ha12112022252728343536414247PreemergenceBarley, Spring1501500000200060515Barley, Winter0020002015156500301510Blackgrass909075757595100956595508010050Bluegrass5050553540758075604515908020Bromegrass, Downy7070554580858585806535809015Buckwheat, Wild1001002510095258010003510756085Canada Thistle-------------Canarygrass909090809010010095959865951005Chamomile90100--10095100100-100--10085Chickweed100100100951001001001001001001009510090Deadnettle605510020-508059580851001565Field Poppy9510010010010010010010010010010095100100Field Violet10010010075100100951009510095100100100Foxtail, Green1001006585201001001007510075100100100Galium10010010085851001001008510085100100100Geranium, Cutleaf-------------Kochia7520959075100606550256010010040Lambsquarters1001001001001001001001009510095100100100Mustard, Wild25401001009560655510010090952565Oat, Wild10010085959510095100909585959540Oilseed Rape20405075353525851006515015Pigweed100100100100100100100100100100100100100100Radish, Wild1001002565800953060100701006085Russian Thistle--70209075351525157075-Ryegrass, Italian1001001001001001001001001001007010010070Speedwell9510010090100100100100100100100100100100Wheat, Spring1010354525252525603030852015Wheat, Winter5530255205040100751510Windgrass10010075608010010010070100659510075 Table DCompounds250 g ai / ha5254575960666769727375798081PreemergenceBarley, Spring05106060100060600005Barley, Winter0054565100075750104545Blackgrass657580100100808075758555608585Bluegrass3525658080305065503035357560Bromegrass, Downy2040309598857065609025608575Buckwheat, Wild10080100956000151030501002015Canada Thistle------95-----Canarygrass359065100100959595951007585100100Chamomile100--100100100100100----100-Chickweed100100100100100100100100100100100100100100Deadnettle25954510010055609870100100907555Field Poppy100100100100100100100100100100100100100100Field Violet8595100100100981009595951001009595Foxtail, Green351001001001007085558510010095100100Galium951001001001007570908590801009095Geranium, Cutleaf------10-----Kochia904510010075850540951009510015Lambsquarters100951001001001001001009510010010010095Mustard, Wild9810030100900080801009510050Oat, Wild3095601001009090959510085909595Oilseed Rape5510025808035251525701003540100Pigweed90100100100100100100100100100100100100100Radish, Wild7510010010090709520509010055100-Russian Thistle035-907090251025753510010035Ryegrass, Italian98100951001009590100901000100100100Speedwell100100100100100100100100100100100-100100Wheat, Spring54510857520101080854503540Wheat, Winter0351080550504575150205Windgrass1095801001008595959095858098100 Table DCompounds250 g ai / ha82838485878890104105108109126129153PreemergenceBarley, Spring10555503515200502040Barley, Winter254035152525302025201051040Blackgrass8085908580906075758080657595Bluegrass8035807570806575757560406075Bromegrass, Downy8540858080759585757565308095Buckwheat, Wild0252010060808095253575258585Canada Thistle------100----95100100Canarygrass9510095959590951009895989090100Chamomile100-100-100-100----100100100Chickweed100100100100100100100100100100100100100100Deadnettle70100753570859810065100958095100Field Poppy100100100951009010010010010010095100100Field Violet100100100100100100100100100100100100100100Foxtail, Green851001001009510095100100100954595100Galium8585901008010095100100100100989598Geranium, Cutleaf------90----159590Kochia10050954510055801001001001009510070Lambsquarters100100100100100100100100100100100100100100Mustard, Wild1525204025709095208510098100100Oat, Wild9590959095959810010095909010098Oilseed Rape60103530452505550408590100100Pigweed10010010010010010010010010010010010098100Radish, Wild100906510095-9510055909590100100Russian Thistle6509575100256075901005015100100Ryegrass, Italian9510010090989010010098100100100100100Speedwell10010095100100100100----100100100Wheat, Spring4035-402030704540404007585Wheat, Winter1025515151550155302006050Windgrass1009510010010095981009595100858095 Table DCompounds125 g ai / ha12112022252728343536414247PreemergenceBarley, Spring100100000000030015Barley, Winter00500510150002555Blackgrass8585556055909585408535809530Bluegrass3530302530407065503510806520Bromegrass, Downy7065204025808570505510707015Buckwheat, Wild65100151008520452002010658070Canada Thistle--------------Canarygrass85859070859510095909540901000Chamomile9595--100100100100-100--10085Chickweed1001001009510010010010010010010095100100Deadnettle0050101505555055501002510Field Poppy9595100951001001009510010070-100100Field Violet100100100258010095100758570100100100Foxtail, Green75100157509510010060657010010060Galium10010010075759585858095759595100Geranium, Cutleaf--------------Kochia350757050403030152045807535Lambsquarters100100100100100981001009510075100100100Mustard, Wild10575100852045307510085952040Oat, Wild9595808570959090858575909535Oilseed Rape520500001050655525010Pigweed100659810098100100100100100100100100100Radish, Wild15152050700603560100509515100Russian Thistle---400406515100104065-Ryegrass, Italian1001001001001001001001001001007010010060Speedwell-9085705095100951001001001007080Wheat, Spring052525101055255070015Wheat, Winter5020150000250045510Windgrass859555507010010090551005808520 Table DCompounds125 g ai / ha5254575960666769727375798081PreemergenceBarley, Spring00104045-00000050Barley, Winter00540500005060001545Blackgrass65507095100757570558040558070Bluegrass2515257565252035253510257520Bromegrass, Downy1515259095803535355010507515Buckwheat, Wild557010100500051560025200Canada Thistle-------95-----Canarygrass2580559595859095859070759095Chamomile100--100100100100100----100-Chickweed1009510010010010010010010010095100100100Deadnettle1070259085555575657090100705Field Poppy100100100100100100100100100100100100100100Field Violet7570100951009510095758010098100100Foxtail, Green1565100859565855060505565100100Galium9085100100956535907080601008085Geranium, Cutleaf-------0------Kochia40303595607507010858010010025Lambsquarters10095100100100100100100959510010010070Mustard, Wild901002510085004060100100500Oat, Wild25855095100858090858580859085Oilseed Rape08505040352515150100403550Pigweed651009810010010010010095100100100100100Radish, Wild551002595957575205010010045100-Russian Thistle025-80356000154025759515Ryegrass, Italian10010080100100908598100100100909585Speedwell95100100100100100100100-100100-95100Wheat, Spring00580655006570350250Wheat, Winter01557055000255020005Windgrass107065100100858075809050509590 Table DCompounds125 g ai / ha82838485878890104105108109126129153PreemergenceBarley, Spring0000002050050025Barley, Winter50501001510101000025Blackgrass7570808580854565605075555585Bluegrass6535656545756570603530302575Bromegrass, Downy8060755575655565707065206585Buckwheat, Wild1502580050405552030108585Canada Thistle------100----95100100Canarygrass9090909090908595959090806095Chamomile100-100-100-100----100100100Chickweed1001001001001001001009510010010010098100Deadnettle25156510656590801595807075100Field Poppy100100100-1009010010010010010090100100Field Violet959510095951001009510010010010085100Foxtail, Green9010075100951007010065100752580100Galium804075756075851008595100859095Geranium, Cutleaf-----65----07085Kochia75307510100159095958080758525Lambsquarters100100951001001008510010010010075100100Mustard, Wild25355350651007509510070100100Oat, Wild9590958590908580858090809098Oilseed Rape35103520300055507575155590Pigweed100100100100100100100100100100100100100100Radish, Wild60903510075-909535100907510098Russian Thistle6515952585153555707035510060Ryegrass, Italian9090100859885100100951001009898100Speedwell1001009010090100100----100100100Wheat, Spring15101515152560350252006070Wheat, Winter0505010255510504545Windgrass10090909585858080807580757580 Table DCompounds62 g ai / ha12112022252728343536414247PreemergenceBarley, Spring00500000000005Barley, Winter005000000002000Blackgrass7075304045909085208530758020Bluegrass1515151530353545252515754520Bromegrass, Downy2550535565555550300555510Buckwheat, Wild1010152020030010200552560Canada Thistle--------------Canarygrass606055353580958550854590950Chamomile95100--10010010095-100--10080Chickweed90100100951001001001009595959510095Deadnettle0015000004015090010Field Poppy95957570010010095100855095100100Field Violet100100100156510090852575109095100Foxtail, Green1510010600909580604525806525Galium9585803065907060358520858595Geranium, Cutleaf--------------Kochia0040253510202010025756010Lambsquarters10060359010095100100609895100100100Mustard, Wild00203565040152510085901520Oat, Wild7090706555908585758045909020Oilseed Rape0000000055100500Pigweed100500409810010010095957575100100Radish, Wild051502505000100085-25Russian Thistle---3002510000152015-Ryegrass, Italian1009590100901001009595856510010030Speedwell50-15700801009510075100957525Wheat, Spring00151500000005505Wheat, Winter000000000002005Windgrass60753540208585752595575855 Table DCompounds62 g ai / ha5254575960666769727375798081PreemergenceBarley, Spring001025100000100000Barley, Winter000253000025400000Blackgrass2030359095707525306030457560Bluegrass10102050451500253515105510Bromegrass, Downy015585906035200400353545Buckwheat, Wild205106525000000902515Canada Thistle-------90------Canarygrass2555109095808580808555609065Chamomile100--9510010095100----100-Chickweed989010010010010010010010090100100100100Deadnettle0602090904030551505510650Field Poppy0551001001001001009010010095100100100Field Violet1035100901008598907575100859580Foxtail, Green060707580358050302035608065Galium100451009585201070608050904065Geranium, Cutleaf-------0------Kochia35601060201502015308055750Lambsquarters9065100100100100100100100959510010095Mustard, Wild10010025957000302580351500Oat, Wild2575309095857575759065809085Oilseed Rape050030153520151557535350Pigweed55100751001001009510085100100100100100Radish, Wild151001085907060007570257550Russian Thistle00-502020001025070950Ryegrass, Italian85907510010085809575100100859065Speedwell10095901001001007510070100100-9560Wheat, Spring0056555000355525000Wheat, Winter005353500010400000Windgrass1050358590757555656515409075 Table DCompounds62 g ai / ha82838485878890104105108109126129153PreemergenceBarley, Spring00000000000000Barley, Winter0000000010000010Blackgrass7560758075853560503525451580Bluegrass451530603560403530152051075Bromegrass, Downy653055356545206565253001575Buckwheat, Wild001565045-60502003060Canada Thistle------95----15100100Canarygrass8585859090907585958075501590Chamomile100-100-95-100----100100100Chickweed10010010010010010019810010010010098100100Deadnettle25020035070801025604575100Field Poppy10010095-10095100100100101004598100Field Violet9080100708595951001001001008585100Foxtail, Green75503555551004570559065207075Galium6025607040707595957075709095Geranium, Cutleaf------60----0075Kochia150151055106575509570205550Lambsquarters956595100100100981001001001001007585Mustard, Wild0002505598700607570100100Oat, Wild8585907585858080808080707595Oilseed Rape35520030002060454001585Pigweed10010010010010010035100100100100100100100Radish, Wild607035256506510015100751510098Russian Thistle150510150151060152005015Ryegrass, Italian8075908095851001009098959080100Speedwell7575759085100100----100100100Wheat, Spring00500103515020505045Wheat, Winter00000010000003520Windgrass8075807080756575805060354580 Table DCompounds31 g ai / ha12112022252728343536414247PreemergenceBarley, Spring00500000000000Barley, Winter00500000000000Blackgrass35655204585858515751570805Bluegrass5010100252530025070350Bromegrass, Downy20105150403545020050455Buckwheat, Wild520152002500150352070Canada Thistle--------------Canarygrass40404525258085852075090900Chamomile9580--95100100100-100--9580Chickweed10090208595951001008595959010090Deadnettle0010000000003500Field Poppy95957570095100100-75-9510060Field Violet959585020908075151515958595Foxtail, Green10651025035957055504545300Galium751007010107060150800757085Geranium, Cutleaf--------------Kochia001003500202500802010Lambsquarters20152575100801001006070752598100Mustard, Wild00025504010158545701510Oat, Wild7580153530858585707535859010Oilseed Rape005000001000000Pigweed702503010010010090502555259070Radish, Wild001000000035025020Russian Thistle---0010000002510-Ryegrass, Italian10085859085959090757520959520Speedwell705507003575951000951007025Wheat, Spring005000000004005Wheat, Winter000000000001005Windgrass1560253507575701525070705 Table DCompounds31 g ai / ha5254575960666769727375798081PreemergenceBarley, Spring00555000000000Barley, Winter0001515000550000Blackgrass2015258590257515155015207055Bluegrass0003035100510151510200Bromegrass, Downy00075601525200200353020Buckwheat, Wild20002000000000015Canada Thistle-------30------Canarygrass20150809025403008020458575Chamomile60--100959095100----95-Chickweed988510010095901009570959010010095Deadnettle000503515151550300550Field Poppy090100100751001008510070010090100Field Violet025958095608585103595805575Foxtail, Green050105570151550201515552075Galium7008595750045204015802525Geranium, Cutleaf-------0------Kochia152510201500010306560350Lambsquarters35651009510055958535959510010055Mustard, Wild85500954500006555000Oat, Wild2575159090757060657555808585Oilseed Rape0150200351010505025350Pigweed608070951003035503570854510095Radish, Wild0250-55302500304025200Russian Thistle00-401500001000100Ryegrass, Italian853555100100807590559595809055Speedwell5010025100100758098510095-6555Wheat, Spring00535350000150000Wheat, Winter00510100005150000Windgrass10020858570303525400257560 Table DCompounds31 g ai / ha82838485878890104105108109126129153PreemergenceBarley, Spring00000000000000Barley, Winter00000000500000Blackgrass7020707570802525351525251075Bluegrass1515154025350352510105070Bromegrass, Downy4520351525201503525001575Buckwheat, Wild35010200015015000040Canada Thistle------50----080100Canarygrass756585808585506585453515585Chamomile100-80-95-100----85100100Chickweed100100100100100100100100100100100709898Deadnettle1002502551565-0006098Field Poppy9510090-100-150100101003090100Field Violet10075656580709510010090858585100Foxtail, Green351530251030252045300203575Galium600203015257565806040507585Geranium, Cutleaf------0----0035Kochia00105010753010602010520Lambsquarters75959525701009075951009510010070Mustard, Wild00025020351010556075100Oat, Wild8080907580807575808075657580Oilseed Rape3052501500155520150075Pigweed10010095955075256010010010098100100Radish, Wild6530-0455095-452558080Russian Thistle10055501000000100Ryegrass, Italian7540805590751001008580807570100Speedwell757070508095100----7090100Wheat, Spring00000020000002525Wheat, Winter000000000000105Windgrass7515755580605070752555253575 TEST E

