WO2024072768A1 - Substituted fluoropyridine as herbicides - Google Patents

Substituted fluoropyridine as herbicides Download PDF

Info

Publication number
WO2024072768A1
WO2024072768A1 PCT/US2023/033659 US2023033659W WO2024072768A1 WO 2024072768 A1 WO2024072768 A1 WO 2024072768A1 US 2023033659 W US2023033659 W US 2023033659W WO 2024072768 A1 WO2024072768 A1 WO 2024072768A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
methyl
propyl
inhibitors
ethyl
Prior art date
Application number
PCT/US2023/033659
Other languages
French (fr)
Inventor
Eric Allen Marshall
Rachel Tran DAO
Thomas Paul Selby
Thomas Martin Stevenson
Original Assignee
Fmc Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fmc Corporation filed Critical Fmc Corporation
Publication of WO2024072768A1 publication Critical patent/WO2024072768A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • This invention relates to certain substituted fluoropyridine herbicides, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation.
  • 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.
  • R 1 is halogen, C 1 –C 4 alkyl, C 3 –C 4 cycloalkyl, C 1 –C 3 haloalkyl, C 1 –C 3 alkoxy, or C 1 –C 3 haloalkoxy;
  • R 2 is H, halogen, CN, C 1 –C 4 alkyl, C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy;
  • R 3 is halogen, C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy;
  • R 4 is H, halogen or methoxy;
  • X is N or CR 5 ; and
  • R 5 is H, halogen, C 1 -C 3 haloalkyl, CH 3 or cyano; provided when R 2 is H, R 5 is other than H.
  • 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 (b17), and salts of compounds of (b1) through (b17), as described below.
  • 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 (b17), and salts of compounds of (b1) through (b17), as described below.
  • compositions, 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.
  • 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”.
  • 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.
  • seedling used either alone or in a combination of words means a young plant developing from the embryo of a seed.
  • 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.
  • 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.
  • 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 CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylthioalkyl denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • alkylsulfinyl examples include CH 3 S(O)-, CH 3 CH 2 S(O)-, CH 3 CH 2 CH 2 S(O)-, (CH 3 ) 2 CHS(O)- and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 -, CH 3 CH 2 S(O) 2 -, CH 3 CH 2 CH 2 S(O) 2 -, (CH 3 ) 2 CHS(O) 2 -, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • Cyanoalkyl denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH 2 and NCCH 2 CH 2 (alternatively identified as CH 2 CH 2 CN).
  • Niroalkyl denotes an alkyl group substituted with one nitro group.
  • nitroalkyl examples include NO 2 CH 2 and NO 2 CH 2 CH 2 (alternatively identified as CH 2 CH 2 NO 2 ).
  • Alkylamino includes an NH radical substituted with straight-chain or branched alkyl. Examples of “alkylamino” include CH 3 CH 2 NH, CH 3 CH 2 CH 2 NH, and (CH 3 ) 2 CHCH 2 NH. Examples of “dialkylamino” include (CH 3 ) 2 N, (CH 3 CH 2 CH 2 ) 2 N and CH 3 CH 2 (CH 3 )N.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • 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.
  • alkylcycloalkyl donotes an alkyl group bonded to a cycloalkyl moiety.
  • halogen either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F 3 C, ClCH 2 , CF 3 CH 2 and CF 3 CCl 2 .
  • haloalkoxy examples include CF 3 O- , CCl 3 CH 2 O-, HCF 2 CH 2 CH 2 O- and CF 3 CH 2 O-.
  • haloalkoxyalkyl examples include CF 3 OCH 2 -, CCl 3 CH 2 OCH 2 -, HCF 2 CH 2 CH 2 OCH 2 - and CF 3 CH 2 OCH 2 -.
  • haloalkylthio examples include CCl 3 S-, CF 3 S-, CCl 3 CH 2 S- and ClCH 2 CH 2 CH 2 S-.
  • haloalkynyl examples include HC ⁇ CCHCl-, CF 3 C ⁇ C-, CCl 3 C ⁇ C- and FCH 2 C ⁇ CCH 2 -.
  • the total number of carbon atoms in a substituent group is indicated by the “C i –C j ” prefix where i and j are numbers from 1 to 4.
  • C 1 –C 4 alkyl can be, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl.
  • a group contains a substituent which can be hydrogen, for example R 2 , then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
  • R 2 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.
  • phenyl means unsubstituted phenyl.
  • benzyl means unsubstituted benzyl.
  • 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 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).
  • 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.
  • polymorphs can have the same chemical composition, they can also differ in composition due to 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.
  • 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.
  • crystallization using selected solvents and temperatures.
  • 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.
  • nitrogen-containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • 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.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane
  • salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms.
  • 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.
  • 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.
  • the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
  • 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.
  • Embodiments of the present invention as described in the Summary of the Invention include those described below.
  • Formula 1 includes stereoisomers, N-oxides and salts thereof, and reference to “a compound of Formula 1” includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.
  • Embodiment 1. A compound of Formula 1, stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Disclosure.
  • J Embodiment 2. A compound of Formula 1 or Embodiment 1 wherein J is J-1, J-2, J-3, J- 5 or J-6.
  • Embodiment 2a A compound of Formula 1 or Embodiment 2 wherein J is J-1, J-2 or J-3.
  • Embodiment 2b A compound of Formula 1 or Embodiment 2 wherein J is J-1, J-2 or J-3.
  • Embodiment 2a wherein J is J-1.
  • Embodiment 2c A compound of Embodiment 2a wherein J is J-2.
  • Embodiment 2d A compound of Embodiment 2a wherein J is J-3.
  • Embodiment 2e A compound of Formula 1 or Embodiment 2 wherein J is J-5 or J-6.
  • Embodiment 2f A compound of Embodiment 2e wherein J is J-5.
  • Embodiment 2g A compound of Embodiment 2e wherein J is J-6.
  • Embodiment 2h A compound of Embodiment 2e wherein J is J-7.
  • Embodiment 2i A compound of Embodiment 2e wherein J is J-8.
  • Embodiment 2j A compound of Embodiment 2a wherein J is J-1.
  • Embodiment 2c A compound of Embodiment 2a wherein J is J is J-2.
  • Embodiment 2d A compound of Embodiment 2a where
  • Embodiment 4a A compound of Embodiment 4 wherein R 1 is halogen, C 1 –C 4 alkyl, C 3 –C 4 cycloalkyl or C 1 –C 3 alkoxy.
  • Embodiment 4b A compound of Embodiment 4 wherein R 1 is halogen, C 1 –C 4 alkyl, C 3 –C 4 cycloalkyl or C 1 –C 3 alkoxy.
  • Embodiment 4a wherein R 1 is F, Cl, C 1 –C 4 alkyl or C 3 –C 4 cycloalkyl or C 1 –C 3 alkoxy.
  • Embodiment 4c A compound of Embodiment 4b wherein R 1 is Cl.
  • Embodiment 4d A compound of Embodiment 4b wherein R 1 is C 1 –C 4 alkyl.
  • Embodiment 4e A compound of Embodiment 4d wherein R 1 is Me or Et.
  • Embodiment 4f A compound of Embodiment 4b wherein R 1 is C 3 –C 4 cycloalkyl.
  • Embodiment 4g A compound of Embodiment 4f wherein R 1 is cyclopropyl.
  • Embodiment 4h A compound of Embodiment 4b wherein R 1 is C 1 –C 3 alkoxy.
  • Embodiment 4i A compound of Embodiment 4h wherein R 1 is OMe.
  • Embodiment 4j A compound of Embodiment 4b wherein R 1 is Cl, Me, Et, cyclopropyl or OMe.
  • Embodiment 4k A compound of Embodiment 4j wherein R 1 is Me, Et or cyclopropyl.
  • Embodiment 4l A compound of Embodiment 4k wherein R 1 is Me or Et.
  • a compound of Formula 1 or any one of the preceding Embodiments wherein R 2 is H, halogen, CN, C 1 –C 4 alkyl, C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy.
  • Embodiment 5a A compound of Formula 1 or any one of the preceding Embodiments wherein R 2 is C 1 –C 3 haloalkyl.
  • Embodiment 5b. A compound of Embodiment 5a wherein R 2 is CF 3 .
  • Embodiment 5c A compound of Embodiment 5a wherein R 2 is CHF 2 . R 3 Embodiment 6.
  • Embodiment 6a A compound of Embodiment 6 wherein R 3 is C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy.
  • Embodiment 6b A compound of Embodiment 6a wherein R 3 is CF 3 or OCF 3 .
  • Embodiment 6c A compound of Embodiment 6b wherein R 3 is CF 3 .
  • Embodiment 6d A compound of Embodiment 6b wherein R 3 is OCF 3 .
  • Embodiment 7b A compound of Embodiment 7a wherein R 4 is H, F or OMe.
  • Embodiment 7c A compound of Embodiment 7b wherein R 4 is H.
  • Embodiment 7d A compound of Embodiment 7b wherein R 4 is F.
  • Embodiment 7b A compound of Embodiment 7b wherein R 4 is OMe.
  • X Embodiment 8 A compound of Formula 1 or any one of the preceding Embodiments wherein X is N or CR 5 .
  • Embodiment 8a A compound of Formula 1 or any one of the preceding Embodiments wherein X is N or CR 5 .
  • Embodiment 8b A compound of Formula 1 or any one of the preceding Embodiments wherein X is CR 5 .
  • R 5 Embodiment 11 A compound of Formula 1 or any one of the preceding Embodiments wherein R 5 is H, halogen, C 1 –C 3 haloalkyl, Me and CN.
  • Embodiment 11a A compound of Embodiment 11 wherein R 5 is H, halogen or C 1 –C 3 haloalkyl.
  • Embodiment 11aa A compound of Embodiment 11a wherein R 5 is H, Cl, Br or CF 3 .
  • Embodiment 11b A compound of Embodiment 11a wherein R 5 is H, Cl, Br or CF 3 .
  • Embodiment 11a wherein R 5 is H.
  • Embodiment 11c A compound of Embodiment 11a wherein R 5 is halogen.
  • Embodiment 11d A compound of Embodiment 11c wherein R 5 is Cl or Br.
  • Embodiment 11e A compound of Embodiment 11a wherein R 5 is C 1 –C 3 haloalkyl.
  • Embodiment 11f A compound of Embodiment 11e wherein R 5 is CF 3 .
  • Embodiments of this invention 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.
  • embodiments of this invention including Embodiments 1–11f 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 1–11f are illustrated by: Embodiment A. A compound of Formula 1 as described in the Summary of the Disclosure wherein J is J-1, J-2 or J-3; Q is O or -CH 2 -.
  • Embodiment B A compound of Formula 1 as described in the Summary of the Disclosure wherein J is J-1, J-2 or J-3; Q is O or -CH 2 -.
  • R 1 is halogen, C 1 –C 4 alkyl, C 3 –C 4 cycloalkyl, C 1 –C 3 haloalkyl, C 1 –C 3 alkoxy, or C 1 – C 3 haloalkoxy
  • R 2 is H, halogen, CN, C 1 –C 4 alkyl, C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy
  • R 3 is halogen, C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy
  • R 4 is H, halogen or OMe
  • X is N or CR 5
  • R 5 is H, halogen, C 1 –C 3 haloalkyl, Me and CN.
  • Embodiment C A compound of Embodiment B wherein R 1 is F, Cl, C 1 –C 4 alkyl or C 3 –C 4 cycloalkyl or C 1 –C 3 alkoxy; and R 3 is C 1 –C 3 haloalkyl or C 1 –C 3 haloalkoxy.
  • Embodiment D A compound of Embodiment C wherein R 2 is C 1 –C 3 haloalkyl; R 4 is H, F or OMe; and R 5 is H, halogen or C 1 –C 3 haloalkyl.
  • Embodiment E A compound of Embodiment C wherein R 2 is C 1 –C 3 haloalkyl; R 4 is H, F or OMe; and R 5 is H, halogen or C 1 –C 3 haloalkyl.
  • Embodiment D wherein R 1 is Cl, Me, Et, cyclopropyl or OMe; R 2 is CF 3 ; and R 5 is H, Cl, Br or CF 3 .
  • Embodiment F A compound of Embodiment E wherein R 5 is CF 3 .
  • Embodiment G A compound of Embodiment A or any one of the preceding Embodiments wherein J is J-1; Q is O.
  • Embodiment H A compound of Embodiment B wherein X is CR 5 .
  • Embodiment I A compound of Embodiment A wherein J is J-2; X is CR 5 ; and R 5 is CF 3 .
  • Specific embodiments include compounds of Formula 1 selected from the group consisting of: 3-ethyl-5-fluoro-2-[3-(trifluoromethoxy)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 20); 3-ethyl-5-fluoro-6-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-[[6-(trifluoromethyl)- 2-pyridinyl]oxy]pyridine (Compound 42); 3-ethyl-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 51); 3-fluoro-5-methoxy-6-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 54); and 2-[3-(d
  • Embodiment AA A compound of Formula 1 as described in the Summary of the Disclosure wherein J is J-1, J-2, J-3, J-4, J-5 or J-6.
  • J is J-1, J-2, J-3, J-4, J-5 or J-6.
  • the compounds in the current invention i.e. with F at the 5-position of the pyridine core
  • the compounds in the current invention demonstrate higher herbicidal activities than the compounds with other substituents (e.g., H) at the 5-position.
  • the compounds in the current invention also show remarkable safety to crops, such as maize, soybeans and wheat.
  • 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).
  • embodiments relating to methods of use are those involving the compounds of embodiments described above.
  • Compounds of the invention are particularly useful for selective control of weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops.
  • herbicidal compositions of the present invention comprising the compounds of embodiments described above.
  • This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol- pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygena
  • Photosystem II inhibitors are chemical compounds that bind to the D-1 protein at the Q B -binding niche and thus block electron transport from Q A to Q B 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 Q B -binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • triazines such as atrazine
  • triazinones such as hexazinone
  • uracils such as bromacil
  • binding site B binds the phenylureas such as diuron
  • binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • 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, metproxybicyclone, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron,
  • AHAS inhibitors 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.
  • AHAS acetohydroxy acid synthase
  • ALS acetolactate synthase
  • 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
  • ACCase inhibitors 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.
  • ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.
  • auxin is a plant hormone that regulates growth in many plant tissues.
  • auxin mimics are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species.
  • 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, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)-2-Pyridinecarboxylic 2-propyn-1-yl ester (CAS No.
  • EPSP synthase inhibitors 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 are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles “leak”, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat, paraquat and 1-(2-carboxyethyl)-4-(2- pyrimidinyl)pyridazinium (CAS No.2285384-11-2).
  • PPO inhibitors 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.
  • PPO inhibitors include acifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5- Isoxazolecarboxylic ethyl ester (CAS No.
  • GS inhibitors 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 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.
  • 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 oxyace
  • auxin transport inhibitors are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein.
  • auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid).
  • PDS inhibitors 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 are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.
  • 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), flusulfinam, iptriazopyrid, isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrion
  • HST homogentisate solanesyltransferase inhibitors
  • HST inhibitors include cyclopyrimorate (6-chloro-3-(2- cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), 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.
  • cyclopyrimorate 6-chloro-3-(2- cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate
  • Cellulose biosynthesis inhibitors 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 (N 2 -[(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.
  • DHODH (dihydroorotate dehydrogenase) inhibitors act through inhibiting catalysis of the fourth step of pyrimidine biosynthesis in plant systems. Inhibition of pyrimidine biosynthesis leads to the cessation of plant growth.
  • DOHDH inhibitors examples include tetflupyrolimet ((3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3- (trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide) and (3S,4R)-N-(2,3-difluorophenyl)-1- methyl-4-[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-oxo-3-pyrrolidinecaboxamide.
  • “Other herbicides” 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.
  • herbicides examples include aclonifen, asulam, amitrole, bixlozone, broclozone, bromobutide, cinmethylin, clomazone, cumyluron, daimuron, difenzoquat, dimesulfazet, epyrifenacil, 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, 2,5- anhydro-3,4-dide
  • “Other herbicides” also include a compound of Formula (b16A) wherein R 12 is H, C 1 –C 6 alkyl, C 1 –C 6 haloalkyl or C 4 –C 8 cycloalkyl; R 13 is H, C 1 –C 6 alkyl or C 1 –C 6 alkoxy; Q 1 is an optionally substituted ring system selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl and pyrazolyl, wherein when substituted said ring system is substituted by 1 to 3 R 14
  • R 12 is H or C 1 –C 6 alkyl; more preferably R 12 is H or methyl.
  • R 13 is H.
  • Q 1 is either a phenyl ring or a pyridinyl ring, each ring substituted by 1 to 3 R 14 ; more preferably Q 1 is a phenyl ring substituted by 1 to 2 R 14 .
  • Q 2 is a phenyl ring substituted by 1 to 3 R 15 ; more preferably Q 2 is a phenyl ring substituted by 1 to 2 R 15 .
  • each R 14 is independently halogen, C 1 –C 4 alkyl, C 1 –C 3 haloalkyl, C 1 –C 3 alkoxy or C 1 –C 3 haloalkoxy; more preferably each R 14 is independently chloro, fluoro, bromo, C 1 –C 2 haloalkyl, C 1 –C 2 haloalkoxy or C 1 –C 2 alkoxy.
  • each R 15 is independently halogen, C 1 –C 4 alkyl, C 1 –C 3 haloalkoxy; more preferably each R 15 is independently chloro, fluoro, bromo, C 1 –C 2 haloalkyl, C 1 –C 2 haloalkoxy or C 1 –C 2 alkoxy.
  • other herbicides include any one of the following (b16A-1) through (b16A-15):
  • herbicides (b16) also include a compound of Formula (b16B) wherein R 18 is H, C 1 –C 6 alkyl, C 1 –C 6 haloalkyl or C 4 –C 8 cycloalkyl; each R 19 is independently halogen, C 1 –C 6 haloalkyl or C 1 –C 6 haloalkoxy; p is an integer of 0, 1, 2 or 3; each R 20 is independently halogen, C 1 –C 6 haloalkyl or C 1 –C 6 haloalkoxy; and q is an integer of 0, 1, 2 or 3.
  • R 18 is H, C 1 –C 6 alkyl, C 1 –C 6 haloalkyl or C 4 –C 8 cycloalkyl
  • each R 19 is independently halogen, C 1 –C 6 haloalkyl or C 1 –C 6 haloalkoxy
  • p is an integer of 0, 1, 2 or 3
  • each R 20 is independently
  • R 18 is H, methyl, ethyl or propyl; more preferably R 18 is H or methyl; most preferably R 18 is H.
