FIELD OF THE INVENTION
This invention relates to certain pyridazinones, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.
BACKGROUND OF THE INVENTION
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:
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wherein
- W is O or S;
- 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, C1-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 1;
- 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;
- G is G1 or W1G1;
- G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11, or P(═O)R12; or C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C1-C4 alkoxyalkyl, C3-C6 cycloalkyl or C4-C7 cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring;
- W1 is C1-C4 alkanediyl or C2-C4 alkenediyl;
- R8 and R10 are independently C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C1-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C4-C7 cycloalkylalkyl; or phenyl, benzyl, or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl;
- R9 is C1-C7 alkyl, C3-C7 alkenyl, C3-C7 alkynyl, C3-C7 cycloalkyl, C2-C7 haloalkyl, C3-C7 haloalkenyl, C2-C7 alkoxyalkyl, C4-C7 cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocycling ring optionally substituted by halogen, C1-C4 alkyl or C1-C4 haloalkyl;
- R11 is H, C1-C7 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C4-C7 cycloalkylalkyl, C1-C7 haloalkyl or C2-C7 alkoxyalkyl;
- R12 is C1-C7 alkyl or C1-C7 alkoxy; and
- n is 0, 1, 2, 3 or 4;
provided that when R4 is H, then X is —C(R6)═C(R7)—.
More particularly, this invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide or a salt thereof. This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).
This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) through (b16); and salts of compounds of (b1) through (b16), as described below.
DETAILS OF THE INVENTION
As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.
Where applicants have defined an invention or a portion thereof with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms “consisting essentially of” or “consisting of.”
Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
As referred to herein, the term “seedling”, used either alone or in a combination of words means a young plant developing from the embryo of a seed.
As referred to herein, the term “broadleaf” used either alone or in words such as “broadleaf weed” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
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.
In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH3SCH2, CH3SCH2CH2, CH3CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH2 and NCCH2CH2 (alternatively identified as CH2CH2CN).
“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F3C, ClCH2, CF3CH2 and CF3CCl2. The terms “haloalkoxy”, “haloalkylthio”, “haloalkenyl”, “haloalkynyl”, and the like, areis defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O—, CCl3CH2O—, HCF2CH2CH2O— and CF3CH2O—. Examples of “haloalkylthio” include CCl3S—, CF3S—, CCl3CH2S— and ClCH2CH2CH2S—. Examples of “haloalkenyl” include (Cl)2C═CHCH2— and CF3CH2CH═CHCH2—. Examples of “haloalkynyl” include HC≡CCHCl—, CF3C≡C—, CCl3C≡C— and FCH2C≡CCH2—.
“Alkoxycarbonyl” denotes a straight-chain or branched alkoxy moieties bonded to a C(═O) moiety. Examples of “alkoxycarbonyl” include CH3OC(═O)—, CH3CH2OC(═O)—, CH3CH2CH2OC(═O)—, (CH3)2CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers.
The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 7. For example, C1-C4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl; C2 alkoxyalkyl designates CH3OCH2—; C3 alkoxyalkyl designates, for example, CH3CH(OCH3)—, CH3OCH2CH2— or CH3CH2OCH2—; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2— and CH3CH2OCH2CH2—.
When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., (R3)n, wherein n is 1, 2, 3 or 4. When a group contains a substituent which can be hydrogen, for example R2 or R4, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R3)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.
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 and are within the scope of the present invention. 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.
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.
Compounds of Formula 1 typically exist in more than one form, and Formula 1 thus include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1. Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.
One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of a compound of Formula 1 are useful for control of undesired vegetation (i.e. are agriculturally suitable). The salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as 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. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
Embodiments of the present invention as described in the Summary of the Invention include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):
Embodiment 1
A compound of Formula 1 wherein W is O.
Embodiment 2
A compound of Formula 1 or Embodiment 1 wherein X is O, S or —C(R6)═C(R7)—.
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(R6)═C(R7)—.
Embodiment 7
A compound of Formula 1 or Embodiment 1 wherein X is NR5.
Embodiment 7a
A compound of Embodiment 2 wherein X is O, S, —CH═CH—, —C(CH3)═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH3)—.
Embodiment 7b
A compound of Embodiment 2 wherein X is —CH═CH—, —C(CH3)═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH3)—
Embodiment 7c
A compound of Embodiment 2 wherein X is —CH═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH3)—.
Embodiment 7d
A compound of Formula 1 or any one of Embodiments 1 through 7a 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.
Embodiment 7e
A compound of Formula 1 or any one of Embodiments 1 through 7a wherein 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.
Embodiment 8
A compound of Formula 1 or any one of Embodiments 1 through 7 wherein R1 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl.
Embodiment 9
A compound of Embodiment 8 wherein R1 is C1-C3 alkyl, allyl, propargyl, CH2CH2CN, C1-C2 haloalkyl or 2-methoxyethyl.
Embodiment 10
A compound of Embodiment 9 wherein R1 is methyl, ethyl, n-propyl or 2-methoxyethyl.
Embodiment 11
A compound of Embodiment 10 wherein R1 is methyl or ethyl.
Embodiment 12
A compound of Embodiment 11 wherein R1 is methyl.
Embodiment 12a
A compound of Formula 1 wherein R1 is other than H.
Embodiment 12b
A compound of Formula 1 wherein R1 is other than phenyl.
Embodiment 12c
A compound of Formula 1 wherein R2 is H, halogen, —CN, —CHO, C1-C7 alkyl, C3-C8 alkylcarbonylalkyl, C3-C8 alkoxycarbonylalkyl, C1-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.
Embodiment 12d
A compound of Formula 1 wherein R2 is H, halogen, —CN, —CHO, C1-C7 alkyl, C1-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.
Embodiment 13
A compound of Formula 1 or any one of Embodiments 1 through 12 wherein R2 is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl or C1-C3 alkoxy.
Embodiment 14
A compound of Embodiment 13 wherein R2 is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy or ethoxy.
Embodiment 15
A compound of Embodiment 14 wherein R2 is H, methyl, ethyl, n-propyl, CF3 or methoxy.
Embodiment 16
A compound of Embodiment 15 wherein R2 is methyl or ethyl.
Embodiment 17
A compound of Embodiment 16 wherein R2 is methyl.
Embodiment 17a
A compound of Formula 1 wherein R2 is other than phenyl.
Embodiment 18
A compound of Formula 1 or any one of Embodiments 1 through 17 wherein 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.
Embodiment 19
A compound of Embodiment 18 wherein each R3 is independently halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.
Embodiment 20
A compound of Embodiment 19 wherein each R3 is independently halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy.
Embodiment 21
A compound of Embodiment 20 wherein each R3 is independently halogen, —CN, methyl, ethyl, methoxy or ethoxy.
Embodiment 22
A compound of Embodiment 21 wherein each R3 is independently F, Cl, Br, methyl, ethyl or methoxy.
Embodiment 23
A compound of Formula 1 or any one of Embodiments 1 through 22 wherein 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.
Embodiment 24
A compound of Embodiment 23 wherein R4 is halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.
Embodiment 25
A compound of Embodiment 24 wherein R4 is halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy.
Embodiment 26
A compound of Embodiment 25 wherein R4 is methyl or ethyl.
Embodiment 27
A compound of Embodiment 26 wherein R4 is methyl.
Embodiment 28
A compound of Formula 1 or any one of Embodiments 1 through 27 wherein R5 is C1-C2 alkyl.
Embodiment 29
A compound of Embodiment 28 wherein R5 is methyl.
Embodiment 30
A compound of Formula 1 or any one of Embodiments 1 through 29 wherein independently, R6 and R7 are H, 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.
Embodiment 31
A compound of Formula 1 or any one of Embodiments 1 through 30 wherein independently, R6 and R7 are H, halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.
Embodiment 32
A compound of Formula 1 or any one of Embodiments 1 through 31 wherein independently, R6 and R7 are H, halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy.
Embodiment 34a
A compound of Formula 1 or any one of Embodiments 1 through 32 wherein independently, R6 and R7 are H, halogen or C1-C2 alkyl.
Embodiment 34b
A compound of Formula 1 or any one of Embodiments 1 through 32 wherein independently, R6 and R7 are H or halogen.
Embodiment 34c
A compound of Formula 1 or any one of Embodiments 1 through 32 wherein R6 is H and R7 is halogen.
Embodiment 34d
A compound of Formula 1 or any one of Embodiments 1 through 32 wherein R6 is halogen and R7 is H.
Embodiment 33
A compound of Formula 1 or any one of Embodiments 1 through 32 wherein independently, R6 and R7 are H or C1-C2 alkyl.
Embodiment 34
A compound of Formula 1 or any one of Embodiments 1 through 33 wherein R6 is H or methyl (i.e. CH3).
Embodiment 35
A compound of Formula 1 or any one of Embodiments 1 through 34 wherein R7 is H or methyl (i.e. CH3).
Embodiment 36
A compound of Embodiment 34 or 35 wherein R6 is H and R7 is H, or R6 is H and R7 is CH3, or R6 is CH3 and R7 is H.
Embodiment 37
A compound of Embodiment 36 wherein R6 is H and R7 is H.
Embodiment 37a
A compound of Formula 1 or any one of Embodiments 1 through 37 wherein G is G1.
Embodiment 37b
A compound of Formula 1 or any one of Embodiments 1 through 37a whereins G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)R12; or C3-C6 cycloalkyl or C4-C7 cycloalkylalkyl.
Embodiment 37b
A compound of Formula 1 or any one of Embodiments 1 through 37a wherein G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)R12; or C4-C7 cycloalkylalkyl.
Embodiment 38
A compound of Formula 1 or any one of Embodiments 1 through 37 wherein G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)R12.
Embodiment 39
A compound of Embodiment 38 wherein G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8 or P(═O)R12.
Embodiment 39a
A compound of Embodiment 39 wherein G1 is H.
Embodiment 39b
A compound of Embodiment 39 wherein G1 is —C(═O)R8.
Embodiment 39c
A compound of Embodiment 39 wherein G1 is —CO2R9.
Embodiment 39d
A compound of Embodiment 39 wherein G1-S(O)2R8.
Embodiment 39e
A compound of Embodiment 39 or P(═O)R12
Embodiment 40
A compound of Formula 1 or any one of Embodiments 1 through 39e wherein R8 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl.
Embodiment 41
A compound of Embodiment 40 wherein R8 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment 42
A compound of Embodiment 41 wherein R8 and R10 are independently C1-C7 alkyl or C2-C7 alkoxyalkyl.
Embodiment 42a
A compound of any one of Embodiments 1 through 40 wherein R8 is C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment 42b
A compound of Embodiment 41 wherein R8 is independently C1-C3 alkyl or C2-C4 alkoxyalkyl.
Embodiment 42c
A compound of Formula 1 or any one of Embodiments 1 through 37 wherein G is WG1.
Embodiment 42d
A compound of Formula 1 or any one of Embodiments 1 through 42a wherein W1 is C1-C2 alkanediyl or C2-C3 alkenediyl.
Embodiment 42e
A compound of Embodiment 42b wherein W1 is —CH2— or —CH═CH—.
Embodiment 42f
A compound of Embodiment 42c wherein W1 is —CH2—.
Embodiment 43
A compound of Formula 1 or any one of Embodiments 1 through 42 wherein R9 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C3 haloalkyl or C2-C7 alkoxyalkyl.
Embodiment 44
A compound of Embodiment 43 wherein R9 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment 45
A compound of Embodiment 44 wherein R9 is C1-C7 alkyl or C2-C7 alkoxyalkyl.
Embodiment 46
A compound of Formula 1 or any one of Embodiments 1 through 45 wherein R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl.
Embodiment 47
A compound of Embodiment 46 wherein R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment 48
A compound of any one of Embodiments 1 through 47 wherein R12 is C1-C3 alkyl or C1-C3 alkoxy.
Embodiment 49
A compound of Embodiment 48 wherein R12 is CH3 or OCH3.
Embodiment 48
A compound of Formula 1 or any one of Embodiments 1 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.
Embodiments of this invention, including Embodiments 1-51 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments 1-51 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
Combinations of Embodiments 1-51 are illustrated by:
Embodiment A
A compound of Formula 1 wherein
- W is O;
- 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, C1-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;
- G is G1;
- G1 is H, —C(═O)R8, —C(═S)R8, —CO2R9, —C(═O)SR9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)R12; or C3-C6 cycloalkyl or C4-C7 cycloalkylalkyl;
- R8 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl;
- R9 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C3 haloalkyl or C2-C7 alkoxyalkyl;
- R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl;
- R12 is C1-C3 alkyl or C1-C3 alkoxy;
- and
- n is 0, 1, 2 or 3.
Embodiment B
A compound of Embodiment A 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, C1-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;
- R4 is halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
- G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8, —CONR10R11, —S(O)2NR10R11 or P(═O)R12;
- R8, R9 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl;
- R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl; and
- R12 is CH3 or OCH3.
Embodiment C
A compound of Embodiment B 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; G1 is H, —C(═O)R8, —CO2R9, —S(O)2R8 or P(═O)R12; R8 and R9 are independently C1-C7 alkyl or C2-C7 alkoxyalkyl; and
- n is 1 or 2.
Specific embodiments include compounds of Formula 1 selected from the group consisting of:
- 4-(2,5-dimethylbenzo[b]thien-3-yl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 1),
- 5-hydroxy-2,6-dimethyl-4-(2,5,7-trimethylbenzo[b]thien-3-yl)-3(2H)-pyridazinone (Compound 2),
- 5-hydroxy-2,6-dimethyl-4-(2,4,6-trimethylbenzo[b]thien-3-yl)-3(2H)-pyridazinone (Compound 3),
- 5-hydroxy-2,6-dimethyl-4-(2-methyl-3-benzofuranyl)-3 (2H)-pyridazinone (Compound 4),
- 5-hydroxy-4-(5-methoxy-3-benzofuranyl)-2,6-dimethyl-3(2H)-pyridazinone (Compound 5),
- 4-(5-chloro-2-methyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3 (2H)-pyridazinone (Compound 6),
- 4-(2,5-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 7),
- 4-(2,4-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 8),
- 4-(2,7-dimethyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 9),
- 4-(2-ethyl-5-methyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 10),
- 5-hydroxy-2,6-dimethyl-4-(1-naphthalenyl)-3(2H)-pyridazinone (Compound 11),
- 5-hydroxy-2,6-dimethyl-4-(2,5,7-trimethyl-3-benzofuranyl)-3 (2H)-pyridazinone (Compound 12),
- 4-(5-ethyl-2-methyl-3-benzofuranyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 13),
- 5-(acetyloxy)-4-(2,5-dimethyl-3-benzofuranyl)-2,6-dimethyl-3(2H)-pyridazinone (Compound 14),
- 5-(acetyloxy)-4-(2,7-dimethyl-3-benzofuranyl)-2,6-dimethyl-3(2H)-pyridazinone (Compound 15),
- 5-(acetyloxy)-2,6-dimethyl-4-(2,5,7-trimethyl-3-benzofuranyl)-3(2H)-pyridazinone (Compound 16),
- 5-(2,5-dimethyl-3-benzofuranyl)-1,6-dihydro-1,3-dimethyl-6-oxo-4-pyridazinyl 2,2-dimethylpropanoate (Compound 17),
- 1,6-dihydro-1,3-dimethyl-6-oxo-5-(2,5,7-trimethyl-3-benzofuranyl)-4-pyridazinyl 2,2-dimethylpropanoate (Compound 18), and
- 4-(2-ethyl-4,6-dimethylbenzo[b]thien-3-yl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone (Compound 19).
Specific embodiments also include compounds of Formula 1 selected from the group consisting of: compound numbers 1, 3, 11, 23, 25, 27, 28, 29, 32, 42, 47, 57, 59 and 60. Compound numbers refer to compounds in Index Table A.
This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention 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 the invention are particularly useful for selective control of weeds in cereal crops in the Family Poaceae such as maize, rice and wheat.
Embodiments of the present invention as described in the Summary of the Invention include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):
Embodiment P1
A compound of Formula 1 wherein W is O.
Embodiment P2
A compound of Formula 1 or Embodiment P1 wherein X is O, S or —C(R6)═C(R7)—.
Embodiment P3
A compound of Embodiment P2 wherein X is O or S.
Embodiment P4
A compound of Embodiment P3 wherein X is O.
Embodiment P5
A compound of Embodiment P3 wherein X is S.
Embodiment P6
A compound of Embodiment P2 wherein X is —C(R6)═C(R7)—.
Embodiment P7
A compound of Formula 1 or Embodiment P1 wherein X is NR5.
Embodiment P8
A compound of Formula 1 or any one of Embodiments P1 through P7 wherein R1 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl.
Embodiment P9
A compound of Embodiment P8 wherein R1 is C1-C3 alkyl, allyl, propargyl, CH2CH2CN, C1-C2 haloalkyl or 2-methoxyethyl.
Embodiment P10
A compound of Embodiment P9 wherein R1 is methyl, ethyl, n-propyl or 2-methoxyethyl.
Embodiment P11
A compound of Embodiment P10 wherein R1 is methyl or ethyl.
Embodiment P12
A compound of Embodiment P11 wherein R1 is methyl.
Embodiment P13
A compound of Formula 1 or any one of Embodiments P1 through P12 wherein R2 is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl or C1-C3 alkoxy.
Embodiment P14
A compound of Embodiment P13 wherein R2 is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy or ethoxy.
Embodiment P15
A compound of Embodiment P14 wherein R2 is H, methyl, ethyl, n-propyl, CF3 or methoxy.
Embodiment P16
A compound of Embodiment P15 wherein R2 is methyl or ethyl.
Embodiment P17
A compound of Embodiment P16 wherein R2 is methyl.
Embodiment P18
A compound of Formula 1 or any one of Embodiments P1 through P17 wherein 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.
Embodiment P19
A compound of Embodiment P18 wherein each R3 is independently halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.
Embodiment P20
A compound of Embodiment P19 wherein each R3 is independently halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy.
Embodiment P21
A compound of Embodiment P20 wherein each R3 is independently halogen, —CN, methyl, ethyl, methoxy or ethoxy.
Embodiment P22
A compound of Embodiment P21 wherein each R3 is independently F, Cl, Br, methyl, ethyl or methoxy.
Embodiment P23
A compound of Formula 1 or any one of Embodiments P1 through P22 wherein 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.
Embodiment P24
A compound of Embodiment P23 wherein R4 is halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.
Embodiment P25
A compound of Embodiment P24 wherein R4 is halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy.
Embodiment P26
A compound of Embodiment P25 wherein R4 is methyl or ethyl.
Embodiment P27
A compound of Embodiment P26 wherein R4 is methyl.
Embodiment P28
A compound of Formula 1 or any one of Embodiments P1 through P27 wherein R5 is C1-C2 alkyl.
Embodiment P29
A compound of Embodiment P28 wherein R5 is methyl.
Embodiment P30
A compound of Formula 1 or any one of Embodiments P1 through P29 wherein independently, R6 and R7 are H, 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.
Embodiment P31
A compound of Formula 1 or any one of Embodiments P1 through P30 wherein independently, R6 and R7 are H, halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy.
Embodiment P32
A compound of Formula 1 or any one of Embodiments P1 through P31 wherein independently, R6 and R7 are H, halogen, —CN, methyl, ethyl, —CH═CH2, —C≡CH, cyclopropyl, CF3, methoxy or ethoxy.
Embodiment P33
A compound of Formula 1 or any one of Embodiments P1 through P32 wherein independently, R6 and R7 are H or C1-C2 alkyl.
Embodiment P34
A compound of Formula 1 or any one of Embodiments P1 through P33 wherein R6 is H or methyl (i.e. CH3).
Embodiment P35
A compound of Formula 1 or any one of Embodiments P1 through P34 wherein R7 is H or methyl (i.e. CH3).
Embodiment P36
A compound of Embodiment P34 or 35 wherein R6 is H and R7 is H, or R6 is H and R7 is CH3, or R6 is CH3 and R7 is H.
Embodiment P37
A compound of Embodiment P36 wherein R6 is H and R7 is H.
Embodiment P38
A compound of Formula 1 or any one of Embodiments P1 through P37 wherein G is H, —C(═O)R8, —CO2R9, —S(O)2R8, —CONR10R11 or —S(O)2NR10R11.
Embodiment P39
A compound of Embodiment P38 wherein G is H, —C(═O)R8, —CO2R9 or —S(O)2R8.
Embodiment P40
A compound of Formula 1 or any one of Embodiments P1 through P39 wherein R8 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl.
Embodiment P41
A compound of Embodiment P40 wherein R8 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment P42
A compound of Embodiment P41 wherein R8 and R10 are independently C1-C7 alkyl or C2-C7 alkoxyalkyl.
Embodiment P43
A compound of Formula 1 or any one of Embodiments 1 through 42 wherein R9 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C3 haloalkyl or C2-C7 alkoxyalkyl.
Embodiment P44
A compound of Embodiment P43 wherein R9 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment P45
A compound of Embodiment P44 wherein R9 is C1-C7 alkyl or C2-C7 alkoxyalkyl.
Embodiment P46
A compound of Formula 1 or any one of Embodiments P1 through P45 wherein R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl.
Embodiment P47
A compound of Embodiment P46 wherein R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment P48
A compound of Formula 1 or any one of Embodiments P1 through P47 wherein n is 0, 1, 2 or 3.
Embodiment P49
A compound of Embodiment P48 wherein n is 0, 1 or 2.
Embodiment P50
A compound of Embodiment P48 wherein n is 1, 2 or 3.
Embodiment P51
A compound of Embodiment P49 or P50 wherein n is 1 or 2.
Embodiments of this invention, including Embodiments P1-P51 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments P1-P51 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
Combinations of Embodiments P1-P51 are illustrated by:
Embodiment PA
A compound of Formula 1 wherein
- W is O;
- X is O, S, —CH═CH—, —C(CH3)═CH— or —CH═C(CH3)—;
- R1 is C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl, C2-C3 cyanoalkyl, C1-C3 haloalkyl or C2-C4 alkoxyalkyl;
- R2 is H, halogen, —CN, C1-C4 alkyl, C3-C5 cycloalkyl, C1-C3 haloalkyl, C2-C4 alkoxyalkyl or C1-C3 alkoxy;
- 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;
- G is H, —C(═O)R8, —CO2R9, —S(O)2R8, —CONR10R11 or —S(O)2NR10R11;
- R8 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl;
- R9 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C3 haloalkyl or C2-C7 alkoxyalkyl;
- R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C1-C3 haloalkyl or C2-C7 alkoxyalkyl; and
- n is 0, 1, 2 or 3.
Embodiment PB
A compound of Embodiment PA wherein
- R1 is C1-C3 alkyl, allyl, propargyl, CH2CH2CN, C1-C2 haloalkyl or 2-methoxyethyl;
- R2 is H, halogen, C1-C3 alkyl, cyclopropyl, C1-C2 haloalkyl, methoxy or ethoxy;
- each R3 is independently halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
- R4 is halogen, —CN, C1-C2 alkyl, —CH═CH2, —C≡CH, cyclopropyl, C1-C2 haloalkyl or C1-C2 alkoxy;
- R8, R9 and R10 are independently H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl; and
- R11 is H, C1-C7 alkyl, C3-C7 cycloalkyl or C2-C7 alkoxyalkyl.
Embodiment PC
A compound of Embodiment PB wherein
- 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;
- G is H, —C(═O)R8, —CO2R9 or —S(O)2R8;
- R8 and R9 are independently C1-C7 alkyl or C2-C7 alkoxyalkyl; and
- n is 1 or 2.
Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above.
This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics and (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide safeners; and salts of compounds of (b1) through (b16).
“Photosystem II inhibitors” (b1) are chemical compounds that bind to the D-1 protein at the QB-binding niche and thus block electron transport from QA to QB in the chloroplast thylakoid membranes. The electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction. The QB-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron, hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine. Of note is a compound of the invention mixed with atrazine, bromoxynil or bentazon. Also of note is a compound of the invention mixed with atrazine, bromoxynil or metribuzin.
“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron. Of note is a compound of the invention mixed with rimsulfuron, thifensulfuron-methyl, tribenuron, nicosulfuron, metsulfuron-methyl, flupyrsulfuron-methyl, cloransulam-methyl, pyroxsulam or florasulam. Also of note is a compound of the invention mixed with nicosulfuron, flupyrsulfuron or chlorimuron.
“ACCase inhibitors” (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl. Of note is a compound of the invention mixed with pinoxaden or quizalofop.
Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics” (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate. Of particular note is a compound of the invention mixed with dicamba, fluroxypyr-meptyl, 2,4-D, halauxifen-methyl or MCPA. Also of note is a compound of the invention mixed with dicamba.
“EPSP synthase inhibitors” (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
“Photosystem I electron diverters” (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles “leak”, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat and paraquat.
“PPO inhibitors” (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out. Examples of PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-3-alaninate) and 3-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]dihydro-1,5-dimethyl-6-thioxo-1,3,5-triazine-2,4(1H,3H)-dione. Of note is a compound of the invention mixed with saflufenacil, flumioxazin or carfentrazone-ethyl.
“GS inhibitors” (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.
“VLCFA elongase inhibitors” (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides. Of note is a compound of the invention mixed with pyroxasulfone, metolachlor, acetochlor, dimethenamid, alachlor or flufenacet. Also of note is a compound of the invention mixed with flufenacet.
“Auxin transport inhibitors” (b10) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).
“PDS inhibitors” (b11) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone norflurzon and picolinafen.
“HPPD inhibitors” (b12) are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase. Examples of HPPD inhibitors include benzobicyclon, benzofenap, bicyclopyrone (4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one), fenquinotrione (2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide. Of note is a mixture of a compound of the invention with mesotrione, isoxaflutole, tembotrione, bicyclopyrone, topramazone or pyrasulfotole. Also of note is a compound of the invention mixed with mesotrione or pyrasulfatole.
HST (homogentisate solenesyltransererase) inhibitors (b13) disrupt a plant's ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disrupting carotenoid biosynthesis. Examples of HST inhibitors include haloxydine, pyriclor, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one and 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.
HST inhibitors also include compounds of Formulae A and B.
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- wherein Rd1 is H, Cl or CF3; Rd2 is H, Cl or Br; Rd3 is H or Cl; Rd4 is H, Cl or CF3; Rd5 is CH3, CH2CH3 or CH2CHF2; and Rd6 is OH, or —OC(═O)-i-Pr; and Re1 is H, F, Cl, CH3 or CH2CH3; Re2 is H or CF3; Re3 is H, CH3 or CH2CH3; Re4 is H, F or Br; Re5 is Cl, CH3, CF3, OCF3 or CH2CH3; Re6 is H, CH3, CH2CHF2 or C≡CH; Re7 is OH, —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and Ae8 is N or CH.
Cellulose biosynthesis inhibitors (b14) inhibit the biosynthesis of cellulose in certain plants. They are most effective when applied preemergence or early postemergence on young or rapidly growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamid, dichlobenil, flupoxam, indaziflam (N2-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine), isoxaben and triaziflam.
Other herbicides (b15) include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and flamprop-M-isopropyl) organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors. Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (b1) through (b14) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrole, bromobutide, cinmethylin, clomazone, cumyluron, cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron, ipfencarbazone (1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide), metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.
“Herbicide safeners” (b16) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro-[4.5]decane (MON 4660).
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.
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 R1, R2, R3, R4, W, X and G in the compounds of Formulae 1-35 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.
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. Z1-G where Z1 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 Z1 is Cl include acid chlorides (G is —(C═O)R8), chloroformates (G is —CO2R9), carbamoyl chlorides (G is —CONR10R11), sulfonyl chlorides (G is —S(O)2R8) and chlorosulfonamides (G is —S(O)2NR10R11). 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.
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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 R30 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 CH3(CO2C2H5)C═NNCH3C(═O)CH2Ar (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. Pat. Nos. 8,541,414 and 8,470,738. 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.
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Substituted hydrazide esters of Formula 3 can be prepared as outlined in Scheme 3 by coupling a hydrazone ester of Formula 4 (where R30 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 CH3(CO2C2H5)C═NNCH3C(═O)Ar (where Ar is a substituted phenyl) have been published in the patent literature, see U.S. Pat. Nos. 8,541,414 and 8,470,738, 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.
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Hydrazone esters of Formula 4 are readily accessible by reaction of an appropriately substituted hydrazine of formula R1NHNH2 with a ketone or aldehyde ester of formula R2(C═O)CO2R30 (where R30 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 CH3(C═O)CO2C2H5. Preparation of hydrazone esters of Formula 4 is illustrated by Step D of Synthesis Example 1.
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 R31 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.
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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 R31 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 R31 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.
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As shown in Scheme 6, substituted benzofuran-3-ones of Formula 8 where R4 is hydrogen or alkyl can be made by first alkylating a salicylate of Formula 11 with an α-bromo ester of Formula 12 (wherein R32 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.
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As illustrated in Scheme 7, substituted benzothiophenes of Formula 6b (i.e. Formula 6 wherein X is S) where R4 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. Pat. No. 5,376,677 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.
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As shown in Scheme 8, by methods also taught in J. Heterocyclic Chem. 1988, 25, 1271-1272 and U.S. Pat. No. 5,376,677, 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. R4CHBr(C═O)CH2CO2R 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.
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As shown in Scheme 9, naphthalene acetic acid esters of Formula 6c (i.e. Formula 6 wherein X is —C(R6)═C(R7)—) 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. Pat. No. 5,376,677.
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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.
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Hydrolysis of leaving groups at the 5-position of the pyridazinone ring can be accomplished as shown in Scheme 11. When the LG group is lower alkoxy, lower alkylsulfide (sulfoxide or sulfone), halide or N-linked azole, it can be removed by hydrolysis with basic reagents such as tetrabutylammonium hydroxide in solvents such as tetrahydrofuran, dimethoxyethane or dioxane at temperatures from 0 to 120° C. Other hydroxide reagents useful for this hydrolysis include potassium, lithium and sodium hydroxide (see, for example, WO 2009/086041). When the LG group is lower alkoxy, hydrolysis of the LG group can also be accomplished with dealkylation reagents such as boron tribromide or morpholine (see, for example, WO 2009/086041, WO 2013/160126 and WO 2013/050421).
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Introduction of a halogen at the 6-position of the pyridazinone can be accomplished by zincation followed by halogenation. For conditions, reagents and examples of zincation of pyridazinones, see Verhelst, T., Ph.D. thesis, University of Antwerp, 2012. Typically the pyridazinone of Formula 26 is treated in tetrahydrofuran with a solution of Zn(TMP)—LiCl or Zn(TMP)2—MgCl2—LiCl (commercially available) at −20 to 30° C. to form a zinc reagent. Subsequent addition of bromine or iodine provides compounds of Formula 27 (wherein R2 is Br or I, respectively). This method is shown in Scheme 12. For preparation of a variety of appropriate zincation reagents, see Wunderlich, S. Ph.D. thesis, University of Munich, 2010 and references cited therein, as well as WO 2008/138946 and WO 2010/092096. Zincation at the 6-position of the pyridazinone ring can be accomplished in the presence of aromatic/heteroaromatic substituents, alkoxy substituents or halogen at the 4-position of the pyridazinone ring, or in the presence of halogen or alkoxy substituents at the 5-position of the pyridazinone ring.
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The R2 substitutent of compounds of Formula 28 (wherein R2 is halogen or sulfonate) can be further transformed into other functional groups. Compounds wherein R2 is alkyl, cycloalkyl or substituted alkyl can be prepared by transition metal catalyzed reactions of compounds of Formula 28 as shown in Scheme 13. For reviews of these types of reactions, see: E. Negishi, Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley and Sons, Inc., New York, 2002, N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Springer, New York, 2002, H. C. Brown et al., Organic Synthesis via Boranes, Aldrich Chemical Co., Milwaukee, Vol. 3, 2002, Suzuki et al., Chemical Reviews 1995, 95, 2457-2483 and Molander et al., Accounts of Chemical Research 2007, 40, 275-286. Also see Gribble and Li editors Palladium in Heterocyclic Chemistry Volume 1, Pergamon Press, Amsterdam, 2000 and Gribble and Li editors Palladium in Heterocyclic Chemistry Volume 2, Pergamon Press, Amsterdam, 2007. For a review of Buchwald-Hartwig chemistry see Yudin and Hartwig, Catalyzed Carbon-Heteroatom Bond Formation, 2010, Wiley, New York.
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Related synthetic methods for the introduction of other functional groups at the R-position of Formula 29 are known in the art. Copper catalyzed reactions are useful for introducing the CF3 group. For a comprehensive recent review of reagents for this reaction see Wu, Neumann and Beller in Chemistry: An Asian Journal, 2012, ASAP, and references cited therein. For introduction of a sulfur containing substitutent at this position, see methods disclosed in WO 2013/160126. For introduction of a cyano group, see WO 2014/031971. For introduction of a nitro group, see J. Am. Chem. Soc., 2009, 12898. For introduction of a fluoro substituent, see J. Am. Chem. Soc., 2014, 3792.
Compounds of Formula 28 can be prepared by reaction of organometallic reagents with pyridazinones of Formula 29 with a reactive group at the 4-position, as shown in Scheme 14. Depending upon the leaving group a transition metal catalyst may be desirable. When the leaving group is lower alkoxy, N-linked azole (such as pyrazole or triazole) or sulfonate, no catalyst is required, and reaction directly with a magnesium reagent can take place at the 4-position. This reaction can be done in a variety of solvents which do not react with organomagnesium reagents. Typical reaction conditions include tetrahydrofuran as the solvent, a reaction temperature of −20 to 65° C., and an excess of the organomagnesium reagent. When the reactive group at the 4-position is halogen, a transition metal catalyst and ligand are helpful. A variety of different coupling partners can be used, including boron (Suzuki Reaction), tin (Stille Reaction), and zinc (Negishi reaction); these reactions can be catalyzed by palladium and nickel catalysts with a wide variety of ligands. Conditions for these reactions are known in the art; see, for example, Palladium-Catalyzed Coupling Reactions: Practical Aspects and Future Development Edited by Arpad Molnar, Wiley, 2013 and references cited within. The organomagnesium reagents used in the non-catalyzed process can be prepared by direct insertion of magnesium into a carbon-halogen bond (optionally in the presence of a lithium halide), by a Grignard exchange reaction with an i-propylmagnesium halide (optionally in the presence of a lithium halide), or by transformation of an organolithium reagent by reaction with a magnesium salt such as magnesium bromide etherate. A variety of groups which are inert toward the organomagnesium reagents can be present at R2 and at the 5-position of the pyridazinone in these reactions.
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Compounds of Formula 29 are known in the art or can be prepared by methods described by Maes and Lemiere in Comprehensive Heterocyclic Chemistry III Volume 8, Katritsky, Ramsden, Scriven and Taylor editors and references cited therein. See also Verhelst, Ph.D. thesis University of Antwerp and references cited therein. Functional group transformations on pyridazinones are also described in Stevenson et. al. J. Heterocyclic Chem. 2005, 42, 427; U.S. Pat. No. 6,077,953; WO 2009/086041 and references cited therein; U.S. Pat. No. 2,782,195; WO 2013/160126; and WO 2013/050421.
Compounds of Formula 1b can also be prepared by hydrolysis of sulfonates of Formula 31 in aqueous base. Suitable bases include sodium, potassium or tetrabutylammonium hydroxide. Typical reaction temperatures range from 0 to 80° C., and typical reaction times are 1-12 hours. This method is shown in Scheme 15.
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Compounds of Formula 31 can be prepared by the cyclization of compounds of Formula 32 by treatment with base. Typical bases useful in this method include potassium, sodium or cesium carbonate. Typical solvents include acetonitrile, tetrahydrofuran or N,N-dimethylformamide. This method is shown in Scheme 16.
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Compounds of Formula 32 can be prepared by the method shown in Scheme 17. In this method, compounds of Formula 33 are coupled with compounds of Formula 34 in the presence of a base. Bases useful in this method include triethylamine, sodium or potassium carbonate, pyridine or diisopropylethylamine.
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Compounds of Formula 33 can be prepared by methods known in the art.
Compounds of Formula 34 can be prepared by several methods. In one method shown in Scheme 18, compounds of Formula 35 are first treated with ClC(O)CO2Me in the presence of aluminum trichloride. Subsequent hydrolysis to the carboxylic acid, followed by treatment with oxalyl chloride, provides the acyl chlorides of Formula 34.
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Compounds of Formula 35 are commercially available or can be prepared by methods known in the art.
As shown in Scheme 20 compounds of formula 1c can be made by rearrangement of compounds of Formula 30. This rearrangement may be carried out at temperatures between 110 and 300° C. Suitable solvents include, but are not limited to, aromatic hydrocarbons such as xylenes, diethylbenzene, and mesitylene as well as halogenated aromatics such as dichlorobenzene. Other high boiling solvents such as Dowtherm A and diglyme may be successfully employed. Many other solvents with lower boiling points can be used in conjunction with microwave heating especially when ionic liquids are added to the medium.
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Compounds of Formula 30 can be prepared as shown in Scheme 21 by alkylation of pyridazinones of Formula 31 with alkyl halides of Formula 32. The reaction can be carried out in a variety of solvents such as acetone, 2-butanone, acetonitrile, dimethylacetamide, N-methylpyrrolidinone, dimethylsulfoxide and dimethylformamide. The presence of an acid acceptor such as, but not limited to, cesium carbonate, potassium carbonate, sodium carbonate, potassium hydroxide or sodium hydroxide is preferred. The leaving group Y can be halogen or sulfonate.
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Compounds of Formula 30 may also be prepared as shown in Scheme 22 by the nucleophilic displacement reaction of pyridazinones of Formula 33 with alcohols of Formula 33. Suitable solvents include dioxanes, dimethoxyethane, tetrahydrofuran, dimethylacetamide, N-methylpyrrolidinone, dimethylsulfoxide and dimethylformamide. Suitable acid acceptors include, but are not limited to, sodium hydride, potassium hydride, potassium t-butoxide, sodium hexamethyldisilazide, potassium hexamethyldisilazide, and lithium hexamethyldisilazide.
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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.
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It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999.
It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular presented to prepare the compounds of Formula 1.
One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.
Examples of intermediates useful in the preparation of compounds of this invention are shown in Tables I-1a through I-3d. The position(s) of the R3 group(s) in Tables I-1a through I-3d is(are) based on the locant numbering shown below.
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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
|
|
![embedded image]()
|
|
X is S, and R is CO2Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, and R is CO2Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, and R is CO2H.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, and R is C(O)Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is CO2Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is CO2Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is CO2H.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is C(O)Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CF—, and R is CO2Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CF—, and R is CO2Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CF—, and R is CO2H.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CF—, and R is C(O)Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
TABLE I-1b
|
|
![embedded image]()
|
|
X is S, R1 is Me, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CCl—, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CCl—, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CCl—, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CCl—, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CCl—, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CCl—, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
TABLE I-2a
|
|
![embedded image]()
|
|
X is S, and R is CO2Na.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, and R is CO2K.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, and R is CO2H.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, and R is C(O)Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is CO2Na.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is CO2K.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is CO2H.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, and R is C(O)Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
TABLE I-2b
|
|
![embedded image]()
|
|
X is S, R1 is Me, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Me, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Me, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
Table I-2c
Table I-2c is identical to Table I-2b, except that R1 is —SO2Ph.
Table I-2d
Table I-2d is identical to Table I-2b, except that R1 is —SO2(4-methylphenyl).
Table I-2e
Table I-2e is identical to Table I-2b, except that R1 is —SO2(4-chlorophenyl).
TABLE I-3a
|
|
![embedded image]()
|
|
X is S, R is Me, R1 is Me, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Me, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Me, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Me, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Me, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Me, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is S, R is Me, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Me, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Me, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Me, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Me, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Me, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Me, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Et, and R2 is Me.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Et, and R2 is Et.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Et, and R2 is Br.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Et, and R2 is I.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Et, and R2 is Cl.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
X is —CH═CH—, R is Me, R1 is Et, and R2 is OMe.
|
(R3)n
R4
|
|
—
H
|
5-Me
H
|
4,6-di-Me
H
|
5,7-di-Me
H
|
—
Me
|
5-Me
Me
|
4,6-di-Me
Me
|
5,7-di-Me
Me
|
—
Et
|
5-Me
Et
|
4,6-di-Me
Et
|
5,7-di-Me
Et
|
|
Table I-3b
Table I-3b is identical to Table I-3a, except that R is phenyl.
Table I-3c
Table I-3c is identical to Table I-3a, except that R is 4-methylphenyl.
Table I-3d
Table I-3d is identical to Table I-3a, except that R is 4-chlorophenyl.
Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting Examples are illustrative of the invention. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCl3 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 1
Preparation 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
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 (MgSO4) 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).
1H 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
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).
1H 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
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 (MgSO4), filtered and concentrated by rotary evaporation to yield the title product as a white solid (0.26 g).
1H 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
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.
1H 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
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 (MgSO4), 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).
1H 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
A solution of methyl 2-[2-[2-(2,5-dimethylbenzo[b]thien-3yl)acetyl]-2-methylhydrazinylidene]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 (MgSO4), 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, a compound of the present invention, as a white solid (118 mg).
1H 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 2
Preparation 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
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).
1H 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
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 (MgSO4), 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.
1H 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
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 (MgSO4) 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.
1H 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
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 (MgSO4), 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).
1H 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
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).
1H 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
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 (MgSO4), 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.
1H 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
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 (MgSO4), 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).
1H 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
A solution of methyl 2-[2-[2-(2,5-dimethyl-3-benzofuranyl)acetyl]-2-methylhydrazinylidene]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 (MgSO4), 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, a compound of the present invention, as a white solid (790 mg).
1H NMR (DMSO-d6) 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 3
Preparation 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
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 (MgSO4), 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.
1H 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
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 (MgSO4), 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.
1H 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
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 (MgSO4), 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.
1H 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
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 (MgSO4), 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).
1H 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
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.
1H 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
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 (MgSO4), 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.
1H 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
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 (MgSO4), 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).
1H 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
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 (MgSO4), 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, a compound of the present invention, as a white solid (72.3 mg).
1H 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).
Synthesis Example 4
Preparation of 4-(2,3-dimethyl-1-naphthalenyl)-5-hydroxy-6-methoxy-2-methyl-3(2H)-pyridazinone (Compound 46)
Step A: Preparation of 5-chloro-4,6-dimethoxy-2-methyl-3(2H)-pyridazinone
4,5-Dichloro-6-methoxy-2-methyl-3(2H)-pyridazinone (2.00 g, 9.57 mmol) and sodium methoxide (2.00 mL of a 25 wt % solution in MeOH) were combined in 1,4-dioxane (20 mL) and stirred at room temperature overnight. The solution was then concentrated to 50% volume and partitioned between water (100 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layers were combined, washed with brine, dried over MgSO4 and concentrated. The resulting residue was absorbed onto silica gel (1 g) and purified by MPLC with a 0-100% ethyl acetate/hexane gradient through a pre-packed 40 g silica gel column. The fractions containing pure desired product were concentrated in vacuo to yield 1.78 g of the title compound as a white solid.
Step B: Preparation of 5-chloro-4-(2,3-dimethyl-1-naphthalenyl)-6-methoxy-2-methyl-3 (2H)-pyridazinone
In a 2-neck 100 mL RB flask flushed with nitrogen fitted with a thermometer, 1-bromo-2,3-dimethylnaphthalene (1.41 g, 6.01 mmol) was dissolved in anhydrous tetrahydrofuran (15 mL) and cooled over a dry ice/acetone bath to −78° C. N-Butyllithium (2.4 mL of a 2.5M solution in hexane) was added dropwise over 15 minutes, and the reaction mixture was stirred at −78° C. for 5 minutes. The cooling bath was then removed and the solution was allowed to warm to −50° C. Magnesium bromide etherate (1.55 g, 6.01 mmol) was then added in one portion, and the reaction mixture was stirred and warmed to −20° C. The product of Step A (0.700 g, 4.00 mmol) was then added in one portion, and the reaction mixture was stirred and warmed to room temperature. After 1 h, the resulting green colored solution was poured into saturated aqueous NH4Cl (100 mL) and extracted into ethyl acetate (4×50 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in dichloromethane, absorbed onto silica gel (1 g) and purified by MPLC with a gradient of 0-100% ethyl acetate/hexane through a 40 g silica gel column. The fractions containing pure desired product were combined and concentrated in vacuo to yield 0.290 g of the title compound.
Step C: Preparation of 4-(2,3-dimethyl-1-naphthalenyl)-5-hydroxy-6-methoxy-2-methyl-3 (21H)-pyridazinone
The product of Step B (0.200 g, 0.608 mmol) was dissolved in 1,4-dioxane (10 mL) and treated with tetrabutylammonium hydroxide (0.800 mL of a 40 wt % solution in water). The resulting solution was heated to reflux and stirred for 2 h. The reaction mixture was then cooled to room temperature and poured into 1N HCl (50 mL) and extracted into ethyl acetate (4×20 mL). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The crude solid was dissolved in dichloromethane and absorbed onto silica gel (1 g). Purification was performed by MPLC with a 40 to 100% ethyl actetate/hexane gradient through a 40 g silica gel column. The fractions containing desired product were combined and concentrated in vacuo to yield 0.130 g of the title compound, a compound of the invention, as a white solid.
Synthesis Example 5
Preparation of 6-chloro-4-(5-chloro-2-methylbenzo[b]thiene-2-yl)-5-hydroxy-2-methylpyridazin-3(2H)-one (Compound 91)
Step A: Preparation of 6-chloro-5-[(5-chlorobenzo[b]thien-2-yl)methoxy]-2-methylpyridazin-3 (2H)-one
A slurry of N,N-dimethylformamide (20 mL) and sodium hydride (0.335 g, 8.37 mmol) was cooled over ice for 15 min under nitrogen. 5-Chloro-[b]thiophene-2-methanol (1.33 g, 6.7 mmol) was added portionwise under a blanket of nitrogen and stirred over ice for 15 min. 5,6-Dichloro-2-methyl-3(2H)-pyridazinone (1.00 g, 5.58 mol) was then added under a blanket of nitrogen. The ice bath was removed and the reaction mixture was allowed to stir at room temperature overnight. The resulting reaction mixture was then poured into a solution of saturated ammonium chloride and ice (200 mL) and extracted into diethyl ether (3×40 mL). The resulting organic layers were combined, dried over MgSO4 and absorbed onto silica gel (4 g). Chromatography using a 40 g silica gel column eluting with a gradient of 0 to 100% ethyl acetate in hexanes gradient afforded the title compound as as a yellow solid. (1.00 g, 53% yield).
1H NMR (500 MHz) δ 7.78-7.71 (m, 2H), 7.37-7.32 (m, 2H), 5.35 (s, 2H), 3.74 (s, 3H).
Step B: Preparation 6-chloro-4-(5-chloro-2-methylbenzo[b]thiene-2-yl)-5-hydroxy-2-methylpyridazin-3(2H)-one
6-Chloro-5-[(5-chlorobenzo[b]thien-2-yl)methoxy]-2-methylpyridazin-3 (2H)-one (i.e. the product obtained in Step A above, 0.250 g, 0.700 mmol) was dissolved in 5 mL xylenes in a 40 mL scintillation vial and stirred at 175° C. overnight. The reaction mixture was then cooled to room temperature and 40 mL of hexane was added. The resulting precipitate was filtered, washed with hexane and dried to give the desired product as an orange solid (0.100 g).
1H NMR (500 MHz) δ 7.71-7.69 (m, 1H), 7.30-7.27 (m, 1H), 7.26-7.24 (m, 1H), 3.80 (s, 3H), 2.43 (s, 3H).
By the procedures described herein together with methods known in the art, the following compounds of 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)2Me means methylsulfonyl, and “-” means no substitution with R3.
TABLE 1
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![embedded image]()
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W is O, X is S, R1 is Me, R2 is Me, and G is H.