[0109] Seeds of plant species selected from corn (Zea mays), soybean (Glycine max), velvetleaf (Abutilon theophrasti), lambsquarters (Chenopodium album), wild poinsettia (Euphorbia heterophylla), pigweed, palmer (palmer pigweed, Amaranthus palmeri), waterhemp (common waterhemp, Amaranthus rudis), surinam grass (Brachiaria decumbens), crabgrass, large (large crabgrass, Digitaria sanguinalis), crabgrass, Brazilian (Brazilian crabgrass, Digitaria horizontalis), panicum, fall (fall panicum, Panicum dichotomiflorum), foxtail, giant (giant foxtail, Setaria faberii), foxtail, green (green foxtail, Setaria viridis), goosegrass (Eleusine indica), johnsongrass (Sorghum halepense), ragweed (common ragweed, Ambrosia elatior), barnyardgrass (Echinochloa crus-galli), sandbur (southern sandbur, Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), Italian ryegrass (Lolium multiflorum), dayflower (Virginia (VA) dayflower, Commelina virginica), field bindweed (Convolvulus arvensis), morningglory (Ipomoea coccinea), nightshade (eastern black nightshade, Solanum ptycanthum), kochia (Kochia scoparia), nutsedge, yellow (yellow nutsedge, Cyperus esculentus), horseweed (Conyza canadensis), and beggarticks (hairy beggarticks, Bidens pilosa), were planted into a silt loam soil and treated preemergence with test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant.