  • each R 19 is independently chloro, fluoro, C 1 – C 3 haloalkyl or C 1 –C 3 haloalkoxy; more preferably each R 19 is independently chloro, fluoro, C 1 fluoroalkyl (i.e. fluoromethyl, difluoromethyl or trifluoromethyl) or C 1 fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy).
  • each R 20 is independently chloro, fluoro, C 1 haloalkyl or C 1 haloalkoxy; more preferably each R 20 is independently chloro, fluoro, C 1 fluoroalkyl (i.e. fluoromethyl, difluorormethyl or trifluromethyl) or C 1 fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy).
  • other herbicides include any one of the following (b15B-1) through (b16B-19):
  • “Other herbicides” (b16) also include a compound of Formula (b16D) Wherein R 1 is C 1 –C 4 alkyl or C 3 –C 6 cycloalkyl; R 2 is H, Cl, Br or I; R 3 is Cl or OR 4 ; R 4 is H or C 1 –C 4 alkyl; R 5 is H, F, Cl or CH 3 ; and R 6 is H or Cl.
  • b16D can be 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone; 6-chloro-4-(7-fluoro-2-methyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone; 6-chloro-4-(7-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone; or 6-chloro-4-(4-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone.
  • herbicide safeners 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.
  • herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N- (aminocarbonyl)
  • Preferred for better control of undesired vegetation e.g., lower use rate such as from greater-than-additive effects, broader spectrum of weeds controlled, or enhanced crop safety
  • a herbicide selected from the group consisting of 4-amino-3-chloro-5-fluoro- 6-(7-fluoro-1H-indol-6-yl)- 2-Pyridinecarboxylic 2-propyn-1-yl ester (CAS No.2251111-17- 6), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)- 2-Pyridinecarboxylic cyanomethyl ester (CAS No.2251111-18-7), 2,5-anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5- ethenyl-4,5-dihydr
  • Reacting a pyridine of Formula 2, where LG 1 represents a leaving group, preferably halogen, with an appropriately substituted phenol or hydroxy heterocycle of Formula J-OH in the presence of a suitable base and solvent results in displacement of the leaving group LG 1 to provide compounds of Formula 1a.
  • suitable bases for this reaction include but are not limited to potassium carbonate, sodium hydroxide, potassium t-butoxide, sodium hydride or potassium hydroxide and compatible solvents such as tetrahydrofuran, acetonitrile, toluene, dioxane or N,N-dimethylformamide.
  • Temperatures for this reaction generally range from 0° C to warming below or heating at the boiling point of the solvent.
  • Reagents of Formula JCH 2 ZnBr and JCH 2 ZnCl are readily generated from the commercially available benzyl and heteroaryl methyl halides in many cases by reacting with an appropriate zinc reagent (i.e. zinc dust, ZnCl 2 , TMPZnCl ⁇ LiCl, or TMP 2 Zn ⁇ 2MgCl 2 ⁇ 2LiCl), usually in the solvent used for the coupling.
  • an appropriate zinc reagent i.e. zinc dust, ZnCl 2 , TMPZnCl ⁇ LiCl, or TMP 2 Zn ⁇ 2MgCl 2 ⁇ 2LiCl
  • Suitable palladium catalysts include but are not limited to tetrakis(triphenylphosphine)palladium [Pd(PPh 3 ) 4 ] and bis(triphenylphosphine) palladium(II) dichloride [PdCl2(PPh3)2, Dichlorobis(triphenylphosphine) palladium(II)].
  • Scheme 2 Intermediates of Formula 2 can be made by reacting a pyridine of Formula 4 (where LG 1 and LG 2 both represent suitable leaving groups such as halogen) and one equivalent or slightly over one equivalent of a pyrazole or triazole of Formula 5 in the presence of an appropriate base and solvent.
  • Displacement of LG 2 by the azole of Formula 5 is generally preferred over displacement of leaving group LG 1 to provide compounds of Formula 1a.
  • appropriate bases for this reaction include but are not limited to potassium carbonate, sodium hydroxide, potassium t- butoxide, sodium hydride or potassium hydroxide and compatible solvents include but not limited to tetrahydrofuran, acetonitrile, toluene, dioxane or N,N-dimethylformamide.
  • Temperatures for this reaction generally range from 0° C to warming below or heating at the boiling point of the solvent.
  • Preferable palladium catalysts include but are not limited to commercially available chloro[2-(di-tert-butylphosphino)- 2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl)] palladium(II) [t-BuXPhos palladium(II) phenethylamine chloride, tBuXPhos-Pd-G1], chloro[(tri-tert-butylphosphine)- 2-(2-aminobiphenyl)] palladium(II) [P(t-Bu)3 Pd G2], methanesulfonato(2-di-t- butylphosphino-2;methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl) (2'-amino
  • Temperatures for this coupling reaction generally range from 0° C to warming below or heating at the boiling point of the solvent.
  • Oxidation of compounds of Formula 1b under appropriate oxidative conditions such as copper iodide and acetic acid in dimethyl sulfoxide or with iron trichloride and air in dimethyl sulfoxide can provide compounds of Formula 1 where Q is carbonyl.
  • various functional groups can be converted into others to provide different compounds of Formula 1.
  • intermediates for the preparation of compounds of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing compounds of Formula 1.
  • the above reactions can also in many cases be performed in alternate order. It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products.
  • the use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M.
  • Step B Preparation of 3-chloro-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine
  • 3-chloro-2,5-difluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine i.e. the product of Step A, 2.77 g, 9.77 mmol
  • m-trifluoromethylphenol (1.19 mL, 9.77 mmol
  • acetonitrile 48.8 mL, 0.2 M
  • potassium carbonate (1.62 g, 11.7 mmol
  • Step C Preparation of 3-ethyl-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine
  • a mixture containing 3-chloro-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl) pyrazol-1-yl]pyridine i.e.
  • Step B the product of Step B, 4.03 g, 9.46 mmol), ethylboronic acid (1.40 g, 18.93 mmol) and potassium carbonate (2.62 g, 18.9 mmol) in toluene (47.3 mL, 0.2 M) and water (4.73 mL, 2 M) was sparged with N 2 for 10 min.
  • RuPhosPd G3 catalyst 0.396 g, 0.473 mmol, 0.05 equiv.
  • the reaction mixture was heated at 80 oC for 18 h.
  • the reaction was cooled to ambient temperature and filtered through a pad of Celite ® diatomaceaous earth filter aid.
  • Step B of Synthesis Example 1 0.19 g, 0.446 mmol) , 0.5 M sodium methoxide in methanol (0.893 mL, 0.446 mmol), tBuXPhos Pd G3 catalyst (0.035 g, 0.045 mmol) and toluene (2.976 mL, 0.15 M) was sparged with nitrogen for 5 min and then heated at 90 oC for 18 h. The reaction was cooled to ambient temperature and filtered through a pad of Celite ® diatomaceaous earth filter aid.
  • Step B Preparation of 2-bromo-3-chloro-5-fluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine To a solution of the crude product from step A (0.23 g, 0.78 mmol) in 3.89 mL of chloroform was added bromine (0.24 g, 1.56 mmol) dropwise over 5 minutes.
  • Step C Preparation of 3-chloro-5-fluoro-2- ⁇ [3-(trifluoromethyl)phenyl] methyl ⁇ -6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine
  • a vial was charged with 2-bromo-3-chloro-5-fluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine (i.e. the product of Step B, 0.22 g, 0.62 mmol) and (Tetrakis(triphenylphosphine)Pd(0) (0.036 g, 0.031 mmol) and purged with N 2 .
  • Step D Preparation of 5-fluoro-3-methyl-2-[[3-(trifluoromethyl)phenyl]methyl]-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine A vial was charged with 3-chloro-5-fluoro-2- ⁇ [3-(trifluoromethyl)phenyl]methyl ⁇ -6- [3-(trifluoromethyl)pyrazol-1-yl]pyridine (i.e.
  • Step C the product of Step C, 0.080 g, 0.19 mmol), potassium carbonate (0.078 g, 0.566 mmol), and 2-dicyclohexylphosphino-2′,6′-diisopropoxy- 1,1′-biphenyl[2-(2'-amino-1,1'-biphenyl)]Pd(II) methanesulfonate (0.013 g, 0.015 mmol) and purged with N 2 .
  • t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Pr means isopropyl, c-Pr means cyclopropyl, t-Bu means tertiary butyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, -CN means cyano, -NO 2 means nitro, TMS means trimethylsilyl, SOMe means methylsulfinyl, C 2 F 5 means CF 2 CF 3 and SO 2 Me means methylsulfonyl.
  • R 1 R 2 R 3 R 4 methyl CF 3 CF 3 H ethyl CF 3 CF 3 H n-propyl CF 3 CF 3 H c-propyl CF 3 CF 3 H Cl CF 3 CF 3 H Br CF 3 CF 3 H methoxy CF 3 CF 3 H methyl CF 3 OCF 3 H ethyl CF 3 OCF 3 H n-propyl CF 3 OCF 3 H c-propyl CF 3 OCF 3 H Cl CF 3 OCF 3 H Br CF 3 OCF 3 H methoxy CF 3 OCF 3 H methyl CF 3 CF 3 F ethyl CF 3 CF 3 F n-propyl CF 3 CF 3 F c-propyl CF 3 CF 3 F Cl CF 3 CF 3 F Br CF 3 F methoxy CF 3 F methyl Cl CF 3 H ethyl Cl CF 3 H n-propyl Cl CF 3 H n-propy
  • 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.
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion, oil-in-water emulsion, flowable concentrate and suspo-emulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film- forming solutions or flowable suspensions are particularly useful for seed treatment.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively, the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient.
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation. Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water, but occasionally another suitable medium like an aromatic or paraffinic hydrocarbon or vegetable oil.
  • Spray volumes can range from about from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare.
  • Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant.
  • Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001–90 0–99.999 0–15 soluble Granules, Tablets and Powders Oil Dispersions, Suspensions, 1–50 40–99 0–50 Emulsions, Solutions (including Emulsifiable Concentrates) Dusts 1–25 70–99 0–5 Granules and Pellets 0.001–99 5–99.999 0–15 High Strength Compositions 90–99 0–10 0–2 Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • clays such
  • 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 tria
  • Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C 6 –C 22 ), 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.
  • 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
  • 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.
  • 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
  • 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 e
  • Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.
  • amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amine
  • 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).
  • 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.
  • 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 ⁇ m can be wet milled using media mills to obtain particles with average diameters below 3 ⁇ m. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S.3,060,084) or further processed by spray drying to form water-dispersible granules.
  • Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill).
  • Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, December 4, 1967, pp 147–48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8–57 and following, and WO 91/13546.
  • Pellets can be prepared as described in U.S.4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S.3,299,566.
  • 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.
  • Example A High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%
  • Example B Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%
  • Example C Granule Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S.
  • 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% C 6 –C 10 fatty acid methyl ester 70.0%
  • Example F Microemulsion Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% Water 20.0%
  • Example G Suspension Concentrate Compound 1 35% butyl polyoxyethylene/polypropylene block copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol
  • the compounds of the inention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures.
  • 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).
  • 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
  • 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.
  • the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth
  • the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation.
  • Undesired vegetation includes at least one selected from the group consisting of grass weeds and broadleaf weeds.
  • Undesired vegetation is selected from the group consisting of annual bluegrass, Benghal dayflower, blackgrass, black nightshade, broadleaf signalgrass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, corn poppies, field violet, giant foxtail, goosegrass, green foxtail, guinea grass, hairy beggarticks, herbicide-resistant black grass, horseweed, Italian rye grass, jimsonweed, Johnson grass (Sorghum halepense), large crabgrass, little seed canary grass, morning glory, Pennsylvania smartweed, pitted morning glory, prickly sida, quackgrass, redroot pigweed, shattercane, shepherd's purse, silky windgrass, sunflower (as weed in potato), wild buckwheat (Polygonum convolvulus), wild mustard (Brass
  • 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).
  • 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.
  • 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 enhanced effects with genetic traits in the desired vegetation, including traits incorporated through genetic modification. For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic/abiotic stresses or storage stability may be greater than expected from the genetic traits in the desired vegetation.
  • Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes.
  • the present invention also pertains to a composition
  • 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.
  • 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), 4- amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)-2-Pyridinecarboxylic 2-propyn-1-yl ester (CAS No.
  • anilofos anisiflupurin, asulam, atrazine, azimsulfuron, bixlozone, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquitrione, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bipyrazone, bispyribac and its sodium salt, broclozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, bipyrazone, cafenstrole, carbetamide, 1-(
  • chlorotoluron chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, cypyrafluone, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, cyprafluone, daimur
  • 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.
  • bioherbicides such as Alternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.
  • Preferred for better control of undesired vegetation e.g., lower use rate such as from enhanced effects, broader spectrum of weeds controlled, or enhanced crop safety
  • a herbicide selected from the group consisting of atrazine, azimsulfuron, S-beflubutamid, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, 2-[(2,4-dichlorophenyl)methyl]- 4,4-dimethyl-3-isoxazolidinone, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3- isoxazolidinone, ethametsulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy- 6-
  • Plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl, and plant growth modifying organisms such as Bacillus cereus strain BP01.
  • plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin A 4 and A 7 , harpin protein, mepiquat chloride, prohexadione calcium, prohydrojasmon, sodium nitrophenolate and trinexapac-methyl
  • plant growth modifying organisms such as Bacillus cereus strain BP01.
  • General references for agricultural protectants i.e. herbicides, herbicide safeners, insecticides
  • the mixing partners are typically used in the amounts similar to amounts customary when the mixture partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between one-half and the full application rate specified on product labels for use of active ingredient alone. These amounts are listed in references such as The Pesticide Manual and The BioPesticide Manual.
  • the weight ratio of these various mixing partners (in total) to the compound of Formula 1 is typically between about 1:3000 and about 3000:1.
  • 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.
  • 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. enhanced) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants.
  • 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.
  • 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 (BC
  • Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener.
  • Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation.
  • Compounds of the invention can also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect.
  • compositions 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)).
  • 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.
  • Compound No. in the Component (a) column is identified in Index Table A.
  • 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 A96 are constructed similarly.
  • TESTS demonstrate the control efficacy of compounds of this invention on specific pathogens.
  • the pathogen control protection afforded by the compounds is not limited, however, to these species. See Index Tables A through E below for compound descriptions.
  • the abbreviation “Cmpd.” stands for “Compound”, and the abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared.
  • the numerical value reported in the column “MS” is the molecular weight of the highest isotopic abundance positively charged parent ion (M+1) formed by addition of H+ (molecular weight of 1) to the molecule having the highest isotopic abundance, or the highest isotopic abundance negatively charged ion (M–1) formed by loss of H+ (molecular weight of 1).
  • “Pyr” means “Pyridine”. “Przl” means “Pyrazol”. “Thzl” means “Thiazole”. “Imdzl” mean “Imidazol”. “Trzl” means “Triazol”. “1,2,4-Trzl” means “1,2,4-Triazol” shown as below. The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g., 37 Cl, 81 Br) is not reported. The reported MS peaks were observed by mass spectrometry using electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI). INDEX TABLE A C mpd. No.
  • plants selected from these crop and weed species and also galium (catchweed bedstraw, Galium aparine) and horseweed (Erigeron canadensis) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (–) response means no test result..
  • test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test.
  • Treated plants and controls were maintained in a greenhouse for 13 days, after which time all species were compared to controls and visually evaluated.
  • Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (–) response means no test result.
  • Treated plants and untreated controls can be maintained in a greenhouse for 13 days for postemergence and 20 days for preemergence testing, after which time the treated plants can be compared to untreated controls and visually evaluated for injury.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides (Formula 1) wherein J is selected from the group consisting of (Formulas) and R1. R2, R3, R4, X and Q are as defined in the disclosure.