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(R3)n
R4
(R3)n
R4
(R3)n
R4
|
|
—
H
—
Me
—
Et
|
4-Me
H
4-Me
Me
4-Me
Et
|
5-Me
H
5-Me
Me
5-Me
Et
|
6-Me
H
6-Me
Me
6-Me
Et
|
7-Me
H
7-Me
Me
7-Me
Et
|
4-Et
H
4-Et
Me
4-Et
Et
|
5-Et
H
5-Et
Me
5-Et
Et
|
6-Et
H
6-Et
Me
6-Et
Et
|
7-Et
H
7-Et
Me
7-Et
Et
|
4-Pr
H
4-Pr
Me
4-Pr
Et
|
5-Pr
H
5-Pr
Me
5-Pr
Et
|
6-Pr
H
6-Pr
Me
6-Pr
Et
|
7-Pr
H
7-Pr
Me
7-Pr
Et
|
4-OMe
H
4-OMe
Me
4-OMe
Et
|
5-OMe
H
5-OMe
Me
5-OMe
Et
|
6-OMe
H
6-OMe
Me
6-OMe
Et
|
7-OMe
H
7-OMe
Me
7-OMe
Et
|
4-CN
H
4-CN
Me
4-CN
Et
|
5-CN
H
5-CN
Me
5-CN
Et
|
6-CN
H
6-CN
Me
6-CN
Et
|
7-CN
H
7-CN
Me
7-CN
Et
|
4-CF3
H
4-CF3
Me
4-CF3
Et
|
5-CF3
H
5-CF3
Me
5-CF3
Et
|
6-CF3
H
6-CF3
Me
6-CF3
Et
|
7-CF3
H
7-CF3
Me
7-CF3
Et
|
4-F
H
4-F
Me
4-F
Et
|
5-F
H
5-F
Me
5-F
Et
|
6-F
H
6-F
Me
6-F
Et
|
7-F
H
7-F
Me
7-F
Et
|
4-Cl
H
4-Cl
Me
4-Cl
Et
|
5-Cl
H
5-Cl
Me
5-Cl
Et
|
6-Cl
H
6-Cl
Me
6-Cl
Et
|
7-Cl
H
7-Cl
Me
7-Cl
Et
|
4-Br
H
4-Br
Me
4-Br
Et
|
5-Br
H
5-Br
Me
5-Br
Et
|
6-Br
H
6-Br
Me
6-Br
Et
|
7-Br
H
7-Br
Me
7-Br
Et
|
4-OCHF2
H
4-OCHF2
Me
4-OCHF2
Et
|
5OCHF2
H
5OCHF2
Me
5OCHF2
Et
|
6-OCHF2
H
6-OCHF2
Me
6-OCHF2
Et
|
7-OCHF2
H
7-OCHF2
Me
7-OCHF2
Et
|
4-(C≡CH)
H
4-(C≡CH)
Me
4-(C≡CH)
Et
|
5-(C≡CH)
H
5-(C≡CH)
Me
5-(C═CH)
Et
|
6-(C≡CH)
H
6-(C≡CH)
Me
6-(C═CH)
Et
|
7-(C≡CH)
H
7-(C≡CH)
Me
7-(C≡CH)
Et
|
4,5-di-Me
H
4,5-di-Me
Me
4,5-di-Me
Et
|
4,6-di-Me
H
4,6-di-Me
Me
4,6-di-Me
Et
|
4,7-di-Me
H
4,7-di-Me
Me
4,7-di-Me
Et
|
5,6-di-Me
H
5,6-di-Me
Me
5,6-di-Me
Et
|
5,7-di-Me
H
5,7-di-Me
Me
5,7-di-Me
Et
|
5-Cl, 7-Me
H
5-Cl, 7-Me
Me
5-Cl, 7-Me
Et
|
5-Cl, 7-OMe
H
5-Cl, 7-OMe
Me
5-Cl, 7-OMe
Et
|
5-F, 7-Me
H
5-F, 7-Me
Me
5-F, 7-Me
Et
|
5-Me, 7-F
H
5-Me, 7-F
Me
5-Me, 7-F
Et
|
5-Me, 7-Cl
H
5-Me, 7-Cl
Me
5-Me, 7-Cl
Et
|
5-Me, 7-CN
H
5-Me, 7-CN
Me
5-Me, 7-CN
Et
|
5-Me, 7-OMe
H
5-Me, 7-OMe
Me
5-Me, 7-OMe
Et
|
5-(C≡CH), 7-Me
H
5-(C≡CH), 7-Me
Me
5-(C≡CH), 7-Me
Et
|
5,7-di-F
H
5,7-di-F
Me
5,7-di-F
Et
|
5,7-di-Cl
H
5,7-di-Cl
Me
5,7-di-Cl
Et
|
5,7-di-Br
H
5,7-di-Br
Me
5,7-di-Br
Et
|
—
Pr
—
F
—
Cl
|
4-Me
Pr
4-Me
F
4-Me
Cl
|
5-Me
Pr
5-Me
F
5-Me
Cl
|
6-Me
Pr
6-Me
F
6-Me
Cl
|
7-Me
Pr
7-Me
F
7-Me
Cl
|
4-Et
Pr
4-Et
F
4-Et
Cl
|
5-Et
Pr
5-Et
F
5-Et
Cl
|
6-Et
Pr
6-Et
F
6-Et
Cl
|
7-Et
Pr
7-Et
F
7-Et
Cl
|
4-Pr
Pr
4-Pr
F
4-Pr
Cl
|
5-Pr
Pr
5-Pr
F
5-Pr
Cl
|
6-Pr
Pr
6-Pr
F
6-Pr
Cl
|
7-Pr
Pr
7-Pr
F
7-Pr
Cl
|
4-OMe
Pr
4-OMe
F
4-OMe
Cl
|
5-OMe
Pr
5-OMe
F
5-OMe
Cl
|
6-OMe
Pr
6-OMe
F
6-OMe
Cl
|
7-OMe
Pr
7-OMe
F
7-OMe
Cl
|
4-CN
Pr
4-CN
F
4-CN
Cl
|
5-CN
Pr
5-CN
F
5-CN
Cl
|
6-CN
Pr
6-CN
F
6-CN
Cl
|
7-CN
Pr
7-CN
F
7-CN
Cl
|
4-CF3
Pr
4-CF3
F
4-CF3
Cl
|
5-CF3
Pr
5-CF3
F
5-CF3
Cl
|
6-CF3
Pr
6-CF3
F
6-CF3
Cl
|
7-CF3
Pr
7-CF3
F
7-CF3
Cl
|
4-F
Pr
4-F
F
4-F
Cl
|
5-F
Pr
5-F
F
5-F
Cl
|
6-F
Pr
6-F
F
6-F
Cl
|
7-F
Pr
7-F
F
7-F
Cl
|
4-Cl
Pr
4-Cl
F
4-Cl
Cl
|
5-Cl
Pr
5-Cl
F
5-Cl
Cl
|
6-Cl
Pr
6-Cl
F
6-Cl
Cl
|
7-Cl
Pr
7-Cl
F
7-Cl
Cl
|
4-Br
Pr
4-Br
F
4-Br
Cl
|
5-Br
Pr
5-Br
F
5-Br
Cl
|
6-Br
Pr
6-Br
F
6-Br
Cl
|
7-Br
Pr
7-Br
F
7-Br
Cl
|
4-OCHF2
Pr
4-OCHF2
F
4-OCHF2
Cl
|
5OCHF2
Pr
5OCHF2
F
5OCHF2
Cl
|
6-OCHF2
Pr
6-OCHF2
F
6-OCHF2
Cl
|
7-OCHF2
Pr
7-OCHF2
F
7-OCHF2
Cl
|
4-(C≡CH)
Pr
4-(C≡CH)
F
4-(C≡CH)
Cl
|
5-(C≡CH)
Pr
5-(C≡CH)
F
5-(C≡CH)
Cl
|
6-(C≡CH)
Pr
6-(C≡CH)
F
6-(C≡CH)
Cl
|
7-(C≡CH)
Pr
7-(C≡CH)
F
7-(C≡CH)
Cl
|
4,5-di-Me
Pr
4,5-di-Me
F
4,5-di-Me
Cl
|
4,6-di-Me
Pr
4,6-di-Me
F
4,6-di-Me
Cl
|
4,7-di-Me
Pr
4,7-di-Me
F
4,7-di-Me
Cl
|
5,6-di-Me
Pr
5,6-di-Me
F
5,6-di-Me
Cl
|
5,7-di-Me
Pr
5,7-di-Me
F
5,7-di-Me
Cl
|
5-Cl, 7-Me
Pr
5-Cl, 7-Me
F
5-Cl, 7-Me
Cl
|
5-Cl, 7-OMe
Pr
5-Cl, 7-OMe
F
5-Cl, 7-OMe
Cl
|
5-F, 7-Me
Pr
5-F, 7-Me
F
5-F, 7-Me
Cl
|
5-Me, 7-F
Pr
5-Me, 7-F
F
5-Me, 7-F
Cl
|
5-Me, 7-Cl
Pr
5-Me, 7-Cl
F
5-Me, 7-Cl
Cl
|
5-Me, 7-CN
Pr
5-Me, 7-CN
F
5-Me, 7-CN
Cl
|
5-Me, 7-OMe
Pr
5-Me, 7-OMe
F
5-Me, 7-OMe
Cl
|
5-(C≡CH), 7-Me
Pr
5-(C≡CH), 7-Me
F
5-(C≡CH), 7-Me
Cl
|
5,7-di-F
Pr
5,7-di-F
F
5,7-di-F
Cl
|
5,7-di-Cl
Pr
5,7-di-Cl
F
5,7-di-Cl
Cl
|
5,7-di-Br
Pr
5,7-di-Br
F
5,7-di-Br
Cl
|
—
Br
—
CN
—
C≡CH
|
4-Me
Br
4-Me
CN
4-Me
C≡CH
|
5-Me
Br
5-Me
CN
5-Me
C≡CH
|
6-Me
Br
6-Me
CN
6-Me
C≡CH
|
7-Me
Br
7-Me
CN
7-Me
C≡CH
|
4-Et
Br
4-Et
CN
4-Et
C≡CH
|
5-Et
Br
5-Et
CN
5-Et
C≡CH
|
6-Et
Br
6-Et
CN
6-Et
C≡CH
|
7-Et
Br
7-Et
CN
7-Et
C≡CH
|
4-Pr
Br
4-Pr
CN
4-Pr
C≡CH
|
5-Pr
Br
5-Pr
CN
5-Pr
C≡CH
|
6-Pr
Br
6-Pr
CN
6-Pr
C≡CH
|
7-Pr
Br
7-Pr
CN
7-Pr
C≡CH
|
4-OMe
Br
4-OMe
CN
4-OMe
C≡CH
|
5-OMe
Br
5-OMe
CN
5-OMe
C≡CH
|
6-OMe
Br
6-OMe
CN
6-OMe
C≡CH
|
7-OMe
Br
7-OMe
CN
7-OMe
C≡CH
|
4-CN
Br
4-CN
CN
4-CN
C≡CH
|
5-CN
Br
5-CN
CN
5-CN
C≡CH
|
6-CN
Br
6-CN
CN
6-CN
C≡CH
|
7-CN
Br
7-CN
CN
7-CN
C≡CH
|
4-CF3
Br
4-CF3
CN
4-CF3
C≡CH
|
5-CF3
Br
5-CF3
CN
5-CF3
C≡CH
|
6-CF3
Br
6-CF3
CN
6-CF3
C≡CH
|
7-CF3
Br
7-CF3
CN
7-CF3
C≡CH
|
4-F
Br
4-F
CN
4-F
C≡CH
|
5-F
Br
5-F
CN
5-F
C≡CH
|
6-F
Br
6-F
CN
6-F
C≡CH
|
7-F
Br
7-F
CN
7-F
C≡CH
|
4-Cl
Br
4-Cl
CN
4-Cl
C≡CH
|
5-Cl
Br
5-Cl
CN
5-Cl
C≡CH
|
6-Cl
Br
6-Cl
CN
6-Cl
C≡CH
|
7-Cl
Br
7-Cl
CN
7-Cl
C≡CH
|
4-Br
Br
4-Br
CN
4-Br
C≡CH
|
5-Br
Br
5-Br
CN
5-Br
C≡CH
|
6-Br
Br
6-Br
CN
6-Br
C≡CH
|
7-Br
Br
7-Br
CN
7-Br
C≡CH
|
4-OCHF2
Br
4-OCHF2
CN
4-OCHF2
C≡CH
|
5OCHF2
Br
5OCHF2
CN
5OCHF2
C≡CH
|
6-OCHF2
Br
6-OCHF2
CN
6-OCHF2
C≡CH
|
7-OCHF2
Br
7-OCHF2
CN
7-OCHF2
C≡CH
|
4-(C≡CH)
Br
4-(C≡CH)
CN
4-(C≡CH)
C≡CH
|
5-(C≡CH)
Br
5-(C≡CH)
CN
5-(C≡CH)
C≡CH
|
6-(C≡CH)
Br
6-(C≡CH)
CN
6-(C≡CH)
C≡CH
|
7-(C≡CH)
Br
7-(C≡CH)
CN
7-(C≡CH)
C≡CH
|
4,5-di-Me
Br
4,5-di-Me
CN
4,5-di-Me
C≡CH
|
4,6-di-Me
Br
4,6-di-Me
CN
4,6-di-Me
C≡CH
|
4,7-di-Me
Br
4,7-di-Me
CN
4,7-di-Me
C≡CH
|
5,6-di-Me
Br
5,6-di-Me
CN
5,6-di-Me
C≡CH
|
5,7-di-Me
Br
5,7-di-Me
CN
5,7-di-Me
C≡CH
|
5-Cl, 7-Me
Br
5-Cl, 7-Me
CN
5-Cl, 7-Me
C≡CH
|
5-Cl, 7-OMe
Br
5-Cl, 7-OMe
CN
5-Cl, 7-OMe
C≡CH
|
5-F, 7-Me
Br
5-F, 7-Me
CN
5-F, 7-Me
C≡CH
|
5-Me, 7-F
Br
5-Me, 7-F
CN
5-Me, 7-F
C≡CH
|
5-Me, 7-Cl
Br
5-Me, 7-Cl
CN
5-Me, 7-Cl
C≡CH
|
5-Me, 7-CN
Br
5-Me, 7-CN
CN
5-Me, 7-CN
C≡CH
|
5-Me, 7-OMe
Br
5-Me, 7-OMe
CN
5-Me, 7-OMe
C≡CH
|
5-(C≡CH), 7-Me
Br
5-(C≡CH), 7-Me
CN
5-(C≡CH), 7-Me
C≡CH
|
5,7-di-F
Br
5,7-di-F
CN
5,7-di-F
C≡CH
|
5,7-di-Cl
Br
5,7-di-Cl
CN
5,7-di-Cl
C≡CH
|
5,7-di-Br
Br
5,7-di-Br
CN
5,7-di-Br
C≡CH
|
—
OMe
—
OCHF2
—
SMe
|
4-Me
OMe
4-Me
OCHF2
4-Me
SMe
|
5-Me
OMe
5-Me
OCHF2
5-Me
SMe
|
6-Me
OMe
6-Me
OCHF2
6-Me
SMe
|
7-Me
OMe
7-Me
OCHF2
7-Me
SMe
|
4-Et
OMe
4-Et
OCHF2
4-Et
SMe
|
5-Et
OMe
5-Et
OCHF2
5-Et
SMe
|
6-Et
OMe
6-Et
OCHF2
6-Et
SMe
|
7-Et
OMe
7-Et
OCHF2
7-Et
SMe
|
4-Pr
OMe
4-Pr
OCHF2
4-Pr
SMe
|
5-Pr
OMe
5-Pr
OCHF2
5-Pr
SMe
|
6-Pr
OMe
6-Pr
OCHF2
6-Pr
SMe
|
7-Pr
OMe
7-Pr
OCHF2
7-Pr
SMe
|
4-OMe
OMe
4-OMe
OCHF2
4-OMe
SMe
|
5-OMe
OMe
5-OMe
OCHF2
5-OMe
SMe
|
6-OMe
OMe
6-OMe
OCHF2
6-OMe
SMe
|
7-OMe
OMe
7-OMe
OCHF2
7-OMe
SMe
|
4-CN
OMe
4-CN
OCHF2
4-CN
SMe
|
5-CN
OMe
5-CN
OCHF2
5-CN
SMe
|
6-CN
OMe
6-CN
OCHF2
6-CN
SMe
|
7-CN
OMe
7-CN
OCHF2
7-CN
SMe
|
4-CF3
OMe
4-CF3
OCHF2
4-CF3
SMe
|
5-CF3
OMe
5-CF3
OCHF2
5-CF3
SMe
|
6-CF3
OMe
6-CF3
OCHF2
6-CF3
SMe
|
7-CF3
OMe
7-CF3
OCHF2
7-CF3
SMe
|
4-F
OMe
4-F
OCHF2
4-F
SMe
|
5-F
OMe
5-F
OCHF2
5-F
SMe
|
6-F
OMe
6-F
OCHF2
6-F
SMe
|
7-F
OMe
7-F
OCHF2
7-F
SMe
|
4-Cl
OMe
4-Cl
OCHF2
4-Cl
SMe
|
5-Cl
OMe
5-Cl
OCHF2
5-Cl
SMe
|
6-Cl
OMe
6-Cl
OCHF2
6-Cl
SMe
|
7-Cl
OMe
7-Cl
OCHF2
7-Cl
SMe
|
4-Br
OMe
4-Br
OCHF2
4-Br
SMe
|
5-Br
OMe
5-Br
OCHF2
5-Br
SMe
|
6-Br
OMe
6-Br
OCHF2
6-Br
SMe
|
7-Br
OMe
7-Br
OCHF2
7-Br
SMe
|
4-OCHF2
OMe
4-OCHF2
OCHF2
4-OCHF2
SMe
|
5OCHF2
OMe
5OCHF2
OCHF2
5OCHF2
SMe
|
6-OCHF2
OMe
6-OCHF2
OCHF2
6-OCHF2
SMe
|
7-OCHF2
OMe
7-OCHF2
OCHF2
7-OCHF2
SMe
|
4-(C≡CH)
OMe
4-(C≡CH)
OCHF2
4-(C≡CH)
SMe
|
5-(C≡CH)
OMe
5-(C≡CH)
OCHF2
5-(C≡CH)
SMe
|
6-(C≡CH)
OMe
6-(C≡CH)
OCHF2
6-(C≡CH)
SMe
|
7-(C≡CH)
OMe
7-(C≡CH)
OCHF2
7-(C≡CH)
SMe
|
4,5-di-Me
OMe
4,5-di-Me
OCHF2
4,5-di-Me
SMe
|
4,6-di-Me
OMe
4,6-di-Me
OCHF2
4,6-di-Me
SMe
|
4,7-di-Me
OMe
4,7-di-Me
OCHF2
4,7-di-Me
SMe
|
5,6-di-Me
OMe
5,6-di-Me
OCHF2
5,6-di-Me
SMe
|
5,7-di-Me
OMe
5,7-di-Me
OCHF2
5,7-di-Me
SMe
|
5-Cl, 7-Me
OMe
5-Cl, 7-Me
OCHF2
5-Cl, 7-Me
SMe
|
5-Cl, 7-OMe
OMe
5-Cl, 7-OMe
OCHF2
5-Cl, 7-OMe
SMe
|
5-F, 7-Me
OMe
5-F, 7-Me
OCHF2
5-F, 7-Me
SMe
|
5-Me, 7-F
OMe
5-Me, 7-F
OCHF2
5-Me, 7-F
SMe
|
5-Me, 7-Cl
OMe
5-Me, 7-Cl
OCHF2
5-Me, 7-Cl
SMe
|
5-Me, 7-CN
OMe
5-Me, 7-CN
OCHF2
5-Me, 7-CN
SMe
|
5-Me, 7-OMe
OMe
5-Me, 7-OMe
OCHF2
5-Me, 7-OMe
SMe
|
5-(C≡CH), 7-Me
OMe
5-(C≡CH), 7-Me
OCHF2
5-(C≡CH), 7-Me
SMe
|
5,7-di-F
OMe
5,7-di-F
OCHF2
5,7-di-F
SMe
|
5,7-di-Cl
OMe
5,7-di-Cl
OCHF2
5,7-di-Cl
SMe
|
5,7-di-Br
OMe
5,7-di-Br
OCHF2
5,7-di-Br
SMe
|
—
SCHF2
—
SCF3
|
4-Me
SCHF2
4-Me
SCF3
|
5-Me
SCHF2
5-Me
SCF3
|
6-Me
SCHF2
6-Me
SCF3
|
7-Me
SCHF2
7-Me
SCF3
|
4-Et
SCHF2
4-Et
SCF3
|
5-Et
SCHF2
5-Et
SCF3
|
6-Et
SCHF2
6-Et
SCF3
|
7-Et
SCHF2
7-Et
SCF3
|
4-Pr
SCHF2
4-Pr
SCF3
|
5-Pr
SCHF2
5-Pr
SCF3
|
6-Pr
SCHF2
6-Pr
SCF3
|
7-Pr
SCHF2
7-Pr
SCF3
|
4-OMe
SCHF2
4-OMe
SCF3
|
5-OMe
SCHF2
5-OMe
SCF3
|
6-OMe
SCHF2
6-OMe
SCF3
|
7-OMe
SCHF2
7-OMe
SCF3
|
4-CN
SCHF2
4-CN
SCF3
|
5-CN
SCHF2
5-CN
SCF3
|
6-CN
SCHF2
6-CN
SCF3
|
7-CN
SCHF2
7-CN
SCF3
|
4-CF3
SCHF2
4-CF3
SCF3
|
5-CF3
SCHF2
5-CF3
SCF3
|
6-CF3
SCHF2
6-CF3
SCF3
|
7-CF3
SCHF2
7-CF3
SCF3
|
4-F
SCHF2
4-F
SCF3
|
5-F
SCHF2
5-F
SCF3
|
6-F
SCHF2
6-F
SCF3
|
7-F
SCHF2
7-F
SCF3
|
4-Cl
SCHF2
4-Cl
SCF3
|
5-Cl
SCHF2
5-Cl
SCF3
|
6-Cl
SCHF2
6-Cl
SCF3
|
7-Cl
SCHF2
7-Cl
SCF3
|
4-Br
SCHF2
4-Br
SCF3
|
5-Br
SCHF2
5-Br
SCF3
|
6-Br
SCHF2
6-Br
SCF3
|
7-Br
SCHF2
7-Br
SCF3
|
4-OCHF2
SCHF2
4-OCHF2
SCF3
|
5OCHF2
SCHF2
5OCHF2
SCF3
|
6-OCHF2
SCHF2
6-OCHF2
SCF3
|
7-OCHF2
SCHF2
7-OCHF2
SCF3
|
4-(C≡CH)
SCHF2
4-(C≡CH)
SCF3
|
5-(C≡CH)
SCHF2
5-(C≡CH)
SCF3
|
6-(C≡CH)
SCHF2
6-(C≡CH)
SCF3
|
7-(C≡CH)
SCHF2
7-(C≡CH)
SCF3
|
4,5-di-Me
SCHF2
4,5-di-Me
SCF3
|
4,6-di-Me
SCHF2
4,6-di-Me
SCF3
|
4,7-di-Me
SCHF2
4,7-di-Me
SCF3
|
5,6-di-Me
SCHF2
5,6-di-Me
SCF3
|
5,7-di-Me
SCHF2
5,7-di-Me
SCF3
|
5-Cl, 7-Me
SCHF2
5-Cl, 7-Me
SCF3
|
5-Cl, 7-OMe
SCHF2
5-Cl, 7-OMe
SCF3
|
5-F, 7-Me
SCHF2
5-F, 7-Me
SCF3
|
5-Me, 7-F
SCHF2
5-Me, 7-F
SCF3
|
5-Me, 7-Cl
SCHF2
5-Me, 7-Cl
SCF3
|
5-Me, 7-CN
SCHF2
5-Me, 7-CN
SCF3
|
5-Me, 7-OMe
SCHF2
5-Me, 7-OMe
SCF3
|
5-(C≡CH), 7-Me
SCHF2
5-(C≡CH), 7-Me
SCF3
|
5,7-di-F
SCHF2
5,7-di-F
SCF3
|
5,7-di-Cl
SCHF2
5,7-di-Cl
SCF3
|
5,7-di-Br
SCHF2
5,7-di-Br
SCF3
|
|
Table 2 is constructed in the same manner except that the Row Heading “W is O, X is S, R1 is Me, R2 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, R1 is Me, R2 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, R1 is Me, R2 is Me, (R3)n is “-” (i.e. n is 0; no substitution with R3), R4 is H, and G is C(O)Me. Tables 3 through 627 are constructed similarly.
|
Table
Row Heading
|
|
|
2
W is O, X is S, R1 is Me, R2 is Me, and G is C(O)Me.
|
3
W is O, X is S, R1 is Me, R2 is Me, and G is C(O)Et.
|
4
W is O, X is S, R1 is Me, R2 is Me, and G is C(O)-i-Pr.
|
5
W is O, X is S, R1 is Me, R2 is Me, and G is C(O)-t-Bu.
|
6
W is O, X is S, R1 is Me, R2 is Me, and G is CO2Me.
|
7
W is O, X is S, R1 is Me, R2 is Me, and G is CO2Et.
|
8
W is O, X is S, R1 is Me, R2 is Me, and G is CO2-i-Pr.
|
9
W is O, X is S, R1 is Me, R2 is Me, and G is CO2-t-Bu.
|
10
W is O, X is S, R1 is Me, R2 is Me, and G is SO2Me.
|
11
W is O, X is S, R1 is Me, R2 is H, and G is C(O)Me.
|
12
W is O, X is S, R1 is Me, R2 is H, and G is C(O)Et.
|
13
W is O, X is S, R1 is Me, R2 is H, and G is C(O)-i-Pr.
|
14
W is O, X is S, R1 is Me, R2 is H, and G is C(O)-t-Bu.
|
15
W is O, X is S, R1 is Me, R2 is H, and G is CO2Me.
|
16
W is O, X is S, R1 is Me, R2 is H, and G is CO2Et.
|
17
W is O, X is S, R1 is Me, R2 is H, and G is CO2-i-Pr.
|
18
W is O, X is S, R1 is Me, R2 is H, and G is CO2-t-Bu.
|
19
W is O, X is S, R1 is Me, R2 is H, and G is SO2Me.
|
20
W is O, X is S, R1 is Me, R2 is Et, and G is C(O)Me.
|
21
W is O, X is S, R1 is Me, R2 is Et, and G is C(O)Et.
|
22
W is O, X is S, R1 is Me, R2 is Et, and G is C(O)-i-Pr.
|
23
W is O, X is S, R1 is Me, R2 is Et, and G is C(O)-t-Bu.
|
24
W is O, X is S, R1 is Me, R2 is Et, and G is CO2Me.
|
25
W is O, X is S, R1 is Me, R2 is Et, and G is CO2Et.
|
26
W is O, X is S, R1 is Me, R2 is Et, and G is CO2-i-Pr.
|
27
W is O, X is S, R1 is Me, R2 is Et, and G is CO2-t-Bu.
|
28
W is O, X is S, R1 is Me, R2 is Et, and G is SO2Me.
|
29
W is O, X is S, R1 is Me, R2 is Pr, and G is C(O)Me.
|
30
W is O, X is S, R1 is Me, R2 is Pr, and G is C(O)Et.
|
31
W is O, X is S, R1 is Me, R2 is Pr, and G is C(O)-i-Pr.
|
32
W is O, X is S, R1 is Me, R2 is Pr, and G is C(O)-t-Bu.
|
33
W is O, X is S, R1 is Me, R2 is Pr, and G is CO2Me.
|
34
W is O, X is S, R1 is Me, R2 is Pr, and G is CO2Et.
|
35
W is O, X is S, R1 is Me, R2 is Pr, and G is CO2-i-Pr.
|
36
W is O, X is S, R1 is Me, R2 is Pr, and G is CO2-t-Bu.
|
37
W is O, X is S, R1 is Me, R2 is Pr, and G is SO2Me.
|
38
W is O, X is S, R1 is Me, R2 is CF3, and G is C(O)Me.
|
39
W is O, X is S, R1 is Me, R2 is CF3, and G is C(O)Et.
|
40
W is O, X is S, R1 is Me, R2 is CF3, and G is C(O)-i-Pr.
|
41
W is O, X is S, R1 is Me, R2 is CF3, and G is C(O)-t-Bu.
|
42
W is O, X is S, R1 is Me, R2 is CF3, and G is CO2Me.
|
43
W is O, X is S, R1 is Me, R2 is CF3, and G is CO2Et.
|
44
W is O, X is S, R1 is Me, R2 is CF3, and G is CO2-i-Pr.
|
45
W is O, X is S, R1 is Me, R2 is CF3, and G is CO2-t-Bu.
|
46
W is O, X is S, R1 is Me, R2 is CF3, and G is SO2Me.
|
47
W is O, X is S, R1 is Me, R2 is Cl, and G is C(O)Me.
|
48
W is O, X is S, R1 is Me, R2 is Cl, and G is C(O)Et.
|
49
W is O, X is S, R1 is Me, R2 is Cl, and G is C(O)-i-Pr.
|
50
W is O, X is S, R1 is Me, R2 is Cl, and G is C(O)-t-Bu.
|
51
W is O, X is S, R1 is Me, R2 is Cl, and G is CO2Me.
|
52
W is O, X is S, R1 is Me, R2 is Cl, and G is CO2Et.
|
53
W is O, X is S, R1 is Me, R2 is Cl, and G is CO2-i-Pr.
|
54
W is O, X is S, R1 is Me, R2 is Cl, and G is CO2-t-Bu.
|
55
W is O, X is S, R1 is Me, R2 is Cl, and G is SO2Me.
|
56
W is O, X is S, R1 is Me, R2 is Br, and G is C(O)Me.
|
57
W is O, X is S, R1 is Me, R2 is Br, and G is C(O)Et.
|
58
W is O, X is S, R1 is Me, R2 is Br, and G is C(O)-i-Pr.
|
59
W is O, X is S, R1 is Me, R2 is Br, and G is C(O)-t-Bu.
|
60
W is O, X is S, R1 is Me, R2 is Br, and G is CO2Me.
|
61
W is O, X is S, R1 is Me, R2 is Br, and G is CO2Et.
|
62
W is O, X is S, R1 is Me, R2 is Br, and G is CO2-i-Pr.
|
63
W is O, X is S, R1 is Me, R2 is Br, and G is CO2-t-Bu.
|
64
W is O, X is S, R1 is Me, R2 is Br, and G is SO2Me.
|
65
W is O, X is S, R1 is Me, R2 is I, and G is C(O)Me.
|
66
W is O, X is S, R1 is Me, R2 is I, and G is C(O)Et.
|
67
W is O, X is S, R1 is Me, R2 is I, and G is C(O)-i-Pr.
|
68
W is O, X is S, R1 is Me, R2 is I, and G is C(O)-t-Bu.
|
69
W is O, X is S, R1 is Me, R2 is I, and G is CO2Me.
|
70
W is O, X is S, R1 is Me, R2 is I, and G is CO2Et.
|
71
W is O, X is S, R1 is Me, R2 is I, and G is CO2-i-Pr.
|
72
W is O, X is S, R1 is Me, R2 is I, and G is CO2-t-Bu.
|
73
W is O, X is S, R1 is Me, R2 is I, and G is SO2Me.
|
74
W is O, X is S, R1 is Me, R2 is OMe, and G is C(O)Me.
|
75
W is O, X is S, R1 is Me, R2 is OMe, and G is C(O)Et.
|
76
W is O, X is S, R1 is Me, R2 is OMe, and G is C(O)-i-Pr.
|
77
W is O, X is S, R1 is Me, R2 is OMe, and G is C(O)-t-Bu.
|
78
W is O, X is S, R1 is Me, R2 is OMe, and G is CO2Me.
|
79
W is O, X is S, R1 is Me, R2 is OMe, and G is CO2Et.
|
80
W is O, X is S, R1 is Me, R2 is OMe, and G is CO2-i-Pr.
|
81
W is O, X is S, R1 is Me, R2 is OMe, and G is CO2-t-Bu.
|
82
W is O, X is S, R1 is Me, R2 is OMe, and G is SO2Me.
|
83
W is O, X is S, R1 is Me, R2 is OEt, and G is C(O)Me.
|
84
W is O, X is S, R1 is Me, R2 is OEt, and G is C(O)Et.
|
85
W is O, X is S, R1 is Me, R2 is OEt, and G is C(O)-i-Pr.
|
86
W is O, X is S, R1 is Me, R2 is OEt, and G is C(O)-t-Bu.
|
87
W is O, X is S, R1 is Me, R2 is OEt, and G is CO2Me.
|
88
W is O, X is S, R1 is Me, R2 is OEt, and G is CO2Et.
|
89
W is O, X is S, R1 is Me, R2 is OEt, and G is CO2-i-Pr.
|
90
W is O, X is S, R1 is Me, R2 is OEt, and G is CO2-t-Bu.
|
91
W is O, X is S, R1 is Me, R2 is OEt, and G is SO2Me.
|
92
W is O, X is S, R1 is Et, R2 is Me, and G is C(O)Me.
|
93
W is O, X is S, R1 is Et, R2 is Me, and G is C(O)Et.
|
94
W is O, X is S, R1 is Et, R2 is Me, and G is C(O)-i-Pr.
|
95
W is O, X is S, R1 is Et, R2 is Me, and G is C(O)-t-Bu.
|
96
W is O, X is S, R1 is Et, R2 is Me, and G is CO2Me.
|
97
W is O, X is S, R1 is Et, R2 is Me, and G is CO2Et.
|
98
W is O, X is S, R1 is Et, R2 is Me, and G is CO2-i-Pr.
|
99
W is O, X is S, R1 is Et, R2 is Me, and G is CO2-t-Bu.
|
100
W is O, X is S, R1 is Et, R2 is Me, and G is SO2Me.
|
101
W is O, X is S, R1 is Et, R2 is H, and G is C(O)Me.
|
102
W is O, X is S, R1 is Et, R2 is H, and G is C(O)Et.
|
103
W is O, X is S, R1 is Et, R2 is H, and G is C(O)-i-Pr.
|
104
W is O, X is S, R1 is Et, R2 is H, and G is C(O)-t-Bu.
|
105
W is O, X is S, R1 is Et, R2 is H, and G is CO2Me.
|
106
W is O, X is S, R1 is Et, R2 is H, and G is CO2Et.
|
107
W is O, X is S, R1 is Et, R2 is H, and G is CO2-i-Pr.
|
108
W is O, X is S, R1 is Et, R2 is H, and G is CO2-t-Bu.
|
109
W is O, X is S, R1 is Et, R2 is H, and G is SO2Me.
|
110
W is O, X is S, R1 is Et, R2 is Et, and G is C(O)Me.
|
111
W is O, X is S, R1 is Et, R2 is Et, and G is C(O)Et.
|
112
W is O, X is S, R1 is Et, R2 is Et, and G is C(O)-i-Pr.
|
113
W is O, X is S, R1 is Et, R2 is Et, and G is C(O)-t-Bu.
|
114
W is O, X is S, R1 is Et, R2 is Et, and G is CO2Me.
|
115
W is O, X is S, R1 is Et, R2 is Et, and G is CO2Et.
|
116
W is O, X is S, R1 is Et, R2 is Et, and G is CO2-i-Pr.
|
117
W is O, X is S, R1 is Et, R2 is Et, and G is CO2-t-Bu.
|
118
W is O, X is S, R1 is Et, R2 is Et, and G is SO2Me.
|
119
W is O, X is S, R1 is Et, R2 is Pr, and G is C(O)Me.
|
120
W is O, X is S, R1 is Et, R2 is Pr, and G is C(O)Et.
|
121
W is O, X is S, R1 is Et, R2 is Pr, and G is C(O)-i-Pr.
|
122
W is O, X is S, R1 is Et, R2 is Pr, and G is C(O)-t-Bu.
|
123
W is O, X is S, R1 is Et, R2 is Pr, and G is CO2Me.
|
124
W is O, X is S, R1 is Et, R2 is Pr, and G is CO2Et.
|
125
W is O, X is S, R1 is Et, R2 is Pr, and G is CO2-i-Pr.
|
126
W is O, X is S, R1 is Et, R2 is Pr, and G is CO2-t-Bu.
|
127
W is O, X is S, R1 is Et, R2 is Pr, and G is SO2Me.
|
128
W is O, X is S, R1 is Et, R2 is CF3, and G is C(O)Me.
|
129
W is O, X is S, R1 is Et, R2 is CF3, and G is C(O)Et.
|
130
W is O, X is S, R1 is Et, R2 is CF3, and G is C(O)-i-Pr.
|
131
W is O, X is S, R1 is Et, R2 is CF3, and G is C(O)-t-Bu.
|
132
W is O, X is S, R1 is Et, R2 is CF3, and G is CO2Me.
|
133
W is O, X is S, R1 is Et, R2 is CF3, and G is CO2Et.
|
134
W is O, X is S, R1 is Et, R2 is CF3, and G is CO2-i-Pr.
|
135
W is O, X is S, R1 is Et, R2 is CF3, and G is CO2-t-Bu.
|
136
W is O, X is S, R1 is Et, R2 is CF3, and G is SO2Me.
|
137
W is O, X is S, R1 is Et, R2 is Cl, and G is C(O)Me.
|
138
W is O, X is S, R1 is Et, R2 is Cl, and G is C(O)Et.
|
139
W is O, X is S, R1 is Et, R2 is Cl, and G is C(O)-i-Pr.
|
140
W is O, X is S, R1 is Et, R2 is Cl, and G is C(O)-t-Bu.
|
141
W is O, X is S, R1 is Et, R2 is Cl, and G is CO2Me.
|
142
W is O, X is S, R1 is Et, R2 is Cl, and G is CO2Et.
|
143
W is O, X is S, R1 is Et, R2 is Cl, and G is CO2-i-Pr.
|
144
W is O, X is S, R1 is Et, R2 is Cl, and G is CO2-t-Bu.
|
145
W is O, X is S, R1 is Et, R2 is Cl, and G is SO2Me.
|
146
W is O, X is S, R1 is Et, R2 is Br, and G is C(O)Me.
|
147
W is O, X is S, R1 is Et, R2 is Br, and G is C(O)Et.
|
148
W is O, X is S, R1 is Et, R2 is Br, and G is C(O)-i-Pr.
|
149
W is O, X is S, R1 is Et, R2 is Br, and G is C(O)-t-Bu.
|
150
W is O, X is S, R1 is Et, R2 is Br, and G is CO2Me.
|
151
W is O, X is S, R1 is Et, R2 is Br, and G is CO2Et.
|
152
W is O, X is S, R1 is Et, R2 is Br, and G is CO2-i-Pr.
|
153
W is O, X is S, R1 is Et, R2 is Br, and G is CO2-t-Bu.
|
154
W is O, X is S, R1 is Et, R2 is Br, and G is SO2Me.
|
155
W is O, X is S, R1 is Et, R2 is I, and G is C(O)Me.
|
156
W is O, X is S, R1 is Et, R2 is I, and G is C(O)Et.
|
157
W is O, X is S, R1 is Et, R2 is I, and G is C(O)-i-Pr.
|
158
W is O, X is S, R1 is Et, R2 is I, and G is C(O)-t-Bu.
|
159
W is O, X is S, R1 is Et, R2 is I, and G is CO2Me.
|
160
W is O, X is S, R1 is Et, R2 is I, and G is CO2Et.
|
161
W is O, X is S, R1 is Et, R2 is I, and G is CO2-i-Pr.
|
162
W is O, X is S, R1 is Et, R2 is I, and G is CO2-t-Bu.
|
163
W is O, X is S, R1 is Et, R2 is I, and G is SO2Me.
|
164
W is O, X is S, R1 is Et, R2 is OMe, and G is C(O)Me.
|
165
W is O, X is S, R1 is Et, R2 is OMe, and G is C(O)Et.
|
166
W is O, X is S, R1 is Et, R2 is OMe, and G is C(O)-i-Pr.
|
167
W is O, X is S, R1 is Et, R2 is OMe, and G is C(O)-t-Bu.
|
168
W is O, X is S, R1 is Et, R2 is OMe, and G is CO2Me.
|
169
W is O, X is S, R1 is Et, R2 is OMe, and G is CO2Et.
|
170
W is O, X is S, R1 is Et, R2 is OMe, and G is CO2-i-Pr.
|
171
W is O, X is S, R1 is Et, R2 is OMe, and G is CO2-t-Bu.
|
172
W is O, X is S, R1 is Et, R2 is OMe, and G is SO2Me.
|
173
W is O, X is S, R1 is Et, R2 is OEt, and G is C(O)Me.
|
174
W is O, X is S, R1 is Et, R2 is OEt, and G is C(O)Et.
|
175
W is O, X is S, R1 is Et, R2 is OEt, and G is C(O)-i-Pr.
|
176
W is O, X is S, R1 is Et, R2 is OEt, and G is C(O)-t-Bu.
|
177
W is O, X is S, R1 is Et, R2 is OEt, and G is CO2Me.
|
178
W is O, X is S, R1 is Et, R2 is OEt, and G is CO2Et.
|
179
W is O, X is S, R1 is Et, R2 is OEt, and G is CO2-i-Pr.
|
180
W is O, X is S, R1 is Et, R2 is OEt, and G is CO2-t-Bu.
|
181
W is O, X is S, R1 is Et, R2 is OEt, and G is SO2Me.
|
182
W is O, X is S, R1 is Pr, R2 is Me, and G is C(O)Me.
|
183
W is O, X is S, R1 is Pr, R2 is Me, and G is C(O)Et.
|
184
W is O, X is S, R1 is Pr, R2 is Me, and G is C(O)-i-Pr.
|
185
W is O, X is S, R1 is Pr, R2 is Me, and G is C(O)-t-Bu.
|
186
W is O, X is S, R1 is Pr, R2 is Me, and G is CO2Me.
|
187
W is O, X is S, R1 is Pr, R2 is Me, and G is CO2Et.
|
188
W is O, X is S, R1 is Pr, R2 is Me, and G is CO2-i-Pr.
|
189
W is O, X is S, R1 is Pr, R2 is Me, and G is CO2-t-Bu.
|
190
W is O, X is S, R1 is Pr, R2 is Me, and G is SO2Me.
|
191
W is O, X is S, R1 is Pr, R2 is H, and G is C(O)Me.
|
192
W is O, X is S, R1 is Pr, R2 is H, and G is C(O)Et.
|
193
W is O, X is S, R1 is Pr, R2 is H, and G is C(O)-i-Pr.
|
194
W is O, X is S, R1 is Pr, R2 is H, and G is C(O)-t-Bu.
|
195
W is O, X is S, R1 is Pr, R2 is H, and G is CO2Me.
|
196
W is O, X is S, R1 is Pr, R2 is H, and G is CO2Et.
|
197
W is O, X is S, R1 is Pr, R2 is H, and G is CO2-i-Pr.
|
198
W is O, X is S, R1 is Pr, R2 is H, and G is CO2-t-Bu.
|
199
W is O, X is S, R1 is Pr, R2 is H, and G is SO2Me.
|
200
W is O, X is S, R1 is Pr, R2 is Et, and G is C(O)Me.
|
201
W is O, X is S, R1 is Pr, R2 is Et, and G is C(O)Et.
|
202
W is O, X is S, R1 is Pr, R2 is Et, and G is C(O)-i-Pr.
|
203
W is O, X is S, R1 is Pr, R2 is Et, and G is C(O)-t-Bu.
|
204
W is O, X is S, R1 is Pr, R2 is Et, and G is CO2Me.
|
205
W is O, X is S, R1 is Pr, R2 is Et, and G is CO2Et.
|
206
W is O, X is S, R1 is Pr, R2 is Et, and G is CO2-i-Pr.
|
207
W is O, X is S, R1 is Pr, R2 is Et, and G is CO2-t-Bu.
|
208
W is O, X is S, R1 is Pr, R2 is Et, and G is SO2Me.
|
209
W is O, X is S, R1 is Pr, R2 is Pr, and G is C(O)Me.
|
210
W is O, X is S, R1 is Pr, R2 is Pr, and G is C(O)Et.
|
211
W is O, X is S, R1 is Pr, R2 is Pr, and G is C(O)-i-Pr.
|
212
W is O, X is S, R1 is Pr, R2 is Pr, and G is C(O)-t-Bu.
|
213
W is O, X is S, R1 is Pr, R2 is Pr, and G is CO2Me.
|
214
W is O, X is S, R1 is Pr, R2 is Pr, and G is CO2Et.
|
215
W is O, X is S, R1 is Pr, R2 is Pr, and G is CO2-i-Pr.
|
216
W is O, X is S, R1 is Pr, R2 is Pr, and G is CO2-t-Bu.
|
217
W is O, X is S, R1 is Pr, R2 is Pr, and G is SO2Me.
|
218
W is O, X is S, R1 is Pr, R2 is CF3, and G is C(O)Me.
|
219
W is O, X is S, R1 is Pr, R2 is CF3, and G is C(O)Et.
|
220
W is O, X is S, R1 is Pr, R2 is CF3, and G is C(O)-i-Pr.
|
221
W is O, X is S, R1 is Pr, R2 is CF3, and G is C(O)-t-Bu.
|
222
W is O, X is S, R1 is Pr, R2 is CF3, and G is CO2Me.
|
223
W is O, X is S, R1 is Pr, R2 is CF3, and G is CO2Et.
|
224
W is O, X is S, R1 is Pr, R2 is CF3, and G is CO2-i-Pr.
|
225
W is O, X is S, R1 is Pr, R2 is CF3, and G is CO2-t-Bu.
|
226
W is O, X is S, R1 is Pr, R2 is CF3, and G is SO2Me.
|
227
W is O, X is S, R1 is Pr, R2 is Cl, and G is C(O)Me.
|
228
W is O, X is S, R1 is Pr, R2 is Cl, and G is C(O)Et.
|
229
W is O, X is S, R1 is Pr, R2 is Cl, and G is C(O)-i-Pr.
|
230
W is O, X is S, R1 is Pr, R2 is Cl, and G is C(O)-t-Bu.
|
231
W is O, X is S, R1 is Pr, R2 is Cl, and G is CO2Me.
|
232
W is O, X is S, R1 is Pr, R2 is Cl, and G is CO2Et.
|
233
W is O, X is S, R1 is Pr, R2 is Cl, and G is CO2-i-Pr.
|
234
W is O, X is S, R1 is Pr, R2 is Cl, and G is CO2-t-Bu.
|
235
W is O, X is S, R1 is Pr, R2 is Cl, and G is SO2Me.
|
236
W is O, X is S, R1 is Pr, R2 is Br, and G is C(O)Me.
|
237
W is O, X is S, R1 is Pr, R2 is Br, and G is C(O)Et.
|
238
W is O, X is S, R1 is Pr, R2 is Br, and G is C(O)-i-Pr.
|
239
W is O, X is S, R1 is Pr, R2 is Br, and G is C(O)-t-Bu.
|
240
W is O, X is S, R1 is Pr, R2 is Br, and G is CO2Me.
|
241
W is O, X is S, R1 is Pr, R2 is Br, and G is CO2Et.
|
242
W is O, X is S, R1 is Pr, R2 is Br, and G is CO2-i-Pr.
|
243
W is O, X is S, R1 is Pr, R2 is Br, and G is CO2-t-Bu.
|
244
W is O, X is S, R1 is Pr, R2 is Br, and G is SO2Me.
|
245
W is O, X is S, R1 is Pr, R2 is I, and G is C(O)Me.
|
246
W is O, X is S, R1 is Pr, R2 is I, and G is C(O)Et.
|
247
W is O, X is S, R1 is Pr, R2 is I, and G is C(O)-i-Pr.
|
248
W is O, X is S, R1 is Pr, R2 is I, and G is C(O)-t-Bu.
|
249
W is O, X is S, R1 is Pr, R2 is I, and G is CO2Me.
|
250
W is O, X is S, R1 is Pr, R2 is I, and G is CO2Et.
|
251
W is O, X is S, R1 is Pr, R2 is I, and G is CO2-i-Pr.
|
252
W is O, X is S, R1 is Pr, R2 is I, and G is CO2-t-Bu.
|
253
W is O, X is S, R1 is Pr, R2 is I, and G is SO2Me.
|
254
W is O, X is S, R1 is Pr, R2 is OMe, and G is C(O)Me.
|
255
W is O, X is S, R1 is Pr, R2 is OMe, and G is C(O)Et.
|
256
W is O, X is S, R1 is Pr, R2 is OMe, and G is C(O)-i-Pr.
|
257
W is O, X is S, R1 is Pr, R2 is OMe, and G is C(O)-t-Bu.
|
258
W is O, X is S, R1 is Pr, R2 is OMe, and G is CO2Me.
|
259
W is O, X is S, R1 is Pr, R2 is OMe, and G is CO2Et.
|
260
W is O, X is S, R1 is Pr, R2 is OMe, and G is CO2-i-Pr.
|
261
W is O, X is S, R1 is Pr, R2 is OMe, and G is CO2-t-Bu.
|
262
W is O, X is S, R1 is Pr, R2 is OMe, and G is SO2Me.
|
263
W is O, X is S, R1 is Pr, R2 is OEt, and G is C(O)Me.
|
264
W is O, X is S, R1 is Pr, R2 is OEt, and G is C(O)Et.
|
265
W is O, X is S, R1 is Pr, R2 is OEt, and G is C(O)-i-Pr.
|
266
W is O, X is S, R1 is Pr, R2 is OEt, and G is C(O)-t-Bu.
|
267
W is O, X is S, R1 is Pr, R2 is OEt, and G is CO2Me.
|
268
W is O, X is S, R1 is Pr, R2 is OEt, and G is CO2Et.
|
269
W is O, X is S, R1 is Pr, R2 is OEt, and G is CO2-i-Pr.
|
270
W is O, X is S, R1 is Pr, R2 is OEt, and G is CO2-t-Bu.
|
271
W is O, X is S, R1 is Pr, R2 is OEt, and G is SO2Me.
|
272
W is O, X is —CH═CH—, R1 is Me, R2 is Me, and
|
G is C(O)Me.
|
273
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is C(O)Et.
|
274
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is C(O)-i-Pr.
|
275
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is C(O)-t-Bu.
|
276
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is CO2Me.
|
277
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is CO2Et.
|
278
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is CO2-i-Pr.
|
279
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is CO2-t-Bu.
|
280
W is O, X is —CH═CH—, R1 is Me, R2 is Me,
|
and G is SO2Me.
|
281
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is C(O)Me.
|
282
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is C(O)Et.
|
283
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is C(O)-i-Pr.
|
284
W is O, X is —CH═CH—, R1 is Me, R2 is H, and
|
G is C(O)-t-Bu.
|
285
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is CO2Me.
|
286
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is CO2Et.
|
287
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is CO2-i-Pr.
|
288
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is CO2-t-Bu.
|
289
W is O, X is —CH═CH—, R1 is Me, R2 is H,
|
and G is SO2Me.
|
290
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is C(O)Me.
|
291
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is C(O)Et.
|
292
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is C(O)-i-Pr.
|
293
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is C(O)-t-Bu.
|
294
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is CO2Me.
|
295
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is CO2Et.
|
296
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is CO2-i-Pr.
|
297
W is O, X is —CH═CH—, R1 is Me, R2 is Et,
|
and G is CO2-t-Bu.
|
298
W is O, X is —CH═CH—, R1 is Me, R2 is Et, and
|
G is SO2Me.
|
299
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is C(O)Me.
|
300
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is C(O)Et.
|
301
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is C(O)-i-Pr.
|
302
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is C(O)-t-Bu.
|
303
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is CO2Me.
|
304
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is CO2Et.
|
305
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is CO2-i-Pr.
|
306
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is CO2-t-Bu.
|
307
W is O, X is —CH═CH—, R1 is Me, R2 is Pr,
|
and G is SO2Me.
|
308
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is C(O)Me.
|
309
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is C(O)Et.
|
310
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is C(O)-i-Pr.
|
311
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is C(O)-t-Bu.
|
312
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is CO2Me.
|
313
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is CO2Et.
|
314
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is CO2-i-Pr.
|
315
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is CO2-t-Bu.
|
316
W is O, X is —CH═CH—, R1 is Me, R2 is CF3,
|
and G is SO2Me.
|
317
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is C(O)Me.
|
318
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is C(O)Et.
|
319
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is C(O)-i-Pr.
|
320
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is C(O)-t-Bu.
|
321
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is CO2Me.
|
322
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is CO2Et.
|
323
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is CO2-i-Pr.
|
324
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is CO2-t-Bu.
|
325
W is O, X is —CH═CH—, R1 is Me, R2 is Cl,
|
and G is SO2Me.
|
326
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is C(O)Me.
|
327
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is C(O)Et.
|
328
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is C(O)-i-Pr.
|
329
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is C(O)-t-Bu.
|
330
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is CO2Me.
|
331
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is CO2Et.
|
332
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is CO2-i-Pr.
|
333
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is CO2-t-Bu.
|
334
W is O, X is —CH═CH—, R1 is Me, R2 is Br,
|
and G is SO2Me.
|
335
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is C(O)Me.
|
336
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is C(O)Et.
|
337
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is C(O)-i-Pr.
|
338
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is C(O)-t-Bu.
|
339
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is CO2Me.
|
340
W is O, X is —CH═CH—, R1 is Me, R2 is I, .
|
and G is CO2Et
|
341
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is CO2-i-Pr.
|
342
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is CO2-t-Bu.
|
343
W is O, X is —CH═CH—, R1 is Me, R2 is I,
|
and G is SO2Me.
|
344
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is C(O)Me.
|
345
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is C(O)Et.
|
346
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is C(O)-i-Pr.
|
347
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is C(O)-t-Bu.
|
348
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is CO2Me.
|
349
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is CO2Et.
|
350
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is CO2-i-Pr.
|
351
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is CO2-t-Bu.
|
352
W is O, X is —CH═CH—, R1 is Me, R2 is OMe,
|
and G is SO2Me.
|
353
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is C(O)Me.
|
354
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is C(O)Et.
|
355
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is C(O)-i-Pr.
|
356
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is C(O)-t-Bu.
|
357
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is CO2Me.
|
358
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is CO2Et.
|
359
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is CO2-i-Pr.
|
360
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is CO2-t-Bu.
|
361
W is O, X is —CH═CH—, R1 is Me, R2 is OEt,
|
and G is SO2Me.
|
362
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is C(O)Me.
|
363
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is C(O)Et.
|
364
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is C(O)-i-Pr.
|
365
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is C(O)-t-Bu.
|
366
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is CO2Me.
|
367
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is CO2Et.
|
368
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is CO2-i-Pr.
|
369
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is CO2-t-Bu.
|
370
W is O, X is —CH═CH—, R1 is Et, R2 is Me,
|
and G is SO2Me.
|
371
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is C(O)Me.
|
372
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is C(O)Et.
|
373
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is C(O)-i-Pr.
|
374
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is C(O)-t-Bu.
|
375
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is CO2Me.
|
376
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is CO2Et.
|
377
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is CO2-i-Pr.
|
378
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is CO2-t-Bu.
|
379
W is O, X is —CH═CH—, R1 is Et, R2 is H,
|
and G is SO2Me.
|
380
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is C(O)Me.
|
381
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is C(O)Et.
|
382
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is C(O)-i-Pr.
|
383
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is C(O)-t-Bu.
|
384
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is CO2Me.
|
385
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is CO2Et.
|
386
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is CO2-i-Pr.
|
387
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is CO2-t-Bu.
|
388
W is O, X is —CH═CH—, R1 is Et, R2 is Et,
|
and G is SO2Me.
|
389
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is C(O)Me.
|
390
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is C(O)Et.
|
391
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is C(O)-i-Pr.
|
392
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is C(O)-t-Bu.
|
393
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is CO2Me.
|
394
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is CO2Et.
|
395
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is CO2-i-Pr.
|
396
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is CO2-t-Bu.
|
397
W is O, X is —CH═CH—, R1 is Et, R2 is Pr,
|
and G is SO2Me.
|
398
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is C(O)Me.
|
399
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is C(O)Et.
|
400
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is C(O)-i-Pr.
|
401
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is C(O)-t-Bu.
|
402
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is CO2Me.
|
403
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is CO2Et.
|
404
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is CO2-i-Pr.
|
405
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is CO2-t-Bu.
|
406
W is O, X is —CH═CH—, R1 is Et, R2 is CF3,
|
and G is SO2Me.
|
407
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is C(O)Me.
|
408
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is C(O)Et.
|
409
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is C(O)-i-Pr.
|
410
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is C(O)-t-Bu.
|
411
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is CO2Me.
|
412
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is CO2Et.
|
413
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is CO2-i-Pr.
|
414
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is CO2-t-Bu.
|
415
W is O, X is —CH═CH—, R1 is Et, R2 is Cl,
|
and G is SO2Me.
|
416
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is C(O)Me.
|
417
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is C(O)Et.
|
418
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is C(O)-i-Pr.
|
419
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is C(O)-t-Bu.
|
420
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is CO2Me.
|
421
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is CO2Et.
|
422
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is CO2-i-Pr.
|
423
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is CO2-t-Bu.
|
424
W is O, X is —CH═CH—, R1 is Et, R2 is Br,
|
and G is SO2Me.
|
425
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is C(O)Me.
|
426
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is C(O)Et.
|
427
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is C(O)-i-Pr.
|
428
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is C(O)-t-Bu.
|
429
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is CO2Me.
|
430
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is CO2Et.
|
431
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is CO2-i-Pr.
|
432
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is CO2-t-Bu.
|
433
W is O, X is —CH═CH—, R1 is Et, R2 is I,
|
and G is SO2Me.
|
434
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is C(O)Me.
|
435
W is O, X is —CH═CH—, R1 is Et,
|
R2 is OMe, and G is C(O)Et.
|
436
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is C(O)-i-Pr.
|
437
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is C(O)-t-Bu.
|
438
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is CO2Me.
|
439
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is CO2Et.
|
440
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is CO2-i-Pr.
|
441
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is CO2-t-Bu.
|
442
W is O, X is —CH═CH—, R1 is Et, R2 is OMe,
|
and G is SO2Me.
|
443
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is C(O)Me.
|
444
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is C(O)Et.
|
445
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is C(O)-i-Pr.
|
446
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is C(O)-t-Bu.
|
447
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is CO2Me.
|
448
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is CO2Et.
|
449
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is CO2-i-Pr.
|
450
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is CO2-t-Bu.
|
451
W is O, X is —CH═CH—, R1 is Et, R2 is OEt,
|
and G is SO2Me.
|
452
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is C(O)Me.
|
453
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is C(O)Et.
|
454
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is C(O)-i-Pr.
|
455
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is C(O)-t-Bu.
|
456
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is CO2Me.
|
457
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is CO2Et.
|
458
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is CO2-i-Pr.
|
459
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is CO2-t-Bu.
|
460
W is O, X is —CH═CH—, R1 is Pr, R2 is Me,
|
and G is SO2Me.
|
461
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is C(O)Me.
|
462
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is C(O)Et.
|
463
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is C(O)-i-Pr.
|
464
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is C(O)-t-Bu.
|
465
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is CO2Me.
|
466
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is CO2Et.
|
467
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is CO2-i-Pr.
|
468
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is CO2-t-Bu.
|
469
W is O, X is —CH═CH—, R1 is Pr, R2 is H,
|
and G is SO2Me.
|
470
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is C(O)Me.
|
471
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is C(O)Et.
|
472
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is C(O)-i-Pr.
|
473
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is C(O)-t-Bu.
|
474
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is CO2Me.
|
475
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is CO2Et.
|
476
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is CO2-i-Pr.
|
477
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is CO2-t-Bu.
|
478
W is O, X is —CH═CH—, R1 is Pr, R2 is Et,
|
and G is SO2Me.
|
479
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is C(O)Me.
|
480
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is C(O)Et.
|
481
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is C(O)-i-Pr.
|
482
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is C(O)-t-Bu.
|
483
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is CO2Me.
|
484
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is CO2Et.
|
485
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is CO2-i-Pr.
|
486
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is CO2-t-Bu.
|
487
W is O, X is —CH═CH—, R1 is Pr, R2 is Pr,
|
and G is SO2Me.
|
488
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is C(O)Me.
|
489
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is C(O)Et.
|
490
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is C(O)-i-Pr.
|
491
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is C(O)-t-Bu.
|
492
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is CO2Me.
|
493
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is CO2Et.
|
494
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is CO2-i-Pr.
|
495
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is CO2-t-Bu.
|
496
W is O, X is —CH═CH—, R1 is Pr, R2 is CF3,
|
and G is SO2Me.
|
497
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is C(O)Me.
|
498
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is C(O)Et.
|
499
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is C(O)-i-Pr.
|
500
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is C(O)-t-Bu.
|
501
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is CO2Me.
|
502
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is CO2Et.
|
503
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is CO2-i-Pr.
|
504
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is CO2-t-Bu.
|
505
W is O, X is —CH═CH—, R1 is Pr, R2 is Cl,
|
and G is SO2Me.
|
506
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is C(O)Me.
|
507
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is C(O)Et.
|
508
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is C(O)-i-Pr.
|
509
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is C(O)-t-Bu.
|
510
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is CO2Me.
|
511
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is CO2Et.
|
512
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is CO2-i-Pr.
|
513
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is CO2-t-Bu.
|
514
W is O, X is —CH═CH—, R1 is Pr, R2 is Br,
|
and G is SO2Me.
|
515
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is C(O)Me.
|
516
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is C(O)Et.
|
517
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is C(O)-i-Pr.
|
518
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is C(O)-t-Bu.
|
519
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is CO2Me.
|
520
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is CO2Et.
|
521
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is CO2-i-Pr.
|
522
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is CO2-t-Bu.
|
523
W is O, X is —CH═CH—, R1 is Pr, R2 is I,
|
and G is SO2Me.
|
524
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is C(O)Me.
|
525
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is C(O)Et.
|
526
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is C(O)-i-Pr.
|
527
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is C(O)-t-Bu.
|
528
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is CO2Me.
|
529
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is CO2Et.
|
530
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is CO2-i-Pr.
|
531
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is CO2-t-Bu.
|
532
W is O, X is —CH═CH—, R1 is Pr, R2 is OMe,
|
and G is SO2Me.
|
533
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is C(O)Me.
|
534
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is C(O)Et.
|
535
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is C(O)-i-Pr.
|
536
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is C(O)-t-Bu.
|
537
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is CO2Me.
|
538
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is CO2Et.
|
539
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is CO2-i-Pr.
|
540
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is CO2-t-Bu.
|
541
W is O, X is —CH═CH—, R1 is Pr, R2 is OEt,
|
and G is SO2Me.
|
542
W is O, X is S, R1 is CH2CF3, R2 is Me,
|
and G is H.
|
543
W is O, X is S, R1 is CH2CF3, R2 is Me,
|
and G is C(O)Me.
|
544
W is O, X is S, R1 is CH2CF3, R2 is Me,
|
and G is CO2Me.
|
545
W is O, X is S, R1 is CH2CF3, R2 is Br,
|
and G is H.
|
546
W is O, X is S, R1 is CH2CF3, R2 is Br,
|
and G is C(O)Me.
|
547
W is O, X is S, R1 is CH2CF3, R2 is Br,
|
and G is CO2Me.
|
548
W is O, X is S, R1 is CH2CH2CN, R2 is Me,
|
and G is H.
|
549
W is O, X is S, R1 is CH2CH2CN, R2 is Me,
|
and G is C(O)Me.
|
550
W is O, X is S, R1 is CH2CH2CN, R2 is Me,
|
and G is CO2Me.
|
551
W is O, X is S, R1 is CH2CH2CN, R2 is Br,
|
and G is H.
|
552
W is O, X is S, R1 is CH2CH2CN, R2 is Br,
|
and G is C(O)Me.
|
553
W is O, X is S, R1 is CH2CH2CN, R2 is Br,
|
and G is CO2Me.
|
554
W is O, X is —CH═CH—, R1 is CH2CF3,
|
R2 is Me, and G is H.
|
555
W is O, X is —CH═CH—, R1 is CH2CF3,
|
R2 is Me, and G is C(O)Me.
|
556
W is O, X is —CH═CH—, R1 is CH2CF3,
|
R2 is Me, and G is CO2Me.
|
557
W is O, X is —CH═CH—, R1 is CH2CF3,
|
R2 is Br, and G is H.
|
558
W is O, X is —CH═CH—, R1 is CH2CF3,
|
R2 is Br, and G is C(O)Me.
|
559
W is O, X is —CH═CH—, R1 is CH2CF3,
|
R2 is Br, and G is CO2Me.
|
560
W is O, X is —CH═CH—, R1 is CH2CH2CN,
|
R2 is Me, and G is H.
|
561
W is O, X is —CH═CH—, R1 is CH2CH2CN,
|
R2 is Me, and G is C(O)Me.
|
562
W is O, X is —CH═CH—, R1 is CH2CH2CN,
|
R2 is Me, and G is CO2Me.
|
563
W is O, X is —CH═CH—, R1 is CH2CH2CN,
|
R2 is Br, and G is H.
|
564
W is O, X is —CH═CH—, R1 is CH2CH2CN,
|
R2 is Br, and G is C(O)Me.
|
565
W is O, X is —CH═CH—, R1 is CH2CH2CN,
|
R2 is Br, and G is CO2Me.
|
566
W is O, X is O, R1 is Me, R2 is Me, and G is H.
|
567
W is O, X is O, R1 is Me, R2 is Me, and G is C(O)Me.
|
568
W is O, X is O, R1 is Me, R2 is Me, and G is CO2Me.
|
569
W is O, X is O, R1 is Me, R2 is Br, and G is H.
|
570
W is O, X is O, R1 is Me, R2 is Br, and G is C(O)Me.
|
571
W is O, X is O, R1 is Me, R2 is Br, and G is CO2Me.
|
572
W is O, X is —CH═C(Me)—, R1 is Me,
|
R2 is Me, and G is H.
|
573
W is O, X is —CH═C(Me)—, R1 is Me,
|
R2 is Me, and G is C(O)Me.
|
574
W is O, X is —CH═C(Me)—, R1 is Me,
|
R2 is Me, and G is CO2Me.
|
575
W is O, X is —CH═C(Me)—, R1 is Me,
|
R2 is Br, and G is H.
|
576
W is O, X is —CH═C(Me)—, R1 is Me,
|
R2 is Br, and G is C(O)Me.
|
577
W is O, X is —CH═C(Me)—, R1 is Me,
|
R2 is Br, and G is CO2Me.
|
578
W is O, X is N(Me), R1 is Me, R2 is Me,
|
and G is H.
|
579
W is O, X is N(Me), R1 is Me, R2 is Me,
|
and G is C(O)Me.
|
580
W is O, X is N(Me), R1 is Me, R2 is Me,
|
and G is CO2Me.
|
581
W is O, X is N(Me), R1 is Me, R2 is Br,
|
and G is H.
|
582
W is O, X is N(Me), R1 is Me, R2 is Br,
|
and G is C(O)Me.
|
583
W is O, X is N(Me), R1 is Me, R2 is Br,
|
and G is CO2Me.
|
584
W is O, X is —CH═C(F)—, R1 is Me, R2 is Me,
|
and G is H.
|
585
W is O, X is —CH═C(F)—, R1 is Me,
|
R2 is Me, and G is C(O)Me.
|
586
W is O, X is —CH═C(F)—, R1 is Me,
|
R2 is Me, and G is CO2Me.
|
587
W is O, X is —CH═C(F)—, R1 is Me, R2 is Br,
|
and G is H.
|
588
W is O, X is —CH═C(F)—, R1 is Me,
|
R2 is Br, and G is C(O)Me.
|
589
W is O, X is —CH═C(F)—, R1 is Me,
|
R2 is Br, and G is CO2Me.
|
590
W is O, X is —CH═C(Cl)—, R1 is Me, R2 is Me,
|
and G is H.
|
591
W is O, X is —CH═C(Cl)—, R1 is Me,
|
R2 is Me, and G is C(O)Me.
|
592
W is O, X is —CH═C(Cl)—, R1 is Me,
|
R2 is Me, and G is CO2Me.
|
593
W is O, X is —CH═C(Cl)—, R1 is Me, R2 is Br,
|
and G is H.
|
594
W is O, X is —CH═C(Cl)—, R1 is Me,
|
R2 is Br, and G is C(O)Me.
|
595
W is O, X is —CH═C(Cl)—, R1 is Me,
|
R2 is Br, and G is CO2Me.
|
596
W is O, X is —CH═C(OMe)—, R1 is Me,
|
R2 is Me, and G is H.
|
597
W is O, X is —CH═C(OMe)—, R1 is Me,
|
R2 is Me, and G is C(O)Me.
|
598
W is O, X is —CH═C(OMe)—, R1 is Me,
|
R2 is Me, and G is CO2Me.
|
599
W is O, X is —CH═C(OMe)—, R1 is Me,
|
R2 is Br, and G is H.
|
600
W is O, X is —CH═C(OMe)—, R1 is Me,
|
R2 is Br, and G is C(O)Me.
|
601
W is O, X is —CH═C(OMe)—, R1 is Me,
|
R2 is Br, and G is CO2Me.
|
602
W is O, X is —CH═C(CN)—, R1 is Me,
|
R2 is Me, and G is H.
|
603
W is O, X is —CH═C(CN)—, R1 is Me,
|
R2 is Me, and G is C(O)Me.
|
604
W is O, X is —CH═C(CN)—, R1 is Me,
|
R2 is Me, and G is CO2Me.
|
605
W is O, X is —CH═C(CN)—, R1 is Me,
|
R2 is Br, and G is H.
|
606
W is O, X is —CH═C(CN)—, R1 is Me,
|
R2 is Br, and G is C(O)Me.
|
607
W is O, X is —CH═C(CN)—, R1 is Me,
|
R2 is Br, and G is CO2Me.
|
608
W is S, X is S, R1 is Me, R2 is Me, and G is H.
|
609
W is S, X is S, R1 is Me, R2 is Me, and G is C(O)Me.
|
610
W is S, X is S, R1 is Me, R2 is Me, and G is CO2Me.
|
611
W is S, X is S, R1 is Me, R2 is Br, and G is H.
|
612
W is S, X is S, R1 is Me, R2 is Br, and G is C(O)Me.
|
613
W is S, X is S, R1 is Me, R2 is Br, and G is CO2Me.
|
614
W is S, X is —CH═CH—, R1 is Me,
|
R2 is Me, and G is H.
|
615
W is S, X is —CH═CH—, R1 is Me,
|
R2 is Me, and G is C(O)Me.
|
616
W is S, X is —CH═CH—, R1 is Me,
|
R2 is Me, and G is CO2Me.
|
617
W is S, X is —CH═CH—, R1 is Me,
|
R2 is Br, and G is H.
|
618
W is S, X is —CH═CH—, R1 is Me,
|
R2 is Br, and G is C(O)Me.
|
619
W is S, X is —CH═CH—, R1 is Me,
|
R2 is Br, and G is CO2Me.
|
620
W is O, X is —CH═CH—, R1 is CH3,
|
R2 is Me, and G is H.
|
621
W is S, X is —CH═CH—, R1 is CH3,
|
R2 is Me, and G is H.
|
622
W is O, X is —CH═CH—, R1 is CH2CH3,
|
R2 is Me, and G is H.
|
623
W is S, X is —CH═CH—, R1 is CH2CH3,
|
R2 is Me, and G is H.
|
624
W is O, X is —CH═CH—, R1 is CH3,
|
R2 is Et, and G is H.
|
625
W is S, X is —CH═CH—, R1 is CH3,
|
R2 is Et, and G is H.
|
626
W is O, X is —CH═CH—, R1 is CH2CH3,
|
R2 is Et, and G is H.
|
627
W is S, X is —CH═CH—, R1 is CH2CH3,
|
R2 is Et, and G is H.
|
|
Formulation/Utility
A compound of this invention will generally be used as a herbicidal active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates and/or suspoemulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.
Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
|
Weight Percent
|
Active
Surfac-
|
Ingredient
Diluent
tant
|
|
Water-Dispersible and Water-soluble
0.001-90
0-99.999
0-15
|
Granules, Tablets and Powders
|
Oil Dispersions, Suspensions,
1-50
40-99
0-50
|
Emulsions, Solutions (including
|
Emulsifiable Concentrates)
|
Dusts
1-25
70-99
0-5
|
Granules and Pellets
0.001-99
5-99.999
0-15
|
High Strength Compositions
90-99
0-10
0-2
|
|
Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.
Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6-C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.
Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.
Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquatemary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.
For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, U K, 2000.
In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting Examples are illustrative of the invention. Percentages are by weight except where otherwise indicated.
Example A
|
High Strength Concentrate
|
|
|
Compound 1
98.5%
|
silica aerogel
0.5%
|
synthetic amorphous
1.0%
|
fine silica
|
|
Example B
|
Wettable Powder
|
|
|
Compound 1
65.0%
|
dodecylphenol polyethylene glycol ether
2.0%
|
sodium ligninsulfonate
4.0%
|
sodium silicoaluminate
6.0%
|
montmorillonite (calcined)
23.0%
|
|
Example C
|
Granule
|
|
|
Compound 1
10.0%
|
attapulgite granules (low volatile
90.0%
|
matter, 0.71/0.30 mm;
|
U.S.S. No. 25-50 sieves)
|
|
Example D
|
Extruded Pellet
|
|
|
Compound 1
25.0%
|
anhydrous sodium sulfate
10.0%
|
crude calcium ligninsulfonate
5.0%
|
sodium alkylnaphthalenesulfonate
1.0%
|
calcium/magnesium bentonite
59.0%
|
|
Example E
|
Emulsifiable Concentrate
|
|
|
Compound 1
10.0%
|
polyoxyethylene sorbitol hexoleate
20.0%
|
C6-C10 fatty acid methyl ester
70.0%
|
|
Example F
|
Microemulsion
|
|
|
Compound 1
5.0%
|
polyvinylpyrrolidone-vinyl
30.0%
|
acetate copolymer
|
alkylpolyglycoside
30.0%
|
glyceryl monooleate
15.0%
|
water
20.0%
|
|
Example G
|
Suspension Concentrate
|
|
|
Compound 1
35%
|
butyl polyoxyethylene/polypropylene
4.0%
|
block copolymer
|
stearic acid/polyethylene
1.0%
|
glycol copolymer
|
styrene acry1ic polymer
1.0%
|
xanthan gum
0.1%
|
propylene glycol
5.0%
|
silicone based defoamer
0.1%
|
1,2-benzisothiazolin-3-one
0.1%
|
water
53.7%
|
|
Example H
|
Emulsion in Water
|
|
|
Compound 1
10.0%
|
butyl polyoxyethylene/polypropylene
4.0%
|
block copolymer
|
stearic acid/polyethylene
1.0%
|
glycol copolymer
|
styrene acry1ic polymer
1.0%
|
xanthan gum
0.1%
|
propylene glycol
5.0%
|
silicone based defoamer
0.1%
|
1,2-benzisothiazolin-3-one
0.1%
|
aromatic petroleum
20.0
|
based hydrocarbon
|
water
58.7%
|
|
Example I
|
Oil Dispersion
|
|
|
Compound 1
25%
|
polyoxyethylene sorbitol hexaoleate
15%
|
organically modified bentonite clay
2.5%
|
fatty acid methyl ester
57.5%
|
|
The present disclosure also includes Examples A through I above except the “Compound 1” is replaced with “Compound 2”, “Compound 3”, “Compound 4”, “Compound 5”, “Compound 6”, “Compound 7”, “Compound 8”, “Compound 9”, “Compound 10”, “Compound 11”, “Compound 12”, “Compound 13”, “Compound 14”, “Compound 15”, “Compound 16”, “Compound 17”, “Compound 18”, “Compound 19”, “Compound 20”, “Compound 21”, “Compound 22”, “Compound 23”, “Compound 24”, “Compound 25”, “Compound 26”, “Compound 27”, “Compound 28”, “Compound 29”, “Compound 30”, “Compound 31”, “Compound 32”, “Compound 33”, “Compound 34”, “Compound 35”, “Compound 36”, “Compound 37”, “Compound 38”, “Compound 39”, “Compound 40”, “Compound 41”, “Compound 42”, “Compound 43”, “Compound 44”, “Compound 45”, “Compound 46”, “Compound 47”, “Compound 48”, “Compound 49”, “Compound 50”, “Compound 51”, “Compound 52”, “Compound 53”, “Compound 54”, “Compound 55”, “Compound 56”, “Compound 57”, “Compound 58”, “Compound 59”, “Compound 60”, “Compound 61”, “Compound 62”, “Compound 63”, “Compound 64”, “Compound 65”, “Compound 66”, “Compound 67”, “Compound 68”, “Compound 69”, “Compound 70”, “Compound 71”, “Compound 72”, “Compound 73”, “Compound 74”, “Compound 75”, “Compound 76”, “Compound 77”, “Compound 78”, “Compound 79”, “Compound 80”, “Compound 81”, “Compound 82”, “Compound 83”, “Compound 84”, “Compound 85”, “Compound 86”, “Compound 87”, “Compound 88”, “Compound 89”, “Compound 90”, “Compound 91”, “Compound 92”, “Compound 93”, “Compound 94”, “Compound 95”, “Compound 96”, “Compound 97”, “Compound 98”, “Compound 99”, “Compound 100”, “Compound 101”, “Compound 102”, “Compound 103”, “Compound 104”, “Compound 105”, “Compound 106”, “Compound 107”, “Compound 108”, “Compound 109”, “Compound 110”, “Compound 111”, “Compound 112”, “Compound 113”, “Compound 114”, “Compound 115”, “Compound 116”, “Compound 117”, “Compound 118”, “Compound 119”, “Compound 120”, “Compound 121”, “Compound 122”, “Compound 123”, “Compound 124”, “Compound 125”, “Compound 126”, “Compound 127”, “Compound 128”, “Compound 129”, “Compound 130”, “Compound 131”, “Compound 132”, “Compound 133”, “Compound 134”, “Compound 135”, “Compound 136”, “Compound 137”, “Compound 138”, “Compound 139”, “Compound 140”, “Compound 141”, “Compound 142”, “Compound 143”, “Compound 144”, “Compound 145”, “Compound 146”, “Compound 147”, “Compound 148”, “Compound 149”, “Compound 150”, “Compound 151”, “Compound 152”, “Compound 153”, “Compound 154”, “Compound 155”, “Compound 156”, “Compound 157”, “Compound 158”, “Compound 159”, “Compound 160”, “Compound 161”, “Compound 162”, “Compound 163”, “Compound 164”, “Compound 165”, “Compound 166”, “Compound 167”, “Compound 168”, “Compound 169”, “Compound 170”, “Compound 171”, “Compound 172”, “Compound 173”, “Compound 174”, “Compound 175”, “Compound 176”, “Compound 177”, “Compound 178”, “Compound 179”, “Compound 180”, “Compound 181”, “Compound 182”, “Compound 183”, “Compound 184”, “Compound 185”, “Compound 186”, “Compound 187” or “Compound 188”.
Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. The compounds of the invention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth.
As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
A herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is about 0.001 to 20 kg/ha with a preferred range of about 0.004 to 1 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
In one common embodiment, a compound of the invention is applied, typically in a formulated composition, to a locus comprising desired vegetation (e.g., crops) and undesired vegetation (i.e. weeds), both of which may be seeds, seedlings and/or larger plants, in contact with a growth medium (e.g., soil). In this locus, a composition comprising a compound of the invention can be directly applied to a plant or a part thereof, particularly of the undesired vegetation, and/or to the growth medium in contact with the plant.
Plant varieties and cultivars of the desired vegetation in the locus treated with a compound of the invention can be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant's genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
Genetically modified plant cultivars in the locus which can be treated according to the invention include those that are resistant against one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, cold temperature, soil salinity, etc.), or that contain other desirable characteristics. Plants can be genetically modified to exhibit traits of, for example, herbicide tolerance, insect-resistance, modified oil profiles or drought tolerance. Useful genetically modified plants containing single gene transformation events or combinations of transformation events are listed in Exhibit C. Additional information for the genetic modifications listed in Exhibit C can be obtained from publicly available databases maintained, for example, by the U.S. Department of Agriculture.
The following abbreviations, T1 through T37, are used in Exhibit C for traits. “tol.” means “tolerance”. A hyphen “-” means the entry is not available.
|
Trait Description
|
|
|
T1
Glyphosate tolerance
|
T2
High lauric acid oil
|
T3
Glufosinate tolerance
|
T4
Phytate breakdown
|
T5
Oxynil tolerance
|
T6
Disease resistance
|
T7
Insect resistance
|
T9
Modified flower color
|
T11
ALS herbicide tol.
|
T12
Dicamba tolerance
|
T13
Anti-allergy
|
T14
Salt tolerance
|
T15
Cold tolerance
|
T16
Imidazolinone herbicide tol.
|
T17
Modified alpha-amylase
|
T18
Pollination control
|
T19
2,4-D tolerance
|
T20
Increased lysine
|
T21
Drought tolerance
|
T22
Delayed ripening/senescence
|
T23
Modified product quality
|
T24
High cellulose
|
T25
Modified starch/carbohydrate
|
T26
Insect & disease resistance
|
T27
High tryptophan
|
T28
Erect leaves semidwarf
|
T29
Semidwarf
|
T30
Low iron tolerance
|
T31
Modified oil/fatty acid
|
T32
HPPD tolerance
|
T33
High oil
|
T34
Aryloxyalkanoate tol.
|
T35
Mesotrione tolerance
|
T36
Reduced nicotine
|
T37
Modified product
|
|
|
Exhibit C
|
Crop
Event Name
Event Code
Trait(s)
Gene(s)
|
|
Alfalfa
J101
MON-00101-8
T1
cp4 epsps (aroA:CP4)
|
Alfalfa
J163
MON-ØØ163-7
T1
cp4 epsps (aroA:CP4)
|
Canola*
23-18-17 (Event 18)
CGN-89465-2
T2
te
|
Canola*
23-198 (Event 23)
CGN-89465-2
T2
te
|
Canola*
61061
DP-Ø61Ø61-7
T1
gat4621
|
Canola*
73496
DP-Ø73496-4
T1
gat4621
|
Canola*
GT200 (RT200)
MON-89249-2
T1
cp4 epsps (aroA:CP4); goxv247
|
Canola*
GT73 (RT73)
MON-ØØØ73-7
T1
cp4 epsps (aroA:CP4); goxv247
|
Canola*
HCN10 (Topas 19/2)
—
T3
bar
|
Canola*
HCN28 (T45)
ACS-BNØØ8-2
T3
pat (syn)
|
Canola*
HCN92 (Topas 19/2)
ACS-BNØØ7-1
T3
bar
|
Canola*
MON88302
MON-883Ø2-9
T1
cp4 epsps (aroA:CP4)
|
Canola*
MPS961
—
T4
phyA
|
Canola*
MPS962
—
T4
phyA
|
Canola*
MPS963
—
T4
phyA
|
Canola*
MPS964
—
T4
phyA
|
Canola*
MPS965
—
T4
phyA
|
Canola*
MS1 (B91-4)
ACS-BNØØ4-7
T3
bar
|
Canola*
MS8
ACS-BNØØ5-8
T3
bar
|
Canola*
OXY-235
ACS-BNØ11-5
T5
bxn
|
Canola*
PHY14
—
T3
bar
|
Canola*
PHY23
—
T3
bar
|
Canola*
PHY35
—
T3
bar
|
Canola*
PHY36
—
T3
bar
|
Canola*
RF1 (B93-101)
ACS-BNØØ1-4
T3
bar
|
Canola*
RF2 (B94-2)
ACS-BNØØ2-5
T3
bar
|
Canola*
RF3
ACS-BNØØ3-6
T3
bar
|
Bean
EMBRAPA 5.1
EMB-PV051-1
T6
ac1 (sense and antisense)
|
Brinjal #
EE-1
—
T7
cry1Ac
|
Cotton
19-51a
DD-Ø1951A-7
T11
S4-HrA
|
Cotton
281-24-236
DAS-24236-5
T3, T7
pat (syn); cry1F
|
Cotton
3006-210-23
DAS-21Ø23-5
T3, T7
pat (syn); cry1Ac
|
Cotton
31707
—
T5, T7
bxn; cry1Ac
|
Cotton
31803
—
T5, T7
bxn; cry1Ac
|
Cotton
31807
—
T5, T7
bxn; cry1Ac
|
Cotton
31808
—
T5, T7
bxn; cry1Ac
|
Cotton
42317
—
T5, T7
bxn; cry1Ac
|
Cotton
BNLA-601
—
T7
cry1Ac
|
Cotton
BXN10211
BXN10211-9
T5
bxn; cry1Ac
|
Cotton
BXN10215
BXN10215-4
T5
bxn; cry1Ac
|
Cotton
BXN10222
BXN10222-2
T5
bxn; cry1Ac
|
Cotton
BXN10224
BXN10224-4
T5
bxn; cry1Ac
|
Cotton
COT102
SYN-IR102-7
T7
vip3A(a)
|
Cotton
COT67B
SYN-IR67B-1
T7
cry1Ab
|
Cotton
COT202
—
T7
vip3A
|
Cotton
Event 1
—
T7
cry1Ac
|
Cotton
GMF Cry1Ac
GTL-GMF311-7
T7
cry1Ab-Ac
|
Cotton
GHB119
BCS-GH005-8
T7
cry2Ae
|
Cotton
GHB614
BCS-GH002-5
Ti
2mepsps
|
Cotton
GK12
—
T7
cry1Ab-Ac
|
Cotton
LLCotton25
ACS-GH001-3
T3
bar
|
Cotton
MLS 9124
—
T7
cry1C
|
Cotton
MON1076
MON-89924-2
T7
cry1Ac
|
Cotton
MON1445
MON-01445-2
Ti
cp4 epsps (aroA:CP4)
|
Cotton
MON15985
MON-15985-7
T7
cry1Ac; cry2Ab2
|
Cotton
MON1698
MON-89383-1
T7
cp4 epsps (aroA:CP4)
|
Cotton
MON531
MON-00531-6
T7
cry1Ac
|
Cotton
MON757
MON-00757-7
T7
cry1Ac
|
Cotton
MON88913
MON-88913-8
T1
cp4 epsps (aroA:CP4)
|
Cotton
Nqwe Chi 6 Bt
—
T7
—
|
Cotton
SKG321
—
T7
cry1A; CpTI
|
Cotton
T303-3
BCS-GH003-6
T3, T7
cry1Ab; bar
|
Cotton
T304-40
BCS-GH004-7
T3, T7
cry1Ab; bar
|
Cotton
CE43-67B
—
T7
cry1Ab
|
Cotton
CE46-02A
—
T7
cry1Ab
|
Cotton
CE44-69D
—
T7
cry1Ab
|
Cotton
1143-14A
—
T7
cry1Ab
|
Cotton
1143-51B
—
T7
cry1Ab
|
Cotton
T342-142
—
T7
cry1Ab
|
Cotton
PV-GHGT07 (1445)
—
T1
cp4 epsps (aroA:CP4)
|
Cotton
EE-GH3
—
T1
mepsps
|
Cotton
EE-GH5
—
T7
cry1Ab
|
Cotton
MON88701
MON-88701-3
T3, T12
Modified dmo; bar
|
Cotton
OsCr11
—
T13
Modified Cry j
|
Flax
FP967
CDC-FL001-2
T11
als
|
Lentil
RH44
—
T16
als
|
Maize
3272
SYN-E3272-5
T17
amy797E
|
Maize
5307
SYN-05307-1
T7
ecry3.1Ab
|
Maize
59122
DAS-59122-7
T3, T7
cry34Ab1; cry35Ab1; pat
|
Maize
676
PH-000676-7
T3, T18
pat; dam
|
Maize
678
PH-000678-9
T3, T18
pat; dam
|
Maize
680
PH-000680-2
T3, T18
pat; dam
|
Maize
98140
DP-098140-6
T1, T11
gat4621; zm-hra
|
Maize
Bt10
—
T3, T7
cry1Ab; pat
|
Maize
Bt176 (176)
SYN-EV176-9
T3, T7
cry1Ab; bar
|
Maize
BVLA430101
—
T4
phyA2
|
Maize
CBH-351
ACS-ZM004-3
T3, T7
cry9C; bar
|
Maize
DAS40278-9
DAS40278-9
T19
aad-1
|
Maize
DBT418
DKB-89614-9
T3, T7
cry1Ac; pinII; bar
|
Maize
DLL25 (B16)
DKB-89790-5
T3
bar
|
Maize
GA21
MON-00021-9
T1
mepsps
|
Maize
GG25
—
T1
mepsps
|
Maize
GJ11
—
T1
mepsps
|
Maize
Fl117
—
T1
mepsps
|
Maize
GAT-ZM1
—
T3
pat
|
Maize
LY038
REN-00038-3
T20
cordapA
|
Maize
MIR162
SYN-IR162-4
T7
vip3Aa20
|
Maize
MIR604
SYN-IR604-5
T7
mcry3A
|
Maize
MON801
MON801
T1, T7
cry1Ab; cp4 epsps
|
(MON80100)
(aroA:CP4); goxv247
|
Maize
MON802
MON-80200-7
T1, T7
cry1Ab; cp4 epsps
|
(aroA:CP4); goxv247
|
Maize
MON809
PH-MON-809-2
T1, T7
cry1Ab; cp4 epsps
|
(aroA:CP4); goxv247
|
Maize
MON810
MON-00810-6
T1, T7
cry1Ab; cp4 epsps
|
(aroA:CP4); goxv247
|
Maize
MON832
—
T1
cp4 epsps (aroA:CP4);
|
goxv247
|
Maize
MON863
MON-00863-5
T7
cry3Bb1
|
Maize
MON87427
MON-87427-7
T1
cp4 epsps (aroA:CP4)
|
Maize
MON87460
MON-87460-4
T21
cspB
|
Maize
MON88017
MON-88017-3
T1, T7
cry3Bb1; cp4 epsps
|
(aroA:CP4)
|
Maize
MON89034
MON-89034-3
T7
cry2Ab2; cry1A.105
|
Maize
MS3
ACS-ZM001-9
T3, T18
bar; barnase
|
Maize
MS6
ACS-ZM005-4
T3, T18
bar; barnase
|
Maize
NK603
MON-00603-6
T1
cp4 epsps (aroA:CP4)
|
Maize
T14
ACS-ZM002-1
T3
pat (syn)
|
Maize
T25
ACS-ZM003-2
T3
pat (syn)
|
Maize
TC1507
DAS-01507-1
T3, T7
cry1Fa2; pat
|
Maize
TC6275
DAS-06275-8
T3, T7
mocry1F; bar
|
Maize
VIP1034
—
T3, T7
vip3A; pat
|
Maize
43A47
DP-043A47-3
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat
|
Maize
40416
DP-040416-8
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat
|
Maize
32316
DP-032316-8
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat
|
Maize
4114
DP-004114-3
T3, T7
cry1F; cry34Ab1; cry35Ab1; pat
|
Melon
Melon A
—
T22
sam-k
|
Melon
Melon B
—
T22
sam-k
|
Papaya
55-1
CUH-CP551-8
T6
prsv cp
|
Papaya
63-1
CUH-CP631-7
T6
prsv cp
|
Papaya
Huanong No. 1
—
T6
prsv rep
|
Papaya
X17-2
UFL-X17CP-6
T6
prsv cp
|
Plum
C-5
ARS-PLMC5-6
T6
ppv cp
|
Canola**
ZSR500
—
T1
cp4 epsps
|
(aroA:CP4); goxv247
|
Canola**
ZSR502
—
T1
cp4 epsps
|
(aroA:CP4); goxv247
|
Canola**
ZSR503
—
T1
cp4 epsps
|
(aroA:CP4); goxv247
|
Rice
7Crp#242-95-7
—
T13
7crp
|
Rice
7Crp#10
—
T13
7crp
|
Rice
GM Shanyou 63
—
T7
cry1Ab; cry1Ac
|
Rice
Huahui-1/TT51-1
—
T7
cry1Ab; cry1Ac
|
Rice
LLRICE06
ACS-OS001-4
T3
bar
|
Rice
LLRICE601
BCS-OS003-7
T3
bar
|
Rice
LLRICE62
ACS-OS002-5
T3
bar
|
Rice
Tarom molaii + cry1Ab
—
T7
cry1Ab (truncated)
|
Rice
GAT-OS2
—
T3
bar
|
Rice
GAT-OS3
—
T3
bar
|
Rice
PE-7
—
T7
Cry1Ac
|
Rice
7Crp#10
—
T13
7crp
|
Rice
KPD627-8
—
T27
OASA1D
|
Rice
KPD722-4
—
T27
OASA1D
|
Rice
KA317
—
T27
OASA1D
|
Rice
HW5
—
T27
OASA1D
|
Rice
HW1
—
T27
OASA1D
|
Rice
B-4-1-18
—
T28
Δ OsBRI1
|
Rice
G-3-3-22
—
T29
OSGA2ox1
|
Rice
AD77
—
T6
DEF
|
Rice
AD51
—
T6
DEF
|
Rice
AD48
—
T6
DEF
|
Rice
AD41
—
T6
DEF
|
Rice
13pNasNa800725atAprt1
—
T30
HvNAS1; HvNAAT-A; APRT
|
Rice
13pAprt1
—
T30
APRT
|
Rice
gHvNAS1-gHvNAAT-1
—
T30
HvNAS1; HvNAAT-A;
|
HvNAAT-B
|
Rice
gHvIDS3-1
—
T30
HvIDS3
|
Rice
gHvNAAT1
—
T30
HvNAAT-A; HvNAAT-B
|
Rice
gHvNAS1-1
—
T30
HvNAS1
|
Rice
NIA-OS006-4
—
T6
WRKY45
|
Rice
NIA-OS005-3
—
T6
WRKY45
|
Rice
NIA-OS004-2
—
T6
WRKY45
|
Rice
NIA-OS003-1
—
T6
WRKY45
|
Rice
NIA-OS002-9
—
T6
WRKY45
|
Rice
NIA-OS001-8
—
T6
WRKY45
|
Rice
OsCr11
—
T13
Modified Cry j
|
Rice
17053
—
T1
cp4 epsps (aroA:CP4)
|
Rice
17314
—
T1
cp4 epsps (aroA:CP4)
|
Rose
WKS82/130-4-1
IFD-52401-4
T9
5AT; bp40 (f3’5’h)
|
Rose
WKS92 /130-9-1
IFD-52901-9
T9
5AT; bp40 (f3’5’h)
|
Soybean
260-05 (G94-1,
—
T9
gm-fad2-1
|
G94-19, G168)
(silencing locus)
|
Soybean
A2704-12
ACS-GM005-3
T3
pat
|
Soybean
A2704-21
ACS-GM004-2
T3
pat
|
Soybean
A5547-127
ACS-GM006-4
T3
pat
|
Soybean
A5547-35
ACS-GM008-6
T3
pat
|
Soybean
CV127
BPS-CV127-9
T16
csr1-2
|
Soybean
DA568416-4
DA568416-4
T3
pat
|
Soybean
DP305423
DP-305423-1
T11, T31
gm-fad2-1 (silencing
|
locus); gm-hra
|
Soybean
DP356043
DP-356043-5
T1, T31
gm-fad2-1 (silencing
|
locus); gat4601
|
Soybean
FG72
MST-FG072-3
T32, T1
2mepsps; hppdPF
|
W336
|
Soybean
GTS 40-3-2 (40-3-2)
MON-04032-6
T1
cp4 epsps (aroA:CP4)
|
Soybean
GU262
ACS-GM003-1
T3
pat
|
Soybean
MON87701
MON-87701-2
T7
cry1Ac
|
Soybean
MON87705
MON-87705-6
T1, T31
fatb1-A (sense & antisense);
|
fad2-1A (sense
|
& antisense); cp4 epsps
|
(aroA:CP4)
|
Soybean
MON87708
MON-87708-9
T1, T12
dmo; cp4 epsps (aroA:CP4)
|
Soybean
MON87769
MON-87769-7
T1, T31
Pj.D6D; Nc.Fad3;
|
cp4 epsps (aroA:CP4)
|
Soybean
MON89788
MON-89788-1
T1
cp4 epsps (aroA:CP4)
|
Soybean
W62
ACS-GM002-9
T3
bar
|
Soybean
W98
ACS-GM001-8
T3
bar
|
Soybean
MON87754
MON-87754-1
T33
dgat2A
|
Soybean
DAS21606
DAS-21606
T34, T3
Modified aad-12; pat
|
Soybean
DA544406
DAS-44406-6
T1, T3, T34
Modified aad-12; 2mepsps; pat
|
Soybean
SYHT04R
SYN-0004R-8
T35
Modified avhppd
|
Soybean
9582.814.19.1
—
T3, T7
cry1Ac, cry1F, PAT
|
Squash
CZW3
SEM-ØZW3-2
T6
cmv cp, zymv cp, wmv cp
|
Squash
ZW20
SEM-0ZW20-7
T6
zymv cp, wmv cp
|
Sugar Beet
GTSB77
SY-GTSB77-8
T1
cp4 epsps (aroA:CP4);
|
(T9100152)
goxv247
|
Sugar Beet
H7-1
KM-000H71-4
T1
cp4 epsps (aroA:CP4)
|
Sugar Beet
T120-7
ACS-BV001-3
T3
pat
|
Sugar Beet
T227-1
—
T1
cp4 epsps (aroA:CP4)
|
Sugarcane
NXI-1T
—
T21
EcbetA
|
Sunflower
X81359
—
T16
als
|
Pepper
PK-SP01
—
T6
cmv cp
|
Tobacco
C/F/93/08-02
—
T5
bxn
|
Tobacco
Vector 21-41
—
T36
NtQPT1 (antisense)
|
Sunflower
X81359
—
T16
als
|
Wheat
MON71800
MON-718ØØ-3
T1
cp4 epsps (aroA:CP4)
|
|
*Argentine (Brassica napus), **Polish (B. rapa), # Eggplant
|
Although most typically, compounds of the invention are used to control undesired vegetation, contact of desired vegetation in the treated locus with compounds of the invention may result in super-additive or synergistic effects with genetic traits in the desired vegetation, including traits incorporated through genetic modification. For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic/abiotic stresses or storage stability may be greater than expected from the genetic traits in the desired vegetation.
Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.
A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron, vemolate, 3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one), 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 3-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]dihydro-1,5-dimethyl-6-thioxo-1,3,5-triazine-2,4(1H,3H)-dione, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5 (2H,4H)-dione, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also include bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A4 and A7, harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
General references for agricultural protectants (i.e. herbicides, herbicide safeners, insecticides, fungicides, nematocides, acaricides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U. K., 2001.
For embodiments where one or more of these various mixing partners are used, the mixing partners are typically used in the amounts similar to amounts customary when the mixture partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between one-half and the full application rate specified on product labels for use of active ingredient alone. These amounts are listed in references such as The Pesticide Manual and The BioPesticide Manual. The weight ratio of these various mixing partners (in total) to the compound of Formula 1 is generally between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone.
In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates giving agronomically satisfactory levels of weed control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load. When safening of herbicidal active ingredients occurs on crops, such combinations can be advantageous for increasing crop protection by reducing weed competition.
Of note is a combination of a compound of the invention with at least one other herbicidal active ingredient. Of particular note is such a combination where the other herbicidal active ingredient has different site of action from the compound of the invention. In certain instances, a combination with at least one other herbicidal active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action.
Compounds of this invention can also be used in combination with herbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl 1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate, 2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and 3-oxo-1-cyclohexen-1-yl 1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
Table A1 lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound No. (Compound Number) (i.e. Compound 1) in the Component (a) column is identified in Index Table A. The second column of Table A1 lists the specific Component (b) compound (e.g., “2,4-D” in the first line). The third, fourth and fifth columns of Table A1 lists ranges of weight ratios for rates at which the Component (a) compound is typically applied to a field-grown crop relative to Component (b) (i.e. (a):(b)). Thus, for example, the first line of Table A1 specifically discloses the combination of Component (a) (i.e. Compound 1 in Index Table A) with 2,4-D is typically applied in a weight ratio between 1:384-6:1. The remaining lines of Table A1 are to be construed similarly.
TABLE A1
|
|
Component
More
Most
|
(a)
Typical
Typical
Typical
|
(Compound
Weight
Weight
Weight
|
No.)
Component (b)
Ratio
Ratio
Ratio
|
|
|
1
2,4-D
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Acetochlor
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Acifluorfen
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Aclonifen
1:1714-2:1
1:571-1:3
1:53-1:6
|
1
Alachlor
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Ametiyn
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Amicarbazone
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Amidosulfuron
1:13-168:1
1:4-56:1
2:1-21:1
|
1
Aminocyclopyrachlor
1:96-24:1
1:32-8:1
1:3-3:1
|
1
Aminopyralid
1:41-56:1
1:13-19:1
1:1-7:1
|
1
Amitrole
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Anilofos
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Asulam
1:1920-2:1
1:640-1:3
1:60-1:7
|
1
Atrazine
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Azimsulfuron
1:13-168:1
1:4-56:1
2:1-21:1
|
1
Beflubutamid
1:685-4:1
1:228-2:1
1:21-1:3
|
1
Benfuresate
1:1234-2:1
1:411-1:2
1:38-1:5
|
1
Bensulfuron-methyl
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Bentazone
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Benzobicyclon
1:171-14:1
1:57-5:1
1:5-2:1
|
1
Benzofenap
1:514-5:1
1:171-2:1
1:16-1:2
|
1
Bicyclopyrone
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Bifenox
1:514-5:1
1:171-2:1
1:16-1:2
|
1
Bispyribac-sodium
1:20-112:1
1:6-38:1
1:1-14:1
|
1
Bromacil
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Bromobutide
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Bromoxynil
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Butachlor
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Butafenacil
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Butylate
1:3085-1:2
1:1028-1:5
1:96-1:11
|
1
Carfenstrole
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Carfentrazone-ethyl
1:257-9:1
1:85-3:1
1:8-2:1
|
1
Chlorimuron-ethyl
1:17-135:1
1:5-45:1
1:1-17:1
|
1
Chlorotoluron
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Chlorsulfuron
1:13-168:1
1:4-56:1
2:1-21:1
|
1
Cincosulfuron
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Cinidon-ethyl
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Cinmethylin
1:68-34:1
1:22-12:1
1:2-5:1
|
1
Clacyfos
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Clethodim
1:96-24:1
1:32-8:1
1:3-3:1
|
1
Clodinafop-
1:41-56:1
1:13-19:1
1:1-7:1
|
propargyl
|
1
Clomazone
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Clomeprop
1:342-7:1
1:114-3:1
1:10-1:2
|
1
Clopyralid
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Cloransulam-
1:24-96:1
1:8-32:1
1:1-12:1
|
methyl
|
1
Cumyluron
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Cyanazine
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Cyclopyrimorate
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Cyclosulfamuron
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Cycloxydim
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Cyhalofop
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Daimuron
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Desmedipham
1:644-4:1
1:214-2:1
1:20-1:3
|
1
Dicamba
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Dichlobenil
1:2742-1:2
1:914-1:4
1:85-1:10
|
1
Dichlorprop
1:1851-2:1
1:617-1:3
1:57-1:7
|
1
Diclofop-methyl
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Diclosulam
1:20-112:1
1:6-38:1
1:1-14:1
|
1
Difenzoquat
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Diflufenican
1:1714-2:1
1:571-1:3
1:53-1:6
|
1
Diflufenzopyr
1:24-96:1
1:8-32:1
1:1-12:1
|
1
Dimethachlor
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Dimethametiyn
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Dimethenamid-P
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Dithiopyr
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Diuron
1:768-3:1
1:256-1:1
1:24-1:3
|
1
EPTC
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Esprocarb
1:2742-1:2
1:914-1:4
1:85-1:10
|
1
Ethalfluralin
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Ethametsulfuron-
1:34-68:1
1:11-23:1
1:1-9:1
|
methyl
|
1
Ethoxyfen
1:17-135:1
1:5-45:1
1:1-17:1
|
1
Ethoxysulfuron
1:41-56:1
1:13-19:1
1:1-7:1
|
1
Etobenzanid
1:514-5:1
1:171-2:1
1:16-1:2
|
1
Fenoxaprop-ethyl
1:240-10:1
1:80-4:1
1:7-2:1
|
1
Fenoxasulfone
1:171-14:1
1:57-5:1
1:5-2:1
|
1
Fenquinotrione
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Fentrazamide
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Flazasulfuron
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Florasulam
1:5-420:1
1:1-140:1
5:1-53:1
|
1
Fluazifop-butyl
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Flucarbazone
1:17-135:1
1:5-45:1
1:1-17:1
|
1
Flucetosulfuron
1:17-135:1
1:5-45:1
1:1-17:1
|
1
Flufenacet
1:514-5:1
1:171-2:1
1:16-1:2
|
1
Flumetsulam
1:48-48:1
1:16-16:1
1:1-6:1
|
1
Flumiclorac-pentyl
1:20-112:1
1:6-38:1
1:1-14:1
|
1
Flumioxazin
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Fluometuron
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Flupyrsulfuron-
1:6-336:1
1:2-112:1
4:1-42:1
|
methyl
|
1
Fluridone
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Fluroxypyr
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Flurtamone
1:1714-2:1
1:571-1:3
1:53-1:6
|
1
Fluthiacet-methyl
1:96-42:1
1:32-14:1
1:1-6:1
|
1
Fomesafen
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Foramsulfuron
1:27-84:1
1:9-28:1
1:1-11:1
|
1
Glufosinate
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Glyphosate
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Halosulfuron-methyl
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Halauxifen
1:41-56:1
1:13-19:1
1:1-7:1
|
1
Halauxifen methyl
1:41-56:1
1:13-19:1
1:1-7:1
|
1
Haloxyfop-methyl
1:68-34:1
1:22-12:1
1:2-5:1
|
1
Hexazinone
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Imazamox
1:27-84:1
1:9-28:1
1:1-11:1
|
1
Imazapic
1:41-56:1
1:13-19:1
1:1-7:1
|
1
Imazapyr
1:171-14:1
1:57-5:1
1:5-2:1
|
1
Imazaquin
1:68-34:1
1:22-12:1
1:2-5:1
|
1
Imazethabenz-
1:342-7:1
1:114-3:1
1:10-1:2
|
methyl
|
1
Imazethapyr
1:48-48:1
1:16-16:1
1:1-6:1
|
1
Imazosulfuron
1:54-42:1
1:18-14:1
1:1-6:1
|
1
Indanofan
1:685-4:1
1:228-2:1
1:21-1:3
|
1
Indaziflam
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Iodosulfuron-
1:6-336:1
1:2-112:1
4:1-42:1
|
methyl
|
1
Ioxynil
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Ipfencarbazone
1:171-14:1
1:57-5:1
1:5-2:1
|
1
Isoproturon
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Isoxaben
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Isoxaflutole
1:120-20:1
1:40-7:1
1:3-3:1
|
1
Lactofen
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Lenacil
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Linuron
1:768-3:1
1:256-1:1
1:24-1:3
|
1
MCPA
1:384-6:1
1:128-2:1
1:12-1:2
|
1
MCPB
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Mecoprop
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Mefenacet
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Mefluidide
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Mesosulfuron-
1:10-224:1
1:3-75:1
3:1-28:1
|
methyl
|
1
Mesotrione
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Metamifop
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Metazachlor
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Metazosulfuron
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Methabenzthiazuron
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Metolachlor
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Metosulam
1:17-135:1
1:5-45:1
1:1-17:1
|
1
Metribuzin
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Metsulfuron-
1:4-560:1
1:1-187:1
7:1-70:1
|
methyl
|
1
Molinate
1:2057-2:1
1:685-1:3
1:64-1:8
|
1
Napropamide
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Napropamide-M
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Naptalam
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Nicosulfuron
1:24-96:1
1:8-32:1
1:1-12:1
|
1
Norflurazon
1:2304-1:1
1:768-1:3
1:72-1:8
|
1
Orbencarb
1:2742-1:2
1:914-1:4
1:85-1:10
|
1
Orthosulfamuron
1:41-56:1
1:13-19:1
1:1-7:1
|
1
Ofyzalin
1:1028-3:1
1:342-1:2
1:32-1:4
|
1
Oxadiargyl
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Oxadiazon
1:1097-3:1
1:365-1:2
1:34-1:4
|
1
Oxasulfuron
1:54-42:1
1:18-14:1
1:1-6:1
|
1
Oxaziclomefone
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Oxyfluorfen
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Paraquat
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Pendimethalin
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Penoxsulam
1:20-112:1
1:6-38:1
1:1-14:1
|
1
Penthoxamid
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Pentoxazone
1:205-12:1
1:68-4:1
1:6-2:1
|
1
Phenmedipham
1:205-12:1
1:68-4:1
1:6-2:1
|
1
Picloram
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Picolinafen
1:68-34:1
1:22-12:1
1:2-5:1
|
1
Pinoxaden
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Pretilachlor
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Primisulfuron-
1:17-135:1
1:5-45:1
1:1-17:1
|
methyl
|
1
Prodiamine
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Profoxydim
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Prometiyn
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Propachlor
1:2304-1:1
1:768-1:3
1:72-1:8
|
1
Propanil
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Propaquizafop
1:96-24:1
1:32-8:1
1:3-3:1
|
1
Propoxycarbazone
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Propyrisulfuron
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Propyzamide
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Prosulfocarb
1:2400-1:2
1:800-1:4
1:75-1:9
|
1
Prosulfuron
1:13-168:1
1:4-56:1
2:1-21:1
|
1
Pyraclonil
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Pyraflufen-ethyl
1:10-224:1
1:3-75:1
3:1-28:1
|
1
Pyrasulfotole
1:27-84:1
1:9-28:1
1:1-11:1
|
1
Pyrazolynate
1:1714-2:1
1:571-1:3
1:53-1:6
|
1
Pyrazosulfuron-
1:20-112:1
1:6-38:1
1:1-14:1
|
ethyl
|
1
Pyrazoxyfen
1:10-224:1
1:3-75:1
3:1-28:1
|
1
Pyribenzoxim
1:20-112:1
1:6-38:1
1:1-14:1
|
1
Pyributicarb
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Pyridate
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Pyriftalid
1:20-112:1
1:6-38:1
1:1-14:1
|
1
Pyriminobac-
1:41-56:1
1:13-19:1
1:1-7:1
|
methyl
|
1
Pyrimisulfan
1:34-68:1
1:11-23:1
1:1-9:1
|
1
Pyrithiobac
1:48-48:1
1:16-16:1
1:1-6:1
|
1
Pyroxasulfone
1:171-14:1
1:57-5:1
1:5-2:1
|
1
Pyroxsulam
1:10-224:1
1:3-75:1
3:1-28:1
|
1
Quinclorac
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Quizalofop-ethyl
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Rimsulfuron
1:27-84:1
1:9-28:1
1:1-11:1
|
1
Saflufenacil
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Sethoxydim
1:192-12:1
1:64-4:1
1:6-2:1
|
1
Simazine
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Sulcotrione
1:240-10:1
1:80-4:1
1:7-2:1
|
1
Sulfentrazone
1:294-8:1
1:98-3:1
1:9-1:2
|
1
Sulfometuron-
1:68-34:1
1:22-12:1
1:2-5:1
|
methyl
|
1
Sulfosulfuron
1:17-135:1
1:5-45:1
1:1-17:1
|
1
Tebuthiuron
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Tefufyltrione
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Tembotrione
1:63-37:1
1:21-13:1
1:1-5:1
|
1
Tepraloxydim
1:51-45:1
1:17-15:1
1:1-6:1
|
1
Terbacil
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Terbuthylazine
1:1714-2:1
1:571-1:3
1:53-1:6
|
1
Terbutiyn
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Thenylchlor
1:171-14:1
1:57-5:1
1:5-2:1
|
1
Thiazopyr
1:768-3:1
1:256-1:1
1:24-1:3
|
1
Thiencarbazone
1:6-336:1
1:2-112:1
4:1-42:1
|
1
Thifensulfuron-
1:10-224:1
1:3-75:1
3:1-28:1
|
methyl
|
1
Tiafenacil
1:85-27:1
1:28-9:1
1:2-4:1
|
1
Thiobencath
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Topramezone
1:13-168:1
1:4-56:1
2:1-21:1
|
1
Tralkoxydim
1:137-17:1
1:45-6:1
1:4-3:1
|
1
Triallate
1:1536-2:1
1:512-1:2
1:48-1:6
|
1
Triasulfuron
1:10-224:1
1:3-75:1
3:1-28:1
|
1
Triaziflam
1:342-7:1
1:114-3:1
1:10-1:2
|
1
Tribenuron-methyl
1:6-336:1
1:2-112:1
4:1-42:1
|
1
Triclopyr
1:384-6:1
1:128-2:1
1:12-1:2
|
1
Trifloxysulfuron
1:5-420:1
1:1-140:1
5:1-53:1
|
1
Trifluralin
1:576-4:1
1:192-2:1
1:18-1:2
|
1
Triflusulfuron-
1:34-68:1
1:11-23:1
1:1-9:1
|
methyl
|
1
Tritosulfuron
1:27-84:1
1:9-28:1
1:1-11:1
|
|
Table A2 is constructed the same as Table A1 above except that entries below the “Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below. Compound No. in the Component (a) column is identified in Index Table A. Thus, for example, in Table A2 the entries below the “Component (a)” column heading all recite “Compound 2” (i.e. Compound 2 identified in Index Table A), and the first line below the column headings in Table A2 specifically discloses a mixture of Compound 2 with 2,4-D. Tables A3 through A60 are constructed similarly.
|
Table
Component (a)
|
Number
Column Entries
|
|
A2
Compound 2
|
A3
Compound 3
|
A4
Compound 4
|
A5
Compound 5
|
A6
Compound 6
|
A7
Compound 7
|
A8
Compound 8
|
A9
Compound 9
|
A10
Compound 10
|
A11
Compound 11
|
A12
Compound 12
|
A13
Compound 13
|
A14
Compound 14
|
A15
Compound 15
|
A16
Compound 16
|
A17
Compound 17
|
A18
Compound 18
|
A19
Compound 19
|
A20
Compound 20
|
A21
Compound 21
|
A22
Compound 22
|
A23
Compound 23
|
A24
Compound 24
|
A25
Compound 25
|
A26
Compound 26
|
A27
Compound 27
|
A28
Compound 28
|
A29
Compound 29
|
A30
Compound 30
|
A31
Compound 31
|
A32
Compound 32
|
A33
Compound 33
|
A34
Compound 34
|
A35
Compound 35
|
A36
Compound 36
|
A37
Compound 37
|
A38
Compound 38
|
A39
Compound 39
|
A40
Compound 40
|
A41
Compound 41
|
A42
Compound 42
|
A43
Compound 43
|
A44
Compound 44
|
A45
Compound 45
|
A46
Compound 46
|
A47
Compound 47
|
A48
Compound 48
|
A49
Compound 49
|
A50
Compound 50
|
A51
Compound 51
|
A52
Compound 52
|
A53
Compound 53
|
A54
Compound 54
|
A55
Compound 55
|
A56
Compound 56
|
A57
Compound 57
|
A58
Compound 58
|
A59
Compound 59
|
A60
Compound 60
|
A61
Compound 61
|
A62
Compound 62
|
A63
Compound 63
|
A64
Compound 64
|
A65
Compound 65
|
A66
Compound 66
|
A67
Compound 67
|
A68
Compound 68
|
A69
Compound 69
|
A70
Compound 70
|
A71
Compound 71
|
A72
Compound 72
|
A73
Compound 73
|
A74
Compound 74
|
A75
Compound 75
|
A76
Compound 76
|
A77
Compound 77
|
A78
Compound 78
|
A79
Compound 79
|
A80
Compound 80
|
A81
Compound 81
|
A82
Compound 82
|
A83
Compound 83
|
A84
Compound 84
|
A85
Compound 85
|
A86
Compound 86
|
A87
Compound 87
|
A88
Compound 88
|
A89
Compound 89
|
A90
Compound 90
|
A91
Compound 91
|
A92
Compound 92
|
A93
Compound 93
|
A94
Compound 94
|
A95
Compound 95
|
A96
Compound 96
|
A97
Compound 97
|
A98
Compound 98
|
A99
Compound 99
|
A100
Compound 100
|
A101
Compound 101
|
A102
Compound 102
|
A103
Compound 103
|
A104
Compound 104
|
A105
Compound 105
|
A106
Compound 106
|
A107
Compound 107
|
A108
Compound 108
|
A109
Compound 109
|
A110
Compound 110
|
A111
Compound 111
|
A112
Compound 112
|
A113
Compound 113
|
A114
Compound 114
|
A115
Compound 115
|
A116
Compound 116
|
A117
Compound 117
|
A118
Compound 118
|
A119
Compound 119
|
A120
Compound 120
|
A121
Compound 121
|
A122
Compound 122
|
A123
Compound 123
|
A124
Compound 124
|
A125
Compound 125
|
A126
Compound 126
|
A127
Compound 127
|
A128
Compound 128
|
A129
Compound 129
|
A130
Compound 130
|
A131
Compound 131
|
A132
Compound 132
|
A133
Compound 133
|
A134
Compound 134
|
A135
Compound 135
|
A136
Compound 136
|
A137
Compound 137
|
A138
Compound 138
|
A139
Compound 139
|
A140
Compound 140
|
A141
Compound 141
|
A142
Compound 142
|
A143
Compound 143
|
A144
Compound 144
|
A145
Compound 145
|
A146
Compound 146
|
A147
Compound 147
|
A148
Compound 148
|
A149
Compound 149
|
A150
Compound 150
|
A151
Compound 151
|
A152
Compound 152
|
A153
Compound 153
|
A154
Compound 154
|
A155
Compound 155
|
A156
Compound 156
|
A157
Compound 157
|
A158
Compound 158
|
A159
Compound 159
|
A160
Compound 160
|
A161
Compound 161
|
A162
Compound 162
|
A163
Compound 163
|
A164
Compound 164
|
A165
Compound 165
|
A166
Compound 166
|
A167
Compound 167
|
A168
Compound 168
|
A169
Compound 169
|
A170
Compound 170
|
A171
Compound 171
|
A172
Compound 172
|
A173
Compound 173
|
A174
Compound 174
|
A175
Compound 175
|
A176
Compound 176
|
A177
Compound 177
|
A178
Compound 178
|
A179
Compound 179
|
A180
Compound 180
|
A181
Compound 181
|
A182
Compound 182
|
A183
Compound 183
|
A184
Compound 184
|
A185
Compound 185
|
A186
Compound 186
|
A187
Compound 187
|
A188
Compound 188
|
|
The following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Table A for compound descriptions. The 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
|
![embedded image]()
|
|
Cmpd.
m.p.
|
No.
R1
R2
X
(R3)n
R4
G
(° C.)