[0110] At the same time, plants from these crop and weed species and also waterhemp_RES1, (ALS & Triazine resistant common waterhemp, Amaranthus rudis), and waterhemp_RES2, (ALS & HPPD resistant common waterhemp, Amaranthus rudis) were planted in pots containing Redi-Earth ®< planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peat moss, vermiculite, wetting agent and starter nutrients were treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 18 cm for postemergence treatments (1- to 4-leaf stage). Treated plants and controls were maintained in a greenhouse for 14 to 21 d, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table ECompounds250 g ai / ha12202528344142475769727579PostemergenceArrowleaf Sida8040808560759080604580908070Barnyardgrass3535805060406035609030503020Beggarticks1001001001001001001001009810010098100100Corn55151555520201553000Crabgrass, Brazil3515505060505050403030705040Dayflower, VA5065506580909070103080806565Field Bindweed9580959080959590909590908595Horseweed--85-80907085758090705090Kochia--9098908595988575959010098Panicum, Fall8590509090605095708050856075Pigweed, Palmer98357085507595957060607510075Poinsettia, Wild3515306040---3020075-10Ragweed--80957510095909595959590100Ryegrass, Italian9075809075909090105085909080Sandbur3030407580907560357010803065Soybean200307560607550301020507510Waterhemp100908590759085901007590909580Waterhemp_RES1100100809580959598956085909075Waterhemp_RES27560607550708580705065657555 Table ECompounds250 g ai / ha818283848588100126153171PostemergenceArrowleaf Sida60906080506075854095Barnyardgrass50505040302550308050Beggarticks10098100100100100100100100100Corn50100550500Crabgrass, Brazil50505020505050505060Dayflower, VA8065703080800509590Field Bindweed8585758090759510095100Horseweed85809085909080808560Kochia759865100809010010070100Panicum, Fall90759090958580359075Pigweed, Palmer50656070805050804070Poinsettia, Wild5050-40--35507580Ragweed809075958580901009098Ryegrass, Italian80808585808585909590Sandbur75757065707050407060Soybean1035153515100302570Waterhemp75906095907090907590Waterhemp_RES1659570958085901006090Waterhemp_RES250605070505070855060 Table ECompounds125 g ai / ha12202528344142475766697275PostemergenceArrowleaf Sida7035708060709570604070708080Barnyardgrass2530605050405030409020204025Beggarticks1001009810010098951009810010010098100Corn5502050015515150200Crabgrass, Brazil2010205050503040252040306050Dayflower, VA306550507090856003550658050Field Bindweed8575909560808590859880809580Horseweed--70-80808075607590857560Kochia--75100758595958060958090100Panicum, Fall8085308070703080557080308050Pigweed, Palmer75555100506590603030804060100Poinsettia, Wild1515303550---2530-565-Ragweed--859070909095959590909060Ryegrass, Italian656570857585858502050908585Sandbur302030706085706025656057520Soybean150403050706030201520253070Waterhemp98758085708590100853080808090Waterhemp_RES19870808560909070804080858095Waterhemp_RES2705507050-8070602050505060 Table ECompounds125 g ai / ha798182838485889099100105109126153PostemergenceArrowleaf Sida60308060705050906070708010040Barnyardgrass2030504040202050503030404050Beggarticks10010098100951001001009590100100100100Corn0500005000202050Crabgrass, Brazil2550505015503070204050504040Dayflower, VA608060751060709075060605090Field Bindweed9575957010060601008090959095100Horseweed95657585858590707575-858585Kochia907095751008080100708010010010055Panicum, Fall6085758085808570707080803090Pigweed, Palmer40-7550808050605040701005030Poinsettia, Wild204040-30--60501030505050Ragweed95859070986070909090959510080Ryegrass, Italian7075758075758085807080858590Sandbur5070706560707050404050704060Soybean15040010506030025204010Waterhemp706085409065609075-90909050Waterhemp_RES170608580807565807585100909050Waterhemp_RES21550604070405070606570607030 Table ECompound125 g ai / ha171PostemergenceArrowleaf Sida90Barnyardgrass50Beggarticks100Corn0Crabgrass, Brazil50Dayflower, VA70Field Bindweed100Horseweed70Kochia100Panicum, Fall60 Table ECompound125 g ai / ha171PostemergencePigweed, Palmer60Poinsettia, Wild40Ragweed90Ryegrass, Italian85Sandbur50Soybean50Waterhemp85Waterhemp_RES175Waterhemp_RES240 Table ECompounds62 g ai / ha12202534414247576669727579PostemergenceArrowleaf Sida7030607560906050206060757050Barnyardgrass2025505040353030852525403015Beggarticks98100951001009595100100908510095100Corn5002000155101001000Crabgrass, Brazil150204040203520203020404020Dayflower, VA01510408040505156050655050Field Bindweed7065859580908575958085809095Horseweed--80-75807540759075605095Kochia--659598958570709080989880Panicum, Fall7570155065255055607020804060Pigweed, Palmer905358080607535206020507035Poinsettia, Wild1502030--1510-04010Ragweed--759085-8590608080907098Ryegrass, Italian50505080808570004070808040Sandbur301520608050502060500702030Soybean10020204040202502010307010Waterhemp9575758085858080507585659060Waterhemp_RES19070708090757570507570809060Waterhemp_RES2705506080806550104040406015 Table ECompounds62 g ai / ha8182838485889099100105109126153171PostemergenceArrowleaf Sida4070506050509050606060805080Barnyardgrass2040503030304040403030504045Beggarticks1009010010010010098100801008510010095Corn00000050515101000Crabgrass, Brazil4030401030155010504030253050Dayflower, VA70506006060807005050209050Field Bindweed65807010050609070807595909085Horseweed7570807585957560708590758060Kochia70986098707095608090951005095Panicum, Fall8065707075806050507065359050Pigweed, Palmer2060407580555030307065502050Poinsettia, Wild4030-30--504002545203030Ragweed6090509550508080859090807075Ryegrass, Italian7070606560658570607090809075Sandbur6060505060605040404560308550Soybean02501500401001520301540Waterhemp6080508550608060758080904080Waterhemp_RES16075658575705070807590953070Waterhemp_RES22050406550506040606050704030 Table ECompounds31 g ai / ha12202534414247576669727579PostemergenceArrowleaf Sida5025406065852040104050707050Barnyardgrass1520304030202010801520302015Beggarticks859585100901009585100808090100100Corn50010001001500000Crabgrass, Brazil1510103040102020152010504020Dayflower, VA0200106050300102520603050Field Bindweed6560759070809070856070708580Horseweed--70-85757540608070604090Kochia--609070907560509575709070Panicum, Fall757005050156040407020755055Pigweed, Palmer2050407550507035107010507040Poinsettia, Wild100035---1010-530-10Ragweed--659090809080508070855590Ryegrass, Italian35304075658050003065807530Sandbur101015507060352050400601020Soybean0020035301020100525700Waterhemp8570708070757575506565658050Waterhemp_RES18070607590757560408065609050Waterhemp_RES2750507040206015204050356020 Table ECompounds31 g ai / ha818283848588909910010510912653171PostemergenceArrowleaf Sida4065505040608030506065754080Barnyardgrass2030403020203030302030402540Beggarticks909098959010090807590901000080Corn00000000050000Crabgrass, Brazil4020301015155510252040102040Dayflower, VA6040505505060600303008540Field Bindweed6085607050508060758080858070Horseweed5060756060757050358580708550Kochia60904080606090506080951005090Panicum, Fall8570706075756030306060108540Pigweed, Palmer3050407065506510207050402050Poinsettia, Wild3040-20--353003025302025Ragweed608560855050757575-85707560Ryegrass, Italian5050606050508050505075708565Sandbur605040504040403020404005030Soybean01001000300010010040Waterhemp5070407050707045807075755080Waterhemp_RES15060706080605050808070755050Waterhemp_RES21050305540405050505050551015 Table ECompounds16 g ai / ha12669099105109PostemergenceArrowleaf Sida3003070105050Barnyardgrass10202030401525Beggarticks70857585708080Corn0005000Crabgrass, Brazil0010505510Dayflower, VA00040403030Field Bindweed65607060507575Horseweed--6050408060Kochia--9090558080Panicum, Fall70603040204050Pigweed, Palmer700504057560Poinsettia, Wild50-2035300Ragweed--7550507080Ryegrass, Italian20202075403050Sandbur052540203060Soybean00020000Waterhemp70707050656060Waterhemp_RES175657050508060Waterhemp_RES20040505040- Table ECompounds250 g ai / ha12202527282934374147575969PreemergenceArrowleaf Sida8059595357098809810090409880Barnyardgrass20703090959090653065951009010Beggarticks10010098100100100100100100100100100100100Corn00000000025002010Crabgrass, Brazil1001009095959090809580607010060Crabgrass, Large656030859090652090603509520Dayflower, VA259003065706090608080808070Field Bindweed10070959870759860100901001009585Foxtail, Giant98989010010010098659090809510060Foxtail, Green9098701001001001006580757010010030Goosegrass25258590859090108060059850Horseweed--10010010098100-100100--100-Johnsongrass4050090709010001002520358020Kochia854010010010010070856510010010010095Lambsquarters10010010010010098989810010010010010090Morningglory100100951001001009590659510010010085Nightshade100100-98981009095989810098-90Nutsedge, Yellow7070956580957080708535707060Panicum, Fall100100981001001009895100989510010070Pigweed, Palmer1001007010085981009010085656010070Poinsettia, Wild3550-------652050-20Ragweed1009898100100989810098100100100100100Ryegrass, Italian1001001001001001001001001001005080100100Sandbur7075758590859070658070809060Soybean7540-700050006540207020Surinam Grass7595909510098100809095359510050Velvetleaf98901001001001001001001001001001009890Waterhemp100981001009510010010010010010080100100 Table ECompounds250 g ai / ha72757981828384858788153PreemergenceArrowleaf Sida65987570956510070805075Barnyardgrass5065507540752035357090Beggarticks100100100100100100100100100100100Corn0352005015015020Crabgrass, Brazil9890100100100801009010090100Crabgrass, Large9030309890207525652080Dayflower, VA5075706535655075357090Field