Description

TITLE SUBSTITUTED FLUOROPYRIDINE AS HERBICIDES FIELD OF THE INVENTION This invention relates to certain substituted fluoropyridine herbicides, their N-oxides, salts and compositions, and methods of their use for controlling undesirable vegetation. 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, all stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides: wherein
Figure imgf000003_0002
J is selected from the group consisting of
Figure imgf000003_0001
Figure imgf000004_0001
Q is O, -CH2- or -(C=O)-; R1 is halogen, C1–C4 alkyl, C3–C4 cycloalkyl, C1–C3 haloalkyl, C1–C3 alkoxy, or C1–C3 haloalkoxy; R2 is H, halogen, CN, C1–C4 alkyl, C1–C3 haloalkyl or C1–C3 haloalkoxy; R3 is halogen, C1–C3 haloalkyl or C1–C3 haloalkoxy; R4 is H, halogen or methoxy; X is N or CR5; and R5 is H, halogen, C1-C3 haloalkyl, CH3 or cyano; provided when R2 is H, R5 is other than H. 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 (b17), and salts of compounds of (b1) through (b17), 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. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH3S(O)-, CH3CH2S(O)-, CH3CH2CH2S(O)-, (CH3)2CHS(O)- and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH3S(O)2-, CH3CH2S(O)2-, CH3CH2CH2S(O)2-, (CH3)2CHS(O)2-, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH2 and NCCH2CH2 (alternatively identified as CH2CH2CN). “Nitroalkyl” denotes an alkyl group substituted with one nitro group. Examples of “nitroalkyl” include NO2CH2 and NO2CH2CH2 (alternatively identified as CH2CH2NO2). “Cyano” means -CN, and “formyl” means HC(=O)-. “Alkylamino” includes an NH radical substituted with straight-chain or branched alkyl. Examples of “alkylamino” include CH3CH2NH, CH3CH2CH2NH, and (CH3)2CHCH2NH. Examples of “dialkylamino” include (CH3)2N, (CH3CH2CH2)2N and CH3CH2(CH3)N. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “alkylcycloalkyl” donotes an alkyl group bonded to a cycloalkyl moiety. 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”, “haloalkoxyalkyl”, “haloalkylthio”, “haloalkenyl”, “haloalkynyl”, and the like, are as defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF3O- , CCl3CH2O-, HCF2CH2CH2O- and CF3CH2O-. Examples of “haloalkoxyalkyl” include CF3OCH2-, CCl3CH2OCH2-, HCF2CH2CH2OCH2- and CF3CH2OCH2-. 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-. 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 4. For example, C1–C4 alkyl can be, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl. When a group contains a substituent which can be hydrogen, for example R2, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency. Unless otherwise indicated as being optionally substituted, the term “phenyl” means unsubstituted phenyl. Unless otherwise indicated as being optionally substituted, the term “benzyl” means unsubstituted benzyl. 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 to 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, 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. 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. Embodiments of the present invention as described in the Summary of the Invention include those described below. In the following Embodiments, Formula 1 includes stereoisomers, N-oxides and salts thereof, and reference to “a compound of Formula 1” includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments. Embodiment 1. A compound of Formula 1, stereoisomers, N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides as described in the Summary of the Disclosure. J Embodiment 2. A compound of Formula 1 or Embodiment 1 wherein J is J-1, J-2, J-3, J- 5 or J-6. Embodiment 2a. A compound of Formula 1 or Embodiment 2 wherein J is J-1, J-2 or J-3. Embodiment 2b. A compound of Embodiment 2a wherein J is J-1. Embodiment 2c. A compound of Embodiment 2a wherein J is J-2. Embodiment 2d. A compound of Embodiment 2a wherein J is J-3. Embodiment 2e. A compound of Formula 1 or Embodiment 2 wherein J is J-5 or J-6. Embodiment 2f. A compound of Embodiment 2e wherein J is J-5. Embodiment 2g. A compound of Embodiment 2e wherein J is J-6. Embodiment 2h. A compound of Embodiment 2e wherein J is J-7. Embodiment 2i. A compound of Embodiment 2e wherein J is J-8. Embodiment 2j. A compound of Embodiment 2e wherein J is J-9. Embodiment 2k. A compound of Embodiment 2e wherein J is J-10. Embodiment 2l. A compound of Embodiment 2e wherein J is J-11. Q Embodiment 3. A compound of Formula 1 or any one of the preceding Embodiments wherein Q is O, -CH2- or -(C=O)-. Embodiment 3a. A compound of Embodiment 9 wherein Q is O or -CH2-. Embodiment 3b. A compound of Embodiment 9a wherein Q is O. Embodiment 3c. A compound of Embodiment 9a wherein Q is -(C=O)-. R1 Embodiment 4. A compound of Formula 1 or any one of the preceding Embodiments wherein R1 is halogen, C1–C4 alkyl, C3–C4 cycloalkyl, C1–C3 haloalkyl, C1–C3 alkoxy or C1–C3 haloalkoxy. Embodiment 4a. A compound of Embodiment 4 wherein R1 is halogen, C1–C4 alkyl, C3–C4 cycloalkyl or C1–C3 alkoxy. Embodiment 4b. A compound of Embodiment 4a wherein R1 is F, Cl, C1–C4 alkyl or C3–C4 cycloalkyl or C1–C3 alkoxy. Embodiment 4c. A compound of Embodiment 4b wherein R1 is Cl. Embodiment 4d. A compound of Embodiment 4b wherein R1 is C1–C4 alkyl. Embodiment 4e. A compound of Embodiment 4d wherein R1 is Me or Et. Embodiment 4f. A compound of Embodiment 4b wherein R1 is C3–C4 cycloalkyl. Embodiment 4g. A compound of Embodiment 4f wherein R1 is cyclopropyl. Embodiment 4h. A compound of Embodiment 4b wherein R1 is C1–C3 alkoxy. Embodiment 4i. A compound of Embodiment 4h wherein R1 is OMe. Embodiment 4j. A compound of Embodiment 4b wherein R1 is Cl, Me, Et, cyclopropyl or OMe. Embodiment 4k. A compound of Embodiment 4j wherein R1 is Me, Et or cyclopropyl. Embodiment 4l. A compound of Embodiment 4k wherein R1 is Me or Et. R2 Embodiment 5. A compound of Formula 1 or any one of the preceding Embodiments wherein R2 is H, halogen, CN, C1–C4 alkyl, C1–C3 haloalkyl or C1–C3 haloalkoxy. Embodiment 5a. A compound of Formula 1 or any one of the preceding Embodiments wherein R2 is C1–C3 haloalkyl. Embodiment 5b. A compound of Embodiment 5a wherein R2 is CF3. Embodiment 5c. A compound of Embodiment 5a wherein R2 is CHF2. R3 Embodiment 6. A compound of Formula 1 or any one of the preceding Embodiments wherein R3 is halogen, C1–C3 haloalkyl or C1–C3 haloalkoxy. Embodiment 6a. A compound of Embodiment 6 wherein R3 is C1–C3 haloalkyl or C1–C3 haloalkoxy. Embodiment 6b. A compound of Embodiment 6a wherein R3 is CF3 or OCF3. Embodiment 6c. A compound of Embodiment 6b wherein R3 is CF3. Embodiment 6d. A compound of Embodiment 6b wherein R3 is OCF3. R4 Embodiment 7. A compound of Formula 1 or any one of the preceding Embodiments wherein R4 is H, halogen or OMe. Embodiment 7b. A compound of Embodiment 7a wherein R4 is H, F or OMe. Embodiment 7c. A compound of Embodiment 7b wherein R4 is H. Embodiment 7d. A compound of Embodiment 7b wherein R4 is F. Embodiment 7b. A compound of Embodiment 7b wherein R4 is OMe. X Embodiment 8. A compound of Formula 1 or any one of the preceding Embodiments wherein X is N or CR5. Embodiment 8a. A compound of Formula 1 or any one of the preceding Embodiments wherein X is N. Embodiment 8b. A compound of Formula 1 or any one of the preceding Embodiments wherein X is CR5. R5 Embodiment 11. A compound of Formula 1 or any one of the preceding Embodiments wherein R5 is H, halogen, C1–C3 haloalkyl, Me and CN. Embodiment 11a. A compound of Embodiment 11 wherein R5 is H, halogen or C1–C3 haloalkyl. Embodiment 11aa. A compound of Embodiment 11a wherein R5 is H, Cl, Br or CF3. Embodiment 11b. A compound of Embodiment 11a wherein R5 is H. Embodiment 11c. A compound of Embodiment 11a wherein R5 is halogen. Embodiment 11d. A compound of Embodiment 11c wherein R5 is Cl or Br. Embodiment 11e. A compound of Embodiment 11a wherein R5 is C1–C3 haloalkyl. Embodiment 11f. A compound of Embodiment 11e wherein R5 is CF3. Embodiments of this invention, including Embodiments 1–11f 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 1–11f 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 1–11f are illustrated by: Embodiment A. A compound of Formula 1 as described in the Summary of the Disclosure wherein J is J-1, J-2 or J-3; Q is O or -CH2-. Embodiment B. A compound of Embodiment A wherein R1 is halogen, C1–C4 alkyl, C3–C4 cycloalkyl, C1–C3 haloalkyl, C1–C3 alkoxy, or C1– C3 haloalkoxy; R2 is H, halogen, CN, C1–C4 alkyl, C1–C3 haloalkyl or C1–C3 haloalkoxy; R3 is halogen, C1–C3 haloalkyl or C1–C3 haloalkoxy; R4 is H, halogen or OMe; X is N or CR5; and R5 is H, halogen, C1–C3 haloalkyl, Me and CN. Embodiment C. A compound of Embodiment B wherein R1 is F, Cl, C1–C4 alkyl or C3–C4 cycloalkyl or C1–C3 alkoxy; and R3 is C1–C3 haloalkyl or C1–C3 haloalkoxy. Embodiment D. A compound of Embodiment C wherein R2 is C1–C3 haloalkyl; R4 is H, F or OMe; and R5 is H, halogen or C1–C3 haloalkyl. Embodiment E. A compound of Embodiment D wherein R1 is Cl, Me, Et, cyclopropyl or OMe; R2 is CF3; and R5 is H, Cl, Br or CF3. Embodiment F. A compound of Embodiment E wherein R5 is CF3. Embodiment G. A compound of Embodiment A or any one of the preceding Embodiments wherein J is J-1; Q is O. Embodiment H. A compound of Embodiment B wherein X is CR5. Embodiment I. A compound of Embodiment A wherein J is J-2; X is CR5; and R5 is CF3. Specific embodiments include compounds of Formula 1 selected from the group consisting of: 3-ethyl-5-fluoro-2-[3-(trifluoromethoxy)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 20); 3-ethyl-5-fluoro-6-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-[[6-(trifluoromethyl)- 2-pyridinyl]oxy]pyridine (Compound 42); 3-ethyl-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 51); 3-fluoro-5-methoxy-6-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 54); and 2-[3-(difluoromethyl)-1H-pyrazol-1-yl]-5-Ethyl-3-fluoro-6-[3- (trifluoromethyl)phenoxy]pyridine (Compound 74). Embodiment AA. A compound of Formula 1 as described in the Summary of the Disclosure wherein J is J-1, J-2, J-3, J-4, J-5 or J-6. Surprisingly, it is discovered that the compounds in the current invention (i.e. with F at the 5-position of the pyridine core) demonstrate higher herbicidal activities than the compounds with other substituents (e.g., H) at the 5-position. In addition, the compounds in the current invention also show remarkable safety to crops, such as maize, soybeans and wheat. This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein). Of note as embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for selective control of weeds in crops such as wheat, barley, maize, soybean, sunflower, cotton, oilseed rape and rice, and specialty crops such as sugarcane, citrus, fruit and nut crops. Also noteworthy as embodiments are herbicidal compositions of the present invention comprising the compounds of embodiments described above. This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol- pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solanesyltransferase (HST) inhibitors, (b14) cellulose biosynthesis inhibitors, (b15) dehydrooritate dehydrogenase (DHODH) inhibitors, (b16) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, hydantocidin, icafolin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b17) herbicide safeners, and salts of compounds of (b1) through (b17). “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, metproxybicyclone, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn and trietazine. “AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2- yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4- (5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro-N-[[(4,6-dimethoxy-2- pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide), prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6- fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron-methyl and tritosulfuron. “ACCase inhibitors” (b3) are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl. Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics” (b4) are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4- pyrimidinecarboxylic acid) and its methyl and ethyl esters and its sodium and potassium salts, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)-2-Pyridinecarboxylic 2-propyn-1-yl ester (CAS No. 2251111-17-6), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)-2- Pyridinecarboxylic cyanomethyl ester (CAS No. 2251111-18-7), aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA, triclopyr, and methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate. “EPSP synthase inhibitors” (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points. Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate). “Photosystem I electron diverters” (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles “leak”, leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include diquat, paraquat and 1-(2-carboxyethyl)-4-(2- pyrimidinyl)pyridazinium (CAS No.2285384-11-2). “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, 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5- Isoxazolecarboxylic ethyl ester (CAS No. 1949837-17-5), cinidon-ethyl, fluazolate, flufenoximacil, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, trifludimoxazin (dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2- propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione) and tiafenacil (methyl N-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate). “GS inhibitors” (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. The GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P ((2S)-2-amino- 4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos. “VLCFA elongase inhibitors” (b9) are herbicides having a wide variety of chemical structures, which inhibit the elongase. Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs. In plants, very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fenoxasulfone (3- [[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)-N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides. “Auxin transport inhibitors” (b10) are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N-(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid). “PDS inhibitors” (b11) are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step. Examples of PDS inhibitors include beflubutamid, 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), flusulfinam, iptriazopyrid, isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5- yl]oxy]ethyl methyl carbonate), topramezone, 5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1- yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 4-(2,6-diethyl-4-methylphenyl)-5- hydroxy-2,6-dimethyl-3(2H)-pyridazinone, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1- cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, 5-[(2-hydroxy-6-oxo- 1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)- pyrimidinone, 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4- (trifluoromethyl)benzamide and 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)- 4-(trifluoromethyl)benzamide. “HST (homogentisate solanesyltransferase) 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 cyclopyrimorate (6-chloro-3-(2- cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-morpholinecarboxylate), 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.
Figure imgf000018_0001
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. “DHODH (dihydroorotate dehydrogenase) inhibitors” (b15) act through inhibiting catalysis of the fourth step of pyrimidine biosynthesis in plant systems. Inhibition of pyrimidine biosynthesis leads to the cessation of plant growth. Examples of DOHDH inhibitors include tetflupyrolimet ((3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3- (trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide) and (3S,4R)-N-(2,3-difluorophenyl)-1- methyl-4-[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-oxo-3-pyrrolidinecaboxamide. “Other herbicides” (b16) 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, bixlozone, broclozone, bromobutide, cinmethylin, clomazone, cumyluron, daimuron, difenzoquat, dimesulfazet, epyrifenacil, 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, 2,5- anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5-ethenyl-4,5-dihydro-5- isoxazolyl]carbonyl]amino]-threo-Pentonic methyl ester (CAS No. 27499989-21-6) and 5- [[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2- thienyl)isoxazole. “Other herbicides” (b16) also include a compound of Formula (b16A) wherein
Figure imgf000019_0001
R12 is H, C1–C6 alkyl, C1–C6 haloalkyl or C4–C8 cycloalkyl; R13 is H, C1–C6 alkyl or C1–C6 alkoxy; Q1 is an optionally substituted ring system selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl and pyrazolyl, wherein when substituted said ring system is substituted by 1 to 3 R14; Q2 is an optionally substituted ring system selected from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, wherein when substituted said ring system is substituted by 1 to 3 R15; each R14 is independently halogen, C1–C6 alkyl, C1–C6 haloalkyl, C1–C6 alkoxy, C1– C6 haloalkoxy, C3–C8 cyaloalkyl, cyano, C1–C6 alkylthio, C1–C6 alkylsulfinyl, C1–C6 alkylsulfonyl, SF5, NHR17; or phenyl optionally substituted by 1 to 3 R16; or pyrazolyl optionally substituted by 1 to 3 R16; each R15 is independently halogen, C1–C6 alkyl, C1–C6 haloalkyl, C1–C6 alkoxy, C1– C6 haloalkoxy, cyano, nitro, C1–C6 alkylthio, C1–C6 alkylsulfinyl, C1–C6 alkylsulfonyl; each R16 is independently halogen, C1–C6 alkyl or C1–C6 haloalkyl; R17 is C1–C4 alkoxycarbonyl. In one Embodiment wherein “other herbicides” (b16) also include a compound of Formula (b16A), it is preferred that R12 is H or C1–C6 alkyl; more preferably R12 is H or methyl. Preferrably R13 is H. Preferably Q1 is either a phenyl ring or a pyridinyl ring, each ring substituted by 1 to 3 R14; more preferably Q1 is a phenyl ring substituted by 1 to 2 R14. Preferably Q2 is a phenyl ring substituted by 1 to 3 R15; more preferably Q2 is a phenyl ring substituted by 1 to 2 R15. Preferably each R14 is independently halogen, C1–C4 alkyl, C1–C3 haloalkyl, C1–C3 alkoxy or C1–C3 haloalkoxy; more preferably each R14 is independently chloro, fluoro, bromo, C1–C2 haloalkyl, C1–C2 haloalkoxy or C1–C2 alkoxy. Preferrably each R15 is independently halogen, C1–C4 alkyl, C1–C3 haloalkoxy; more preferably each R15 is independently chloro, fluoro, bromo, C1–C2 haloalkyl, C1–C2 haloalkoxy or C1–C2 alkoxy. Specifically preferred as “other herbicides” (b16) include any one of the following (b16A-1) through (b16A-15):