M + 1
NMR
|
|
1 (Ex. 1)
Me
Me
S
5-Me
Me
H
301.5
**
|
2
Me
Me
S
5,7-di-Me
Me
H
*
|
3
Me
Me
S
4,6-di-Me
Me
H
224-
315.5
*
|
227
|
4
Me
Me
O
—
Me
H
238-
271.5
*
|
240
|
5
Me
Me
O
5-OMe
Me
H
301.5
*
|
6
Me
Me
O
5-Cl
Me
H
*
|
7
Me
Me
O
5-Me
Me
H
**
|
(Ex. 2)
|
8
Me
Me
O
4-Me
Me
H
*
|
9
Me
Me
O
7-Me
Me
H
285.5
*
|
10
Me
Me
O
5-Me
Et
H
299.5
*
|
11
Me
Me
—CH═CH—
—
H
H
267
*
|
12
Me
Me
O
5,7-di-Me
Me
H
**
|
(Ex. 3)
|
13
Me
Me
O
5-Et
Me
H
*
|
14
Me
Me
O
5-Me
Me
—C(═O)Me
*
|
15
Me
Me
O
7-Me
Me
—C(═O)Me
*
|
16
Me
Me
O
5,7-di-Me
Me
—C(═O)Me
341.0
*
|
17
Me
Me
O
5-Me
Me
—C(═O)-t-Bu
369.0
*
|
18
Me
Me
O
5,7-di-Me
Me
—C(═O)-t-Bu
383.0
*
|
19
Me
Me
S
4,6-di-Me
Et
H
*
|
20
Me
Br
—CH═CH—
—
H
H
332
|
21
Me
Me
—CH═C(Me)—
—
Me
H
*
|
22
Me
Me
S
5-Br
Me
H
367
|
23
Me
Br
—CH═CH—
—
Me
H
343
|
24
Me
H
—CH═CF—
—
H
H
*
|
25
Me
Me
S
5-Me
Me
—C(═O)Me
*
|
26
Me
Me
S
5-Me
Me
—C(═O)-t-Bu
385.4
|
27
Me
Me
S
5,7-di-Me
Me
—C(═O)Me
140-
|
145
|
28
Me
Me
S
5,7-di-Me
Me
—C(═O)Et
134-
|
137
|
29
Me
I
—CH═CH—
—
Me
H
393
|
30
Me
OMe
—CH═CH—
5-Me
Me
H
311
|
31
Me
Me
N(Me)
5-Me
Me
H
94-98
|
32
Me
Me
—CH═CH—
—
Et
H
226-
|
229
|
33
Me
OMe
S
—
Me
H
303
|
34
Me
Me
—C(Me)═CH—
—
Me
H
295
|
35
Me
Me
S
5-Cl, 7-Me
Me
H
335
|
36
Me
OMe
—CH═CH—
—
Me
—C(═O)O-i-Pr
*
|
37
Me
Me
—CH═CH—
—
Et
—C(═)OEt
367.6
|
38
Me
Me
—CH═CH—
—
Et
—C(═O)-c-Pr
363.6
|
39
Me
Me
—CH═CH—
—
Et
—C(═O)O-i-Pr
112-
|
116
|
40
Me
Me
—CH═CH—
—
OMe
H
297
|
41
Me
Me
—CH═CF—
—
H
H
*
|
42
Me
Me
S
5-Me
Me
—C(═O)Et
125-
|
130
|
43
Me
Me
S
5,7-di-Me
Me
—C(═O)-t-Bu
399.4
|
44
Me
Me
S
4,6-di-Me
Me
—C(═O)Me
357
|
45
Me
Me
S
4,6-di-Me
Me
—C(═O)-t-Bu
399
|
46
Me
OMe
—C(Me)═CH—
—
Me
H
311
|
(Ex. 4)
|
47
Me
Me
S
5-Me
Et
H
203-
|
205
|
48
Me
H
S
—
Me
H
273
|
49
Me
H
—CH═CH—
—
H
H
251.5#
|
50
Me
H
—CH═C(Me)—
—
H
H
267
|
51
Me
H
—CH═C(Me)—
—
Me
H
*
|
52
Me
Br
—CH═C(Me)—
—
H
H
347.4
|
53
Me
Me
S
5-OMe
Me
H
187-
|
189
|
54
Me
OMe
—CH═CH—
—
Me
H
297
|
55
Me
OMe
—CH═CH—
—
H
H
283
|
56
Me
H
—CH═CH—
—
Me
H
249-
|
251
|
57
Me
Me
S
5,7-di-Me
Et
H
200-
|
202
|
58
Me
Me
—CH═C(OMe)—
—
H
H
297
|
59
Me
Me
—CH═CH—
—
Me
H
269-
|
273
|
60
Me
Me
—CH═CH—
5-Me
Me
H
230-
|
233
|
61
Me
Ph
O
5-Me
Me
H
259-
|
263
|
62
Me
Me
—CH═C(Cl)—
—
H
—C(═O)Et
*
|
63
Me
Me
—CH═C(Cl)—
—
H
—C(═O)OMe
359
|
64
Et
Et
O
5-Me
Me
H
215-
|
219
|
65
Me
Me
S
—
Me
H
225-
|
228
|
66
Me
Me
S
5-Me
Me
—C(═O)O-i-Pr
128-
|
129
|
67
Me
Me
S
5,7-di-Me
Me
—C(═O)O-i-Pr
123-
|
125
|
68
Me
Me
O
5-OEt
Et
H
170-
|
174
|
69
Me
Me
—CH═CH—
5-Me
H
H
282
|
70
Me
Me
—CH═CH—
5-I
H
H
393
|
71
Me
Me
—CH═CH—
5-c-Pr
H
H
307
|
72
Me
Me
—CH═CH—
—
Me
—C(═O)O-i-Pr
230-
|
235
|
73
Me
Me
—CH═CH—
—
Me
—C(═O)OEt
146-
|
150
|
74
Me
Me
N(Me)
5-Cl
Me
H
314-
|
318
|
75
Me
Me
—CH═C(Br)—
—
H
H
285-
|
289
|
76
Me
Me
—CH═CH—
—
Me
—C(═O)-c-Pr
349
|
77
Me
Et
O
5-Cl
Me
H
242-
|
248
|
78
Me
Me
—CH═CH—
—
Me
—C(═O)Et
*
|
79
Me
Me
S
5-Me
Br
H
367.2
|
80
Me
Me
S
5-Me
Me
—C(═O)OMe
359.5
|
81
Me
Me
S
5,7-di-Me
Me
—C(═O)OMe
373.5
|
82
Me
Me
S
5-Me
Me
—C(═O)OEt
373.5
|
83
Me
Me
S
5,7-di-Me
Me
—C(═O)OEt
387.5
|
84
Me
Me
S
5-Me
Me
—C(═O)CH2CH2Cl
407.4
|
85
Me
Me
S
5,7-di-Me
Me
—C(═O)OCH2CH2Cl
421.4
|
86
Me
OMe
—CH═CH—
—
CF2H
H
331#
|
87
Me
Me
S
5-Me
Me
—C(═O)OCH2C≡CH
383.3
|
88
Me
Me
S
5,7-di-Me
Me
—C(═O)CH2C≡CH
397.3
|
89
Me
Cl
S
—
Me
H
307
|
90
Me
Me
—CH═CF—
—
H
—C(═O)Me
*
|
91 (Ex. 5)
Me
Cl
S
5-Cl
Me
H
**
|
92
Me
Me
—CH═CH—
5-OEt
H
H
309
|
93
Me
Me
—CH═CH—
5-OCF2H
H
H
333
|
94
Me
Cl
S
—
Me
—C(═O)O-i-Pr
*
|
95
Me
Me
NMe
—
Cl
H
237-
|
239
|
96
Me
Me
—CH═CH—
5-OEt
H
H
297
|
97
Me
H
S
—
Me
—C(═O)OMe
331
|
98
Me
CN
—CH═CH—
—
Me
—C(═O)Me
*
|
99
Me
Me
—CH═CMe—
—
Me
—C(═O)Me
*
|
100
Me
OMe
S
5-Cl
Me
H
337
|
101
Me
Cl
S
5-Cl
Me
—C(═O)OMe
*
|
102
Me
CF3
—CH═CH—
—
Me
H
335
|
103
Me
Me
—CH═CH—
5-Me
Et
H
186-
|
189
|
104
Me
Me
S
5-Cl
Me
H
254-
|
257
|
105
Me
Me
S
5-Me
Me
—C(═O)-n-Pr
115-
|
117
|
106
Me
Me
S
5,7-di-Me
Me
—C(═O)-n-Pr
113-
|
115
|
107
Me
Me
S
5-Me
Et
—C(═O)-n-Pr
80-82
|
108
Me
Me
S
5-Cl
Me
—C(═O)Me
203-
|
206
|
109
Me
Me
S
5-Cl
Me
—C(═O)Et
125-
|
127
|
110
Me
Me
—CH═CH—
6-Me
Me
H
295
|
111
Me
Cl
S
5-Cl
Me
—C(═O)Et
*
|
112
Me
OMe
S
5-Cl
Me
—C(═O)OMe
395
|
113
Me
Me
—CH═CF—
—
H
—C(═O)Et—
*
|
114
Me
Cl
S
5-Cl
Me
—SO2Me
*
|
115
Me
Me
—CF═CH—
—
H
—SO2Me
363
|
116
Me
Cl
S
5-Cl
Me
—C(═O)Me
*
|
117
Me
Et
O
—
Me
H
210-
|
215
|
118
Me
Et
O
5-Me
Me
H
334-
|
338
|
119
Me
i-Pr
O
5-Me
Me
H
245-
|
250
|
120
Me
H
S
—
Me
—C(═O)Me
*
|
121
Me
Me
S
5-CF3
Me
H
355
|
122
Me
OMe
S
5-Cl
Me
—C(═O)Me
*
|
123
Me
Me
—CH═CF—
—
H
—C(═O)CH2CF3
*
|
124
Me
Me
—CH═CH—
5-
H
—C(═O)Me
*
|
OC(═O)Me
|
125
Me
Cl
—CH═CH—
—
Me
H
301
|
126
Me
Me
—CH═CH—
5-Br
H
H
347
|
127
Me
Me
—CH═CH—
5-CN
H
H
292
|
128
Me
CN
—CH═CH—
—
Me
—C(═O)-t-Bu
*
|
129
Me
Br
—CH═CH—
—
Me
—C(═O)Me
*
|
130
Me
Me
—CH═CF—
—
H
—C(═O)OMe
*
|
131
Me
OMe
S
5-Cl
Me
—C(═O)Et
*
|
132
Me
Me
S
5-CF3
Me
—C(═O)Me
*
|
133
Me
Me
—CH═CBr—
—
H
—C(═O)Et
117-
|
120
|
134
Me
Me
—CH═CBr—
—
H
—C(═O)Et
120-
|
124
|
135
Me
OMe
S
5-Cl
Me
—SO2Me
415
|
136
Me
OMe
—CH═CH—
—
Me
—(C═O)OMe
355
|
137
Me
Br
—CH═CH—
—
Me
—C(═O)OMe
*
|
138
Me
OMe
—CH═CH—
—
Me
—C(═O)Me
*
|
139
Me
Me
—CH═CCl—
—
H
H
301
|
140
Me
Cl
S
5-CF3
Me
H
375
|
141
Me
OMe
S
—
Me
—C(═O)Me
*
|
142
Me
H
—CH═CH—
—
Me
—SO2Me
345
|
143
Me
H
—CH═CH—
—
Me
—C(═O)OMe
325
|
144
Me
Me
—CH═CH—
5-Cl
Me
H
280-
|
284
|
145
Me
Me
—CH═CBr—
—
H
—C(═O)OMe
403
|
146
Me
Me
—CH═CH—
—
CF3
—C(═O)OEt
115-
|
118
|
147
Me
Me
—CH═CH—
—
CF3
—C(═O)Et
132-
|
135
|
148
Me
Me
—CH═CH—
—
CF3
—C(═O)Me
181-
|
184
|
149
Me
Me
—CH═CH—
—
CF3
—C(═O)OMe
130-
|
133
|
150
Me
Me
—CH═CH—
5-C≡CH
H
H
291
|
151
Me
Me
—CH═CH—
5-F,7-Me
Me
H
319.1
|
152
Me
Cl
S
5-CF3
Me
—C(═)Me
*
|
153
Me
Me
—CH═CMe—
—
Me
—C(═O)Me
*
|
154
Me
Me
—CH═CMe—
—
Me
—SO2Me
373
|
155
Me
Br
—CH═CH—
—
Me
—SO2Me
*
|
156
Me
Br
—CH═CH—
—
Me
—C(═O)Et
*
|
157
Me
Me
—CH═CCl—
—
H
—C(═O)Me
343
|
158
Me
Me
—CH═CCl—
—
H
—SO2CF3
?
433
|
159
Me
Me
—CH═CCl—
—
H
—C(═O)CF3
*
|
160
Me
Me
S
5-Me
Me
—CH2CN
340
|
161
Me
Me
—CH═CH—
5-NO2
Me
H
312
|
162
Me
Me
—CH═CH—
—
NO2
—C(═O)OMe
162-
|
166
|
163
Me
Me
—CH═CH—
—
NO2
—C(═O)-t-Bu
239-
|
243
|
164
Me
Me
—CH═CH—
—
NO2
—C(═O)Me
189-
|
193
|
165
Me
Me
—CH═CH—
—
NO2
H
264-
|
268
|
166
Me
Me
—CH═CH—
—
NO2
—C(═O)OEt
147-
|
150
|
167
Me
Me
—CH═CH—
—
NO2
—C(═O)-c-Pr
165-
|
170
|
168
Bn
Me
—CH═CH—
—
H
H
343
|
169
H
Me
—CH═CH—
—
H
H
253
|
170
Me
Me
S
—
Me
—C(═O)-N-morph
168-
|
171
|
171
Me
Me
—CH═CH—
—
H
—C(═O)CH2SMe
*
|
172
CH2CO2Me
Me
—CH═CH—
—
H
H
325
|
173
H
Me
—CH═CH—
—
H
—CH2CF2H
317
|
174
Me
Me
S
5,7-di-Me
Me
—C(═O)-N-morph
428
|
175
H
Me
—CH═CH—
—
H
—CF2H
303
|
176
Me
Br
—CH═CH—
—
Me
—C(═O)-N-morph
*
|
177
Me
NO2
—CH═CH—
—
Me
H
312
|
178
Me
Me
—CH═CH—
—
H
—CH2C(═O)Me
323
|
179
Me
Me
—CH═CH—
—
H
—CH2C≡CH
305
|
180
Me
Me
—CH═CH—
—
H
—CH2CH═CHPh
383
|
181
Me
Me
—CH═CH—
—
H
—CH2C(═O)-c-Pr
349
|
182
Me
Me
—CH═CH—
—
H
—CH2C(═O)OMe
339
|
183
Me
Me
—CH═CH—
—
H
—C(═O)CH═CHPh
397
|
184
Me
Me
—CH═CH—
—
H
—CH2C(═O)Ph
385
|
185
Me
Me
—CH═CCl—
—
H
—SO2N(Me)2
408
|
186
Me
Me
—CH═CCl—
—
H
—P(═O)(OMe)2
410
|
187
Me
Me
—CH═CCl—
—
H
—P(═O)(Me)2
377
|
188
Me
Me
S
5,7-di-Me
Me
—CH2CN
354
|
|
*See Index Table B for 1H NMR data.
|
**See Synthesis Example for 1H NMR data.
|
#M-1 peak.
|
INDEX TABLE B
|
|
Cmpd. No.
1H NMR Data (CDCl3 solution unless indicated otherwise)a
|
|
|
2
δ 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)
|
3
δ 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-d6) 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).
|
5
δ 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).
|
6
δ 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).
|
8
δ 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-d6) 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-d6) 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-d6) 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).
|
13
δ 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).
|
14
δ 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).
|
15
δ 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).
|
16
δ 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).
|
17
δ 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).
|
18
δ 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).
|
19
δ 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).
|
21
δ 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).
|
24
δ 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).
|
25
δ 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).
|
36
δ 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).
|
41
δ 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).
|
51
δ 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).
|
62
δ 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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).
|
99
δ 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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).
|
125
δ 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).
|
129
δ 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).
|
130
δ 7.82, (m, 2H), 7.29 (m, 4H), 3.88 (s, 1H),
|
2.30 (s, 3H) 1.80 (s, 3H).
|
131
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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
(500 MHz) 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).
|
160
δ 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
(500 MHz) 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
(500 MHz) 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).
|
|
a1H 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 Examples of the Invention
Test A
Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), ryegrass, Italian (Italian ryegrass, Lolium multiflorum), crabgrass, large (large crabgrass, Digitaria sanguinalis), foxtail, giant (giant foxtail, Setaria faberii), momingglory (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.
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 A
|
|
Compounds
|
1000 g ai/ha
1
3
4
5
6
7
10
11
13
32
60
178
179
180
|
|
Postemergence
|
Barnyardgrass
90
50
70
40
70
90
90
80
80
90
90
0
10
0
|
Blackgrass
—
—
—
—
—
—
—
—
30
90
90
30
40
30
|
Corn
40
0
0
0
0
10
20
50
20
50
50
0
10
0
|
Crabgrass, Large
90
10
50
80
50
50
70
70
—
—
—
—
—
—
|
Foxtail, Giant
80
10
80
80
70
90
80
90
80
90
90
0
10
0
|
Galium
—
—
—
—
—
—
—
—
70
100
100
70
90
80
|
Kochia
—
—
—
—
—
—
—
—
30
100
100
10
10
40
|
Morningglory
100
90
70
70
40
100
100
90
—
—
—
—
—
—
|
Pigweed
100
0
50
10
50
100
90
90
20
100
100
70
0
50
|
Ragweed
—
—
—
—
—
—
—
—
30
100
100
60
40
0
|
Ryegrass, Italian
—
—
—
—
—
—
—
—
70
100
100
70
70
70
|
Velvetleaf
100
70
60
—
—
100
100
100
—
—
—
—
—
—
|
Wheat
0
0
0
0
20
20
0
60
20
100
70
0
0
0
|
|
Compounds
|
1000 g ai/ha
181
182
183
184
|
|
Postemergence
|
Barnyardgrass
0
0
40
20
|
Blackgrass
20
10
80
30
|
Corn
0
0
10
0
|
Crabgrass, Large
—
—
—
—
|
Foxtail, Giant
0
0
70
20
|
Galium
80
50
90
90
|
Kochia
0
0
90
80
|
Morningglory
—
—
—
—
|
Pigweed
30
0
90
80
|
Ragweed
30
30
70
30
|
Ryegrass, Italian
80
0
100
80
|
Velvetleaf
—
—
—
—
|
Wheat
0
0
0
0
|
|
Compounds
|
500 g ai/ha
2
8
9
12
14
15
16
17
18
19
20
21
22
23
|
|
Postemergence
|
Barnyardgrass
80
0
90
40
70
90
90
0
40
80
100
90
50
90
|
Blackgrass
—
—
—
50
30
50
30
40
20
0
40
90
70
80
|
Corn
20
0
0
0
20
20
0
0
20
0
30
60
0
50
|
Crabgrass, Large
70
30
50
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
90
30
90
70
70
90
80
0
20
60
100
100
90
90
|
Galium
—
—
—
90
90
90
100
60
60
80
100
100
100
100
|
Kochia
—
—
—
60
90
50
60
0
0
0
100
100
100
100
|
Morningglory
100
10
80
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
80
0
50
80
0
40
0
0
0
100
100
100
100
|
Ragweed
—
—
—
70
90
50
70
0
0
0
100
100
100
100
|
Ryegrass, Italian
—
—
—
70
80
90
80
60
50
0
100
100
100
100
|
Velvetleaf
100
60
10
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
20
0
0
0
0
0
0
0
0
0
30
60
0
80
|
|
Compounds
|
500 g ai/ha
24
25
26
27
28
29
30
31
33
34
35
36
37
38
|
|
Postemergence
|
Barnyardgrass
50
90
30
90
90
80
30
10
90
90
90
80
90
40
|
Blackgrass
50
90
70
90
90
80
60
20
40
90
80
80
100
60
|
Corn
0
20
0
20
20
40
0
0
10
0
30
40
40
10
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
60
90
60
90
90
90
60
10
90
90
90
90
90
50
|
Galium
100
100
90
100
100
90
90
70
100
100
100
100
100
100
|
Kochia
80
100
90
90
90
90
80
0
100
80
100
100
90
80
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
90
100
90
100
90
40
70
90
90
90
100
50
|
Ragweed
60
100
90
100
100
100
70
20
90
100
80
90
90
70
|
Ryegrass, Italian
90
100
90
100
100
100
60
0
70
100
100
80
100
50
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
70
0
0
0
0
60
10
0
0
40
40
30
80
20
|
|
Compounds
|
500 g ai/ha
39
40
41
42
43
44
45
46
47
48
49
50
51
52
|
|
Postemergence
|
Barnyardgrass
10
60
90
90
30
0
0
80
80
50
20
0
80
50
|
Blackgrass
70
80
90
90
80
0
0
70
70
30
30
10
60
30
|
Corn
0
10
70
20
0
0
0
0
10
0
0
0
0
20
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
60
80
100
100
70
0
0
80
80
60
20
0
80
50
|
Galium
100
100
100
100
90
70
0
90
100
90
80
80
100
100
|
Kochia
30
90
100
100
10
0
0
40
90
80
10
20
90
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
80
100
90
100
10
0
0
90
100
70
40
50
90
30
|
Ragweed
90
90
100
100
0
0
0
90
100
20
10
20
70
100
|
Ryegrass, Italian
60
90
100
100
60
0
0
80
80
60
50
40
90
80
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
10
50
80
20
0
0
0
20
0
0
0
0
0
0
|
|
Compounds
|
500 g ai/ha
53
54
55
56
57
58
59
61
62
63
64
65
66
67
|
|
Postemergence
|
Barnyardgrass
20
90
90
60
100
0
90
0
90
90
0
90
90
70
|
Blackgrass
30
40
80
50
60
50
100
0
80
80
0
70
80
80
|
Corn
0
30
20
10
30
0
60
0
30
40
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
30
90
90
60
90
10
100
0
90
90
0
90
90
90
|
Galium
80
100
100
100
100
100
100
0
100
100
0
100
90
90
|
Kochia
80
100
100
100
100
90
100
0
100
100
0
90
90
30
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
70
100
90
90
100
20
100
0
100
100
0
90
90
20
|
Ragweed
70
100
100
90
100
60
100
0
100
100
0
90
90
70
|
Ryegrass, Italian
70
100
100
100
90
80
100
0
100
100
0
100
100
90
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
20
20
0
50
10
20
100
0
50
40
0
0
0
0
|
|
Compounds
|
500 g ai/ha
68
69
70
71
72
73
74
75
76
77
78
79
80
81
|
|
Postemergence
|
Barnyardgrass
80
40
10
20
60
90
10
60
30
0
30
80
80
90
|
Blackgrass
10
40
30
40
90
90
40
70
10
0
80
80
80
90
|
Corn
0
0
0
20
40
60
0
20
0
0
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
50
40
25
20
90
100
20
50
20
0
70
80
80
100
|
Galium
0
90
90
90
100
100
20
100
80
60
100
90
90
100
|
Kochia
0
80
60
70
90
100
30
90
40
10
90
90
90
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
90
80
80
90
100
50
50
20
0
90
90
90
100
|
Ragweed
0
80
70
70
90
100
10
90
20
0
80
90
90
100
|
Ryegrass, Italian
0
90
80
90
100
100
0
100
80
60
100
90
90
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
20
70
90
0
20
0
0
60
0
0
0
|
|
Compounds
|
500 g ai/ha
82
83
84
85
86
87
88
89
90
91
92
93
94
95
|
|
Postemergence
|
Barnyardgrass
50
90
40
80
10
80
90
80
100
90
0
20
40
10
|
Blackgrass
70
100
80
90
30
80
90
60
90
60
20
0
30
10
|
Corn
0
0
0
0
0
0
0
0
30
30
0
30
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
70
100
80
90
70
80
100
80
100
100
0
10
50
0
|
Galium
90
100
90
100
100
90
100
90
100
100
30
90
90
60
|
Kochia
80
100
80
70
80
90
100
90
100
90
70
30
60
10
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
80
100
90
100
90
90
100
90
100
100
30
60
70
0
|
Ragweed
70
100
90
90
80
90
100
90
100
100
0
50
60
10
|
Ryegrass, Italian
80
100
80
90
50
80
100
90
100
100
0
90
50
50
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
20
0
0
0
0
0
0
30
30
0
20
20
0
|
|
Compounds
|
500 g ai/ha
96
97
98
99
100
101
102
103
104
105
106
107
108
109
|
|
Postemergence
|
Barnyardgrass
20
90
90
90
30
30
90
90
100
90
90
100
90
90
|
Blackgrass
20
90
30
80
70
40
70
90
90
90
90
90
90
90
|
Corn
0
70
20
40
20
20
20
60
20
30
20
30
0
30
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
20
100
100
90
80
50
90
90
100
90
90
90
90
90
|
Galium
50
100
100
100
100
90
100
100
100
100
100
100
100
100
|
Kochia
70
100
60
70
100
30
40
90
100
90
90
90
100
90
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
70
100
100
90
90
70
90
100
90
90
90
90
100
90
|
Ragweed
50
100
100
100
90
80
100
100
100
100
90
90
100
100
|
Ryegrass, Italian
60
100
100
100
100
50
80
100
100
100
100
90
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
80
30
30
20
20
20
20
20
20
20
20
20
30
|
|
Compounds
|
500 g ai/ha
110
111
112
113
114
115
116
117
118
119
120
121
122
123
|
|
Postemergence
|
Barnyardgrass
10
90
20
90
90
90
90
40
0
0
10
50
30
70
|
Blackgrass
60
70
80
90
60
70
70
0
0
0
10
50
40
50
|
Corn
20
20
30
70
30
20
30
0
0
0
0
20
20
20
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
100
50
90
90
90
100
20
0
0
10
80
60
60
|
Galium
90
100
90
100
100
100
100
0
0
0
70
90
70
90
|
Kochia
70
90
30
100
60
90
60
10
0
0
30
80
70
70
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
30
100
90
90
100
20
0
0
50
90
70
70
|
Ragweed
100
100
80
100
80
100
100
0
0
0
10
90
60
90
|
Ryegrass, Italian
90
100
100
100
90
100
100
0
0
0
80
100
70
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
40
30
30
70
40
30
50
0
0
0
0
20
0
20
|
|
Compounds
|
500 g ai/ha
124
125
126
127
128
129
130
131
132
133
134
135
136
137
|
|
Postemergence
|
Barnyardgrass
30
90
60
50
80
100
90
20
30
90
60
0
100
100
|
Blackgrass
0
80
70
50
20
100
70
50
50
60
70
30
90
100
|
Corn
0
30
20
10
0
80
30
10
10
50
50
20
30
70
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
90
60
60
70
100
90
80
80
90
80
0
100
100
|
Galium
30
90
100
100
70
100
100
100
100
100
100
90
100
100
|
Kochia
0
100
90
80
0
90
100
80
80
100
100
0
100
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
100
100
100
90
100
100
90
90
100
100
20
100
100
|
Ragweed
0
100
90
80
30
100
100
90
100
100
100
60
100
100
|
Ryegrass, Italian
0
100
100
90
50
100
100
90
100
100
100
70
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
80
20
20
0
80
30
20
20
30
30
0
30
90
|
|
Compounds
|
500 g ai/ha
138
139
140
141
142
143
144
145
146
147
148
149
150
151
|
|
Postemergence
|
Barnyardgrass
100
100
90
50
20
60
100
90
30
40
30
20
30
90
|
Blackgrass
90
90
50
50
20
60
100
80
70
90
80
70
50
90
|
Corn
20
40
30
0
0
20
90
60
30
0
0
30
0
30
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
100
100
90
70
20
60
100
80
70
80
70
80
30
90
|
Galium
100
100
90
90
80
100
100
100
90
100
90
100
80
100
|
Kochia
100
100
70
30
20
90
100
100
100
100
90
100
70
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
90
30
50
90
100
100
90
90
90
100
80
100
|
Ragweed
100
100
100
40
20
70
100
100
100
90
90
90
30
90
|
Ryegrass, Italian
100
100
100
90
90
100
100
100
100
100
90
100
90
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
20
30
70
0
0
50
100
30
70
80
60
70
20
20
|
|
Compounds
|
500 g ai/ha
152
153
154
155
156
157
158
159
160
161
162
163
164
165
|
|
Postemergence
|
Barnyardgrass
40
90
90
80
90
80
50
80
20
80
50
0
20
30
|
Blackgrass
30
90
90
70
90
70
60
70
20
90
40
20
40
50
|
Corn
0
80
40
20
30
40
0
40
0
0
30
0
20
20
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
50
90
90
90
90
80
60
80
20
80
40
0
30
50
|
Galium
70
100
100
90
100
100
90
100
90
100
100
60
100
100
|
Kochia
40
90
50
80
100
100
100
100
60
90
90
20
90
90
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
60
100
90
100
100
100
100
80
90
90
90
20
80
80
|
Ragweed
90
90
80
100
100
100
100
100
80
90
100
0
100
90
|
Ryegrass, Italian
90
100
100
90
100
100
100
100
90
100
90
70
90
90
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
50
30
20
50
60
50
0
30
0
20
20
0
0
0
|
|
Compounds
|
500 g ai/ha
166
167
168
169
170
171
172
173
174
175
176
177
185
186
|
|
Postemergence
|
Barnyardgrass
20
20
40
20
10
90
70
0
10
0
10
0
30
100
|
Blackgrass
30
40
30
20
10
90
30
0
0
20
30
0
20
80
|
Corn
20
20
20
30
0
40
0
0
0
20
0
0
30
30
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
40
40
40
30
10
90
80
0
10
0
10
0
20
90
|
Galium
90
90
30
70
80
100
40
0
80
0
100
0
90
100
|
Kochia
70
70
20
100
70
100
20
0
0
0
70
0
100
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
80
80
40
70
80
100
30
0
60
0
90
0
90
100
|
Ragweed
70
70
0
80
80
100
0
0
20
0
100
0
50
100
|
Ryegrass, Italian
90
80
60
100
50
100
60
0
40
30
100
0
80
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
20
0
20
30
0
70
20
0
0
20
0
0
0
40
|
|
Compounds
|
500 g ai/ha
187
188
|
|
Postemergence
|
Barnyardgrass
80
20
|
Blackgrass
70
60
|
Corn
30
0
|
Crabgrass, Large
—
—
|
Foxtail, Giant
80
80
|
Galium
100
90
|
Kochia
100
20
|
Morningglory
—
—
|
Pigweed
90
80
|
Ragweed
100
50
|
Ryegrass, Italian
100
80
|
Velvetleaf
—
—
|
Wheat
30
0
|
|
Compounds
|
125 g ai/ha
2
8
9
12
14
15
16
17
18
19
20
21
22
23
|
|
Postemergence
|
Barnyardgrass
30
0
10
0
10
70
20
0
0
20
30
90
30
80
|
Blackgrass
—
—
—
20
20
0
10
10
0
0
30
90
50
70
|
Corn
0
0
0
0
0
0
0
0
0
0
20
50
0
40
|
Crabgrass, Large
50
0
10
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
80
0
10
10
10
70
20
0
0
20
30
100
60
90
|
Galium
—
—
—
60
80
70
90
50
40
30
90
100
90
100
|
Kochia
—
—
—
0
80
50
50
0
0
0
90
100
100
100
|
Morningglory
100
0
40
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
70
0
30
60
0
30
0
0
0
100
100
100
100
|
Ragweed
—
—
—
10
70
50
30
0
0
0
80
100
90
90
|
Ryegrass, Italian
—
—
—
60
60
50
50
50
10
0
100
100
80
100
|
Velvetleaf
100
60
0
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
20
0
0
0
0
0
0
0
0
0
20
10
0
50
|
|
Compounds
|
125 g ai/ha
24
25
26
27
28
29
30
31
33
34
35
36
37
38
|
|
Postemergence
|
Barnyardgrass
40
20
10
90
80
70
0
0
40
30
50
50
60
0
|
Blackgrass
30
60
30
90
90
70
20
0
10
80
70
60
60
50
|
Corn
0
0
0
0
0
10
0
0
0
0
0
20
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
90
10
90
90
80
0
0
40
30
90
80
80
0
|
Galium
80
100
70
100
100
90
70
20
90
90
100
100
100
80
|
Kochia
70
100
80
70
70
80
60
0
90
70
80
90
60
30
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
70
90
80
90
90
90
90
20
40
90
80
90
100
50
|
Ragweed
30
100
60
100
80
90
40
0
90
90
50
90
90
40
|
Ryegrass, Italian
70
100
60
100
90
90
70
0
50
100
80
70
90
0
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
30
0
0
0
0
40
10
0
0
20
20
20
40
10
|
|
Compounds
|
125 g ai/ha
39
40
41
42
43
44
45
46
47
48
49
50
51
52
|
|
Postemergence
|
Barnyardgrass
0
10
30
30
0
0
0
20
40
10
0
0
20
10
|
Blackgrass
30
60
70
80
30
0
0
20
60
0
10
0
30
20
|
Corn
0
0
20
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
60
70
90
0
0
0
50
80
50
0
0
50
40
|
Galium
90
90
80
100
50
30
0
70
90
90
50
60
90
100
|
Kochia
30
80
100
100
0
0
0
30
90
70
0
0
70
40
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
50
80
60
90
0
0
0
70
100
60
20
20
70
10
|
Ragweed
50
70
70
100
0
0
0
80
100
0
0
0
70
90
|
Ryegrass, Italian
90
90
100
100
40
0
0
30
70
50
30
20
60
70
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
|
Compounds
|
125 g ai/ha
53
54
55
56
57
58
59
61
62
63
64
65
66
67
|
|
Postemergence
|
Barnyardgrass
0
30
60
10
90
0
80
0
70
60
0
20
20
20
|
Blackgrass
0
20
70
30
30
20
90
0
70
70
0
20
60
70
|
Corn
0
20
0
0
20
0
20
0
10
0
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
60
70
20
80
0
90
0
80
70
0
20
70
80
|
Galium
60
100
100
90
100
70
100
0
100
100
0
90
90
80
|
Kochia
70
100
90
90
80
20
100
0
100
100
0
90
90
20
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
60
90
70
80
100
0
100
0
100
100
0
80
80
20
|
Ragweed
60
100
90
70
100
0
90
0
100
100
0
50
70
50
|
Ryegrass, Italian
40
60
100
90
70
60
100
0
100
100
0
90
90
70
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
20
0
10
0
0
50
0
0
0
0
0
0
0
|
|
Compounds
|
125 g ai/ha
68
69
70
71
72
73
74
75
76
77
78
79
80
81
|
|
Postemergence
|
Barnyardgrass
70
10
0
0
20
40
0
0
0
0
20
50
70
30
|
Blackgrass
0
30
10
30
70
90
20
50
0
0
30
70
80
90
|
Corn
0
0
0
0
20
20
0
0
0
0
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
10
30
0
30
90
0
50
0
0
20
70
80
90
|
Galium
0
80
70
70
90
100
10
90
70
20
80
90
90
100
|
Kochia
0
60
50
50
60
90
30
80
20
0
50
80
90
60
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
80
80
70
90
100
40
30
10
0
60
90
90
100
|
Ragweed
0
80
40
70
70
90
0
60
0
0
40
90
80
90
|
Ryegrass, Italian
0
80
60
30
100
100
0
90
40
20
80
80
80
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
0
20
40
0
0
0
0
0
0
0
0
|
|
Compounds
|
125 g ai/ha
82
83
84
85
86
87
88
89
90
91
92
93
94
95
|
|
Postemergence
|
Barnyardgrass
30
40
20
30
30
40
30
40
80
90
0
0
0
0
|
Blackgrass
70
90
70
90
10
80
90
30
70
30
0
0
0
0
|
Corn
0
0
0
0
0
0
0
0
20
20
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
50
90
50
90
50
70
90
70
80
90
0
0
30
0
|
Galium
90
100
90
90
90
90
100
90
100
100
10
70
80
20
|
Kochia
30
70
70
30
70
90
70
80
100
70
60
20
30
0
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
60
100
80
90
90
80
100
80
100
90
20
30
30
0
|
Ragweed
70
90
80
90
80
80
90
80
100
100
0
0
10
0
|
Ryegrass, Italian
70
90
70
90
0
80
100
80
100
90
0
40
30
10
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
0
0
0
0
0
20
20
0
0
0
0
|
|
Compounds
|
125 g ai/ha
96
97
98
99
100
101
102
103
104
105
106
107
108
109
|
|
Postemergence
|
Barnyardgrass
0
30
90
20
30
0
40
40
70
50
70
60
30
30
|
Blackgrass
0
90
30
60
40
20
20
70
90
80
90
80
80
80
|
Corn
0
10
20
20
0
0
20
20
0
0
0
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
80
90
40
80
30
70
90
80
70
90
70
60
70
|
Galium
20
100
100
100
90
70
100
100
100
100
100
100
100
100
|
Kochia
60
90
30
30
70
20
20
50
90
90
70
80
90
90
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
60
90
100
70
80
30
90
90
90
90
90
90
90
90
|
Ragweed
0
90
100
100
90
60
100
100
100
90
90
90
70
80
|
Ryegrass, Italian
20
100
90
100
90
30
20
100
100
100
90
60
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
20
30
20
0
0
20
0
20
0
0
30
0
20
|
|
Compounds
|
125 g ai/ha
110
111
112
113
114
115
116
117
118
119
120
121
122
123
|
|
Postemergence
|
Barnyardgrass
0
40
20
40
20
20
20
0
0
0
0
30
20
40
|
Blackgrass
20
30
40
90
20
20
30
0
0
0
0
20
30
30
|
Corn
0
0
0
20
0
0
0
0
0
0
0
20
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
70
20
40
70
20
70
0
0
0
0
60
40
50
|
Galium
70
90
70
100
90
80
70
0
0
0
40
70
60
80
|
Kochia
50
40
20
100
30
70
30
0
0
0
0
70
40
70
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
70
100
20
90
90
70
70
0
0
0
20
90
30
60
|
Ragweed
60
70
60
90
70
80
70
0
0
0
0
90
50
50
|
Ryegrass, Italian
70
90
80
100
90
100
90
0
0
0
20
90
50
90
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
20
20
30
20
20
20
0
0
0
0
0
0
0
|
|
Compounds
|
125 g ai/ha
124
125
126
127
128
129
130
131
132
133
134
135
136
137
|
|
Postemergence
|
Barnyardgrass
20
90
30
10
50
90
60
0
0
20
20
0
20
70
|
Blackgrass
0
70
60
20
0
60
60
30
30
60
60
0
60
90
|
Corn
0
20
0
0
0
10
0
0
0
10
20
0
30
30
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
90
20
10
50
90
70
50
60
20
20
0
90
100
|
Galium
0
90
100
90
40
100
100
70
80
100
100
60
100
100
|
Kochia
0
100
90
70
0
70
100
60
50
90
100
0
100
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
100
90
90
70
90
100
60
60
90
90
0
90
100
|
Ragweed
0
90
90
60
10
100
70
100
100
100
100
30
100
100
|
Ryegrass, Italian
0
100
90
80
20
100
100
90
100
100
100
40
90
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
50
0
0
0
20
0
0
0
20
30
0
0
50
|
|
Compounds
|
125 g ai/ha
138
139
140
141
142
143
144
145
146
147
148
149
150
151
|
|
Postemergence
|
Barnyardgrass
20
20
50
20
10
20
100
20
0
10
10
20
0
70
|
Blackgrass
80
60
30
0
10
40
90
40
20
60
60
30
0
90
|
Corn
0
30
20
0
0
0
60
20
0
0
0
20
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
90
70
40
20
10
20
100
20
10
30
30
40
0
80
|
Galium
100
100
70
70
70
90
100
100
80
90
90
90
30
100
|
Kochia
100
100
30
10
0
70
100
100
70
80
80
80
40
70
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
60
70
0
20
90
100
100
90
90
90
90
40
90
|
Ragweed
100
100
90
60
0
70
100
100
90
90
90
90
0
90
|
Ryegrass, Italian
90
100
70
70
80
80
100
100
70
90
90
70
40
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
30
20
0
0
0
90
20
0
20
20
20
0
0
|
|
Compounds
|
125 g ai/ha
152
153
154
155
156
157
158
159
160
161
162
163
164
165
|
|
Postemergence
|
Barnyardgrass
20
90
90
30
70
50
10
40
10
20
20
0
20
20
|
Blackgrass
20
90
70
60
60
60
50
70
10
80
20
0
20
20
|
Corn
0
0
0
0
0
0
0
20
0
0
20
0
0
0
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
30
90
90
80
90
60
30
50
10
80
20
0
20
20
|
Galium
60
100
100
90
100
100
80
100
70
80
90
30
80
100
|
Kochia
30
40
20
70
80
100
90
100
30
60
70
0
60
60
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
50
80
90
90
90
90
80
60
80
50
80
0
80
80
|
Ragweed
70
80
80
100
90
100
90
100
70
80
80
0
70
90
|
Ryegrass, Italian
30
100
90
90
90
100
90
100
30
100
60
20
70
80
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
30
0
0
30
30
0
0
0
0
0
0
0
0
0
|
|
Compounds
|
125 g ai/ha
166
167
168
169
170
171
172
173
174
175
176
177
185
186
|
|
Postemergence
|
Barnyardgrass
10
20
0
0
0
40
40
0
0
0
0
0
10
70
|
Blackgrass
10
20
20
10
0
80
20
0
0
0
30
0
0
40
|
Corn
20
0
0
0
0
20
0
0
0
0
0
0
0
20
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
20
30
0
0
40
40
0
0
0
0
0
0
70
|
Galium
70
70
0
30
40
90
20
0
30
0
90
0
70
100
|
Kochia
50
50
20
40
0
100
0
0
0
0
30
0
70
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
40
70
0
20
70
90
0
0
40
0
30
0
50
100
|
Ragweed
30
60
0
0
40
100
0
0
20
0
40
0
10
100
|
Ryegrass, Italian
40
70
60
70
0
100
20
0
10
20
30
0
70
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
0
0
30
20
0
0
0
0
0
0
0
|
|
Compounds
|
125 g ai/ha
187
188
|
|
Postemergence
|
Barnyardgrass
30
10
|
Blackgrass
40
10
|
Corn
0
0
|
Crabgrass, Large
—
—
|
Foxtail, Giant
50
20
|
Galium
90
70
|
Kochia
90
10
|
Morningglory
—
—
|
Pigweed
70
50
|
Ragweed
100
20
|
Ryegrass, Italian
100
20
|
Velvetleaf
—
—
|
Wheat
0
0
|
|
Compounds
|
1000 g ai/ha
181
182
183
184
|
|
Preemergence
|
Barnyardgrass
0
0
40
10
|
Corn
—
—
—
—
|
Crabgrass, Large
—
—
—
—
|
Foxtail, Giant
0
0
60
30
|
Kochia
10
0
70
20
|
Morningglory
—
—
—
—
|
Pigweed
30
0
90
90
|
Ragweed
10
0
80
70
|
Ryegrass, Italian
60
0
90
90
|
Velvetleaf
—
—
—
—
|
Wheat
—
—
—
—
|
|
Compounds
|
1000 g ai/ha
1
3
4
5
6
7
10
11
13
32
60
178
179
180
|
|
Preemergence
|
Barnyardgrass
90
80
100
90
100
100
100
90
60
100
80
0
0
0
|
Corn
0
0
10
0
30
30
10
20
—
—
—
—
—
—
|
Crabgrass, Large
90
80
80
90
—
90
90
80
—
—
—
—
—
—
|
Foxtail, Giant
100
60
80
80
50
90
100
90
50
100
90
0
30
10
|
Kochia
—
—
—
—
—
—
—
—
20
100
80
0
30
0
|
Morningglory
90
80
60
0
10
80
90
90
—
—
—
—
—
—
|
Pigweed
100
0
70
0
—
100
100
100
0
100
100
0
80
40
|
Ragweed
—
—
—
—
—
—
—
—
0
90
100
0
50
40
|
Ryegrass, Italian
—
—
—
—
—
—
—
—
60
100
100
60
30
50
|
Velvetleaf
100
70
40
0
20
80
90
80
—
—
—
—
—
—
|
Wheat
0
0
0
0
0
0
0
50
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
2
8
9
12
14
15
16
17
18
19
20
21
22
23
|
|
Preemergence
|
Barnyardgrass
80
0
100
80
40
90
70
0
0
90
90
100
70
90
|
Corn
10
0
0
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
100
60
90
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
100
60
100
90
10
70
30
0
0
0
90
100
90
90
|
Kochia
—
—
—
10
50
0
30
0
0
0
100
90
100
100
|
Morningglory
100
0
0
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
0
60
90
0
70
0
0
0
100
100
100
100
|
Ragweed
—
—
—
30
30
30
0
10
0
20
90
100
90
90
|
Ryegrass, Italian
—
—
—
50
—
100
80
40
20
0
100
100
100
90
|
Velvetleaf
90
30
0
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
24
25
26
27
28
29
30
31
33
34
35
36
37
38
|
|
Preemergence
|
Barnyardgrass
60
90
10
100
90
90
10
0
90
80
90
30
90
10
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
80
90
50
100
100
90
60
0
70
90
100
90
90
40
|
Kochia
50
100
30
90
90
100
40
0
80
60
70
80
80
40
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
100
100
100
100
90
0
20
100
90
100
100
80
|
Ragweed
0
100
40
100
90
90
70
30
100
90
80
90
90
70
|
Ryegrass, Italian
80
100
70
100
100
90
50
0
60
100
90
70
100
70
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
39
40
41
42
43
44
45
46
47
48
49
50
51
52
|
|
Preemergence
|
Barnyardgrass
10
50
90
100
10
0
0
60
90
0
0
0
90
70
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
60
70
90
100
50
0
0
90
80
10
10
0
90
60
|
Kochia
0
80
100
100
20
0
0
30
90
10
0
0
30
80
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
80
100
100
100
10
0
0
100
100
30
40
0
100
60
|
Ragweed
70
80
90
100
10
10
0
80
90
60
10
0
80
80
|
Ryegrass, Italian
50
100
100
100
70
0
0
50
90
60
30
10
90
80
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
53
54
55
56
57
58
59
61
62
63
64
65
66
67
|
|
Preemergence
|
Barnyardgrass
20
90
90
50
100
20
100
0
90
90
0
90
70
90
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
50
100
100
70
100
0
100
0
90
70
0
90
90
100
|
Kochia
70
100
100
90
100
80
90
0
90
100
0
90
70
20
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
70
100
100
100
100
20
100
0
100
100
0
100
100
100
|
Ragweed
50
100
100
90
100
80
100
0
90
90
0
80
90
80
|
Ryegrass, Italian
50
100
100
100
100
100
100
0
100
100
0
100
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
68
69
70
71
72
73
74
75
76
77
78
79
80
81
|
|
Preemergence
|
Barnyardgrass
40
60
30
20
100
100
0
80
30
10
70
70
90
100
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
50
50
30
50
100
100
0
90
20
10
60
90
90
100
|
Kochia
0
90
40
20
100
100
0
90
0
0
100
90
90
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
100
100
100
100
100
50
100
50
0
100
100
100
100
|
Ragweed
20
80
80
20
90
90
0
90
50
0
90
80
90
100
|
Ryegrass, Italian
0
100
90
70
100
100
0
100
70
40
100
100
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
82
83
84
85
86
87
88
89
90
91
92
93
94
95
|
|
Preemergence
|
Barnyardgrass
70
100
60
100
40
80
100
60
100
100
0
0
40
0
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
90
100
90
100
70
100
100
80
100
100
0
0
50
0
|
Kochia
90
100
80
30
40
90
100
90
100
100
20
30
70
10
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
90
100
100
100
100
100
100
100
0
90
90
20
|
Ragweed
80
100
90
90
90
80
90
90
100
90
0
20
80
20
|
Ryegrass, Italian
90
100
90
100
40
100
100
90
100
90
0
40
50
60
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
96
97
98
99
100
101
102
103
104
105
106
107
108
109
|
|
Preemergence
|
Barnyardgrass
0
100
100
90
20
30
60
90
100
100
100
100
100
100
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
100
100
80
90
60
90
100
100
100
100
100
100
100
|
Kochia
30
100
40
70
70
40
30
40
100
100
90
90
100
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
100
100
100
90
100
100
100
100
100
100
100
100
|
Ragweed
0
100
90
80
80
40
90
100
100
100
100
100
100
100
|
Ryegrass, Italian
40
100
90
100
100
100
60
100
100
100
100
100
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
110
111
112
113
114
115
116
117
118
119
120
121
122
123
|
|
Preemergence
|
Barnyardgrass
20
100
20
100
80
50
100
50
30
0
30
50
30
80
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
40
100
60
100
90
50
100
30
20
0
20
80
70
70
|
Kochia
100
100
80
100
100
90
100
0
0
0
0
30
70
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
100
100
100
100
90
30
10
0
70
100
100
100
|
Ragweed
40
90
80
90
90
90
90
0
0
0
30
80
80
70
|
Ryegrass, Italian
80
100
100
100
90
100
100
0
0
0
30
90
90
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
124
125
126
127
128
129
130
131
132
133
134
135
136
137
|
|
Preemergence
|
Barnyardgrass
0
90
80
40
90
100
100
40
70
50
90
0
80
100
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
100
70
60
90
100
90
90
90
70
90
30
100
100
|
Kochia
20
90
90
90
0
90
100
20
90
100
100
0
90
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
100
100
100
100
100
100
100
100
100
100
70
100
100
|
Ragweed
0
90
80
70
70
90
90
60
90
100
90
60
90
100
|
Ryegrass, Italian
30
100
100
90
30
100
100
90
90
100
100
60
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
138
139
140
141
142
143
144
145
146
147
148
149
150
151
|
|
Preemergence
|
Barnyardgrass
100
100
70
90
70
80
100
90
50
60
60
70
10
100
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
100
100
80
70
60
70
100
90
50
40
50
90
30
100
|
Kochia
100
100
30
60
0
70
100
100
70
80
90
90
20
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
100
60
50
100
100
100
100
100
100
100
100
100
|
Ragweed
100
100
90
60
40
90
100
100
80
90
80
90
30
90
|
Ryegrass, Italian
100
100
90
80
80
100
100
100
80
100
100
90
70
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
152
153
154
155
156
157
158
159
160
161
162
163
164
165
|
|
Preemergence
|
Barnyardgrass
40
100
100
80
100
90
60
80
10
60
20
0
20
30
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
90
100
100
90
90
80
40
80
30
70
40
0
40
40
|
Kochia
70
90
20
90
100
100
40
100
20
30
90
0
100
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
100
100
100
100
100
100
100
100
90
70
100
90
|
Ragweed
100
90
90
90
90
90
80
80
80
90
90
0
90
90
|
Ryegrass, Italian
100
100
100
90
100
100
80
100
80
100
100
50
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
166
167
168
169
170
171
172
173
174
175
176
177
185
186
|
|
Preemergence
|
Barnyardgrass
10
20
20
30
0
100
50
0
0
0
10
0
50
80
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
30
20
40
30
0
100
90
0
10
0
10
0
30
70
|
Kochia
90
100
0
90
0
100
0
0
0
20
20
0
10
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
0
100
100
100
0
0
20
60
90
0
60
100
|
Ragweed
90
80
0
20
20
90
0
0
0
20
70
0
40
80
|
Ryegrass, Italian
90
100
40
100
40
100
20
0
0
20
90
0
40
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
500 g ai/ha
187
188
|
|
Preemergence
|
Barnyardgrass
90
30
|
Corn
—
—
|
Crabgrass, Large
—
—
|
Foxtail, Giant
70
90
|
Kochia
100
20
|
Morningglory
—
—
|
Pigweed
100
90
|
Ragweed
80
30
|
Ryegrass, Italian
100
80
|
Velvetleaf
—
—
|
Wheat
—
—
|
Barnyardgrass
70
10
|
Corn
—
—
|
Crabgrass, Large
—
—
|
Foxtail, Giant
20
10
|
Kochia
60
20
|
Morningglory
—
—
|
Pigweed
90
60
|
Ragweed
70
10
|
Ryegrass, Italian
100
20
|
Velvetleaf
—
—
|
Wheat
—
—
|
|
Compounds
|
125 g ai/ha
2
8
9
12
14
15
16
17
18
19
20
21
22
23
|
|
Preemergence
|
Barnyardgrass
50
0
50
20
0
20
10
0
0
30
30
90
10
90
|
Corn
0
0
0
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
90
10
20
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
100
40
70
20
0
10
0
0
0
0
40
90
70
90
|
Kochia
—
—
—
0
10
0
0
0
0
0
80
30
70
80
|
Morningglory
80
0
0
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
70
0
10
70
0
0
0
0
0
80
100
100
100
|
Ragweed
—
—
—
0
0
0
0
0
0
0
30
100
90
90
|
Ryegrass, Italian
—
—
—
20
30
50
30
10
0
0
90
100
100
80
|
Velvetleaf
80
0
0
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
0
0
0
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
24
25
26
27
28
29
30
31
33
34
35
36
37
38
|
|
Preemergence
|
Barnyardgrass
30
30
0
90
90
70
0
0
20
20
60
0
30
0
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
60
90
30
90
100
80
0
0
50
40
90
80
70
0
|
Kochia
30
90
30
40
50
60
0
0
30
30
40
10
30
40
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
70
100
80
100
100
100
80
0
20
90
60
100
100
0
|
Ragweed
0
90
20
90
90
90
0
0
80
80
70
80
80
0
|
Ryegrass, Italian
80
100
30
100
100
80
30
0
20
100
90
70
90
40
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
39
40
41
42
43
44
45
46
47
48
49
50
51
52
|
|
Preemergence
|
Barnyardgrass
0
10
20
80
0
0
0
20
70
0
0
0
30
50
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
40
70
80
0
0
0
50
70
0
0
0
50
40
|
Kochia
0
50
90
80
50
0
0
30
10
0
0
0
0
0
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
80
90
100
100
0
0
0
30
70
30
0
0
70
10
|
Ragweed
10
30
80
90
0
0
0
50
80
10
0
0
30
20
|
Ryegrass, Italian
40
60
100
100
10
0
0
30
60
20
0
0
50
80
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
53
54
55
56
57
58
59
61
62
63
64
65
66
67
|
|
Preemergence
|
Barnyardgrass
0
40
90
10
100
0
80
0
50
80
0
60
20
30
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
50
60
80
30
100
0
90
0
50
40
0
60
60
80
|
Kochia
50
50
70
40
100
20
90
0
90
100
0
60
60
20
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
50
100
70
60
100
0
100
0
100
100
0
100
100
90
|
Ragweed
0
90
90
80
90
70
90
0
70
80
0
70
80
80
|
Ryegrass, Italian
10
30
100
100
90
70
90
0
100
100
0
90
90
90
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
68
69
70
71
72
73
74
75
76
77
78
79
80
81
|
|
Preemergence
|
Barnyardgrass
10
10
0
0
10
40
0
40
0
0
0
50
70
90
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
10
0
0
70
90
0
50
0
0
20
90
80
100
|
Kochia
0
20
10
0
50
50
0
80
0
0
20
70
90
30
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
90
60
30
100
100
30
100
20
0
60
100
90
100
|
Ragweed
0
80
70
0
90
90
0
70
0
0
60
80
80
90
|
Ryegrass, Italian
0
70
60
0
100
100
0
100
50
10
100
80
90
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
82
83
84
85
86
87
88
89
90
91
92
93
94
95
|
|
Preemergence
|
Barnyardgrass
40
70
20
70
0
50
90
50
60
90
0
0
0
0
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
70
100
70
100
20
80
100
50
50
80
0
0
20
0
|
Kochia
70
30
70
0
0
80
60
70
70
60
0
0
30
0
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
90
100
80
100
100
100
100
100
0
20
70
0
|
Ragweed
80
90
80
90
40
70
90
80
90
80
0
0
50
0
|
Ryegrass, Italian
80
100
70
100
0
90
100
80
100
90
0
20
20
10
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
96
97
98
99
100
101
102
103
104
105
106
107
108
109
|
|
Preemergence
|
Barnyardgrass
0
20
40
60
20
0
40
40
80
20
80
70
20
20
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
60
90
50
70
30
70
80
70
90
100
70
90
90
|
Kochia
0
80
20
20
30
0
10
20
100
100
20
20
90
100
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
30
100
100
100
100
90
80
100
100
100
100
100
100
100
|
Ragweed
0
90
60
80
40
40
90
90
90
100
90
90
90
100
|
Ryegrass, Italian
0
100
20
100
90
60
60
90
100
100
100
80
100
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
110
111
112
113
114
115
116
117
118
119
120
121
122
123
|
|
Preemergence
|
Barnyardgrass
0
70
10
70
30
10
70
0
0
0
0
20
0
0
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
80
50
70
40
30
80
0
0
0
0
80
30
70
|
Kochia
0
60
20
90
30
30
30
0
0
0
0
0
30
50
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
90
90
100
100
70
90
0
0
0
0
100
100
100
|
Ragweed
30
80
40
70
80
40
90
0
0
0
0
60
—
60
|
Ryegrass, Italian
20
90
90
100
80
100
80
0
0
0
30
80
70
90
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
124
125
126
127
128
129
130
131
132
133
134
135
136
137
|
|
Preemergence
|
Barnyardgrass
0
70
40
10
50
90
30
0
0
20
20
0
10
90
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
0
90
10
50
80
90
30
80
70
40
50
20
80
90
|
Kochia
0
60
50
0
0
70
60
0
60
40
70
0
60
30
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
0
100
100
70
90
100
90
80
90
80
100
30
100
100
|
Ragweed
0
80
70
30
70
90
60
40
80
90
80
30
80
90
|
Ryegrass, Italian
0
100
90
60
10
100
100
90
90
100
100
20
90
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
138
139
140
141
142
143
144
145
146
147
148
149
150
151
|
|
Preemergence
|
Barnyardgrass
10
20
50
50
10
20
90
20
0
30
10
0
0
90
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
90
60
50
30
10
20
100
30
0
10
20
30
0
90
|
Kochia
40
100
0
0
0
10
100
90
20
50
30
40
0
30
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
100
100
50
40
60
80
100
90
100
90
100
100
80
100
|
Ragweed
90
90
70
60
20
10
90
80
80
80
80
80
0
90
|
Ryegrass, Italian
100
100
70
70
50
70
100
100
80
70
80
90
20
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
152
153
154
155
156
157
158
159
160
161
162
163
164
165
|
|
Preemergence
|
Barnyardgrass
40
100
70
50
70
70
10
50
10
10
10
0
10
10
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
40
100
90
60
80
50
10
60
10
10
10
0
10
10
|
Kochia
30
80
0
20
50
100
30
100
20
0
60
0
60
60
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
90
100
100
100
100
100
10
100
50
100
80
30
80
100
|
Ragweed
80
80
80
90
90
60
50
80
30
90
50
0
50
50
|
Ryegrass, Italian
90
100
90
70
90
100
80
100
20
100
40
10
60
40
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Compounds
|
125 g ai/ha
166
167
168
169
170
171
172
173
174
175
176
177
185
186
|
|
Preemergence
|
Barnyardgrass
10
10
0
0
0
70
20
0
0
0
0
0
0
40
|
Corn
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Crabgrass, Large
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Foxtail, Giant
10
10
0
0
0
50
60
0
0
0
0
0
0
50
|
Kochia
30
60
0
20
0
100
0
0
0
0
0
0
0
80
|
Morningglory
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Pigweed
80
100
0
50
30
90
0
0
0
0
0
0
20
100
|
Ragweed
70
70
0
0
0
70
0
0
0
0
20
0
0
70
|
Ryegrass, Italian
40
80
0
80
0
100
0
0
0
20
0
0
0
100
|
Velvetleaf
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Wheat
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
|
Test B
Plant species in the flooded paddy test selected from rice (Oryza sativa), sedge, umbrella (small-flower umbrella sedge, Cyperus difformis), ducksalad (Heteranthera limosa), and barnyardgrass (Echinochloa crus-galli) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 to 15 d, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
TABLE B
|
|
250 g ai/ha
Compounds
|
Flood
1
2
3
4
5
7
8
9
10
11
12
13
14
15
|
|
Barnyardgrass
0
30
0
0
0
20
30
0
0
0
0
0
0
0
|
Ducksalad
20
80
20
0
45
60
20
0
30
0
30
0
0
20
|
Rice
0
35
0
0
0
0
0
0
0
0
0
0
0
0
|
Sedge, Umbrella
0
85
0
0
75
60
70
0
0
0
0
0
0
0
|
|
250 g ai/ha
Compounds
|
Flood
16
17
18
19
20
21
22
23
24
25
26
27
28
29
|
|
Barnyardgrass
0
0
0
0
0
70
0
0
0
30
0
30
60
0
|
Ducksalad
30
0
30
0
50
0
0
75
0
20
0
30
80
55
|
Rice
0
0
0
0
0
55
0
0
0
0
0
40
40
0
|
Sedge, Umbrella
0
0
0
0
50
65
0
95
0
60
0
80
95
60
|
|
250 g ai/ha
Compounds
|
Flood
31
32
33
34
35
36
41
42
43
44
45
46
47
48
|
|
Barnyardgrass
0
0
0
0
0
0
30
0
0
0
0
0
0
0
|
Ducksalad
0
0
0
0
75
30
40
0
0
0
0
0
0
0
|
Rice
0
0
0
0
0
20
0
0
0
0
0
0
0
0
|
Sedge, Umbrella
0
0
0
0
65
70
40
0
0
0
0
0
0
0
|
|
250 g ai/ha
Compounds
|
Flood
49
50
51
53
54
55
56
57
58
59
60
62
63
65
|
|
Barnyardgrass
0
0
0
0
0
0
0
0
0
0
35
20
0
0
|
Ducksalad
0
0
0
0
0
0
0
0
0
0
20
20
30
0
|
Rice
0
0
0
0
0
0
0
0
0
0
35
0
0
0
|
Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
30
75
65
0
|
|
250 g ai/ha
Compounds
|
Flood
66
67
68
72
73
74
75
79
81
82
83
84
85
86
|
|
Barnyardgrass
0
0
0
0
0
0
0
0
60
0
60
0
50
0
|
Ducksalad
0
0
0
0
0
0
0
0
70
0
70
0
50
20
|
Rice
0
0
0
0
0
0
15
0
60
0
30
0
50
15
|
Sedge, Umbrella
0
0
30
0
0
0
0
0
80
0
90
0
80
60
|
|
250 g ai/ha
Compounds
|
Flood
87
88
89
91
92
93
94
98
99
100
101
102
103
110
|
|
Barnyardgrass
0
50
0
0
0
0
0
45
0
0
0
0
30
0
|
Ducksalad
0
50
65
0
0
0
0
75
0
0
0
0
0
0
|
Rice
0
40
0
0
0
0
0
30
0
0
0
0
0
0
|
Sedge, Umbrella
0
80
40
40
40
50
0
60
0
0
0
50
50
0
|
|
250 g ai/ha
Compounds
|
Flood
111
112
113
114
115
116
117
118
119
121
122
123
124
125
|
|
Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
20
0
0
|
Ducksalad
75
0
0
50
0
50
0
0
0
0
0
30
0
80
|
Rice
0
0
0
0
0
0
0
0
0
0
0
15
0
0
|
Sedge, Umbrella
75
0
0
70
0
70
0
0
0
0
0
70
0
75
|
|
250 g ai/ha
Compounds
|
Flood
126
127
128
130
131
132
133
134
135
136
137
138
139
143
|
|
Barnyardgrass
0
0
0
0
0
0
0
0
0
0
25
0
0
0
|
Ducksalad
30
0
30
0
0
0
0
0
0
0
40
0
0
0
|
Rice
0
0
0
0
0
0
20
0
0
0
0
0
0
0
|
Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
65
0
0
0
|
|
250 g ai/ha
Compounds
|
Flood
144
145
146
147
148
149
150
151
152
153
154
155
156
157
|
|
Barnyardgrass
30
0
0
0
0
0
0
45
0
0
50
0
0
20
|
Ducksalad
40
0
0
0
0
0
0
40
0
0
60
50
60
0
|
Rice
30
0
0
0
0
0
0
20
0
0
50
20
0
0
|
Sedge, Umbrella
0
0
0
0
0
0
0
70
0
0
80
65
75
75
|
|
250 g ai/ha
Compounds
|
Flood
158
159
160
162
163
164
165
166
167
168
169
170
171
172
|
|
Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Ducksalad
0
0
0
0
0
0
0
0
0
40
0
0
0
0
|
Rice
20
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Sedge, Umbrella
65
50
0
0
0
0
0
0
0
0
0
60
60
0
|
|
250 g ai/ha
Compounds
|
Flood
173
174
175
176
177
179
180
181
183
184
185
186
187
188
|
|
Barnyardgrass
0
0
0
0
0
0
0
0
0
0
0
15
0
0
|
Ducksalad
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Rice
0
0
0
0
0
0
0
0
0
0
0
0
20
0
|
Sedge, Umbrella
0
0
0
0
0
0
0
0
0
0
0
40
0
0
|
|
Test C
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.