Bindweed9098100100951009895100100100Foxtail, Giant807590100951009010095100100Foxtail, Green70909010090701001008010095Goosegrass80565809025352075075Horseweed100-100100100-100---100Johnsongrass35156510050200075060Kochia9810010010010075100981009890Lambsquarters100100100100100100100100100100100Morningglory951001001001001009510090100100Nightshade1001001009810010010010098100100Nutsedge, Yellow3565759065754065606595Panicum, Fall9890901001009810010098100100Pigweed, Palmer901007510010080100909010095Poinsettia, Wild20-556020-30-20-75Ragweed1001001001001009810098100100100Ryegrass, Italian100100100100100100100100100100100Sandbur7070759075807590858590Soybean1570500-00000-Surinam Grass90908095909595907595100Velvetleaf90981009598100909595100100Waterhemp100100100901007510085100100100 Table ECompounds125 g ai / ha12202125272829343741475759PreemergenceArrowleaf Sida750855090755098659098755098Barnyardgrass02510906080656535040507560Beggarticks1001009510010010010010010098100100100100Corn000300000000000Crabgrass, Brazil1005070100959580708090100040100Crabgrass, Large353035100805090405080800080Dayflower, VA15250801530651070407003080Field Bindweed9535859860709095408575909895Foxtail, Giant9598751009810010095408070409598Foxtail, Green9095651009810010090256550309095Goosegrass35255095808075501075500598Horseweed--100100100100100100-100100--100Johnsongrass3035-60807580650100003080Kochia350986598806025501007575100Lambsquarters100989510010010010010010098100100100100Morningglory90100901009590958035509010010098Nightshade10098--9595988598989810098-Nutsedge, Yellow5065758020987030406575306075Panicum, Fall9598651001001009898901009580100100Pigweed, Palmer10090598100859510090100752540100Poinsettia, Wild3030--------40025-Ragweed1009870100981009570100959098100100Ryegrass, Italian100100981009810095951001001003065100Sandbur7070659080908090655075103090Soybean401520350007015-200030Surinam Grass80908510090100100959575753585100Velvetleaf908080909895701001007095759595Waterhemp1008585100100859898100981009040100 Table ECompounds125 g ai / ha66697275798081828384858788105PreemergenceArrowleaf Sida655085907525708535805070050Barnyardgrass1515503540203530351030103035Beggarticks10010098100100100100100100100100100100100Corn2000000000002000Crabgrass, Brazil655090908010090100509080902575Crabgrass, Large1503002035908040150652075Dayflower, VA207050606510355253530101010Field Bindweed409565100100100751003510020956570Foxtail, Giant905070358585985010085957010075Foxtail, Green700650806595759575156010040Goosegrass103060060207070530560510Horseweed--100-100100100100-100---100Johnsongrass003510-80653500070020Kochia905060100100100351000100010025100Lambsquarters100-100100100100100100100100100100100100Morningglory405080609075100909590505010060Nightshade1009010090100981009810050100981598Nutsedge, Yellow5030307065358040706035655040Panicum, Fall98759080809810098100959810010098Pigweed, Palmer100609550707075100509050757090Poinsettia, Wild-2010-6040300-10-15-10Ragweed10095908010010010010095100909810098Ryegrass, Italian100100100100100989010098989598100100Sandbur7050604080757060756080758075Soybean010040400000000075Surinam Grass5020756060759585859070809070Velvetleaf80608010095909095707070907095Waterhemp90100100100100100901007590709075100 Table ECompounds125 g ai / ha109153PreemergenceArrowleaf Sida3560Barnyardgrass2570Beggarticks100100Corn010Crabgrass, Brazil70100Crabgrass, Large3575Dayflower, VA2590Field Bindweed80100Foxtail, Giant8095Foxtail, Green6090Goosegrass5060Horseweed100100Johnsongrass40-Kochia10050 Table ECompounds125 g ai / ha109153PreemergenceLambsquarters98100Morningglory6590Nightshade9895Nutsedge, Yellow4080Panicum, Fall95100Pigweed, Palmer8560Poinsettia, Wild3060Ragweed10095Ryegrass, Italian98100Sandbur7585Soybean030Surinam Grass4090Velvetleaf6590Waterhemp9885 Table ECompounds62 g ai / ha12202125272829343741475759PreemergenceArrowleaf Sida65070080650902085500095Barnyardgrass000706050202500250025Beggarticks10010085100100100100981009898100100100Corn00000000000000Crabgrass, Brazil80606098907070751085650090Crabgrass, Large200358515503525075700050Dayflower, VA20200605101003554002540Field Bindweed801565959840090509070509575Foxtail, Giant3595209895981008040706503595Foxtail, Green70954010098100987506025202090Goosegrass5510956575602053500095Horseweed--100100100100100100-100100--100Johnsongrass020-206075807000003025Kochia509008025005090856590Lambsquarters989895100100100100100100100100100100100Morningglory9890759870859065254050754095Nightshade9598--8010098702580809898-Nutsedge, Yellow15355075201520080065-3035Panicum, Fall90953510010010095958010090509898Pigweed, Palmer10050070906065700908503598Poinsettia, Wild3030--------40020-Ragweed75756598959590857590709510095Ryegrass, Italian100989510095958075100951003035100Sandbur2015080654065754035700070Soybean150035-0050350350030Surinam Grass5075651008095989575757507090Velvetleaf75606590100803595905085-6595Waterhemp10080659510090809010075989075100 Table ECompounds62 g ai / ha66697275798081828384858788105PreemergenceArrowleaf Sida4060357580356070250060040Barnyardgrass201030203020251530000020Beggarticks95958080100100100100100100100100100100Corn00000000000000Crabgrass, Brazil25206020309095100108550804035Crabgrass, Large0000035757051000550Dayflower, VA060151070015510200050Field Bindweed5040059070050590598550Foxtail, Giant405065570809865983565659835Foxtail, Green35035070507070405025207530Goosegrass1010400603040250305000Horseweed--100-100100100100-100---100Johnsongrass0000-8090-00065020Kochia60-351007010020900750100035Lambsquarters100-80100100981007598100100100100100Morningglory3030303085708580207030353070Nightshade15808001001009098501009590598Nutsedge, Yellow65020106040301065035605010Panicum, Fall95208050709510095959085909890Pigweed, Palmer65607585707075902010030655098Poinsettia, Wild-2515-60050-0-15-10Ragweed9085906510010010080759880958595Ryegrass, Italian90909010080989595959580959895Sandbur1040351070704035703050656570Soybean01503550000000000Surinam Grass55403550209065606570157510Velvetleaf2020408580707075357030606570Waterhemp80100100601001009090659080909090 Table ECompounds62 g ai / ha109153PreemergenceArrowleaf Sida3070Barnyardgrass1050Beggarticks100100Corn00Crabgrass, Brazi4070Crabgrass, Large4070Dayflower, VA2585Field Bindweed40100Foxtail, Giant4095Foxtail, Green4075Goosegrass2540Horseweed100100Johnsongrass00Kochia8530 Table ECompounds62 g ai / ha109153PreemergenceLambsquarters100100Morningglory2090Nightshade6585Nutsedge, Yellow4070Panicum, Fall90100Pigweed, Palmer10060Poinsettia, Wild2550Ragweed100100Ryegrass, Italian98100Sandbur6585Soybean-50Surinam Grass6080Velvetleaf2590Waterhemp7070 Table ECompounds31 g ai / ha12202125272829343741475759PreemergenceArrowleaf Sida00004040-70070200080Barnyardgrass0004020152000010000Beggarticks100100201001009010080908065100100100Corn00000000000000Crabgrass, Brazil1035409075707030070800060Crabgrass, Large003065-35-005065000Dayflower, VA0150800050350150010Field Bindweed200353580008057530507065Foxtail, Giant507559580958570565300585Foxtail, Green15350956575656500200065Goosegrass15020902035350535001090Horseweed--100100100100100100-100100--100Johnsongrass0350-75707070000000Kochia000020000009002080Lambsquarters6510070100981001001001010035100100100Morningglory607520906585503501530258575Nightshade9075--9090805090258090-Nutsedge, Yellow1000001020000250050Panicum, Fall75850100951009085709080509595Pigweed, Palmer902006565-090001503595Poinsettia, Wild3025--------1500-Ragweed7035309575959590705058090100Ryegrass, Italian95959010095807065908598510100Sandbur101508035301575020500070Soybean00035000700000035Surinam Grass2535109565858575550100585Velvetleaf7530080605007020302003090Waterhemp9065095100956580100075508075 Table ECompounds31 g ai / ha66697275798081828384858788105PreemergenceArrowleaf Sida020205075040201500000Barnyardgrass15100203000000000-Beggarticks7090703510085801001009090908580Corn00000000000000Crabgrass, Brazil2505007565750801060150Crabgrass, Large00000050000000Dayflower, VA05005001000100000Field Bindweed50010 0602506506040020Foxtail, Giant540350605075309551525950Foxtail, Green0030055152020010020500Goosegrass5020050020200205000Horseweed--0-1001009090-100---0Johnsongrass0000700700000-00Kochia00259850900200006500Lambsquarters901090100100100989810015701001000Morningglory02020060656070252025202520Nightshade070008075809035809550050Nutsedge, Yellow50-05010350650-0100Panicum, Fall6020751080909890908595959065Pigweed, Palmer040353075353590075250650Poinsettia, Wild-00-50000-0-0-10Ragweed6540035100709085709060982065Ryegrass, Italian65809010075707575808080759590Sandbur0500060651002000251015Soybean000040000000000Surinam Grass20055401070356506010250Velvetleaf03050357020100025001550Waterhemp6550905075706085658535756080 Table ECompounds31 g ai / ha109153PreemergenceArrowleaf Sida3550Barnyardgrass020Beggarticks75100Corn00Crabgrass, Brazil6090Crabgrass, Large070Dayflower, VA2580Field Bindweed090Foxtail, Giant3575Foxtail, Green050Goosegrass2040Horseweed10090Johnsongrass00Kochia1040 Table ECompounds31 g ai / ha109153PreemergenceLambsquarters95100Morningglory085Nightshade6570Nutsedge, Yellow050Panicum, Fall80100Pigweed, Palmer2050Poinsettia, Wild1040Ragweed5100Ryegrass, Italian75100Sandbur4080Soybean030Surinam Grass3050Velvetleaf085Waterhemp060 Table ECompounds16 g ai / ha126680105109PreemergenceArrowleaf Sida0000040Barnyardgrass0000200Beggarticks10090651009020Corn000000Crabgrass, Brazil00065-70Crabgrass, Large000000Dayflower, VA000000Field Bindweed50020200Foxtail, Giant0400000Foxtail, Green000000Goosegrass005000Horseweed---10000Johnsongrass000-00Kochia0002500Lambsquarters655056500Morningglory20000400Nightshade8035075025Nutsedge, Yellow000500Panicum, Fall657510802575Pigweed, Palmer20002000Poinsettia, Wild200-0010Ragweed35202570500Ryegrass, Italian705040507560Sandbur000000Soybean000000Surinam Grass055000Velvetleaf3500000Waterhemp356500700 Test F