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Figure imgf000023_0001
Other herbicides (b16) also include a compound of Formula (b16B) wherein
Figure imgf000023_0002
R18 is H, C1–C6 alkyl, C1–C6 haloalkyl or C4–C8 cycloalkyl; each R19 is independently halogen, C1–C6 haloalkyl or C1–C6 haloalkoxy; p is an integer of 0, 1, 2 or 3; each R20 is independently halogen, C1–C6 haloalkyl or C1–C6 haloalkoxy; and q is an integer of 0, 1, 2 or 3. In one Embodiment wherein “other herbicides” (b16) also include a compound of Formula (b15B), it is preferred that R18 is H, methyl, ethyl or propyl; more preferably R18 is H or methyl; most preferably R18 is H. Preferrably each R19 is independently chloro, fluoro, C1– C3 haloalkyl or C1–C3 haloalkoxy; more preferably each R19 is independently chloro, fluoro, C1 fluoroalkyl (i.e. fluoromethyl, difluoromethyl or trifluoromethyl) or C1 fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy). Preferably each R20 is independently chloro, fluoro, C1 haloalkyl or C1 haloalkoxy; more preferably each R20 is independently chloro, fluoro, C1 fluoroalkyl (i.e. fluoromethyl, difluorormethyl or trifluromethyl) or C1 fluoroalkoxy (i.e. trifluoromethoxy, difluoromethoxy or fluoromethoxy). Specifically preferred as “other herbicides” (b16) include any one of the following (b15B-1) through (b16B-19):
Figure imgf000024_0001
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000027_0001
wherein R1 is Cl, Br or CN; and R2 is C(=O)CH2CH2CF3, CH2CH2CH2CH2CF3 or 3-CHF2-isoxazol-5-yl. “Other herbicides” (b16) also include a compound of Formula (b16D)
Figure imgf000027_0002
Wherein R1 is C1–C4 alkyl or C3–C6 cycloalkyl; R2 is H, Cl, Br or I; R3 is Cl or OR4; R4 is H or C1–C4 alkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl. Particularly, b16D can be 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone; 6-chloro-4-(7-fluoro-2-methyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone; 6-chloro-4-(7-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone; or 6-chloro-4-(4-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2- methyl-3(2H)-pyridazinone. “Herbicide safeners” (b17) are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation. Examples of herbicide safeners include but are not limited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone, naphthalic anhydride, oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide and N- (aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa- 4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)- ethanone and 2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]- benzamide. Preferred for better control of undesired vegetation (e.g., lower use rate such as from greater-than-additive effects, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of 4-amino-3-chloro-5-fluoro- 6-(7-fluoro-1H-indol-6-yl)- 2-Pyridinecarboxylic 2-propyn-1-yl ester (CAS No.2251111-17- 6), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)- 2-Pyridinecarboxylic cyanomethyl ester (CAS No.2251111-18-7), 2,5-anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5- ethenyl-4,5-dihydro-5-isoxazolyl]carbonyl]amino]-threo-Pentonic methyl ester (CAS No. 27499989-21-6), atrazine, azimsulfuron, beflubutamid, beflubutamid-M, bixlozone, broclozone, benzisothiazolinone, 1-(2-carboxyethyl)-4-(2-pyrimidinyl)pyridazinium (CAS No. 2285384-11-2) and salts thereof, carfentrazone-ethyl, chlorimuron-ethyl, 3-[2-chloro-5- [3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]- 4,5-dihydro-5-methyl-5-isoxazolecarboxylic ethyl ester (CAS No. 1949837-17-5), chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, ethametsulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1- cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, pethoxamid, picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl and tribenuron-methyl. One or more of the following methods and variations as described in Schemes 1–3 can be used to prepare the compounds of Formula 1. The definitions of R1, R2, X and J in the compounds of Formulae 1–4 below are as defined above in the Summary of the Invention unless otherwise noted. Compounds of Formulae 1a and 1b are various subsets of the compounds of Formulae 1; and all substituents for Formulae 1a and 1b are as defined above for Formula 1 unless otherwise noted in the disclosure including the schemes. Compounds of Formula 1a (i.e., compounds of Formula 1 wherein Q is O) can be prepared as outlined in Scheme 1. Reacting a pyridine of Formula 2, where LG1 represents a leaving group, preferably halogen, with an appropriately substituted phenol or hydroxy heterocycle of Formula J-OH in the presence of a suitable base and solvent results in displacement of the leaving group LG1 to provide compounds of Formula 1a. Examples of appropriate bases for this reaction include but are not limited to potassium carbonate, sodium hydroxide, potassium t-butoxide, sodium hydride or potassium hydroxide and compatible solvents such as tetrahydrofuran, acetonitrile, toluene, dioxane or N,N-dimethylformamide. Temperatures for this reaction generally range from 0° C to warming below or heating at the boiling point of the solvent. Scheme 1 Compounds of Formula 1b (i.e., compounds of Formula 1 where Q is CH2) can be made by a general synthetic route, usually referred to as a “Negishi Cross-coupling”, as outlined in Scheme 2. Reacting a bromopyridine of Formula 3 with an appropriately substituted benzyl, pyridylmethyl or pyrazolyl methyl zinc reagent of Formula JCH2ZnBr or JCH2ZnCl in the presence of a suitable palladium catalyst in a solvent such as tetrahydrofuran, acetonitrile, toluene, dioxane or N,N-dimethylformamide provides compounds of Formula 1b. Temperatures for this reaction generally range from -78° C to warming below or heating at the boiling point of the solvent. Reagents of Formula JCH2ZnBr and JCH2ZnCl are readily generated from the commercially available benzyl and heteroaryl methyl halides in many cases by reacting with an appropriate zinc reagent (i.e. zinc dust, ZnCl2, TMPZnCl ^LiCl, or TMP2Zn ^2MgCl2 ^2LiCl), usually in the solvent used for the coupling. Suitable palladium catalysts include but are not limited to tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] and bis(triphenylphosphine) palladium(II) dichloride [PdCl2(PPh3)2, Dichlorobis(triphenylphosphine) palladium(II)]. Scheme 2 Intermediates of Formula 2 can be made by reacting a pyridine of Formula 4 (where LG1 and LG2 both represent suitable leaving groups such as halogen) and one equivalent or slightly over one equivalent of a pyrazole or triazole of Formula 5 in the presence of an appropriate base and solvent. Displacement of LG2 by the azole of Formula 5 is generally preferred over displacement of leaving group LG1 to provide compounds of Formula 1a. However, one skilled in the art will recognize that some displacement of LG1 can occur to give rise to an undesired regioisomeic side-product. Examples of appropriate bases for this reaction include but are not limited to potassium carbonate, sodium hydroxide, potassium t- butoxide, sodium hydride or potassium hydroxide and compatible solvents include but not limited to tetrahydrofuran, acetonitrile, toluene, dioxane or N,N-dimethylformamide. Temperatures for this reaction generally range from 0° C to warming below or heating at the boiling point of the solvent. Scheme 3 Compounds of Formula 1 where R1 is bromine or chlorine can also be converted to compounds of Formula 1 where R1 is alkyl or cycloalkyl by reacting with an alkyl or cycloalkyl boronic acid of R1B(OH)2 (where R1 is alkyl or cycloalkyl) in the presence of an appropriate palladium catalyst in a suitable solvent such tetrahydrofuran, acetonitrile, toluene, dioxane or N,N-dimethylformamide or dichloromethane. Preferable palladium catalysts include but are not limited to commercially available chloro[2-(di-tert-butylphosphino)- 2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl)] palladium(II) [t-BuXPhos palladium(II) phenethylamine chloride, tBuXPhos-Pd-G1], chloro[(tri-tert-butylphosphine)- 2-(2-aminobiphenyl)] palladium(II) [P(t-Bu)3 Pd G2], methanesulfonato(2-di-t- butylphosphino-2;methanesulfonato(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl) (2'-amino-1,1'-biphenyl-2-yl)palladium(II) [tBuXPhos-Pd-G3], 2-Dicyclohexylphosphino- 2′,6′-diisopropoxybiphenyl [RuPhos], (2-Dicyclohexyl phosphino-2′,6′-diisopropoxy-1,1′- biphenyl)[2-(2′-amino-1,1′-biphenyl)] palladium (II) methanesulfonate [RuPhos-G3] or Pd2(dba)3 with SPhos. Temperatures for this coupling reaction generally range from 0° C to warming below or heating at the boiling point of the solvent. Oxidation of compounds of Formula 1b under appropriate oxidative conditions such as copper iodide and acetic acid in dimethyl sulfoxide or with iron trichloride and air in dimethyl sulfoxide can provide compounds of Formula 1 where Q is carbonyl. It is recognized by one skilled in the art that various functional groups can be converted into others to provide different compounds of Formula 1. For a valuable resource that illustrates the interconversion of functional groups in a simple and straightforward fashion, see Larock, R. C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. For example, intermediates for the preparation of compounds of Formula 1 may contain aromatic nitro groups, which can be reduced to amino groups, and then be converted via reactions well known in the art such as the Sandmeyer reaction, to various halides, providing compounds of Formula 1. The above reactions can also in many cases be performed in alternate order. It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the partcular presented to prepare the compounds of Formula 1. One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following non-limiting Examples are illustrative of the invention. Steps in the following Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. All NMR spectra are reported in CDCl3 downfield from tetramethylsilane at 500 MHz unless otherwise indicated where s means singlet, brs means broad singlet, d means doublet, t means triplet and m means multiplet. SYNTHESIS EXAMPLE 1 Preparation of 3-ethyl-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine (Compound 51) Step A: Preparation of 3-chloro-2,5-difluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine In a round-bottom flask, 3-chloro-2,5,6-trifluoropyridine (3.0 g, 17.9 mmol), 3- (trifluoromethyl)-1H-pyrazole (2.44 g, 17.9 mmol) and potassium carbonate (2.97 g, 21.5 mmol) were combined in acetonitrile (59.7 mL, 0.3 M). The reaction mixture was heated at 50 ºC for 5 h. The reaction was cooled to ambient temperature and filtered through a pad of Celite® diatomaceaous earth filter aid. The filtrate was concentrated in vacuo. The crude material was purified by column chromatography, eluting with 0 to 10% ethyl acetate in heptane gradient to afford the titled compound (2.77 g, 54.5%). 1H NMR (CDCl3) δ ppm 8.30–8.32 (m, 1H), 7.85–7.88 (m, 1H), 6.76–6.78 (m, 1H). Step B: Preparation of 3-chloro-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine To a stirred solution of 3-chloro-2,5-difluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine (i.e. the product of Step A, 2.77 g, 9.77 mmol) and m-trifluoromethylphenol (1.19 mL, 9.77 mmol) in acetonitrile (48.8 mL, 0.2 M) was added potassium carbonate (1.62 g, 11.7 mmol). The reaction mixture was heated at 60 ºC for 18 h. The reaction was cooled to room temperature and filtered through a pad of Celite® diatomaceaous earth filter aid. The filtrate was concentrated in vacuo and the crude material was purified by column chromatography, eluting with 0 to 10% ethyl acetate in heptane to afford the titled compound (4.03 g, 96.9% yield). 1H NMR (CDCl3) δ ppm 7.81–7.92 (m, 2H), 7.50–7.61 (m, 3H), 7.37–7.45 (m, 1H), 6.62– 6.65 (m, 1H). Step C: Preparation of 3-ethyl-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine A mixture containing 3-chloro-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl) pyrazol-1-yl]pyridine (i.e. the product of Step B, 4.03 g, 9.46 mmol), ethylboronic acid (1.40 g, 18.93 mmol) and potassium carbonate (2.62 g, 18.9 mmol) in toluene (47.3 mL, 0.2 M) and water (4.73 mL, 2 M) was sparged with N2 for 10 min. To this was added RuPhosPd G3 catalyst (0.396 g, 0.473 mmol, 0.05 equiv.). The reaction mixture was heated at 80 ºC for 18 h. The reaction was cooled to ambient temperature and filtered through a pad of Celite® diatomaceaous earth filter aid. The filtrate was concentrated in vacuo and the crude material was purified by column chromatography to afford the titled compound (3.22 g, 81% yield). 1H NMR (CDCl3) δ ppm 7.88–7.91 (m, 1H), 7.56–7.61 (m, 1H), 7.46–7.56 (m, 3H), 7.33– 7.38 (m, 1H), 6.62–6.66 (m, 1H), 2.81 (q, J=7.5 Hz, 2H), 1.34 (t, J=7.5 Hz, 3H). SYNTHESIS EXAMPLE 2 Preparation of 3-fluoro-5-methoxy-6-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)- 1H-pyrazol-1-yl]pyridine (Compound 54) Step A: Preparation of 3-fluoro-5-methoxy-6-[3-(trifluoromethyl)phenoxy]-2-[3- (trifluoromethyl)-1H-pyrazol-1-yl]pyridine A vial charged with 3-chloro-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3- (trifluoromethyl) pyrazol-1-yl]pyridine (i.e. the product of Step B of Synthesis Example 1, 0.19 g, 0.446 mmol) , 0.5 M sodium methoxide in methanol (0.893 mL, 0.446 mmol), tBuXPhos Pd G3 catalyst (0.035 g, 0.045 mmol) and toluene (2.976 mL, 0.15 M) was sparged with nitrogen for 5 min and then heated at 90 ºC for 18 h. The reaction was cooled to ambient temperature and filtered through a pad of Celite® diatomaceaous earth filter aid. The filtrate was concentrated in vacuo and purified by column chromatography, eluting with 0 to 20% ethyl acetate in hexanes to afford the titled compound (0.155 g, 82% yield). 1H NMR (CDCl3) δ ppm 7.80–7.87 (m, 1H), 7.47–7.56 (m, 3H), 7.34–7.40 (m, 1H), 7.25– 7.28 (m, 1H), 6.59–6.65 (m, 1H), 4.00 (s, 3H). SYNTHESIS EXAMPLE 3 Preparation of 3-Fluoro-5-methyl-6-[[3-(trifluoromethyl)phenyl]methyl]-2-[3- (trifluoromethyl)-1H-pyrazol-1-yl]pyridine (Compound 61) Step A: Preparation of {3-chloro-5-fluoro-6-[3-(trifluoromethyl)pyrazol-1-yl]-2- pyridyl}hydrazine To a solution of 3-chloro-2,5-difluoro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridine (i.e. the product of Step A of Synthesis Example 1, 0.25 g, 0.88 mmol) in 4.4 ml of acetonitrile was added hydrazine hydrate (0.044 g, 0.88 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated to dryness to provide 0.26 g of crude product used in the subsequent step without purification. Step B: Preparation of 2-bromo-3-chloro-5-fluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine To a solution of the crude product from step A (0.23 g, 0.78 mmol) in 3.89 mL of chloroform was added bromine (0.24 g, 1.56 mmol) dropwise over 5 minutes. The reaction mixture was stirred at room temperature for 30 minutes and then heated at 40 ºC overnight. The reaction was partitioned between saturated sodium bicarbonate and dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The crude material was purified via silica gel chromatography (hexane: ethyl acetate gradient) to provide 0.22 g of the title compound. 1H NMR (CDCl3, 500 MHz) δ ppm 8.35–8.40 (m, 1 H), 7.78 (m, 1 H), 6.75–6.80 (m, 1 H). Step C: Preparation of 3-chloro-5-fluoro-2-{[3-(trifluoromethyl)phenyl] methyl}-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine A vial was charged with 2-bromo-3-chloro-5-fluoro-6-[3-(trifluoromethyl)pyrazol-1- yl]pyridine (i.e. the product of Step B, 0.22 g, 0.62 mmol) and (Tetrakis(triphenylphosphine)Pd(0) (0.036 g, 0.031 mmol) and purged with N2. 3.12 mL of tetrahydrofuran and 1.75 mL (0.874 mmol) of 0.5M chloro({[3- (trifluoromethyl)phenyl]methyl})zinc were added and the reaction mixture was heated at 70 ºC overnight. The crude reaction mixture was concentrated onto Celite® diatomaceaous earth filter aid and purified via silica gel chromatography (hexane: ethyl acetate gradient) to provide 0.23 g of the title compound. 1H NMR (CDCl3, 500 MHz) δ ppm 8.22–8.26 (m, 1 H), 7.69–7.74 (m, 1 H), 7.57–7.61 (m, 1 H), 7.49–7.54 (m, 1 H), 7.40–7.49 (m, 2 H), 6.73 (d, 1 H), 4.34 (s, 2 H). Step D: Preparation of 5-fluoro-3-methyl-2-[[3-(trifluoromethyl)phenyl]methyl]-6-[3- (trifluoromethyl)pyrazol-1-yl]pyridine A vial was charged with 3-chloro-5-fluoro-2-{[3-(trifluoromethyl)phenyl]methyl}-6- [3-(trifluoromethyl)pyrazol-1-yl]pyridine (i.e. the product of Step C, 0.080 g, 0.19 mmol), potassium carbonate (0.078 g, 0.566 mmol), and 2-dicyclohexylphosphino-2′,6′-diisopropoxy- 1,1′-biphenyl[2-(2'-amino-1,1'-biphenyl)]Pd(II) methanesulfonate (0.013 g, 0.015 mmol) and purged with N2. 0.94 mL of toluene, 0.094 mL of water, and 0.024 g (0.189 mmol) of trimethyl-1,3,5,2,4,6-trioxatriborinane were added and the reaction mixture was heated at 80 ºC overnight. The crude reaction mixture was concentrated onto Celite® diatomaceaous earth filter aid and was purified via silica gel chromatography (hexane: ethyl acetate gradient) to provide 0.067 g of the title compound. 