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 C
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
1
2
10
11
14
16
20
21
22
23
25
26
27
28
|
|
Barnyard-
5
20
98
15
60
90
45
90
15
85
25
35
50
40
|
grass
|
Blackgrass
75
80
15
75
20
40
45
95
20
85
80
75
90
90
|
Chickweed
100
98
90
90
90
90
100
100
98
100
100
100
100
95
|
Corn
40
10
5
0
5
0
10
20
5
25
10
5
15
15
|
Crabgrass,
35
10
75
10
35
30
30
55
5
45
20
25
45
45
|
Large
|
Foxtail,
90
95
90
30
50
80
80
95
35
90
85
65
95
95
|
Giant
|
Galium
95
98
85
90
90
80
100
100
95
100
95
95
100
100
|
Johnsongrass
15
5
25
5
5
5
10
35
5
40
10
5
10
30
|
Kochia
100
75
95
100
90
25
100
100
95
100
100
100
90
100
|
Lambs-
100
100
98
90
90
20
100
98
90
98
98
98
98
100
|
quarters
|
Morning-
100
100
100
98
100
40
100
100
100
100
100
100
100
100
|
glory
|
Nutsedge,
—
98
—
45
—
—
95
90
65
85
90
25
95
90
|
Yellow
|
Oat, Wild
100
85
25
70
45
40
40
100
80
100
95
90
100
100
|
Oilseed
40
75
0
0
0
0
25
100
75
10
5
5
70
70
|
Rape
|
Pigweed
100
98
95
95
90
50
100
98
98
98
98
95
90
90
|
Ragweed
95
98
98
95
98
30
100
95
100
98
95
90
90
90
|
Ryegrass,
98
90
55
90
85
70
90
95
90
95
95
90
90
95
|
Italian
|
Soybean
5
5
0
0
5
0
0
20
0
15
10
10
0
5
|
Velvetleaf
100
100
70
80
40
35
100
90
80
90
98
70
95
90
|
Waterhemp
100
100
90
95
40
5
90
80
90
98
98
95
90
85
|
Wheat
15
5
0
5
5
0
0
35
0
30
5
5
5
5
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
29
32
33
34
36
37
41
42
47
51
52
54
56
57
|
|
Barnyard-
40
90
80
35
40
90
60
40
90
20
10
20
10
98
|
grass
|
Blackgrass
75
80
10
60
20
85
60
70
30
10
30
40
40
25
|
Chickweed
100
100
95
95
95
95
100
100
98
90
100
100
70
100
|
Corn
20
40
20
5
5
30
20
5
5
0
0
10
0
10
|
Crabgrass,
40
70
25
25
35
35
35
20
35
10
10
55
20
35
|
Large
|
Foxtail,
80
90
70
35
80
85
65
80
85
35
35
90
50
95
|
Giant
|
Galium
100
100
95
95
95
95
100
95
90
95
100
98
90
100
|
Johnsongrass
25
35
40
5
5
35
35
25
25
0
15
10
10
10
|
Kochia
85
95
50
85
90
80
100
100
98
75
70
95
100
95
|
Lambs-
90
100
100
100
100
100
98
98
85
—
98
100
85
90
|
quarters
|
Morning-
100
100
98
98
100
98
98
100
100
75
100
100
50
100
|
glory
|
Nutsedge,
75
85
65
85
65
60
80
95
90
90
95
70
60
90
|
Yellow
|
Oat, Wild
95
100
45
90
85
90
95
95
50
10
0
85
40
60
|
Oilseed
0
90
50
20
90
50
0
0
10
5
0
70
0
5
|
Rape
|
Pigweed
98
95
80
98
100
95
95
98
98
85
55
100
90
100
|
Ragweed
95
98
98
95
95
98
100
100
100
25
98
98
60
95
|
Ryegrass,
95
95
75
90
80
90
90
95
30
70
60
80
90
60
|
Italian
|
Soybean
25
35
0
5
15
25
15
15
15
0
0
10
0
5
|
Velvetleaf
90
85
85
90
95
90
90
95
95
70
100
100
70
100
|
Waterhemp
98
98
75
98
98
98
85
95
100
—
55
95
90
100
|
Wheat
10
40
0
0
5
35
5
0
0
0
0
0
5
5
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
59
60
65
66
67
69
72
73
75
78
79
80
81
82
|
|
Barnyard-
70
65
50
35
45
55
65
60
20
25
40
35
60
30
|
grass
|
Blackgrass
90
90
40
60
80
70
90
90
35
30
50
50
90
40
|
Chickweed
98
98
90
95
95
100
90
95
95
80
90
98
95
98
|
Corn
50
35
5
25
20
10
25
60
10
0
35
5
0
5
|
Crabgrass,
60
65
25
45
40
30
60
75
20
10
35
35
55
30
|
Large
|
Foxtail,
90
90
60
80
85
25
85
85
10
25
90
90
90
80
|
Giant
|
Galium
98
100
90
95
90
98
95
95
90
95
95
95
95
95
|
Johnsongrass
35
45
5
15
10
15
45
50
10
5
10
15
70
10
|
Kochia
90
100
100
98
80
98
90
100
95
90
90
90
80
90
|
Lambs-
98
100
100
100
100
98
95
98
100
100
100
100
100
100
|
quarters
|
Morning-
100
100
95
100
100
98
100
95
75
65
98
98
98
100
|
glory
|
Nutsedge,
95
95
65
85
85
65
85
90
70
60
85
95
90
85
|
Yellow
|
Oat, Wild
98
95
70
90
100
85
95
95
35
60
90
95
95
90
|
Oilseed
55
80
5
0
75
0
85
85
80
5
80
80
45
75
|
Rape
|
Pigweed
98
98
100
100
85
95
98
98
98
80
98
95
90
90
|
Ragweed
98
100
90
100
95
98
90
90
100
75
98
98
85
95
|
Ryegrass,
95
95
85
85
85
95
90
90
85
90
85
85
90
85
|
Italian
|
Soybean
25
50
10
5
10
35
30
45
10
20
5
20
0
10
|
Velvetleaf
95
95
75
95
98
98
95
90
85
60
90
90
90
90
|
Waterhemp
100
98
85
100
70
100
85
100
100
90
95
95
80
98
|
Wheat
15
15
0
0
0
0
35
40
0
10
0
15
0
5
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
83
84
85
87
88
89
90
91
97
98
99
100
102
104
|
|
Barnyard-
45
40
50
45
60
40
70
65
35
98
35
40
40
55
|
grass
|
Blackgrass
90
60
90
65
90
5
40
30
0
70
65
25
10
55
|
Chickweed
100
100
100
98
100
100
98
100
60
100
90
95
98
100
|
Corn
10
10
5
5
15
5
25
20
5
15
10
10
10
30
|
Crabgrass,
55
30
45
35
55
10
75
40
25
70
50
15
15
55
|
Large
|
Foxtail,
90
85
90
85
90
30
75
80
5
100
50
90
75
85
|
Giant
|
Galium
100
95
100
98
100
95
95
98
90
98
98
95
95
98
|
Johnsongrass
10
20
25
10
5
5
20
10
5
10
5
10
10
5
|
Kochia
80
95
70
95
85
100
100
98
85
80
95
95
50
100
|
Lambs-
98
98
100
100
98
100
100
100
60
100
98
98
100
100
|
quarters
|
Morning-
98
100
100
100
98
98
100
100
30
100
100
100
100
100
|
glory
|
Nutsedge,
90
90
90
85
85
75
85
85
5
60
85
50
75
75
|
Yellow
|
Oat, Wild
95
90
90
90
100
40
95
90
10
100
95
95
25
90
|
Oilseed
70
50
15
20
80
0
5
90
35
25
55
90
30
98
|
Rape
|
Pigweed
90
100
90
98
90
95
100
100
75
100
95
100
100
100
|
Ragweed
85
95
90
100
90
98
100
100
35
100
100
98
100
100
|
Ryegrass,
95
85
95
85
90
80
90
95
55
85
95
95
30
90
|
Italian
|
Soybean
10
5
15
5
25
0
70
20
5
25
5
5
10
10
|
Velvetleaf
90
98
95
90
90
80
98
100
30
100
100
65
100
90
|
Waterhemp
80
90
85
90
90
50
100
80
10
100
98
98
85
95
|
Wheat
0
0
0
0
0
0
30
5
0
30
10
5
5
10
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
105
106
107
108
109
111
113
114
115
121
123
125
126
127
|
|
Barnyard-
20
40
90
60
65
40
45
40
45
30
70
70
50
25
|
grass
|
Blackgrass
60
75
30
55
80
35
60
15
35
50
45
80
40
35
|
Chickweed
100
98
98
98
100
98
100
98
90
98
98
95
100
95
|
Corn
30
10
15
30
50
10
15
0
15
5
20
5
25
10
|
Crabgrass,
30
30
65
40
60
25
70
25
25
40
75
60
30
25
|
Large
|
Foxtail,
85
95
75
85
85
85
70
85
35
85
80
98
25
40
|
Giant
|
Galium
100
100
98
95
100
95
95
95
95
95
95
95
98
90
|
Johnsongrass
0
10
20
5
5
10
20
15
20
5
25
20
25
15
|
Kochia
100
80
90
100
100
95
100
95
90
95
98
90
95
90
|
Lambs-
100
98
98
98
100
100
100
100
98
100
100
100
95
98
|
quarters
|
Morning-
100
98
100
100
100
100
100
100
100
98
100
100
98
98
|
glory
|
Nutsedge,
90
80
85
75
80
75
95
35
80
75
90
90
85
70
|
Yellow
|
Oat, Wild
90
90
35
90
90
98
90
85
90
90
95
95
85
60
|
Oilseed
75
95
45
95
95
100
0
80
0
55
5
10
85
100
|
Rape
|
Pigweed
98
90
98
98
100
98
98
95
90
98
98
98
95
95
|
Ragweed
100
98
98
100
100
100
100
100
98
98
98
98
95
90
|
Ryegrass,
80
35
90
90
90
95
95
95
95
90
95
95
90
90
|
Italian
|
Soybean
40
10
10
15
25
10
55
5
65
0
65
10
35
35
|
Velvetleaf
100
100
100
100
100
90
98
85
65
80
95
98
95
55
|
Waterhemp
98
80
90
98
100
70
100
45
90
70
100
100
100
95
|
Wheat
5
5
0
10
35
25
15
15
5
0
20
35
5
30
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
129
130
132
133
134
136
137
138
139
145
153
154
161
162
|
|
Barnyard-
85
55
25
35
55
40
65
40
60
70
90
95
55
25
|
grass
|
Blackgrass
80
60
45
30
98
45
0
80
10
90
90
85
65
40
|
Chickweed
100
100
95
—
—
—
—
—
—
—
98
95
80
95
|
Corn
30
15
10
5
15
10
20
15
15
10
10
5
40
0
|
Crabgrass,
60
60
25
20
40
35
35
25
40
20
75
75
20
10
|
Large
|
Foxtail,
95
70
75
55
45
90
95
80
60
55
95
95
35
40
|
Giant
|
Galium
100
98
95
100
100
95
95
95
100
100
98
95
95
98
|
Johnson-
25
20
10
10
25
5
15
20
25
20
15
20
25
10
|
grass
|
Kochia
95
100
95
100
100
100
100
100
100
100
85
80
90
90
|
Lambs-
98
100
100
100
100
100
100
98
100
100
95
95
85
95
|
quarters
|
Morning-
100
100
98
95
100
100
100
100
100
100
100
100
98
90
|
glory
|
Nutsedge,
95
85
85
98
90
85
90
80
85
95
90
80
50
30
|
Yellow
|
Oat, Wild
98
95
90
95
95
90
90
90
90
100
95
90
90
70
|
Oilseed
5
0
40
98
100
98
98
98
95
90
90
95
90
0
|
Rape
|
Pigweed
98
90
65
95
100
98
100
98
98
100
85
85
98
90
|
Ragweed
95
98
98
5
30
5
40
5
0
25
90
90
85
90
|
Ryegrass,
95
95
95
5
40
35
60
70
60
40
95
95
90
80
|
Italian
|
Soybean
25
50
20
40
85
15
20
25
60
70
5
25
40
0
|
Velvetleaf
100
98
75
100
100
98
95
98
100
100
95
90
100
70
|
Waterhemp
98
98
75
100
100
100
90
100
100
100
90
70
95
65
|
Wheat
55
15
0
80
90
90
95
90
90
90
10
5
15
10
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
164
165
171
176
|
|
Barnyard-
35
25
60
20
|
grass
|
Blackgrass
45
25
55
0
|
Chickweed
98
98
95
—
|
Corn
5
5
20
5
|
Crabgrass,
10
20
55
30
|
Large
|
Foxtail,
30
25
75
40
|
Giant
|
Galium
100
100
95
60
|
Johnson-
10
15
20
10
|
grass
|
Kochia
95
90
98
100
|
Lambs-
98
98
100
90
|
quarters
|
Morning-
90
95
100
100
|
glory
|
Nutsedge,
40
35
—
5
|
Yellow
|
Oat, Wild
80
70
95
35
|
Oilseed
0
5
30
95
|
Rape
|
Pigweed
85
85
100
75
|
Ragweed
90
85
100
0
|
Ryegrass,
85
70
95
10
|
Italian
|
Soybean
5
15
50
10
|
Velvetleaf
70
50
100
80
|
Waterhemp
75
75
100
55
|
Wheat
20
15
20
40
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
1
2
10
11
14
16
20
21
22
23
25
26
27
28
|
|
Barnyard-
5
15
90
5
55
70
30
75
10
75
20
30
25
35
|
grass
|
Blackgrass
60
85
10
30
5
5
10
90
20
70
60
60
85
80
|
Chickweed
98
95
90
85
90
90
100
100
95
100
100
100
100
98
|
Corn
5
5
5
0
0
0
5
20
5
10
5
5
0
5
|
Crabgrass,
25
15
65
0
30
20
10
40
5
35
20
20
30
40
|
Large
|
Foxtail,
60
90
50
10
50
70
45
90
40
85
70
40
90
85
|
Giant
|
Galium
95
98
70
90
80
85
100
100
95
100
100
95
100
100
|
Johnsongrass
0
5
5
5
0
0
10
20
5
10
5
5
—
—
|
Kochia
95
65
95
100
90
20
90
95
95
100
100
90
90
95
|
Lambs-
100
98
65
90
80
40
100
95
90
95
98
90
90
100
|
quarters
|
Morning-
100
100
100
90
100
60
100
100
100
100
100
100
100
100
|
glory
|
Nutsedge,
—
98
—
30
—
—
85
90
65
85
90
20
—
85
|
Yellow
|
Oat, Wild
85
90
5
60
40
10
25
98
80
100
90
95
95
100
|
Oilseed
5
70
0
0
0
10
5
100
90
45
20
5
80
5
|
Rape
|
Pigweed
98
90
70
90
70
30
98
95
90
98
95
98
85
90
|
Ragweed
95
95
70
95
50
0
95
90
90
95
95
85
85
85
|
Ryegrass,
95
85
20
90
65
60
80
95
90
95
90
90
90
90
|
Italian
|
Soybean
5
50
0
0
5
0
35
10
0
10
10
10
0
0
|
Velvetleaf
95
100
40
45
40
20
85
85
80
85
85
60
90
85
|
Waterhemp
100
85
50
95
50
5
60
85
75
85
95
85
10
85
|
Wheat
10
5
0
5
5
0
0
35
5
35
0
0
5
0
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
29
32
33
34
36
37
40
41
42
47
51
52
54
56
|
|
Barnyard-
40
65
50
35
35
60
25
40
30
85
10
5
55
5
|
grass
|
Blackgrass
60
80
5
35
5
80
45
50
60
30
0
30
60
5
|
Chickweed
100
100
90
90
95
90
90
90
100
98
70
98
95
55
|
Corn
30
30
5
5
5
20
20
10
5
10
0
0
5
0
|
Crabgrass,
50
75
20
20
25
25
10
25
20
40
10
5
35
5
|
Large
|
Foxtail,
60
80
60
25
70
60
20
30
35
75
15
10
75
0
|
Giant
|
Galium
100
100
95
95
95
95
90
100
100
90
90
100
98
90
|
Johnsongrass
—
15
5
5
5
5
5
10
—
20
0
10
10
5
|
Kochia
75
90
40
60
55
5
0
100
100
95
50
5
90
90
|
Lambs-
85
98
98
95
98
95
80
95
100
98
65
75
100
85
|
quarters
|
Morning-
100
100
95
95
98
98
80
100
100
100
75
100
98
50
|
glory
|
Nutsedge,
—
80
45
85
55
65
20
65
—
80
85
90
55
50
|
Yellow
|
Oat, Wild
85
100
40
90
65
90
60
90
90
30
5
0
60
20
|
Oilseed
5
60
30
50
50
40
5
5
10
5
5
0
40
0
|
Rape
|
Pigweed
98
90
65
80
95
95
85
75
98
98
70
10
98
85
|
Ragweed
95
98
90
95
95
98
85
95
98
98
5
80
95
60
|
Ryegrass,
85
90
70
90
60
90
80
90
90
25
60
45
85
65
|
Italian
|
Soybean
20
30
0
15
5
15
30
20
10
10
0
0
10
0
|
Velvetleaf
85
85
75
100
95
85
20
85
85
95
50
55
98
15
|
Waterhemp
80
85
65
90
95
80
80
90
98
100
80
10
95
95
|
Wheat
30
25
0
10
0
30
10
30
0
0
0
0
0
5
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
57
59
60
65
66
67
69
72
73
75
78
79
80
81
|
|
Barnyard-
95
55
35
35
30
35
35
50
55
15
30
30
35
35
|
grass
|
Blackgrass
5
85
85
10
40
65
30
80
90
20
5
35
40
90
|
Chickweed
95
98
95
90
95
95
95
90
95
95
70
90
95
95
|
Corn
5
65
30
5
5
10
5
20
20
10
10
25
5
10
|
Crabgrass,
30
25
50
20
35
35
25
35
60
5
10
30
30
40
|
Large
|
Foxtail,
85
85
70
35
65
80
10
75
75
5
20
75
70
90
|
Giant
|
Galium
95
98
100
90
95
95
98
95
95
90
80
95
95
95
|
Johnsongrass
5
25
55
5
5
5
10
5
40
5
5
10
5
5
|
Kochia
70
85
100
90
90
35
95
90
90
95
85
90
90
80
|
Lambs-
95
98
95
95
100
90
100
90
95
100
75
98
98
98
|
quarters
|
Morning-
100
100
100
95
100
100
95
95
95
100
65
100
100
100
|
glory
|
Nutsedge,
90
95
90
60
85
80
70
70
80
50
35
80
85
90
|
Yellow
|
Oat, Wild
45
90
95
50
90
90
80
90
95
40
60
85
90
95
|
Oilseed
0
40
85
0
10
75
50
20
70
90
0
70
60
85
|
Rape
|
Pigweed
85
95
95
98
100
80
90
95
95
100
75
98
95
85
|
Ragweed
85
95
98
80
90
98
95
95
90
100
60
98
98
70
|
Ryegrass,
50
90
95
85
85
85
95
90
90
85
85
85
85
90
|
Italian
|
Soybean
0
10
40
5
10
5
20
15
25
35
5
5
5
5
|
Velvetleaf
100
90
90
65
85
85
85
85
85
85
35
90
55
90
|
Waterhemp
85
98
98
75
90
75
95
85
85
100
80
80
85
85
|
Wheat
0
10
30
0
0
0
0
5
35
0
5
0
10
0
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
82
83
84
85
87
88
89
90
91
97
98
99
100
102
|
|
Barnyard-
25
30
25
40
35
40
20
50
45
15
98
35
30
35
|
grass
|
Blackgrass
35
90
55
90
60
90
0
25
10
0
50
50
5
5
|
Chickweed
90
95
95
95
95
100
100
95
100
15
100
90
95
95
|
Corn
10
10
30
0
30
20
10
10
10
0
15
10
5
10
|
Crabgrass,
20
40
20
40
25
55
5
35
25
10
45
30
25
20
|
Large
|
Foxtail,
60
85
65
90
75
90
20
55
75
5
98
30
75
60
|
Giant
|
Galium
95
100
95
100
95
100
95
95
98
85
98
98
95
95
|
Johnson-
10
5
10
50
5
5
0
10
5
0
10
10
5
0
|
grass
|
Kochia
90
65
90
60
90
100
90
100
90
70
60
90
95
20
|
Lambs-
98
85
98
100
98
95
100
98
100
50
100
85
98
70
|
quarters
|
Morning-
100
100
98
100
100
98
98
100
100
30
100
100
100
100
|
glory
|
Nutsedge,
85
85
85
95
80
80
70
90
45
0
50
75
20
60
|
Yellow
|
Oat, Wild
90
90
90
95
85
100
30
90
90
5
95
90
85
10
|
Oilseed
50
45
50
10
50
60
0
0
95
0
10
60
10
5
|
Rape
|
Pigweed
90
90
95
85
90
90
80
95
100
60
100
98
100
95
|
Ragweed
95
90
98
85
95
85
90
95
95
25
98
95
95
100
|
Ryegrass,
85
90
85
90
85
90
75
90
95
50
65
95
90
25
|
Italian
|
Soybean
5
0
10
0
10
5
0
55
10
5
25
5
5
10
|
Velvetleaf
95
90
85
85
90
85
75
98
98
10
75
98
40
100
|
Waterhemp
90
60
95
85
90
85
50
100
75
5
100
95
95
80
|
Wheat
5
0
5
0
0
0
0
10
10
0
15
10
0
5
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
104
105
106
107
108
109
111
113
114
115
121
123
125
126
|
|
Barnyard-
45
25
20
40
40
55
45
35
40
35
25
40
80
35
|
grass
|
Blackgrass
50
50
60
5
35
50
20
45
5
20
15
45
60
10
|
Chickweed
100
98
95
95
95
95
100
98
98
90
90
90
95
95
|
Corn
50
30
10
20
25
35
15
10
0
5
5
20
5
20
|
Crabgrass,
35
20
30
35
25
60
25
25
20
20
20
30
40
30
|
Large
|
Foxtail,
75
75
90
70
75
80
70
30
50
20
70
35
95
15
|
Giant
|
Galium
98
95
95
100
95
100
95
95
95
95
95
95
95
98
|
Johnsongrass
5
0
10
0
5
5
15
10
5
10
5
20
20
15
|
Kochia
95
95
80
90
95
100
90
95
90
90
95
95
90
95
|
Lambs-
100
100
95
90
98
100
100
100
100
90
98
100
98
95
|
quarters
|
Morning-
100
100
100
98
98
100
100
100
100
95
100
98
100
98
|
glory
|
Nutsedge,
60
75
90
75
70
80
65
85
25
65
85
85
85
70
|
Yellow
|
Oat, Wild
90
90
90
40
90
90
90
90
65
80
80
90
95
90
|
Oilseed
95
60
85
80
85
95
95
0
40
0
85
0
5
60
|
Rape
|
Pigweed
100
100
90
98
98
100
90
95
95
70
90
80
98
95
|
Ragweed
98
98
75
98
98
100
98
98
98
95
95
95
98
95
|
Ryegrass,
90
90
90
60
90
90
95
95
80
95
90
90
95
90
|
Italian
|
Soybean
10
10
0
20
15
30
5
40
0
20
0
20
10
20
|
Velvetleaf
98
90
90
95
100
98
98
90
55
70
75
85
95
98
|
Waterhemp
100
100
75
95
90
90
55
90
55
90
75
100
98
95
|
Wheat
5
5
0
0
5
10
15
5
5
0
25
15
30
0
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
127
129
130
132
133
134
136
137
138
139
143
145
153
154
|
|
Barnyard-
25
70
35
25
45
40
35
50
30
40
30
30
70
90
|
grass
|
Blackgrass
5
60
55
25
70
50
30
0
50
60
20
30
90
60
|
Chickweed
90
100
98
95
—
—
—
—
—
—
80
—
98
90
|
Corn
5
30
5
5
5
10
10
10
15
15
5
5
25
5
|
Crabgrass,
10
35
15
10
5
15
25
35
20
30
30
10
50
70
|
Large
|
Foxtail,
25
85
40
60
40
35
70
80
65
30
20
25
90
95
|
Giant
|
Galium
85
100
95
95
98
100
90
90
95
100
90
98
98
95
|
Johnsongrass
10
15
5
5
20
5
5
15
20
15
20
20
10
20
|
Kochia
95
90
100
95
100
100
100
100
100
100
60
100
80
60
|
Lambs-
85
95
100
100
100
100
95
98
95
100
75
100
95
90
|
quarters
|
Morning-
85
100
85
95
100
100
100
100
98
100
70
100
98
98
|
glory
|
Nutsedge,
60
85
80
75
95
95
75
85
75
70
35
85
95
85
|
Yellow
|
Oat, Wild
55
100
85
70
95
95
85
90
80
90
60
95
95
90
|
Oilseed
25
5
0
5
98
100
98
98
98
98
5
95
90
98
|
Rape
|
Pigweed
90
98
90
70
100
100
85
98
90
98
75
75
85
90
|
Ragweed
60
95
98
95
5
5
0
30
5
0
70
5
95
85
|
Ryegrass,
80
95
95
95
35
20
30
30
10
35
90
30
95
90
|
Italian
|
Soybean
30
20
25
0
75
70
10
15
10
65
20
55
10
20
|
Velvetleaf
25
95
98
65
100
100
90
90
95
95
50
98
90
85
|
Waterhemp
85
85
80
80
100
100
95
85
98
100
90
100
90
85
|
Wheat
5
40
10
0
55
65
45
90
80
60
15
85
10
10
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
161
162
164
165
171
176
|
|
Barnyard-
45
25
30
25
40
10
|
grass
|
Blackgrass
60
30
40
20
40
0
|
Chickweed
70
95
95
95
90
—
|
Corn
15
0
5
0
10
0
|
Crabgrass,
5
10
10
20
40
20
|
Large
|
Foxtail,
10
15
15
15
50
35
|
Giant
|
Galium
95
95
100
98
95
60
|
Johnsongrass
20
5
5
10
15
5
|
Kochia
80
90
90
85
98
95
|
Lambsquarters
80
90
85
85
98
80
|
Morningglory
95
85
90
85
100
98
|
Nutsedge,
20
30
25
25
75
5
|
Yellow
|
Oat, Wild
80
70
70
65
90
10
|
Oilseed
95
0
0
0
0
95
|
Rape
|
Pigweed
90
85
85
75
90
50
|
Ragweed
95
75
85
75
100
0
|
Ryegrass,
90
70
80
55
95
0
|
Italian
|
Soybean
40
0
10
15
60
15
|
Velvetleaf
90
30
25
20
100
75
|
Waterhemp
85
70
70
75
98
60
|
Wheat
10
5
10
10
30
10
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
1
2
10
11
14
16
20
21
22
23
25
26
27
28
|
|
Barnyard-
5
10
90
0
5
70
10
45
5
60
20
25
20
25
|
grass
|
Blackgrass
50
65
0
15
0
5
10
90
0
60
55
55
70
70
|
Chickweed
95
95
90
65
90
80
98
100
90
100
98
95
100
95
|
Corn
25
5
0
0
0
0
5
65
5
30
5
10
5
5
|
Crabgrass,
10
15
30
0
5
20
10
35
5
20
15
20
25
20
|
Large
|
Foxtail,
15
65
60
5
45
60
25
80
15
65
35
25
75
80
|
Giant
|
Galium
95
95
50
90
55
80
100
100
90
100
95
95
100
100
|
Johnson-
0
5
0
0
0
0
10
20
5
5
5
5
0
5
|
grass
|
Kochia
95
55
85
95
85
0
80
90
95
95
95
70
80
70
|
Lambs-
100
85
80
90
80
60
85
90
85
95
95
85
85
98
|
quarters
|
Morning-
100
100
90
80
85
50
100
100
100
100
100
100
100
98
|
glory
|
Nutsedge,
—
95
—
15
—
—
65
90
50
70
75
10
80
85
|
Yellow
|
Oat, Wild
70
80
5
45
30
5
5
98
50
95
70
80
95
95
|
Oilseed
0
70
0
0
0
0
0
80
15
15
0
0
70
60
|
Rape
|
Pigweed
95
60
60
90
70
30
90
95
75
98
90
85
80
85
|
Ragweed
95
80
30
40
90
0
85
90
75
90
85
70
75
75
|
Ryegrass,
90
75
5
70
60
50
60
95
70
90
85
90
85
85
|
Italian
|
Soybean
0
0
0
0
0
0
0
0
0
10
0
5
0
0
|
Velvetleaf
85
100
45
5
20
5
25
85
50
85
80
30
85
85
|
Waterhemp
95
65
45
80
10
5
40
75
70
55
95
85
60
75
|
Wheat
0
0
0
0
0
0
0
5
0
30
0
0
0
0
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
29
32
33
34
35
36
37
40
41
42
47
51
52
54
|
|
Barnyard-
25
30
25
25
20
25
20
15
35
30
55
5
5
30
|
grass
|
Blackgrass
50
60
0
10
45
5
40
15
35
35
20
0
10
5
|
Chickweed
95
95
90
90
95
95
90
60
95
100
90
55
90
95
|
Corn
10
20
5
5
5
0
10
0
5
5
5
0
0
0
|
Crabgrass,
20
30
20
10
20
30
20
5
10
15
30
5
0
25
|
Large
|
Foxtail,
35
50
40
20
75
55
35
15
15
30
65
5
5
55
|
Giant
|
Galium
95
100
90
95
95
95
95
85
100
90
90
90
100
98
|
Johnsongrass
5
25
5
5
20
5
5
5
10
5
10
0
10
5
|
Kochia
60
50
5
45
40
55
0
80
100
100
90
15
0
90
|
Lambs-
85
90
95
90
70
98
90
70
95
95
85
50
60
95
|
quarters
|
Morning-
100
100
95
98
100
98
95
65
95
100
100
55
100
98
|
glory
|
Nutsedge,
35
80
15
60
85
40
40
15
65
75
70
70
80
35
|
Yellow
|
Oat, Wild
55
90
30
85
60
60
80
50
90
90
10
5
0
50
|
Oilseed
0
60
55
30
10
40
20
30
0
5
0
5
0
80
|
Rape
|
Pigweed
95
90
50
85
55
85
100
65
75
95
90
65
5
95
|
Ragweed
90
90
95
98
40
90
95
75
85
85
98
5
65
95
|
Ryegrass,
80
90
45
80
55
60
85
65
90
90
10
50
40
80
|
Italian
|
Soybean
10
25
0
5
5
0
5
60
15
5
10
0
0
5
|
Velvetleaf
80
70
60
80
100
85
70
10
65
85
90
20
25
90
|
Waterhemp
80
80
30
85
45
95
80
65
75
85
75
50
10
90
|
Wheat
5
15
0
5
5
0
0
10
0
0
0
0
0
50
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
56
57
59
60
65
66
67
69
72
73
75
78
79
80
|
|
Barnyard-
5
95
30
25
15
20
35
35
40
40
25
25
25
30
|
grass
|
Blackgrass
5
5
80
60
5
15
60
20
70
85
5
5
10
35
|
Chickweed
10
95
98
95
90
95
95
90
90
90
90
60
90
95
|
Corn
0
5
45
25
5
0
5
0
10
20
5
0
0
5
|
Crabgrass,
5
20
20
35
20
30
35
25
25
35
10
5
25
25
|
Large
|
Foxtail,
0
70
60
60
20
55
75
10
70
65
5
5
60
55
|
Giant
|
Galium
85
95
98
100
85
95
95
95
95
90
90
80
95
95
|
Johnsongrass
0
5
5
35
5
5
5
10
5
5
5
5
5
5
|
Kochia
90
65
85
90
90
90
30
90
85
90
85
70
90
90
|
Lambs-
50
70
95
90
95
100
95
90
85
95
100
70
95
95
|
quarters
|
Morning-
50
100
100
98
85
95
95
95
90
90
100
40
100
100
|
glory
|
Nutsedge,
5
90
85
85
50
70
70
65
60
80
20
25
80
80
|
Yellow
|
Oat, Wild
10
35
75
95
35
80
85
60
95
90
35
50
60
90
|
Oilseed
0
0
50
5
0
10
50
10
35
70
70
0
25
50
|
Rape
|
Pigweed
75
80
95
85
90
98
85
85
90
85
95
60
98
90
|
Ragweed
0
90
95
90
85
85
75
90
90
90
85
20
95
90
|
Ryegrass,
60
30
90
90
80
80
80
90
90
90
80
65
60
85
|
Italian
|
Soybean
0
0
15
20
5
10
5
25
15
15
35
0
0
15
|
Velvetleaf
0
95
85
85
20
75
85
80
85
85
50
10
85
90
|
Waterhemp
75
65
90
90
75
90
70
90
65
75
100
90
90
80
|
Wheat
0
0
20
5
0
0
0
0
30
30
0
5
0
5
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
81
82
83
84
85
87
88
89
90
91
97
98
99
100
|
|
Barnyard-
35
25
25
20
45
25
40
15
35
30
5
85
25
25
|
grass
|
Blackgrass
85
35
80
35
80
35
80
0
15
5
0
30
30
5
|
Chickweed
90
90
95
90
95
90
100
95
90
98
0
100
90
90
|
Corn
5
30
5
20
0
5
0
5
10
0
0
0
5
10
|
Crabgrass,
35
20
25
10
30
10
20
5
15
20
5
25
20
15
|
Large
|
Foxtail,
85
25
85
55
85
55
85
10
25
45
5
95
15
45
|
Giant
|
Galium
95
95
90
95
100
95
100
95
95
90
80
95
95
95
|
Johnson-
5
5
5
5
15
5
5
0
10
5
0
5
10
0
|
grass
|
Kochia
75
90
60
90
70
90
50
90
100
90
0
20
85
90
|
Lambs-
95
98
85
90
98
98
85
90
98
100
20
100
75
90
|
quarters
|
Morning-
100
100
90
98
98
98
100
95
100
100
40
100
95
100
|
glory
|
Nutsedge,
85
80
80
85
85
80
85
60
80
40
0
15
55
25
|
Yellow
|
Oat, Wild
90
85
90
90
90
90
95
10
70
70
5
80
70
70
|
Oilseed
65
40
0
45
10
50
5
0
0
90
0
0
5
60
|
Rape
|
Pigweed
85
90
85
90
85
90
85
75
80
90
50
100
75
85
|
Ragweed
75
98
85
90
85
95
85
90
85
98
10
98
90
95
|
Ryegrass,
85
85
90
80
90
80
90
75
90
80
30
45
90
90
|
Italian
|
Soybean
0
10
0
5
0
0
0
0
50
5
0
10
5
5
|
Velvetleaf
85
80
90
90
85
85
85
75
75
75
20
70
85
50
|
Waterhemp
60
98
85
85
65
80
85
40
100
50
5
100
75
90
|
Wheat
0
0
0
0
0
0
0
0
10
5
0
10
0
0
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
102
104
105
106
107
108
109
111
113
114
115
121
123
125
|
|
Barnyard-
20
35
25
15
50
35
30
30
35
35
20
20
25
40
|
grass
|
Blackgrass
5
35
40
50
5
35
25
5
25
0
10
15
35
45
|
Chickweed
95
98
95
98
90
90
95
98
90
95
75
90
90
95
|
Corn
0
80
15
10
10
40
15
10
10
0
5
5
15
0
|
Crabgrass,
10
30
30
40
20
10
40
20
15
20
20
5
35
35
|
Large
|
Foxtail,
35
70
50
75
55
40
50
45
25
20
15
50
20
90
|
Giant
|
Galium
95
95
98
95
95
98
100
95
95
95
90
90
95
95
|
Johnson-
0
5
0
10
0
0
5
10
10
5
10
5
10
5
|
grass
|
Kochia
0
95
95
85
85
95
95
85
98
90
90
90
95
90
|
Lambs-
70
98
85
90
90
95
100
100
98
95
90
95
98
98
|
quarters
|
Morning-
100
100
98
98
98
100
98
100
100
100
85
98
90
95
|
glory
|
Nutsedge,
55
45
70
85
80
60
50
40
70
10
60
40
75
85
|
Yellow
|
Oat, Wild
5
90
60
90
20
90
80
70
90
60
60
90
85
90
|
Oilseed
0
70
30
80
55
90
90
10
0
85
0
60
0
0
|
Rape
|
Pigweed
80
98
98
80
95
95
95
90
75
85
70
85
80
95
|
Ragweed
95
90
95
85
90
95
95
90
95
90
85
90
90
98
|
Ryegrass,
5
90
90
90
50
90
90
90
95
70
90
90
90
90
|
Italian
|
Soybean
10
0
0
0
5
5
15
5
30
0
20
0
10
5
|
Velvetleaf
75
85
85
85
98
85
80
80
95
55
25
35
75
90
|
Waterhemp
60
90
100
80
85
85
85
45
90
55
75
65
90
95
|
Wheat
0
5
0
0
0
5
5
10
15
5
5
5
5
15
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
126
127
129
130
132
133
134
136
137
138
139
143
145
151
|
|
Barnyard-
30
20
65
30
30
30
20
25
40
25
20
25
15
50
|
grass
|
Blackgrass
5
5
40
35
5
35
45
5
0
5
50
5
0
35
|
Chickweed
90
90
98
95
90
—
—
—
—
—
—
70
—
98
|
Corn
10
0
20
5
5
5
10
5
15
0
0
0
5
25
|
Crabgrass,
20
5
30
15
15
5
10
20
30
20
10
10
10
40
|
Large
|
Foxtail,
15
5
75
20
40
25
25
45
60
60
30
5
25
75
|
Giant
|
Galium
95
80
100
95
95
95
95
90
90
90
95
90
95
95
|
Johnson-
10
5
15
5
5
10
10
5
10
10
5
25
10
20
|
grass
|
Kochia
90
85
60
95
90
100
100
95
100
95
100
60
98
30
|
Lambs-
95
80
95
98
90
98
98
90
90
90
95
60
98
98
|
quarters
|
Morning-
95
75
100
80
80
100
100
98
98
100
100
65
98
98
|
glory
|
Nutsedge,
60
35
75
75
55
90
80
55
85
65
75
40
90
85
|
Yellow
|
Oat, Wild
80
20
90
80
60
90
90
75
70
80
90
55
95
90
|
Oilseed
80
0
0
0
10
98
100
98
98
98
95
0
98
20
|
Rape
|
Pigweed
90
85
95
70
55
98
100
80
98
85
95
65
100
70
|
Ragweed
90
55
90
90
95
0
5
0
20
0
0
30
0
85
|
Ryegrass,
85
75
90
90
85
10
15
10
30
5
10
60
15
85
|
Italian
|
Soybean
10
10
10
15
0
40
70
10
10
10
55
15
40
25
|
Velvetleaf
85
30
95
70
40
90
90
95
90
90
80
25
90
65
|
Waterhemp
90
85
70
85
60
100
100
80
65
95
100
55
100
75
|
Wheat
0
5
35
5
0
35
50
45
90
40
55
35
50
0
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
153
154
161
162
164
165
171
176
|
|
Barnyard-
60
85
35
20
25
15
35
5
|
grass
|
Blackgrass
85
65
40
15
15
15
30
0
|
Chickweed
95
90
70
90
90
90
90
—
|
Corn
35
5
5
0
0
0
0
10
|
Crabgrass,
50
70
5
5
5
5
20
5
|
Large
|
Foxtail,
85
90
5
15
10
5
25
15
|
Giant
|
Galium
95
95
80
90
95
85
95
5
|
Johnson-
5
5
5
5
5
5
5
5
|
grass
|
Kochia
70
50
70
80
85
40
95
90
|
Lambs-
90
85
90
95
85
75
95
80
|
quarters
|
Morning-
100
98
90
85
85
70
100
85
|
glory
|
Nutsedge,
90
60
10
25
20
30
75
5
|
Yellow
|
Oat, Wild
95
80
50
60
45
45
90
5
|
Oilseed
90
90
70
0
0
0
0
95
|
Rape
|
Pigweed
75
85
80
80
80
70
80
30
|
Ragweed
90
75
80
85
80
55
100
0
|
Ryegrass,
95
90
80
70
60
50
95
0
|
Italian
|
Soybean
10
20
30
0
0
10
30
10
|
Velvetleaf
85
85
65
15
60
25
70
25
|
Waterhemp
65
80
90
65
70
70
95
40
|
Wheat
20
5
0
10
5
5
15
5
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
1
2
10
11
14
16
20
21
22
23
25
26
27
28
|
|
Barnyard-
0
10
35
0
5
5
5
35
5
40
15
20
15
20
|
grass
|
Blackgrass
20
45
0
5
0
0
5
80
0
50
30
50
50
50
|
Chickweed
95
95
90
60
90
75
90
95
90
100
90
95
95
95
|
Corn
0
0
0
0
0
0
5
5
0
10
5
0
0
5
|
Crabgrass,
20
10
10
0
5
5
5
30
0
5
5
5
5
25
|
Large
|
Foxtail,
35
20
70
5
20
55
0
55
10
30
35
15
60
60
|
Giant
|
Galium
90
95
5
75
50
60
98
98
90
95
90
90
100
100
|
Johnson-
0
5
0
0
0
0
5
10
5
5
0
5
10
5
|
grass
|
Kochia
95
50
60
85
85
0
50
80
90
95
95
80
75
70
|
Lambs-
85
85
50
80
80
10
80
85
70
85
90
75
85
85
|
quarters
|
Morning-
100
100
55
70
65
45
100
85
100
100
100
98
100
95
|
glory
|
Nutsedge,
—
80
—
5
—
—
45
85
35
60
65
5
85
75
|
Yellow
|
Oat, Wild
50
75
5
40
10
5
0
90
40
85
60
60
85
95
|
Oilseed
0
65
0
0
0
0
0
65
5
5
0
0
5
5
|
Rape
|
Pigweed
95
80
55
50
55
40
75
70
85
90
90
75
55
60
|
Ragweed
90
80
5
0
15
0
80
85
70
85
90
15
70
65
|
Ryegrass,
80
60
5
70
40
10
55
90
60
85
70
85
80
80
|
Italian
|
Soybean
0
0
0
0
0
0
0
0
0
5
0
5
0
0
|
Velvetleaf
80
100
40
0
10
5
25
75
20
70
70
5
80
70
|
Waterhemp
95
65
40
80
5
5
70
40
75
80
75
75
65
60
|
Wheat
0
0
0
0
0
0
0
0
0
10
0
0
0
0
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
29
32
33
34
35
36
37
40
41
42
47
51
52
54
|
|
Barnyard-
15
10
25
20
20
15
25
5
25
20
15
5
5
15
|
grass
|
Blackgrass
40
30
0
10
15
5
35
5
30
30
0
0
0
15
|
Chickweed
95
90
85
90
95
80
90
55
95
90
90
50
95
95
|
Corn
0
0
0
0
5
0
0
0
5
0
0
0
0
0
|
Crabgrass,
10
10
10
5
20
25
10
5
5
10
20
0
0
20
|
Large
|
Foxtail,
30
15
20
10
50
30
25
5
15
25
50
5
0
20
|
Giant
|
Galium
90
90
90
90
90
90
90
80
100
95
80
85
90
95
|
Johnson-
0
5
0
5
20
0
0
0
5
5
10
0
5
5
|
grass
|
Kochia
60
50
20
10
30
50
0
70
100
90
75
0
0
50
|
Lambs-
80
85
90
90
80
90
90
70
90
85
85
5
55
95
|
quarters
|
Morning-
85
90
85
85
100
90
90
55
95
75
100
5
98
95
|
glory
|
Nutsedge,
25
55
5
45
75
20
20
0
65
65
40
35
60
10
|
Yellow
|
Oat, Wild
60
70
35
80
40
50
60
35
55
75
5
0
0
45
|
Oilseed
0
10
40
30
—
40
40
5
0
0
0
0
0
70
|
Rape
|
Pigweed
95
75
30
90
60
70
85
35
65
85
90
60
30
85
|
Ragweed
80
85
85
85
25
90
90
45
70
90
80
10
55
90
|
Ryegrass,
70
85
30
80
35
55
80
50
80
65
0
35
10
50
|
Italian
|
Soybean
0
15
0
5
0
0
10
5
15
0
0
0
0
5
|
Velvetleaf
35
10
10
50
100
65
20
5
30
45
70
5
5
45
|
Waterhemp
70
70
25
85
25
85
85
65
75
75
90
30
10
85
|
Wheat
5
5
0
5
0
0
30
10
10
0
0
0
0
0
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
56
57
59
60
65
66
67
69
72
73
75
78
79
80
|
|
Barnyard-
0
90
20
20
10
15
25
25
35
25
25
15
20
25
|
grass
|
Blackgrass
0
5
65
50
5
10
40
15
60
40
5
0
5
15
|
Chickweed
5
90
90
90
55
90
90
90
90
90
95
30
90
90
|
Corn
0
0
5
10
5
0
5
0
5
5
5
0
0
0
|
Crabgrass,
0
10
15
15
5
25
35
5
10
30
5
5
20
10
|
Large
|
Foxtail,
0
70
45
45
10
40
70
5
50
40
5
15
35
25
|
Giant
|
Galium
80
95
95
100
85
90
90
90
80
90
90
70
95
90
|
Johnson-
0
5
5
5
5
5
5
5
5
5
5
5
5
5
|
grass
|
Kochia
70
50
95
90
90
90
0
90
60
90
90
45
50
90
|
Lambs-
0
70
90
85
90
90
85
85
85
90
100
40
85
95
|
quarters
|
Morning-
35
95
95
90
75
90
95
90
80
75
98
20
100
100
|
glory
|
Nutsedge,
0
90
65
85
25
65
65
40
30
80
25
0
85
65
|
Yellow
|
Oat, Wild
5
20
80
85
25
55
80
45
85
75
40
35
50
90
|
Oilseed
0
0
5
5
0
0
40
40
40
10
70
0
20
5
|
Rape
|
Pigweed
80
60
90
85
90
95
100
70
85
80
85
50
90
85
|
Ragweed
0
60
90
85
55
85
70
70
80
85
95
10
90
98
|
Ryegrass,
40
25
85
90
65
60
80
85
85
85
80
55
50
80
|
Italian
|
Soybean
0
0
0
15
5
0
5
10
10
0
20
0
0
0
|
Velvetleaf
0
90
80
40
10
55
70
40
45
40
70
0
75
70
|
Waterhemp
55
50
85
65
60
98
60
85
70
75
100
75
85
85
|
Wheat
0
0
0
5
0
0
0
0
30
10
0
0
0
0
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
81
82
83
84
85
87
88
89
90
91
97
98
99
100
|
|
Barnyard-
25
20
25
10
25
25
35
5
30
25
0
60
25
10
|
grass
|
Blackgrass
60
10
40
10
70
10
40
0
10
0
0
5
20
5
|
Chickweed
90
90
90
90
90
90
95
90
90
95
0
95
90
90
|
Corn
0
35
5
0
0
5
0
5
5
0
0
5
0
5
|
Crabgrass,
25
10
20
5
35
5
25
0
5
15
0
10
20
5
|
Large
|
Foxtail,
80
35
75
40
75
35
80
5
20
10
5
90
5
20
|
Giant
|
Galium
90
90
90
90
95
90
95
90
90
90
45
95
90
90
|
Johnson-
5
5
5
0
5
0
5
0
5
0
0
0
5
0
|
grass
|
Kochia
40
90
40
85
30
90
30
85
95
75
0
0
20
80
|
Lambs-
95
90
95
90
85
95
85
85
95
98
0
98
75
80
|
quarters
|
Morning-
95
100
98
90
98
98
95
90
100
100
10
100
75
100
|
glory
|
Nutsedge,
70
65
85
80
75
70
65
40
70
20
0
10
30
5
|
Yellow
|
Oat, Wild
85
55
90
85
90
85
90
5
70
50
5
70
60
50
|
Oilseed
45
35
50
5
5
10
20
0
0
60
0
0
0
30
|
Rape
|
Pigweed
80
85
80
85
85
75
65
80
75
98
20
100
75
75
|
Ragweed
70
90
70
85
75
90
80
80
85
75
0
100
70
98
|
Ryegrass,
85
80
80
80
85
80
80
45
85
60
10
40
85
65
|
Italian
|
Soybean
0
10
0
0
0
0
0
0
40
0
0
5
0
0
|
Velvetleaf
75
70
85
60
75
75
75
25
35
50
0
55
35
20
|
Waterhemp
60
85
85
80
85
85
60
30
85
50
5
98
75
85
|
Wheat
0
0
0
0
0
0
0
0
5
0
0
10
0
0
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
102
104
105
106
107
108
109
111
113
114
115
121
123
125
|
|
Barnyard-
20
20
10
15
35
20
25
10
25
30
10
20
20
35
|
grass
|
Blackgrass
0
15
15
45
0
15
20