[0111] This test evaluated the effect of mixtures of Compuond 1 or Compound 2 with various commercial herbicides on multiple plant species. Seeds of multiple plant species selected were planted into Sandy Loam soil and treated either Post-emergence or Pre-emergence with test chemicals formulated in a non-phytotoxic solvent mixture. Plants were grown in a greenhouse using supplemental lighting to maintain a photoperiod of approximately 16 h; daytime and nighttime temperatures were approximately 24-30 and 19-21 °C, respectively. Balanced fertilizer was applied through the watering system. Treated plants and controls were maintained in a greenhouse for 20 d, after which time all species were compared to controls and visually evaluated. Plant response ratings summarized in Tables F1 through F4 and 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. Application rates (i.e. "Rate") are expressed in grams of active ingredient per hectare (g a.i. / ha). In the following tables KCHSC is kochia (Kochia scoparia), LOLMU in Italian Ryegrass (Lolium multiflorum), AMBEL is common ragweed (Ambrosia elatior), ECHCG is barnyardgrass (Echinochloa crus-galli), SETVI is giant foxtail (Setaria faberii), AMARE is redroot pigweed (Amaranthus retroflexus), ALOMY is blackgrass (Alopecurus myosuroides) and GALAP is galium (Galium aparine). "Obsd." is observed effect. "Exp." is expected effect calculated from Colby's Equation.