1H NMR (CDCl3, 500 MHz) δ ppm 8.22–8.25 (m, 1H), 7.48–7.52 (m, 2H), 7.35–7.47 (m, 3H), 6.69–6.73 (m, 1H), 4.22 (s, 2H), 2.34 (s, 3H). By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 10 can be prepared. The following abbreviations are used in the Tables which follow: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, i-Pr means isopropyl, c-Pr means cyclopropyl, t-Bu means tertiary butyl, Ph means phenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, -CN means cyano, -NO2 means nitro, TMS means trimethylsilyl, SOMe means methylsulfinyl, C2F5 means CF2CF3 and SO2Me means methylsulfonyl. TABLE 1 R1 R2 R3 R4 methyl CF 3 CF 3 H ethyl CF 3 CF 3 H n-propyl CF 3 CF 3 H c-propyl CF 3 CF 3 H Cl CF 3 CF 3 H Br CF 3 CF 3 H methoxy CF 3 CF 3 H methyl CF 3 OCF 3 H ethyl CF 3 OCF 3 H n-propyl CF 3 OCF 3 H c-propyl CF 3 OCF 3 H Cl CF 3 OCF 3 H Br CF 3 OCF 3 H methoxy CF 3 OCF 3 H methyl CF 3 CF 3 F ethyl CF 3 CF 3 F n-propyl CF 3 CF 3 F c-propyl CF 3 CF 3 F Cl CF 3 CF 3 F Br CF 3 CF 3 F methoxy CF 3 CF 3 F methyl Cl CF 3 H ethyl Cl CF 3 H n-propyl Cl CF 3 H c-propyl Cl CF 3 H Cl Cl CF 3 H Br Cl CF 3 H methoxy Cl CF 3 H R1 R2 R3 R4 methyl Br CF 3 H ethyl Br CF 3 H n-propyl Br CF 3 H c-propyl Br CF 3 H Cl Br CF 3 H Br Br CF 3 H methoxy Br CF 3 H TABLE 2 R1 R 2 R 3 methyl CF 3 CF 3 ethyl CF 3 CF 3 n-propyl CF 3 CF 3 c-propyl CF 3 CF 3 Cl CF 3 CF 3 Br CF 3 CF 3 methoxy CF 3 CF 3 methyl CF 3 OCF 3 ethyl CF 3 OCF 3 n-propyl CF 3 OCF 3 c-propyl CF 3 OCF 3 Cl CF 3 OCF 3 Br CF 3 OCF 3 methoxy CF 3 OCF 3 methyl Cl CF 3 ethyl Cl CF 3 n-propyl Cl CF 3 c-propyl Cl CF 3 Cl Cl CF 3 R 1 R 2 R 3 Br Cl CF 3 methoxy Cl CF 3 methyl Br CF 3 ethyl Br CF 3 n-propyl Br CF 3 c-propyl Br CF 3 Cl Br CF 3 Br Br CF 3 methoxy Br CF 3 Table 3 R1 R 2 R 3 methyl CF 3 CF 3 ethyl CF 3 CF 3 n-propyl CF 3 CF 3 c-propyl CF 3 CF 3 Cl CF 3 CF 3 Br CF 3 CF 3 methoxy CF 3 CF 3 methyl CF 3 OCF 3 ethyl CF 3 OCF 3 n-propyl CF 3 OCF 3 c-propyl CF 3 OCF 3 Cl CF 3 OCF 3 Br CF 3 OCF 3 methoxy CF 3 OCF 3 methyl Cl CF 3 ethyl Cl CF 3 n-propyl Cl CF 3 c-propyl Cl CF 3 R 1 R 2 R 3 Cl Cl CF 3 Br Cl CF 3 methoxy Cl CF 3 methyl Br CF 3 ethyl Br CF 3 n-propyl Br CF 3 c-propyl Br CF 3 Cl Br CF 3 Br Br CF 3 methoxy Br CF 3 TABLE 4 R1 R2 R3 R4 methyl CF 3 CF 3 H ethyl CF 3 CF 3 H n-propyl CF 3 CF 3 H c-propyl CF 3 CF 3 H Cl CF 3 CF 3 H Br CF 3 CF 3 H methoxy CF 3 CF 3 H methyl CF 3 OCF 3 H ethyl CF 3 OCF 3 H n-propyl CF 3 OCF 3 H c-propyl CF 3 OCF 3 H Cl CF 3 OCF 3 H Br CF 3 OCF 3 H methoxy CF 3 OCF 3 H methyl CF 3 CF 3 F ethyl CF 3 CF 3 F n-propyl CF 3 CF 3 F R1 R2 R3 R4 c-propyl CF 3 CF 3 F Cl CF 3 CF 3 F Br CF 3 CF 3 F methoxy CF 3 CF 3 F methyl Cl CF 3 H ethyl Cl CF 3 H n-propyl Cl CF 3 H c-propyl Cl CF 3 H Cl Cl CF 3 H Br Cl CF 3 H methoxy Cl CF 3 H methyl Br CF 3 H ethyl Br CF 3 H n-propyl Br CF 3 H c-propyl Br CF 3 H Cl Br CF 3 H Br Br CF 3 H methoxy Br CF 3 H Table 5 R1 R 2 R 3 methyl CF 3 CF 3 ethyl CF 3 CF 3 n-propyl CF 3 CF 3 c-propyl CF 3 CF 3 Cl CF 3 CF 3 Br CF 3 CF 3 methoxy CF 3 CF 3 methyl CF 3 OCF 3 ethyl CF 3 OCF 3 n-propyl CF 3 OCF 3 R 1 R 2 R 3 c-propyl CF 3 OCF 3 Cl CF 3 OCF 3 Br CF 3 OCF 3 methoxy CF 3 OCF 3 methyl Cl CF 3 ethyl Cl CF 3 n-propyl Cl CF 3 c-propyl Cl CF 3 Cl Cl CF 3 Br Cl CF 3 methoxy Cl CF 3 methyl Br CF 3 ethyl Br CF 3 n-propyl Br CF 3 c-propyl Br CF 3 Cl Br CF 3 Br Br CF 3 methoxy Br CF 3 Table 6 R1 R 2 R 3 methyl CF 3 CF 3 ethyl CF 3 CF 3 n-propyl CF 3 CF 3 c-propyl CF 3 CF 3 Cl CF 3 CF 3 Br CF 3 CF 3 methoxy CF 3 CF 3 methyl CF 3 OCF 3 ethyl CF 3 OCF 3 n-propyl CF 3 OCF 3 R 1 R 2 R 3 c-propyl CF 3 OCF 3 Cl CF 3 OCF 3 Br CF 3 OCF 3 methoxy CF 3 OCF 3 methyl Cl CF 3 ethyl Cl CF 3 n-propyl Cl CF 3 c-propyl Cl CF 3 Cl Cl CF 3 Br Cl CF 3 methoxy Cl CF 3 methyl Br CF 3 ethyl Br CF 3 n-propyl Br CF 3 c-propyl Br CF 3 Cl Br CF 3 Br Br CF 3 methoxy Br CF 3 Table 7 R1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 R 1 R 2 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br Table 8 R1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 R 1 R 2 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br TABLE 9 R1 R5 R3 R4 methyl CF 3 CF 3 H ethyl CF 3 CF 3 H n-propyl CF 3 CF 3 H c-propyl CF 3 CF 3 H Cl CF 3 CF 3 H Br CF 3 CF 3 H methoxy CF 3 CF 3 H methyl CF 3 OCF 3 H R1 R5 R3 R4 ethyl CF 3 OCF 3 H n-propyl CF 3 OCF 3 H c-propyl CF 3 OCF 3 H Cl CF 3 OCF 3 H Br CF 3 OCF 3 H methoxy CF 3 OCF 3 H methyl CF 3 CF 3 F ethyl CF 3 CF 3 F n-propyl CF 3 CF 3 F c-propyl CF 3 CF 3 F Cl CF 3 CF 3 F Br CF 3 CF 3 F methoxy CF 3 CF 3 F methyl Cl CF 3 H ethyl Cl CF 3 H n-propyl Cl CF 3 H c-propyl Cl CF 3 H Cl Cl CF 3 H Br Cl CF 3 H methoxy Cl CF 3 H methyl Br CF 3 H ethyl Br CF 3 H n-propyl Br CF 3 H c-propyl Br CF 3 H Cl Br CF 3 H Br Br CF 3 H methoxy Br CF 3 H TABLE 10
R1 R2 R3 R4 methyl CF 3 CF 3 H ethyl CF 3 CF 3 H n-propyl CF 3 CF 3 H c-propyl CF 3 CF 3 H Cl CF 3 CF 3 H Br CF 3 CF 3 H methoxy CF 3 CF 3 H methyl CF 3 OCF 3 H ethyl CF 3 OCF 3 H n-propyl CF 3 OCF 3 H c-propyl CF 3 OCF 3 H Cl CF 3 OCF 3 H Br CF 3 OCF 3 H methoxy CF 3 OCF 3 H methyl CF 3 CF 3 F ethyl CF 3 CF 3 F n-propyl CF 3 CF 3 F c-propyl CF 3 CF 3 F Cl CF 3 CF 3 F Br CF 3 CF 3 F methoxy CF 3 CF 3 F methyl Cl CF 3 H ethyl Cl CF 3 H n-propyl Cl CF 3 H c-propyl Cl CF 3 H Cl Cl CF 3 H Br Cl CF 3 H methoxy Cl CF 3 H methyl Br CF 3 H ethyl Br CF 3 H n-propyl Br CF 3 H c-propyl Br CF 3 H Cl Br CF 3 H Br Br CF 3 H methoxy Br CF 3 H Table 11 R1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br Table 12 R 1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br Table 13 R 1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br Table 14 R 1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br Table 15 R 1 R 2 methyl CF 3 ethyl CF 3 n-propyl CF 3 c-propyl CF 3 Cl CF 3 Br CF 3 methoxy CF 3 methyl OCF 3 ethyl OCF 3 n-propyl OCF 3 c-propyl OCF 3 Cl OCF 3 Br OCF 3 methoxy OCF 3 methyl Cl ethyl Cl n-propyl Cl c-propyl Cl Cl Cl Br Cl methoxy Cl methyl Br ethyl Br n-propyl Br c-propyl Br Cl Br Br Br methoxy Br 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 Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001–90 0–99.999 0–15 soluble Granules, Tablets and Powders Oil Dispersions, Suspensions, 1–50 40–99 0–50 Emulsions, Solutions (including Emulsifiable Concentrates) Dusts 1–25 70–99 0–5 Granules and Pellets 0.001–99 5–99.999 0–15 High Strength Compositions 90–99 0–10 0–2 Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C6–C22), such as plant seed and fruit oils (e.g., oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents. Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin- based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides. Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N- alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts. Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides. Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon’s Emulsifiers and Detergents, annual American and International Editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987. Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon’s Volume 2: Functional Materials, annual International and North American editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222. The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S.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, December 4, 1967, pp 147–48, Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8–57 and following, and WO 91/13546. Pellets can be prepared as described in U.S.4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S.3,299,566. For further information regarding the art of formulation, see T. S. Woods, “The Formulator’s Toolbox – Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food–Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120–133. See also U.S.3,235,361, Col.6, line 16 through Col.7, line 19 and Examples 10–41; U.S.3,309,192, Col.5, line 43 through Col.7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138–140, 162–164, 166, 167 and 169–182; U.S.2,891,855, Col.3, line 66 through Col.5, line 17 and Examples 1–4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81–96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000. In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Table A. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated. Example A High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0% Example B Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0% Example C Granule Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No.25–50 sieves) Example D Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0% Example E Emulsifiable Concentrate Compound 1 10.0% polyoxyethylene sorbitol hexoleate 20.0% C6–C10 fatty acid methyl ester 70.0% Example F Microemulsion Compound 1 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% Water 20.0% Example G Suspension Concentrate Compound 1 35% butyl polyoxyethylene/polypropylene block copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% Water 53.7% Example H Emulsion in Water Compound 1 10.0% butyl polyoxyethylene/polypropylene block copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% aromatic petroleum based hydrocarbon 20.0 water 58.7% Example I Oil Dispersion Compound 1 25% polyoxyethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5% The present disclosure also includes Examples A through I above except that “Compound 1” is replaced in each of the Examples A through I with the respective compounds from Index Table A as shown below. Compound # Compound # Compound # Compound # Compound # 2 18 34 50 66 3 19 35 51 67 4 20 36 52 68 5 21 37 53 69 6 22 38 54 70 7 23 39 55 71 8 24 40 56 72 9 25 41 57 73 10 26 42 58 74 11 27 43 59 75 12 28 44 60 76 13 29 45 61 77 14 30 46 62 78 15 31 47 63 79 16 32 48 64 80 17 33 49 65 81 Compound # Compound # Compound # Compound # Compound # 82 85 88 91 94 83 86 89 92 95 84 87 90 93 96 Test results indicate that the compounds of the present invention are highly active preemergent and/or postemergent herbicides and/or plant growth regulants. The compounds of the inention generally show highest activity for postemergence weed control (i.e. applied after weed seedlings emerge from the soil) and preemergence weed control (i.e. applied before weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures. Many of the compounds of this invention, by virtue of selective metabolism in crops versus weeds, or by selective activity at the locus of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixture of crops and weeds, are useful for the selective control of grass and broadleaf weeds within a crop/weed mixture. One skilled in the art will recognize that the preferred combination of these selectivity factors within a compound or group of compounds can readily be determined by performing routine biological and/or biochemical assays. Compounds of this invention may show tolerance to important agronomic crops including, but is not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass). Compounds of this invention can be used in crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and/or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful to modify plant growth. As the compounds of the invention have both preemergent and postemergent herbicidal activity, to control undesired vegetation by killing or injuring the vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving contacting a herbicidally effective amount of a compound of the invention, or a composition comprising said compound and at least one of a surfactant, a solid diluent or a liquid diluent, to the foliage or other part of the undesired vegetation or to the environment of the undesired vegetation such as the soil or water in which the undesired vegetation is growing or which surrounds the seed or other propagule of the undesired vegetation. Undesired vegetation includes at least one selected from the group consisting of grass weeds and broadleaf weeds. Undesired vegetation is selected from the group consisting of annual bluegrass, Benghal dayflower, blackgrass, black nightshade, broadleaf signalgrass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, corn poppies, field violet, giant foxtail, goosegrass, green foxtail, guinea grass, hairy beggarticks, herbicide-resistant black grass, horseweed, Italian rye grass, jimsonweed, Johnson grass (Sorghum halepense), large crabgrass, little seed canary grass, morning glory, Pennsylvania smartweed, pitted morning glory, prickly sida, quackgrass, redroot pigweed, shattercane, shepherd's purse, silky windgrass, sunflower (as weed in potato), wild buckwheat (Polygonum convolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua), wild pointsettia, yellow foxtail, and yellow nutsedge (Cyperus esculentus). 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. 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 enhanced effects with genetic traits in the desired vegetation, including traits incorporated through genetic modification. For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic/abiotic stresses or storage stability may be greater than expected from the genetic traits in the desired vegetation. Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including herbicides, herbicide safeners, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Mixtures of the compounds of the invention with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any resistant biotypes. Thus the present invention also pertains to a composition comprising a compound of Formula 1 (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically effective amount) and can further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents can be formulated in compositions comprising at least one of a surfactant, solid or liquid diluent. For mixtures of the present invention, one or more other biologically active compounds or agents can be formulated together with a compound of Formula 1, to form a premix, or one or more other biologically active compounds or agents can be formulated separately from the compound of Formula 1, and the formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron, aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts (e.g., sodium, potassium), 4- amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)-2-Pyridinecarboxylic 2-propyn-1-yl ester (CAS No. 2251111-17-6), 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)- 2- Pyridinecarboxylic cyanomethyl ester (CAS No. 2251111-18-7), aminopyralid, amitrole, ammonium sulfamate, 2,5-anhydro-3,4-dideoxy-4-[[[(5S)-3-(3,5-difluorophenyl)-5-ethenyl- 4,5-dihydro-5-isoxazolyl]carbonyl]amino]-threo-Pentonic methyl ester (CAS No. 27499989- 21-6), anilofos, anisiflupurin, asulam, atrazine, azimsulfuron, bixlozone, beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, benquitrione, benquinotrione, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bipyrazone, bispyribac and its sodium salt, broclozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate, butachlor, butafenacil, butamifos, butralin, butroxydim, butylate, bipyrazone, cafenstrole, carbetamide, 1-(2-carboxyethyl)-4-(2-pyrimidinyl)pyridazinium (CAS No. 2285384-11-2) and salts thereof, carfentrazone-ethyl, catechin, chlomethoxyfen, chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl, 3-[2-chloro-5-[3,6-dihydro-3-methyl- 2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5- Isoxazolecarboxylic ethyl ester (CAS No. 1949837-17-5), chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, cypyrafluone, 2,4-D and its butotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamine and trolamine salts, cyprafluone, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron, dimesulfazet, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and its sodium salt, dinitramine, dinoterb, dioxopyritrione, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC, epyrifenacil, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, fluchloraminopyr, flufenacet, flufenoximacil, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol, flurenol- butyl, fluridone, flurochloridone, fluroxypyr, flurtamone, flusulfinam, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium, glufosinate, glufosinate-ammonium, L- glufosinate-ammonium, glufosinate-P, glyphosate and its salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin, icafolin, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iofensulfuron, iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium, ipfencarbazone, iptriazopyrid, isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen, lancotrione, lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g., MCPA- dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts (e.g., MCPB- sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium, monoammonium, monosodium and disodium salts, methyldymron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metproxybicyclone, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, 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, pyriflubenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA, TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr- triethylammonium, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron-methyl, tripyrasulfone, tritosulfuron, vernolate, 3-(2-chloro-3,6- difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one, 5-chloro-3-[(2-hydroxy-6- oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone, 2-chloro-N-(1- methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide, 7-(3,5-dichloro-4- pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one), 4-(2,6-diethyl- 4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6- difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previously methioxolin), 4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1- yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione, methyl 4-amino-3-chloro-6-(4- chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, 2-methyl-3- (methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and 2-methyl- N-(4-methyl-1,2,5-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. Preferred for better control of undesired vegetation (e.g., lower use rate such as from enhanced effects, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of atrazine, azimsulfuron, S-beflubutamid, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, cloransulam-methyl, 2-[(2,4-dichlorophenyl)methyl]- 4,4-dimethyl-3-isoxazolidinone, 2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3- isoxazolidinone, ethametsulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy- 6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, pethoxamid, picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl and tribenuron-methyl. Compounds of this invention can also be used in combination with plant growth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine, epocholeone, gibberellic acid, gibberellin 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 typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components may expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula 1 alone. In certain instances, combinations of a compound of this invention with other biologically active (particularly herbicidal) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. enhanced) effect on weeds and/or a less-than-additive effect (i.e. safening) on crops or other desirable plants. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. Ability to use greater amounts of active ingredients to provide more effective weed control without excessive crop injury is also desirable. When the enhanced effects of herbicidal mixtures of 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-l-yl 1-(3,4-dimethylphenyl)-l,6-dihydro-6-oxo-2-phenyl-5- pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and 2- methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide to increase safety to certain crops. Antidotally effective amounts of the herbicide safeners can be applied at the same time as the compounds of this invention, or applied as seed treatments. Therefore an aspect of the present invention relates to a herbicidal mixture comprising a compound of this invention and an antidotally effective amount of a herbicide safener. Seed treatment is particularly useful for selective weed control, because it physically restricts antidoting to the crop plants. Therefore a particularly useful embodiment of the present invention is a method for selectively controlling the growth of undesired vegetation in a crop comprising contacting the locus of the crop with a herbicidally effective amount of a compound of this invention wherein seed from which the crop is grown is treated with an antidotally effective amount of safener. Antidotally effective amounts of safeners can be easily determined by one skilled in the art through simple experimentation. Compounds of the invention can also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and/or chemically modified nucleotides influencing the amount of a particular target through down regulation, interference, suppression or silencing of the genetically derived transcript that render a safening effect. Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. Table A1 lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions and methods of the present invention. Compound 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 (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight 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 Ametryn 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 Component (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight Ratio 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-propargyl 1:41 – 56:1 1:13 – 19:1 1:1 – 7:1 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-methyl 1:24 – 96:1 1:8 – 32:1 1:1 – 12:1 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 Component (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight Ratio 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 Dimethametryn 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-methyl 1:34 – 68:1 1:11 – 23:1 1:1 – 9:1 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 Florpyrauxifen-benzyl 1:96 – 24:1 1:32 – 8:1 1:3 – 3:1 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 Component (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight Ratio 1 Flupyrsulfuron-methyl 1:6 – 336:1 1:2 – 112:1 4:1 – 42:1 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-methyl 1:342 – 7:1 1:114 – 3:1 1:10 – 1:2 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-methyl 1:6 – 336:1 1:2 – 112:1 4:1 – 42:1 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 Component (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight Ratio 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-methyl 1:10 – 224:1 1:3 – 75:1 3:1 – 28:1 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-methyl 1:4 – 560:1 1:1 – 187:1 7:1 – 70:1 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 Oryzalin 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 Component (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight Ratio 1 Pretilachlor 1:384 – 6:1 1:128 – 2:1 1:12 – 1:2 1 Primisulfuron-methyl 1:17 – 135:1 1:5 – 45:1 1:1 – 17:1 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 Prometryn 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-ethyl 1:20 – 112:1 1:6 – 38:1 1:1 – 14:1 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-methyl 1:41 – 56:1 1:13 – 19:1 1:1 – 7:1 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 Component (a) Typical More Typical Most Typical (Compound No.) Component (b) Weight Ratio Weight Ratio Weight Ratio 1 Sulfentrazone 1:294 – 8:1 1:98 – 3:1 1:9 – 1:2 1 Sulfometuron-methyl 1:68 – 34:1 1:22 – 12:1 1:2 – 5:1 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 Tefuryltrione 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 Terbutryn 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-methyl 1:10 – 224:1 1:3 – 75:1 3:1 – 28:1 1 Tiafenacil 1:85 – 27:1 1:28 – 9:1 1:2 – 4:1 1 Thiobencarb 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-methyl 1:34 – 68:1 1:11 – 23:1 1:1 – 9:1 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 A96 are constructed similarly. Table Component (a) Table Component (a) Table Component (a) Number Column Entries Number Column Entries Number Column Entries A2 Compound 2 A34 Compound 34 A66 Compound 66 A3 Compound 3 A35 Compound 35 A67 Compound 67 A4 Compound 4 A68 Compound 68 A5 Compound 5 A37 Compound 37 A69 Compound 69 A6 Compound 6 A70 Compound 70 A7 Compound 7 A71 Compound 71 A8 Compound 8 A40 Compound 40 A72 Compound 72 A9 Compound 9 A41 Compound 41 A73 Compound 73 A10 Compound 10 A42 Compound 42 A74 Compound 74 A11 Compound 11 A43 Compound 43 A75 Compound 75 A12 Compound 12 A44 Compound 44 A76 Compound 76 A13 Compound 13 A45 Compound 45 A77 Compound 77 A14 Compound 14 A46 Compound 46 A78 Compound 78 A15 Compound 15 A47 Compound 47 A79 Compound 79 A16 Compound 16 A48 Compound 48 A80 Compound 80 A17 Compound 17 A49 Compound 49 A81 Compound 81 A18 Compound 18 A50 Compound 50 A82 Compound 82 A19 Compound 19 A51 Compound 51 A83 Compound 83 A20 Compound 20 A52 Compound 52 A84 Compound 84 A21 Compound 21 A53 Compound 53 A85 Compound 85 A22 Compound 22 A54 Compound 54 A86 Compound 86 A23 Compound 23 A55 Compound 55 A87 Compound 87 A24 Compound 24 A56 Compound 56 A88 Compound 88 A25 Compound 25 A57 Compound 57 A89 Compound 89 A26 Compound 26 A58 Compound 58 A90 Compound 90 A27 Compound 27 A59 Compound 59 A91 Compound 91 A28 Compound 28 A60 Compound 60 A92 Compound 92 A29 Compound 29 A61 Compound 61 A93 Compound 93 A30 Compound 30 A62 Compound 62 A94 Compound 94 A31 Compound 31 A63 Compound 63 A95 Compound 95 A32 Compound 32 A64 Compound 64 A96 Compound 96 A33 Compound 33 A65 Compound 65 Preferred for better control of undesired vegetation (e.g., lower use rate such as from enhanced effects, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group consisting of chlorimuron-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron, pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, metolachlor and S-metolachlor. The following TESTS demonstrate the control efficacy of compounds of this invention on specific pathogens. The pathogen control protection afforded by the compounds is not limited, however, to these species. See Index Tables A through E below for compound descriptions. The abbreviation “Cmpd.” stands for “Compound”, and the abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. The numerical value reported in the column “MS” is the molecular weight of the highest isotopic abundance positively charged parent ion (M+1) formed by addition of H+ (molecular weight of 1) to the molecule having the highest isotopic abundance, or the highest isotopic abundance negatively charged ion (M–1) formed by loss of H+ (molecular weight of 1). “Pyr” means “Pyridine”. “Przl” means “Pyrazol”. “Thzl” means “Thiazole”. “Imdzl” mean “Imidazol”. “Trzl” means “Triazol”. “1,2,4-Trzl” means “1,2,4-Triazol” shown as below. The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g., 37Cl, 81Br) is not reported. The reported MS peaks were observed by mass spectrometry using electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI). INDEX TABLE A Cmpd. No. G Q R 1 R 3 R 4 MS (M+1) 1 3-CF 3 -1,2,4-Trzl-1-yl O Et CF 3 F 439 3 3-CF 3 -1,2,4-Trzl-1-yl O Cl CF 3 F 445 6 3-CF 3 -1,2,4-Trzl-1-yl O c-Pro CF 3 H 433 7 3-CF 3 -1,2,4-Trzl-1-yl O Et CF 3 H 421 8 3-CF 3 -Przl-1-yl O c-Pro CF 3 F 450 9 3-CF 3 -Przl-1-yl O Et CF 3 F 438 12 3-CF 3 -Przl-1-yl O Cl CF 3 H 426 13 4-CF 3 -Przl-1-yl O Et OCF 3 H 436 20 3-CF 3 -Przl-1-yl O Et OCF 3 H 436 21 3-CF 3 -Przl-1-yl O Me OCF 3 H 422 22 3-CF 3 -Przl-1-yl O c-Pro OCF 3 H 448 26 4-CF 3 -Przl-1-yl O c-Pro OCF 3 H 448 27 4-CF 3 -Przl-1-yl O Me OCF 3 H 422 32 3-CF 3 -1,2,4-Trzl-1-yl O c-Pro CF 3 F 451 33 4-CF 3 -Przl-1-yl O Et CF 3 H 420 34 3-CF 3 -Przl-1-yl O Cl OCF 3 H 442 40 3-CF 3 -1,2,4-Trzl-1-yl O Me CF 3 H 407 41 3-CF 3 -Przl-1-yl O Me CF 3 F 424 43 3-CF3-1,2,4-Trzl-1-yl O Cl CF3 H 427 50 3-CF3- Przl-1-yl O Pro CF3 H 434 51 3-CF3- Przl-1-yl O Et CF3 H 420 52 3-CF3- Przl-1-yl O c-Pro CF3 H 432 53 3-CF 3 - Przl-1-yl O Me CF 3 H 406 54 3-CF 3 - Przl-1-yl O OMe CF 3 H 422 57 3-Me-Przl-1-yl O Me CF3 H 352 58 3-t-Bu-Przl-1-yl O Me CF3 H 394 59 3-t-Bu-Przl-1-yl O Et CF3 H 408 60 3-Me-Przl-1-yl O Cl CF3 H 372 61 3-CF 3 -Przl-1-yl CH 2 Me CF 3 H 404 62 3-CF 3 -Przl-1-yl CH 2 Cl CF 3 H 424 71 3-CHF 2 -Przl-1-yl O Cl CF 3 H 408 73 3-CHF 2 -Przl-1-yl O Me CF 3 H 388 74 3-CHF 2 -Przl-1-yl O Et CF 3 H 402 78 3-Me-Przl-1-yl O Et CF 3 H 366 80 3-Br-Przl-1-yl O Et CF 3 H 430 82 3-Cl-Przl-1-yl O Et CF 3 H 386 84 3-t-Bu-Przl-1-yl O Cl CF 3 H 414 85 3-CF 3 -Przl-1-yl O Me OCHF 2 H 404 86 3-CF 3 -Przl-1-yl O Et OCHF 2 H 418 87 3-CF 3 -Przl-1-yl CH 2 Et CF 3 H 418 88 3-i-Pro-Przl-1-yl O Me CF 3 H 380 90 3-CF 3 -Przl-1-yl O OEt CF 3 H 436 91 3-i-Pro-Przl-1-yl O Et CF 3 H 394 96 3-i-Pro-Przl-1-yl O Cl CF 3 H 400 INDEX TABLE B Cmpd. No. G Q R1 R3 MS (M+1) 2 3-CF 3 -1,2,4-Trzl-1-yl O Et CF 3 422 5 3-CF3-1,2,4-Trzl-1-yl O Cl CF3 428 14 4-CF3-Przl-1-yl O Et CF3 421 23 3-CF3-Przl-1-yl O Et CF3 421 25 3-CF 3 -Przl-1-yl CH 2 Cl CF 3 425 29 3-CF 3 -Przl-1-yl CH 2 Me CF 3 405 30 3-CF 3 -Przl-1-yl CH 2 Et CF 3 419 31 3-CF 3 -Przl-1-yl CH 2 c-Pro CF 3 431 35 3-CF3-1,2,4-Trzl-1-yl O Pro CF3 436 37 4-CF3-Przl-1-yl O Me CF3 407 46 3-CF3-Przl-1-yl O c-Pro CF3 433 47 3-CF3-Przl-1-yl O Me CF3 407 63 3-CF3-Przl-1-yl O Cl CF3 427 64 3-CF3-Przl-1-yl O Et CHF2 403 65 3-CF3-1,2,4-Trzl-1-yl O c-Pro CF3 434 66 3-CHF2-Przl-1-yl O Me CF3 389 67 3-CF3-Przl-1-yl O Me OCHF2 405 68 3-CF3-Przl-1-yl O Et OCHF2 419 69 3-CF 3 -Przl-1-yl O Cl OCHF 2 425 70 3-CHF2-Przl-1-yl O Cl CF3 409 72 3-CHF2-Przl-1-yl O Et CF3 403 75 3-CF3-Przl-1-yl O OMe CF3 423 76 3-CF3-Przl-1-yl O OEt CF3 437 79 3-Br-Przl-1-yl O Et CF3 432 83 3-Cl-Przl-1-yl O Et CF3 387 89 3-CF3-Przl-1-yl O Me CHF2 389 INDEX TABLE C Cmpd. No. G R1 R3 MS (M+1) 4 3-CF 3 -Przl-1-yl Cl CF 3 427 10 4-CF 3 -Przl-1-yl Et CF 3 421 11 4-CF 3 -Przl-1-yl Me CF 3 407 24 3-CF 3 -Przl-1-yl Pro CF 3 435 42 3-CF 3 -Przl-1-yl Et CF 3 421 48 3-CF 3 -Przl-1-yl c-Pro CF 3 433 49 3-CF 3 -Przl-1-yl Me CF 3 407 55 3-CHF 2 -Przl-1-yl Me CF 3 389 56 3-CHF2-Przl-1-yl Et CF3 403 77 3-CHF 2 -Przl-1-yl OMe CF 3 405 81 3-Cl-Przl-1-yl Et CF3 387 92 3-Br-Przl-1-yl Et CF3 432 93 3-CHF 2 -Przl-1-yl Cl CF 3 409 94 3-Cl-Przl-1-yl Cl CF3 393 95 3-Br-Przl-1-yl Cl CF3 437 INDEX TABLE D Cmpd. No. G R1 MS (M+1) 15 3-CF3-Przl-1-yl Et 424 16 3-CF3-Przl-1-yl Me 410 17 3-CF3-Przl-1-yl Cl 430 28 3-CF3-Przl-1-yl c-Pro 436 INDEX TABLE E Cmpd. No. G R1 MS (M+1) 18 3-CF3-Przl-1-yl Cl 430 19 3-CF3-Przl-1-yl Et 424 44 3-CF3-Przl-1-yl c-Pro 436 45 3-CF3-Przl-1-yl Me 410 BIOLOGICAL EXAMPLES OF THE INVENTION TEST A Seeds of plant species selected from barnyardgrass (Echinochloa crus-galli), blackgrass (Alopecurus myosuroides), corn (Zea mays), foxtail, giant (giant foxtail, Setaria faberi), goosegrass (Eleusine indica), kochia (Bassia scoparia), oat, wild (wild oat, Avena fatua), pigweed, palmer (palmer amaranth, palmer pigweed, Amaranthus palmeri), ragweed (common ragweed, Ambrosia artemisiifolia), ryegrass, Italian (italian ryegrass, Lolium multiflorum), soybean (Glycine max), and wheat (Triticum aestivum) were planted into a blend of loam soil and sand and treated preemergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, plants selected from these crop and weed species and also galium (catchweed bedstraw, Galium aparine) and horseweed (Erigeron canadensis) were planted in pots containing the same blend of loam soil and sand and treated with postemergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were in the one- to two-leaf stage for the postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for 10 days, after which time all treated plants were compared to untreated controls and visually evaluated for injury. Plant response ratings, summarized in Table A, are based on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (–) response means no test result.. Table A Compounds 500 g ai/ha 12 53 Preemergence Blackgrass 90 90 Corn 20 60 Foxtail, Giant 100100 Goosegrass 100100 Kochia 100100 Oat, Wild 60100 Pigweed, Palmer 100100 Ragweed 80 90 Ryegrass, Italian 100100 Soybean 20 70 Wheat 30 80 Table A Compounds 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Preemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 80 90 40 90 90 90 90 80 90 50 0 90 40 90 Corn 20 80 0 40 70 10 20 10 10 0 0 20 10 50 Foxtail, Giant 100100 90100100100100100100 90 90100 50100 Goosegrass 100100100 100100100100100100 90 60100 90100 Kochia 100100100 100100 90100 90100 0 0100 10100 Oat, Wild 30 90 10 30 80 - - - - - - 60 10 90 Pigweed, Palmer 0 0 0 100 0100100100100 70 90100 90100 Ragweed 100100 10 50 70100100 90100 0 0 20 0100 Ryegrass, Italian 100 90 70 70100 - - - - - - 100 80100 Soybean 40 70 0 10 50 20 60 20 60 0 0 0 0 50 Wheat 30 90 0 10 70 30 30 10 20 0 0 10 0 50 Table A Compounds 125 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Preemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 90 80 10 - - - - - 50 90 90 30 80 70 Corn 30 20 0 0 0 50 10 10 40 40 60 0 0 0 Foxtail, Giant 100100 90 0 10 90100100100100100 10 10100 Goosegrass 100100 90 0 20100100100100100100 20 80100 Kochia 100100 80 0 0100100100100 90 90 40 0 90 Oat, Wild 90 80 10 0 0 70100 90 90 70100 0 10 30 Pigweed, Palmer 100100100 0 60100100100100100100 20 90100 Ragweed 100 80 0 0 0100100 70100 90 70 0 0 50 Ryegrass, Italian 100100 50 0 20100100100100100100 20 40 70 Soybean 40 20 0 0 0 50 40 40 60 20 40 0 0 40 Wheat 30 10 0 0 0 20 20 40 50 20 50 0 0 10 Table A Compounds 125 g ai/ha 29 30 31 32 33 34 35 37 40 41 42 Preemergence Barnyardgrass - - - - - - - - - - - Blackgrass 100 90 50 60 50 - 90 90 80 70 90 Corn 60 60 40 0 0 10 50 50 30 10 40 Foxtail, Giant 100100100100100100100 100 100100100 Goosegrass 100100100 100100100100 100 100100100 Kochia 100100100 70 70 10 90 100 100100100 Oat, Wild 90 70 60 20 30 60 70 100 - - 100 Pigweed, Palmer 100100100100 90100100 100 100100100 Ragweed 100 90 50 50 30 50 90 90 100100100 Ryegrass, Italian 100100100100 80 90100 100 - - 100 Soybean 70 60 50 10 0 0 50 50 40 40 60 Wheat 60 50 30 20 0 10 60 50 30 10 40 Table A Compounds 125 g ai/ha 43 44 45 46 47 48 49 50 51 52 53 54 55 56 Preemergence Barnyardgrass - - - - - - - - - - - 90 90100 Blackgrass 40 - - 90100 90 90 80 50 80 90 90 90 90 Corn 0 0 0 30 50 10 60 10 10 10 50 20 50 60 Foxtail, Giant 100 0 0100100100100100100 100100 - 100100 Goosegrass 100 0 0 100100100100100100 100100 - - - Kochia 90 0 0 100100100100 90100100100100100100 Oat, Wild - 0 0 80 90 50 90 40 50 40 90 90 90 90 Pigweed, Palmer 100 0 0100100100100100100 100100100100100 Ragweed 20 0 0 100100 60100 70100 90 90 90 60 80 Ryegrass, Italian - 0 0100100100100100100 100100100100100 Soybean 10 0 0 40 70 30 60 40 40 30 40 20 50 30 Wheat 10 0 0 70 90 30 60 20 20 30 40 30 20 20 Table A Compounds 125 g ai/ha 57 58 59 60 61 62 63 64 65 66 67 68 69 70 Preemergence Barnyardgrass 60 10 10 0 90 60 - 100 - 100100 90 80100 Blackgrass 70 70 90 10100 90 90 90 80 90 90 90 90100 Corn 20 0 0 0 30 10 50 50 40 80 30 30 10 30 Foxtail, Giant - - - - - - 100100100 90 90 90100 - Goosegrass - - - - - - 100 - 100 - - - - - Kochia 60 70 60 0100 90100100100100100100100100 Oat, Wild 70 0 70 0 70 40 90100 90 90 80 80 50100 Pigweed, Palmer 100100100 10100100100100100 100100100100100 Ragweed 30 0 0 0 100 20 90 60 60100100 90 30 - Ryegrass, Italian 80 80 90 0100100100100 90100100100 90100 Soybean 10 0 10 10 30 0 50 40 60 50 30 20 10 60 Wheat 10 0 10 0 40 10 20 20 60 60 30 10 10 40 Table A Compounds 125 g ai/ha 71 72 73 74 75 76 77 78 79 80 81 82 83 84 Preemergence Barnyardgrass 80100 90 90 0 0100100 90 90 90 80100 0 Blackgrass 100 90 90 90 90100 90 80100 90 90 90100 0 Corn 10 70 40 20 70 30 70 10 40 10 40 30 30 0 Foxtail, Giant - 100100100 - - - - 100100100100100 0 Goosegrass - - - - - - - - - - - - - - Kochia 100100100 100100100100 90100100100100100 0 Oat, Wild 80 80 90 90 80 90 50 70 60 50 70 80 80 0 Pigweed, Palmer 100100100100100100100100100 100100100100 0 Ragweed - 100 90100 90 90 0 80100 80 70 60100 0 Ryegrass, Italian 90100100100100100100 90100100100100 90 0 Soybean 0 50 40 30 60 30 60 60 40 10 30 20 40 0 Wheat 20 30 30 20 80 50 80 20 30 30 20 40 30 0 Table A Compounds 125 g ai/ha 85 86 87 88 89 90 91 92 93 94 95 96 Preemergence Barnyardgrass 70 90 90 90100 90 80 90 40 10 0 0 Blackgrass 100 80100 70 90100 60 80 90 0 0 50 Corn 10 10 10 30 40 10 30 30 10 0 0 0 Foxtail, Giant 50 70 - - 90 - - 100 - - - - Goosegrass - - - - - - - - - - - - Kochia 100100100 100100 90100100100 0 0 0 Oat, Wild 90 50100 60 90 90 80 80 80 10 10 0 Pigweed, Palmer 100100100100100100100100100 100 90 70 Ragweed 70 80100 40 80 70 80 60 - 0 0 50 Ryegrass, Italian 100100100100100100100100 90 20 30 90 Soybean 10 20 - 20 40 10 20 50 20 10 0 10 Wheat 20 10 30 20 30 30 30 20 30 0 0 0 Table A Compounds 31 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 13 14 15 Preemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 30 80 10 40 50 30 20 40 10 0 0 10 60 20 Corn 0 50 0 0 30 0 10 0 - 0 0 0 30 10 Foxtail, Giant 80100 10 80100 80100 60 90 10 0 10 90 90 Goosegrass 100100 30 70100100100 80100 20 10 30100 90 Kochia 90100 0 20100 90100 20100 0 0 0100100 Oat, Wild 10 30 0 0 20 - - - - - - 0 80 20 Pigweed, Palmer 0 0 0 100 0100100 90100 30 0 20100100 Ragweed 70 40 0 0 0 30 60 30 80 0 0 0 40 20 Ryegrass, Italian 90 90 0 30 70 - - - - - - 0100 90 Soybean 20 50 0 0 0 10 20 10 40 0 0 0 40 30 Wheat 0 40 0 0 20 10 10 0 10 0 0 0 20 10 Table A Compounds 31 g ai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28 29 Preemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 10 0 - - - - - 30 90 80 0 10 20 80 Corn 0 0 0 0 10 10 10 20 10 20 0 0 0 30 Foxtail, Giant 30 10 0 0 60 30 90100100100 0 0 70100 Goosegrass 90 20 0 0100100 90100100100 10 20 50 90 Kochia 90 0 0 0 80 90100100 80 70 10 0 30100 Oat, Wild 10 0 0 0 20 80 50 40 20 60 0 0 10 40 Pigweed, Palmer 100 50 0 0 90100100100100100 20 20 70100 Ragweed 10 0 0 0 80 40 40 80 40 20 0 0 - 60 Ryegrass, Italian 40 0 0 0100100 90100 80 90 0 0 20 40 Soybean 0 0 0 0 40 20 20 40 10 10 0 0 0 10 Wheat 0 0 0 0 10 10 10 10 