0
15
0
0
0
15
20
|
Chickweed
95
90
90
95
90
90
80
95
90
90
80
90
90
95
|
Corn
0
5
10
0
5
5
0
5
5
0
5
0
10
5
|
Crabgrass,
5
20
20
25
15
5
35
10
5
10
10
10
10
25
|
Large
|
Foxtail,
20
50
40
70
15
30
45
15
20
10
5
20
20
70
|
Giant
|
Galium
90
95
95
95
95
90
98
95
95
95
85
90
95
95
|
Johnson-
0
10
5
5
0
0
0
10
0
5
5
0
5
5
|
grass
|
Kochia
0
95
95
70
70
90
95
80
95
30
70
90
95
85
|
Lambs-
75
90
85
85
85
90
95
90
98
95
70
90
95
90
|
quarters
|
Morning-
100
98
100
100
95
98
95
100
98
95
55
98
95
95
|
glory
|
Nutsedge,
20
55
55
65
80
30
45
35
70
10
40
45
55
35
|
Yellow
|
Oat, Wild
5
80
60
50
20
80
80
55
90
40
55
65
70
85
|
Oilseed
0
85
5
60
25
80
70
80
0
15
0
70
0
0
|
Rape
|
Pigweed
75
95
85
70
85
90
95
85
65
80
30
75
65
95
|
Ragweed
95
85
90
80
85
90
80
98
90
90
60
75
75
95
|
Ryegrass,
0
90
85
85
40
90
90
85
90
60
90
85
90
85
|
Italian
|
Soybean
0
0
5
0
0
10
0
0
15
0
10
0
10
0
|
Velvetleaf
30
50
75
80
75
70
75
40
70
25
15
10
65
85
|
Waterhemp
25
70
80
65
75
85
80
40
85
25
65
60
80
85
|
Wheat
0
0
0
0
0
0
0
10
5
0
0
5
5
0
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
126
127
129
130
132
133
134
136
137
138
139
143
144
145
|
|
Barnyard-
25
10
50
30
15
15
10
15
25
25
25
20
65
20
|
grass
|
Blackgrass
5
0
35
30
5
45
50
10
0
5
20
5
35
5
|
Chickweed
90
50
98
90
90
—
—
—
—
—
—
45
—
—
|
Corn
10
0
0
5
0
5
5
0
5
0
5
5
30
10
|
Crabgrass,
10
0
20
10
15
0
5
10
30
15
20
10
30
15
|
Large
|
Foxtail,
5
5
60
20
30
25
15
35
45
35
20
5
70
20
|
Giant
|
Galium
90
75
95
95
90
90
95
90
85
90
95
65
95
90
|
Johnson-
10
5
10
5
0
5
10
5
10
10
5
10
10
10
|
grass
|
Kochia
90
40
50
95
85
98
95
95
100
90
95
30
98
95
|
Lambs-
80
70
95
90
90
95
100
90
90
90
98
50
90
98
|
quarters
|
Morning-
95
65
98
75
65
100
98
98
100
98
98
50
98
95
|
glory
|
Nutsedge,
35
10
60
55
30
75
75
15
65
45
55
10
75
70
|
Yellow
|
Oat, Wild
60
10
85
60
40
90
90
50
70
50
90
40
90
95
|
Oilseed
60
0
0
0
5
95
95
95
95
95
95
0
95
98
|
Rape
|
Pigweed
85
70
95
50
50
80
80
75
90
80
80
50
90
70
|
Ragweed
85
10
90
85
65
0
0
0
10
0
0
0
35
0
|
Ryegrass,
80
50
70
90
80
5
5
5
10
5
5
55
70
5
|
Italian
|
Soybean
5
0
0
10
0
55
75
5
10
10
45
0
25
40
|
Velvetleaf
30
20
85
75
30
85
80
75
85
85
70
20
85
85
|
Waterhemp
75
70
75
70
40
95
98
80
85
90
98
40
95
95
|
Wheat
0
0
10
0
0
25
30
35
75
60
45
5
95
40
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
151
153
154
161
162
164
165
171
176
|
|
Barnyard-
40
40
70
20
10
10
10
15
5
|
grass
|
Blackgrass
45
80
60
10
10
5
5
5
0
|
Chickweed
95
90
90
65
90
80
70
90
—
|
Corn
20
20
15
0
0
0
0
0
0
|
Crabgrass,
35
55
65
0
0
0
0
5
10
|
Large
|
Foxtail,
60
80
85
0
5
5
0
10
5
|
Giant
|
Galium
95
95
95
80
90
90
85
95
0
|
Johnson-
10
10
5
10
5
5
0
5
5
|
grass
|
Kochia
60
40
50
70
70
60
45
95
90
|
Lambs-
95
85
90
80
85
70
70
90
60
|
quarters
|
Morning-
98
98
95
90
60
80
75
90
85
|
glory
|
Nutsedge,
80
85
70
5
20
20
20
50
5
|
Yellow
|
Oat, Wild
70
90
55
60
50
35
40
65
0
|
Oilseed
65
90
75
50
0
0
0
0
95
|
Rape
|
Pigweed
75
85
65
80
75
70
75
60
20
|
Ragweed
60
70
70
70
70
70
40
75
0
|
Ryegrass,
60
90
80
70
60
50
40
90
0
|
Italian
|
Soybean
5
5
10
15
0
0
10
10
5
|
Velvetleaf
60
85
70
45
5
25
20
35
0
|
Waterhemp
55
70
75
85
45
60
65
75
20
|
Wheat
0
15
0
0
0
5
5
0
0
|
|
16 g ai/ha
|
Post-
Compounds
|
emergence
35
40
143
144
151
|
|
Barnyard-
10
5
15
35
30
|
grass
|
Blackgrass
5
5
0
20
40
|
Chickweed
90
50
30
—
95
|
Corn
0
0
0
5
25
|
Crabgrass,
5
5
5
25
30
|
Large
|
Foxtail,
35
5
5
60
40
|
Giant
|
Galium
90
30
60
90
95
|
Johnson-
15
0
10
10
5
|
grass
|
Kochia
30
20
0
98
10
|
Lambs-
75
50
10
90
80
|
quarters
|
Morning-
100
5
30
98
98
|
glory
|
Nutsedge,
60
0
10
60
55
|
Yellow
|
Oat, Wild
30
5
30
90
50
|
Oilseed
0
0
60
95
50
|
Rape
|
Pigweed
25
15
50
85
55
|
Ragweed
0
25
0
35
35
|
Ryegrass,
30
10
45
45
40
|
Italian
|
Soybean
0
35
0
25
5
|
Velvetleaf
75
5
30
90
60
|
Waterhemp
30
20
25
90
55
|
Wheat
0
0
0
95
0
|
|
8 g ai/ha
|
Post-
Compounds
|
emergence
35
144
151
|
|
Barnyard-
10
25
25
|
grass
|
Blackgrass
0
30
10
|
Chickweed
90
—
90
|
Corn
0
0
20
|
Crabgrass,
5
20
5
|
Large
|
Foxtail,
25
50
20
|
Giant
|
Galium
90
90
95
|
Johnson-
10
10
5
|
grass
|
Kochia
—
90
0
|
Lambs-
35
90
80
|
quarters
|
Morning-
100
95
95
|
glory
|
Nutsedge,
45
60
55
|
Yellow
|
Oat, Wild
10
90
35
|
Oilseed
0
95
30
|
Rape
|
Pigweed
35
85
65
|
Ragweed
0
10
10
|
Ryegrass,
10
35
40
|
Italian
|
Soybean
0
40
0
|
Velvetleaf
60
70
15
|
Waterhemp
0
90
30
|
Wheat
0
90
0
|
|
4 g ai/ha
|
Post-
Compound
|
emergence
144
|
|
Barnyard-
15
|
grass
|
Blackgrass
30
|
Corn
0
|
Crabgrass,
20
|
Large
|
Foxtail,
45
|
Giant
|
Galium
80
|
Johnson-
20
|
grass
|
Kochia
90
|
Lambs-
80
|
quarters
|
Morning-
90
|
glory
|
Nutsedge,
10
|
Yellow
|
Oat, Wild
80
|
Oilseed
85
|
Rape
|
Pigweed
80
|
Ragweed
10
|
Ryegrass,
20
|
Italian
|
Soybean
45
|
Velvetleaf
50
|
Waterhemp
90
|
Wheat
90
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
10
11
20
21
22
23
25
27
28
29
32
34
|
|
Barnyard-
90
98
5
80
85
100
60
85
85
90
95
90
100
75
|
grass
|
Blackgrass
90
95
0
85
80
90
45
90
90
90
90
85
90
90
|
Corn
5
10
5
0
35
65
35
65
10
0
15
45
35
0
|
Crabgrass,
100
95
0
40
60
100
35
95
90
98
85
90
100
30
|
Large
|
Foxtail,
100
100
0
90
85
100
85
100
100
100
100
95
85
70
|
Giant
|
Galium
100
100
45
95
95
100
95
100
98
95
95
98
98
100
|
Johnson-
5
5
0
0
10
50
0
35
20
25
10
20
45
20
|
grass
|
Lambs-
100
100
30
100
90
100
90
95
95
98
90
90
90
75
|
quarters
|
Morningglory
100
100
55
100
100
100
100
98
100
100
100
98
98
95
|
Nutsedge,
75
95
0
30
95
85
70
90
80
95
70
85
60
65
|
Yellow
|
Oilseed
20
65
0
0
20
100
80
100
35
98
90
70
100
90
|
Rape
|
Pigweed
100
100
30
100
100
100
100
100
100
100
100
100
100
100
|
Ragweed
98
98
5
90
75
100
100
90
95
95
90
90
98
95
|
Ryegrass,
100
98
80
100
95
95
95
95
95
95
95
90
95
95
|
Italian
|
Soybean
0
0
0
0
30
20
5
55
5
0
50
0
55
5
|
Velvetleaf
98
100
50
90
100
98
98
100
98
98
95
100
90
98
|
Waterhemp
100
100
90
100
100
100
100
100
100
100
100
100
100
100
|
Wheat
20
10
0
10
30
40
0
90
5
10
10
50
70
25
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
36
37
41
42
47
54
57
59
60
66
67
69
72
73
|
|
Barnyard-
70
80
95
80
100
85
100
95
90
70
80
75
80
85
|
grass
|
Blackgrass
30
90
90
90
90
80
80
98
90
30
60
35
90
90
|
Corn
0
20
40
35
5
0
35
65
45
0
0
5
20
25
|
Crabgrass,
65
25
70
85
95
60
100
100
95
85
65
10
85
75
|
Large
|
Foxtail,
85
85
85
100
100
90
100
100
100
85
100
60
85
95
|
Giant
|
Galium
100
100
98
98
98
100
98
98
100
98
90
98
95
98
|
Johnson-
5
0
35
30
0
10
0
65
60
65
30
35
85
55
|
grass
|
Lambs-
80
90
90
90
100
80
100
95
90
98
85
95
90
90
|
quarters
|
Morning-
95
98
98
98
95
98
100
100
100
90
90
90
90
95
|
glory
|
Nutsedge,
65
60
80
80
85
70
95
90
85
65
70
90
70
95
|
Yellow
|
Oilseed
95
90
100
20
10
100
60
95
90
5
20
40
80
85
|
Rape
|
Pigweed
100
100
100
100
100
100
100
100
100
100
100
85
100
98
|
Ragweed
95
98
100
100
100
100
100
100
95
95
98
95
95
98
|
Ryegrass,
85
95
95
90
50
90
85
100
95
90
90
90
90
90
|
Italian
|
Soybean
20
65
55
5
30
20
0
25
75
0
0
5
0
0
|
Velvetleaf
90
90
98
98
100
95
100
100
98
85
75
90
85
85
|
Waterhemp
100
100
100
100
100
100
100
100
100
100
85
95
90
95
|
Wheat
0
45
65
5
0
0
5
85
70
40
0
5
40
60
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
75
79
80
81
82
83
84
85
87
88
89
90
91
97
|
|
Barnyard-
85
85
85
98
90
90
85
90
85
100
65
95
95
35
|
grass
|
Blackgrass
30
85
90
90
80
90
85
90
90
90
45
55
60
5
|
Corn
10
5
25
30
25
10
0
10
10
20
0
30
25
0
|
Crabgrass,
50
30
75
98
80
85
85
85
85
80
75
85
85
60
|
Large
|
Foxtail,
75
95
98
100
100
100
100
100
95
100
75
95
98
55
|
Giant
|
Galium
98
98
95
95
95
95
98
95
98
98
98
—
98
90
|
Johnson-
10
30
35
98
40
70
30
40
40
60
5
65
25
0
|
grass
|
Lambs-
90
100
98
95
98
100
100
100
100
90
90
100
100
25
|
quarters
|
Morning-
100
98
98
95
95
98
95
98
95
100
90
98
98
30
|
glory
|
Nutsedge,
75
90
80
95
90
95
80
80
80
95
90
90
90
0
|
Yellow
|
Oilseed
98
30
0
95
85
50
80
90
80
30
90
90
100
0
|
Rape
|
Pigweed
100
100
100
100
100
100
100
100
100
95
100
100
100
65
|
Ragweed
100
100
100
98
95
95
98
98
90
98
90
95
100
10
|
Ryegrass,
90
90
90
90
90
90
95
90
90
90
90
95
95
30
|
Italian
|
Soybean
55
0
0
0
0
0
0
0
0
100
5
100
20
20
|
Velvetleaf
98
95
95
98
90
90
90
90
90
85
85
95
100
30
|
Waterhemp
100
100
100
100
100
100
100
100
100
98
75
100
85
20
|
Wheat
5
0
0
0
0
0
0
5
0
10
0
40
40
0
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
99
102
104
105
106
107
108
109
111
113
114
116
121
125
|
|
Barnyard-
85
85
80
90
95
98
85
80
85
95
95
95
60
98
|
grass
|
Blackgrass
90
70
60
90
85
10
85
90
20
60
10
35
60
90
|
Corn
30
30
10
25
20
15
15
0
15
35
5
25
5
55
|
Crabgrass,
80
55
60
80
80
85
70
80
80
90
80
90
35
98
|
Large
|
Foxtail,
90
90
100
100
100
98
95
90
—
—
—
—
95
100
|
Giant
|
Galium
98
95
98
98
95
95
95
90
100
98
100
100
100
100
|
Johnson-
20
0
30
60
15
20
20
65
20
30
0
10
10
70
|
grass
|
Lambs-
95
100
95
95
100
95
100
100
95
100
95
95
100
100
|
quarters
|
Morning-
95
98
98
95
98
98
98
98
98
100
90
98
90
98
|
glory
|
Nutsedge,
90
75
85
85
90
90
80
80
90
85
95
95
50
90
|
Yellow
|
Oilseed
98
35
95
10
90
80
90
90
100
90
100
100
85
100
|
Rape
|
Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Ragweed
95
100
100
100
95
100
98
100
98
95
98
100
98
100
|
Ryegrass,
100
70
95
95
90
30
95
95
95
95
95
90
100
95
|
Italian
|
Soybean
20
5
0
0
0
15
0
0
0
80
—
5
0
35
|
Velvetleaf
95
100
90
95
90
90
90
90
100
100
100
100
95
100
|
Waterhemp
100
85
100
100
90
98
100
100
85
98
80
100
100
100
|
Wheat
65
25
0
5
0
5
10
15
40
50
35
15
15
90
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
129
131
132
133
134
136
137
138
139
145
152
153
154
161
|
|
Barnyard-
90
35
45
95
90
95
100
98
95
95
70
100
95
30
|
grass
|
Blackgrass
80
90
50
50
75
90
90
90
90
60
35
95
90
45
|
Corn
40
15
10
10
5
5
55
15
15
15
15
65
5
5
|
Crabgrass,
85
80
40
65
60
95
80
80
50
55
10
100
100
40
|
Large
|
Foxtail,
98
98
98
90
80
98
100
100
95
95
90
100
100
80
|
Giant
|
Galium
98
95
98
100
98
100
100
98
100
98
100
100
100
95
|
Johnson-
25
20
25
40
5
10
20
20
25
5
5
70
75
10
|
grass
|
Lambs-
90
95
100
95
100
100
95
100
98
100
98
98
95
80
|
quarters
|
Morning-
98
95
90
95
100
98
98
98
98
100
90
98
90
85
|
glory
|
Nutsedge,
95
75
75
95
90
80
95
90
90
90
85
95
85
60
|
Yellow
|
Oilseed
90
80
90
90
98
100
90
100
100
98
100
100
98
90
|
Rape
|
Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Ragweed
95
98
100
98
98
100
100
95
100
90
90
100
95
85
|
Ryegrass,
95
95
95
100
100
90
100
95
100
100
90
95
90
85
|
Italian
|
Soybean
20
0
0
80
75
20
30
15
80
80
10
45
20
100
|
Velvetleaf
98
95
95
100
100
100
100
100
100
100
75
90
85
80
|
Waterhemp
100
100
98
100
100
100
98
100
100
100
75
100
100
95
|
Wheat
85
20
50
40
40
45
90
5
10
5
85
50
30
0
|
|
250 g ai/ha
|
Pre-
Compound
|
emergence
171
|
|
Barnyard-
95
|
grass
|
Blackgrass
90
|
Corn
40
|
Crabgrass,
80
|
Large
|
Foxtail,
—
|
Giant
|
Galium
100
|
Johnson-
35
|
grass
|
Lambs-
100
|
quarters
|
Morning-
98
|
glory
|
Nutsedge,
90
|
Yellow
|
Oilseed
90
|
Rape
|
Pigweed
100
|
Ragweed
98
|
Ryegrass,
95
|
Italian
|
Soybean
70
|
Velvetleaf
100
|
Waterhemp
100
|
Wheat
70
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
10
11
20
21
22
23
25
27
28
29
32
34
|
|
Barnyard-
25
95
5
10
60
100
5
85
70
90
90
80
85
65
|
grass
|
Blackgrass
90
95
0
50
40
90
40
90
90
90
90
85
90
85
|
Corn
0
0
0
0
5
40
0
30
0
5
30
0
0
10
|
Crabgrass,
80
98
0
40
15
85
0
75
95
95
80
55
70
25
|
Large
|
Foxtail,
100
98
0
50
65
100
55
85
90
100
100
90
85
75
|
Giant
|
Galium
95
100
5
90
95
98
95
100
95
95
95
98
100
90
|
Johnson-
5
5
0
0
0
35
0
35
5
5
5
25
10
0
|
grass
|
Lambs-
100
100
—
100
85
98
90
95
85
95
85
80
85
80
|
quarters
|
Morning-
100
98
25
100
98
100
100
95
95
100
98
95
98
85
|
glory
|
Nutsedge,
70
70
0
10
95
85
70
85
70
90
85
85
45
35
|
Yellow
|
Oilseed
—
65
0
0
0
100
5
90
5
98
85
5
90
90
|
Rape
|
Pigweed
100
100
10
100
100
100
100
100
100
98
100
100
100
100
|
Ragweed
100
100
0
80
70
100
90
95
98
100
95
85
95
90
|
Ryegrass,
100
98
25
100
95
90
95
95
95
90
95
90
95
85
|
Italian
|
Soybean
0
0
0
0
30
0
0
5
0
10
0
0
40
0
|
Velvetleaf
100
100
10
90
100
98
75
100
90
85
90
100
85
85
|
Waterhemp
100
100
100
100
100
100
100
100
100
100
85
100
100
100
|
Wheat
5
0
0
0
35
30
0
90
0
0
0
45
50
5
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
36
37
41
42
47
54
57
59
60
66
67
69
72
73
|
|
Barnyard-
65
70
85
60
85
65
100
90
85
40
40
20
55
70
|
grass
|
Blackgrass
20
90
85
90
40
55
70
90
90
35
40
60
70
85
|
Corn
0
0
5
10
0
10
0
50
30
0
0
0
0
5
|
Crabgrass,
20
20
65
80
60
75
98
85
85
75
10
10
65
75
|
Large
|
Foxtail,
85
85
85
90
85
75
90
98
100
80
98
25
85
85
|
Giant
|
Galium
100
95
98
95
98
100
95
98
98
95
90
90
95
95
|
Johnson-
5
5
35
5
0
5
0
45
40
55
10
30
80
35
|
grass
|
Lambs-
85
85
100
85
100
80
100
95
95
85
85
90
85
80
|
quarters
|
Morning-
90
90
95
98
100
95
100
100
98
80
80
85
90
90
|
glory
|
Nutsedge,
20
40
75
40
75
25
90
85
85
30
55
25
60
50
|
Yellow
|
Oilseed
60
60
40
5
0
90
30
95
90
0
0
0
80
90
|
Rape
|
Pigweed
100
100
100
100
100
100
100
100
100
100
95
100
98
100
|
Ragweed
95
95
95
95
98
95
100
100
95
90
100
90
100
95
|
Ryegrass,
35
90
95
90
45
80
70
100
95
80
85
90
90
90
|
Italian
|
Soybean
30
20
50
0
10
0
0
15
65
0
0
5
0
0
|
Velvetleaf
85
85
95
90
100
90
95
98
95
70
60
75
80
85
|
Waterhemp
100
95
100
100
100
100
100
100
100
100
65
100
90
90
|
Wheat
0
5
50
0
0
0
0
75
45
0
0
0
30
35
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
75
79
80
81
82
83
84
85
87
88
89
90
91
97
|
|
Barnyard-
50
65
75
80
70
85
60
80
65
85
25
75
20
0
|
grass
|
Blackgrass
30
60
80
90
65
80
90
90
85
90
40
50
60
0
|
Corn
0
5
10
20
20
0
0
0
0
0
0
5
10
0
|
Crabgrass,
25
20
40
90
70
70
70
80
80
80
25
75
50
0
|
Large
|
Foxtail,
70
85
85
98
90
100
90
100
90
98
65
90
90
5
|
Giant
|
Galium
90
95
95
95
90
95
95
95
98
98
98
—
98
0
|
Johnson-
20
40
30
45
60
60
5
65
40
60
0
60
0
0
|
grass
|
Lambs-
85
100
90
85
98
95
100
90
85
90
98
85
80
20
|
quarters
|
Morning-
95
98
90
90
95
95
95
95
95
95
85
98
90
20
|
glory
|
Nutsedge,
65
90
80
80
60
85
70
75
85
95
80
85
80
0
|
Yellow
|
Oilseed
90
30
50
40
0
50
80
40
85
10
30
50
100
0
|
Rape
|
Pigweed
100
100
100
95
100
100
100
100
100
95
100
100
100
65
|
Ragweed
90
98
95
95
90
95
95
98
95
95
80
85
90
0
|
Ryegrass,
90
90
90
90
85
90
85
90
90
90
90
95
95
30
|
Italian
|
Soybean
45
5
0
0
0
0
0
0
100
0
0
10
10
10
|
Velvetleaf
90
95
90
85
85
85
85
85
90
85
90
95
85
20
|
Waterhemp
100
100
100
90
100
100
100
90
100
95
40
100
65
10
|
Wheat
10
0
0
0
0
0
0
0
0
0
0
35
30
0
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
99
102
104
105
106
107
108
109
111
113
114
116
121
125
|
|
Barnyard-
55
30
40
60
85
80
35
70
55
65
60
70
55
90
|
grass
|
Blackgrass
90
45
30
55
90
10
60
85
5
55
5
30
45
55
|
Corn
10
20
15
5
10
10
5
0
0
20
5
60
0
20
|
Crabgrass,
60
30
55
75
75
75
65
70
85
75
75
50
10
75
|
Large
|
Foxtail,
65
85
75
90
100
85
85
85
—
—
—
—
90
98
|
Giant
|
Galium
98
95
90
95
95
90
95
90
100
98
100
100
98
100
|
Johnson-
0
0
20
20
5
10
30
40
0
20
0
0
0
60
|
grass
|
Lambs-
100
85
95
90
100
95
90
90
90
90
90
90
98
100
|
quarters
|
Morning-
90
85
100
100
98
95
98
90
95
98
75
85
85
95
|
glory
|
Nutsedge,
60
75
75
40
80
70
70
90
75
85
65
85
20
95
|
Yellow
|
Oilseed
90
10
85
10
30
20
90
85
100
60
100
95
30
85
|
Rape
|
Pigweed
100
98
100
100
100
100
100
100
98
100
100
100
90
100
|
Ragweed
95
90
95
98
95
85
98
95
90
85
95
95
98
98
|
Ryegrass,
100
50
90
90
85
35
90
90
85
90
90
70
95
95
|
Italian
|
Soybean
5
5
0
0
0
0
0
0
0
65
20
0
0
30
|
Velvetleaf
90
85
90
90
85
85
85
80
95
98
85
100
85
100
|
Waterhemp
98
75
100
100
80
95
100
100
75
98
65
80
85
100
|
Wheat
30
—
5
10
0
0
15
10
20
35
5
5
10
90
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
129
131
132
133
134
136
137
138
139
145
152
153
154
161
|
|
Barnyard-
100
10
35
50
70
90
90
90
75
75
30
100
90
10
|
grass
|
Blackgrass
70
40
40
50
40
70
30
40
60
60
30
95
85
5
|
Corn
15
5
0
10
10
0
10
5
10
0
10
40
5
5
|
Crabgrass,
75
60
10
35
40
60
70
70
20
55
10
98
90
20
|
Large
|
Foxtail,
95
90
85
75
70
100
95
100
85
75
65
100
100
25
|
Giant
|
Galium
100
95
90
100
98
100
98
98
100
100
95
100
98
95
|
Johnson-
10
0
55
30
5
20
20
30
35
5
0
65
50
0
|
grass
|
Lambs-
85
85
85
95
100
100
100
100
95
100
90
100
85
65
|
quarters
|
Morning-
90
85
95
90
95
98
90
98
95
98
75
98
85
75
|
glory
|
Nutsedge,
90
65
45
70
95
70
90
95
85
95
55
80
70
55
|
Yellow
|
Oilseed
90
85
30
90
90
90
50
90
98
90
95
98
98
90
|
Rape
|
Pigweed
98
100
100
100
100
100
100
100
100
100
100
100
100
98
|
Ragweed
95
98
95
95
95
100
95
98
95
85
75
98
90
30
|
Ryegrass,
95
95
95
100
100
85
100
90
100
100
90
90
90
85
|
Italian
|
Soybean
5
0
0
65
65
10
40
20
60
75
5
20
5
0
|
Velvetleaf
98
85
90
90
90
100
100
98
100
95
65
95
85
50
|
Waterhemp
100
98
95
95
98
98
95
98
100
98
85
95
95
75
|
Wheat
55
20
20
10
15
45
90
5
15
0
25
30
0
0
|
|
125 g ai/ha
|
Pre-
Compound
|
emergence
171
|
|
Barnyard-
75
|
grass
|
Blackgrass
45
|
Corn
0
|
Crabgrass,
60
|
Large
|
Foxtail,
—
|
Giant
|
Galium
98
|
Johnson-
10
|
grass
|
Lambs-
95
|
quarters
|
Morning-
95
|
glory
|
Nutsedge,
70
|
Yellow
|
Oilseed
50
|
Rape
|
Pigweed
100
|
Ragweed
95
|
Ryegrass,
95
|
Italian
|
Soybean
55
|
Velvetleaf
95
|
Waterhemp
100
|
Wheat
45
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
10
11
20
21
22
23
25
27
28
29
32
34
|
|
Barnyard-
5
70
5
0
30
100
5
85
30
80
75
35
65
55
|
grass
|
Blackgrass
90
90
0
40
5
90
20
85
85
90
90
50
90
50
|
Corn
0
0
0
0
0
15
0
0
0
0
0
0
0
0
|
Crabgrass,
40
55
0
0
15
85
0
45
75
80
60
5
35
10
|
Large
|
Foxtail,
75
100
0
35
30
100
15
85
85
100
100
75
80
65
|
Giant
|
Galium
100
100
5
90
100
98
90
100
95
95
95
95
95
95
|
Johnson-
5
0
0
0
0
10
0
5
0
5
0
5
0
0
|
grass
|
Lambs-
95
100
0
100
85
98
45
85
85
95
85
80
70
90
|
quarters
|
Morning-
100
100
0
100
98
98
85
90
95
98
98
95
90
80
|
glory
|
Nutsedge,
35
45
0
5
85
85
45
90
30
90
75
80
45
25
|
Yellow
|
Oilseed
5
20
0
0
0
100
5
90
0
95
20
0
90
25
|
Rape
|
Pigweed
100
100
0
100
100
100
100
100
100
100
100
100
100
100
|
Ragweed
80
100
0
50
45
100
75
85
95
100
90
85
90
80
|
Ryegrass,
100
98
0
95
95
90
90
90
95
90
90
90
90
85
|
Italian
|
Soybean
0
0
0
0
20
0
0
0
0
0
25
0
10
10
|
Velvetleaf
90
95
0
10
90
90
60
90
85
85
85
90
85
80
|
Waterhemp
100
100
0
100
100
95
80
100
100
85
75
100
100
100
|
Wheat
0
0
0
0
0
5
0
85
0
0
0
5
45
0
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
35
36
37
41
42
47
54
57
59
60
66
67
69
72
|
|
Barnyard-
25
25
30
40
30
20
35
90
70
40
20
20
5
20
|
grass
|
Blackgrass
55
30
30
80
85
30
55
60
90
90
30
30
30
50
|
Corn
0
0
0
0
0
0
10
—
20
10
0
0
0
0
|
Crabgrass,
5
20
5
35
70
30
40
35
70
75
65
70
5
80
|
Large
|
Foxtail,
85
75
75
80
80
50
80
80
95
85
75
80
5
70
|
Giant
|
Galium
95
100
90
100
90
95
95
90
95
95
90
90
90
90
|
Johnson-
10
5
0
50
0
0
0
0
25
20
25
20
10
25
|
grass
|
Lambs-
100
80
60
90
80
100
85
100
90
85
85
80
100
65
|
quarters
|
Morning-
98
80
80
95
98
100
90
100
100
98
85
80
85
85
|
glory
|
Nutsedge,
40
20
20
75
60
45
5
30
80
45
35
20
35
10
|
Yellow
|
Oilseed
90
60
40
50
0
0
90
0
80
85
0
0
0
35
|
Rape
|
Pigweed
80
100
98
100
100
100
100
100
100
100
100
90
100
98
|
Ragweed
40
90
90
85
90
85
90
95
95
90
85
85
70
90
|
Ryegrass,
70
30
85
95
90
20
50
65
100
95
50
40
90
90
|
Italian
|
Soybean
0
0
30
20
0
0
90
0
0
45
0
0
0
0
|
Velvetleaf
85
80
80
90
90
90
85
80
90
85
60
35
55
45
|
Waterhemp
50
100
95
95
98
98
100
98
100
100
90
80
95
90
|
Wheat
5
0
0
5
0
0
0
0
60
40
0
0
0
0
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
73
75
79
80
81
82
83
84
85
87
88
89
90
91
|
|
Barnyard-
25
25
15
65
70
55
70
25
60
35
40
15
65
15
|
grass
|
Blackgrass
80
30
50
80
80
60
80
60
85
30
90
40
40
30
|
Corn
0
5
0
10
10
0
0
0
10
10
0
0
0
10
|
Crabgrass,
30
10
25
15
75
20
65
10
85
65
80
0
70
20
|
Large
|
Foxtail,
70
45
85
85
98
85
100
75
98
80
90
60
75
65
|
Giant
|
Galium
98
90
95
95
95
90
90
95
90
95
98
98
—
98
|
Johnson-
10
20
35
5
5
65
75
5
30
25
70
75
55
0
|
grass
|
Lambs-
70
100
95
90
90
90
85
85
90
80
85
85
80
25
|
quarters
|
Morning-
90
85
95
90
85
90
90
90
90
90
90
85
85
85
|
glory
|
Nutsedge,
35
40
45
25
70
60
90
40
85
35
75
75
45
45
|
Yellow
|
Oilseed
85
70
35
30
5
0
0
0
85
30
20
0
35
98
|
Rape
|
Pigweed
100
100
100
100
95
100
100
100
100
100
100
100
100
98
|
Ragweed
95
85
95
95
95
90
100
95
90
90
85
80
90
75
|
Ryegrass,
90
90
90
70
90
85
90
85
85
90
90
80
95
70
|
Italian
|
Soybean
0
20
0
0
100
100
0
0
0
0
10
0
0
10
|
Velvetleaf
80
85
85
85
65
80
70
65
80
85
70
80
90
70
|
Waterhemp
90
100
100
100
85
100
90
100
80
100
100
50
90
60
|
Wheat
20
0
0
0
0
0
0
0
0
0
0
0
0
5
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
97
99
102
104
105
106
107
108
109
111
113
114
116
121
|
|
Barnyard-
0
15
10
25
30
45
45
35
35
20
35
10
30
10
|
grass
|
Blackgrass
0
70
50
15
50
50
5
0
30
5
50
5
5
45
|
Corn
0
20
10
0
0
0
0
10
0
0
0
5
0
0
|
Crabgrass,
0
35
5
55
50
70
30
70
65
5
35
5
20
10
|
Large
|
Foxtail,
5
35
75
85
80
95
80
85
85
—
—
—
—
55
|
Giant
|
Galium
0
—
—
85
90
90
90
90
90
80
90
98
85
90
|
Johnson-
0
0
0
20
20
5
0
5
30
0
10
0
0
0
|
grass
|
Lambs-
0
80
85
85
85
90
100
90
90
95
85
98
98
80
|
quarters
|
Morning-
30
85
75
95
90
90
85
90
85
70
95
55
80
55
|
glory
|
Nutsedge,
0
70
70
45
45
70
50
80
70
20
70
40
35
25
|
Yellow
|
Oilseed
0
40
10
30
5
0
0
90
85
98
0
98
80
85
|
Rape
|
Pigweed
35
100
85
100
100
98
100
100
100
90
75
90
100
98
|
Ragweed
0
90
75
90
90
90
90
90
90
75
95
75
90
95
|
Ryegrass,
5
90
25
85
90
70
35
85
90
90
95
85
30
90
|
Italian
|
Soybean
10
0
5
0
0
0
0
0
0
—
45
0
0
0
|
Velvetleaf
0
75
85
80
85
60
60
75
75
70
95
60
85
75
|
Waterhemp
10
100
65
90
95
75
75
90
90
65
100
75
70
95
|
Wheat
0
0
5
5
10
0
0
10
10
5
30
0
0
0
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
125
129
131
132
133
134
136
137
138
139
145
151
152
153
|
|
Barnyard-
70
70
0
5
40
40
50
85
55
55
35
85
5
100
|
grass
|
Blackgrass
55
30
40
45
60
40
80
40
55
55
30
65
5
90
|
Corn
0
5
0
0
5
0
5
10
5
0
0
10
10
0
|
Crabgrass,
45
25
20
0
30
30
5
20
40
30
50
70
0
100
|
Large
|
Foxtail,
100
90
85
70
65
75
85
85
85
65
60
98
35
100
|
Giant
|
Galium
100
98
90
90
95
98
98
98
98
90
98
95
45
98
|
Johnson-
55
5
0
10
35
5
5
5
15
35
5
25
0
50
|
grass
|
Lambs-
100
80
70
60
90
90
90
100
95
90
90
85
75
100
|
quarters
|
Morning-
95
90
55
65
85
90
95
85
90
90
80
98
40
90
|
glory
|
Nutsedge,
95
85
35
35
55
45
35
85
60
60
85
95
20
85
|
Yellow
|
Oilseed
0
50
40
85
85
90
30
90
90
98
90
98
85
100
|
Rape
|
Pigweed
100
98
100
100
100
100
100
100
98
98
98
100
100
100
|
Ragweed
100
85
95
85
75
95
98
95
100
90
65
85
40
95
|
Ryegrass,
95
90
80
90
95
100
55
95
90
100
100
90
50
95
|
Italian
|
Soybean
5
0
0
0
55
45
10
20
0
35
55
10
5
10
|
Velvetleaf
100
85
55
60
90
90
95
100
90
85
85
75
40
90
|
Waterhemp
100
95
98
85
100
98
100
98
100
100
98
45
85
95
|
Wheat
45
50
0
40
0
0
10
80
35
10
0
0
10
10
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
154
161
171
|
|
Barnyard-
80
0
35
|
grass
|
Blackgrass
50
0
40
|
Corn
5
5
0
|
Crabgrass,
85
30
45
|
Large
|
Foxtail,
95
25
—
|
Giant
|
Galium
95
70
90
|
Johnson-
45
0
5
|
grass
|
Lambs-
60
40
95
|
quarters
|
Morning-
85
40
90
|
glory
|
Nutsedge,
20
20
55
|
Yellow
|
Oilseed
85
20
5
|
Rape
|
Pigweed
95
98
60
|
Ragweed
95
15
80
|
Ryegrass,
55
40
95
|
Italian
|
Soybean
5
0
0
|
Velvetleaf
60
40
90
|
Waterhemp
85
70
95
|
Wheat
0
0
5
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
10
11
20
21
22
23
25
27
28
29
32
34
|
|
Barnyard-
5
35
0
0
5
80
5
10
0
55
45
10
20
60
|
grass
|
Blackgrass
60
85
0
35
0
90
5
45
85
85
85
50
70
5
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass,
35
55
0
0
10
35
0
5
70
55
25
5
0
0
|
Large
|
Foxtail,
55
80
0
0
5
100
5
30
75
100
85
75
55
0
|
Giant
|
Galium
90
95
0
85
90
98
90
98
90
90
95
95
90
95
|
Johnson-
0
0
0
0
0
10
0
5
0
0
0
10
0
0
|
grass
|
Lambs-
80
100
0
70
80
90
25
85
80
70
65
75
80
80
|
quarters
|
Morning-
95
98
0
100
85
95
30
85
85
85
80
80
80
70
|
glory
|
Nutsedge,
40
30
0
0
80
75
55
40
40
70
50
15
25
25
|
Yellow
|
Oilseed
0
0
0
0
0
90
0
50
0
5
0
0
25
10
|
Rape
|
Pigweed
100
100
0
0
100
100
60
100
100
98
100
100
100
100
|
Ragweed
90
65
0
15
35
95
30
85
80
80
70
80
85
80
|
Ryegrass,
95
95
0
90
75
90
90
85
90
85
85
90
85
45
|
Italian
|
Soybean
0
0
0
0
0
0
0
0
0
0
0
0
0
10
|
Velvetleaf
70
75
0
0
60
85
10
85
80
70
55
85
75
70
|
Waterhemp
100
75
10
90
90
90
75
100
100
80
70
100
98
85
|
Wheat
0
0
0
0
0
0
0
75
0
0
0
0
15
0
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
35
36
37
41
42
47
54
57
59
60
66
67
69
72
|
|
Barnyard-
5
10
10
10
0
5
15
5
30
10
0
5
0
10
|
grass
|
Blackgrass
50
0
10
70
40
0
50
30
85
90
10
60
30
40
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass,
5
70
5
30
55
0
40
0
25
20
75
10
0
60
|
Large
|
Foxtail,
60
75
65
45
75
15
70
45
80
75
70
75
0
60
|
Giant
|
Galium
90
100
100
90
90
90
95
80
98
90
90
70
50
90
|
Johnson-
10
0
0
0
0
0
0
0
5
5
10
10
20
0
|
grass
|
Lambs-
20
70
85
75
85
100
80
100
70
80
80
80
10
60
|
quarters
|
Morning-
25
80
70
85
85
90
80
100
98
85
80
70
70
75
|
glory
|
Nutsedge,
20
10
0
60
55
35
5
10
80
45
35
10
5
10
|
Yellow
|
Oilseed
90
50
0
5
0
0
70
0
65
30
0
0
0
30
|
Rape
|
Pigweed
75
90
98
75
100
100
100
100
100
100
100
75
100
90
|
Ragweed
5
85
85
85
90
50
90
70
90
80
75
60
60
85
|
Ryegrass,
65
30
50
95
85
0
55
45
100
90
55
30
85
90
|
Italian
|
Soybean
0
100
0
0
35
0
0
0
0
0
0
0
0
80
|
Velvetleaf
40
55
25
85
85
65
80
50
85
75
15
10
35
30
|
Waterhemp
40
100
90
85
80
100
98
90
95
100
85
70
85
75
|
Wheat
0
0
0
0
0
0
0
0
60
10
0
0
0
0
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
73
75
79
80
81
82
83
84
85
87
88
89
90
91
|
|
Barnyard-
10
5
10
10
30
10
50
5
35
5
35
5
35
0
|
grass
|
Blackgrass
50
20
20
70
60
50
70
60
50
40
55
5
25
0
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass,
0
75
25
10
90
25
75
10
80
10
55
20
35
0
|
Large
|
Foxtail,
55
5
65
70
80
60
85
70
90
70
85
10
75
5
|
Giant
|
Galium
90
90
95
90
90
90
90
90
90
95
90
95
—
95
|
Johnson-
0
0
10
5
25
45
65
5
40
5
50
0
50
0
|
grass
|
Lambs-
75
65
100
90
75
85
80
60
85
55
60
40
75
10
|
quarters
|
Morning-
85
70
90
85
80
85
85
85
85
85
85
80
85
25
|
glory
|
Nutsedge,
0
15
25
20
60
35
85
15
70
10
40
60
55
10
|
Yellow
|
Oilseed
90
30
0
0
0
0
0
0
5
30
20
0
30
80
|
Rape
|
Pigweed
95
85
100
100
98
95
100
100
100
75
90
95
100
70
|
Ragweed
85
80
90
90
85
85
85
85
80
90
90
30
80
35
|
Ryegrass,
75
90
20
35
80
80
90
80
85
35
85
20
90
30
|
Italian
|
Soybean
0
0
0
0
0
0
30
0
0
0
0
0
0
0
|
Velvetleaf
25
35
80
55
35
65
35
40
50
55
10
70
85
55
|
Waterhemp
85
100
100
100
85
100
60
100
60
100
100
75
75
25
|
Wheat
0
0
0
0
0
0
0
0
0
0
0
0
5
0
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
97
99
102
104
105
106
107
108
109
111
113
114
116
121
|
|
Barnyard-
0
5
5
10
0
25
15
5
10
10
10
5
5
5
|
grass
|
Blackgrass
0
50
0
5
20
10
0
10
35
0
10
0
0
10
|
Corn
5
5
5
5
0
0
0
5
5
0
0
0
0
0
|
Crabgrass,
0
30
0
40
20
70
30
5
40
5
0
0
0
0
|
Large
|
Foxtail,
0
40
30
75
60
85
60
65
65
—
—
—
—
20
|
Giant
|
Galium
0
—
—
90
85
90
90
90
90
80
100
98
60
90
|
Johnson-
0
0
0
10
10
5
0
0
0
0
0
0
0
0
|
grass
|
Lambs-
0
25
70
85
95
90
90
85
80
90
90
90
65
60
|
quarters
|
Morning-
25
80
45
80
85
85
80
80
85
50
85
25
55
25
|
glory
|
Nutsedge,
0
20
15
30
40
60
30
35
40
0
55
10
0
10
|
Yellow
|
Oilseed
0
0
0
5
0
0
0
5
5
0
0
30
85
0
|
Rape
|
Pigweed
5
95
75
100
98
98
100
100
100
98
70
98
95
100
|
Ragweed
0
70
70
85
90
85
75
75
95
60
65
55
85
35
|
Ryegrass,
5
90
15
55
40
50
15
60
70
10
95
40
5
75
|
Italian
|
Soybean
15
0
0
0
0
0
75
0
0
—
0
0
—
0
|
Velvetleaf
0
60
65
40
60
40
30
50
60
65
60
45
70
60
|
Waterhemp
0
85
75
75
90
70
75
75
80
50
85
50
55
70
|
Wheat
0
0
0
5
0
15
0
0
0
0
0
0
0
0
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
125
129
131
132
133
134
136
137
138
139
144
145
151
152
|
|
Barnyard-
55
15
0
0
0
5
25
35
30
20
35
10
70
5
|
grass
|
Blackgrass
50
5
0
20
30
20
70
30
45
50
90
10
60
5
|
Corn
0
0
0
0
5
0
0
0
5
0
0
0
10
15
|
Crabgrass,
40
5
0
0
0
5
0
20
0
5
60
5
30
0
|
Large
|
Foxtail,
95
85
35
40
30
25
75
65
80
35
90
35
85
0
|
Giant
|
Galium
100
95
85
90
95
100
90
98
95
90
100
90
95
50
|
Johnson-
40
5
0
15
5
0
5
0
10
5
60
10
0
0
|
grass
|
Lambs-
90
85
60
50
90
75
95
90
95
100
100
90
80
50
|
quarters
|
Morning-
90
85
35
40
45
75
80
70
80
85
90
75
90
10
|
glory
|
Nutsedge,
65
55
10
10
20
30
5
55
5
65
40
35
70
5
|
Yellow
|
Oilseed
85
5
20
70
5
55
10
0
85
20
70
5
98
50
|
Rape
|
Pigweed
100
100
60
100
100
75
100
100
100
70
100
70
100
80
|
Ragweed
95
70
65
70
70
70
95
80
95
75
98
55
90
85
|
Ryegrass,
85
90
10
45
90
98
50
85
55
95
100
100
90
10
|
Italian
|
Soybean
0
0
0
0
5
40
10
30
0
25
5
0
20
0
|
Velvetleaf
95
70
0
60
55
75
75
80
85
60
90
40
60
15
|
Waterhemp
98
90
95
90
80
90
98
85
95
100
100
85
35
20
|
Wheat
40
35
0
25
0
0
0
15
0
0
90
0
0
0
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
153
154
161
171
|
|
Barnyard-
85
65
0
5
|
grass
|
Blackgrass
90
5
5
30
|
Corn
0
5
0
0
|
Crabgrass,
80
70
30
0
|
Large
|
Foxtail,
98
85
10
—
|
Giant
|
Galium
95
98
80
90
|
Johnson-
25
10
0
0
|
grass
|
Lambs-
95
15
0
98
|
quarters
|
Morning-
95
45
10
85
|
glory
|
Nutsedge,
80
0
0
45
|
Yellow
|
Oilseed
95
80
10
0
|
Rape
|
Pigweed
100
55
75
70
|
Ragweed
95
80
40
65
|
Ryegrass,
90
40
5
90
|
Italian
|
Soybean
20
0
0
—
|
Velvetleaf
85
40
0
70
|
Waterhemp
80
30
20
85
|
Wheat
0
0
0
0
|
|
16 g ai/ha
|
Pre-
Compounds
|
emergence
35
144
151
|
|
Barnyard-
5
5
20
|
grass
|
Blackgrass
40
70
60
|
Corn
0
0
30
|
Crabgrass,
0
25
10
|
Large
|
Foxtail,
25
75
75
|
Giant
|
Galium
90
95
95
|
Johnson-
0
25
0
|
grass
|
Lambs-
5
65
80
|
quarters
|
Morning-
25
80
90
|
glory
|
Nutsedge,
20
25
30
|
Yellow
|
Oilseed
5
5
85
|
Rape
|
Pigweed
75
100
95
|
Ragweed
0
95
85
|
Ryegrass,
50
100
50
|
Italian
|
Soybean
0
0
0
|
Velvetleaf
0
85
55
|
Waterhemp
40
100
10
|
Wheat
0
70
0
|
|
8 g ai/ha
|
Pre-
Compounds
|
emergence
35
144
151
|
|
Barnyard-
0
0
5
|
grass
|
Blackgrass
5
55
30
|
Corn
0
0
20
|
Crabgrass,
0
5
0
|
Large
|
Foxtail,
5
60
40
|
Giant
|
Galium
90
95
98
|
Johnson-
0
25
0
|
grass
|
Lambs-
5
35
60
|
quarters
|
Morning-
10
60
80
|
glory
|
Nutsedge,
0
5
40
|
Yellow
|
Oilseed
0
0
85
|
Rape
|
Pigweed
40
100
70
|
Ragweed
0
90
55
|
Ryegrass,
40
95
15
|
Italian
|
Soybean
0
0
0
|
Velvetleaf
0
70
40
|
Waterhemp
—
100
5
|
Wheat
0
55
0
|
|
4 g ai/ha
|
Pre-
Compound
|
emergence
144
|
|
Barnyard-
0
|
grass
|
Blackgrass
30
|
Corn
0
|
Crabgrass,
0
|
Large
|
Foxtail,
30
|
Giant
|
Galium
90
|
Johnson-
0
|
grass
|
Lambs-
25
|
quarters
|
Morning-
25
|
glory
|
Nutsedge,
5
|
Yellow
|
Oilseed
0
|
Rape
|
Pigweed
75
|
Ragweed
70
|
Ryegrass,
80
|
Italian
|
Soybean
10
|
Velvetleaf
25
|
Waterhemp
80
|
Wheat
0
|
|
Test D
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.