[0112] Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations," Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form: P a + b = P a + P b − P a P b / 100 wherein P a+b is the percentage effect of the mixture expected from additive contribution of the individual components: P a is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and P b is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.

[0113] The results and additive effects expected from Colby's Equation are listed in Tables F1 through F4. Table F1: Observed and Expected Results from Compound 1 Alone and in Combination with Mesotrione when applied Post-emergence.TreatmentRateKCHSCLOLMUAMBELECHCGObsd.Exp.Obsd.Exp.Obsd.Exp.Obsd.Exp.11660.065.095.00.0162100.0100.0100.00.0mesotrione40.00.00.00.0mesotrione1690.00.075.020.01 + mesotrione16 + 4100.060.065.065.075.095.020.00.01 + mesotrione16+16100.096.095.065.0100.098.875.020.01 + mesotrione62+4100.0100.0100.0100.0100.0100.060.00.01 + mesotrione62+16100.0100.0100.0100.0100.0100.0100.020.0 TreatmentRateSETVIAMAREALOMYGALAPObsd.Exp.Obsd.Exp.Obsd.Exp.Obsd.Exp.1160.030.00.065.016240.0100.035.0100.0mesotrione40.00.00.00.0mesotrione160.030.00.035.01 + mesotrione16+40.00.0100.030.00.00.0100.065.01 + mesotrione16+1620.00.0100.051.050.00.0100.077.31 + mesotrione62+470.040.0100.0100.065.035.0100.0100.01 + mesotrione62+1695.040.0100.0100.075.035.0100.0100.0