10 10 0 0 0 20 Table A Compounds 31 g ai/ha 30 31 32 33 34 35 37 40 41 42 43 Preemergence Barnyardgrass - - - - - - - - - - - Blackgrass 50 20 10 30 - 50 50 30 50 50 10 Corn 20 10 0 0 0 20 - 0 0 30 0 Foxtail, Giant 100100 50 40 20 70 60 90 30100 70 Goosegrass 90 90 90 60 30 90 100 100100100 40 Kochia 100 90 90 0 0 80 100 100 10100 70 Oat, Wild 30 20 0 0 10 40 30 - - 30 - Pigweed, Palmer 100100 90 20 90100 100 100100100 80 Ragweed 30 30 10 0 0 20 20 20 10 90 - Ryegrass, Italian 70 50 20 10 40 90 90 - - 100 - Soybean 30 10 0 0 0 20 0 10 10 40 0 Wheat 10 10 0 0 0 10 10 0 0 10 0 Table A Compounds 31 g ai/ha 44 45 46 47 48 49 50 51 52 54 55 56 57 58 Preemergence Barnyardgrass - - - - - - - - - 50 30 90 10 0 Blackgrass - - 50 70 80 90 30 50 50 70 50 80 20 20 Corn 0 0 10 30 0 10 10 10 10 10 10 10 0 0 Foxtail, Giant 0 0100 100100100 80100 90 - 100100 - - Goosegrass 0 0100 100100100100 90100 - - - - - Kochia 0 0100 100 80 90 90100 20 90 80100 20 0 Oat, Wild 0 0 40 50 20 30 30 30 20 50 20 40 0 0 Pigweed, Palmer 0 0100 100100100 90100100100100100 90 10 Ragweed 0 0 70 80 10 10 10 60 20 60 10 50 0 0 Ryegrass, Italian 0 0100100100100 30100 80 90 90 90 30 0 Soybean 0 0 30 40 20 20 10 30 10 20 0 20 0 0 Wheat 0 0 20 20 10 10 10 10 10 20 0 10 0 0 Table A Compounds 31 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72 Preemergence Barnyardgrass 10 0 30 0 - 90 - 90 80 80 50 80 10 90 Blackgrass 30 0 90 10 80 80 30 70 80 70 30 70 50 50 Corn 0 0 0 0 10 20 20 30 10 10 0 10 0 40 Foxtail, Giant - - - - 100 80100 70 50 40 90 - - 90 Goosegrass - - - - 100 - 90 - - - - - - - Kochia 10 0 90 0100100100100100 100 10100 60100 Oat, Wild 10 0 50 0 30 40 30 30 30 30 20 40 10 40 Pigweed, Palmer 80 0100 90100100100100100 100 90100100100 Ragweed 0 0 20 0 40 30 10 70 50 70 0 - - 40 Ryegrass, Italian 20 0 50 10 40 80 30 90 90100 60 90 60 90 Soybean 0 0 10 0 20 10 20 20 20 20 0 50 0 10 Wheat 0 0 10 0 0 0 10 20 10 10 10 10 0 10 Table A Compounds 31 g ai/ha 73 74 75 76 77 78 79 80 81 82 83 84 85 86 Preemergence Barnyardgrass 70 70 0 0 60 50 80 30 50 60 70 0 20 40 Blackgrass 80 70 50 50 20 40 50 40 50 70 60 0 60 50 Corn 10 10 20 20 40 0 20 0 10 20 20 0 0 0 Foxtail, Giant 70100 - - - - 80 80100 90 90 0 0 0 Goosegrass - - - - - - - - - - - - - - Kochia 80 90100100100 70100 80 90 90100 0 80100 Oat, Wild 50 20 60 40 20 20 40 40 20 80 30 0 30 20 Pigweed, Palmer 100100100100100100100100100 100100 0100100 Ragweed 30 80 40 70 0 60 20 0 0 20 40 0 0 30 Ryegrass, Italian 90100 90 90 90 70 80 90 80100 60 0 70 40 Soybean 10 10 40 20 0 20 10 0 0 10 10 0 0 10 Wheat 10 10 30 20 20 0 10 0 10 10 20 0 10 0 Table A Compounds 31 g ai/ha 87 88 89 90 91 92 93 94 95 96 Preemergence Barnyardgrass 50 20 70 50 30 30 10 0 0 0 Blackgrass 50 10 70 80 40 80 40 0 0 10 Corn 10 10 10 10 0 10 0 0 0 0 Foxtail, Giant - - 30 - - 90 - - - - Goosegrass - - - - - - - - - - Kochia 100 20100 90 90100 90 0 0 0 Oat, Wild 70 20 20 70 50 40 20 0 0 0 Pigweed, Palmer 100100100100 90100100 0 20 0 Ragweed 40 20 40 30 30 0 - 0 0 0 Ryegrass, Italian 90 90 80 90 90 60 50 10 10 20 Soybean - 20 10 0 10 20 0 0 0 0 Wheat 10 10 10 10 10 10 0 0 0 0 Table A Compounds 500 g ai/ha 12 53 Postemergence Blackgrass 100100 Corn 20 50 Foxtail, Giant 90 90 Galium 90100 Goosegrass 90 90 Horseweed 90100 Kochia 100100 Oat, Wild 30100 Pigweed, Palmer 100100 Ragweed 70100 Ryegrass, Italian 100100 Soybean 60100 Wheat 20 40 Table A Compounds 125 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Postemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 80 90 20 50 90 90 80 80 60 10 10 60 10 90 Corn 40 80 30 40 80 10 40 20 20 10 10 20 20 60 Foxtail, Giant 70 90 30 30 90 90 90 80 90 30 20 40 20 90 Galium 100100 60 50100100100 80100 40 40 60100100 Goosegrass 90 90 40 - 90 90 90 90 90 20 10 50 50 90 Horseweed 80 70 30 40 70 80 90 70 90 10 0 60 80100 Kochia 90 90 90 90 90 90100100100 70 70100 80 90 Oat, Wild 60 90 20 30100 90 90 80 60 10 10 30 20 80 Pigweed, Palmer 90100100100100100 90100100 50 60100 70 80 Ragweed 70 60 40 50 70100100100100 20 20 60 60 80 Ryegrass, Italian 100100 30 70100100100100100 30 0 70 60100 Soybean 70 80 40 50 90 70 80 60 90 20 10 50 50 70 Wheat 20 50 10 20 60 20 20 10 10 10 10 10 10 40 Table A Compounds 125 g ai/ha 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Postemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 80 60 20 0 10 70 90 90 80 90 90 10 10 40 Corn 60 30 10 0 0 40 20 30 50 40 70 10 10 30 Foxtail, Giant 90 60 20 0 10 60 20 60 90 90 90 20 10 50 Galium 100100 40 0 20100100100100100100 70 90 90 Goosegrass 90 80 20 0 10 90 90 90 90 90 90 30 30 60 Horseweed 50 50 0 0 0100100100100 80 60 50 30 60 Kochia 90 90 90 0 40 90 90 90100 90 90 50 50 80 Oat, Wild 90 40 20 0 10 30 50 60 80 50 90 20 10 40 Pigweed, Palmer 100100 80 30 70 90100100100100100 80 60100 Ragweed 90 80 30 0 10100 90100100 60 60 50 40 50 Ryegrass, Italian 100 70 30 0 0100 90100100100100 10 20 60 Soybean 80 80 30 0 20 90 80 80 90 80 80 10 20 50 Wheat 30 10 0 0 10 20 20 40 30 30 40 10 10 10 Table A Compounds 125 g ai/ha 29 30 31 32 33 34 35 37 40 41 42 Postemergence Barnyardgrass - - - - - - - - - - - Blackgrass 90 90 90 80 30 50 90 90 90 40 70 Corn 80 70 50 30 10 20 80 50 40 10 30 Foxtail, Giant 90 90 90 50 70 10 90 90 90 50100 Galium 100100100 100100 70100 100 100100100 Goosegrass 90 90 90 70 50 50 90 90 90 80 90 Horseweed 90 80 80 80100 90 80 100 80 70100 Kochia 90 90 90 90 90 90 90 90 100100100 Oat, Wild 90 80 80 50 30 20 80 90 90 60 90 Pigweed, Palmer 100100100100 70100 90 100 90100100 Ragweed 80 70 60 80 60 70 70 100 80100100 Ryegrass, Italian 90100 80 80 50 70100 100 100 90100 Soybean 80 70 60 60 40 40 70 90 70100 90 Wheat 50 40 20 20 10 10 50 40 30 10 30 Table A Compounds 125 g ai/ha 43 44 45 46 47 48 49 50 51 52 53 54 55 56 Postemergence Barnyardgrass - - - - - - - - - - - 90 90 90 Blackgrass 70 0 0 90 90 90 80 50 70 90 90 90100 90 Corn 10 0 0 60 70 20 60 40 30 20 30 40 70 70 Foxtail, Giant 60 10 10 90 90 90 90 90100 80 90 - 90 90 Galium 100 10 0100100100100100100 100100100100100 Goosegrass 60 10 10 90 90 70 90 90 90 90 90 - - - Horseweed 30 0 0 100100 80 50100100100100 - 50 70 Kochia 90 20 10 90100100100100100 90100 90 90 90 Oat, Wild 30 0 0 90 90 40 90 50 50 50100 90 90100 Pigweed, Palmer 100 80 50100100100 90100100100100100100100 Ragweed 50 0 0 100100 80 70100100100100 90 50 70 Ryegrass, Italian 100 0 0100100 90100 70100100100 90100100 Soybean 50 0 0 80100 80 90 90 90 80100 80100 80 Wheat 10 0 0 40 50 30 30 20 30 30 20 30 60 30 Table A Compounds 125 g ai/ha 57 58 59 60 61 62 63 64 65 66 67 68 69 70 Postemergence Barnyardgrass 20 10 20 0 90 30 - 100 - 100 90 90 90100 Blackgrass 30 10 20 0 90 80 90 90 90 90100 90 80 90 Corn 10 10 10 0 30 20 70 80 70 90 70 60 40 70 Foxtail, Giant - - - - - - 90 90 90 80 80 80 90 - Galium 70 80 90 50100 90100 90100100100100100 90 Goosegrass - - - - - - 90 - 90 - - - - - Horseweed 30 - - 20100 50 90 80 70 90 70 90 50100 Kochia 90 90 90 20 90 90 90 90 90 90 90 90 90 90 Oat, Wild 20 20 30 20 90 40 80 80 90 90100 40 50 90 Pigweed, Palmer 80 80100 50100100100100100 100100100100100 Ragweed 10 50 80 20 - - 50 70 60 90 70 80 70 80 Ryegrass, Italian 60 20 40 20100 40100100100100100100100 90 Soybean 70 60 70 10100 60 70100 70100 80 70 70 90 Wheat 20 10 10 10 20 10 30 50 50 70 50 30 30 80 Table A Compounds 125 g ai/ha 71 72 73 74 75 76 77 78 79 80 81 82 83 84 Postemergence Barnyardgrass 40 90 90 90100 90100100 90 80 90 90 90 0 Blackgrass 80 90 90 90 90 90 90 40 90100100 90 90 0 Corn 20 90 60 50 80 70 90 30 50 40 50 40 70 0 Foxtail, Giant - 90 70 90 - - - - 80 90 90 90 90 0 Galium 90100100 100100 90100 90100 70100100100 0 Goosegrass - - - - - - - - - - - - - - Horseweed 100 90100 80 90 90 80100 80 90 70 80 70 0 Kochia 90 90 90 90 90 90 90 90 90 90100 90 90 10 Oat, Wild 40 90 90 60 90100100 30 80 90100100100 10 Pigweed, Palmer 100100100100100100100 90100100100100100 10 Ragweed 70100 90 80 90 80 80 60 70 80 70100 70 0 Ryegrass, Italian 60100 90 90 90 80 90 40100100100 90100 0 Soybean 70 90100 80 80 80 80 80 80 70 80 80 70 0 Wheat 20 70 30 20 80 50 80 20 50 30 30 20 40 0 Table A Compounds 125 g ai/ha 85 86 87 88 89 90 91 92 93 94 95 96 Postemergence Barnyardgrass 70 90100100 90 80100 80 30 10 10 10 Blackgrass 70 80 90 90 90 90 80 90 50 20 40 10 Corn 40 40 40 40 90 20 30 40 20 10 10 10 Foxtail, Giant 30 60 - - 80 - - 90 - - - - Galium 100100100 - 100 90 - 100 - 70 80 - Goosegrass - - - - - - - - - - - - Horseweed 100100100 80 60 - 90 70 50 20 0 30 Kochia 90 90 90 90 90 90 90 90 90 70 60 50 Oat, Wild 60 40100 40 80 80 80 70 40 20 10 20 Pigweed, Palmer 100100100100100100100100100 80 70 70 Ragweed 80 70 - 70 90 80 90 60 50 40 40 30 Ryegrass, Italian 90 90100 70100 90 90 90 50 20 20 20 Soybean 80 80 90 80 80 80 90 80 70 30 30 40 Wheat 20 20 20 20 60 30 40 30 20 10 10 10 Table A Compounds 31 g ai/ha 1 2 3 4 5 6 7 8 9 10 11 13 14 15 Postemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 30 90 0 10 50 50 50 40 50 0 0 0 30 20 Corn 30 70 10 10 50 10 10 10 20 10 0 0 40 40 Foxtail, Giant 30 70 10 10 30 50 50 30 80 10 10 10 50 50 Galium 60100 20 10 70100 80 70100 10 10 30100100 Goosegrass 70 70 20 - 20 80 80 50 60 10 0 10 70 60 Horseweed 60 40 10 0 20 30 60 20 60 0 0 10 80 10 Kochia 90 90 50 90 90 90 90100100 20 70 40 90 90 Oat, Wild 30 60 10 20 20 70 50 30 30 0 10 10 40 30 Pigweed, Palmer 90100 70 80100100 70100 70 60 60 30 50 90 Ragweed 60 40 20 10 40 40100 70 80 10 10 20 70 60 Ryegrass, Italian 50100 10 20 70 80100 50 80 0 0 10 60 70 Soybean 60 60 30 20 60 50 60 40 50 0 0 10 50 70 Wheat 10 30 10 10 10 10 10 10 10 0 0 0 20 20 Table A Compounds 31 g ai/ha 16 17 18 19 20 21 22 23 24 25 26 27 28 29 Postemergence Barnyardgrass - - - - - - - - - - - - - - Blackgrass 10 10 0 0 60 70 60 30 50 80 0 0 20 80 Corn 20 10 0 0 10 20 20 30 20 50 10 10 10 60 Foxtail, Giant 10 10 0 10 20 10 20 60 70 90 10 10 10 90 Galium 90 20 0 0 90 80 80100 70 80 10 30 50100 Goosegrass 30 20 0 0 80 50 70 60 80 80 10 10 20 80 Horseweed 30 0 0 0 100 60 50 80 30 20 10 10 20 60 Kochia 90 40 0 10 90 90 90100 90 90 10 20 70 90 Oat, Wild 30 10 0 0 20 20 30 50 30 50 10 0 30 70 Pigweed, Palmer 90 60 30 60 90 80 90100100100 40 30 90100 Ragweed 30 20 0 10 90 70 80 60 40 30 0 0 50 70 Ryegrass, Italian 60 0 0 0 50 70 40100 40 50 0 0 20 70 Soybean 50 20 0 0 60 30 50 90 50 60 10 0 40 60 Wheat 10 0 0 0 10 10 20 30 10 20 0 0 10 20 Table A Compounds 31 g ai/ha 30 31 32 33 34 35 37 40 41 42 43 Postemergence Barnyardgrass - - - - - - - - - - - Blackgrass 60 40 30 10 20 50 40 50 30 50 10 Corn 50 40 20 10 10 60 40 10 10 50 10 Foxtail, Giant 80 80 20 10 10 80 30 30 20 50 20 Galium 100 80 60 30 60100100 70 70100 90 Goosegrass 70 50 40 10 10 70 50 30 60 60 30 Horseweed 60 40 60 30 10 30 70 20 30 80 0 Kochia 90 80 80 60 40 90 90 90 90100 70 Oat, Wild 40 50 20 10 10 40 50 40 20 30 20 Pigweed, Palmer 100100100 50 70 80 70 80 70 90 90 Ragweed 70 30 50 30 50 70 70 40 50100 20 Ryegrass, Italian 50 60 60 10 20 60 40 50 40 60 40 Soybean 50 40 50 30 20 60 60 50 50 60 20 Wheat 20 10 20 10 10 20 20 10 10 20 10 Table A Compounds 31 g ai/ha 44 45 46 47 48 49 50 51 52 54 55 56 57 58 Postemergence Barnyardgrass - - - - - - - - - 50 60 80 10 0 Blackgrass 0 0 70 70 40 50 30 40 50 60 50 70 10 0 Corn 0 0 30 50 20 20 10 30 20 20 20 50 10 10 Foxtail, Giant 0 10 50 50 30 30 20 30 40 - 50 70 - - Galium 0 0100 100 70 70100 70 70 90 70100 50 40 Goosegrass 10 10 50 70 40 50 40 70 60 - - - - - Horseweed 0 0 60 70 20 30 50100 40 - 30 40 20 - Kochia 0 20 90100100 90 90100 80 80 90 90 60 30 Oat, Wild 0 0 50 70 20 40 20 30 30 60 30 30 20 10 Pigweed, Palmer 30 40100100100 90100100100100100 90 70 70 Ragweed 0 0 60 70 50 60100 90 50 80 40 60 0 30 Ryegrass, Italian 0 0 60 80 70 40 50 70 50 40 50 50 40 10 Soybean 0 0 60 80 50 60 50 60 60 70 60 60 70 40 Wheat 0 0 30 30 20 20 20 20 20 20 10 30 10 0 Table A Compounds 31 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72 Postemergence Barnyardgrass 10 0 10 10 - 80 - 90 90 90 60 60 20 80 Blackgrass 10 0 80 10 60 70 50 90 70 90 50 70 30 70 Corn 10 0 10 10 50 60 60 70 50 40 20 30 10 70 Foxtail, Giant - - - - 90 80 80 70 40 50 50 - - 80 Galium 90 0 80 50 80 70 80100 70100 70 90 90 70 Goosegrass - - - - 70 - 50 - - - - - - - Horseweed - 0 60 30 30 60 30 70 50 80 30100 60 30 Kochia 60 10 80 50 90 90 90 90 90 90 90 90 70 90 Oat, Wild 30 10 40 20 50 70 80 50 30 30 20 30 20 30 Pigweed, Palmer 80 10100100100100100100100 100100100100 90 Ragweed 50 0 - - 50 40 60 60 50 70 60 60 60100 Ryegrass, Italian 10 0 30 0 70 80 70 80 70 90 70 50 30 80 Soybean 70 10 70 40 50 80 50 80 50 50 50 70 60 70 Wheat 10 0 20 10 20 30 50 30 20 20 20 20 10 30 Table A Compounds 31 g ai/ha 73 74 75 76 77 78 79 80 81 82 83 84 85 86 Postemergence Barnyardgrass 70 80 70 70 80 40 60 30 40 40 60 0 20 40 Blackgrass 70 80 80 60 70 30 30 40 60 60 70 0 50 30 Corn 40 30 40 50 50 10 30 20 30 20 60 0 10 20 Foxtail, Giant 40 90 - - - - 60 60 70 60 60 0 20 20 Galium 100 70100 90100 90100 60 70 60 70 0 60 60 Goosegrass - - - - - - - - - - - - - - Horseweed 50 70 90 80 90 40 30 40 30 50 50 0 40 60 Kochia 90 90 80 90 90 90 90 80 80 90 90 10 90 90 Oat, Wild 30 30 80 40100 20 50 50 50 70 50 10 40 30 Pigweed, Palmer 90100100100 90 80 90 90 90 80 80 10100 70 Ragweed 70 70 80 90 70 50 40 30 30 30 40 0 40 40 Ryegrass, Italian 80 70 70 70 80 20 60 70 90 70 60 0 40 40 Soybean 60 50 80 70 80 60 60 50 60 60 60 0 40 60 Wheat 20 20 30 20 40 20 30 20 20 20 30 0 20 20 Table A Compounds 31 g ai/ha 87 88 89 90 91 92 93 94 95 96 Postemergence Barnyardgrass 40 50 80 40 60 30 20 0 10 0 Blackgrass 70 30 80 70 - 30 30 0 10 0 Corn 10 10 60 10 20 20 10 10 10 0 Foxtail, Giant - - 40 - - 80 - - - - Galium 80 - 70 90 - 60 90 30 30 - Goosegrass - - - - - - - - - - Horseweed 100 80 50 - 80 30 50 0 0 0 Kochia 90 70 90 80 90 80 70 10 40 20 Oat, Wild 40 30 40 50 30 40 20 10 10 10 Pigweed, Palmer 100 60100100 90 80100 60 60 40 Ragweed - 50 60 70 70 30 60 30 40 10 Ryegrass, Italian 70 40 60 30 40 60 20 0 10 0 Soybean 70 70 60 70 70 60 50 10 20 10 Wheat 10 10 20 20 10 30 20 0 0 0 TEST B Plant species in the flooded paddy test selected from barnyardgrass (Echinochloa crus- galli), ducksalad (Heteranthera limosa), rice (Oryza sativa), and sedge, umbrella (small- flower umbrella sedge, Cyperus difformis) were grown to the 2-leaf stage for testing. At time of treatment, test pots were flooded to 3 cm above the soil surface, treated by application of test compounds directly to the paddy water, and then maintained at that water depth for the duration of the test. Treated plants and controls were maintained in a greenhouse for 13 days, after which time all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (–) response means no test result. Table B Compounds 250 g ai/ha 1 2 3 6 7 8 9 10 11 12 13 14 15 16 Flood Barnyardgrass 60 80 10 0 90 0 65 0 0 30 15 55 25 10 Ducksalad 98 95 20 65100 0 70 0 0 35 0100 15 0 Rice 20 15 0 0 45 0 35 0 0 15 25 10 20 0 Sedge, Umbrella 98 98 75 70 95 0 90 0 0 70 20 95 70 45 Table B Compounds 250 g ai/ha 17 18 19 20 21 22 23 24 25 26 27 28 29 30 Flood Barnyardgrass 0 0 0 60 65 35 75 50 90 0 0 20 75 65 Ducksalad 0 0 0 70 75 35 90 85 85 0 0 0 90 95 Rice 0 0 0 45 55 40 35 20 65 0 0 20 70 70 Sedge, Umbrella 0 0 0 90 85 70 98 80 90 0 0 10 98 98 Table B Compounds 250 g ai/ha 31 32 33 34 35 37 40 41 42 43 44 Flood Barnyardgrass 60 45 0 20 65 50 55 25 85 25 0 Ducksalad 95 55 0 60 90 85 85 55 98 35 0 Rice 30 15 0 20 15 40 45 15 65 25 0 Sedge, Umbrella 98 98 0 65 90 90 75 45 98 15 0 Table B Compounds 250 g ai/ha 45 46 47 48 49 50 51 52 53 54 55 56 57 58 Flood Barnyardgrass 0 35 50 50 45 60 55 60 70 45 70 80 0 15 Ducksalad 0 30 75 75 70 10 75 60 60 98 70 75 0 45 Rice 0 25 25 25 30 10 45 40 60 45 15 25 0 10 Sedge, Umbrella 0 90 95 85 98 98 95 95 75 98 95 90 0 70 Table B Compounds 250 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72 Flood Barnyardgrass 0 0 65 40 85 90 35 90 95 85 75 55 20 95 Ducksalad 0 0100 100 98 95 95 95 95 95 65 95 95 90 Rice 0 0 20 10 70 45 65 25 65 25 10 20 15 30 Sedge, Umbrella 25 0100100 98 95 95 98 98 98 75 95 95 98 Table B Compounds 250 g ai/ha 73 74 75 76 77 78 79 80 81 82 83 84 85 86 Flood Barnyardgrass 95 95 50 75 60 20 70 70 50 90 90 0 70 65 Ducksalad 75 95 80 60 85 65 85 85 45 80 45 0 40 45 Rice 35 45 25 15 15 5 15 20 10 15 35 0 20 25 Sedge, Umbrella 95 98 95100 85 75 95 95 98 80 80 0 70 85 Table B Compounds 250 g ai/ha 87 88 89 90 91 92 93 94 95 96 Flood Barnyardgrass 75 50 70 50 65 50 60 15 0 0 Ducksalad 100 60 65 95 70 50 85 45 15 0 Rice 15 5 15 10 20 10 10 0 0 0 Sedge, Umbrella 100 95 90 95 98 98 95 55 95 50 Test C Seeds of plant species corn (Zea mays), Soybean (Glycine max), winter wheat (Triticum aestivum), oilseed rape (Brassica napus), horseweed (Conyza canadensis), common ragweed (Ambrosia artemisiifolia), palmer amaranth (Amaranthus palmeri), common waterhemp (Amaranthus tuberculatus), galium (Galium aparine), field poppy (Papaver rhoeas), kochia (Kochia scoparia), giant foxtail (Setaria faberi), goosegrass (Eleusine indica), Italian ryegrass (Lolium multiflorum), blackgrass (Alopecurus myosuroides), and wild oat (Avena fatua) can be planted into pots containing a silt loam soil and treated preemergence with a directed soil spray and into pots containing a commercial potting mix and treated postmergence with a directed foiliar spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Treated plants and untreated controls can be maintained in a greenhouse for 13 days for postemergence and 20 days for preemergence testing, after which time the treated plants can be compared to untreated controls and visually evaluated for injury. TEST D Seeds of plant species oilseed rape (Brassica napus), winter wheat (Triticum aestivum), spring wheat (Triticum aestivum), winter barley (Hordeum vulgare), spring barley (Hordeum vulgare), galium (Galium aparine), kochia (Kochia scoparia), common chickweed (Stellaria media), field poppy (Papaver rhoeas), wild radish (Raphanus raphanistrum), Italian ryegrass (Lolium multiflorum), blackgrass (Alopecurus myosuroides), and wild oat (Avena fatua) can be planted into pots containing a silt loam soil and treated preemergence with a directed soil spray and into pots containing a commercial potting mix and treated postmergence with a directed foiliar spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. Treated plants and untreated controls can be maintained in a greenhouse for 13 days for postemergence and 20 days for preemergence testing, after which time the treated plants can be compared to untreated controls and visually evaluated for injury.