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 D
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
1
2
11
20
21
22
23
25
27
28
34
35
36
41
|
|
Barley,
10
5
10
0
30
15
30
10
10
10
5
15
10
20
|
Spring
|
Barley,
10
10
40
0
40
5
30
10
5
5
20
15
10
35
|
Winter
|
Blackgrass
80
90
70
60
90
70
80
80
90
85
75
85
70
75
|
Bluegrass
5
15
15
40
50
25
40
40
40
50
20
40
35
35
|
Bromegrass,
20
20
50
15
80
25
75
65
70
70
70
30
65
45
|
Downy
|
Buckwheat,
100
100
95
100
100
100
100
100
100
100
100
100
100
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
70
75
55
55
95
65
90
85
90
85
85
80
80
80
|
Chamomile
100
100
90
100
100
100
100
100
100
95
100
100
100
100
|
Chickweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Deadnettle
70
60
100
65
100
70
85
45
60
70
100
80
100
100
|
Field Poppy
95
100
100
100
100
100
100
100
100
100
100
100
100
95
|
Field Violet
95
80
90
45
100
95
75
95
85
90
95
98
90
100
|
Foxtail,
85
100
70
70
95
75
90
75
80
90
70
95
90
65
|
Green
|
Galium
100
100
90
100
100
98
100
100
100
100
100
100
100
100
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
100
70
100
100
85
100
80
100
75
75
95
70
100
100
|
Lambs-
100
100
85
95
95
98
80
95
85
90
100
98
100
85
|
quarters
|
Mustard,
65
55
95
100
100
100
100
85
75
70
100
100
100
100
|
Wild
|
Oat, Wild
95
100
98
75
100
100
95
90
98
95
95
98
95
85
|
Oilseed Rape
60
70
55
5
100
100
85
60
85
85
90
100
100
55
|
Pigweed
100
95
100
100
98
100
100
100
95
90
100
98
100
85
|
Radish, Wild
60
60
85
65
100
85
100
75
90
95
95
100
100
95
|
Russian
—
—
—
98
85
85
80
90
70
85
85
95
90
75
|
Thistle
|
Ryegrass,
85
90
90
90
80
90
85
90
85
85
95
90
90
90
|
Italian
|
Speedwell
70
90
100
100
100
100
95
80
100
100
100
100
100
100
|
Wheat,
15
25
25
20
50
15
60
20
20
20
45
30
10
40
|
Spring
|
Wheat,
5
10
25
25
40
15
70
20
10
15
25
20
15
35
|
Winter
|
Windgrass
70
70
20
40
85
55
85
85
90
85
75
85
75
75
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
42
47
52
54
57
59
60
66
67
69
72
73
75
79
|
|
Barley,
10
0
0
10
10
60
50
15
20
5
15
40
0
10
|
Spring
|
Barley,
10
15
0
30
25
60
50
5
10
5
35
35
5
5
|
Winter
|
Blackgrass
85
65
40
75
75
85
90
75
95
65
80
90
70
50
|
Bluegrass
35
15
30
35
15
75
60
35
30
25
55
65
15
15
|
Bromegrass,
70
5
10
75
35
85
80
70
70
40
75
85
30
20
|
Downy
|
Buckwheat,
100
100
100
100
100
100
100
100
100
98
100
100
100
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
98
—
—
—
—
|
Thistle
|
Canarygrass
80
0
0
75
25
90
90
85
95
75
85
90
50
45
|
Chamomile
100
—
100
100
100
100
100
100
100
80
100
100
100
100
|
Chickweed
100
100
100
100
100
100
100
100
100
98
100
100
100
100
|
Deadnettle
55
30
35
100
100
100
95
40
60
80
100
100
100
40
|
Field Poppy
100
100
100
100
100
100
100
95
100
80
100
100
100
98
|
Field Violet
90
—
75
90
85
95
85
95
95
98
95
90
100
95
|
Foxtail,
80
80
40
80
90
85
75
98
100
15
75
80
60
80
|
Green
|
Galium
100
80
100
100
98
100
100
100
100
100
100
100
100
100
|
Geranium,
—
—
—
—
—
—
—
—
—
65
—
—
—
—
|
Cutleaf
|
Kochia
100
100
65
100
75
100
95
100
50
98
100
100
100
95
|
Lambs-
90
70
90
100
85
95
80
100
100
100
100
100
100
100
|
quarters
|
Mustard,
80
25
100
100
40
100
100
70
65
80
100
100
100
50
|
Wild
|
Oat, Wild
95
40
15
90
85
98
100
100
100
85
98
100
80
85
|
Oilseed Rape
70
70
80
100
65
90
80
75
90
20
90
95
100
30
|
Pigweed
100
100
80
100
100
100
100
100
100
100
100
100
100
100
|
Radish, Wild
65
20
85
100
90
100
95
45
95
75
95
100
100
65
|
Russian
90
—
55
100
—
85
85
80
85
70
85
85
85
65
|
Thistle
|
Ryegrass,
85
45
80
95
85
90
95
98
100
85
100
98
98
90
|
Italian
|
Speedwell
45
50
100
100
100
100
100
75
100
100
80
100
100
65
|
Wheat,
20
15
5
25
10
80
55
5
5
0
70
85
15
5
|
Spring
|
Wheat,
15
5
15
30
15
80
40
0
0
0
60
75
0
0
|
Winter
|
Windgrass
98
15
5
75
15
85
98
100
90
55
85
85
65
65
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
80
81
82
83
84
85
87
88
90
104
105
108
109
126
|
|
Barley,
25
10
5
10
10
20
5
15
40
15
15
20
25
10
|
Spring
|
Barley,
15
10
0
15
0
10
5
10
35
15
15
15
20
0
|
Winter
|
Blackgrass
90
85
80
80
85
90
90
95
65
70
65
75
75
45
|
Bluegrass
45
40
35
25
35
40
45
35
30
30
25
35
45
15
|
Bromegrass,
75
75
60
70
75
60
65
65
55
65
65
65
75
25
|
Downy
|
Buckwheat,
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
98
—
—
—
—
100
|
Thistle
|
Canarygrass
90
100
85
90
80
90
90
95
75
85
80
80
90
75
|
Chamomile
100
100
100
100
100
85
100
95
100
100
100
100
100
100
|
Chickweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Deadnettle
50
60
35
60
40
45
60
45
100
85
30
90
95
85
|
Field Poppy
100
100
100
100
100
95
100
100
90
80
80
75
85
85
|
Field Violet
100
100
100
100
100
90
100
80
100
98
100
100
100
100
|
Foxtail,
95
100
90
100
95
85
90
80
75
90
80
95
85
25
|
Green
|
Galium
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Geranium,
—
—
—
—
—
—
—
—
95
—
—
—
—
90
|
Cutleaf
|
Kochia
100
95
100
90
100
75
95
70
100
100
100
100
100
100
|
Lambs-
100
100
100
100
100
95
100
90
100
100
95
100
100
100
|
quarters
|
Mustard,
100
80
70
70
75
80
60
75
100
90
75
100
100
100
|
Wild
|
Oat, Wild
100
98
95
95
100
100
100
100
100
100
100
100
100
90
|
Oilseed Rape
75
85
80
95
75
80
75
80
70
95
60
100
85
85
|
Pigweed
100
100
100
100
100
85
100
90
100
100
100
100
100
98
|
Radish, Wild
65
100
60
100
45
80
60
85
95
95
70
90
100
95
|
Russian
80
90
85
85
85
90
75
85
90
85
50
90
90
85
|
Thistle
|
Ryegrass,
100
95
90
90
100
90
98
95
100
95
95
100
100
90
|
Italian
|
Speedwell
80
100
85
100
80
100
80
100
100
70
75
80
100
100
|
Wheat,
30
20
5
20
10
20
10
35
50
30
25
30
30
5
|
Spring
|
Wheat,
15
5
0
10
0
10
5
5
40
25
20
20
35
0
|
Winter
|
Windgrass
98
95
85
95
85
85
100
85
90
85
85
85
90
55
|
|
250 g ai/ha
|
Post-
Compounds
|
emergence
129
153
|
|
Barley,
30
30
|
Spring
|
Barley,
35
25
|
Winter
|
Blackgrass
75
80
|
Bluegrass
30
40
|
Bromegrass,
80
70
|
Downy
|
Buckwheat,
100
100
|
Wild
|
Canada
100
100
|
Thistle
|
Canarygrass
80
85
|
Chamomile
100
100
|
Chickweed
100
100
|
Deadnettle
95
90
|
Field Poppy
98
100
|
Field Violet
75
100
|
Foxtail,
95
85
|
Green
|
Galium
100
100
|
Geranium,
75
98
|
Cutleaf
|
Kochia
85
35
|
Lambs-
100
75
|
quarters
|
Mustard,
100
100
|
Wild
|
Oat, Wild
100
98
|
Oilseed Rape
70
98
|
Pigweed
100
85
|
Radish, Wild
98
100
|
Russian
90
55
|
Thistle
|
Ryegrass,
90
90
|
Italian
|
Speedwell
75
100
|
Wheat,
70
50
|
Spring
|
Wheat,
55
35
|
Winter
|
Windgrass
90
75
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
1
2
11
20
21
22
23
25
27
28
34
35
36
41
|
|
Barley,
5
5
10
0
10
15
25
0
5
5
0
10
0
10
|
Spring
|
Barley,
5
15
25
0
30
0
25
0
5
5
0
0
5
5
|
Winter
|
Blackgrass
70
80
70
50
85
45
75
80
90
85
70
75
45
70
|
Bluegrass
5
5
5
30
35
25
35
30
30
35
15
35
40
25
|
Bromegrass,
10
10
25
10
75
25
60
50
55
40
40
25
55
35
|
Downy
|
Buckwheat,
100
100
60
100
100
100
100
100
100
100
100
100
100
95
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
50
55
30
45
85
40
85
80
85
80
75
70
55
80
|
Chamomile
85
90
75
100
100
85
85
100
95
90
100
100
100
80
|
Chickweed
90
100
80
100
100
98
100
100
100
100
100
100
100
95
|
Deadnettle
35
60
100
55
95
45
75
20
30
35
100
20
100
80
|
Field Poppy
100
100
80
100
100
100
100
100
100
100
100
100
90
75
|
Field Violet
90
75
75
25
100
75
75
85
75
85
95
75
90
90
|
Foxtail,
75
95
65
40
85
70
80
70
80
85
55
95
80
50
|
Green
|
Galium
95
100
90
100
100
98
100
100
100
100
100
95
100
100
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
95
65
85
85
75
100
75
100
55
50
85
65
100
85
|
Lambs-
90
95
80
90
90
95
75
90
85
90
100
98
100
75
|
quarters
|
Mustard,
40
40
75
100
100
100
100
70
30
70
100
100
100
100
|
Wild
|
Oat, Wild
80
90
85
60
85
85
95
90
90
90
95
85
85
85
|
Oilseed Rape
35
55
20
5
100
95
65
45
70
65
75
100
95
25
|
Pigweed
100
85
95
100
90
98
85
95
95
100
100
85
100
80
|
Radish, Wild
30
65
60
70
100
100
100
65
85
85
90
100
100
90
|
Russian
—
—
—
80
80
75
75
80
70
80
80
85
85
75
|
Thistle
|
Ryegrass,
85
85
85
80
85
85
85
85
85
80
95
80
90
85
|
Italian
|
Speedwell
60
80
100
100
100
65
75
25
100
100
100
80
100
100
|
Wheat,
10
10
25
15
40
10
60
15
10
10
15
25
0
30
|
Spring
|
Wheat,
0
5
15
15
35
15
55
5
5
5
15
15
5
25
|
Winter
|
Windgrass
50
55
15
30
85
35
75
85
80
85
65
70
70
60
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
42
47
52
54
57
59
60
66
67
69
72
73
75
79
|
|
Barley,
5
0
5
0
10
40
40
5
10
0
10
30
0
5
|
Spring
|
Barley,
0
15
0
5
25
45
40
0
5
5
30
20
0
0
|
Winter
|
Blackgrass
80
35
15
70
55
85
85
75
85
35
75
80
65
40
|
Bluegrass
20
10
30
25
15
55
35
30
20
15
40
55
15
10
|
Bromegrass,
40
5
0
55
25
70
65
65
65
20
65
70
15
10
|
Downy
|
Buckwheat,
100
90
100
100
85
100
100
100
100
95
100
100
100
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
100
—
—
—
—
|
Thistle
|
Canarygrass
80
0
0
65
15
90
85
70
85
70
80
80
30
40
|
Chamomile
100
—
100
100
100
85
100
100
100
80
85
90
85
100
|
Chickweed
100
95
90
100
100
100
100
100
100
90
100
100
100
100
|
Deadnettle
35
30
35
100
85
90
95
35
40
75
100
100
95
20
|
Field Poppy
100
100
90
100
100
95
85
95
100
70
100
100
100
95
|
Field Violet
90
—
75
95
75
95
100
95
90
85
95
90
95
85
|
Foxtail,
65
70
10
70
75
75
65
90
100
15
70
75
55
75
|
Green
|
Galium
100
75
98
100
90
100
100
100
100
90
100
100
95
100
|
Geranium,
—
—
—
—
—
—
—
—
—
55
—
—
—
—
|
Cutleaf
|
Kochia
95
95
55
100
65
95
90
100
40
95
100
100
100
85
|
Lambs-
85
70
75
95
75
90
80
100
100
95
90
100
100
90
|
quarters
|
Mustard,
70
15
90
100
30
100
98
55
40
80
100
100
100
40
|
Wild
|
Oat, Wild
85
20
5
90
65
95
95
100
100
80
95
95
85
80
|
Oilseed Rape
60
55
65
100
65
85
75
65
85
10
80
75
95
20
|
Pigweed
90
100
75
100
100
100
100
100
85
98
100
100
100
100
|
Radish, Wild
20
5
80
100
100
100
95
30
70
60
90
100
100
0
|
Russian
85
—
45
90
—
85
80
75
75
50
80
80
85
55
|
Thistle
|
Ryegrass,
85
30
75
90
75
90
90
95
98
80
95
95
95
85
|
Italian
|
Speedwell
45
40
100
100
25
100
90
70
75
100
100
100
100
35
|
Wheat,
15
15
0
15
10
70
40
0
0
0
60
70
5
0
|
Spring
|
Wheat,
10
10
15
25
10
55
35
0
0
0
50
65
0
0
|
Winter
|
Windgrass
90
15
5
70
10
80
90
85
90
35
80
75
40
35
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
80
81
82
83
84
85
87
88
90
104
105
108
109
126
|
|
Barley,
15
0
0
5
5
15
0
5
35
10
10
15
10
10
|
Spring
|
Barley,
5
0
0
0
5
5
5
5
25
10
10
10
5
0
|
Winter
|
Blackgrass
90
80
75
75
85
90
85
90
55
65
65
65
65
30
|
Bluegrass
35
30
30
15
30
25
45
30
25
20
20
25
25
15
|
Bromegrass,
70
65
60
50
65
35
65
35
40
55
25
40
60
20
|
Downy
|
Buckwheat,
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
100
—
—
—
—
98
|
Thistle
|
Canarygrass
85
95
75
80
80
85
85
85
75
80
75
80
80
45
|
Chamomile
100
100
100
100
100
90
100
95
98
95
100
95
95
98
|
Chickweed
100
100
95
100
90
100
100
100
98
100
100
100
100
100
|
Deadnettle
35
35
25
55
20
40
35
35
100
70
20
75
70
80
|
Field Poppy
100
100
95
100
90
80
85
100
75
75
80
65
75
75
|
Field Violet
95
100
100
100
100
75
100
80
100
95
95
100
100
90
|
Foxtail,
90
95
85
90
85
85
80
80
70
85
75
75
75
25
|
Green
|
Galium
95
100
100
100
100
100
100
100
100
100
95
100
100
100
|
Geranium,
—
—
—
—
—
—
—
—
75
—
—
—
—
80
|
Cutleaf
|
Kochia
100
90
100
80
100
70
90
60
100
100
95
100
100
95
|
Lambs-
100
100
95
100
95
95
100
90
100
100
90
100
95
100
|
quarters
|
Mustard,
70
60
40
65
70
30
25
25
100
85
40
95
90
90
|
Wild
|
Oat, Wild
100
95
95
90
98
95
98
100
98
95
95
100
95
80
|
Oilseed Rape
65
75
60
75
70
70
65
75
15
90
25
75
75
75
|
Pigweed
100
100
100
100
95
85
100
75
95
100
100
100
100
98
|
Radish, Wild
50
95
50
100
55
75
30
85
75
90
20
85
90
75
|
Russian
80
90
75
80
75
80
65
80
75
65
50
75
75
80
|
Thistle
|
Ryegrass,
98
95
90
90
98
85
95
90
95
95
90
95
95
90
|
Italian
|
Speedwell
85
95
85
75
75
80
75
85
100
55
65
70
75
100
|
Wheat,
15
0
0
5
0
15
5
5
40
20
20
20
25
0
|
Spring
|
Wheat,
5
5
0
5
0
0
0
5
40
20
10
20
25
0
|
Winter
|
Windgrass
95
90
80
90
80
80
85
85
70
85
80
75
80
30
|
|
125 g ai/ha
|
Post-
Compounds
|
emergence
129
153
|
|
Barley,
30
15
|
Spring
|
Barley,
30
10
|
Winter
|
Blackgrass
60
75
|
Bluegrass
20
30
|
Bromegrass,
65
65
|
Downy
|
Buckwheat,
100
100
|
Wild
|
Canada
100
100
|
Thistle
|
Canarygrass
75
80
|
Chamomile
100
100
|
Chickweed
100
85
|
Deadnettle
70
80
|
Field Poppy
80
100
|
Field Violet
70
95
|
Foxtail,
85
85
|
Green
|
Galium
100
100
|
Geranium,
75
90
|
Cutleaf
|
Kochia
80
30
|
Lambs-
95
65
|
quarters
|
Mustard,
98
100
|
Wild
|
Oat, Wild
95
90
|
Oilseed Rape
15
85
|
Pigweed
100
80
|
Radish, Wild
80
100
|
Russian
85
45
|
Thistle
|
Ryegrass,
90
90
|
Italian
|
Speedwell
65
90
|
Wheat,
50
40
|
Spring
|
Wheat,
40
25
|
Winter
|
Windgrass
55
65
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
1
2
11
20
21
22
23
25
27
28
34
35
36
41
|
|
Barley,
5
0
0
0
5
0
15
0
0
5
0
0
0
5
|
Spring
|
Barley,
5
10
20
0
10
0
15
0
0
0
0
0
0
5
|
Winter
|
Blackgrass
50
70
40
40
85
20
70
75
80
80
40
65
35
65
|
Bluegrass
5
10
5
25
30
15
35
20
25
30
15
25
15
30
|
Bromegrass,
10
10
15
10
60
10
45
25
25
25
30
25
20
20
|
Downy
|
Buckwheat,
75
95
45
100
100
98
100
100
100
100
100
100
100
90
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
35
40
20
30
80
35
75
80
80
75
65
30
40
70
|
Chamomile
75
80
65
95
95
80
85
95
90
90
80
100
95
75
|
Chickweed
80
95
90
100
100
95
100
98
100
100
100
100
100
98
|
Deadnettle
35
60
100
35
100
10
65
10
5
35
100
20
100
100
|
Field Poppy
95
95
85
60
100
85
100
80
100
90
100
100
70
80
|
Field Violet
75
85
65
15
95
70
45
75
70
75
100
75
85
90
|
Foxtail,
65
80
25
35
80
45
75
65
80
75
45
90
45
55
|
Green
|
Galium
90
100
85
75
100
90
100
100
100
100
100
98
100
100
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
85
60
75
65
45
95
75
95
55
40
85
20
95
95
|
Lambs-
90
90
80
85
85
85
75
90
85
85
95
100
95
65
|
quarters
|
Mustard,
30
35
70
100
100
95
95
40
40
45
85
100
100
100
|
Wild
|
Oat, Wild
70
80
75
25
85
85
75
80
85
85
85
90
80
80
|
Oilseed Rape
15
45
15
0
100
30
60
30
65
65
70
98
85
5
|
Pigweed
90
80
65
100
85
95
75
100
85
90
100
80
100
80
|
Radish, Wild
20
55
30
40
100
75
75
35
75
100
85
100
90
80
|
Russian
—
—
—
75
75
70
75
75
75
75
80
75
85
70
|
Thistle
|
Ryegrass,
75
80
85
70
80
80
80
85
85
80
95
75
80
85
|
Italian
|
Speedwell
55
65
100
15
100
60
100
15
70
85
75
75
90
100
|
Wheat,
0
0
15
15
30
10
50
0
5
5
10
20
0
20
|
Spring
|
Wheat,
0
0
15
10
25
5
40
0
5
5
25
15
0
20
|
Winter
|
Windgrass
25
25
10
30
80
20
70
75
75
80
50
65
50
55
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
42
47
52
54
57
59
60
66
67
69
72
73
75
79
|
|
Barley,
0
0
0
0
10
30
25
0
5
0
5
25
0
5
|
Spring
|
Barley,
0
10
0
0
30
30
25
0
0
0
20
15
0
0
|
Winter
|
Blackgrass
75
25
15
40
45
80
80
70
75
30
70
70
20
20
|
Bluegrass
20
10
5
15
15
40
25
25
15
15
35
30
10
10
|
Bromegrass,
20
0
0
55
20
70
55
60
60
15
55
55
0
5
|
Downy
|
Buckwheat,
95
75
100
100
85
100
95
100
100
70
100
100
100
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
100
—
—
—
—
|
Thistle
|
Canarygrass
75
0
0
55
5
80
80
65
85
25
50
70
15
20
|
Chamomile
70
—
100
100
100
80
80
90
100
70
80
85
90
95
|
Chickweed
100
95
100
100
100
98
100
85
100
80
100
95
100
95
|
Deadnettle
25
20
25
100
90
80
75
15
30
65
90
90
90
15
|
Field Poppy
85
100
80
100
100
75
75
85
100
70
90
100
100
85
|
Field Violet
80
—
65
75
70
80
95
95
80
80
95
95
100
75
|
Foxtail,
50
60
5
65
75
70
40
80
90
10
65
70
25
70
|
Green
|
Galium
100
75
95
100
90
100
100
100
100
85
100
100
95
100
|
Geranium,
—
—
—
—
—
—
—
—
—
30
—
—
—
—
|
Cutleaf
|
Kochia
90
70
20
95
55
95
85
95
35
85
95
80
100
80
|
Lambs-
85
50
75
95
75
85
80
95
100
95
95
95
100
80
|
quarters
|
Mustard,
70
0
75
100
30
100
75
40
35
35
100
100
100
20
|
Wild
|
Oat, Wild
85
15
5
85
25
90
90
95
98
75
85
95
70
70
|
Oilseed Rape
50
20
5
95
25
70
70
20
80
10
70
70
95
5
|
Pigweed
90
75
40
100
85
85
95
100
80
80
100
100
100
100
|
Radish, Wild
10
10
65
100
100
95
75
25
65
20
80
95
100
0
|
Russian
75
—
35
80
—
80
80
80
60
20
75
80
80
55
|
Thistle
|
Ryegrass,
80
10
50
85
50
90
90
95
90
75
95
85
95
75
|
Italian
|
Speedwell
50
10
85
100
15
100
80
70
75
85
75
100
100
30
|
Wheat,
10
10
0
0
10
45
35
0
0
0
50
55
0
0
|
Spring
|
Wheat,
5
5
10
5
10
40
30
0
0
0
35
35
0
0
|
Winter
|
Windgrass
75
10
5
45
10
80
85
80
85
15
75
70
15
20
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
80
81
82
83
84
85
87
88
90
104
105
108
109
126
|
|
Barley,
10
0
5
5
0
0
0
0
25
10
5
10
5
0
|
Spring
|
Barley,
0
0
0
0
0
0
0
0
15
10
10
5
0
5
|
Winter
|
Blackgrass
80
75
70
70
75
80
75
85
35
40
25
45
30
20
|
Bluegrass
35
20
20
10
20
20
25
25
15
10
10
10
15
10
|
Bromegrass,
65
35
45
35
65
30
65
25
30
30
20
30
30
10
|
Downy
|
Buckwheat,
100
100
100
100
80
100
100
85
90
95
95
100
95
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
100
—
—
—
—
100
|
Thistle
|
Canarygrass
80
85
55
75
65
85
80
80
45
65
50
50
55
35
|
Chamomile
95
100
100
100
98
75
100
100
75
85
85
85
85
95
|
Chickweed
100
100
90
100
90
100
90
95
90
100
90
100
100
98
|
Deadnettle
25
35
10
25
10
15
15
15
80
50
10
50
50
70
|
Field Poppy
80
100
85
100
80
90
85
85
70
65
75
55
50
55
|
Field Violet
85
85
100
80
100
65
85
75
98
90
90
95
95
85
|
Foxtail,
90
95
80
90
80
80
75
75
55
70
70
70
65
10
|
Green
|
Galium
95
100
100
100
100
95
100
100
100
90
95
95
100
100
|
Geranium,
—
—
—
—
—
—
—
—
65
—
—
—
—
40
|
Cutleaf
|
Kochia
100
85
95
75
95
65
90
55
100
95
95
100
100
80
|
Lambs-
100
100
95
100
90
85
100
80
90
100
95
95
95
98
|
quarters
|
Mustard,
50
60
35
25
50
25
35
20
95
75
25
75
85
80
|
Wild
|
Oat, Wild
98
90
90
85
95
85
95
95
90
90
85
95
95
70
|
Oilseed Rape
55
70
45
70
45
70
40
65
5
75
15
70
70
65
|
Pigweed
100
100
100
100
95
80
100
75
90
100
100
100
85
100
|
Radish, Wild
50
90
20
90
40
65
20
60
75
75
15
75
75
70
|
Russian
70
85
75
80
70
75
65
75
75
60
45
70
75
40
|
Thistle
|
Ryegrass,
95
90
85
85
95
85
95
90
90
95
85
90
85
90
|
Italian
|
Speedwell
75
80
75
70
70
70
75
65
100
35
50
65
60
65
|
Wheat,
10
0
0
0
0
0
0
0
35
15
10
20
15
0
|
Spring
|
Wheat,
0
0
0
0
0
0
0
10
35
15
5
15
15
0
|
Winter
|
Windgrass
90
80
75
85
75
70
85
80
50
75
70
70
65
20
|
|
62 g ai/ha
|
Post-
Compounds
|
emergence
129
153
|
|
Barley,
25
5
|
Spring
|
Barley,
20
5
|
Winter
|
Blackgrass
45
70
|
Bluegrass
15
15
|
Bromegrass,
40
35
|
Downy
|
Buckwheat,
100
95
|
Wild
|
Canada
100
98
|
Thistle
|
Canarygrass
55
75
|
Chamomile
98
95
|
Chickweed
100
85
|
Deadnettle
40
75
|
Field Poppy
75
95
|
Field Violet
70
90
|
Foxtail,
80
80
|
Green
|
Galium
100
100
|
Geranium,
70
90
|
Cutleaf
|
Kochia
70
15
|
Lambs-
90
65
|
quarters
|
Mustard,
80
98
|
Wild
|
Oat, Wild
90
85
|
Oilseed Rape
5
85
|
Pigweed
98
75
|
Radish, Wild
75
85
|
Russian
80
20
|
Thistle
|
Ryegrass,
85
90
|
Italian
|
Speedwell
60
75
|
Wheat,
35
30
|
Spring
|
Wheat,
35
15
|
Winter
|
Windgrass
35
30
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
1
2
11
20
21
22
25
27
28
34
35
36
41
42
|
|
Barley,
0
0
0
0
0
0
0
0
5
0
0
0
0
0
|
Spring
|
Barley,
5
10
20
0
0
0
0
0
0
0
0
0
0
0
|
Winter
|
Blackgrass
40
65
25
15
80
15
65
75
75
25
30
25
55
75
|
Bluegrass
0
5
5
10
20
10
10
15
20
10
35
10
15
15
|
Bromegrass,
0
10
15
0
45
10
5
15
15
20
5
10
10
0
|
Downy
|
Buckwheat,
70
85
45
80
100
90
80
100
100
100
95
100
80
80
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
20
25
10
10
80
20
70
75
75
30
20
15
55
50
|
Chamomile
65
70
40
70
90
80
75
80
85
75
100
95
75
75
|
Chickweed
80
85
45
90
90
85
98
95
100
95
90
100
98
95
|
Deadnettle
35
60
75
25
90
10
5
5
10
95
15
80
85
5
|
Field Poppy
95
75
35
30
85
75
70
85
80
100
100
60
55
65
|
Field Violet
85
60
65
5
95
70
65
75
80
75
65
70
100
70
|
Foxtail,
50
70
5
15
70
15
60
70
65
40
75
35
45
35
|
Green
|
Galium
80
85
85
70
100
90
100
100
100
95
98
100
100
100
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
70
50
60
35
35
80
90
45
35
60
25
85
85
70
|
Lambs-
75
90
60
85
80
80
90
80
80
90
75
95
70
80
|
quarters
|
Mustard,
25
25
65
75
100
90
20
15
35
80
98
100
90
25
|
Wild
|
Oat, Wild
40
55
40
20
80
65
75
75
75
75
85
35
70
75
|
Oilseed Rape
0
20
0
0
80
30
5
55
65
65
95
75
0
10
|
Pigweed
80
70
35
80
80
85
80
75
75
100
80
100
75
85
|
Radish, Wild
10
25
50
50
95
85
15
65
85
65
85
80
90
5
|
Russian
—
—
—
70
70
65
70
65
70
70
70
80
70
70
|
Thistle
|
Ryegrass,
65
70
80
55
80
75
75
80
75
90
65
75
80
75
|
Italian
|
Speedwell
25
50
0
5
100
60
10
35
60
65
70
60
100
10
|
Wheat,
0
0
15
0
20
5
0
0
0
0
15
0
15
0
|
Spring
|
Wheat,
0
0
10
0
20
5
0
0
5
5
10
0
10
0
|
Winter
|
Windgrass
10
10
10
25
70
15
70
75
70
40
25
40
40
70
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
47
52
54
57
59
60
66
67
69
72
73
75
79
80
|
|
Barley,
0
0
0
10
25
15
0
0
0
5
10
0
0
0
|
Spring
|
Barley,
10
0
0
20
20
10
0
0
0
10
15
0
0
0
|
Winter
|
Blackgrass
25
10
25
15
70
75
65
70
20
40
65
15
10
75
|
Bluegrass
5
5
10
5
25
15
0
5
0
20
15
10
5
15
|
Bromegrass,
5
0
10
15
35
30
50
60
0
45
25
0
5
55
|
Downy
|
Buckwheat,
60
100
100
80
65
90
95
100
60
95
95
100
70
100
|
Wild
|
Canada
—
—
—
—
—
—
—
—
85
—
—
—
—
—
|
Thistle
|
Canarygrass
0
0
35
5
75
80
55
75
25
40
60
15
5
55
|
Chamomile
—
85
90
100
80
75
85
95
65
75
70
80
85
80
|
Chickweed
90
90
100
100
100
85
75
85
75
98
90
100
95
90
|
Deadnettle
20
35
100
70
80
70
15
40
20
85
75
75
5
35
|
Field Poppy
80
85
70
100
70
60
70
80
65
80
75
100
75
60
|
Field Violet
—
35
85
80
75
80
85
80
75
90
90
95
75
90
|
Foxtail,
50
5
55
75
65
35
75
80
10
60
65
0
20
70
|
Green
|
Galium
65
90
100
90
100
100
85
90
75
95
95
90
95
90
|
Geranium,
—
—
—
—
—
—
—
—
15
—
—
—
—
—
|
Cutleaf
|
Kochia
45
0
15
40
95
70
85
10
60
80
100
95
70
100
|
Lambs-
45
75
95
75
90
80
95
90
75
80
95
100
85
95
|
quarters
|
Mustard,
0
20
100
30
90
75
10
25
20
85
85
100
20
35
|
Wild
|
Oat, Wild
10
5
75
15
80
85
85
95
70
85
85
50
70
95
|
Oilseed Rape
20
0
75
20
60
65
0
70
0
65
65
70
0
15
|
Pigweed
75
35
100
85
80
75
95
75
80
95
100
100
100
100
|
Radish, Wild
5
35
80
40
95
65
5
55
0
75
75
95
0
10
|
Russian
—
20
80
—
80
80
75
55
15
70
75
80
50
70
|
Thistle
|
Ryegrass,
10
40
80
25
80
80
85
85
75
95
70
90
70
85
|
Italian
|
Speedwell
10
70
75
100
65
85
55
70
70
75
70
80
25
65
|
Wheat,
10
0
0
0
40
30
0
0
0
40
45
0
0
0
|
Spring
|
Wheat,
5
0
0
5
35
25
0
0
0
25
25
0
0
0
|
Winter
|
Windgrass
10
0
35
10
75
80
75
85
15
65
70
10
15
75
|
|
31 g ai/ha
|
Post-
Compounds
|
emergence
81
82
83
84
85
87
88
90
104
105
108
109
126
129
|
|
Barley,
0
0
0
0
0
0
0
10
0
0
0
0
0
20
|
Spring
|
Barley,
0
0
0
0
0
0
0
0
0
0
5
5
0
10
|
Winter
|
Blackgrass
65
45
65
65
75
65
75
15
35
15
20
20
15
35
|
Bluegrass
5
10
0
20
10
25
10
5
10
10
5
5
0
10
|
Bromegrass,
15
55
25
40
30
45
15
20
20
10
25
30
5
25
|
Downy
|
Buckwheat,
100
85
100
85
95
85
80
80
90
65
90
95
70
100
|
Wild
|
Canada
—
—
—
—
—
—
—
98
—
—
—
—
98
100
|
Thistle
|
Canarygrass
75
50
50
50
75
55
65
25
45
40
40
40
20
30
|
Chamomile
100
90
95
95
75
90
85
70
80
80
75
80
70
100
|
Chickweed
100
80
100
85
90
85
85
80
95
90
90
100
80
100
|
Deadnettle
15
10
15
5
10
10
5
70
45
10
35
20
40
35
|
Field Poppy
100
70
100
70
70
70
70
65
15
70
20
45
25
70
|
Field Violet
75
95
90
85
65
80
75
90
85
85
90
90
85
65
|
Foxtail,
80
75
75
75
75
70
70
25
30
70
65
55
10
80
|
Green
|
Galium
100
90
100
90
85
85
100
98
85
85
90
100
90
90
|
Geranium,
—
—
—
—
—
—
—
45
—
—
—
—
30
60
|
Cutleaf
|
Kochia
60
90
70
85
40
85
45
85
95
85
90
95
75
60
|
Lambs-
95
95
95
90
80
95
80
90
95
85
90
90
90
75
|
quarters
|
Mustard,
50
25
25
25
10
10
10
80
70
5
70
60
80
80
|
Wild
|
Oat, Wild
85
90
80
85
75
85
80
75
85
80
85
95
60
90
|
Oilseed Rape
70
25
65
10
65
15
65
0
70
0
45
65
60
5
|
Pigweed
100
90
100
95
75
95
75
80
100
85
95
85
98
98
|
Radish, Wild
75
25
75
20
60
15
35
65
70
5
75
75
40
60
|
Russian
75
65
75
70
65
60
75
30
55
40
65
60
30
70
|
Thistle
|
Ryegrass,
85
85
80
80
80
90
80
75
90
75
90
85
85
80
|
Italian
|
Speedwell
75
70
65
70
35
70
25
100
30
45
60
50
60
35
|
Wheat,
0
0
0
0
0
0
0
25
10
0
15
5
0
25
|
Spring
|
Wheat,
0
0
0
0
0
0
0
20
5
0
10
10
0
30
|
Winter
|
Windgrass
70
70
75
75
60
80
65
30
55
60
65
60
0
20
|
|
31 g ai/ha
|
Post-
Compound
|
emergence
153
|
|
Barley,
5
|
Spring
|
Barley,
0
|
Winter
|
Blackgrass
65
|
Bluegrass
15
|
Bromegrass,
25
|
Downy
|
Buckwheat,
95
|
Wild
|
Canada
98
|
Thistle
|
Canarygrass
75
|
Chamomile
70
|
Chickweed
80
|
Deadnettle
70
|
Field Poppy
75
|
Field Violet
85
|
Foxtail,
80
|
Green
|
Galium
100
|
Geranium,
75
|
Cutleaf
|
Kochia
20
|
Lambs-
75
|
quarters
|
Mustard,
98
|
Wild
|
Oat, Wild
85
|
Oilseed Rape
70
|
Pigweed
80
|
Radish, Wild
80
|
Russian
25
|
Thistle
|
Ryegrass,
80
|
Italian
|
Speedwell
75
|
Wheat,
20
|
Spring
|
Wheat,
10
|
Winter
|
Windgrass
25
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
11
20
22
25
27
28
34
35
36
41
42
47
|
|
Barley,
15
0
15
0
0
0
0
0
20
0
0
60
5
15
|
Spring
|
Barley,
0
0
20
0
0
20
15
15
65
0
0
30
15
10
|
Winter
|
Blackgrass
90
90
75
75
75
95
100
95
65
95
50
80
100
50
|
Bluegrass
50
50
55
35
40
75
80
75
60
45
15
90
80
20
|
Bromegrass,
70
70
55
45
80
85
85
85
80
65
35
80
90
15
|
Downy
|
Buckwheat,
100
100
25
100
95
25
80
100
0
35
10
75
60
85
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
90
90
90
80
90
100
100
95
95
98
65
95
100
5
|
Chamomile
90
100
—
—
100
95
100
100
—
100
—
—
100
85
|
Chickweed
100
100
100
95
100
100
100
100
100
100
100
95
100
90
|
Deadnettle
60
55
100
20
—
50
80
5
95
80
85
100
15
65
|
Field Poppy
95
100
100
100
100
100
100
100
100
100
100
95
100
100
|
Field Violet
100
100
100
75
100
100
95
100
95
100
95
100
100
100
|
Foxtail,
100
100
65
85
20
100
100
100
75
100
75
100
100
100
|
Green
|
Galium
100
100
100
85
85
100
100
100
85
100
85
100
100
100
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
75
20
95
90
75
100
60
65
50
25
60
100
100
40
|
Lambs-
100
100
100
100
100
100
100
100
95
100
95
100
100
100
|
quarters
|
Mustard,
25
40
100
100
95
60
65
55
100
100
90
95
25
65
|
Wild
|
Oat, Wild
100
100
85
95
95
100
95
100
90
95
85
95
95
40
|
Oilseed Rape
20
40
5
0
75
35
35
25
85
100
65
15
0
15
|
Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Radish, Wild
100
100
25
65
80
0
95
30
60
100
70
100
60
85
|
Russian
—
—
—
70
20
90
75
35
15
25
15
70
75
—
|
Thistle
|
Ryegrass,
100
100
100
100
100
100
100
100
100
100
70
100
100
70
|
Italian
|
Speedwell
95
100
100
90
100
100
100
100
100
100
100
100
100
100
|
Wheat,
10
10
35
45
25
25
25
25
60
30
30
85
20
15
|
Spring
|
Wheat,
5
5
30
25
5
20
5
0
40
10
0
75
15
10
|
Winter
|
Windgrass
100
100
75
60
80
100
100
100
70
100
65
95
100
75
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
52
54
57
59
60
66
67
69
72
73
75
79
80
81
|
|
Barley,
0
5
10
60
60
10
0
0
60
60
0
0
0
5
|
Spring
|
Barley,
0
0
5
45
65
10
0
0
75
75
0
10
45
45
|
Winter
|
Blackgrass
65
75
80
100
100
80
80
75
75
85
55
60
85
85
|
Bluegrass
35
25
65
80
80
30
50
65
50
30
35
35
75
60
|
Bromegrass,
20
40
30
95
98
85
70
65
60
90
25
60
85
75
|
Downy
|
Buckwheat,
100
80
100
95
60
0
0
15
10
30
50
100
20
15
|
Wild
|
Canada
—
—
—
—
—
—
—
95
—
—
—
—
—
—
|
Thistle
|
Canarygrass
35
90
65
100
100
95
95
95
95
100
75
85
100
100
|
Chamomile
100
—
—
100
100
100
100
100
—
—
—
—
100
—
|
Chickweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Deadnettle
25
95
45
100
100
55
60
98
70
100
100
90
75
55
|
Field Poppy
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Field Violet
85
95
100
100
100
98
100
95
95
95
100
100
95
95
|
Foxtail,
35
100
100
100
100
70
85
55
85
100
100
95
100
100
|
Green
|
Galium
95
100
100
100
100
75
70
90
85
90
80
100
90
95
|
Geranium,
—
—
—
—
—
—
—
10
—
—
—
—
—
—
|
Cutleaf
|
Kochia
90
45
100
100
75
85
0
5
40
95
100
95
100
15
|
Lambs-
100
95
100
100
100
100
100
100
95
100
100
100
100
95
|
quarters
|
Mustard,
98
100
30
100
90
0
0
80
80
100
95
10
0
50
|
Wild
|
Oat, Wild
30
95
60
100
100
90
90
95
95
100
85
90
95
95
|
Oilseed Rape
55
100
25
80
80
35
25
15
25
70
100
35
40
100
|
Pigweed
90
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Radish, Wild
75
100
100
100
90
70
95
20
50
90
100
55
100
—
|
Russian
0
35
—
90
70
90
25
10
25
75
35
100
100
35
|
Thistle
|
Ryegrass,
98
100
95
100
100
95
90
100
90
100
0
100
100
100
|
Italian
|
Speedwell
100
100
100
100
100
100
100
100
100
100
100
—
100
100
|
Wheat,
5
45
10
85
75
20
10
10
80
85
45
0
35
40
|
Spring
|
Wheat,
0
35
10
80
55
0
5
0
45
75
15
0
20
5
|
Winter
|
Windgrass
10
95
80
100
100
85
95
95
90
95
85
80
98
100
|
|
250 g ai/ha
|
Pre-
Compounds
|
emergence
82
83
84
85
87
88
90
104
105
108
109
126
129
153
|
|
Barley,
10
5
5
5
5
0
35
15
20
0
5
0
20
40
|
Spring
|
Barley,
25
40
35
15
25
25
30
20
25
20
10
5
10
40
|
Winter
|
Blackgrass
80
85
90
85
80
90
60
75
75
80
80
65
75
95
|
Bluegrass
80
35
80
75
70
80
65
75
75
75
60
40
60
75
|
Bromegrass,
85
40
85
80
80
75
95
85
75
75
65
30
80
95
|
Downy
|
Buckwheat,
0
25
20
100
60
80
80
95
25
35
75
25
85
85
|
Wild
|
Canada
—
—
—
—
—
—
100
—
—
—
—
95
100
100
|
Thistle
|
Canarygrass
95
100
95
95
95
90
95
100
98
95
98
90
90
100
|
Chamomile
100
—
100
—
100
—
100
—
—
—
—
100
100
100
|
Chickweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Deadnettle
70
100
75
35
70
85
98
100
65
100
95
80
95
100
|
Field Poppy
100
100
100
95
100
90
100
100
100
100
100
95
100
100
|
Field Violet
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Foxtail,
85
100
100
100
95
100
95
100
100
100
95
45
95
100
|
Green
|
Galium
85
85
90
100
80
100
95
100
100
100
100
98
95
98
|
Geranium,
—
—
—
—
—
—
90
—
—
—
—
15
95
90
|
Cutleaf
|
Kochia
100
50
95
45
100
55
80
100
100
100
100
95
100
70
|
Lambs-
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
quarters
|
Mustard,
15
25
20
40
25
70
90
95
20
85
100
98
100
100
|
Wild
|
Oat, Wild
95
90
95
90
95
95
98
100
100
95
90
90
100
98
|
Oilseed Rape
60
10
35
30
45
25
0
55
50
40
85
90
100
100
|
Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
98
100
|
Radish, Wild
100
90
65
100
95
—
95
100
55
90
95
90
100
100
|
Russian
65
0
95
75
100
25
60
75
90
100
50
15
100
100
|
Thistle
|
Ryegrass,
95
100
100
90
98
90
100
100
98
100
100
100
100
100
|
Italian
|
Speedwell
100
100
95
100
100
100
100
—
—
—
—
100
100
100
|
Wheat,
40
35
—
40
20
30
70
45
40
40
40
0
75
85
|
Spring
|
Wheat,
10
25
5
15
15
15
50
15
5
30
20
0
60
50
|
Winter
|
Windgrass
100
95
100
100
100
95
98
100
95
95
100
85
80
95
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
11
20
22
25
27
28
34
35
36
41
42
47
|
|
Barley,
10
0
10
0
0
0
0
0
0
0
0
30
0
15
|
Spring
|
Barley,
0
0
5
0
0
5
10
15
0
0
0
25
5
5
|
Winter
|
Blackgrass
85
85
55
60
55
90
95
85
40
85
35
80
95
30
|
Bluegrass
35
30
30
25
30
40
70
65
50
35
10
80
65
20
|
Bromegrass,
70
65
20
40
25
80
85
70
50
55
10
70
70
15
|
Downy
|
Buckwheat,
65
100
15
100
85
20
45
20
0
20
10
65
80
70
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
85
85
90
70
85
95
100
95
90
95
40
90
100
0
|
Chamomile
95
95
—
—
100
100
100
100
—
100
—
—
100
85
|
Chickweed
100
100
100
95
100
100
100
100
100
100
100
95
100
100
|
Deadnettle
0
0
50
10
15
0
55
5
50
55
50
100
25
10
|
Field Poppy
95
95
100
95
100
100
100
95
100
100
70
—
100
100
|
Field Violet
100
100
100
25
80
100
95
100
75
85
70
100
100
100
|
Foxtail,
75
100
15
75
0
95
100
100
60
65
70
100
100
60
|
Green
|
Galium
100
100
100
75
75
95
85
85
80
95
75
95
95
100
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
35
0
75
70
50
40
30
30
15
20
45
80
75
35
|
Lambs-
100
100
100
100
100
98
100
100
95
100
75
100
100
100
|
quarters
|
Mustard,
10
5
75
100
85
20
45
30
75
100
85
95
20
40
|
Wild
|
Oat, Wild
95
95
80
85
70
95
90
90
85
85
75
90
95
35
|
Oilseed Rape
5
20
5
0
0
0
0
10
50
65
55
25
0
10
|
Pigweed
100
65
98
100
98
100
100
100
100
100
100
100
100
100
|
Radish, Wild
15
15
20
50
70
0
60
35
60
100
50
95
15
100
|
Russian
—
—
—
40
0
40
65
15
10
0
10
40
65
—
|
Thistle
|
Ryegrass,
100
100
100
100
100
100
100
100
100
100
70
100
100
60
|
Italian
|
Speedwell
—
90
85
70
50
95
100
95
100
100
100
100
70
80
|
Wheat,
0
5
25
25
10
10
5
5
25
5
0
70
0
15
|
Spring
|
Wheat,
5
0
20
15
0
0
0
0
25
0
0
45
5
10
|
Winter
|
Windgrass
85
95
55
50
70
100
100
90
55
100
5
80
85
20
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
52
54
57
59
60
66
67
69
72
73
75
79
80
81
|
|
Barley,
0
0
10
40
45
—
0
0
0
0
0
0
5
0
|
Spring
|
Barley,
0
0
5
40
50
0
0
0
50
60
0
0
15
45
|
Winter
|
Blackgrass
65
50
70
95
100
75
75
70
55
80
40
55
80
70
|
Bluegrass
25
15
25
75
65
25
20
35
25
35
10
25
75
20
|
Bromegrass,
15
15
25
90
95
80
35
35
35
50
10
50
75
15
|
Downy
|
Buckwheat,
55
70
10
100
50
0
0
5
15
60
0
25
20
0
|
Wild
|
Canada
—
—
—
—
—
—
—
95
—
—
—
—
—
—
|
Thistle
|
Canarygrass
25
80
55
95
95
85
90
95
85
90
70
75
90
95
|
Chamomile
100
—
—
100
100
100
100
100
—
—
—
—
100
—
|
Chickweed
100
95
100
100
100
100
100
100
100
100
95
100
100
100
|
Deadnettle
10
70
25
90
85
55
55
75
65
70
90
100
70
5
|
Field Poppy
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Field Violet
75
70
100
95
100
95
100
95
75
80
100
98
100
100
|
Foxtail,
15
65
100
85
95
65
85
50
60
50
55
65
100
100
|
Green
|
Galium
90
85
100
100
95
65
35
90
70
80
60
100
80
85
|
Geranium,
—
—
—
—
—
—
—
0
—
—
—
—
—
—
|
Cutleaf
|
Kochia
40
30
35
95
60
75
0
70
10
85
80
100
100
25
|
Lambs-
100
95
100
100
100
100
100
100
95
95
100
100
100
70
|
quarters
|
Mustard,
90
100
25
100
85
0
0
40
60
100
100
5
0
0
|
Wild
|
Oat, Wild
25
85
50
95
100
85
80
90
85
85
80
85
90
85
|
Oilseed Rape
0
85
0
50
40
35
25
15
15
0
100
40
35
50
|
Pigweed
65
100
98
100
100
100
100
100
95
100
100
100
100
100
|
Radish, Wild
55
100
25
95
95
75
75
20
50
100
100
45
100
—
|
Russian
0
25
—
80
35
60
0
0
15
40
25
75
95
15
|
Thistle
|
Ryegrass,
100
100
80
100
100
90
85
98
100
100
100
90
95
85
|
Italian
|
Speedwell
95
100
100
100
100
100
100
100
—
100
100
—
95
100
|
Wheat,
0
0
5
80
65
5
0
0
65
70
35
0
25
0
|
Spring
|
Wheat,
0
15
5
70
55
0
0
0
25
50
20
0
0
5
|
Winter
|
Windgrass
10
70
65
100
100
85
80
75
80
90
50
50
95
90
|
|
125 g ai/ha
|
Pre-
Compounds
|
emergence
82
83
84
85
87
88
90
104
105
108
109
126
129
153
|
|
Barley,
0
0
0
0
0
0
20
5
0
0
5
0
0
25
|
Spring
|
Barley,
5
0
5
0
10
0
15
10
10
10
0
0
0
25
|
Winter
|
Blackgrass
75
70
80
85
80
85
45
65
60
50
75
55
55
85
|
Bluegrass
65
35
65
65
45
75
65
70
60
35
30
30
25
75
|
Bromegrass,
80
60
75
55
75
65
55
65
70
70
65
20
65
85
|
Downy
|
Buckwheat,
15
0
25
80
0
50
40
55
5
20
30
10
85
85
|
Wild
|
Canada
—
—
—
—
—
—
100
—
—
—
—
95
100
100
|
Thistle
|
Canarygrass
90
90
90
90
90
90
85
95
95
90
90
80
60
95
|
Chamomile
100
—
100
—
100
—
100
—
—
—
—
100
100
100
|
Chickweed
100
100
100
100
100
100
100
95
100
100
100
100
98
100
|
Deadnettle
25
15
65
10
65
65
90
80
15
95
80
70
75
100
|
Field Poppy
100
100
100
—
100
90
100
100
100
100
100
90
100
100
|
Field Violet
95
95
100
95
95
100
100
95
100
100
100
100
85
100
|
Foxtail,
90
100
75
100
95
100
70
100
65
100
75
25
80
100
|
Green
|
Galium
80
40
75
75
60
75
85
100
85
95
100
85
90
95
|
Geranium,
—
—
—
—
—
—
65
—
—
—
—
0
70
85
|
Cutleaf
|
Kochia
75
30
75
10
100
15
90
95
95
80
80
75
85
25
|
Lambs-
100
100
95
100
100
100
85
100
100
100
100
75
100
100
|
quarters
|
Mustard,
25
35
5
35
0
65
100
75
0
95
100
70
100
100
|
Wild
|
Oat, Wild
95
90
95
85
90
90
85
80
85
80
90
80
90
98
|
Oilseed Rape
35
10
35
20
30
0
0
55
50
75
75
15
55
90
|
Pigweed
100
100
100
100
100
100
100
100
100
100
100
100
100
100
|
Radish, Wild
60
90
35
100
75
—
90
95
35
100
90
75
100
98
|
Russian
65
15
95
25
85
15
35
55
70
70
35
5
100
60
|
Thistle
|
Ryegrass,
90
90
100
85
98
85
100
100
95
100
100
98
98
100
|
Italian
|
Speedwell
100
100
90
100
90
100
100
—
—
—
—
100
100
100
|
Wheat,
15
10
15
15
15
25
60
35
0
25
20
0
60
70
|
Spring
|
Wheat,
0
5
0
5
0
10
25
5
5
10
5
0
45
45
|
Winter
|
Windgrass
100
90
90
95
85
85
80
80
80
75
80
75
75
80
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
11
20
22
25
27
28
34
35
36
41
42
47
|
|
Barley,
0
0
5
0
0
0
0
0
0
0
0
0
0
5
|
Spring
|
Barley,
0
0
5
0
0
0
0
0
0
0
0
20
0
0
|
Winter
|
Blackgrass
70
75
30
40
45
90
90
85
20
85
30
75
80
20
|
Bluegrass
15
15
15
15
30
35
35
45
25
25
15
75
45
20
|
Bromegrass,
25
50
5
35
5
65
55
55
50
30
0
55
55
10
|
Downy
|
Buckwheat,
10
10
15
20
20
0
30
0
10
20
0
55
25
60
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
60
60
55
35
35
80
95
85
50
85
45
90
95
0
|
Chamomile
95
100
—
—
100
100
100
95
—
100
—
—
100
80
|
Chickweed
90
100
100
95
100
100
100
100
95
95
95
95
100
95
|
Deadnettle
0
0
15
0
0
0
0
0
40
15
0
90
0
10
|
Field Poppy
95
95
75
70
0
100
100
95
100
85
50
95
100
100
|
Field Violet
100
100
100
15
65
100
90
85
25
75
10
90
95
100
|
Foxtail,
15
100
10
60
0
90
95
80
60
45
25
80
65
25
|
Green
|
Galium
95
85
80
30
65
90
70
60
35
85
20
85
85
95
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
0
0
40
25
35
10
20
20
10
0
25
75
60
10
|
Lambs-
100
60
35
90
100
95
100
100
60
98
95
100
100
100
|
quarters
|
Mustard,
0
0
20
35
65
0
40
15
25
100
85
90
15
20
|
Wild
|
Oat, Wild
70
90
70
65
55
90
85
85
75
80
45
90
90
20
|
Oilseed Rape
0
0
0
0
0
0
0
0
55
10
0
5
0
0
|
Pigweed
100
50
0
40
98
100
100
100
95
95
75
75
100
100
|
Radish, Wild
0
5
15
0
25
0
50
0
0
100
0
85
—
25
|
Russian
—
—
—
30
0
25
10
0
0
0
15
20
15
—
|
Thistle
|
Ryegrass,
100
95
90
100
90
100
100
95
95
85
65
100
100
30
|
Italian
|
Speedwell
50
—
15
70
0
80
100
95
100
75
100
95
75
25
|
Wheat,
0
0
15
15
0
0
0
0
0
0
0
55
0
5
|
Spring
|
Wheat,
0
0
0
0
0
0
0
0
0
0
0
20
0
5
|
Winter
|
Windgrass
60
75
35
40
20
85
85
75
25
95
5
75
85
5
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
52
54
57
59
60
66
67
69
72
73
75
79
80
81
|
|
Barley,
0
0
10
25
10
0
0
0
0
10
0
0
0
0
|
Spring
|
Barley,
0
0
0
25
30
0
0
0
25
40
0
0
0
0
|
Winter
|
Blackgrass
20
30
35
90
95
70
75
25
30
60
30
45
75
60
|
Bluegrass
10
10
20
50
45
15
0
0
25
35
15
10
55
10
|
Bromegrass,
0
15
5
85
90
60
35
20
0
40
0
35
35
45
|
Downy
|
Buckwheat,
20
5
10
65
25
0
0
0
0
0
0
90
25
15
|
Wild
|
Canada
—
—
—
—
—
—
—
90
—
—
—
—
—
—
|
Thistle
|
Canarygrass
25
55
10
90
95
80
85
80
80
85
55
60
90
65
|
Chamomile
100
—
—
95
100
100
95
100
—
—
—
—
100
—
|
Chickweed
98
90
100
100
100
100
100
100
100
90
100
100
100
100
|
Deadnettle
0
60
20
90
90
40
30
55
15
0
55
10
65
0
|
Field Poppy
0
55
100
100
100
100
100
90
100
100
95
100
100
100
|
Field Violet
10
35
100
90
100
85
98
90
75
75
100
85
95
80
|
Foxtail,
0
60
70
75
80
35
80
50
30
20
35
60
80
65
|
Green
|
Galium
100
45
100
95
85
20
10
70
60
80
50
90
40
65
|
Geranium,
—
—
—
—
—
—
—
0
—
—
—
—
—
—
|
Cutleaf
|
Kochia
35
60
10
60
20
15
0
20
15
30
80
55
75
0
|
Lambs-
90
65
100
100
100
100
100
100
100
95
95
100
100
95
|
quarters
|
Mustard,
100
100
25
95
70
0
0
30
25
80
35
15
0
0
|
Wild
|
Oat, Wild
25
75
30
90
95
85
75
75
75
90
65
80
90
85
|
Oilseed Rape
0
50
0
30
15
35
20
15
15
5
75
35
35
0
|
Pigweed
55
100
75
100
100
100
95
100
85
100
100
100
100
100
|
Radish, Wild
15
100
10
85
90
70
60
0
0
75
70
25
75
50
|
Russian
0
0
—
50
20
20
0
0
10
25
0
70
95
0
|
Thistle
|
Ryegrass,
85
90
75
100
100
85
80
95
75
100
100
85
90
65
|
Italian
|
Speedwell
100
95
90
100
100
100
75
100
70
100
100
—
95
60
|
Wheat,
0
0
5
65
55
0
0
0
35
55
25
0
0
0
|
Spring
|
Wheat,
0
0
5
35
35
0
0
0
10
40
0
0
0
0
|
Winter
|
Windgrass
10
50
35
85
90
75
75
55
65
65
15
40
90
75
|
|
62 g ai/ha
|
Pre-
Compounds
|
emergence
82
83
84
85
87
88
90
104
105
108
109
126
129
153
|
|
Barley,
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Spring
|
Barley,
0
0
0
0
0
0
0
0
10
0
0
0
0
10
|
Winter
|
Blackgrass
75
60
75
80
75
85
35
60
50
35
25
45
15
80
|
Bluegrass
45
15
30
60
35
60
40
35
30
15
20
5
10
75
|
Bromegrass,
65
30
55
35
65
45
20
65
65
25
30
0
15
75
|
Downy
|
Buckwheat,
0
0
15
65
0
45
—
60
5
0
20
0
30
60
|
Wild
|
Canada
—
—
—
—
—
—
95
—
—
—
—
15
100
100
|
Thistle
|
Canarygrass
85
85
85
90
90
90
75
85
95
80
75
50
15
90
|
Chamomile
100
—
100
—
95
—
100
—
—
—
—
100
100
100
|
Chickweed
100
100
100
100
100
100
198
100
100
100
100
98
100
100
|
Deadnettle
25
0
20
0
35
0
70
80
10
25
60
45
75
100
|
Field Poppy
100
100
95
—
100
95
100
100
100
10
100
45
98
100
|
Field Violet
90
80
100
70
85
95
95
100
100
100
100
85
85
100
|
Foxtail,
75
50
35
55
55
100
45
70
55
90
65
20
70
75
|
Green
|
Galium
60
25
60
70
40
70
75
95
95
70
75
70
90
95
|
Geranium,
—
—
—
—
—
—
60
—
—
—
—
0
0
75
|
Cutleaf
|
Kochia
15
0
15
10
55
10
65
75
50
95
70
20
55
50
|
Lambs-
95
65
95
100
100
100
98
100
100
100
100
100
75
85
|
quarters
|
Mustard,
0
0
0
25
0
55
98
70
0
60
75
70
100
100
|
Wild
|
Oat, Wild
85
85
90
75
85
85
80
80
80
80
80
70
75
95
|
Oilseed Rape
35
5
20
0
30
0
0
20
60
45
40
0
15
85
|
Pigweed
100
100
100
100
100
100
35
100
100
100
100
100
100
100
|
Radish, Wild
60
70
35
25
65
0
65
100
15
100
75
15
100
98
|
Russian
15
0
5
10
15
0
15
10
60
15
20
0
50
15
|
Thistle
|
Ryegrass,
80
75
90
80
95
85
100
100
90
98
95
90
80
100
|
Italian
|
Speedwell
75
75
75
90
85
100
100
—
—
—
—
100
100
100
|
Wheat,
0
0
5
0
0
10
35
15
0
20
5
0
50
45
|
Spring
|
Wheat,
0
0
0
0
0
0
10
0
0
0
0
0
35
20
|
Winter
|
Windgrass
80
75
80
70
80
75
65
75
80
50
60
35
45
80
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
1
2
11
20
22
25
27
28
34
35
36
41
42
47
|
|
Barley,
0
0
5
0
0
0
0
0
0
0
0
0
0
0
|
Spring
|
Barley,
0
0
5
0
0
0
0
0
0
0
0
0
0
0
|
Winter
|
Blackgrass
35
65
5
20
45
85
85
85
15
75
15
70
80
5
|
Bluegrass
5
0
10
10
0
25
25
30
0
25
0
70
35
0
|
Bromegrass,
20
10
5
15
0
40
35
45
0
20
0
50
45
5
|
Downy
|
Buckwheat,
5
—
20
15
20
0
25
0
0
15
0
35
20
70
|
Wild
|
Canada
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Thistle
|
Canarygrass
40
40
45
25
25
80
85
85
20
75
0
90
90
0
|
Chamomile
95
80
—
—
95
100
100
100
—
100
—
—
95
80
|
Chickweed
100
90
20
85
95
95
100
100
85
95
95
90
100
90
|
Deadnettle
0
0
10
0
0
0
0
0
0
0
0
35
0
0
|
Field Poppy
95
95
75
70
0
95
100
100
—
75
—
95
100
60
|
Field Violet
95
95
85
0
20
90
80
75
15
15
15
95
85
95
|
Foxtail,
10
65
10
25
0
35
95
70
55
50
45
45
30
0
|
Green
|
Galium
75
100
70
10
10
70
60
15
0
80
0
75
70
85
|
Geranium,
—
—
—
—
—
—
—
—
—
—
—
—
—
—
|
Cutleaf
|
Kochia
0
0
10
0
35
0
0
20
25
0
0
80
20
10
|
Lambs-
20
15
25
75
100
80
100
100
60
70
75
25
98
100
|
quarters
|
Mustard,
0
0
0
25
5
0
40
10
15
85
45
70
15
10
|
Wild
|
Oat, Wild
75
80
15
35
30
85
85
85
70
75
35
85
90
10
|
Oilseed Rape
0
0
5
0
0
0
0
0
10
0
0
0
0
0
|
Pigweed
70
25
0
30
100
100
100
90
50
25
55
25
90
70
|
Radish, Wild
0
0
10
0
0
0
0
0
0
35
0
25
0
20
|
Russian
—
—
—
0
0
10
0
0
0
0
0
25
10
—
|
Thistle
|
Ryegrass,
100
85
85
90
85
95
90
90
75
75
20
95
95
20
|
Italian
|
Speedwell
70
55
0
70
0
35
75
95
100
0
95
100
70
25
|
Wheat,
0
0
5
0
0
0
0
0
0
0
0
40
0
5
|
Spring
|
Wheat,
0
0
0
0
0
0
0
0
0
0
0
10
0
5
|
Winter
|
Windgrass
15
60
25
35
0
75
75
70
15
25
0
70
70
5
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
52
54
57
59
60
66
67
69
72
73
75
79
80
81
|
|
Barley,
0
0
5
5
5
0
0
0
0
0
0
0
0
0
|
Spring
|
Barley,
0
0
0
15
15
0
0
0
5
5
0
0
0
0
|
Winter
|
Blackgrass
20
15
25
85
90
25
75
15
15
50
15
20
70
55
|
Bluegrass
0
0
0
30
35
10
0
5
10
15
15
10
20
0
|
Bromegrass,
0
0
0
75
60
15
25
20
0
20
0
35
30
20
|
Downy
|
Buckwheat,
20
0
0
20
0
0
0
0
0
0
0
0
0
15
|
Wild
|
Canada
—
—
—
—
—
—
—
30
—
—
—
—
—
—
|
Thistle
|
Canarygrass
20
15
0
80
90
25
40
30
0
80
20
45
85
75
|
Chamomile
60
—
—
100
95
90
95
100
—
—
—
—
95
—
|
Chickweed
98
85
100
100
95
90
100
95
70
95
90
100
100
95
|
Deadnettle
0
0
0
50
35
15
15
15
5
0
30
0
55
0
|
Field Poppy
0
90
100
100
75
100
100
85
100
70
0
100
90
100
|
Field Violet
0
25
95
80
95
60
85
85
10
35
95
80
55
75
|
Foxtail,
0
50
10
55
70
15
15
50
20
15
15
55
20
75
|
Green
|
Galium
70
0
85
95
75
0
0
45
20
40
15
80
25
25
|
Geranium,
—
—
—
—
—
—
—
0
—
—
—
—
—
—
|
Cutleaf
|
Kochia
15
25
10
20
15
0
0
0
10
30
65
60
35
0
|
Lambs-
35
65
100
95
100
55
95
85
35
95
95
100
100
55
|
quarters
|
Mustard,
85
50
0
95
45
0
0
0
0
65
55
0
0
0
|
Wild
|
Oat, Wild
25
75
15
90
90
75
70
60
65
75
55
80
85
85
|
Oilseed Rape
0
15
0
20
0
35
10
10
5
0
50
25
35
0
|
Pigweed
60
80
70
95
100
30
35
50
35
70
85
45
100
95
|
Radish, Wild
0
25
0
—
55
30
25
0
0
30
40
25
20
0
|
Russian
0
0
—
40
15
0
0
0
0
10
0
0
10
0
|
Thistle
|
Ryegrass,
85
35
55
100
100
80
75
90
55
95
95
80
90
55
|
Italian
|
Speedwell
50
100
25
100
100
75
80
98
5
100
95
—
65
55
|
Wheat,
0
0
5
35
35
0
0
0
0
15
0
0
0
0
|
Spring
|
Wheat,
0
0
5
10
10
0
0
0
5
15
0
0
0
0
|
Winter
|
Windgrass
10
0
20
85
85
70
30
35
25
40
0
25
75
60
|
|
31 g ai/ha
|
Pre-
Compounds
|
emergence
82
83
84
85
87
88
90
104
105
108
109
126
129
153
|
|
Barley,
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Spring
|
Barley,
0
0
0
0
0
0
0
0
5
0
0
0
0
0
|
Winter
|
Blackgrass
70
20
70
75
70
80
25
25
35
15
25
25
10
75
|
Bluegrass
15
15
15
40
25
35
0
35
25
10
10
5
0
70
|
Bromegrass,
45
20
35
15
25
20
15
0
35
25
0
0
15
75
|
Downy
|
Buckwheat,
35
0
10
20
0
0
15
0
15
0
0
0
0
40
|
Wild
|
Canada
—
—
—
—
—
—
50
—
—
—
—
0
80
100
|
Thistle
|
Canarygrass
75
65
85
80
85
85
50
65
85
45
35
15
5
85
|
Chamomile
100
—
80
—
95
—
100
—
—
—
—
85
100
100
|
Chickweed
100
100
100
100
100
100
100
100
100
100
100
70
98
98
|
Deadnettle
10
0
25
0
25
5
15
65
—
0
0
0
60
98
|
Field Poppy
95
100
90
—
100
—
15
0
100
10
100
30
90
100
|
Field Violet
100
75
65
65
80
70
95
100
100
90
85
85
85
100
|
Foxtail,
35
15
30
25
10
30
25
20
45
30
0
20
35
75
|
Green
|
Galium
60
0
20
30
15
25
75
65
80
60
40
50
75
85
|
Geranium,
—
—
—
—
—
—
0
—
—
—
—
0
0
35
|
Cutleaf
|
Kochia
0
0
10
5
0
10
75
30
10
60
20
10
5
20
|
Lambs-
75
95
95
25
70
100
90
75
95
100
95
100
100
70
|
quarters
|
Mustard,
0
0
0
25
0
20
35
10
10
5
5
60
75
100
|
Wild
|
Oat, Wild
80
80
90
75
80
80
75
75
80
80
75
65
75
80
|
Oilseed Rape
30
5
25
0
15
0
0
15
55
20
15
0
0
75
|
Pigweed
100
100
95
95
50
75
25
60
100
100
100
98
100
100
|
Radish, Wild
65
30
—
0
45
5
0
95
—
45
25
5
80
80
|
Russian
10
0
5
5
5
0
10
0
0
0
0
0
10
0
|
Thistle
|
Ryegrass,
75
40
80
55
90
75
100
100
85
80
80
75
70
100
|
Italian
|
Speedwell
75
70
70
50
80
95
100
—
—
—
—
70
90
100
|
Wheat,
0
0
0
0
0
0
20
0
0
0
0
0
25
25
|
Spring
|
Wheat,
0
0
0
0
0
0
0
0
0
0
0
0
10
5
|
Winter
|
Windgrass
75
15
75
55
80
60
50
70
75
25
55
25
35
75
|
|
Test E
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 (southem sandbur, Cenchrus echinatus), arrowleaf sida (Sida rhombifolia), Italian ryegrass (Lolium multiflorum), dayflower (Virginia (VA) dayflower, Commelina virginica), field bindweed (Convolvulus arvensis), momingglory (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.