[0114] As can be seen from the results listed in Table F1, most of the observed results for weed species were greater / equal than expected, thereby showing highly synergistic effect of Compound 1 and mesotrione on all above weed species in Post emergence herbicidal application. Table F2: Observed and Expected Results from Compound 1 Alone and in Combination with Mesotrione when applied Pre-emergence.TreatmentRateKCHSCLOLMUAMBELObsd.Exp.Obsd.Exp.Obsd.Exp.116065651622510090mesotrione4000mesotrione16500301 + mesotrione16+4500656585651 + mesotrione16+ 610025100100100901 + mesotrione62+450508065100761 + mesotrione62+161006310010010093 TreatmentRateECHCGSETVIAMAREObsd.Exp.Obsd.Exp.Obsd.Exp.1160020162206090mesotrione4000mesotrione1600201 + mesotrione16 + 4000098201 + mesotrione16 + 1610205060100901 + mesotrione62 + 420000100361 + mesotrione62 + 164520906010092

[0115] As can be seen from the results listed in Table F2, most of the observed results for weed species were greater / equal than expected, thereby showing highly synergistic effect of Compound 1 and mesotrione on all above weed species in Pre-emergence herbicidal application. Table F3: Observed and Expected Results from Compoune 2 Alone and in Combination with Atrazine when applied Post-emergenceTreatmentRateKCHSCLOLMUAMBELECHCGObsd.Exp.Obsd.Exp.Obsd.Exp.Obsd.Exp.2161650754052626275958020atrazine62621001510202 + atrazine16 + 62100100100100797546502 + atrazine62 + 621001001001009610082100 TreatmentRateSETVIAMAREALOMYGALAPObsd.Exp.Obsd.Exp.Obsd.Exp.Obsd.Exp.216152520100262808060100atrazine6257560502 + atrazine16 + 6224851910081100681002 + atrazine62 + 623695811009510084100

[0116] As can be seen from the results listed in Table F3, most of the observed results for weed species were greater / equal than expected, thereby showing highly synergistic effect of Compound 2 and atrazine on all above weed species in Post emergence herbicidal application. Table F4: Observed and Expected Results from Compound 2 Alone and in Combination with Atrazine when applied Pre-emergenceTreatmentRateKCHSCLOLMUAMBELObsd.Exp.Obsd.Exp.Obsd.Exp.2161600302626205095atrazine6262100100102 + atrazine16 + 62100100100651001002 + atrazine62 + 62100100100100100100 TreatmentRateECHCGSETVIAMAREObsd.Exp.Obsd.Exp.Obsd.Exp.21606025262259875atrazine6205852 +atrazine16 + 623725070621002+atrazine62 + 6296502510098100

[0117] As can be seen from the results listed in Table F4, most of the observed results for weed species were greater / equal than expected, thereby showing synergistic / additive effect of Compound 2 and atrazine on all above weed species in Pre-emergence herbicidal application.

Claims

1. A compound selected from Formula 3, N-oxides and salts thereof, wherein R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, benzyl or phenyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl; X is O, S or NR5; or X is -C(R6)=C(R7)-, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 3; each R3 is independently halogen, -CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R4, R6 and R7 are independently H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R5 is H, C1-C3 alkyl or C1-C3 haloalkyl; n is 0, 1, 2, 3 or 4; and R30 is alkyl; provided that when R4 is H, then X is -C(R6)=C(R7)-; and with the proviso that the compound is not:

2. The compound of Claim 1 wherein X is O, S, -CH=CH-, -C(CH3)=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH3)-; R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, benzyl or phenyl; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy or C1-C5 alkylthio; each R3 is independently halogen, -CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio; R4 is halogen, -CN, C1-C3 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C2 haloalkoxy, C1-C2 alkylthio or C1-C2 haloalkylthio; and n is 0, 1, 2 or 3.

3. The compound of Claim 2 wherein X is -CH=CH-, -C(CH3)=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH3)-; R1 is H, C1-C7 alkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy or benzyl; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C2-C7 alkoxyalkyl or C1-C7 alkoxy; each R3 is independently halogen, -CN, C1-C2 alkyl, -CH=CH2, -C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy; and R4 is halogen, -CN, C1-C2 alkyl, -CH=CH2, -C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.