Claims

CLAIMS What is claimed is: 1. A compound selected from Formula 1, all stereoisomers, N-oxides, and salts thereof wherein J is selected from the group consisting of J-1 , J-2 , J-3 , , J-4 , J-5 J-6 J-7 J-8 J-9 J-10 J-11 Q is O, -CH2- or -(C=O)-; R1 is halogen, C1–C4 alkyl, C3–C4 cycloalkyl, C1–C3 haloalkyl, C1–C3 alkoxy, or C1– C3 haloalkoxy; R2 is H, halogen, CN, C1–C4 alkyl, C1–C3 haloalkyl or C1–C3 haloalkoxy; R3 is halogen, C1–C3 haloalkyl or C1–C3 haloalkoxy; R4 is H, halogen or methoxy; X is N or CR5; R5 is H, halogen, C1-C3 haloalkyl, CH3 or cyano; provided when R2 is H, R5 is other than H.
2. The compound of Claim 1 wherein J is J-1, J-2, J-3, J-4, J-5 or J-6.
3. The compound of Claim 2 wherein J is J-1, J-2 or J-3; Q is O or -CH2-.
4. The compound of Claim 3 wherein R1 is F, Cl, C1–C4 alkyl or C3–C4 cycloalkyl or C1–C3 alkoxy; and R3 is C1–C3 haloalkyl or C1–C3 haloalkoxy.
5. The compound of Claim 4 wherein R2 is C1–C3 haloalkyl; R4 is H, F or OMe; and R5 is H, halogen or C1–C3 haloalkyl.
6. The compound of Claim 5 wherein R1 is Cl, Me, Et, cyclopropyl or OMe; R2 is CF3; and R5 is H, Cl, Br or CF3.
7. The compound of Claim 6 wherein R5 is CF3.
8. The compound of Claim 2 wherein J is J-1; Q is O.
9. The compound of Claim 3 wherein X is CR5.
10. The compound of Claim 2 wherein J is J-2; X is CR5; and R5 is CF3.
11. The compound of Claim 1 selected from the group consisting of 3-ethyl-5-fluoro-2-[3-(trifluoromethoxy)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine; 3-ethyl-5-fluoro-6-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-[[6-(trifluoromethyl)- 2-pyridinyl]oxy]pyridine; 3-ethyl-5-fluoro-2-[3-(trifluoromethyl)phenoxy]-6-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine; 3-fluoro-5-methoxy-6-[3-(trifluoromethyl)phenoxy]-2-[3-(trifluoromethyl)-1H- pyrazol-1-yl]pyridine; and 2-[3-(difluoromethyl)-1H-pyrazol-1-yl]-5-Ethyl-3-fluoro-6-[3- (trifluoromethyl)phenoxy]pyridine.
12. A herbicidal composition comprising a compound of Claim 1 and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
13. A herbicidal composition comprising a compound of Claim 1, at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners, and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
14. A herbicidal mixture comprising (a) a compound of Claim 1, and (b) at least one additional active ingredient selected from (b1) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13) homogentisate solanesyltransferase (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, hydantocidin, icafolin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, (b16) herbicide safeners, and salts of compounds of (b1) through (b16).
15. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of Claim 1.
PCT/US2023/033659 2022-09-30 2023-09-26 Substituted fluoropyridine as herbicides WO2024072768A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202263411686P 2022-09-30 2022-09-30
US63/411,686 2022-09-30

Publications (1)

Publication Number Publication Date
WO2024072768A1 true WO2024072768A1 (en) 2024-04-04

Family

ID=88504897

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2023/033659 WO2024072768A1 (en) 2022-09-30 2023-09-26 Substituted fluoropyridine as herbicides

Country Status (1)

Country Link
WO (1) WO2024072768A1 (en)

Citations (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3235361A (en) 1962-10-29 1966-02-15 Du Pont Method for the control of undesirable vegetation
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
DE3246493A1 (en) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING WATER-DISPERSIBLE GRANULES
WO1991013546A1 (en) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Water-dispersible or water-soluble pesticide granules from heat-activated binders
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
WO1998040379A1 (en) * 1997-03-11 1998-09-17 E.I. Du Pont De Nemours And Company Heteroaryl azole herbicides
US20010011064A1 (en) * 1997-05-30 2001-08-02 American Cyanamid Company Herbicidal 3,5-difluoropyridines
US6448204B1 (en) * 1999-11-17 2002-09-10 Basf Aktiengesellschaft Herbicidal 2-aryloxy-4-methyl-6-pyrazol-1-yl-pyridines
WO2003022843A1 (en) * 2001-09-07 2003-03-20 Basf Aktiengesellschaft Pyrazolyl-substituted thienyloxypyridines
WO2003022831A1 (en) * 2001-09-07 2003-03-20 Basf Aktiengesellschaft 4-alkyl-substitute thienyloxy-pyridines
WO2003024222A1 (en) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
DE10234875A1 (en) * 2002-07-25 2004-02-05 Bayer Cropscience Gmbh 4-trifluoromethylpyrazolyl substituted pyridines and pyrimidines
WO2004013129A1 (en) * 2002-07-25 2004-02-12 Bayer Cropscience Gmbh 4-trifluoromethylpyrazolyl substituted pyridines and pyrimidines
WO2019101513A1 (en) * 2017-11-23 2019-05-31 Basf Se Herbicidal pyridylethers

Patent Citations (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3235361A (en) 1962-10-29 1966-02-15 Du Pont Method for the control of undesirable vegetation
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
DE3246493A1 (en) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING WATER-DISPERSIBLE GRANULES
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
WO1991013546A1 (en) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Water-dispersible or water-soluble pesticide granules from heat-activated binders
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
WO1998040379A1 (en) * 1997-03-11 1998-09-17 E.I. Du Pont De Nemours And Company Heteroaryl azole herbicides
US20010011064A1 (en) * 1997-05-30 2001-08-02 American Cyanamid Company Herbicidal 3,5-difluoropyridines
US6448204B1 (en) * 1999-11-17 2002-09-10 Basf Aktiengesellschaft Herbicidal 2-aryloxy-4-methyl-6-pyrazol-1-yl-pyridines
WO2003022843A1 (en) * 2001-09-07 2003-03-20 Basf Aktiengesellschaft Pyrazolyl-substituted thienyloxypyridines
WO2003022831A1 (en) * 2001-09-07 2003-03-20 Basf Aktiengesellschaft 4-alkyl-substitute thienyloxy-pyridines
WO2003024222A1 (en) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
DE10234875A1 (en) * 2002-07-25 2004-02-05 Bayer Cropscience Gmbh 4-trifluoromethylpyrazolyl substituted pyridines and pyrimidines
WO2004013129A1 (en) * 2002-07-25 2004-02-12 Bayer Cropscience Gmbh 4-trifluoromethylpyrazolyl substituted pyridines and pyrimidines
WO2019101513A1 (en) * 2017-11-23 2019-05-31 Basf Se Herbicidal pyridylethers

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
"Comprehensive Heterocyclic Chemistry II", 1996, PERGAMON PRESS
"Perry's Chemical Engineer's Handbook", 1963, MCGRAW-HILL, pages: 8 - 57
"Polymorphism in the Pharmaceutical Industry", 2006, WILEY-VCH
"The BioPesticide Manual,", 2001, BRITISH CROP PROTECTION COUNCIL
"The Pesticide Manual", 2003, BRITISH CROP PROTECTION COUNCIL
A. S. DAVIDSONB. MILWIDSKY: "Synthetic Detergents", 1987, JOHN WILEY AND SONS
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 November 1967 (1967-11-04), pages 147 - 48
CAS, no. 27499989-21-6
G. W. H. CHEESEMANE. S. G. WERSTIUK: "Comprehensive Heterocyclic Chemistry", vol. 22, 1984, PERGAMON PRESS, pages: 390 - 392
GREENE, T. WWUTS, P. G. M: "Protective Groups in Organic Synthesis", 1991, WILEY
HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC PUBLICATIONS
LAROCK, R. C: "Comprehensive Organic Transformations: A Guide to Functional Group Preparations", 1999, THE ROYAL SOCIETY OF CHEMISTR, article "The Formulator's Toolbox - Product Forms for Modem Agriculture", pages: 120 - 133
RICHMOND, UK: "Developments in formulation technology", 2000, PJB PUBLICATIONS
SISELYWOOD: "McCutcheon's Emulsifiers and Detergents", 1964, MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO
WATKINS ET AL.: "Handbook of Insecticide Dust Diluents and Carriers", 1950, DORLAND BOOKS

Similar Documents

Publication Publication Date Title
AU2016259529B2 (en) Aryl substituted bicyclic compounds as herbicides
AU2018277041B2 (en) Herbicidal 3-substituted lactams
US11292770B2 (en) Pyridazinone herbicides
WO2016196019A1 (en) Substituted cyclic amides as herbicides
AU2018277537B2 (en) Herbicidal amides
EP3645515B1 (en) 4-(3,4-dihydronaphth-1-yl or 2h-chromen-4-yl)-5-hydroxy-2h-pyradizin-3-ones as herbicides
AU2018262478B2 (en) Pyrimidinyloxy benzo-fused compounds as herbicides
AU2015290153A1 (en) Bis(aryl)catechol derivatives as herbicides
EP2912022B1 (en) Substituted triazoles as herbicides
WO2021183980A1 (en) Substituted pyrimidines and triazines as herbicides
WO2015191377A1 (en) Herbicidal substituted 3-arylpyrazoles
EP3185684A1 (en) Herbicidal triazoles
CA3127789A1 (en) Diamino-substituted pyridines and pyrimidines as herbicides
WO2024072768A1 (en) Substituted fluoropyridine as herbicides
WO2023129493A1 (en) Substituted cyclopropylpyrimidne herbicides
EP4188093A1 (en) Substituted haloalkyl sulfonanilide herbicides
EP4294791A1 (en) Herbicidal cyclic amides n-substituted with a haloalkylsulfonylanilide group
WO2022140309A1 (en) Substituted pyridazinone herbicides
WO2024015425A1 (en) Herbicidal benzoxazines
IL269625A (en) Novel pyridazinone herbicides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23793148

Country of ref document: EP

Kind code of ref document: A1