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 E
|
|
250 g ai/ha
Compounds
|
Postemergence
1
2
20
25
28
34
41
42
47
57
69
72
75
79
|
|
Arrowleaf Sida
80
40
80
85
60
75
90
80
60
45
80
90
80
70
|
Barnyardgrass
35
35
80
50
60
40
60
35
60
90
30
50
30
20
|
Beggarticks
100
100
100
100
100
100
100
100
98
100
100
98
100
100
|
Corn
5
5
15
15
5
5
5
20
20
15
5
30
0
0
|
Crabgrass, Brazil
35
15
50
50
60
50
50
50
40
30
30
70
50
40
|
Dayflower, VA
50
65
50
65
80
90
90
70
10
30
80
80
65
65
|
Field Bindweed
95
80
95
90
80
95
95
90
90
95
90
90
85
95
|
Horseweed
—
—
85
—
80
90
70
85
75
80
90
70
50
90
|
Kochia
—
—
90
98
90
85
95
98
85
75
95
90
100
98
|
Panicum, Fall
85
90
50
90
90
60
50
95
70
80
50
85
60
75
|
Pigweed, Palmer
98
35
70
85
50
75
95
95
70
60
60
75
100
75
|
Poinsettia, Wild
35
15
30
60
40
—
—
—
30
20
0
75
—
10
|
Ragweed
—
—
80
95
75
100
95
90
95
95
95
95
90
100
|
Ryegrass, Italian
90
75
80
90
75
90
90
90
10
50
85
90
90
80
|
Sandbur
30
30
40
75
80
90
75
60
35
70
10
80
30
65
|
Soybean
20
0
30
75
60
60
75
50
30
10
20
50
75
10
|
Waterhemp
100
90
85
90
75
90
85
90
100
75
90
90
95
80
|
Waterhemp_RES1
100
100
80
95
80
95
95
98
95
60
85
90
90
75
|
Waterhemp_RES2
75
60
60
75
50
70
85
80
70
50
65
65
75
55
|
|
250 g ai/ha
Compounds
|
Postemergence
81
82
83
84
85
88
100
126
153
171
|
|
Arrowleaf Sida
60
90
60
80
50
60
75
85
40
95
|
Barnyardgrass
50
50
50
40
30
25
50
30
80
50
|
Beggarticks
100
98
100
100
100
100
100
100
100
100
|
Corn
5
0
10
0
5
5
0
5
0
0
|
Crabgrass, Brazil
50
50
50
20
50
50
50
50
50
60
|
Dayflower, VA
80
65
70
30
80
80
0
50
95
90
|
Field Bindweed
85
85
75
80
90
75
95
100
95
100
|
Horseweed
85
80
90
85
90
90
80
80
85
60
|
Kochia
75
98
65
100
80
90
100
100
70
100
|
Panicum, Fall
90
75
90
90
95
85
80
35
90
75
|
Pigweed, Palmer
50
65
60
70
80
50
50
80
40
70
|
Poinsettia, Wild
50
50
—
40
—
—
35
50
75
80
|
Ragweed
80
90
75
95
85
80
90
100
90
98
|
Ryegrass, Italian
80
80
85
85
80
85
85
90
95
90
|
Sandbur
75
75
70
65
70
70
50
40
70
60
|
Soybean
10
35
15
35
15
10
0
30
25
70
|
Waterhemp
75
90
60
95
90
70
90
90
75
90
|
Waterhemp_RES1
65
95
70
95
80
85
90
100
60
90
|
Waterhemp_RES2
50
60
50
70
50
50
70
85
50
60
|
|
125 g ai/ha
Compounds
|
Postemergence
1
2
20
25
28
34
41
42
47
57
66
69
72
75
|
|
Arrowleaf Sida
70
35
70
80
60
70
95
70
60
40
70
70
80
80
|
Barnyardgrass
25
30
60
50
50
40
50
30
40
90
20
20
40
25
|
Beggarticks
100
100
98
100
100
98
95
100
98
100
100
100
98
100
|
Corn
5
5
0
20
5
0
0
15
5
15
15
0
20
0
|
Crabgrass, Brazil
20
10
20
50
50
50
30
40
25
20
40
30
60
50
|
Dayflower, VA
30
65
50
50
70
90
85
60
0
35
50
65
80
50
|
Field Bindweed
85
75
90
95
60
80
85
90
85
98
80
80
95
80
|
Horseweed
—
—
70
—
80
80
80
75
60
75
90
85
75
60
|
Kochia
—
—
75
100
75
85
95
95
80
60
95
80
90
100
|
Panicum, Fall
80
85
30
80
70
70
30
80
55
70
80
30
80
50
|
Pigweed, Palmer
75
5
55
100
50
65
90
60
30
30
80
40
60
100
|
Poinsettia, Wild
15
15
30
35
50
—
—
—
25
30
—
5
65
—
|
Ragweed
—
—
85
90
70
90
90
95
95
95
90
90
90
60
|
Ryegrass, Italian
65
65
70
85
75
85
85
85
0
20
50
90
85
85
|
Sandbur
30
20
30
70
60
85
70
60
25
65
60
5
75
20
|
Soybean
15
0
40
30
50
70
60
30
20
15
20
25
30
70
|
Waterhemp
98
75
80
85
70
85
90
100
85
30
80
80
80
90
|
Waterhemp_RES1
98
70
80
85
60
90
90
70
80
40
80
85
80
95
|
Waterhemp_RES2
70
5
50
70
50
—
80
70
60
20
50
50
50
60
|
|
125 g ai/ha
Compounds
|
Postemergence
79
81
82
83
84
85
88
90
99
100
105
109
126
153
|
|
Arrowleaf Sida
60
30
80
60
70
50
50
90
60
70
70
80
100
40
|
Barnyardgrass
20
30
50
40
40
20
20
50
50
30
30
40
40
50
|
Beggarticks
100
100
98
100
95
100
100
100
95
90
100
100
100
100
|
Corn
0
5
0
0
0
0
5
0
0
0
20
20
5
0
|
Crabgrass, Brazil
25
50
50
50
15
50
30
70
20
40
50
50
40
40
|
Dayflower, VA
60
80
60
75
10
60
70
90
75
0
60
60
50
90
|
Field Bindweed
95
75
95
70
100
60
60
100
80
90
95
90
95
100
|
Horseweed
95
65
75
85
85
85
90
70
75
75
—
85
85
85
|
Kochia
90
70
95
75
100
80
80
100
70
80
100
100
100
55
|
Panicum, Fall
60
85
75
80
85
80
85
70
70
70
80
80
30
90
|
Pigweed, Palmer
40
—
75
50
80
80
50
60
50
40
70
100
50
30
|
Poinsettia, Wild
20
40
40
—
30
—
—
60
50
10
30
50
50
50
|
Ragweed
95
85
90
70
98
60
70
90
90
90
95
95
100
80
|
Ryegrass, Italian
70
75
75
80
75
75
80
85
80
70
80
85
85
90
|
Sandbur
50
70
70
65
60
70
70
50
40
40
50
70
40
60
|
Soybean
15
0
40
0
10
5
0
60
30
0
25
20
40
10
|
Waterhemp
70
60
85
40
90
65
60
90
75
—
90
90
90
50
|
Waterhemp_RES1
70
60
85
80
80
75
65
80
75
85
100
90
90
50
|
Waterhemp_RES2
15
50
60
40
70
40
50
70
60
65
70
60
70
30
|
|
125 g ai/ha
Compound
|
Postemergence
171
|
|
Arrowleaf Sida
90
|
Barnyardgrass
50
|
Beggarticks
100
|
Corn
0
|
Crabgrass, Brazil
50
|
Dayflower, VA
70
|
Field Bindweed
100
|
Horseweed
70
|
Kochia
100
|
Panicum, Fall
60
|
Pigweed, Palmer
60
|
Poinsettia, Wild
40
|
Ragweed
90
|
Ryegrass, Italian
85
|
Sandbur
50
|
Soybean
50
|
Waterhemp
85
|
Waterhemp_RES1
75
|
Waterhemp_RES2
40
|
|
62 g ai/ha
Compounds
|
Postemergence
1
2
20
25
34
41
42
47
57
66
69
72
75
79
|
|
Arrowleaf Sida
70
30
60
75
60
90
60
50
20
60
60
75
70
50
|
Barnyardgrass
20
25
50
50
40
35
30
30
85
25
25
40
30
15
|
Beggarticks
98
100
95
100
100
95
95
100
100
90
85
100
95
100
|
Corn
5
0
0
20
0
0
15
5
10
10
0
10
0
0
|
Crabgrass, Brazil
15
0
20
40
40
20
35
20
20
30
20
40
40
20
|
Dayflower, VA
0
15
10
40
80
40
50
5
15
60
50
65
50
50
|
Field Bindweed
70
65
85
95
80
90
85
75
95
80
85
80
90
95
|
Horseweed
—
—
80
—
75
80
75
40
75
90
75
60
50
95
|
Kochia
—
—
65
95
98
95
85
70
70
90
80
98
98
80
|
Panicum, Fall
75
70
15
50
65
25
50
55
60
70
20
80
40
60
|
Pigweed, Palmer
90
5
35
80
80
60
75
35
20
60
20
50
70
35
|
Poinsettia, Wild
15
0
20
30
—
—
—
15
10
—
0
40
—
10
|
Ragweed
—
—
75
90
85
—
85
90
60
80
80
90
70
98
|
Ryegrass, Italian
50
50
50
80
80
85
70
0
0
40
70
80
80
40
|
Sandbur
30
15
20
60
80
50
50
20
60
50
0
70
20
30
|
Soybean
10
0
20
20
40
40
20
25
0
20
10
30
70
10
|
Waterhemp
95
75
75
80
85
85
80
80
50
75
85
65
90
60
|
Waterhemp_RES1
90
70
70
80
90
75
75
70
50
75
70
80
90
60
|
Waterhemp_RES2
70
5
50
60
80
80
65
50
10
40
40
40
60
15
|
|
62 g ai/ha
Compounds
|
Postemergence
81
82
83
84
85
88
90
99
100
105
109
126
153
171
|
|
Arrowleaf Sida
40
70
50
60
50
50
90
50
60
60
60
80
50
80
|
Barnyardgrass
20
40
50
30
30
30
40
40
40
30
30
50
40
45
|
Beggarticks
100
90
100
100
100
100
98
100
80
100
85
100
100
95
|
Corn
0
0
0
0
0
0
5
0
5
15
10
10
0
0
|
Crabgrass, Brazil
40
30
40
10
30
15
50
10
50
40
30
25
30
50
|
Dayflower, VA
70
50
60
0
60
60
80
70
0
50
50
20
90
50
|
Field Bindweed
65
80
70
100
50
60
90
70
80
75
95
90
90
85
|
Horseweed
75
70
80
75
85
95
75
60
70
85
90
75
80
60
|
Kochia
70
98
60
98
70
70
95
60
80
90
95
100
50
95
|
Panicum, Fall
80
65
70
70
75
80
60
50
50
70
65
35
90
50
|
Pigweed, Palmer
20
60
40
75
80
55
50
30
30
70
65
50
20
50
|
Poinsettia, Wild
40
30
—
30
—
—
50
40
0
25
45
20
30
30
|
Ragweed
60
90
50
95
50
50
80
80
85
90
90
80
70
75
|
Ryegrass, Italian
70
70
60
65
60
65
85
70
60
70
90
80
90
75
|
Sandbur
60
60
50
50
60
60
50
40
40
45
60
30
85
50
|
Soybean
0
25
0
15
0
0
40
10
0
15
20
30
15
40
|
Waterhemp
60
80
50
85
50
60
80
60
75
80
80
90
40
80
|
Waterhemp_RES1
60
75
65
85
75
70
50
70
80
75
90
95
30
70
|
Waterhemp_RES2
20
50
40
65
50
50
60
40
60
60
50
70
40
30
|
|
31 g ai/ha
Compounds
|
Postemergence
1
2
20
25
34
41
42
47
57
66
69
72
75
79
|
|
Arrowleaf Sida
50
25
40
60
65
85
20
40
10
40
50
70
70
50
|
Barnyardgrass
15
20
30
40
30
20
20
10
80
15
20
30
20
15
|
Beggarticks
85
95
85
100
90
100
95
85
100
80
80
90
100
100
|
Corn
5
0
0
10
0
0
10
0
15
0
0
0
0
0
|
Crabgrass, Brazil
15
10
10
30
40
10
20
20
15
20
10
50
40
20
|
Dayflower, VA
0
20
0
10
60
50
30
0
10
25
20
60
30
50
|
Field Bindweed
65
60
75
90
70
80
90
70
85
60
70
70
85
80
|
Horseweed
—
—
70
—
85
75
75
40
60
80
70
60
40
90
|
Kochia
—
—
60
90
70
90
75
60
50
95
75
70
90
70
|
Panicum, Fall
75
70
0
50
50
15
60
40
40
70
20
75
50
55
|
Pigweed, Palmer
20
50
40
75
50
50
70
35
10
70
10
50
70
40
|
Poinsettia, Wild
10
0
0
35
—
—
—
10
10
—
5
30
—
10
|
Ragweed
—
—
65
90
90
80
90
80
50
80
70
85
55
90
|
Ryegrass, Italian
35
30
40
75
65
80
50
0
0
30
65
80
75
30
|
Sandbur
10
10
15
50
70
60
35
20
50
40
0
60
10
20
|
Soybean
0
0
20
0
35
30
10
20
10
0
5
25
70
0
|
Waterhemp
85
70
70
80
70
75
75
75
50
65
65
65
80
50
|
Waterhemp_RES1
80
70
60
75
90
75
75
60
40
80
65
60
90
50
|
Waterhemp_RES2
75
0
50
70
40
20
60
15
20
40
50
35
60
20
|
|
31 g ai/ha
Compounds
|
Postemergence
81
82
83
84
85
88
90
99
100
105
109
126
153
171
|
|
Arrowleaf Sida
40
65
50
50
40
60
80
30
50
60
65
75
40
80
|
Barnyardgrass
20
30
40
30
20
20
30
30
30
20
30
40
25
40
|
Beggarticks
90
90
98
95
90
100
90
80
75
90
90
100
100
80
|
Corn
0
0
0
0
0
0
0
0
0
5
0
0
0
0
|
Crabgrass, Brazil
40
20
30
10
15
15
55
10
25
20
40
10
20
40
|
Dayflower, VA
60
40
50
5
50
50
60
60
0
30
30
0
85
40
|
Field Bindweed
60
85
60
70
50
50
80
60
75
80
80
85
80
70
|
Horseweed
50
60
75
60
60
75
70
50
35
85
80
70
85
50
|
Kochia
60
90
40
80
60
60
90
50
60
80
95
100
50
90
|
Panicum, Fall
85
70
70
60
75
75
60
30
30
60
60
10
85
40
|
Pigweed, Palmer
30
50
40
70
65
50
65
10
20
70
50
40
20
50
|
Poinsettia, Wild
30
40
—
20
—
—
35
30
0
30
25
30
20
25
|
Ragweed
60
85
60
85
50
50
75
75
75
—
85
70
75
60
|
Ryegrass, Italian
50
50
60
60
50
50
80
50
50
50
75
70
85
65
|
Sandbur
60
50
40
50
40
40
40
30
20
40
40
0
50
30
|
Soybean
0
10
0
10
0
0
30
0
0
10
0
10
0
40
|
Waterhemp
50
70
40
70
50
70
70
45
80
70
75
75
50
80
|
Waterhemp_RES1
50
60
70
60
80
60
50
50
80
80
70
75
50
50
|
Waterhemp_RES2
10
50
30
55
40
40
50
50
50
50
50
55
10
15
|
|
16 g ai/ha
Compounds
|
Postemergence
1
2
66
90
99
105
109
|
|
Arrowleaf Sida
30
0
30
70
10
50
50
|
Barnyardgrass
10
20
20
30
40
15
25
|
Beggarticks
70
85
75
85
70
80
80
|
Corn
0
0
0
5
0
0
0
|
Crabgrass, Brazil
0
0
10
50
5
5
10
|
Dayflower, VA
0
0
0
40
40
30
30
|
Field Bindweed
65
60
70
60
50
75
75
|
Horseweed
—
—
60
50
40
80
60
|
Kochia
—
—
90
90
55
80
80
|
Panicum, Fall
70
60
30
40
20
40
50
|
Pigweed, Palmer
70
0
50
40
5
75
60
|
Poinsettia, Wild
5
0
—
20
35
30
0
|
Ragweed
—
—
75
50
50
70
80
|
Ryegrass, Italian
20
20
20
75
40
30
50
|
Sandbur
0
5
25
40
20
30
60
|
Soybean
0
0
0
20
0
0
0
|
Waterhemp
70
70
70
50
65
60
60
|
Waterhemp_RES1
75
65
70
50
50
80
60
|
Waterhemp_RES2
0
0
40
50
50
40
—
|
|
250 g ai/ha
Compounds
|
Preemergence
1
2
20
25
27
28
29
34
37
41
47
57
59
69
|
|
Arrowleaf Sida
80
5
95
95
35
70
98
80
98
100
90
40
98
80
|
Barnyardgrass
20
70
30
90
95
90
90
65
30
65
95
100
90
10
|
Beggarticks
100
100
98
100
100
100
100
100
100
100
100
100
100
100
|
Corn
0
0
0
0
0
0
0
0
0
25
0
0
20
10
|
Crabgrass, Brazil
100
100
90
95
95
90
90
80
95
80
60
70
100
60
|
Crabgrass, Large
65
60
30
85
90
90
65
20
90
60
35
0
95
20
|
Dayflower, VA
25
90
0
30
65
70
60
90
60
80
80
80
80
70
|
Field Bindweed
100
70
95
98
70
75
98
60
100
90
100
100
95
85
|
Foxtail, Giant
98
98
90
100
100
100
98
65
90
90
80
95
100
60
|
Foxtail, Green
90
98
70
100
100
100
100
65
80
75
70
100
100
30
|
Goosegrass
25
25
85
90
85
90
90
10
80
60
0
5
98
50
|
Horseweed
—
—
100
100
100
98
100
—
100
100
—
—
100
—
|
Johnsongrass
40
50
0
90
70
90
100
0
100
25
20
35
80
20
|
Kochia
85
40
100
100
100
100
70
85
65
100
100
100
100
95
|
Lambsquarters
100
100
100
100
100
98
98
98
100
100
100
100
100
90
|
Morningglory
100
100
95
100
100
100
95
90
65
95
100
100
100
85
|
Nightshade
100
100
—
98
98
100
90
95
98
98
100
98
—
90
|
Nutsedge, Yellow
70
70
95
65
80
95
70
80
70
85
35
70
70
60
|
Panicum, Fall
100
100
98
100
100
100
98
95
100
98
95
100
100
70
|
Pigweed, Palmer
100
100
70
100
85
98
100
90
100
85
65
60
100
70
|
Poinsettia, Wild
35
50
—
—
—
—
—
—
—
65
20
50
—
20
|
Ragweed
100
98
98
100
100
98
98
100
98
100
100
100
100
100
|
Ryegrass, Italian
100
100
100
100
100
100
100
100
100
100
50
80
100
100
|
Sandbur
70
75
75
85
90
85
90
70
65
80
70
80
90
60
|
Soybean
75
40
—
70
0
0
50
0
0
65
40
20
70
20
|
Surinam Grass
75
95
90
95
100
98
100
80
90
95
35
95
100
50
|
Velvetleaf
98
90
100
100
100
100
100
100
100
100
100
100
98
90
|
Waterhemp
100
98
100
100
95
100
100
100
100
100
100
80
100
100
|
|
250 g ai/ha
Compounds
|
Preemergence
72
75
79
81
82
83
84
85
87
88
153
|
|
Arrowleaf Sida
65
98
75
70
95
65
100
70
80
50
75
|
Barnyardgrass
50
65
50
75
40
75
20
35
35
70
90
|
Beggarticks
100
100
100
100
100
100
100
100
100
100
100
|
Corn
0
35
20
0
5
0
15
0
15
0
20
|
Crabgrass, Brazil
98
90
100
100
100
80
100
90
100
90
100
|
Crabgrass, Large
90
30
30
98
90
20
75
25
65
20
80
|
Dayflower, VA
50
75
70
65
35
65
50
75
35
70
90
|
Field Bindweed
90
98
100
100
95
100
98
95
100
100
100
|
Foxtail, Giant
80
75
90
100
95
100
90
100
95
100
100
|
Foxtail, Green
70
90
90
100
90
70
100
100
80
100
95
|
Goosegrass
80
5
65
80
90
25
35
20
75
0
75
|
Horseweed
100
—
100
100
100
—
100
—
—
—
100
|
Johnsongrass
35
15
65
100
50
20
0
0
75
0
60
|
Kochia
98
100
100
100
100
75
100
98
100
98
90
|
Lambsquarters
100
100
100
100
100
100
100
100
100
100
100
|
Morningglory
95
100
100
100
100
100
95
100
90
100
100
|
Nightshade
100
100
100
98
100
100
100
100
98
100
100
|
Nutsedge, Yellow
35
65
75
90
65
75
40
65
60
65
95
|
Panicum, Fall
98
90
90
100
100
98
100
100
98
100
100
|
Pigweed, Palmer
90
100
75
100
100
80
100
90
90
100
95
|
Poinsettia, Wild
20
—
55
60
20
—
30
—
20
—
75
|
Ragweed
100
100
100
100
100
98
100
98
100
100
100
|
Ryegrass, Italian
100
100
100
100
100
100
100
100
100
100
100
|
Sandbur
70
70
75
90
75
80
75
90
85
85
90
|
Soybean
15
70
50
0
—
0
0
0
0
0
—
|
Surinam Grass
90
90
80
95
90
95
95
90
75
95
100
|
Velvetleaf
90
98
100
95
98
100
90
95
95
100
100
|
Waterhemp
100
100
100
90
100
75
100
85
100
100
100
|
|
125 g ai/ha
Compounds
|
Preemergence
1
2
20
21
25
27
28
29
34
37
41
47
57
59
|
|
Arrowleaf Sida
75
0
85
50
90
75
50
98
65
90
98
75
50
98
|
Barnyardgrass
0
25
10
90
60
80
65
65
35
0
40
50
75
60
|
Beggarticks
100
100
95
100
100
100
100
100
100
98
100
100
100
100
|
Corn
0
0
0
30
0
0
0
0
0
0
0
0
0
0
|
Crabgrass, Brazil
100
50
70
100
95
95
80
70
80
90
100
0
40
100
|
Crabgrass, Large
35
30
35
100
80
50
90
40
50
80
80
0
0
80
|
Dayflower, VA
15
25
0
80
15
30
65
10
70
40
70
0
30
80
|
Field Bindweed
95
35
85
98
60
70
90
95
40
85
75
90
98
95
|
Foxtail, Giant
95
98
75
100
98
100
100
95
40
80
70
40
95
98
|
Foxtail, Green
90
95
65
100
98
100
100
90
25
65
50
30
90
95
|
Goosegrass
35
25
50
95
80
80
75
50
10
75
50
0
5
98
|
Horseweed
—
—
100
100
100
100
100
100
—
100
100
—
—
100
|
Johnsongrass
30
35
—
60
80
75
80
65
0
100
0
0
30
80
|
Kochia
35
0
98
65
98
80
60
25
5
0
100
75
75
100
|
Lambsquarters
100
98
95
100
100
100
100
100
100
98
100
100
100
100
|
Morningglory
90
100
90
100
95
90
95
80
35
50
90
100
100
98
|
Nightshade
100
98
—
—
95
95
98
85
98
98
98
100
98
—
|
Nutsedge, Yellow
50
65
75
80
20
98
70
30
40
65
75
30
60
75
|
Panicum, Fall
95
98
65
100
100
100
98
98
90
100
95
80
100
100
|
Pigweed, Palmer
100
90
5
98
100
85
95
100
90
100
75
25
40
100
|
Poinsettia, Wild
30
30
—
—
—
—
—
—
—
—
40
0
25
—
|
Ragweed
100
98
70
100
98
100
95
70
100
95
90
98
100
100
|
Ryegrass, Italian
100
100
98
100
98
100
95
95
100
100
100
30
65
100
|
Sandbur
70
70
65
90
80
90
80
90
65
50
75
10
30
90
|
Soybean
40
15
20
35
0
0
0
70
15
—
20
0
0
30
|
Surinam Grass
80
90
85
100
90
100
100
95
95
75
75
35
85
100
|
Velvetleaf
90
80
80
90
98
95
70
100
100
70
95
75
95
95
|
Waterhemp
100
85
85
100
100
85
98
98
100
98
100
90
40
100
|
|
125 g ai/ha
Compounds
|
Preemergence
66
69
72
75
79
80
81
82
83
84
85
87
88
105
|
|
Arrowleaf Sida
65
50
85
90
75
25
70
85
35
80
50
70
0
50
|
Barnyardgrass
15
15
50
35
40
20
35
30
35
10
30
10
30
35
|
Beggarticks
100
100
98
100
100
100
100
100
100
100
100
100
100
100
|
Corn
20
0
0
0
0
0
0
0
0
0
0
20
0
0
|
Crabgrass, Brazil
65
50
90
90
80
100
90
100
50
90
80
90
25
75
|
Crabgrass, Large
15
0
30
0
20
35
90
80
40
15
0
65
20
75
|
Dayflower, VA
20
70
50
60
65
10
35
5
25
35
30
10
10
10
|
Field Bindweed
40
95
65
100
100
100
75
100
35
100
20
95
65
70
|
Foxtail, Giant
90
50
70
35
85
85
98
50
100
85
95
70
100
75
|
Foxtail, Green
70
0
65
0
80
65
95
75
95
75
15
60
100
40
|
Goosegrass
10
30
60
0
60
20
70
70
5
30
5
60
5
10
|
Horseweed
—
—
100
—
100
100
100
100
—
100
—
—
—
100
|
Johnsongrass
0
0
35
10
—
80
65
35
0
0
0
70
0
20
|
Kochia
90
50
60
100
100
100
35
100
0
100
0
100
25
100
|
Lambsquarters
100
—
100
100
100
100
100
100
100
100
100
100
100
100
|
Morningglory
40
50
80
60
90
75
100
90
95
90
50
50
100
60
|
Nightshade
100
90
100
90
100
98
100
98
100
50
100
98
15
98
|
Nutsedge, Yellow
50
30
30
70
65
35
80
40
70
60
35
65
50
40
|
Panicum, Fall
98
75
90
80
80
98
100
98
100
95
98
100
100
98
|
Pigweed, Palmer
100
60
95
50
70
70
75
100
50
90
50
75
70
90
|
Poinsettia, Wild
—
20
10
—
60
40
30
0
—
10
—
15
—
10
|
Ragweed
100
95
90
80
100
100
100
100
95
100
90
98
100
98
|
Ryegrass, Italian
100
100
100
100
100
98
90
100
98
98
95
98
100
100
|
Sandbur
70
50
60
40
80
75
70
60
75
60
80
75
80
75
|
Soybean
0
10
0
40
40
0
0
0
0
0
0
0
0
75
|
Surinam Grass
50
20
75
60
60
75
95
85
85
90
70
80
90
70
|
Velvetleaf
80
60
80
100
95
90
90
95
70
70
70
90
70
95
|
Waterhemp
90
100
100
100
100
100
90
100
75
90
70
90
75
100
|
|
125 g ai/ha
Compounds
|
Preemergence
109
153
|
|
Arrowleaf Sida
35
60
|
Barnyardgrass
25
70
|
Beggarticks
100
100
|
Corn
0
10
|
Crabgrass, Brazil
70
100
|
Crabgrass, Large
35
75
|
Dayflower, VA
25
90
|
Field Bindweed
80
100
|
Foxtail, Giant
80
95
|
Foxtail, Green
60
90
|
Goosegrass
50
60
|
Horseweed
100
100
|
Johnsongrass
40
—
|
Kochia
100
50
|
Lambsquarters
98
100
|
Morningglory
65
90
|
Nightshade
98
95
|
Nutsedge, Yellow
40
80
|
Panicum, Fall
95
100
|
Pigweed, Palmer
85
60
|
Poinsettia, Wild
30
60
|
Ragweed
100
95
|
Ryegrass, Italian
98
100
|
Sandbur
75
85
|
Soybean
0
30
|
Surinam Grass
40
90
|
Velvetleaf
65
90
|
Waterhemp
98
85
|
|
62 g ai/ha
Compounds
|
Preemergence
1
2
20
21
25
27
28
29
34
37
41
47
57
59
|
|
Arrowleaf Sida
65
0
70
0
80
65
0
90
20
85
50
0
0
95
|
Barnyardgrass
0
0
0
70
60
50
20
25
0
0
25
0
0
25
|
Beggarticks
100
100
85
100
100
100
100
98
100
98
98
100
100
100
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass, Brazil
80
60
60
98
90
70
70
75
10
85
65
0
0
90
|
Crabgrass, Large
20
0
35
85
15
50
35
25
0
75
70
0
0
50
|
Dayflower, VA
20
20
0
60
5
10
10
0
35
5
40
0
25
40
|
Field Bindweed
80
15
65
95
98
40
0
90
50
90
70
50
95
75
|
Foxtail, Giant
35
95
20
98
95
98
100
80
40
70
65
0
35
95
|
Foxtail, Green
70
95
40
100
98
100
98
75
0
60
25
20
20
90
|
Goosegrass
5
5
10
95
65
75
60
20
5
35
0
0
0
95
|
Horseweed
—
—
100
100
100
100
100
100
—
100
100
—
—
100
|
Johnsongrass
0
20
—
20
60
75
80
70
0
0
0
0
30
25
|
Kochia
5
0
90
0
80
25
0
0
5
0
90
85
65
90
|
Lambsquarters
98
98
95
100
100
100
100
100
100
100
100
100
100
100
|
Morningglory
98
90
75
98
70
85
90
65
25
40
50
75
40
95
|
Nightshade
95
98
—
—
80
100
98
70
25
80
80
98
98
—
|
Nutsedge, Yellow
15
35
50
75
20
15
20
0
80
0
65
—
30
35
|
Panicum, Fall
90
95
35
100
100
100
95
95
80
100
90
50
98
98
|
Pigweed, Palmer
100
50
0
70
90
60
65
70
0
90
85
0
35
98
|
Poinsettia, Wild
30
30
—
—
—
—
—
—
—
—
40
0
20
—
|
Ragweed
75
75
65
98
95
95
90
85
75
90
70
95
100
95
|
Ryegrass, Italian
100
98
95
100
95
95
80
75
100
95
100
30
35
100
|
Sandbur
20
15
0
80
65
40
65
75
40
35
70
0
0
70
|
Soybean
15
0
0
35
—
0
0
50
35
0
35
0
0
30
|
Surinam Grass
50
75
65
100
80
95
98
95
75
75
75
0
70
90
|
Velvetleaf
75
60
65
90
100
80
35
95
90
50
85
—
65
95
|
Waterhemp
100
80
65
95
100
90
80
90
100
75
98
90
75
100
|
|
62 g ai/ha
Compounds
|
Preemergence
66
69
72
75
79
80
81
82
83
84
85
87
88
105
|
|
Arrowleaf Sida
40
60
35
75
80
35
60
70
25
0
0
60
0
40
|
Barnyardgrass
20
10
30
20
30
20
25
15
30
0
0
0
0
20
|
Beggarticks
95
95
80
80
100
100
100
100
100
100
100
100
100
100
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass, Brazil
25
20
60
20
30
90
95
100
10
85
50
80
40
35
|
Crabgrass, Large
0
0
0
0
0
35
75
70
5
10
0
0
5
50
|
Dayflower, VA
0
60
15
10
70
0
15
5
10
20
0
0
5
0
|
Field Bindweed
50
40
0
5
90
70
0
50
5
90
5
98
5
50
|
Foxtail, Giant
40
50
65
5
70
80
98
65
98
35
65
65
98
35
|
Foxtail, Green
35
0
35
0
70
50
70
70
40
50
25
20
75
30
|
Goosegrass
10
10
40
0
60
30
40
25
0
30
5
0
0
0
|
Horseweed
—
—
100
—
100
100
100
100
—
100
—
—
—
100
|
Johnsongrass
0
0
0
0
—
80
90
—
0
0
0
65
0
20
|
Kochia
60
—
35
100
70
100
20
90
0
75
0
100
0
35
|
Lambsquarters
100
—
80
100
100
98
100
75
98
100
100
100
100
100
|
Morningglory
30
30
30
30
85
70
85
80
20
70
30
35
30
70
|
Nightshade
15
80
80
0
100
100
90
98
50
100
95
90
5
98
|
Nutsedge, Yellow
65
0
20
10
60
40
30
10
65
0
35
60
50
10
|
Panicum, Fall
95
20
80
50
70
95
100
95
95
90
85
90
98
90
|
Pigweed, Palmer
65
60
75
85
70
70
75
90
20
100
30
65
50
98
|
Poinsettia, Wild
—
25
15
—
60
0
5
0
—
0
—
15
—
10
|
Ragweed
90
85
90
65
100
100
100
80
75
98
80
95
85
95
|
Ryegrass, Italian
90
90
90
100
80
98
95
95
95
95
80
95
98
95
|
Sandbur
10
40
35
10
70
70
40
35
70
30
50
65
65
70
|
Soybean
0
15
0
35
50
0
0
0
0
0
0
0
0
0
|
Surinam Grass
5
5
40
35
50
20
90
65
60
65
70
15
75
10
|
Velvetleaf
20
20
40
85
80
70
70
75
35
70
30
60
65
70
|
Waterhemp
80
100
100
60
100
100
90
90
65
90
80
90
90
90
|
|
62 g ai/ha
Compounds
|
Preemergence
109
153
|
|
Arrowleaf Sida
30
70
|
Barnyardgrass
10
50
|
Beggarticks
100
100
|
Corn
0
0
|
Crabgrass, Brazil
40
70
|
Crabgrass, Large
40
70
|
Dayflower, VA
25
85
|
Field Bindweed
40
100
|
Foxtail, Giant
40
95
|
Foxtail, Green
40
75
|
Goosegrass
25
40
|
Horseweed
100
100
|
Johnsongrass
0
0
|
Kochia
85
30
|
Lambsquarters
100
100
|
Morningglory
20
90
|
Nightshade
65
85
|
Nutsedge, Yellow
40
70
|
Panicum, Fall
90
100
|
Pigweed, Palmer
100
60
|
Poinsettia, Wild
25
50
|
Ragweed
100
100
|
Ryegrass, Italian
98
100
|
Sandbur
65
85
|
Soybean
—
50
|
Surinam Grass
60
80
|
Velvetleaf
25
90
|
Waterhemp
70
70
|
|
31 g ai/ha
Compounds
|
Preemergence
1
2
20
21
25
27
28
29
34
37
41
47
57
59
|
|
Arrowleaf Sida
0
0
0
0
40
40
—
70
0
70
20
0
0
80
|
Barnyardgrass
0
0
0
40
20
15
20
0
0
0
10
0
0
0
|
Beggarticks
100
100
20
100
100
90
100
80
90
80
65
100
100
100
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass, Brazil
10
35
40
90
75
70
70
30
0
70
80
0
0
60
|
Crabgrass, Large
0
0
30
65
—
35
—
0
0
50
65
0
0
0
|
Dayflower, VA
0
15
0
80
0
0
5
0
35
0
15
0
0
10
|
Field Bindweed
20
0
35
35
80
0
0
80
5
75
30
50
70
65
|
Foxtail, Giant
50
75
5
95
80
95
85
70
5
65
30
0
5
85
|
Foxtail, Green
15
35
0
95
65
75
65
65
0
0
20
0
0
65
|
Goosegrass
15
0
20
90
20
35
35
0
5
35
0
0
10
90
|
Horseweed
—
—
100
100
100
100
100
100
—
100
100
—
—
100
|
Johnsongrass
0
35
0
—
75
70
70
70
0
0
0
0
0
0
|
Kochia
0
0
0
0
20
0
0
0
0
0
90
0
20
80
|
Lambsquarters
65
100
70
100
98
100
100
100
10
100
35
100
100
100
|
Morningglory
60
75
20
90
65
85
50
35
0
15
30
25
85
75
|
Nightshade
90
75
—
—
90
90
80
5
0
90
25
80
90
—
|
Nutsedge, Yellow
10
0
0
0
0
10
20
0
0
0
25
0
0
50
|
Panicum, Fall
75
85
0
100
95
100
90
85
70
90
80
50
95
95
|
Pigweed, Palmer
90
20
0
65
65
—
0
90
0
0
15
0
35
95
|
Poinsettia, Wild
30
25
—
—
—
—
—
—
—
—
15
0
0
—
|
Ragweed
70
35
30
95
75
95
95
90
70
50
5
80
90
100
|
Ryegrass, Italian
95
95
90
100
95
80
70
65
90
85
98
5
10
100
|
Sandbur
10
15
0
80
35
30
15
75
0
20
50
0
0
70
|
Soybean
0
0
0
35
0
0
0
70
0
0
0
0
0
35
|
Surinam Grass
25
35
10
95
65
85
85
75
5
50
10
0
5
85
|
Velvetleaf
75
30
0
80
60
50
0
70
20
30
20
0
30
90
|
Waterhemp
90
65
0
95
100
95
65
80
100
0
75
50
80
75
|
|
31 g ai/ha
Compounds
|
Preemergence
66
69
72
75
79
80
81
82
83
84
85
87
88
105
|
|
Arrowleaf Sida
0
20
20
50
75
0
40
20
15
0
0
0
0
0
|
Barnyardgrass
15
10
0
20
30
0
0
0
0
0
0
0
0
—
|
Beggarticks
70
90
70
35
100
85
80
100
100
90
90
90
85
80
|
Corn
0
0
0
0
0
0
0
0
0
0
0
0
0
0
|
Crabgrass, Brazil
25
0
50
0
—
75
65
75
0
80
10
60
15
0
|
Crabgrass, Large
0
0
0
0
0
0
50
—
0
0
0
0
0
0
|
Dayflower, VA
0
50
0
10
50
0
10
0
0
10
0
0
0
0
|
Field Bindweed
5
0
0
0
60
25
0
65
0
60
—
40
0
20
|
Foxtail, Giant
5
40
35
0
60
50
75
30
95
5
15
25
95
0
|
Foxtail, Green
0
0
30
0
55
15
20
20
0
10
0
20
50
0
|
Goosegrass
5
0
20
0
50
0
20
20
0
20
5
0
0
0
|
Horseweed
—
—
0
—
100
100
90
90
—
100
—
—
—
0
|
Johnsongrass
0
0
0
0
70
0
70
0
0
0
0
—
0
0
|
Kochia
0
0
25
98
50
90
0
20
0
0
0
65
0
0
|
Lambsquarters
90
10
90
100
100
100
98
98
100
15
70
100
100
0
|
Morningglory
0
20
20
0
60
65
60
70
25
20
25
20
25
20
|
Nightshade
0
70
0
0
80
75
80
90
35
80
95
50
0
50
|
Nutsedge, Yellow
5
0
—
0
50
10
35
0
65
0
—
0
10
0
|
Panicum, Fall
60
20
75
10
80
90
98
90
90
85
95
95
90
65
|
Pigweed, Palmer
0
40
35
30
75
35
35
90
0
75
25
0
65
0
|
Poinsettia, Wild
—
0
0
—
50
0
0
0
—
0
—
0
—
10
|
Ragweed
65
40
0
35
100
70
90
85
70
90
60
98
20
65
|
Ryegrass, Italian
65
80
90
100
75
70
75
75
80
80
80
75
95
90
|
Sandbur
0
50
0
0
60
65
10
0
20
0
0
25
10
15
|
Soybean
0
0
0
0
40
0
0
0
0
0
0
0
0
0
|
Surinam Grass
20
0
5
5
40
10
70
35
65
0
60
10
25
0
|
Velvetleaf
0
30
50
35
70
20
10
0
0
25
0
0
15
50
|
Waterhemp
65
50
90
50
75
70
60
85
65
85
35
75
60
80
|
|
31 g ai/ha
Compounds
|
Preemergence
109
153
|
|
Arrowleaf Sida
35
50
|
Barnyardgrass
0
20
|
Beggarticks
75
100
|
Corn
0
0
|
Crabgrass, Brazil
60
90
|
Crabgrass, Large
0
70
|
Dayflower, VA
25
80
|
Field Bindweed
0
90
|
Foxtail, Giant
35
75
|
Foxtail, Green
0
50
|
Goosegrass
20
40
|
Horseweed
100
90
|
Johnsongrass
0
0
|
Kochia
10
40
|
Lambsquarters
95
100
|
Morningglory
0
85
|
Nightshade
65
70
|
Nutsedge, Yellow
0
50
|
Panicum, Fall
80
100
|
Pigweed, Palmer
20
50
|
Poinsettia, Wild
10
40
|
Ragweed
5
100
|
Ryegrass, Italian
75
100
|
Sandbur
40
80
|
Soybean
0
30
|
Surinam Grass
30
50
|
Velvetleaf
0
85
|
Waterhemp
0
60
|
|
16 g ai/ha
Compounds
|
Preemergence
1
2
66
80
105
109
|
|
Arrowleaf Sida
0
0
0
0
0
40
|
Barnyardgrass
0
0
0
0
20
0
|
Beggarticks
100
90
65
100
90
20
|
Corn
0
0
0
0
0
0
|
Crabgrass, Brazil
0
0
0
65
—
70
|
Crabgrass, Large
0
0
0
0
0
0
|
Dayflower, VA
0
0
0
0
0
0
|
Field Bindweed
5
0
0
20
20
0
|
Foxtail, Giant
0
40
0
0
0
0
|
Foxtail, Green
0
0
0
0
0
0
|
Goosegrass
0
0
5
0
0
0
|
Horseweed
—
—
—
100
0
0
|
Johnsongrass
0
0
0
—
0
0
|
Kochia
0
0
0
25
0
0
|
Lambsquarters
65
50
5
65
0
0
|
Morningglory
20
0
0
0
40
0
|
Nightshade
80
35
0
75
0
25
|
Nutsedge, Yellow
0
0
0
5
0
0
|
Panicum, Fall
65
75
10
80
25
75
|
Pigweed, Palmer
20
0
0
20
0
0
|
Poinsettia, Wild
20
0
—
0
0
10
|
Ragweed
35
20
25
70
50
0
|
Ryegrass, Italian
70
50
40
50
75
60
|
Sandbur
0
0
0
0
0
0
|
Soybean
0
0
0
0
0
0
|
Surinam Grass
0
5
5
0
0
0
|
Velvetleaf
35
0
0
0
0
0
|
Waterhemp
35
65
0
0
70
0
|
|
Test F
This test evaluated the effect of mixtures of Compound 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.
Colby's Equation was used to determine the herbicidal effects expected from the mixtures. Colby's Equation (Colby, S. R. “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations,” Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effect of herbicidal mixtures, and for two active ingredients is of the form:
Pa+b=Pa+Pb−(PaPb/100)
wherein Pa+b is the percentage effect of the mixture expected from additive contribution of the individual components:
Pa is the observed percentage effect of the first active ingredient at the same use rate as in the mixture, and
Pb is the observed percentage effect of the second active ingredient at the same use rate as in the mixture.
The results and additive effects expected from Colby's Equation are listed in Tables F1 through F4.
TABLE F1
|
|
Observed and Expected Results from Compound 1 Alone and in
|
Combination with Mesotrione when applied Post-emergence.
|
|
|
KCHSC
LOLMU
AMBEL
ECHCG
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
1
16
60.0
65.0
95.0
0.0
|
1
62
100.0
100.0
100.0
0.0
|
mesotrione
4
0.0
0.0
0.0
0.0
|
mesotrione
16
90.0
0.0
75.0
20.0
|
1 + mesotrione
16 + 4
100.0
60.0
65.0
65.0
75.0
95.0
20.0
0.0
|
1 + mesotrione
16 + 16
100.0
96.0
95.0
65.0
100.0
98.8
75.0
20.0
|
1 + mesotrione
62 + 4
100.0
100.0
100.0
100.0
100.0
100.0
60.0
0.0
|
1 + mesotrione
62 + 16
100.0
100.0
100.0
100.0
100.0
100.0
100.0
20.0
|
|
SETVI
AMARE
ALOMY
GALAP
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
1
16
0.0
30.0
0.0
65.0
|
1
62
40.0
100.0
35.0
100.0
|
mesotrione
4
0.0
0.0
0.0
0.0
|
mesotrione
16
0.0
30.0
0.0
35.0
|
1 + mesotrione
16 + 4
0.0
0.0
100.0
30.0
0.0
0.0
100.0
65.0
|
1 + mesotrione
16 + 16
20.0
0.0
100.0
51.0
50.0
0.0
100.0
77.3
|
1 + mesotrione
62 + 4
70.0
40.0
100.0
100.0
65.0
35.0
100.0
100.0
|
1 + mesotrione
62 + 16
95.0
40.0
100.0
100.0
75.0
35.0
100.0
100.0
|
|
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.
|
|
|
KCHSC
LOLMU
AMBEL
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
1
16
0
65
65
|
1
62
25
100
90
|
mesotrione
4
0
0
0
|
mesotrione
16
50
0
30
|
1 + mesotrione
16 + 4
50
0
65
65
85
65
|
1 + mesotrione
16 + 6
100
25
100
100
100
90
|
1 + mesotrione
62 + 4
50
50
80
65
100
76
|
1 + mesotrione
62 + 16
100
63
100
100
100
93
|
|
ECHCG
SETVI
AMARE
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
1
16
0
0
20
|
1
62
20
60
90
|
mesotrione
4
0
0
0
|
mesotrione
16
0
0
20
|
1 + mesotrione
16 + 4
0
0
0
0
98
20
|
1 + mesotrione
16 + 16
10
20
50
60
100
90
|
1 + mesotrione
62 + 4
20
0
0
0
100
36
|
1 + mesotrione
62 + 16
45
20
90
60
100
92
|
|
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-emergence
|
|
|
KCHSC
LOLMU
AMBEL
ECHCG
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
2
16
16
50
75
40
5
|
2
62
62
75
95
80
20
|
atrazine
62
62
100
15
10
20
|
2 + atrazine
16 + 62
100
100
100
100
79
75
46
50
|
2 + atrazine
62 + 62
100
100
100
100
96
100
82
100
|
|
SETVT
AMARE
ALOMY
GALAP
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
2
16
15
25
20
100
|
2
62
80
80
60
100
|
atrazine
62
5
75
60
50
|
2 + atrazine
16 + 62
24
85
19
100
81
100
68
100
|
2 + atrazine
62 + 62
36
95
81
100
95
100
84
100
|
|
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-emergence
|
|
|
KCHSC
LOLMU
AMBEL
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
2
16
16
0
0
30
|
2
62
62
0
50
95
|
atrazine
62
62
100
100
10
|
2 + atrazine
16 + 62
100
100
100
65
100
100
|
2 + atrazine
62 + 62
100
100
100
100
100
100
|
|
ECHCG
SETVI
AMARE
|
Treatment
Rate
Obsd.
Exp.
Obsd.
Exp.
Obsd.
Exp.
|
|
2
16
0
60
25
|
2
62
25
98
75
|
atrazine
62
0
5
85
|
2 + atrazine
16 + 62
37
25
0
70
62
100
|
2 + atrazine
62 + 62
96
50
25
100
98
100
|
|
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.