4. The compound of Claim 3 wherein X is -CH=CH-, -CH=CF-, -CH=CCl- or -CH=C(CH3)-; R1 is methyl, ethyl, n-propyl or 2-methoxyethyl; R2 is H, methyl, ethyl, n-propyl, CF3 or methoxy; each R3 is independently halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy or ethoxy; R4 is halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy or ethoxy; and n is 1 or 2.

5. The compound of any of Claims 1-4, wherein R30 is C1-C6 alkyl.

6. The compound of Claim 5, wherein R30 is methyl or ethyl.

7. A compound of Claim 1 wherein R30 is Me; and X is -CH=CH-, R1 is Me, and R2 is Me, and (R3)n and R4 are defined as in the following tables: (R3)nR4-H5-MeH4,6-di-MeH5,7-di-MeH (R3)nR4-Me5-MeMe4,6-di-MeMe5,7-di-MeMe (R3)nR4-Et5-MeEt4,6-di-MeEt5,7-di-MeEt or X is -CH=CH-, R1 is Me, and R2 is Et, and (R3)n and R4 are defined as in the following tables: (R3)nR4-H5-MeH4,6-di-MeH5,7-di-MeH (R3)nR4-Me5-MeMe4,6-di-MeMe5,7-di-MeMe (R3)nR4-Et5-MeEt4,6-di-MeEt5,7-di-MeEt.

8. A compound of Claim 1 selected from: methyl 2-[2-[2-(2,5-dimethylbenzo[b]thien-3yl)acetyl]-2-methylhydrazinylidene]propanoate; methyl 2-[2-[2-(2,5-dimethyl-3-benzofuranyl)acetyl]-2-methylhydrazinylidene]propanoate; and 2,5,7-trimethyl-3-benzofuranacetic acid 2-(2-methoxy-1-methyl-2-oxoethylidene)-1-methylhydrazide.

9. A method for preparing a compound of Formula 1b wherein R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, benzyl or phenyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl; X is O, S or NR5; or X is -C(R6)=C(R7)-, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 1b; each R3 is independently halogen, -CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R4, R6 and R7 are independently H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R5 is H, C1-C3 alkyl or C1-C3 haloalkyl; and n is 0, 1, 2, 3 or 4; provided that when R4 is H, then X is -C(R6)=C(R7); comprising cyclizing a compound of Formula 3 in the presence of solvent and base wherein R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, benzyl or phenyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl; X is O, S or NR5; or X is -C(R6)=C(R7)-, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 3; each R3 is independently halogen, -CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R4, R6 and R7 are independently H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R5 is H, C1-C3 alkyl or C1-C3 haloalkyl; n is 0, 1, 2, 3 or 4; and R30 is alkyl; provided that when R4 is H, then X is -C(R6)=C(R7)-.

10. The method of Claim 9 for preparing a compound of Formula 1b wherein R1 is methyl or ethyl; R2 is methyl or ethyl; X is -C(R6)=C(R7)-; each R3 is independently F, Cl, Br, methyl, ethyl or methoxy; R4 is halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy or ethoxy; R6 and R7 are H or halogen; and n is 0, 1 or 2; comprising cyclizing the compound of Formula 3 in the presence of solvent and base wherein, in Formula 3, R1 is methyl or ethyl; R2 is methyl or ethyl; X is -C(R6)=C(R7)-; each R3 is independently F, Cl, Br, methyl, ethyl or methoxy; R4 is halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy or ethoxy; R6 and R7 are H or halogen; and n is 0, 1 or 2.

11. A method for preparing a compound of Formula 3 wherein R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, benzyl or phenyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl; X is O, S or NR5; or X is -C(R6)=C(R7)-, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 3; each R3 is independently halogen, -CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R4, R6 and R7 are independently H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R5 is H, C1-C3 alkyl or C1-C3 haloalkyl; n is 0, 1, 2, 3 or 4; and R30 is alkyl; provided that when R4 is H, then X is -C(R6)=C(R7); comprising reacting a hydrazine ester of Formula 4 wherein R1 is H, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C3-C7 alkylthioalkyl, C1-C7 alkoxy, benzyl or phenyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S; R2 is H, halogen, -CN, -CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C2-C4 alkylcarbonyl, C2-C7 alkylcarbonyloxy, C4-C7 alkylcycloalkyl, C3-C7 alkenyl, C3-C7 alkynyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C2-C3 cyanoalkyl, C1-C4 nitroalkyl, C2-C7 haloalkoxyalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C1-C7 alkoxy, C1-C5 alkylthio, C2-C3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl; and R30 is alkyl; with an acid chloride of Formula 5 wherein X is O, S or NR5; or X is -C(R6)=C(R7)-, wherein the carbon atom bonded to R6 is also bonded to the carbon atom bonded to R4, and the carbon atom bonded to R7 is also bonded to the phenyl ring moiety in Formula 5; each R3 is independently halogen, -CN, nitro, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R4, R6 and R7 are independently H, halogen, nitro, -CN, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C5 cycloalkyl, C4-C5 cycloalkylalkyl, C1-C5 haloalkyl, C3-C5 haloalkenyl, C3-C5 haloalkynyl, C2-C5 alkoxyalkyl, C1-C5 alkoxy, C1-C5 haloalkoxy, C1-C5 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C5 haloalkylthio or C2-C5 alkoxycarbonyl; R5 is H, C1-C3 alkyl or C1-C3 haloalkyl; and n is 0, 1, 2, 3 or 4; provided that when R4 is H, then X is -C(R6)=C(R7); in the presence of solvent and base.

12. The method of Claim 11 for preparing a compound of Formula 3 wherein R1 is methyl or ethyl; R2 is methyl or ethyl; X is -C(R6)=C(R7)-; each R3 is independently F, Cl, Br, methyl, ethyl or methoxy; R4 is halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy or ethoxy; R6 and R7 are H or halogen; and n is 0, 1 or 2; comprising reacting a hydrazine ester of Formula 4 wherein R1 is methyl or ethyl; R2 is methyl or ethyl with an acid chloride of Formula 5 wherein X is -C(R6)=C(R7)-; each R3 is independently F, Cl, Br, methyl, ethyl or methoxy; R4 is halogen, -CN, methyl, ethyl, -CH=CH2, -C≡CH, cyclopropyl, CF3, methoxy or ethoxy; R6 and R7 are H or halogen; and n is 0, 1 or 2; in the presence of solvent and base.

13. The method of any of Claims 9-12, wherein R30 is C1-C6 alkyl.

14. The method of Claim 13, wherein R30 is methyl or ethyl.